#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2221720.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_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)
_[local]_cod_data_source_file hk2661.cif
_[local]_cod_data_source_block I
_[local]_cod_cif_authors_sg_H-M 'P 21'
_cod_database_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
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
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_distance
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
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)