#------------------------------------------------------------------------------
#$Date: 2017-04-28 03:15:48 +0200 (vie 28 de abr de 2017) $
#$Revision: 195832 $
#$URL: svn://www.crystallography.net/cod/cif/1/54/58/1545893.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_1545893
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         'C4 H12 Cu2 I2 N2'
_chemical_formula_sum            'C4 H12 Cu2 I2 N2'
_chemical_formula_weight         469.04
_space_group_crystal_system      tetragonal
_space_group_IT_number           86
_space_group_name_Hall           '-P 4bc'
_space_group_name_H-M_alt        'P 42/n'
_symmetry_space_group_name_Hall  '-P 4bc'
_symmetry_space_group_name_H-M   'P 42/n :2'
_atom_sites_solution_hydrogens   mixed
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.7663(3)
_cell_length_b                   11.7663(3)
_cell_length_c                   7.5184(3)
_cell_measurement_reflns_used    796
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.0270
_cell_measurement_theta_min      3.2500
_cell_volume                     1040.89(6)
_computing_cell_refinement       CrysAlisPro,
_computing_data_collection       CrysAlisPro,
_computing_data_reduction        CrysAlisPro,
_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 0.993
_diffrn_measured_fraction_theta_max 0.818
_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  0.0244
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.818
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            1764
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.818
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.177
_diffrn_reflns_theta_min         2.448
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    9.958
_exptl_absorpt_correction_T_max  0.336
_exptl_absorpt_correction_T_min  0.154
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) 
(compiled Jan 14 2014,18:38:05) 
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    2.993
_exptl_crystal_description       blocks
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.645
_refine_diff_density_min         -0.690
_refine_diff_density_rms         0.156
_refine_ls_extinction_coef       0.00321(17)
_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   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     52
_refine_ls_number_reflns         1049
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0263
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0144P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0452
_refine_ls_wR_factor_ref         0.0469
_reflns_Friedel_coverage         0.000
_reflns_number_gt                912
_reflns_number_total             1049
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7cy00538e2.cif
_cod_data_source_block           Cu4I4L1_2
_cod_original_cell_volume        1040.90(7)
_cod_database_code               1545893
_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. 
;
_shelx_res_file
; 
  
    RD1404.res created by SHELXL-2014/7 
  
TITL RD1404 in P4(2)/n 
REM P4(2)/n (#86 in standard setting) 
REM AXD_DMEDA_CuI_with_NaI 
CELL 0.71073  11.766303  11.766303   7.518433  90.0000  90.0000  90.0000 
ZERR    4.00   0.000293   0.000293   0.000331   0.0000   0.0000   0.0000 
LATT  1 
SYMM -x+1/2,-y+1/2, z 
SYMM -y, x+1/2, z+1/2 
SYMM  y+1/2,-x, z+1/2 
SFAC C H Cu I N 
UNIT 16 48 8 8 8 
TEMP -100 
  
L.S. 6 
FMAP 2 
PLAN 10 
  
ACTA 
  
DFIX 0.9000 0.0001 N1 H1 
  
REM Instructions for potential hydrogen bonds 
EQIV $1 y, -x+3/2, -z+1/2 
HTAB N1 I1_$1 
  
WGHT    0.014400 
EXTI    0.003206 
FVAR       3.03764 
CU1   3    0.646952    0.702177    0.628681    11.00000    0.01874    0.02196 = 
         0.02128   -0.00284   -0.00376   -0.00286 
I1    4    0.824286    0.574048    0.534365    11.00000    0.02048    0.01872 = 
         0.01869   -0.00458    0.00140    0.00114 
N1    5    0.517010    0.658108    0.457618    11.00000    0.03030    0.01475 = 
         0.02010    0.00563   -0.00648   -0.00214 
H1    2    0.530891    0.697459    0.357295    11.00000    0.03845 
C2    1    0.506606    0.535933    0.415737    11.00000    0.02588    0.02064 = 
         0.01972   -0.00108   -0.00610   -0.00947 
AFIX  23 
H2A   2    0.575040    0.510760    0.350037    11.00000   -1.20000 
H2B   2    0.439815    0.523978    0.337875    11.00000   -1.20000 
AFIX   0 
C3    1    0.406625    0.710355    0.503967    11.00000    0.02195    0.03221 = 
         0.04847   -0.00534   -0.01041    0.00209 
AFIX 137 
H3A   2    0.382379    0.683401    0.621317    11.00000   -1.50000 
H3B   2    0.349667    0.689054    0.414900    11.00000   -1.50000 
H3C   2    0.414668    0.793240    0.506404    11.00000   -1.50000 
  
AFIX   0 
HKLF 4 
  
REM  RD1404 in P4(2)/n 
REM R1 =  0.0263 for     912 Fo > 4sig(Fo)  and  0.0333 for all    1049 data 
REM     52 parameters refined using      1 restraints 
  
