#------------------------------------------------------------------------------
#$Date: 2016-03-21 11:07:37 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178681 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/92/4079259.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_4079259
loop_
_publ_author_name
'Lazreg, Faïma'
'Slawin, Alexandra M. Z.'
'Cazin, Catherine S. J.'
_publ_section_title
;
 Heteroleptic Bis(N-heterocyclic carbene)Copper(I) Complexes: Highly
 Efficient Systems for the [3+2] Cycloaddition of Azides and Alkynes
;
_journal_issue                   22
_journal_name_full               Organometallics
_journal_page_first              7969
_journal_paper_doi               10.1021/om3006195
_journal_volume                  31
_journal_year                    2012
_chemical_formula_moiety         'C42 H60 B Cu F4 N4'
_chemical_formula_sum            'C42 H60 B Cu F4 N4'
_chemical_formula_weight         771.29
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           63
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-C 2c 2'
_symmetry_space_group_name_H-M   'C m c m'
_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                   20.475(5)
_cell_length_b                   15.838(4)
_cell_length_c                   13.143(3)
_cell_measurement_reflns_used    5031
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      27.9
_cell_measurement_theta_min      3.2
_cell_volume                     4262.1(18)
_computing_cell_refinement       'CrystalClear (Rigaku Corp., 2004)'
_computing_data_collection       'CrystalClear (Rigaku Corp., 2004)'
_computing_data_reduction        'CrystalClear (Rigaku Corp., 2004)'
_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      93(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0699
_diffrn_reflns_av_sigmaI/netI    0.0380
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11003
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         3.00
_exptl_absorpt_coefficient_mu    0.562
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.600
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1640
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.631
_refine_diff_density_min         -0.911
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.793
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         2087
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.793
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0557
_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)+(0.1150P)²+31.7990P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1495
_refine_ls_wR_factor_ref         0.1616
_reflns_number_gt                1788
_reflns_number_total             2087
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om3006195_si_002.cif
_cod_data_source_block           3d
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        4262.1(16)
_cod_original_sg_symbol_H-M      Cmcm
_cod_database_code               4079259
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y, -z+1/2'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x, y, -z-1/2'
'x, -y, z-1/2'
'-x, y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, y+1/2, -z-1/2'
'x+1/2, -y+1/2, z-1/2'
'-x+1/2, 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
Cu1 Cu 0.0000 0.16146(4) 0.2500 0.0144(3) Uani 1 4 d S
C1 C 0.0000 0.2813(4) 0.2500 0.0151(11) Uani 1 4 d S
N2 N 0.05214(17) 0.3345(2) 0.2500 0.0166(7) Uani 1 2 d S
C3 C 0.0326(2) 0.4180(3) 0.2500 0.0194(9) Uani 1 2 d S
H3A H 0.0602 0.4661 0.2500 0.023 Uiso 1 2 calc SR
C4 C 0.1188(2) 0.3066(3) 0.2500 0.0203(9) Uani 1 2 d S
C5 C 0.14976(15) 0.29471(19) 0.3439(2) 0.0236(7) Uani 1 1 d .
C6 C 0.21561(16) 0.2718(2) 0.3411(3) 0.0351(9) Uani 1 1 d .
H6A H 0.2384 0.2634 0.4033 0.042 Uiso 1 1 calc R
C7 C 0.2486(2) 0.2611(3) 0.2500 0.0411(14) Uani 1 2 d S
H7A H 0.2936 0.2464 0.2500 0.049 Uiso 1 2 calc SR
C8 C 0.11376(17) 0.3035(2) 0.4440(2) 0.0291(8) Uani 1 1 d .
H8A H 0.0688 0.3245 0.4287 0.035 Uiso 1 1 calc R
C9 C 0.1463(2) 0.3670(2) 0.5151(3) 0.0437(10) Uani 1 1 d .
H9A H 0.1497 0.4218 0.4808 0.066 Uiso 1 1 calc R
H9B H 0.1901 0.3470 0.5331 0.066 Uiso 1 1 calc R
H9C H 0.1200 0.3731 0.5769 0.066 Uiso 1 1 calc R
C10 C 0.1071(2) 0.2170(2) 0.4962(3) 0.0468(10) Uani 1 1 d .
