#------------------------------------------------------------------------------ #$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2015385.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_2015385 loop_ _publ_author_name 'Bhatt, Prashant M.' 'Desiraju, Gautam R.' _publ_section_title ; Form I of desloratadine, a tricyclic antihistamine ; _journal_coeditor_code SK3005 _journal_issue 6 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o362 _journal_page_last o363 _journal_volume 62 _journal_year 2006 _chemical_formula_iupac 'C19 H19 Cl N2' _chemical_formula_moiety 'C19 H19 Cl N2' _chemical_formula_sum 'C19 H19 Cl N2' _chemical_formula_weight 310.81 _chemical_melting_point 158 _chemical_name_common Desloratadine _chemical_name_systematic ; 8-chloro-11-(4-piperidinylidene)-6,11-dihydro-5H- benzo[4,5]cyclohepta[2,1-b]pyridine ; _space_group_IT_number 4 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 107.365(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 6.9336(12) _cell_length_b 11.998(2) _cell_length_c 9.4691(16) _cell_measurement_reflns_used 2389 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 25.89 _cell_measurement_theta_min 2.25 _cell_volume 751.8(2) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 1999)' _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 100(2) _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method '\f and \w' _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 0.0233 _diffrn_reflns_av_sigmaI/netI 0.0400 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_number 4424 _diffrn_reflns_theta_full 26.04 _diffrn_reflns_theta_max 26.04 _diffrn_reflns_theta_min 2.25 _exptl_absorpt_coefficient_mu 0.252 _exptl_absorpt_correction_type none _exptl_crystal_colour Colourless _exptl_crystal_density_diffrn 1.373 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Plate _exptl_crystal_F_000 328 _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.11 _refine_diff_density_max 0.211 _refine_diff_density_min -0.211 _refine_ls_abs_structure_details 'Flack (1983), with 1106 Friedel pairs' _refine_ls_abs_structure_Flack 0.04(5) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 208 _refine_ls_number_reflns 2661 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.047 _refine_ls_R_factor_all 0.0334 _refine_ls_R_factor_gt 0.0320 _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^)+(0.035P)^2^+0.1332P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0744 _refine_ls_wR_factor_ref 0.0754 _reflns_number_gt 2550 _reflns_number_total 2661 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file sk3005.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21' _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. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2015385 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' loop_ _atom_site_type_symbol _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 Cl Cl1 1.30938(7) -0.26310(4) 0.25228(5) 0.02176(14) Uani d . 1 N N1 1.0382(3) 0.35354(15) 0.23443(18) 0.0183(4) Uani d . 