# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_2a
_database_code_depnum_ccdc_archive 'CCDC 1048449'
_audit_update_record             
;
2015-02-09 deposited with the CCDC.
2015-06-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H25 B Cl4 Cu N3'
_chemical_formula_sum            'C20 H25 B Cl4 Cu N3'
_chemical_formula_weight         523.58

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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

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

_cell_length_a                   16.9427(9)
_cell_length_b                   19.9103(10)
_cell_length_c                   6.8692(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2317.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173
_cell_measurement_reflns_used    1437
_cell_measurement_theta_min      4.4080
_cell_measurement_theta_max      73.3130

_exptl_crystal_description       needles
_exptl_crystal_colour            'Pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_F_000             1072
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    5.663
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.379
_exptl_absorpt_correction_T_max  0.885
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33a (release 28-03-2014 CrysAlis171 .NET)
(compiled Mar 28 2014,12:25:20)
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_special_details           
;
 ?
;

_diffrn_ambient_temperature      173
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_measurement_device_type  'Agilent Xcalibur PX Ultra A'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 10.4115
_diffrn_reflns_number            4503
_diffrn_reflns_av_unetI/netI     0.0423
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_theta_min         4.441
_diffrn_reflns_theta_max         73.587
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             2289
_reflns_number_gt                1925
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'CrysAlisPro, Agilent Technologies'
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CIFTAB-2013 (Sheldrick, 2013)'

_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)+(0.0561P)²+1.2096P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2289
_refine_ls_number_parameters     161
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0440
_refine_ls_wR_factor_ref         0.1181
_refine_ls_wR_factor_gt          0.1103
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_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 0.42597(3) 0.2500 0.32057(8) 0.03201(19) Uani 1 2 d S T P . .
N1 N 0.38151(13) 0.32399(12) 0.1661(3) 0.0324(5) Uani 1 1 d . . . . .
C1 C 0.35518(14) 0.31369(14) -0.0133(4) 0.0304(5) Uani 1 1 d . . . . .
C2 C 0.3492(2) 0.2500 -0.0995(5) 0.0308(7) Uani 1 2 d S T P . .
H2A H 0.3396 0.2500 -0.2358 0.037 Uiso 1 2 calc R U P . .
C3 C 0.3306(2) 0.37280(15) -0.1373(5) 0.0424(7) Uani 1 1 d . . . . .
H3A H 0.2800 0.3904 -0.0904 0.064 Uiso 1 1 calc R U . . .
H3B H 0.3250 0.3583 -0.2730 0.064 Uiso 1 1 calc R U . . .
H3C H 0.3708 0.4080 -0.1291 0.064 Uiso 1 1 calc R U . . .
C4 C 0.37168(17) 0.38841(14) 0.2496(4) 0.0346(6) Uani 1 1 d . . . . .
C5 C 0.43183(18) 0.43662(15) 0.2522(5) 0.0402(6) Uani 1 1 d . . . . .
Cl5 Cl 0.52047(5) 0.41892(4) 0.13739(14) 0.0527(2) Uani 1 1 d . . . . .
C6 C 0.4236(2) 0.49847(17) 0.3442(5) 0.0473(8) Uani 1 1 d . . . . .
H6A H 0.4656 0.5301 0.3427 0.057 Uiso 1 1 calc R U . . .
C7 C 0.3533(2) 0.51336(17) 0.4378(5) 0.0502(8) Uani 1 1 d . . . . .
H7A H 0.3472 0.5553 0.5022 0.060 Uiso 1 1 calc R U . . .
C8 C 0.2919(2) 0.46769(17) 0.4384(5) 0.0456(7) Uani 1 1 d . . . . .
H8A H 0.2438 0.4780 0.5028 0.055 Uiso 1 1 calc R U . . .
C9 C 0.30132(18) 0.40651(16) 0.3437(4) 0.0389(6) Uani 1 1 d . . . . .
Cl9 Cl 0.22395(5) 0.34951(4) 0.34634(13) 0.0496(2) Uani 1 1 d . . . . .
B11 B 0.5178(4) 0.2123(3) 0.5170(9) 0.0327(12) Uani 0.5 1 d . . P A -1
N12 N 0.5682(2) 0.2514(10) 0.6672(5) 0.0376(12) Uani 0.5 1 d . . P A -1
C13 C 0.6537(3) 0.247(2) 0.6231(9) 0.054(3) Uani 0.5 1 d . . P A -1
H13A H 0.6639 0.2648 0.4929 0.081 Uiso 0.5 1 calc R U P A -1
H13B H 0.6702 0.1994 0.6275 0.081 Uiso 0.5 1 calc R U P A -1
H13C H 0.6837 0.2723 0.7197 0.081 Uiso 0.5 1 calc R U P A -1
C14 C 0.5563(4) 0.2343(5) 0.8694(9) 0.053(4) Uani 0.5 1 d . . P A -1
H14A H 0.5918 0.2613 0.9507 0.080 Uiso 0.5 1 calc R U P A -1
H14B H 0.5677 0.1865 0.8890 0.080 Uiso 0.5 1 calc R U P A -1
H14C H 0.5015 0.2436 0.9058 0.080 Uiso 0.5 1 calc R U P A -1
C15 C 0.5461(5) 0.3289(3) 0.6523(11) 0.0524(17) Uani 0.5 1 d . . P A -1
H15A H 0.4918 0.3357 0.6976 0.079 Uiso 0.5 1 calc R U P A -1
H15B H 0.5505 0.3437 0.5167 0.079 Uiso 0.5 1 calc R U P A -1
H15C H 0.5823 0.3552 0.7335 0.079 Uiso 0.5 1 calc R U P A -1

