# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_h
_database_code_depnum_ccdc_archive 'CCDC 2042523'
loop_
_audit_author_name
_audit_author_address
'Qin Hou'
;Shandong Agricultural University
China
;
_audit_update_record             
;
2020-11-05 deposited with the CCDC.	2020-12-28 downloaded from the CCDC.
;
_audit_creation_date             2019-05-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C3 H6 Br Cu N6'
_chemical_formula_sum            'C3 H6 Br Cu N6'
_chemical_formula_weight         269.59
_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'
Br Br -0.2901 2.4595 '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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.849(6)
_cell_length_b                   9.074(15)
_cell_length_c                   10.642(17)
_cell_angle_alpha                81.17(4)
_cell_angle_beta                 79.73(2)
_cell_angle_gamma                77.77(2)
_cell_volume                     354.9(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    511
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.171
_cell_measurement_theta_min      2.313
_shelx_estimated_absorpt_T_max   0.338
_shelx_estimated_absorpt_T_min   0.212
_exptl_absorpt_coefficient_mu    8.643
_exptl_absorpt_correction_T_max  0.2854
_exptl_absorpt_correction_T_min  0.1457
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellowish
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    ?
_exptl_crystal_density_diffrn    2.523
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.16
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_av_unetI/netI     0.1048
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            1723
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.092
_diffrn_reflns_theta_max         25.092
_diffrn_reflns_theta_min         1.959
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                851
_reflns_number_total             1235
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.60A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.60A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         1.148
_refine_diff_density_min         -1.143
_refine_diff_density_rms         0.239
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     102
_refine_ls_number_reflns         1235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0985
_refine_ls_R_factor_gt           0.0686
_refine_ls_restrained_S_all      0.985
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1148P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1737
_refine_ls_wR_factor_ref         0.1887
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups
2.a Rotating group:
 N4(H4A,H4B), N6(H6A,H6B)
2.b X=CH2 refined with riding coordinates:
 N5(H5A,H5B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
N4 N 0.358(3) 0.0736(13) 0.3551(10) 0.043(3) Uani 1 1 d . . . . .
H4A H 0.536145 0.011092 0.383983 0.052 Uiso 1 1 d GR . . . .
H4B H 0.245397 0.129350 0.414130 0.052 Uiso 1 1 d GR . . . .
Br1 Br 0.1387(3) 0.67989(13) 0.41167(11) 0.0303(4) Uani 1 1 d . . . . .
Cu1 Cu 0.4118(5) 0.3791(2) 0.43868(15) 0.0484(6) Uani 1 1 d . . . . .
N1 N 0.557(2) 0.2959(10) 0.2704(8) 0.027(2) Uani 1 1 d . . . . .
N6 N 0.814(3) 0.5027(10) 0.1770(10) 0.031(2) Uani 1 1 d . . . . .
H6A H 0.870209 0.551353 0.102554 0.037 Uiso 1 1 d GR . . . .
H6B H 0.635574 0.558112 0.219655 0.037 Uiso 1 1 d GR . . . .
N2 N 0.531(3) 0.1118(10) 0.1382(9) 0.033(2) Uani 1 1 d . . . . .
C1 C 0.484(3) 0.1617(12) 0.2505(11) 0.029(3) Uani 1 1 d . . . . .
C2 C 0.671(3) 0.2030(12) 0.0380(11) 0.029(3) Uani 1 1 d . . . . .
N3 N 0.769(3) 0.3356(10) 0.0454(9) 0.026(2) Uani 1 1 d . . . . .
C3 C 0.713(3) 0.3742(11) 0.1632(11) 0.025(3) Uani 1 1 d . . . . .
N5 N 0.710(3) 0.1606(11) -0.0785(10) 0.041(3) Uani 1 1 d . . . . .
H5A H 0.646285 0.077986 -0.087800 0.049 Uiso 1 1 calc R . . . .
H5B H 0.798091 0.215643 -0.144592 0.049 Uiso 1 1 calc R . . . .

