# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_170814hq5
_database_code_depnum_ccdc_archive 'CCDC 1986480'
loop_
_audit_author_name
_audit_author_address
'Qin Hou'
;Shandong Agricultural University
China
;
_audit_update_record             
;
2020-07-10 deposited with the CCDC.	2020-08-04 downloaded from the CCDC.
;
_audit_creation_date             2020-07-05
_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         'C6 H12 Cu2 I2 N12'
_chemical_formula_sum            'C6 H12 Cu2 I2 N12'
_chemical_formula_weight         633.16
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N Br Cu'
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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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                   4.0787(3)
_cell_length_b                   9.0943(6)
_cell_length_c                   10.9148(7)
_cell_angle_alpha                82.327(6)
_cell_angle_beta                 80.162(6)
_cell_angle_gamma                77.648(6)
_cell_volume                     387.69(5)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2062
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.9230
_cell_measurement_theta_min      3.8020
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.740
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51110
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.712
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       columnar
_exptl_crystal_F_000             296
_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  0.0332
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2914
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.347
_diffrn_reflns_theta_min         3.134
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9737
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -3.00  88.00   1.00    1.00    --   18.81  57.00 150.00   91
  2  ω    -13.00  90.00   1.00    1.00    --   18.81  77.00-120.00  103
  3  ω    -13.00  90.00   1.00    1.00    --   18.81  77.00  30.00  103
  4  ω    -50.00  40.00   1.00    1.00    --   18.81 -57.00 -90.00   90
  5  ω    -50.00   6.00   1.00    1.00    --   18.81 -57.00   0.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1532167000
_diffrn_orient_matrix_UB_12      -0.0037923000
_diffrn_orient_matrix_UB_13      -0.0208063000
_diffrn_orient_matrix_UB_21      -0.0534437000
_diffrn_orient_matrix_UB_22      -0.0385856000
_diffrn_orient_matrix_UB_23      0.0584519000
_diffrn_orient_matrix_UB_31      -0.0778503000
_diffrn_orient_matrix_UB_32      0.0702630000
_diffrn_orient_matrix_UB_33      0.0233479000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1259
_reflns_number_total             1390
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.543
_refine_diff_density_min         -0.657
_refine_diff_density_rms         0.122
_refine_ls_extinction_coef       0.0042(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     103
_refine_ls_number_reflns         1390
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0259
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0120P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0492
_refine_ls_wR_factor_ref         0.0521
_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), N5(H5A,H5B)
2.b X=CH2 refined with riding coordinates:
 N6(H6A,H6B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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
I1 I 0.12779(7) 0.69117(3) 0.41383(3) 0.02628(15) Uani 1 1 d . . . . .
Cu1 Cu 0.57492(16) 0.60688(7) 0.57099(6) 0.0390(2) Uani 1 1 d . . . . .
N1 N 0.4282(9) 0.6968(4) 0.7356(4) 0.0260(9) Uani 1 1 d . . . . .
N6 N 0.1812(10) 0.4956(4) 0.8268(4) 0.0365(11) Uani 1 1 d . . . . .
H6A H 0.085803 0.446042 0.890726 0.044 Uiso 1 1 calc R . . . .
H6B H 0.213018 0.463328 0.754327 0.044 Uiso 1 1 calc R . . . .
N3 N 0.2240(10) 0.6674(4) 0.9547(4) 0.0282(9) Uani 1 1 d . . . . .
N2 N 0.4590(10) 0.8837(4) 0.8664(4) 0.0335(10) Uani 1 1 d . . . . .
N4 N 0.6060(12) 0.9197(5) 0.6536(4) 0.0484(12) Uani 1 1 d . . . . .
H4A H 0.737725 0.975067 0.674816 0.058 Uiso 1 1 d GR . . . .
H4B H 0.733422 0.868918 0.592316 0.058 Uiso 1 1 d GR . . . .
N5 N 0.3000(12) 0.8404(5) 1.0765(4) 0.0520(13) Uani 1 1 d . . . . .
H5A H 0.302280 0.936404 1.068677 0.062 Uiso 1 1 d GR . . . .
H5B H 0.112019 0.824784 1.122757 0.062 Uiso 1 1 d GR . . . .
C2 C 0.2799(11) 0.6229(5) 0.8401(5) 0.0252(11) Uani 1 1 d . . . . .
C3 C 0.3263(12) 0.7973(5) 0.9619(5) 0.0299(11) Uani 1 1 d . . . . .
C1 C 0.4987(12) 0.8314(5) 0.7563(5) 0.0294(11) Uani 1 1 d . . . . .