1 N N2 0.3026(3) 0.21123(17) -0.0094(2) 0.0217(5) Uani d . 1 C C1 1.0218(3) 0.27342(18) 0.3292(2) 0.0151(4) Uani d . 1 C C2 1.1542(3) 0.44150(19) 0.2915(2) 0.0206(5) Uani d . 1 C C3 1.2556(3) 0.45345(19) 0.4397(2) 0.0209(5) Uani d . 1 C C4 1.2392(3) 0.37022(18) 0.5353(2) 0.0176(5) Uani d . 1 C C5 1.1214(3) 0.27722(18) 0.4815(2) 0.0162(4) Uani d . 1 C C6 1.0939(3) 0.18222(18) 0.5774(2) 0.0178(4) Uani d . 1 C C7 1.2008(3) 0.07625(19) 0.5542(2) 0.0169(4) Uani d . 1 C C8 1.1423(3) 0.02314(18) 0.4010(2) 0.0143(4) Uani d . 1 C C9 1.2325(3) -0.07951(18) 0.3917(2) 0.0151(4) Uani d . 1 C C10 1.1965(3) -0.13316(19) 0.2576(2) 0.0171(5) Uani d . 1 C C11 1.0735(3) -0.08755(19) 0.1277(2) 0.0170(4) Uani d . 1 C C12 0.9822(3) 0.01259(19) 0.1379(2) 0.0167(4) Uani d . 1 C C13 1.0077(3) 0.06879(18) 0.2721(2) 0.0140(4) Uani d . 1 C C14 0.8931(3) 0.17469(18) 0.2692(2) 0.0146(4) Uani d . 1 C C15 0.6896(3) 0.17988(18) 0.2193(2) 0.0154(4) Uani d . 1 C C16 0.5509(3) 0.0826(2) 0.1640(2) 0.0184(4) Uani d . 1 C C17 0.4130(3) 0.10602(19) 0.0057(2) 0.0194(5) Uani d . 1 C C18 0.4355(3) 0.3050(2) 0.0511(2) 0.0214(5) Uani d . 1 C C19 0.5733(3) 0.28702(19) 0.2100(2) 0.0187(5) Uani d . 1 H H1 0.214(3) 0.206(2) 0.034(2) 0.018(6) Uiso d . 1 H H2 1.1673 0.4990 0.2260 0.025 Uiso calc R 1 H H3 1.3352 0.5178 0.4751 0.025 Uiso calc R 1 H H4 1.3084 0.3764 0.6380 0.021 Uiso calc R 1 H H6A 0.9477 0.1666 0.5559 0.021 Uiso calc R 1 H H6B 1.1464 0.2048 0.6825 0.021 Uiso calc R 1 H H7A 1.1802 0.0197 0.6244 0.020 Uiso calc R 1 H H7B 1.3474 0.0924 0.5827 0.020 Uiso calc R 1 H H9 1.3195 -0.1127 0.4785 0.018 Uiso calc R 1 H H11 1.054(3) -0.1273(19) 0.039(2) 0.015(6) Uiso d . 1 H H12 0.8977 0.0453 0.0497 0.020 Uiso calc R 1 H H16A 0.4670 0.0697 0.2307 0.022 Uiso calc R 1 H H16B 0.6318 0.0146 0.1640 0.022 Uiso calc R 1 H H17A 0.4968 0.1067 -0.0626 0.023 Uiso calc R 1 H H17B 0.3145 0.0443 -0.0250 0.023 Uiso calc R 1 H H18A 0.3515 0.3720 0.0494 0.026 Uiso calc R 1 H H18B 0.5211 0.3198 -0.0138 0.026 Uiso calc R 1 H H19A 0.6686 0.3502 0.2396 0.022 Uiso calc R 1 H H19B 0.4904 0.2840 0.2789 0.022 Uiso calc R 1 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 0.0233(2) 0.0149(3) 0.0290(3) 0.0025(2) 0.0108(2) -0.0017(2) N1 0.0201(8) 0.0158(10) 0.0183(8) 0.0005(8) 0.0047(7) 0.0004(8) N2 0.0170(8) 0.0229(13) 0.0233(9) -0.0007(8) 0.0033(7) -0.0006(8) C8 0.0132(9) 0.0145(11) 0.0162(10) -0.0022(9) 0.0062(8) -0.0003(8) C9 0.0127(9) 0.0151(12) 0.0171(10) 0.0004(9) 0.0040(7) 0.0033(8) C10 0.0133(9) 0.0113(12) 0.0293(11) -0.0021(9) 0.0103(8) 0.0005(9) C14 0.0203(10) 0.0127(12) 0.0111(9) 0.0005(9) 0.0049(8) 0.0005(8) C18 0.0175(10) 0.0218(14) 0.0231(11) 0.0045(10) 0.0034(9) 0.0034(9) C5 0.0120(9) 0.0172(12) 0.0195(10) 0.0038(9) 0.0051(8) -0.0024(9) C4 0.0140(9) 0.0163(12) 0.0211(10) 0.0048(9) 0.0028(8) -0.0056(9) C1 0.0114(9) 0.0162(11) 0.0172(9) 0.0033(8) 0.0038(7) -0.0018(8) C13 0.0126(9) 0.0136(11) 0.0163(9) -0.0036(9) 0.0050(7) -0.0002(8) C15 0.0180(10) 0.0153(12) 0.0120(9) -0.0005(9) 0.0029(8) -0.0010(8) C7 0.0177(9) 0.0168(12) 0.0155(9) 