#------------------------------------------------------------------------------
#$Date: 2015-10-29 06:07:48 +0200 (Thu, 29 Oct 2015) $
#$Revision: 169810 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/12/2241215.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_2241215
loop_
_publ_author_name
'Vittaya, Luksamee'
'Leesakul, Nararak'
'Saithong, Saowanit'
'Chainok, Kittipong'
_publ_section_title
;
 Crystal structure of
 dichloridobis[2-(phenyldiazenyl)pyridine-κN¹]zinc
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m201
_journal_page_last               m202
_journal_paper_doi               10.1107/S2056989015019143
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          '[Zn Cl2 (C11 H9 N3)2]'
_chemical_formula_moiety         'C22 H18 Cl2 N6 Zn'
_chemical_formula_sum            'C22 H18 Cl2 N6 Zn'
_chemical_formula_weight         502.69
_chemical_name_systematic
;
Dichloridobis[2-(phenyldiazenyl)pyridine-κN¹]zinc
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.7960(4)
_cell_length_b                   10.1905(3)
_cell_length_c                   16.1305(5)
_cell_measurement_reflns_used    9900
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.20
_cell_measurement_theta_min      3.22
_cell_volume                     2267.76(12)
_computing_cell_refinement
;
SAINT (Bruker, 2013)
;
_computing_data_collection
;
SMART (Bruker, 2013)
;
_computing_data_reduction
;
SAINT (Bruker, 2013)
;
_computing_molecular_graphics
;
Mercury  (Macrae et al.,  2008)
;
_computing_publication_material
;
WinGX (Farrugia, 2012) and publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_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 APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            65168
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.276
_diffrn_reflns_theta_min         3.544
_exptl_absorpt_coefficient_mu    1.340
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.7077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2013)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.222
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         2820
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0297
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0384P)²+0.7794P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0729
_refine_ls_wR_factor_ref         0.0834
_reflns_number_gt                2160
_reflns_number_total             2820
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            zl2646sup1.cif
_cod_data_source_block           I
_cod_database_code               2241215
_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   0.644
_shelx_estimated_absorpt_t_max   0.689
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, 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_occupancy
Zn Zn1 1.0000 0.21091(3) 0.7500 0.04573(11) Uani d 1
Cl Cl1 0.96785(4) 0.08709(5) 0.63805(3) 0.06114(15) Uani d 1
N N1 0.86977(11) 0.30520(15) 0.76959(10) 0.0468(3) Uani d 1
N N2 0.95560(12) 0.45206(15) 0.84789(10) 0.0514(4) Uani d 1
N N3 0.95301(13) 0.55766(16) 0.88646(11) 0.0584(4) Uani d 1
C C1 0.78854(15) 0.2566(2) 0.73676(13) 0.0571(5) Uani d 1
H H1 0.7927 0.1832 0.7026 0.069 Uiso calc 1
C C2 0.69884(17) 0.3110(2) 0.75155(14) 0.0676(6) Uani d 1
