#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/46/2234647.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_2234647
loop_
_publ_author_name
'Xu, Jun'
_publ_section_title
;
 N'-(2,6-Dichlorobenzylidene)furan-2-carbohydrazide
;
_journal_coeditor_code           HB6741
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1455
_journal_paper_doi               10.1107/S160053681201639X
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C12 H8 Cl2 N2 O2'
_chemical_formula_moiety         'C12 H8 Cl2 N2 O2'
_chemical_formula_sum            'C12 H8 Cl2 N2 O2'
_chemical_formula_weight         283.10
_chemical_name_systematic
;
N'-(2,6-Dichlorobenzylidene)furan-2-carbohydrazide
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 91.565(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.9046(3)
_cell_length_b                   19.1113(12)
_cell_length_c                   12.9469(9)
_cell_measurement_reflns_used    2790
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.31
_cell_measurement_theta_min      3.19
_cell_volume                     1213.10(14)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_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'
_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  0.0278
_diffrn_reflns_av_sigmaI/netI    0.0501
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4654
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.32
_exptl_absorpt_coefficient_mu    0.529
_exptl_absorpt_correction_T_max  0.847
_exptl_absorpt_correction_T_min  0.814
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.550
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.298
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2464
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0795
_refine_ls_R_factor_gt           0.0470
_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)+(0.0537P)²+0.2769P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1065
_refine_ls_wR_factor_ref         0.1264
_reflns_number_gt                1679
_reflns_number_total             2464
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb6741.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2234647
_cod_database_fobs_code          2234647
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
Cl Cl1 0.43228(17) 0.43978(4) 0.09622(7) 0.0649(3) Uani d . 1 1
Cl Cl2 -0.28672(16) 0.52357(5) 0.38143(7) 0.0679(3) Uani d . 1 1
O O1 0.5843(3) 0.68141(9) 0.10167(15) 0.0429(5) Uani d . 1 1
N N1 0.1507(4) 0.63974(10) 0.09980(16) 0.0345(5) Uani d . 1 1
H H1A -0.0175 0.6482 0.0838 0.041 Uiso calc R 1 1
C C5 0.3496(5) 0.68267(12) 0.06671(19) 0.0322(6) Uani d . 1 1
N N2 0.2201(4) 0.58266(10) 0.15913(16) 0.0342(5) Uani d . 1 1
O O 0.4344(4) 0.78012(11) -0.04747(17) 0.0591(6) Uani d . 1 1
C C7 0.0788(5) 0.47943(13) 0.2441(2) 0.0367(6) Uani d . 1 1
C C4 0.2594(5) 0.72916(12) -0.0172(2) 0.0341(6) Uani d . 1 1
C C12 -0.0570(5) 0.46354(15) 0.3342(2) 0.0452(7) Uani d . 1 1
C C6 0.0226(5) 0.54460(13) 0.1877(2) 0.0357(6) Uani d . 1 1
H H6A -0.1564 0.5581 0.1729 0.043 Uiso calc R 1 1
C C3 0.0404(5) 0.72915(15) -0.0800(2) 0.0464(7) Uani d . 1 1
H H3A -0.1086 0.6993 -0.0761 0.056 Uiso calc R 1 1
C C11 -0.0117(7) 0.40168(19) 0.3879(3) 0.0630(9) Uani d . 1 1
H H11A -0.1082 0.3920 0.4471 0.076 Uiso calc R 1 1
C C8 0.2643(5) 0.42899(14) 0.2112(2) 0.0440(7) Uani d . 1 1
C C9 0.3144(6) 0.36796(16) 0.2651(3) 0.0596(9) Uani d . 1 1
H H9A 0.4412 0.3358 0.2418 0.071 Uiso calc R 1 1
C C1 0.3139(6) 0.81122(17) -0.1316(3) 0.0603(9) Uani d . 1 1
H H1B 0.3901 0.8477 -0.1686 0.072 Uiso calc R 1 1
C C10 0.1756(7) 0.35512(19) 0.3533(3) 0.0698(10) Uani d . 1 1
H H10A 0.2094 0.3141 0.3901 0.084 Uiso calc R 1 1
C C2 0.0749(6) 0.78259(17) -0.1535(2) 0.0578(8) Uani d . 1 1
H H2B -0.0466 0.7951 -0.2068 0.069 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'
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
C5 N1 N2 119.29(19)
C5 N1 H1A 120.4
N2 N1 H1A 120.4
O1 C5 N1 123.3(2)
O1 C5 C4 123.3(2)
N1 C5 C4 113.4(2)
C6 N2 N1 115.94(19)
C1 O C4 106.2(2)
C12 C7 C8 115.8(2)
C12 C7 C6 121.0(2)
C8 C7 C6 123.3(2)
C3 C4 O 109.2(2)
C3 C4 C5 132.6(2)
O C4 C5 117.9(2)
C11 C12 C7 122.2(3)
C11 C12 Cl2 119.0(2)
C7 C12 Cl2 118.8(2)
N2 C6 C7 119.7(2)
N2 C6 H6A 120.2
C7 C6 H6A 120.2
C4 C3 C2 107.7(2)
C4 C3 H3A 126.2
C2 C3 H3A 126.2
C10 C11 C12 119.4(3)
C10 C11 H11A 120.3
C12 C11 H11A 120.3
C9 C8 C7 122.5(3)
C9 C8 Cl1 117.0(2)
C7 C8 Cl1 120.5(2)
C10 C9 C8 119.3(3)
C10 C9 H9A 120.4
C8 C9 H9A 120.4
C2 C1 O 110.8(3)
C2 C1 H1B 124.6
O C1 H1B 124.6
C11 C10 C9 120.8(3)
C11 C10 H10A 119.6
C9 C10 H10A 119.6
C1 C2 C3 106.1(3)
C1 C2 H2B 126.9
C3 C2 H2B 126.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C8 1.733(3)
Cl2 C12 1.731(3)
O1 C5 1.226(3)
N1 C5 1.353(3)
N1 N2 1.372(3)
N1 H1A 0.8600
C5 C4 1.463(3)
N2 C6 1.275(3)
O C1 1.362(4)
O C4 1.363(3)
C7 C12 1.392(4)
C7 C8 1.400(4)
C7 C6 1.466(3)
C4 C3 1.329(4)
C12 C11 1.387(4)
C6 H6A 0.9300
C3 C2 1.410(4)
C3 H3A 0.9300
C11 C10 1.363(5)
C11 H11A 0.9300
C8 C9 1.378(4)
C9 C10 1.367(4)
C9 H9A 0.9300
C1 C2 1.318(4)
C1 H1B 0.9300
C10 H10A 0.9300
C2 H2B 0.9300
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
N1 H1A O1 1_455 0.86 2.07 2.890(2) 159
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 5270497
