# Electronic Supplementary Material (ESI) for Photochemical & Photobiological Sciences.
# This journal is © The Royal Society of Chemistry and Owner Societies 2018

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1818389'
_audit_update_record             
;
2018-10-23 deposited with the CCDC.
2018-12-06 downloaded from the CCDC.
;
_audit_creation_date             2018-09-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C11 H16 Br2 Cu2 N4'
_chemical_formula_sum            'C11 H16 Br2 Cu2 N4'
_chemical_formula_weight         491.18
_chemical_absolute_configuration unk
_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      orthorhombic
_space_group_IT_number           34
_space_group_name_H-M_alt        'P n n 2'
_space_group_name_Hall           'P 2 -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   17.5605(14)
_cell_length_b                   9.4899(7)
_cell_length_c                   9.6110(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1601.6(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14529
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.350
_cell_measurement_theta_min      3.017
_shelx_estimated_absorpt_T_max   0.432
_shelx_estimated_absorpt_T_min   0.385
_exptl_absorpt_coefficient_mu    7.636
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.037
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14529
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         3.017
_diffrn_ambient_temperature      173.0
_diffrn_detector_area_resol_mean 9.00cm
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.880
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2654
_reflns_number_total             2945
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 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         0.838
_refine_diff_density_min         -0.837
_refine_diff_density_rms         0.138
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.16(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2945
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0385
_refine_ls_restrained_S_all      1.089
_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)+(0.0497P)²+4.6007P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0936
_refine_ls_wR_factor_ref         0.0979
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.84(3)
 0.16(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B)
3.b Me refined with riding coordinates:
 C4(H4A,H4B,H4C), C8(H8A,H8B,H8C)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C5(H5), C6(H6)
;
_atom_sites_solution_hydrogens   geom
_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
Cu1 Cu 0.57430(9) -0.03988(16) 0.20642(17) 0.0331(4) Uani 1 1 d . . . . .
Cu2 Cu 0.52937(9) 0.15705(16) 0.39200(16) 0.0338(4) Uani 1 1 d . . . . .
Br1 Br 0.45713(6) -0.21605(11) 0.13861(11) 0.0226(3) Uani 1 1 d . . . . .
Br2 Br 0.60826(6) -0.07743(10) 0.46007(12) 0.0207(2) Uani 1 1 d . . . . .
N1 N 0.6553(6) 0.8619(12) 1.0963(10) 0.035(3) Uani 1 1 d . . . . .
N2 N 0.5595(6) 0.2885(10) 0.5449(11) 0.027(2) Uani 1 1 d . . . . .
N3 N 0.7206(6) 0.7726(12) 0.9235(10) 0.037(3) Uani 1 1 d . . . . .
N4 N 0.5982(6) 0.4648(10) 0.6747(10) 0.028(2) Uani 1 1 d . . . . .
C1 C 0.7043(8) 0.7584(14) 1.1504(16) 0.041(3) Uani 1 1 d . . . . .
H1 H 0.708571 0.731821 1.245398 0.050 Uiso 1 1 calc R . . . .
C2 C 0.7439(8) 0.7042(15) 1.0445(16) 0.044(3) Uani 1 1 d . . . . .
H2 H 0.781260 0.632050 1.050519 0.053 Uiso 1 1 calc R . . . .
C3 C 0.6679(7) 0.8636(12) 0.9608(15) 0.032(3) Uani 1 1 d . . . . .
C4 C 0.6290(10) 0.9638(17) 0.8685(16) 0.053(4) Uani 1 1 d . . . . .
H4A H 0.592363 1.019287 0.922492 0.079 Uiso 1 1 calc R . . . .
H4B H 0.666548 1.026900 0.826073 0.079 Uiso 1 1 calc R . . . .
H4C H 0.602040 0.911928 0.795308 0.079 Uiso 1 1 calc R . . . .
C5 C 0.5773(8) 0.3594(14) 0.7612(14) 0.034(3) Uani 1 1 d . . . . .
H5 H 0.579008 0.360823 0.860010 0.040 Uiso 1 1 calc R . . . .
C6 C 0.5531(8) 0.2497(13) 0.6789(13) 0.034(3) Uani 1 1 d . . . . .
H6 H 0.534902 0.161283 0.711269 0.040 Uiso 1 1 calc R . . . .
C7 C 0.5883(6) 0.4183(11) 0.5406(13) 0.025(3) Uani 1 1 d . . . . .
C8 C 0.6070(7) 0.5023(13) 0.4150(12) 0.032(3) Uani 1 1 d . . . . .
H8A H 0.627287 0.594200 0.443254 0.047 Uiso 1 1 calc R . . . .
H8B H 0.645242 0.452218 0.359616 0.047 Uiso 1 1 calc R . . . .
H8C H 0.560898 0.516082 0.359218 0.047 Uiso 1 1 calc R . . . .
C9 C 0.7497(8) 0.7338(14) 0.7885(15) 0.040(3) Uani 1 1 d . . . . .
H9A H 0.805774 0.724134 0.794204 0.049 Uiso 1 1 calc R . . . .
H9B H 0.738260 0.810159 0.721518 0.049 Uiso 1 1 calc R . . . .
C10 C 0.7161(8) 0.5972(15) 0.7351(18) 0.050(4) Uani 1 1 d . . . . .
H10A H 0.740063 0.574035 0.644718 0.060 Uiso 1 1 calc R . . . .
H10B H 0.728863 0.520723 0.801165 0.060 Uiso 1 1 calc R . . . .
C11 C 0.6307(7) 0.6018(12) 0.7162(15) 0.034(3) Uani 1 1 d . . . . .
H11A H 0.606871 0.632168 0.804619 0.041 Uiso 1 1 calc R . . . .
H11B H 0.618122 0.672878 0.644430 0.041 Uiso 1 1 calc R . . . .


_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 Cu1 2.717(3) 2_655 ?
Cu1 Cu2 2.781(2) 2_655 ?
Cu1 Cu2 2.701(2) . ?
Cu1 Br1 2.5745(18) 2_655 ?
Cu1 Br1 2.730(2) . ?
Cu1 Br2 2.535(2) . ?
Cu1 N1 2.004(10) 1_544 ?
Cu2 Br1 2.5101(19) 2_655 ?
Cu2 Br2 2.6155(19) 2_655 ?
Cu2 Br2 2.7016(19) . ?
Cu2 N2 1.999(10) . ?
N1 C1 1.406(17) . ?
N1 C3 1.321(17) . ?
N2 C6 1.344(17) . ?
N2 C7 1.332(15) . ?
N3 C2 1.393(18) . ?
N3 C3 1.316(16) . ?
N3 C9 1.442(15) . ?
N4 C5 1.352(17) . ?
N4 C7 1.373(16) . ?
N4 C11 1.475(15) . ?
C1 H1 0.9500 . ?
C1 C2 1.34(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.47(2) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5 0.9500 . ?
C5 C6 1.375(18) . ?
C6 H6 0.9500 . ?
C7 C8 1.484(17) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.514(18) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.511(19) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?

