# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 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_3
_database_code_depnum_ccdc_archive 'CCDC 1855114'
_audit_update_record             
;
2018-07-11 deposited with the CCDC.
2018-09-03 downloaded from the CCDC.
;
_audit_creation_date             2017-09-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_formula_moiety         'C21 H24 Br Cu N2 Se'
_chemical_formula_sum            'C21 H24 Br Cu N2 Se'
_chemical_formula_weight         526.85
_chemical_oxdiff_formula         'C21 H24 N2 Se Cu Br'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cu -1.96878 0.60861 13.33800 7.16760 5.61580 1.67350 3.58280 0.24700 11.39660
64.81260 1.19099998474
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.67402 1.33011 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Se -0.79210 1.18296 17.00060 5.81960 3.97310 4.35430 2.40980 0.27260 15.23720
43.81630 2.84089994431
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   11.2243(6)
_cell_length_b                   15.3677(7)
_cell_length_c                   13.7853(6)
_cell_angle_alpha                90
_cell_angle_beta                 112.650(6)
_cell_angle_gamma                90
_cell_volume                     2194.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2570
_cell_measurement_temperature    298
_cell_measurement_theta_max      70.5780
_cell_measurement_theta_min      4.2300
_exptl_absorpt_coefficient_mu    5.472
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70307
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.5946
_exptl_crystal_description       block
_exptl_crystal_F_000             1035.9767
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5465
_diffrn_reflns_theta_full        70.9743
_diffrn_reflns_theta_max         70.97
_diffrn_reflns_theta_min         4.27
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1293
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 1.0000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -108.00  -39.00   1.0000    2.6400
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000  -60.0000 69

#__ type_ start__ end____ width___ exp.time_
  2 omega -104.00  -61.00   1.0000    2.6400
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000  150.0000 43

#__ type_ start__ end____ width___ exp.time_
  3 omega   44.00   70.00   1.0000    2.6400
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -38.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega  -12.00   40.00   1.0000    2.6400
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -38.0000  -60.0000 52

#__ type_ start__ end____ width___ exp.time_
  5 omega   23.00   51.00   1.0000    2.6400
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000 -180.0000 28

#__ type_ start__ end____ width___ exp.time_
  6 omega   63.00   89.00   1.0000    2.6400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
  7 omega   54.00   80.00   1.0000    2.6400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
  8 omega   37.00   93.00   1.0000    2.6400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   90.0000 56

#__ type_ start__ end____ width___ exp.time_
  9 omega   54.00   98.00   1.0000    2.6400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000  -30.0000 44

#__ type_ start__ end____ width___ exp.time_
 10 omega   67.00   93.00   1.0000    2.6400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 11 omega   40.00   68.00   1.0000    2.6400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -30.0000 28

#__ type_ start__ end____ width___ exp.time_
 12 omega   42.00  104.00   1.0000    2.6400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000  -90.0000 62

#__ type_ start__ end____ width___ exp.time_
 13 omega  106.00  132.00   1.0000    2.6400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 14 omega  149.00  177.00   1.0000    2.6400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000    0.0000 28

