#------------------------------------------------------------------------------ #$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $ #$Revision: 176789 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/22/17/2221720.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_2221720 loop_ _publ_author_name 'Feng, Qi' 'Tang, Qiong' 'Xu, Hao' 'Yao, Cheng' _publ_section_title ; tert-Butyl N'-[4-(2-pyridyl)benzylidene]hydrazinecarboxylate ; _journal_coeditor_code HK2661 _journal_issue 5 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1127 _journal_paper_doi 10.1107/S1600536809012835 _journal_volume 65 _journal_year 2009 _chemical_formula_iupac 'C17 H19 N3 O2' _chemical_formula_moiety 'C17 H19 N3 O2' _chemical_formula_sum 'C17 H19 N3 O2' _chemical_formula_weight 297.35 _chemical_name_systematic ; tert-Butyl N'-[4-(2-pyridyl)benzylidene]hydrazinecarboxylate ; _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 _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 91.01(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 5.3080(11) _cell_length_b 6.3010(13) _cell_length_c 23.459(5) _cell_measurement_reflns_used 25 _cell_measurement_temperature 294(2) _cell_measurement_theta_max 13 _cell_measurement_theta_min 9 _cell_volume 784.5(3) _computing_cell_refinement 'CAD-4 Software (Enraf--Nonius, 1985)' _computing_data_collection 'CAD-4 Software (Enraf--Nonius, 1985)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 294(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Nonius--Nonius CAD-4' _diffrn_measurement_method \w/2\q _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 0.0277 _diffrn_reflns_av_sigmaI/netI 0.0448 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_number 1743 _diffrn_reflns_theta_full 25.27 _diffrn_reflns_theta_max 25.27 _diffrn_reflns_theta_min 1.74 _diffrn_standards_decay_% 1 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_T_max 0.9916 _exptl_absorpt_correction_T_min 0.9751 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North et al., 1968)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.259 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 316 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.164 _refine_diff_density_min -0.214 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 199 _refine_ls_number_reflns 1566 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.003 _refine_ls_R_factor_all 0.0697 _refine_ls_R_factor_gt 0.0508 _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^)+(0.1P)^2^+0.33P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1387 _refine_ls_wR_factor_ref 0.1703 _reflns_number_gt 1249 _reflns_number_total 1566 _reflns_threshold_expression I>2\s(I) _cod_data_source_file hk2661.