#------------------------------------------------------------------------------ #$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $ #$Revision: 201957 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/82/2018250.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2018250 loop_ _publ_author_name 'Kirchner, Michael T.' 'Bl\"aser, Dieter' 'Boese, Roland' 'Thakur, Tejender S.' 'Desiraju, Gautam R.' _publ_section_title ; Weak C---H···O hydrogen bonds in anisaldehyde, salicylaldehyde and cinnamaldehyde ; _journal_coeditor_code FG3222 _journal_issue 10 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o387 _journal_page_last o390 _journal_paper_doi 10.1107/S0108270111035840 _journal_volume 67 _journal_year 2011 _chemical_formula_iupac 'C7 H6 O2' _chemical_formula_moiety 'C7 H6 O2' _chemical_formula_sum 'C7 H6 O2' _chemical_formula_weight 122.12 _chemical_name_common Salicylylaldehyde _chemical_name_systematic ; 2-hydroxybenzaldehyde ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL97 _cell_angle_alpha 90.00 _cell_angle_beta 103.262(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 6.3945(3) _cell_length_b 13.8939(9) _cell_length_c 6.9172(4) _cell_measurement_reflns_used 1182 _cell_measurement_temperature 233(2) _cell_measurement_theta_max 24.35 _cell_measurement_theta_min 2.94 _cell_volume 598.17(6) _computing_cell_refinement 'APEX2 (Bruker, 2006)' _computing_data_collection 'APEX2 (Bruker, 2006)' _computing_data_reduction 'APEX2 [or SAINT?] (Bruker, 2006)' _computing_molecular_graphics 'Mercury (Macrae et al., 2008)' _computing_publication_material 'publCIF (Westrip, 2010)' _computing_structure_refinement 'SHELXTL (Sheldrick, 2008)' _computing_structure_solution 'APEX2 (Bruker, 2006)' _diffrn_ambient_temperature 233(2) _diffrn_detector_area_resol_mean 512 _diffrn_measured_fraction_theta_full 0.844 _diffrn_measured_fraction_theta_max 0.641 _diffrn_measurement_device_type 'Siemens SMART three-axis goniometer with APEXII area-detector system' _diffrn_measurement_method 'Data collection strategy APEX2/COSMO with chi = 0' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0556 _diffrn_reflns_av_sigmaI/netI 0.0378 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_number 8643 _diffrn_reflns_theta_full 24.00 _diffrn_reflns_theta_max 36.24 _diffrn_reflns_theta_min 2.93 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.356 _exptl_crystal_density_method 'not measured' _exptl_crystal_description cylinder _exptl_crystal_F_000 256 _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _refine_diff_density_max 0.317 _refine_diff_density_min -0.183 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.998 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 82 _refine_ls_number_reflns 1853 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.998 _refine_ls_R_factor_all 0.1095 _refine_ls_R_factor_gt 0.0573 