#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:47:15 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179596 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/60/4506014.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_4506014
loop_
_publ_author_name
'Gai, Yan-Li'
'Jiang, Fei-Long'
'Xiong, Ke-Cai'
'Chen, Lian'
'Yuan, Da-Qiang'
'Zhang, Lin-Jie'
'Zhou, Kang'
'Hong, Mao-Chun'
_publ_section_title
;
 Temperature-Dependent in Situ Reduction of 4,4′-Azobispyridine via
 Solvothermal Reaction
;
_journal_issue                   4
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2079
_journal_paper_doi               10.1021/cg3000813
_journal_volume                  12
_journal_year                    2012
_chemical_formula_sum            'C24 H18 N4 O5 Zn'
_chemical_formula_weight         507.79
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.345(4)
_cell_length_b                   14.624(4)
_cell_length_c                   10.661(3)
_cell_measurement_reflns_used    4538
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.4470
_cell_measurement_theta_min      2.7858
_cell_volume                     2080.6(10)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  Mercury70_(2x2_bin_mode)
_diffrn_measurement_method       CCD_Profile_fitting
_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  0.0269
_diffrn_reflns_av_sigmaI/netI    0.0160
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14966
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.79
_exptl_absorpt_coefficient_mu    1.228
_exptl_absorpt_correction_T_max  0.7095
_exptl_absorpt_correction_T_min  0.6393
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cuboid
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.463
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2370
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.122
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0319
_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)+(0.0386P)²+0.8989P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0776
_refine_ls_wR_factor_ref         0.0795
_reflns_number_gt                2208
_reflns_number_total             2370
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg3000813_si_001.cif
_cod_data_source_block           complex_4
_cod_depositor_comments
;
The following automatic conversions were performed:

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

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' 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_original_cell_volume        2080.4(10)
_cod_original_sg_symbol_H-M      Pbcn
_cod_database_code               4506014
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Zn1 Zn 1.0000 0.060441(18) 0.2500 0.02211(11) Uani 1 2 d S
O1 O 1.00968(8) 0.12002(9) 0.08272(11) 0.0268(3) Uani 1 1 d .
O2 O 0.95154(13) 0.20225(10) -0.07541(12) 0.0458(4) Uani 1 1 d .
O3 O 1.0000 -0.07766(13) 0.2500 0.0315(4) Uani 1 2 d S
N1 N 1.16344(12) 0.05986(9) 0.25930(13) 0.0246(3) Uani 1 1 d .
N2 N 1.47670(12) 0.06440(10) 0.30067(17) 0.0328(4) Uani 1 1 d .
C1 C 0.95993(12) 0.18690(11) 0.03812(15) 0.0252(3) Uani 1 1 d .
C2 C 0.90243(12) 0.24710(11) 0.12828(15) 0.0244(3) Uani 1 1 d .
C3 C 0.94486(13) 0.28296(12) 0.23819(14) 0.0240(3) Uani 1 1 d .
C4 C 0.88264(14) 0.32929(12) 0.32272(16) 0.0301(4) Uani 1 1 d .
H4 H 0.9099 0.3538 0.3956 0.036 Uiso 1 1 calc R
C5 C 0.78134(15) 0.33914(13) 0.29944(19) 0.0351(4) Uani 1 1 d .
H5 H 0.7408 0.3688 0.3576 0.042 Uiso 1 1 calc R
C6 C 0.73997(13) 0.30506(13) 0.19018(19) 0.0344(4) Uani 1 1 d .
H6 H 0.6719 0.3122 0.1743 0.041 Uiso 1 1 calc R
C7 C 0.80057(13) 0.26032(12) 0.10471(17) 0.0297(4) Uani 1 1 d .
H7 H 0.7730 0.2387 0.0303 0.036 Uiso 1 1 calc R
C8 C 1.20930(13) 0.02686(13) 0.36134(17) 0.0300(4) Uani 1 1 d .
H8 H 1.1702 0.0011 0.4242 0.036 Uiso 1 1 calc R
C9 C 1.31210(13) 0.02925(13) 0.37789(17) 0.0312(4) Uani 1 1 d .
H9 H 1.3414 0.0070 0.4510 0.037 Uiso 1 1 calc R
C10 C 1.37009(13) 0.06561(12) 0.28257(19) 0.0287(4) Uani 1 1 d .
