#------------------------------------------------------------------------------ #$Date: 2012-03-01 13:37:06 +0200 (Thu, 01 Mar 2012) $ #$Revision: 36529 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/50/27/4502706.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_4502706 loop_ _publ_author_name 'Mahapatra, Sudarshan' 'Venugopala, K. N.' 'Guru Row, Tayur N.' _publ_section_title ; A Device to Crystallize Organic Solids: Structure of Ciprofloxacin, Midazolam, and Ofloxacin as Targets ; _journal_issue 4 _journal_name_full 'Crystal Growth & Design' _journal_page_first 1866 _journal_volume 10 _journal_year 2010 _chemical_compound_source 'see text' _chemical_formula_iupac '8-chloro- 6-(2-fluorophenyl)- 1-methyl- 4H-imidazo[1,5-a] [1,4]benzodiazepine' _chemical_formula_moiety 'C18 H13 Cl F N3' _chemical_formula_sum 'C18 H13 Cl F N3' _chemical_formula_weight 325.76 _chemical_name_common Medazolam _chemical_name_systematic ; ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_Int_Tables_number 14 _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 _cell_angle_beta 92.497(5) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.5588(3) _cell_length_b 13.6840(5) _cell_length_c 15.1242(8) _cell_measurement_reflns_used 3073 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 26.0 _cell_measurement_theta_min 3.0 _cell_volume 1562.88(12) _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.32 ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.32 ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.32 ; _computing_molecular_graphics 'SHELXL97 (Sheldrick, 1997)' _computing_publication_material 'PLATON (Spek, 2003)' _computing_structure_refinement 'SHELXS 97 (Sheldrick, 1997)' _computing_structure_solution ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.32 ; _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 16.0839 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Goniometer Xcalibur, detector: Eos (Nova)' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0880 _diffrn_reflns_av_sigmaI/netI 0.1226 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 16196 _diffrn_reflns_reduction_process ' ?' _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 26.00 _diffrn_reflns_theta_min 2.98 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.257 _exptl_absorpt_correction_T_max 0.9949 _exptl_absorpt_correction_T_min 0.9269 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour ' colorless' _exptl_crystal_density_diffrn 1.385 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_description ' Plate' _exptl_crystal_F_000 672 _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.02 _refine_diff_density_max 0.281 _refine_diff_density_min -0.243 _refine_diff_density_rms 0.041 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.811 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 208 _refine_ls_number_reflns 3073 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.811 _refine_ls_R_factor_all 0.1328 _refine_ls_R_factor_gt 0.0453 _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^)+(0.0440P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0902 _refine_ls_wR_factor_ref 0.1029 _reflns_number_gt 