#------------------------------------------------------------------------------
#$Date: 2017-05-05 08:49:52 +0300 (Fri, 05 May 2017) $
#$Revision: 196234 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/92/2239263.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_2239263
loop_
_publ_author_name
'Agarwal, Palak'
'Mishra, Pragati'
'Gupta, Nikita'
Neelam
'Sahoo, Priyaranjan'
'Kumar, Satish'
_publ_section_title
;
 (Z)-3-[2-(2,4-Dinitrophenyl)hydrazin-1-ylidene]isobenzofuran-1(3H)-one
 dichloromethane hemisolvate
;
_journal_coeditor_code           FJ2664
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o418
_journal_paper_doi               10.1107/S1600536814004929
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C14 H8 N4 O6, 1/2(C H2 Cl2)'
_chemical_formula_moiety         'C14 H8 N4 O6, 0.5(C H2 Cl2)'
_chemical_formula_sum            'C14.5 H9 Cl N4 O6'
_chemical_formula_weight         370.70
_chemical_name_systematic
'(Z)-3-[2-(2,4-Dinitrophenyl)hydrazin-1-ylidene]isobenzofuran-1(3H)-one dichloromethane hemisolvate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_method
;
CrysAlis Pro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_cell_angle_alpha                90.0
_cell_angle_beta                 93.816(7)
_cell_angle_gamma                90.0
_cell_formula_units_Z            8
_cell_length_a                   14.0834(11)
_cell_length_b                   8.2605(6)
_cell_length_c                   26.561(2)
_cell_measurement_reflns_used    3399
_cell_measurement_temperature    297.15(2)
_cell_measurement_theta_max      29.1855
_cell_measurement_theta_min      2.9809
_cell_volume                     3083.1(4)
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2011)
;
_computing_data_collection
;
CrysAlis PRO (Agilent, 2011)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2011)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al.,
2008)
;
_computing_publication_material
'OLEX2 (Dolomanov et al., 2009) and publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      297.15(2)
_diffrn_detector_area_resol_mean 15.9853
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.910
_diffrn_measurement_device_type  'Agilent Xcalibur Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            20814
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.250
_diffrn_reflns_theta_min         2.987
_exptl_absorpt_coefficient_mu    0.292
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82444
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent, 2011)'
_exptl_crystal_colour            'clear yellow--red'
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rect. prism'
_exptl_crystal_F_000             1512
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.441
_refine_diff_density_min         -0.346
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         3832
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0934
_refine_ls_R_factor_gt           0.0568
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0530P)²+3.2470P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1233
_refine_ls_wR_factor_ref         0.1413