C11 C 1.32410(13) 0.10226(13) 0.17715(17) 0.0304(4) Uani 1 1 d .
H11 H 1.3616 0.1291 0.1135 0.036 Uiso 1 1 calc R
C12 C 1.22108(13) 0.09763(12) 0.16971(16) 0.0281(4) Uani 1 1 d .
H12 H 1.1899 0.1218 0.0992 0.034 Uiso 1 1 calc R
H3A H 0.9858 -0.1156 0.3116 0.062(8) Uiso 1 1 d R
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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O1 Zn1 O1 128.04(8) 4_755 .
O1 Zn1 O3 115.98(4) 4_755 .
O1 Zn1 O3 115.98(4) . .
O1 Zn1 N1 88.71(5) 4_755 4_755
O1 Zn1 N1 91.48(5) . 4_755
O3 Zn1 N1 89.78(4) . 4_755
O1 Zn1 N1 91.48(5) 4_755 .
O1 Zn1 N1 88.71(5) . .
O3 Zn1 N1 89.78(4) . .
N1 Zn1 N1 179.55(7) 4_755 .
C1 O1 Zn1 129.57(11) . .
Zn1 O3 H3A 129.1 . .
C8 N1 C12 117.63(16) . .
C8 N1 Zn1 119.69(12) . .
C12 N1 Zn1 122.51(12) . .
N2 N2 C10 112.2(2) 4_855 .
O2 C1 O1 123.51(16) . .
O2 C1 C2 118.07(15) . .
O1 C1 C2 118.30(14) . .
C7 C2 C3 119.44(16) . .
C7 C2 C1 117.41(15) . .
C3 C2 C1 122.92(15) . .
C4 C3 C2 118.62(16) . .
C4 C3 C3 118.42(16) . 4_755
C2 C3 C3 122.59(17) . 4_755
C5 C4 C3 120.99(17) . .
C5 C4 H4 119.5 . .
C3 C4 H4 119.5 . .
C6 C5 C4 120.30(17) . .
C6 C5 H5 119.8 . .
C4 C5 H5 119.8 . .
C5 C6 C7 119.50(17) . .
C5 C6 H6 120.3 . .
C7 C6 H6 120.2 . .
C6 C7 C2 121.09(17) . .
C6 C7 H7 119.5 . .
C2 C7 H7 119.5 . .
N1 C8 C9 123.23(17) . .
N1 C8 H8 118.4 . .
C9 C8 H8 118.4 . .
C8 C9 C10 118.08(17) . .
C8 C9 H9 121.0 . .
C10 C9 H9 121.0 . .
C9 C10 C11 119.72(17) . .
C9 C10 N2 116.80(17) . .
C11 C10 N2 123.48(17) . .
C12 C11 C10 117.93(17) . .
C12 C11 H11 121.0 . .
C10 C11 H11 121.0 . .
N1 C12 C11 123.34(17) . .
N1 C12 H12 118.3 . .
C11 C12 H12 118.3 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 O1 1.9890(13) 4_755
Zn1 O1 1.9890(13) .
Zn1 O3 2.0196(19) .
Zn1 N1 2.1833(17) 4_755
Zn1 N1 2.1833(17) .
O1 C1 1.274(2) .
O2 C1 1.236(2) .
O3 H3A 0.8808 .
N1 C8 1.338(2) .
N1 C12 1.345(2) .
N2 N2 1.246(4) 4_855
N2 C10 1.436(2) .
C1 C2 1.513(2) .
C2 C7 1.396(2) .
C2 C3 1.403(2) .
C3 C4 1.400(2) .
C3 C3 1.493(3) 4_755
C4 C5 1.382(3) .
C4 H4 0.9300 .
C5 C6 1.382(3) .
C5 H5 0.9300 .
C6 C7 1.383(3) .
C6 H6 0.9300 .
C7 H7 0.9300 .
C8 C9 1.383(2) .
C8 H8 0.9300 .
C9 C10 1.384(3) .
C9 H9 0.9300 .
C10 C11 1.388(3) .
C11 C12 1.379(2) .
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_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3A O2 0.88 1.81 2.6836(19) 173.6 8_556