1385 _reflns_number_total 3073 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file cg901565q_si_002.cif _[local]_cod_data_source_block medazole _[local]_cod_cif_authors_sg_H-M 'P 21/n' _cod_depositor_comments ; The following automatic conversions were performed: '__refine_special_details' tag replaced with '_refine_special_details'. Automatic conversion script Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 4502706 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,1/2+y,1/2-z 3 -x,-y,-z 4 1/2+x,1/2-y,1/2+z 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 Cl1 0.0441(5) 0.0487(5) 0.1012(8) -0.0063(4) 0.0193(5) 0.0102(4) F1 0.0563(12) 0.0685(12) 0.0717(15) -0.0049(10) -0.0145(11) -0.0056(9) N1 0.0354(15) 0.0497(14) 0.0323(15) -0.0040(12) -0.0013(12) 0.0006(11) N2 0.0391(15) 0.0487(14) 0.0283(15) -0.0024(12) 0.0047(13) 0.0050(11) N3 0.0519(18) 0.0627(16) 0.0393(17) -0.0037(14) 0.0092(15) 0.0053(14) C1 0.0370(18) 0.0323(15) 0.039(2) -0.0010(14) 0.0053(16) 0.0047(13) C2 0.042(2) 0.0406(17) 0.048(2) -0.0003(16) 0.0018(19) 0.0055(15) C3 0.044(2) 0.044(2) 0.099(3) 0.002(2) 0.014(3) 0.0000(15) C4 0.069(3) 0.052(2) 0.098(4) 0.018(2) 0.043(3) 0.006(2) C5 0.087(3) 0.071(2) 0.058(3) 0.017(2) 0.021(3) 0.012(2) C6 0.060(2) 0.061(2) 0.045(2) 0.0097(17) 0.009(2) 0.0032(16) C7 0.0371(17) 0.0341(16) 0.0315(18) -0.0078(13) 0.0020(15) -0.0005(13) C8 0.0308(17) 0.0525(17) 0.043(2) -0.0071(15) -0.0033(15) -0.0013(14) C9 0.0328(17) 0.0448(17) 0.0359(19) 0.0001(15) 0.0017(16) 0.0004(14) C10 0.0397(19) 0.0553(19) 0.051(2) -0.0023(17) 0.0095(19) 0.0064(15) C11 0.047(2) 0.0514(18) 0.0308(19) 0.0005(16) 0.0035(17) 0.0017(16) C12 0.068(3) 0.093(2) 0.036(2) -0.0046(19) -0.008(2) 0.007(2) C13 0.0338(17) 0.0362(16) 0.0395(19) 0.0007(15) 0.0068(15) 0.0012(13) C14 0.053(2) 0.0510(19) 0.047(2) 0.0147(16) 0.0084(18) 0.0116(16) C15 0.048(2) 0.0421(18) 0.068(3) 0.0152(17) 0.0030(19) 0.0075(15) C16 0.0351(17) 0.0349(16) 0.059(2) -0.0008(16) 0.0105(17) -0.0017(14) C17 0.0358(18) 0.0384(16) 0.045(2) -0.0016(15) 0.0085(16) -0.0047(13) C18 0.0294(16) 0.0327(15) 0.0368(18) -0.0005(14) 0.0027(14) -0.0018(12) loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv Cl1 Cl Uani 0.20944(10) 0.48454(5) 0.47922(6) 1.000 0.0642(4) F1 F Uani 0.3513(2) 0.11799(11) 0.43903(13) 1.000 0.0660(8) N1 N Uani 0.8354(3) 0.18684(15) 0.50779(14) 1.000 0.0392(8) N2 N Uani 0.7505(3) 0.23848(15) 0.31737(15) 1.000 0.0386(8) N3 N Uani 0.8992(3) 0.15513(16) 0.21978(17) 1.000 0.0511(10) C1 C Uani 0.5535(4) 0.14588(17) 0.5585(2) 1.000 0.0360(10) C2 C Uani 0.3980(4) 0.10417(19) 0.5255(2) 1.000 0.0435(11) C3 C Uani 0.2890(4) 0.0475(2) 0.5737(3) 1.000 0.0620(14) C4 C Uani 0.3389(5) 0.0305(2) 0.6606(3) 1.000 0.0719(18) C5 C Uani 0.4916(5) 0.0705(2) 0.6976(3) 1.000 0.0715(16) C6 C Uani 0.5990(4) 0.1276(2) 0.6466(2) 1.000 0.0551(12) C7 C Uani 0.6692(4) 0.20491(17) 0.50179(18) 1.000 0.0342(10) C8 C Uani 0.9496(3) 0.24550(19) 0.45114(18) 1.000 0.0422(10) C9 C Uani 0.9138(4) 0.21808(18) 0.35748(19) 1.000 0.0378(10) C10 C Uani 1.0026(4) 0.16784(19) 0.2960(2) 1.000 0.0485(11) C11 C Uani 0.7478(4) 0.1986(2) 0.2339(2) 1.000 0.0430(11) C12 C Uani 0.5917(4) 0.1982(2) 0.1720(2) 1.000 