#------------------------------------------------------------------------------
#$Date: 2016-02-18 14:25:00 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176728 $
#$URL: svn://www.crystallography.net/cod/cif/8/10/21/8102191.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_8102191
loop_
_publ_author_name
'Jin, Jian-Yu'
'Zhang, Kang'
'Zhang, Li-Xue'
'Zhang, An-Jiang'
'Liu, Yu-Zhen'
_publ_section_title
;
Crystal structure of N,N'-bis(4-methoxy-benzylidene)hydrazine, 
C₁₆H₁₆N₂O₂
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              391
_journal_page_last               392
_journal_volume                  222
_journal_year                    2007
_chemical_formula_moiety         'C16 H16 N2 O2'
_chemical_formula_sum            'C16 H16 N2 O2'
_chemical_formula_weight         268.31
_chemical_name_systematic
; 
N,N'-bis-(4-methoxy-benzylidene)-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                109.976(6)
_cell_angle_beta                 93.920(6)
_cell_angle_gamma                111.081(6)
_cell_formula_units_Z            2
_cell_length_a                   8.539(2)
_cell_length_b                   9.230(2)
_cell_length_c                   10.702(3)
_cell_measurement_reflns_used    1284
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.16
_cell_measurement_theta_min      2.68
_cell_volume                     721.9(3)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL(Bruker, 2002)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       phi/omega
_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  0.0258
_diffrn_reflns_av_sigmaI/netI    0.0619
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3788
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.07
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9909
_exptl_absorpt_correction_T_min  0.9832
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.256
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2499
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.256
_refine_ls_R_factor_all          0.1090
_refine_ls_R_factor_gt           0.0806
_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/[σ²(Fo²)+(0.0565P)²+0.2981P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1550
_refine_ls_wR_factor_ref         0.1781
_reflns_number_gt                1677
_reflns_number_total             2499
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            1267-2115.cff
_cod_data_source_block           lx26m
_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.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed
to 'multi-scan' 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_cell_volume        721.8(3)
_cod_database_code               8102191
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_Wyckoff_symbol
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4755(4) 0.3463(4) 0.8657(3) 0.0662(10) Uani 1 2 i d . . .
O2 O 1.0374(5) 0.1960(4) 0.1143(3) 0.0741(10) Uani 1 2 i d . . .
N1 N 0.9728(5) 0.0599(4) 0.5424(4) 0.0593(11) Uani 1 2 i d . . .
N2 N 0.5624(5) 0.4669(5) 0.4831(4) 0.0629(11) Uani 1 2 i d . . .
C1 C 0.3060(6) 0.2584(7) 0.8801(6) 0.0843(17) Uani 1 2 i d . . .
H1A H 0.2283 0.2012 0.7926 0.127 Uiso 1 2 i calc R . .
H1B H 0.2691 0.3376 0.9404 0.127 Uiso 1 2 i calc R . .
H1C H 0.3069 0.1773 0.9170 0.127 Uiso 1 2 i calc R . .
C2 C 0.5525(5) 0.2503(6) 0.7896(4) 0.0522(12) Uani 1 2 i d . . .
C3 C 0.4804(6) 0.0786(6) 0.7273(5) 0.0611(13) Uani 1 2 i d . . .
H3 H 0.3714 0.0172 0.7360 0.073 Uiso 1 2 i calc R . .
C4 C 0.5696(6) -0.0042(6) 0.6511(5) 0.0618(13) Uani 1 2 i d . . .
H4 H 0.5189 -0.1212 0.6071 0.074 Uiso 1 2 i calc R . .
C5 C 0.7328(5) 0.0844(5) 0.6393(4) 0.0494(11) Uani 1 2 i d . . .
C6 C 0.8053(6) 0.2594(5) 0.7033(5) 0.0550(12) Uani 1 2 i d . . .
H6 H 0.9147 0.3211 0.6954 0.066 Uiso 1 2 i calc R . .
C7 C 0.7167(6) 0.3408(5) 0.7776(5) 0.0581(13) Uani 1 2 i d . . .
H7 H 0.7664 0.4580 0.8208 0.070 Uiso 1 2 i calc R . .
C8 C 0.8208(6) -0.0081(6) 0.5555(5) 0.0571(12) Uani 1 2 i d . . .
H8 H 0.7613 -0.1243 0.5088 0.069 Uiso 1 2 i calc R . .
C9 C 1.1426(6) 0.1442(7) 0.1822(5) 0.0831(17) Uani 1 2 i d . . .
H9A H 1.2185 0.2388 0.2622 0.125 Uiso 1 2 i calc R . .
H9B H 1.2091 0.1022 0.1224 0.125 Uiso 1 2 i calc R . .
H9C H 1.0713 0.0567 0.2080 0.125 Uiso 1 2 i calc R . .
C10 C 0.9331(6) 0.2578(6) 0.1834(5) 0.0617(13) Uani 1 2 i d . . .
C11 C 0.9271(6) 0.2857(5) 0.3176(5) 0.0573(12) Uani 1 2 i d . . .
H11 H 0.9980 0.2604 0.3687 0.069 Uiso 1 2 i calc R . .
C12 C 0.8163(6) 0.3509(5) 0.3757(5) 0.0566(12) Uani 1 2 i d . . .
