#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/47/2224703.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_2224703
loop_
_publ_author_name
'Howie, R. Alan'
'de Souza, Marcus V. N.'
'Wardell, Solange M. S. V.'
'Wardell, James L.'
'Tiekink, Edward R. T.'
_publ_section_title
;
 N'-[(E)-2,6-Dichlorobenzylidene]pyrazine-2-carbohydrazide
;
_journal_coeditor_code           LH2969
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o178
_journal_page_last               o179
_journal_paper_doi               10.1107/S1600536809053343
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C12 H8 Cl2 N4 O'
_chemical_formula_moiety         'C12 H8 Cl2 N4 O'
_chemical_formula_sum            'C12 H8 Cl2 N4 O'
_chemical_formula_weight         295.12
_chemical_name_systematic
;
N'-[(E)-2,6-Dichlorobenzylidene]pyrazine-2-carbohydrazide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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
_cell_angle_beta                 111.709(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.9325(3)
_cell_length_b                   24.5997(13)
_cell_length_c                   7.6136(4)
_cell_measurement_reflns_used    11372
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.9
_cell_volume                     1206.31(11)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'publCIF (Westrip, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Enraf--Nonius KappaCCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  '10 cm confocal mirrors'
_diffrn_radiation_source         'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.052
_diffrn_reflns_av_sigmaI/netI    0.048
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8211
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         3.0
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.534
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.760
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.625
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.015
_refine_diff_density_max         0.40
_refine_diff_density_min         -0.34
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.14
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2108
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.14
_refine_ls_R_factor_all          0.062
_refine_ls_R_factor_gt           0.052
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0128P)²+2.8931P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.106
_refine_ls_wR_factor_ref         0.112
_reflns_number_gt                1858
_reflns_number_total             2108
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh2969.cif
_cod_data_source_block           I
_cod_original_cell_volume        1206.31(10)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2224703
_cod_database_fobs_code          2224703
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, z+1/2'
'-x, -y, -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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.21383(14) 0.04241(3) -0.00147(12) 0.0280(2) Uani d . 1 . .
Cl Cl2 0.35539(13) 0.19347(3) 0.56395(11) 0.0216(2) Uani d . 1 . .
O O1 0.4468(3) 0.31301(9) 0.2140(3) 0.0211(5) Uani d . 1 . .
N N1 0.2594(4) 0.41462(11) -0.2597(4) 0.0229(6) Uani d . 1 . .
N N2 0.2914(4) 0.30126(11) -0.2806(4) 0.0174(6) Uani d . 1 . .
N N3 0.2987(4) 0.24065(10) 0.0247(4) 0.0169(6) Uani d . 1 . .
H H3N 0.2381 0.2284 -0.0915 0.020 Uiso calc R 1 . .
N N4 0.3326(4) 0.20678(11) 0.1769(4) 0.0177(6) Uani d . 1 . .
C C1 0.3138(4) 0.32651(13) -0.1186(4) 0.0157(7) Uani d . 1 . .
C C2 0.2997(5) 0.38272(13) -0.1084(5) 0.0195(7) Uani d . 1 . .
H H2 0.3195 0.3990 0.0102 0.023 Uiso calc R 1 . .
C C3 0.2393(5) 0.38910(14) -0.4200(5) 0.0216(7) Uani d . 1 . .
H H3 0.2127 0.4101 -0.5312 0.026 Uiso calc R 1 . .
C C4 0.2556(5) 0.33325(13) -0.4310(4) 0.0202(7) Uani d . 1 . .
H H4 0.2409 0.3172 -0.5488 0.024 Uiso calc R 1 . .
C C5 0.3600(5) 0.29311(12) 0.0566(4) 0.0150(6) Uani d . 1 . .
C C6 0.2611(5) 0.15869(13) 0.1347(4) 0.0171(7) Uani d . 1 . .
H H6 0.1945 0.1492 0.0053 0.020 Uiso calc R 1 . .
C C7 0.2784(5) 0.11748(13) 0.2801(4) 0.0170(7) Uani d . 1 . .
C C8 0.2472(5) 0.06223(14) 0.2280(4) 0.0191(7) Uani d . 1 . .
C C9 0.2446(5) 0.02134(14) 0.3508(5) 0.0231(7) Uani d . 1 . .
H H9 0.2212 -0.0153 0.3084 0.028 Uiso calc R 1 . .
C C10 0.2764(5) 0.03408(14) 0.5368(5) 0.0243(8) Uani d . 1 . .
H H10 0.2743 0.0063 0.6227 0.029 Uiso calc R 1 . .
C C11 0.3110(5) 0.08741(13) 0.5960(5) 0.0198(7) Uani d . 1 . .
H H11 0.3330 0.0963 0.7234 0.024 Uiso calc R 1 . .
C C12 0.3142(5) 0.12832(13) 0.4710(5) 0.0184(7) Uani 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'
Cl Cl 0.1484 0.1585 '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_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 N1 C2 . . 115.5(3) ?
C4 N2 C1 . . 116.0(3) ?
C5 N3 N4 . . 118.8(3) ?
C5 N3 H3N . . 120.6 ?
N4 N3 H3N . . 120.6 ?
C6 N4 N3 . . 114.8(3) ?