0.0660(14) C13 C Uani 0.6198(3) 0.29712(18) 0.35729(18) 1.000 0.0364(10) C14 C Uani 0.5352(4) 0.37056(19) 0.3090(2) 1.000 0.0502(11) C15 C Uani 0.4104(4) 0.42797(19) 0.3470(2) 1.000 0.0527(13) C16 C Uani 0.3703(4) 0.41193(19) 0.4332(2) 1.000 0.0428(10) C17 C Uani 0.4527(3) 0.34066(18) 0.48270(19) 1.000 0.0395(10) C18 C Uani 0.5809(3) 0.28174(17) 0.44554(18) 1.000 0.0329(9) H3 H Uiso 0.18484 0.02142 0.54861 1.000 0.0745 H4 H Uiso 0.26852 -0.00870 0.69501 1.000 0.0861 H5 H Uiso 0.52286 0.05935 0.75686 1.000 0.0856 H6 H Uiso 0.70287 0.15386 0.67174 1.000 0.0661 H8A H Uiso 0.92561 0.31450 0.45914 1.000 0.0508 H8B H Uiso 1.07312 0.23365 0.46773 1.000 0.0508 H10 H Uiso 1.11798 0.14503 0.30436 1.000 0.0580 H12A H Uiso 0.49773 0.23471 0.19698 1.000 0.0990 H12B H Uiso 0.55364 0.13206 0.16159 1.000 0.0990 H12C H Uiso 0.62213 0.22745 0.11697 1.000 0.0990 H14 H Uiso 0.56302 0.38113 0.25050 1.000 0.0600 H15 H Uiso 0.35363 0.47736 0.31448 1.000 0.0631 H17 H Uiso 0.42357 0.33126 0.54120 1.000 0.0476 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 '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_publ_flag C7 N1 C8 116.7(2) yes C9 N2 C11 107.5(2) yes C9 N2 C13 123.4(2) yes C11 N2 C13 129.0(2) yes C10 N3 C11 105.9(2) yes C2 C1 C6 116.4(3) no C2 C1 C7 121.9(3) no C6 C1 C7 121.7(3) no F1 C2 C1 118.3(3) yes F1 C2 C3 117.2(3) yes C1 C2 C3 124.5(3) no C2 C3 C4 117.5(3) no C3 C4 C5 120.9(3) no C4 C5 C6 120.0(4) no C1 C6 C5 120.7(3) no N1 C7 C1 117.0(2) yes N1 C7 C18 126.2(2) yes C1 C7 C18 116.8(2) no N1 C8 C9 109.3(2) yes N2 C9 C8 119.5(2) yes N2 C9 C10 105.1(2) yes C8 C9 C10 135.2(3) no N3 C10 C9 111.0(3) yes N2 C11 N3 110.5(3) yes N2 C11 C12 124.4(3) yes N3 C11 C12 125.0(3) yes N2 C13 C14 119.9(2) yes N2 C13 C18 119.9(2) yes C14 C13 C18 120.2(2) no C13 C14 C15 120.4(3) no C14 C15 C16 119.5(3) no Cl1 C16 C15 118.5(2) yes Cl1 C16 C17 120.0(2) yes C15 C16 C17 121.5(3) no C16 C17 C18 120.0(3) no C7 C18 C13 123.0(2) no C7 C18 C17 118.6(2) no C13 C18 C17 118.5(2) no C2 C3 H3 121.00 no C4 C3 H3 121.00 no C3 C4 H4 120.00 no C5 C4 H4 119.00 no C4 C5 H5 120.00 no C6 C5 H5 120.00 no C1 C6 H6 120.00 no C5 C6 H6 120.00 no N1 C8 H8A 110.00 no N1 C8 H8B 110.00 no C9 C8 H8A 110.00 no C9 C8 H8B 110.00 no H8A C8 H8B 108.00 no N3 C10 H10 125.00 no C9 C10 H10 124.00 no C11 C12 H12A 110.00 no C11 C12 H12B 109.00 no C11 C12 H12C 109.00 no H12A C12 H12B 109.00 no H12A C12 H12C 109.00 no H12B C12 H12C 109.00 no C13 C14 H14 120.00 no C15 C14 H14 120.00 no C14 C15 H15 120.00 no C16 C15 H15 120.00 no C16 C17 H17 120.00 no C18 C17 H17 120.00 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Cl1 C16 1.739(3) yes F1 C2 1.353(4) yes N1 C7 1.280(4) yes N1 C8 1.479(3) yes N2 C9 1.380(4) yes N2 C11 1.375(4) yes N2 C13 1.427(3) yes N3 C10 1.375(4) yes N3 C11 1.315(4) yes C1 C2 1.380(4) no C1 C6 1.384(4) no C1 C7 1.489(4) no C2 C3 1.365(5) no C3 C4 1.371(6) no C4 C5 1.374(5) no C5 C6 1.385(5) no C7 C18 1.492(4) no C8 C9 1.479(4) no C9 C10 1.357(4) no C11 C12 1.474(4) no C13 C14 1.383(4) no C13 C18 1.395(4) no C14 C15 1.373(4) no C15 C16 1.369(4) no C16 C17 1.363(4) no C17 C18 1.397(3) no C3 H3 0.9300 no C4 H4 0.9300 no C5 H5 0.9300 no C6 H6 0.9300 no C8 H8A 0.9700 