#__ type_ start__ end____ width___ exp.time_
 15 omega   62.00   93.00   1.0000    2.6400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   30.0000 31
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0801366000
_diffrn_orient_matrix_UB_12      -0.0506179000
_diffrn_orient_matrix_UB_13      -0.0503291000
_diffrn_orient_matrix_UB_21      0.0181776000
_diffrn_orient_matrix_UB_22      -0.0746619000
_diffrn_orient_matrix_UB_23      0.0789322000
_diffrn_orient_matrix_UB_31      -0.1240615000
_diffrn_orient_matrix_UB_32      -0.0435755000
_diffrn_orient_matrix_UB_33      -0.0767900000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -13
_reflns_limit_k_max              18
_reflns_limit_k_min              0
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                2727
_reflns_number_total             3449
_reflns_odcompleteness_completeness 83.31
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.8168
_refine_diff_density_min         -0.8436
_refine_diff_density_rms         0.0976
_refine_ls_d_res_high            0.8155
_refine_ls_d_res_low             10.3585
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0298
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    36
_refine_ls_number_parameters     241
_refine_ls_number_reflns         3449
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0556
_refine_ls_restrained_S_all      1.0298
_refine_ls_shift/su_max          0.0014
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1512P)²+0.6865P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1715
_refine_ls_wR_factor_ref         0.2135
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C8(H8), C16(H16), C19(H19)
2.b Idealised Me refined as rotating group:
 C10(H10a,H10b,H10c), C11(H11a,H11b,H11c), C12(H12a,H12b,H12c), C15(H15a,H15b,
 H15c), C18(H18a,H18b,H18c), C21(H21a,H21b,H21c)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
Br1 Br 0.38614(7) 0.12694(6) 0.15360(8) 0.1037(4) Uani 1.000000 .
Se1 Se 0.00452(7) 0.24622(6) 0.08944(5) 0.0859(4) Uani 1.000000 .
Cu1 Cu 0.18926(8) 0.18482(6) 0.09667(7) 0.0728(4) Uani 1.000000 .
N1 N -0.0768(4) 0.2277(3) -0.1367(3) 0.0542(9) Uani 1.000000 .
N2 N -0.2160(4) 0.2931(3) -0.0895(3) 0.0518(9) Uani 1.000000 .
C1 C -0.0991(5) 0.2556(3) -0.0524(4) 0.0542(11) Uani 1.000000 .
C2 C -0.1819(6) 0.2495(3) -0.2275(4) 0.0611(13) Uani 1.000000 .
H2 H -0.1900(6) 0.2383(3) -0.2960(4) 0.0734(15) Uiso 1.000000 R
C3 C -0.2695(6) 0.2895(4) -0.1991(4) 0.0621(12) Uani 1.000000 .
H3 H -0.3497(6) 0.3106(4) -0.2435(4) 0.0745(15) Uiso 1.000000 R
C4 C -0.2841(5) 0.3259(3) -0.0264(4) 0.0540(11) Uani 1.000000 .
C5 C -0.2595(6) 0.4092(4) 0.0129(5) 0.0684(14) Uani 1.000000 .
C6 C -0.3264(7) 0.4395(4) 0.0720(5) 0.0756(17) Uani 1.000000 .
H6 H -0.3088(7) 0.4947(4) 0.1017(5) 0.091(2) Uiso 1.000000 R
C7 C -0.4189(6) 0.3885(4) 0.0873(4) 0.0718(15) Uani 1.000000 .
C8 C -0.4417(6) 0.3058(4) 0.0466(5) 0.0691(14) Uani 1.000000 .
H8 H -0.5041(6) 0.2715(4) 0.0570(5) 0.0829(17) Uiso 1.000000 R
C9 C -0.3723(6) 0.2723(4) -0.0103(4) 0.0616(12) Uani 1.000000 .
C10 C -0.3953(8) 0.1803(4) -0.0511(7) 0.089(2) Uani 1.000000 .
H10a H -0.438(6) 0.1812(4) -0.1263(8) 0.133(3) Uiso 1.000000 GR
H10b H -0.3141(10) 0.1507(14) -0.032(5) 0.133(3) Uiso 1.000000 GR
H10c H -0.448(6) 0.1506(14) -0.021(4) 0.133(3) Uiso 1.000000 GR
C11 C -0.1568(9) 0.4655(4) -0.0028(8) 0.096(2) Uani 1.000000 .
H11a H -0.0746(15) 0.454(3) 0.053(3) 0.145(4) Uiso 1.000000 GR
H11b H -0.152(4) 0.452(3) -0.069(2) 0.145(4) Uiso 1.000000 GR
H11c H -0.179(3) 0.5258(4) -0.002(5) 0.145(4) Uiso 1.000000 GR
C12 C -0.4933(8) 0.4211(6) 0.1509(6) 0.098(2) Uani 1.000000 .
H12a H -0.439(2) 0.419(4) 0.2243(7) 0.147(4) Uiso 1.000000 GR
H12b H -0.521(6) 0.4799(17) 0.131(4) 0.147(4) Uiso 1.000000 GR
H12c H -0.568(4) 0.385(3) 0.138(4) 0.147(4) Uiso 1.000000 GR
C13 C 0.0306(5) 0.1752(3) -0.1361(4) 0.0551(11) Uani 1.000000 .
C14 C 0.1386(5) 0.2149(3) -0.1411(4) 0.0564(11) Uani 1.000000 .
C15 C 0.1550(7) 0.3125(3) -0.1347(5) 0.0686(14) Uani 1.000000 .
H15a H 0.0724(10) 0.3399(3) -0.169(4) 0.103(2) Uiso 1.000000 GR
H15b H 0.191(5) 0.3301(5) -0.0623(5) 0.103(2) Uiso 1.000000 GR
H15c H 0.212(4) 0.3297(5) -0.169(4) 0.103(2) Uiso 1.000000 GR
C16 C 0.2333(6) 0.1625(4) -0.1515(4) 0.0629(13) Uani 1.000000 .
H16 H 0.3058(6) 0.1884(4) -0.1563(4) 0.0755(15) Uiso 1.000000 R
C17 C 0.2234(6) 0.0729(4) -0.1548(5) 0.0675(14) Uani 1.000000 .
C18 C 0.3273(8) 0.0173(4) -0.1655(8) 0.095(2) Uani 1.000000 .
H18a H 0.344(5) 0.036(3) -0.225(3) 0.143(3) Uiso 1.000000 GR
H18b H 0.405(2) 0.023(3) -0.103(2) 0.143(3) Uiso 1.000000 GR
H18c H 0.300(3) -0.0423(8) -0.175(5) 0.143(3) Uiso 1.000000 GR
C19 C 0.1122(6) 0.0367(3) -0.1507(5) 0.0683(14) Uani 1.000000 .
H19 H 0.1029(6) -0.0235(3) -0.1555(5) 0.0820(17) Uiso 1.000000 R
C20 C 0.0150(6) 0.0852(4) -0.1397(5) 0.0632(13) Uani 1.000000 .
C21 C -0.1049(7) 0.0436(4) -0.1365(7) 0.0836(19) Uani 1.000000 .
H21a H -0.113(3) 0.058(3) -0.072(2) 0.125(3) Uiso 1.000000 GR
H21b H -0.1791(9) 0.064(3) -0.195(3) 0.125(3) Uiso 1.000000 GR
H21c H -0.099(2) -0.0184(5) -0.141(5) 0.125(3) Uiso 1.000000 GR


