#------------------------------------------------------------------------------
#$Date: 2016-03-21 10:26:36 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178651 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/62/4076265.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_4076265
loop_
_publ_author_name
'Kaur, Harneet'
'Zinn, Fabiano Kauer'
'Stevens, Edwin D.'
'Nolan, Steven P.'
_publ_section_title
;
 (NHC)CuI(NHC = N-Heterocyclic Carbene) Complexes as Efficient Catalysts
 for the Reduction of Carbonyl Compounds
;
_journal_issue                   5
_journal_name_full               Organometallics
_journal_page_first              1157
_journal_paper_doi               10.1021/om034285a
_journal_volume                  23
_journal_year                    2004
_chemical_formula_sum            'C27 H36 Cl Cu N2'
_chemical_formula_weight         487.57
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           56
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ab 2ac'
_symmetry_space_group_name_H-M   'P c 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                   10.6855(10)
_cell_length_b                   12.7453(12)
_cell_length_c                   19.1833(18)
_cell_measurement_reflns_used    10508
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.341
_cell_measurement_theta_min      2.124
_cell_volume                     2612.6(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0312
_diffrn_reflns_av_sigmaI/netI    0.0134
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            19466
_diffrn_reflns_theta_full        22.49
_diffrn_reflns_theta_max         22.49
_diffrn_reflns_theta_min         2.49
_exptl_absorpt_coefficient_mu    0.954
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.810105
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.692
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.172
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         1717
_refine_ls_number_restraints     130
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0359
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1410
_refine_ls_wR_factor_ref         0.1712
_reflns_number_gt                1209
_reflns_number_total             1717
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om034285asi20031107_035155.cif
_cod_data_source_block           nol138m
_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.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      Pccn
_cod_database_code               4076265
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, 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
Cu1 Cu -0.2500 0.2500 0.27661(5) 0.0446(9) Uani 1 2 d SU
Cl1 Cl -0.2500 0.2500 0.16769(15) 0.0545(11) Uani 1 2 d SU
C1 C -0.1741(6) 0.4316(4) 0.3943(3) 0.0604(15) Uani 1 1 d U
N1 N -0.2197(5) 0.3304(4) 0.4184(3) 0.0631(14) Uani 1 1 d U
C2 C -0.2627(6) 0.5079(5) 0.3786(3) 0.0639(17) Uani 1 1 d U
C3 C -0.2178(8) 0.6040(6) 0.3547(4) 0.0784(19) Uani 1 1 d U
H3 H -0.278(6) 0.659(6) 0.338(4) 0.10(2) Uiso 1 1 d .
C4 C -0.0915(8) 0.6198(6) 0.3462(4) 0.086(2) Uani 1 1 d U
H4 H -0.073(7) 0.689(7) 0.335(4) 0.10(2) Uiso 1 1 d .
C5 C -0.0056(8) 0.5429(6) 0.3634(4) 0.0764(18) Uani 1 1 d U
H5 H 0.079(5) 0.562(4) 0.350(3) 0.040(12) Uiso 1 1 d .
C6 C -0.0465(6) 0.4465(5) 0.3867(3) 0.0654(16) Uani 1 1 d U
C7 C -0.4038(7) 0.4906(6) 0.3896(4) 0.0743(18) Uani 1 1 d U
H7 H -0.417(4) 0.421(4) 0.414(2) 0.036(11) Uiso 1 1 d .
C8 C -0.4630(8) 0.5831(7) 0.4316(6) 0.093(2) Uani 1 1 d U
H8A H -0.554(7) 0.559(5) 0.434(4) 0.077(18) Uiso 1 1 d .
H8B H -0.452(6) 0.580(5) 0.478(4) 0.07(2) Uiso 1 1 d .
H8C H -0.454(8) 0.655(8) 0.393(6) 0.16(4) Uiso 1 1 d .
C9 C -0.4679(7) 0.4776(7) 0.3203(4) 0.095(2) Uani 1 1 d U
H9A H -0.4531 0.5400 0.2916 0.142 Uiso 1 1 calc R
H9B H -0.5581 0.4688 0.3277 0.142 Uiso 1 1 calc R
H9C H -0.4344 0.4157 0.2966 0.142 Uiso 1 1 calc R
C10 C 0.0476(7) 0.3583(6) 0.4018(4) 0.0759(18) Uani 1 1 d U
H10 H -0.004(5) 0.311(5) 0.421(3) 0.063(17) Uiso 1 1 d .
