# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Andreas Lemmerer' _publ_contact_author_email ANDREAS.LEMMERER@GMAIL.COM _publ_section_title ; Z' > 1 polymorphs of 3-hydroxybenzyl alcohol and the crystal structures of its isomers 2-hydroxybenzyl alcohol and 4-hydroxybenzyl alcohol. ; _publ_requested_category FO loop_ _publ_author_name 'Andreas Lemmerer' C.Esterhuysen # Attachment 'Hydroxybenzyl_alcohol_Lemmerer_diols.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 738805' _audit_creation_date 2009-04-28T15:59:09-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 2-hydroxybenzylalcohol ; _chemical_formula_moiety 'C7 H8 O2' _chemical_formula_sum 'C7 H8 O2' _chemical_formula_weight 124.13 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.0471(12) _cell_length_b 5.3712(4) _cell_length_c 8.5718(8) _cell_angle_alpha 90 _cell_angle_beta 106.483(3) _cell_angle_gamma 90 _cell_volume 620.16(9) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1016 _cell_measurement_theta_min 3.02 _cell_measurement_theta_max 27.64 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.57 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.33 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 264 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0476 _diffrn_reflns_av_unetI/netI 0.0562 _diffrn_reflns_number 3797 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.51 _diffrn_reflns_theta_max 28 _diffrn_reflns_theta_full 28 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _reflns_number_total 1488 _reflns_number_gt 976 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SMART, Bruker (1998)' _computing_cell_refinement 'Bruker SAINT+, Bruker (1999)' _computing_data_reduction 'Bruker SAINT+' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999) ; _computing_publication_material ; WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2003) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0370P)^2^] 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_number_reflns 1488 _refine_ls_number_parameters 88 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0679 _refine_ls_R_factor_gt 0.0383 _refine_ls_wR_factor_ref 0.0865 _refine_ls_wR_factor_gt 0.0772 _refine_ls_goodness_of_fit_ref 0.917 _refine_ls_restrained_S_all 0.917 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.213 _refine_diff_density_min -0.176 _refine_diff_density_rms 0.039 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.71560(10) 0.3970(2) 0.66693(16) 0.0252(3) Uani 1 1 d . . . C2 C 0.70672(9) 0.6073(2) 0.75796(16) 0.0250(3) Uani 1 1 d . . . C3 C 0.78981(10) 0.7287(3) 0.85256(16) 0.0300(3) Uani 1 1 d . . . H3 H 0.7827 0.8718 0.9135 0.036 Uiso 1 1 calc R . . C4 C 0.88320(11) 0.6417(3) 0.85831(18) 0.0361(4) Uani 1 1 d . . . H4 H 0.9404 0.7255 0.923 0.043 Uiso 1 1 calc R . . C5 C 0.89397(11) 0.4331(3) 0.77034(19) 0.0385(4) Uani 1 1 d . . . H5 H 0.9583 0.3728 0.7749 0.046 Uiso 1 1 calc R . . C6 C 0.81067(11) 0.3132(3) 0.67602(17) 0.0339(4) Uani 1 1 d . . . H6 H 0.8184 0.1699 0.6158 0.041 Uiso 1 1 calc R . . C7 C 0.62571(10) 0.2690(2) 0.56158(16) 0.0288(3) Uani 1 1 d . . . H7A H 0.6445 0.1047 0.5271 0.035 Uiso 1 1 calc R . . H7B H 0.5768 0.2419 0.6234 0.035 Uiso 1 1 calc R . . O1 O 0.58259(7) 0.41994(17) 0.42152(12) 0.0306(3) Uani 1 1 d . . . O2 O 0.61279(7) 0.68704(17) 0.75092(12) 0.0306(3) Uani 1 1 d . . . H1 H 0.5205(12) 0.386(3) 0.381(2) 0.046 Uiso 1 1 d . . . H2 H 0.6134(11) 0.814(3) 0.810(2) 0.046 Uiso 1 1 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 C1 0.0324(8) 0.0225(7) 0.0216(7) 0.0043(6) 0.0091(6) 0.0026(6) C2 0.0279(8) 0.0248(7) 0.0230(7) 0.0049(6) 0.0084(6) 0.0041(6) C3 0.0328(8) 0.0291(7) 0.0284(8) -0.0015(6) 0.0090(7) -0.0009(6) C4 0.0286(8) 0.0464(9) 0.0315(8) 0.0044(7) 0.0057(7) -0.0027(7) C5 0.0308(8) 0.0485(9) 0.0380(9) 0.0075(8) 0.0124(8) 0.0129(7) C6 0.0428(9) 0.0317(8) 0.0300(8) 0.0043(7) 0.0146(7) 0.0111(7) C7 0.0421(9) 0.0210(7) 0.0252(7) 0.0011(6) 0.0123(7) 0.0014(6) O1 0.0302(5) 0.0354(6) 0.0252(5) 0.0046(4) 0.0064(5) -0.0060(4) O2 0.0283(5) 0.0280(5) 0.0349(6) -0.0094(5) 0.0079(5) 0.0019(4) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C6 1.3902(19) . ? C1 C2 1.3983(18) . ? C1 C7 1.4952(19) . ? C2 O2 1.3721(15) . ? C2 C3 1.3814(19) . ? C3 C4 1.3805(19) . ? C3 H3 0.95 . ? C4 C5 1.383(2) . ? C4 H4 0.95 . ? C5 C6 1.379(2) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? C7 O1 1.4329(16) . ? C7 H7A 0.99 . ? C7 H7B 0.99 . ? O1 H1 0.861(17) . ? O2 H2 0.851(17) . ? 