# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_twin5
_database_code_depnum_ccdc_archive 'CCDC 2032012'
loop_
_audit_author_name
_audit_author_address
'Simon J. Teat'
;Advanced Light Source, Lawrence Berkeley National Laboratory
United States of America
;
_audit_update_record             
;
2020-09-14 deposited with the CCDC.	2020-10-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H23 Br3 Cu2 N4'
_chemical_formula_weight         614.17

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0034 0.0017
'XDISP Program in WinGX S.Brennan & P.L.Cowan Rev.Sci.Instrum.63,850 1992'
H H 0.0000 0.0000
'XDISP Program in WinGX S.Brennan & P.L.Cowan Rev.Sci.Instrum.63,850 1992'
N N 0.0065 0.0035
'XDISP Program in WinGX S.Brennan & P.L.Cowan Rev.Sci.Instrum.63,850 1992'
Cu Cu 0.3203 1.3289
'XDISP Program in WinGX S.Brennan & P.L.Cowan Rev.Sci.Instrum.63,850 1992'
Br Br -0.4677 2.5495
'XDISP Program in WinGX S.Brennan & P.L.Cowan Rev.Sci.Instrum.63,850 1992'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   8.9746(3)
_cell_length_b                   10.9880(4)
_cell_length_c                   11.0013(4)
_cell_angle_alpha                94.159(2)
_cell_angle_beta                 109.7270(10)
_cell_angle_gamma                106.2770(10)
_cell_volume                     963.35(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9649
_cell_measurement_theta_min      3.0342
_cell_measurement_theta_max      29.1018

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.117
_exptl_crystal_F_000             596
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    8.972
_shelx_estimated_absorpt_T_min   0.534
_shelx_estimated_absorpt_T_max   0.775
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.550
_exptl_absorpt_correction_T_max  0.775
_exptl_absorpt_process_details   'TWINABS 2012/1 Bruker AXS Madison WI USA'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.7288
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source beamline 12.2.1'
_diffrn_measurement_device_type  'Bruker D8 with PHOTONII detector'
_diffrn_measurement_method       'ω/θ shutterless scans'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            57103
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.015
_diffrn_reflns_theta_max         29.114
_diffrn_reflns_theta_full        25.930
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             4764
_reflns_number_gt                4579
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'Bruker APEX 3'
_computing_cell_refinement       'Bruker SAINT v8.38a'
_computing_data_reduction        'Bruker SAINT v8.38a'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL & local programs'
_refine_special_details          
;
 Several crystals were tried and this was the best crystal. The diffraction
 pattern showed twinning. Using Cell_now two orientation matrices were
 determined, the relationship between these components was determined to be
 180 degrees about reciprocal axis 0 1 -1.  The data were integrated using the
 two matrices in SAINT, TWINABS was used to produce a merged HKLF4 file,
 for structure solution and initial refinement, and HKLF5 file for final
 structure refinement. The HKLF5 file contained the merged reflections first
 component and those that overlapped with this component, which were split
 into 2 reflection. TWINABS indicated the twin faction to be 78:22 The structure
 was solved using the HKLF4 file, but the best refinement was given by the
 HKLF5 file.  

 All non-hydrogen atoms were refined anisotropically. Hydrogen
 atoms were found in the rotational fourier map for the
 methyl groups, the rest were placed geometrically
 constrained and refined using a riding model. 

 Refined as a 2-component twin.

