# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2016

####################################################################### 
# 
# 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_nyy15060203
_audit_block_doi                 10.5517/ccdc.csd.cc1k1klr
_database_code_depnum_ccdc_archive 'CCDC 1431474'
_audit_update_record             
;
2016-03-28 deposited with the CCDC.
2016-05-10 downloaded from the CCDC.
;
_audit_creation_date             2016-03-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C18 H20 N4), Cu4 I8'
_chemical_formula_sum            'C36 H40 Cu4 I8 N8'
_chemical_formula_weight         1854.12
_chemical_melting_point          ?
_chemical_oxdiff_formula         C9H9N2I2Cu1
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           63
_space_group_name_H-M_alt        'C m c m'
_space_group_name_Hall           '-C 2c 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x, -y, -z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, y, -z-1/2'
'-x, y, z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, y+1/2, -z-1/2'
'-x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   16.9299(6)
_cell_length_b                   14.8450(8)
_cell_length_c                   19.6945(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4949.7(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1718
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      27.7730
_cell_measurement_theta_min      3.5890
_shelx_estimated_absorpt_T_max   0.378
_shelx_estimated_absorpt_T_min   0.347
_exptl_absorpt_coefficient_mu    6.720
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79195
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.488
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             3408
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0401
_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       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            6572
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         2.933
_diffrn_ambient_temperature      291.15
_diffrn_detector_area_resol_mean 16.2312
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -7.00   19.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.2885  -99.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega  -53.00   65.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7885    0.0000  -60.0000 118
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0187831000
_diffrn_orient_matrix_UB_12      -0.0383544000
_diffrn_orient_matrix_UB_13      -0.0141301000
_diffrn_orient_matrix_UB_21      -0.0024269000
_diffrn_orient_matrix_UB_22      0.0196943000
_diffrn_orient_matrix_UB_23      -0.0327595000
_diffrn_orient_matrix_UB_31      0.0373916000
_diffrn_orient_matrix_UB_32      0.0205069000
_diffrn_orient_matrix_UB_33      0.0050102000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2097
_reflns_number_total             2702
_reflns_odcompleteness_completeness 99.72
_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, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         1.875
_refine_diff_density_min         -2.727
_refine_diff_density_rms         0.221
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     143
_refine_ls_number_reflns         2702
_refine_ls_number_restraints     43
_refine_ls_R_factor_all          0.0740
_refine_ls_R_factor_gt           0.0569
_refine_ls_restrained_S_all      1.102
_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)+(0.0874P)²+74.8485P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1578
_refine_ls_wR_factor_ref         0.1712
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
2. Restrained distances
 N1-C5
 1.37 with sigma of 0.02
 N1-C6
 1.37 with sigma of 0.02
 N1-C6A
 1.36 with sigma of 0.02
 C4-C5
 1.38 with sigma of 0.02
 C2-C1
 1.38 with sigma of 0.02
 C6A-C8
 1.55 with sigma of 0.02
 Cu2-I4
 2.3 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C6) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C10) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(C1) \\sim Ueq, Uanis(N1) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(I4) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C6) = Uanis(C6A)
4. Others
 Sof(C6A)=Sof(H6AA)=Sof(H6AB)=1-FVAR(1)
 Sof(C6)=Sof(H6A)=Sof(H6B)=FVAR(1)
5.a Riding coordinates:
 C6A(H6AA,H6AB)
5.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
5.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C7(H7), C9(H9), C10(H10)
5.d X=CH2 refined with riding coordinates:
 N2(H2A,H2B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
C1 C 0.3531(9) 0.8373(12) 0.4683(7) 0.080(4) Uani 1 1 d D U . . .
H1 H 0.4040 0.8142 0.4646 0.096 Uiso 1 1 calc R . . . .
C2 C 0.3210(8) 0.8471(9) 0.5315(6) 0.064(3) Uani 1 1 d D . . . .
H2 H 0.3514 0.8368 0.5701 0.077 Uiso 1 1 calc R . . . .
C3 C 0.2428(7) 0.8726(8) 0.5375(6) 0.051(3) Uani 1 1 d . . . . .
C4 C 0.2020(8) 0.8909(9) 0.4776(6) 0.061(3) Uani 1 1 d D . . . .
H4 H 0.1495 0.9093 0.4795 0.073 Uiso 1 1 calc R . . . .
C5 C 0.2379(6) 0.8824(9) 0.4169(5) 0.058(3) Uani 1 1 d D . . . .
H5 H 0.2089 0.8926 0.3776 0.069 Uiso 1 1 calc R . . . .
C6 C 0.3529(13) 0.841(2) 0.3475(9) 0.069(6) Uani 0.71(5) 1 d D U . A 1
H6A H 0.3179 0.8559 0.3101 0.083 Uiso 0.71(5) 1 calc R . . A 1
H6B H 0.3661 0.7776 0.3444 0.083 Uiso 0.71(5) 1 calc R . . A 1
C7 C 0.5000 0.8541(13) 0.3443(8) 0.057(4) Uani 1 2 d S T P A .
H7 H 0.5000 0.7915 0.3454 0.069 Uiso 1 2 calc RS T P . .
C8 C 0.4297(8) 0.8996(10) 0.3435(6) 0.066(3) Uani 1 1 d D . . . .
C9 C 0.4274(12) 0.9908(12) 0.3397(10) 0.097(5) Uani 1 1 d . U . . .
H9 H 0.3800 1.0223 0.3407 0.116 Uiso 1 1 calc R . . . .
C10 C 0.5000 1.035(2) 0.3342(16) 0.117(9) Uani 1 2 d S TU P . .
H10 H 0.5000 1.0967 0.3265 0.140 Uiso 1 2 calc RS T P . .
N1 N 0.3144(6) 0.8597(9) 0.4117(5) 0.069(3) Uani 1 1 d D U . . .
N2 N 0.2090(7) 0.8801(9) 0.5968(5) 0.078(3) Uani 1 1 d . . . . .
H2A H 0.2355 0.8692 0.6332 0.094 Uiso 1 1 calc R . . . .
H2B H 0.1603 0.8960 0.5996 0.094 Uiso 1 1 calc R . . . .
Cu1 Cu 0.57820(12) 0.32518(15) 0.2500 0.0567(6) Uani 1 2 d S T P . .
Cu2 Cu 0.5000 0.47871(19) 0.31998(14) 0.0733(7) Uani 1 2 d DS T P . .
I1 I 0.5000 0.30813(7) 0.36951(5) 0.0438(3) Uani 1 2 d S T P . .
I2 I 0.69041(6) 0.20560(7) 0.2500 0.0476(3) Uani 1 2 d S T P . .
I3 I 0.63653(6) 0.49555(7) 0.2500 0.0453(3) Uani 1 2 d S T P . .
I4 I 0.5000 0.59837(10) 0.41643(7) 0.0715(4) Uani 1 2 d DS TU P . .
C6A C 0.3397(15) 0.885(5) 0.3467(14) 0.069(6) Uani 0.29(5) 1 d D . . A 2
H6AA H 0.2946 0.9059 0.3092 0.083 Uiso 0.29(5) 1 d R . . A 2
H6AB H 0.3491 0.8376 0.3186 0.083 Uiso 0.29(5) 1 d R . . A 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
C1 H1 0.9300 . ?
C1 C2 1.366(14) . ?
C1 N1 1.335(17) . ?
C2 H2 0.9300 . ?
C2 C3 1.382(17) . ?
C3 C4 1.394(16) . ?
C3 N2 1.306(15) . ?
C4 H4 0.9300 . ?
C4 C5 1.346(13) . ?
C5 H5 0.9300 . ?
C5 N1 1.343(12) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C8 1.57(3) . ?
C6 N1 1.449(15) . ?
C7 H7 0.9300 . ?
C7 C8 1.368(16) 11_655 ?
C7 C8 1.368(16) . ?
C8 C9 1.36(2) . ?
C8 C6A 1.539(19) . ?
C9 H9 0.9300 . ?
C9 C10 1.40(2) . ?
C10 C9 1.40(2) 11_655 ?
C10 H10 0.9300 . ?
N1 C6A 1.402(19) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
Cu1 Cu1 2.648(4) 11_655 ?
Cu1 Cu2 2.974(3) 10_556 ?
Cu1 Cu2 2.974(3) . ?
Cu1 I1 2.7122(13) . ?
Cu1 I1 2.7122(13) 10_556 ?
Cu1 I2 2.600(2) . ?
Cu1 I3 2.715(2) . ?
Cu2 Cu1 2.974(3) 11_655 ?
Cu2 Cu2 2.756(5) 10_556 ?
Cu2 I1 2.714(3) . ?
Cu2 I3 2.7028(16) . ?
Cu2 I3 2.7028(16) 11_655 ?
Cu2 I4 2.601(3) . ?
I1 Cu1 2.7122(13) 11_655 ?
I3 Cu2 2.7028(16) 10_556 ?
C6A H6AA 1.1050 . ?
C6A H6AB 0.9128 . ?

