<?xml version="1.0"?>

<SMIRFF version="0.1" aromaticity_model="OEAroModel_MDL">

<!-- SMIRKS (SMIRKS Force Field) mockup1.0 for alkanes, ethers, and alcohols -->
<Date>Date: Tue May  3 2016</Date>
<Author>C. I. Bayly, OpenEye Scientific Software</Author>
<!-- This mockup is based on frcmod.Frosst_AlkEthOH, the minimal subset of parm99/parm@Frosst -->
<!-- required for alkanes, ethers, and alcohols (excluding ketals and 3-memb-rings) -->

<!-- WARNING: AMBER functional forms drop the factor of 2 in the bond energy term, so cross-comparing this file with a corresponding .frcmod file, it will appear that the values here are twice as large as they should be. -->
<HarmonicBondForce length_unit="angstroms" k_unit="kilocalories_per_mole/angstrom**2">
   <Bond smirks="[#6X4:1]-[#6X4:2]" length="1.526" k="620.0" id="b0001" parent_id="b0001"/> <!-- CT-CT from frcmod.Frosst_AlkEthOH -->
   <Bond smirks="[#6X4:1]-[#1:2]" length="1.090" k="680.0" id="b0002" parent_id="b0002"/> <!-- CT-H_ from frcmod.Frosst_AlkEthOH -->
   <Bond smirks="[#8:1]~[#1:2]" length="1.410" k="640.0" id="b0003" parent_id="b0003"/> <!-- DEBUG O-H -->
   <Bond smirks="[#6X4:1]-[O&amp;X2&amp;H1:2]" length="1.410" k="640.0" id="b0004" parent_id="b0004"/> <!-- CT-OH from frcmod.Frosst_AlkEthOH -->
   <Bond smirks="[#6X4:1]-[O&amp;X2&amp;H0:2]" length="1.370" k="640.0" id="b0005" parent_id="b0005"/> <!--CT-OS from frcmod.Frosst_AlkEthOH -->
   <Bond smirks="[#8X2:1]-[#1:2]" length="0.960" k="1106.0" id="b0006" parent_id="b0003"/> <!-- OH-HO from frcmod.Frosst_AlkEthOH -->
</HarmonicBondForce>
<!-- WARNING: AMBER functional forms drop the factor of 2 in the angle energy term, so cross-comparing this file with a corresponding .frcmod file, it will appear that the values here are twice as large as they should be. -->
<HarmonicAngleForce angle_unit="degrees" k_unit="kilocalories_per_mole/radian**2">
   <Angle smirks="[a,A:1]-[#6X4:2]-[a,A:3]" angle="109.50" k="100.0" id="a0001" parent_id="a0001"/> <!-- consensus matches all X-Csp3-X -->
   <Angle smirks="[#1:1]-[#6X4:2]-[#1:3]" angle="109.50" k="70.0" id="a0002" parent_id="a0001"/> <!-- H1-CT-H1 from frcmod.Frosst_AlkEthOH -->
   <Angle smirks="[#6X4:1]-[#6X4:2]-[#6X4:3]" angle="109.50" k="80.0" id="a0003" parent_id="a0001"/> <!-- CT-CT-CT from frcmod.Frosst_AlkEthOH -->
   <Angle smirks="[#8X2:1]-[#6X4:2]-[#8X2:3]" angle="109.50" k="140.0" id="a0004" parent_id="a0001"/> <!-- O_-CT-O_ from frcmod.Frosst_AlkEthOH -->
   <Angle smirks="[#6X4:1]-[#8X2:2]-[#1:3]" angle="108.50" k="110.0" id="a0005" parent_id="a0005"/> <!-- CT-OH-HO from frcmod.Frosst_AlkEthOH -->
   <Angle smirks="[#6X4:1]-[#8X2:2]-[#6X4:3]" angle="109.50" k="120.0" id="a0006" parent_id="a0006"/> <!-- CT-OS-CT from frcmod.Frosst_AlkEthOH -->
