#------------------------------------------------------------------------------
#$Date: 2016-03-23 03:39:23 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179255 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/75/4317556.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_4317556
loop_
_publ_author_name
'Donald J. Darensbourg'
'Jacob R. Wildeson'
'Jason C. Yarbrough'
_publ_section_title
;
 Solid-State Structures of Zinc(II) Benzoate Complexes. Catalyst
 Precursors for the Coupling of Carbon Dioxide and Epoxides
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              973
_journal_page_last               980
_journal_paper_doi               10.1021/ic0107983
_journal_volume                  41
_journal_year                    2002
_chemical_formula_sum            'C29 H21 Cl4 N3 O4 Zn'
_chemical_formula_weight         682.66
_chemical_name_systematic
;
  ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 106.76(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.688(17)
_cell_length_b                   9.213(10)
_cell_length_c                   22.59(3)
_cell_measurement_temperature    110(2)
_cell_volume                     2927(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.638
_diffrn_measured_fraction_theta_max 0.638
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.1304
_diffrn_reflns_av_sigmaI/netI    0.3506
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            4058
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.45
_exptl_absorpt_coefficient_mu    1.244
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colouless
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1384
_refine_diff_density_max         0.581
_refine_diff_density_min         -0.658
_refine_diff_density_rms         0.116
_refine_ls_extinction_coef       0.0133(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.832
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     371
_refine_ls_number_reflns         3282
_refine_ls_number_restraints     216
_refine_ls_restrained_S_all      0.809
_refine_ls_R_factor_all          0.2153
_refine_ls_R_factor_gt           0.0771
_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)+(0.0604P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1428
_refine_ls_wR_factor_ref         0.1887
_reflns_number_gt                1134
_reflns_number_total             3282
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic0107983_4.cif
_cod_data_source_block           2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4317556
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.24119(13) 0.39317(18) 0.24738(10) 0.0264(6) Uani 1 1 d . . .
N1 N 0.3887(9) 0.4123(13) 0.2897(6) 0.034(2) Uani 1 1 d U . .
N2 N 0.2374(8) 0.1677(11) 0.2555(6) 0.024(2) Uani 1 1 d U . .
N3 N 0.1007(9) 0.4612(13) 0.2060(6) 0.036(3) Uani 1 1 d U . .
O1 O 0.2143(7) 0.4149(11) 0.3278(5) 0.039(3) Uani 1 1 d U . .
O2 O 0.2408(7) 0.6333(10) 0.3737(5) 0.037(3) Uani 1 1 d U . .
O3 O 0.2623(7) 0.3767(10) 0.1558(5) 0.036(2) Uani 1 1 d U . .
O4 O 0.2752(7) 0.5962(10) 0.1946(5) 0.030(2) Uani 1 1 d U . .
Cl1 Cl 0.3893(3) 0.3618(5) 0.4658(2) 0.0453(13) Uani 1 1 d . . .
Cl2 Cl 0.0214(3) 0.5226(5) 0.3849(2) 0.0436(13) Uani 1 1 d . . .
Cl3 Cl 0.4818(3) 0.4521(5) 0.1479(2) 0.0446(13) Uani 1 1 d . . .
Cl4 Cl 0.1265(3) 0.6718(5) 0.0580(2) 0.0417(13) Uani 1 1 d . . .
C1 C 0.4531(10) 0.3180(16) 0.2816(7) 0.033(3) Uani 1 1 d U . .
H1 H 0.4306 0.2372 0.2553 0.040 Uiso 1 1 calc R . .
C2 C 0.5500(11) 0.3290(16) 0.3086(8) 0.036(3) Uani 1 1 d U . .
H2 H 0.5928 0.2610 0.2996 0.043 Uiso 1 1 calc R . .
C3 C 0.5819(11) 0.4409(16) 0.3484(8) 0.036(3) Uani 1 1 d U . .
H3 H 0.6480 0.4509 0.3686 0.043 Uiso 1 1 calc R . .
C4 C 0.5213(11) 0.5355(17) 0.3590(8) 0.036(3) Uani 1 1 d U . .
H4 H 0.5442 0.6125 0.3874 0.044 Uiso 1 1 calc R . .
C5 C 0.4248(11) 0.5249(16) 0.3298(7) 0.031(3) Uani 1 1 d U . .
H5 H 0.3829 0.5962 0.3375 0.038 Uiso 1 1 calc R . .
C6 C 0.2123(10) 0.0767(15) 0.2043(8) 0.027(2) Uani 1 1 d U . .
H6 H 0.1970 0.1166 0.1639 0.032 Uiso 1 1 calc R . .
C7 C 0.2095(10) -0.0724(15) 0.2122(8) 0.028(2) Uani 1 1 d U . .
H7 H 0.1852 -0.1336 0.1773 0.034 Uiso 1 1 calc R . .
C8 C 0.2412(10) -0.1305(16) 0.2692(7) 0.030(3) Uani 1 1 d U . .
H8 H 0.2436 -0.2329 0.2743 0.036 Uiso 1 1 calc R . .
