#------------------------------------------------------------------------------ #$Date: 2017-10-13 01:08:28 +0100 (Fri, 13 Oct 2017) $ #$Revision: 201955 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/83/2008311.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_2008311 loop_ _publ_author_name 'Zucco, C\'esar' 'Neves, Ademir' 'Vencato, Ivo' 'Szpoganicz, Bruno' 'Bertoldi, Fabiano C.' _publ_section_title ; 1-Chloro-2,4-dimorpholino-5-nitrobenzene ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 654 _journal_page_last 656 _journal_paper_doi 10.1107/S0108270198014516 _journal_volume 55 _journal_year 1999 _chemical_formula_moiety 'C14 H18 Cl N3 O4' _chemical_formula_sum 'C14 H18 Cl N3 O4' _chemical_formula_weight 327.76 _chemical_melting_point 447.0(10) _chemical_name_systematic ; 1-chloro-2,4-dimorpholino-5-nitrobenzene ; _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _cell_angle_alpha 90.00 _cell_angle_beta 125.00(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 22.997(5) _cell_length_b 8.069(2) _cell_length_c 20.001(4) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 18.50 _cell_measurement_theta_min 9.99 _cell_volume 3040.2(16) _computing_cell_refinement 'SET4 in CAD-4 EXPRESS' _computing_data_collection 'CAD-4 EXPRESS (Enraf-Nonius, 1994)' _computing_data_reduction 'MolEN (Fair, 1990)' _computing_molecular_graphics 'ZORTEP (Zsolnai et al., 1996)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_measurement_device_type 'Nonius CAD-4' _diffrn_measurement_method \w/2\q _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 0.019 _diffrn_reflns_av_sigmaI/netI 0.026 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 2771 _diffrn_reflns_theta_full 24.98 _diffrn_reflns_theta_max 25.0 _diffrn_reflns_theta_min 2.49 _diffrn_standards_decay_% -1.1 _diffrn_standards_interval_time 60 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.273 _exptl_absorpt_correction_T_max 0.931 _exptl_absorpt_correction_T_min 0.901 _exptl_absorpt_correction_type '\y scan' _exptl_absorpt_process_details '(MoLEN; Fair, 1990)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.432 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prismatic _exptl_crystal_F_000 1376 _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.26 _refine_diff_density_max 0.344 _refine_diff_density_min -0.306 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.105 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 199 _refine_ls_number_reflns 2683 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.105 _refine_ls_R_factor_all 0.066 _refine_ls_R_factor_gt 0.042 _refine_ls_shift/su_max 0.018 _refine_ls_shift/su_mean 0.002 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.050P)^2^+4.07P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.124 _reflns_number_gt 2064 _reflns_number_total 2683 _reflns_threshold_expression I>2\s(I) _cod_data_source_file bk1415.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '446-448' was changed to '447.0(10)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '446-448' was changed to '447.0(10)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^)+(0.050P)^2^+4.07P] where P=(Fo^2^+2Fc^2^)/3' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/[\s^2^(Fo^2^)+(0.050P)^2^+4.07P] where P=(Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_cell_volume 3040.2(12) _cod_original_sg_symbol_H-M 'C 2/c' _cod_database_code 2008311 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' loop_ _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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol Cl 0.15081(4) 0.05925(10) 0.38101(5) 0.0554(2) Uani d . 