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
Br1 Cu1 2.2259(11) . ?
Se1 Cu1 2.2452(11) . ?
Se1 C1 1.856(5) . ?
N1 C1 1.350(6) . ?
N1 C2 1.391(7) . ?
N1 C13 1.448(6) . ?
N2 C1 1.341(6) . ?
N2 C3 1.396(6) . ?
N2 C4 1.451(6) . ?
C2 C3 1.338(8) . ?
C4 C5 1.376(8) . ?
C4 C9 1.370(7) . ?
C5 C6 1.383(8) . ?
C5 C11 1.521(9) . ?
C6 C7 1.381(9) . ?
C7 C8 1.374(9) . ?
C7 C12 1.510(8) . ?
C8 C9 1.399(7) . ?
C9 C10 1.506(8) . ?
C13 C14 1.383(7) . ?
C13 C20 1.393(7) . ?
C14 C15 1.510(7) . ?
C14 C16 1.384(7) . ?
C16 C17 1.381(8) . ?
C17 C18 1.499(8) . ?
C17 C19 1.388(8) . ?
C19 C20 1.378(8) . ?
C20 C21 1.506(8) . ?

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
C1 Se1 Cu1 105.84(15) . . ?
Se1 Cu1 Br1 163.36(6) . . ?
C2 N1 C1 108.9(4) . . ?
C13 N1 C1 127.0(4) . . ?
C13 N1 C2 123.7(4) . . ?
C3 N2 C1 110.2(4) . . ?
C4 N2 C1 125.7(4) . . ?
C4 N2 C3 123.8(4) . . ?
N1 C1 Se1 129.3(4) . . ?
N2 C1 Se1 124.0(4) . . ?
N2 C1 N1 106.6(5) . . ?
C3 C2 N1 108.2(5) . . ?
C2 C3 N2 106.0(5) . . ?
C5 C4 N2 119.1(5) . . ?
C9 C4 N2 117.9(4) . . ?
C9 C4 C5 123.0(5) . . ?
C6 C5 C4 118.1(6) . . ?
C11 C5 C4 121.4(5) . . ?
C11 C5 C6 120.4(6) . . ?
C7 C6 C5 120.7(6) . . ?
C8 C7 C6 119.7(5) . . ?
C12 C7 C6 121.2(6) . . ?
C12 C7 C8 119.1(6) . . ?
C9 C8 C7 120.9(6) . . ?
C8 C9 C4 117.6(5) . . ?
C10 C9 C4 122.3(5) . . ?
C10 C9 C8 120.1(5) . . ?
C14 C13 N1 119.9(4) . . ?
C20 C13 N1 117.4(5) . . ?
C20 C13 C14 122.5(5) . . ?
C15 C14 C13 121.6(5) . . ?
C16 C14 C13 118.1(5) . . ?
C16 C14 C15 120.2(5) . . ?
C17 C16 C14 121.9(5) . . ?
C18 C17 C16 121.1(6) . . ?
C19 C17 C16 117.5(5) . . ?
C19 C17 C18 121.5(5) . . ?
C20 C19 C17 123.4(5) . . ?
C19 C20 C13 116.6(5) . . ?
C21 C20 C13 121.5(5) . . ?
C21 C20 C19 121.9(5) . . ?

