#------------------------------------------------------------------------------ #$Date: 2013-08-29 18:37:19 +0300 (Thu, 29 Aug 2013) $ #$Revision: 88064 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/47/2014748.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_2014748 loop_ _publ_author_name 'Davey, Roger J.' 'Gillon, Amy L.' 'Quayle, Michael J.' 'Rashad, Omar' _publ_section_title ; 4'-Octyloxybiphenyl-4-carbonitrile polymorph III ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o143 _journal_page_last o144 _journal_volume 61 _journal_year 2005 _chemical_formula_moiety 'C21 H25 N O' _chemical_formula_sum 'C21 H25 N O' _chemical_formula_weight 307.42 _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 'WinGX routine CIF_UPDATE' _cell_angle_alpha 90 _cell_angle_beta 94.98(3) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 73.814(15) _cell_length_b 7.0080(14) _cell_length_c 6.8710(14) _cell_measurement_reflns_used 35865 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 50 _cell_measurement_theta_min 5 _cell_volume 3540.9(13) _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_collection 'Collect (Nonius, 2000)' _computing_data_reduction 'HKL Denzo (Otwinowski & Minor 1997) and Scalepack' _computing_molecular_graphics 'program (reference)?' _computing_publication_material 'program (reference)?' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_measured_fraction_theta_full 0.990 _diffrn_measured_fraction_theta_max 0.990 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\f or \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0324 _diffrn_reflns_limit_h_max 88 _diffrn_reflns_limit_h_min -87 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_number 6626 _diffrn_reflns_theta_full 25.0 _diffrn_reflns_theta_max 25.0 _diffrn_reflns_theta_min 2.92 _exptl_absorpt_coefficient_mu 0.07 _exptl_absorpt_correction_T_max 0.996 _exptl_absorpt_correction_T_min 0.976 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SORTAV; Blessing, 1995)' _exptl_crystal_colour transparent _exptl_crystal_density_diffrn 1.153 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 1328 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.222 _refine_diff_density_min -0.234 _refine_ls_extinction_coef 0.0017(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 0.992 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 210 _refine_ls_number_reflns 3073 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.992 _refine_ls_R_factor_gt 0.0585 _refine_ls_shift/su_max 0 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0687P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.1592 _reflns_number_gt 1551 _reflns_number_total 3073 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file sq1183.