# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cuclbmin_90k
_database_code_depnum_ccdc_archive 'CCDC 1427586'
_audit_update_record             
;
2015-09-25 deposited with the CCDC.
2016-01-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H30 Cl3 Cu N4'
_chemical_formula_weight         448.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   12.854(2)
_cell_length_b                   11.2524(13)
_cell_length_c                   15.806(4)
_cell_angle_alpha                90
_cell_angle_beta                 109.355(16)
_cell_angle_gamma                90
_cell_volume                     2156.9(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       flaky
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_F_000             936
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    1.390
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.6453
_exptl_absorpt_correction_T_max  0.7600
_exptl_absorpt_process_details   'Coppens (1970)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 6.67
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_voltage           50
_diffrn_source_current           40
_diffrn_source_power             2.00
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    '0.5 mm diameter, monocapillary'
_diffrn_measurement_method       'rotation method'
_diffrn_measurement_details      
; 209 frames, detector distance = 120 mm
;
_diffrn_reflns_number            19229
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.366
_diffrn_reflns_theta_max         26.755
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_point_group_measured_fraction_full 0.927
_reflns_number_total             8389
_reflns_number_gt                7844
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.747
_reflns_Friedel_fraction_max     0.824
_reflns_Friedel_fraction_full    0.846

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Pseudo symmetry elements B and C were detected by ADDSYM.
ADDSYM uses the coordinates of the ordered structural model only. 
A lowering of the symmetry is caused by the disordered atoms. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0407P)²+1.5046P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0024(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 3140 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.014(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         8387
_refine_ls_number_parameters     479
_refine_ls_number_restraints     37
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_ref         0.0836
_refine_ls_wR_factor_gt          0.0802
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.50156(4) 0.94940(7) 0.24719(3) 0.02048(13) Uani 1 1 d . . . . .
Cl1 Cl 0.36914(7) 0.84080(10) 0.14753(6) 0.0205(2) Uani 1 1 d . . . . .
Cl2 Cl 0.64495(8) 0.84116(11) 0.33584(7) 0.0246(2) Uani 1 1 d . . . . .
Cl3 Cl 0.50478(8) 1.14699(11) 0.25717(6) 0.0224(2) Uani 1 1 d . . . . .
Cu2 Cu 0.97965(4) 0.94179(7) 0.74134(3) 0.02138(13) Uani 1 1 d . . . . .
Cl4 Cl 0.85721(8) 0.82562(11) 0.64135(7) 0.0252(2) Uani 1 1 d . . . . .
Cl5 Cl 1.13037(7) 0.84892(10) 0.83673(6) 0.0211(2) Uani 1 1 d . . . . .
Cl6 Cl 0.95990(8) 1.13778(11) 0.74822(6) 0.0227(2) Uani 1 1 d . . . . .
N1 N -0.0039(3) 0.1486(3) 0.0141(2) 0.0203(7) Uani 1 1 d . . . . .
N2 N 0.1310(3) 0.0947(3) 0.1314(2) 0.0207(7) Uani 1 1 d . . . . .
C1 C 0.0416(3) 0.1629(4) 0.1028(3) 0.0220(8) Uani 1 1 d . . . . .
H1 H 0.0152 0.2121 0.1384 0.026 Uiso 1 1 calc R U . . .
C2 C 0.0583(3) 0.0686(4) -0.0144(3) 0.0239(9) Uani 1 1 d . . . . .
H2 H 0.0449 0.0428 -0.0730 0.029 Uiso 1 1 calc R U . . .
C3 C 0.1431(3) 0.0344(4) 0.0591(2) 0.0233(8) Uani 1 1 d . . . . .
H3 H 0.1986 -0.0193 0.0605 0.028 Uiso 1 1 calc R U . . .
C4 C -0.1061(3) 0.2054(4) -0.0421(3) 0.0266(9) Uani 1 1 d . . . . .
H4A H -0.1255 0.2682 -0.0091 0.040 Uiso 1 1 calc R U . . .
H4B H -0.1642 0.1476 -0.0593 0.040 Uiso 1 1 calc R U . . .
H4C H -0.0953 0.2376 -0.0949 0.040 Uiso 1 1 calc R U . . .
C5 C 0.2020(3) 0.0800(4) 0.2251(3) 0.0291(9) Uani 0.501(10) 1 d D U P A 1
H5A H 0.1903 0.1473 0.2592 0.035 Uiso 0.501(10) 1 calc R U P A 1