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
I1 0.0290(2) 0.0272(2) 0.0239(2) -0.00225(13) 0.00003(14) -0.01163(13)
Cu1 0.0502(4) 0.0418(4) 0.0261(4) -0.0092(3) -0.0009(3) -0.0115(3)
N1 0.034(2) 0.024(2) 0.022(2) -0.0070(17) 0.0013(18) -0.0099(17)
N6 0.056(3) 0.036(2) 0.023(3) -0.010(2) 0.005(2) -0.026(2)
N3 0.043(2) 0.025(2) 0.019(2) -0.0041(18) 0.0000(19) -0.0139(18)
N2 0.051(3) 0.026(2) 0.025(3) -0.0063(19) 0.004(2) -0.0158(19)
N4 0.079(3) 0.035(3) 0.030(3) -0.006(2) 0.016(3) -0.026(2)
N5 0.089(4) 0.044(3) 0.029(3) -0.013(2) 0.012(3) -0.036(3)
C2 0.029(3) 0.024(3) 0.023(3) -0.003(2) -0.004(2) -0.006(2)
C3 0.048(3) 0.022(3) 0.022(3) -0.007(2) -0.001(2) -0.012(2)
C1 0.037(3) 0.021(2) 0.029(3) -0.002(2) -0.001(2) -0.006(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
I1 Cu1 2.6412(7) . ?
I1 Cu1 2.7716(8) 1_455 ?
I1 Cu1 2.7180(7) 2_666 ?
Cu1 Cu1 2.8619(12) 2_666 ?
Cu1 N1 2.018(4) . ?
N1 C2 1.361(6) . ?
N1 C1 1.370(6) . ?
N6 H6A 0.8600 . ?
N6 H6B 0.8600 . ?
N6 C2 1.337(5) . ?
N3 C2 1.333(6) . ?
N3 C3 1.350(5) . ?
N2 C3 1.329(6) . ?
N2 C1 1.322(6) . ?
N4 H4A 0.8862 . ?
N4 H4B 0.8900 . ?
N4 C1 1.354(6) . ?
N5 H5A 0.8681 . ?
N5 H5B 0.8703 . ?
N5 C3 1.340(6) . ?

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 I1 Cu1 64.54(2) . 2_666 ?
Cu1 I1 Cu1 97.77(2) . 1_455 ?
Cu1 I1 Cu1 87.03(2) 2_666 1_455 ?
I1 Cu1 I1 92.97(2) 2_666 1_655 ?
I1 Cu1 I1 115.46(2) . 2_666 ?
I1 Cu1 I1 97.77(2) . 1_655 ?
I1 Cu1 Cu1 59.03(2) . 2_666 ?
I1 Cu1 Cu1 100.01(3) 1_655 2_666 ?
I1 Cu1 Cu1 56.43(2) 2_666 2_666 ?
N1 Cu1 I1 118.21(11) . 1_655 ?
N1 Cu1 I1 115.52(11) . 2_666 ?
N1 Cu1 I1 114.02(11) . . ?
N1 Cu1 Cu1 141.71(11) . 2_666 ?
C2 N1 Cu1 123.2(3) . . ?
C2 N1 C1 113.4(4) . . ?
C1 N1 Cu1 123.2(3) . . ?
H6A N6 H6B 120.0 . . ?
C2 N6 H6A 120.0 . . ?
C2 N6 H6B 120.0 . . ?
C2 N3 C3 114.6(4) . . ?
C1 N2 C3 114.9(4) . . ?
H4A N4 H4B 105.1 . . ?
C1 N4 H4A 108.6 . . ?
C1 N4 H4B 114.6 . . ?
H5A N5 H5B 108.9 . . ?
C3 N5 H5A 108.0 . . ?
C3 N5 H5B 111.4 . . ?
N6 C2 N1 117.4(4) . . ?
N3 C2 N1 125.3(4) . . ?
N3 C2 N6 117.3(4) . . ?
N2 C3 N3 126.0(4) . . ?
N2 C3 N5 117.3(4) . . ?
N5 C3 N3 116.7(4) . . ?
N2 C1 N1 125.7(4) . . ?
N2 C1 N4 118.0(4) . . ?
N4 C1 N1 116.3(4) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N6 H6A N3 0.86 2.21 3.062(6) 172.3 2_567 yes
N5 H5A N2 0.87 2.31 3.055(5) 143.4 2_677 yes

_shelx_res_file                  
;
TITL 170814hq5_a.res in P-1
    170814hq5.res
    created by SHELXL-2018/3 at 23:22:27 on 05-Jul-2020
REM Old TITL 170814hq5 in P1 #1
REM SHELXT solution in P-1
REM R1 0.153, Rweak 0.014, Alpha 0.031, Orientation as input
REM Formula found by SHELXT: C9 Br Cu
CELL 0.71073 4.0787 9.0943 10.9148 82.327 80.162 77.648
ZERR 1 0.0003 0.0006 0.0007 0.006 0.006 0.006
LATT 1
SFAC C H Cu I N
UNIT 6 12 2 2 12
EQIV $1 -X,1-Y,2-Z
EQIV $2 1-X,2-Y,2-Z