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 C6 C1 C2 117.81(13) . . ? C6 C1 C7 121.21(12) . . ? C2 C1 C7 120.98(12) . . ? O2 C2 C3 121.34(11) . . ? O2 C2 C1 117.68(12) . . ? C3 C2 C1 120.98(12) . . ? C4 C3 C2 119.80(13) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 C5 120.34(14) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C6 C5 C4 119.48(13) . . ? C6 C5 H5 120.3 . . ? C4 C5 H5 120.3 . . ? C5 C6 C1 121.58(13) . . ? C5 C6 H6 119.2 . . ? C1 C6 H6 119.2 . . ? O1 C7 C1 109.25(10) . . ? O1 C7 H7A 109.8 . . ? C1 C7 H7A 109.8 . . ? O1 C7 H7B 109.8 . . ? C1 C7 H7B 109.8 . . ? H7A C7 H7B 108.3 . . ? C7 O1 H1 111.1(11) . . ? C2 O2 H2 112.2(10) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 O2 -178.92(11) . . . . ? C7 C1 C2 O2 1.92(18) . . . . ? C6 C1 C2 C3 0.58(19) . . . . ? C7 C1 C2 C3 -178.59(12) . . . . ? O2 C2 C3 C4 179.23(12) . . . . ? C1 C2 C3 C4 -0.2(2) . . . . ? C2 C3 C4 C5 -0.2(2) . . . . ? C3 C4 C5 C6 0.3(2) . . . . ? C4 C5 C6 C1 0.0(2) . . . . ? C2 C1 C6 C5 -0.5(2) . . . . ? C7 C1 C6 C5 178.70(12) . . . . ? C6 C1 C7 O1 -106.57(14) . . . . ? C2 C1 C7 O1 72.56(15) . . . . ? 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 O1 H1 O2 0.86(2) 1.93(2) 2.783(1) 169(2) 3_666 O2 H2 O1 0.85(2) 1.84(2) 2.670(1) 166(2) 4_576 # Attachment 'archive corrected for 2a.cif' data_2a2 _database_code_depnum_ccdc_archive 'CCDC 738806' _audit_creation_date 2009-03-24T16:16:42-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 3-hydroxybenzylalcohol Form I ; _chemical_formula_moiety 'C7 H8 O2' _chemical_formula_sum 'C7 H8 O2' _chemical_formula_weight 124.13 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/b _symmetry_space_group_name_Hall '-P 2xab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, -y, -z' '-x+1/2, y+1/2, z' _cell_length_a 8.1989(12) _cell_length_b 11.5438(18) _cell_length_c 14.516(2) _cell_angle_alpha 113.323(5) _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1261.6(3) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1615 _cell_measurement_theta_min 2.92 _cell_measurement_theta_max 26.47 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.307 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1 0 0 0.04 -1 0 0 0.04 -3 0 2 0.1 0 0 -1 0.1 0 1 0 0.25 0 -1 0 0.25 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0446 _diffrn_reflns_av_unetI/netI 0.0674 _diffrn_reflns_number 8388 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.53 _diffrn_reflns_theta_max 27.99 _diffrn_reflns_theta_full 27.99 _diffrn_measured_fraction_theta_full 0.969 _diffrn_measured_fraction_theta_max 0.969 _reflns_number_total 2941 _reflns_number_gt 1596 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SMART, Bruker (1998)' _computing_cell_refinement 'Bruker SAINT+, Bruker (1999)' _computing_data_reduction 'Bruker SAINT+' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999) ; _computing_publication_material ; WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2003) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0599P)^2^] 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_number_reflns 2941 _refine_ls_number_parameters 175 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1159 _refine_ls_R_factor_gt 0.0504 _refine_ls_wR_factor_ref 0.1215 _refine_ls_wR_factor_gt 0.1037 _refine_ls_goodness_of_fit_ref 0.957 _refine_ls_restrained_S_all 0.957 