C11 C 0.1595(8) 0.3951(7) 0.4453(5) 0.106(3) Uani 1 1 d U
H11A H 0.2087 0.4457 0.4184 0.159 Uiso 1 1 calc R
H11B H 0.2120 0.3346 0.4572 0.159 Uiso 1 1 calc R
H11C H 0.1293 0.4284 0.4882 0.159 Uiso 1 1 calc R
C12 C 0.0899(7) 0.3079(6) 0.3341(4) 0.088(2) Uani 1 1 d U
H12A H 0.1321 0.3605 0.3051 0.133 Uiso 1 1 calc R
H12B H 0.0170 0.2803 0.3091 0.133 Uiso 1 1 calc R
H12C H 0.1480 0.2504 0.3443 0.133 Uiso 1 1 calc R
C13 C -0.2500 0.2500 0.3784(4) 0.0297(18) Uani 1 2 d SU
C14 C -0.2317(6) 0.3014(6) 0.4865(4) 0.0647(19) Uani 1 1 d U
H14 H -0.211(8) 0.350(6) 0.527(3) 0.061(18) Uiso 1 1 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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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
C13 Cu1 Cl1 180.0 . .
C6 C1 C2 123.5(6) . .
C6 C1 N1 119.0(5) . .
C2 C1 N1 117.4(5) . .
C13 N1 C14 108.9(6) . .
C13 N1 C1 125.8(5) . .
C14 N1 C1 125.2(5) . .
C1 C2 C3 116.8(6) . .
C1 C2 C7 122.5(6) . .
C3 C2 C7 120.6(6) . .
C4 C3 C2 120.4(7) . .
C3 C4 C5 121.3(7) . .
C6 C5 C4 119.9(7) . .
C5 C6 C1 117.9(6) . .
C5 C6 C10 120.4(6) . .
C1 C6 C10 121.6(6) . .
C9 C7 C2 109.9(6) . .
C9 C7 C8 110.8(7) . .
C2 C7 C8 111.1(6) . .
C12 C10 C6 110.1(6) . .
C12 C10 C11 111.3(7) . .
C6 C10 C11 112.9(6) . .
N1 C13 N1 108.9(8) 2_455 .
N1 C13 Cu1 125.5(4) 2_455 .
N1 C13 Cu1 125.5(4) . .
N1 C14 C14 106.6(4) . 2_455
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 C13 1.953(8) .
Cu1 Cl1 2.089(4) .
C1 C6 1.384(9) .
C1 C2 1.390(8) .
C1 N1 1.455(8) .
N1 C13 1.320(7) .
N1 C14 1.363(8) .
C2 C3 1.393(9) .
C2 C7 1.539(10) .
C3 C4 1.374(11) .
C4 C5 1.383(11) .
C5 C6 1.378(10) .
C6 C10 1.535(9) .
C7 C9 1.505(10) .
C7 C8 1.561(11) .
C10 C12 1.518(10) .
C10 C11 1.532(10) .
C13 N1 1.320(7) 2_455
C14 C14 1.368(15) 2_455
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_4
C6 C1 N1 C13 -90.2(6) .
C2 C1 N1 C13 88.4(7) .
C6 C1 N1 C14 86.1(8) .
C2 C1 N1 C14 -95.4(7) .
C6 C1 C2 C3 -0.7(10) .
N1 C1 C2 C3 -179.2(6) .
C6 C1 C2 C7 -178.1(6) .
N1 C1 C2 C7 3.4(9) .
C1 C2 C3 C4 1.2(11) .
C7 C2 C3 C4 178.7(6) .
C2 C3 C4 C5 -2.3(12) .
C3 C4 C5 C6 2.7(11) .
C4 C5 C6 C1 -2.1(10) .
C4 C5 C6 C10 176.4(7) .
C2 C1 C6 C5 1.1(9) .
N1 C1 C6 C5 179.6(5) .
C2 C1 C6 C10 -177.4(6) .
N1 C1 C6 C10 1.1(8) .
C1 C2 C7 C9 -107.8(7) .
C3 C2 C7 C9 75.0(9) .
C1 C2 C7 C8 129.3(8) .
C3 C2 C7 C8 -48.0(9) .
C5 C6 C10 C12 -78.0(8) .
C1 C6 C10 C12 100.5(8) .
C5 C6 C10 C11 47.1(9) .
C1 C6 C10 C11 -134.4(7) .
C14 N1 C13 N1 -0.5(3) 2_455
C1 N1 C13 N1 176.2(7) 2_455
C14 N1 C13 Cu1 179.5(3) .
C1 N1 C13 Cu1 -3.8(7) .
Cl1 Cu1 C13 N1 170(100) 2_455
Cl1 Cu1 C13 N1 -10(100) .
C13 N1 C14 C14 1.3(8) 2_455
C1 N1 C14 C14 -175.5(7) 2_455