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 Cu1 Cu2 58.84(6) 2_655 2_655 ?
Cu1 Cu1 Br1 56.41(6) 2_655 . ?
Cu2 Cu1 Cu1 61.75(6) . 2_655 ?
Cu2 Cu1 Cu2 70.24(7) . 2_655 ?
Cu2 Cu1 Br1 111.17(7) . . ?
Br1 Cu1 Cu1 62.05(6) 2_655 2_655 ?
Br1 Cu1 Cu2 54.18(5) . 2_655 ?
Br1 Cu1 Cu2 56.76(5) 2_655 . ?
Br1 Cu1 Cu2 113.53(7) 2_655 2_655 ?
Br1 Cu1 Br1 110.84(7) 2_655 . ?
Br2 Cu1 Cu1 105.37(4) . 2_655 ?
Br2 Cu1 Cu2 62.03(5) . . ?
Br2 Cu1 Cu2 58.73(5) . 2_655 ?
Br2 Cu1 Br1 108.71(7) . . ?
Br2 Cu1 Br1 115.24(7) . 2_655 ?
N1 Cu1 Cu1 144.3(3) 1_544 2_655 ?
N1 Cu1 Cu2 151.4(3) 1_544 . ?
N1 Cu1 Cu2 128.2(3) 1_544 2_655 ?
N1 Cu1 Br1 117.2(3) 1_544 2_655 ?
N1 Cu1 Br1 97.1(3) 1_544 . ?
N1 Cu1 Br2 106.0(3) 1_544 . ?
Cu1 Cu2 Cu1 59.40(7) . 2_655 ?
Cu1 Cu2 Br2 55.96(5) . . ?
Br1 Cu2 Cu1 59.08(5) 2_655 . ?
Br1 Cu2 Cu1 61.88(5) 2_655 2_655 ?
Br1 Cu2 Br2 111.73(7) 2_655 . ?
Br1 Cu2 Br2 113.23(7) 2_655 2_655 ?
Br2 Cu2 Cu1 99.31(6) . 2_655 ?
Br2 Cu2 Cu1 103.60(7) 2_655 . ?
Br2 Cu2 Cu1 55.94(5) 2_655 2_655 ?
Br2 Cu2 Br2 100.10(6) 2_655 . ?
N2 Cu2 Cu1 153.5(3) . 2_655 ?
N2 Cu2 Cu1 147.1(3) . . ?
N2 Cu2 Br1 123.3(3) . 2_655 ?
N2 Cu2 Br2 101.5(3) . . ?
N2 Cu2 Br2 104.0(3) . 2_655 ?
Cu1 Br1 Cu1 61.54(6) 2_655 . ?
Cu2 Br1 Cu1 64.16(6) 2_655 2_655 ?
Cu2 Br1 Cu1 63.94(5) 2_655 . ?
Cu1 Br2 Cu2 65.33(6) . 2_655 ?
Cu1 Br2 Cu2 62.01(5) . . ?
Cu2 Br2 Cu2 72.75(6) 2_655 . ?
C1 N1 Cu1 124.3(9) . 1_566 ?
C3 N1 Cu1 129.3(9) . 1_566 ?
C3 N1 C1 105.7(11) . . ?
C6 N2 Cu2 120.7(8) . . ?
C7 N2 Cu2 130.9(9) . . ?
C7 N2 C6 108.4(11) . . ?
C2 N3 C9 121.9(12) . . ?
C3 N3 C2 106.6(11) . . ?
C3 N3 C9 131.4(13) . . ?
C5 N4 C7 107.8(10) . . ?
C5 N4 C11 126.2(11) . . ?
C7 N4 C11 125.9(10) . . ?
N1 C1 H1 126.1 . . ?
C2 C1 N1 107.8(13) . . ?
C2 C1 H1 126.1 . . ?
N3 C2 H2 126.2 . . ?
C1 C2 N3 107.7(12) . . ?
C1 C2 H2 126.2 . . ?
N1 C3 C4 121.7(12) . . ?
N3 C3 N1 112.2(13) . . ?
N3 C3 C4 126.0(13) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N4 C5 H5 126.6 . . ?
N4 C5 C6 106.9(12) . . ?
C6 C5 H5 126.6 . . ?
N2 C6 C5 108.5(12) . . ?
N2 C6 H6 125.7 . . ?
C5 C6 H6 125.7 . . ?
N2 C7 N4 108.4(11) . . ?
N2 C7 C8 127.3(11) . . ?
N4 C7 C8 124.2(10) . . ?
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 . . ?
N3 C9 H9A 109.1 . . ?
N3 C9 H9B 109.1 . . ?
N3 C9 C10 112.7(12) . . ?
H9A C9 H9B 107.8 . . ?
C10 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
C9 C10 H10A 108.8 . . ?
C9 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C11 C10 C9 113.8(11) . . ?
C11 C10 H10A 108.8 . . ?
C11 C10 H10B 108.8 . . ?
N4 C11 C10 113.0(10) . . ?
N4 C11 H11A 109.0 . . ?
N4 C11 H11B 109.0 . . ?
C10 C11 H11A 109.0 . . ?
C10 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.84(3)
2 0.16(3)

####################################################################### 
# 
# 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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1837238'
_audit_update_record             
;
2018-10-23 deposited with the CCDC.
2018-12-06 downloaded from the CCDC.
;
_audit_creation_date             2018-09-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C11 H16 Br2 Cu2 N4'
_chemical_formula_sum            'C11 H16 Br2 Cu2 N4'
_chemical_formula_weight         491.18
_chemical_absolute_configuration unk
_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      orthorhombic
_space_group_IT_number           34
_space_group_name_H-M_alt        'P n n 2'
_space_group_name_Hall           'P 2 -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   17.6696(5)
_cell_length_b                   9.5533(3)
_cell_length_c                   9.5747(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1616.24(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6483
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      28.277
_cell_measurement_theta_min      3.013
_shelx_estimated_absorpt_T_max   0.435
_shelx_estimated_absorpt_T_min   0.389
_exptl_absorpt_coefficient_mu    7.567
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.019
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            15474
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.343
_diffrn_reflns_theta_min         3.012
_diffrn_ambient_temperature      299.19
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.881
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2531
_reflns_number_total             2882
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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         0.325
_refine_diff_density_min         -0.510
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.059(18)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2882
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0294
_refine_ls_restrained_S_all      1.024
_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)+(0.0251P)²+0.5586P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0575
_refine_ls_wR_factor_ref         0.0607
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.941(18)
 0.059(18)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B)
3.b Me refined with riding coordinates:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5)
;
_atom_sites_solution_hydrogens   geom
_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
Cu1 Cu 0.07669(6) 0.04121(12) 0.54366(12) 0.0583(3) Uani 1 1 d . . . . .
Cu2 Cu 0.02923(6) -0.15941(11) 0.35660(12) 0.0591(3) Uani 1 1 d . . . . .
Br1 Br 0.04356(4) -0.20720(8) 0.60702(8) 0.0449(2) Uani 1 1 d . . . . .
Br2 Br 0.10658(4) 0.07721(7) 0.29005(9) 0.03846(18) Uani 1 1 d . . . . .
N1 N 0.1559(3) 0.1414(7) 0.6541(7) 0.0492(17) Uani 1 1 d . . . . .
N2 N 0.0989(3) 0.5355(6) 1.0755(7) 0.0420(16) Uani 1 1 d . . . . .
N3 N 0.2212(3) 0.2297(7) 0.8274(7) 0.0481(18) Uani 1 1 d . . . . .
N4 N 0.0601(3) 0.7097(6) 1.2040(7) 0.0412(15) Uani 1 1 d . . . . .
C1 C 0.2030(5) 0.2449(9) 0.6007(10) 0.059(2) Uani 1 1 d . . . . .
H1 H 0.205781 0.272250 0.507601 0.071 Uiso 1 1 calc R . . . .
C2 C 0.2437(5) 0.2987(10) 0.7058(11) 0.067(3) Uani 1 1 d . . . . .
H2 H 0.280038 0.368785 0.698987 0.081 Uiso 1 1 calc R . . . .
C3 C 0.1687(4) 0.1385(7) 0.7882(10) 0.0465(18) Uani 1 1 d . . . . .
C4 C 0.0775(5) 0.6381(9) 0.9871(9) 0.051(2) Uani 1 1 d . . . . .
H4 H 0.078709 0.635281 0.889997 0.061 Uiso 1 1 calc R . . . .
C5 C 0.0537(4) 0.7461(8) 1.0681(8) 0.047(2) Uani 1 1 d . . . . .
H5 H 0.035908 0.831533 1.035229 0.057 Uiso 1 1 calc R . . . .
C6 C 0.0887(4) 0.5815(7) 1.2062(9) 0.0390(17) Uani 1 1 d . . . . .
C7 C 0.2483(5) 0.2671(9) 0.9646(10) 0.060(2) Uani 1 1 d . . . . .
H7A H 0.302989 0.275467 0.961840 0.072 Uiso 1 1 calc R . . . .
H7B H 0.235720 0.192748 1.029544 0.072 Uiso 1 1 calc R . . . .
C8 C 0.2150(4) 0.4026(9) 1.0168(10) 0.061(3) Uani 1 1 d . . . . .
H8A H 0.237730 0.424918 1.106342 0.073 Uiso 1 1 calc R . . . .
H8B H 0.228344 0.476775 0.952167 0.073 Uiso 1 1 calc R . . . .
C9 C 0.1314(4) 0.3999(8) 1.0333(10) 0.050(2) Uani 1 1 d . . . . .
H9A H 0.108781 0.371536 0.945396 0.060 Uiso 1 1 calc R . . . .
H9B H 0.118250 0.330084 1.102715 0.060 Uiso 1 1 calc R . . . .
C10 C 0.1317(6) 0.0382(10) 0.8839(11) 0.079(3) Uani 1 1 d . . . . .
H10A H 0.149132 0.054188 0.977468 0.119 Uiso 1 1 calc R . . . .
H10B H 0.077837 0.050900 0.880072 0.119 Uiso 1 1 calc R . . . .
H10C H 0.144065 -0.055631 0.856166 0.119 Uiso 1 1 calc R . . . .
C11 C 0.1067(4) 0.4996(8) 1.3348(8) 0.049(2) Uani 1 1 d . . . . .
H11A H 0.126771 0.409831 1.308878 0.074 Uiso 1 1 calc R . . . .
H11B H 0.143544 0.549351 1.389318 0.074 Uiso 1 1 calc R . . . .
H11C H 0.061517 0.486818 1.388913 0.074 Uiso 1 1 calc R . . . .