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.191 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.047 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 -0.1520(2) 0.49403(15) 0.38265(13) 0.0297(4) Uani 1 1 d . . . C2 C -0.0162(2) 0.41668(16) 0.35650(13) 0.0325(4) Uani 1 1 d . . . H2A H -0.0292 0.3299 0.3351 0.039 Uiso 1 1 calc R . . C3 C 0.1379(2) 0.46617(16) 0.36161(13) 0.0316(4) Uani 1 1 d . . . C4 C 0.1590(2) 0.59496(16) 0.39214(14) 0.0354(5) Uani 1 1 d . . . H4A H 0.2626 0.6289 0.3947 0.042 Uiso 1 1 calc R . . C5 C 0.0234(2) 0.67232(16) 0.41873(14) 0.0391(5) Uani 1 1 d . . . H5 H 0.0365 0.7591 0.4403 0.047 Uiso 1 1 calc R . . C6 C -0.1308(2) 0.62297(16) 0.41376(14) 0.0364(5) Uani 1 1 d . . . H6 H -0.2209 0.6763 0.4313 0.044 Uiso 1 1 calc R . . C7 C -0.3184(2) 0.43706(17) 0.37738(15) 0.0394(5) Uani 1 1 d . . . H7A H -0.3163 0.3509 0.3279 0.047 Uiso 1 1 calc R . . H7B H -0.3431 0.4343 0.4418 0.047 Uiso 1 1 calc R . . O1 O -0.44575(16) 0.50336(13) 0.35221(11) 0.0463(4) Uani 1 1 d . . . H1 H -0.424(3) 0.5150(19) 0.2970(18) 0.069 Uiso 1 1 d . . . O2 O 0.26751(16) 0.38398(12) 0.33460(12) 0.0501(4) Uani 1 1 d . . . H2 H 0.352(3) 0.427(2) 0.3391(19) 0.075 Uiso 1 1 d . . . C8 C 0.4957(2) 0.12230(16) 0.12813(13) 0.0314(4) Uani 1 1 d . . . C9 C 0.6310(2) 0.07587(16) 0.15902(14) 0.0337(5) Uani 1 1 d . . . H9 H 0.6182 0.0145 0.1849 0.04 Uiso 1 1 calc R . . C10 C 0.7856(2) 0.12008(15) 0.15175(13) 0.0325(4) Uani 1 1 d . . . C11 C 0.8069(2) 0.21119(16) 0.11373(14) 0.0374(5) Uani 1 1 d . . . H11 H 0.9107 0.2403 0.1082 0.045 Uiso 1 1 calc R . . C12 C 0.6714(2) 0.25849(17) 0.08405(14) 0.0419(5) Uani 1 1 d . . . H12 H 0.6844 0.3205 0.0588 0.05 Uiso 1 1 calc R . . C13 C 0.5170(2) 0.21548(17) 0.09116(14) 0.0395(5) Uani 1 1 d . . . H13 H 0.427 0.2488 0.0712 0.047 Uiso 1 1 calc R . . C14 C 0.3299(2) 0.06990(17) 0.13271(15) 0.0406(5) Uani 1 1 d . . . H14A H 0.3024 0.0075 0.0667 0.049 Uiso 1 1 calc R . . H14B H 0.3341 0.0272 0.1783 0.049 Uiso 1 1 calc R . . O3 O 0.20458(16) 0.16217(13) 0.16461(12) 0.0537(4) Uani 1 1 d . . . H3 H 0.237(3) 0.224(2) 0.2207(18) 0.081 Uiso 1 1 d . . . O4 O 0.91465(17) 0.07193(13) 0.18575(11) 0.0501(4) Uani 1 1 d . . . H4 H 1.010(3) 0.103(2) 0.1719(18) 0.075 Uiso 1 1 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 C1 0.0226(10) 0.0367(10) 0.0306(10) 0.0143(8) -0.0004(8) -0.0022(7) C2 0.0276(11) 0.0285(9) 0.0395(11) 0.0116(8) -0.0005(8) -0.0006(8) C3 0.0220(10) 0.0354(10) 0.0355(10) 0.0119(8) -0.0016(8) 0.0018(8) C4 0.0235(10) 0.0402(11) 0.0426(11) 0.0166(9) -0.0050(9) -0.0061(8) C5 0.0348(12) 0.0294(10) 0.0501(12) 0.0127(9) -0.0053(9) -0.0014(8) C6 0.0226(10) 0.0358(10) 0.0476(12) 0.0132(9) -0.0008(9) 0.0063(8) C7 0.0227(11) 0.0451(11) 0.0520(13) 0.0210(9) 0.0011(9) 0.0003(8) O1 0.0200(8) 0.0645(9) 0.0613(9) 0.0324(8) -0.0008(7) 0.0007(6) O2 0.0211(8) 0.0386(8) 0.0809(11) 0.0133(7) 0.0029(7) 0.0039(6) C8 0.0265(11) 0.0367(10) 0.0266(10) 0.0076(8) 0.0010(8) -0.0010(8) C9 0.0307(11) 0.0356(10) 0.0374(11) 0.0172(8) -0.0015(8) -0.0043(8) C10 0.0262(10) 0.0360(10) 0.0348(11) 0.0134(8) -0.0022(8) -0.0004(8) C11 0.0288(11) 0.0407(10) 0.0439(12) 0.0179(9) 0.0011(9) -0.0068(8) C12 0.0373(12) 0.0463(11) 0.0494(12) 0.0266(10) 0.0009(10) -0.0028(9) C13 0.0289(11) 0.0488(11) 0.0443(12) 0.0224(10) -0.0025(9) 0.0049(9) C14 0.0268(11) 0.0457(11) 0.0459(12) 0.0146(9) 0.0021(9) 0.0004(9) O3 0.0220(8) 0.0550(9) 0.0695(10) 0.0092(7) 0.0012(7) 0.0005(6) O4 0.0241(8) 0.0627(9) 0.0781(11) 0.0434(8) -0.0052(8) -0.0026(7) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 1.383(2) . ? C1 C6 1.385(2) . ? C1 C7 1.503(2) . ? C2 C3 1.377(2) . ? C2 H2A 0.93 . ? C3 O2 1.374(2) . ? C3 C4 1.384(2) . ? C4 C5 1.382(2) . ? C4 H4A 0.93 . ? C5 C6 1.377(2) . ? C5 H5 0.93 . ? C6 H6 0.93 . ? C7 O1 1.425(2) . ? C7 H7A 0.97 . ? C7 H7B 0.97 . ? O1 H1 0.88(2) . ? O2 H2 0.84(2) . ? C8 C9 1.382(2) . ? C8 C13 1.390(3) . ? C8 C14 1.499(2) . ? C9 C10 1.387(2) . ? C9 H9 0.93 . ? C10 O4 1.374(2) . ? C10 C11 1.379(3) . ? C11 C12 1.380(3) . ? C11 H11 0.93 . ? C12 C13 1.378(2) . ? C12 H12 0.93 . ? C13 H13 0.93 . ? C14 O3 1.419(2) . ? C14 H14A 0.97 . ? C14 H14B 0.97 . ? O3 H3 0.89(2) . ? O4 H4 0.91(2) . ? 