H5B H 0.2782 0.0827 0.2271 0.035 Uiso 0.501(10) 1 calc R U P A 1
C6 C 0.1853(14) -0.0331(11) 0.2715(7) 0.0346(17) Uani 0.501(10) 1 d D U P A 1
H6A H 0.1904 -0.1014 0.2357 0.042 Uiso 0.501(10) 1 calc R U P A 1
H6B H 0.1124 -0.0327 0.2771 0.042 Uiso 0.501(10) 1 calc R U P A 1
C7 C 0.2731(7) -0.0427(7) 0.3650(5) 0.0256(19) Uani 0.501(10) 1 d D U P A 1
H7A H 0.3458 -0.0500 0.3596 0.031 Uiso 0.501(10) 1 calc R U P A 1
H7B H 0.2719 0.0280 0.3998 0.031 Uiso 0.501(10) 1 calc R U P A 1
C8 C 0.2478(9) -0.1493(8) 0.4102(6) 0.039(3) Uani 0.501(10) 1 d D U P A 1
H8A H 0.1804 -0.1367 0.4226 0.059 Uiso 0.501(10) 1 calc R U P A 1
H8B H 0.3068 -0.1630 0.4654 0.059 Uiso 0.501(10) 1 calc R U P A 1
H8C H 0.2399 -0.2173 0.3718 0.059 Uiso 0.501(10) 1 calc R U P A 1
C5A C 0.2020(3) 0.0800(4) 0.2251(3) 0.0291(9) Uani 0.499(10) 1 d D U P A 2
H5C H 0.1863 0.1408 0.2626 0.035 Uiso 0.499(10) 1 calc R U P A 2
H5D H 0.2791 0.0854 0.2300 0.035 Uiso 0.499(10) 1 calc R U P A 2
C6A C 0.1762(14) -0.0424(10) 0.2534(6) 0.0346(17) Uani 0.499(10) 1 d D U P A 2
H6A1 H 0.2065 -0.1018 0.2235 0.042 Uiso 0.499(10) 1 calc R U P A 2
H6A2 H 0.0968 -0.0528 0.2329 0.042 Uiso 0.499(10) 1 calc R U P A 2
C7A C 0.2213(6) -0.0653(10) 0.3549(5) 0.034(2) Uani 0.499(10) 1 d D U P A 2
H7A1 H 0.2012 -0.0001 0.3867 0.040 Uiso 0.499(10) 1 calc R U P A 2
H7A2 H 0.1898 -0.1379 0.3691 0.040 Uiso 0.499(10) 1 calc R U P A 2
C8A C 0.3433(7) -0.0761(10) 0.3833(5) 0.039(3) Uani 0.499(10) 1 d D U P A 2
H8A1 H 0.3625 -0.1402 0.3512 0.058 Uiso 0.499(10) 1 calc R U P A 2
H8A2 H 0.3721 -0.0917 0.4465 0.058 Uiso 0.499(10) 1 calc R U P A 2
H8A3 H 0.3740 -0.0033 0.3704 0.058 Uiso 0.499(10) 1 calc R U P A 2
N3 N 0.5126(3) 0.1690(3) 0.5207(2) 0.0259(8) Uani 1 1 d . . . . .
N4 N 0.6217(3) 0.0907(3) 0.6428(2) 0.0186(6) Uani 1 1 d . . . . .
C9 C 0.5362(4) 0.1625(4) 0.6094(3) 0.0271(9) Uani 1 1 d . . . . .
H9 H 0.4988 0.2020 0.6423 0.033 Uiso 1 1 calc R U . . .
C10 C 0.5863(3) 0.0997(4) 0.4969(3) 0.0253(9) Uani 1 1 d . . . . .
H10 H 0.5884 0.0883 0.4392 0.030 Uiso 1 1 calc R U . . .
C11 C 0.6549(3) 0.0513(4) 0.5729(2) 0.0234(8) Uani 1 1 d . . . . .
H11 H 0.7137 0.0007 0.5775 0.028 Uiso 1 1 calc R U . . .
C12 C 0.4264(5) 0.2425(5) 0.4597(4) 0.0473(14) Uani 1 1 d . . . . .
H12A H 0.3571 0.2249 0.4674 0.071 Uiso 1 1 calc R U . . .
H12B H 0.4217 0.2259 0.3990 0.071 Uiso 1 1 calc R U . . .
H12C H 0.4439 0.3249 0.4727 0.071 Uiso 1 1 calc R U . . .
C13 C 0.6715(3) 0.0585(4) 0.7379(2) 0.0198(7) Uani 1 1 d . . . . .
H13A H 0.6428 0.1105 0.7740 0.024 Uiso 1 1 calc R U . . .
H13B H 0.7507 0.0701 0.7563 0.024 Uiso 1 1 calc R U . . .
C14 C 0.6473(3) -0.0691(4) 0.7545(2) 0.0215(7) Uani 1 1 d . . . . .
H14A H 0.6838 -0.1211 0.7242 0.026 Uiso 1 1 calc R U . . .
H14B H 0.5686 -0.0830 0.7291 0.026 Uiso 1 1 calc R U . . .
C15 C 0.6858(3) -0.0998(4) 0.8540(2) 0.0235(8) Uani 1 1 d . . . . .
H15A H 0.7631 -0.0793 0.8804 0.028 Uiso 1 1 calc R U . . .
H15B H 0.6788 -0.1848 0.8606 0.028 Uiso 1 1 calc R U . . .
C16 C 0.6203(3) -0.0351(4) 0.9049(3) 0.0299(9) Uani 1 1 d . . . . .
H16A H 0.6315 0.0490 0.9025 0.045 Uiso 1 1 calc R U . . .
H16B H 0.6449 -0.0609 0.9662 0.045 Uiso 1 1 calc R U . . .
H16C H 0.5433 -0.0528 0.8778 0.045 Uiso 1 1 calc R U . . .
N5 N 0.8473(3) 0.1205(3) 0.3655(2) 0.0193(7) Uani 1 1 d . . . . .
N6 N 0.9556(3) 0.2025(4) 0.4863(2) 0.0314(9) Uani 1 1 d . . . . .
C17 C 0.9251(4) 0.2022(4) 0.3969(3) 0.0302(10) Uani 1 1 d . . . . .
H17 H 0.9536 0.2510 0.3625 0.036 Uiso 1 1 calc R U . . .
C18 C 0.8949(3) 0.1176(4) 0.5125(3) 0.0252(9) Uani 1 1 d . . . . .
H18 H 0.8992 0.0995 0.5710 0.030 Uiso 1 1 calc R U . . .
C19 C 0.8281(3) 0.0659(4) 0.4371(2) 0.0219(8) Uani 1 1 d . . . . .
H19 H 0.7783 0.0047 0.4339 0.026 Uiso 1 1 calc R U . . .
C20 C 1.0375(5) 0.2814(6) 0.5470(4) 0.0561(17) Uani 1 1 d . . . . .
H20A H 1.1022 0.2841 0.5294 0.084 Uiso 1 1 calc R U . . .
H20B H 1.0568 0.2519 0.6072 0.084 Uiso 1 1 calc R U . . .
H20C H 1.0072 0.3599 0.5440 0.084 Uiso 1 1 calc R U . . .
C21 C 0.7937(3) 0.0910(4) 0.2699(2) 0.0206(8) Uani 1 1 d . . . . .
H21A H 0.7876 0.1623 0.2340 0.025 Uiso 1 1 calc R U . . .