1 . . Cl O1 -0.25118(9) -0.0655(2) 0.32608(11) 0.0459(5) Uani d . 1 . . O O2 0.16220(11) -0.5551(2) 0.47285(13) 0.0579(5) Uani d . 1 . . O O3 -0.06423(12) 0.4367(3) 0.28079(14) 0.0652(6) Uani d . 1 . . O O4 -0.09679(13) 0.3835(3) 0.35911(14) 0.0634(6) Uani d . 1 . . O N1 -0.11667(10) 0.0347(2) 0.36372(11) 0.0317(4) Uani d . 1 . . N N2 0.09947(10) -0.2358(2) 0.42920(12) 0.0364(5) Uani d . 1 . . N N3 -0.06845(10) 0.3455(2) 0.32643(12) 0.0358(5) Uani d . 1 . . N C1 -0.18293(12) 0.0612(3) 0.28189(14) 0.0402(6) Uani d . 1 . . C H1A -0.1907 -0.0312 0.2466 0.060 Uiso calc R 1 . . H H1B -0.1789 0.1614 0.2580 0.060 Uiso calc R 1 . . H C2 -0.24482(13) 0.0761(3) 0.28852(17) 0.0469(6) Uani d . 1 . . C H2A -0.2386 0.1739 0.3202 0.070 Uiso calc R 1 . . H H2B -0.2882 0.0899 0.2344 0.070 Uiso calc R 1 . . H C3 -0.18823(13) -0.0833(3) 0.40638(15) 0.0411(6) Uani d . 1 . . C H3A -0.1930 -0.1778 0.4328 0.062 Uiso calc R 1 . . H H3B -0.1815 0.0148 0.4382 0.062 Uiso calc R 1 . . H C4 -0.12422(12) -0.1075(3) 0.40373(15) 0.0355(5) Uani d . 1 . . C H4A -0.0818 -0.1188 0.4588 0.053 Uiso calc R 1 . . H H4B -0.1299 -0.2081 0.3740 0.053 Uiso calc R 1 . . H C5 -0.05375(11) 0.0420(3) 0.36762(13) 0.0306(5) Uani d . 1 . . C C6 -0.03242(12) 0.1830(3) 0.34536(13) 0.0335(5) Uani d . 1 . . C C7 0.02870(12) 0.1820(3) 0.34670(13) 0.0357(5) Uani d . 1 . . C H7 0.0408 0.2757 0.3301 0.043 Uiso calc R 1 . . H C8 0.07133(12) 0.0446(3) 0.37214(14) 0.0364(5) Uani d . 1 . . C C9 0.05403(12) -0.0982(3) 0.39710(13) 0.0325(5) Uani d . 1 . . C C10 -0.00883(12) -0.0946(3) 0.39247(14) 0.0335(5) Uani d . 1 . . C H10 -0.0217 -0.1901 0.4070 0.040 Uiso calc R 1 . . H C11 0.09202(15) -0.3459(3) 0.48193(17) 0.0448(6) Uani d . 1 . . C H11A 0.0491 -0.4115 0.4493 0.067 Uiso calc R 1 . . H H11B 0.0886 -0.2811 0.5204 0.067 Uiso calc R 1 . . H C12 0.15584(17) -0.4580(4) 0.52726(19) 0.0538(7) Uani d . 1 . . C H12A 0.1983 -0.3915 0.5608 0.081 Uiso calc R 1 . . H H12B 0.1517 -0.5304 0.5630 0.081 Uiso calc R 1 . . H C13 0.16922(15) -0.4511(4) 0.42062(19) 0.0541(7) Uani d . 1 . . C H13A 0.1727 -0.5193 0.3831 0.081 Uiso calc R 1 . . H H13B 0.2127 -0.3875 0.4531 0.081 Uiso calc R 1 . . H C14 0.10705(14) -0.3332(4) 0.37220(16) 0.0457(6) Uani d . 1 . . C H14A 0.1151 -0.2595 0.3399 0.069 Uiso calc R 1 . . H H14B 0.0639 -0.3954 0.3353 0.069 Uiso calc R 1 . . H 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 Cl 0.0465(4) 0.0647(5) 0.0716(5) 0.0012(3) 0.0436(4) 0.0085(4) O1 0.0317(9) 0.0514(11) 0.0523(11) -0.0052(8) 0.0228(8) 0.0005(9) O2 0.0641(13) 0.0406(11) 0.0774(14) 0.0121(9) 0.0456(12) -0.0006(10) O3 0.0708(14) 0.0560(13) 0.0834(15) 0.0163(11) 0.0528(13) 0.0344(12) O4 0.0902(16) 0.0469(12) 0.0777(15) 0.0204(11) 0.0625(14) 0.0144(10) N1 0.0287(9) 0.0331(11) 0.0340(10) 0.0010(8) 0.0184(8) 0.0044(8) N2 0.0410(11) 0.0369(11) 0.0395(11) 0.0056(9) 0.0279(9) -0.0007(9) N3 0.0374(11) 0.0320(11) 0.0387(11) -0.0013(8) 0.0223(9) 0.0058(9) C1 0.0347(13) 0.0447(14) 0.0353(12) -0.0009(11) 0.0167(11) 0.0034(11) C2 0.0307(13) 0.0506(16) 0.0490(15) 0.0031(11) 0.0167(12) 0.0077(13) C3 0.0379(13) 0.0452(14) 0.0462(14) -0.0002(11) 0.0276(12) 0.0044(12) C4 0.0361(12) 0.0341(13) 0.0409(13) 0.0002(10) 0.0248(11) 0.0045(10) C5 0.0289(11) 0.0342(12) 0.0299(11) -0.0012(9) 0.0175(10) -0.0009(9) C6 0.0344(12) 0.0336(13) 