#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/97/2209761.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_2209761
loop_
_publ_author_name
'Cui-Cui Yuan'
'Li Wu'
'Zhi-Yong Xing'
'Xue-Fang Shi'
_publ_section_title
;
 4-Chlorobenzaldehyde (pyrazin-2-ylcarbonyl)hydrazone
;
_journal_coeditor_code           BT2126
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3274
_journal_page_last               o3275
_journal_paper_doi               10.1107/S1600536806026006
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C12 H9 Cl N4 O'
_chemical_formula_moiety         'C12 H9 Cl N4 O'
_chemical_formula_sum            'C12 H9 Cl N4 O'
_chemical_formula_weight         260.68
_chemical_melting_point          .479E-305
_chemical_name_systematic
;
4-Chlorobenzaldehyde (pyrazine-2-carbonyl)hydrazone
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                84.883(5)
_cell_angle_beta                 80.500(5)
_cell_angle_gamma                73.769(4)
_cell_formula_units_Z            2
_cell_length_a                   5.8860(16)
_cell_length_b                   7.818(2)
_cell_length_c                   13.500(4)
_cell_measurement_reflns_used    1017
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.73
_cell_measurement_theta_min      2.72
_cell_volume                     587.7(3)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0154
_diffrn_reflns_av_sigmaI/netI    0.0354
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3000
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.72
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.317
_exptl_absorpt_correction_T_max  0.9690
_exptl_absorpt_correction_T_min  0.9248
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.186
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2055
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0389
_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)+(0.044P)²+0.1868P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0870
_refine_ls_wR_factor_ref         0.1067
_reflns_number_gt                1350
_reflns_number_total             2055
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt2126.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2209761
_cod_database_fobs_code          2209761
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
Cl Cl1 0.86529(15) -0.25496(11) 0.97972(6) 0.0746(3) Uani d . 1
O O1 0.0420(3) 0.3083(2) 0.46929(13) 0.0599(5) Uani d . 1
N N1 0.0684(4) 0.6053(3) 0.19755(17) 0.0571(6) Uani d . 1
N N2 0.4740(3) 0.4499(3) 0.29061(15) 0.0455(5) Uani d . 1
N N3 0.4343(4) 0.2867(3) 0.47414(16) 0.0508(6) Uani d . 1
H H3A 0.554(5) 0.311(4) 0.441(2) 0.061 Uiso d . 1
N N4 0.4422(4) 0.1945(3) 0.56590(15) 0.0479(5) Uani d . 1
C C1 0.4860(4) 0.5378(3) 0.20140(19) 0.0522(7) Uani d . 1
H H1 0.6338 0.5489 0.1691 0.063 Uiso calc R 1
C C2 0.2867(5) 0.6125(3) 0.1555(2) 0.0529(7) Uani d . 1
H H2 0.3053 0.6704 0.0927 0.063 Uiso calc R 1
C C3 0.0565(4) 0.5184(3) 0.2872(2) 0.0519(7) Uani d . 1
H H3 -0.0923 0.5105 0.3200 0.062 Uiso calc R 1
C C4 0.2557(4) 0.4399(3) 0.33318(18) 0.0400(6) Uani d . 1
C C5 0.2314(5) 0.3387(3) 0.43219(18) 0.0446(6) Uani d . 1
C C6 0.6497(5) 0.1414(3) 0.59197(19) 0.0475(6) Uani d . 1
H H6 0.7781 0.1645 0.5481 0.057 Uiso calc R 1
C C7 0.6948(4) 0.0457(3) 0.68795(18) 0.0427(6) Uani d . 1
C C8 0.5124(4) 0.0270(3) 0.76430(19) 0.0487(6) Uani d . 1
H H8 0.3539 0.0776 0.7552 0.058 Uiso calc R 1
C C9 0.5636(5) -0.0660(3) 0.85358(19) 0.0511(7) Uani d . 1
H H9 0.4403 -0.0793 0.9039 0.061 Uiso calc R 1
C C10 0.7990(5) -0.1388(3) 0.86747(19) 0.0485(6) Uani d . 1
C C11 0.9826(5) -0.1205(4) 0.7936(2) 0.0547(7) Uani d . 1