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 0.0315(3) 0.0383(3) 0.0262(3) 0.000 -0.0058(2) 0.000
N1 0.0287(10) 0.0396(11) 0.0290(11) -0.0035(9) -0.0014(9) 0.0006(9)
C1 0.0219(11) 0.0424(14) 0.0269(12) 0.0020(10) 0.0013(9) 0.0024(10)
C2 0.0266(16) 0.045(2) 0.0210(16) 0.000 0.0011(13) 0.000
C3 0.0470(17) 0.0432(15) 0.0372(15) 0.0039(12) -0.0037(13) 0.0071(13)
C4 0.0357(13) 0.0387(13) 0.0293(13) -0.0023(11) -0.0058(11) 0.0054(11)
C5 0.0369(14) 0.0397(14) 0.0441(16) -0.0042(13) -0.0014(13) 0.0041(12)
Cl5 0.0384(4) 0.0498(4) 0.0699(6) -0.0131(4) 0.0093(4) -0.0039(3)
C6 0.0492(18) 0.0403(16) 0.0523(19) -0.0070(14) -0.0092(15) 0.0023(13)
C7 0.062(2) 0.0411(16) 0.0476(19) -0.0053(14) -0.0048(16) 0.0163(15)
C8 0.0511(18) 0.0518(17) 0.0338(15) 0.0015(13) 0.0028(13) 0.0203(14)
C9 0.0390(15) 0.0468(15) 0.0310(14) 0.0037(12) -0.0022(12) 0.0085(12)
Cl9 0.0365(4) 0.0615(5) 0.0509(4) 0.0023(3) 0.0072(3) 0.0015(3)
B11 0.033(3) 0.033(3) 0.032(3) 0.001(2) -0.011(2) 0.003(2)
N12 0.0266(18) 0.057(3) 0.0286(17) 0.002(8) -0.0003(16) -0.023(6)
C13 0.025(2) 0.090(7) 0.047(3) -0.017(11) 0.002(2) 0.007(10)
C14 0.034(2) 0.096(11) 0.029(3) 0.012(3) -0.009(2) -0.013(3)
C15 0.071(5) 0.034(3) 0.052(4) -0.010(3) -0.014(3) 0.000(3)

_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 N1 1.966(2) . ?
Cu1 N1 1.966(2) 7_565 ?
Cu1 B11 2.191(6) . ?
N1 C1 1.326(4) . ?
N1 C4 1.415(4) . ?
C1 C2 1.403(3) . ?
C1 C3 1.511(4) . ?
C2 C1 1.403(3) 7_565 ?
C4 C5 1.400(4) . ?
C4 C9 1.403(4) . ?
C5 C6 1.391(5) . ?
C5 Cl5 1.733(3) . ?
C6 C7 1.386(5) . ?
C7 C8 1.381(5) . ?
C8 C9 1.390(5) . ?
C9 Cl9 1.734(3) . ?
B11 N12 1.549(11) . ?
N12 C14 1.444(8) . ?
N12 C13 1.483(7) . ?
N12 C15 1.59(2) . ?

