#------------------------------------------------------------------------------ #$Date: 2013-12-28 13:58:47 +0000 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/37/2003707.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_2003707 loop_ _publ_author_name 'Bachechi, F.' 'Gavuzzo, E.' 'Cerreto, F.' 'Scalzo, M.' _publ_section_title ; A 1,5-Diarylpyrrole Derivative ; _journal_issue 7 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1431 _journal_page_last 1434 _journal_volume 51 _journal_year 1995 _chemical_formula_moiety 'C20 H16 Cl3 N1 O2' _chemical_formula_sum 'C20 H16 Cl3 N O2' _chemical_formula_weight 408.71 _chemical_name_systematic ; 1-(2,4-dichlorophenyl)-5-(4-chlorophenyl)-3-etoxycarbonyl- 2-methyl-pyrrole ; _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _cell_angle_alpha 90.00 _cell_angle_beta 92.37(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 6.504(2) _cell_length_b 13.121(2) _cell_length_c 22.192(2) _cell_measurement_reflns_used 15 _cell_measurement_temperature 295 _cell_measurement_theta_max 40.0 _cell_measurement_theta_min 39.0 _cell_volume 1892.2(7) _computing_cell_refinement 'MSC/AFC Diffractometer Control Software' _computing_data_collection ; MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1988) ; _computing_data_reduction ; TEXSAN (Molecular Structure Corporation, 1985) ; _computing_molecular_graphics TEXSAN _computing_structure_refinement TEXSAN _computing_structure_solution ; TEXSAN (Molecular Structure Corporation, 1985) ; _diffrn_ambient_temperature 298 _diffrn_measurement_device 'Rigaku AFC5R' _diffrn_measurement_method 'profile data from \w-2\q' _diffrn_radiation_monochromator 'equatorial mounted graphite' _diffrn_radiation_source ; Rigaku AFC5R diffractometer on a 12KW Rotating Anode Generator ; _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.027 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 3046 _diffrn_reflns_theta_max 62.0 _diffrn_reflns_theta_min 2.5 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 150 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 4.594 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_correction_T_min 0.78 _exptl_absorpt_correction_type 'empirical via \y scan at \c = 90\%' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.434 _exptl_crystal_description prism _exptl_crystal_F_000 840.0 _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _refine_diff_density_max 1.45 _refine_diff_density_min -1.65 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_obs 2.36 _refine_ls_matrix_type full _refine_ls_number_parameters 235 _refine_ls_number_reflns 1955 _refine_ls_R_factor_obs 0.048 _refine_ls_shift/esd_max 0.69 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme 'sigma with w = 1/[\s^2^(F)]' _refine_ls_wR_factor_obs 0.064 _reflns_number_observed 1955 _reflns_number_total 3046 _reflns_observed_criterion >3\s(I) _[local]_cod_data_source_file na1117.cif _[local]_cod_data_source_block Bachechi _[local]_cod_cif_authors_sg_H-M 'P 21/c' _[local]_cod_chemical_formula_sum_orig 'C20 H16 Cl3 N1 O2' _cod_database_code 2003707 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_source _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag C Carbon 'International Tables Vol IV Tables 2.2A, 2.2C, 2.3.1' .002 .002 O Oxygen 'International Tables Vol IV Tables 2.2A, 2.2C, 2.3.1' .008 .006 H Hydrogen 'International Tables Vol IV Tables 2.2A, 2.2C, 2.3.1' .000 .000 N Nitrogen 'International Tables Vol IV Tables 2.2A, 2.2C, 2.3.1' .004 .003 Cl Chlorine 'International