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'C 2/c' _cod_original_cell_volume 3540.9(12) _cod_database_code 2014748 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 C1 0.00861(4) 0.7581(4) 0.4897(4) 0.0311(7) Uani d . 1 . . C C2 0.02773(4) 0.7545(4) 0.4531(4) 0.0299(7) Uani d . 1 . . C C3 0.03421(3) 0.5998(4) 0.3505(4) 0.0311(7) Uani d . 1 . . C H3 0.0265 0.4996 0.3112 0.037 Uiso calc R 1 . . H C4 0.05217(3) 0.5972(4) 0.3080(4) 0.0299(7) Uani d . 1 . . C H4 0.0564 0.4947 0.239 0.036 Uiso calc R 1 . . H C5 0.06405(3) 0.7453(4) 0.3664(4) 0.0265(7) Uani d . 1 . . C C6 0.05735(4) 0.8966(4) 0.4713(4) 0.0331(7) Uani d . 1 . . C H6 0.0651 0.9958 0.5132 0.04 Uiso calc R 1 . . H C7 0.03931(4) 0.9019(4) 0.5144(4) 0.0348(8) Uani d . 1 . . C H7 0.035 1.0039 0.5839 0.042 Uiso calc R 1 . . H C8 0.08311(4) 0.7460(4) 0.3120(4) 0.0281(7) Uani d . 1 . . C C9 0.08753(4) 0.6594(4) 0.1392(4) 0.0319(7) Uani d . 1 . . C H9 0.0784 0.5975 0.0608 0.038 Uiso calc R 1 . . H C10 0.10516(4) 0.6629(4) 0.0805(4) 0.0325(7) Uani d . 1 . . C H10 0.1078 0.6031 -0.0346 0.039 Uiso calc R 1 . . H C11 0.11866(4) 0.7559(4) 0.1949(4) 0.0285(7) Uani d . 1 . . C C12 0.11484(4) 0.8367(4) 0.3713(4) 0.0312(7) Uani d . 1 . . C H12 0.1241 0.8938 0.4517 0.037 Uiso calc R 1 . . H C13 0.09727(3) 0.8324(4) 0.4276(4) 0.0299(7) Uani d . 1 . . C H13 0.0949 0.8885 0.5453 0.036 Uiso calc R 1 . . H C14 0.14020(3) 0.7111(4) -0.0449(4) 0.0337(8) Uani d . 1 . . C H14A 0.1312 0.7604 -0.1437 0.04 Uiso calc R 1 . . H H14B 0.1399 0.5728 -0.0504 0.04 Uiso calc R 1 . . H C15 0.15880(4) 0.7827(4) -0.0802(4) 0.0339(8) Uani d . 1 . . C H15A 0.1675 0.7388 0.0244 0.041 Uiso calc R 1 . . H H15B 0.1588 0.9211 -0.0776 0.041 Uiso calc R 1 . . H C16 0.16482(4) 0.7153(4) -0.2747(4) 0.0342(8) Uani d . 1 . . C H16A 0.1561 0.76 -0.379 0.041 Uiso calc R 1 . . H H16B 0.1647 0.5769 -0.2774 0.041 Uiso calc R 1 . . H C17 0.18371(4) 0.7850(4) -0.3129(4) 0.0334(8) Uani d . 1 . . C H17A 0.1923 0.7417 -0.2076 0.04 Uiso calc R 1 . . H H17B 0.1838 0.9234 -0.3118 0.04 Uiso calc R 1 . . H C18 0.18993(4) 0.7156(4) -0.5066(4) 0.0345(8) Uani d . 1 . . C H18A 0.1895 0.5773 -0.5088 0.041 Uiso calc R 1 . . H H18B 0.1814 0.7616 -0.6117 0.041 Uiso calc R 1 . . H C19 0.20894(4) 0.7787(4) -0.5461(4) 0.0366(8) Uani d . 1 . . C H19A 0.2093 0.917 -0.5503 0.044 Uiso calc R 1 . . H H19B 0.2174 0.7374 -0.4387 0.044 Uiso calc R 1 . . H C20 0.21507(4) 0.7014(4) -0.7342(4) 0.0508(9) Uani d . 1 . . C H20A 0.2065 0.7425 -0.8411 0.061 Uiso calc R 1 . . H H20B 0.2147 0.5631 -0.7295 0.061 Uiso calc R 1 . . H C21 0.23403(4) 0.7624(5) -0.7774(5) 0.0660(11) Uani d . 1 . . C H21A 0.2346 0.8991 -0.7825 0.099 Uiso calc R 1 . . H H21B 0.2367 0.7105 -0.9009 0.099 Uiso calc R 1 . . H H21C 0.2427 0.7162 -0.6764 0.099 Uiso calc R 1 . . H N1 -0.00632(4) 0.7582(3) 0.5162(3) 0.0445(7) Uani d . 