#------------------------------------------------------------------------------
#$Date: 2016-03-23 03:39:23 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179255 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/75/4317554.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_4317554
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            'C34 H26 F4 N4 O4 Zn'
_chemical_formula_weight         695.96
_chemical_name_systematic
;
  ?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 108.8850(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.6569(7)
_cell_length_b                   10.9364(7)
_cell_length_c                   12.8998(8)
_cell_measurement_temperature    110(2)
_cell_volume                     1556.00(17)
_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 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0443
_diffrn_reflns_av_sigmaI/netI    0.0300
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6822
_diffrn_reflns_theta_full        23.27
_diffrn_reflns_theta_max         23.27
_diffrn_reflns_theta_min         1.67
_exptl_absorpt_coefficient_mu    0.859
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.033(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     424
_refine_ls_number_reflns         3512
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.136
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0256
_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)+(0.0344P)²+0.5636P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0660
_refine_ls_wR_factor_ref         0.0663
_reflns_number_gt                3471
_reflns_number_total             3512
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic0107983_2.cif
_cod_data_source_block           1b
_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               4317554
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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 0.11810(3) 0.26110(3) 0.21299(2) 0.01947(11) Uani 1 1 d . . .
O1 O 0.25744(18) 0.1757(2) 0.32781(16) 0.0260(5) Uani 1 1 d . . .
O2 O 0.2878(2) 0.0985(3) 0.17944(17) 0.0341(6) Uani 1 1 d . . .
O3 O -0.0066(2) 0.3772(2) 0.23622(16) 0.0237(6) Uani 1 1 d . . .
O4 O 0.09386(19) 0.3681(3) 0.41510(16) 0.0307(6) Uani 1 1 d . . .
N1 N 0.2422(2) 0.4086(3) 0.20942(19) 0.0223(6) Uani 1 1 d . . .
N2 N 0.05172(18) 0.2627(3) 0.03989(15) 0.0197(5) Uani 1 1 d . . .
N3 N -0.0026(2) 0.1103(3) 0.2222(2) 0.0220(7) Uani 1 1 d . . .
F1 F 0.55598(17) 0.1748(2) 0.32289(15) 0.0395(5) Uani 1 1 d . . .
F2 F 0.28764(16) -0.1116(2) 0.38376(14) 0.0329(5) Uani 1 1 d . . .
F3 F 0.01181(16) 0.64344(19) 0.40278(14) 0.0323(5) Uani 1 1 d . . .
F4 F -0.21468(15) 0.2821(2) 0.31663(14) 0.0364(5) Uani 1 1 d . . .
C1 C 0.2466(3) 0.5144(4) 0.2628(2) 0.0288(8) Uani 1 1 d . . .
H1 H 0.1915 0.5262 0.3023 0.035 Uiso 1 1 calc R . .
C2 C 0.3268(3) 0.6069(4) 0.2633(3) 0.0346(9) Uani 1 1 d . . .
H2 H 0.3268 0.6802 0.3028 0.042 Uiso 1 1 calc R . .
C3 C 0.4073(3) 0.5920(4) 0.2058(3) 0.0341(9) Uani 1 1 d . . .
H3 H 0.4634 0.6545 0.2043 0.041 Uiso 1 1 calc R . .
C4 C 0.4034(3) 0.4830(4) 0.1507(3) 0.0339(9) Uani 1 1 d . . .
H4 H 0.4574 0.4692 0.1103 0.041 Uiso 1 1 calc R . .
C5 C 0.3213(3) 0.3947(4) 0.1545(3) 0.0294(8) Uani 1 1 d . . .
H5 H 0.3204 0.3202 0.1164 0.035 Uiso 1 1 calc R . .
C6 C -0.0342(3) 0.3446(3) -0.0089(2) 0.0249(8) Uani 1 1 d . . .
H6 H -0.0589 0.4011 0.0357 0.030 Uiso 1 1 calc R . .
C7 C -0.0884(3) 0.3504(3) -0.1210(2) 0.0261(8) Uani 1 1 d . . .
H7 H -0.1494 0.4094 -0.1528 0.031 Uiso 1 1 calc R . .
C8 C -0.0523(2) 0.2688(4) -0.18616(19) 0.0275(7) Uani 1 1 d . . .
H8 H -0.0879 0.2709 -0.2636 0.033 Uiso 1 1 calc R . .
C9 C 0.0356(3) 0.1849(4) -0.1372(2) 0.0307(8) Uani 1 1 d . . .
H9 H 0.0619 0.1280 -0.1804 0.037 Uiso 1 1 calc R . .
C10 C 0.0860(3) 0.1835(3) -0.0242(2) 0.0254(8) Uani 1 1 d . . .
H10 H 0.1467 0.1247 0.0091 0.030 Uiso 1 1 calc R . .
C11 C -0.1024(3) 0.0802(3) 0.1398(2) 0.0259(8) Uani 1 1 d . . .
H11 H -0.1163 0.1183 0.0706 0.031 Uiso 1 1 calc R . .
C12 C -0.1859(3) -0.0037(4) 0.1507(2) 0.0319(8) Uani 1 1 d . . .