_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 Cu1 2.822(2) 2 ?
Cu1 Cu2 2.8260(15) 2 ?
Cu1 Cu2 2.7540(15) . ?
Cu1 Br1 2.7198(14) 2 ?
Cu1 Br1 2.5184(13) . ?
Cu1 Br2 2.5087(14) . ?
Cu1 N1 1.998(6) . ?
Cu2 Br1 2.4539(14) . ?
Cu2 Br2 2.6041(12) 2 ?
Cu2 Br2 2.7173(13) . ?
Cu2 N4 1.999(6) 1_544 ?
N1 C1 1.390(10) . ?
N1 C3 1.305(11) . ?
N2 C4 1.349(10) . ?
N2 C6 1.338(10) . ?
N2 C9 1.474(9) . ?
N3 C2 1.396(11) . ?
N3 C3 1.327(9) . ?
N3 C7 1.442(10) . ?
N4 C5 1.351(10) . ?
N4 C6 1.326(9) . ?
C1 H1 0.9300 . ?
C1 C2 1.339(12) . ?
C2 H2 0.9300 . ?
C3 C10 1.478(13) . ?
C4 H4 0.9300 . ?
C4 C5 1.357(11) . ?
C5 H5 0.9300 . ?
C6 C11 1.494(11) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.507(10) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.486(10) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?

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 Cu1 Cu2 58.36(4) 2 2 ?
Cu2 Cu1 Cu1 60.89(4) . 2 ?
Cu2 Cu1 Cu2 70.38(5) . 2 ?
Br1 Cu1 Cu1 54.01(4) 2 2 ?
Br1 Cu1 Cu1 60.92(4) . 2 ?
Br1 Cu1 Cu2 108.24(5) 2 . ?
Br1 Cu1 Cu2 55.26(4) . . ?
Br1 Cu1 Cu2 52.48(4) 2 2 ?
Br1 Cu1 Cu2 112.04(5) . 2 ?
Br1 Cu1 Br1 108.30(5) . 2 ?
Br2 Cu1 Cu1 103.91(3) . 2 ?
Br2 Cu1 Cu2 61.97(4) . . ?
Br2 Cu1 Cu2 58.07(4) . 2 ?
Br2 Cu1 Br1 114.29(5) . . ?
Br2 Cu1 Br1 107.48(5) . 2 ?
N1 Cu1 Cu1 143.73(19) . 2 ?
N1 Cu1 Cu2 127.4(2) . 2 ?
N1 Cu1 Cu2 153.0(2) . . ?
N1 Cu1 Br1 98.61(19) . 2 ?
N1 Cu1 Br1 119.1(2) . . ?
N1 Cu1 Br2 107.4(2) . . ?
Cu1 Cu2 Cu1 60.75(5) . 2 ?
Br1 Cu2 Cu1 61.53(4) . 2 ?
Br1 Cu2 Cu1 57.49(4) . . ?
Br1 Cu2 Br2 109.39(5) . . ?
Br1 Cu2 Br2 112.97(5) . 2 ?
Br2 Cu2 Cu1 98.59(4) . 2 ?
Br2 Cu2 Cu1 54.58(4) . . ?
Br2 Cu2 Cu1 103.29(4) 2 . ?
Br2 Cu2 Cu1 54.85(4) 2 2 ?
Br2 Cu2 Br2 98.93(4) 2 . ?
N4 Cu2 Cu1 145.86(18) 1_544 . ?
N4 Cu2 Cu1 153.37(19) 1_544 2 ?
N4 Cu2 Br1 124.75(19) 1_544 . ?
N4 Cu2 Br2 102.22(18) 1_544 . ?
N4 Cu2 Br2 105.13(19) 1_544 2 ?
Cu1 Br1 Cu1 65.07(4) . 2 ?
Cu2 Br1 Cu1 65.98(4) . 2 ?
Cu2 Br1 Cu1 67.25(4) . . ?
Cu1 Br2 Cu2 67.08(4) . 2 ?
Cu1 Br2 Cu2 63.46(4) . . ?
Cu2 Br2 Cu2 74.34(4) 2 . ?
C1 N1 Cu1 124.5(6) . . ?
C3 N1 Cu1 129.2(6) . . ?
C3 N1 C1 105.9(7) . . ?
C4 N2 C9 125.1(7) . . ?
C6 N2 C4 108.1(6) . . ?
C6 N2 C9 126.7(6) . . ?
C2 N3 C7 123.2(7) . . ?
C3 N3 C2 105.8(7) . . ?
C3 N3 C7 130.7(8) . . ?
C5 N4 Cu2 121.4(5) . 1_566 ?
C6 N4 Cu2 132.1(6) . 1_566 ?
C6 N4 C5 106.5(7) . . ?
N1 C1 H1 125.7 . . ?
C2 C1 N1 108.6(8) . . ?
C2 C1 H1 125.7 . . ?
N3 C2 H2 126.5 . . ?
C1 C2 N3 107.0(7) . . ?
C1 C2 H2 126.5 . . ?
N1 C3 N3 112.7(8) . . ?
N1 C3 C10 123.2(8) . . ?
N3 C3 C10 124.0(9) . . ?
N2 C4 H4 126.9 . . ?
N2 C4 C5 106.3(8) . . ?
C5 C4 H4 126.9 . . ?
N4 C5 C4 109.2(7) . . ?
N4 C5 H5 125.4 . . ?
C4 C5 H5 125.4 . . ?
N2 C6 C11 124.8(6) . . ?
N4 C6 N2 109.8(7) . . ?
N4 C6 C11 125.4(7) . . ?
N3 C7 H7A 109.1 . . ?
N3 C7 H7B 109.1 . . ?
N3 C7 C8 112.7(7) . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 H7A 109.1 . . ?
C8 C7 H7B 109.1 . . ?
C7 C8 H8A 108.7 . . ?
C7 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C9 C8 C7 114.1(7) . . ?
C9 C8 H8A 108.7 . . ?
C9 C8 H8B 108.7 . . ?
N2 C9 C8 113.7(6) . . ?
N2 C9 H9A 108.8 . . ?
N2 C9 H9B 108.8 . . ?
C8 C9 H9A 108.8 . . ?
C8 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
C3 C10 H10A 109.5 . . ?
C3 C10 H10B 109.5 . . ?
C3 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C6 C11 H11A 109.5 . . ?
C6 C11 H11B 109.5 . . ?
C6 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.941(18)
2 0.059(18)

