#------------------------------------------------------------------------------ #$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: svn://www.crystallography.net/cod/cif/2/2200811.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_2200811 loop_ _publ_author_name 'Light, Mark E.' 'Camiolo, Salvatore' 'Gale, Philip A.' 'Hursthouse, Michael B.' _publ_section_title ; Methyl 5-methyl-3,4-diphenyl-1H-pyrrole-2-carboxylate ; _journal_issue 12 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1245 _journal_page_last o1246 _journal_volume 57 _journal_year 2001 _chemical_formula_iupac 'C19 H17 N O2' _chemical_formula_moiety 'C19 H17 N O2' _chemical_formula_sum 'C19 H17 N O2' _chemical_formula_weight 291.34 _chemical_name_systematic ; Methyl 5-methyl-3,4-diphenyl-1H-pyrrole-2-carboxylate ; _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' _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 118.186(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 16 _cell_length_a 34.1913(12) _cell_length_b 10.7042(4) _cell_length_c 19.1129(9) _cell_measurement_reflns_used 28010 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 25.0 _cell_measurement_theta_min 3.3 _cell_volume 6165.6(4) _computing_cell_refinement ; SCALEPACK (Otwinowski & Minor, 1997) and COLLECT ; _computing_data_collection ; COLLECT (Hooft, 1998) ; _computing_data_reduction ; DENZO (Otwinowski & Minor, 1997), COLLECT and maXus (Mackay et al., 1998) ; _computing_molecular_graphics 'CAMERON (Watkin et al., 1993)' _computing_publication_material 'WINGX (Farrugia, 1998)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 120(2) _diffrn_detector_area_resol_mean '9.091 pixels mm^1^' _diffrn_measured_fraction_theta_full .995 _diffrn_measured_fraction_theta_max .995 _diffrn_measurement_device_type 'Nonius KappaCCD area-detector' _diffrn_measurement_method '\f and \w scans to fill the asymmetric unit' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Nonius FR591 Rotating anode' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .1023 _diffrn_reflns_av_sigmaI/netI .0910 _diffrn_reflns_limit_h_max 40 _diffrn_reflns_limit_h_min -40 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 28010 _diffrn_reflns_theta_full 25.0 _diffrn_reflns_theta_max 25.0 _diffrn_reflns_theta_min 3.3 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu .08 _exptl_absorpt_correction_T_max .996 _exptl_absorpt_correction_T_min .992 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SORTAV; Blessing, 1997)' _exptl_crystal_colour Colourless _exptl_crystal_density_diffrn 1.255 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Plate _exptl_crystal_F_000 2464 _exptl_crystal_size_max .10 _exptl_crystal_size_mid .10 _exptl_crystal_size_min .05 _refine_diff_density_max .37 _refine_diff_density_min -.36 _refine_ls_extinction_coef none _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.00 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 397 _refine_ls_number_reflns 5420 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.00 _refine_ls_R_factor_all .128 _refine_ls_R_factor_gt .060 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0881P)^2^+0.4211P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .171 _reflns_number_gt 3071 _reflns_number_total 5420 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file ya6076.