0.0298(11) -0.0009(10) 0.0168(10) 0.0017(10) C7 0.0381(13) 0.0388(13) 0.0324(12) -0.0023(11) 0.0215(11) 0.0046(10) C8 0.0332(12) 0.0460(15) 0.0349(12) -0.0020(11) 0.0223(11) 0.0001(11) C9 0.0347(12) 0.0350(13) 0.0304(11) 0.0009(10) 0.0201(10) -0.0017(10) C10 0.0355(12) 0.0314(12) 0.0371(12) -0.0010(10) 0.0227(10) 0.0015(10) C11 0.0569(16) 0.0373(14) 0.0546(16) 0.0061(12) 0.0404(14) 0.0033(12) C12 0.0662(18) 0.0423(15) 0.0613(17) 0.0189(14) 0.0413(16) 0.0099(13) C13 0.0464(16) 0.0571(18) 0.0653(18) 0.0079(13) 0.0359(15) -0.0122(15) C14 0.0471(14) 0.0531(16) 0.0460(14) 0.0013(12) 0.0320(13) -0.0109(13) 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' Cl Cl 0.1484 0.1585 '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 C2 O1 C3 109.3(2) yes C12 O2 C13 110.1(2) yes C5 N1 C4 116.3(2) yes C5 N1 C1 115.5(2) yes C4 N1 C1 110.4(2) yes C9 N2 C11 116.5(2) yes C9 N2 C14 117.1(2) yes C11 N2 C14 110.4(2) yes O4 N3 O3 123.8(2) no O4 N3 C6 119.17(19) no O3 N3 C6 116.9(2) no N1 C1 C2 109.9(2) no O1 C2 C1 111.8(2) no O1 C3 C4 110.7(2) no N1 C4 C3 109.86(19) no C10 C5 N1 121.1(2) no C10 C5 C6 115.5(2) no N1 C5 C6 123.4(2) no C7 C6 C5 121.4(2) no C7 C6 N3 114.9(2) no C5 C6 N3 123.5(2) no C8 C7 C6 120.8(2) no C7 C8 C9 120.6(2) no C7 C8 Cl 118.05(18) no C9 C8 Cl 121.14(18) no C10 C9 C8 117.0(2) no C10 C9 N2 121.2(2) no C8 C9 N2 121.6(2) no C5 C10 C9 124.6(2) no N2 C11 C12 108.8(2) no O2 C12 C11 111.4(2) no O2 C13 C14 112.2(2) no N2 C14 C13 109.1(2) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cl C8 . 1.736(2) yes O1 C2 . 1.420(3) no O1 C3 . 1.424(3) no O2 C12 . 1.415(3) no O2 C13 . 1.419(4) no O3 N3 . 1.219(3) yes O4 N3 . 1.198(3) yes N1 C5 . 1.405(3) yes N1 C4 . 1.465(3) yes N1 C1 . 1.478(3) yes N2 C9 . 1.403(3) yes N2 C11 . 1.462(3) yes N2 C14 . 1.475(3) yes N3 C6 . 1.480(3) yes C1 C2 . 1.508(3) no C3 C4 . 1.516(3) no C5 C10 . 1.393(3) no C5 C6 . 1.408(3) no C6 C7 . 1.390(3) no C7 C8 . 1.370(3) no C8 C9 . 1.401(3) no C9 C10 . 1.395(3) no C11 C12 . 1.506(4) no C13 C14 . 1.516(4) 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 C5 N1 N2 C9 -5.2(3) C4 N1 N2 C9 -175.4(3) C1 N1 N2 C9 72.2(3) C5 N1 N2 C11 158.2(3) C4 N1 N2 C11 -12.01(18) C1 N1 N2 C11 -124.4(2) C5 N1 N2 C14 -88.9(3) C4 N1 N2 C14 100.9(2) C1 N1 N2 C14 -11.5(3) C5 N1 C1 C2 -171.4(2) C4 N1 C1 C2 54.1(3) N2 N1 C1 C2 154.62(16) C3 O1 C2 C1 60.5(3) N1 C1 C2 O1 -57.1(3) C2 O1 C3 C4 -61.0(3) C5 N1 C4 C3 170.72(19) C1 N1 C4 C3 -55.2(3) N2 N1 C4 C3 176.36(18) O1 C3 C4 N1 59.1(3) C4 N1 C5 C10 13.2(3) C1 N1 C5 C10 -118.6(2) N2 N1 C5 C10 2.24(13) C4 N1 C5 C6 -168.4(2) C1 N1 C5 C6 59.8(3) N2 N1 C5 C6 -179.3(4) C10 C5 C6 C7 1.5(3) N1 C5 C6 C7 -177.0(2) C10 C5 C6 N3 -172.8(2) N1 C5 C6 N3 8.7(3) O4 N3 C6 C7 -144.7(2) O3 N3 C6 C7 31.8(3) O4 N3 C6 C5 29.9(3) O3 N3 C6 C5 -153.6(2) C5 C6 C7 C8 -1.9(3) N3 C6 C7 C8 172.8(2) C6 C7 C8 C9 0.2(4) C6 C7 C8 Cl -174.19(18) C7 C8 C9 C10 1.8(3) Cl C8 C9 C10 176.02(17) C7 C8 C9 N2 -175.1(2) Cl C8 C9 N2 -0.8(3) C11 N2 C9 C10 -20.5(3) C14 N2 C9 C10 113.3(2) N1 N2 C9 C10 -1.89(12) C11 N2 C9 C8 156.2(2) C14 N2 C9 C8 -70.0(3) N1 N2 C9 C8 174.8(4) N1 C5 C10 C9 179.2(2) C6 C5 C10 C9 0.7(3) C8 C9 C10 C5 -2.3(3) N2 C9 C10 C5 174.6(2) C9 N2 C11 C12 -165.5(2) C14 N2 C11 C12 57.8(3) N1 N2 C11 C12 -175.1(2) C13 O2 C12 C11 59.7(3) N2 C11 C12 O2 -59.9(3) C12 O2 C13 C14 -57.9(3) C9 N2 C14 C13 167.8(2) C11 N2 C14 C13 -55.8(3) N1 N2 C14 C13 -156.91(17) O2 C13 C14 N2 55.9(3) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 2076251