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
N4 0.049(7) 0.044(6) 0.031(6) 0.008(5) 0.001(5) -0.010(5)
Br1 0.0292(7) 0.0360(7) 0.0266(7) -0.0036(5) 0.0002(5) -0.0122(5)
Cu1 0.0569(12) 0.0642(12) 0.0281(10) -0.0137(8) 0.0029(8) -0.0226(10)
N1 0.027(5) 0.037(5) 0.019(5) -0.007(4) -0.007(4) -0.005(4)
N6 0.036(6) 0.031(5) 0.026(6) -0.010(4) 0.007(5) -0.012(5)
N2 0.044(6) 0.028(5) 0.027(6) -0.005(4) 0.001(5) -0.013(5)
C1 0.035(7) 0.018(5) 0.033(7) -0.003(5) -0.005(6) -0.006(5)
C2 0.042(7) 0.030(6) 0.016(6) 0.002(5) -0.001(5) -0.012(5)
N3 0.031(5) 0.031(5) 0.019(5) -0.009(4) -0.002(4) -0.009(4)
C3 0.023(6) 0.019(5) 0.030(7) 0.010(5) -0.006(5) -0.005(5)
N5 0.066(7) 0.037(6) 0.026(6) -0.001(5) -0.002(6) -0.030(6)

_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
N4 C1 1.347(15) . ?
Br1 Cu1 2.699(5) . ?
Br1 Cu1 2.479(3) 2_666 ?
Br1 Cu1 2.516(3) 2_566 ?
Cu1 Cu1 2.967(5) 2_666 ?
Cu1 N1 1.992(10) . ?
N1 C1 1.360(13) . ?
N1 C3 1.363(13) . ?
N6 C3 1.339(13) . ?
N2 C1 1.312(15) . ?
N2 C2 1.351(14) . ?
C2 N3 1.352(13) . ?
C2 N5 1.328(15) . ?
N3 C3 1.322(15) . ?

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
Cu1 Br1 Cu1 100.83(14) 2_666 2_566 ?
Cu1 Br1 Cu1 69.76(8) 2_666 . ?
Cu1 Br1 Cu1 87.49(10) 2_566 . ?
Br1 Cu1 Br1 110.24(7) 2_666 . ?
Br1 Cu1 Br1 92.51(10) 2_566 . ?
Br1 Cu1 Br1 100.83(14) 2_666 2_566 ?
Br1 Cu1 Cu1 51.63(10) . 2_666 ?
Br1 Cu1 Cu1 101.35(12) 2_566 2_666 ?
Br1 Cu1 Cu1 58.62(9) 2_666 2_666 ?
N1 Cu1 Br1 120.7(3) . 2_566 ?
N1 Cu1 Br1 117.1(3) . 2_666 ?
N1 Cu1 Br1 112.4(3) . . ?
N1 Cu1 Cu1 136.7(3) . 2_666 ?
C1 N1 Cu1 122.8(8) . . ?
C1 N1 C3 114.4(10) . . ?
C3 N1 Cu1 122.6(7) . . ?
C1 N2 C2 115.0(9) . . ?
N4 C1 N1 116.9(11) . . ?
N2 C1 N4 118.0(10) . . ?
N2 C1 N1 125.1(10) . . ?
N2 C2 N3 125.8(10) . . ?
N5 C2 N2 117.3(10) . . ?
N5 C2 N3 116.9(9) . . ?
C3 N3 C2 114.1(9) . . ?
N6 C3 N1 117.7(10) . . ?
N3 C3 N1 125.4(9) . . ?
N3 C3 N6 116.9(9) . . ?

_shelx_res_file                  
;
TITL h in P-1
    h.res
    created by SHELXL-2018/3 at 17:05:56 on 07-May-2019
CELL 0.71073 3.8494 9.0742 10.6423 81.174 79.73 77.767
ZERR 2 0.0058 0.0147 0.0168 0.039 0.023 0.022
LATT 1
SFAC C H Br Cu N
UNIT 6 12 2 2 12

L.S. 4
PLAN  20
SIZE 0.26 0.21 0.16
TEMP 23
BOND
fmap 2
acta
SHEL 999 0.83
OMIT -3 50.2
OMIT 0 1 1
OMIT 0 1 0
OMIT 1 7 6
REM <olex2.extras>
REM <HklSrc "%.\\h.hkl">
REM </olex2.extras>

