#------------------------------------------------------------------------------ #$Date: 2012-02-26 23:34:47 +0200 (Sun, 26 Feb 2012) $ #$Revision: 35909 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/20/69/7206989.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7206989 loop_ _publ_author_name 'Puigjaner, Cristina' 'Barbas, Rafael' 'Portell, Anna' 'Valverde, Ismael' 'Vila, Xavier' 'Alcob\'e, Xavier' 'Font-Bardia, Merc\`e' 'Prohens, Rafel' _publ_section_title ; A cocrystal is the key intermediates for the production of a new polymorph of Vorinostat ; _journal_issue 2 _journal_name_full CrystEngComm _journal_page_first 362 _journal_volume 14 _journal_year 2012 _chemical_formula_moiety 'C14 H20 N2 O3' _chemical_formula_sum 'C14 H20 N2 O3' _chemical_formula_weight 264.32 _chemical_name_systematic ; ? ; _space_group_IT_number 5 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'C 2y' _symmetry_space_group_name_H-M 'C 1 2 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 104.15(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 15.027(11) _cell_length_b 5.096(3) _cell_length_c 18.258(7) _cell_measurement_reflns_used 1027 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 31 _cell_measurement_theta_min 3 _cell_volume 1355.7(14) _computing_cell_refinement AUTOMAR _computing_data_collection MARXDS _computing_data_reduction MARSCALE _computing_molecular_graphics 'ORTEP (Brueggermann and Smith, 1990)' _computing_publication_material 'PLATON (Spek, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.975 _diffrn_measured_fraction_theta_max 0.750 _diffrn_measurement_device_type 'MAR345 with image plate detector' _diffrn_measurement_method 'phi scan' _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 0.0312 _diffrn_reflns_av_sigmaI/netI 0.0325 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 5776 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 32.21 _diffrn_reflns_theta_min 2.30 _diffrn_standards_number none _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.295 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 568 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.06 _refine_diff_density_max 0.192 _refine_diff_density_min -0.289 _refine_diff_density_rms 0.046 _refine_ls_extinction_coef 0.015(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.105 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 174 _refine_ls_number_reflns 3257 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.105 _refine_ls_R_factor_all 0.0588 _refine_ls_R_factor_gt 0.0519 _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^)+(0.0979P)^2^+0.1528P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1541 _refine_ls_wR_factor_ref 0.1593 _reflns_number_gt 2807 _reflns_number_total 3257 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file c1ce05799e.txt _[local]_cod_data_source_block anom16a _[local]_cod_cif_authors_sg_H-M C2 _cod_database_code 7206989 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags O1 O 0.63410(13) 0.1173(3) 0.56466(10) 0.0505(4) Uani 1 1 d . O2 O 0.64414(13) -0.1767(4) 0.04461(10) 0.0544(5) Uani 1 1 d . O3 O 0.67880(14) 0.2290(4) -0.03760(10) 0.0581(5) Uani 1 1 d . H3 H 0.7263 0.1427 -0.0275 0.087 Uiso 1 1 calc R N1 N 0.63137(13) -0.3093(4) 0.59959(10) 0.0420(4) Uani 1 1 d . H1 H 0.6282 -0.4674 0.5827 0.050 Uiso 1 1 calc R N2 N 0.64623(14) 0.2569(4) 0.02681(10) 0.0436(4) Uani 1 1 d . H2 H 0.6390 0.4107 0.0438 0.052 Uiso 1 1 calc R C1 C 0.68217(15) -0.0814(5) 0.72187(12) 0.0437(5) Uani 1 1 d . H1A H 0.7127 0.0439 0.7001 0.052 Uiso 1 1 calc R C2 C 0.68553(15) -0.0697(4) 0.79791(12) 0.0436(5) Uani 1 1 d . H2A H 0.7182 0.0642 0.8272 0.052 Uiso 1 1 calc R C3 C 0.64052(16) -0.2561(5) 0.83103(13) 0.0451(5) Uani 1 1 d . H3A H 0.6422 -0.2454 0.8822 0.054 Uiso 1 1 calc R C4 C 0.59331(16) -0.4569(5) 0.78799(13) 0.0475(5) Uani 1 1 d . H4 H 0.5639 -0.5835 0.8103 0.057 Uiso 1 1 calc R C5 C 0.58957(15) -0.4708(5) 0.71083(12) 0.0442(5) Uani 1 1 d . H5 H 0.5580 -0.6067 0.6816 0.053 Uiso 1 1 calc R C6 C 0.63355(14) -0.2791(4) 0.67799(11) 0.0379(4) Uani 1 1 d . C7 C 0.63371(15) -0.1160(4) 0.54917(11) 0.0394(4) Uani 1 1 d . C8 C 0.64061(17) -0.2157(5) 0.47260(12) 0.0463(5) Uani 1 1 d . H8A H 0.7041 -0.2611 0.4756 0.056 Uiso 1 1 calc R H8B H 0.6047 -0.3754 0.4614 0.056 Uiso 1 1 calc R C9 C 0.60875(16) -0.0271(5) 0.40782(12) 0.0430(5) Uani 1 1 d . H9A H 0.6371 0.1427 0.4216 0.052 Uiso 1 1 calc R H9B H 0.5428 -0.0050 0.3983 0.052 Uiso 1 1 calc R C10 C 0.63282(15) -0.1236(5) 0.33595(12) 0.0409(4) Uani 1 1 d . H10A H 0.6991 -0.1254 0.3443 0.049 Uiso 1 1 calc R H10B H 0.6115 -0.3030 0.3265 0.049 Uiso 1 1 calc R C11 C 0.59270(14) 0.0387(5) 0.26602(12) 0.0396(4) Uani 1 1 d . H11A H 0.6095 0.2211 0.2764 0.047 Uiso 1 1 calc R H11B H 0.5263 0.0271 0.2543 0.047 Uiso 1 1 calc R C12 C 0.62598(16) -0.0518(5) 0.19776(12) 0.0429(5) Uani 1 1 d . H12A H 0.6119 -0.2366 0.1890 0.052 Uiso 1 1 calc R H12B H 0.6921 -0.0317 0.2085 0.052 Uiso 1 1 calc R C13 C 0.58135(17) 0.1044(5) 0.12556(12) 0.0452(5) Uani 1 1 d . H13A H 0.5167 0.0597 0.1096 0.054 Uiso 1 1 calc R H13B H 0.5859 0.2906 0.1369 0.054 Uiso 1 1 calc R C14 C 0.62649(15) 0.0479(5) 0.06168(12) 0.0423(4) Uani 1 1 d . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0682(11) 0.0385(10) 0.0470(8) 0.0010(6) 0.0180(8) 0.0003(7) O2 0.0707(12) 0.0424(10) 0.0539(10) 0.0004(7) 0.0226(8) 0.0019(7) O3 0.0728(12) 0.0558(11) 0.0504(9) -0.0008(8) 0.0242(8) -0.0002(9) N1 0.0539(10) 0.0322(10) 0.0411(9) -0.0023(6) 0.0137(7) -0.0007(7) N2 0.0550(11) 0.0371(10) 0.0408(8) -0.0004(7) 0.0156(7) 0.0002(7) C1 0.0493(11) 0.0389(12) 0.0437(10) 0.0012(8) 0.0128(9) -0.0042(9) C2 0.0506(11) 0.0406(12) 