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.1022P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1511 _refine_ls_wR_factor_ref 0.1850 _reflns_number_gt 1002 _reflns_number_total 1853 _reflns_threshold_expression I>2\s(I) _iucr_refine_instructions_details ; TITL C7 H6 O2 in P2(1)/c CELL 0.71073 6.3945 13.8939 6.9172 90.000 103.262 90.000 ZERR 4.00 0.0003 0.0009 0.0004 0.000 0.003 0.000 LATT 1 SYMM -X, 0.5+Y, 0.5-Z SFAC C H O UNIT 28 24 8 ACTA 48 CONF TEMP -40 OMIT -1 2 2 OMIT -2 6 5 OMIT -1 6 5 OMIT -3 5 5 OMIT -2 5 3 EQIV $1 1-x, y+0.5, 1.5-z EQIV $2 -x, 1-y, 1-z EQIV $3 x-1, y, z EQIV $4 x-1, 1.5-y, -0.5+z HTAB O2 O1 HTAB C3 O1_$1 HTAB C7 O1_$2 HTAB C6 O2_$3 HTAB C6 O2_$4 MOVE 0.5 0 0 1 L.S. 8 BOND $H FMAP 2 PLAN 10 REM EXTI 0.000000 WGHT 0.1022 0.0000 FVAR 0.83042 O1 3 -0.244384 0.540613 0.661583 11.00000 0.06618 0.03681 = 0.07429 0.00329 0.01295 0.00315 O2 3 0.052586 0.674534 0.731028 11.00000 0.03405 0.05942 = 0.07833 0.00585 0.00412 0.00718 AFIX 3 H2 2 -0.034533 0.608011 0.705875 11.00000 -1.50000 AFIX 0 C1 1 -0.326174 0.707598 0.645120 11.00000 0.03506 0.03426 = 0.03282 -0.00142 0.00687 -0.00427 C2 1 -0.110817 0.738418 0.695549 11.00000 0.03337 0.04282 = 0.03940 0.00092 0.00595 -0.00224 C3 1 -0.065600 0.836374 0.708712 11.00000 0.04650 0.04918 = 0.05008 -0.00319 0.00838 -0.01590 AFIX 3 H3 2 0.081110 0.858114 0.743233 11.00000 -1.20000 AFIX 0 C4 1 -0.232269 0.901394 0.671532 11.00000 0.07035 0.03451 = 0.05164 -0.00204 0.01540 -0.00905 AFIX 3 H4 2 -0.200699 0.969244 0.683752 11.00000 -1.20000 AFIX 0 C5 1 -0.444649 0.872268 0.621077 11.00000 0.05590 0.04060 = 0.05129 0.00153 0.01340 0.00812 AFIX 3 H5 2 -0.558829 0.918989 0.593338 11.00000 -1.20000 AFIX 0 C6 1 -0.490930 0.775281 0.607947 11.00000 0.03494 0.04480 = 0.04172 -0.00085 0.00622 0.00112 AFIX 3 H6 2 -0.637629 0.753511 0.574157 11.00000 -1.20000 AFIX 0 C7 1 -0.377813 0.605894 0.631970 11.00000 0.04876 0.03931 = 0.04755 -0.00029 0.01084 -0.00695 AFIX 3 H7 2 -0.527063 0.587974 0.602610 11.00000 -1.20000 HKLF 4 REM C7 H6 O2 in P2(1)/c REM R1 = 0.0573 for 1002 Fo > 4sig(Fo) and 0.1095 for all 1853 data REM 82 parameters refined using 0 restraints END REM Highest difference peak 0.315, deepest hole -0.181, 1-sigma level 0.050 Q1 1 -0.3502 0.6569 0.6334 11.00000 0.05 0.31 Q2 1 -0.0858 0.7848 0.6814 11.00000 0.05 0.30 Q3 1 -0.4797 0.8268 0.6137 11.00000 0.05 0.25 Q4 1 -0.2200 0.7213 0.6797 11.00000 0.05 0.21 Q5 1 0.0478 0.6732 0.5025 11.00000 0.05 0.20 Q6 1 -0.2387 0.9693 0.8981 11.00000 0.05 0.19 Q7 1 -0.2591 0.9628 0.6321 11.00000 0.05 0.18 Q8 1 -0.2549 0.5422 0.9134 11.00000 0.05 0.18 Q9 1 -0.2178 0.9571 0.4836 11.00000 0.05 0.17 Q10 1 -0.3415 0.8915 0.6631 11.00000 0.05 0.17 ; _cod_data_source_file fg3222.cif _cod_data_source_block II _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2018250 _cod_database_fobs_code 2018250 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' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_symmetry_multiplicity O O1 0.2556(2) 0.54061(8) 0.6616(2) 0.0596(5) Uani d . 