# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Iain Oswald' _publ_contact_author_email IAIN.OSWALD@ED.AC.UK _publ_section_title ; Structural similarities of 2-chlorophenol and 2-methylphenol ; loop_ _publ_author_name 'Iain Oswald' 'Wilson A. Crichton' # Attachment 'CPIII.cif' data_CPIII _database_code_depnum_ccdc_archive 'CCDC 698227' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-Chlorophenol ; _chemical_name_common 2-Chlorophenol _chemical_melting_point ? _chemical_formula_moiety 'C6 H5 Cl O' _chemical_formula_sum 'C6 H5 Cl O' _chemical_formula_weight 128.55 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 5.5826(10) _cell_length_b 9.587(3) _cell_length_c 10.054(4) _cell_angle_alpha 90.00 _cell_angle_beta 96.19(2) _cell_angle_gamma 90.00 _cell_volume 534.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 190 _cell_measurement_theta_min 4.00 _cell_measurement_theta_max 19.05 _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.596 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 264 _exptl_absorpt_coefficient_mu 0.585 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.124 _exptl_absorpt_correction_T_max 0.93 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 1282 _diffrn_reflns_av_R_equivalents 0.1171 _diffrn_reflns_av_sigmaI/netI 0.1597 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 4.00 _diffrn_reflns_theta_max 23.28 _reflns_number_total 397 _reflns_number_gt 194 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0565P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 397 _refine_ls_number_parameters 37 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.1576 _refine_ls_R_factor_gt 0.0670 _refine_ls_wR_factor_ref 0.1400 _refine_ls_wR_factor_gt 0.1195 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.023 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.1836(9) 0.0928(7) 0.3919(6) 0.033(3) Uiso 1 1 d G . . C2 C 0.0167(11) 0.1777(7) 0.3857(7) 0.034(3) Uiso 1 1 d GD . . C3 C 0.1649(8) 0.1583(6) 0.2846(7) 0.037(3) Uiso 1 1 d G . . H3 H 0.2990 0.2150 0.2804 0.045 Uiso 1 1 calc R . . C4 C 0.1128(9) 0.0540(7) 0.1899(6) 0.044(3) Uiso 1 1 d G . . H4 H 0.2119 0.0410 0.1223 0.052 Uiso 1 1 calc R . . C5 C -0.0876(11) -0.0309(7) 0.1962(7) 0.049(3) Uiso 1 1 d G . . H5 H -0.1224 -0.1007 0.1328 0.059 Uiso 1 1 calc R . . C6 C -0.2358(8) -0.0115(6) 0.2972(7) 0.045(3) Uiso 1 1 d G . . H6 H -0.3698 -0.0683 0.3014 0.054 Uiso 1 1 calc R . . O7 O -0.3282(13) 0.1134(8) 0.4930(10) 0.052(3) Uani 1 1 d D . . H71 H -0.28(4) 0.187(17) 0.53(3) 0.077 Uiso 0.50 1 d PD . . H72 H -0.40(3) 0.037(9) 0.49(3) 0.077 Uiso 0.50 1 d PD . . Cl8 Cl 0.0925(5) 0.2981(3) 0.5080(4) 0.0585(14) Uani 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O7 0.044(5) 0.047(9) 0.066(11) 0.002(6) 0.016(6) -0.002(4) Cl8 0.0623(18) 0.053(3) 0.059(4) -0.0045(18) 0.003(2) -0.0035(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.3900 . ? C1 C6 1.3900 . ? C1 O7 1.378(8) . ? C2 C3 1.3900 . ? C2 Cl8 1.706(5) . ? C3 C4 1.3900 . ? C3 H3 0.9300 . ? C4 C5 1.3900 . ? C4 H4 0.9300 . ? C5 C6 1.3900 . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? O7 H71 0.821(11) . ? O7 H72 0.822(11) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 120.0 . . ? C2 C1 O7 119.2(5) . . ? C6 C1 O7 120.8(5) . . ? C3 C2 C1 120.0 . . ? C3 C2 Cl8 119.8(4) . . ? C1 C2 Cl8 120.1(4) . . ? C2 C3 C4 120.0 . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C5 C4 C3 120.0 . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C4 C5 C6 120.0 . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C5 C6 C1 120.0 . . ? C5 C6 H6 120.0 . . ? C1 C6 H6 120.0 . . ? C1 O7 H71 106(10) . . ? C1 O7 H72 96(10) . . ? H71 O7 H72 158(10) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O7 H72 O7 0.822(11) 2.14(4) 2.913(13) 156(10) 3_456 _diffrn_measured_fraction_theta_max 0.513 _diffrn_reflns_theta_full 23.28 _diffrn_measured_fraction_theta_full 0.513 _refine_diff_density_max 0.256 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.067 # Attachment 'MPCP.cif' data_MPCP _database_code_depnum_ccdc_archive 'CCDC 698228' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (0.45)2-METHYLPHENOL:(0.55)2-CHLOROPHENOL ; _chemical_name_common (0.45)2-METHYLPHENOL:(0.55)2-CHLOROPHENOL _chemical_melting_point ? _chemical_formula_moiety 0.45(C7H8O)0.55(C6H5OCl) _chemical_formula_sum 'C6.45 H6.34 Cl0.55 O' _chemical_formula_weight 119.45 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Trigonal _symmetry_space_group_name_H-M P3(2) _symmetry_space_group_name_Hall P32 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+2/3' '-x+y, -x, z+1/3' _cell_length_a 16.1628(2) _cell_length_b 16.1628(2) _cell_length_c 5.9006(1) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 1334.93(3) _cell_formula_units_Z 9 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6449 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 29.96 _exptl_crystal_description CYLINDER _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 2 _exptl_crystal_size_mid 0.61 _exptl_crystal_size_min 0.61 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.337 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 562 _exptl_absorpt_coefficient_mu 0.328 _exptl_absorpt_correction_type Multiscan _exptl_absorpt_correction_T_min 0.508 _exptl_absorpt_correction_T_max 0.82 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 33656 _diffrn_reflns_av_R_equivalents 0.0334 _diffrn_reflns_av_sigmaI/netI 0.0255 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.52 _diffrn_reflns_theta_max 30.64 _reflns_number_total 5463 _reflns_number_gt 4855 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0593P)^2^+0.1877P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.02(5) _refine_ls_number_reflns 5463 _refine_ls_number_parameters 223 _refine_ls_number_restraints 181 _refine_ls_R_factor_all 0.0480 _refine_ls_R_factor_gt 0.0405 _refine_ls_wR_factor_ref 0.1024 _refine_ls_wR_factor_gt 0.0990 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.020 _refine_ls_shift/su_mean 0.002 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C11 C 0.12010(6) 0.16849(6) 0.52419(19) 0.0271(3) Uani 1 1 d GU A . C21 C 0.13147(7) 0.23672(7) 0.36478(18) 0.0306(3) Uani 1 1 d GDU . . C31 C 0.20978(8) 0.32856(7) 0.3772(2) 0.0387(4) Uani 1 1 d GU A . H31 H 0.2175 0.3752 0.2683 0.046 Uiso 1 1 calc R . . C41 C 0.27672(7) 0.35218(6) 0.5491(2) 0.0420(4) Uani 1 1 d GU . . H41 H 0.3302 0.4149 0.5576 0.050 Uiso 1 1 calc R A . C51 C 0.26536(7) 0.28395(8) 0.7085(2) 0.0369(4) Uani 1 1 d GU A . H51 H 0.3111 0.3001 0.8260 0.044 Uiso 1 1 calc R . . C61 C 0.18705(7) 0.19211(7) 0.69608(18) 0.0314(3) Uani 1 1 d GU . . H61 H 0.1793 0.1455 0.8050 0.038 Uiso 1 1 calc R A . O71 O 0.04178(9) 0.07817(9) 0.5089(2) 0.0344(3) Uani 1 1 d D . . H71 H 0.0468(14) 0.0414(13) 0.602(3) 0.035(5) Uiso 1 1 d D . . C81 C 0.0585(12) 0.2133(11) 0.180(3) 0.030(2) Uani 0.47 1 d PDU A 1 H811 H 0.0667 0.1751 0.0623 0.045 Uiso 0.47 1 