H H2 0.6434 0.2755 0.7275 0.081 Uiso calc 1
C C3 0.69288(16) 0.4185(2) 0.80247(16) 0.0730(6) Uani d 1
H H3 0.6330 0.4563 0.8140 0.088 Uiso calc 1
C C4 0.77541(15) 0.4698(2) 0.83614(14) 0.0627(5) Uani d 1
H H4 0.7726 0.5429 0.8706 0.075 Uiso calc 1
C C5 0.86318(13) 0.41115(18) 0.81815(11) 0.0484(4) Uani d 1
C C6 1.04406(15) 0.60029(19) 0.91730(12) 0.0555(5) Uani d 1
C C7 1.04401(19) 0.7222(2) 0.95484(16) 0.0696(6) Uani d 1
H H7 0.9866 0.7696 0.9593 0.084 Uiso calc 1
C C8 1.1291(2) 0.7733(3) 0.98561(16) 0.0789(7) Uani d 1
H H8 1.1293 0.8553 1.0110 0.095 Uiso calc 1
C C9 1.2132(2) 0.7037(3) 0.97888(15) 0.0763(7) Uani d 1
H H9 1.2707 0.7390 0.9990 0.092 Uiso calc 1
C C10 1.21338(17) 0.5810(2) 0.94239(14) 0.0706(6) Uani d 1
H H10 1.2709 0.5338 0.9386 0.085 Uiso calc 1
C C11 1.12915(16) 0.5283(2) 0.91168(13) 0.0623(5) Uani d 1
H H11 1.1291 0.4455 0.8874 0.075 Uiso calc 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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 '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 Zn1 N1 . 3_756 124.45(9)
N1 Zn1 Cl1 . 3_756 108.09(4)
N1 Zn1 Cl1 3_756 3_756 102.29(5)
N1 Zn1 Cl1 . . 102.29(5)
N1 Zn1 Cl1 3_756 . 108.09(4)
Cl1 Zn1 Cl1 3_756 . 111.68(3)
C1 N1 C5 . . 118.37(17)
C1 N1 Zn1 . . 119.85(13)
C5 N1 Zn1 . . 121.69(13)
N3 N2 C5 . . 113.33(16)
N2 N3 C6 . . 114.51(17)
N1 C1 C2 . . 122.4(2)
N1 C1 H1 . . 118.8
C2 C1 H1 . . 118.8
C3 C2 C1 . . 118.6(2)
C3 C2 H2 . . 120.7
C1 C2 H2 . . 120.7
C4 C3 C2 . . 119.6(2)
C4 C3 H3 . . 120.2
C2 C3 H3 . . 120.2
C3 C4 C5 . . 118.8(2)
C3 C4 H4 . . 120.6
C5 C4 H4 . . 120.6
N1 C5 C4 . . 122.15(19)
N1 C5 N2 . . 111.89(15)
C4 C5 N2 . . 125.96(18)
C7 C6 C11 . . 120.3(2)
C7 C6 N3 . . 115.36(19)
C11 C6 N3 . . 124.36(19)
C8 C7 C6 . . 119.8(2)
C8 C7 H7 . . 120.1
C6 C7 H7 . . 120.1
C9 C8 C7 . . 120.0(2)
C9 C8 H8 . . 120.0
C7 C8 H8 . . 120.0
C8 C9 C10 . . 120.4(2)
C8 C9 H9 . . 119.8
C10 C9 H9 . . 119.8
C11 C10 C9 . . 120.4(2)
C11 C10 H10 . . 119.8
C9 C10 H10 . . 119.8
C10 C11 C6 . . 119.1(2)
C10 C11 H11 . . 120.5
C6 C11 H11 . . 120.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Zn1 N1 . 2.0618(15)
Zn1 N1 3_756 2.0619(15)
Zn1 Cl1 3_756 2.2471(5)
Zn1 Cl1 . 2.2472(5)
N1 C1 . 1.335(3)
N1 C5 . 1.337(2)
N2 N3 . 1.244(2)
N2 C5 . 1.425(2)
N3 C6 . 1.419(3)
C1 C2 . 1.377(3)
C1 H1 . 0.9300
C2 C3 . 1.372(3)
C2 H2 . 0.9300
C3 C4 . 1.365(3)
C3 H3 . 0.9300
C4 C5 . 1.381(3)
C4 H4 . 0.9300
C6 C7 . 1.382(3)
C6 C11 . 1.387(3)
C7 C8 . 1.377(3)
C7 H7 . 0.9300
C8 C9 . 1.364(4)
C8 H8 . 0.9300
C9 C10 . 1.382(3)
C9 H9 . 0.9300
C10 C11 . 1.372(3)
C10 H10 . 0.9300
C11 H11 . 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
C3 H3 Cl1 6_567 0.93 2.75 3.675(2) 172.9
C1 H1 Cl1 . 0.93 2.81 3.411(2) 123.6
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 N2 N3 C6 179.59(15)
C5 N1 C1 C2 -0.4(3)
Zn1 N1 C1 C2 176.25(16)
N1 C1 C2 C3 -0.5(3)
C1 C2 C3 C4 0.9(3)
C2 C3 C4 C5 -0.3(3)
C1 N1 C5 C4 1.0(3)
Zn1 N1 C5 C4 -175.57(14)
C1 N1 C5 N2 -179.50(16)
Zn1 N1 C5 N2 3.9(2)
C3 C4 C5 N1 -0.7(3)
C3 C4 C5 N2 179.92(19)
N3 N2 C5 N1 173.32(16)
N3 N2 C5 C4 -7.2(3)
N2 N3 C6 C7 175.28(19)
N2 N3 C6 C11 -4.7(3)
C11 C6 C7 C8 1.0(3)
N3 C6 C7 C8 -179.0(2)
C6 C7 C8 C9 0.1(4)
C7 C8 C9 C10 -1.0(4)
C8 C9 C10 C11 0.7(4)
C9 C10 C11 C6 0.4(3)
C7 C6 C11 C10 -1.3(3)
N3 C6 C11 C10 178.7(2)

_cod_database_fobs_code 2241215