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 118.85(16) . . ? C2 C1 C7 119.65(15) . . ? C6 C1 C7 121.50(15) . . ? C3 C2 C1 121.01(16) . . ? C3 C2 H2A 119.5 . . ? C1 C2 H2A 119.5 . . ? O2 C3 C2 118.00(15) . . ? O2 C3 C4 121.88(15) . . ? C2 C3 C4 120.13(15) . . ? C5 C4 C3 118.88(16) . . ? C5 C4 H4A 120.6 . . ? C3 C4 H4A 120.6 . . ? C6 C5 C4 121.05(16) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C5 C6 C1 120.08(16) . . ? C5 C6 H6 120 . . ? C1 C6 H6 120 . . ? O1 C7 C1 114.17(15) . . ? O1 C7 H7A 108.7 . . ? C1 C7 H7A 108.7 . . ? O1 C7 H7B 108.7 . . ? C1 C7 H7B 108.7 . . ? H7A C7 H7B 107.6 . . ? C7 O1 H1 112.2(15) . . ? C3 O2 H2 107.1(16) . . ? C9 C8 C13 118.87(16) . . ? C9 C8 C14 119.87(16) . . ? C13 C8 C14 121.25(16) . . ? C8 C9 C10 120.52(16) . . ? C8 C9 H9 119.7 . . ? C10 C9 H9 119.7 . . ? O4 C10 C11 121.83(16) . . ? O4 C10 C9 117.59(16) . . ? C11 C10 C9 120.56(17) . . ? C10 C11 C12 118.80(18) . . ? C10 C11 H11 120.6 . . ? C12 C11 H11 120.6 . . ? C13 C12 C11 121.14(18) . . ? C13 C12 H12 119.4 . . ? C11 C12 H12 119.4 . . ? C12 C13 C8 120.10(17) . . ? C12 C13 H13 119.9 . . ? C8 C13 H13 119.9 . . ? O3 C14 C8 114.00(15) . . ? O3 C14 H14A 108.8 . . ? C8 C14 H14A 108.8 . . ? O3 C14 H14B 108.8 . . ? C8 C14 H14B 108.8 . . ? H14A C14 H14B 107.6 . . ? C14 O3 H3 108.3(15) . . ? C10 O4 H4 109.3(15) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.4(3) . . . . ? C7 C1 C2 C3 -179.27(17) . . . . ? C1 C2 C3 O2 179.95(16) . . . . ? C1 C2 C3 C4 -0.8(3) . . . . ? O2 C3 C4 C5 -179.69(17) . . . . ? C2 C3 C4 C5 1.0(3) . . . . ? C3 C4 C5 C6 -1.0(3) . . . . ? C4 C5 C6 C1 0.6(3) . . . . ? C2 C1 C6 C5 -0.3(3) . . . . ? C7 C1 C6 C5 179.34(18) . . . . ? C2 C1 C7 O1 -147.79(16) . . . . ? C6 C1 C7 O1 32.6(2) . . . . ? C13 C8 C9 C10 -1.0(3) . . . . ? C14 C8 C9 C10 177.60(16) . . . . ? C8 C9 C10 O4 178.65(15) . . . . ? C8 C9 C10 C11 0.1(3) . . . . ? O4 C10 C11 C12 -177.82(16) . . . . ? C9 C10 C11 C12 0.7(3) . . . . ? C10 C11 C12 C13 -0.5(3) . . . . ? C11 C12 C13 C8 -0.4(3) . . . . ? C9 C8 C13 C12 1.2(3) . . . . ? C14 C8 C13 C12 -177.43(16) . . . . ? C9 C8 C14 O3 140.39(17) . . . . ? C13 C8 C14 O3 -41.0(3) . . . . ? 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 O1 H1 O4 0.88(2) 1.97(2) 2.836(2) 167(2) 4 O2 H2 O1 0.84(2) 1.86(2) 2.6856(19) 172(2) 1_655 O3 H3 O2 0.89(2) 1.94(2) 2.812(2) 166(2) . O4 H4 O3 0.91(2) 1.76(2) 2.661(2) 170(2) 1_655 _chemical_name_common '3-hydroxybenzylalcohol Form I' ###END data_2b _database_code_depnum_ccdc_archive 'CCDC 738807' _audit_creation_date 2009-06-23T14:20:50-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 3-hydroxybenzylalcohol Z' = 3 ; _chemical_formula_moiety 'C7 H8 O2' _chemical_formula_sum 'C7 H8 O2' _chemical_formula_weight 124.13 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.1867(11) _cell_length_b 17.190(2) _cell_length_c 13.7935(18) _cell_angle_alpha 90 _cell_angle_beta 101.432(2) _cell_angle_gamma 90 _cell_volume 1902.6(4) _cell_formula_units_Z 12 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4707 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 27.68 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.42 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.3 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 0 -1 0.26 0 0 1 0.26 0 -1 0 0.25 0 1 0 0.25 1 1 0 0.21 -1 -1 0 0.21 6 -2 -3 0.22 -6 4 -1 0.22 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0243 _diffrn_reflns_av_unetI/netI 0.0269 _diffrn_reflns_number 15562 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 28 _diffrn_reflns_theta_full 28 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 4586 _reflns_number_gt 3251 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SMART, Bruker (1998)' _computing_cell_refinement 'Bruker SAINT+, Bruker (1999)' _computing_data_reduction 'Bruker SAINT+' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999) ; _computing_publication_material ; WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2003) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0539P)^2^+0.3505P] 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 SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.041(2) _refine_ls_number_reflns 4586 _refine_ls_number_parameters 263 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0614 _refine_ls_R_factor_gt 0.0382 _refine_ls_wR_factor_ref 0.1113 _refine_ls_wR_factor_gt 0.0963 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.155 _refine_diff_density_min -0.193 _refine_diff_density_rms 0.042 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.30546(14) 0.69874(7) 0.37258(9) 0.0346(3) Uani 1 1 d . . . C2 C 0.42949(15) 0.65989(7) 0.33693(9) 0.0357(3) Uani 1 1 d . . . H2A H 0.4085 0.6108 0.3088 0.043 Uiso 1 1 calc R . . C3 C 0.58527(15) 0.69395(7) 0.34303(9) 0.0359(3) Uani 1 1 d . . . C4 C 0.61872(16) 0.76628(8) 0.38631(10) 0.0402(3) Uani 1 1 d . . . H4A H 0.7233 0.7888 0.3912 0.048 Uiso 1 1 calc R . . C5 C 0.49490(17) 0.80460(8) 0.42219(11) 0.0451(3) Uani 1 1 d . . . H5A H 0.5167 0.8532 0.4514 0.054 Uiso 1 1 calc R . . C6 C 0.33905(16) 0.77167(8) 0.41530(10) 0.0416(3) Uani 1 1 d . . . H6A H 0.2565 0.7984 0.4393 0.05 Uiso 1 1 calc R . . C7 C 0.13661(15) 0.66147(8) 0.36463(11) 0.0429(3) Uani 1 1 d . . . H7A H 0.1231 0.6214 0.3142 0.051 Uiso 1 1 calc R . . H7B H 0.1309 0.6367 0.4271 0.051 Uiso 1 1 calc R . . O1 O 0.00359(11) 0.71606(7) 0.34050(8) 0.0530(3) Uani 1 1 d . . . H1 H 0.018(2) 0.7434(12) 0.2917(14) 0.079 Uiso 1 1 d . . . O2 O 0.69995(12) 0.65375(6) 0.30255(9) 0.0534(3) Uani 1 1 d . . . H2 H 0.799(3) 0.6783(11) 0.3156(14) 0.08 Uiso 1 1 d . . . C8 C 0.88040(14) 0.53699(7) 0.11747(9) 0.0326(3) Uani 1 1 d . . . C9 C 1.02318(14) 0.49202(7) 0.13864(9) 0.0345(3) Uani 1 1 d . . . H9 H 1.0164 0.4403 0.1572 0.041 Uiso 1 1 calc R . . C10 C 1.17624(14) 0.52369(7) 0.13224(9) 0.0340(3) Uani 1 1 d . . . C11 C 1.18749(15) 0.60047(8) 0.10363(9) 0.0371(3) Uani 1 1 d . . . H11 H 1.2901 0.6217 0.0988 0.045 Uiso 1 1 calc R . . C12 C 1.04446(16) 0.64514(8) 0.08238(10) 0.0407(3) Uani 1 1 d . . . H12 H 1.0511 0.6967 0.063 0.049 Uiso 1 1 calc R . . C13 C 0.89155(15) 0.61397(8) 0.08966(10) 0.0390(3) Uani 1 1 d . . . H13 H 0.7962 0.6447 0.0759 0.047 Uiso 1 1 calc R . . C14 C 0.71526(15) 0.49969(8) 0.12173(10) 0.0401(3) Uani 1 1 d . . . H14A H 0.6726 0.4744 0.0589 0.048 Uiso 1 1 calc R . . H14B H 0.7329 0.4598 0.1725 0.048 Uiso 1 1 calc R . . O3 O 0.59357(11) 0.55300(6) 0.14209(8) 0.0497(3) Uani 1 1 d . . . H3 H 0.631(2) 0.5794(11) 0.1930(14) 0.075 Uiso 1 1 d . . . O4 O 1.31366(11) 0.47662(6) 0.15600(8) 0.0493(3) Uani 1 1 d . . . H4 H 1.404(2) 0.5019(11) 0.1529(14) 0.074 Uiso 1 1 d . . . C15 C 1.60151(15) 0.37757(8) 0.37146(9) 0.0383(3) Uani 1 1 d . . . C16 C 1.72613(15) 0.33517(8) 0.34166(9) 0.0379(3) Uani 1 1 d . . . H16 H 1.7052 0.2846 0.3187 0.046 Uiso 1 1 calc R . . C17 C 1.88246(16) 0.36776(8) 0.34581(10) 0.0392(3) Uani 1 1 d . . . C18 C 1.91519(17) 0.44280(8) 0.37968(10) 0.0448(3) Uani 1 1 d . . . H18 H 2.0203 0.4644 0.3829 0.054 Uiso 1 1 calc R . . C19 C 1.79053(19) 0.48537(9) 0.40862(11) 0.0519(4) Uani 1 1 d . . . H19 H 1.8116 0.5362 0.4308 0.062 Uiso 1 1 calc R . . C20 C 1.63413(18) 0.45343(9) 0.40501(11) 0.0491(4) Uani 1 1 d . . . H20 H 1.551 0.4826 0.425 0.059 Uiso 1 1 calc R . . C21 C 1.43383(16) 0.34081(9) 0.36960(11) 0.0484(4) Uani 1 1 d . . . H21A H 1.426 0.2931 0.3314 0.058 Uiso 1 1 calc R . . H21B H 1.4249 0.3272 0.4366 0.058 Uiso 1 1 calc R . . O5 O 1.29835(12) 0.39032(8) 0.32824(9) 0.0633(3) Uani 1 1 d . . . H5 H 1.319(3) 0.4098(12) 0.2743(16) 0.095 Uiso 1 1 d . . . O6 O 2.00044(13) 0.32314(6) 0.31413(9) 0.0569(3) Uani 1 1 d . . . H6 H 2.097(3) 0.3477(12) 0.3219(15) 