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'C 2/c' _cod_depositor_comments ; 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 2.4.1 from 2010-06-29. '_exptl_absorpt_correction_type' value 'Multi-scan' changed to 'multi-scan' 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_database_code 2200811 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_type_symbol C1 .18316(10) -.2849(3) .1393(2) .0387(8) Uani d . 1 C H1A .2111 -.2737 .1375 .058 Uiso calc R 1 H H1B .1608 -.3208 .0891 .058 Uiso calc R 1 H H1C .1879 -.3413 .1830 .058 Uiso calc R 1 H C2 .16731(10) -.1613(3) .15216(17) .0308(7) Uani d . 1 C C3 .12978(9) -.1280(3) .15895(16) .0283(7) Uani d . 1 C C4 .12983(9) .0051(3) .16501(16) .0276(7) Uani d . 1 C C5 .16766(9) .0479(3) .16284(17) .0300(7) Uani d . 1 C C6 .18825(10) .1682(3) .17113(17) .0308(7) Uani d . 1 C C7 .18855(11) .3832(3) .1993(2) .0423(8) Uani d . 1 C H7A .1710 .4447 .2106 .063 Uiso calc R 1 H H7B .1900 .4077 .1512 .063 Uiso calc R 1 H H7C .2186 .3795 .2441 .063 Uiso calc R 1 H C8 .09577(9) -.2166(3) .15584(17) .0287(7) Uani d . 1 C C9 .10818(10) -.3274(3) .19974(17) .0345(7) Uani d . 1 C H9 .1387 -.3439 .2335 .041 Uiso calc R 1 H C10 .07689(11) -.4131(3) .19489(18) .0390(8) Uani d . 1 C H10 .0860 -.4881 .2250 .047 Uiso calc R 1 H C11 .03201(11) -.3899(3) .14597(19) .0404(8) Uani d . 1 C H11 .0104 -.4490 .1421 .048 Uiso calc R 1 H C12 .01920(10) -.2803(3) .10311(19) .0396(8) Uani d . 1 C H12 -.0114 -.2638 .0700 .048 Uiso calc R 1 H C13 .05045(10) -.1941(3) .10771(18) .0348(7) Uani d . 1 C H13 .0411 -.1189 .0779 .042 Uiso calc R 1 H C14 .09599(9) .0843(3) .17112(17) .0278(7) Uani d . 1 C C15 .08629(10) .0709(3) .23329(18) .0349(8) Uani d . 1 C H15 .1005 .0072 .2716 .042 Uiso calc R 1 H C16 .05599(11) .1495(3) .2404(2) .0402(8) Uani d . 1 C H16 .0498 .1398 .2835 .048 Uiso calc R 1 H C17 .03497(10) .2416(3) .18471(19) .0360(8) Uani d . 1 C H17 .0149 .2970 .1901 .043 Uiso calc R 1 H C18 .04326(10) .2528(3) .12127(19) .0356(8) Uani d . 1 C H18 .0281 .3147 .0820 .043 Uiso calc R 1 H C19 .07334(10) .1753(3) .11396(18) .0337(7) Uani d . 1 C H19 .0787 .1839 .0697 .040 Uiso calc R 1 H C20 .28778(11) .3862(3) .12216(19) .0367(8) Uani d . 1 C H20A .2616 .3719 .1292 .055 Uiso calc R 1 H H20B .2800 .4424 .0770 .055 Uiso calc R 1 H H20C .3113 .4241 .1704 .055 Uiso calc R 1 H C21 .30371(9) .2643(3) .10665(17) .0298(7) Uani d . 1 C C22 .33940(9) .2377(3) .09254(16) .0290(7) Uani d . 1 C C23 .34072(9) .1051(3) .08523(16) .0293(7) Uani d . 1 C C24 .30615(9) .0562(3) .09607(17) .0294(7) Uani d . 1 C C25 .28822(10) -.0669(3) .09481(18) .0325(7) Uani d . 1 C C26 .30009(13) -.2860(3) .0947(2) .0501(9) Uani d . 1 C H26A .3182 -.3449 .0830 .075 Uiso calc R 1 H H26B .2686 -.3029 .0596 .075 Uiso calc R 1 H H26C .3065 -.2957 .1501 .075 Uiso calc R 1 H C27 .37110(10) .3290(3) .09083(17) .0298(7) Uani d . 1 C C28 .35697(10) .4332(3) .04101(17) .0337(7) Uani d . 1 C H28 .3261 .4471 .0084 .040 Uiso calc R 1 H C29 .38728(11) .5168(3) .03829(19) .0391(8) Uani d . 1 C H29 .3771 .5872 .0040 .047 Uiso calc R 1 H C30 .43201(11) .4977(3) .0851(2) .0406(8) Uani d . 1 C H30 .4528 .5537 .0823 .049 Uiso calc R 1 H C31 .44675(11) .3968(3) .13635(19) .0367(8) Uani d . 1 C H31 .4776 .3850 .1698 .044 Uiso calc R 1 H C32 .41665(10) .3131(3) .13905(18) .0344(7) Uani d . 1 C H32 .4271 .2438 .1742 .041 Uiso calc R 1 H C33 .37190(9) .0390(3) .06410(18) .0295(7) Uani d . 