calc PR A 1 H821 H 0.0673 0.2727 0.1128 0.045 Uiso 0.47 1 calc PR A 1 H831 H -0.0059 0.1770 0.2438 0.045 Uiso 0.47 1 calc PR A 1 Cl81 Cl 0.0478(3) 0.2072(3) 0.1557(6) 0.0351(5) Uani 0.53 1 d PD A 2 C12 C 0.49515(5) 0.23722(6) 0.04056(19) 0.0276(3) Uani 1 1 d GU B . C22 C 0.43754(7) 0.23725(7) 0.21542(17) 0.0303(3) Uani 1 1 d GDU . . C32 C 0.34158(7) 0.16735(8) 0.22331(19) 0.0364(4) Uani 1 1 d GU B . H32 H 0.3022 0.1674 0.3428 0.044 Uiso 1 1 calc R . . C42 C 0.30322(5) 0.09741(8) 0.0563(2) 0.0402(4) Uani 1 1 d GU . . H42 H 0.2376 0.0496 0.0617 0.048 Uiso 1 1 calc R B . C52 C 0.36082(7) 0.09738(7) -0.1185(2) 0.0397(4) Uani 1 1 d GU B . H52 H 0.3346 0.0496 -0.2327 0.048 Uiso 1 1 calc R . . C62 C 0.45679(7) 0.16728(7) -0.12643(18) 0.0331(3) Uani 1 1 d GU . . H62 H 0.4962 0.1673 -0.2459 0.040 Uiso 1 1 calc R B . O72 O 0.58959(8) 0.30858(8) 0.0340(2) 0.0311(2) Uani 1 1 d D . . H72 H 0.6204(14) 0.2956(15) -0.063(3) 0.031(5) Uiso 1 1 d D . . C82 C 0.4786(13) 0.3205(9) 0.379(2) 0.066(5) Uani 0.37 1 d PDU B 1 H812 H 0.4266 0.3208 0.4632 0.100 Uiso 0.37 1 calc PR B 1 H822 H 0.5141 0.3803 0.2940 0.100 Uiso 0.37 1 calc PR B 1 H832 H 0.5218 0.3142 0.4848 0.100 Uiso 0.37 1 calc PR B 1 Cl82 Cl 0.48671(12) 0.32207(8) 0.4232(2) 0.0331(2) Uani 0.63 1 d PD B 2 C13 C 0.39238(7) -0.16507(6) 0.5298(2) 0.0309(3) Uani 1 1 d GU C . C23 C 0.37884(7) -0.11707(8) 0.35106(19) 0.0354(3) Uani 1 1 d GDU . . C33 C 0.43694(9) -0.01868(8) 0.3305(2) 0.0434(4) Uani 1 1 d GU C . H33 H 0.4277 0.0141 0.2083 0.052 Uiso 1 1 calc R . . C43 C 0.50857(9) 0.03171(6) 0.4887(3) 0.0469(5) Uani 1 1 d GU . . H43 H 0.5483 0.0990 0.4746 0.056 Uiso 1 1 calc R C . C53 C 0.52210(8) -0.01628(8) 0.6674(2) 0.0456(4) Uani 1 1 d GU C . H53 H 0.5711 0.0182 0.7756 0.055 Uiso 1 1 calc R . . C63 C 0.46401(8) -0.11467(8) 0.68804(19) 0.0376(4) Uani 1 1 d GU . . H63 H 0.4733 -0.1475 0.8102 0.045 Uiso 1 1 calc R C . O73 O 0.33535(9) -0.26295(8) 0.5466(2) 0.0334(3) Uani 1 1 d D . . H73 H 0.3555(17) -0.2843(16) 0.649(3) 0.044(6) Uiso 1 1 d D . . C83 C 0.2992(7) -0.1696(9) 0.1808(19) 0.046(2) Uani 0.50 1 d PDU C 1 H813 H 0.3205 -0.1973 0.0626 0.069 Uiso 0.50 1 calc PR C 1 H823 H 0.2824 -0.1248 0.1118 0.069 Uiso 0.50 1 calc PR C 1 H833 H 0.2431 -0.2206 0.2578 0.069 Uiso 0.50 1 calc PR C 1 Cl83 Cl 0.28748(19) -0.1808(2) 0.1632(4) 0.0403(5) Uani 0.50 1 d PD C 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C11 0.0233(6) 0.0295(7) 0.0300(7) -0.0022(6) 0.0016(5) 0.0144(6) C21 0.0290(7) 0.0345(8) 0.0316(7) 0.0010(6) 0.0021(6) 0.0183(6) C31 0.0362(9) 0.0344(8) 0.0441(9) 0.0052(7) 0.0013(7) 0.0166(7) C41 0.0368(9) 0.0285(8) 0.0534(11) -0.0018(7) -0.0032(8) 0.0108(7) C51 0.0307(8) 0.0363(8) 0.0415(9) -0.0066(7) -0.0072(7) 0.0151(7) C61 0.0296(7) 0.0338(8) 0.0327(8) 0.0001(6) -0.0009(6) 0.0174(6) O71 0.0276(5) 0.0303(6) 0.0400(6) 0.0039(5) -0.0059(4) 0.0104(4) C81 0.032(4) 0.024(3) 0.032(4) 0.002(2) -0.004(2) 0.012(3) Cl81 0.0319(8) 0.0474(11) 0.0278(7) 0.0030(6) -0.0054(5) 0.0212(8) C12 0.0266(7) 0.0273(7) 0.0281(7) 0.0028(5) -0.0003(5) 0.0129(6) C22 0.0343(8) 0.0307(7) 0.0283(7) 0.0050(6) 0.0023(6) 0.0180(6) C32 0.0325(8) 0.0416(9) 0.0364(8) 0.0132(7) 0.0075(6) 0.0195(7) C42 0.0267(8) 0.0398(9) 0.0460(9) 0.0121(7) -0.0027(6) 0.0106(7) C52 0.0338(8) 0.0374(9) 0.0389(9) 0.0002(7) -0.0078(7) 0.0111(7) C62 0.0319(8) 0.0336(8) 0.0308(8) -0.0001(6) -0.0007(6) 0.0142(7) O72 0.0262(5) 0.0294(5) 0.0320(6) -0.0043(4) 0.0031(4) 0.0096(4) C82 0.055(5) 0.086(7) 0.034(6) -0.018(4) -0.004(4) 