####################################################################### 
# 
# 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_1_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1837240'
_audit_update_record             
;
2018-10-23 deposited with the CCDC.
2018-12-06 downloaded from the CCDC.
;
_audit_creation_date             2018-09-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C18 H14 Cu I N4'
_chemical_formula_sum            'C18 H14 Cu I N4'
_chemical_formula_weight         476.77
_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'
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      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_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.0197(8)
_cell_length_b                   7.6791(6)
_cell_length_c                   22.4578(18)
_cell_angle_alpha                90
_cell_angle_beta                 101.735(3)
_cell_angle_gamma                90
_cell_volume                     1691.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5967
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      25.110
_cell_measurement_theta_min      3.112
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.122
_exptl_absorpt_correction_T_max  0.709
_exptl_absorpt_correction_T_min  0.673
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.872
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0721
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            11716
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.145
_diffrn_reflns_theta_max         25.145
_diffrn_reflns_theta_min         2.810
_diffrn_ambient_temperature      297.3
_diffrn_detector_area_resol_mean 9.00cm
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_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                2573
_reflns_number_total             3005
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.660
_refine_diff_density_min         -0.827
_refine_diff_density_rms         0.111
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3005
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0367
_refine_ls_restrained_S_all      1.077
_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)+(0.0568P)²+1.1327P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.1007
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11),
 C12(H12), C13(H13), C15(H15), C16(H16), C18(H18)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
Cu1 Cu 0.64716(6) 0.99648(9) 0.22324(3) 0.03881(19) Uani 1 1 d . . . . .
I1 I 0.60951(3) 0.64376(4) 0.21014(2) 0.03554(14) Uani 1 1 d . . . . .
N1 N 0.5174(4) 1.0706(5) 0.27493(17) 0.0339(9) Uani 1 1 d . . . . .
N2 N 0.1677(4) 2.4280(5) 0.64040(16) 0.0315(8) Uani 1 1 d . . . . .
N3 N 0.4053(4) 1.2432(5) 0.32622(16) 0.0309(9) Uani 1 1 d . . . . .
N4 N 0.1917(4) 2.2601(5) 0.56371(16) 0.0290(8) Uani 1 1 d . . . . .
C1 C 0.4121(5) 0.9782(8) 0.2911(2) 0.0411(13) Uani 1 1 d . . . . .
H1 H 0.391934 0.861902 0.281743 0.049 Uiso 1 1 calc R . . . .
C2 C 0.3427(6) 1.0825(7) 0.3225(2) 0.0448(13) Uani 1 1 d . . . . .
H2 H 0.267337 1.051952 0.338446 0.054 Uiso 1 1 calc R . . . .
C3 C 0.5093(5) 1.2278(7) 0.2969(2) 0.0353(11) Uani 1 1 d . . . . .
H3 H 0.568600 1.318110 0.292709 0.042 Uiso 1 1 calc R . . . .
C4 C 0.2050(5) 1.5735(7) 0.3906(2) 0.0354(11) Uani 1 1 d . . . . .
H4 H 0.114093 1.600320 0.389777 0.042 Uiso 1 1 calc R . . . .
C5 C 0.3069(5) 1.6775(6) 0.4245(2) 0.0294(10) Uani 1 1 d . . . . .
C6 C 0.4417(5) 1.6352(6) 0.4234(2) 0.0386(12) Uani 1 1 d . . . . .
H6 H 0.511493 1.702878 0.445519 0.046 Uiso 1 1 calc R . . . .
C7 C 0.4745(5) 1.4955(7) 0.3904(2) 0.0401(12) Uani 1 1 d . . . . .
H7 H 0.565163 1.470503 0.390010 0.048 Uiso 1 1 calc R . . . .
C8 C 0.3715(5) 1.3933(6) 0.3580(2) 0.0304(10) Uani 1 1 d . . . . .
C9 C 0.2364(5) 1.4305(7) 0.3582(2) 0.0373(11) Uani 1 1 d . . . . .
H9 H 0.167334 1.360404 0.336715 0.045 Uiso 1 1 calc R . . . .
C10 C 0.1606(5) 2.4237(7) 0.5402(2) 0.0365(11) Uani 1 1 d . . . . .
H10 H 0.151179 2.457706 0.499858 0.044 Uiso 1 1 calc R . . . .
C11 C 0.1463(5) 2.5257(7) 0.5879(2) 0.0348(11) Uani 1 1 d . . . . .
H11 H 0.125269 2.643808 0.585414 0.042 Uiso 1 1 calc R . . . .
C12 C 0.1954(5) 2.2704(7) 0.6240(2) 0.0340(11) Uani 1 1 d . . . . .
H12 H 0.215215 2.177000 0.650685 0.041 Uiso 1 1 calc R . . . .
C13 C 0.3530(5) 1.8598(6) 0.5187(2) 0.0389(12) Uani 1 1 d . . . . .
H13 H 0.426148 1.787291 0.534188 0.047 Uiso 1 1 calc R . . . .
C14 C 0.2737(5) 1.8266(6) 0.4611(2) 0.0298(10) Uani 1 1 d . . . . .
C15 C 0.1642(5) 1.9363(7) 0.43929(19) 0.0340(11) Uani 1 1 d . . . . .
H15 H 0.108990 1.914660 0.401452 0.041 Uiso 1 1 calc R . . . .
C16 C 0.1363(5) 2.0777(7) 0.4733(2) 0.0352(11) Uani 1 1 d . . . . .
H16 H 0.063243 2.150686 0.458061 0.042 Uiso 1 1 calc R . . . .
C17 C 0.2176(5) 2.1097(6) 0.52989(19) 0.0280(10) Uani 1 1 d . . . . .
C18 C 0.3240(5) 1.9994(6) 0.5530(2) 0.0376(11) Uani 1 1 d . . . . .
H18 H 0.376411 2.018750 0.591632 0.045 Uiso 1 1 calc R . . . .


