#------------------------------------------------------------------------------
#$Date: 2017-04-28 04:15:48 +0300 (Fri, 28 Apr 2017) $
#$Revision: 195832 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/58/1545895.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_1545895
loop_
_publ_author_name
'Jin, Xiaodong'
'Davies, Robert P.'
_publ_section_title
;
 Copper-catalysed aromatic-Finkelstein reactions with amine-based ligand
 systems
;
_journal_name_full               'Catal. Sci. Technol.'
_journal_paper_doi               10.1039/C7CY00538E
_journal_year                    2017
_chemical_formula_moiety         'C8 H24 Cu2 I2 N4'
_chemical_formula_sum            'C8 H24 Cu2 I2 N4'
_chemical_formula_weight         557.19
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-03-17 deposited with the CCDC.
2017-04-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.026(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.3569(10)
_cell_length_b                   11.5554(8)
_cell_length_c                   11.4189(9)
_cell_measurement_reflns_used    1988
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.0970
_cell_measurement_theta_min      2.8280
_cell_volume                     1755.7(2)
_computing_cell_refinement       CrysAlisPro,
_computing_data_collection       CrysAlisPro,
_computing_data_reduction        'CrysAlisPro, Rigaku OD'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 16.0382
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.861
_diffrn_measurement_device_type  'Agilent Xcalibur 3 E'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_av_unetI/netI     0.0644
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.861
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6270
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.861
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.010
_diffrn_reflns_theta_min         2.513
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    5.925
_exptl_absorpt_correction_T_max  0.470
_exptl_absorpt_correction_T_min  0.261
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015) 
Analytical numeric absorption correction using a multifaceted crystal 
   model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    2.108
_exptl_crystal_description       blocks
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.140
_refine_diff_density_min         -1.237
_refine_diff_density_rms         0.291
_refine_ls_extinction_coef       0.0030(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         6270
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.115
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0436
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0809P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1533
_refine_ls_wR_factor_ref         0.1608
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4326
_reflns_number_total             6270
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7cy00538e2.cif
_cod_data_source_block           Cu2I2L1_2
_cod_database_code               1545895
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Cu1A Cu 0.05466(10) 0.41629(12) 0.54300(13) 0.0345(4) Uani 1 1 d . .
I1A I -0.05636(6) 0.52670(7) 0.67923(7) 0.0359(3) Uani 1 1 d . .
N1A N 0.0453(7) 0.2315(8) 0.5480(9) 0.034(2) Uani 1 1 d . .
H1A H 0.0172 0.2112 0.6139 0.041 Uiso 1 1 calc R U
C2A C 0.1518(9) 0.1968(10) 0.5615(13) 0.045(4) Uani 1 1 d . .
H2AA H 0.1822 0.2084 0.4863 0.054 Uiso 1 1 calc R U
H2AB H 0.1573 0.1137 0.5823 0.054 Uiso 1 1 calc R U
C3A C 0.2067(9) 0.2679(11) 0.6560(13) 0.047(3) Uani 1 1 d . .
H3AA H 0.1758 0.2563 0.7308 0.057 Uiso 1 1 calc R U
H3AB H 0.2775 0.2421 0.6676 0.057 Uiso 1 1 calc R U
N4A N 0.2034(6) 0.3912(9) 0.6252(9) 0.041(3) Uani 1 1 d . .
H4A H 0.2470 0.4032 0.5707 0.049 Uiso 1 1 calc R U
C5A C -0.0103(11) 0.1743(11) 0.4485(13) 0.054(4) Uani 1 1 d . .
H5AA H -0.0805 0.1998 0.4429 0.081 Uiso 1 1 calc R U
H5AB H 0.0197 0.1945 0.3759 0.081 Uiso 1 1 calc R U
H5AC H -0.0074 0.0903 0.4598 0.081 Uiso 1 1 calc R U
C6A C 0.2351(12) 0.4628(14) 0.7277(16) 0.076(5) Uani 1 1 d . .
H6AA H 0.2323 0.5447 0.7051 0.115 Uiso 1 1 calc R U
H6AB H 0.1900 0.4492 0.7896 0.115 Uiso 1 1 calc R U
H6AC H 0.3040 0.4425 0.7570 0.115 Uiso 1 1 calc R U
Cu1B Cu 0.55000(11) 0.45864(13) 0.59175(14) 0.0388(4) Uani 1 1 d . .
I1B I 0.56620(5) 0.67930(6) 0.53771(7) 0.0363(3) Uani 1 1 d . .
N1B N 0.6947(7) 0.3835(9) 0.6348(10) 0.041(3) Uani 1 1 d . .
H1B H 0.7400 0.4409 0.6326 0.050 Uiso 1 1 calc R U
C2B C 0.6931(10) 0.3496(12) 0.7582(13) 0.054(4) Uani 1 1 d . .