0.017(4) Cl82 0.0421(5) 0.0365(4) 0.0238(5) -0.0013(3) 0.0050(4) 0.0220(4) C13 0.0299(7) 0.0294(7) 0.0357(8) 0.0009(6) 0.0061(6) 0.0165(6) C23 0.0328(8) 0.0382(8) 0.0380(8) 0.0045(7) 0.0052(6) 0.0199(7) C33 0.0470(10) 0.0385(9) 0.0486(10) 0.0082(8) 0.0187(8) 0.0244(8) C43 0.0494(10) 0.0342(9) 0.0553(12) -0.0001(8) 0.0200(9) 0.0195(8) C53 0.0401(9) 0.0384(9) 0.0506(10) -0.0146(8) 0.0032(8) 0.0137(8) C63 0.0352(8) 0.0343(8) 0.0418(9) -0.0048(7) 0.0026(7) 0.0164(7) O73 0.0337(6) 0.0274(5) 0.0320(6) 0.0002(4) -0.0067(5) 0.0100(5) C83 0.046(4) 0.048(4) 0.054(5) 0.001(3) 0.013(3) 0.031(3) Cl83 0.0365(7) 0.0526(10) 0.0302(6) 0.0100(6) -0.0074(5) 0.0212(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C11 O71 1.3762(14) . ? C11 C21 1.3900 . ? C11 C61 1.3900 . ? C21 C31 1.3900 . ? C21 C81 1.511(8) . ? C21 Cl81 1.712(2) . ? C31 C41 1.3900 . ? C31 H31 0.9500 . ? C41 C51 1.3900 . ? C41 H41 0.9500 . ? C51 C61 1.3900 . ? C51 H51 0.9500 . ? C61 H61 0.9500 . ? O71 H71 0.845(9) . ? C81 H811 0.9800 . ? C81 H821 0.9800 . ? C81 H831 0.9800 . ? C12 O72 1.3789(13) . ? C12 C22 1.3900 . ? C12 C62 1.3900 . ? C22 C32 1.3900 . ? C22 C82 1.512(8) . ? C22 Cl82 1.7103(15) . ? C32 C42 1.3900 . ? C32 H32 0.9500 . ? C42 C52 1.3900 . ? C42 H42 0.9500 . ? C52 C62 1.3900 . ? C52 H52 0.9500 . ? C62 H62 0.9500 . ? O72 H72 0.849(9) . ? C82 H812 0.9800 . ? C82 H822 0.9800 . ? C82 H832 0.9800 . ? C13 O73 1.3799(14) . ? C13 C23 1.3900 . ? C13 C63 1.3900 . ? C23 C33 1.3900 . ? C23 C83 1.514(8) . ? C23 Cl83 1.718(2) . ? C33 C43 1.3900 . ? C33 H33 0.9500 . ? C43 C53 1.3900 . ? C43 H43 0.9500 . ? C53 C63 1.3900 . ? C53 H53 0.9500 . ? C63 H63 0.9500 . ? O73 H73 0.837(9) . ? C83 H813 0.9800 . ? C83 H823 0.9800 . ? C83 H833 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O71 C11 C21 118.94(8) . . ? O71 C11 C61 121.06(8) . . ? C21 C11 C61 120.0 . . ? C11 C21 C31 120.0 . . ? C11 C21 C81 120.9(6) . . ? C31 C21 C81 119.1(6) . . ? C11 C21 Cl81 119.57(15) . . ? C31 C21 Cl81 120.42(15) . . ? C81 C21 Cl81 1.5(7) . . ? C41 C31 C21 120.0 . . ? C41 C31 H31 120.0 . . ? C21 C31 H31 120.0 . . ? C51 C41 C31 120.0 . . ? C51 C41 H41 120.0 . . ? C31 C41 H41 120.0 . . ? C61 C51 C41 120.0 . . ? C61 C51 H51 120.0 . . ? C41 C51 H51 120.0 . . ? C51 C61 C11 120.0 . . ? C51 C61 H61 120.0 . . ? C11 C61 H61 120.0 . . ? C11 O71 H71 110.1(14) . . ? C21 C81 H811 109.5 . . ? C21 C81 H821 109.5 . . ? C21 C81 H831 109.5 . . ? O72 C12 C22 118.83(8) . . ? O72 C12 C62 121.16(8) . . ? C22 C12 C62 120.0 . . ? C12 C22 C32 120.0 . . ? C12 C22 C82 118.5(7) . . ? C32 C22 C82 121.1(7) . . ? C12 C22 Cl82 119.32(8) . . ? C32 C22 Cl82 120.66(8) . . ? C82 C22 Cl82 7.5(7) . . ? C22 C32 C42 120.0 . . ? C22 C32 H32 120.0 . . ? C42 C32 H32 120.0 . . ? C52 C42 C32 120.0 . . ? C52 C42 H42 120.0 . . ? C32 C42 H42 120.0 . . ? C42 C52 C62 120.0 . . ? C42 C52 H52 120.0 . . ? C62 C52 H52 120.0 . . ? C52 C62 C12 120.0 . . ? C52 C62 H62 120.0 . . ? C12 C62 H62 120.0 . . ? C12 O72 H72 110.6(15) . . ? C22 C82 H812 109.5 . . ? C22 C82 H822 109.5 . . ? C22 C82 H832 109.5 . . ? O73 C13 C23 119.54(9) . . ? O73 C13 C63 120.45(9) . . ? C23 C13 C63 120.0 . . ? C33 C23 C13 120.0 . . ? C33 C23 C83 118.8(5) . . ? C13 C23 C83 121.2(5) . . ? C33 C23 Cl83 121.08(11) . . ? C13 C23 Cl83 118.89(11) . . ? C83 C23 Cl83 2.3(6) . . ? C23 C33 C43 120.0 . . ? C23 C33 H33 120.0 . . ? C43 C33 H33 120.0 . . ? C53 C43 C33 120.0 . . ? C53 C43 H43 120.0 . . ? C33 C43 H43 120.0 . . ? C43 C53 C63 120.0 . . ? C43 C53 H53 120.0 . . ? C63 C53 H53 120.0 . . ? C53 C63 C13 120.0 . . ? C53 C63 H63 120.0 . . ? C13 C63 H63 120.0 . . ? C13 O73 H73 110.5(17) . . ? C23 C83 H813 109.5 . . ? C23 C83 H823 109.5 . . ? C23 C83 H833 109.5 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 30.64 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.644 _refine_diff_density_min -0.242 _refine_diff_density_rms 0.050 # Attachment 'MPI.CIF' data_MPI _database_code_depnum_ccdc_archive 'CCDC 698229' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-methylphenol ; _chemical_name_common 2-methylphenol _chemical_melting_point ? _chemical_formula_moiety 'C7 H8 O' _chemical_formula_sum 'C7 H8 O' _chemical_formula_weight 108.13 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Trigonal _symmetry_space_group_name_H-M P3(2) _symmetry_space_group_name_Hall 'P 32' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+2/3' '-x+y, -x, z+1/3' _cell_length_a 16.4153(2) _cell_length_b 16.4153(2) _cell_length_c 5.7931(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 1351.88(5) _cell_formula_units_Z 9 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6079 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 29.49 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.62 _exptl_crystal_size_mid 0.54 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.195 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 522 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.847 _exptl_absorpt_correction_T_max 0.98 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count 0 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 14653 _diffrn_reflns_av_R_equivalents 0.0532 _diffrn_reflns_av_sigmaI/netI 0.0375 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.48 _diffrn_reflns_theta_max 30.00 _reflns_number_total 2622 _reflns_number_gt 2538 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0742P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 10(10) _refine_ls_number_reflns 2622 _refine_ls_number_parameters 233 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0445 _refine_ls_R_factor_gt 0.0431 _refine_ls_wR_factor_ref 0.1048 _refine_ls_wR_factor_gt 0.1038 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C11 C 0.11895(13) 0.16725(14) 0.5049(3) 0.0219(3) Uani 1 1 d . . . C21 C 0.12625(14) 0.23789(15) 0.3578(4) 0.0243(4) Uani 1 1 d . . . C31 C 0.20067(16) 0.32918(15) 0.3955(4) 0.0310(4) Uani 1 1 d . . . H31 H 0.2074 0.3785 0.2974 0.037 Uiso 1 1 calc R . . C41 C 0.26515(16) 0.34961(16) 0.5731(4) 0.0323(5) Uani 1 1 d . . . H41 H 0.3154 0.4121 0.5949 0.039 Uiso 1 1 calc R . . C51 C 0.25568(16) 0.27805(17) 0.7184(4) 0.0283(4) Uani 1 1 d . . . H51 H 0.2991 0.2916 0.8409 0.034 Uiso 1 1 calc R . . C61 C 0.18264(14) 0.18676(14) 0.6841(4) 0.0242(4) Uani 1 1 d . . . H61 H 0.1761 0.1376 0.7828 0.029 Uiso 1 1 calc R . . O71 O 0.04571(11) 0.07696(10) 0.4683(3) 0.0285(3) Uani 1 1 d D . . H71 H 0.045(2) 0.0386(17) 0.560(5) 0.033(8) Uiso 1 1 d D . . C81 C 0.05686(15) 0.21609(16) 0.1666(4) 0.0293(4) Uani 1 1 d . . . H811 H 0.0644 0.1770 0.0505 0.044 Uiso 1 1 calc R . . H821 H 0.0679 0.2749 0.0951 0.044 Uiso 1 1 calc R . . H831 H -0.0071 0.1822 0.2292 0.044 Uiso 1 1 calc R . . C12 C 0.49588(14) 0.23219(14) 0.0479(3) 0.0221(3) Uani 1 1 d . . . C22 C 0.43711(15) 0.23395(15) 0.2196(3) 0.0250(4) Uani 1 1 d . . . C32 C 0.34249(16) 0.16428(17) 0.2116(4) 0.0307(4) Uani 1 1 d . . . H32 H 0.3006 0.1642 0.3247 0.037 Uiso 1 1 calc R . . C42 