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'P 21' _cod_database_code 2221720 _cod_database_fobs_code 2221720 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 _atom_site_disorder_assembly _atom_site_disorder_group O O1 0.5696(5) 1.5114(6) 0.37089(14) 0.0589(9) Uani d . 1 . . O O2 0.8570(6) 1.3033(6) 0.32757(16) 0.0688(10) Uani d . 1 . . N N1 0.4371(6) 1.2553(6) 0.31524(16) 0.0524(9) Uani d . 1 . . H H1A 0.2891 1.3001 0.3235 0.063 Uiso calc R 1 . . N N2 0.4651(7) 1.0839(6) 0.27985(16) 0.0507(9) Uani d . 1 . . N N3 0.1499(6) 0.2707(7) 0.06762(16) 0.0545(10) Uani d . 1 . . C C1 0.5928(11) 1.7923(13) 0.4341(3) 0.099(2) Uani d . 1 . . H H1B 0.5025 1.8791 0.4071 0.149 Uiso calc R 1 . . H H1C 0.6959 1.8808 0.4583 0.149 Uiso calc R 1 . . H H1D 0.4751 1.7155 0.4569 0.149 Uiso calc R 1 . . C C2 0.9263(10) 1.7590(10) 0.3637(2) 0.0684(14) Uani d . 1 . . H H2B 0.8254 1.8437 0.3381 0.103 Uiso calc R 1 . . H H2C 1.0257 1.6612 0.3423 0.103 Uiso calc R 1 . . H H2D 1.0356 1.8496 0.3859 0.103 Uiso calc R 1 . . C C3 0.9018(11) 1.4977(13) 0.4441(2) 0.0815(18) Uani d . 1 . . H H3A 1.0048 1.4006 0.4233 0.122 Uiso calc R 1 . . H H3B 0.7854 1.4195 0.4669 0.122 Uiso calc R 1 . . H H3C 1.0069 1.5841 0.4684 0.122 Uiso calc R 1 . . C C4 0.7575(8) 1.6377(9) 0.40286(19) 0.0569(12) Uani d . 1 . . C C5 0.6416(8) 1.3524(7) 0.3368(2) 0.0506(10) Uani d . 1 . . C C6 0.2709(8) 1.0167(8) 0.25407(19) 0.0505(10) Uani d . 1 . . H H6A 0.1184 1.0872 0.2581 0.061 Uiso calc R 1 . . C C7 0.2841(8) 0.8282(8) 0.21781(17) 0.0476(10) Uani d . 1 . . C C8 0.4830(8) 0.6875(9) 0.2220(2) 0.0544(12) Uani d . 1 . . H H8A 0.6092 0.7110 0.2493 0.065 Uiso calc R 1 . . C C9 0.4994(8) 0.5144(8) 0.18695(19) 0.0532(11) Uani d . 1 . . H H9A 0.6369 0.4236 0.1905 0.064 Uiso calc R 1 . . C C10 0.3124(7) 0.4726(7) 0.14596(16) 0.0410(9) Uani d . 1 . . C C11 0.1129(8) 0.6120(8) 0.1429(2) 0.0567(12) Uani d . 1 . . H H11A -0.0145 0.5891 0.1159 0.068 Uiso calc R 1 . . C C12 0.0966(8) 0.7830(9) 0.17841(19) 0.0566(12) Uani d . 1 . . H H12A -0.0441 0.8706 0.1759 0.068 Uiso calc R 1 . . C C13 0.3321(7) 0.2892(7) 0.10648(16) 0.0412(9) Uani d . 1 . . C C14 0.5270(9) 0.1443(8) 0.1101(2) 0.0564(12) Uani d . 1 . . H H14A 0.6522 0.1580 0.1381 0.068 Uiso calc R 1 . . C C15 0.5332(9) -0.0208(9) 0.0717(2) 0.0612(13) Uani d . 1 . . H H15A 0.6635 -0.1194 0.0735 0.073 Uiso calc R 1 . . C C16 0.3498(9) -0.0394(8) 0.0314(2) 0.0566(12) Uani d . 1 . . H H16A 0.3513 -0.1501 0.0052 0.068 Uiso calc R 1 . . C C17 0.1603(9) 0.1099(9) 0.0301(2) 0.0590(12) Uani d . 