H21B H 0.7198 0.0616 0.2607 0.025 Uiso 1 1 calc R U . . .
C22 C 0.8577(3) -0.0010(4) 0.2395(3) 0.0267(9) Uani 1 1 d . . . . .
H22A H 0.8658 -0.0713 0.2767 0.032 Uiso 1 1 calc R U . . .
H22B H 0.9308 0.0294 0.2469 0.032 Uiso 1 1 calc R U . . .
C23 C 0.8002(3) -0.0346(4) 0.1412(3) 0.0284(9) Uani 1 1 d . . . . .
H23A H 0.7283 -0.0677 0.1348 0.034 Uiso 1 1 calc R U . . .
H23B H 0.7888 0.0368 0.1049 0.034 Uiso 1 1 calc R U . . .
C24 C 0.8639(5) -0.1231(5) 0.1060(3) 0.0396(12) Uani 1 1 d . . . . .
H24A H 0.9312 -0.0872 0.1048 0.059 Uiso 1 1 calc R U . . .
H24B H 0.8203 -0.1467 0.0464 0.059 Uiso 1 1 calc R U . . .
H24C H 0.8808 -0.1916 0.1443 0.059 Uiso 1 1 calc R U . . .
N7 N 0.5289(3) 0.6852(3) 0.0090(2) 0.0202(7) Uani 1 1 d . . . . .
N8 N 0.6616(3) 0.6282(3) 0.1266(2) 0.0209(7) Uani 1 1 d . . . . .
C25 C 0.5758(3) 0.7015(4) 0.0974(3) 0.0203(8) Uani 1 1 d . . . . .
H25 H 0.5524 0.7548 0.1324 0.024 Uiso 1 1 calc R U . . .
C26 C 0.5859(4) 0.5980(4) -0.0182(3) 0.0252(9) Uani 1 1 d . . . . .
H26 H 0.5702 0.5691 -0.0762 0.030 Uiso 1 1 calc R U . . .
C27 C 0.6691(3) 0.5622(4) 0.0555(3) 0.0257(9) Uani 1 1 d . . . . .
H27 H 0.7213 0.5041 0.0576 0.031 Uiso 1 1 calc R U . . .
C28 C 0.4293(3) 0.7444(4) -0.0488(3) 0.0265(9) Uani 1 1 d . . . . .
H28A H 0.3657 0.6985 -0.0504 0.040 Uiso 1 1 calc R U . . .
H28B H 0.4327 0.7512 -0.1084 0.040 Uiso 1 1 calc R U . . .
H28C H 0.4241 0.8222 -0.0256 0.040 Uiso 1 1 calc R U . . .
C29 C 0.7322(3) 0.6122(4) 0.2209(3) 0.0241(8) Uani 1 1 d . . . . .
H29A H 0.7350 0.6858 0.2535 0.029 Uiso 1 1 calc R U . B 1
H29B H 0.8066 0.5926 0.2232 0.029 Uiso 1 1 calc R U . B 1
C30 C 0.6881(4) 0.5152(5) 0.2639(3) 0.0380(12) Uani 0.642(13) 1 d D . P C 1
H30A H 0.6813 0.4433 0.2287 0.046 Uiso 0.642(13) 1 calc R U P C 1
H30B H 0.6149 0.5371 0.2634 0.046 Uiso 0.642(13) 1 calc R U P C 1
C31 C 0.7607(8) 0.4891(11) 0.3611(4) 0.050(2) Uani 0.642(13) 1 d D . P C 1
H31A H 0.8339 0.4654 0.3628 0.060 Uiso 0.642(13) 1 calc R U P C 1
H31B H 0.7674 0.5598 0.3976 0.060 Uiso 0.642(13) 1 calc R U P C 1
C32 C 0.7081(7) 0.3918(8) 0.3961(5) 0.051(3) Uani 0.642(13) 1 d D . P C 1
H32A H 0.6387 0.4187 0.3994 0.077 Uiso 0.642(13) 1 calc R U P C 1
H32B H 0.7555 0.3694 0.4548 0.077 Uiso 0.642(13) 1 calc R U P C 1
H32C H 0.6962 0.3245 0.3567 0.077 Uiso 0.642(13) 1 calc R U P C 1
C30A C 0.6881(4) 0.5152(5) 0.2639(3) 0.0380(12) Uani 0.358(13) 1 d D . P C 2
H30C H 0.6682 0.4474 0.2239 0.046 Uiso 0.358(13) 1 calc R U P C 2
H30D H 0.6223 0.5426 0.2751 0.046 Uiso 0.358(13) 1 calc R U P C 2
C31A C 0.7752(15) 0.4778(18) 0.3529(6) 0.050(2) Uani 0.358(13) 1 d D . P C 2
H31C H 0.7603 0.3977 0.3683 0.060 Uiso 0.358(13) 1 calc R U P C 2
H31D H 0.8479 0.4789 0.3468 0.060 Uiso 0.358(13) 1 calc R U P C 2
C32A C 0.7720(17) 0.5616(16) 0.4247(8) 0.100(10) Uani 0.358(13) 1 d D . P C 2
H32D H 0.8054 0.6356 0.4175 0.150 Uiso 0.358(13) 1 calc R U P C 2
H32E H 0.8118 0.5281 0.4822 0.150 Uiso 0.358(13) 1 calc R U P C 2
H32F H 0.6968 0.5752 0.4207 0.150 Uiso 0.358(13) 1 calc R U P C 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 Cl3 2.2284(12) . ?
Cu1 Cl1 2.2571(11) . ?
Cu1 Cl2 2.2654(12) . ?
Cu2 Cl6 2.2267(12) . ?
Cu2 Cl4 2.2438(11) . ?
Cu2 Cl5 2.2764(11) . ?
N1 C1 1.338(5) . ?
N1 C2 1.376(5) . ?
N1 C4 1.466(5) . ?
N2 C1 1.330(5) . ?
N2 C3 1.382(5) . ?
N2 C5 1.469(5) . ?
C2 C3 1.359(5) . ?
C5 C6 1.518(7) . ?
C6 C7 1.537(6) . ?
C7 C8 1.487(8) . ?
C6A C7A 1.537(6) . ?
C7A C8A 1.487(8) . ?
N3 C9 1.334(5) . ?
N3 C10 1.372(5) . ?
N3 C12 1.460(6) . ?
N4 C9 1.325(5) . ?
N4 C11 1.383(5) . ?
N4 C13 1.471(4) . ?
C10 C11 1.348(5) . ?
C13 C14 1.510(6) . ?
C14 C15 1.523(5) . ?
C15 C16 1.528(6) . ?
N5 C17 1.328(5) . ?
N5 C19 1.380(5) . ?
N5 C21 1.476(5) . ?
N6 C17 1.335(5) . ?
N6 C18 1.382(5) . ?
N6 C20 1.465(5) . ?
C18 C19 1.348(5) . ?
C21 C22 1.496(6) . ?
C22 C23 1.531(5) . ?
C23 C24 1.508(6) . ?
N7 C25 1.339(5) . ?
N7 C26 1.375(5) . ?
N7 C28 1.464(5) . ?
N8 C25 1.332(5) . ?
N8 C27 1.377(5) . ?
N8 C29 1.476(5) . ?
C26 C27 1.356(6) . ?
C29 C30 1.494(6) . ?
C30 C31 1.537(6) . ?
C31 C32 1.487(8) . ?
C31A C32A 1.487(8) . ?

