# 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_2010src1025
_database_code_depnum_ccdc_archive 'CCDC 1029551'
_audit_update_record             
;
2014-10-16 deposited with the CCDC.
2015-02-13 downloaded from the CCDC.
;
_audit_creation_date             2014-10-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'Cl3 Cu, C13 H30 N'
_chemical_formula_sum            'C13 H30 Cl3 Cu N'
_chemical_formula_weight         370.27
_chemical_melting_point          ?
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'
N N 0.0061 0.0033 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.2771(4)
_cell_length_b                   15.6784(5)
_cell_length_c                   12.5521(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.016(2)
_cell_angle_gamma                90.00
_cell_volume                     1797.88(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_exptl_absorpt_coefficient_mu    1.647
_exptl_absorpt_correction_T_max  0.781
_exptl_absorpt_correction_T_min  0.547
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            'clear dark orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             780
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            21158
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.99
_diffrn_ambient_temperature      120.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3459
_reflns_number_total             4122
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.815
_refine_diff_density_rms         0.110
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         4122
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0377
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0475P)²+0.7265P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0898
_refine_ls_wR_factor_ref         0.0951
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C9(H9A,H9B), C10(H10A,H10B), C5(H5A,H5B), C6(H6A,H6B), C2(H2A,
 H2B), C11(H11A,H11B), C7(H7A,H7B), C3(H3A,H3B)
2.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C4(H4A,H4B,H4C), C13(H13A,H13B,H13C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Cu1 Cu 0.55533(3) 0.094988(17) 0.96323(2) 0.02338(10) Uani 1 d . . .
Cl1 Cl 0.76034(6) 0.12566(4) 0.90568(5) 0.02860(14) Uani 1 d . . .
Cl2 Cl 0.44849(7) 0.21984(4) 0.95138(5) 0.03394(15) Uani 1 d . . .
Cl3 Cl 0.35339(6) 0.00732(4) 0.91017(5) 0.02770(14) Uani 1 d . . .
N1 N 0.09467(19) 0.13464(12) 1.18099(15) 0.0215(4) Uani 1 d . . .
C1 C -0.0346(2) 0.19457(14) 1.17953(19) 0.0243(5) Uani 1 d . . .
H1A H -0.1181 0.1728 1.1266 0.029 Uiso 1 calc . . R
H1B H -0.0638 0.1934 1.2517 0.029 Uiso 1 calc . . R
C12 C 0.1637(3) -0.09470(15) 1.3886(2) 0.0346(6) Uani 1 d . . .
H12A H 0.2078 -0.0957 1.3231 0.052 Uiso 1 calc . . GR
H12B H 0.1542 -0.1532 1.4141 0.052 Uiso 1 calc . . GR
H12C H 0.2262 -0.0618 1.4450 0.052 Uiso 1 calc . . GR
C9 C 0.0519(2) 0.04677(14) 1.21573(19) 0.0244(5) Uani 1 d . . .
H9A H -0.0343 0.0271 1.1636 0.029 Uiso 1 calc . . R
H9B H 0.1333 0.0070 1.2107 0.029 Uiso 1 calc . . R
C10 C 0.0157(3) 0.04050(15) 1.3287(2) 0.0322(6) Uani 1 d . . .
H10A H -0.0809 0.0669 1.3300 0.039 Uiso 1 calc . . R
H10B H 0.0901 0.0719 1.3802 0.039 Uiso 1 calc . . R
C5 C 0.2272(2) 0.17012(15) 1.2563(2) 0.0267(5) Uani 1 d . . .
H5A H 0.2575 0.2236 1.2247 0.032 Uiso 1 calc . . R
H5B H 0.1976 0.1848 1.3261 0.032 Uiso 1 calc . . R
C6 C 0.3581(3) 0.11106(16) 1.2784(3) 0.0378(6) Uani 1 d . . .
H6A H 0.3822 0.0904 1.2091 0.045 Uiso 1 calc . . R
H6B H 0.3342 0.0610 1.3202 0.045 Uiso 1 calc . . R
C4 C -0.1169(3) 0.43184(16) 1.1175(2) 0.0355(6) Uani 1 d . . .
