#------------------------------------------------------------------------------ #$Date: 2010-01-30 15:59:17 +0200 (Sat, 30 Jan 2010) $ #$Revision: 966 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2015258.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_2015258 _space_group_IT_number 14 _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _[local]_cod_cif_authors_sg_H-M 'P 21/c' loop_ _publ_author_name 'Villiers, Claude' 'Thu\'ery, Pierre' 'Ephritikhine, Michel' _publ_section_title ; Di-tert-butyl ketone hydrazone and di-tert-butyl ketone triphenylphosphoranylidenehydrazone ; _journal_coeditor_code HJ3003 _journal_issue 4 _journal_name_full 'Acta Crystallographica, Section C' _journal_page_first o234 _journal_page_last o236 _journal_volume 62 _journal_year 2006 _chemical_formula_iupac 'C9 H20 N2' _chemical_formula_moiety 'C9 H20 N2' _chemical_formula_sum 'C9 H20 N2' _chemical_formula_weight 156.27 _chemical_name_systematic ; Di-tert-butyl ketone hydrazone ; _symmetry_cell_setting monoclinic _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL97 _cell_angle_alpha 90.00 _cell_angle_beta 101.111(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 11.5299(8) _cell_length_b 8.0975(4) _cell_length_c 10.8937(8) _cell_measurement_reflns_used 23020 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 25.67 _cell_measurement_theta_min 3.09 _cell_volume 998.01(11) _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_collection 'COLLECT (Nonius, 1998)' _computing_data_reduction HKL2000 _computing_molecular_graphics 'SHELXTL (Bruker, 1999)' _computing_publication_material 'SHELXTL and PLATON (Spek, 2003)' _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 'Nonius KappaCCD area-detector' _diffrn_measurement_method 'two \f and two \w scans with 2\% steps' _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 0.0382 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 23020 _diffrn_reflns_theta_full 25.67 _diffrn_reflns_theta_max 25.67 _diffrn_reflns_theta_min 3.09 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.062 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.040 _exptl_crystal_description irregular _exptl_crystal_F_000 352 _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.16 _refine_diff_density_max 0.268 _refine_diff_density_min -0.147 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 112 _refine_ls_number_reflns 1884 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.035 _refine_ls_R_factor_all 0.0427 _refine_ls_R_factor_gt 0.0389 _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^)+(0.0544P)^2^+0.3197P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1021 _refine_ls_wR_factor_ref 0.1049 _reflns_number_gt 1717 _reflns_number_total 1884 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file hj3003.cif loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' 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' 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 N N1 0.12987(9) 0.09362(13) 0.01219(9) 0.0245(2) Uani d . 1 H H1 0.0533(13) 0.1035(17) -0.0336(13) 0.029 Uiso d . 1 H H2 0.1610(12) 0.1948(19) 0.0312(13) 0.029 Uiso d . 1 N N2 0.12725(8) -0.01011(11) 0.11434(8) 0.0206(2) Uani d . 1 C C1 0.20987(9) -0.01413(13) 0.21226(10) 0.0192(2) Uani d . 1 C C2 0.32112(9) 0.09921(13) 0.23046(10) 0.0218(3) Uani d . 1 C C3 0.28322(11) 0.27995(14) 0.24534(11) 0.0276(3) Uani d . 1 H H3A 0.3505 0.3512 0.2504 0.041 Uiso calc R 1 H H3B 0.2516 0.2903 0.3203 0.041 Uiso calc R 1 H H3C 0.2239 0.3107 0.1745 0.041 Uiso calc R 1 C C4 0.41908(11) 0.06408(16) 0.34566(11) 0.0306(3) Uani d . 