_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
_database_code_depnum_ccdc_archive 'CCDC 1855115'
_audit_update_record             
;
2018-07-11 deposited with the CCDC.
2018-09-03 downloaded from the CCDC.
;
_audit_creation_date             2017-09-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_formula_moiety         'C21 H24 Cl Cu N2 S'
_chemical_formula_sum            'C21 H24 Cl Cu N2 S'
_chemical_formula_weight         435.50
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.36843 0.69943 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.33537 0.55136 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cu -1.96878 0.60861 13.33800 7.16760 5.61580 1.67350 3.58280 0.24700 11.39660
64.81260 1.19099998474
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   11.0627(5)
_cell_length_b                   15.3677(6)
_cell_length_c                   13.7074(6)
_cell_angle_alpha                90
_cell_angle_beta                 113.378(5)
_cell_angle_gamma                90
_cell_volume                     2139.06(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2277
_cell_measurement_temperature    298
_cell_measurement_theta_max      70.7310
_cell_measurement_theta_min      4.3520
_exptl_absorpt_coefficient_mu    3.540
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77068
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.3522
_exptl_crystal_description       block
_exptl_crystal_F_000             900.6827
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.19
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5620
_diffrn_reflns_theta_full        70.9745
_diffrn_reflns_theta_max         70.97
_diffrn_reflns_theta_min         4.35
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1293
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 1.0000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -5.00   25.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000 -120.0000 30

#__ type_ start__ end____ width___ exp.time_
  2 omega  -49.00   29.00   1.0000    3.0700
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   57.0000   90.0000 78

#__ type_ start__ end____ width___ exp.time_
  3 omega   24.00   91.00   1.0000    3.0700
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -19.0000  150.0000 67

#__ type_ start__ end____ width___ exp.time_
  4 omega   68.00   95.00   1.0000    3.0700
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -124.0000  124.0000 27

#__ type_ start__ end____ width___ exp.time_
  5 omega   23.00   48.00   1.0000    3.0700
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -124.0000  124.0000 25

#__ type_ start__ end____ width___ exp.time_
  6 omega  -16.00   19.00   1.0000    3.0700
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -19.0000  150.0000 35

#__ type_ start__ end____ width___ exp.time_
  7 omega   36.00   65.00   1.0000    3.0700
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  -30.0000 29

#__ type_ start__ end____ width___ exp.time_
  8 omega   60.00   99.00   1.0000    3.0700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000   60.0000 39

#__ type_ start__ end____ width___ exp.time_
  9 omega   45.00   80.00   1.0000    3.0700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000   30.0000 35

#__ type_ start__ end____ width___ exp.time_
 10 omega   46.00   73.00   1.0000    3.0700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   30.0000 27

#__ type_ start__ end____ width___ exp.time_
 11 omega   47.00   78.00   1.0000    3.0700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -150.0000 31

#__ type_ start__ end____ width___ exp.time_
 12 omega   37.00  111.00   1.0000    3.0700
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -150.0000 74

#__ type_ start__ end____ width___ exp.time_
 13 omega   50.00   82.00   1.0000    3.0700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -120.0000 32