H4A H -0.0747 0.4375 1.0515 0.053 Uiso 1 calc . . GR
H4B H -0.0482 0.4545 1.1791 0.053 Uiso 1 calc . . GR
H4C H -0.2089 0.4639 1.1092 0.053 Uiso 1 calc . . GR
C2 C -0.0062(2) 0.28647(15) 1.1512(2) 0.0274(5) Uani 1 d . . .
H2A H 0.0667 0.3119 1.2095 0.033 Uiso 1 calc . . R
H2B H 0.0347 0.2881 1.0835 0.033 Uiso 1 calc . . R
C13 C 0.1287(3) 0.12538(17) 1.0687(2) 0.0305(5) Uani 1 d . . .
H13A H 0.0387 0.1115 1.0182 0.046 Uiso 1 calc . . GR
H13B H 0.2003 0.0795 1.0679 0.046 Uiso 1 calc . . GR
H13C H 0.1691 0.1790 1.0468 0.046 Uiso 1 calc . . GR
C11 C 0.0129(3) -0.05347(15) 1.3633(2) 0.0332(6) Uani 1 d . . .
H11A H -0.0341 -0.0573 1.4282 0.040 Uiso 1 calc . . R
H11B H -0.0482 -0.0861 1.3047 0.040 Uiso 1 calc . . R
C7 C 0.4905(3) 0.15790(17) 1.3425(2) 0.0368(6) Uani 1 d . . .
H7A H 0.4592 0.1877 1.4041 0.044 Uiso 1 calc . . R
H7B H 0.5650 0.1151 1.3727 0.044 Uiso 1 calc . . R
C3 C -0.1466(3) 0.33800(15) 1.1370(2) 0.0318(5) Uani 1 d . . .
H3A H -0.1916 0.3324 1.2027 0.038 Uiso 1 calc . . R
H3B H -0.2166 0.3152 1.0749 0.038 Uiso 1 calc . . R
C8 C 0.5597(3) 0.2210(2) 1.2788(3) 0.0584(9) Uani 1 d . . .
H8A H 0.5866 0.1929 1.2154 0.088 Uiso 1 calc . . GR
H8B H 0.6476 0.2444 1.3239 0.088 Uiso 1 calc . . GR
H8C H 0.4904 0.2672 1.2552 0.088 Uiso 1 calc . . GR

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 0.01820(15) 0.02624(17) 0.02642(17) 0.00037(10) 0.00587(11) 0.00111(10)
Cl1 0.0207(3) 0.0349(3) 0.0314(3) 0.0009(2) 0.0079(2) -0.0021(2)
Cl2 0.0344(3) 0.0308(3) 0.0389(3) 0.0030(2) 0.0128(3) 0.0089(3)
Cl3 0.0193(3) 0.0336(3) 0.0291(3) 0.0044(2) 0.0010(2) -0.0012(2)
N1 0.0156(8) 0.0249(9) 0.0241(10) -0.0012(7) 0.0033(7) -0.0006(7)
C1 0.0167(10) 0.0278(12) 0.0295(12) -0.0025(9) 0.0067(9) 0.0009(9)
C12 0.0357(14) 0.0298(13) 0.0384(15) 0.0038(10) 0.0066(11) -0.0042(11)
C9 0.0196(10) 0.0208(11) 0.0339(13) -0.0045(9) 0.0073(9) -0.0016(9)
C10 0.0342(13) 0.0246(12) 0.0423(15) -0.0016(10) 0.0188(11) -0.0033(10)
C5 0.0197(11) 0.0276(12) 0.0311(12) 0.0017(9) -0.0002(9) -0.0055(9)
C6 0.0222(12) 0.0280(13) 0.0585(18) 0.0036(12) -0.0064(12) -0.0026(10)
C4 0.0291(13) 0.0323(13) 0.0469(16) 0.0083(12) 0.0116(11) 0.0058(11)
C2 0.0211(11) 0.0306(12) 0.0307(13) 0.0048(10) 0.0053(9) 0.0019(9)
C13 0.0241(12) 0.0424(14) 0.0269(13) -0.0009(10) 0.0094(9) 0.0052(11)
C11 0.0331(13) 0.0255(12) 0.0450(15) 0.0005(11) 0.0182(11) -0.0048(11)
C7 0.0240(12) 0.0359(14) 0.0457(16) 0.0082(12) -0.0075(11) -0.0035(11)
C3 0.0234(12) 0.0323(13) 0.0395(15) 0.0041(11) 0.0049(10) 0.0028(10)
C8 0.0334(15) 0.081(2) 0.056(2) 0.0220(17) -0.0054(14) -0.0267(16)

_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 2.2019(6) . ?
