#------------------------------------------------------------------------------
#$Date: 2016-07-27 04:33:42 +0300 (Wed, 27 Jul 2016) $
#$Revision: 184681 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/37/1543740.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_1543740
loop_
_publ_author_name
'Mohamooda Sumaya, U.'
'Reuben Jonathan, D.'
'Dravida Thendral, E. R. A.'
'Revathi, B. K.'
'Usha, G.'
_publ_section_title
;
 N,N'-(Ethane-1,2-diyl)bis(2-chlorobenzamide)
;
_journal_issue                   7
_journal_name_full               IUCrData
_journal_page_first              x161190
_journal_paper_doi               10.1107/S2414314616011901
_journal_volume                  1
_journal_year                    2016
_chemical_formula_iupac          'C16 H14 Cl2 N2 O2'
_chemical_formula_moiety         'C16 H14 Cl2 N2 O2'
_chemical_formula_sum            'C16 H14 Cl2 N2 O2'
_chemical_formula_weight         337.19
_chemical_name_systematic
;
N,N'-(Ethane-1,2-diyl)bis(2-chlorobenzamide)
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           'SHELXL-2014/7.(Sheldrick, 2014)'
_cell_angle_alpha                90
_cell_angle_beta                 104.189(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.9667(6)
_cell_length_b                   23.701(3)
_cell_length_c                   7.1113(8)
_cell_measurement_reflns_used    6198
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.26
_cell_measurement_theta_min      2.57
_cell_volume                     811.57(17)
_computing_cell_refinement
;
APEX2 and SAINT (Bruker, 2004)
;
_computing_data_collection
;
APEX2 (Bruker, 2004)
;
_computing_data_reduction
;
SAINT and XPREP (Bruker, 2004)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SIR92 (Altomare et al.,  1993)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       'ω and φ 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  0.0609
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            11558
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         3.077
_exptl_absorpt_coefficient_mu    0.407
_exptl_absorpt_correction_T_max  0.922
_exptl_absorpt_correction_T_min  0.885
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2004)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_description       block
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.317
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.168
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     105
_refine_ls_number_reflns         11558
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.168
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0641
_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)+1.3152P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1512
_refine_ls_wR_factor_ref         0.1561
_reflns_number_gt                1429
_reflns_number_total             1429
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            su4058sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        811.59(17)
_cod_database_code               1543740
_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.
;
_shelx_estimated_absorpt_t_min   0.886
_shelx_estimated_absorpt_t_max   0.923
loop_
_space_group_symop_operation_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_occupancy
C C1 0.5857(8) -0.00874(16) 0.5990(6) 0.0425(11) Uani d 1
H H1A 0.4843 -0.0367 0.6536 0.051 Uiso calc 1
H H1B 0.7574 -0.0259 0.5855 0.051 Uiso calc 1
C C2 0.4659(8) 0.06093(16) 0.8173(6) 0.0365(10) Uani d 1
C C3 0.5714(8) 0.10688(16) 0.9594(6) 0.0371(10) Uani d 1
C C4 0.8101(9) 0.09869(18) 1.1056(7) 0.0508(12) Uani d 1
H H4 0.9088 0.0652 1.1089 0.061 Uiso calc 1
C C5 0.9046(11) 0.1387(2) 1.2456(7) 0.0681(15) Uani d 1
H H5 1.0635 0.1321 1.3439 0.082 Uiso calc 1
C C6 0.7609(13) 0.1887(2) 1.2385(9) 0.0773(17) Uani d 1
H H6 0.8235 0.2160 1.3331 0.093 Uiso calc 1
C C7 0.5285(12) 0.1986(2) 1.0949(9) 0.0700(16) Uani d 1
H H7 0.4339 0.2327 1.0904 0.084 Uiso calc 1
C C8 0.4345(9) 0.15789(17) 0.9560(7) 0.0475(11) Uani d 1
N N1 0.6494(7) 0.03913(15) 0.7298(5) 0.0407(9) Uani d 1
O O1 0.2278(6) 0.04316(12) 0.7882(5) 0.0564(9) Uani d 1
Cl Cl1 0.1434(3) 0.17296(5) 0.7711(2) 0.0786(6) Uani d 1
H H1 0.822(10) 0.0537(18) 0.761(7) 0.069(15) 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
N1 C1 C1 . 3_656 111.5(4)
N1 C1 H1A . . 109.3
C1 C1 H1A 3_656 . 109.3
N1 C1 H1B . . 109.3
C1 C1 H1B 3_656 . 109.3
H1A C1 H1B . . 108.0
O1 C2 N1 . . 122.2(4)
O1 C2 C3 . . 122.0(3)
N1 C2 C3 . . 115.7(3)
C8 C3 C4 . . 117.5(4)
C8 C3 C2 . . 122.5(4)
C4 C3 C2 . . 120.0(4)
C5 C4 C3 . . 121.7(4)
C5 C4 H4 . . 119.1
C3 C4 H4 . . 119.1
C4 C5 C6 . . 119.1(5)
C4 C5 H5 . . 120.5
C6 C5 H5 . . 120.5
C7 C6 C5 . . 120.8(5)
C7 C6 H6 . . 119.6
C5 C6 H6 . . 119.6
C6 C7 C8 . . 119.5(5)
C6 C7 H7 . . 120.3
C8 C7 H7 . . 120.3
C7 C8 C3 . . 121.4(5)
C7 C8 Cl1 . . 118.1(4)
C3 C8 Cl1 . . 120.5(3)
C2 N1 C1 . . 122.5(3)
C2 N1 H1 . . 117(3)
C1 N1 H1 . . 120(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 N1 . 1.452(5)
C1 C1 3_656 1.513(8)
C1 H1A . 0.9700
C1 H1B . 0.9700
C2 O1 . 1.224(4)
C2 N1 . 1.328(5)
C2 C3 . 1.490(5)
C3 C8 . 1.384(5)
C3 C4 . 1.386(6)
C4 C5 . 1.371(6)
C4 H4 . 0.9300
C5 C6 . 1.379(7)
C5 H5 . 0.9300
C6 C7 . 1.362(8)
C6 H6 . 0.9300
C7 C8 . 1.378(6)
C7 H7 . 0.9300
C8 Cl1 . 1.736(5)
N1 H1 . 0.90(5)
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 H1 O1 1_655 0.90(5) 1.99(5) 2.801(4) 149(4)
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
O1 C2 C3 C8 . -52.3(6)
N1 C2 C3 C8 . 130.1(4)
O1 C2 C3 C4 . 125.5(5)
N1 C2 C3 C4 . -52.1(5)
C8 C3 C4 C5 . 1.8(7)
C2 C3 C4 C5 . -176.2(4)
C3 C4 C5 C6 . -1.1(7)
C4 C5 C6 C7 . -0.1(8)
C5 C6 C7 C8 . 0.7(8)
C6 C7 C8 C3 . 0.0(8)
C6 C7 C8 Cl1 . -178.1(4)
C4 C3 C8 C7 . -1.2(6)
C2 C3 C8 C7 . 176.7(4)
C4 C3 C8 Cl1 . 176.9(3)
C2 C3 C8 Cl1 . -5.2(5)
O1 C2 N1 C1 . -2.5(6)
C3 C2 N1 C1 . 175.2(4)
C1 C1 N1 C2 3_656 78.1(6)

_cod_database_fobs_code 1543740