END 
  
WGHT      0.0150      0.0000 
  
REM Highest difference peak  0.645,  deepest hole -0.690,  1-sigma level  0.156 
Q1    1   0.9127  0.5527  0.5253  11.00000  0.05    0.65 
Q2    1   0.8665  0.6408  0.5150  11.00000  0.05    0.57 
Q3    1   0.2910  0.6615  0.7558  11.00000  0.05    0.54 
Q4    1   0.8085  0.4816  0.5026  11.00000  0.05    0.52 
Q5    1   0.3220  0.7139  0.4241  11.00000  0.05    0.51 
Q6    1   0.3443  0.6473  0.4865  11.00000  0.05    0.49 
Q7    1   0.2921  0.5248  0.3567  11.00000  0.05    0.48 
Q8    1   0.7892  0.6404  0.4723  11.00000  0.05    0.46 
Q9    1   0.6538  0.4671  0.4662  11.00000  0.05    0.46 
Q10   1   0.3667  0.7114  0.3182  11.00000  0.05    0.45 
;
_shelx_res_checksum              35498
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-y, x+1/2, z+1/2'
'y+1/2, -x, z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'y, -x-1/2, -z-1/2'
'-y-1/2, x, -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
Cu1 Cu 0.64695(5) 0.70218(5) 0.62868(8) 0.02066(18) Uani 1 1 d . .
I1 I 0.82429(3) 0.57405(3) 0.53437(4) 0.01930(12) Uani 1 1 d . .
N1 N 0.5170(4) 0.6581(3) 0.4576(4) 0.0217(10) Uani 1 1 d D .
H1 H 0.5309(15) 0.6975(5) 0.3573(5) 0.038(17) Uiso 1 1 d D .
C2 C 0.5066(4) 0.5359(4) 0.4157(6) 0.0221(11) Uani 1 1 d . .
H2A H 0.5750 0.5108 0.3500 0.026 Uiso 1 1 calc R U
H2B H 0.4398 0.5240 0.3379 0.026 Uiso 1 1 calc R U
C3 C 0.4066(4) 0.7104(5) 0.5040(8) 0.0342(14) Uani 1 1 d . .
H3A H 0.3824 0.6834 0.6213 0.051 Uiso 1 1 calc R U
H3B H 0.3497 0.6891 0.4149 0.051 Uiso 1 1 calc R U
H3C H 0.4147 0.7932 0.5064 0.051 Uiso 1 1 calc R U
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0187(4) 0.0220(4) 0.0213(3) -0.0028(3) -0.0038(3) -0.0029(3)
I1 0.0205(2) 0.0187(2) 0.01869(19) -0.00458(14) 0.00140(13) 0.00114(14)
N1 0.030(3) 0.015(2) 0.020(2) 0.0056(19) -0.0065(19) -0.0021(18)
C2 0.026(3) 0.021(3) 0.020(3) -0.001(2) -0.006(2) -0.009(2)
C3 0.022(3) 0.032(3) 0.048(4) -0.005(3) -0.010(3) 0.002(3)
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
N1 Cu1 Cu1 150.58(9) . 8_757
N1 Cu1 Cu1 141.78(11) . 7_577
Cu1 Cu1 Cu1 61.17(3) 8_757 7_577
N1 Cu1 I1 105.76(11) . .
Cu1 Cu1 I1 61.10(2) 8_757 .
Cu1 Cu1 I1 111.88(2) 7_577 .
N1 Cu1 Cu1 141.04(9) . 2_665
Cu1 Cu1 Cu1 59.416(13) 8_757 2_665
Cu1 Cu1 Cu1 59.415(13) 7_577 2_665
I1 Cu1 Cu1 61.89(2) . 2_665
N1 Cu1 I1 108.74(10) . 7_577
Cu1 Cu1 I1 62.18(3) 8_757 7_577
Cu1 Cu1 I1 60.24(3) 7_577 7_577
I1 Cu1 I1 115.69(2) . 7_577
Cu1 Cu1 I1 109.733(14) 2_665 7_577
N1 Cu1 I1 99.85(9) . 2_665
Cu1 Cu1 I1 109.45(2) 8_757 2_665
Cu1 Cu1 I1 60.082(19) 7_577 2_665
I1 Cu1 I1 112.10(2) . 2_665
Cu1 Cu1 I1 59.00(2) 2_665 2_665
I1 Cu1 I1 113.13(2) 7_577 2_665
Cu1 I1 Cu1 58.66(2) . 8_757
Cu1 I1 Cu1 59.11(2) . 2_665
Cu1 I1 Cu1 57.74(2) 8_757 2_665
C2 N1 C3 112.5(4) . .
C2 N1 Cu1 116.0(3) . .
C3 N1 Cu1 113.5(3) . .
N1 C2 C2 111.7(5) . 5_666
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N1 2.064(4) .
Cu1 Cu1 2.6271(10) 8_757
Cu1 Cu1 2.6271(10) 7_577
Cu1 I1 2.6701(7) .
Cu1 Cu1 2.6734(12) 2_665
Cu1 I1 2.6927(7) 7_577
Cu1 I1 2.7477(7) 2_665
I1 Cu1 2.6927(7) 8_757
I1 Cu1 2.7477(7) 2_665
N1 C2 1.477(6) .
N1 C3 1.479(6) .
C2 C2 1.531(9) 5_666
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
N1 H1 I1 0.9000(1) 2.999(4) 3.765(3) 144.1(6) 7_576