Cu1 Cl2 2.1874(6) . ?
Cu1 Cl3 2.3123(6) 3_657 ?
Cu1 Cl3 2.3256(6) . ?
Cl3 Cu1 2.3123(6) 3_657 ?
N1 C1 1.521(3) . ?
N1 C9 1.518(3) . ?
N1 C5 1.520(3) . ?
N1 C13 1.504(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.518(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C12 C11 1.524(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.517(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.537(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.514(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.533(3) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C4 C3 1.525(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.517(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.485(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?

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 Cl3 98.22(2) . 3_657 ?
Cl1 Cu1 Cl3 137.21(2) . . ?
Cl2 Cu1 Cl1 100.91(3) . . ?
Cl2 Cu1 Cl3 140.80(3) . 3_657 ?
Cl2 Cu1 Cl3 100.17(2) . . ?
Cl3 Cu1 Cl3 88.13(2) 3_657 . ?
Cu1 Cl3 Cu1 91.87(2) 3_657 . ?
C9 N1 C1 108.61(16) . . ?
C9 N1 C5 112.14(17) . . ?
C5 N1 C1 109.40(17) . . ?
C13 N1 C1 109.98(17) . . ?
C13 N1 C9 106.83(17) . . ?
C13 N1 C5 109.85(17) . . ?
N1 C1 H1A 108.6 . . ?
N1 C1 H1B 108.6 . . ?
H1A C1 H1B 107.5 . . ?
C2 C1 N1 114.86(18) . . ?
C2 C1 H1A 108.6 . . ?
C2 C1 H1B 108.6 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
N1 C9 H9A 108.3 . . ?
N1 C9 H9B 108.3 . . ?
H9A C9 H9B 107.4 . . ?
C10 C9 N1 116.03(18) . . ?
C10 C9 H9A 108.3 . . ?
C10 C9 H9B 108.3 . . ?
C9 C10 H10A 109.6 . . ?
C9 C10 H10B 109.6 . . ?
C9 C10 C11 110.1(2) . . ?
H10A C10 H10B 108.2 . . ?
C11 C10 H10A 109.6 . . ?
C11 C10 H10B 109.6 . . ?
N1 C5 H5A 108.5 . . ?
N1 C5 H5B 108.5 . . ?
H5A C5 H5B 107.5 . . ?
C6 C5 N1 115.3(2) . . ?
C6 C5 H5A 108.5 . . ?
C6 C5 H5B 108.5 . . ?
C5 C6 H6A 109.6 . . ?
C5 C6 H6B 109.6 . . ?
C5 C6 C7 110.3(2) . . ?
H6A C6 H6B 108.1 . . ?
C7 C6 H6A 109.6 . . ?
C7 C6 H6B 109.6 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
C3 C2 C1 110.63(19) . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
N1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C11 C10 113.9(2) . . ?
C12 C11 H11A 108.8 . . ?
C12 C11 H11B 108.8 . . ?
C10 C11 H11A 108.8 . . ?
C10 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C6 C7 H7A 108.6 . . ?
C6 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
C8 C7 C6 114.7(2) . . ?
C8 C7 H7A 108.6 . . ?
C8 C7 H7B 108.6 . . ?
C4 C3 H3A 109.4 . . ?
C4 C3 H3B 109.4 . . ?
C2 C3 C4 111.0(2) . . ?
C2 C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: water'