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
C2 C1 H1 118.7 . . ?
N1 C1 H1 118.7 . . ?
N1 C1 C2 122.6(13) . . ?
C1 C2 H2 120.4 . . ?
C1 C2 C3 119.2(12) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 C4 117.2(11) . . ?
N2 C3 C2 121.2(11) . . ?
N2 C3 C4 121.6(11) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.6(12) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 119.1 . . ?
N1 C5 C4 121.9(11) . . ?
N1 C5 H5 119.1 . . ?
H6A C6 H6B 108.4 . . ?
C8 C6 H6A 110.1 . . ?
C8 C6 H6B 110.1 . . ?
N1 C6 H6A 110.1 . . ?
N1 C6 H6B 110.1 . . ?
N1 C6 C8 108.1(14) . . ?
C8 C7 H7 119.5 . . ?
C8 C7 H7 119.5 11_655 . ?
C8 C7 C8 120.9(18) . 11_655 ?
C7 C8 C6 116.7(17) . . ?
C7 C8 C6A 142(3) . . ?
C9 C8 C6 122.2(18) . . ?
C9 C8 C7 121.2(16) . . ?
C9 C8 C6A 96(3) . . ?
C8 C9 H9 121.7 . . ?
C8 C9 C10 116.6(19) . . ?
C10 C9 H9 121.7 . . ?
C9 C10 C9 123(3) 11_655 . ?
C9 C10 H10 118.4 . . ?
C9 C10 H10 118.4 11_655 . ?
C1 N1 C5 118.1(11) . . ?
C1 N1 C6 117.4(15) . . ?
C1 N1 C6A 132.8(16) . . ?
C5 N1 C6 123.3(14) . . ?
C5 N1 C6A 107.3(18) . . ?
C3 N2 H2A 120.0 . . ?
C3 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
Cu1 Cu1 Cu2 63.57(5) 11_655 . ?
Cu1 Cu1 Cu2 63.57(5) 11_655 10_556 ?
Cu1 Cu1 I1 60.78(4) 11_655 10_556 ?
Cu1 Cu1 I1 60.78(4) 11_655 . ?
Cu1 Cu1 I3 111.33(5) 11_655 . ?
Cu2 Cu1 Cu2 55.21(11) . 10_556 ?
I1 Cu1 Cu2 104.85(8) . 10_556 ?
I1 Cu1 Cu2 56.78(6) . . ?
I1 Cu1 Cu2 104.86(8) 10_556 . ?
I1 Cu1 Cu2 56.78(6) 10_556 10_556 ?
I1 Cu1 I1 120.40(8) 10_556 . ?
I1 Cu1 I3 105.34(6) . . ?
I1 Cu1 I3 105.34(6) 10_556 . ?
I2 Cu1 Cu1 136.94(5) . 11_655 ?
I2 Cu1 Cu2 148.04(6) . . ?
I2 Cu1 Cu2 148.04(6) . 10_556 ?
I2 Cu1 I1 107.03(5) . 10_556 ?
I2 Cu1 I1 107.03(5) . . ?
I2 Cu1 I3 111.73(8) . . ?
I3 Cu1 Cu2 56.51(6) . . ?
I3 Cu1 Cu2 56.51(6) . 10_556 ?
Cu1 Cu2 Cu1 52.86(9) . 11_655 ?
Cu2 Cu2 Cu1 62.40(5) 10_556 11_655 ?
Cu2 Cu2 Cu1 62.40(5) 10_556 . ?
I1 Cu2 Cu1 56.74(6) . 11_655 ?
I1 Cu2 Cu1 56.74(6) . . ?
I1 Cu2 Cu2 111.07(6) . 10_556 ?
I3 Cu2 Cu1 102.43(9) 11_655 . ?
I3 Cu2 Cu1 56.90(6) 11_655 11_655 ?
I3 Cu2 Cu1 102.43(9) . 11_655 ?
I3 Cu2 Cu1 56.90(6) . . ?
I3 Cu2 Cu2 59.34(5) . 10_556 ?
I3 Cu2 Cu2 59.34(5) 11_655 10_556 ?
I3 Cu2 I1 105.64(7) . . ?
I3 Cu2 I1 105.64(7) 11_655 . ?
I3 Cu2 I3 117.57(10) . 11_655 ?
I4 Cu2 Cu1 149.52(7) . 11_655 ?
I4 Cu2 Cu1 149.52(7) . . ?
I4 Cu2 Cu2 136.92(7) . 10_556 ?
I4 Cu2 I1 112.01(10) . . ?
I4 Cu2 I3 108.01(7) . . ?
I4 Cu2 I3 108.01(7) . 11_655 ?
Cu1 I1 Cu1 58.43(7) . 11_655 ?
Cu1 I1 Cu2 66.48(7) . . ?
Cu1 I1 Cu2 66.48(7) 11_655 . ?
Cu2 I3 Cu1 66.59(7) 10_556 . ?
Cu2 I3 Cu1 66.59(7) . . ?
Cu2 I3 Cu2 61.32(10) 10_556 . ?
C8 C6A H6AA 128.3 . . ?
C8 C6A H6AB 84.8 . . ?
N1 C6A C8 112.1(19) . . ?
N1 C6A H6AA 118.2 . . ?
N1 C6A H6AB 113.4 . . ?
H6AA C6A H6AB 86.0 . . ?