_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 I1 2.8246(7) 2_655 ?
Cu1 I1 2.7422(8) . ?
Cu1 N1 1.994(4) . ?
Cu1 N2 1.999(4) 4_695 ?
N1 C1 1.381(6) . ?
N1 C3 1.313(6) . ?
N2 C11 1.378(6) . ?
N2 C12 1.311(6) . ?
N3 C2 1.379(6) . ?
N3 C3 1.346(6) . ?
N3 C8 1.432(6) . ?
N4 C10 1.374(6) . ?
N4 C12 1.349(5) . ?
N4 C17 1.435(6) . ?
C1 H1 0.9300 . ?
C1 C2 1.349(7) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C4 C5 1.394(7) . ?
C4 C9 1.389(7) . ?
C5 C6 1.394(7) . ?
C5 C14 1.486(6) . ?
C6 H6 0.9300 . ?
C6 C7 1.381(7) . ?
C7 H7 0.9300 . ?
C7 C8 1.380(7) . ?
C8 C9 1.384(6) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C10 C11 1.356(7) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C13 C14 1.397(7) . ?
C13 C18 1.385(7) . ?
C14 C15 1.391(6) . ?
C15 H15 0.9300 . ?
C15 C16 1.388(7) . ?
C16 H16 0.9300 . ?
C16 C17 1.386(6) . ?
C17 C18 1.378(6) . ?
C18 H18 0.9300 . ?

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
I1 Cu1 I1 122.51(2) . 2_655 ?
N1 Cu1 I1 104.64(12) . . ?
N1 Cu1 I1 99.90(11) . 2_655 ?
N1 Cu1 N2 131.45(17) . 4_695 ?
N2 Cu1 I1 97.79(11) 4_695 2_655 ?
N2 Cu1 I1 102.98(12) 4_695 . ?
Cu1 I1 Cu1 104.687(17) . 2_645 ?
C1 N1 Cu1 129.1(3) . . ?
C3 N1 Cu1 125.4(3) . . ?
C3 N1 C1 105.4(4) . . ?
C11 N2 Cu1 127.7(3) . 4_596 ?
C12 N2 Cu1 126.7(3) . 4_596 ?
C12 N2 C11 105.5(4) . . ?
C2 N3 C8 126.9(4) . . ?
C3 N3 C2 106.2(4) . . ?
C3 N3 C8 126.8(4) . . ?
C10 N4 C17 125.8(4) . . ?
C12 N4 C10 106.8(4) . . ?
C12 N4 C17 127.4(4) . . ?
N1 C1 H1 125.2 . . ?
C2 C1 N1 109.6(5) . . ?
C2 C1 H1 125.2 . . ?
N3 C2 H2 126.7 . . ?
C1 C2 N3 106.7(4) . . ?
C1 C2 H2 126.7 . . ?
N1 C3 N3 112.2(4) . . ?
N1 C3 H3 123.9 . . ?
N3 C3 H3 123.9 . . ?
C5 C4 H4 119.3 . . ?
C9 C4 H4 119.3 . . ?
C9 C4 C5 121.3(4) . . ?
C4 C5 C14 121.4(4) . . ?
C6 C5 C4 117.5(4) . . ?
C6 C5 C14 121.1(4) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 C5 121.9(4) . . ?
C7 C6 H6 119.1 . . ?
C6 C7 H7 120.3 . . ?
C8 C7 C6 119.4(4) . . ?
C8 C7 H7 120.3 . . ?
C7 C8 N3 119.5(4) . . ?
C7 C8 C9 120.6(4) . . ?
C9 C8 N3 119.9(4) . . ?
C4 C9 H9 120.3 . . ?
C8 C9 C4 119.4(4) . . ?
C8 C9 H9 120.3 . . ?
N4 C10 H10 126.9 . . ?
C11 C10 N4 106.1(4) . . ?
C11 C10 H10 126.9 . . ?
N2 C11 H11 125.1 . . ?
C10 C11 N2 109.7(4) . . ?
C10 C11 H11 125.1 . . ?
N2 C12 N4 111.8(4) . . ?
N2 C12 H12 124.1 . . ?
N4 C12 H12 124.1 . . ?
C14 C13 H13 119.6 . . ?
C18 C13 H13 119.6 . . ?
C18 C13 C14 120.8(4) . . ?
C13 C14 C5 120.3(4) . . ?
C15 C14 C5 121.4(4) . . ?
C15 C14 C13 118.3(4) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 C14 120.9(4) . . ?
C16 C15 H15 119.5 . . ?
C15 C16 H16 120.1 . . ?
C17 C16 C15 119.8(4) . . ?
C17 C16 H16 120.1 . . ?
C16 C17 N4 119.5(4) . . ?
C18 C17 N4 120.3(4) . . ?
C18 C17 C16 120.1(4) . . ?
C13 C18 H18 120.0 . . ?
C17 C18 C13 120.0(4) . . ?
C17 C18 H18 120.0 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_1_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1818392'
_audit_update_record             
;
2018-10-23 deposited with the CCDC.
2018-12-06 downloaded from the CCDC.
;
_audit_creation_date             2018-09-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C16 H18 Cu I N4'
_chemical_formula_sum            'C16 H18 Cu I N4'
_chemical_formula_weight         456.78
_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'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   10.2473(6)
_cell_length_b                   11.2320(6)
_cell_length_c                   14.7127(8)
_cell_angle_alpha                90
_cell_angle_beta                 98.832(2)
_cell_angle_gamma                90
_cell_volume                     1673.32(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9931
_cell_measurement_temperature    149(2)
_cell_measurement_theta_max      30.512
_cell_measurement_theta_min      2.802
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.151
_exptl_absorpt_correction_T_max  0.707