#__ type_ start__ end____ width___ exp.time_
 14 omega   97.00  164.00   1.0000    3.0700
omega____ theta____ kappa____ phi______ frames
    -      108.0000   56.0000  -29.0000 67
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0286885000
_diffrn_orient_matrix_UB_12      0.0956321000
_diffrn_orient_matrix_UB_13      -0.0171368000
_diffrn_orient_matrix_UB_21      -0.0546980000
_diffrn_orient_matrix_UB_22      0.0290397000
_diffrn_orient_matrix_UB_23      0.0821440000
_diffrn_orient_matrix_UB_31      0.1384988000
_diffrn_orient_matrix_UB_32      -0.0084057000
_diffrn_orient_matrix_UB_33      0.0891226000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -13
_reflns_limit_k_max              18
_reflns_limit_k_min              0
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                2713
_reflns_number_total             3448
_reflns_odcompleteness_completeness 86.07
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.6079
_refine_diff_density_min         -0.2990
_refine_diff_density_rms         0.0922
_refine_ls_d_res_high            0.8155
_refine_ls_d_res_low             10.1545
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0623
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    36
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3448
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0506
_refine_ls_restrained_S_all      1.0623
_refine_ls_shift/su_max          0.0002
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1022P)²+0.1605P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1450
_refine_ls_wR_factor_ref         0.1700
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H10a,H10b,H10c} of C10, {H20a,H20b,H20c} of C20, {H11a,
  H11b,H11c} of C11
 At 1.5 times of:
  {H12a,H12b,H12c} of C12, {H19a,H19b,H19c} of C19, {H21a,H21b,H21c} of C21
2.a Riding coordinates:
 C10(H10a,H10b,H10c), C11(H11a,H11b,H11c), C20(H20a,H20b,H20c)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C8(H8), C15(H15), C17(H17)
2.c Idealised Me refined as rotating group:
 C12(H12a,H12b,H12c), C19(H19a,H19b,H19c), C21(H21a,H21b,H21c)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
Cu1 Cu 0.68296(5) 0.31041(4) 0.60280(5) 0.0703(3) Uani 1.000000 .
Cl1 Cl 0.87811(11) 0.35500(11) 0.65913(13) 0.1145(5) Uani 1.000000 .
S1 S 0.49471(10) 0.26325(9) 0.58605(7) 0.0782(4) Uani 1.000000 .
N1 N 0.4217(3) 0.27285(18) 0.3689(2) 0.0517(6) Uani 1.000000 .
N2 N 0.2818(3) 0.20755(18) 0.4184(2) 0.0509(6) Uani 1.000000 .
C1 C 0.3998(3) 0.2483(2) 0.4550(2) 0.0512(7) Uani 1.000000 .
C2 C 0.3150(4) 0.2480(2) 0.2775(2) 0.0594(9) Uani 1.000000 .
H2 H 0.3058(4) 0.2577(2) 0.2079(2) 0.0713(11) Uiso 1.000000 R
C3 C 0.2281(4) 0.2079(2) 0.3075(3) 0.0579(8) Uani 1.000000 .
H3 H 0.1474(4) 0.1846(2) 0.2630(3) 0.0695(10) Uiso 1.000000 R
C4 C 0.2155(3) 0.1738(2) 0.4820(3) 0.0533(8) Uani 1.000000 .
C5 C 0.2464(4) 0.0904(2) 0.5241(3) 0.0649(9) Uani 1.000000 .
C6 C 0.1755(4) 0.0591(3) 0.5808(3) 0.0736(11) Uani 1.000000 .
H6 H 0.1945(4) 0.0038(3) 0.6105(3) 0.0883(13) Uiso 1.000000 R
C7 C 0.0790(4) 0.1065(3) 0.5944(3) 0.0720(11) Uani 1.000000 .
C8 C 0.0521(4) 0.1896(3) 0.5521(3) 0.0700(11) Uani 1.000000 .
H8 H -0.0132(4) 0.2224(3) 0.5613(3) 0.0840(13) Uiso 1.000000 R
C9 C 0.1213(4) 0.2247(3) 0.4958(3) 0.0606(9) Uani 1.000000 .
C10 C 0.3548(5) 0.0389(3) 0.5123(4) 0.0947(15) Uani 1.000000 .
H10a H 0.4105(5) 0.0754(3) 0.4911(4) 0.1136(18) Uiso 1.000000 R
H10b H 0.3186(5) -0.0066(3) 0.4608(4) 0.1136(18) Uiso 1.000000 R
H10c H 0.4054(5) 0.0137(3) 0.5804(4) 0.1136(18) Uiso 1.000000 R
C11 C 0.0019(5) 0.0712(4) 0.6559(4) 0.1028(18) Uani 1.000000 .
H11a H -0.0349(5) 0.1157(4) 0.6851(4) 0.123(2) Uiso 1.000000 R
H11b H 0.0636(5) 0.0372(4) 0.7126(4) 0.123(2) Uiso 1.000000 R
H11c H -0.0673(5) 0.0342(4) 0.6101(4) 0.123(2) Uiso 1.000000 R
C12 C 0.0949(5) 0.3159(3) 0.4528(4) 0.0852(13) Uani 1.000000 .
H12a H 0.038(3) 0.3448(9) 0.480(2) 0.128(2) Uiso 1.000000 GR
H12b H 0.1765(6) 0.3471(8) 0.474(3) 0.128(2) Uiso 1.000000 GR
H12c H 0.053(3) 0.3140(3) 0.3766(4) 0.128(2) Uiso 1.000000 GR
C13 C 0.5269(3) 0.3262(2) 0.3671(2) 0.0499(7) Uani 1.000000 .
C14 C 0.6363(3) 0.2875(2) 0.3598(2) 0.0519(7) Uani 1.000000 .
C15 C 0.7293(4) 0.3415(2) 0.3479(3) 0.0595(8) Uani 1.000000 .
H15 H 0.8029(4) 0.3167(2) 0.3422(3) 0.0714(10) Uiso 1.000000 R
C16 C 0.7170(4) 0.4311(2) 0.3440(3) 0.0637(9) Uani 1.000000 .
C17 C 0.6057(4) 0.4673(2) 0.3522(3) 0.0636(9) Uani 1.000000 .
H17 H 0.5968(4) 0.5275(2) 0.3505(3) 0.0763(11) Uiso 1.000000 R
C18 C 0.5086(4) 0.4167(2) 0.3627(3) 0.0574(8) Uani 1.000000 .
C19 C 0.6551(4) 0.1903(2) 0.3667(3) 0.0666(10) Uani 1.000000 .
H19a H 0.660(3) 0.1702(3) 0.4346(10) 0.0998(15) Uiso 1.000000 GR
H19b H 0.5820(15) 0.1629(2) 0.3113(15) 0.0998(15) Uiso 1.000000 GR
H19c H 0.7351(16) 0.1758(3) 0.359(2) 0.0998(15) Uiso 1.000000 GR
C20 C 0.8191(5) 0.4882(3) 0.3312(4) 0.0921(15) Uani 1.000000 .
H20a H 0.8687(5) 0.5154(3) 0.3984(4) 0.1105(18) Uiso 1.000000 R
H20b H 0.7802(5) 0.5322(3) 0.2782(4) 0.1105(18) Uiso 1.000000 R
H20c H 0.8766(5) 0.4526(3) 0.3109(4) 0.1105(18) Uiso 1.000000 R
C21 C 0.3876(4) 0.4564(3) 0.3692(4) 0.0772(11) Uani 1.000000 .
H21a H 0.3106(4) 0.4281(14) 0.3192(18) 0.1158(17) Uiso 1.000000 GR
H21b H 0.3909(15) 0.4489(18) 0.4398(8) 0.1158(17) Uiso 1.000000 GR
H21c H 0.3843(17) 0.5173(5) 0.353(2) 0.1158(17) Uiso 1.000000 GR