0.0018(9) 0.0039(8) 0.0021(8) C11 0.0165(10) 0.0155(12) 0.0180(10) -0.0042(9) 0.0037(8) -0.0029(9) C6 0.0182(10) 0.0188(12) 0.0165(10) 0.0014(9) 0.0057(8) -0.0013(8) C2 0.0195(10) 0.0178(12) 0.0264(11) -0.0003(10) 0.0097(9) 0.0021(9) C17 0.0171(10) 0.0216(13) 0.0171(10) -0.0008(10) 0.0017(8) 0.0003(9) C12 0.0133(10) 0.0173(12) 0.0173(10) -0.0027(9) 0.0012(8) 0.0013(8) C3 0.0162(10) 0.0152(13) 0.0314(12) -0.0003(10) 0.0071(9) -0.0053(9) C19 0.0153(10) 0.0187(12) 0.0212(10) -0.0001(9) 0.0042(8) -0.0017(9) C16 0.0165(9) 0.0186(12) 0.0203(10) -0.0016(9) 0.0059(8) 0.0006(9) 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' 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 C15 C14 C1 122.80(18) C15 C14 C13 122.69(18) C1 C14 C13 114.49(16) C18 N2 C17 112.13(16) C18 N2 H1 109.8(16) C17 N2 H1 109.0(17) C9 C10 C11 121.9(2) C9 C10 Cl1 118.84(16) C11 C10 Cl1 119.25(17) C10 C9 C8 120.57(18) C10 C9 H9 119.7 C8 C9 H9 119.7 C9 C8 C13 118.86(18) C9 C8 C7 115.59(17) C13 C8 C7 125.55(18) C2 N1 C1 117.04(17) N2 C18 C19 114.31(18) N2 C18 H18A 108.7 C19 C18 H18A 108.7 N2 C18 H18B 108.7 C19 C18 H18B 108.7 H18A C18 H18B 107.6 C4 C5 C1 117.4(2) C4 C5 C6 123.66(18) C1 C5 C6 118.96(18) C3 C4 C5 119.84(19) C3 C4 H4 120.1 C5 C4 H4 120.1 N1 C1 C5 123.38(19) N1 C1 C14 118.35(17) C5 C1 C14 118.26(18) C12 C13 C8 118.04(19) C12 C13 C14 118.01(17) C8 C13 C14 123.95(17) C14 C15 C16 125.43(19) C14 C15 C19 123.06(19) C16 C15 C19 111.50(16) C6 C7 C8 118.99(16) C6 C7 H7A 107.6 C8 C7 H7A 107.6 C6 C7 H7B 107.6 C8 C7 H7B 107.6 H7A C7 H7B 107.0 C12 C11 C10 117.23(19) C12 C11 H11 124.2(13) C10 C11 H11 118.6(13) C5 C6 C7 112.99(16) C5 C6 H6A 109.0 C7 C6 H6A 109.0 C5 C6 H6B 109.0 C7 C6 H6B 109.0 H6A C6 H6B 107.8 N1 C2 C3 123.8(2) N1 C2 H2 118.1 C3 C2 H2 118.1 N2 C17 C16 113.96(17) N2 C17 H17A 108.8 C16 C17 H17A 108.8 N2 C17 H17B 108.8 C16 C17 H17B 108.8 H17A C17 H17B 107.7 C11 C12 C13 123.22(19) C11 C12 H12 118.4 C13 C12 H12 118.4 C4 C3 C2 118.6(2) C4 C3 H3 120.7 C2 C3 H3 120.7 C15 C19 C18 109.99(17) C15 C19 H19A 109.7 C18 C19 H19A 109.7 C15 C19 H19B 109.7 C18 C19 H19B 109.7 H19A C19 H19B 108.2 C15 C16 C17 110.08(17) C15 C16 H16A 109.6 C17 C16 H16A 109.6 C15 C16 H16B 109.6 C17 C16 H16B 109.6 H16A C16 H16B 108.2 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Cl1 C10 1.752(2) C14 C15 1.349(3) C14 C1 1.490(3) C14 C13 1.494(3) N2 C18 1.458(3) N2 C17 1.461(3) N2 H1 0.84(2) C10 C9 1.378(3) C10 C11 1.384(3) C9 C8 1.396(3) C9 H9 0.9500 C8 C13 1.407(3) C8 C7 1.524(3) N1 C2 1.339(3) N1 C1 1.343(3) C18 C19 1.538(3) C18 H18A 0.9900 C18 H18B 0.9900 C5 C4 1.387(3) C5 C1 1.401(3) C5 C6 1.505(3) C4 C3 1.375(3) C4 H4 0.9500 C13 C12 1.403(3) C15 C16 1.503(3) C15 C19 1.506(3) C7 C6 1.521(3) C7 H7A 0.9900 C7 H7B 0.9900 C11 C12 1.375(3) C11 H11 0.94(2) C6 H6A 0.99 C6 H6B 0.99 C2 C3 1.376(3) C2 H2 0.95 C17 C16 1.545(3) C17 H17A 0.99 C17 H17B 0.99 C12 H12 0.95 C3 H3 0.9500 C19 H19A 0.99 C19 H19B 0.99 C16 H16A 0.99 C16 H16B 0.99 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 C11 H11 N1 2_745 0.940(18) 2.485(18) 3.357(3) 154.4(18)