_exptl_absorpt_correction_T_min  0.671
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.813
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15359
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         2.802
_diffrn_ambient_temperature      148.74
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_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                2820
_reflns_number_total             3062
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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 (Sheldrick, 2008)'
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.488
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3062
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0236
_refine_ls_R_factor_gt           0.0209
_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)+(0.0249P)²+1.6766P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0530
_refine_ls_wR_factor_ref         0.0550
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B)
2.b Me refined with riding coordinates:
 C4(H4A,H4B,H4C), C8(H8A,H8B,H8C)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C14(H14)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
Cu1 Cu 0.10173(4) 0.44912(3) 0.55602(2) 0.03891(10) Uani 1 1 d . . . . .
I1 I 0.14423(2) 0.53683(2) 0.39512(2) 0.03618(7) Uani 1 1 d . . . . .
N1 N 0.1268(2) 0.26923(19) 0.54385(14) 0.0342(5) Uani 1 1 d . . . . .
N2 N 0.7774(2) 0.03073(18) 0.83944(15) 0.0339(5) Uani 1 1 d . . . . .
N3 N 0.1669(2) 0.08142(18) 0.58124(14) 0.0302(4) Uani 1 1 d . . . . .
N4 N 0.6024(2) 0.07851(19) 0.74005(15) 0.0351(5) Uani 1 1 d . . . . .
C1 C 0.1214(3) 0.2026(2) 0.46533(17) 0.0365(6) Uani 1 1 d . . . . .
H1 H 0.103197 0.233306 0.404528 0.044 Uiso 1 1 calc R . . . .
C2 C 0.1456(3) 0.0876(2) 0.48683(17) 0.0363(6) Uani 1 1 d . . . . .
H2 H 0.147581 0.023313 0.445073 0.044 Uiso 1 1 calc R . . . .
C3 C 0.1535(2) 0.1936(2) 0.61353(17) 0.0319(5) Uani 1 1 d . . . . .
C4 C 0.1640(3) 0.2280(3) 0.71149(18) 0.0448(7) Uani 1 1 d . . . . .
H4A H 0.184248 0.157449 0.750275 0.067 Uiso 1 1 calc R . . . .
H4B H 0.234556 0.286927 0.726297 0.067 Uiso 1 1 calc R . . . .
H4C H 0.080023 0.262394 0.722782 0.067 Uiso 1 1 calc R . . . .
C5 C 0.6491(3) 0.0142(2) 0.81603(17) 0.0320(5) Uani 1 1 d . . . . .
C6 C 0.8133(3) 0.1084(3) 0.77536(18) 0.0412(6) Uani 1 1 d . . . . .
H6 H 0.900419 0.136844 0.774702 0.049 Uiso 1 1 calc R . . . .
C7 C 0.7072(3) 0.1384(3) 0.71363(19) 0.0425(6) Uani 1 1 d . . . . .
H7 H 0.705374 0.190220 0.662429 0.051 Uiso 1 1 calc R . . . .
C8 C 0.5647(3) -0.0630(3) 0.8650(2) 0.0499(7) Uani 1 1 d . . . . .
H8A H 0.473287 -0.059573 0.833625 0.075 Uiso 1 1 calc R . . . .
H8B H 0.596666 -0.145257 0.865316 0.075 Uiso 1 1 calc R . . . .
H8C H 0.568670 -0.035043 0.928509 0.075 Uiso 1 1 calc R . . . .
C9 C 0.5333(3) -0.2160(3) 0.5635(2) 0.0495(7) Uani 1 1 d . . . . .
H9 H 0.607014 -0.258611 0.548235 0.059 Uiso 1 1 calc R . . . .
C10 C 0.4073(3) -0.2594(2) 0.5377(2) 0.0449(7) Uani 1 1 d . . . . .
H10 H 0.393695 -0.331679 0.503993 0.054 Uiso 1 1 calc R . . . .
C11 C 0.3015(3) -0.1976(2) 0.56089(18) 0.0379(6) Uani 1 1 d . . . . .
H11 H 0.214961 -0.228316 0.543188 0.045 Uiso 1 1 calc R . . . .
C12 C 0.3181(2) -0.0913(2) 0.60967(16) 0.0307(5) Uani 1 1 d . . . . .
C13 C 0.4464(3) -0.0468(2) 0.63548(18) 0.0330(6) Uani 1 1 d . . . . .
C14 C 0.5519(3) -0.1103(3) 0.6118(2) 0.0445(7) Uani 1 1 d . . . . .
H14 H 0.639009 -0.080645 0.629154 0.053 Uiso 1 1 calc R . . . .
C15 C 0.1982(3) -0.0288(2) 0.63452(19) 0.0342(6) Uani 1 1 d . . . . .
H15A H 0.121425 -0.083237 0.623241 0.041 Uiso 1 1 calc R . . . .
H15B H 0.213841 -0.009242 0.700918 0.041 Uiso 1 1 calc R . . . .
C16 C 0.4691(3) 0.0698(2) 0.6885(2) 0.0426(7) Uani 1 1 d . . . . .
H16A H 0.453864 0.137114 0.644731 0.051 Uiso 1 1 calc R . . . .
H16B H 0.404268 0.076276 0.731679 0.051 Uiso 1 1 calc R . . . .


