#------------------------------------------------------------------------------ #$Date: 2012-02-03 19:16:24 +0200 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/20/02/2200228.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_2200228 loop_ _publ_author_name 'Vi\H-1,4-benzodiazepine-3-carboxylate ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o356 _journal_page_last o357 _journal_volume 57 _journal_year 2001 _chemical_formula_iupac 'C18 H15 Cl N2 O3' _chemical_formula_moiety 'C18 H15 Cl N2 O3' _chemical_formula_sum 'C18 H15 Cl N2 O3' _chemical_formula_weight 342.77 _chemical_name_systematic ; Ethyl 7-chloro-2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepine-3-carboxylate ; _space_group_IT_number 61 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M 'P b c a' _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 15.4280(10) _cell_length_b 9.346(2) _cell_length_c 22.506(5) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 11.78 _cell_measurement_theta_min 4.36 _cell_volume 3245.1(10) _computing_cell_refinement 'SET4 and CELDIM in CAD-4 Software (Enraf-Nonius, 1989)' _computing_data_collection 'CAD-4 Software (Enraf Nonius, 1989)' _computing_data_reduction 'HELENA (Spek, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'PLATON (Spek, 1990)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full .887 _diffrn_measured_fraction_theta_max .887 _diffrn_measurement_device_type 'Enraf-Nonius CAD-4' _diffrn_measurement_method \q/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .7107 _diffrn_reflns_av_R_equivalents .081 _diffrn_reflns_av_sigmaI/netI .274 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 3730 _diffrn_reflns_reduction_process ; ? ; _diffrn_reflns_theta_full 26.29 _diffrn_reflns_theta_max 26.32 _diffrn_reflns_theta_min 2.06 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .254 _exptl_absorpt_correction_T_max .943 _exptl_absorpt_correction_T_min .821 _exptl_absorpt_correction_type '\y scan' _exptl_absorpt_process_details '(North et al., 1968)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.403 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 1424 _exptl_crystal_size_max .20 _exptl_crystal_size_mid .09 _exptl_crystal_size_min .03 _refine_diff_density_max .34 _refine_diff_density_min -.54 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref .835 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_constraints 0 _refine_ls_number_parameters 218 _refine_ls_number_reflns 3286 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all .835 _refine_ls_R_factor_all .392 _refine_ls_R_factor_gt .075 _refine_ls_shift/su_max .002 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.1031P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .214 _reflns_number_gt 837 _reflns_number_total 3286 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file tk6008.cif _[local]_cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_cell_volume 3245(2) _cod_database_code 2200228 loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2-x,-y,1/2+z 1/2+x,1/2-y,-z -x,1/2+y,1/2-z -x,-y,-z 1/2+x,y,1/2-z 