1 1 O O2 0.55260(18) 0.67452(9) 0.7310(2) 0.0587(5) Uani d . 1 1 H H2 0.4655 0.6080 0.7059 0.088 Uiso d R 1 1 C C1 0.1738(2) 0.70760(10) 0.6451(3) 0.0341(5) Uani d . 1 1 C C2 0.3892(2) 0.73841(11) 0.6956(3) 0.0389(5) Uani d . 1 1 C C3 0.4344(3) 0.83638(12) 0.7087(3) 0.0490(5) Uani d . 1 1 H H3 0.5811 0.8581 0.7432 0.059 Uiso d R 1 1 C C4 0.2677(3) 0.90140(12) 0.6715(3) 0.0519(6) Uani d . 1 1 H H4 0.2993 0.9692 0.6837 0.062 Uiso d R 1 1 C C5 0.0553(3) 0.87229(12) 0.6211(3) 0.0491(5) Uani d . 1 1 H H5 -0.0589 0.9190 0.5933 0.059 Uiso d R 1 1 C C6 0.0090(2) 0.77528(12) 0.6079(3) 0.0409(5) Uani d . 1 1 H H6 -0.1377 0.7535 0.5742 0.049 Uiso d R 1 1 C C7 0.1222(3) 0.60588(11) 0.6320(3) 0.0452(5) Uani d . 1 1 H H7 -0.0271 0.5880 0.6026 0.054 Uiso d R 1 1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0661(8) 0.0368(6) 0.0743(13) 0.0031(6) 0.0129(7) 0.0033(6) O2 0.0340(5) 0.0593(8) 0.0783(13) 0.0071(5) 0.0041(6) 0.0058(7) C1 0.0350(6) 0.0342(7) 0.0327(13) -0.0043(5) 0.0068(6) -0.0015(6) C2 0.0334(6) 0.0428(7) 0.0394(13) -0.0023(6) 0.0060(6) 0.0009(7) C3 0.0465(8) 0.0491(9) 0.0501(15) -0.0159(7) 0.0084(8) -0.0032(8) C4 0.0702(12) 0.0345(7) 0.0515(16) -0.0090(7) 0.0154(10) -0.0020(8) C5 0.0559(10) 0.0405(8) 0.0514(16) 0.0080(7) 0.0134(8) 0.0015(8) C6 0.0349(7) 0.0446(8) 0.0418(14) 0.0011(6) 0.0062(6) -0.0008(7) C7 0.0488(9) 0.0392(8) 0.0474(16) -0.0069(6) 0.0109(8) -0.0003(7) 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C2 O2 H2 100.7 C6 C1 C2 119.78(13) C6 C1 C7 119.68(13) C2 C1 C7 120.53(14) O2 C2 C3 119.43(14) O2 C2 C1 121.18(14) C3 C2 C1 119.40(14) C4 C3 C2 119.36(15) C4 C3 H3 120.6 C2 C3 H3 120.0 C3 C4 C5 121.94(15) C3 C4 H4 119.2 C5 C4 H4 118.8 C6 C5 C4 119.08(16) C6 C5 H5 120.3 C4 C5 H5 120.6 C5 C6 C1 120.43(14) C5 C6 H6 120.4 C1 C6 H6 119.2 O1 C7 C1 124.69(15) O1 C7 H7 117.5 C1 C7 H7 117.8 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C7 1.230(2) O2 C2 1.3499(19) O2 H2 1.0726 C1 C6 1.392(2) C1 C2 1.4075(19) C1 C7 1.449(2) C2 C3 1.390(2) C3 C4 1.375(3) C3 H3 0.9621 C4 C5 1.383(3) C4 H4 0.9637 C5 C6 1.378(2) C5 H5 0.9628 C6 H6 0.9620 C7 H7 0.9618 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA O2 H2 O1 . 1.07 1.61 2.6231(18) 155.9 C3 H3 O1 2_656 0.96 2.76 3.460(2) 129.9 C7 H7 O1 3_566 0.96 2.73 3.443(2) 131.6 C6 H6 O2 1_455 0.96 2.70 3.513(2) 142.6 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 C6 C1 C2 O2 -179.50(17) C7 C1 C2 O2 0.6(3) C6 C1 C2 C3 0.4(3) C7 C1 C2 C3 -179.50(19) O2 C2 C3 C4 179.66(19) C1 C2 C3 C4 -0.2(3) C2 C3 C4 C5 0.0(3) C3 C4 C5 C6 0.1(3) C4 C5 C6 C1 0.1(3) C2 C1 C6 C5 -0.3(3) C7 C1 C6 C5 179.58(18) C6 C1 C7 O1 179.85(19) C2 C1 C7 O1 -0.3(3) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 13863618