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
C1 C2 C3 C4 -3(2) . . . . ?
C1 C2 C3 N2 178.0(15) . . . . ?
C1 N1 C6A C8 -8(7) . . . . ?
C2 C1 N1 C5 -8(2) . . . . ?
C2 C1 N1 C6 -176.3(19) . . . . ?
C2 C1 N1 C6A 155(4) . . . . ?
C2 C3 C4 C5 1.1(19) . . . . ?
C3 C4 C5 N1 -3(2) . . . . ?
C4 C5 N1 C1 6(2) . . . . ?
C4 C5 N1 C6 173.5(19) . . . . ?
C4 C5 N1 C6A -161(3) . . . . ?
C5 N1 C6A C8 157(4) . . . . ?
C6 C8 C9 C10 -178(2) . . . . ?
C7 C8 C9 C10 2(3) . . . . ?
C7 C8 C6A N1 72(6) . . . . ?
C8 C6 N1 C1 -64(3) . . . . ?
C8 C6 N1 C5 128.6(17) . . . . ?
C8 C7 C8 C6 -177.6(11) 11_655 . . . ?
C8 C7 C8 C9 2(3) 11_655 . . . ?
C8 C7 C8 C6A -176(2) 11_655 . . . ?
C8 C9 C10 C9 -7(4) . . . 11_655 ?
C9 C8 C6A N1 -107(5) . . . . ?
N1 C1 C2 C3 7(2) . . . . ?
N1 C6 C8 C7 113(2) . . . . ?
N1 C6 C8 C9 -66(3) . . . . ?
N2 C3 C4 C5 -179.8(14) . . . . ?
C6A C8 C9 C10 -179(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_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_nyy154032301
_audit_block_doi                 10.5517/ccdc.csd.cc1k1kms
_database_code_depnum_ccdc_archive 'CCDC 1431475'
_audit_update_record             
;
2016-03-28 deposited with the CCDC.
2016-05-10 downloaded from the CCDC.
;
_audit_creation_date             2016-03-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H10 N2, C2 Cu N2 S2'
_chemical_formula_sum            'C11 H10 Cu N4 S2'
_chemical_formula_weight         325.89
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N4O4S2Cu2
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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                   10.8207(6)
_cell_length_b                   12.6826(6)
_cell_length_c                   9.6580(5)
_cell_angle_alpha                90
_cell_angle_beta                 108.391(6)
_cell_angle_gamma                90
_cell_volume                     1257.72(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1444
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      27.7670
_cell_measurement_theta_min      3.9580
_shelx_estimated_absorpt_T_max   0.748
_shelx_estimated_absorpt_T_min   0.578
_exptl_absorpt_coefficient_mu    2.053
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77828
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.721
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             660
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5579
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.366
_diffrn_reflns_theta_min         2.945
_diffrn_ambient_temperature      291.15
_diffrn_detector_area_resol_mean 16.2312
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -25.00    9.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.2104  -99.0000  -60.0000 34