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
_geom_angle_publ_flag
Cl3 Cu1 Cl1 125.57(4) . . ?
Cl3 Cu1 Cl2 120.02(4) . . ?
Cl1 Cu1 Cl2 114.29(4) . . ?
Cl6 Cu2 Cl4 123.14(4) . . ?
Cl6 Cu2 Cl5 120.53(4) . . ?
Cl4 Cu2 Cl5 116.32(4) . . ?
C1 N1 C2 108.8(3) . . ?
C1 N1 C4 125.1(3) . . ?
C2 N1 C4 126.0(3) . . ?
C1 N2 C3 108.9(3) . . ?
C1 N2 C5 125.9(3) . . ?
C3 N2 C5 125.1(3) . . ?
N2 C1 N1 108.4(3) . . ?
C3 C2 N1 107.1(3) . . ?
C2 C3 N2 106.9(3) . . ?
N2 C5 C6 116.2(4) . . ?
C5 C6 C7 110.3(6) . . ?
C8 C7 C6 108.1(6) . . ?
C8A C7A C6A 108.8(8) . . ?
C9 N3 C10 108.7(3) . . ?
C9 N3 C12 125.6(4) . . ?
C10 N3 C12 125.6(4) . . ?
C9 N4 C11 108.2(3) . . ?
C9 N4 C13 125.5(3) . . ?
C11 N4 C13 126.4(3) . . ?
N4 C9 N3 108.8(3) . . ?
C11 C10 N3 107.0(4) . . ?
C10 C11 N4 107.4(4) . . ?
N4 C13 C14 111.5(3) . . ?
C13 C14 C15 112.3(3) . . ?
C14 C15 C16 112.9(3) . . ?
C17 N5 C19 108.6(3) . . ?
C17 N5 C21 125.3(3) . . ?
C19 N5 C21 126.1(3) . . ?
C17 N6 C18 108.6(3) . . ?
C17 N6 C20 126.1(4) . . ?
C18 N6 C20 125.3(4) . . ?
N5 C17 N6 108.6(4) . . ?
C19 C18 N6 106.9(4) . . ?
C18 C19 N5 107.4(4) . . ?
N5 C21 C22 111.3(3) . . ?
C21 C22 C23 111.4(3) . . ?
C24 C23 C22 113.6(3) . . ?
C25 N7 C26 108.8(3) . . ?
C25 N7 C28 126.0(4) . . ?
C26 N7 C28 125.1(4) . . ?
C25 N8 C27 108.9(3) . . ?
C25 N8 C29 125.9(3) . . ?
C27 N8 C29 124.9(3) . . ?
N8 C25 N7 108.2(3) . . ?
C27 C26 N7 107.1(4) . . ?
C26 C27 N8 107.0(4) . . ?
N8 C29 C30 110.5(3) . . ?
C29 C30 C31 113.5(5) . . ?
C32 C31 C30 108.2(6) . . ?