_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 Cu1 2.7048(7) 3_566 ?
Cu1 I1 2.6610(4) . ?
Cu1 I1 2.7296(4) 3_566 ?
Cu1 N1 2.048(2) . ?
Cu1 N2 2.039(2) 2_656 ?
N1 C1 1.370(3) . ?
N1 C3 1.327(3) . ?
N2 C5 1.320(3) . ?
N2 C6 1.375(3) . ?
N3 C2 1.374(3) . ?
N3 C3 1.362(3) . ?
N3 C15 1.474(3) . ?
N4 C5 1.355(3) . ?
N4 C7 1.373(4) . ?
N4 C16 1.461(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.345(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.480(4) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C8 1.487(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.348(4) . ?
C7 H7 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9 0.9500 . ?
C9 C10 1.377(4) . ?
C9 C14 1.382(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.374(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.391(4) . ?
C12 C13 1.404(4) . ?
C12 C15 1.508(4) . ?
C13 C14 1.383(4) . ?
C13 C16 1.524(4) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?

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 Cu1 I1 58.635(14) 3_566 3_566 ?
I1 Cu1 Cu1 61.149(14) . 3_566 ?
I1 Cu1 I1 119.784(13) . 3_566 ?
N1 Cu1 Cu1 117.32(6) . 3_566 ?
N1 Cu1 I1 104.33(6) . . ?
N1 Cu1 I1 102.32(6) . 3_566 ?
N2 Cu1 Cu1 126.31(6) 2_656 3_566 ?
N2 Cu1 I1 109.95(6) 2_656 . ?
N2 Cu1 I1 104.71(6) 2_656 3_566 ?
N2 Cu1 N1 116.09(8) 2_656 . ?
Cu1 I1 Cu1 60.217(13) . 3_566 ?
C1 N1 Cu1 128.53(17) . . ?
C3 N1 Cu1 125.26(17) . . ?
C3 N1 C1 106.2(2) . . ?
C5 N2 Cu1 126.82(18) . 2_646 ?
C5 N2 C6 105.7(2) . . ?
C6 N2 Cu1 127.37(18) . 2_646 ?
C2 N3 C15 124.6(2) . . ?
C3 N3 C2 107.3(2) . . ?
C3 N3 C15 128.1(2) . . ?
C5 N4 C7 107.6(2) . . ?
C5 N4 C16 125.2(2) . . ?
C7 N4 C16 126.6(2) . . ?
N1 C1 H1 124.9 . . ?
C2 C1 N1 110.1(2) . . ?
C2 C1 H1 124.9 . . ?
N3 C2 H2 126.8 . . ?
C1 C2 N3 106.3(2) . . ?
C1 C2 H2 126.8 . . ?
N1 C3 N3 110.0(2) . . ?
N1 C3 C4 124.1(2) . . ?
N3 C3 C4 125.8(2) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C5 N4 110.6(2) . . ?
N2 C5 C8 125.8(2) . . ?
N4 C5 C8 123.6(2) . . ?
N2 C6 H6 124.8 . . ?
C7 C6 N2 110.3(2) . . ?
C7 C6 H6 124.8 . . ?
N4 C7 H7 127.1 . . ?
C6 C7 N4 105.8(2) . . ?
C6 C7 H7 127.1 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 H9 120.1 . . ?
C10 C9 C14 119.7(3) . . ?
C14 C9 H9 120.1 . . ?
C9 C10 H10 120.2 . . ?
C11 C10 C9 119.6(3) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 119.2 . . ?
C10 C11 C12 121.6(3) . . ?
C12 C11 H11 119.2 . . ?
C11 C12 C13 118.7(2) . . ?
C11 C12 C15 119.1(2) . . ?
C13 C12 C15 122.2(2) . . ?
C12 C13 C16 120.5(2) . . ?
C14 C13 C12 119.0(2) . . ?
C14 C13 C16 120.6(2) . . ?
C9 C14 C13 121.4(3) . . ?
C9 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
N3 C15 C12 112.4(2) . . ?
N3 C15 H15A 109.1 . . ?
N3 C15 H15B 109.1 . . ?
C12 C15 H15A 109.1 . . ?
C12 C15 H15B 109.1 . . ?
H15A C15 H15B 107.9 . . ?
N4 C16 C13 112.4(2) . . ?
N4 C16 H16A 109.1 . . ?
N4 C16 H16B 109.1 . . ?
C13 C16 H16A 109.1 . . ?
C13 C16 H16B 109.1 . . ?
H16A C16 H16B 107.9 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_p21n
_database_code_depnum_ccdc_archive 'CCDC 1818394'
_audit_update_record             
;
2018-10-23 deposited with the CCDC.
2018-12-06 downloaded from the CCDC.
;
_audit_creation_date             2018-09-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H14 Cu I N4'
_chemical_formula_sum            'C18 H14 Cu I N4'
_chemical_formula_weight         476.77
_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'
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      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_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.9207(5)
_cell_length_b                   7.6320(4)
_cell_length_c                   22.4684(12)
_cell_angle_alpha                90
_cell_angle_beta                 101.502(2)
_cell_angle_gamma                90
_cell_volume                     1667.03(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9939
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.117
_cell_measurement_theta_min      2.453
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.168
_exptl_absorpt_correction_T_max  0.706
_exptl_absorpt_correction_T_min  0.669
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.900
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            23355
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.125
_diffrn_reflns_theta_min         2.825
_diffrn_ambient_temperature      173.0
_diffrn_detector_area_resol_mean 9.00cm
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_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                3225
_reflns_number_total             3666
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.577
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3666
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0213
_refine_ls_restrained_S_all      1.076
_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)+(0.0171P)²+1.6280P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0440
_refine_ls_wR_factor_ref         0.0460
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12),
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.39129(2) -0.36368(2) 0.78952(2) 0.01971(5) Uani 1 1 d . . . . .
Cu1 Cu 0.35204(3) -0.01208(4) 0.77590(2) 0.02042(7) Uani 1 1 d . . . . .
N1 N 0.4844(2) 0.0633(3) 0.72474(9) 0.0190(4) Uani 1 1 d . . . . .
N2 N 0.5975(2) 0.2393(3) 0.67372(9) 0.0177(4) Uani 1 1 d . . . . .
N3 N 0.80680(19) 1.2650(3) 0.43559(8) 0.0160(4) Uani 1 1 d . . . . .
N4 N 0.83032(19) 1.4351(3) 0.35867(8) 0.0168(4) Uani 1 1 d . . . . .
C1 C 0.5924(3) -0.0271(3) 0.70910(11) 0.0229(5) Uani 1 1 d . . . . .
H1 H 0.613832 -0.146426 0.718575 0.028 Uiso 1 1 calc R . . . .
C2 C 0.6636(3) 0.0795(3) 0.67817(11) 0.0235(5) Uani 1 1 d . . . . .
H2 H 0.743103 0.049944 0.662683 0.028 Uiso 1 1 calc R . . . .
C3 C 0.4902(2) 0.2227(3) 0.70236(11) 0.0198(5) Uani 1 1 d . . . . .
H3 H 0.427121 0.313995 0.705888 0.024 Uiso 1 1 calc R . . . .
C4 C 0.6308(2) 0.3903(3) 0.64170(10) 0.0171(5) Uani 1 1 d . . . . .
C5 C 0.7670(2) 0.4307(3) 0.64182(10) 0.0194(5) Uani 1 1 d . . . . .
H5 H 0.838738 0.360153 0.663917 0.023 Uiso 1 1 calc R . . . .
C6 C 0.7980(2) 0.5753(3) 0.60939(10) 0.0195(5) Uani 1 1 d . . . . .
H6 H 0.891462 0.605102 0.610644 0.023 Uiso 1 1 calc R . . . .
C7 C 0.6940(2) 0.6777(3) 0.57497(10) 0.0169(5) Uani 1 1 d . . . . .
C8 C 0.5581(2) 0.6332(3) 0.57590(11) 0.0218(5) Uani 1 1 d . . . . .
H8 H 0.485768 0.701306 0.552972 0.026 Uiso 1 1 calc R . . . .
C9 C 0.5258(2) 0.4925(3) 0.60936(11) 0.0218(5) Uani 1 1 d . . . . .
H9 H 0.432519 0.466222 0.610132 0.026 Uiso 1 1 calc R . . . .
C10 C 0.7269(2) 0.8273(3) 0.53831(10) 0.0162(5) Uani 1 1 d . . . . .
C11 C 0.8370(2) 0.9388(3) 0.55971(10) 0.0189(5) Uani 1 1 d . . . . .
H11 H 0.894680 0.916441 0.598064 0.023 Uiso 1 1 calc R . . . .
C12 C 0.8637(2) 1.0818(3) 0.52587(10) 0.0195(5) Uani 1 1 d . . . . .
H12 H 0.938197 1.157948 0.541315 0.023 Uiso 1 1 calc R . . . .
C13 C 0.7812(2) 1.1135(3) 0.46932(10) 0.0161(5) Uani 1 1 d . . . . .
C14 C 0.6736(3) 1.0023(3) 0.44617(11) 0.0215(5) Uani 1 1 d . . . . .
H14 H 0.618993 1.022332 0.406956 0.026 Uiso 1 1 calc R . . . .
C15 C 0.6460(2) 0.8616(3) 0.48070(11) 0.0210(5) Uani 1 1 d . . . . .
H15 H 0.570830 0.786608 0.465113 0.025 Uiso 1 1 calc R . . . .
C16 C 0.8389(2) 1.4302(3) 0.45899(10) 0.0189(5) Uani 1 1 d . . . . .
H16 H 0.849533 1.464954 0.500261 0.023 Uiso 1 1 calc R . . . .
C17 C 0.8522(2) 1.5330(3) 0.41143(10) 0.0181(5) Uani 1 1 d . . . . .
H17 H 0.873407 1.654491 0.413946 0.022 Uiso 1 1 calc R . . . .
C18 C 0.8020(2) 1.2748(3) 0.37488(10) 0.0188(5) Uani 1 1 d . . . . .
H18 H 0.781076 1.178997 0.347607 0.023 Uiso 1 1 calc R . . . .