0.085 Uiso 1 1 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 C1 0.0245(6) 0.0445(7) 0.0348(6) 0.0020(5) 0.0062(5) -0.0014(5) C2 0.0283(6) 0.0367(6) 0.0424(7) -0.0035(5) 0.0075(5) -0.0011(5) C3 0.0249(6) 0.0414(7) 0.0423(7) -0.0013(5) 0.0087(5) 0.0010(5) C4 0.0265(6) 0.0438(7) 0.0496(7) -0.0020(6) 0.0060(5) -0.0054(5) C5 0.0370(7) 0.0415(7) 0.0550(8) -0.0120(6) 0.0049(6) -0.0018(6) C6 0.0306(7) 0.0495(8) 0.0460(7) -0.0087(6) 0.0104(5) 0.0042(6) C7 0.0268(6) 0.0522(8) 0.0515(8) 0.0014(6) 0.0120(6) -0.0029(6) O1 0.0239(5) 0.0683(7) 0.0688(7) 0.0069(5) 0.0144(5) 0.0007(5) O2 0.0285(5) 0.0542(6) 0.0820(8) -0.0192(5) 0.0219(5) -0.0026(4) C8 0.0221(6) 0.0412(7) 0.0349(6) -0.0016(5) 0.0070(5) -0.0021(5) C9 0.0264(6) 0.0366(6) 0.0415(7) 0.0032(5) 0.0093(5) -0.0017(5) C10 0.0226(6) 0.0433(7) 0.0370(6) 0.0018(5) 0.0075(5) 0.0026(5) C11 0.0251(6) 0.0450(7) 0.0430(7) 0.0008(6) 0.0113(5) -0.0063(5) C12 0.0365(7) 0.0365(6) 0.0506(7) 0.0050(6) 0.0121(6) -0.0012(5) C13 0.0269(6) 0.0434(7) 0.0469(7) 0.0029(6) 0.0082(5) 0.0053(5) C14 0.0226(6) 0.0474(7) 0.0512(8) -0.0009(6) 0.0094(5) -0.0024(5) O3 0.0230(5) 0.0610(6) 0.0675(7) -0.0096(5) 0.0145(4) -0.0014(4) O4 0.0228(5) 0.0534(6) 0.0734(7) 0.0146(5) 0.0132(4) 0.0053(4) C15 0.0288(6) 0.0514(8) 0.0345(6) 0.0044(6) 0.0054(5) 0.0012(6) C16 0.0306(6) 0.0408(7) 0.0423(7) 0.0000(5) 0.0072(5) -0.0025(5) C17 0.0295(6) 0.0455(7) 0.0427(7) 0.0029(6) 0.0076(5) -0.0004(5) C18 0.0363(7) 0.0488(8) 0.0472(8) 0.0018(6) 0.0028(6) -0.0097(6) C19 0.0540(9) 0.0455(8) 0.0530(8) -0.0068(7) 0.0032(7) -0.0028(7) C20 0.0419(8) 0.0561(9) 0.0490(8) -0.0060(7) 0.0085(6) 0.0107(7) C21 0.0296(7) 0.0644(9) 0.0520(8) 0.0092(7) 0.0097(6) 0.0009(6) O5 0.0264(5) 0.0895(9) 0.0752(8) 0.0275(7) 0.0130(5) 0.0060(5) O6 0.0317(5) 0.0575(6) 0.0860(8) -0.0100(6) 0.0225(5) -0.0025(5) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 1.3845(17) . ? C1 C6 1.3893(18) . ? C1 C7 1.5077(17) . ? C2 C3 1.3906(17) . ? C2 H2A 0.93 . ? C3 O2 1.3706(15) . ? C3 C4 1.3830(18) . ? C4 C5 1.3802(18) . ? C4 H4A 0.93 . ? C5 C6 1.3818(19) . ? C5 H5A 0.93 . ? C6 H6A 0.93 . ? C7 O1 1.4261(17) . ? C7 H7A 0.97 . ? C7 H7B 0.97 . ? O1 H1 0.85(2) . ? O2 H2 0.90(2) . ? C8 C9 1.3834(16) . ? C8 C13 1.3858(18) . ? C8 C14 1.5079(16) . ? C9 C10 1.3850(16) . ? C9 H9 0.93 . ? C10 O4 1.3717(15) . ? C10 C11 1.3858(18) . ? C11 C12 1.3823(18) . ? C11 H11 0.93 . ? C12 C13 1.3835(17) . ? C12 H12 0.93 . ? C13 H13 0.93 . ? C14 O3 1.4220(16) . ? C14 H14A 0.97 . ? C14 H14B 0.97 . ? O3 H3 0.841(19) . ? O4 H4 0.864(19) . ? C15 C16 1.3811(18) . ? C15 C20 1.392(2) . ? C15 C21 1.5067(18) . ? C16 C17 1.3878(17) . ? C16 H16 0.93 . ? C17 O6 1.3710(16) . ? C17 C18 1.3800(19) . ? C18 C19 1.378(2) . ? C18 H18 0.93 . ? C19 C20 1.385(2) . ? C19 H19 0.93 . ? C20 H20 0.93 . ? C21 O5 1.4244(17) . ? C21 H21A 0.97 . ? C21 H21B 0.97 . ? O5 H5 0.86(2) . ? O6 H6 0.88(2) . ? 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 119.24(11) . . ? C2 C1 C7 119.71(11) . . ? C6 C1 C7 121.05(11) . . ? C1 C2 C3 120.25(11) . . ? C1 C2 H2A 119.9 . . ? C3 C2 H2A 119.9 . . ? O2 C3 C4 122.42(11) . . ? O2 C3 C2 117.21(11) . . ? C4 C3 C2 120.36(11) . . ? C5 C4 C3 119.16(12) . . ? C5 C4 H4A 120.4 . . ? C3 C4 H4A 120.4 . . ? C4 C5 C6 120.90(12) . . ? C4 C5 H5A 119.5 . . ? C6 C5 H5A 119.5 . . ? C5 C6 C1 120.08(12) . . ? C5 C6 H6A 120 . . ? C1 C6 H6A 120 . . ? O1 C7 C1 112.59(11) . . ? O1 C7 H7A 109.1 . . ? C1 C7 H7A 109.1 . . ? O1 C7 H7B 109.1 . . ? C1 C7 H7B 109.1 . . ? H7A C7 H7B 107.8 . . ? C7 O1 H1 109.1(14) . . ? C3 O2 H2 110.3(12) . . ? C9 C8 C13 119.52(11) . . ? C9 C8 C14 118.73(11) . . ? C13 C8 C14 121.70(11) . . ? C8 C9 C10 120.28(11) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? O4 C10 C9 117.55(11) . . ? O4 C10 C11 122.15(11) . . ? C9 C10 C11 120.30(11) . . ? C12 C11 C10 119.22(11) . . ? C12 C11 H11 120.4 . . ? C10 C11 H11 120.4 . . ? C11 C12 C13 120.67(12) . . ? C11 C12 H12 119.7 . . ? C13 C12 H12 119.7 . . ? C12 