_refine_diff_density_max         0.575
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.067

_shelxl_version_number           2012-9

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cuclbmim_213k
_database_code_depnum_ccdc_archive 'CCDC 1427587'
_audit_update_record             
;
2015-09-25 deposited with the CCDC.
2016-01-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H30 Cl3 Cu N4'
_chemical_formula_weight         448.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

_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, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   12.983(4)
_cell_length_b                   11.352(3)
_cell_length_c                   15.982(5)
_cell_angle_alpha                90
_cell_angle_beta                 110.11(3)
_cell_angle_gamma                90
_cell_volume                     2212.1(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    213(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       flaky
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_F_000             936
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    1.355
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.7199
_exptl_absorpt_correction_T_max  0.7965
_exptl_absorpt_process_details   'Coppens 1970'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      213(2)
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 6.67
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_voltage           50
_diffrn_source_current           40
_diffrn_source_power             2.00
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    '0.5 mm diameter, monocapillary'
_diffrn_measurement_method       'rotation method'
_diffrn_measurement_details      
; 70 frames, detector distance = 120 mm
;
_diffrn_reflns_number            6529
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.357
_diffrn_reflns_theta_max         26.730
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.837
_diffrn_reflns_point_group_measured_fraction_full 0.851
_reflns_number_total             3932
_reflns_number_gt                2931
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.608
_reflns_Friedel_fraction_max     0.668
_reflns_Friedel_fraction_full    0.692

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0411P)²+5.1850P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0025(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 890 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.001(16)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3932
_refine_ls_number_parameters     280
_refine_ls_number_restraints     127
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.1307
_refine_ls_wR_factor_gt          0.1096
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_restrained_S_all      1.146
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.001