1/2-x,1/2+y,z 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cl1 .0603(10) .0627(10) .0832(13) -.0100(10) .0037(10) .0168(10) O10 .061(3) .100(4) .039(3) -.012(3) .010(2) .006(3) O12 .189(6) .062(4) .067(4) -.020(4) -.030(4) .001(3) O13 .088(4) .077(4) .060(3) .006(3) -.016(3) .005(3) N1 .045(3) .066(4) .046(3) .005(3) .009(3) -.018(3) N4 .055(3) .054(3) .028(3) -.011(3) .003(3) -.007(3) C2 .047(4) .069(5) .032(4) -.005(4) -.017(4) -.011(4) C3 .057(4) .045(4) .033(3) -.005(3) .007(3) -.007(3) C5 .043(4) .044(4) .038(4) -.012(3) .007(3) -.006(3) C6 .044(4) .041(4) .048(4) -.001(3) .000(3) -.005(3) C7 .032(3) .044(4) .079(5) -.012(3) -.010(3) .014(4) C8 .040(3) .046(4) .082(5) .001(3) -.017(4) -.020(4) C9 .048(4) .054(4) .049(4) .004(3) -.004(3) -.013(4) C11 .078(5) .054(5) .039(5) -.011(4) .010(4) -.011(4) C14 .167(9) .112(7) .067(6) .043(7) .014(6) .019(6) C15 .229(14) .212(13) .084(8) .043(11) -.004(9) .045(9) C16 .049(4) .041(4) .032(3) -.012(3) .011(3) .001(3) C17 .064(4) .048(4) .048(4) -.011(4) -.001(4) .002(4) C18 .070(5) .062(5) .066(5) -.016(4) .001(4) -.018(4) C19 .083(5) .069(5) .056(5) -.023(4) .000(5) -.015(4) C20 .069(5) .085(6) .055(5) .001(4) -.013(4) .006(4) C21 .064(4) .059(4) .059(5) .010(4) -.004(4) -.004(4) C51 .033(3) .054(4) .044(4) -.006(3) -.003(3) -.005(3) C91 .027(3) .060(4) .044(4) -.006(3) .000(3) -.004(4) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy _atom_site_type_symbol Cl1 .29888(11) -.32134(18) .409440(9) .0687(6) Uani 1.000 Cl O10 .4591(3) .1813(5) .14223(10) .0667(19) Uani 1.000 O O12 .3472(5) .4576(6) .2002(2) .106(3) Uani 1.000 O O13 .2746(3) .2977(5) .1475(2) .075(2) Uani 1.000 O N1 .4465(3) -.0007(6) .2079(2) .0523(19) Uani 1.000 N N4 .3972(3) .2492(6) .2808(2) .0457(17) Uani 1.000 N C2 .4249(4) .1296(8) .1863(2) .049(3) Uani 1.000 C C3 .3585(4) .2072(6) .2240(2) .045(2) Uani 1.000 C C5 .4084(4) .1492(6) .3189(2) .042(2) Uani 1.000 C C6 .3557(3) -.0843(6) .3561(2) .044(2) Uani 1.000 C C7 .3398(4) -.2231(7) .3488(3) .052(2) Uani 1.000 C C8 .3562(4) -.2950(7) .2960(3) .056(2) Uani 1.000 C C9 .3899(4) -.2177(7) .2508(3) .050(2) Uani 1.000 C C11 .3270(5) .3373(8) .1909(3) .057(3) Uani 1.000 C C14 .2369(8) .4081(10) .1079(3) .115(4) Uani 1.000 C C15 .2723(9) .3933(12) .0536(4) .175(7) Uani 1.000 C C16 .4433(4) .1955(6) .3782(2) .041(2) Uani 1.000 C C17 .4134(4) .3206(7) .4032(2) .053(2) Uani 1.000 C C18 .4411(5) .3634(8) .4594(3) .066(3) Uani 1.000 C C19 .4977(5) .2781(8) .4896(3) .069(3) Uani 1.000 C C20 .5297(5) .1566(8) .4646(3) .070(3) Uani 1.000 C C21 .5021(4) .1102(7) .4088(3) .061(3) Uani 1.000 C C51 .3898(3) -.0018(6) .3105(2) .044(2) Uani 1.000 C C91 .4071(3) -.0731(7) .2561(2) .044(2) Uani 1.000 C H1 .488710 -.044040 .190580 .0625 Uiso 1.000 H H3 .309320 .143350 .231560 .0540 Uiso 1.000 H H6 .343690 -.041680 .392510 .0534 Uiso 1.000 H H8 .344570 -.392090 .291950 .0672 Uiso 1.000 H H9 .401800 -.263150 .214950 .0600 Uiso 1.000 H H14A .249120 .502660 .123470 .1384 Uiso 1.000 H H14B .174500 .396310 .105620 .1384 Uiso 1.000 H H15A .243640 .317200 .032700 .2627 Uiso 1.000 H H15B .265570 .480880 .031750 .2627 Uiso 1.000 H H15C .332790 .371380 .057440 .2627 Uiso 1.000 H H17 .374130 .377000 .382390 .0638 Uiso 1.000 H H18 .421410 .448480 .475950 .0793 Uiso 1.000 H H19 .514610 .303500 .527790 .0831 Uiso 1.000 H H20 .570870 .103340 .485210 .0836 Uiso 1.000 H H21 .522320 .024990 .392640 .0726 Uiso 1.000 H loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cl1 C7 . . 