rdkit/Code/GraphMol/ForceFieldHelpers/UFF/Builder.cpp

//  Copyright (C) 2004-2018 Greg Landrum and Rational Discovery LLC
//
//   @@ All Rights Reserved @@
//  This file is part of the RDKit.
//  The contents are covered by the terms of the BSD license
//  which is included in the file license.txt, found at the root
//  of the RDKit source tree.
//
#include <cmath>

#include <RDGeneral/Invariant.h>
#include <GraphMol/RDKitBase.h>
#include <GraphMol/SmilesParse/SmilesParse.h>
#include <GraphMol/Substruct/SubstructMatch.h>

#include <ForceField/ForceField.h>
#include <ForceField/UFF/Params.h>
#include <ForceField/UFF/Contribs.h>

#include "AtomTyper.h"
#include "Builder.h"
namespace RDKit {
namespace UFF {
using namespace ForceFields::UFF;

namespace Tools {
// ------------------------------------------------------------------------
//
//
//
// ------------------------------------------------------------------------
void addBonds(const ROMol &mol, const AtomicParamVect &params,
              ForceFields::ForceField *field) {
  PRECONDITION(mol.getNumAtoms() == params.size(), "bad parameters");
  PRECONDITION(field, "bad forcefield");

  for (const auto bond : mol.bonds()) {
    int idx1 = bond->getBeginAtomIdx();
    int idx2 = bond->getEndAtomIdx();

    // FIX: recognize amide bonds here.

    if (params[idx1] && params[idx2]) {
      BondStretchContrib *contrib;
      contrib =
          new BondStretchContrib(field, idx1, idx2, bond->getBondTypeAsDouble(),
                                 params[idx1], params[idx2]);
      field->contribs().push_back(ForceFields::ContribPtr(contrib));
    }
  }
}

unsigned int twoBitCellPos(unsigned int nAtoms, int i, int j) {
  if (j < i) {
    std::swap(i, j);
  }

  return i * (nAtoms - 1) + i * (1 - i) / 2 + j;
}

void setTwoBitCell(boost::shared_array<std::uint8_t> &res, unsigned int pos,
                   std::uint8_t value) {
  unsigned int twoBitPos = pos / 4;
  unsigned int shift = 2 * (pos % 4);
  std::uint8_t twoBitMask = 3 << shift;
  res[twoBitPos] = ((res[twoBitPos] & (~twoBitMask)) | (value << shift));
}

std::uint8_t getTwoBitCell(boost::shared_array<std::uint8_t> &res,
                           unsigned int pos) {
  unsigned int twoBitPos = pos / 4;
  unsigned int shift = 2 * (pos % 4);
  std::uint8_t twoBitMask = 3 << shift;

  return ((res[twoBitPos] & twoBitMask) >> shift);
}

// ------------------------------------------------------------------------
//
// the two-bit matrix returned by this contains:
//   0: if atoms i and j are directly connected
//   1: if atoms i and j are connected via an atom
//   2: if atoms i and j are in a 1,4 relationship
//   3: otherwise
//
//  NOTE: the caller is responsible for calling delete []
//  on the result
//
// ------------------------------------------------------------------------
boost::shared_array<std::uint8_t> buildNeighborMatrix(const ROMol &mol) {
  const std::uint8_t RELATION_1_X_INIT = RELATION_1_X | (RELATION_1_X << 2) |
                                         (RELATION_1_X << 4) |
                                         (RELATION_1_X << 6);
  unsigned int nAtoms = mol.getNumAtoms();
  unsigned nTwoBitCells = (nAtoms * (nAtoms + 1) - 1) / 8 + 1;
  boost::shared_array<std::uint8_t> res(new std::uint8_t[nTwoBitCells]);
  std::memset(res.get(), RELATION_1_X_INIT, nTwoBitCells);
  for (const auto bondi : mol.bonds()) {
    setTwoBitCell(
        res,
        twoBitCellPos(nAtoms, bondi->getBeginAtomIdx(), bondi->getEndAtomIdx()),
        RELATION_1_2);
    unsigned int bondiBeginAtomIdx = bondi->getBeginAtomIdx();
    unsigned int bondiEndAtomIdx = bondi->getEndAtomIdx();
    for (const auto bondj : mol.bonds()) {
      if (bondj == bondi) {
        continue;
      }
      int idx1 = -1;
      int idx3 = -1;
      unsigned int bondjBeginAtomIdx = bondj->getBeginAtomIdx();
      unsigned int bondjEndAtomIdx = bondj->getEndAtomIdx();
      if (bondiBeginAtomIdx == bondjBeginAtomIdx) {
        idx1 = bondiEndAtomIdx;
        idx3 = bondjEndAtomIdx;
      } else if (bondiBeginAtomIdx == bondjEndAtomIdx) {
        idx1 = bondiEndAtomIdx;
        idx3 = bondjBeginAtomIdx;
      } else if (bondiEndAtomIdx == bondjBeginAtomIdx) {
        idx1 = bondiBeginAtomIdx;
        idx3 = bondjEndAtomIdx;
      } else if (bondiEndAtomIdx == bondjEndAtomIdx) {
        idx1 = bondiBeginAtomIdx;
        idx3 = bondjBeginAtomIdx;
      }
      if (idx1 > -1) {
        setTwoBitCell(res, twoBitCellPos(nAtoms, idx1, idx3), RELATION_1_3);
      }
    }
  }
  return res;
}

