#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/91/2239170.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_2239170
loop_
_publ_author_name
'Wang, Jinglin'
'He, Rong'
'Xin, Zhijuan'
'Shen, Huiling'
'Wang, Cairong'
_publ_contact_author
;
Wang Jinglin
Department of Chemistry, Changzhi University, Changzhi, Shanxi 046011,
People's Republic of China
;
_publ_section_title
;
 (E)-N'-(2-Chlorobenzylidene)-1-methyl-4-nitro-1H-pyrrole-2-carbohydrazide
;
_journal_coeditor_code           FF2124
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o99
_journal_paper_doi               10.1107/S1600536813034119
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C13 H11 Cl N4 O3'
_chemical_formula_moiety         'C13 H11 Cl N4 O3'
_chemical_formula_sum            'C13 H11 Cl N4 O3'
_chemical_formula_weight         306.71
_chemical_name_systematic
(E)-N'-(2-Chlorobenzylidene)-1-methyl-4-nitro-1H-pyrrole-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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.5230(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.7649(13)
_cell_length_b                   12.4993(11)
_cell_length_c                   8.1263(10)
_cell_measurement_reflns_used    1539
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.211
_cell_measurement_theta_min      3.0
_cell_volume                     1391.7(2)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1999)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics
'DIAMOND (Brandenburg, 1999) and SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'PLATON (Spek, 2009) and SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD'
_diffrn_measurement_method       'phi and omega 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  0.0712
_diffrn_reflns_av_sigmaI/netI    0.0655
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            6871
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.49
_exptl_absorpt_coefficient_mu    0.290
_exptl_absorpt_correction_T_max  0.9550
_exptl_absorpt_correction_T_min  0.9179
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.330
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2452
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0980
_refine_ls_R_factor_gt           0.0605
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0787P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1428
_refine_ls_wR_factor_ref         0.1641
_reflns_number_gt                1435
_reflns_number_total             2452
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            ff2124sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2239170
_cod_database_fobs_code          2239170
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 0.29032(9) 1.16858(8) 1.00653(18) 0.1044(6) Uani d . 1 1
N N1 0.14340(19) 0.51021(19) 1.0868(3) 0.0508(7) Uani d . 1 1
N N2 -0.0430(2) 0.5940(3) 1.3388(4) 0.0712(9) Uani d . 1 1
N N3 0.24317(19) 0.7725(2) 1.0085(3) 0.0512(8) Uani d . 1 1
H H3 0.2231 0.7996 1.0964 0.061 Uiso calc R 1 1
N N4 0.30201(18) 0.83156(19) 0.9133(3) 0.0470(7) Uani d . 1 1
O O1 0.24317(17) 0.62828(16) 0.8366(3) 0.0587(7) Uani d . 1 1
O O2 -0.0656(2) 0.6852(3) 1.3780(4) 0.1057(12) Uani d . 1 1
O O3 -0.08399(19) 0.5122(3) 1.3789(3) 0.0907(9) Uani d . 1 1
C C1 0.2175(2) 0.6716(2) 0.9618(4) 0.0465(8) Uani d . 1 1
C C2 0.1506(2) 0.6203(2) 1.0708(4) 0.0451(8) Uani d . 1 1
C C3 0.0829(2) 0.6674(3) 1.1612(4) 0.0514(8) Uani d . 1 1
H H3A 0.0711 0.7403 1.1715 0.062 Uiso calc R 1 1
C C4 0.0352(2) 0.5839(3) 1.2344(4) 0.0561(9) Uani d . 1 1