C9 C 0.2692(10) -0.0437(15) 0.3185(8) 0.030(3) Uani 1 1 d U . .
H9 H 0.2927 -0.0819 0.3591 0.036 Uiso 1 1 calc R . .
C10 C 0.2624(9) 0.1051(16) 0.3077(7) 0.026(2) Uani 1 1 d U . .
H10 H 0.2782 0.1661 0.3431 0.032 Uiso 1 1 calc R . .
C11 C 0.0665(11) 0.5793(16) 0.2251(8) 0.038(3) Uani 1 1 d U . .
H11 H 0.1013 0.6194 0.2638 0.045 Uiso 1 1 calc R . .
C12 C -0.0167(11) 0.6486(16) 0.1926(8) 0.040(3) Uani 1 1 d U . .
H12 H -0.0382 0.7343 0.2078 0.048 Uiso 1 1 calc R . .
C13 C -0.0666(11) 0.5873(17) 0.1373(8) 0.041(3) Uani 1 1 d U . .
H13 H -0.1234 0.6341 0.1142 0.049 Uiso 1 1 calc R . .
C14 C -0.0398(11) 0.4621(17) 0.1128(8) 0.039(3) Uani 1 1 d U . .
H14 H -0.0762 0.4199 0.0750 0.047 Uiso 1 1 calc R . .
C15 C 0.0451(11) 0.4046(17) 0.1488(8) 0.038(3) Uani 1 1 d U . .
H15 H 0.0681 0.3199 0.1338 0.045 Uiso 1 1 calc R . .
C16 C 0.2229(12) 0.5044(17) 0.3761(9) 0.037(2) Uani 1 1 d U . .
C17 C 0.2024(12) 0.4356(16) 0.4300(8) 0.035(2) Uani 1 1 d U . .
C18 C 0.2734(11) 0.3614(16) 0.4727(8) 0.035(3) Uani 1 1 d U . .
C19 C 0.2585(11) 0.2930(16) 0.5235(8) 0.036(3) Uani 1 1 d U . .
H19 H 0.3095 0.2473 0.5534 0.043 Uiso 1 1 calc R . .
C20 C 0.1645(11) 0.2924(16) 0.5301(7) 0.036(3) Uani 1 1 d U . .
H20 H 0.1514 0.2394 0.5628 0.043 Uiso 1 1 calc R . .
C21 C 0.0943(11) 0.3672(15) 0.4897(7) 0.034(3) Uani 1 1 d U . .
H21 H 0.0324 0.3718 0.4949 0.041 Uiso 1 1 calc R . .
C22 C 0.1151(11) 0.4384(16) 0.4398(7) 0.034(3) Uani 1 1 d U . .
C23 C 0.2791(12) 0.5082(16) 0.1545(8) 0.034(2) Uani 1 1 d U . .
C24 C 0.3047(11) 0.5687(16) 0.0975(7) 0.032(2) Uani 1 1 d U . .
C25 C 0.3955(11) 0.5474(16) 0.0905(8) 0.034(3) Uani 1 1 d U . .
C26 C 0.4267(11) 0.6113(17) 0.0456(7) 0.037(3) Uani 1 1 d U . .
H26 H 0.4912 0.6054 0.0453 0.045 Uiso 1 1 calc R . .
C27 C 0.3558(11) 0.6890(16) -0.0019(8) 0.036(3) Uani 1 1 d U . .
H27 H 0.3721 0.7266 -0.0367 0.043 Uiso 1 1 calc R . .
C28 C 0.2679(11) 0.7085(16) 0.0025(8) 0.036(3) Uani 1 1 d U . .
H28 H 0.2229 0.7615 -0.0286 0.044 Uiso 1 1 calc R . .
C29 C 0.2412(11) 0.6507(15) 0.0532(7) 0.031(2) Uani 1 1 d U . .
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'
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
_geom_angle_publ_flag
O1 Zn1 N2 90.1(5) . . ?
O1 Zn1 N3 87.0(5) . . ?
N2 Zn1 N3 106.8(5) . . ?
O1 Zn1 N1 91.5(5) . . ?
N2 Zn1 N1 95.3(5) . . ?
N3 Zn1 N1 157.8(5) . . ?
O1 Zn1 O3 176.3(4) . . ?
N2 Zn1 O3 91.7(4) . . ?
N3 Zn1 O3 89.4(5) . . ?
N1 Zn1 O3 91.6(5) . . ?
O1 Zn1 O4 121.0(4) . . ?
N2 Zn1 O4 148.5(4) . . ?
N3 Zn1 O4 82.0(4) . . ?
N1 Zn1 O4 79.8(4) . . ?
O3 Zn1 O4 57.7(4) . . ?
O1 Zn1 C23 149.6(5) . . ?
N2 Zn1 C23 120.2(5) . . ?
N3 Zn1 C23 85.9(5) . . ?
N1 Zn1 C23 84.2(5) . . ?
O3 Zn1 C23 29.0(4) . . ?
O4 Zn1 C23 28.7(4) . . ?