// ------------------------------------------------------------------------
//
//
//
// ------------------------------------------------------------------------
void addAngles(const ROMol &mol, const AtomicParamVect &params,
               ForceFields::ForceField *field) {
  PRECONDITION(mol.getNumAtoms() == params.size(), "bad parameters");
  PRECONDITION(field, "bad forcefield");
  ROMol::ADJ_ITER nbr1Idx;
  ROMol::ADJ_ITER end1Nbrs;
  ROMol::ADJ_ITER nbr2Idx;
  ROMol::ADJ_ITER end2Nbrs;
  RingInfo *rings = mol.getRingInfo();

  unsigned int nAtoms = mol.getNumAtoms();
  for (unsigned int j = 0; j < nAtoms; j++) {
    if (!params[j]) {
      continue;
    }
    const Atom *atomJ = mol.getAtomWithIdx(j);
    if (atomJ->getDegree() == 1) {
      continue;
    }
    boost::tie(nbr1Idx, end1Nbrs) = mol.getAtomNeighbors(atomJ);
    for (; nbr1Idx != end1Nbrs; nbr1Idx++) {
      const Atom *atomI = mol[*nbr1Idx];
      unsigned int i = atomI->getIdx();
      if (!params[i]) {
        continue;
      }
      boost::tie(nbr2Idx, end2Nbrs) = mol.getAtomNeighbors(atomJ);
      for (; nbr2Idx != end2Nbrs; nbr2Idx++) {
        if (nbr2Idx < (nbr1Idx + 1)) {
          continue;
        }
        const Atom *atomK = mol[*nbr2Idx];
        unsigned int k = atomK->getIdx();
        if (!params[k]) {
          continue;
        }
        // skip special cases:
        if (!(atomJ->getHybridization() == Atom::SP3D &&
              atomJ->getDegree() == 5)) {
          const Bond *b1 = mol.getBondBetweenAtoms(i, j);
          const Bond *b2 = mol.getBondBetweenAtoms(k, j);
          // FIX: recognize amide bonds here.
          AngleBendContrib *contrib;
          int order = 0;
          switch (atomJ->getHybridization()) {
            case Atom::SP:
              order = 1;
              break;
            case Atom::SP2:
              order = 3;
              // the following is a hack to get decent geometries
              // with 3- and 4-membered rings incorporating sp2 atoms
              // if the central atom is in a ring of size 3
              if (rings->isAtomInRingOfSize(j, 3)) {
                // if the central atom and one of the bonded atoms, but not the
                //  other one are inside a ring, then this angle is between a
                // ring substituent and a ring edge
                if (rings->isAtomInRingOfSize(i, 3) !=
                    rings->isAtomInRingOfSize(k, 3)) {
                  order = 30;
                }
                // if all atoms are inside the ring, then this is one of ring
                // angles
                else if (rings->isAtomInRingOfSize(i, 3) &&
                         rings->isAtomInRingOfSize(k, 3)) {
                  order = 35;
                }
              }
              // if the central atom is in a ring of size 4
              else if (rings->isAtomInRingOfSize(j, 4)) {
                // if the central atom and one of the bonded atoms, but not the
                //  other one are inside a ring, then this angle is between a
                // ring substituent and a ring edge
                if (rings->isAtomInRingOfSize(i, 4) !=
                    rings->isAtomInRingOfSize(k, 4)) {
                  order = 40;
                }
                // if all atoms are inside the ring, then this is one of ring
                // angles
                else if (rings->isAtomInRingOfSize(i, 4) &&
                         rings->isAtomInRingOfSize(k, 4)) {
                  order = 45;
                }
              }
              // end of the hack
              break;
            case Atom::SP3D2:
              order = 4;
              break;
            default:
              order = 0;
              break;
          }