H H11 1.1409 -0.1706 0.8033 0.066 Uiso calc R 1
C C12 0.9299(5) -0.0273(3) 0.7048(2) 0.0522(7) Uani d . 1
H H12 1.0542 -0.0129 0.6554 0.063 Uiso calc R 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Cl1 0.0772(6) 0.0819(6) 0.0582(5) -0.0101(4) -0.0222(4) 0.0172(4)
O1 0.0577(12) 0.0717(13) 0.0549(12) -0.0335(10) 0.0028(9) 0.0036(9)
N1 0.0459(13) 0.0710(16) 0.0555(15) -0.0166(11) -0.0157(11) 0.0100(12)
N2 0.0392(12) 0.0512(13) 0.0452(12) -0.0145(9) -0.0063(10) 0.0094(10)
N3 0.0516(14) 0.0604(15) 0.0402(13) -0.0224(11) 0.0000(11) 0.0110(11)
N4 0.0556(14) 0.0517(13) 0.0365(12) -0.0197(11) -0.0027(10) 0.0076(10)
C1 0.0422(15) 0.0647(18) 0.0485(16) -0.0177(13) -0.0045(13) 0.0106(13)
C2 0.0542(17) 0.0617(18) 0.0446(15) -0.0201(14) -0.0133(13) 0.0133(13)
C3 0.0385(14) 0.0639(18) 0.0535(16) -0.0165(13) -0.0036(13) -0.0002(14)
C4 0.0379(13) 0.0403(14) 0.0423(14) -0.0139(11) -0.0008(11) -0.0027(11)
C5 0.0472(15) 0.0457(15) 0.0428(15) -0.0178(12) -0.0018(13) -0.0034(12)
C6 0.0492(16) 0.0526(16) 0.0418(14) -0.0213(12) 0.0018(12) 0.0020(12)
C7 0.0473(15) 0.0440(15) 0.0406(14) -0.0193(12) -0.0053(12) -0.0013(11)
C8 0.0401(14) 0.0561(17) 0.0493(16) -0.0135(12) -0.0079(12) 0.0045(12)
C9 0.0478(16) 0.0592(17) 0.0452(15) -0.0173(13) -0.0029(12) 0.0057(13)
C10 0.0522(16) 0.0462(16) 0.0465(15) -0.0112(12) -0.0111(13) 0.0011(12)
C11 0.0407(15) 0.0617(18) 0.0607(18) -0.0084(13) -0.0142(14) -0.0017(14)
C12 0.0421(15) 0.0619(18) 0.0527(16) -0.0174(13) 0.0008(13) -0.0063(13)
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
C2 N1 C3 115.2(2)
C1 N2 C4 115.9(2)
C5 N3 N4 121.5(2)
C5 N3 H3A 117(2)
N4 N3 H3A 122(2)
C6 N4 N3 114.4(2)
N2 C1 C2 122.1(2)
N2 C1 H1 118.9
C2 C1 H1 118.9
N1 C2 C1 122.6(2)
N1 C2 H2 118.7
C1 C2 H2 118.7
N1 C3 C4 122.8(2)
N1 C3 H3 118.6
C4 C3 H3 118.6
N2 C4 C3 121.4(2)
N2 C4 C5 118.4(2)
C3 C4 C5 120.2(2)
O1 C5 N3 124.7(2)
O1 C5 C4 121.3(2)
N3 C5 C4 113.9(2)
N4 C6 C7 122.9(2)
N4 C6 H6 118.6
C7 C6 H6 118.6
C12 C7 C8 118.2(2)
C12 C7 C6 118.9(2)
C8 C7 C6 122.9(2)
C9 C8 C7 120.9(2)
C9 C8 H8 119.6
C7 C8 H8 119.6
C10 C9 C8 119.5(2)
C10 C9 H9 120.3
C8 C9 H9 120.3
C11 C10 C9 120.8(2)
C11 C10 Cl1 119.4(2)
C9 C10 Cl1 119.8(2)
C10 C11 C12 119.3(2)
C10 C11 H11 120.3
C12 C11 H11 120.3
C11 C12 C7 121.3(2)
C11 C12 H12 119.3
C7 C12 H12 119.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C10 1.739(3)
O1 C5 1.222(3)
N1 C2 1.330(3)
N1 C3 1.335(3)
N2 C1 1.334(3)
N2 C4 1.339(3)
N3 C5 1.350(3)
N3 N4 1.378(3)
N3 H3A 0.83(3)
N4 C6 1.272(3)
C1 C2 1.376(3)
C1 H1 0.9300
C2 H2 0.9300
C3 C4 1.381(3)
C3 H3 0.9300
C4 C5 1.498(3)
C6 C7 1.463(3)
C6 H6 0.9300
C7 C12 1.390(3)
C7 C8 1.390(3)
C8 C9 1.383(3)
C8 H8 0.9300
C9 C10 1.380(3)
C9 H9 0.9300
C10 C11 1.374(4)
C11 C12 1.380(4)
C11 H11 0.9300
C12 H12 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
N3 H3A N2 . 0.83(3) 2.27(3) 2.689(3) 111(2)
C6 H6 O1 1_655 0.93 2.24(3) 3.133(3) 160(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
C5 N3 N4 C6 174.4(2)
C4 N2 C1 C2 -0.4(4)
C3 N1 C2 C1 -0.7(4)
N2 C1 C2 N1 1.3(4)
C2 N1 C3 C4 -0.5(4)
C1 N2 C4 C3 -0.8(4)
C1 N2 C4 C5 178.4(2)
N1 C3 C4 N2 1.4(4)
N1 C3 C4 C5 -177.8(2)
N4 N3 C5 O1 -1.0(4)
N4 N3 C5 C4 179.1(2)
N2 C4 C5 O1 -171.9(2)
C3 C4 C5 O1 7.3(4)
N2 C4 C5 N3 8.1(3)
C3 C4 C5 N3 -172.7(2)
N3 N4 C6 C7 178.2(2)
N4 C6 C7 C12 171.8(2)
N4 C6 C7 C8 -9.4(4)
C12 C7 C8 C9 -1.7(4)
C6 C7 C8 C9 179.5(2)
C7 C8 C9 C10 0.9(4)
C8 C9 C10 C11 -0.3(4)
C8 C9 C10 Cl1 179.70(19)
C9 C10 C11 C12 0.4(4)
Cl1 C10 C11 C12 -179.5(2)
C10 C11 C12 C7 -1.3(4)
C8 C7 C12 C11 1.9(4)
C6 C7 C12 C11 -179.3(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 5271582