#__ type_ start__ end____ width___ exp.time_
  2 omega  -84.00  -28.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.2104  -37.0000 -180.0000 56

#__ type_ start__ end____ width___ exp.time_
  3 omega  -42.00   87.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7885    0.0000 -150.0000 129

#__ type_ start__ end____ width___ exp.time_
  4 omega   32.00   57.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7885 -178.0000 -120.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0683333000
_diffrn_orient_matrix_UB_12      -0.0071602000
_diffrn_orient_matrix_UB_13      -0.0293719000
_diffrn_orient_matrix_UB_21      0.0101481000
_diffrn_orient_matrix_UB_22      -0.0479960000
_diffrn_orient_matrix_UB_23      -0.0325309000
_diffrn_orient_matrix_UB_31      0.0001457000
_diffrn_orient_matrix_UB_32      -0.0277787000
_diffrn_orient_matrix_UB_33      0.0637966000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2036
_reflns_number_total             2556
_reflns_odcompleteness_completeness 99.78
_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, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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         0.279
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     171
_refine_ls_number_reflns         2556
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0369
_refine_ls_restrained_S_all      1.042
_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)+(0.0291P)²+0.5694P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0756
_refine_ls_wR_factor_ref         0.0831
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Rigid bond restraints
 Cu1, S1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 Cu1, S2
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3. Uiso/Uaniso restraints and constraints
Uanis(S1) \\sim Ueq, Uanis(Cu1) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.01
4.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C10(H10), C11(H11)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     heavy
_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
N3 N 0.7631(2) 0.85446(18) 0.6354(2) 0.0309(6) Uani 1 1 d . . . . .
N4 N 0.3687(3) 0.8859(3) 0.5597(4) 0.0485(8) Uani 1 1 d . . . . .
H4A H 0.319(4) 0.865(3) 0.489(5) 0.075(16) Uiso 1 1 d . . . . .
H4B H 0.336(4) 0.896(3) 0.630(4) 0.070(14) Uiso 1 1 d . . . . .
C3 C 0.7169(3) 0.8854(2) 0.7433(3) 0.0384(8) Uani 1 1 d . . . . .
H3 H 0.7753 0.8993 0.8353 0.046 Uiso 1 1 calc R . . . .
C4 C 0.5874(3) 0.8969(3) 0.7212(3) 0.0410(8) Uani 1 1 d . . . . .
H4 H 0.5587 0.9188 0.7977 0.049 Uiso 1 1 calc R . . . .
C5 C 0.4965(3) 0.8760(2) 0.5842(3) 0.0328(7) Uani 1 1 d . . . . .
C6 C 0.5472(3) 0.8458(2) 0.4731(3) 0.0336(7) Uani 1 1 d . . . . .
H6 H 0.4910 0.8324 0.3799 0.040 Uiso 1 1 calc R . . . .
C7 C 0.6769(3) 0.8360(2) 0.5006(3) 0.0340(7) Uani 1 1 d . . . . .
H7 H 0.7083 0.8162 0.4252 0.041 Uiso 1 1 calc R . . . .
C8 C 0.9042(3) 0.8416(3) 0.6587(3) 0.0396(8) Uani 1 1 d . . . . .
H8A H 0.9200 0.7718 0.6266 0.048 Uiso 1 1 calc R . . . .
H8B H 0.9513 0.8473 0.7620 0.048 Uiso 1 1 calc R . . . .
C9 C 0.9545(3) 0.9236(2) 0.5764(3) 0.0281(6) Uani 1 1 d . . . . .
C10 C 1.0048(3) 0.8952(2) 0.4665(3) 0.0339(7) Uani 1 1 d . . . . .
H10 H 1.0083 0.8244 0.4430 0.041 Uiso 1 1 calc R . . . .
C11 C 0.9502(3) 1.0290(2) 0.6087(3) 0.0341(7) Uani 1 1 d . . . . .
H11 H 0.9165 1.0495 0.6821 0.041 Uiso 1 1 calc R . . . .
Cu1 Cu 0.71258(4) 0.38208(3) 0.56850(4) 0.03917(14) Uani 1 1 d . U . . .
S1 S 0.73259(8) 0.55766(7) 0.67167(9) 0.0417(2) Uani 1 1 d . U . . .
S2 S 0.86860(8) 0.38073(6) 0.44027(8) 0.0345(2) Uani 1 1 d . U . . .
N1 N 0.4704(3) 0.61797(19) 0.5619(3) 0.0369(6) Uani 1 1 d . . . . .
N2 N 0.7662(2) 0.2317(2) 0.2184(3) 0.0389(6) Uani 1 1 d . . . . .
C1 C 0.5775(3) 0.5928(2) 0.6062(3) 0.0289(6) Uani 1 1 d . . . . .
C2 C 0.8064(3) 0.2924(2) 0.3102(3) 0.0292(6) Uani 1 1 d . . . . .