          contrib =
              new AngleBendContrib(field, i, j, k, b1->getBondTypeAsDouble(),
                                   b2->getBondTypeAsDouble(), params[i],
                                   params[j], params[k], order);
          field->contribs().push_back(ForceFields::ContribPtr(contrib));
        }
      }
    }
  }
}

// ------------------------------------------------------------------------
//
//
//
// ------------------------------------------------------------------------
void addTrigonalBipyramidAngles(const Atom *atom, const ROMol &mol, int confId,
                                const AtomicParamVect &params,
                                ForceFields::ForceField *field) {
  PRECONDITION(atom, "bad atom");
  PRECONDITION(atom->getHybridization() == Atom::SP3D, "bad hybridization");
  PRECONDITION(atom->getDegree() == 5, "bad degree");
  PRECONDITION(mol.getNumAtoms() == params.size(), "bad parameters");
  PRECONDITION(field, "bad forcefield");

  const Bond *ax1 = nullptr, *ax2 = nullptr;
  const Bond *eq1 = nullptr, *eq2 = nullptr, *eq3 = nullptr;

  const Conformer &conf = mol.getConformer(confId);
  //------------------------------------------------------------
  // identify the axial and equatorial bonds:
  double mostNeg = 100.0;
  ROMol::OEDGE_ITER beg1, end1;
  boost::tie(beg1, end1) = mol.getAtomBonds(atom);
  unsigned int aid = atom->getIdx();
  while (beg1 != end1) {
    const Bond *bond1 = mol[*beg1];
    unsigned int oaid = bond1->getOtherAtomIdx(aid);
    RDGeom::Point3D v1 =
        conf.getAtomPos(aid).directionVector(conf.getAtomPos(oaid));

    ROMol::OEDGE_ITER beg2, end2;
    boost::tie(beg2, end2) = mol.getAtomBonds(atom);
    while (beg2 != end2) {
      const Bond *bond2 = mol[*beg2];
      if (bond2->getIdx() > bond1->getIdx()) {
        unsigned int oaid2 = bond2->getOtherAtomIdx(aid);
        RDGeom::Point3D v2 =
            conf.getAtomPos(aid).directionVector(conf.getAtomPos(oaid2));
        double dot = v1.dotProduct(v2);
        if (dot < mostNeg) {
          mostNeg = dot;
          ax1 = bond1;
          ax2 = bond2;
        }
      }
      ++beg2;
    }
    ++beg1;
  }
  CHECK_INVARIANT(ax1, "axial bond not found");
  CHECK_INVARIANT(ax2, "axial bond not found");

  boost::tie(beg1, end1) = mol.getAtomBonds(atom);
  while (beg1 != end1) {
    const Bond *bond = mol[*beg1];
    ++beg1;
    if (bond == ax1 || bond == ax2) {
      continue;
    }
    if (!eq1) {
      eq1 = bond;
    } else if (!eq2) {
      eq2 = bond;
    } else if (!eq3) {
      eq3 = bond;
    }
  }

  CHECK_INVARIANT(eq1, "equatorial bond not found");
  CHECK_INVARIANT(eq2, "equatorial bond not found");
  CHECK_INVARIANT(eq3, "equatorial bond not found");

  //------------------------------------------------------------
  // alright, add the angles:
  AngleBendContrib *contrib;
  int atomIdx = atom->getIdx();
  int i, j;