0.0389(10) -0.0006(8) 0.0093(8) -0.0026(9) C3 0.0518(12) 0.0419(12) 0.0414(10) 0.0009(9) 0.0110(8) 0.0014(9) C4 0.0525(12) 0.0445(13) 0.0470(11) 0.0033(9) 0.0151(9) -0.0042(10) C5 0.0529(11) 0.0364(12) 0.0441(10) -0.0013(8) 0.0134(9) -0.0049(9) C6 0.0425(10) 0.0348(11) 0.0369(9) 0.0022(7) 0.0109(7) 0.0007(8) C7 0.0465(10) 0.0340(12) 0.0382(9) -0.0019(8) 0.0113(8) 0.0029(8) C8 0.0548(13) 0.0433(14) 0.0422(10) -0.0017(8) 0.0147(9) 0.0038(9) C9 0.0467(11) 0.0423(12) 0.0411(10) -0.0007(8) 0.0130(8) 0.0035(8) C10 0.0457(10) 0.0376(11) 0.0398(9) -0.0001(8) 0.0114(8) 0.0004(8) C11 0.0447(10) 0.0353(11) 0.0403(9) -0.0006(7) 0.0134(8) 0.0018(8) C12 0.0489(11) 0.0390(12) 0.0422(10) -0.0003(8) 0.0138(8) 0.0021(8) C13 0.0545(12) 0.0392(12) 0.0443(10) 0.0028(8) 0.0169(9) 0.0035(8) C14 0.0523(11) 0.0366(12) 0.0394(9) 0.0000(8) 0.0139(8) -0.0011(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' O O 0.0106 0.0060 '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 N2 O3 H3 109.5 C7 N1 C6 127.08(19) C7 N1 H1 116.5 C6 N1 H1 116.5 C14 N2 O3 119.79(19) C14 N2 H2 120.1 O3 N2 H2 120.1 C2 C1 C6 120.0(2) C2 C1 H1A 120.0 C6 C1 H1A 120.0 C1 C2 C3 120.5(2) C1 C2 H2A 119.8 C3 C2 H2A 119.8 C4 C3 C2 119.9(2) C4 C3 H3A 120.1 C2 C3 H3A 120.1 C3 C4 C5 120.1(2) C3 C4 H4 120.0 C5 C4 H4 120.0 C6 C5 C4 119.4(2) C6 C5 H5 120.3 C4 C5 H5 120.3 C1 C6 C5 120.07(19) C1 C6 N1 122.58(19) C5 C6 N1 117.19(19) O1 C7 N1 123.4(2) O1 C7 C8 122.9(2) N1 C7 C8 113.7(2) C9 C8 C7 115.5(2) C9 C8 H8A 108.4 C7 C8 H8A 108.4 C9 C8 H8B 108.4 C7 C8 H8B 108.4 H8A C8 H8B 107.5 C8 C9 C10 111.87(19) C8 C9 H9A 109.2 C10 C9 H9A 109.2 C8 C9 H9B 109.2 C10 C9 H9B 109.2 H9A C9 H9B 107.9 C11 C10 C9 114.78(19) C11 C10 H10A 108.6 C9 C10 H10A 108.6 C11 C10 H10B 108.6 C9 C10 H10B 108.6 H10A C10 H10B 107.5 C10 C11 C12 112.40(19) C10 C11 H11A 109.1 C12 C11 H11A 109.1 C10 C11 H11B 109.1 C12 C11 H11B 109.1 H11A C11 H11B 107.9 C11 C12 C13 112.41(19) C11 C12 H12A 109.1 C13 C12 H12A 109.1 C11 C12 H12B 109.1 C13 C12 H12B 109.1 H12A C12 H12B 107.9 C14 C13 C12 112.1(2) C14 C13 H13A 109.2 C12 C13 H13A 109.2 C14 C13 H13B 109.2 C12 C13 H13B 109.2 H13A C13 H13B 107.9 O2 C14 N2 122.9(2) O2 C14 C13 122.4(2) N2 C14 C13 114.6(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C7 1.222(3) O2 C14 1.232(3) O3 N2 1.387(2) O3 H3 0.8200 N1 C7 1.355(3) N1 C6 1.432(3) N1 H1 0.8600 N2 C14 1.312(3) N2 H2 0.8600 C1 C2 1.378(3) C1 C6 1.380(3) C1 H1A 0.9300 C2 C3 1.388(3) C2 H2A 0.9300 C3 C4 1.377(4) C3 H3A 0.9300 C4 C5 1.398(3) C4 H4 0.9300 C5 C6 1.394(3) C5 H5 0.9300 C7 C8 1.515(3) C8 C9 1.508(3) C8 H8A 0.9700 C8 H8B 0.9700 C9 C10 1.526(3) C9 H9A 0.9700 C9 H9B 0.9700 C10 C11 1.517(3) C10 H10A 0.9700 C10 H10B 0.9700 C11 C12 1.523(3) C11 H11A 0.9700 C11 H11B 0.9700 C12 C13 1.545(3) C12 H12A 0.9700 C12 H12B 0.9700 C13 C14 1.513(3) C13 H13A 0.9700 C13 H13B 0.9700