L.S. 4
PLAN  20
HTAB N6 N3_$1
HTAB N5 N2_$2
BOND $H
list 4
fmap 2
acta
SHEL 999 0.83
OMIT 0 -1 2
OMIT 0 -1 3
OMIT 1 0 0
OMIT 1 0 1
OMIT 1 3 1
OMIT 0 -2 3
OMIT 1 3 3
OMIT 1 2 2
REM <olex2.extras>
REM <HklSrc "%.\\170814hq5.hkl">
REM </olex2.extras>

WGHT    0.012000
EXTI    0.004153
FVAR       0.67187
I1    4    0.127785    0.691172    0.413826    11.00000    0.02901    0.02718 =
         0.02395   -0.00225    0.00003   -0.01163
CU1   3    0.574916    0.606881    0.570988    11.00000    0.05022    0.04175 =
         0.02606   -0.00916   -0.00089   -0.01150
N1    5    0.428235    0.696841    0.735611    11.00000    0.03407    0.02382 =
         0.02151   -0.00701    0.00126   -0.00987
N6    5    0.181164    0.495621    0.826809    11.00000    0.05588    0.03628 =
         0.02318   -0.01045    0.00489   -0.02580
AFIX  93
H6A   2    0.085803    0.446042    0.890726    11.00000   -1.20000
H6B   2    0.213018    0.463328    0.754327    11.00000   -1.20000
AFIX   0
N3    5    0.223964    0.667435    0.954655    11.00000    0.04265    0.02473 =
         0.01948   -0.00408    0.00000   -0.01387
N2    5    0.458958    0.883682    0.866377    11.00000    0.05104    0.02574 =
         0.02522   -0.00635    0.00401   -0.01580
N4    5    0.606003    0.919668    0.653636    11.00000    0.07879    0.03507 =
         0.03043   -0.00636    0.01605   -0.02623
AFIX   7
H4A   2    0.737725    0.975067    0.674816    11.00000   -1.20000
H4B   2    0.733422    0.868918    0.592316    11.00000   -1.20000
AFIX   0
N5    5    0.299969    0.840364    1.076537    11.00000    0.08894    0.04357 =
         0.02922   -0.01313    0.01186   -0.03592
AFIX   7
H5A   2    0.302280    0.936404    1.068677    11.00000   -1.20000
H5B   2    0.112019    0.824784    1.122757    11.00000   -1.20000
AFIX   0
C2    1    0.279903    0.622913    0.840124    11.00000    0.02887    0.02419 =
         0.02309   -0.00296   -0.00387   -0.00581
C3    1    0.326284    0.797327    0.961920    11.00000    0.04822    0.02191 =
         0.02152   -0.00729   -0.00070   -0.01165
C1    1    0.498683    0.831411    0.756328    11.00000    0.03671    0.02088 =
         0.02932   -0.00208   -0.00103   -0.00585
HKLF 4




REM  170814hq5_a.res in P-1
REM wR2 = 0.0521, GooF = S = 1.044, Restrained GooF = 1.044 for all data
REM R1 = 0.0259 for 1259 Fo > 4sig(Fo) and 0.0299 for all 1390 data
REM 103 parameters refined using 0 restraints

END

WGHT      0.0120      0.0000

REM Highest difference peak  0.543,  deepest hole -0.657,  1-sigma level  0.122
Q1    1   0.4916  0.7159  0.5816  11.00000  0.05    0.54
Q2    1   0.2697  0.7423  1.1437  11.00000  0.05    0.52
Q3    1   0.0186  0.7653  0.3481  11.00000  0.05    0.49
Q4    1   0.2808  0.5447  0.4294  11.00000  0.05    0.47
Q5    1   0.1179  0.5745  0.3960  11.00000  0.05    0.46
Q6    1   0.5530  0.7536  0.4374  11.00000  0.05    0.45
Q7    1   0.2224  0.6148  0.4841  11.00000  0.05    0.44
Q8    1   0.4555  0.6438  0.6777  11.00000  0.05    0.43
Q9    1   0.4014  0.5755  0.6027  11.00000  0.05    0.43
Q10   1   0.4544  0.7613  0.7459  11.00000  0.05    0.42
Q11   1   0.0659  0.7983  0.4361  11.00000  0.05    0.42
Q12   1   0.5254  1.0254  0.6639  11.00000  0.05    0.42
Q13   1  -0.1193  0.6712  0.3780  11.00000  0.05    0.42
Q14   1   0.0869  0.6586  0.9148  11.00000  0.05    0.41
Q15   1   0.7711  0.5296  0.4960  11.00000  0.05    0.40
Q16   1   0.7249  0.5846  0.6138  11.00000  0.05    0.39
Q17   1   0.3965  0.9184  1.1120  11.00000  0.05    0.39
Q18   1   0.2029  0.7256  0.9766  11.00000  0.05    0.39
Q19   1   0.2307  0.7106  0.3228  11.00000  0.05    0.39
Q20   1   0.2818  0.8634  0.9064  11.00000  0.05    0.38
;
_shelx_res_checksum              41770
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.664
_oxdiff_exptl_absorpt_empirical_full_min 0.692