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 Cl1 2.0985(13) . ?
Cu1 S1 2.1296(11) . ?
S1 C1 1.699(3) . ?
N1 C1 1.349(4) . ?
N1 C2 1.391(4) . ?
N1 C13 1.433(4) . ?
N2 C1 1.352(4) . ?
N2 C3 1.396(4) . ?
N2 C4 1.441(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.337(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.390(5) . ?
C4 C9 1.375(5) . ?
C5 C6 1.391(5) . ?
C5 C10 1.498(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.366(6) . ?
C7 C8 1.384(6) . ?
C7 C11 1.517(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.393(5) . ?
C9 C12 1.504(6) . ?
C10 H10a 0.9600 . ?
C10 H10b 0.9600 . ?
C10 H10c 0.9601 . ?
C11 H11a 0.9599 . ?
C11 H11b 0.9600 . ?
C11 H11c 0.9600 . ?
C12 H12a 0.9600 . ?
C12 H12b 0.9600 . ?
C12 H12c 0.9600 . ?
C13 C14 1.387(4) . ?
C13 C18 1.404(5) . ?
C14 C15 1.382(5) . ?
C14 C19 1.506(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.382(5) . ?
C16 C17 1.395(5) . ?
C16 C20 1.495(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.379(5) . ?
C18 C21 1.505(5) . ?
C19 H19a 0.9600 . ?
C19 H19b 0.9600 . ?
C19 H19c 0.9600 . ?
C20 H20a 0.9600 . ?
C20 H20b 0.9600 . ?
C20 H20c 0.9599 . ?
C21 H21a 0.9600 . ?
C21 H21b 0.9600 . ?
C21 H21c 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
S1 Cu1 Cl1 165.94(6) . . ?
C1 S1 Cu1 109.13(11) . . ?
C2 N1 C1 109.2(3) . . ?
C13 N1 C1 127.2(3) . . ?
C13 N1 C2 123.1(3) . . ?
C3 N2 C1 109.5(3) . . ?
C4 N2 C1 126.2(3) . . ?
C4 N2 C3 124.2(3) . . ?
N1 C1 S1 129.6(3) . . ?
N2 C1 S1 123.7(2) . . ?
N2 C1 N1 106.7(3) . . ?
H2 C2 N1 126.09(18) . . ?
C3 C2 N1 107.8(3) . . ?
C3 C2 H2 126.1(2) . . ?
C2 C3 N2 106.8(3) . . ?
H3 C3 N2 126.60(18) . . ?
H3 C3 C2 126.6(2) . . ?
C5 C4 N2 118.8(3) . . ?
C9 C4 N2 118.3(3) . . ?
C9 C4 C5 122.9(3) . . ?
C6 C5 C4 116.8(3) . . ?
C10 C5 C4 121.2(3) . . ?
C10 C5 C6 122.0(4) . . ?
H6 C6 C5 118.8(2) . . ?
C7 C6 C5 122.4(4) . . ?
C7 C6 H6 118.8(2) . . ?
C8 C7 C6 119.0(3) . . ?
C11 C7 C6 121.8(4) . . ?
C11 C7 C8 119.2(4) . . ?
H8 C8 C7 119.5(2) . . ?
C9 C8 C7 121.0(4) . . ?
C9 C8 H8 119.5(2) . . ?
C8 C9 C4 117.9(4) . . ?
C12 C9 C4 121.1(3) . . ?
C12 C9 C8 120.9(4) . . ?
H10a C10 C5 111.2 . . ?
H10b C10 C5 110.3 . . ?
H10b C10 H10a 109.5 . . ?
H10c C10 C5 106.9 . . ?
H10c C10 H10a 109.5 . . ?
H10c C10 H10b 109.5 . . ?
H11a C11 C7 113.6 . . ?
H11b C11 C7 105.6 . . ?
H11b C11 H11a 109.5 . . ?
H11c C11 C7 109.1 . . ?
H11c C11 H11a 109.5 . . ?
H11c C11 H11b 109.5 . . ?
H12a C12 C9 109.5 . . ?
H12b C12 C9 109.5 . . ?
H12b C12 H12a 109.5 . . ?
H12c C12 C9 109.5 . . ?
H12c C12 H12a 109.5 . . ?
H12c C12 H12b 109.5 . . ?
C14 C13 N1 119.6(3) . . ?
C18 C13 N1 117.6(3) . . ?
C18 C13 C14 122.5(3) . . ?
C15 C14 C13 117.5(3) . . ?
C19 C14 C13 121.6(3) . . ?
C19 C14 C15 120.9(3) . . ?
H15 C15 C14 118.8(2) . . ?
C16 C15 C14 122.4(3) . . ?
C16 C15 H15 118.8(2) . . ?
C17 C16 C15 118.1(3) . . ?
C20 C16 C15 121.4(3) . . ?
C20 C16 C17 120.5(3) . . ?
H17 C17 C16 118.9(2) . . ?
C18 C17 C16 122.2(3) . . ?
C18 C17 H17 118.9(2) . . ?
C17 C18 C13 117.2(3) . . ?
C21 C18 C13 121.0(3) . . ?
C21 C18 C17 121.8(3) . . ?
H19a C19 C14 109.5 . . ?
H19b C19 C14 109.5 . . ?
H19b C19 H19a 109.5 . . ?
H19c C19 C14 109.5 . . ?
H19c C19 H19a 109.5 . . ?
H19c C19 H19b 109.5 . . ?
H20a C20 C16 108.2 . . ?
H20b C20 C16 111.6 . . ?
H20b C20 H20a 109.5 . . ?
H20c C20 C16 108.5 . . ?
H20c C20 H20a 109.5 . . ?
H20c C20 H20b 109.5 . . ?
H21a C21 C18 109.5 . . ?
H21b C21 C18 109.5 . . ?
H21b C21 H21a 109.5 . . ?
H21c C21 C18 109.5 . . ?
H21c C21 H21a 109.5 . . ?
H21c C21 H21b 109.5 . . ?

