#------------------------------------------------------------------------------
#$Date: 2016-03-21 08:55:59 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178614 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/25/4072598.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_4072598
loop_
_publ_author_name
'Anantharaman, Ganapathi'
'Elango, Kandasamy'
_publ_section_title
;
 Synthesis and Characterization of NHC-Stabilized Zinc Aryloxide and Zinc
 Hydroxyaryloxide†
;
_journal_issue                   4
_journal_name_full               Organometallics
_journal_page_first              1089
_journal_paper_doi               10.1021/om060867r
_journal_volume                  26
_journal_year                    2007
_chemical_formula_sum            'C45 H58 N2 O2 Zn'
_chemical_formula_weight         724.30
_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                 115.14(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   24.015(5)
_cell_length_b                   9.998(2)
_cell_length_c                   18.294(4)
_cell_measurement_temperature    '100 K(2)'
_cell_volume                     3976.3(17)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Stoe IPDS'
_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  0.0420
_diffrn_reflns_av_sigmaI/netI    0.0531
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13023
_diffrn_reflns_theta_full        28.33
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         2.24
_exptl_absorpt_coefficient_mu    0.656
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         1.105
_refine_diff_density_min         -1.118
_refine_diff_density_rms         0.134
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.162
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         4943
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.162
_refine_ls_R_factor_all          0.0801
_refine_ls_R_factor_gt           0.0506
_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)+(0.0000P)²+25.8316P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.1397
_reflns_number_gt                3782
_reflns_number_total             4943
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om060867rsi20060922_074227.cif
_cod_data_source_block           complex2
_cod_original_cell_volume        3976.5(14)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4072598
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
Zn1 Zn 0.0000 0.49690(5) 0.2500 0.01725(13) Uani 1 2 d S
O1 O 0.05165(11) 0.4260(2) 0.20672(15) 0.0240(5) Uani 1 1 d .
N1 N 0.04660(12) 0.7781(3) 0.29366(16) 0.0184(5) Uani 1 1 d .
C1 C 0.0000 0.6952(4) 0.2500 0.0200(9) Uani 1 2 d S
C3 C 0.10593(14) 0.7254(3) 0.34835(19) 0.0194(6) Uani 1 1 d .
C12 C 0.05343(15) 0.3058(3) 0.1766(2) 0.0215(7) Uani 1 1 d .
C8 C 0.14912(15) 0.7001(3) 0.3178(2) 0.0205(6) Uani 1 1 d .
C7 C 0.20431(15) 0.6410(3) 0.3699(2) 0.0229(7) Uani 1 1 d .
H7 H 0.2343 0.6246 0.3515 0.027 Uiso 1 1 calc R
C14 C 0.11347(17) 0.1129(3) 0.1736(2) 0.0251(7) Uani 1 1 d .
H14 H 0.1510 0.0684 0.1921 0.030 Uiso 1 1 calc R
C16 C 0.00621(16) 0.1197(3) 0.0876(2) 0.0244(7) Uani 1 1 d .
H16 H -0.0285 0.0795 0.0484 0.029 Uiso 1 1 calc R
C21 C 0.16863(16) 0.3096(3) 0.2621(2) 0.0252(7) Uani 1 1 d .
H21 H 0.1565 0.3734 0.2934 0.030 Uiso 1 1 calc R
C17 C 0.00085(16) 0.2460(3) 0.1156(2) 0.0249(7) Uani 1 1 d .
C18 C -0.06016(16) 0.3197(4) 0.0780(2) 0.0251(7) Uani 1 1 d .
H18 H -0.0543 0.4061 0.1056 0.030 Uiso 1 1 calc R
C6 C 0.21585(15) 0.6060(3) 0.4482(2) 0.0246(7) Uani 1 1 d .
C5 C 0.17140(16) 0.6345(4) 0.4758(2) 0.0261(7) Uani 1 1 d .
H5 H 0.1792 0.6126 0.5287 0.031 Uiso 1 1 calc R
C13 C 0.11097(15) 0.2384(3) 0.2041(2) 0.0227(7) Uani 1 1 d .
C2 C 0.02946(15) 0.9115(3) 0.2777(2) 0.0225(7) Uani 1 1 d .
H2 H 0.0538 0.9860 0.3008 0.027 Uiso 1 1 calc R
C9 C 0.13517(16) 0.7295(4) 0.2311(2) 0.0256(7) Uani 1 1 d .
H9A H 0.1052 0.6669 0.1966 0.038 Uiso 1 1 calc R
H9B H 0.1722 0.7218 0.2234 0.038 Uiso 1 1 calc R
H9C H 0.1192 0.8187 0.2179 0.038 Uiso 1 1 calc R
C15 C 0.06142(17) 0.0523(4) 0.1163(2) 0.0280(8) Uani 1 1 d .
H15 H 0.0637 -0.0329 0.0973 0.034 Uiso 1 1 calc R
C4 C 0.11570(15) 0.6947(3) 0.4270(2) 0.0226(7) Uani 1 1 d .
C22 C 0.19609(17) 0.3896(4) 0.2139(2) 0.0308(8) Uani 1 1 d .