</HarmonicAngleForce>
<PeriodicTorsionForce phase_unit="degrees" k_unit="kilocalories_per_mole">
   <Proper smirks="[a,A:1]-[#6X4:2]-[#6X4:3]-[a,A:4]" idivf1="9" periodicity1="3" phase1="0.0" k1="1.40" id="t0001" parent_id="t0001"/> <!-- X -CT-CT-X from frcmod.Frosst_AlkEthOH -->
   <Proper smirks="[a,A:1]-[#6X4:2]-[#8X2:3]-[#1:4]" idivf1="3" periodicity1="3" phase1="0.0" k1="0.50" id="t0002" parent_id="t0002"/> <!--X -CT-OH-X from frcmod.Frosst_AlkEthOH -->
   <Proper smirks="[a,A:1]-[#6X4:2]-[#8X2:3]-[!#1:4]" idivf1="3" periodicity1="3" phase1="0.0" k1="1.15" id="t0003" parent_id="t0003"/> <!-- X -CT-OS-X from frcmod.Frosst_AlkEthOH -->
   <Proper smirks="[#1:1]-[#6X4:2]-[#6X4:3]-[#1:4]" idivf1="1" periodicity1="3" phase1="0.0" k1="0.15" id="t0004" parent_id="t0001"/> <!-- HC-CT-CT-HC from frcmod.Frosst_AlkEthOH; note discrepancy with parm@frosst which applies this ONLY to HC-CT-CT-HC and other hydrogens get the generic X -CT-CT-X -->
   <Proper smirks="[#1:1]-[#6X4:2]-[#6X4:3]-[#6X4:4]" idivf1="1" periodicity1="3" phase1="0.0" k1="0.16" id="t0005" parent_id="t0001"/> <!-- HC-CT-CT-CT from frcmod.Frosst_AlkEthOH -->
   <Proper smirks="[#6X4:1]-[#6X4:2]-[#8X2:3]-[#1:4]" idivf1='1' periodicity1="3" phase1="0.0" k1="0.16" idivf2="1" periodicity2="1" phase2="0.0" k2="0.25" id="t0006" parent_id="t0002"/> <!-- HO-OH-CT-CT from frcmod.Frosst_AlkEthOH -->
   <Proper smirks="[#6X4:1]-[#6X4:2]-[#6X4:3]-[#6X4:4]" idivf1="1" periodicity1="3" phase1="0.0" k1="0.18" idivf2="1" periodicity2="2" phase2="180.0" k2="0.25" idivf3="1" periodicity3="1" phase3="180.0" k3="0.20" id="t0007" parent_id="t0001"/> <!-- CT-CT-CT-CT from frcmod.Frosst_AlkEthOH -->
   <Proper smirks="[#6X4:1]-[#6X4:2]-[#8X2:3]-[#6X4:4]" idivf1="1" periodicity1="3" phase1="0.0" k1="0.383" idivf2="1" periodicity2="2" phase2="180.0" k2="0.1" id="t0008" parent_id="t0003"/> <!-- CT-CT-OS-CT from frcmod.Frosst_AlkEthOH -->
   <Proper smirks="[#6X4:1]-[#8X2:2]-[#6X4:3]-[O&amp;X2&amp;H0:4]" idivf1="1" periodicity1="3" phase1="0.0" k1="0.10" idivf2="1" periodicity2="2" phase2="180.0" k2="0.85" idivf3="1" periodicity3="1" phase3="180.0" k3="1.35" id="t0009" parent_id="t0003"/> <!-- CT-OS-CT-OS from frcmod.Frosst_AlkEthOH -->
   <Proper smirks="[#8X2:1]-[#6X4:2]-[#6X4:3]-[#8X2:4]" idivf1="1" periodicity1="3" phase1="0.0" k1="0.144" idivf2="1" periodicity2="2" phase2="0.0" k2="1.175" id="t0010" parent_id="t0001"/> <!-- O_-CT-CT-O_ from frcmod.Frosst_AlkEthOH -->
   <Proper smirks="[#8X2:1]-[#6X4:2]-[#6X4:3]-[#1:4]" idivf1="1" periodicity1="3" phase1="0.0" k1="0.0" idivf2="1" periodicity2="1" phase2="0.0" k2="0.25" id="t0011" parent_id="t0001"/> <!-- H_-CT-CT-O_ from frcmod.Frosst_AlkEthOH; discrepancy with parm@frosst with H2,H3-CT-CT-O_ per C Bayly -->