_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
N3 C3 1.349(4) . ?
N3 C7 1.361(4) . ?
N3 C8 1.480(4) . ?
N4 H4A 0.77(4) . ?
N4 H4B 0.87(4) . ?
N4 C5 1.333(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.357(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.403(4) . ?
C5 C6 1.404(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.349(4) . ?
C7 H7 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.511(4) . ?
C9 C10 1.385(4) . ?
C9 C11 1.378(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.383(4) 3_776 ?
C11 C10 1.383(4) 3_776 ?
C11 H11 0.9300 . ?
Cu1 S1 2.4212(9) . ?
Cu1 S2 2.3882(9) . ?
Cu1 N1 1.983(3) 3_666 ?
Cu1 N2 1.996(3) 4_566 ?
S1 C1 1.657(3) . ?
S2 C2 1.659(3) . ?
N1 Cu1 1.983(3) 3_666 ?
N1 C1 1.147(4) . ?
N2 Cu1 1.996(3) 4_565 ?
N2 C2 1.151(4) . ?

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
C3 N3 C7 118.7(3) . . ?
C3 N3 C8 122.1(3) . . ?
C7 N3 C8 119.3(2) . . ?
H4A N4 H4B 114(4) . . ?
C5 N4 H4A 122(3) . . ?
C5 N4 H4B 122(3) . . ?
N3 C3 H3 119.2 . . ?
N3 C3 C4 121.7(3) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.7(3) . . ?
C5 C4 H4 119.6 . . ?
N4 C5 C4 122.0(3) . . ?
N4 C5 C6 121.6(3) . . ?
C4 C5 C6 116.4(3) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 C5 120.6(3) . . ?
C7 C6 H6 119.7 . . ?
N3 C7 H7 119.1 . . ?
C6 C7 N3 121.9(3) . . ?
C6 C7 H7 119.1 . . ?
N3 C8 H8A 109.3 . . ?
N3 C8 H8B 109.3 . . ?
N3 C8 C9 111.7(2) . . ?
H8A C8 H8B 107.9 . . ?
C9 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
C10 C9 C8 121.2(3) . . ?
C11 C9 C8 120.4(3) . . ?
C11 C9 C10 118.4(3) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.7(3) 3_776 . ?
C11 C10 H10 119.6 3_776 . ?
C9 C11 C10 120.8(3) . 3_776 ?
C9 C11 H11 119.6 . . ?
C10 C11 H11 119.6 3_776 . ?
S2 Cu1 S1 103.53(3) . . ?
N1 Cu1 S1 101.73(7) 3_666 . ?
N1 Cu1 S2 113.49(8) 3_666 . ?
N1 Cu1 N2 117.62(10) 3_666 4_566 ?
N2 Cu1 S1 113.48(8) 4_566 . ?
N2 Cu1 S2 106.25(8) 4_566 . ?
C1 S1 Cu1 98.16(10) . . ?
C2 S2 Cu1 102.31(10) . . ?
C1 N1 Cu1 157.8(2) . 3_666 ?
C2 N2 Cu1 174.2(2) . 4_565 ?
N1 C1 S1 179.3(3) . . ?
N2 C2 S2 178.0(3) . . ?

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
N3 C3 C4 C5 0.4(5) . . . . ?
N3 C8 C9 C10 -116.7(3) . . . . ?
N3 C8 C9 C11 62.7(4) . . . . ?
N4 C5 C6 C7 -179.8(3) . . . . ?
C3 N3 C7 C6 -1.4(4) . . . . ?
C3 N3 C8 C9 -111.8(3) . . . . ?
C3 C4 C5 N4 179.5(3) . . . . ?
C3 C4 C5 C6 -1.5(4) . . . . ?
C4 C5 C6 C7 1.2(4) . . . . ?
C5 C6 C7 N3 0.2(5) . . . . ?
C7 N3 C3 C4 1.1(4) . . . . ?
C7 N3 C8 C9 67.2(4) . . . . ?
C8 N3 C3 C4 -179.9(3) . . . . ?
C8 N3 C7 C6 179.5(3) . . . . ?
C8 C9 C10 C11 179.6(3) . . . 3_776 ?
C8 C9 C11 C10 -179.6(3) . . . 3_776 ?
C10 C9 C11 C10 -0.2(5) . . . 3_776 ?
C11 C9 C10 C11 0.2(5) . . . 3_776 ?