;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0317P)²+0.3169P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'Dual space'
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4764
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0213
_refine_ls_R_factor_gt           0.0203
_refine_ls_wR_factor_ref         0.0540
_refine_ls_wR_factor_gt          0.0535
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.002
_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 0.89410(3) 0.88854(2) 0.39185(2) 0.01588(6) Uani 1 1 d . . . . .
Cu2 Cu 0.61826(3) 0.62789(2) 0.12385(2) 0.01458(6) Uani 1 1 d . . . . .
Br1 Br 0.79339(2) 1.03119(2) 0.50493(2) 0.01665(6) Uani 1 1 d . . . . .
Br2 Br 0.30970(2) 0.51328(2) 0.02352(2) 0.01261(5) Uani 1 1 d . . . . .
Br3 Br 0.75933(2) 0.85917(2) 0.14644(2) 0.01242(5) Uani 1 1 d . . . . .
N1 N 0.82279(19) 0.70100(15) 0.41330(16) 0.0138(3) Uani 1 1 d . . . . .
N2 N 0.71151(19) 0.60691(15) 0.31774(16) 0.0134(3) Uani 1 1 d . . . . .
N3 N 0.69638(19) 0.49460(15) 0.36166(16) 0.0133(3) Uani 1 1 d . . . . .
C1 C 0.8817(2) 0.64862(18) 0.52168(18) 0.0129(3) Uani 1 1 d . . . . .
C2 C 1.0056(2) 0.70649(19) 0.64720(19) 0.0156(4) Uani 1 1 d . . . . .
H2A H 1.061202 0.796990 0.671156 0.019 Uiso 1 1 calc R U . . .
C3 C 1.0408(2) 0.6248(2) 0.73233(19) 0.0178(4) Uani 1 1 d . . . . .
H3A H 1.124250 0.660034 0.817702 0.021 Uiso 1 1 calc R U . . .
C4 C 0.9582(2) 0.4893(2) 0.6987(2) 0.0187(4) Uani 1 1 d . . . . .
H4A H 0.987249 0.437100 0.762110 0.022 Uiso 1 1 calc R U . . .
C5 C 0.8370(2) 0.43197(19) 0.57642(19) 0.0171(4) Uani 1 1 d . . . . .
H5A H 0.781555 0.341431 0.552793 0.021 Uiso 1 1 calc R U . . .
C6 C 0.8009(2) 0.51545(18) 0.48941(18) 0.0130(3) Uani 1 1 d . . . . .
C7 C 0.5745(2) 0.37286(17) 0.28086(18) 0.0134(3) Uani 1 1 d . . . . .
H7A H 0.627548 0.304483 0.291142 0.016 Uiso 1 1 calc R U . . .
H7B H 0.538296 0.381521 0.187285 0.016 Uiso 1 1 calc R U . . .
C8 C 0.4224(2) 0.33399(19) 0.3196(2) 0.0159(4) Uani 1 1 d . . . . .
H8A H 0.372649 0.404217 0.313691 0.019 Uiso 1 1 calc R U . . .
H8B H 0.457659 0.320749 0.411784 0.019 Uiso 1 1 calc R U . . .
C9 C 0.2916(2) 0.21005(18) 0.2299(2) 0.0165(4) Uani 1 1 d . . . . .
H9A H 0.196081 0.186189 0.259207 0.020 Uiso 1 1 calc R U . . .
H9B H 0.249237 0.226834 0.139387 0.020 Uiso 1 1 calc R U . . .
C10 C 0.3572(2) 0.09647(18) 0.22747(19) 0.0144(3) Uani 1 1 d . . . . .
H10A H 0.436770 0.110886 0.181621 0.017 Uiso 1 1 calc R U . . .
H10B H 0.416181 0.086506 0.318210 0.017 Uiso 1 1 calc R U . . .
C11 C 0.2083(2) -0.02315(17) 0.15566(19) 0.0132(3) Uani 1 1 d . . . . .
H11A H 0.142466 -0.005518 0.070578 0.016 Uiso 1 1 calc R U . . .
H11B H 0.136242 -0.039396 0.207799 0.016 Uiso 1 1 calc R U . . .
N4 N 0.24900(17) -0.14472(14) 0.12911(15) 0.0115(3) Uani 1 1 d . . . . .
C12 C 0.3541(2) -0.1749(2) 0.2539(2) 0.0183(4) Uani 1 1 d . . . . .
H12A H 0.364588 -0.260087 0.235768 0.027 Uiso 1 1 calc R U . . .
H12B H 0.300962 -0.174630 0.318388 0.027 Uiso 1 1 calc R U . . .
H12C H 0.465499 -0.109540 0.288964 0.027 Uiso 1 1 calc R U . . .
C13 C 0.0856(2) -0.25285(18) 0.0680(2) 0.0174(4) Uani 1 1 d . . . . .
H13A H 0.107161 -0.334244 0.053413 0.026 Uiso 1 1 calc R U . . .
H13B H 0.019156 -0.236107 -0.016128 0.026 Uiso 1 1 calc R U . . .
H13C H 0.023879 -0.258747 0.127010 0.026 Uiso 1 1 calc R U . . .
C14 C 0.3388(2) -0.13216(19) 0.0360(2) 0.0155(4) Uani 1 1 d . . . . .
H14A H 0.352192 -0.215054 0.012156 0.023 Uiso 1 1 calc R U . . .
H14B H 0.449272 -0.066259 0.078077 0.023 Uiso 1 1 calc R U . . .
H14C H 0.273926 -0.106943 -0.043374 0.023 Uiso 1 1 calc R U . . .