C13 C8 120.01(12) . . ? C12 C13 H13 120 . . ? C8 C13 H13 120 . . ? O3 C14 C8 113.72(11) . . ? O3 C14 H14A 108.8 . . ? C8 C14 H14A 108.8 . . ? O3 C14 H14B 108.8 . . ? C8 C14 H14B 108.8 . . ? H14A C14 H14B 107.7 . . ? C14 O3 H3 110.9(13) . . ? C10 O4 H4 111.0(12) . . ? C16 C15 C20 119.28(12) . . ? C16 C15 C21 119.87(12) . . ? C20 C15 C21 120.84(12) . . ? C15 C16 C17 120.28(12) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? O6 C17 C18 121.95(12) . . ? O6 C17 C16 117.59(12) . . ? C18 C17 C16 120.46(12) . . ? C19 C18 C17 119.30(13) . . ? C19 C18 H18 120.4 . . ? C17 C18 H18 120.4 . . ? C18 C19 C20 120.78(13) . . ? C18 C19 H19 119.6 . . ? C20 C19 H19 119.6 . . ? C19 C20 C15 119.90(13) . . ? C19 C20 H20 120.1 . . ? C15 C20 H20 120.1 . . ? O5 C21 C15 113.00(12) . . ? O5 C21 H21A 109 . . ? C15 C21 H21A 109 . . ? O5 C21 H21B 109 . . ? C15 C21 H21B 109 . . ? H21A C21 H21B 107.8 . . ? C21 O5 H5 108.1(14) . . ? C17 O6 H6 111.3(13) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.63(19) . . . . ? C7 C1 C2 C3 179.42(12) . . . . ? C1 C2 C3 O2 -177.29(12) . . . . ? C1 C2 C3 C4 1.16(19) . . . . ? O2 C3 C4 C5 177.54(13) . . . . ? C2 C3 C4 C5 -0.8(2) . . . . ? C3 C4 C5 C6 0.0(2) . . . . ? C4 C5 C6 C1 0.5(2) . . . . ? C2 C1 C6 C5 -0.2(2) . . . . ? C7 C1 C6 C5 179.73(13) . . . . ? C2 C1 C7 O1 -141.10(12) . . . . ? C6 C1 C7 O1 38.95(17) . . . . ? C13 C8 C9 C10 0.09(19) . . . . ? C14 C8 C9 C10 177.85(11) . . . . ? C8 C9 C10 O4 178.76(11) . . . . ? C8 C9 C10 C11 -0.64(19) . . . . ? O4 C10 C11 C12 -178.85(12) . . . . ? C9 C10 C11 C12 0.52(19) . . . . ? C10 C11 C12 C13 0.1(2) . . . . ? C11 C12 C13 C8 -0.7(2) . . . . ? C9 C8 C13 C12 0.57(19) . . . . ? C14 C8 C13 C12 -177.12(12) . . . . ? C9 C8 C14 O3 153.87(12) . . . . ? C13 C8 C14 O3 -28.42(17) . . . . ? C20 C15 C16 C17 0.43(19) . . . . ? C21 C15 C16 C17 -178.13(12) . . . . ? C15 C16 C17 O6 -179.24(12) . . . . ? C15 C16 C17 C18 0.0(2) . . . . ? O6 C17 C18 C19 178.66(13) . . . . ? C16 C17 C18 C19 -0.5(2) . . . . ? C17 C18 C19 C20 0.7(2) . . . . ? C18 C19 C20 C15 -0.3(2) . . . . ? C16 C15 C20 C19 -0.3(2) . . . . ? C21 C15 C20 C19 178.25(13) . . . . ? C16 C15 C21 O5 -134.96(13) . . . . ? C20 C15 C21 O5 46.50(18) . . . . ? 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 O1 H1 O6 0.85(2) 1.99(2) 2.8124(16) 164.3(19) 2_755 O2 H2 O1 0.90(2) 1.76(2) 2.6617(14) 173.7(18) 1_655 O3 H3 O2 0.841(19) 1.975(19) 2.8093(16) 171.7(18) . O4 H4 O3 0.864(19) 1.818(19) 2.6807(14) 177.7(19) 1_655 O5 H5 O4 0.86(2) 1.99(2) 2.8247(16) 163(2) . O6 H6 O5 0.88(2) 1.79(2) 2.6706(15) 173.8(19) 1_655 ###END data_3 _database_code_depnum_ccdc_archive 'CCDC 738808' _audit_creation_date 2009-03-24T16:32:09-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 4-hydroxybenzylalcohol ; _chemical_formula_moiety 'C7 H8 O2' _chemical_formula_sum 'C7 H8 O2' _chemical_formula_weight 124.13 _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pna2(1) _symmetry_space_group_name_Hall 'P 2c -2n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 9.448(7) _cell_length_b 10.894(8) _cell_length_c 5.873(4) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 604.5(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1057 _cell_measurement_theta_min 3.74 _cell_measurement_theta_max 24.15 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.364 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 264 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.1 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0461 _diffrn_reflns_av_unetI/netI 0.037 _diffrn_reflns_number 4228 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.85 _diffrn_reflns_theta_max 27.99 _diffrn_reflns_theta_full 27.99 _diffrn_measured_fraction_theta_full 0.975 _diffrn_measured_fraction_theta_max 0.975 _reflns_number_total 780 _reflns_number_gt 616 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SMART, Bruker (1998)' _computing_cell_refinement 'Bruker SAINT+, Bruker (1999)' _computing_data_reduction 'Bruker SAINT+' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999) ; _computing_publication_material ; WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2003) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0906P)^2^] 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_number_reflns 780 _refine_ls_number_parameters 88 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.062 _refine_ls_R_factor_gt 0.0443 _refine_ls_wR_factor_ref 0.13 _refine_ls_wR_factor_gt 0.118 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 10(10) _refine_diff_density_max 0.22 _refine_diff_density_min -0.184 _refine_diff_density_rms 0.052 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.4477(3) 0.1783(2) 0.5818(5) 0.0327(6) Uani 1 1 d . . . C2 C 0.4195(3) 0.2294(3) 0.3724(5) 0.0380(7) Uani 1 1 d . . . H2A H 0.4669 0.3005 0.3289 0.046 Uiso 1 1 calc R . . C3 C 0.3234(3) 0.1778(3) 0.2271(6) 0.0380(7) Uani 1 1 d . . . H3 H 0.3058 0.2137 0.0862 0.046 Uiso 1 1 calc R . . C4 C 0.2528(3) 0.0726(2) 0.2899(5) 0.0319(6) Uani 1 1 d . . . C5 C 0.2783(3) 0.0209(2) 0.4983(5) 0.0332(6) Uani 1 1 d . . . H5 H 0.2295 -0.0494 0.5425 0.04 Uiso 1 1 calc R . . C6 C 0.3757(3) 0.0727(2) 0.6415(5) 0.0343(6) Uani 1 1 d . . . H6 H 0.3937 0.0362 0.7817 0.041 Uiso 1 1 calc R . . C7 C 0.5514(3) 0.2363(2) 0.7399(6) 0.0403(7) Uani 1 1 d . . . H7A H 0.5696 0.182 0.8674 0.048 Uiso 1 1 calc R . . H7B H 0.6401 0.2507 0.6611 0.048 Uiso 1 1 calc R . . O1 O 0.4962(2) 0.34847(18) 0.8194(4) 0.0426(6) Uani 1 1 d . . . H1 H 0.560(4) 0.389(3) 0.869(10) 0.064 Uiso 1 1 d . . . O2 O 0.1593(2) 0.02516(19) 0.1383(4) 0.0439(6) Uani 1 1 d . . . H2 H 0.115(4) -0.034(3) 0.170(9) 0.066 Uiso 1 1 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 C1 0.0335(12) 0.0314(13) 0.0330(15) -0.0031(11) -0.0017(12) 0.0057(11) C2 0.0415(14) 0.0355(14) 0.0371(16) 0.0033(11) 0.0007(14) -0.0084(12) C3 0.0471(15) 0.0368(14) 0.0300(14) 0.0056(12) -0.0016(14) -0.0025(12) C4 0.0359(13) 0.0291(12) 0.0307(15) -0.0015(11) -0.0011(12) 0.0006(9) C5 0.0395(14) 0.0276(12) 0.0326(16) 0.0021(10) 0.0015(13) -0.0014(11) C6 0.0419(15) 0.0308(12) 0.0301(15) 0.0020(12) -0.0003(13) 0.0062(11) C7 0.0382(14) 0.0351(13) 0.0475(19) -0.0015(14) -0.0100(15) 0.0055(12) O1 0.0462(11) 0.0368(10) 0.0447(14) -0.0074(10) -0.0135(10) 0.0057(8) O2 0.0549(12) 0.0408(12) 0.0359(12) 0.0047(10) -0.0098(11) -0.0140(9) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 1.376(4) . ? C1 C6 1.382(4) . ? C1 C7 1.490(4) . ? C2 C3 1.367(4) . ? C2 H2A 0.93 . ? C3 C4 1.376(4) . ? C3 H3 0.93 . ? C4 O2 1.356(3) . ? C4 C5 1.370(4) . ? C5 C6 1.369(4) . ? C5 H5 0.93 . ? C6 H6 0.93 . ? C7 O1 1.408(4) . ? C7 H7A 0.97 . ? C7 H7B 0.97 . ? O1 H1 0.80(4) . ? O2 H2 0.79(3) . ? 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 117.9(3) . . ? C2 C1 C7 120.8(3) . . ? C6 C1 C7 121.2(3) . . ? C3 C2 C1 121.4(3) . . ? C3 C2 H2A 119.3 . . ? C1 C2 H2A 119.3 . . ? C2 C3 C4 119.8(3) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? O2 C4 C5 123.0(2) . . ? O2 C4 C3 117.2(3) . . ? C5 C4 C3 119.8(3) . . ? C6 C5 C4 119.9(3) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C5 C6 C1 121.2(3) . . ? C5 C6 H6 119.4 . . ? C1 C6 H6 119.4 . . ? O1 C7 C1 109.4(2) . . ? O1 C7 H7A 109.8 . . ? C1 C7 H7A 109.8 . . ? O1 C7 H7B 109.8 . . ? C1 C7 H7B 109.8 . . ? H7A C7 H7B 108.3 . . ? C7 O1 H1 109(3) . . ? C4 O2 H2 120(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.0(4) . . . . ? C7 C1 C2 C3 -179.2(3) . . . . ? C1 C2 C3 C4 0.0(5) . . . . ? C2 C3 C4 O2 -179.6(3) . . . . ? C2 C3 C4 C5 0.6(4) . . . . ? O2 C4 C5 C6 179.0(3) . . . . ? C3 C4 C5 C6 -1.2(4) . . . . ? C4 C5 C6 C1 1.2(4) . . . . ? C2 C1 C6 C5 -0.6(4) . . . . ? C7 C1 C6 C5 178.6(3) . . . . ? C2 C1 C7 O1 68.6(4) . . . . ? C6 C1 C7 O1 -110.6(3) . . . . ? 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 O1 H1 O2 0.80(4) 2.06(5) 2.789(3) 151(5) 4_556 O2 H2 O1 0.79(3) 1.87(4) 2.645(3) 164(5) 3_544