1 H H4A 0.4808 0.1447 0.3500 0.046 Uiso calc R 1 H H4B 0.4510 -0.0442 0.3384 0.046 Uiso calc R 1 H H4C 0.3864 0.0699 0.4202 0.046 Uiso calc R 1 C C5 0.38405(10) 0.07964(15) 0.11793(11) 0.0282(3) Uani d . 1 H H5A 0.4509 0.1525 0.1282 0.042 Uiso calc R 1 H H5B 0.3300 0.1067 0.0420 0.042 Uiso calc R 1 H H5C 0.4103 -0.0324 0.1138 0.042 Uiso calc R 1 C C6 0.18503(9) -0.14007(14) 0.31124(10) 0.0222(3) Uani d . 1 C C7 0.28249(11) -0.27168(15) 0.34220(13) 0.0333(3) Uani d . 1 H H7A 0.3503 -0.2246 0.3959 0.050 Uiso calc R 1 H H7B 0.3043 -0.3094 0.2663 0.050 Uiso calc R 1 H H7C 0.2537 -0.3631 0.3838 0.050 Uiso calc R 1 C C8 0.16816(11) -0.05157(17) 0.43156(11) 0.0321(3) Uani d . 1 H H8A 0.1509 -0.1315 0.4906 0.048 Uiso calc R 1 H H8B 0.1038 0.0252 0.4122 0.048 Uiso calc R 1 H H8C 0.2392 0.0068 0.4670 0.048 Uiso calc R 1 C C9 0.06898(10) -0.23344(15) 0.26280(11) 0.0290(3) Uani d . 1 H H9A 0.0751 -0.2920 0.1877 0.044 Uiso calc R 1 H H9B 0.0048 -0.1561 0.2453 0.044 Uiso calc R 1 H H9C 0.0547 -0.3105 0.3252 0.044 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 N1 0.0230(5) 0.0280(5) 0.0210(5) -0.0030(4) 0.0009(4) 0.0050(4) N2 0.0206(5) 0.0218(5) 0.0193(5) 0.0009(4) 0.0038(4) 0.0014(3) C1 0.0184(5) 0.0185(5) 0.0206(5) 0.0013(4) 0.0031(4) -0.0008(4) C2 0.0201(5) 0.0225(6) 0.0221(5) -0.0017(4) 0.0023(4) 0.0002(4) C3 0.0291(6) 0.0233(6) 0.0290(6) -0.0031(5) 0.0028(5) -0.0023(5) C4 0.0241(6) 0.0339(7) 0.0303(6) -0.0044(5) -0.0035(5) 0.0023(5) C5 0.0207(6) 0.0340(6) 0.0303(6) -0.0037(5) 0.0058(5) -0.0022(5) C6 0.0219(5) 0.0219(6) 0.0225(6) 0.0007(4) 0.0036(4) 0.0030(4) C7 0.0304(6) 0.0261(6) 0.0435(7) 0.0047(5) 0.0074(5) 0.0095(5) C8 0.0351(7) 0.0381(7) 0.0240(6) -0.0018(5) 0.0083(5) 0.0006(5) C9 0.0281(6) 0.0306(6) 0.0280(6) -0.0062(5) 0.0047(5) 0.0061(5) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag N1 N2 1.3992(13) yes N1 H1 0.930(15) ? N1 H2 0.903(16) ? C1 N2 1.2864(14) yes C1 C2 1.5585(14) yes C1 C6 1.5504(15) yes C2 C3 1.5448(16) ? C2 C4 1.5444(15) ? C2 C5 1.5482(15) ? C3 H3A 0.9600 ? C3 H3B 0.9600 ? C3 H3C 0.9600 ? C4 H4A 0.9600 ? C4 H4B 0.9600 ? C4 H4C 0.9600 ? C5 H5A 0.9600 ? C5 H5B 0.9600 ? C5 H5C 0.9600 ? C6 C7 1.5382(15) ? C6 C9 1.5389(15) ? C6 C8 1.5387(16) ? C7 H7A 0.9600 ? C7 H7B 0.9600 ? C7 H7C 0.9600 ? C8 H8A 0.9600 ? C8 H8B 0.9600 ? C8 H8C 0.9600 ? C9 H9A 0.9600 ? C9 H9B 0.9600 ? C9 H9C 0.9600 ? 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 N2 N1 H1 108.4(8) ? N2 N1 H2 115.5(9) ? H1 N1 H2 109.8(12) ? N1 N2 C1 123.28(9) yes N2 C1 C2 123.39(9) yes N2 C1 C6 112.76(9) yes C2 C1 C6 123.83(9) yes C3 C2 C4 105.46(9) ? C3 C2 C5 111.43(9) ? C4 C2 C5 104.10(9) ? C3 C2 C1 109.19(9) ? C4 C2 C1 116.74(9) ? C5 C2 C1 109.80(9) ? C2 C3 H3A 109.5 ? C2 C3 H3B 109.5 ? H3A C3 H3B 109.5 ? C2 C3 H3C 109.5 ? H3A C3 H3C 109.5 ? H3B C3 H3C 109.5 ? C2 C4 H4A 109.5 ? C2 C4 H4B 109.5 ? H4A C4 H4B 109.5 ? C2 C4 H4C 109.5 ? H4A C4 H4C 109.5 ? H4B C4 H4C 109.5 ? C2 C5 H5A 109.5 ? C2 C5 H5B 109.5 ? H5A C5 H5B 109.5 ? C2 C5 H5C 109.5 ? H5A C5 H5C 109.5 ? H5B C5 H5C 109.5 ? C7 C6 C9 106.56(10) ? C7 C6 C8 110.05(10) ? C9 C6 C8 106.06(9) ? C7 C6 C1 112.53(9) ? C9 C6 C1 110.46(9) ? C8 C6 C1 110.90(9) ? C6 C7 H7A 109.5 ? C6 C7 H7B 109.5 ? H7A C7 H7B 109.5 ? C6 C7 H7C 109.5 ? H7A C7 H7C 109.5 ? H7B C7 H7C 109.5 ? C6 C8 H8A 109.5 ? C6 C8 H8B 109.5 ? H8A C8 H8B 109.5 ? C6 C8 H8C 109.5 ? H8A C8 H8C 109.5 ? H8B C8 H8C 109.5 ? C6 C9 H9A 109.5 ? C6 C9 H9B 109.5 ? H9A C9 H9B 109.5 ? C6 C9 H9C 109.5 ? H9A C9 H9C 109.5 ? H9B C9 H9C 109.5 ? 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 N1 H1 N2 3 0.930(15) 2.230(15) 3.0937(13) 154.1(12) _cod_database_code 2015258