C 0.30795(15) 0.09494(17) 0.0425(4) 0.0332(5) Uani 1 1 d . . . H42 H 0.2432 0.0482 0.0411 0.040 Uiso 1 1 calc R . . C52 C 0.36822(16) 0.09398(16) -0.1247(4) 0.0311(4) Uani 1 1 d . . . H52 H 0.3452 0.0462 -0.2394 0.037 Uiso 1 1 calc R . . C62 C 0.46228(15) 0.16334(14) -0.1225(3) 0.0253(4) Uani 1 1 d . . . H62 H 0.5038 0.1638 -0.2374 0.030 Uiso 1 1 calc R . . O72 O 0.58909(10) 0.30268(11) 0.0511(3) 0.0262(3) Uani 1 1 d D . . H72 H 0.6217(17) 0.295(2) -0.043(4) 0.030(7) Uiso 1 1 d D . . C82 C 0.47562(17) 0.30725(17) 0.4073(4) 0.0309(4) Uani 1 1 d . . . H812 H 0.4235 0.3030 0.4994 0.046 Uiso 1 1 calc R . . H822 H 0.5108 0.3699 0.3378 0.046 Uiso 1 1 calc R . . H832 H 0.5176 0.2965 0.5070 0.046 Uiso 1 1 calc R . . C13 C 0.40198(14) -0.16408(14) 0.5298(4) 0.0248(4) Uani 1 1 d . . . C23 C 0.38985(15) -0.11351(15) 0.3543(4) 0.0277(4) Uani 1 1 d . . . C33 C 0.45191(19) -0.01624(17) 0.3472(4) 0.0354(5) Uani 1 1 d . . . H33 H 0.4448 0.0202 0.2300 0.042 Uiso 1 1 calc R . . C43 C 0.52357(18) 0.02787(16) 0.5084(5) 0.0374(5) Uani 1 1 d . . . H43 H 0.5659 0.0937 0.4981 0.045 Uiso 1 1 calc R . . C53 C 0.53345(16) -0.02358(17) 0.6839(4) 0.0347(5) Uani 1 1 d . . . H53 H 0.5819 0.0069 0.7955 0.042 Uiso 1 1 calc R . . C63 C 0.47222(16) -0.12034(16) 0.6966(4) 0.0291(4) Uani 1 1 d . . . H63 H 0.4782 -0.1562 0.8174 0.035 Uiso 1 1 calc R . . O73 O 0.34215(11) -0.26067(10) 0.5396(2) 0.0263(3) Uani 1 1 d D . . H73 H 0.352(2) -0.286(2) 0.651(4) 0.038(8) Uiso 1 1 d D . . C83 C 0.31346(17) -0.16157(18) 0.1774(4) 0.0342(5) Uani 1 1 d . . . H813 H 0.3272 -0.2021 0.0803 0.051 Uiso 1 1 calc R . . H823 H 0.3103 -0.1142 0.0809 0.051 Uiso 1 1 calc R . . H833 H 0.2530 -0.1998 0.2555 0.051 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C11 0.0177(8) 0.0214(8) 0.0265(9) -0.0015(7) 0.0013(6) 0.0097(7) C21 0.0215(8) 0.0251(9) 0.0267(9) 0.0001(7) 0.0008(7) 0.0120(8) C31 0.0284(10) 0.0232(9) 0.0356(11) 0.0037(8) -0.0008(8) 0.0087(8) C41 0.0258(9) 0.0239(9) 0.0393(12) -0.0033(8) -0.0026(8) 0.0064(8) C51 0.0254(9) 0.0319(10) 0.0279(9) -0.0052(7) -0.0043(7) 0.0145(8) C61 0.0230(8) 0.0252(9) 0.0267(9) -0.0002(7) -0.0001(7) 0.0139(7) O71 0.0242(7) 0.0209(7) 0.0363(8) 0.0030(6) -0.0066(6) 0.0081(6) C81 0.0276(10) 0.0299(10) 0.0302(10) 0.0022(8) -0.0030(7) 0.0142(8) C12 0.0216(8) 0.0206(8) 0.0237(9) 0.0029(7) 0.0007(7) 0.0102(7) C22 0.0275(9) 0.0266(9) 0.0237(9) 0.0042(7) 0.0032(7) 0.0156(8) C32 0.0263(10) 0.0357(11) 0.0313(10) 0.0107(8) 0.0068(8) 0.0165(9) C42 0.0213(9) 0.0319(11) 0.0380(12) 0.0074(9) -0.0010(8) 0.0072(8) C52 0.0288(10) 0.0240(9) 0.0346(11) 0.0003(8) -0.0080(8) 0.0087(8) C62 0.0254(9) 0.0243(9) 0.0253(9) -0.0004(7) -0.0005(7) 0.0117(8) O72 0.0223(7) 0.0230(6) 0.0294(7) -0.0046(5) 0.0023(5) 0.0083(6) C82 0.0349(11) 0.0355(11) 0.0268(10) -0.0020(8) 0.0042(8) 0.0210(9) C13 0.0241(9) 0.0233(9) 0.0274(9) 0.0012(7) 0.0060(7) 0.0120(7) C23 0.0279(10) 0.0293(10) 0.0290(10) 0.0026(8) 0.0055(8) 0.0166(9) C33 0.0383(12) 0.0298(10) 0.0408(12) 0.0085(9) 0.0169(10) 0.0192(10) C43 0.0373(12) 0.0235(10) 0.0485(14) -0.0025(9) 0.0159(10) 0.0131(9) C53 0.0281(10) 0.0295(10) 0.0405(12) -0.0092(9) 0.0039(9) 0.0098(9) C63 0.0273(10) 0.0277(10) 0.0318(10) -0.0026(8) 0.0032(8) 0.0135(8) O73 0.0248(7) 0.0213(7) 0.0266(7) 0.0012(5) -0.0042(6) 0.0069(6) C83 0.0332(11) 0.0400(12) 0.0307(10) 0.0071(9) 0.0011(8) 0.0193(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C11 O71 1.380(2) . ? C11 C61 1.392(3) . ? C11 C21 1.395(3) . ? C21 C31 