1.762(7) no O10 C2 . . 1.223(6) no O12 C11 . . 1.186(9) no O13 C11 . . 1.321(9) no O13 C14 . . 1.482(10) no N1 C2 . . 1.353(9) no N1 C91 . . 1.415(7) no N4 C3 . . 1.464(7) no N4 C5 . . 1.280(7) no N1 H1 . . .8603 no C2 C3 . . 1.515(8) no C3 C11 . . 1.507(9) no C5 C51 . . 1.453(8) no C5 C16 . . 1.502(7) no C6 C51 . . 1.387(7) no C6 C7 . . 1.331(9) no C7 C8 . . 1.388(9) no C8 C9 . . 1.352(9) no C9 C91 . . 1.383(9) no C14 C15 . . 1.346(13) no C16 C21 . . 1.390(9) no C16 C17 . . 1.378(8) no C17 C18 . . 1.393(8) no C18 C19 . . 1.364(11) no C19 C20 . . 1.360(10) no C20 C21 . . 1.395(10) no C51 C91 . . 1.419(7) no C3 H3 . . .9803 no C6 H6 . . .9296 no C8 H8 . . .9299 no C9 H9 . . .9299 no C14 H14A . . .9696 no C14 H14B . . .9702 no C15 H15A . . .9607 no C15 H15B . . .9608 no C15 H15C . . .9593 no C17 H17 . . .9297 no C18 H18 . . .9294 no C19 H19 . . .9288 no C20 H20 . . .9308 no C21 H21 . . .9297 no loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl .1484 .1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 1 -3 2 -1 1 -4 1 3 -2 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 C11 O13 C14 119.3(6) no C2 N1 C91 126.9(5) no C3 N4 C5 116.3(5) no C91 N1 H1 116.53 no C2 N1 H1 116.61 no O10 C2 C3 123.8(6) no O10 C2 N1 122.7(6) no N1 C2 C3 113.4(4) no C2 C3 C11 109.2(5) no N4 C3 C2 110.0(5) no N4 C3 C11 110.3(5) no N4 C5 C51 126.6(5) no N4 C5 C16 115.6(5) no C16 C5 C51 117.8(4) no C7 C6 C51 121.4(5) no Cl1 C7 C6 118.6(5) no C6 C7 C8 123.0(6) no Cl1 C7 C8 118.4(5) no C7 C8 C9 117.1(6) no C8 C9 C91 122.1(6) no O13 C11 C3 109.7(6) no O12 C11 O13 123.9(7) no O12 C11 C3 126.4(7) no O13 C14 C15 108.4(9) no C17 C16 C21 120.2(5) no C5 C16 C21 120.5(5) no C5 C16 C17 119.2(5) no C16 C17 C18 120.8(6) no C17 C18 C19 118.7(7) no C18 C19 C20 121.0(7) no C19 C20 C21 121.4(7) no C16 C21 C20 117.8(6) no C5 C51 C91 122.1(5) no C6 C51 C91 116.6(5) no C5 C51 C6 121.3(4) no C9 C91 C51 119.8(5) no N1 C91 C9 118.9(5) no N1 C91 C51 121.1(5) no N4 C3 H3 109.12 no C2 C3 H3 109.19 no C11 C3 H3 109.14 no C7 C6 H6 119.34 no C51 C6 H6 119.26 no C7 C8 H8 121.44 no C9 C8 H8 121.51 no C8 C9 H9 118.95 no C91 C9 H9 118.93 no O13 C14 H14A 109.98 no O13 C14 H14B 109.99 no C15 C14 H14A 110.06 no C15 C14 H14B 110.06 no H14A C14 H14B 108.40 no C14 C15 H15A 109.50 no C14 C15 H15B 109.45 no C14 C15 H15C 109.58 no H15A C15 H15B 109.35 no H15A C15 H15C 109.48 no H15B C15 H15C 109.47 no C16 C17 H17 119.63 no C18 C17 H17 119.59 no C17 C18 H18 120.61 no C19 C18 H18 120.68 no C18 C19 H19 119.41 no C20 C19 H19 119.61 no C19 C20 H20 119.24 no C21 C20 H20 119.35 no C16 C21 H21 121.13 no C20 C21 H21 121.07 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 C6 3.629(6) 7_545 no Cl1 C15 3.489(10) 2_555 