#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/90/2239037.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_2239037
loop_
_publ_author_name
'Taha, Muhammad'
'Shah, Syed Adnan Ali'
'Sultan, Sadia'
'Ismail, Nor Hadiani'
'Yousuf, Sammer'
_publ_section_title
;
 2-{[2-(2-Hydroxy-5-methoxybenzylidene)hydrazin-1-ylidene]methyl}-4-methoxyphenol
;
_journal_coeditor_code           RZ5090
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o131
_journal_paper_doi               10.1107/S1600536813034636
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C16 H16 N2 O4'
_chemical_formula_moiety         'C16 H16 N2 O4'
_chemical_formula_sum            'C16 H16 N2 O4'
_chemical_formula_weight         300.31
_chemical_name_common
2-{[2-(2-Hydroxy-5-methoxybenzylidene)hydrazin-1-ylidene]methyl}-4-methoxyphenol
_chemical_name_systematic
;
2,2'-[Hydrazine-1,2-diylidenebis(methan-1-yl-1-ylidene)]bis(4-methoxyphenol)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 91.192(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.7132(4)
_cell_length_b                   15.9369(10)
_cell_length_c                   6.8022(4)
_cell_measurement_reflns_used    1747
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.02
_cell_measurement_theta_min      2.56
_cell_volume                     727.59(8)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON
(Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type
;
Bruker SMART APEX CCD area-detector
;
_diffrn_measurement_method       'ω scan'
_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  0.0155
_diffrn_reflns_av_sigmaI/netI    0.0165
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            4243
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         2.56
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.9832
_exptl_absorpt_correction_T_min  0.9444
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.136
_refine_diff_density_min         -0.124
_refine_ls_extinction_coef       0.031(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXTL (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     106
_refine_ls_number_reflns         1327
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0344
_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)+(0.0505P)²+0.0718P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.1011
_reflns_number_gt                1093
_reflns_number_total             1327
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz5090sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2239037
_cod_database_fobs_code          2239037
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_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_symmetry_multiplicity
O O1 0.45722(17) 0.62697(7) -0.27087(17) 0.0865(4) Uani d . 1 1
O O2 -0.21947(15) 0.62524(8) 0.17505(19) 0.0767(4) Uani d . 1 1
H H2 -0.199(3) 0.5903(15) 0.284(3) 0.118(8) Uiso d . 1 1
N N1 -0.01775(16) 0.52608(7) 0.41923(16) 0.0588(3) Uani d . 1 1
C C1 0.1157(2) 0.67416(8) -0.2207(2) 0.0626(4) Uani d . 1 1
H H1C 0.1136 0.7055 -0.3361 0.075 Uiso calc R 1 1
C C2 -0.0501(2) 0.67158(9) -0.1050(2) 0.0636(4) Uani d . 1 1
H H2B -0.1632 0.7015 -0.1436 0.076 Uiso calc R 1 1
C C3 -0.0522(2) 0.62571(8) 0.0666(2) 0.0562(4) Uani d . 1 1
C C4 0.12003(18) 0.58088(7) 0.12530(19) 0.0518(3) Uani d . 1 1
C C5 0.28603(19) 0.58474(8) 0.0070(2) 0.0585(4) Uani d . 1 1
H H5A 0.4008 0.5559 0.0453 0.070 Uiso calc R 1 1
C C6 0.2857(2) 0.63003(8) -0.1651(2) 0.0594(4) Uani d . 1 1
C C7 0.4762(3) 0.68202(11) -0.4318(2) 0.0842(5) Uani d . 1 1
H H7A 0.6065 0.6762 -0.4856 0.126 Uiso calc R 1 1
H H7B 0.4577 0.7388 -0.3884 0.126 Uiso calc R 1 1
H H7C 0.3773 0.6686 -0.5307 0.126 Uiso calc R 1 1
C C8 0.12864(19) 0.53066(8) 0.3019(2) 0.0564(4) Uani d . 1 1
H H8A 0.2442 0.5006 0.3314 0.068 Uiso calc R 1 1
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'
O O 0.0106 0.0060 '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_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
C6 O1 C7 . 118.38(12)
C3 O2 H2 . 109.0(13)
C8 N1 N1 3_566 113.84(13)
C2 C1 C6 . 119.96(14)
C2 C1 H1C . 120.0
C6 C1 H1C . 120.0
C1 C2 C3 . 121.54(12)
C1 C2 H2B . 119.2
C3 C2 H2B . 119.2
O2 C3 C2 . 119.17(12)
O2 C3 C4 . 121.76(13)
C2 C3 C4 . 119.07(13)
C5 C4 C3 . 118.45(12)
C5 C4 C8 . 119.20(11)
C3 C4 C8 . 122.35(12)
C6 C5 C4 . 121.95(12)
C6 C5 H5A . 119.0
C4 C5 H5A . 119.0
O1 C6 C5 . 116.20(12)
O1 C6 C1 . 124.77(13)
C5 C6 C1 . 119.03(13)
O1 C7 H7A . 109.5
O1 C7 H7B . 109.5
H7A C7 H7B . 109.5
O1 C7 H7C . 109.5
H7A C7 H7C . 109.5
H7B C7 H7C . 109.5
N1 C8 C4 . 122.15(12)
N1 C8 H8A . 118.9
C4 C8 H8A . 118.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C6 . 1.3713(17)
O1 C7 . 1.4105(18)
O2 C3 . 1.3563(16)
O2 H2 . 0.93(2)
N1 C8 . 1.2809(15)
N1 N1 3_566 1.394(2)
C1 C2 . 1.377(2)
C1 C6 . 1.386(2)
C1 H1C . 0.9300
C2 C3 . 1.377(2)
C2 H2B . 0.9300
C3 C4 . 1.4101(18)
C4 C5 . 1.3894(17)
C4 C8 . 1.4436(18)
C5 C6 . 1.3752(19)
C5 H5A . 0.9300
C7 H7A . 0.9600
C7 H7B . 0.9600
C7 H7C . 0.9600
C8 H8A . 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_publ_flag
O2 H2 N1 0.94(2) 1.82(2) 2.6451(16) 145.0(18) 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
C6 C1 C2 C3 . -0.1(2)
C1 C2 C3 O2 . -179.95(12)
C1 C2 C3 C4 . 0.4(2)
O2 C3 C4 C5 . -179.65(11)
C2 C3 C4 C5 . -0.03(18)
O2 C3 C4 C8 . 1.09(19)
C2 C3 C4 C8 . -179.29(12)
C3 C4 C5 C6 . -0.68(19)
C8 C4 C5 C6 . 178.60(12)
C7 O1 C6 C5 . -170.46(14)
C7 O1 C6 C1 . 10.2(2)
C4 C5 C6 O1 . -178.37(12)
C4 C5 C6 C1 . 1.0(2)
C2 C1 C6 O1 . 178.72(13)
C2 C1 C6 C5 . -0.6(2)
N1 N1 C8 C4 3_566 179.45(12)
C5 C4 C8 N1 . 178.39(12)
C3 C4 C8 N1 . -2.36(19)