WGHT    0.114800
FVAR       0.28546
N4    5    0.357634    0.073639    0.355081    11.00000    0.04943    0.04360 =
         0.03084    0.00754    0.00058   -0.00980
AFIX   7
H4A   2    0.536145    0.011092    0.383983    11.00000   -1.20000
H4B   2    0.245397    0.129350    0.414130    11.00000   -1.20000
AFIX   0
BR1   3    0.138700    0.679891    0.411675    11.00000    0.02922    0.03602 =
         0.02662   -0.00360    0.00022   -0.01219
CU1   4    0.411779    0.379139    0.438680    11.00000    0.05692    0.06417 =
         0.02811   -0.01366    0.00290   -0.02260
N1    5    0.557239    0.295879    0.270432    11.00000    0.02687    0.03710 =
         0.01865   -0.00702   -0.00727   -0.00520
N6    5    0.813613    0.502662    0.176984    11.00000    0.03635    0.03098 =
         0.02595   -0.00965    0.00744   -0.01180
AFIX   7
H6A   2    0.870209    0.551353    0.102554    11.00000   -1.20000
H6B   2    0.635574    0.558112    0.219655    11.00000   -1.20000
AFIX   0
N2    5    0.530606    0.111831    0.138188    11.00000    0.04402    0.02836 =
         0.02667   -0.00510    0.00073   -0.01339
C1    1    0.484395    0.161698    0.250540    11.00000    0.03518    0.01802 =
         0.03311   -0.00253   -0.00460   -0.00562
C2    1    0.671024    0.202965    0.037989    11.00000    0.04214    0.02950 =
         0.01578    0.00193   -0.00134   -0.01155
N3    5    0.769001    0.335552    0.045382    11.00000    0.03137    0.03087 =
         0.01857   -0.00910   -0.00163   -0.00908
C3    1    0.713420    0.374229    0.163159    11.00000    0.02296    0.01948 =
         0.03008    0.01000   -0.00628   -0.00548
N5    5    0.709672    0.160551   -0.078478    11.00000    0.06580    0.03702 =
         0.02624   -0.00122   -0.00166   -0.02958
AFIX  93
H5A   2    0.646285    0.077986   -0.087800    11.00000   -1.20000
H5B   2    0.798091    0.215643   -0.144592    11.00000   -1.20000
AFIX   0
HKLF 4




REM  h in P-1
REM wR2 = 0.1887, GooF = S = 0.985, Restrained GooF = 0.985 for all data
REM R1 = 0.0686 for 851 Fo > 4sig(Fo) and 0.0985 for all 1235 data
REM 102 parameters refined using 0 restraints

END

WGHT      0.1148      0.0000

REM Highest difference peak  1.148,  deepest hole -1.143,  1-sigma level  0.239
Q1    1   0.3552  0.5341  0.4053  11.00000  0.05    1.15
Q2    1   0.2261  0.5742  0.4421  11.00000  0.05    1.12
Q3    1   0.5076  0.3994  0.5576  11.00000  0.05    1.10
Q4    1  -0.1023  0.5872  0.3449  11.00000  0.05    0.96
Q5    1   0.6089  0.2662  0.4412  11.00000  0.05    0.94
Q6    1   0.0632  0.7554  0.3365  11.00000  0.05    0.86
Q7    1   0.7806 -0.0215  0.0356  11.00000  0.05    0.82
Q8    1   0.1953  0.0741  0.1537  11.00000  0.05    0.79
Q9    1  -0.2178  0.7645  0.3820  11.00000  0.05    0.75
Q10   1  -0.0119  0.6533  0.2810  11.00000  0.05    0.71
Q11   1   0.0703  0.0028  0.2469  11.00000  0.05    0.71
Q12   1   0.7159  0.2085  0.2979  11.00000  0.05    0.71
Q13   1   0.2533  0.3571  0.2987  11.00000  0.05    0.67
Q14   1   0.4251 -0.0799  0.5033  11.00000  0.05    0.66
Q15   1   0.8030  0.5217  0.2609  11.00000  0.05    0.65
Q16   1   0.0267  0.1934  0.2998  11.00000  0.05    0.64
Q17   1   0.9562 -0.0995  0.3988  11.00000  0.05    0.61
Q18   1   0.5948  0.6080  0.3311  11.00000  0.05    0.61
Q19   1   0.0492 -0.0196  0.3588  11.00000  0.05    0.60
Q20   1   0.3368 -0.0867  0.3936  11.00000  0.05    0.59
;
_shelx_res_checksum              40718
_olex2_submission_special_instructions 'No special instructions were received'