no Cl1 C17 3.536(7) 7_545 no Cl1 H15A 2.8498 2_555 no Cl1 H17 3.1104 1_545 no Cl1 H6 3.0376 7_545 no O10 O13 3.049(7) . no O10 C7 3.235(8) 4_655 no O10 C8 3.178(8) 4_655 no O12 C9 3.309(9) 1_565 no O12 N4 2.771(8) . no O12 C8 3.165(9) 1_565 no O13 O10 3.049(7) . no O10 H19 2.7169 8_554 no O12 H9 2.7637 1_565 no O12 H14A 2.3338 . no O12 H8 2.4975 1_565 no O13 H14A 2.8351 7_545 no N1 N4 2.954(8) . no N4 O12 2.771(8) . no N4 N1 2.954(8) . no N4 C9 3.374(8) 4_655 no N4 H17 2.6035 . no N4 H1 2.6926 4_655 no C2 C8 3.472(9) 4_655 no C2 C9 3.493(9) 4_655 no C6 C21 3.133(8) . no C6 Cl1 3.629(6) 7_555 no C7 O10 3.235(8) 4_645 no C8 O12 3.165(9) 1_545 no C8 O10 3.178(8) 4_645 no C8 C2 3.472(9) 4_645 no C9 O12 3.309(9) 1_545 no C9 C2 3.493(9) 4_645 no C9 N4 3.374(8) 4_645 no C15 Cl1 3.489(10) 2_554 no C17 Cl1 3.536(7) 7_555 no C20 C20 3.457(11) 5_656 no C21 C6 3.133(8) . no C6 H21 2.8856 . no C8 H3 2.9922 7_545 no C11 H15C 3.0206 . no C16 H1 3.0702 4_655 no C16 H6 2.7173 . no C17 H1 2.8868 4_655 no C19 H18 2.9487 5_666 no C20 H20 3.0968 5_656 no C21 H6 2.8500 . no C51 H3 2.5568 . no C51 H21 2.7670 . no C91 H3 2.5839 . no H1 H9 2.5092 . no H1 N4 2.6926 4_645 no H1 C16 3.0702 4_645 no H1 C17 2.8868 4_645 no H3 C51 2.5568 . no H3 C91 2.5839 . no H3 C8 2.9922 7_555 no H6 C16 2.7173 . no H6 C21 2.8500 . no H6 Cl1 3.0376 7_555 no H8 O12 2.4975 1_545 no H9 O12 2.7637 1_545 no H9 H1 2.5092 . no H14A O12 2.3338 . no H14A O13 2.8351 7_555 no H15A Cl1 2.8498 2_554 no H15C C11 3.0206 . no H17 Cl1 3.1104 1_565 no H17 N4 2.6035 . no H18 C19 2.9487 5_666 no H18 H19 2.5219 5_666 no H19 H18 2.5219 5_666 no H19 O10 2.7169 8_555 no H20 C20 3.0968 5_656 no H21 C6 2.8856 . no H21 C51 2.7670 . no 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 _geom_hbond_publ_flag N1 H1 N4 4_645 .860 2.693 3.368(9) 136.38 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 C14 O13 C11 C3 -178.7(6) no C11 O13 C14 C15 111.1(9) no C14 O13 C11 O12 -.9(11) no C91 N1 C2 C3 7.5(8) no C91 N1 C2 O10 -175.7(5) no C2 N1 C91 C9 136.9(6) no C2 N1 C91 C51 -46.7(8) no C3 N4 C5 C51 2.6(8) no C5 N4 C3 C2 -75.0(6) no C3 N4 C5 C16 -176.6(5) no C5 N4 C3 C11 164.6(5) no O10 C2 C3 C11 13.5(8) no O10 C2 C3 N4 -107.6(6) no N1 C2 C3 N4 69.1(6) no N1 C2 C3 C11 -169.8(5) no C2 C3 C11 O13 74.0(7) no N4 C3 C11 O12 17.1(10) no N4 C3 C11 O13 -165.1(5) no C2 C3 C11 O12 -103.7(8) no N4 C5 C16 C17 40.0(8) no C16 C5 C51 C91 -141.5(5) no N4 C5 C51 C91 39.4(9) no N4 C5 C51 C6 -142.0(6) no C16 C5 C51 C6 37.2(7) no N4 C5 C16 C21 -142.8(6) no C51 C5 C16 C17 -139.2(6) no C51 C5 C16 C21 37.9(8) no C51 C6 C7 C8 .3(9) no C51 C6 C7 Cl1 178.5(4) no C7 C6 C51 C5 -179.0(5) no C7 C6 C51 C91 -.3(7) no C6 C7 C8 C9 .1(9) no Cl1 C7 C8 C9 -178.1(5) no C7 C8 C9 C91 -.4(9) no C8 C9 C91 C51 .4(8) no C8 C9 C91 N1 176.8(6) no C5 C16 C21 C20 -177.7(6) no C5 C16 C17 C18 176.9(6) no C17 C16 C21 C20 -.6(9) no C21 C16 C17 C18 -.3(9) no C16 C17 C18 C19 -.8(10) no C17 C18 C19 C20 2.8(11) no C18 C19 C20 C21 -3.9(12) no C19 C20 C21 C16 2.7(10) no C5 C51 C91 N1 2.3(7) no C5 C51 C91 C9 178.6(5) no C6 C51 C91 N1 -176.4(4) no C6 C51 C91 C9 .0(7) no