#------------------------------------------------------------------------------
#$Date: 2016-03-24 01:31:19 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179533 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/02/4500200.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_4500200
loop_
_publ_author_name
'Bhattacharya, Saurav'
'Sanyal, Udishnu'
'Natarajan, Srinivasan'
_publ_section_title
;
 Liquid−Liquid Interphase (Biphasic) as the Reaction Medium in the
 Assembly of a Hierarchy of Structures of 4,4′-Azodibenzoic Acid
 with Zinc and Cadmium
;
_journal_issue                   3
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              735
_journal_paper_doi               10.1021/cg101251a
_journal_volume                  11
_journal_year                    2011
_chemical_formula_sum            'C14 H10 Cd N2 O5'
_chemical_formula_weight         398.64
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.5690(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.8013(13)
_cell_length_b                   6.3249(5)
_cell_length_c                   28.897(2)
_cell_measurement_temperature    293(2)
_cell_volume                     2700.0(4)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics
'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)'
_computing_publication_material  'PLATON (Spek, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.941
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_device_type  'Bruker SMART CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0276
_diffrn_reflns_av_sigmaI/netI    0.0283
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            9450
_diffrn_reflns_theta_full        26.36
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         2.76
_exptl_absorpt_coefficient_mu    1.644
_exptl_absorpt_correction_T_max  0.808
_exptl_absorpt_correction_T_min  0.739
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_density_diffrn    1.961
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_refine_diff_density_max         3.400
_refine_diff_density_min         -1.129
_refine_diff_density_rms         0.161
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2581
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0561
_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)+(0.0762P)²+27.9419P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1385
_refine_ls_wR_factor_ref         0.1439
_reflns_number_gt                2314
_reflns_number_total             2581
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg101251a_si_002.cif
_cod_data_source_block           Compound(V)
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_sg_symbol_H-M      C2/c
_cod_database_code               4500200
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, 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
Cd1 Cd 0.62662(3) 0.18962(7) 0.505452(15) 0.0270(2) Uani 1 1 d .
O1 O 0.4920(3) 0.1647(8) 0.45999(16) 0.0361(11) Uani 1 1 d .
O2 O 0.4358(4) -0.1305(9) 0.42973(17) 0.0442(13) Uani 1 1 d .
O3 O 0.6756(3) -0.0918(8) 0.46097(16) 0.0360(11) Uani 1 1 d .
O4 O 0.7364(3) 0.2204(8) 0.44828(15) 0.0316(10) Uani 1 1 d .
O5 O 0.6093(4) 0.5423(8) 0.49780(19) 0.0430(12) Uani 1 1 d D
N1 N 0.6270(8) 0.3119(19) 0.2509(4) 0.095(3) Uiso 1 1 d .
N2 N 0.8531(8) -0.3235(19) 0.2665(4) 0.094(3) Uiso 1 1 d .
C1 C 0.4799(4) 0.0357(11) 0.4272(2) 0.0302(14) Uani 1 1 d .
C2 C 0.5188(4) 0.0888(14) 0.3824(2) 0.0359(16) Uani 1 1 d .
C3 C 0.5483(6) 0.2856(15) 0.3723(3) 0.052(2) Uani 1 1 d .
H3 H 0.5453 0.3935 0.3940 0.062 Uiso 1 1 calc R
C4 C 0.5830(7) 0.327(2) 0.3295(4) 0.076(4) Uani 1 1 d .
H4 H 0.6010 0.4636 0.3227 0.091 Uiso 1 1 calc R
C5 C 0.5912(6) 0.176(3) 0.2981(4) 0.089(5) Uani 1 1 d .
C6 C 0.5632(6) -0.022(2) 0.3068(2) 0.076(4) Uani 1 1 d .
H6 H 0.5689 -0.1259 0.2843 0.091 Uiso 1 1 calc R
C7 C 0.5262(5) -0.0759(18) 0.3482(3) 0.054(2) Uani 1 1 d .
H7 H 0.5069 -0.2130 0.3536 0.064 Uiso 1 1 calc R
C8 C 0.8231(6) -0.196(2) 0.3102(3) 0.074(4) Uani 1 1 d .
C9 C 0.7827(7) -0.3359(18) 0.3397(4) 0.064(3) Uani 1 1 d .
H9 H 0.7757 -0.4774 0.3315 0.077 Uiso 1 1 calc R
C10 C 0.7526(6) -0.2634(14) 0.3816(3) 0.0475(19) Uani 1 1 d .
H10 H 0.7264 -0.3582 0.4014 0.057 Uiso 1 1 calc R
C11 C 0.7609(4) -0.0530(12) 0.3943(2) 0.0314(14) Uani 1 1 d .
C12 C 0.8026(5) 0.0819(16) 0.3653(2) 0.048(2) Uani 1 1 d .
H12 H 0.8108 0.2223 0.3741 0.058 Uiso 1 1 calc R
C13 C 0.8328(6) 0.015(2) 0.3232(3) 0.066(3) Uani 1 1 d .