H12 H 0.8132 0.3686 0.4662 0.068 Uiso 1 2 i calc R . .
C13 C 0.7095(6) 0.3910(5) 0.3045(5) 0.0576(12) Uani 1 2 i d . . .
C14 C 0.7159(7) 0.3619(6) 0.1690(5) 0.0727(15) Uani 1 2 i d . . .
H14 H 0.6451 0.3879 0.1183 0.087 Uiso 1 2 i calc R . .
C15 C 0.8253(7) 0.2952(6) 0.1089(5) 0.0742(15) Uani 1 2 i d . . .
H15 H 0.8270 0.2752 0.0178 0.089 Uiso 1 2 i calc R . .
C16 C 0.5888(6) 0.4577(5) 0.3650(5) 0.0603(13) Uani 1 2 i d . . .
H16 H 0.5292 0.4949 0.3160 0.072 Uiso 1 2 i 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
C2 O1 C1 117.1(4) . . ?
C10 O2 C9 117.7(4) . . ?
C8 N1 N1 112.1(5) . 2_756 ?
C16 N2 N2 111.2(5) . 2_666 ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 O1 125.1(4) . . ?
C3 C2 C7 119.6(4) . . ?
O1 C2 C7 115.2(4) . . ?
C2 C3 C4 119.9(4) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 120.9(4) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 118.8(4) . . ?
C4 C5 C8 119.0(4) . . ?
C6 C5 C8 122.1(4) . . ?
C7 C6 C5 120.2(4) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C2 120.6(4) . . ?
C6 C7 H7 119.7 . . ?
C2 C7 H7 119.7 . . ?
N1 C8 C5 124.0(4) . . ?
N1 C8 H8 118.0 . . ?
C5 C8 H8 118.0 . . ?
O2 C9 H9A 109.5 . . ?
O2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O2 C10 C11 125.9(5) . . ?
O2 C10 C15 115.0(5) . . ?
C11 C10 C15 119.1(5) . . ?
C12 C11 C10 119.8(4) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 C13 122.2(5) . . ?
C11 C12 H12 118.9 . . ?
C13 C12 H12 118.9 . . ?
C12 C13 C14 117.6(5) . . ?
C12 C13 C16 122.5(5) . . ?
C14 C13 C16 119.9(5) . . ?
C15 C14 C13 120.9(5) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C10 120.3(5) . . ?
C14 C15 H15 119.8 . . ?
C10 C15 H15 119.8 . . ?
N2 C16 C13 122.4(4) . . ?
N2 C16 H16 118.8 . . ?
C13 C16 H16 118.8 . . ?
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
O1 C2 1.371(5) . ?
O1 C1 1.431(5) . ?
O2 C10 1.353(5) . ?
O2 C9 1.422(5) . ?
N1 C8 1.264(5) . ?
N1 N1 1.416(6) 2_756 ?
N2 C16 1.279(5) . ?
N2 N2 1.417(7) 2_666 ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.362(6) . ?
C2 C7 1.391(6) . ?
C3 C4 1.380(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.379(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.388(6) . ?
C5 C8 1.459(6) . ?
C6 C7 1.361(6) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.379(6) . ?
C10 C15 1.385(6) . ?
C11 C12 1.370(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.374(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.390(6) . ?
C13 C16 1.461(6) . ?
C14 C15 1.376(6) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 O1 C2 C3 -0.1(6) . . . . ?
C1 O1 C2 C7 179.7(4) . . . . ?
O1 C2 C3 C4 178.8(4) . . . . ?
C7 C2 C3 C4 -1.0(7) . . . . ?
C2 C3 C4 C5 1.3(7) . . . . ?
C3 C4 C5 C6 -1.3(7) . . . . ?
C3 C4 C5 C8 -178.8(4) . . . . ?
C4 C5 C6 C7 0.8(7) . . . . ?
C8 C5 C6 C7 178.3(4) . . . . ?
C5 C6 C7 C2 -0.5(7) . . . . ?
C3 C2 C7 C6 0.5(7) . . . . ?
O1 C2 C7 C6 -179.2(4) . . . . ?
N1 N1 C8 C5 178.7(4) 2_756 . . . ?
C4 C5 C8 N1 -176.9(5) . . . . ?
C6 C5 C8 N1 5.6(7) . . . . ?
C9 O2 C10 C11 4.4(7) . . . . ?
C9 O2 C10 C15 -175.8(4) . . . . ?
O2 C10 C11 C12 179.3(4) . . . . ?
C15 C10 C11 C12 -0.5(7) . . . . ?
C10 C11 C12 C13 -0.3(7) . . . . ?
C11 C12 C13 C14 0.5(6) . . . . ?
C11 C12 C13 C16 178.9(4) . . . . ?
C12 C13 C14 C15 0.1(7) . . . . ?
C16 C13 C14 C15 -178.4(4) . . . . ?
C13 C14 C15 C10 -0.8(8) . . . . ?
O2 C10 C15 C14 -178.8(4) . . . . ?
C11 C10 C15 C14 1.0(7) . . . . ?
N2 N2 C16 C13 -178.9(4) 2_666 . . . ?
C12 C13 C16 N2 -7.3(7) . . . . ?
C14 C13 C16 N2 171.0(4) . . . . ?