1.398(3) . ? C21 C81 1.498(3) . ? C31 C41 1.392(3) . ? C31 H31 0.9500 . ? C41 C51 1.389(3) . ? C41 H41 0.9500 . ? C51 C61 1.388(3) . ? C51 H51 0.9500 . ? C61 H61 0.9500 . ? O71 H71 0.8200(10) . ? C81 H811 0.9800 . ? C81 H821 0.9800 . ? C81 H831 0.9800 . ? C12 O72 1.382(2) . ? C12 C62 1.390(3) . ? C12 C22 1.396(3) . ? C22 C32 1.395(3) . ? C22 C82 1.507(3) . ? C32 C42 1.390(4) . ? C32 H32 0.9500 . ? C42 C52 1.390(4) . ? C42 H42 0.9500 . ? C52 C62 1.387(3) . ? C52 H52 0.9500 . ? C62 H62 0.9500 . ? O72 H72 0.8200(11) . ? C82 H812 0.9800 . ? C82 H822 0.9800 . ? C82 H832 0.9800 . ? C13 O73 1.387(2) . ? C13 C23 1.388(3) . ? C13 C63 1.397(3) . ? C23 C33 1.401(3) . ? C23 C83 1.502(3) . ? C33 C43 1.389(4) . ? C33 H33 0.9500 . ? C43 C53 1.382(4) . ? C43 H43 0.9500 . ? C53 C63 1.394(3) . ? C53 H53 0.9500 . ? C63 H63 0.9500 . ? O73 H73 0.8200(10) . ? C83 H813 0.9800 . ? C83 H823 0.9800 . ? C83 H833 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O71 C11 C61 120.82(18) . . ? O71 C11 C21 117.72(17) . . ? C61 C11 C21 121.46(18) . . ? C11 C21 C31 117.45(19) . . ? C11 C21 C81 120.94(18) . . ? C31 C21 C81 121.61(19) . . ? C41 C31 C21 121.7(2) . . ? C41 C31 H31 119.1 . . ? C21 C31 H31 119.1 . . ? C51 C41 C31 119.6(2) . . ? C51 C41 H41 120.2 . . ? C31 C41 H41 120.2 . . ? C61 C51 C41 119.8(2) . . ? C61 C51 H51 120.1 . . ? C41 C51 H51 120.1 . . ? C51 C61 C11 119.94(19) . . ? C51 C61 H61 120.0 . . ? C11 C61 H61 120.0 . . ? C11 O71 H71 113(2) . . ? C21 C81 H811 109.5 . . ? C21 C81 H821 109.5 . . ? H811 C81 H821 109.5 . . ? C21 C81 H831 109.5 . . ? H811 C81 H831 109.5 . . ? H821 C81 H831 109.5 . . ? O72 C12 C62 120.88(18) . . ? O72 C12 C22 117.42(18) . . ? C62 C12 C22 121.69(19) . . ? C32 C22 C12 117.2(2) . . ? C32 C22 C82 121.95(19) . . ? C12 C22 C82 120.83(19) . . ? C42 C32 C22 121.7(2) . . ? C42 C32 H32 119.1 . . ? C22 C32 H32 119.1 . . ? C52 C42 C32 119.9(2) . . ? C52 C42 H42 120.0 . . ? C32 C42 H42 120.0 . . ? C62 C52 C42 119.4(2) . . ? C62 C52 H52 120.3 . . ? C42 C52 H52 120.3 . . ? C52 C62 C12 120.0(2) . . ? C52 C62 H62 120.0 . . ? C12 C62 H62 120.0 . . ? C12 O72 H72 113(2) . . ? C22 C82 H812 109.5 . . ? C22 C82 H822 109.5 . . ? H812 C82 H822 109.5 . . ? C22 C82 H832 109.5 . . ? H812 C82 H832 109.5 . . ? H822 C82 H832 109.5 . . ? O73 C13 C23 118.81(19) . . ? O73 C13 C63 119.34(18) . . ? C23 C13 C63 121.84(19) . . ? C13 C23 C33 117.6(2) . . ? C13 C23 C83 121.15(19) . . ? C33 C23 C83 121.3(2) . . ? C43 C33 C23 121.2(2) . . ? C43 C33 H33 119.4 . . ? C23 C33 H33 119.4 . . ? C53 C43 C33 120.2(2) . . ? C53 C43 H43 119.9 . . ? C33 C43 H43 119.9 . . ? C43 C53 C63 119.8(2) . . ? C43 C53 H53 120.1 . . ? C63 C53 H53 120.1 . . ? C53 C63 C13 119.3(2) . . ? C53 C63 H63 120.4 . . ? C13 C63 H63 120.4 . . ? C13 O73 H73 114(3) . . ? C23 C83 H813 109.5 . . ? C23 C83 H823 109.5 . . ? H813 C83 H823 109.5 . . ? C23 C83 H833 109.5 . . ? H813 C83 H833 109.5 . . ? H823 C83 H833 109.5 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.366 _refine_diff_density_min -0.239 _refine_diff_density_rms 0.054 # Attachment 'MPII.cif' data_MPII _database_code_depnum_ccdc_archive 'CCDC 698230' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-methylphenol ; _chemical_name_common 2-methylphenol _chemical_melting_point ? _chemical_formula_moiety 'C7 H8 O' _chemical_formula_sum 'C7 H8 O' _chemical_formula_weight 108.13 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 5.9637(4) _cell_length_b 4.7006(3) _cell_length_c 