  // Axial-Axial
  i = ax1->getOtherAtomIdx(atomIdx);
  j = ax2->getOtherAtomIdx(atomIdx);
  if (params[i] && params[j]) {
    contrib = new AngleBendContrib(
        field, i, atomIdx, j, ax1->getBondTypeAsDouble(),
        ax2->getBondTypeAsDouble(), params[i], params[atomIdx], params[j], 2);
    field->contribs().push_back(ForceFields::ContribPtr(contrib));
  }
  // Equatorial-Equatorial
  i = eq1->getOtherAtomIdx(atomIdx);
  j = eq2->getOtherAtomIdx(atomIdx);
  if (params[i] && params[j]) {
    contrib = new AngleBendContrib(
        field, i, atomIdx, j, eq1->getBondTypeAsDouble(),
        eq2->getBondTypeAsDouble(), params[i], params[atomIdx], params[j], 3);
    field->contribs().push_back(ForceFields::ContribPtr(contrib));
  }
  i = eq1->getOtherAtomIdx(atomIdx);
  j = eq3->getOtherAtomIdx(atomIdx);
  if (params[i] && params[j]) {
    contrib = new AngleBendContrib(
        field, i, atomIdx, j, eq1->getBondTypeAsDouble(),
        eq3->getBondTypeAsDouble(), params[i], params[atomIdx], params[j], 3);
    field->contribs().push_back(ForceFields::ContribPtr(contrib));
  }
  i = eq2->getOtherAtomIdx(atomIdx);
  j = eq3->getOtherAtomIdx(atomIdx);
  if (params[i] && params[j]) {
    contrib = new AngleBendContrib(
        field, i, atomIdx, j, eq2->getBondTypeAsDouble(),
        eq3->getBondTypeAsDouble(), params[i], params[atomIdx], params[j], 3);
    field->contribs().push_back(ForceFields::ContribPtr(contrib));
  }

  // Axial-Equatorial
  i = ax1->getOtherAtomIdx(atomIdx);
  j = eq1->getOtherAtomIdx(atomIdx);
  if (params[i] && params[j]) {
    contrib = new AngleBendContrib(
        field, i, atomIdx, j, ax1->getBondTypeAsDouble(),
        eq1->getBondTypeAsDouble(), params[i], params[atomIdx], params[j]);
    field->contribs().push_back(ForceFields::ContribPtr(contrib));
  }
  i = ax1->getOtherAtomIdx(atomIdx);
  j = eq2->getOtherAtomIdx(atomIdx);
  if (params[i] && params[j]) {
    contrib = new AngleBendContrib(
        field, i, atomIdx, j, ax1->getBondTypeAsDouble(),
        eq2->getBondTypeAsDouble(), params[i], params[atomIdx], params[j]);
    field->contribs().push_back(ForceFields::ContribPtr(contrib));
  }
  i = ax1->getOtherAtomIdx(atomIdx);
  j = eq3->getOtherAtomIdx(atomIdx);
  if (params[i] && params[j]) {
    contrib = new AngleBendContrib(
        field, i, atomIdx, j, ax1->getBondTypeAsDouble(),
        eq3->getBondTypeAsDouble(), params[i], params[atomIdx], params[j]);
    field->contribs().push_back(ForceFields::ContribPtr(contrib));
  }
  i = ax2->getOtherAtomIdx(atomIdx);
  j = eq1->getOtherAtomIdx(atomIdx);
  if (params[i] && params[j]) {
    contrib = new AngleBendContrib(
        field, i, atomIdx, j, ax2->getBondTypeAsDouble(),
        eq1->getBondTypeAsDouble(), params[i], params[atomIdx], params[j]);
    field->contribs().push_back(ForceFields::ContribPtr(contrib));
  }
  i = ax2->getOtherAtomIdx(atomIdx);
  j = eq2->getOtherAtomIdx(atomIdx);
  if (params[i] && params[j]) {
    contrib = new AngleBendContrib(
        field, i, atomIdx, j, ax2->getBondTypeAsDouble(),
        eq2->getBondTypeAsDouble(), params[i], params[atomIdx], params[j]);
    field->contribs().push_back(ForceFields::ContribPtr(contrib));
  }
  i = ax2->getOtherAtomIdx(atomIdx);
  j = eq3->getOtherAtomIdx(atomIdx);
  if (params[i] && params[j]) {
    contrib = new AngleBendContrib(
        field, i, atomIdx, j, ax2->getBondTypeAsDouble(),
        eq3->getBondTypeAsDouble(), params[i], params[atomIdx], params[j]);
    field->contribs().push_back(ForceFields::ContribPtr(contrib));
  }
}