_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 2.7200(4) . ?
I1 Cu1 2.8028(4) 2_546 ?
Cu1 N1 1.995(2) . ?
Cu1 N4 2.0025(19) 4_576 ?
N1 C1 1.377(3) . ?
N1 C3 1.322(3) . ?
N2 C2 1.379(3) . ?
N2 C3 1.356(3) . ?
N2 C4 1.431(3) . ?
N3 C13 1.433(3) . ?
N3 C16 1.379(3) . ?
N3 C18 1.357(3) . ?
N4 C17 1.381(3) . ?
N4 C18 1.322(3) . ?
C1 C2 1.356(4) . ?
C4 C5 1.385(3) . ?
C4 C9 1.386(3) . ?
C5 C6 1.390(3) . ?
C6 C7 1.398(3) . ?
C7 C8 1.395(3) . ?
C7 C10 1.481(3) . ?
C8 C9 1.385(3) . ?
C10 C11 1.393(3) . ?
C10 C15 1.405(3) . ?
C11 C12 1.386(3) . ?
C12 C13 1.388(3) . ?
C13 C14 1.382(3) . ?
C14 C15 1.384(3) . ?
C16 C17 1.353(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
Cu1 I1 Cu1 104.516(8) . 2_546 ?
I1 Cu1 I1 123.137(12) . 2_556 ?
N1 Cu1 I1 100.27(6) . 2_556 ?
N1 Cu1 I1 104.69(6) . . ?
N1 Cu1 N4 130.96(8) . 4_576 ?
N4 Cu1 I1 102.98(6) 4_576 . ?
N4 Cu1 I1 97.33(6) 4_576 2_556 ?
C1 N1 Cu1 129.60(17) . . ?
C3 N1 Cu1 124.62(16) . . ?
C3 N1 C1 105.6(2) . . ?
C2 N2 C4 126.5(2) . . ?
C3 N2 C2 106.9(2) . . ?
C3 N2 C4 126.6(2) . . ?
C16 N3 C13 126.04(19) . . ?
C18 N3 C13 126.99(19) . . ?
C18 N3 C16 106.97(19) . . ?
C17 N4 Cu1 127.63(16) . 4_675 ?
C18 N4 Cu1 126.55(16) . 4_675 ?
C18 N4 C17 105.64(19) . . ?
C2 C1 N1 110.0(2) . . ?
C1 C2 N2 106.2(2) . . ?
N1 C3 N2 111.4(2) . . ?
C5 C4 N2 120.1(2) . . ?
C5 C4 C9 120.4(2) . . ?
C9 C4 N2 119.4(2) . . ?
C4 C5 C6 119.6(2) . . ?
C5 C6 C7 121.2(2) . . ?
C6 C7 C10 121.3(2) . . ?
C8 C7 C6 117.7(2) . . ?
C8 C7 C10 121.1(2) . . ?
C9 C8 C7 121.7(2) . . ?
C8 C9 C4 119.3(2) . . ?
C11 C10 C7 121.5(2) . . ?
C11 C10 C15 117.9(2) . . ?
C15 C10 C7 120.5(2) . . ?
C12 C11 C10 121.0(2) . . ?
C11 C12 C13 119.8(2) . . ?
C12 C13 N3 119.4(2) . . ?
C14 C13 N3 120.1(2) . . ?
C14 C13 C12 120.5(2) . . ?
C13 C14 C15 119.3(2) . . ?
C14 C15 C10 121.4(2) . . ?
C17 C16 N3 106.30(19) . . ?
C16 C17 N4 109.9(2) . . ?
N4 C18 N3 111.2(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_yjh-1
_database_code_depnum_ccdc_archive 'CCDC 1837154'
_audit_update_record             
;
2018-10-23 deposited with the CCDC.
2018-12-06 downloaded from the CCDC.
;
_audit_creation_date             2018-10-19
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H5 Cu I N'
_chemical_formula_sum            'C4 H5 Cu I N'
_chemical_formula_weight         257.53
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N Cu I'
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      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   4.27490(10)
_cell_length_b                   16.1161(4)
_cell_length_c                   17.0121(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1172.04(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1396
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.3760
_cell_measurement_theta_min      4.3790
_shelx_estimated_absorpt_T_max   0.377
_shelx_estimated_absorpt_T_min   0.329
_exptl_absorpt_coefficient_mu    8.859
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72128
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    2.919
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            2543
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.340
_diffrn_reflns_theta_min         3.483
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9737
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     69.00  95.00   1.00    1.27    --   18.81-178.00 -30.00   26
  2  ω    -30.00  87.00   1.00    1.27    --   18.81   0.00-150.00  117
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0050766000
_diffrn_orient_matrix_UB_12      0.0021765000
_diffrn_orient_matrix_UB_13      -0.0414606000
_diffrn_orient_matrix_UB_21      -0.0237386000
_diffrn_orient_matrix_UB_22      0.0397677000
_diffrn_orient_matrix_UB_23      0.0002140000
_diffrn_orient_matrix_UB_31      0.0496910000
_diffrn_orient_matrix_UB_32      0.0187510000
_diffrn_orient_matrix_UB_33      0.0043024000
_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                882
_reflns_number_total             1065
_reflns_odcompleteness_completeness 99.36
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.739
_refine_diff_density_min         -1.138
_refine_diff_density_rms         0.222
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     64
_refine_ls_number_reflns         1065
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0319
_refine_ls_restrained_S_all      1.063
_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)+(0.0293P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0697
_refine_ls_wR_factor_ref         0.0764
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1)
;
_atom_sites_solution_hydrogens   geom
_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
I1 I 0.96240(10) -0.13313(3) -0.51728(3) 0.02999(18) Uani 1 1 d . . . . .
Cu1 Cu 0.9585(2) -0.29789(6) -0.54700(5) 0.0420(3) Uani 1 1 d . . . . .
N1 N 0.9736(11) -0.3105(4) -0.6684(3) 0.0358(14) Uani 1 1 d . . . . .
C1 C 0.9878(17) -0.2397(5) -0.7102(4) 0.057(2) Uani 1 1 d . . . . .
H1 H 0.980663 -0.189244 -0.683808 0.069 Uiso 1 1 calc R . . . .
C2 C 0.9851(12) -0.3818(4) -0.7087(4) 0.0291(15) Uani 1 1 d . . . . .
C3 C 0.9597(14) -0.4612(4) -0.6627(4) 0.0366(17) Uani 1 1 d . . . . .
H3A H 0.743936 -0.468889 -0.646605 0.044 Uiso 1 1 calc R . . . .
H3B H 1.085717 -0.456493 -0.615478 0.044 Uiso 1 1 calc R . . . .
C4 C 1.0640(15) -0.5363(4) -0.7081(4) 0.0391(16) Uani 1 1 d . . . . .
H4A H 0.993538 -0.585956 -0.681238 0.047 Uiso 1 1 calc R . . . .
H4B H 1.290723 -0.537561 -0.709928 0.047 Uiso 1 1 calc R . . . .


_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 2.6325(9) 3_544 ?
I1 Cu1 2.6593(9) 3_444 ?
I1 Cu1 2.7031(10) . ?
Cu1 N1 2.075(6) . ?
N1 C1 1.345(9) . ?
N1 C2 1.340(8) . ?
C1 C1 1.358(14) 4_753 ?
C1 H1 0.9300 . ?
C2 C2 1.412(13) 4_753 ?
C2 C3 1.503(9) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.504(9) . ?
C4 C4 1.525(13) 4_753 ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?

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 107.77(4) 3_544 3_444 ?
Cu1 I1 Cu1 70.60(3) 3_544 . ?
Cu1 I1 Cu1 70.20(3) 3_444 . ?
I1 Cu1 I1 107.77(4) 3_444 3_544 ?
I1 Cu1 I1 109.19(3) 3_544 . ?
I1 Cu1 I1 110.00(3) 3_444 . ?
N1 Cu1 I1 113.40(14) . 3_444 ?
N1 Cu1 I1 106.36(16) . . ?
N1 Cu1 I1 110.06(14) . 3_544 ?
C1 N1 Cu1 116.4(5) . . ?
C2 N1 Cu1 126.4(5) . . ?
C2 N1 C1 117.1(6) . . ?
N1 C1 C1 122.1(4) . 4_753 ?
N1 C1 H1 119.0 . . ?
C1 C1 H1 119.0 4_753 . ?
N1 C2 C2 120.8(4) . 4_753 ?
N1 C2 C3 117.5(6) . . ?
C2 C2 C3 121.7(4) 4_753 . ?
C2 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
C2 C3 C4 113.3(6) . . ?
H3A C3 H3B 107.7 . . ?
C4 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
C3 C4 C4 112.0(5) . 4_753 ?
C3 C4 H4A 109.2 . . ?
C3 C4 H4B 109.2 . . ?
C4 C4 H4A 109.2 4_753 . ?
C4 C4 H4B 109.2 4_753 . ?
H4A C4 H4B 107.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 N1 C1 C1 177.1(8) . . . 4_753 ?
Cu1 N1 C2 C2 -175.9(5) . . . 4_753 ?
Cu1 N1 C2 C3 5.1(8) . . . . ?
N1 C2 C3 C4 -163.7(5) . . . . ?
C1 N1 C2 C2 0.8(10) . . . 4_753 ?
C1 N1 C2 C3 -178.2(6) . . . . ?
C2 N1 C1 C1 0.1(13) . . . 4_753 ?
C2 C2 C3 C4 17.3(10) 4_753 . . . ?
C2 C3 C4 C4 -44.5(9) . . . 4_753 ?

_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 1.321
_oxdiff_exptl_absorpt_empirical_full_min 0.924