19.769(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.792(10) _cell_angle_gamma 90.00 _cell_volume 553.53(10) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 633 _cell_measurement_theta_min 3.52 _cell_measurement_theta_max 21.40 _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.298 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 232 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.327 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details SADABS _exptl_special_details ? _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 2367 _diffrn_reflns_av_R_equivalents 0.0629 _diffrn_reflns_av_sigmaI/netI 0.0403 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.52 _diffrn_reflns_theta_max 23.25 _reflns_number_total 307 _reflns_number_gt 217 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker-Nonius Apex II' _computing_cell_refinement 'Bruker-Nonius Apex II' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0762P)^2^+1.8389P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 307 _refine_ls_number_parameters 17 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1286 _refine_ls_R_factor_gt 0.0870 _refine_ls_wR_factor_ref 0.2256 _refine_ls_wR_factor_gt 0.1957 _refine_ls_goodness_of_fit_ref 1.122 _refine_ls_restrained_S_all 1.122 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4767(4) 0.5171(6) 0.8262(3) 0.0303(19) Uiso 1 1 d G . . C2 C 0.5026(5) 0.6422(7) 0.8898(3) 0.034(2) Uiso 1 1 d G . . C3 C 0.6836(7) 0.5678(9) 0.9331(3) 0.048(2) Uiso 1 1 d G . . H3 H 0.7009 0.6515 0.9757 0.057 Uiso 1 1 calc R . . C4 C 0.8387(7) 0.3683(10) 0.9129(4) 0.049(2) Uiso 1 1 d G . . H4 H 0.9598 0.3185 0.9419 0.059 Uiso 1 1 calc R . . C5 C 0.8129(6) 0.2432(9) 0.8493(4) 0.042(2) Uiso 1 1 d G . . H5 H 0.9167 0.1097 0.8357 0.050 Uiso 1 1 calc R . . C6 C 0.6319(6) 0.3176(8) 0.8059(3) 0.041(2) Uiso 1 1 d G . . H6 H 0.6146 0.2339 0.7634 0.050 Uiso 1 1 calc R . . O7 O 0.2985(6) 0.5903(8) 0.7840(4) 0.0398(17) Uiso 1 1 d G . . H7 H 0.2248 0.4478 0.7741 0.060 Uiso 1 1 calc R . . C8 C 0.3307(8) 0.8567(11) 0.9117(4) 0.046(2) Uiso 1 1 d G . . H81 H 0.3641 1.0401 0.8933 0.069 Uiso 1 1 calc R . . H82 H 0.3355 0.8676 0.9602 0.069 Uiso 1 1 calc R . . H83 H 0.1836 0.7982 0.8954 0.069 Uiso 1 1 calc R . . _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O7 1.3621 . ? C1 C2 1.3900 . ? C1 C6 1.3900 . ? C2 C3 1.3900 . ? C2 C8 1.5158 . ? C3 C4 1.3900 . ? C3 H3 0.9300 . ? C4 C5 1.3900 . ? C4 H4 0.9300 . ? C5 C6 1.3900 . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? O7 H7 0.8200 . ? C8 H81 0.9600 . ? C8 H82 0.9600 . ? C8 H83 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O7 C1 C2 119.7 . . ? O7 C1 C6 120.3 . . ? C2 C1 C6 120.0 . . ? C1 C2 C3 120.0 . . ? C1 C2 C8 119.5 . . ? C3 C2 C8 120.5 . . ? C4 C3 C2 120.0 . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C5 C4 C3 120.0 . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C4 C5 C6 120.0 . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C5 C6 C1 120.0 . . ? C5 C6 H6 120.0 . . ? C1 C6 H6 120.0 . . ? C1 O7 H7 109.5 . . ? C2 C8 H81 109.5 . . ? C2 C8 H82 109.5 . . ? H81 C8 H82 109.5 . . ? C2 C8 H83 109.5 . . ? H81 C8 H83 109.5 . . ? H82 C8 H83 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O7 H7 O7 0.82 2.04 2.756(8) 146.1 2_546 _diffrn_measured_fraction_theta_max 0.383 _diffrn_reflns_theta_full 23.25 _diffrn_measured_fraction_theta_full 0.383 _refine_diff_density_max 0.215 _refine_diff_density_min -0.200 _refine_diff_density_rms 0.052