#------------------------------------------------------------------------------
#$Date: 2016-02-18 14:25:00 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176728 $
#$URL: svn://www.crystallography.net/cod/cif/8/10/26/8102698.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_8102698
loop_
_publ_author_name
'Zhi-Gang Yin'
'Zong-Lei Fei'
'Heng-Yu Qian'
'Chun-Xia Zhang'
_publ_section_title
;
 Crystal structure of
 1-(1,3-diphenylallylidene)-2-(2-nitrophenyl)hydrazine, C21H17N3O2
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              343
_journal_volume                  225
_journal_year                    2010
_chemical_formula_structural     'C21 H17 N3 O2'
_chemical_formula_sum            'C21 H17 N3 O2'
_chemical_formula_weight         343.38
_chemical_name_systematic
;
1-(1,3-diphenylallylidene)-2-(2-nitrophenyl)hydrazine
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                93.016(11)
_cell_angle_beta                 93.753(12)
_cell_angle_gamma                110.370(14)
_cell_formula_units_Z            2
_cell_length_a                   8.1686(13)
_cell_length_b                   9.8684(14)
_cell_length_c                   11.7741(15)
_cell_measurement_reflns_used    1976
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.3484
_cell_measurement_theta_min      3.0480
_cell_volume                     885.0(2)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART CCD area detector'
_diffrn_measurement_method       'ω scans'
_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  0.0219
_diffrn_reflns_av_sigmaI/netI    0.0709
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7008
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         3.05
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_T_min  0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS(Bruker, 1998)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.089
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.027
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.732
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3654
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.732
_refine_ls_R_factor_all          0.1009
_refine_ls_R_factor_gt           0.0353
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0376P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0692
_refine_ls_wR_factor_ref         0.0758
_reflns_number_gt                1603
_reflns_number_total             3654
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-2967.cff
_cod_data_source_block           m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               8102698
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
N2 N -0.00523(15) 0.28701(12) 0.85703(10) 0.0516(3) Uani 1 1 d . . .
H2A H -0.0239 0.3191 0.7928 0.062 Uiso 1 1 calc R . .
N1 N 0.11366(15) 0.21849(12) 0.86928(10) 0.0527(3) Uani 1 1 d . . .
C16 C -0.09403(18) 0.30406(14) 0.94769(12) 0.0449(4) Uani 1 1 d . . .
C9 C 0.19166(18) 0.20294(15) 0.77952(13) 0.0487(4) Uani 1 1 d . . .
N3 N -0.26771(19) 0.42515(14) 0.83878(14) 0.0668(4) Uani 1 1 d . . .
C21 C -0.22135(18) 0.37024(14) 0.94244(13) 0.0504(4) Uani 1 1 d . . .
C7 C 0.38746(18) 0.07978(15) 0.71224(13) 0.0530(4) Uani 1 1 d . . .
H7A H 0.3642 0.1028 0.6388 0.064 Uiso 1 1 calc R . .
C6 C 0.50412(18) -0.00393(15) 0.72596(13) 0.0489(4) Uani 1 1 d . . .
C8 C 0.31251(19) 0.12543(15) 0.79494(13) 0.0544(4) Uani 1 1 d . . .
H8A H 0.3394 0.1063 0.8690 0.065 Uiso 1 1 calc R . .
O2 O -0.20491(17) 0.40508(14) 0.74974(11) 0.0845(4) Uani 1 1 d . . .
O1 O -0.37074(16) 0.49072(13) 0.84073(11) 0.0947(4) Uani 1 1 d . . .
C10 C 0.16005(19) 0.25656(16) 0.66735(12) 0.0470(4) Uani 1 1 d . . .
C18 C -0.1502(2) 0.26734(17) 1.14430(14) 0.0651(5) Uani 1 1 d . . .
H18A H -0.1255 0.2326 1.2128 0.078 Uiso 1 1 calc R . .
C5 C 0.59680(19) -0.00339(15) 0.82896(14) 0.0585(4) Uani 1 1 d . . .