H12 H -0.2552 -0.0235 0.0900 0.038 Uiso 1 1 calc R . .
C13 C -0.1676(3) -0.0586(4) 0.2510(2) 0.0320(8) Uani 1 1 d . . .
H13 H -0.2244 -0.1158 0.2610 0.038 Uiso 1 1 calc R . .
C14 C -0.0650(3) -0.0286(4) 0.3365(2) 0.0296(8) Uani 1 1 d . . .
H14 H -0.0497 -0.0651 0.4065 0.036 Uiso 1 1 calc R . .
C15 C 0.0151(3) 0.0555(3) 0.3187(2) 0.0271(8) Uani 1 1 d . . .
H15 H 0.0860 0.0752 0.3777 0.032 Uiso 1 1 calc R . .
C16 C 0.3134(3) 0.1084(3) 0.2798(2) 0.0209(7) Uani 1 1 d . . .
C17 C 0.4182(3) 0.0349(3) 0.3520(2) 0.0218(7) Uani 1 1 d . . .
C18 C 0.5376(3) 0.0697(3) 0.3698(2) 0.0262(8) Uani 1 1 d . . .
C19 C 0.6359(3) 0.0030(4) 0.4334(2) 0.0323(9) Uani 1 1 d . . .
H19 H 0.7163 0.0301 0.4442 0.039 Uiso 1 1 calc R . .
C20 C 0.6146(3) -0.1033(4) 0.4804(2) 0.0352(9) Uani 1 1 d . . .
H20 H 0.6812 -0.1503 0.5242 0.042 Uiso 1 1 calc R . .
C21 C 0.4982(3) -0.1430(4) 0.4655(2) 0.0320(8) Uani 1 1 d . . .
H21 H 0.4835 -0.2168 0.4980 0.038 Uiso 1 1 calc R . .
C22 C 0.4029(3) -0.0716(3) 0.4011(2) 0.0243(7) Uani 1 1 d . . .
C23 C 0.0053(3) 0.3970(3) 0.3367(2) 0.0214(7) Uani 1 1 d . . .
C24 C -0.0997(3) 0.4614(3) 0.3566(2) 0.0206(7) Uani 1 1 d . . .
C25 C -0.2074(3) 0.4017(3) 0.3453(2) 0.0251(8) Uani 1 1 d . . .
C26 C -0.3047(3) 0.4574(4) 0.3641(2) 0.0307(8) Uani 1 1 d . . .
H26 H -0.3777 0.4136 0.3553 0.037 Uiso 1 1 calc R . .
C27 C -0.2937(3) 0.5784(4) 0.3960(2) 0.0321(9) Uani 1 1 d . . .
H27 H -0.3603 0.6183 0.4088 0.039 Uiso 1 1 calc R . .
C28 C -0.1877(3) 0.6432(4) 0.4098(2) 0.0281(8) Uani 1 1 d . . .
H28 H -0.1800 0.7264 0.4321 0.034 Uiso 1 1 calc R . .
C29 C -0.0935(3) 0.5817(3) 0.3898(2) 0.0231(8) Uani 1 1 d . . .
N1A N 0.5762(3) 0.7954(4) 0.0907(3) 0.0547(11) Uani 1 1 d . . .
C1A C 0.4977(5) 0.8737(4) 0.1067(3) 0.0523(12) Uani 1 1 d . . .
H1A H 0.5245 0.9248 0.1695 0.063 Uiso 1 1 calc R . .
C2A C 0.3806(4) 0.8868(5) 0.0398(4) 0.0525(11) Uani 1 1 d . . .
H2A H 0.3282 0.9446 0.0562 0.063 Uiso 1 1 calc R . .
C3A C 0.3415(4) 0.8158(4) -0.0498(3) 0.0474(11) Uani 1 1 d . . .
H3A H 0.2608 0.8241 -0.0983 0.057 Uiso 1 1 calc R . .
C4A C 0.4169(3) 0.7322(4) -0.0711(3) 0.0429(11) Uani 1 1 d . . .
H4A H 0.3899 0.6809 -0.1338 0.052 Uiso 1 1 calc R . .
C5A C 0.5336(4) 0.7236(4) 0.0001(3) 0.0461(11) Uani 1 1 d . . .
H5A H 0.5865 0.6650 -0.0145 0.055 Uiso 1 1 calc 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'
F F 0.0171 0.0103 '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
O3 Zn1 O1 128.46(8) . . ?
O3 Zn1 N2 96.68(9) . . ?
O1 Zn1 N2 134.85(10) . . ?
O3 Zn1 N1 92.97(10) . . ?
O1 Zn1 N1 88.64(10) . . ?
N2 Zn1 N1 89.43(10) . . ?
O3 Zn1 N3 87.72(10) . . ?
O1 Zn1 N3 89.44(10) . . ?
N2 Zn1 N3 92.37(10) . . ?
N1 Zn1 N3 177.98(10) . . ?
C16 O1 Zn1 109.02(17) . . ?
C23 O3 Zn1 114.2(2) . . ?
C1 N1 C5 116.8(3) . . ?