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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.25615(8) 0.3591(5) 0.25155(7) 0.0508(3) Uani 1 1 d . . . . .
Cl1 Cl 0.26490(19) 0.5541(5) 0.25335(14) 0.0624(6) Uani 1 1 d . . . . .
Cl2 Cl 0.38956(14) 0.2487(6) 0.34683(15) 0.0564(6) Uani 1 1 d . . . . .
Cl3 Cl 0.11701(14) 0.2565(5) 0.15477(13) 0.0511(6) Uani 1 1 d . . . . .
N1 N 0.2756(5) 0.5925(8) 0.5161(4) 0.0564(18) Uani 1 1 d . . . . .
N2 N 0.3866(5) 0.5163(8) 0.6365(4) 0.0500(16) Uani 1 1 d . . . . .
C1 C 0.3047(7) 0.5914(10) 0.6045(5) 0.060(2) Uani 1 1 d . . . . .
H1 H 0.2728 0.6359 0.6380 0.072 Uiso 1 1 calc R U . . .
C2 C 0.3419(7) 0.5167(9) 0.4921(6) 0.056(2) Uani 1 1 d . . . . .
H2 H 0.3396 0.5014 0.4343 0.068 Uiso 1 1 calc R U . . .
C3 C 0.4107(5) 0.4682(10) 0.5663(4) 0.0490(18) Uani 1 1 d . . . . .
H3 H 0.4647 0.4126 0.5700 0.059 Uiso 1 1 calc R U . . .
C4 C 0.1898(9) 0.6667(12) 0.4558(7) 0.089(4) Uani 1 1 d . . . . .
H4A H 0.1229 0.6564 0.4679 0.134 Uiso 1 1 calc R U . . .
H4B H 0.1783 0.6446 0.3952 0.134 Uiso 1 1 calc R U . . .
H4C H 0.2119 0.7477 0.4646 0.134 Uiso 1 1 calc R U . . .
C5 C 0.4414(6) 0.4877(7) 0.7312(5) 0.064(2) Uani 0.47(2) 1 d D U P A 1
H5A H 0.4438 0.5578 0.7664 0.077 Uiso 0.47(2) 1 calc R U P A 1
H5B H 0.5164 0.4644 0.7405 0.077 Uiso 0.47(2) 1 calc R U P A 1
C6 C 0.3852(18) 0.3897(17) 0.7640(11) 0.089(6) Uani 0.47(2) 1 d D U P A 1
H6A H 0.3814 0.3178 0.7303 0.106 Uiso 0.47(2) 1 calc R U P A 1
H6B H 0.3117 0.4124 0.7602 0.106 Uiso 0.47(2) 1 calc R U P A 1
C7 C 0.460(2) 0.375(2) 0.8604(12) 0.108(7) Uani 0.47(2) 1 d D U P A 1
H7A H 0.5354 0.3664 0.8642 0.129 Uiso 0.47(2) 1 calc R U P A 1
H7B H 0.4538 0.4423 0.8957 0.129 Uiso 0.47(2) 1 calc R U P A 1
C8 C 0.421(3) 0.267(2) 0.8922(16) 0.121(8) Uani 0.47(2) 1 d D U P A 1
H8A H 0.3439 0.2575 0.8616 0.181 Uiso 0.47(2) 1 calc R U P A 1
H8B H 0.4357 0.2730 0.9551 0.181 Uiso 0.47(2) 1 calc R U P A 1
H8C H 0.4594 0.1999 0.8805 0.181 Uiso 0.47(2) 1 calc R U P A 1
C5A C 0.4414(6) 0.4877(7) 0.7312(5) 0.064(2) Uani 0.53(2) 1 d D U P A 2
H5A1 H 0.4213 0.5451 0.7678 0.077 Uiso 0.53(2) 1 calc R U P A 2
H5A2 H 0.5203 0.4906 0.7457 0.077 Uiso 0.53(2) 1 calc R U P A 2
C6A C 0.4077(12) 0.3653(9) 0.7505(8) 0.065(4) Uani 0.53(2) 1 d D U P A 2
H6A1 H 0.4366 0.3086 0.7189 0.078 Uiso 0.53(2) 1 calc R U P A 2
H6A2 H 0.3284 0.3603 0.7259 0.078 Uiso 0.53(2) 1 calc R U P A 2
C7A C 0.4440(15) 0.328(2) 0.8478(8) 0.080(5) Uani 0.53(2) 1 d D U P A 2
H7A1 H 0.4415 0.2431 0.8502 0.096 Uiso 0.53(2) 1 calc R U P A 2
H7A2 H 0.5198 0.3519 0.8764 0.096 Uiso 0.53(2) 1 calc R U P A 2
C8A C 0.3792(13) 0.377(2) 0.8998(9) 0.089(6) Uani 0.53(2) 1 d D U P A 2
H8A1 H 0.3856 0.4609 0.9022 0.133 Uiso 0.53(2) 1 calc R U P A 2
H8A2 H 0.4064 0.3452 0.9592 0.133 Uiso 0.53(2) 1 calc R U P A 2
H8A3 H 0.3036 0.3550 0.8720 0.133 Uiso 0.53(2) 1 calc R U P A 2
N3 N 0.2337(5) 0.5864(8) 0.9876(4) 0.0520(17) Uani 1 1 d . . . . .
N4 N 0.1055(5) 0.5263(8) 0.8695(4) 0.0489(16) Uani 1 1 d . . . . .
C9 C 0.1909(6) 0.5971(9) 0.8989(5) 0.055(2) Uani 1 1 d . . . . .
H9 H 0.2171 0.6461 0.8640 0.066 Uiso 1 1 calc R U . . .
C10 C 0.1723(7) 0.5068(9) 1.0131(6) 0.057(2) Uani 1 1 d . . . . .
H10 H 0.1835 0.4834 1.0713 0.069 Uiso 1 1 calc R U . . .
C11 C 0.0933(6) 0.4676(11) 0.9405(4) 0.0528(19) Uani 1 1 d . . . . .
H11 H 0.0403 0.4114 0.9384 0.063 Uiso 1 1 calc R U . . .
C12 C 0.3300(8) 0.6481(11) 1.0458(6) 0.078(3) Uani 1 1 d . . . . .
H12A H 0.3857 0.5919 1.0759 0.118 Uiso 1 1 calc R U . . .
H12B H 0.3104 0.6930 1.0890 0.118 Uiso 1 1 calc R U . . .
H12C H 0.3573 0.7001 1.0110 0.118 Uiso 1 1 calc R U . . .
C13 C 0.0380(7) 0.5080(8) 0.7753(5) 0.067(2) Uani 0.652(18) 1 d D U P B 1
H13A H 0.0494 0.5728 0.7399 0.081 Uiso 0.652(18) 1 calc R U P B 1
H13B H -0.0389 0.5070 0.7693 0.081 Uiso 0.652(18) 1 calc R U P B 1
C14 C 0.0675(10) 0.3927(9) 0.7408(7) 0.068(4) Uani 0.652(18) 1 d D U P B 1
H14A H 0.0572 0.3279 0.7767 0.082 Uiso 0.652(18) 1 calc R U P B 1
H14B H 0.1441 0.3941 0.7458 0.082 Uiso 0.652(18) 1 calc R U P B 1
C15 C -0.0037(14) 0.3738(16) 0.6441(8) 0.087(4) Uani 0.652(18) 1 d D U P B 1
H15A H -0.0792 0.3619 0.6403 0.105 Uiso 0.652(18) 1 calc R U P B 1
H15B H -0.0011 0.4434 0.6098 0.105 Uiso 0.652(18) 1 calc R U P B 1
C16 C 0.0338(16) 0.2707(15) 0.6061(12) 0.104(6) Uani 0.652(18) 1 d D U P B 1
H16A H 0.1031 0.2881 0.5997 0.156 Uiso 0.652(18) 1 calc R U P B 1
H16B H -0.0192 0.2525 0.5487 0.156 Uiso 0.652(18) 1 calc R U P B 1
H16C H 0.0419 0.2043 0.6450 0.156 Uiso 0.652(18) 1 calc R U P B 1
C13A C 0.0380(7) 0.5080(8) 0.7753(5) 0.067(2) Uani 0.348(18) 1 d D U P B 2
H13C H 0.0231 0.5831 0.7445 0.081 Uiso 0.348(18) 1 calc R U P B 2
H13D H -0.0314 0.4723 0.7712 0.081 Uiso 0.348(18) 1 calc R U P B 2
C14A C 0.0993(18) 0.428(2) 0.7322(11) 0.079(6) Uani 0.348(18) 1 d D U P B 2
H14C H 0.1105 0.3528 0.7629 0.095 Uiso 0.348(18) 1 calc R U P B 2
H14D H 0.1712 0.4620 0.7425 0.095 Uiso 0.348(18) 1 calc R U P B 2
C15A C 0.0467(18) 0.404(3) 0.6330(12) 0.094(7) Uani 0.348(18) 1 d D U P B 2
H15C H 0.0488 0.4757 0.6001 0.112 Uiso 0.348(18) 1 calc R U P B 2
H15D H 0.0881 0.3441 0.6153 0.112 Uiso 0.348(18) 1 calc R U P B 2
C16A C -0.0681(19) 0.365(4) 0.611(2) 0.100(8) Uani 0.348(18) 1 d D U P B 2
H16D H -0.0728 0.2822 0.5992 0.150 Uiso 0.348(18) 1 calc R U P B 2
H16E H -0.1136 0.4064 0.5585 0.150 Uiso 0.348(18) 1 calc R U P B 2
H16F H -0.0927 0.3821 0.6596 0.150 Uiso 0.348(18) 1 calc R U P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 Cl1 2.216(3) . ?
Cu1 Cl2 2.253(2) . ?
Cu1 Cl3 2.257(2) . ?
N1 C1 1.332(11) . ?
N1 C2 1.362(10) . ?
N1 C4 1.463(10) . ?
N2 C1 1.321(10) . ?
N2 C3 1.376(9) . ?
N2 C5A 1.471(9) . ?
N2 C5 1.471(9) . ?
C2 C3 1.334(11) . ?
C5 C6 1.519(7) . ?
C6 C7 1.520(7) . ?
C7 C8 1.477(14) . ?
C5A C6A 1.520(7) . ?
C6A C7A 1.520(7) . ?
C7A C8A 1.477(14) . ?
N3 C9 1.339(10) . ?
N3 C10 1.356(10) . ?
N3 C12 1.456(10) . ?
N4 C9 1.319(9) . ?
N4 C11 1.371(9) . ?
N4 C13A 1.473(10) . ?
N4 C13 1.473(10) . ?
C10 C11 1.334(11) . ?
C13 C14 1.520(7) . ?
C14 C15 1.520(7) . ?
C15 C16 1.477(14) . ?
C13A C14A 1.520(7) . ?
C14A C15A 1.520(7) . ?
C15A C16A 1.477(14) . ?

