#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/75/2227518.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_2227518
loop_
_publ_author_name
'Ather, Abdul Qayyum'
'Tahir, M. Nawaz'
'Khan, Misbahul Ain'
'Athar, Muhammad Makshoof'
_publ_section_title
;
 3-[(2E)-2-(Butan-2-ylidene)hydrazinyl]-6-chloropyridazine
;
_journal_coeditor_code           HB5623
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2499
_journal_paper_doi               10.1107/S160053681003504X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C8 H11 Cl N4'
_chemical_formula_moiety         'C8 H11 Cl N4'
_chemical_formula_sum            'C8 H11 Cl N4'
_chemical_formula_weight         198.66
_chemical_name_systematic
;
3-[(2E)-2-(Butan-2-ylidene)hydrazinyl]-6-chloropyridazine
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                113.8580(10)
_cell_angle_beta                 91.370(2)
_cell_angle_gamma                104.880(2)
_cell_formula_units_Z            4
_cell_length_a                   8.0623(4)
_cell_length_b                   11.6768(5)
_cell_length_c                   12.1314(5)
_cell_measurement_reflns_used    2652
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.25
_cell_measurement_theta_min      2.07
_cell_volume                     998.85(8)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material
'WinGX (Farrugia, 1999) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 8.10
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       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  0.0309
_diffrn_reflns_av_sigmaI/netI    0.0298
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14983
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         2.07
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.342
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.201
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3585
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0353
_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)+(0.0426P)²+0.1867P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0880
_refine_ls_wR_factor_ref         0.0988
_reflns_number_gt                2652
_reflns_number_total             3585
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5623.cif
_cod_data_source_block           I
_cod_database_code               2227518
_cod_database_fobs_code          2227518
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
Cl Cl1 0.56878(7) 1.01144(5) 0.14461(4) 0.0711(2) Uani . . 1.000
N N1 0.65078(7) 0.81818(4) -0.01826(4) 0.0494(5) Uani . . 1.000
N N2 0.69138(9) 0.70411(6) -0.06328(4) 0.0477(5) Uani . . 1.000
N N3 0.73568(11) 0.52631(8) -0.04789(4) 0.0485(5) Uani . . 1.000
N N4 0.75811(18) 0.46292(14) 0.02371(12) 0.0446(5) Uani . . 1.000
C C1 0.6218(2) 0.86549(17) 0.09480(15) 0.0457(6) Uani . . 1.000
C C2 0.6309(2) 0.80724(18) 0.17388(15) 0.0482(6) Uani . . 1.000
C C3 0.6692(2) 0.69257(17) 0.12939(14) 0.0456(6) Uani . . 1.000
C C4 0.6972(2) 0.64155(16) 0.00695(14) 0.0403(6) Uani . . 1.000
C C5 0.8018(2) 0.35764(18) -0.02463(16) 0.0446(6) Uani . . 1.000
C C6 0.8294(3) 0.29374(19) 0.05683(17) 0.0546(7) Uani . . 1.000
C C7 0.8037(3) 0.3631(2) 0.18693(18) 0.0706(9) Uani . . 1.000
C C8 0.8324(3) 0.29472(19) -0.15401(16) 0.0571(7) Uani . . 1.000
Cl Cl2 0.61890(8) 0.92216(5) 0.55956(5) 0.0741(2) Uani . . 1.000
N N5 0.4684(2) 0.70148(16) 0.37821(14) 0.0577(6) Uani . . 1.000
