#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:47:55 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179674 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/26/4512663.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_4512663
loop_
_publ_author_name
'Ferguson, Jayne L.'
'Fitchett, Christopher M.'
_publ_section_title
;
 N,N′-Dimethylene-2,2′-biimidazole---A Mimic of Carboxylate
 for the Formation of Complexes with Copper(I) And the Anion Directed
 Formation of a Solvent Pocket
;
_journal_issue                   3
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1280
_journal_paper_doi               10.1021/cg5016803
_journal_volume                  15
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H24 Cu2 N12, 2(B1 F4), 2(C3 H2.5 F0.5)'
_chemical_formula_sum            'C30 H29 B2 Cu2 F9 N12'
_chemical_formula_weight         877.35
_space_group_crystal_system      cubic
_space_group_IT_number           213
_space_group_name_Hall           'P 4bd 2ab 3'
_space_group_name_H-M_alt        'P 41 3 2'
_symmetry_space_group_name_Hall  'P 4bd 2ab 3'
_symmetry_space_group_name_H-M   'P 41 3 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-07-14
_audit_creation_method
;
  Olex2 1.2-beta
  (compiled 2013.04.25 svn.r2679, GUI svn.r4466)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.0849(2)
_cell_length_b                   15.0849(2)
_cell_length_c                   15.0849(2)
_cell_measurement_reflns_used    2214
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      73.6144
_cell_measurement_theta_min      2.9270
_cell_volume                     3432.63(8)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector_area_resol_mean 21.3001
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -34.00   23.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.9688   38.0000  -30.0000 57

  2 omega   92.00  178.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7801   45.0000  -60.0000 86

  3 omega -115.00  -65.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.9688  -46.0000 -155.0000 50
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0285706000
_diffrn_orient_matrix_UB_12      0.0753424000
_diffrn_orient_matrix_UB_13      0.0627234000
_diffrn_orient_matrix_UB_21      -0.0980452000
_diffrn_orient_matrix_UB_22      0.0209834000
_diffrn_orient_matrix_UB_23      0.0193193000
_diffrn_orient_matrix_UB_31      0.0014414000
_diffrn_orient_matrix_UB_32      -0.0656020000
_diffrn_orient_matrix_UB_33      0.0782943000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3343
_diffrn_reflns_theta_full        66.49
_diffrn_reflns_theta_max         66.49
_diffrn_reflns_theta_min         6.56
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.365
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55868
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.698
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1768
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.545
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.07(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1019
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0547
_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)+(0.1240P)²+1.2113P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1562
_refine_ls_wR_factor_ref         0.1576
_reflns_number_gt                989
_reflns_number_total             1019
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg5016803_si_002.cif
_cod_data_source_block           8
_cod_depositor_comments
'Adding full bibliography for 4512656--4512665.cif.'
_cod_database_code               4512663
#BEGIN Tags that were not found in dictionaries:
_chemical_oxdiff_formula         'C30 H29 N12 F9 B2 Cu'
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Shared sites
{C1A, C1B}
3. Restrained distances
 F3-C1A
 -1.36 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(C1A) = Uanis(C1B)
5. Others
 Fixed Sof: F11(0.16666) F12(0.16666) C1A(0.16667) F1(0.5) F2(0.5) F3(0.16667)
 C1B(0.33333) H1B(0.33333)
6.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
6.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C1B(H1B)
;
#END Tags that were not found in dictionaries
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-y+1/4, x+3/4, z+1/4'
3 '-x+1/2, -y, z+1/2'
4 'y+1/4, -x+1/4, z+3/4'
5 'x+1/4, -z+1/4, y+3/4'
6 'x+1/2, -y+1/2, -z'
7 'x+3/4, z+1/4, -y+1/4'
8 'z+3/4, y+1/4, -x+1/4'
9 '-x, y+1/2, -z+1/2'
10 '-z+1/4, y+3/4, x+1/4'
11 'z, x, y'
12 'y, z, x'
13 '-y+1/2, -z, x+1/2'
14 'z+1/2, -x+1/2, -y'
15 '-y, z+1/2, -x+1/2'
16 '-z+1/2, -x, y+1/2'
17 '-z, x+1/2, -y+1/2'
18 'y+1/2, -z+1/2, -x'
19 'y+3/4, x+1/4, -z+1/4'
20 '-y+3/4, -x+3/4, -z+3/4'
21 '-x+1/4, z+3/4, y+1/4'
22 '-x+3/4, -z+3/4, -y+3/4'
23 'z+1/4, -y+1/4, x+3/4'
24 '-z+3/4, -y+3/4, -x+3/4'
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
Cu1 Cu 0.57324(3) 0.92676(3) 0.07324(3) 0.0420(4) Uani 1 3 d S . .