Tables Vol IV Tables 2.2A, 2.2C, 2.3.1' .132 .159 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_B_iso_or_equiv Cl1 0.8185(2) 0.7468(1) 0.02791(5) 6.94(7) Cl2 0.1788(2) 0.4999(1) 0.06449(5) 5.75(6) Cl3 0.8160(2) 0.0747(1) 0.03820(6) 7.45(8) O1 -0.0855(5) 0.3567(2) 0.3204(1) 5.9(2) O2 -0.0912(5) 0.5267(2) 0.3161(1) 6.4(2) N1 0.3676(5) 0.4742(2) 0.1888(1) 3.4(1) C2 0.2362(6) 0.5142(3) 0.2296(2) 3.6(2) C3 0.1256(6) 0.4347(3) 0.2521(2) 3.7(2) C4 0.1912(6) 0.3443(3) 0.2241(2) 3.9(2) C5 0.3387(6) 0.3681(3) 0.1850(2) 3.5(2) C6 0.4796(6) 0.5367(3) 0.1487(2) 3.4(2) C7 0.6583(6) 0.5844(3) 0.1691(2) 4.1(2) C8 0.7634(6) 0.6487(3) 0.1322(2) 4.6(2) C9 0.6896(7) 0.6641(3) 0.0744(2) 4.3(2) C10 0.5117(7) 0.6183(3) 0.0526(2) 4.2(2) C11 0.4064(6) 0.5546(3) 0.0902(2) 3.6(2) C12 0.2350(7) 0.6255(3) 0.2440(2) 4.7(2) C13 -0.0240(6) 0.4464(3) 0.2982(2) 4.5(2) C14 -0.2305(8) 0.3602(4) 0.3710(2) 6.2(3) C15 -0.4353(9) 0.3763(4) 0.3442(3) 7.4(3) C17 0.4594(6) 0.3008(3) 0.1467(2) 3.5(2) C18 0.6597(6) 0.3203(3) 0.1313(2) 4.4(2) C19 0.7694(7) 0.2522(3) 0.0974(2) 4.9(2) C20 0.6790(7) 0.1623(3) 0.0795(2) 4.6(2) C21 0.4812(7) 0.1398(3) 0.0942(2) 4.8(2) C22 0.3726(6) 0.2085(3) 0.1277(2) 4.2(2) H1 0.140272 0.277771 0.231478 ? H2 0.236027 0.192515 0.137969 ? H3 0.419480 0.077412 0.081540 ? H4 0.905884 0.267585 0.086719 ? H5 0.723583 0.382023 0.144279 ? H6 0.709545 0.572779 0.209185 ? H7 0.885455 0.681820 0.146773 ? H8 0.461782 0.630153 0.012387 ? H9 -0.225596 0.297744 0.392662 ? H10 -0.194607 0.414710 0.397654 ? H11 -0.438419 0.438672 0.322412 ? H12 -0.469537 0.321695 0.317508 ? H13 -0.532080 0.379077 0.375063 ? H14 0.367247 0.645441 0.259519 ? H15 0.201216 0.663151 0.208376 ? H16 0.135684 0.638706 0.273230 ? loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 1 0 -1 -1 -1 2 0 1 3 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 C13 O1 C14 117.1(3) yes C2 N1 C5 109.4(3) yes C2 N1 C6 122.5(3) yes C5 N1 C6 126.8(3) yes N1 C2 C3 107.3(3) yes N1 C2 C12 121.5(3) yes C3 C2 C12 131.1(3) yes C2 C3 C4 107.8(3) yes C2 C3 C13 123.6(3) yes C4 C3 C13 128.5(3) yes C3 C4 C5 108.8(3) yes N1 C5 C4 106.6(3) yes N1 C5 C17 123.6(3) yes C4 C5 C17 129.7(3) yes N1 C6 C7 119.9(3) yes N1 C6 C11 121.1(3) yes C7 C6 C11 118.9(3) yes C6 C7 C8 121.1(3) yes C7 C8 C9 119.0(4) yes Cl1 C9 C8 119.4(3) yes Cl1 C9 C10 119.0(3) yes C8 C9 C10 121.6(4) yes C9 C10 C11 118.9(3) yes Cl2 C11 C6 119.9(3) yes Cl2 C11 C10 119.5(3) yes C6 C11 C10 120.6(4) yes O1 C14 C15 107.0(4) yes O1 C13 O2 121.5(4) yes O1 C13 C3 112.7(3) yes O2 C13 C3 125.8(4) yes C5 C17 C18 124.1(3) yes C5 C17 C22 118.4(3) yes C18 C17 C22 117.3(3) yes C17 C18 C19 121.8(4) yes C18 C19 C20 119.3(4) yes Cl3 C20 C19 119.9(4) yes Cl3 C20 C21 119.3(3) yes C19 C20 C21 120.7(4) yes C20 C21 C22 119.6(4) yes C17 C22 C21 121.3(4) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Cl1 C9 1.736(4) yes Cl2 C11 1.721(4) yes Cl3 C20 1.739(4) yes O1 C14 1.497(5) yes O1 C13 1.344(5) yes O2 C13 1.213(5) yes N1 C2 1.375(5) yes N1 C5 1.407(4) yes N1 C6 1.432(4) yes C2 C3 1.372(5) yes C2 C12 1.495(5) yes C3 C4 1.413(5) yes C3 C13 1.449(5) yes C4 C5 1.356(5) yes C5 C17 1.475(5) yes C6 C7 1.380(5) yes C6 C11 1.383(5) yes C7 C8 1.375(5) yes C8 C9 1.367(5) yes C9 C10 1.374(6) yes C10 C11 1.383(5) yes C14 C15 1.452(7) yes C17 C18 1.384(5) yes C17 C22 1.394(5) yes C18 C19 1.385(5) yes C19 C20 1.369(6) yes C20 C21 1.373(6) yes C21 C22 1.380(5) yes 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 C2 N1 C6 C7 80.6(5) N1 C5 C17 C18 28.9(6) _journal_paper_doi 10.1107/S0108270195000734