_reflns_number_gt                2568
_reflns_number_total             3832
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fj2664sup1.cif
_cod_data_source_block           I
_cod_depositor_comments
;

2017-04-15
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C29 H18 Cl2 N8 O12'
_cod_original_formula_weight         741.41
_cod_original_formula_moiety         '2(C14 H8 N4 O6), C H2 Cl2'
_cod_original_formula_units_Z            4
_cod_original_cell_volume        3083.2(3)
_cod_database_code               2239263
_cod_database_fobs_code          2239263
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           .2013
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_occupancy
Cl Cl1 0.39898(6) 0.54376(10) 0.73756(3) 0.0797(3) Uani d 1
O O2 0.41801(11) 0.47047(18) 0.54833(5) 0.0411(4) Uani d 1
O O3 0.30079(13) 0.1587(2) 0.45274(6) 0.0566(5) Uani d 1
O O4 0.48996(13) 0.4056(2) 0.62423(6) 0.0562(5) Uani d 1
O O5 0.24791(13) 0.0449(2) 0.38349(7) 0.0554(5) Uani d 1
N N6 0.33004(14) 0.4709(2) 0.45706(7) 0.0407(4) Uani d 1
H H6 0.3319(18) 0.386(3) 0.4723(9) 0.049 Uiso d 1
N N7 0.26939(13) 0.1660(2) 0.40803(7) 0.0408(4) Uani d 1
N N8 0.16035(16) 0.4760(3) 0.26002(7) 0.0529(5) Uani d 1
N N9 0.35397(13) 0.6171(2) 0.47867(6) 0.0403(4) Uani d 1
C C10 0.21556(15) 0.3263(3) 0.33550(8) 0.0381(5) Uani d 1
H H10 0.1961 0.2307 0.3195 0.046 Uiso calc 1
C C11 0.42937(14) 0.7496(3) 0.55314(8) 0.0357(5) Uani d 1
C C12 0.39564(15) 0.6131(3) 0.52246(8) 0.0371(5) Uani d 1
C C13 0.47111(15) 0.6872(3) 0.59783(8) 0.0377(5) Uani d 1
C C14 0.46430(15) 0.5103(3) 0.59583(8) 0.0400(5) Uani d 1
O O15 0.1569(2) 0.6044(3) 0.23776(8) 0.0904(8) Uani d 1
O O16 0.13589(19) 0.3503(3) 0.23967(7) 0.0891(8) Uani d 1
C C17 0.28732(14) 0.4683(3) 0.40931(7) 0.0355(5) Uani d 1
C C18 0.25776(14) 0.3240(3) 0.38441(8) 0.0351(5) Uani d 1
C C19 0.20337(15) 0.4720(3) 0.31152(8) 0.0396(5) Uani d 1
C C20 0.42629(17) 0.9146(3) 0.54405(9) 0.0443(5) Uani d 1
H H20 0.3976 0.9565 0.5143 0.053 Uiso calc 1
C C21 0.46757(18) 1.0142(3) 0.58095(10) 0.0508(6) Uani d 1
H H21 0.4676 1.1255 0.5757 0.061 Uiso calc 1
C C22 0.23198(16) 0.6165(3) 0.33451(8) 0.0440(5) Uani d 1
H H22 0.2230 0.7141 0.3174 0.053 Uiso calc 1
C C23 0.50939(17) 0.9519(3) 0.62607(9) 0.0495(6) Uani d 1
H H23 0.5361 1.0227 0.6503 0.059 Uiso calc 1
C C24 0.27340(16) 0.6143(3) 0.38250(8) 0.0410(5) Uani d 1
H H24 0.2928 0.7112 0.3978 0.049 Uiso calc 1
C C25 0.51179(16) 0.7874(3) 0.63543(9) 0.0449(6) Uani d 1
H H25 0.5393 0.7456 0.6655 0.054 Uiso calc 1
C C26 0.5000 0.4238(5) 0.7500 0.0587(10) Uani d 1
H H26 0.4913 0.3631 0.7795 0.070 Uiso d 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'
Cl Cl 0.1484 0.1585 '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_1
_geom_angle_site_symmetry_3
_geom_angle
C12 O2 C14 . . 108.59(16)
N9 N6 H6 . . 123.9(18)
C17 N6 H6 . . 116.5(18)
C17 N6 N9 . . 118.88(18)
O3 N7 C18 . . 118.66(18)
O5 N7 O3 . . 122.09(19)
O5 N7 C18 . . 119.25(17)
O15 N8 C19 . . 118.5(2)
O16 N8 O15 . . 122.1(2)
O16 N8 C19 . . 119.2(2)
C12 N9 N6 . . 116.54(18)
C18 C10 H10 . . 120.7
C19 C10 H10 . . 120.7