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
N1 Cu1 N1 97.08(14) . 7_565 ?
N1 Cu1 B11 149.42(17) . . ?
N1 Cu1 B11 110.36(17) 7_565 . ?
C1 N1 C4 118.5(2) . . ?
C1 N1 Cu1 121.0(2) . . ?
C4 N1 Cu1 120.35(18) . . ?
N1 C1 C2 123.8(3) . . ?
N1 C1 C3 119.7(3) . . ?
C2 C1 C3 116.5(3) . . ?
C1 C2 C1 129.3(3) 7_565 . ?
C5 C4 C9 115.9(3) . . ?
C5 C4 N1 122.7(3) . . ?
C9 C4 N1 121.3(3) . . ?
C6 C5 C4 122.6(3) . . ?
C6 C5 Cl5 118.3(3) . . ?
C4 C5 Cl5 119.1(2) . . ?
C7 C6 C5 119.1(3) . . ?
C8 C7 C6 120.5(3) . . ?
C7 C8 C9 119.3(3) . . ?
C8 C9 C4 122.5(3) . . ?
C8 C9 Cl9 118.8(3) . . ?
C4 C9 Cl9 118.6(2) . . ?
N12 B11 Cu1 129.0(8) . . ?
C14 N12 C13 108.5(8) . . ?
C14 N12 B11 116.5(9) . . ?
C13 N12 B11 111.7(12) . . ?
C14 N12 C15 104.9(10) . . ?
C13 N12 C15 106.3(18) . . ?
B11 N12 C15 108.3(7) . . ?

_refine_diff_density_max         0.857
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.083

_shelxl_version_number           2013-4
####################################################################### 
# 
# 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_2b
_database_code_depnum_ccdc_archive 'CCDC 1048450'
_audit_update_record             
;
2015-02-09 deposited with the CCDC.
2015-06-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H23 B Cl4 Cu N3'
_chemical_formula_sum            'C23 H23 B Cl4 Cu N3'
_chemical_formula_weight         557.59

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'
Cl Cl 0.1484 0.1585 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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'

_cell_length_a                   11.0385(2)
_cell_length_b                   15.6053(3)
_cell_length_c                   14.7655(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.005(2)
_cell_angle_gamma                90
_cell_volume                     2524.50(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    173
_cell_measurement_reflns_used    3450
_cell_measurement_theta_min      2.7960
_cell_measurement_theta_max      27.5120

_exptl_crystal_description       blocks
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_F_000             1136
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.14
_exptl_absorpt_coefficient_mu    1.305
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.699
_exptl_absorpt_correction_T_max  0.846
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33a (release 28-03-2014 CrysAlis171 .NET)
(compiled Mar 28 2014,12:25:20)
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_special_details           
;
 ?
;

_diffrn_ambient_temperature      173
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Agilent Xcalibur 3 E'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 16.0382
_diffrn_reflns_number            8915
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.542
_diffrn_reflns_theta_max         28.231
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.813
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.813
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.813
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             5062
_reflns_number_gt                4141
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'CrysAlisPro, Agilent Technologies'
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CIFTAB-2013 (Sheldrick, 2013)'