N1 N 0.4766(2) 0.9425(2) 0.1605(2) 0.0423(8) Uani 1 1 d . . .
N2 N 0.3888(3) 0.9429(2) 0.2769(3) 0.0555(10) Uani 1 1 d . . .
C3 C 0.4620(3) 0.9085(3) 0.2390(3) 0.0458(9) Uani 1 1 d . . .
C5 C 0.4077(3) 1.0034(3) 0.1472(3) 0.0531(11) Uani 1 1 d . . .
H5 H 0.4000 1.0379 0.0967 0.064 Uiso 1 1 calc R . .
C6 C 0.3630(4) 0.9231(4) 0.3692(4) 0.0781(17) Uani 1 1 d . . .
H6A H 0.3006 0.9358 0.3778 0.094 Uiso 1 1 calc R . .
H6B H 0.3969 0.9596 0.4098 0.094 Uiso 1 1 calc R . .
C7 C 0.3545(3) 1.0042(3) 0.2186(4) 0.0608(12) Uani 1 1 d . . .
H7 H 0.3045 1.0392 0.2270 0.073 Uiso 1 1 calc R . .
B4 B 0.8862(3) 0.3862(3) 0.1138(3) 0.059(2) Uani 1 3 d S . .
F11 F 0.9414(5) 0.4414(5) 0.0586(5) 0.150(8) Uani 0.50 3 d SP A 1
F12 F 0.8310(4) 0.3310(4) 0.1690(4) 0.086(3) Uani 0.50 3 d SP A 2
C1A C 0.5661(6) 1.1250 0.3161(6) 0.244(16) Uani 0.33 2 d SPD B 1
C2 C 0.6250 1.0620(5) 0.3120(5) 0.099(3) Uani 1 2 d S . .
H2 H 0.6250 1.0184 0.2684 0.119 Uiso 1 2 calc SR B 1
F1 F 0.9701(6) 0.3665(10) 0.1386(10) 0.119(4) Uani 0.50 1 d P A 2
F2 F 0.9426(8) 0.3315(5) 0.1473(10) 0.106(4) Uani 0.50 1 d P A 1
F3 F 0.5040(9) 1.1250 0.2540(9) 0.29(3) Uani 0.33 2 d SPD B 1
C1B C 0.5661(6) 1.1250 0.3161(6) 0.244(16) Uani 0.67 2 d SP B 2
H1B H 0.5225 1.1250 0.2725 0.293 Uiso 0.67 2 calc SPR B 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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
N1 Cu1 Cu1 96.34(10) 13_664 19_455
N1 Cu1 Cu1 96.34(10) 14_566 19_455
N1 Cu1 Cu1 96.34(10) . 19_455
N1 Cu1 N1 118.80(4) 13_664 14_566
N1 Cu1 N1 118.80(4) 13_664 .
N1 Cu1 N1 118.80(4) 14_566 .
C3 N1 Cu1 132.8(3) . .
C3 N1 C5 105.2(4) . .
C5 N1 Cu1 122.0(3) . .