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
_geom_angle_publ_flag
Cl1 Cu1 Cl2 121.52(10) . . ?
Cl1 Cu1 Cl3 123.37(10) . . ?
Cl2 Cu1 Cl3 115.1(3) . . ?
C1 N1 C2 108.5(7) . . ?
C1 N1 C4 125.3(8) . . ?
C2 N1 C4 126.1(8) . . ?
C1 N2 C3 108.7(6) . . ?
C1 N2 C5A 125.5(7) . . ?
C3 N2 C5A 125.8(6) . . ?
C1 N2 C5 125.5(7) . . ?
C3 N2 C5 125.8(6) . . ?
N2 C1 N1 108.2(7) . . ?
C3 C2 N1 107.7(7) . . ?
C2 C3 N2 106.9(7) . . ?
N2 C5 C6 113.5(9) . . ?
C5 C6 C7 102.6(13) . . ?
C8 C7 C6 105.6(16) . . ?
N2 C5A C6A 109.9(8) . . ?
C5A C6A C7A 116.8(14) . . ?
C8A C7A C6A 116.0(14) . . ?
C9 N3 C10 107.8(6) . . ?
C9 N3 C12 125.8(7) . . ?
C10 N3 C12 126.4(7) . . ?
C9 N4 C11 108.8(6) . . ?
C9 N4 C13A 125.6(7) . . ?
C11 N4 C13A 125.5(6) . . ?
C9 N4 C13 125.6(7) . . ?
C11 N4 C13 125.5(6) . . ?
N4 C9 N3 108.3(7) . . ?
C11 C10 N3 108.5(7) . . ?
C10 C11 N4 106.6(7) . . ?
N4 C13 C14 110.9(8) . . ?
C13 C14 C15 110.5(10) . . ?
C16 C15 C14 111.1(13) . . ?
N4 C13A C14A 109.1(9) . . ?
C13A C14A C15A 117.4(18) . . ?
C16A C15A C14A 111(2) . . ?

_refine_diff_density_max         0.299
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.062

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cuclbmin_233k
_database_code_depnum_ccdc_archive 'CCDC 1427588'
_audit_update_record             
;
2015-09-25 deposited with the CCDC.
2016-01-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          320
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H30 Cl3 Cu N4'
_chemical_formula_weight         448.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

_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, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   12.990(6)
_cell_length_b                   11.404(4)
_cell_length_c                   8.386(4)
_cell_angle_alpha                90
_cell_angle_beta                 116.30(3)
_cell_angle_gamma                90
_cell_volume                     1113.8(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    233(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       flaky
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_F_000             468
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    1.346
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.8026
_exptl_absorpt_correction_T_max  0.9139
_exptl_absorpt_process_details   'Coppens 1970'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      233(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 6.67
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_voltage           50
_diffrn_source_current           40
_diffrn_source_power             2.00
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    '0.5 mm diameter, monocapillary'
_diffrn_measurement_method       'rotation method'
_diffrn_measurement_details      
; 73 frames, detector distance = 120 mm
;

_diffrn_reflns_number            3438
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.500
_diffrn_reflns_theta_max         26.732
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.915
_diffrn_reflns_point_group_measured_fraction_full 0.928
_reflns_number_total             2170
_reflns_number_gt                1853
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.754
_reflns_Friedel_fraction_max     0.830
_reflns_Friedel_fraction_full    0.849

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0213P)²+4.6134P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0069(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 694 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2170
_refine_ls_number_parameters     145
_refine_ls_number_restraints     57
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_ref         0.1108
_refine_ls_wR_factor_gt          0.0984
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.001