1 C C34 .37957(10) .0885(3) .00430(17) .0335(7) Uani d . 1 C H34 .3652 .1639 -.0212 .040 Uiso calc R 1 H C35 .40780(10) .0300(3) -.0187(2) .0388(8) Uani d . 1 C H35 .4127 .0655 -.0595 .047 Uiso calc R 1 H C36 .42864(10) -.0790(3) .0170(2) .0412(8) Uani d . 1 C H36 .4475 -.1203 .0005 .049 Uiso calc R 1 H C37 .42189(10) -.1281(3) .0773(2) .0400(8) Uani d . 1 C H37 .4365 -.2033 .1027 .048 Uiso calc R 1 H C38 .39424(9) -.0696(3) .10128(18) .0343(7) Uani d . 1 C H38 .3905 -.1038 .1436 .041 Uiso calc R 1 H N1 .18954(8) -.0552(2) .15491(14) .0314(6) Uani d . 1 N H1 .2145 -.0523 .1520 .038 Uiso calc R 1 H N2 .28444(8) .1557(2) .10873(14) .0324(6) Uani d . 1 N H2 .2613 .1489 .1170 .039 Uiso calc R 1 H O1 .22208(7) .18485(19) .16545(13) .0410(6) Uani d . 1 O O2 .16790(7) .26184(18) .18756(12) .0363(5) Uani d . 1 O O3 .25634(7) -.08671(19) .10541(13) .0394(5) Uani d . 1 O O4 .31039(7) -.15943(19) .08193(15) .0467(6) Uani d . 1 O 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 C1 .0339(17) .0348(18) .050(2) .0033(15) .0224(16) .0018(16) C2 .0288(16) .0283(16) .0341(17) .0008(14) .0139(14) .0011(13) C3 .0256(15) .0304(17) .0291(16) .0023(14) .0130(13) .0026(13) C4 .0262(15) .0299(16) .0272(16) .0000(14) .0129(13) .0034(13) C5 .0282(16) .0308(17) .0300(17) .0043(14) .0129(14) .0030(13) C6 .0265(16) .0356(18) .0293(16) .0004(15) .0122(14) .0014(14) C7 .046(2) .0297(17) .051(2) -.0079(16) .0222(17) -.0082(15) C8 .0295(16) .0309(16) .0326(16) -.0012(14) .0205(14) -.0043(14) C9 .0364(17) .0341(18) .0341(17) -.0031(15) .0176(15) .0004(14) C10 .049(2) .0325(17) .0393(18) -.0074(16) .0234(16) .0000(15) C11 .043(2) .0384(19) .046(2) -.0149(17) .0267(17) -.0118(16) C12 .0302(17) .046(2) .045(2) -.0059(16) .0206(15) -.0154(17) C13 .0336(18) .0336(17) .0404(18) .0018(15) .0201(15) -.0035(15) C14 .0243(15) .0270(15) .0331(16) -.0026(14) .0143(13) .0020(14) C15 .0360(17) .0335(17) .0375(18) .0027(15) .0191(15) .0073(14) C16 .0442(19) .0428(19) .045(2) .0076(17) .0305(17) .0063(16) C17 .0323(17) .0334(18) .045(2) .0010(15) .0203(16) -.0028(16) C18 .0314(17) .0304(17) .0423(19) .0075(15) .0152(15) .0083(14) C19 .0325(17) .0389(18) .0321(17) .0045(15) .0173(14) .0066(15) C20 .0394(18) .0284(16) .0491(19) .0022(15) .0266(16) -.0024(15) C21 .0274(15) .0280(17) .0339(17) -.0010(14) .0145(14) -.0013(13) C22 .0300(16) .0280(16) .0277(16) .0019(14) .0127(13) .0004(13) C23 .0272(16) .0298(16) .0278(16) .0016(14) .0104(13) -.0011(13) C24 .0286(16) .0267(16) .0351(17) .0031(14) .0168(14) -.0009(13) C25 .0313(17) .0309(17) .0393(18) -.0001(15) .0199(15) -.0033(14) C26 .060(2) .0239(17) .078(3) -.0026(17) .041(2) -.0040(17) C27 .0359(18) .0261(16) .0329(17) -.0004(14) .0208(15) -.0043(13) C28 .0367(17) .0305(17) .0341(17) -.0008(15) .0168(14) -.0026(14) C29 .048(2) .0337(18) .0399(19) -.0027(17) .0248(17) .0006(15) C30 .044(2) .0372(19) .050(2) -.0135(17) .0301(18) -.0124(17) C31 .0333(17) .0381(19) .0440(19) -.0025(16) .0226(15) -.0121(16) C32 .0348(18) .0303(17) .0391(18) .0024(15) .0184(15) -.0056(14) C33 .0260(15) .0261(16) .0370(17) -.0052(14) .0152(14) -.0064(14) C34 .0325(17) .0330(17) .0375(18) -.0020(15) .0187(15) -.0049(14) C35 .0392(18) .0409(19) .0432(19) -.0096(17) .0250(16) -.0131(16) C36 .0300(17) .044(2) .053(2) -.0025(17) .0225(16) -.0156(18) C37 .0317(17) .0312(17) .053(2) .0009(15) .0162(16) -.0085(16) C38 .0282(16) .0318(17) .0401(18) -.0042(15) .0139(14) -.0031(15) N1 .0241(12) .0302(14) .0413(15) -.0004(12) .0167(12) .0018(11) N2 .0298(14) .0303(14) .0419(15) -.0009(12) .0208(12) -.0017(12) O1 .0349(12) .0372(13) .0590(15) -.0052(10) .0287(11) -.0065(11) O2 .0338(12) .0281(11) .0513(13) .0015(10) .0235(11) .0005(10) O3 .0376(12) .0332(12) .0571(14) -.0045(10) .0302(11) -.0043(11) O4 .0509(14) .0260(12) .0778(17) -.0041(11) .0424(13) -.0092(11) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 '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' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .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_publ_flag N1 C2 C3 107.9(3) no N1 C2 C1 120.6(3) no C3 C2 C1 131.4(3) no C2 C3 C4 107.2(2) no C2 C3 C8 125.0(3) no C4 C3 C8 127.8(3) no C5 C4 C3 107.0(2) no C5 C4 C14 125.8(3) no C3 C4 C14 127.2(2) no N1 C5 C4 107.4(2) no N1 C5 C6 117.7(3) no C4 C5 C6 134.8(3) no O1 C6 O2 121.9(3) no O1 C6 C5 123.6(3) no O2 C6 C5 114.5(3) no C9 C8 C13 117.9(3) no C9 C8 C3 120.6(3) no C13 C8 C3 121.4(3) no C10 C9 C8 121.2(3) no C9 C10 C11 120.0(3) no C12 C11 C10 119.5(3) no C11 C12 C13 120.7(3) no C12 C13 C8 120.6(3) no C15 C14 C19 118.4(3) no C15 C14 C4 121.4(3) no C19 C14 C4 120.2(3) no C14 C15 C16 120.9(3) no C17 C16 C15 120.0(3) no C18 C17 C16 119.6(3) no C17 C18 C19 120.7(3) no C18 C19 C14 120.4(3) no N2 C21 C22 108.3(2) no N2 C21 C20 121.2(3) no C22 C21 C20 130.4(3) no C21 C22 C23 107.0(3) no C21 C22 C27 126.1(3) no C23 C22 C27 126.9(3) no C24 C23 C22 106.9(2) no C24 C23 C33 129.0(3) no C22 C23 C33 124.0(3) no N2 C24 C23 107.4(2) no N2 C24 C25 116.4(3) no C23 C24 C25 136.1(3) no O3 C25 O4 122.1(3) no O3 C25 C24 124.1(3) no O4 C25 C24 113.8(3) no C32 C27 C28 117.8(3) no C32 C27 C22 120.5(3) no C28 C27 C22 121.6(3) no C29 C28 C27 121.1(3) no C30 C29 C28 120.0(3) no C29 C30 C31 119.9(3) no C30 C31 C32 120.2(3) no C31 C32 C27 120.9(3) no C38 C33 C34 117.9(3) no C38 C33 C23 123.5(3) no C34 C33 C23 118.6(3) no C35 C34 C33 121.2(3) no C36 C35 C34 120.2(3) no C35 C36 C37 119.2(3) no C38 C37 C36 120.9(3) no C37 C38 C33 120.5(3) no C2 N1 C5 110.6(2) no C21 N2 C24 110.4(2) no C6 O2 C7 116.1(2) no C25 O4 C26 117.2(2) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag C1 C2 1.493(4) no C2 N1 1.353(4) no C2 C3 1.396(4) no C3 C4 1.430(4) no C3 C8 1.479(4) no C4 C5 1.391(4) no C4 C14 1.483(4) no C5 N1 1.381(4) no C5 C6 1.440(4) no C6 O1 1.225(3) no C6 O2 1.339(4) no C7 O2 1.445(4) no C8 C9 1.398(4) no C8 C13 1.399(4) no C9 C10 1.379(4) no C10 C11 1.391(5) no C11 C12 1.379(5) no C12 C13 1.383(4) no C14 C15 1.384(4) no C14 C19 1.394(4) no C15 C16 1.390(4) no C16 C17 1.377(4) no C17 C18 1.375(4) no C18 C19 1.379(4) no C20 C21 1.497(4) no C21 N2 1.346(4) no C21 C22 1.398(4) no C22 C23 1.429(4) no C22 C27 1.471(4) no C23 C24 1.395(4) no C23 C33 1.486(4) no C24 N2 1.383(4) no C24 C25 1.449(4) no C25 O3 1.218(3) no C25 O4 1.339(4) no C26 O4 1.449(4) no C27 C32 1.396(4) no C27 C28 1.396(4) no C28 C29 1.389(4) no C29 C30 1.374(4) no C30 C31 1.383(5) no C31 C32 1.384(4) no C33 C38 1.388(4) no C33 C34 1.393(4) no C34 C35 1.386(4) no C35 C36 1.369(4) no C36 C37 1.383(5) no C37 C38 1.380(4) no 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_publ_flag N1 H1 O3 .88 2.05 2.875(3) 156.7 yes N2 H2 O1 .88 1.99 2.829(3) 157.9 yes