N N6 0.3743(2) 0.57428(16) 0.32230(13) 0.0577(6) Uani . . 1.000
N N7 0.2290(2) 0.38112(15) 0.32596(13) 0.0557(6) Uani . . 1.000
N N8 0.1391(2) 0.31693(16) 0.38987(13) 0.0527(6) Uani . . 1.000
C C9 0.4960(2) 0.75931(18) 0.49629(16) 0.0499(6) Uani . . 1.000
C C10 0.4326(3) 0.69965(19) 0.57130(16) 0.0572(7) Uani . . 1.000
C C11 0.3386(3) 0.57264(19) 0.51703(16) 0.0560(7) Uani . . 1.000
C C12 0.3135(2) 0.51037(18) 0.38917(15) 0.0461(6) Uani . . 1.000
C C13 0.0646(3) 0.19453(19) 0.33475(16) 0.0514(7) Uani . . 1.000
C C14 -0.0380(3) 0.1305(2) 0.40720(18) 0.0656(8) Uani . . 1.000
C C15 -0.0180(3) 0.2152(2) 0.5419(2) 0.0842(10) Uani . . 1.000
C C16 0.06718(9) 0.10973(7) 0.20380(5) 0.0690(8) Uani . . 1.000
H H2 0.61145 0.84592 0.25415 0.0578 Uiso . . 1.000
H H3 0.67676 0.64881 0.17770 0.0547 Uiso . . 1.000
H H3A 0.74569 0.49409 -0.12405 0.0582 Uiso . . 1.000
H H6A 0.75051 0.20566 0.02287 0.0655 Uiso . . 1.000
H H6B 0.94655 0.28638 0.05598 0.0655 Uiso . . 1.000
H H7A 0.88583 0.44865 0.22347 0.1059 Uiso . . 1.000
H H7B 0.68809 0.37098 0.18942 0.1059 Uiso . . 1.000
H H7C 0.82074 0.31382 0.23104 0.1059 Uiso . . 1.000
H H8A 0.72987 0.27583 -0.20780 0.0858 Uiso . . 1.000
H H8B 0.92751 0.35314 -0.16869 0.0858 Uiso . . 1.000
H H8C 0.85936 0.21485 -0.16845 0.0858 Uiso . . 1.000
H H7 0.23145 0.34080 0.24923 0.0668 Uiso . . 1.000
H H10 0.45400 0.74553 0.65567 0.0687 Uiso . . 1.000
H H11 0.29214 0.52778 0.56265 0.0673 Uiso . . 1.000
H H14A -0.00369 0.05316 0.39609 0.0787 Uiso . . 1.000
H H14B -0.15974 0.10162 0.37404 0.0787 Uiso . . 1.000
H H15A 0.10043 0.23887 0.57731 0.1264 Uiso . . 1.000
H H15B -0.09207 0.16776 0.57958 0.1264 Uiso . . 1.000
H H15C -0.04957 0.29300 0.55442 0.1264 Uiso . . 1.000
H H16A -0.00022 0.13112 0.15265 0.1035 Uiso . . 1.000
H H16B 0.01880 0.01944 0.18790 0.1035 Uiso . . 1.000
H H16C 0.18459 0.12428 0.18693 0.1035 Uiso . . 1.000
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'
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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 N1 C1 . . . 118.43(10) no
N1 N2 C4 . . . 119.67(8) no
N4 N3 C4 . . . 117.38(10) no
N3 N4 C5 . . . 118.39(13) no
C4 N3 H3A . . . 121.00 no
N4 N3 H3A . . . 121.00 no
N6 N5 C9 . . . 119.09(18) no
N5 N6 C12 . . . 119.53(15) no
N8 N7 C12 . . . 117.28(14) no
N7 N8 C13 . . . 119.01(15) no
N8 N7 H7 . . . 121.00 no
C12 N7 H7 . . . 121.00 no
N1 C1 C2 . . . 124.75(16) no
Cl1 C1 C2 . . . 119.92(13) no
Cl1 C1 N1 . . . 115.33(13) no
C1 C2 C3 . . . 117.28(16) no
C2 C3 C4 . . . 117.42(17) no
N2 C4 N3 . . . 114.99(12) no
N3 C4 C3 . . . 122.59(16) no
N2 C4 C3 . . . 122.41(16) no
C6 C5 C8 . . . 117.44(18) no
N4 C5 C8 . . . 125.76(19) no
N4 C5 C6 . . . 116.78(16) no
C5 C6 C7 . . . 115.54(19) no
C3 C2 H2 . . . 121.00 no
C1 C2 H2 . . . 121.00 no
C4 C3 H3 . . . 121.00 no
C2 C3 H3 . . . 121.00 no
C5 C6 H6A . . . 108.00 no
C7 C6 H6B . . . 108.00 no
C5 C6 H6B . . . 108.00 no
H6A C6 H6B . . . 107.00 no
C7 C6 H6A . . . 108.00 no
H7A C7 H7B . . . 110.00 no
H7A C7 H7C . . . 109.00 no
C6 C7 H7C . . . 109.00 no
H7B C7 H7C . . . 109.00 no
C6 C7 H7B . . . 109.00 no
C6 C7 H7A . . . 109.00 no
H8A C8 H8C . . . 109.00 no
C5 C8 H8A . . . 109.00 no
H8B C8 H8C . . . 109.00 no
H8A C8 H8B . . . 109.00 no
C5 C8 H8C . . . 109.00 no
C5 C8 H8B . . . 109.00 no
Cl2 C9 C10 . . . 119.98(14) no
Cl2 C9 N5 . . . 115.69(16) no