_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_14
_database_code_depnum_ccdc_archive 'CCDC 1855122'
_audit_update_record             
;
2018-07-11 deposited with the CCDC.
2018-09-03 downloaded from the CCDC.
;
_audit_creation_date             2017-09-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C21 H33 Cu N6 Se3, B F4'
_chemical_formula_sum            'C21 H33 B Cu F4 N6 Se3'
_chemical_formula_weight         756.78
_chemical_absolute_configuration unk
_chemical_oxdiff_formula         'C21 H24 N2 S Cu O F Cl B'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
B 0.00963 0.00408 2.05450 1.33260 1.09790 0.70680 23.21850 1.02100 60.34980
0.14030 -0.193200007081
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.07537 0.05506 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cu -1.96878 0.60861 13.33800 7.16760 5.61580 1.67350 3.58280 0.24700 11.39660
64.81260 1.19099998474
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Se -0.79210 1.18296 17.00060 5.81960 3.97310 4.35430 2.40980 0.27260 15.23720
43.81630 2.84089994431
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      tetragonal
_space_group_IT_number           92
_space_group_name_H-M_alt        'P 41 21 2'
_space_group_name_Hall           ' P 4abw 2nw'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -y+1/2,x+1/2,z+1/4
3 y+1/2,-x+1/2,z+3/4
4 x+1/2,-y+1/2,-z+3/4
5 -x+1/2,y+1/2,-z+1/4
6 -x,-y,z+1/2
7 y,x,-z
8 -y,-x,-z+1/2