_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)+(0.0260P)²+1.2350P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0009(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5062
_refine_ls_number_parameters     305
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0327
_refine_ls_wR_factor_ref         0.0731
_refine_ls_wR_factor_gt          0.0680
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.001
_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 0.73838(2) 0.00459(2) 0.77252(2) 0.02444(9) Uani 1 1 d . . . . .
H1 H 0.875(2) 0.0152(14) 0.8526(16) 0.035(6) Uiso 1 1 d . . . . .
H2 H 0.7430(19) 0.0962(13) 0.8458(14) 0.027(6) Uiso 1 1 d . . . . .
H3 H 0.854(2) 0.0794(15) 0.9466(16) 0.039(7) Uiso 1 1 d . . . . .
N1 N 0.74878(15) 0.01325(10) 0.64173(11) 0.0221(4) Uani 1 1 d . . . . .
C1 C 0.68702(18) -0.03898(14) 0.58236(14) 0.0235(5) Uani 1 1 d . . . . .
C2 C 0.61358(19) -0.10620(14) 0.60767(14) 0.0268(5) Uani 1 1 d . . . . .
H2A H 0.5855 -0.1448 0.5600 0.032 Uiso 1 1 calc R U . . .
N3 N 0.61667(15) -0.08548(11) 0.76921(11) 0.0228(4) Uani 1 1 d . . . . .
C3 C 0.57552(19) -0.12500(13) 0.69234(15) 0.0259(5) Uani 1 1 d . . . . .
C4 C 0.6906(2) -0.02687(16) 0.48129(15) 0.0331(5) Uani 1 1 d . . . . .
H4A H 0.6336 0.0187 0.4588 0.050 Uiso 1 1 calc R U . . .
H4B H 0.6671 -0.0805 0.4492 0.050 Uiso 1 1 calc R U . . .
H4C H 0.7734 -0.0110 0.4703 0.050 Uiso 1 1 calc R U . . .
C5 C 0.4811(2) -0.19555(16) 0.69357(17) 0.0410(6) Uani 1 1 d . . . . .
H5A H 0.5165 -0.2435 0.7306 0.061 Uiso 1 1 calc R U . . .
H5B H 0.4559 -0.2153 0.6311 0.061 Uiso 1 1 calc R U . . .
H5C H 0.4099 -0.1734 0.7198 0.061 Uiso 1 1 calc R U . . .
C6 C 0.80956(19) 0.08430(13) 0.60907(13) 0.0222(4) Uani 1 1 d . . . . .
C7 C 0.93468(19) 0.08365(14) 0.60217(15) 0.0272(5) Uani 1 1 d . . . . .
Cl7 Cl 1.01589(6) -0.00917(4) 0.63216(5) 0.04664(18) Uani 1 1 d . . . . .
C8 C 0.9948(2) 0.15343(15) 0.57160(16) 0.0338(5) Uani 1 1 d . . . . .
H8A H 1.0799 0.1504 0.5672 0.041 Uiso 1 1 calc R U . . .
C9 C 0.9314(2) 0.22735(15) 0.54755(16) 0.0350(6) Uani 1 1 d . . . . .
H9A H 0.9722 0.2751 0.5253 0.042 Uiso 1 1 calc R U . . .
C10 C 0.8082(2) 0.23209(14) 0.55576(15) 0.0322(5) Uani 1 1 d . . . . .
H10A H 0.7640 0.2832 0.5399 0.039 Uiso 1 1 calc R U . . .
C11 C 0.75012(19) 0.16193(14) 0.58722(14) 0.0264(5) Uani 1 1 d . . . . .
Cl11 Cl 0.59728(5) 0.17025(4) 0.60373(4) 0.04021(16) Uani 1 1 d . . . . .
C12 C 0.56217(18) -0.10116(13) 0.84906(14) 0.0221(4) Uani 1 1 d . . . . .
C13 C 0.45287(19) -0.06270(14) 0.86592(15) 0.0261(5) Uani 1 1 d . . . . .
Cl13 Cl 0.37619(6) 0.00135(5) 0.78086(4) 0.04814(18) Uani 1 1 d . . . . .
C14 C 0.4041(2) -0.07254(14) 0.94707(15) 0.0295(5) Uani 1 1 d . . . . .
H14A H 0.3291 -0.0457 0.9556 0.035 Uiso 1 1 calc R U . . .
C15 C 0.4653(2) -0.12156(14) 1.01554(15) 0.0289(5) Uani 1 1 d . . . . .
H15A H 0.4333 -0.1278 1.0721 0.035 Uiso 1 1 calc R U . . .
C16 C 0.5729(2) -0.16160(14) 1.00198(15) 0.0286(5) Uani 1 1 d . . . . .
H16A H 0.6151 -0.1958 1.0489 0.034 Uiso 1 1 calc R U . . .
C17 C 0.61894(18) -0.15164(13) 0.91993(15) 0.0245(5) Uani 1 1 d . . . . .
Cl17 Cl 0.75206(6) -0.20541(4) 0.90262(5) 0.04610(18) Uani 1 1 d . . . . .