C19 C10 C18 . . 118.7(2)
C13 C11 C12 . . 107.21(19)
C20 C11 C12 . . 131.4(2)
C20 C11 C13 . . 121.4(2)
O2 C12 C11 . . 109.01(17)
N9 C12 O2 . . 123.53(19)
N9 C12 C11 . . 127.5(2)
C11 C13 C14 . . 108.41(19)
C11 C13 C25 . . 121.6(2)
C25 C13 C14 . . 130.0(2)
O2 C14 C13 . . 106.77(18)
O4 C14 O2 . . 119.9(2)
O4 C14 C13 . . 133.3(2)
N6 C17 C18 . . 123.03(19)
N6 C17 C24 . . 119.6(2)
C24 C17 C18 . . 117.35(18)
C10 C18 N7 . . 116.37(19)
C10 C18 C17 . . 121.29(19)
C17 C18 N7 . . 122.34(18)
C10 C19 N8 . . 119.2(2)
C10 C19 C22 . . 121.89(19)
C22 C19 N8 . . 118.9(2)
C11 C20 H20 . . 121.4
C21 C20 C11 . . 117.2(2)
C21 C20 H20 . . 121.4
C20 C21 H21 . . 119.2
C20 C21 C23 . . 121.6(2)
C23 C21 H21 . . 119.2
C19 C22 H22 . . 120.3
C24 C22 C19 . . 119.5(2)
C24 C22 H22 . . 120.3
C21 C23 H23 . . 119.3
C25 C23 C21 . . 121.4(2)
C25 C23 H23 . . 119.3
C17 C24 H24 . . 119.3
C22 C24 C17 . . 121.3(2)
C22 C24 H24 . . 119.3
C13 C25 H25 . . 121.6
C23 C25 C13 . . 116.9(2)
C23 C25 H25 . . 121.6
Cl1 C26 Cl1 . 2_656 110.9(2)
Cl1 C26 H26 . . 108.0
Cl1 C26 H26 2_656 . 107.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Cl1 C26 . 1.747(2)
O2 C12 . 1.389(3)
O2 C14 . 1.419(3)
O3 N7 . 1.241(2)
O4 C14 . 1.188(3)
O5 N7 . 1.221(2)
N6 H6 . 0.81(3)
N6 N9 . 1.370(3)
N6 C17 . 1.367(3)
N7 C18 . 1.453(3)
N8 O15 . 1.214(3)
N8 O16 . 1.210(3)
N8 C19 . 1.459(3)
N9 C12 . 1.268(3)
C10 H10 . 0.9300
C10 C18 . 1.392(3)
C10 C19 . 1.367(3)
C11 C12 . 1.453(3)
C11 C13 . 1.388(3)
C11 C20 . 1.385(3)
C13 C14 . 1.466(3)
C13 C25 . 1.391(3)
C17 C18 . 1.413(3)
C17 C24 . 1.407(3)
C19 C22 . 1.389(3)
C20 H20 . 0.9300
C20 C21 . 1.378(3)
C21 H21 . 0.9300
C21 C23 . 1.398(4)
C22 H22 . 0.9300
C22 C24 . 1.366(3)
C23 H23 . 0.9300
C23 C25 . 1.382(3)
C24 H24 . 0.9300
C25 H25 . 0.9300
C26 Cl1 2_656 1.747(2)
C26 H26 . 0.9440
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
N6 H6 O3 0.81(3) 1.99(3) 2.613(3) 134(2)
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
O3 N7 C18 C10 -175.26(19)
O3 N7 C18 C17 4.7(3)
O5 N7 C18 C10 4.6(3)
O5 N7 C18 C17 -175.45(19)
N6 N9 C12 O2 0.6(3)
N6 N9 C12 C11 179.12(19)
N6 C17 C18 N7 0.8(3)
N6 C17 C18 C10 -179.2(2)
N6 C17 C24 C22 179.2(2)
N8 C19 C22 C24 -179.2(2)
N9 N6 C17 C18 -178.27(18)
N9 N6 C17 C24 3.3(3)
C10 C19 C22 C24 -0.1(3)
C11 C13 C14 O2 0.5(2)
C11 C13 C14 O4 179.2(3)
C11 C13 C25 C23 -0.5(3)
C11 C20 C21 C23 -1.1(3)
C12 O2 C14 O4 -179.9(2)
C12 O2 C14 C13 -1.0(2)
C12 C11 C13 C14 0.1(2)
C12 C11 C13 C25 179.23(19)
C12 C11 C20 C21 -178.3(2)
C13 C11 C12 O2 -0.7(2)
C13 C11 C12 N9 -179.4(2)
C13 C11 C20 C21 0.9(3)
C14 O2 C12 N9 179.8(2)
C14 O2 C12 C11 1.0(2)
C14 C13 C25 C23 178.5(2)
O15 N8 C19 C10 -174.2(2)
O15 N8 C19 C22 5.0(4)
O16 N8 C19 C10 0.4(4)
O16 N8 C19 C22 179.5(2)
C17 N6 N9 C12 -178.2(2)
C18 C10 C19 N8 179.22(19)
C18 C10 C19 C22 0.1(3)
C18 C17 C24 C22 0.7(3)
C19 C10 C18 N7 -179.73(18)
C19 C10 C18 C17 0.3(3)
C19 C22 C24 C17 -0.3(3)
C20 C11 C12 O2 178.5(2)
C20 C11 C12 N9 -0.1(4)
C20 C11 C13 C14 -179.2(2)
C20 C11 C13 C25 -0.1(3)
C20 C21 C23 C25 0.5(4)
C21 C23 C25 C13 0.3(3)
C24 C17 C18 N7 179.32(19)
C24 C17 C18 C10 -0.7(3)
C25 C13 C14 O2 -178.5(2)
C25 C13 C14 O4 0.2(4)
