#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/81/2218109.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_2218109
loop_
_publ_author_name
'Chattopadhyay, Basab'
'Basu, Sharmila'
'Ghosh, Somnath'
'Helliwell, Madeleine'
'Mukherjee, Monika'
_publ_section_title
;
 2,2'-Diazinodimethylidyne)di-o-phenylene) dibenzoate
;
_journal_coeditor_code           FJ2111
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o866
_journal_paper_doi               10.1107/S1600536808010155
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C28 H20 N2 O4'
_chemical_formula_moiety         'C28 H20 N2 O4'
_chemical_formula_sum            'C28 H20 N2 O4'
_chemical_formula_weight         448.46
_chemical_name_common            N,N'-di-(2,2'-dibenzoyloxy)benzylidenehydrazine
_chemical_name_systematic
;
2,2'-(Diazinodimethylidyne)di-o-phenylene dibenzoate
;
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_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                73.201(2)
_cell_angle_beta                 82.066(3)
_cell_angle_gamma                74.441(2)
_cell_formula_units_Z            1
_cell_length_a                   5.5442(9)
_cell_length_b                   7.9966(13)
_cell_length_c                   13.455(2)
_cell_measurement_reflns_used    1976
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.54
_cell_measurement_theta_min      2.44
_cell_volume                     548.95(15)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.1167
_diffrn_reflns_av_sigmaI/netI    0.0685
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2797
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.58
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             234
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.281
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1885
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0514
_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)+(0.0874P)²+0.0721P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1301
_refine_ls_wR_factor_ref         0.1345
_reflns_number_gt                1692
_reflns_number_total             1885
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fj2111.cif
_cod_data_source_block           I
_cod_original_cell_volume        548.94(15)
_cod_database_code               2218109
_cod_database_fobs_code          2218109
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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 -0.60203(19) -0.17401(13) 0.23034(8) 0.0250(3) Uani d . 1
O O2 -0.3270(2) -0.15072(14) 0.33163(8) 0.0299(3) Uani d . 1
N N1 -0.1081(2) 0.06358(16) 0.01102(9) 0.0256(3) Uani d . 1
C C1 -0.2578(3) -0.01150(19) 0.07886(11) 0.0246(4) Uani d . 1
H H1 -0.2140 -0.1383 0.1073 0.029 Uiso calc R 1
C C2 -0.4964(3) 0.09474(19) 0.11375(11) 0.0239(4) Uani d . 1
C C3 -0.5716(3) 0.2813(2) 0.07164(12) 0.0273(4) Uani d . 1
H H3 -0.4643 0.3410 0.0206 0.033 Uiso calc R 1
C C4 -0.7999(3) 0.3799(2) 0.10330(12) 0.0291(4) Uani d . 1
H H4 -0.8471 0.5066 0.0747 0.035 Uiso calc R 1
C C5 -0.9593(3) 0.2945(2) 0.17645(12) 0.0287(4) Uani d . 1
H H5 -1.1170 0.3624 0.1972 0.034 Uiso calc R 1
C C6 -0.8898(3) 0.1100(2) 0.21961(11) 0.0263(4) Uani d . 1
H H6 -0.9986 0.0508 0.2700 0.032 Uiso calc R 1