H10A H 0.0862 0.1771 0.4495 0.070 Uiso 1 1 calc R
H10B H 0.0804 0.2228 0.5577 0.070 Uiso 1 1 calc R
H10C H 0.1506 0.1960 0.5147 0.070 Uiso 1 1 calc R
C11 C 0.0000 0.0417(4) 0.2500 0.0211(13) Uani 1 4 d S
N12 N 0.05228(17) -0.0105(2) 0.2500 0.0202(8) Uani 1 2 d S
C13 C 0.0333(2) -0.0950(3) 0.2500 0.0272(10) Uani 1 2 d S
H13A H 0.0611 -0.1429 0.2500 0.033 Uiso 1 2 calc SR
C14 C 0.1202(2) 0.0180(3) 0.2500 0.0205(9) Uani 1 2 d S
H14A H 0.1198 0.0811 0.2500 0.025 Uiso 1 2 calc SR
C15 C 0.15653(16) -0.0102(2) 0.1549(2) 0.0310(8) Uani 1 1 d .
H15A H 0.1327 0.0092 0.0937 0.037 Uiso 1 1 calc R
H15B H 0.1588 -0.0726 0.1530 0.037 Uiso 1 1 calc R
C16 C 0.22532(18) 0.0263(2) 0.1549(3) 0.0405(9) Uani 1 1 d .
H16A H 0.2492 0.0053 0.0945 0.049 Uiso 1 1 calc R
H16B H 0.2227 0.0886 0.1498 0.049 Uiso 1 1 calc R
C17 C 0.2628(2) 0.0027(4) 0.2500 0.0475(15) Uani 1 2 d S
H17A H 0.2712 -0.0588 0.2500 0.057 Uiso 1 2 calc SR
H17B H 0.3054 0.0321 0.2500 0.057 Uiso 1 2 calc SR
B1 B 0.5000 0.1621(7) 0.2500 0.090(6) Uani 1 4 d S
F1 F 0.4435(4) 0.2126(3) 0.2500 0.114(2) Uani 1 2 d S
F2 F 0.5000 0.1112(4) 0.1663(5) 0.151(3) Uani 1 2 d S
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'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 '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
C11 Cu1 C1 180.0 . .
N2 C1 N2 103.4(5) . 3
N2 C1 Cu1 128.3(2) . .
N2 C1 Cu1 128.3(2) 3 .
C1 N2 C3 111.4(3) . .
C1 N2 C4 123.8(3) . .
C3 N2 C4 124.8(3) . .
C3 C3 N2 106.8(2) 3 .
C3 C3 H3A 126.6 3 .
N2 C3 H3A 126.6 . .
C5 C4 C5 123.6(4) 10_556 .
C5 C4 N2 118.2(2) 10_556 .
C5 C4 N2 118.2(2) . .
C6 C5 C4 116.7(3) . .
C6 C5 C8 121.1(3) . .
C4 C5 C8 122.2(3) . .
C7 C6 C5 121.7(4) . .
C7 C6 H6A 119.1 . .
C5 C6 H6A 119.1 . .
C6 C7 C6 119.6(4) . 10_556
C6 C7 H7A 120.2 . .
C6 C7 H7A 120.2 10_556 .
C5 C8 C9 112.3(3) . .
C5 C8 C10 110.4(3) . .
C9 C8 C10 110.6(3) . .
C5 C8 H8A 107.8 . .
C9 C8 H8A 107.8 . .
C10 C8 H8A 107.8 . .
C8 C9 H9A 109.5 . .
C8 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C8 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
C8 C10 H10A 109.5 . .
C8 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C8 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
N12 C11 N12 104.7(5) . 3
N12 C11 Cu1 127.6(3) . .
N12 C11 Cu1 127.6(3) 3 .
C11 N12 C13 111.4(4) . .
C11 N12 C14 124.4(4) . .
C13 N12 C14 124.1(4) . .
C13 C13 N12 106.2(2) 3 .
C13 C13 H13A 126.9 3 .
N12 C13 H13A 126.9 . .
N12 C14 C15 112.0(2) . 10_556
N12 C14 C15 112.0(2) . .
C15 C14 C15 110.5(4) 10_556 .
N12 C14 H14A 107.4 . .
C15 C14 H14A 107.4 10_556 .
C15 C14 H14A 107.4 . .
C14 C15 C16 109.9(3) . .
C14 C15 H15A 109.7 . .
C16 C15 H15A 109.7 . .
C14 C15 H15B 109.7 . .
C16 C15 H15B 109.7 . .
H15A C15 H15B 108.2 . .