// ------------------------------------------------------------------------
//
//
//
// ------------------------------------------------------------------------
void addAngleSpecialCases(const ROMol &mol, int confId,
                          const AtomicParamVect &params,
                          ForceFields::ForceField *field) {
  PRECONDITION(mol.getNumAtoms() == params.size(), "bad parameters");
  PRECONDITION(field, "bad forcefield");

  unsigned int nAtoms = mol.getNumAtoms();
  for (unsigned int i = 0; i < nAtoms; i++) {
    const Atom *atom = mol.getAtomWithIdx(i);
    // trigonal bipyramidal:
    if ((atom->getHybridization() == Atom::SP3D && atom->getDegree() == 5)) {
      addTrigonalBipyramidAngles(atom, mol, confId, params, field);
    }
  }
}

// ------------------------------------------------------------------------
//
//
//
// ------------------------------------------------------------------------
void addNonbonded(const ROMol &mol, int confId, const AtomicParamVect &params,
                  ForceFields::ForceField *field,
                  boost::shared_array<std::uint8_t> neighborMatrix,
                  double vdwThresh, bool ignoreInterfragInteractions) {
  PRECONDITION(mol.getNumAtoms() == params.size(), "bad parameters");
  PRECONDITION(field, "bad forcefield");

  INT_VECT fragMapping;
  if (ignoreInterfragInteractions) {
    std::vector<ROMOL_SPTR> molFrags =
        MolOps::getMolFrags(mol, true, &fragMapping);
  }

  unsigned int nAtoms = mol.getNumAtoms();
  const Conformer &conf = mol.getConformer(confId);
  for (unsigned int i = 0; i < nAtoms; i++) {
    if (!params[i]) {
      continue;
    }
    for (unsigned int j = i + 1; j < nAtoms; j++) {
      if (!params[j] ||
          (ignoreInterfragInteractions && fragMapping[i] != fragMapping[j])) {
        continue;
      }
      if (getTwoBitCell(neighborMatrix, twoBitCellPos(nAtoms, i, j)) >=
          RELATION_1_4) {
        double dist = (conf.getAtomPos(i) - conf.getAtomPos(j)).length();
        if (dist < vdwThresh *
                       UFF::Utils::calcNonbondedMinimum(params[i], params[j])) {
          vdWContrib *contrib;
          contrib = new vdWContrib(field, i, j, params[i], params[j]);
          field->contribs().push_back(ForceFields::ContribPtr(contrib));
        }
      }
    }
  }
}

const std::string DefaultTorsionBondSmarts::ds_string =
    "[!$(*#*)&!D1]~[!$(*#*)&!D1]";
boost::scoped_ptr<const ROMol> DefaultTorsionBondSmarts::ds_instance;
#ifdef RDK_BUILD_THREADSAFE_SSS
std::once_flag DefaultTorsionBondSmarts::ds_flag;
#endif
void DefaultTorsionBondSmarts::create() {
  ds_instance.reset(SmartsToMol(ds_string));
}

const ROMol *DefaultTorsionBondSmarts::query() {
#ifdef RDK_BUILD_THREADSAFE_SSS
  std::call_once(ds_flag, create);
#else
  static bool created = false;
  if (!created) {
    created = true;
    create();
  }
#endif
  return ds_instance.get();
}

// ------------------------------------------------------------------------
//
//
//
// ------------------------------------------------------------------------
void addTorsions(const ROMol &mol, const AtomicParamVect &params,
                 ForceFields::ForceField *field,
                 const std::string &torsionBondSmarts) {
  PRECONDITION(mol.getNumAtoms() == params.size(), "bad parameters");
  PRECONDITION(field, "bad forcefield");