_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 2.0360(16) . ?
Cu1 Br1 2.4680(3) . ?
Cu1 Br1 2.5003(3) 2_776 ?
Cu1 Br3 2.5113(3) . ?
Cu1 Cu1 2.9608(5) 2_776 ?
Cu2 N2 2.0683(17) . ?
Cu2 Br3 2.4526(3) . ?
Cu2 Br2 2.5005(3) . ?
Cu2 Br2 2.5214(3) 2_665 ?
N1 N2 1.314(2) . ?
N1 C1 1.370(2) . ?
N2 N3 1.346(2) . ?
N3 C6 1.360(2) . ?
N3 C7 1.458(2) . ?
C1 C6 1.396(3) . ?
C1 C2 1.410(3) . ?
C2 C3 1.365(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.421(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.377(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.396(3) . ?
C5 H5A 0.9500 . ?
C7 C8 1.523(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.528(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.524(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.513(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 N4 1.514(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
N4 C14 1.495(2) . ?
N4 C12 1.500(2) . ?
N4 C13 1.502(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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
N1 Cu1 Br1 114.69(5) . . ?
N1 Cu1 Br1 105.84(4) . 2_776 ?
Br1 Cu1 Br1 106.846(10) . 2_776 ?
N1 Cu1 Br3 99.45(5) . . ?
Br1 Cu1 Br3 111.798(11) . . ?
Br1 Cu1 Br3 118.242(12) 2_776 . ?
N1 Cu1 Cu1 125.37(5) . 2_776 ?
Br1 Cu1 Cu1 53.925(9) . 2_776 ?
Br1 Cu1 Cu1 52.921(8) 2_776 2_776 ?
Br3 Cu1 Cu1 135.165(15) . 2_776 ?
N2 Cu2 Br3 100.00(5) . . ?
N2 Cu2 Br2 110.17(4) . . ?
Br3 Cu2 Br2 126.306(11) . . ?
N2 Cu2 Br2 111.94(5) . 2_665 ?
Br3 Cu2 Br2 113.554(11) . 2_665 ?
Br2 Cu2 Br2 95.184(10) . 2_665 ?
Cu1 Br1 Cu1 73.154(10) . 2_776 ?
Cu2 Br2 Cu2 84.816(10) . 2_665 ?
Cu2 Br3 Cu1 92.677(10) . . ?
N2 N1 C1 108.10(16) . . ?
N2 N1 Cu1 123.39(13) . . ?
C1 N1 Cu1 128.46(12) . . ?
N1 N2 N3 108.99(15) . . ?
N1 N2 Cu2 123.59(13) . . ?
N3 N2 Cu2 126.16(12) . . ?
N2 N3 C6 110.17(15) . . ?
N2 N3 C7 122.19(15) . . ?
C6 N3 C7 127.52(16) . . ?
N1 C1 C6 108.35(16) . . ?
N1 C1 C2 130.81(18) . . ?
C6 C1 C2 120.80(18) . . ?
C3 C2 C1 116.05(18) . . ?
C3 C2 H2A 122.0 . . ?
C1 C2 H2A 122.0 . . ?
C2 C3 C4 122.83(18) . . ?
C2 C3 H3A 118.6 . . ?
C4 C3 H3A 118.6 . . ?
C5 C4 C3 121.52(18) . . ?
C5 C4 H4A 119.2 . . ?
C3 C4 H4A 119.2 . . ?
C4 C5 C6 115.67(18) . . ?
C4 C5 H5A 122.2 . . ?
C6 C5 H5A 122.2 . . ?
N3 C6 C5 132.42(18) . . ?
N3 C6 C1 104.38(16) . . ?
C5 C6 C1 123.13(17) . . ?
N3 C7 C8 111.22(15) . . ?
N3 C7 H7A 109.4 . . ?
C8 C7 H7A 109.4 . . ?
N3 C7 H7B 109.4 . . ?
C8 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C7 C8 C9 110.84(16) . . ?
C7 C8 H8A 109.5 . . ?
C9 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
C10 C9 C8 113.85(15) . . ?
C10 C9 H9A 108.8 . . ?
C8 C9 H9A 108.8 . . ?
C10 C9 H9B 108.8 . . ?
C8 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
C11 C10 C9 107.52(14) . . ?
C11 C10 H10A 110.2 . . ?
C9 C10 H10A 110.2 . . ?
C11 C10 H10B 110.2 . . ?
C9 C10 H10B 110.2 . . ?
H10A C10 H10B 108.5 . . ?
C10 C11 N4 115.72(14) . . ?
C10 C11 H11A 108.4 . . ?
N4 C11 H11A 108.4 . . ?
C10 C11 H11B 108.4 . . ?
N4 C11 H11B 108.4 . . ?
H11A C11 H11B 107.4 . . ?
C14 N4 C12 109.23(14) . . ?
C14 N4 C13 109.21(15) . . ?
C12 N4 C13 109.14(15) . . ?
C14 N4 C11 110.87(14) . . ?
C12 N4 C11 111.24(15) . . ?
C13 N4 C11 107.10(13) . . ?
N4 C12 H12A 109.5 . . ?
N4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N4 C13 H13A 109.5 . . ?
N4 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N4 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N4 C14 H14A 109.5 . . ?
N4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_refine_diff_density_max         0.648
_refine_diff_density_min         -0.543
_refine_diff_density_rms         0.126