H5A H 0.5872 0.0530 0.8922 0.070 Uiso 1 1 calc R . .
C20 C -0.3086(2) 0.38418(16) 1.03736(16) 0.0646(5) Uani 1 1 d . . .
H20A H -0.3914 0.4291 1.0322 0.077 Uiso 1 1 calc R . .
C17 C -0.06335(19) 0.25269(16) 1.05237(13) 0.0563(4) Uani 1 1 d . . .
H17A H 0.0188 0.2072 1.0594 0.068 Uiso 1 1 calc R . .
C1 C 0.52096(19) -0.09015(16) 0.63360(13) 0.0591(4) Uani 1 1 d . . .
H1B H 0.4603 -0.0924 0.5635 0.071 Uiso 1 1 calc R . .
C2 C 0.6270(2) -0.17302(17) 0.64449(14) 0.0658(5) Uani 1 1 d . . .
H2B H 0.6368 -0.2306 0.5820 0.079 Uiso 1 1 calc R . .
C15 C 0.2747(2) 0.38458(16) 0.63441(13) 0.0580(4) Uani 1 1 d . . .
H15A H 0.3766 0.4354 0.6809 0.070 Uiso 1 1 calc R . .
C19 C -0.2744(2) 0.33300(18) 1.13744(15) 0.0710(5) Uani 1 1 d . . .
H19A H -0.3337 0.3420 1.2005 0.085 Uiso 1 1 calc R . .
C4 C 0.7029(2) -0.08499(18) 0.83931(15) 0.0667(5) Uani 1 1 d . . .
H4A H 0.7651 -0.0825 0.9089 0.080 Uiso 1 1 calc R . .
C14 C 0.2404(2) 0.43835(17) 0.53331(14) 0.0677(5) Uani 1 1 d . . .
H14A H 0.3187 0.5252 0.5125 0.081 Uiso 1 1 calc R . .
C3 C 0.7171(2) -0.16982(18) 0.74719(15) 0.0681(5) Uani 1 1 d . . .
H3A H 0.7881 -0.2254 0.7546 0.082 Uiso 1 1 calc R . .
C13 C 0.0920(3) 0.3647(2) 0.46370(14) 0.0693(5) Uani 1 1 d . . .
H13A H 0.0679 0.4017 0.3961 0.083 Uiso 1 1 calc R . .
C11 C 0.0124(2) 0.18304(18) 0.59563(14) 0.0723(5) Uani 1 1 d . . .
H11A H -0.0665 0.0960 0.6157 0.087 Uiso 1 1 calc R . .
C12 C -0.0201(2) 0.2370(2) 0.49408(14) 0.0801(5) Uani 1 1 d . . .
H12A H -0.1198 0.1852 0.4460 0.096 Uiso 1 1 calc R . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 N2 N1 119.40(11) . . ?
C16 N2 H2A 120.3 . . ?
N1 N2 H2A 120.3 . . ?
C9 N1 N2 116.66(11) . . ?
N2 C16 C17 120.39(13) . . ?
N2 C16 C21 123.42(13) . . ?
C17 C16 C21 116.17(14) . . ?
N1 C9 C8 114.99(13) . . ?
N1 C9 C10 123.80(12) . . ?
C8 C9 C10 121.20(14) . . ?
O1 N3 O2 121.01(15) . . ?
O1 N3 C21 119.05(16) . . ?
O2 N3 C21 119.94(13) . . ?
C20 C21 C16 121.05(14) . . ?
C20 C21 N3 117.31(14) . . ?
C16 C21 N3 121.64(14) . . ?
C8 C7 C6 125.90(14) . . ?
C8 C7 H7A 117.0 . . ?
C6 C7 H7A 117.0 . . ?
C5 C6 C1 117.80(13) . . ?
C5 C6 C7 122.63(14) . . ?
C1 C6 C7 119.55(14) . . ?
C7 C8 C9 125.32(14) . . ?
C7 C8 H8A 117.3 . . ?
C9 C8 H8A 117.3 . . ?
C11 C10 C15 118.02(14) . . ?