1 . . N O1 0.13627(2) 0.7761(2) 0.1462(3) 0.0354(5) 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 0.0336(19) 0.035(2) 0.0236(16) -0.0013(14) -0.0014(14) 0.0000(14) C2 0.0251(17) 0.0366(18) 0.0278(16) 0.0015(15) 0.0006(13) 0.0020(15) C3 0.0284(17) 0.0324(19) 0.0318(17) -0.0048(14) -0.0009(14) 0.0004(14) C4 0.0300(18) 0.0305(18) 0.0292(17) 0.0014(14) 0.0033(13) 0.0000(14) C5 0.0251(17) 0.0277(17) 0.0261(15) 0.0001(14) -0.0012(13) 0.0031(14) C6 0.0314(18) 0.0304(19) 0.0375(18) -0.0020(14) 0.0023(14) -0.0028(15) C7 0.0341(18) 0.0387(19) 0.0319(17) 0.0035(15) 0.0046(14) -0.0057(15) C8 0.0287(17) 0.0285(17) 0.0270(15) 0.0023(14) 0.0017(13) 0.0020(14) C9 0.0321(18) 0.0280(18) 0.0352(17) 0.0003(13) 0.0008(14) -0.0023(14) C10 0.0316(18) 0.0319(18) 0.0342(17) 0.0021(14) 0.0050(14) -0.0048(14) C11 0.0229(17) 0.0278(18) 0.0348(17) 0.0014(13) 0.0023(13) 0.0026(14) C12 0.0302(18) 0.0325(18) 0.0300(16) -0.0014(14) -0.0022(13) -0.0010(14) C13 0.0292(18) 0.0319(18) 0.0278(16) 0.0023(14) -0.0024(13) 0.0001(14) C14 0.0315(18) 0.036(2) 0.0336(17) 0.0015(14) 0.0047(14) -0.0049(15) C15 0.0299(18) 0.0338(19) 0.0384(17) 0.0002(14) 0.0057(14) -0.0023(15) C16 0.0314(18) 0.0366(19) 0.0345(17) -0.0020(14) 0.0023(14) 0.0007(15) C17 0.0306(18) 0.0366(19) 0.0328(16) 0.0006(14) 0.0025(13) 0.0005(14) C18 0.0343(18) 0.039(2) 0.0301(16) 0.0013(14) 0.0021(14) -0.0004(14) C19 0.0328(18) 0.039(2) 0.0385(18) 0.0007(14) 0.0029(15) -0.0002(15) C20 0.049(2) 0.057(2) 0.049(2) -0.0041(17) 0.0161(17) -0.0034(18) C21 0.045(2) 0.088(3) 0.068(3) -0.001(2) 0.021(2) 0.001(2) N1 0.0435(18) 0.0455(18) 0.0450(17) -0.0034(14) 0.0063(14) -0.0015(13) O1 0.0271(12) 0.0448(13) 0.0348(11) -0.0015(9) 0.0056(9) -0.0046(10) 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 C1 N1 . 1.132(3) y C1 C2 . 1.455(4) y C2 C7 . 1.383(3) n C2 C3 . 1.400(3) n C3 C4 . 1.382(3) n C3 H3 . 0.93 ? C4 C5 . 1.395(3) n C4 H4 . 0.93 ? C5 C6 . 1.397(3) n C5 C8 . 1.487(3) y C6 C7 . 1.389(3) n C6 H6 . 0.93 ? C7 H7 . 0.93 ? C8 C13 . 1.395(4) n C8 C9 . 1.397(3) n C9 C10 . 1.395(3) n C9 H9 . 0.93 ? C10 C11 . 1.378(4) n C10 H10 . 0.93 ? C11 O1 . 1.377(3) y C11 C12 . 1.389(3) n C12 C13 . 1.385(3) n C12 H12 . 0.93 ? C13 H13 . 0.93 ? C14 O1 . 1.443(3) y C14 C15 . 1.502(3) n C14 H14A . 0.97 ? C14 H14B . 0.97 ? C15 C16 . 1.520(3) n C15 H15A . 0.97 ? C15 H15B . 0.97 ? C16 C17 . 1.522(3) n C16 H16A . 0.97 ? C16 H16B . 0.97 ? C17 C18 . 1.525(3) n C17 H17A . 0.97 ? C17 H17B . 0.97 ? C18 C19 . 1.518(3) n C18 H18A . 0.97 ? C18 H18B . 0.97 ? C19 C20 . 1.506(4) n C19 H19A . 0.97 ? C19 H19B . 0.97 ? C20 C21 . 1.518(4) n C20 H20A . 0.97 ? C20 H20B . 0.97 ? C21 H21A . 0.96 ? C21 H21B . 0.96 ? C21 H21C . 