#------------------------------------------------------------------------------ #$Date: 2019-09-18 14:05:15 +0300 (Wed, 18 Sep 2019) $ #$Revision: 218433 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/20/02/7200223.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7200223 loop_ _publ_author_name 'Skovsgaard, Signe' 'Bond, Andrew D.' _publ_section_title ; Co-crystallisation of benzoic acid derivatives with N-containing bases in solution and by mechanical grinding: stoichiometric variants, polymorphism and twinning ; _journal_coden_ASTM CRECF4 _journal_issue 3 _journal_name_full CrystEngComm _journal_page_first 444 _journal_page_last 453 _journal_paper_doi 10.1039/b810660f _journal_volume 11 _journal_year 2009 _chemical_formula_moiety 'C7 H6 O2, C4 H5 N3' _chemical_formula_sum 'C11 H11 N3 O2' _chemical_formula_weight 217.23 _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 90.980(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 5.3467(4) _cell_length_b 17.2757(13) _cell_length_c 11.5764(9) _cell_measurement_reflns_used 8371 _cell_measurement_temperature 180(2) _cell_measurement_theta_max 26.15 _cell_measurement_theta_min 2.36 _cell_volume 1069.13(14) _computing_cell_refinement 'SAINT v.7.06a (Bruker, 2003)' _computing_data_collection 'APEX2 v.1.0-22 (Bruker Nonius, 2004)' _computing_data_reduction 'SAINT v.7.06a' _computing_molecular_graphics 'SHELXTL v.6.10' _computing_publication_material 'SHELXTL v.6.10' _computing_structure_refinement 'SHELXTL v.6.10' _computing_structure_solution 'SHELXTL v.6.10 (Sheldrick, 2000)' _diffrn_ambient_temperature 180(2) _diffrn_measured_fraction_theta_full 0.982 _diffrn_measured_fraction_theta_max 0.982 _diffrn_measurement_device_type 'Bruker-Nonius X8APEX-II CCD' _diffrn_measurement_method 'thin-slice \w and \f scans' _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 0.0254 _diffrn_reflns_av_sigmaI/netI 0.0168 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 15086 _diffrn_reflns_theta_full 26.36 _diffrn_reflns_theta_max 26.36 _diffrn_reflns_theta_min 3.52 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_T_max 0.981 _exptl_absorpt_correction_T_min 0.872 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS v.2.10 (Sheldrick, 2003) Ratio of minimum to maximum apparent transmission: 0.888565 ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.350 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 456 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.188 _refine_diff_density_min -0.199 _refine_diff_density_rms 0.043 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.155 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 157 _refine_ls_number_reflns 2153 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.155 _refine_ls_R_factor_all 0.0486 _refine_ls_R_factor_gt 0.0416 _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^)+(0.0301P)^2^+0.9362P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1154 _refine_ls_wR_factor_ref 0.1178 _reflns_number_gt 1839 _reflns_number_total 2153 _reflns_threshold_expression I>2\s(I) _cod_data_source_file B810660F.txt _cod_data_source_block 4 _cod_depositor_comments ; Replaced the incorrect bibliographical reference to the original publication with a proper one. Antanas Vaitkus, 2019-09-18 ; _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 7200223 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' 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 N1 N 0.7123(3) 0.50714(9) 0.20997(13) 0.0291(4) Uani 1 1 d . . . N2 N 0.4272(3) 0.54709(9) 0.35605(14) 0.0302(4) Uani 1 1 d . . . N3 N 0.7693(4) 0.47157(12) 0.40039(16) 0.0389(5) Uani 1 1 d . . . H31 H 0.715(5) 0.4663(14) 0.475(2) 0.047(7) Uiso 1 1 d . . . H32 H 0.909(5) 0.4480(15) 0.371(2) 0.052(7) Uiso 1 1 d . . . C1 C 0.6336(4) 0.50898(11) 0.32078(16) 0.0278(4) Uani 1 1 d . . . C2 C 0.2959(4) 0.58417(12) 0.27524(18) 0.0333(5) Uani 1 1 d . . . H2A H 0.1481 0.6104 0.2973 0.040 Uiso 1 1 calc R . . C3 C 0.3632(4) 0.58668(13) 0.16007(19) 0.0366(5) Uani 1 1 d . . . H3A H 0.2673 0.6141 0.1036 0.044 Uiso 1 1 calc R . . C4 C 0.5770(4) 0.54710(12) 0.13282(17) 0.0323(5) Uani 1 1 d . . . H4A H 0.6311 0.5483 0.0551 0.039 Uiso 1 1 calc R . . O11 O 0.1810(3) 0.38678(8) 0.29751(11) 0.0343(4) Uani 1 1 d . . . O12 O 0.0412(3) 0.40903(8) 0.11734(12) 0.0351(4) Uani 1 1 d . . . H12 H -0.073(6) 0.4412(18) 0.148(3) 0.066(9) Uiso 1 1 d . . . C11 C 0.3558(3) 0.31390(11) 0.14493(17) 0.0272(4) Uani 1 1 d . . . C12 C 0.3240(4) 0.28588(12) 0.03333(17) 0.0326(5) Uani 1 1 d . . . H12A H 0.1905 0.3045 -0.0143 0.039 Uiso 1 1 calc R . . C13 C 0.4873(4) 0.23076(12) -0.00844(19) 0.0371(5) Uani 1 1 d . . . H13A H 0.4645 0.2111 -0.0846 0.045 Uiso 1 1 calc R . . C14 C 0.6838(4) 0.20411(12) 0.06024(19) 0.0358(5) Uani 1 1 d . . . H14A H 0.7972 0.1670 0.0308 0.043 Uiso 1 1 calc R . . C15 C 0.7146(4) 0.23162(12) 0.17179(19) 0.0372(5) Uani 1 1 d . . . H15A H 0.8484 0.2130 0.2192 0.045 Uiso 1 1 calc R . . C16 C 0.5509(4) 0.28625(12) 0.21445(18) 0.0335(5) Uani 1 1 d . . . H16A H 0.5717 0.3049 0.2912 0.040 Uiso 1 1 calc R . . C17 C 0.1848(3) 0.37326(11) 0.19421(16) 0.0272(4) Uani 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 N1 0.0328(9) 0.0294(9) 0.0252(8) -0.0016(7) 0.0039(7) 0.0000(7) N2 0.0308(9) 0.0281(9) 0.0319(9) -0.0037(7) 0.0061(7) -0.0001(7) N3 0.0377(10) 0.0530(12) 0.0263(9) 0.0025(8) 0.0074(8) 0.0135(9) C1 0.0292(10) 0.0266(10) 0.0279(10) -0.0024(8) 0.0048(8) -0.0024(8) C2 0.0297(10) 0.0294(10) 0.0408(12) -0.0021(9) 0.0023(8) 0.0011(8) C3 0.0377(12) 0.0353(11) 0.0368(12) 0.0041(9) -0.0037(9) 0.0011(9) C4 0.0396(11) 0.0318(11) 0.0256(10) 0.0000(8) 0.0020(8) -0.0037(9) O11 0.0398(8) 0.0361(8) 0.0270(7) -0.0023(6) 0.0044(6) 0.0039(6) O12 0.0416(8) 0.0343(8) 0.0294(7) 0.0016(6) 0.0054(6) 0.0122(7) C11 0.0281(10) 0.0228(9) 0.0310(10) 0.0008(8) 0.0058(7) -0.0027(7) C12 0.0379(11) 0.0309(10) 0.0290(10) 0.0017(8) 0.0000(8) 0.0048(9) C13 0.0473(12) 0.0339(11) 0.0302(11) -0.0022(9) 0.0045(9) 0.0056(9) C14 0.0366(11) 0.0277(10) 