  // find all of the torsion bonds:
  std::vector<MatchVectType> matchVect;
  const ROMol *defaultQuery = DefaultTorsionBondSmarts::query();
  const ROMol *query = (torsionBondSmarts == DefaultTorsionBondSmarts::string())
                           ? defaultQuery
                           : SmartsToMol(torsionBondSmarts);
  TEST_ASSERT(query);
  unsigned int nHits = SubstructMatch(mol, *query, matchVect);
  if (query != defaultQuery) {
    delete query;
  }

  for (unsigned int i = 0; i < nHits; i++) {
    MatchVectType match = matchVect[i];
    TEST_ASSERT(match.size() == 2);
    int idx1 = match[0].second;
    int idx2 = match[1].second;
    if (!params[idx1] || !params[idx2]) {
      continue;
    }
    const Bond *bond = mol.getBondBetweenAtoms(idx1, idx2);
    std::vector<TorsionAngleContrib *> contribsHere;
    TEST_ASSERT(bond);
    const Atom *atom1 = mol.getAtomWithIdx(idx1);
    const Atom *atom2 = mol.getAtomWithIdx(idx2);

    if ((atom1->getHybridization() == Atom::SP2 ||
         atom1->getHybridization() == Atom::SP3) &&
        (atom2->getHybridization() == Atom::SP2 ||
         atom2->getHybridization() == Atom::SP3)) {
      ROMol::OEDGE_ITER beg1, end1;
      boost::tie(beg1, end1) = mol.getAtomBonds(atom1);
      while (beg1 != end1) {
        const Bond *tBond1 = mol[*beg1];
        if (tBond1 != bond) {
          int bIdx = tBond1->getOtherAtomIdx(idx1);
          ROMol::OEDGE_ITER beg2, end2;
          boost::tie(beg2, end2) = mol.getAtomBonds(atom2);
          while (beg2 != end2) {
            const Bond *tBond2 = mol[*beg2];
            if (tBond2 != bond && tBond2 != tBond1) {
              int eIdx = tBond2->getOtherAtomIdx(idx2);
              // make sure this isn't a three-membered ring:
              if (eIdx != bIdx) {
                // we now have a torsion involving atoms (bonds):
                //  bIdx - (tBond1) - idx1 - (bond) - idx2 - (tBond2) - eIdx
                TorsionAngleContrib *contrib;

                // if either of the end atoms is SP2 hybridized, set a flag
                // here.
                bool hasSP2 = false;
                if (mol.getAtomWithIdx(bIdx)->getHybridization() == Atom::SP2 ||
                    mol.getAtomWithIdx(eIdx)->getHybridization() == Atom::SP2) {
                  hasSP2 = true;
                }
                // std::cout << "Torsion: " << bIdx << "-" << idx1 << "-" <<
                // idx2 << "-" << eIdx << std::endl;
                // if(okToIncludeTorsion(mol,bond,bIdx,idx1,idx2,eIdx)){
                // std::cout << "  INCLUDED" << std::endl;
                contrib = new TorsionAngleContrib(
                    field, bIdx, idx1, idx2, eIdx, bond->getBondTypeAsDouble(),
                    atom1->getAtomicNum(), atom2->getAtomicNum(),
                    atom1->getHybridization(), atom2->getHybridization(),
                    params[idx1], params[idx2], hasSP2);
                field->contribs().push_back(ForceFields::ContribPtr(contrib));
                contribsHere.push_back(contrib);
                //}
              }
            }
            beg2++;
          }
        }
        beg1++;
      }
    }
    // now divide the force constant for each contribution to the torsion energy
    // about this bond by the number of contribs about this bond:
    for (auto chI = contribsHere.begin(); chI != contribsHere.end(); ++chI) {
      (*chI)->scaleForceConstant(contribsHere.size());
    }
  }
}

// ------------------------------------------------------------------------
//
//
//
// ------------------------------------------------------------------------
void addInversions(const ROMol &mol, const AtomicParamVect &params,
                   ForceFields::ForceField *field) {
  PRECONDITION(mol.getNumAtoms() == params.size(), "bad parameters");
  PRECONDITION(field, "bad forcefield");

  unsigned int idx[4];
  unsigned int n[4];
  const Atom *atom[4];
  ROMol::ADJ_ITER nbrIdx;
  ROMol::ADJ_ITER endNbrs;