_shelx_SHELXL_version_number     2014/7
_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_nyy15041302
_audit_block_doi                 10.5517/ccdc.csd.cc1lcl5q
_database_code_depnum_ccdc_archive 'CCDC 1470893'
_audit_update_record             
;
2016-03-28 deposited with the CCDC.
2016-05-10 downloaded from the CCDC.
;
_audit_creation_date             2016-03-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H20 N4, Br3 Cu'
_chemical_formula_sum            'C18 H20 Br3 Cu N4'
_chemical_formula_weight         595.65
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N4O4S2Br1Cu1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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                   12.7090(4)
_cell_length_b                   9.2371(4)
_cell_length_c                   18.0149(6)
_cell_angle_alpha                90
_cell_angle_beta                 96.508(3)
_cell_angle_gamma                90
_cell_volume                     2101.21(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3008
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      72.1720
_cell_measurement_theta_min      4.9260
_shelx_estimated_absorpt_T_max   0.353
_shelx_estimated_absorpt_T_min   0.290
_exptl_absorpt_coefficient_mu    8.223
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78729
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            cyan
_exptl_crystal_density_diffrn    1.883
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7520
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.073
_diffrn_reflns_theta_max         67.073
_diffrn_reflns_theta_min         3.500
_diffrn_ambient_temperature      291.15
_diffrn_detector_area_resol_mean 16.2312
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -2.00   41.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000   30.0000 43

#__ type_ start__ end____ width___ exp.time_
  2 omega   19.00   68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   37.0000 -180.0000 49

#__ type_ start__ end____ width___ exp.time_
  3 omega   35.00   63.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000  -60.0000 28

#__ type_ start__ end____ width___ exp.time_
  4 omega   27.00   69.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   77.0000 -120.0000 42

#__ type_ start__ end____ width___ exp.time_
  5 omega   40.00  117.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000  -30.0000 77

#__ type_ start__ end____ width___ exp.time_
  6 omega  -12.00   82.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -37.0000   90.0000 94

#__ type_ start__ end____ width___ exp.time_
  7 omega   83.00  126.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   77.0000 -120.0000 43

#__ type_ start__ end____ width___ exp.time_
  8 omega   50.00  116.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  -30.0000 66

#__ type_ start__ end____ width___ exp.time_
  9 omega   54.00   80.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega   43.00   69.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 11 omega   42.00   90.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000   30.0000 48

#__ type_ start__ end____ width___ exp.time_
 12 omega   51.00   90.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -120.0000 39

#__ type_ start__ end____ width___ exp.time_
 13 omega  112.00  140.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000   30.0000 28

#__ type_ start__ end____ width___ exp.time_
 14 omega   43.00   70.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -30.0000 27

#__ type_ start__ end____ width___ exp.time_
 15 omega   92.00  175.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000    0.0000 83

#__ type_ start__ end____ width___ exp.time_
 16 omega   51.00  107.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000 -150.0000 56

#__ type_ start__ end____ width___ exp.time_
 17 omega   61.00  170.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   15.0000  120.0000 109