0.0435(12) 0.0019(9) 0.0111(9) 0.0048(9) C15 0.0317(11) 0.0357(11) 0.0441(12) 0.0023(9) -0.0017(9) 0.0034(9) C16 0.0347(11) 0.0334(11) 0.0325(11) -0.0028(9) -0.0001(8) -0.0011(9) C17 0.0292(10) 0.0242(9) 0.0285(10) 0.0004(8) 0.0062(8) -0.0042(8) 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' N N 0.0061 0.0033 '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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 N1 C1 116.61(17) . . ? C2 N2 C1 116.53(17) . . ? C1 N3 H31 121.5(16) . . ? C1 N3 H32 113.3(16) . . ? H31 N3 H32 125(2) . . ? N3 C1 N2 117.69(18) . . ? N3 C1 N1 117.99(18) . . ? N2 C1 N1 124.31(18) . . ? N2 C2 C3 123.42(19) . . ? N2 C2 H2A 118.3 . . ? C3 C2 H2A 118.3 . . ? C4 C3 C2 115.83(19) . . ? C4 C3 H3A 122.1 . . ? C2 C3 H3A 122.1 . . ? N1 C4 C3 123.27(19) . . ? N1 C4 H4A 118.4 . . ? C3 C4 H4A 118.4 . . ? C17 O12 H12 114.2(18) . . ? C12 C11 C16 119.84(18) . . ? C12 C11 C17 121.94(18) . . ? C16 C11 C17 118.21(17) . . ? C13 C12 C11 119.81(19) . . ? C13 C12 H12A 120.1 . . ? C11 C12 H12A 120.1 . . ? C12 C13 C14 120.3(2) . . ? C12 C13 H13A 119.8 . . ? C14 C13 H13A 119.8 . . ? C15 C14 C13 119.93(19) . . ? C15 C14 H14A 120.0 . . ? C13 C14 H14A 120.0 . . ? C14 C15 C16 120.1(2) . . ? C14 C15 H15A 120.0 . . ? C16 C15 H15A 120.0 . . ? C15 C16 C11 120.03(19) . . ? C15 C16 H16A 120.0 . . ? C11 C16 H16A 120.0 . . ? O11 C17 O12 123.57(18) . . ? O11 C17 C11 121.78(18) . . ? O12 C17 C11 114.65(16) . . ? 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 N1 C4 1.332(3) . ? N1 C1 1.357(2) . ? N2 C2 1.325(3) . ? N2 C1 1.354(2) . ? N3 C1 1.330(3) . ? N3 H31 0.92(3) . ? N3 H32 0.92(3) . ? C2 C3 1.387(3) . ? C2 H2A 0.950 . ? C3 C4 1.373(3) . ? C3 H3A 0.950 . ? C4 H4A 0.950 . ? O11 C17 1.219(2) . ? O12 C17 1.319(2) . ? O12 H12 0.91(3) . ? C11 C12 1.387(3) . ? C11 C16 1.391(3) . ? C11 C17 1.494(3) . ? C12 C13 1.385(3) . ? C12 H12A 0.950 . ? C13 C14 1.385(3) . ? C13 H13A 0.950 . ? C14 C15 1.383(3) . ? C14 H14A 0.950 . ? C15 C16 1.384(3) . ? C15 H15A 0.950 . ? C16 H16A 0.950 . ? 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 O12 H12 N1 0.91(3) 1.77(3) 2.679(2) 178(3) 1_455 N3 H32 O11 0.92(3) 2.00(3) 2.916(2) 172(2) 1_655 N3 H31 N2 0.92(3) 2.12(3) 3.043(2) 177(2) 3_666 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 C2 N2 C1 N3 179.70(19) . . . . ? C2 N2 C1 N1 0.4(3) . . . . ? C4 N1 C1 N3 -177.99(19) . . . . ? C4 N1 C1 N2 1.3(3) . . . . ? C1 N2 C2 C3 -1.4(3) . . . . ? N2 C2 C3 C4 0.7(3) . . . . ? C1 N1 C4 C3 -2.1(3) . . . . ? C2 C3 C4 N1 1.2(3) . . . . ? C16 C11 C12 C13 -0.3(3) . . . . ? C17 C11 C12 C13 -179.91(19) . . . . ? C11 C12 C13 C14 -0.7(3) . . . . ? C12 C13 C14 C15 1.1(3) . . . . ? C13 C14 C15 C16 -0.6(3) . . . . ? C14 C15 C16 C11 -0.4(3) . . . . ? C12 C11 C16 C15 0.8(3) . . . . ? C17 C11 C16 C15 -179.54(18) . . . . ? C12 C11 C17 O11 165.38(19) . . . . ? C16 C11 C17 O11 -14.3(3) . . . . ? C12 C11 C17 O12 -14.7(3) . . . . ? C16 C11 C17 O12 165.69(17) . . . . ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 30653524