#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:12:46 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178553 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/61/4066152.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_4066152
loop_
_publ_author_name
'Al Thagfi, Jameel'
'Dastgir, Sarim'
'Lough, Alan J.'
'Lavoie, Gino G.'
_publ_section_title
;
 Synthesis and Structural Characterization of the First Copper(I)
 Complexes with Bis(imino)-N-heterocyclic Carbene NCN Pincer Ligands
;
_journal_issue                   14
_journal_name_full               Organometallics
_journal_page_first              3133
_journal_paper_doi               10.1021/om100321n
_journal_volume                  29
_journal_year                    2010
_chemical_formula_moiety         'C35 H35 N4, B F4'
_chemical_formula_sum            'C35 H35 B F4 N4'
_chemical_formula_weight         598.48
_chemical_name_systematic
; 
? 
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 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                 113.5240(19)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.1346(3)
_cell_length_b                   31.4177(11)
_cell_length_c                   7.5643(2)
_cell_measurement_reflns_used    11654
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.6
_cell_volume                     1554.65(10)
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius B.V., 1997-2002)'
_computing_data_reduction        Denzo-SMN
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL V6.1'
_computing_structure_refinement  'SHELXTL V6.1 (Sheldrick, 2008)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150(1)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ scans and ω scans with κ offsets'
_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  0.0593
_diffrn_reflns_av_sigmaI/netI    0.0612
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            11654
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.59
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.751
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements 
Sortav (Blessing 1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             628
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         3575
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.1133
_refine_ls_R_factor_gt           0.0629
_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)+(0.1104P)²+0.1891P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1673
_refine_ls_wR_factor_ref         0.1995
_reflns_number_gt                2169
_reflns_number_total             3575
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            om100321n_si_002.cif
_cod_data_source_block           k09240
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_cell_volume        1554.65(9)
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               4066152
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-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
N1 N 0.1248(3) 0.21548(5) 0.2080(2) 0.0300(4) Uani 1 1 d .
N2 N 0.0720(3) 0.14330(5) 0.1642(3) 0.0362(5) Uani 1 1 d .
C1 C 0.2331(5) 0.2500 0.2903(4) 0.0301(6) Uani 1 2 d S
H1 H 0.3659 0.2500 0.3912 0.036 Uiso 1 2 calc SR
C2 C -0.0653(3) 0.22855(6) 0.0715(3) 0.0341(5) Uani 1 1 d .
H2 H -0.1739 0.2106 -0.0065 0.041 Uiso 1 1 calc R
C3 C 0.2010(3) 0.17237(6) 0.2490(3) 0.0320(5) Uani 1 1 d .
C4 C 0.4178(3) 0.16918(6) 0.3866(3) 0.0336(5) Uani 1 1 d .
C5 C 0.4642(4) 0.14752(7) 0.5595(3) 0.0420(6) Uani 1 1 d .
H5A H 0.3600 0.1333 0.5847 0.050 Uiso 1 1 calc R
C6 C 0.6656(4) 0.14705(7) 0.6948(3) 0.0492(7) Uani 1 1 d .
H6A H 0.6990 0.1323 0.8133 0.059 Uiso 1 1 calc R
C7 C 0.8159(4) 0.16766(8) 0.6587(3) 0.0509(7) Uani 1 1 d .
H7A H 0.9523 0.1676 0.7532 0.061 Uiso 1 1 calc R
C8 C 0.7702(4) 0.18850(8) 0.4853(4) 0.0476(6) Uani 1 1 d .
H8A H 0.8753 0.2024 0.4604 0.057 Uiso 1 1 calc R
C9 C 0.5712(3) 0.18912(7) 0.3481(3) 0.0387(5) Uani 1 1 d .
H9A H 0.5397 0.2031 0.2283 0.046 Uiso 1 1 calc R
C10 C 0.1381(4) 0.09966(6) 0.1856(3) 0.0373(5) Uani 1 1 d .
C11 C 0.2622(4) 0.08397(7) 0.0976(3) 0.0395(5) Uani 1 1 d .
C12 C 0.3111(4) 0.04067(7) 0.1172(3) 0.0472(6) Uani 1 1 d .
H12A H 0.3977 0.0299 0.0596 0.057 Uiso 1 1 calc R
C13 C 0.2384(4) 0.01283(7) 0.2171(4) 0.0534(7) Uani 1 1 d .
C14 C 0.1090(5) 0.02940(7) 0.2956(4) 0.0583(7) Uani 1 1 d .
H14A H 0.0545 0.0107 0.3619 0.070 Uiso 1 1 calc R
C15 C 0.0549(4) 0.07228(7) 0.2818(3) 0.0466(6) Uani 1 1 d .
C16 C -0.0851(5) 0.08873(8) 0.3702(5) 0.0669(8) Uani 1 1 d .
H16A H -0.1664 0.0652 0.3874 0.100 Uiso 1 1 calc R
H16B H -0.1766 0.1102 0.2853 0.100 Uiso 1 1 calc R
H16C H -0.0040 0.1015 0.4958 0.100 Uiso 1 1 calc R
C17 C 0.2946(6) -0.03383(8) 0.2343(5) 0.0715(9) Uani 1 1 d .
H17A H 0.3159 -0.0428 0.1197 0.107 Uiso 1 1 calc R
H17B H 0.1837 -0.0506 0.2450 0.107 Uiso 1 1 calc R
H17C H 0.4204 -0.0383 0.3495 0.107 Uiso 1 1 calc R
C18 C 0.3413(4) 0.11147(7) -0.0213(4) 0.0503(6) Uani 1 1 d .