H13 H 0.8593 0.1111 0.3037 0.080 Uiso 1 1 calc R
C14 C 0.7245(4) 0.0280(10) 0.4371(2) 0.0261(12) Uani 1 1 d .
H5A H 0.624(8) 0.665(11) 0.481(4) 0.10(4) Uiso 1 1 d D
H5B H 0.646(8) 0.434(13) 0.486(4) 0.14(6) Uiso 1 1 d D
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'
Cd Cd -0.8075 1.2024 '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
O2 Cd1 O5 101.7(2) 5_656 .
O2 Cd1 O1 94.58(19) 5_656 .
O5 Cd1 O1 85.60(19) . .
O2 Cd1 O3 120.4(2) 5_656 .
O5 Cd1 O3 137.46(18) . .
O1 Cd1 O3 85.52(17) . .
O2 Cd1 O4 162.1(2) 5_656 .
O5 Cd1 O4 85.98(17) . .
O1 Cd1 O4 102.13(16) . .
O3 Cd1 O4 55.64(16) . .
O2 Cd1 O4 87.20(18) 5_656 7_656
O5 Cd1 O4 84.72(19) . 7_656
O1 Cd1 O4 170.32(17) . 7_656
O3 Cd1 O4 101.80(17) . 7_656
O4 Cd1 O4 77.38(16) . 7_656
O2 Cd1 C14 146.7(2) 5_656 .
O5 Cd1 C14 111.29(18) . .
O1 Cd1 C14 92.36(17) . .
O3 Cd1 C14 28.00(18) . .
O4 Cd1 C14 27.78(17) . .
O4 Cd1 C14 91.33(17) 7_656 .
C1 O1 Cd1 123.2(4) . .
C1 O2 Cd1 116.7(4) . 5_656
C14 O3 Cd1 92.9(4) . .
C14 O4 Cd1 90.5(3) . .
C14 O4 Cd1 117.5(4) . 7_656
Cd1 O4 Cd1 102.62(16) . 7_656
N2 N1 C5 94.7(13) 4_655 .
N2 N1 C8 54.0(10) 4_655 4_655
C5 N1 C8 148.6(10) . 4_655
N1 N2 C8 93.8(13) 4_645 .
O2 C1 O1 123.8(6) . .
O2 C1 C2 118.4(6) . .
O1 C1 C2 117.8(6) . .
C3 C2 C7 118.3(7) . .
C3 C2 C1 122.8(8) . .
C7 C2 C1 118.9(7) . .
C2 C3 C4 120.2(10) . .
C5 C4 C3 121.9(11) . .
C4 C5 C6 119.9(9) . .
C4 C5 N1 103.3(11) . .
C6 C5 N1 136.3(11) . .
C5 C6 C7 122.0(11) . .
C6 C7 C2 117.7(10) . .
C9 C8 C13 119.1(8) . .
C9 C8 N2 108.7(10) . .
C13 C8 N2 132.2(11) . .
C9 C8 N1 140.6(9) . 4_645
C13 C8 N1 100.3(9) . 4_645
N2 C8 N1 32.2(5) . 4_645
C8 C9 C10 119.9(9) . .
C11 C10 C9 121.2(9) . .
C12 C11 C10 118.2(7) . .
C12 C11 C14 120.0(7) . .
C10 C11 C14 121.8(7) . .
C11 C12 C13 122.0(9) . .
C12 C13 C8 119.6(10) . .
O4 C14 O3 120.4(5) . .
O4 C14 C11 119.7(6) . .
O3 C14 C11 119.7(6) . .
O4 C14 Cd1 61.7(3) . .
O3 C14 Cd1 59.1(3) . .
C11 C14 Cd1 168.6(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cd1 O2 2.172(5) 5_656
Cd1 O5 2.255(5) .
Cd1 O1 2.323(5) .
Cd1 O3 2.337(5) .
Cd1 O4 2.396(4) .
Cd1 O4 2.426(5) 7_656
Cd1 C14 2.720(6) .
O1 C1 1.255(8) .
O2 C1 1.242(8) .
O2 Cd1 2.172(5) 5_656
O3 C14 1.279(8) .
O4 C14 1.268(8) .
O4 Cd1 2.426(5) 7_656
N1 N2 1.043(15) 4_655
N1 C5 1.723(16) .
N1 C8 1.955(16) 4_655
N2 N1 1.043(15) 4_645
N2 C8 1.585(15) .
C1 C2 1.486(8) .
C2 C3 1.357(12) .
C2 C7 1.446(12) .
C3 C4 1.394(13) .
C4 C5 1.325(19) .
C5 C6 1.35(2) .
C6 C7 1.388(11) .
C8 C9 1.389(17) .
C8 C13 1.395(17) .
C8 N1 1.955(16) 4_645
C9 C10 1.394(12) .
C10 C11 1.384(11) .
C11 C12 1.369(11) .
C11 C14 1.472(8) .
C12 C13 1.389(10) .