B21 B 0.8427(2) 0.08095(17) 0.87546(18) 0.0293(6) Uani 1 1 d . . . . .
N22 N 0.92472(16) 0.15488(11) 0.84064(12) 0.0250(4) Uani 1 1 d . . . . .
C23 C 1.0477(2) 0.15149(15) 0.85399(16) 0.0326(5) Uani 1 1 d . . . . .
C24 C 1.1150(2) 0.22082(18) 0.82693(18) 0.0446(7) Uani 1 1 d . . . . .
H24A H 1.2017 0.2187 0.8359 0.054 Uiso 1 1 calc R U . . .
C25 C 1.0579(3) 0.29120(17) 0.78787(18) 0.0467(7) Uani 1 1 d . . . . .
H25A H 1.1042 0.3383 0.7701 0.056 Uiso 1 1 calc R U . . .
C26 C 0.9327(3) 0.29356(16) 0.77433(18) 0.0463(7) Uani 1 1 d . . . . .
H26A H 0.8910 0.3421 0.7471 0.056 Uiso 1 1 calc R U . . .
C27 C 0.8693(2) 0.22468(15) 0.80076(16) 0.0358(6) Uani 1 1 d . . . . .
H27A H 0.7826 0.2260 0.7907 0.043 Uiso 1 1 calc R U . . .
C28 C 1.1074(2) 0.07514(17) 0.8992(2) 0.0495(7) Uani 1 1 d . . . . .
H28A H 1.0792 0.0674 0.9590 0.074 Uiso 1 1 calc R U . . .
H28B H 1.1961 0.0832 0.9069 0.074 Uiso 1 1 calc R U . . .
H28C H 1.0864 0.0244 0.8614 0.074 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 0.02599(15) 0.02554(15) 0.02252(15) -0.00293(11) 0.00588(11) -0.00820(11)
N1 0.0234(9) 0.0213(9) 0.0227(9) 0.0003(7) 0.0072(7) -0.0033(7)
C1 0.0216(11) 0.0276(11) 0.0221(11) -0.0024(9) 0.0060(9) 0.0020(9)
C2 0.0293(12) 0.0273(11) 0.0247(12) -0.0103(9) 0.0069(9) -0.0077(10)
N3 0.0248(9) 0.0236(9) 0.0213(9) -0.0028(7) 0.0079(7) -0.0049(8)
C3 0.0259(11) 0.0233(11) 0.0299(12) -0.0046(9) 0.0085(9) -0.0053(9)
C4 0.0358(13) 0.0396(14) 0.0251(12) -0.0040(10) 0.0087(10) -0.0082(11)
C5 0.0496(16) 0.0416(14) 0.0343(14) -0.0117(11) 0.0154(12) -0.0252(13)
C6 0.0268(11) 0.0231(11) 0.0171(10) -0.0001(8) 0.0044(8) -0.0023(9)
C7 0.0270(11) 0.0257(11) 0.0296(12) 0.0046(9) 0.0070(9) 0.0028(10)
Cl7 0.0332(3) 0.0382(4) 0.0725(5) 0.0209(3) 0.0224(3) 0.0124(3)
C8 0.0287(12) 0.0373(14) 0.0367(14) 0.0069(11) 0.0087(10) -0.0065(11)
C9 0.0404(14) 0.0297(13) 0.0350(14) 0.0100(10) 0.0050(11) -0.0115(11)
C10 0.0412(14) 0.0235(11) 0.0306(13) 0.0058(10) -0.0013(10) 0.0028(10)
C11 0.0254(11) 0.0284(12) 0.0245(11) -0.0014(9) 0.0001(9) 0.0022(10)
Cl11 0.0266(3) 0.0415(4) 0.0523(4) -0.0002(3) 0.0039(3) 0.0082(3)
C12 0.0241(11) 0.0201(10) 0.0231(11) -0.0036(8) 0.0071(9) -0.0086(9)
C13 0.0263(11) 0.0238(11) 0.0284(12) -0.0004(9) 0.0036(9) -0.0005(9)
Cl13 0.0456(4) 0.0616(4) 0.0380(4) 0.0141(3) 0.0082(3) 0.0217(3)
C14 0.0288(12) 0.0258(12) 0.0363(13) -0.0021(10) 0.0141(10) -0.0001(10)
C15 0.0361(13) 0.0260(12) 0.0271(12) -0.0035(9) 0.0135(10) -0.0085(10)
C16 0.0320(12) 0.0274(12) 0.0264(12) 0.0041(9) 0.0031(10) -0.0051(10)
C17 0.0221(11) 0.0211(11) 0.0317(12) -0.0014(9) 0.0085(9) -0.0038(9)
Cl17 0.0358(3) 0.0530(4) 0.0522(4) 0.0121(3) 0.0163(3) 0.0180(3)
B21 0.0321(14) 0.0315(14) 0.0251(14) -0.0065(11) 0.0062(11) -0.0100(12)
N22 0.0271(9) 0.0251(9) 0.0230(9) -0.0072(8) 0.0039(8) -0.0043(8)
C23 0.0294(12) 0.0365(13) 0.0326(13) -0.0067(10) 0.0069(10) -0.0027(11)
C24 0.0367(14) 0.0492(17) 0.0492(16) -0.0076(13) 0.0098(12) -0.0148(13)
C25 0.0621(19) 0.0377(15) 0.0421(16) -0.0039(12) 0.0144(14) -0.0190(14)
C26 0.067(2) 0.0286(13) 0.0414(16) 0.0003(11) -0.0006(14) -0.0032(13)
C27 0.0424(14) 0.0301(13) 0.0338(13) -0.0056(10) 0.0002(11) -0.0021(11)
C28 0.0329(14) 0.0436(16) 0.071(2) -0.0019(14) 0.0010(13) 0.0044(12)