H18A H 0.2380 0.1328 -0.0914 0.075 Uiso 1 1 calc R
H18B H 0.3706 0.0936 -0.1134 0.075 Uiso 1 1 calc R
H18C H 0.4668 0.1259 0.0639 0.075 Uiso 1 1 calc R
F2 F 0.5087(3) 0.2500 0.7661(4) 0.0703(7) Uani 1 2 d S
F3 F 0.1694(4) 0.2500 0.6205(3) 0.0709(11) Uani 0.887(6) 2 d SPD
F1 F 0.3141(4) 0.21479(7) 0.8966(3) 0.0980(11) Uani 0.887(6) 1 d P
B1 B 0.3300(6) 0.2500 0.7953(5) 0.0395(8) Uani 1 2 d SD
F1A F 0.221(3) 0.2152(6) 0.689(3) 0.082(7) Uiso 0.113(6) 1 d P
F3A F 0.358(5) 0.2500 0.981(2) 0.114(11) Uiso 0.113(6) 2 d SPD
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'
F F 0.0171 0.0103 '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'
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
C1 N1 C2 108.46(17) . .
C1 N1 C3 124.30(19) . .
C2 N1 C3 127.14(16) . .
C3 N2 C10 119.26(19) . .
N1 C1 N1 108.9(3) . 4_565
C2 C2 N1 107.07(10) 4_565 .
N2 C3 N1 115.43(19) . .
N2 C3 C4 130.29(18) . .
N1 C3 C4 114.27(16) . .
C9 C4 C5 120.4(2) . .
C9 C4 C3 120.68(18) . .
C5 C4 C3 118.9(2) . .
C4 C5 C6 119.0(2) . .
C7 C6 C5 120.6(2) . .
C6 C7 C8 120.4(2) . .
C7 C8 C9 120.0(2) . .
C8 C9 C4 119.6(2) . .
C11 C10 C15 120.82(19) . .
C11 C10 N2 121.75(19) . .
C15 C10 N2 117.10(19) . .
C10 C11 C12 118.2(2) . .
C10 C11 C18 122.83(19) . .
C12 C11 C18 118.9(2) . .
C13 C12 C11 122.8(2) . .
C14 C13 C12 117.1(2) . .
C14 C13 C17 121.8(2) . .
C12 C13 C17 121.0(2) . .
C13 C14 C15 122.9(2) . .
C14 C15 C10 118.0(2) . .
C14 C15 C16 120.9(2) . .
C10 C15 C16 121.0(2) . .
F1A F3 F1A 130.8(17) 4_565 .
F1A F3 B1 65.6(9) 4_565 .
F1A F3 B1 65.6(9) . .
F3A F1 B1 61.2(5) . .
F3A F1 F1A 117.5(9) . .
B1 F1 F1A 59.3(7) . .
F3A B1 F3 137.2(14) . .
F3A B1 F1 54.9(3) . 4_565
F3 B1 F1 108.5(2) . 4_565
F3A B1 F1 54.9(3) . .
F3 B1 F1 108.5(2) . .
F1 B1 F1 107.0(3) 4_565 .
F3A B1 F2 114.2(14) . .
F3 B1 F2 108.6(3) . .
F1 B1 F2 112.1(2) 4_565 .
F1 B1 F2 112.1(2) . .
F3A B1 F1A 114.9(10) . .
F3 B1 F1A 51.7(8) . .
F1 B1 F1A 143.2(8) 4_565 .
F1 B1 F1A 62.8(8) . .
F2 B1 F1A 104.1(8) . .
F3A B1 F1A 114.9(10) . 4_565
F3 B1 F1A 51.7(8) . 4_565
F1 B1 F1A 62.8(8) 4_565 4_565
F1 B1 F1A 143.2(8) . 4_565
F2 B1 F1A 104.1(8) . 4_565
F1A B1 F1A 103.1(17) . 4_565
F3 F1A B1 62.7(9) . .
F3 F1A F1 113.9(13) . .
B1 F1A F1 58.0(7) . .
F1 F3A F1 123.8(13) . 4_565
F1 F3A B1 63.9(5) . .
F1 F3A B1 63.9(5) 4_565 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.333(2) .
N1 C2 1.399(3) .
N1 C3 1.446(2) .
N2 C3 1.273(3) .
N2 C10 1.438(2) .
C1 N1 1.333(2) 4_565
C2 C2 1.348(4) 4_565
C3 C4 1.484(3) .
C4 C9 1.389(3) .
C4 C5 1.392(3) .
C5 C6 1.392(3) .
C6 C7 1.371(4) .
C7 C8 1.383(4) .
C8 C9 1.385(3) .
C10 C11 1.393(3) .
C10 C15 1.403(3) .
C11 C12 1.398(3) .
C11 C18 1.510(3) .
C12 C13 1.385(3) .
C13 C14 1.383(4) .
C13 C17 1.512(3) .
C14 C15 1.394(3) .
C15 C16 1.499(3) .
F2 B1 1.378(4) .
F3 F1A 1.201(19) 4_565
F3 F1A 1.201(19) .
F3 B1 1.361(4) .
F1 F3A 1.254(8) .
F1 B1 1.376(3) .
F1 F1A 1.443(19) .
B1 F3A 1.342(11) .
B1 F1 1.376(3) 4_565
B1 F1A 1.395(17) .
B1 F1A 1.395(17) 4_565
F3A F1 1.254(8) 4_565