0.96 ? 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 0 '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 0.006 '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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag N1 C1 C2 . . 178.8(3) y C7 C2 C3 . . 120.1(2) ? C7 C2 C1 . . 121.2(3) ? C3 C2 C1 . . 118.7(3) ? C4 C3 C2 . . 119.5(3) ? C4 C3 H3 . . 120.2 ? C2 C3 H3 . . 120.2 ? C3 C4 C5 . . 121.3(3) ? C3 C4 H4 . . 119.3 ? C5 C4 H4 . . 119.3 ? C4 C5 C6 . . 118.2(2) ? C4 C5 C8 . . 121.0(2) ? C6 C5 C8 . . 120.8(2) ? C7 C6 C5 . . 121.2(3) ? C7 C6 H6 . . 119.4 ? C5 C6 H6 . . 119.4 ? C2 C7 C6 . . 119.6(3) ? C2 C7 H7 . . 120.2 ? C6 C7 H7 . . 120.2 ? C13 C8 C9 . . 117.0(2) ? C13 C8 C5 . . 122.5(2) ? C9 C8 C5 . . 120.5(3) ? C10 C9 C8 . . 122.0(3) ? C10 C9 H9 . . 119 ? C8 C9 H9 . . 119 ? C11 C10 C9 . . 119.3(3) ? C11 C10 H10 . . 120.3 ? C9 C10 H10 . . 120.3 ? O1 C11 C10 . . 124.1(2) y O1 C11 C12 . . 116.0(2) y C10 C11 C12 . . 119.9(2) ? C13 C12 C11 . . 120.1(3) ? C13 C12 H12 . . 120 ? C11 C12 H12 . . 120 ? C12 C13 C8 . . 121.6(3) ? C12 C13 H13 . . 119.2 ? C8 C13 H13 . . 119.2 ? O1 C14 C15 . . 107.5(2) y O1 C14 H14A . . 110.2 ? C15 C14 H14A . . 110.2 ? O1 C14 H14B . . 110.2 ? C15 C14 H14B . . 110.2 ? H14A C14 H14B . . 108.5 ? C14 C15 C16 . . 112.3(2) ? C14 C15 H15A . . 109.2 ? C16 C15 H15A . . 109.2 ? C14 C15 H15B . . 109.2 ? C16 C15 H15B . . 109.2 ? H15A C15 H15B . . 107.9 ? C15 C16 C17 . . 113.2(2) ? C15 C16 H16A . . 108.9 ? C17 C16 H16A . . 108.9 ? C15 C16 H16B . . 108.9 ? C17 C16 H16B . . 108.9 ? H16A C16 H16B . . 107.8 ? C16 C17 C18 . . 113.5(2) ? C16 C17 H17A . . 108.9 ? C18 C17 H17A . . 108.9 ? C16 C17 H17B . . 108.9 ? C18 C17 H17B . . 108.9 ? H17A C17 H17B . . 107.7 ? C19 C18 C17 . . 114.6(2) ? C19 C18 H18A . . 108.6 ? C17 C18 H18A . . 108.6 ? C19 C18 H18B . . 108.6 ? C17 C18 H18B . . 108.6 ? H18A C18 H18B . . 107.6 ? C20 C19 C18 . . 113.5(2) ? C20 C19 H19A . . 108.9 ? C18 C19 H19A . . 108.9 ? C20 C19 H19B . . 108.9 ? C18 C19 H19B . . 108.9 ? H19A C19 H19B . . 107.7 ? C19 C20 C21 . . 114.7(3) ? C19 C20 H20A . . 108.6 ? C21 C20 H20A . . 108.6 ? C19 C20 H20B . . 108.6 ? C21 C20 H20B . . 108.6 ? H20A C20 H20B . . 107.6 ? C20 C21 H21A . . 109.5 ? C20 C21 H21B . . 109.5 ? H21A C21 H21B . . 109.5 ? C20 C21 H21C . . 109.5 ? H21A C21 H21C . . 109.5 ? H21B C21 H21C . . 109.5 ? C1 N1 H3 . 5_566 131 ? C1 N1 H7 . 5_576 134.7 ? H3 N1 H7 5_566 5_576 94.2 ? C1 N1 C7 . 5_576 133.8(2) ? H3 N1 C7 5_566 5_576 94.4 ? C1 N1 C3 . 5_566 131.3(2) ? H7 N1 C3 5_576 5_566 92.5 ? C7 N1 C3 5_576 5_566 94.92(9) ? C11 O1 C14 . . 117.2(2) y loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag C7 H7 N1 5_576 5_576 0.93 2.74 3.400(4) 129 y C3 H3 N1 5_566 5_566 0.93 2.68 3.420(3) 137 y _cod_database_fobs_code 2014748