C11 C10 C9 121.04(14) . . ?
C15 C10 C9 120.88(14) . . ?
C17 C18 C19 121.02(15) . . ?
C17 C18 H18A 119.5 . . ?
C19 C18 H18A 119.5 . . ?
C4 C5 C6 121.13(15) . . ?
C4 C5 H5A 119.4 . . ?
C6 C5 H5A 119.4 . . ?
C19 C20 C21 120.81(15) . . ?
C19 C20 H20A 119.6 . . ?
C21 C20 H20A 119.6 . . ?
C18 C17 C16 121.89(14) . . ?
C18 C17 H17A 119.1 . . ?
C16 C17 H17A 119.1 . . ?
C2 C1 C6 120.94(14) . . ?
C2 C1 H1B 119.5 . . ?
C6 C1 H1B 119.5 . . ?
C3 C2 C1 119.83(15) . . ?
C3 C2 H2B 120.1 . . ?
C1 C2 H2B 120.1 . . ?
C10 C15 C14 120.86(15) . . ?
C10 C15 H15A 119.6 . . ?
C14 C15 H15A 119.6 . . ?
C20 C19 C18 119.05(16) . . ?
C20 C19 H19A 120.5 . . ?
C18 C19 H19A 120.5 . . ?
C3 C4 C5 120.11(15) . . ?
C3 C4 H4A 119.9 . . ?
C5 C4 H4A 119.9 . . ?
C13 C14 C15 120.33(16) . . ?
C13 C14 H14A 119.8 . . ?
C15 C14 H14A 119.8 . . ?
C2 C3 C4 120.18(15) . . ?
C2 C3 H3A 119.9 . . ?
C4 C3 H3A 119.9 . . ?
C12 C13 C14 119.33(15) . . ?
C12 C13 H13A 120.3 . . ?
C14 C13 H13A 120.3 . . ?
C10 C11 C12 120.72(15) . . ?
C10 C11 H11A 119.6 . . ?
C12 C11 H11A 119.6 . . ?
C13 C12 C11 120.71(17) . . ?
C13 C12 H12A 119.6 . . ?
C11 C12 H12A 119.6 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N2 C16 1.3643(16) . ?
N2 N1 1.3676(14) . ?
N2 H2A 0.8600 . ?
N1 C9 1.2984(16) . ?
C16 C17 1.3973(18) . ?
C16 C21 1.4074(18) . ?
C9 C8 1.4523(19) . ?
C9 C10 1.4883(19) . ?
N3 O1 1.2279(15) . ?
N3 O2 1.2332(16) . ?
N3 C21 1.4417(18) . ?
C21 C20 1.3899(19) . ?
C7 C8 1.3227(18) . ?
C7 C6 1.4693(19) . ?
C7 H7A 0.9300 . ?
C6 C5 1.3857(19) . ?
C6 C1 1.3889(19) . ?
C8 H8A 0.9300 . ?
C10 C11 1.373(2) . ?
C10 C15 1.3781(19) . ?
C18 C17 1.3603(19) . ?
C18 C19 1.382(2) . ?
C18 H18A 0.9300 . ?
C5 C4 1.377(2) . ?
C5 H5A 0.9300 . ?
C20 C19 1.356(2) . ?
C20 H20A 0.9300 . ?
C17 H17A 0.9300 . ?
C1 C2 1.3875(19) . ?
C1 H1B 0.9300 . ?
C2 C3 1.367(2) . ?
C2 H2B 0.9300 . ?
C15 C14 1.3797(19) . ?
C15 H15A 0.9300 . ?
C19 H19A 0.9300 . ?
C4 C3 1.371(2) . ?
C4 H4A 0.9300 . ?
C14 C13 1.365(2) . ?
C14 H14A 0.9300 . ?
C3 H3A 0.9300 . ?
C13 C12 1.357(2) . ?
C13 H13A 0.9300 . ?
C11 C12 1.381(2) . ?
C11 H11A 0.9300 . ?
C12 H12A 0.9300 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A O2 0.86 1.996 2.612 127.64 .