no C8 H8B 0.9700 no C10 H10 0.9300 no C12 H12A 0.9600 no C12 H12B 0.9600 no C12 H12C 0.9600 no C14 H14 0.9300 no C15 H15 0.9300 no C17 H17 0.9300 no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_2 _geom_contact_publ_flag Cl1 Cl1 3.2822(11) 3_566 no Cl1 C17 3.528(2) 3_666 no Cl1 H8A 3.0900 3_666 no F1 C17 3.204(3) . no F1 C18 2.833(3) . no F1 H8B 2.6800 1_455 no F1 H10 2.6600 1_455 no N1 N2 3.007(3) . no N2 N3 2.211(3) . no N2 N1 3.007(3) . no N3 N2 2.211(3) . no N1 H6 2.7500 . no N1 H12C 2.9100 4_555 no N3 H4 2.7200 3_656 no N3 H17 2.7200 4_554 no C1 C3 3.553(4) 3_656 no C2 C2 3.347(4) 3_656 no C2 C17 3.330(4) . no C2 C3 3.531(4) 3_656 no C3 C2 3.531(4) 3_656 no C3 C1 3.553(4) 3_656 no C4 C11 3.591(4) 3_656 no C4 C14 3.548(5) 4_455 no C8 C12 3.549(4) 4_555 no C11 C4 3.591(4) 3_656 no C12 C14 3.181(4) . no C12 C8 3.549(4) 4_454 no C14 C4 3.548(5) 4_554 no C14 C12 3.181(4) . no C17 Cl1 3.528(2) 3_666 no C17 C2 3.330(4) . no C17 F1 3.204(3) . no C18 F1 2.833(3) . no C1 H17 2.7300 . no C4 H14 2.8100 4_455 no C8 H12C 2.8000 4_555 no C10 H4 3.0000 3_656 no C11 H4 2.8200 3_656 no C11 H14 2.8800 . no C12 H14 2.7800 . no C13 H8A 2.7300 . no C13 H12A 2.7000 . no C14 H12A 2.5200 . no C18 H8A 2.6400 . no H4 N3 2.7200 3_656 no H4 C10 3.0000 3_656 no H4 C11 2.8200 3_656 no H4 H14 2.5100 4_455 no H6 N1 2.7500 . no H8A C13 2.7300 . no H8A C18 2.6400 . no H8A Cl1 3.0900 3_666 no H8B F1 2.6800 1_655 no H8B H12C 2.3300 4_555 no H10 F1 2.6600 1_655 no H12A C13 2.7000 . no H12A C14 2.5200 . no H12A H14 2.2100 . no H12C N1 2.9100 4_454 no H12C C8 2.8000 4_454 no H12C H8B 2.3300 4_454 no H14 C11 2.8800 . no H14 C12 2.7800 . no H14 H12A 2.2100 . no H14 C4 2.8100 4_554 no H14 H4 2.5100 4_554 no H17 C1 2.7300 . no H17 N3 2.7200 4_455 no 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_publ_flag C8 N1 C7 C1 179.8(2) no C8 N1 C7 C18 -2.3(4) no C7 N1 C8 C9 -68.8(3) no C11 N2 C9 C8 -175.2(2) no C11 N2 C9 C10 0.7(3) no C13 N2 C9 C8 9.0(4) no C13 N2 C9 C10 -175.2(2) no C9 N2 C11 N3 -0.2(3) no C9 N2 C11 C12 175.3(3) no C13 N2 C11 N3 175.4(2) no C13 N2 C11 C12 -9.1(4) no C9 N2 C13 C14 132.5(3) no C9 N2 C13 C18 -45.9(3) no C11 N2 C13 C14 -42.4(4) no C11 N2 C13 C18 139.2(3) no C11 N3 C10 C9 0.8(3) no C10 N3 C11 N2 -0.4(3) no C10 N3 C11 C12 -175.9(3) no C6 C1 C2 F1 -178.2(2) no C6 C1 C2 C3 0.2(4) no C7 C1 C2 F1 0.0(4) no C7 C1 C2 C3 178.4(3) no C2 C1 C6 C5 -0.2(4) no C7 C1 C6 C5 -178.4(3) no C2 C1 C7 N1 -133.8(3) no C2 C1 C7 C18 48.1(3) no C6 C1 C7 N1 44.3(4) no C6 C1 C7 C18 -133.8(3) no F1 C2 C3 C4 177.8(3) no C1 C2 C3 C4 -0.6(4) no C2 C3 C4 C5 1.0(5) no C3 C4 C5 C6 -1.1(5) no C4 C5 C6 C1 0.7(5) no N1 C7 C18 C13 45.9(4) no N1 C7 C18 C17 -134.5(3) no C1 C7 C18 C13 -136.2(3) no C1 C7 C18 C17 43.4(3) no N1 C8 C9 N2 66.2(3) no N1 C8 C9 C10 -108.1(3) no N2 C9 C10 N3 -0.9(3) no C8 C9 C10 N3 173.9(3) no N2 C13 C14 C15 -179.4(2) no C18 C13 C14 C15 -1.0(4) no N2 C13 C18 C7 -0.6(4) no N2 C13 C18 C17 179.8(2) no C14 C13 C18 C7 -179.0(2) no C14 C13 C18 C17 1.3(4) no C13 C14 C15 C16 0.0(4) no C14 C15 C16 Cl1 -179.1(2) no C14 C15 C16 C17 0.6(4) no Cl1 C16 C17 C18 179.46(19) no C15 C16 C17 C18 -0.2(4) no C16 C17 C18 C7 179.6(2) no C16 C17 C18 C13 -0.7(4) no