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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 1.0000 0.5571(8) 0.0000 0.0555(5) Uani 1 2 d S T P . .
Cl1 Cl 0.96047(18) 0.6633(8) 0.1930(3) 0.0587(6) Uani 1 1 d . . . . .
Cl2 Cl 1.0000 0.3625(8) 0.0000 0.0719(9) Uani 1 2 d S T P . .
N1 N 0.2569(6) 0.8265(10) 0.4722(9) 0.0576(17) Uani 1 1 d . . . . .
N2 N 0.2565(5) 0.8949(10) 0.2331(8) 0.0511(16) Uani 1 1 d D . . . .
C1 C 0.2053(7) 0.8217(11) 0.2967(11) 0.059(2) Uani 1 1 d . . . . .
H1 H 0.1429 0.7743 0.2289 0.071 Uiso 1 1 calc R U . . .
C2 C 0.3463(8) 0.9033(10) 0.5215(12) 0.060(2) Uani 1 1 d . . . . .
H2 H 0.3985 0.9215 0.6375 0.072 Uiso 1 1 calc R U . . .
C3 C 0.3453(6) 0.9477(12) 0.3739(9) 0.0543(18) Uani 1 1 d . . . . .
H3 H 0.3952 1.0038 0.3675 0.065 Uiso 1 1 calc R U . . .
C4 C 0.2269(10) 0.7575(13) 0.5941(14) 0.095(4) Uani 1 1 d . . . . .
H4A H 0.1592 0.7897 0.5960 0.142 Uiso 1 1 calc R U . . .
H4B H 0.2893 0.7602 0.7116 0.142 Uiso 1 1 calc R U . . .
H4C H 0.2128 0.6776 0.5541 0.142 Uiso 1 1 calc R U . . .
C5 C 0.204(3) 0.9246(19) 0.0411(14) 0.060(4) Uani 0.38(2) 1 d D U P A 1
H5A H 0.1396 0.8728 -0.0221 0.072 Uiso 0.38(2) 1 calc R U P A 1
H5B H 0.2603 0.9107 -0.0039 0.072 Uiso 0.38(2) 1 calc R U P A 1
C6 C 0.163(2) 1.0510(16) 0.002(2) 0.067(6) Uani 0.38(2) 1 d D U P A 1
H6A H 0.2268 1.1037 0.0657 0.080 Uiso 0.38(2) 1 calc R U P A 1
H6B H 0.1047 1.0651 0.0419 0.080 Uiso 0.38(2) 1 calc R U P A 1
C7 C 0.114(3) 1.075(2) -0.197(3) 0.110(10) Uani 0.38(2) 1 d D U P A 1
H7A H 0.1003 1.1587 -0.2183 0.132 Uiso 0.38(2) 1 calc R U P A 1
H7B H 0.1685 1.0512 -0.2402 0.132 Uiso 0.38(2) 1 calc R U P A 1
C8 C 0.013(3) 1.016(3) -0.287(3) 0.139(14) Uani 0.38(2) 1 d D U P A 1
H8A H 0.0095 0.9851 -0.3958 0.209 Uiso 0.38(2) 1 calc R U P A 1
H8B H -0.0506 1.0681 -0.3135 0.209 Uiso 0.38(2) 1 calc R U P A 1
H8C H 0.0087 0.9523 -0.2148 0.209 Uiso 0.38(2) 1 calc R U P A 1
C5A C 0.2326(17) 0.9148(19) 0.0451(12) 0.060(4) Uani 0.62(2) 1 d D U P A 2
H5A1 H 0.2022 0.8437 -0.0230 0.072 Uiso 0.62(2) 1 calc R U P A 2
H5A2 H 0.3033 0.9348 0.0387 0.072 Uiso 0.62(2) 1 calc R U P A 2
C6A C 0.146(2) 1.0139(18) -0.033(2) 0.113(8) Uani 0.62(2) 1 d D U P A 2
H6A1 H 0.1750 1.0840 0.0387 0.136 Uiso 0.62(2) 1 calc R U P A 2
H6A2 H 0.0743 0.9923 -0.0319 0.136 Uiso 0.62(2) 1 calc R U P A 2
C7A C 0.126(2) 1.039(2) -0.223(2) 0.174(11) Uani 0.62(2) 1 d D U P A 2
H7A1 H 0.1983 1.0390 -0.2298 0.209 Uiso 0.62(2) 1 calc R U P A 2
H7A2 H 0.0776 0.9781 -0.3015 0.209 Uiso 0.62(2) 1 calc R U P A 2
C8A C 0.073(3) 1.1456(19) -0.277(3) 0.195(14) Uani 0.62(2) 1 d D U P A 2
H8A1 H 0.1149 1.2040 -0.1902 0.293 Uiso 0.62(2) 1 calc R U P A 2
H8A2 H -0.0040 1.1412 -0.2909 0.293 Uiso 0.62(2) 1 calc R U P A 2
H8A3 H 0.0720 1.1663 -0.3892 0.293 Uiso 0.62(2) 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 Cl2 2.219(13) . ?
Cu1 Cl1 2.255(7) . ?
Cu1 Cl1 2.255(7) 2_755 ?
N1 C1 1.320(11) . ?
N1 C2 1.364(10) . ?
N1 C4 1.472(11) . ?
N2 C1 1.319(10) . ?
N2 C3 1.371(9) . ?
N2 C5A 1.483(10) . ?
N2 C5 1.483(10) . ?
C2 C3 1.332(11) . ?
C5 C6 1.522(11) . ?
C6 C7 1.522(11) . ?
C7 C8 1.37(3) . ?
C5A C6A 1.522(11) . ?
C6A C7A 1.522(11) . ?
C7A C8A 1.37(3) . ?

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
_geom_angle_publ_flag
Cl2 Cu1 Cl1 122.5(3) . . ?
Cl2 Cu1 Cl1 122.5(3) . 2_755 ?
Cl1 Cu1 Cl1 115.06(11) . 2_755 ?
C1 N1 C2 107.9(7) . . ?
C1 N1 C4 126.3(7) . . ?
C2 N1 C4 125.7(7) . . ?
C1 N2 C3 108.2(6) . . ?
C1 N2 C5A 128.4(10) . . ?
C3 N2 C5A 123.2(10) . . ?
C1 N2 C5 120.9(17) . . ?
C3 N2 C5 129.8(16) . . ?
N2 C1 N1 109.1(7) . . ?
C3 C2 N1 107.8(7) . . ?
C2 C3 N2 107.0(7) . . ?
N2 C5 C6 113.6(15) . . ?
C5 C6 C7 110.3(13) . . ?
C8 C7 C6 110.5(17) . . ?
N2 C5A C6A 109.8(11) . . ?
C5A C6A C7A 110.2(12) . . ?
C8A C7A C6A 110.2(17) . . ?

_refine_diff_density_max         0.356
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.066


_exptl_crystal_recrystallization_method 'From the Melt'
_chemical_properties_physical    
'Air-sensitive, Moisture-sensitive, Hygroscopic'