#__ type_ start__ end____ width___ exp.time_
 18 omega  -77.00  -32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000 -150.0000 45
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1204778000
_diffrn_orient_matrix_UB_12      -0.0019197000
_diffrn_orient_matrix_UB_13      -0.0038195000
_diffrn_orient_matrix_UB_21      -0.0093171000
_diffrn_orient_matrix_UB_22      0.1396682000
_diffrn_orient_matrix_UB_23      -0.0469785000
_diffrn_orient_matrix_UB_31      0.0167372000
_diffrn_orient_matrix_UB_32      0.0911629000
_diffrn_orient_matrix_UB_33      0.0720102000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3053
_reflns_number_total             3746
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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         0.572
_refine_diff_density_min         -0.587
_refine_diff_density_rms         0.090
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3746
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0383
_refine_ls_restrained_S_all      1.030
_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)+(0.0451P)²+1.1663P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0943
_refine_ls_wR_factor_ref         0.1018
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
2.a Rotating group:
 N2(H2A,H2B), N4(H4A,H4B)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C5(H5), C9(H9), C10(H10), C12(H12), C13(H13),
 C14(H14), C15(H15), C17(H17), C18(H18)
;
_atom_sites_solution_hydrogens   mixed
_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
C1 C 1.0555(4) 0.6298(7) 0.6382(3) 0.0694(15) Uani 1 1 d . . . . .
H1 H 1.1290 0.6360 0.6451 0.083 Uiso 1 1 calc R . . . .
C2 C 0.9979(6) 0.7117(7) 0.5837(4) 0.0829(19) Uani 1 1 d . . . . .
H2 H 1.0333 0.7718 0.5534 0.100 Uiso 1 1 calc R . . . .
C3 C 0.8892(5) 0.7058(6) 0.5736(3) 0.0680(14) Uani 1 1 d . . . . .
H3 H 0.8515 0.7634 0.5375 0.082 Uiso 1 1 calc R . . . .
C4 C 0.8365(4) 0.6150(5) 0.6167(2) 0.0487(10) Uani 1 1 d . . . . .
C5 C 0.8941(3) 0.5318(5) 0.6710(2) 0.0435(9) Uani 1 1 d . . . . .
H5 H 0.8585 0.4701 0.7005 0.052 Uiso 1 1 calc R . . . .
C6 C 1.0031(3) 0.5386(5) 0.6823(2) 0.0468(10) Uani 1 1 d . . . . .
C7 C 1.0639(4) 0.4440(6) 0.7407(3) 0.0595(13) Uani 1 1 d . . . . .
H7A H 1.1122 0.5034 0.7732 0.071 Uiso 1 1 calc R . . . .
H7B H 1.0148 0.3983 0.7709 0.071 Uiso 1 1 calc R . . . .
C8 C 0.7169(4) 0.6092(7) 0.6081(3) 0.0618(14) Uani 1 1 d . . . . .
H8A H 0.6944 0.5359 0.6415 0.074 Uiso 1 1 calc R . . . .
H8B H 0.6897 0.7017 0.6229 0.074 Uiso 1 1 calc R . . . .
C9 C 0.6966(4) 0.4518(5) 0.4978(3) 0.0562(12) Uani 1 1 d . . . . .
H9 H 0.7460 0.3905 0.5236 0.067 Uiso 1 1 calc R . . . .
C10 C 0.6531(4) 0.4133(5) 0.4290(3) 0.0535(11) Uani 1 1 d . . . . .
H10 H 0.6724 0.3268 0.4079 0.064 Uiso 1 1 calc R . . . .
C11 C 0.5775(3) 0.5058(5) 0.3890(2) 0.0472(10) Uani 1 1 d . . . . .
C12 C 0.5520(4) 0.6333(5) 0.4250(2) 0.0491(11) Uani 1 1 d . . . . .
H12 H 0.5027 0.6970 0.4010 0.059 Uiso 1 1 calc R . . . .
C13 C 0.5983(4) 0.6646(5) 0.4943(2) 0.0494(11) Uani 1 1 d . . . . .
H13 H 0.5797 0.7492 0.5176 0.059 Uiso 1 1 calc R . . . .
C14 C 1.2301(3) 0.3139(6) 0.7241(2) 0.0509(11) Uani 1 1 d . . . . .
H14 H 1.2647 0.3741 0.7604 0.061 Uiso 1 1 calc R . . . .
C15 C 1.2866(4) 0.2127(6) 0.6917(3) 0.0546(12) Uani 1 1 d . . . . .
H15 H 1.3586 0.2022 0.7071 0.065 Uiso 1 1 calc R . . . .
C16 C 1.2372(4) 0.1234(5) 0.6352(3) 0.0492(10) Uani 1 1 d . . . . .
C17 C 1.1267(4) 0.1405(5) 0.6186(3) 0.0519(11) Uani 1 1 d . . . . .
H17 H 1.0896 0.0814 0.5829 0.062 Uiso 1 1 calc R . . . .
C18 C 1.0750(3) 0.2408(6) 0.6536(3) 0.0543(12) Uani 1 1 d . . . . .
H18 H 1.0021 0.2491 0.6420 0.065 Uiso 1 1 calc R . . . .
N1 N 0.6709(3) 0.5757(4) 0.5304(2) 0.0488(9) Uani 1 1 d . . . . .
N2 N 0.5350(3) 0.4739(5) 0.3195(2) 0.0631(11) Uani 1 1 d . . . . .
H2A H 0.5562 0.3892 0.3080 0.076 Uiso 1 1 d GR . . . .
H2B H 0.4671 0.4740 0.3181 0.076 Uiso 1 1 d GR . . . .
N3 N 1.1248(3) 0.3307(5) 0.7054(2) 0.0496(9) Uani 1 1 d . . . . .
N4 N 1.2919(4) 0.0312(5) 0.5970(3) 0.0677(12) Uani 1 1 d . . . . .
H4A H 1.3543 0.0207 0.6211 0.081 Uiso 1 1 d GR . . . .
H4B H 1.2616 -0.0530 0.5933 0.081 Uiso 1 1 d GR . . . .
Br1 Br 0.31766(4) 0.71540(6) 0.26141(3) 0.06098(16) Uani 1 1 d . . . . .
Br2 Br 0.17134(4) 0.88843(6) 0.43679(3) 0.05689(15) Uani 1 1 d . . . . .
Br3 Br 0.45081(4) 1.05184(7) 0.37016(3) 0.06517(18) Uani 1 1 d . . . . .
Cu1 Cu 0.31088(6) 0.88124(9) 0.36180(4) 0.0635(2) Uani 1 1 d . . . . .


_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
C1 H1 0.9300 . ?
C1 C2 1.381(9) . ?
C1 C6 1.379(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.375(9) . ?
C3 H3 0.9300 . ?
C3 C4 1.368(7) . ?
C4 C5 1.387(6) . ?
C4 C8 1.511(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.378(6) . ?
C6 C7 1.511(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 N3 1.486(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 N1 1.487(6) . ?
C9 H9 0.9300 . ?
C9 C10 1.346(7) . ?
C9 N1 1.344(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.420(6) . ?
C11 C12 1.401(6) . ?
C11 N2 1.339(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.349(6) . ?
C13 H13 0.9300 . ?
C13 N1 1.346(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.351(7) . ?
C14 N3 1.351(6) . ?
C15 H15 0.9300 . ?
C15 C16 1.403(7) . ?
C16 C17 1.411(6) . ?
C16 N4 1.337(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.336(7) . ?
C18 H18 0.9300 . ?
C18 N3 1.351(6) . ?
N2 H2A 0.8599 . ?
N2 H2B 0.8607 . ?
N4 H4A 0.8656 . ?
N4 H4B 0.8663 . ?
Br1 Cu1 2.3792(10) . ?
Br2 Cu1 2.3489(9) . ?
Br3 Cu1 2.3680(11) . ?