N5 C9 C10 . . . 124.3(2) no
C9 C10 C11 . . . 117.37(17) no
C10 C11 C12 . . . 117.67(19) no
N7 C12 C11 . . . 122.28(19) no
N6 C12 N7 . . . 115.75(15) no
N6 C12 C11 . . . 121.96(19) no
N8 C13 C14 . . . 116.84(17) no
N8 C13 C16 . . . 125.68(18) no
C14 C13 C16 . . . 117.47(17) no
C13 C14 C15 . . . 115.48(19) no
C9 C10 H10 . . . 121.00 no
C11 C10 H10 . . . 121.00 no
C10 C11 H11 . . . 121.00 no
C12 C11 H11 . . . 121.00 no
C13 C14 H14A . . . 108.00 no
C13 C14 H14B . . . 108.00 no
C15 C14 H14A . . . 108.00 no
C15 C14 H14B . . . 108.00 no
H14A C14 H14B . . . 107.00 no
C14 C15 H15A . . . 109.00 no
C14 C15 H15B . . . 109.00 no
C14 C15 H15C . . . 109.00 no
H15A C15 H15B . . . 110.00 no
H15A C15 H15C . . . 109.00 no
H15B C15 H15C . . . 110.00 no
C13 C16 H16A . . . 109.00 no
C13 C16 H16B . . . 109.00 no
C13 C16 H16C . . . 109.00 no
H16A C16 H16B . . . 109.00 no
H16A C16 H16C . . . 109.00 no
H16B C16 H16C . . . 109.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C1 . . 1.734(2) no
Cl2 C9 . . 1.733(2) no
N1 N2 . . 1.3504(9) no
N1 C1 . . 1.3075(17) no
N2 C4 . . 1.3345(19) no
N3 N4 . . 1.3843(18) no
N3 C4 . . 1.360(2) no
N4 C5 . . 1.276(3) no
N3 H3A . . 0.8600 no
N5 C9 . . 1.297(2) no
N5 N6 . . 1.350(3) no
N6 C12 . . 1.333(3) no
N7 N8 . . 1.381(2) no
N7 C12 . . 1.357(3) no
N8 C13 . . 1.272(3) no
N7 H7 . . 0.8600 no
C1 C2 . . 1.392(3) no
C2 C3 . . 1.347(3) no
C3 C4 . . 1.408(2) no
C5 C8 . . 1.498(3) no
C5 C6 . . 1.501(3) no
C6 C7 . . 1.503(3) no
C2 H2 . . 0.9300 no
C3 H3 . . 0.9300 no
C6 H6B . . 0.9700 no
C6 H6A . . 0.9700 no
C7 H7A . . 0.9600 no
C7 H7C . . 0.9600 no
C7 H7B . . 0.9600 no
C8 H8A . . 0.9600 no
C8 H8C . . 0.9600 no
C8 H8B . . 0.9600 no
C9 C10 . . 1.388(3) no
C10 C11 . . 1.348(3) no
C11 C12 . . 1.405(2) no
C13 C16 . . 1.4981(19) no
C13 C14 . . 1.505(3) no
C14 C15 . . 1.508(3) no
C10 H10 . . 0.9300 no
C11 H11 . . 0.9300 no
C14 H14A . . 0.9700 no
C14 H14B . . 0.9700 no
C15 H15A . . 0.9600 no
C15 H15B . . 0.9600 no
C15 H15C . . 0.9600 no
C16 H16A . . 0.9600 no
C16 H16B . . 0.9600 no
C16 H16C . . 0.9600 no
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 H3A N6 2_665 0.86 2.30 3.0674(15) 148 yes
N7 H7 N2 2_665 0.86 2.24 3.0689(15) 161 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 N1 N2 C4 . . . . 1.45(15) no
N2 N1 C1 Cl1 . . . . -179.47(8) no
N2 N1 C1 C2 . . . . 0.5(2) no
N1 N2 C4 N3 . . . . 178.67(10) no
N1 N2 C4 C3 . . . . -2.6(2) no
C4 N3 N4 C5 . . . . -176.95(15) no
N4 N3 C4 N2 . . . . 174.58(12) no
N4 N3 C4 C3 . . . . -4.1(2) no
N3 N4 C5 C6 . . . . 178.44(15) no
N3 N4 C5 C8 . . . . 0.2(3) no
C9 N5 N6 C12 . . . . -0.8(3) no
N6 N5 C9 Cl2 . . . . 179.70(14) no
N6 N5 C9 C10 . . . . -1.0(3) no
N5 N6 C12 N7 . . . . -176.31(16) no
N5 N6 C12 C11 . . . . 2.5(3) no
C12 N7 N8 C13 . . . . -176.99(19) no
N8 N7 C12 N6 . . . . -169.24(16) no
N8 N7 C12 C11 . . . . 12.0(3) no
N7 N8 C13 C16 . . . . 1.2(3) no
N7 N8 C13 C14 . . . . -177.43(18) no
N1 C1 C2 C3 . . . . -1.3(3) no
Cl1 C1 C2 C3 . . . . 178.68(14) no
C1 C2 C3 C4 . . . . 0.2(3) no
C2 C3 C4 N2 . . . . 1.8(3) no
C2 C3 C4 N3 . . . . -179.62(16) no
N4 C5 C6 C7 . . . . -0.6(3) no
C8 C5 C6 C7 . . . . 177.78(19) no
Cl2 C9 C10 C11 . . . . -179.66(18) no
N5 C9 C10 C11 . . . . 1.1(3) no
C9 C10 C11 C12 . . . . 0.6(3) no
C10 C11 C12 N6 . . . . -2.3(3) no
C10 C11 C12 N7 . . . . 176.4(2) no
N8 C13 C14 C15 . . . . -8.9(3) no
C16 C13 C14 C15 . . . . 172.35(18) no