1 . . H H17A 0.0346 0.0991 0.0021 0.071 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 O1 0.0443(15) 0.052(2) 0.081(2) -0.0021(15) 0.0055(14) -0.0195(18) O2 0.0480(17) 0.057(2) 0.102(2) 0.0030(18) 0.0129(16) -0.022(2) N1 0.0446(18) 0.042(2) 0.070(2) 0.0005(18) 0.0065(15) -0.015(2) N2 0.057(2) 0.036(2) 0.059(2) 0.0007(18) 0.0094(16) -0.0084(18) N3 0.0498(19) 0.047(2) 0.066(2) -0.001(2) -0.0026(16) -0.010(2) C1 0.070(3) 0.100(6) 0.129(5) -0.010(4) 0.012(3) -0.068(5) C2 0.072(3) 0.055(3) 0.078(3) -0.008(3) -0.005(2) 0.007(3) C3 0.081(3) 0.096(5) 0.066(3) -0.007(4) -0.020(2) 0.018(4) C4 0.050(2) 0.055(3) 0.065(3) -0.004(2) 0.003(2) -0.011(3) C5 0.049(2) 0.035(2) 0.067(3) 0.003(2) 0.0086(19) -0.008(2) C6 0.046(2) 0.044(2) 0.061(2) -0.001(2) 0.0100(18) -0.006(2) C7 0.048(2) 0.044(2) 0.051(2) -0.003(2) 0.0120(17) -0.001(2) C8 0.052(2) 0.049(3) 0.062(3) 0.010(2) -0.0083(19) -0.011(2) C9 0.049(2) 0.042(2) 0.068(3) 0.010(2) -0.0021(19) -0.004(2) C10 0.0413(19) 0.041(2) 0.0405(18) -0.0016(19) 0.0030(14) 0.0036(18) C11 0.046(2) 0.050(3) 0.074(3) 0.003(2) -0.008(2) -0.010(3) C12 0.042(2) 0.056(3) 0.072(3) 0.014(2) -0.0091(19) -0.010(3) C13 0.0380(18) 0.040(2) 0.0461(19) -0.004(2) 0.0050(15) -0.0028(19) C14 0.059(3) 0.046(3) 0.064(3) 0.009(2) 0.003(2) -0.001(2) C15 0.061(3) 0.049(3) 0.073(3) 0.011(3) 0.009(2) -0.003(3) C16 0.062(3) 0.046(3) 0.062(3) -0.004(2) 0.008(2) -0.013(2) C17 0.061(3) 0.055(3) 0.061(3) -0.008(3) -0.002(2) -0.013(3) 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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C5 O1 C4 . . 120.6(3) ? C5 N1 N2 . . 119.6(3) ? C5 N1 H1A . . 120.2 ? N2 N1 H1A . . 120.2 ? C6 N2 N1 . . 117.3(4) ? C13 N3 C17 . . 118.7(4) ? C4 C1 H1B . . 109.5 ? C4 C1 H1C . . 109.5 ? H1B C1 H1C . . 109.5 ? C4 C1 H1D . . 109.5 ? H1B C1 H1D . . 109.5 ? H1C C1 H1D . . 109.5 ? C4 C2 H2B . . 109.5 ? C4 C2 H2C . . 109.5 ? H2B C2 H2C . . 109.5 ? C4 C2 H2D . . 109.5 ? H2B C2 H2D . . 109.5 ? H2C C2 H2D . . 109.5 ? C4 C3 H3A . . 109.5 ? C4 C3 H3B . . 109.5 ? H3A C3 H3B . . 109.5 ? C4 C3 H3C . . 109.5 ? H3A C3 H3C . . 109.5 ? H3B C3 H3C . . 109.5 ? O1 C4 C2 . . 111.7(4) ? O1 C4 C3 . . 110.1(5) ? C2 C4 C3 . . 112.8(4) ? O1 C4 C1 . . 101.7(4) ? C2 C4 C1 . . 109.0(5) ? C3 C4 C1 . . 111.0(5) ? O2 C5 N1 . . 125.4(4) ? O2 C5 O1 . . 125.4(4) ? N1 C5 O1 . . 109.2(3) ? N2 C6 C7 . . 120.3(4) ? N2 C6 H6A . . 119.8 ? C7 C6 H6A . . 119.8 ? C12 C7 C8 . . 117.2(4) ? C12 C7 C6 . . 121.2(4) ? C8 C7 C6 . . 121.6(4) ? C9 C8 C7 . . 121.7(4) ? C9 C8 H8A . . 119.1 ? C7 C8 H8A . . 119.1 ? C8 C9 C10 . . 120.8(4) ? C8 C9 H9A . . 119.6 ? C10 C9 H9A . . 119.6 ? C11 C10 C9 . . 116.9(4) ? C11 C10 C13 . . 121.8(4) ? C9 C10 C13 . . 121.3(4) ? C12 C11 C10 . . 121.9(4) ? C12 C11 H11A . . 