C1 N1 Zn1 123.0(2) . . ?
C5 N1 Zn1 120.1(3) . . ?
C6 N2 C10 117.9(2) . . ?
C6 N2 Zn1 117.6(2) . . ?
C10 N2 Zn1 124.4(2) . . ?
C15 N3 C11 117.5(3) . . ?
C15 N3 Zn1 118.6(2) . . ?
C11 N3 Zn1 123.3(2) . . ?
N1 C1 C2 123.4(3) . . ?
C1 C2 C3 119.3(4) . . ?
C2 C3 C4 117.6(3) . . ?
C5 C4 C3 119.8(3) . . ?
N1 C5 C4 123.1(4) . . ?
N2 C6 C7 122.8(3) . . ?
C6 C7 C8 118.8(3) . . ?
C9 C8 C7 118.8(2) . . ?
C8 C9 C10 119.5(3) . . ?
N2 C10 C9 122.1(3) . . ?
N3 C11 C12 123.0(3) . . ?
C11 C12 C13 119.1(3) . . ?
C12 C13 C14 118.5(3) . . ?
C13 C14 C15 118.9(3) . . ?
N3 C15 C14 123.0(3) . . ?
O2 C16 O1 125.0(3) . . ?
O2 C16 C17 118.3(3) . . ?
O1 C16 C17 116.7(2) . . ?
C22 C17 C18 115.6(3) . . ?
C22 C17 C16 122.7(3) . . ?
C18 C17 C16 121.6(3) . . ?
F1 C18 C19 119.7(3) . . ?
F1 C18 C17 117.1(3) . . ?
C19 C18 C17 123.2(3) . . ?
C20 C19 C18 118.5(3) . . ?
C19 C20 C21 121.1(3) . . ?
C20 C21 C22 117.8(4) . . ?
F2 C22 C17 117.9(3) . . ?
F2 C22 C21 118.2(3) . . ?
C17 C22 C21 123.8(3) . . ?
O4 C23 O3 125.3(3) . . ?
O4 C23 C24 119.5(2) . . ?
O3 C23 C24 115.2(2) . . ?
C29 C24 C25 116.0(3) . . ?
C29 C24 C23 122.4(3) . . ?
C25 C24 C23 121.6(3) . . ?
F4 C25 C26 119.5(3) . . ?
F4 C25 C24 117.4(3) . . ?
C26 C25 C24 123.1(4) . . ?
C25 C26 C27 118.3(3) . . ?
C26 C27 C28 121.5(3) . . ?
C29 C28 C27 117.2(3) . . ?
F3 C29 C24 117.8(3) . . ?
F3 C29 C28 118.3(3) . . ?
C24 C29 C28 123.9(3) . . ?
C1A N1A C5A 115.5(3) . . ?
N1A C1A C2A 124.8(4) . . ?
C3A C2A C1A 118.3(4) . . ?
C2A C3A C4A 120.1(4) . . ?
C3A C4A C5A 118.4(4) . . ?
N1A C5A C4A 122.8(4) . . ?
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 O3 2.024(2) . ?
Zn1 O1 2.036(2) . ?
Zn1 N2 2.1135(18) . ?
Zn1 N1 2.177(3) . ?
Zn1 N3 2.195(3) . ?
O1 C16 1.270(4) . ?
O2 C16 1.235(4) . ?
O3 C23 1.277(4) . ?
O4 C23 1.230(4) . ?
N1 C1 1.338(5) . ?
N1 C5 1.342(4) . ?
N2 C6 1.339(4) . ?
N2 C10 1.344(4) . ?
N3 C15 1.336(4) . ?
N3 C11 1.339(4) . ?
F1 C18 1.347(4) . ?
F2 C22 1.360(4) . ?
F3 C29 1.363(4) . ?
F4 C25 1.354(4) . ?
C1 C2 1.376(5) . ?
C2 C3 1.381(5) . ?
C3 C4 1.382(6) . ?
C4 C5 1.371(5) . ?
C6 C7 1.380(4) . ?
C7 C8 1.382(5) . ?
C8 C9 1.368(5) . ?
C9 C10 1.384(4) . ?
C11 C12 1.378(5) . ?
C12 C13 1.378(5) . ?
C13 C14 1.378(5) . ?
C14 C15 1.382(5) . ?
C16 C17 1.507(4) . ?
C17 C22 1.365(5) . ?
C17 C18 1.389(4) . ?
C18 C19 1.382(5) . ?
C19 C20 1.370(6) . ?
C20 C21 1.378(5) . ?
C21 C22 1.391(5) . ?
C23 C24 1.504(4) . ?
C24 C29 1.379(5) . ?
C24 C25 1.380(5) . ?
C25 C26 1.376(5) . ?
C26 C27 1.380(5) . ?
C27 C28 1.385(5) . ?
C28 C29 1.381(5) . ?
N1A C1A 1.318(6) . ?
N1A C5A 1.361(6) . ?
C1A C2A 1.366(6) . ?
C2A C3A 1.344(6) . ?
C3A C4A 1.357(6) . ?
C4A C5A 1.376(6) . ?