H2BA H 0.7628 0.3379 0.7933 0.064 Uiso 1 1 calc R U
H2BB H 0.6566 0.2754 0.7629 0.064 Uiso 1 1 calc R U
C3B C 0.6434(10) 0.4393(12) 0.8258(12) 0.052(4) Uani 1 1 d . .
H3BA H 0.6449 0.4154 0.9092 0.062 Uiso 1 1 calc R U
H3BB H 0.6806 0.5131 0.8224 0.062 Uiso 1 1 calc R U
N4B N 0.5388(7) 0.4563(8) 0.7780(9) 0.039(3) Uani 1 1 d . .
H4B H 0.5029 0.3939 0.7957 0.047 Uiso 1 1 calc R U
C5B C 0.7290(11) 0.2893(13) 0.5640(16) 0.074(5) Uani 1 1 d . .
H5BA H 0.7292 0.3148 0.4821 0.110 Uiso 1 1 calc R U
H5BB H 0.7971 0.2667 0.5940 0.110 Uiso 1 1 calc R U
H5BC H 0.6836 0.2230 0.5680 0.110 Uiso 1 1 calc R U
C6B C 0.4952(11) 0.5598(11) 0.8310(13) 0.053(4) Uani 1 1 d . .
H6BA H 0.4255 0.5698 0.7981 0.080 Uiso 1 1 calc R U
H6BB H 0.4968 0.5495 0.9164 0.080 Uiso 1 1 calc R U
H6BC H 0.5344 0.6284 0.8137 0.080 Uiso 1 1 calc R U
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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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
N1A Cu1A N4A 84.7(4) . .
N1A Cu1A Cu1A 136.9(3) . 3_566
N4A Cu1A Cu1A 138.1(3) . 3_566
N1A Cu1A I1A 116.1(3) . .
N4A Cu1A I1A 111.3(3) . .
Cu1A Cu1A I1A 61.31(6) 3_566 .
N1A Cu1A I1A 106.4(3) . 3_566
N4A Cu1A I1A 111.8(3) . 3_566
Cu1A Cu1A I1A 59.57(6) 3_566 3_566
I1A Cu1A I1A 120.89(5) . 3_566
Cu1A I1A Cu1A 59.11(5) . 3_566
C5A N1A C2A 112.3(10) . .
C5A N1A Cu1A 117.2(8) . .
C2A N1A Cu1A 102.5(7) . .
N1A C2A C3A 109.5(10) . .
N4A C3A C2A 111.0(10) . .
C6A N4A C3A 110.9(11) . .
C6A N4A Cu1A 117.7(8) . .
C3A N4A Cu1A 104.1(7) . .
N1B Cu1B N4B 84.6(4) . .
N1B Cu1B Cu1B 137.2(3) . 3_666
N4B Cu1B Cu1B 137.5(3) . 3_666
N1B Cu1B I1B 111.4(3) . 3_666
N4B Cu1B I1B 117.8(3) . 3_666
Cu1B Cu1B I1B 61.41(6) 3_666 3_666
N1B Cu1B I1B 110.8(3) . .
N4B Cu1B I1B 105.0(3) . .
Cu1B Cu1B I1B 59.78(6) 3_666 .
I1B Cu1B I1B 121.20(6) 3_666 .
Cu1B I1B Cu1B 58.80(6) 3_666 .
C5B N1B C2B 111.5(11) . .
C5B N1B Cu1B 119.9(9) . .
C2B N1B Cu1B 103.9(7) . .
N1B C2B C3B 111.0(10) . .
N4B C3B C2B 110.8(11) . .
C3B N4B C6B 110.6(10) . .
C3B N4B Cu1B 103.0(8) . .
C6B N4B Cu1B 117.3(8) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1A N1A 2.141(9) .
Cu1A N4A 2.142(9) .
Cu1A Cu1A 2.567(3) 3_566
Cu1A I1A 2.5789(16) .
Cu1A I1A 2.6237(17) 3_566
I1A Cu1A 2.6237(17) 3_566
N1A C5A 1.460(15) .
N1A C2A 1.474(14) .
C2A C3A 1.496(18) .
C3A N4A 1.467(15) .
N4A C6A 1.465(17) .
Cu1B N1B 2.137(9) .
Cu1B N4B 2.145(10) .
Cu1B Cu1B 2.569(3) 3_666
Cu1B I1B 2.5948(16) 3_666
Cu1B I1B 2.6368(17) .
I1B Cu1B 2.5948(16) 3_666
N1B C5B 1.453(17) .
N1B C2B 1.465(17) .
C2B C3B 1.48(2) .
C3B N4B 1.468(15) .
N4B C6B 1.483(15) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1A H1A I1A 0.90 3.19 3.904(10) 137.6 2_546
N4A H4A I1B 0.90 3.03 3.821(10) 147.1 3_666
N1B H1B I1A 0.90 2.90 3.709(9) 150.4 1_655
N4B H4B I1B 0.90 3.31 4.143(9) 155.9 2_646