C17 C16 C15 112.0(3) . .
C17 C16 H16A 109.2 . .
C15 C16 H16A 109.2 . .
C17 C16 H16B 109.2 . .
C15 C16 H16B 109.2 . .
H16A C16 H16B 107.9 . .
C16 C17 C16 111.4(4) 10_556 .
C16 C17 H17A 109.3 10_556 .
C16 C17 H17A 109.3 . .
C16 C17 H17B 109.3 10_556 .
C16 C17 H17B 109.3 . .
H17A C17 H17B 108.0 . .
F2 B1 F2 107.5(10) . 10_556
F2 B1 F1 109.6(2) . 3_655
F2 B1 F1 109.7(2) 10_556 3_655
F2 B1 F1 109.6(2) . .
F2 B1 F1 109.6(2) 10_556 .
F1 B1 F1 110.7(8) 3_655 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 C11 1.897(6) .
Cu1 C1 1.898(6) .
C1 N2 1.360(5) .
C1 N2 1.360(5) 3
N2 C3 1.381(5) .
N2 C4 1.435(5) .
C3 C3 1.334(9) 3
C3 H3A 0.9500 .
C4 C5 1.400(4) 10_556
C4 C5 1.400(4) .
C5 C6 1.397(5) .
C5 C8 1.514(5) .
C6 C7 1.385(5) .
C6 H6A 0.9500 .
C7 C6 1.385(5) 10_556
C7 H7A 0.9500 .
C8 C9 1.526(5) .
C8 C10 1.537(5) .
C8 H8A 1.0000 .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
C11 N12 1.352(5) .
C11 N12 1.352(5) 3
N12 C13 1.394(6) .
N12 C14 1.463(5) .
C13 C13 1.363(10) 3
C13 H13A 0.9500 .
C14 C15 1.521(4) 10_556
C14 C15 1.521(4) .
C14 H14A 1.0000 .
C15 C16 1.523(5) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C16 C17 1.513(5) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C17 C16 1.513(5) 10_556
C17 H17A 0.9900 .
C17 H17B 0.9900 .
B1 F2 1.364(8) .
B1 F2 1.364(8) 10_556
B1 F1 1.406(8) 3_655
B1 F1 1.406(8) .
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_1
_geom_torsion_site_symmetry_4
C11 Cu1 C1 N2 0(30) . .
C11 Cu1 C1 N2 0(100) . 3
N2 C1 N2 C3 0.0 3 .
Cu1 C1 N2 C3 180.0 . .
N2 C1 N2 C4 180.0 3 .
Cu1 C1 N2 C4 0.0 . .
C1 N2 C3 C3 0.0 . 3
C4 N2 C3 C3 180.0 . 3
C1 N2 C4 C5 90.8(3) . 10_556
C3 N2 C4 C5 -89.2(3) . 10_556
C1 N2 C4 C5 -90.8(3) . .
C3 N2 C4 C5 89.2(3) . .
C5 C4 C5 C6 1.6(6) 10_556 .
N2 C4 C5 C6 -176.7(3) . .
C5 C4 C5 C8 -176.6(3) 10_556 .
N2 C4 C5 C8 5.1(5) . .
C4 C5 C6 C7 -0.2(5) . .
C8 C5 C6 C7 178.0(4) . .
C5 C6 C7 C6 -1.1(7) . 10_556
C6 C5 C8 C9 57.1(4) . .
C4 C5 C8 C9 -124.7(4) . .
C6 C5 C8 C10 -66.9(4) . .
C4 C5 C8 C10 111.2(4) . .
C1 Cu1 C11 N12 0(30) . .
C1 Cu1 C11 N12 0(100) . 3
N12 C11 N12 C13 0.0 3 .
Cu1 C11 N12 C13 180.0 . .
N12 C11 N12 C14 180.0 3 .
Cu1 C11 N12 C14 0.0 . .
C11 N12 C13 C13 0.0 . 3
C14 N12 C13 C13 180.0 . 3
C11 N12 C14 C15 117.6(3) . 10_556
C13 N12 C14 C15 -62.4(3) . 10_556
C11 N12 C14 C15 -117.6(3) . .
C13 N12 C14 C15 62.4(3) . .
N12 C14 C15 C16 175.8(3) . .
C15 C14 C15 C16 -58.6(5) 10_556 .
C14 C15 C16 C17 56.1(4) . .
C15 C16 C17 C16 -53.7(5) . 10_556