C C5 0.0737(2) 0.4884(3) 1.1897(4) 0.0573(9) Uani d . 1 1
H H5 0.0554 0.4209 1.2235 0.069 Uiso calc R 1 1
C C6 0.2046(3) 0.4285(3) 1.0169(5) 0.0659(10) Uani d . 1 1
H H6A 0.2708 0.4362 1.0642 0.099 Uiso calc R 1 1
H H6B 0.2017 0.4376 0.8992 0.099 Uiso calc R 1 1
H H6C 0.1810 0.3586 1.0416 0.099 Uiso calc R 1 1
C C7 0.3117(2) 0.9297(2) 0.9548(4) 0.0483(8) Uani d . 1 1
H H7 0.2764 0.9569 1.0373 0.058 Uiso calc R 1 1
C C8 0.3779(2) 1.0000(2) 0.8743(4) 0.0467(8) Uani d . 1 1
C C9 0.3778(2) 1.1102(2) 0.8944(4) 0.0571(9) Uani d . 1 1
C C10 0.4438(3) 1.1761(3) 0.8256(5) 0.0698(11) Uani d . 1 1
H H10 0.4413 1.2498 0.8406 0.084 Uiso calc R 1 1
C C11 0.5133(3) 1.1319(3) 0.7348(5) 0.0698(11) Uani d . 1 1
H H11 0.5587 1.1756 0.6900 0.084 Uiso calc R 1 1
C C12 0.5154(3) 1.0231(3) 0.7108(5) 0.0659(10) Uani d . 1 1
H H12 0.5620 0.9933 0.6491 0.079 Uiso calc R 1 1
C C13 0.4481(2) 0.9577(3) 0.7784(4) 0.0568(9) Uani d . 1 1
H H13 0.4497 0.8843 0.7598 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'
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 C2 108.5(3)
C5 N1 C6 124.2(3)
C2 N1 C6 127.1(2)
O3 N2 O2 124.7(3)
O3 N2 C4 118.2(4)
O2 N2 C4 117.1(3)
C1 N3 N4 119.4(2)
C1 N3 H3 120.3
N4 N3 H3 120.3
C7 N4 N3 114.6(2)
O1 C1 N3 123.5(3)
O1 C1 C2 123.1(3)
N3 C1 C2 113.3(3)
C3 C2 N1 108.5(3)
C3 C2 C1 128.8(3)
N1 C2 C1 122.6(3)
C2 C3 C4 106.1(3)
C2 C3 H3A 126.9
C4 C3 H3A 126.9
C5 C4 C3 109.2(3)
C5 C4 N2 124.3(3)
C3 C4 N2 126.4(3)
N1 C5 C4 107.6(3)
N1 C5 H5 126.2
C4 C5 H5 126.2
N1 C6 H6A 109.5
N1 C6 H6B 109.5
H6A C6 H6B 109.5
N1 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
N4 C7 C8 120.8(3)
N4 C7 H7 119.6
C8 C7 H7 119.6
C9 C8 C13 116.7(3)
C9 C8 C7 122.4(3)
C13 C8 C7 120.9(3)
C10 C9 C8 122.4(3)
C10 C9 Cl1 118.5(3)
C8 C9 Cl1 119.1(2)
C11 C10 C9 119.6(3)
C11 C10 H10 120.2
C9 C10 H10 120.2
C12 C11 C10 119.8(3)
C12 C11 H11 120.1
C10 C11 H11 120.1
C11 C12 C13 120.2(3)
C11 C12 H12 119.9
C13 C12 H12 119.9
C12 C13 C8 121.3(3)
C12 C13 H13 119.4
C8 C13 H13 119.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C9 1.739(3)
N1 C5 1.359(4)
N1 C2 1.387(4)
N1 C6 1.472(4)
N2 O3 1.227(4)
N2 O2 1.232(4)
N2 C4 1.439(4)
N3 C1 1.354(4)
N3 N4 1.386(3)
N3 H3 0.8600
N4 C7 1.276(4)
O1 C1 1.234(3)
C1 C2 1.483(4)
C2 C3 1.374(4)
C3 C4 1.397(4)
C3 H3A 0.9300
C4 C5 1.369(5)
C5 H5 0.9300
C6 H6A 0.9600
C6 H6B 0.9600
C6 H6C 0.9600
C7 C8 1.465(4)
C7 H7 0.9300
C8 C9 1.387(4)
C8 C13 1.402(4)
C9 C10 1.383(5)
C10 C11 1.379(5)
C10 H10 0.9300
C11 C12 1.374(5)
C11 H11 0.9300
C12 C13 1.388(4)
C12 H12 0.9300
C13 H13 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
_geom_hbond_publ_flag
N3 H3 O1 4_576 0.860 2.144 2.941(3) 154.03 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
C1 N3 N4 C7 171.3(3)
N4 N3 C1 O1 -0.5(5)
N4 N3 C1 C2 -177.2(3)
C5 N1 C2 C3 -1.6(4)
C6 N1 C2 C3 -177.2(3)
C5 N1 C2 C1 -177.7(3)
C6 N1 C2 C1 6.7(5)
O1 C1 C2 C3 -147.4(4)
N3 C1 C2 C3 29.3(5)
O1 C1 C2 N1 27.9(5)
N3 C1 C2 N1 -155.5(3)
N1 C2 C3 C4 0.8(4)
C1 C2 C3 C4 176.6(3)
C2 C3 C4 C5 0.3(4)
C2 C3 C4 N2 -178.9(3)
O3 N2 C4 C5 -6.7(6)
O2 N2 C4 C5 175.1(4)
O3 N2 C4 C3 172.3(3)
O2 N2 C4 C3 -5.9(6)
C2 N1 C5 C4 1.7(4)
C6 N1 C5 C4 177.5(3)
C3 C4 C5 N1 -1.2(4)
N2 C4 C5 N1 178.0(3)
N3 N4 C7 C8 175.1(3)
N4 C7 C8 C9 168.3(3)
N4 C7 C8 C13 -14.7(5)
C13 C8 C9 C10 -0.6(6)
C7 C8 C9 C10 176.4(4)
C13 C8 C9 Cl1 178.0(3)
C7 C8 C9 Cl1 -4.9(5)
C8 C9 C10 C11 -0.7(6)
Cl1 C9 C10 C11 -179.4(3)
C9 C10 C11 C12 1.2(6)
C10 C11 C12 C13 -0.4(6)
C11 C12 C13 C8 -1.0(6)
C9 C8 C13 C12 1.5(5)
C7 C8 C13 C12 -175.6(3)