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
C2 C1 H1 120.3 . . ?
C6 C1 H1 120.3 . . ?
C6 C1 C2 119.5(5) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 C1 121.1(5) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.9(5) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 119.2(5) . . ?
C3 C4 C8 121.0(5) . . ?
C5 C4 C8 119.7(4) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 C4 121.3(4) . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C7 120.8(5) . . ?
C5 C6 C1 119.1(5) . . ?
C5 C6 C7 120.1(4) . . ?
C6 C7 H7A 109.4 . . ?
C6 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
N3 C7 C6 111.1(4) . . ?
N3 C7 H7A 109.4 . . ?
N3 C7 H7B 109.4 . . ?
C4 C8 H8A 109.0 . . ?
C4 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
N1 C8 C4 112.7(4) . . ?
N1 C8 H8A 109.0 . . ?
N1 C8 H8B 109.0 . . ?
C10 C9 H9 118.9 . . ?
N1 C9 H9 118.9 . . ?
N1 C9 C10 122.2(4) . . ?
C9 C10 H10 120.3 . . ?
C9 C10 C11 119.5(4) . . ?
C11 C10 H10 120.3 . . ?
C12 C11 C10 116.7(4) . . ?
N2 C11 C10 121.3(5) . . ?
N2 C11 C12 121.9(4) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.6(4) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 119.3 . . ?
N1 C13 C12 121.3(4) . . ?
N1 C13 H13 119.3 . . ?
C15 C14 H14 118.9 . . ?
C15 C14 N3 122.2(4) . . ?
N3 C14 H14 118.9 . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.3(4) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C17 116.1(4) . . ?
N4 C16 C15 122.2(4) . . ?
N4 C16 C17 121.7(5) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.6(4) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 H18 118.8 . . ?
C17 C18 N3 122.4(4) . . ?
N3 C18 H18 118.8 . . ?
C9 N1 C8 120.0(4) . . ?
C9 N1 C13 119.7(4) . . ?
C13 N1 C8 120.2(4) . . ?
C11 N2 H2A 108.7 . . ?
C11 N2 H2B 108.9 . . ?
H2A N2 H2B 109.5 . . ?
C14 N3 C7 121.5(4) . . ?
C18 N3 C7 120.1(4) . . ?
C18 N3 C14 118.3(4) . . ?
C16 N4 H4A 108.3 . . ?
C16 N4 H4B 111.1 . . ?
H4A N4 H4B 108.2 . . ?
Br2 Cu1 Br1 123.38(4) . . ?
Br2 Cu1 Br3 123.72(4) . . ?
Br3 Cu1 Br1 112.65(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
N2 H2A Br1 0.86 2.68 3.457(5) 151.4 2_645
N4 H4A Br3 0.87 2.55 3.346(4) 152.7 3_766

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
C1 C2 C3 C4 -1.6(10) . . . . ?
C1 C6 C7 N3 -67.3(6) . . . . ?
C2 C1 C6 C5 -0.2(8) . . . . ?
C2 C1 C6 C7 178.0(5) . . . . ?
C2 C3 C4 C5 1.1(8) . . . . ?
C2 C3 C4 C8 178.4(6) . . . . ?
C3 C4 C5 C6 -0.1(7) . . . . ?
C3 C4 C8 N1 56.1(7) . . . . ?
C4 C5 C6 C1 -0.3(7) . . . . ?
C4 C5 C6 C7 -178.5(4) . . . . ?
C4 C8 N1 C9 59.2(7) . . . . ?
C4 C8 N1 C13 -125.2(5) . . . . ?
C5 C4 C8 N1 -126.6(5) . . . . ?
C5 C6 C7 N3 110.9(5) . . . . ?
C6 C1 C2 C3 1.2(10) . . . . ?
C6 C7 N3 C14 125.8(5) . . . . ?
C6 C7 N3 C18 -54.6(6) . . . . ?
C8 C4 C5 C6 -177.5(4) . . . . ?
C9 C10 C11 C12 -0.6(7) . . . . ?
C9 C10 C11 N2 177.8(5) . . . . ?
C10 C9 N1 C8 176.7(5) . . . . ?
C10 C9 N1 C13 1.0(7) . . . . ?
C10 C11 C12 C13 0.2(7) . . . . ?
C11 C12 C13 N1 0.8(8) . . . . ?
C12 C13 N1 C8 -177.1(5) . . . . ?
C12 C13 N1 C9 -1.4(7) . . . . ?
C14 C15 C16 C17 -3.8(7) . . . . ?
C14 C15 C16 N4 173.7(5) . . . . ?
C15 C14 N3 C7 -179.1(5) . . . . ?
C15 C14 N3 C18 1.3(7) . . . . ?
C15 C16 C17 C18 2.5(7) . . . . ?
C16 C17 C18 N3 0.6(8) . . . . ?
C17 C18 N3 C7 177.8(5) . . . . ?
C17 C18 N3 C14 -2.6(7) . . . . ?
N1 C9 C10 C11 0.0(8) . . . . ?
N2 C11 C12 C13 -178.1(5) . . . . ?
N3 C14 C15 C16 2.0(7) . . . . ?
N4 C16 C17 C18 -175.0(5) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