H22A H 0.2083 0.3293 0.1825 0.046 Uiso 1 1 calc R
H22B H 0.2313 0.4386 0.2504 0.046 Uiso 1 1 calc R
H22C H 0.1659 0.4508 0.1785 0.046 Uiso 1 1 calc R
C23 C 0.21732(17) 0.2168(4) 0.3218(2) 0.0325(8) Uani 1 1 d .
H23A H 0.1992 0.1639 0.3499 0.049 Uiso 1 1 calc R
H23B H 0.2503 0.2692 0.3601 0.049 Uiso 1 1 calc R
H23C H 0.2330 0.1590 0.2931 0.049 Uiso 1 1 calc R
C11 C 0.27458(16) 0.5355(4) 0.5016(2) 0.0325(8) Uani 1 1 d .
H11A H 0.2666 0.4418 0.5036 0.049 Uiso 1 1 calc R
H11B H 0.2901 0.5723 0.5551 0.049 Uiso 1 1 calc R
H11C H 0.3045 0.5474 0.4802 0.049 Uiso 1 1 calc R
C19 C -0.07946(19) 0.3489(5) -0.0109(2) 0.0401(10) Uani 1 1 d .
H19A H -0.0841 0.2663 -0.0397 0.060 Uiso 1 1 calc R
H19B H -0.0486 0.4026 -0.0170 0.060 Uiso 1 1 calc R
H19C H -0.1179 0.3963 -0.0322 0.060 Uiso 1 1 calc R
C10 C 0.06802(18) 0.7231(4) 0.4580(2) 0.0347(9) Uani 1 1 d .
H10A H 0.0568 0.8159 0.4501 0.052 Uiso 1 1 calc R
H10B H 0.0846 0.7023 0.5146 0.052 Uiso 1 1 calc R
H10C H 0.0323 0.6690 0.4293 0.052 Uiso 1 1 calc R
C20 C -0.11058(18) 0.2471(4) 0.0906(3) 0.0389(10) Uani 1 1 d .
H20A H -0.1476 0.2993 0.0686 0.058 Uiso 1 1 calc R
H20B H -0.0983 0.2339 0.1474 0.058 Uiso 1 1 calc R
H20C H -0.1178 0.1619 0.0640 0.058 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'
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
O1 Zn1 O1 135.47(14) 2
O1 Zn1 C1 112.26(7) 2
O1 Zn1 C1 112.26(7) .
C12 O1 Zn1 131.4(2) .
C1 N1 C2 111.6(3) .
C1 N1 C3 120.7(3) .
C2 N1 C3 127.6(3) .
N1 C1 N1 104.2(4) 2
N1 C1 Zn1 127.92(19) 2
N1 C1 Zn1 127.92(19) .
C4 C3 C8 123.2(3) .
C4 C3 N1 118.6(3) .
C8 C3 N1 118.0(3) .
O1 C12 C17 122.2(3) .
O1 C12 C13 118.6(3) .
C17 C12 C13 119.1(3) .
C7 C8 C3 117.1(3) .
C7 C8 C9 121.7(3) .
C3 C8 C9 121.1(3) .
C6 C7 C8 122.0(3) .
C13 C14 C15 121.5(3) .
C15 C16 C17 122.0(3) .
C13 C21 C23 114.1(3) .
C13 C21 C22 109.2(3) .
C23 C21 C22 110.0(3) .
C16 C17 C12 118.9(3) .
C16 C17 C18 119.8(3) .
C12 C17 C18 121.3(3) .
C20 C18 C19 110.9(3) .
C20 C18 C17 112.3(3) .
C19 C18 C17 112.1(3) .
C7 C6 C5 118.5(3) .
C7 C6 C11 120.7(3) .
C5 C6 C11 120.8(3) .
C4 C5 C6 122.1(3) .
C14 C13 C12 119.2(3) .
C14 C13 C21 121.6(3) .
C12 C13 C21 119.0(3) .
C2 C2 N1 106.31(18) 2
C16 C15 C14 119.1(3) .
C3 C4 C5 117.0(3) .
C3 C4 C10 121.9(3) .
C5 C4 C10 121.1(3) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 O1 1.872(2) 2
Zn1 O1 1.872(2) .
Zn1 C1 1.983(4) .
O1 C12 1.330(4) .
N1 C1 1.348(4) .
N1 C2 1.390(4) .
N1 C3 1.448(4) .
C1 N1 1.348(4) 2
C3 C4 1.390(5) .
C3 C8 1.394(4) .
C12 C17 1.414(5) .
C12 C13 1.424(5) .
C8 C7 1.393(5) .
C8 C9 1.505(4) .
C7 C6 1.384(5) .
C14 C13 1.384(5) .
C14 C15 1.385(5) .
C16 C15 1.378(5) .
C16 C17 1.389(5) .
C21 C13 1.518(5) .
C21 C23 1.529(5) .
C21 C22 1.533(5) .
C17 C18 1.519(5) .
C18 C20 1.512(5) .
C18 C19 1.518(5) .
C6 C5 1.391(5) .
C6 C11 1.506(5) .
C5 C4 1.391(5) .
C2 C2 1.346(7) 2
C4 C10 1.506(5) .