  for (idx[1] = 0; idx[1] < mol.getNumAtoms(); ++idx[1]) {
    atom[1] = mol.getAtomWithIdx(idx[1]);
    int at2AtomicNum = atom[1]->getAtomicNum();
    // if the central atom is not carbon, nitrogen, oxygen,
    // phosphorous, arsenic, antimonium or bismuth, skip it
    if (((at2AtomicNum != 6) && (at2AtomicNum != 7) && (at2AtomicNum != 8) &&
         (at2AtomicNum != 15) && (at2AtomicNum != 33) && (at2AtomicNum != 51) &&
         (at2AtomicNum != 83)) ||
        (atom[1]->getDegree() != 3)) {
      continue;
    }
    // if the central atom is carbon, nitrogen or oxygen
    // but hybridization is not sp2, skip it
    if (((at2AtomicNum == 6) || (at2AtomicNum == 7) || (at2AtomicNum == 8)) &&
        (atom[1]->getHybridization() != Atom::SP2)) {
      continue;
    }
    boost::tie(nbrIdx, endNbrs) = mol.getAtomNeighbors(atom[1]);
    unsigned int i = 0;
    bool isBoundToSP2O = false;
    for (; nbrIdx != endNbrs; ++nbrIdx) {
      atom[i] = mol[*nbrIdx];
      idx[i] = atom[i]->getIdx();
      // if the central atom is sp2 carbon and is
      // bound to sp2 oxygen, set a flag
      if (!isBoundToSP2O) {
        isBoundToSP2O =
            ((at2AtomicNum == 6) && (atom[i]->getAtomicNum() == 8) &&
             (atom[i]->getHybridization() == Atom::SP2));
      }
      if (!i) {
        ++i;
      }
      ++i;
    }
    for (unsigned int i = 0; i < 3; ++i) {
      n[1] = 1;
      switch (i) {
        case 0:
          n[0] = 0;
          n[2] = 2;
          n[3] = 3;
          break;

        case 1:
          n[0] = 0;
          n[2] = 3;
          n[3] = 2;
          break;

        case 2:
          n[0] = 2;
          n[2] = 3;
          n[3] = 0;
          break;
      }
      InversionContrib *contrib;
      contrib = new InversionContrib(field, idx[n[0]], idx[n[1]], idx[n[2]],
                                     idx[n[3]], at2AtomicNum, isBoundToSP2O);
      field->contribs().push_back(ForceFields::ContribPtr(contrib));
    }
  }
}
}  // end of namespace Tools

// ------------------------------------------------------------------------
//
//
//
// ------------------------------------------------------------------------
ForceFields::ForceField *constructForceField(ROMol &mol,
                                             const AtomicParamVect &params,
                                             double vdwThresh, int confId,
                                             bool ignoreInterfragInteractions) {
  PRECONDITION(mol.getNumAtoms() == params.size(), "bad parameters");

  if (MolOps::needsHs(mol)) {
    BOOST_LOG(rdWarningLog)
        << "Molecule does not have explicit Hs. Consider calling AddHs()"
        << std::endl;
  }

  std::unique_ptr<ForceFields::ForceField> res(new ForceFields::ForceField());

  // add the atomic positions:
  Conformer &conf = mol.getConformer(confId);
  for (unsigned int i = 0; i < mol.getNumAtoms(); i++) {
    res->positions().push_back(&conf.getAtomPos(i));
  }

  Tools::addBonds(mol, params, res.get());
  Tools::addAngles(mol, params, res.get());
  Tools::addAngleSpecialCases(mol, confId, params, res.get());
  boost::shared_array<std::uint8_t> neighborMat =
      Tools::buildNeighborMatrix(mol);
  Tools::addNonbonded(mol, confId, params, res.get(), neighborMat, vdwThresh,
                      ignoreInterfragInteractions);
  Tools::addTorsions(mol, params, res.get());
  Tools::addInversions(mol, params, res.get());

  return res.release();
}

// ------------------------------------------------------------------------
//
//
//
// ------------------------------------------------------------------------
ForceFields::ForceField *constructForceField(ROMol &mol, double vdwThresh,
                                             int confId,
                                             bool ignoreInterfragInteractions) {
  bool foundAll;
  AtomicParamVect params;
  boost::tie(params, foundAll) = getAtomTypes(mol);
  return constructForceField(mol, params, vdwThresh, confId,
                             ignoreInterfragInteractions);
}
}  // namespace UFF
}  // namespace RDKit