C3 N2 C6 122.5(4) . .
C3 N2 C7 107.2(4) . .
C7 N2 C6 129.7(4) . .
N1 C3 N2 111.8(4) . .
N1 C3 C3 130.3(2) . 24_565
N2 C3 C3 118.0(3) . 24_565
N1 C5 H5 125.3 . .
C7 C5 N1 109.5(5) . .
C7 C5 H5 125.3 . .
N2 C6 C6 108.5(4) . 24_565
N2 C6 H6A 110.0 . .
N2 C6 H6B 110.0 . .
C6 C6 H6A 110.0 24_565 .
C6 C6 H6B 110.0 24_565 .
H6A C6 H6B 108.4 . .
N2 C7 H7 126.8 . .
C5 C7 N2 106.4(4) . .
C5 C7 H7 126.8 . .
F12 B4 F11 180.0(8) . .
F1 B4 F11 75.3(7) 18_556 .
F1 B4 F11 75.3(7) 17_645 .
F1 B4 F11 75.2(7) . .
F1 B4 F12 104.8(7) . .
F1 B4 F12 104.7(7) 17_645 .
F1 B4 F12 104.7(7) 18_556 .
F1 B4 F1 113.8(5) 18_556 17_645
F1 B4 F1 113.8(5) 17_645 .
F1 B4 F1 113.8(5) 18_556 .
F2 B4 F11 102.4(8) . .
F2 B4 F11 102.4(8) 17_645 .
F2 B4 F11 102.4(8) 18_556 .
F2 B4 F12 77.6(8) 18_556 .
F2 B4 F12 77.6(8) 17_645 .
F2 B4 F12 77.6(8) . .
F2 B4 F1 109.5(10) 18_556 17_645
F2 B4 F1 109.5(10) . 18_556
F2 B4 F1 134.1(9) 17_645 18_556
F2 B4 F1 29.9(6) 18_556 18_556
F2 B4 F1 29.9(6) 17_645 17_645
F2 B4 F1 29.9(6) . .
F2 B4 F1 109.5(10) 17_645 .
F2 B4 F1 134.1(9) . 17_645
F2 B4 F1 134.1(9) 18_556 .
F2 B4 F2 115.5(5) 18_556 17_645
F2 B4 F2 115.5(5) 18_556 .
F2 B4 F2 115.5(5) 17_645 .
C2 C1A C2 126.5(13) . 18_466
C2 C1A F3 116.7(7) 18_466 .
C2 C1A F3 116.7(7) . .
C1A C2 C1A 113.5(13) . 17_656
C1A C2 H2 123.3 . .
C1A C2 H2 123.3 17_656 .
C1A C2 C1B 113.5(13) . 17_656
C1B C2 C1A 0.0 17_656 17_656
C1B C2 H2 123.3 17_656 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 Cu1 2.7045(17) 19_455
Cu1 N1 1.979(3) .
Cu1 N1 1.979(3) 13_664
Cu1 N1 1.979(3) 14_566
N1 C3 1.308(6) .
N1 C5 1.402(5) .
N2 C3 1.347(5) .
N2 C6 1.476(6) .
N2 C7 1.377(7) .
C3 C3 1.455(9) 24_565
C5 H5 0.9300 .
C5 C7 1.343(7) .
C6 C6 1.500(11) 24_565
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C7 H7 0.9300 .
B4 F11 1.442(16) .
B4 F12 1.442(14) .
B4 F1 1.353(11) .
B4 F1 1.353(11) 17_645
B4 F1 1.353(11) 18_556
B4 F2 1.289(10) 18_556
B4 F2 1.289(10) 17_645
B4 F2 1.289(10) .
C1A C2 1.303(8) 18_466
C1A C2 1.303(8) .
C1A F3 1.323(18) .
C2 C1A 1.303(8) 17_656
C2 H2 0.9300 .
C2 C1B 1.303(8) 17_656