>C1 N1 C5 115.2(13) . . ?
C1 N1 Zn1 124.0(11) . . ?
C5 N1 Zn1 120.7(10) . . ?
C10 N2 C6 115.8(13) . . ?
C10 N2 Zn1 121.8(11) . . ?
C6 N2 Zn1 122.3(10) . . ?
C11 N3 C15 115.4(14) . . ?
C11 N3 Zn1 121.2(11) . . ?
C15 N3 Zn1 122.0(10) . . ?
C16 O1 Zn1 144.2(10) . . ?
C23 O3 Zn1 92.2(11) . . ?
C23 O4 Zn1 84.9(9) . . ?
N1 C1 C2 124.9(15) . . ?
C3 C2 C1 117.5(16) . . ?
C4 C3 C2 120.0(16) . . ?
C3 C4 C5 121.4(17) . . ?
N1 C5 C4 120.9(15) . . ?
C7 C6 N2 120.1(15) . . ?
C8 C7 C6 120.0(16) . . ?
C9 C8 C7 119.8(15) . . ?
C8 C9 C10 117.0(16) . . ?
N2 C10 C9 126.8(16) . . ?
N3 C11 C12 124.4(17) . . ?
C13 C12 C11 116.7(16) . . ?
C12 C13 C14 124.6(16) . . ?
C15 C14 C13 113.4(17) . . ?
C14 C15 N3 125.5(16) . . ?
O2 C16 O1 122.2(17) . . ?
O2 C16 C17 123.4(17) . . ?
O1 C16 C17 114.3(13) . . ?
C22 C17 C18 116.9(15) . . ?
C22 C17 C16 123.4(15) . . ?
C18 C17 C16 119.7(15) . . ?
C19 C18 C17 122.6(15) . . ?
C19 C18 Cl1 117.7(12) . . ?
C17 C18 Cl1 119.6(13) . . ?
C18 C19 C20 118.5(15) . . ?
C21 C20 C19 119.9(15) . . ?
C20 C21 C22 118.5(15) . . ?
C17 C22 C21 123.4(15) . . ?
C17 C22 Cl2 118.6(13) . . ?
C21 C22 Cl2 117.8(12) . . ?
O4 C23 O3 125.2(16) . . ?
O4 C23 C24 116.8(13) . . ?
O3 C23 C24 118.0(15) . . ?
O4 C23 Zn1 66.5(9) . . ?
O3 C23 Zn1 58.8(9) . . ?
C24 C23 Zn1 176.4(11) . . ?
C29 C24 C25 117.4(14) . . ?
C29 C24 C23 121.7(14) . . ?
C25 C24 C23 120.8(15) . . ?
C26 C25 C24 124.0(16) . . ?
C26 C25 Cl3 116.0(13) . . ?
C24 C25 Cl3 119.5(13) . . ?
C25 C26 C27 116.2(15) . . ?
C28 C27 C26 120.9(15) . . ?
C27 C28 C29 120.6(16) . . ?
C24 C29 C28 120.4(14) . . ?
C24 C29 Cl4 118.8(12) . . ?
C28 C29 Cl4 120.7(13) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O1 1.977(11) . ?
Zn1 N2 2.087(11) . ?
Zn1 N3 2.100(13) . ?
Zn1 N1 2.108(12) . ?
Zn1 O3 2.183(11) . ?
Zn1 O4 2.348(10) . ?
Zn1 C23 2.551(17) . ?
N1 C1 1.336(17) . ?
N1 C5 1.379(18) . ?
N2 C10 1.268(16) . ?
N2 C6 1.389(17) . ?
N3 C11 1.322(18) . ?
N3 C15 1.415(19) . ?
O1 C16 1.345(18) . ?
O2 C16 1.220(17) . ?
O3 C23 1.239(16) . ?
O4 C23 1.228(16) . ?
Cl1 C18 1.755(16) . ?
Cl2 C22 1.746(16) . ?
Cl3 C25 1.763(17) . ?
Cl4 C29 1.731(15) . ?
C1 C2 1.381(19) . ?
C2 C3 1.360(19) . ?
C3 C4 1.32(2) . ?
C4 C5 1.38(2) . ?
C6 C7 1.39(2) . ?
C7 C8 1.348(19) . ?
C8 C9 1.336(19) . ?
C9 C10 1.391(19) . ?
C11 C12 1.39(2) . ?
C12 C13 1.37(2) . ?
C13 C14 1.38(2) . ?
C14 C15 1.38(2) . ?
C16 C17 1.48(2) . ?
C17 C22 1.36(2) . ?
C17 C18 1.38(2) . ?
C18 C19 1.38(2) . ?
C19 C20 1.430(19) . ?
C20 C21 1.35(2) . ?
C21 C22 1.41(2) . ?
C23 C24 1.55(2) . ?
C24 C29 1.38(2) . ?
C24 C25 1.40(2) . ?
C25 C26 1.36(2) . ?
C26 C27 1.45(2) . ?
C27 C28 1.336(19) . ?
C28 C29 1.42(2) . ?