N2 C1 C2 . . 121.8(3) ?
N2 C1 C5 . . 118.7(3) ?
C2 C1 C5 . . 119.5(3) ?
N1 C2 C1 . . 122.2(3) ?
N1 C2 H2 . . 118.9 ?
C1 C2 H2 . . 118.9 ?
N1 C3 C4 . . 122.7(3) ?
N1 C3 H3 . . 118.7 ?
C4 C3 H3 . . 118.7 ?
N2 C4 C3 . . 121.8(3) ?
N2 C4 H4 . . 119.1 ?
C3 C4 H4 . . 119.1 ?
O1 C5 N3 . . 124.4(3) ?
O1 C5 C1 . . 121.2(3) ?
N3 C5 C1 . . 114.5(3) ?
N4 C6 C7 . . 122.2(3) ?
N4 C6 H6 . . 118.9 ?
C7 C6 H6 . . 118.9 ?
C12 C7 C8 . . 115.0(3) ?
C12 C7 C6 . . 125.5(3) ?
C8 C7 C6 . . 119.4(3) ?
C9 C8 C7 . . 123.5(3) ?
C9 C8 Cl1 . . 116.4(3) ?
C7 C8 Cl1 . . 120.0(2) ?
C8 C9 C10 . . 119.4(3) ?
C8 C9 H9 . . 120.3 ?
C10 C9 H9 . . 120.3 ?
C11 C10 C9 . . 119.5(3) ?
C11 C10 H10 . . 120.3 ?
C9 C10 H10 . . 120.3 ?
C10 C11 C12 . . 120.6(3) ?
C10 C11 H11 . . 119.7 ?
C12 C11 H11 . . 119.7 ?
C11 C12 C7 . . 121.9(3) ?
C11 C12 Cl2 . . 115.6(2) ?
C7 C12 Cl2 . . 122.5(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C8 . 1.745(3) ?
Cl2 C12 . 1.732(3) ?
O1 C5 . 1.227(4) ?
N1 C3 . 1.333(4) ?
N1 C2 . 1.335(4) ?
N2 C4 . 1.335(4) ?
N2 C1 . 1.338(4) ?
N3 C5 . 1.352(4) ?
N3 N4 . 1.375(3) ?
N3 H3N . 0.8800 ?
N4 C6 . 1.277(4) ?
C1 C2 . 1.390(4) ?
C1 C5 . 1.497(4) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.384(5) ?
C3 H3 . 0.9500 ?
C4 H4 . 0.9500 ?
C6 C7 . 1.473(4) ?
C6 H6 . 0.9500 ?
C7 C12 . 1.407(4) ?
C7 C8 . 1.410(5) ?
C8 C9 . 1.378(5) ?
C9 C10 . 1.386(5) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.379(5) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.391(4) ?
C11 H11 . 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
N3 H3n O1 2_454 0.88 2.26 3.003(3) 142
N3 H3n N2 . 0.88 2.41 2.746(4) 103
C6 H6 O1 2_454 0.95 2.43 3.214(4) 140
C10 H10 N1 4_656 0.95 2.53 3.448(4) 162
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_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 N3 N4 C6 . . . . 176.7(3) ?
C4 N2 C1 C2 . . . . 0.2(4) ?
C4 N2 C1 C5 . . . . -178.4(3) ?
C3 N1 C2 C1 . . . . -1.8(5) ?
N2 C1 C2 N1 . . . . 1.3(5) ?
C5 C1 C2 N1 . . . . 179.9(3) ?
C2 N1 C3 C4 . . . . 1.0(5) ?
C1 N2 C4 C3 . . . . -1.1(4) ?
N1 C3 C4 N2 . . . . 0.5(5) ?
N4 N3 C5 O1 . . . . 0.7(5) ?
N4 N3 C5 C1 . . . . -179.4(3) ?
N2 C1 C5 O1 . . . . 155.9(3) ?
C2 C1 C5 O1 . . . . -22.7(4) ?
N2 C1 C5 N3 . . . . -24.0(4) ?
C2 C1 C5 N3 . . . . 157.4(3) ?
N3 N4 C6 C7 . . . . -178.3(3) ?
N4 C6 C7 C12 . . . . 19.9(5) ?
N4 C6 C7 C8 . . . . -163.6(3) ?
C12 C7 C8 C9 . . . . 2.0(5) ?
C6 C7 C8 C9 . . . . -174.9(3) ?
C12 C7 C8 Cl1 . . . . -176.8(2) ?
C6 C7 C8 Cl1 . . . . 6.3(4) ?
C7 C8 C9 C10 . . . . -0.8(5) ?
Cl1 C8 C9 C10 . . . . 178.1(3) ?
C8 C9 C10 C11 . . . . -0.3(5) ?
C9 C10 C11 C12 . . . . 0.0(5) ?
C10 C11 C12 C7 . . . . 1.3(5) ?
C10 C11 C12 Cl2 . . . . 179.0(3) ?
C8 C7 C12 C11 . . . . -2.2(4) ?
C6 C7 C12 C11 . . . . 174.4(3) ?
C8 C7 C12 Cl2 . . . . -179.8(2) ?
C6 C7 C12 Cl2 . . . . -3.1(5) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4660398