119.0 ? C10 C11 H11A . . 119.0 ? C11 C12 C7 . . 121.4(4) ? C11 C12 H12A . . 119.3 ? C7 C12 H12A . . 119.3 ? N3 C13 C14 . . 121.5(4) ? N3 C13 C10 . . 116.1(4) ? C14 C13 C10 . . 122.5(3) ? C15 C14 C13 . . 119.1(4) ? C15 C14 H14A . . 120.5 ? C13 C14 H14A . . 120.5 ? C16 C15 C14 . . 119.9(5) ? C16 C15 H15A . . 120.1 ? C14 C15 H15A . . 120.1 ? C15 C16 C17 . . 118.3(5) ? C15 C16 H16A . . 120.9 ? C17 C16 H16A . . 120.9 ? N3 C17 C16 . . 122.6(4) ? N3 C17 H17A . . 118.7 ? C16 C17 H17A . . 118.7 ? 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 O1 C5 . 1.341(5) ? O1 C4 . 1.471(5) ? O2 C5 . 1.208(5) ? N1 C5 . 1.338(6) ? N1 N2 . 1.372(5) ? N1 H1A . 0.8600 ? N2 C6 . 1.259(6) ? N3 C13 . 1.322(5) ? N3 C17 . 1.344(6) ? C1 C4 . 1.508(8) ? C1 H1B . 0.9600 ? C1 H1C . 0.9600 ? C1 H1D . 0.9600 ? C2 C4 . 1.503(7) ? C2 H2B . 0.9600 ? C2 H2C . 0.9600 ? C2 H2D . 0.9600 ? C3 C4 . 1.508(8) ? C3 H3A . 0.9600 ? C3 H3B . 0.9600 ? C3 H3C . 0.9600 ? C6 C7 . 1.463(6) ? C6 H6A . 0.9300 ? C7 C12 . 1.376(6) ? C7 C8 . 1.381(6) ? C8 C9 . 1.369(7) ? C8 H8A . 0.9300 ? C9 C10 . 1.395(6) ? C9 H9A . 0.9300 ? C10 C11 . 1.377(6) ? C10 C13 . 1.486(6) ? C11 C12 . 1.365(7) ? C11 H11A . 0.9300 ? C12 H12A . 0.9300 ? C13 C14 . 1.381(6) ? C14 C15 . 1.377(7) ? C14 H14A . 0.9300 ? C15 C16 . 1.351(7) ? C15 H15A . 0.9300 ? C16 C17 . 1.377(7) ? C16 H16A . 0.9300 ? C17 H17A . 0.9300 ? 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 _geom_hbond_publ_flag N1 H1A O2 1_455 0.86 2.30 3.113(5) 158 yes C16 H16A Cg2 2_645 0.93 2.80 3.588(4) 144 yes loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C5 N1 N2 C6 . . . . -170.0(5) ? C5 O1 C4 C2 . . . . 63.9(6) ? C5 O1 C4 C3 . . . . -62.3(5) ? C5 O1 C4 C1 . . . . -180.0(5) ? N2 N1 C5 O2 . . . . 0.7(7) ? N2 N1 C5 O1 . . . . -178.7(3) ? C4 O1 C5 O2 . . . . -2.8(7) ? C4 O1 C5 N1 . . . . 176.6(4) ? N1 N2 C6 C7 . . . . -177.0(4) ? N2 C6 C7 C12 . . . . -163.2(5) ? N2 C6 C7 C8 . . . . 17.4(7) ? C12 C7 C8 C9 . . . . 2.5(7) ? C6 C7 C8 C9 . . . . -178.1(4) ? C7 C8 C9 C10 . . . . -0.8(7) ? C8 C9 C10 C11 . . . . -0.3(7) ? C8 C9 C10 C13 . . . . 178.0(4) ? C9 C10 C11 C12 . . . . -0.4(7) ? C13 C10 C11 C12 . . . . -178.8(4) ? C10 C11 C12 C7 . . . . 2.3(7) ? C8 C7 C12 C11 . . . . -3.3(7) ? C6 C7 C12 C11 . . . . 177.3(4) ? C17 N3 C13 C14 . . . . -1.8(6) ? C17 N3 C13 C10 . . . . 178.8(4) ? C11 C10 C13 N3 . . . . 1.4(6) ? C9 C10 C13 N3 . . . . -176.9(4) ? C11 C10 C13 C14 . . . . -178.0(4) ? C9 C10 C13 C14 . . . . 3.7(6) ? N3 C13 C14 C15 . . . . 1.1(7) ? C10 C13 C14 C15 . . . . -179.6(4) ? C13 C14 C15 C16 . . . . -0.2(7) ? C14 C15 C16 C17 . . . . 0.1(7) ? C13 N3 C17 C16 . . . . 1.7(7) ? C15 C16 C17 N3 . . . . -0.8(7) ?