_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 N3 1.9409(17) . ?
Cu1 N1 1.9532(17) . ?
Cu1 B21 2.152(3) . ?
N1 C1 1.324(3) . ?
N1 C6 1.411(3) . ?
C1 C2 1.404(3) . ?
C1 C4 1.510(3) . ?
C2 C3 1.398(3) . ?
N3 C3 1.323(3) . ?
N3 C12 1.409(2) . ?
C3 C5 1.518(3) . ?
C6 C11 1.397(3) . ?
C6 C7 1.397(3) . ?
C7 C8 1.380(3) . ?
C7 Cl7 1.732(2) . ?
C8 C9 1.373(3) . ?
C9 C10 1.382(3) . ?
C10 C11 1.378(3) . ?
C11 Cl11 1.739(2) . ?
C12 C17 1.396(3) . ?
C12 C13 1.397(3) . ?
C13 C14 1.381(3) . ?
C13 Cl13 1.742(2) . ?
C14 C15 1.377(3) . ?
C15 C16 1.379(3) . ?
C16 C17 1.378(3) . ?
C17 Cl17 1.738(2) . ?
B21 N22 1.590(3) . ?
N22 C23 1.348(3) . ?
N22 C27 1.349(3) . ?
C23 C24 1.398(3) . ?
C23 C28 1.480(3) . ?
C24 C25 1.359(4) . ?
C25 C26 1.373(4) . ?
C26 C27 1.365(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
N3 Cu1 N1 98.58(7) . . ?
N3 Cu1 B21 136.72(9) . . ?
N1 Cu1 B21 124.69(9) . . ?
C1 N1 C6 119.04(17) . . ?
C1 N1 Cu1 121.64(14) . . ?
C6 N1 Cu1 118.69(13) . . ?
N1 C1 C2 123.45(19) . . ?
N1 C1 C4 120.29(19) . . ?
C2 C1 C4 116.24(19) . . ?
C3 C2 C1 129.9(2) . . ?
C3 N3 C12 120.02(17) . . ?
C3 N3 Cu1 121.57(14) . . ?
C12 N3 Cu1 118.01(13) . . ?
N3 C3 C2 124.09(19) . . ?
N3 C3 C5 119.50(19) . . ?
C2 C3 C5 116.41(19) . . ?
C11 C6 C7 115.48(19) . . ?
C11 C6 N1 122.07(18) . . ?
C7 C6 N1 122.32(18) . . ?
C8 C7 C6 122.5(2) . . ?
C8 C7 Cl7 119.26(17) . . ?
C6 C7 Cl7 118.21(16) . . ?
C9 C8 C7 119.8(2) . . ?
C8 C9 C10 119.9(2) . . ?
C11 C10 C9 119.4(2) . . ?
C10 C11 C6 122.8(2) . . ?
C10 C11 Cl11 119.18(17) . . ?
C6 C11 Cl11 117.97(16) . . ?
C17 C12 C13 115.31(19) . . ?
C17 C12 N3 121.80(19) . . ?
C13 C12 N3 122.74(19) . . ?
C14 C13 C12 122.9(2) . . ?
C14 C13 Cl13 118.88(17) . . ?
C12 C13 Cl13 118.19(16) . . ?
C15 C14 C13 119.4(2) . . ?
C14 C15 C16 120.0(2) . . ?
C17 C16 C15 119.5(2) . . ?
C16 C17 C12 122.9(2) . . ?
C16 C17 Cl17 118.92(17) . . ?
C12 C17 Cl17 118.20(16) . . ?
N22 B21 Cu1 116.76(16) . . ?
C23 N22 C27 119.4(2) . . ?
C23 N22 B21 121.80(19) . . ?
C27 N22 B21 118.8(2) . . ?
N22 C23 C24 119.3(2) . . ?
N22 C23 C28 118.8(2) . . ?
C24 C23 C28 121.9(2) . . ?
C25 C24 C23 120.7(3) . . ?
C24 C25 C26 119.3(3) . . ?
C27 C26 C25 118.6(3) . . ?
N22 C27 C26 122.7(2) . . ?

_refine_diff_density_max         0.283
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.059

_shelxl_version_number           2013-4

#===END