   <Proper smirks="[#1:1]-[#6X4:2]-[#6X4:3]-[OX2:4]" idivf1="1" periodicity1="3" phase1="0.0" k1="0.0" idivf2="1" periodicity2="1" phase2="0.0" k2="0.25" id="t0012" parent_id="t0001"/> <!-- HC,H1-CT-CT-OH,OS from frcmod.Frosst_AlkEthOH ; note corresponding H2 and H3 params missing so they presumably get generic parameters (another parm@frosst bug) -->
   <Improper smirks="[a,A:1]~[#6X3:2]([a,A:3])~[OX1:4]" periodicity1="2" phase1="180.0" k1="10.5" id="i0001" parent_id="i0001"/> <!-- X -X -C -O  from frcmod.Frosst_AlkEthOH; none in set but here as format placeholder -->
</PeriodicTorsionForce>
<!-- WARNING: AMBER formats typically use r_0/2=r_min/2 to describe the relevant distance parameter, where r0 = 2^(1/6)*sigma. The difference is important, and the two conventions can be used here by specifying sigma or rmin_half. -->
<NonbondedForce coulomb14scale="0.833333" lj14scale="0.5" sigma_unit="angstroms" epsilon_unit="kilocalories_per_mole">
   <!-- sigma is in angstroms, epsilon is in kcal/mol -->
   <Atom smirks="[#1:1]" rmin_half="1.4870" epsilon="0.0157" id="n0001" parent_id="n0001"/> <!-- making HC the generic hydrogen -->
   <Atom smirks="[$([#1]-C):1]" rmin_half="1.4870" epsilon="0.0157" id="n0002" parent_id="n0001"/> <!-- HC from frcmod.Frosst_AlkEthOH -->
   <Atom smirks="[$([#1]-C-[#7,#8,F,#16,Cl,Br]):1]" rmin_half="1.3870" epsilon="0.0157" id="n0003" parent_id="n0002"/> <!-- H1 from frcmod.Frosst_AlkEthOH -->
   <Atom smirks="[$([#1]-C(-[#7,#8,F,#16,Cl,Br])-[#7,#8,F,#16,Cl,Br]):1]" rmin_half="1.2870" epsilon="0.0157" id="n0004" parent_id="n0003"/> <!--H2 from frcmod.Frosst_AlkEthOH -->
   <Atom smirks="[$([#1]-C(-[#7,#8,F,#16,Cl,Br])(-[#7,#8,F,#16,Cl,Br])-[#7,#8,F,#16,Cl,Br]):1]" rmin_half="1.1870" epsilon="0.0157" id="n0005" parent_id="n0004"/> <!--H3 from frcmod.Frosst_AlkEthOH -->
   <Atom smirks="[#1$(*-[#8]):1]" rmin_half="0.0000" epsilon="0.0000" id="n0006" parent_id="n0001"/> <!-- HO from frcmod.Frosst_AlkEthOH -->
   <Atom smirks="[#6:1]" rmin_half="1.9080" epsilon="0.1094" id="n0007" parent_id="n0007"/> <!-- making CT the generic carbon -->
   <Atom smirks="[#6X4:1]" rmin_half="1.9080" epsilon="0.1094" id="n0008" parent_id="n0007"/> <!-- CT from frcmod.Frosst_AlkEthOH-->
   <Atom smirks="[#8:1]" rmin_half="1.6837" epsilon="0.1700" id="n0009" parent_id="n0009"/> <!-- making OS the generic oxygen -->
   <Atom smirks="[#8X2:1]" rmin_half="1.6837" epsilon="0.1700" id="n0010" parent_id="n0009"/> <!-- OS from frcmod.Frosst_AlkEthOH -->
   <Atom smirks="[#8X2+0$(*-[#1]):1]" rmin_half="1.7210" epsilon="0.2104" id="n0011" parent_id="n0009"/> <!-- OH from frcmod.Frosst_AlkEthOH -->
</NonbondedForce>

</SMIRFF>