C C7 -0.6600(3) 0.01385(19) 0.18816(11) 0.0240(4) Uani d . 1
C C8 -0.4341(3) -0.24172(19) 0.30508(11) 0.0228(4) Uani d . 1
C C9 -0.3993(3) -0.43981(19) 0.34806(11) 0.0231(4) Uani d . 1
C C10 -0.2123(3) -0.5285(2) 0.41615(12) 0.0264(4) Uani d . 1
H H10 -0.1100 -0.4633 0.4326 0.032 Uiso calc R 1
C C11 -0.1736(3) -0.7120(2) 0.46053(12) 0.0283(4) Uani d . 1
H H11 -0.0454 -0.7729 0.5076 0.034 Uiso calc R 1
C C12 -0.3236(3) -0.8067(2) 0.43577(12) 0.0293(4) Uani d . 1
H H12 -0.2985 -0.9326 0.4664 0.035 Uiso calc R 1
C C13 -0.5087(3) -0.7186(2) 0.36691(12) 0.0287(4) Uani d . 1
H H13 -0.6087 -0.7845 0.3496 0.034 Uiso calc R 1
C C14 -0.5495(3) -0.5342(2) 0.32285(12) 0.0264(4) Uani d . 1
H H14 -0.6781 -0.4733 0.2761 0.032 Uiso calc R 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'
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_3
_geom_angle
C8 O1 C7 . 116.52(10)
C1 N1 N1 2 111.37(15)
N1 C1 C2 . 121.02(13)
N1 C1 H1 . 119.5
C2 C1 H1 . 119.5
C7 C2 C3 . 117.32(14)
C7 C2 C1 . 121.33(13)
C3 C2 C1 . 121.33(13)
C4 C3 C2 . 120.94(14)
C4 C3 H3 . 119.5
C2 C3 H3 . 119.5
C5 C4 C3 . 120.14(14)
C5 C4 H4 . 119.9
C3 C4 H4 . 119.9
C4 C5 C6 . 120.20(14)
C4 C5 H5 . 119.9
C6 C5 H5 . 119.9
C7 C6 C5 . 118.95(14)
C7 C6 H6 . 120.5
C5 C6 H6 . 120.5
C6 C7 C2 . 122.43(14)
C6 C7 O1 . 117.04(13)
C2 C7 O1 . 120.43(13)
O2 C8 O1 . 123.28(13)
O2 C8 C9 . 125.08(13)
O1 C8 C9 . 111.63(12)
C10 C9 C14 . 120.38(14)
C10 C9 C8 . 117.36(13)
C14 C9 C8 . 122.25(13)
C9 C10 C11 . 120.26(13)
C9 C10 H10 . 119.9
C11 C10 H10 . 119.9
C10 C11 C12 . 119.53(14)
C10 C11 H11 . 120.2
C12 C11 H11 . 120.2
C13 C12 C11 . 120.28(14)
C13 C12 H12 . 119.9
C11 C12 H12 . 119.9
C12 C13 C14 . 120.35(13)
C12 C13 H13 . 119.8
C14 C13 H13 . 119.8
C13 C14 C9 . 119.19(14)
C13 C14 H14 . 120.4
C9 C14 H14 . 120.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C8 . 1.3580(18)
O1 C7 . 1.4073(17)
O2 C8 . 1.2045(17)
N1 C1 . 1.274(2)
N1 N1 2 1.408(2)
C1 C2 . 1.466(2)
C1 H1 . 0.9500
C2 C7 . 1.390(2)
C2 C3 . 1.401(2)
C3 C4 . 1.384(2)
C3 H3 . 0.9500
C4 C5 . 1.383(2)
C4 H4 . 0.9500
C5 C6 . 1.387(2)
C5 H5 . 0.9500
C6 C7 . 1.381(2)
C6 H6 . 0.9500
C8 C9 . 1.489(2)
C9 C10 . 1.382(2)
C9 C14 . 1.393(2)
C10 C11 . 1.384(2)
C10 H10 . 0.9500
C11 C12 . 1.392(2)
C11 H11 . 0.9500
C12 C13 . 1.380(2)
C12 H12 . 0.9500
C13 C14 . 1.389(2)
C13 H13 . 0.9500
C14 H14 . 0.9500
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
C6 H6 O2 1_455 0.95 2.64 3.519(2) 153.5 y
C5 H5 Cg1 1_465 0.95 2.79 3.510(2) 133 y
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
N1 N1 C1 C2 2 -179.77(13)
N1 C1 C2 C7 . -179.63(13)
N1 C1 C2 C3 . 1.9(2)
C7 C2 C3 C4 . 0.0(2)
C1 C2 C3 C4 . 178.48(13)
C2 C3 C4 C5 . -0.9(2)
C3 C4 C5 C6 . 1.0(2)
C4 C5 C6 C7 . -0.1(2)
C5 C6 C7 C2 . -0.8(2)
C5 C6 C7 O1 . -177.14(12)
C3 C2 C7 C6 . 0.9(2)
C1 C2 C7 C6 . -177.63(13)
C3 C2 C7 O1 . 177.10(12)
C1 C2 C7 O1 . -1.4(2)
C8 O1 C7 C6 . -104.90(14)
C8 O1 C7 C2 . 78.69(16)
C7 O1 C8 O2 . -3.9(2)
C7 O1 C8 C9 . 176.64(11)
O2 C8 C9 C10 . -6.7(2)
O1 C8 C9 C10 . 172.76(12)
O2 C8 C9 C14 . 172.44(14)
O1 C8 C9 C14 . -8.13(19)
C14 C9 C10 C11 . -0.4(2)
C8 C9 C10 C11 . 178.68(12)
C9 C10 C11 C12 . 0.3(2)
C10 C11 C12 C13 . 0.4(2)
C11 C12 C13 C14 . -1.0(2)
C12 C13 C14 C9 . 0.8(2)
C10 C9 C14 C13 . -0.1(2)
C8 C9 C14 C13 . -179.14(12)