_symmetry_Int_Tables_number      92
_cell_length_a                   16.4174(2)
_cell_length_b                   16.4174(2)
_cell_length_c                   22.1831(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5979.02(16)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4920
_cell_measurement_temperature    298
_cell_measurement_theta_max      71.3255
_cell_measurement_theta_min      3.3463
_exptl_absorpt_coefficient_mu    5.613
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67767
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.6813
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2955.9276
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12308
_diffrn_reflns_theta_full        71.4667
_diffrn_reflns_theta_max         71.47
_diffrn_reflns_theta_min         3.35
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean 16.1293
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 1.0000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -2.00   40.00   1.0000    2.8000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   38.0000  -30.0000 42

#__ type_ start__ end____ width___ exp.time_
  2 omega  -37.00   23.00   1.0000   11.2100
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   25.0000  150.0000 60

#__ type_ start__ end____ width___ exp.time_
  3 omega  -20.00   24.00   1.0000   11.2100
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   38.0000    0.0000 44

#__ type_ start__ end____ width___ exp.time_
  4 omega  -20.00   25.00   1.0000   11.2100
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   38.0000  -90.0000 45

#__ type_ start__ end____ width___ exp.time_
  5 omega   98.00  157.00   1.0000   11.2100
omega____ theta____ kappa____ phi______ frames
    -      110.2786   77.0000   90.0000 59

#__ type_ start__ end____ width___ exp.time_
  6 omega   41.00   86.00   1.0000   11.2100
omega____ theta____ kappa____ phi______ frames
    -      110.2786  -38.0000 -180.0000 45

#__ type_ start__ end____ width___ exp.time_
  7 omega   46.00   81.00   1.0000   11.2100
omega____ theta____ kappa____ phi______ frames
    -      110.2786  -38.0000   30.0000 35

#__ type_ start__ end____ width___ exp.time_
  8 omega   44.00   96.00   1.0000   11.2100
omega____ theta____ kappa____ phi______ frames
    -      110.2786  -50.0000 -120.0000 52

#__ type_ start__ end____ width___ exp.time_
  9 omega   38.00  114.00   1.0000   11.2100
omega____ theta____ kappa____ phi______ frames
    -      110.2786 -111.0000 -180.0000 76

#__ type_ start__ end____ width___ exp.time_
 10 omega   40.00   66.00   1.0000   11.2100
omega____ theta____ kappa____ phi______ frames
    -      110.2786  -38.0000  120.0000 26
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0442655000
_diffrn_orient_matrix_UB_12      -0.0594867000
_diffrn_orient_matrix_UB_13      0.0425447000
_diffrn_orient_matrix_UB_21      0.0827586000
_diffrn_orient_matrix_UB_22      0.0300796000
_diffrn_orient_matrix_UB_23      -0.0240328000
_diffrn_orient_matrix_UB_31      0.0021519000
_diffrn_orient_matrix_UB_32      0.0659902000
_diffrn_orient_matrix_UB_33      0.0493472000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.938
_reflns_limit_h_max              20
_reflns_limit_h_min              -20
_reflns_limit_k_max              14
_reflns_limit_k_min              -13
_reflns_limit_l_max              26
_reflns_limit_l_min              -26
_reflns_number_gt                4859
_reflns_number_total             5646
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.3487
_refine_diff_density_min         -0.4325
_refine_diff_density_rms         0.0625
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_d_res_high            0.8131
_refine_ls_d_res_low             13.1964
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0445
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    51
_refine_ls_number_parameters     331
_refine_ls_number_reflns         5646
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0395
_refine_ls_restrained_S_all      1.0445
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0577P)²+2.2142P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1120
_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 Ternary CH refined with riding coordinates:
 C4(H4), C11(H11), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7a,H7b), C14(H14a,H14b), C21(H21a,H21b)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C3(H3), C2(H2), C10(H10), C16(H16), C17(H17)
2.d Idealised Me refined as rotating group:
 C13(H13a,H13b,H13c), C6(H6a,H6b,H6c), C5(H5a,H5b,H5c), C12(H12a,H12b,H12c),
 C20(H20a,H20b,H20c), C19(H19a,H19b,H19c)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
Se1 Se 0.50081(4) 0.73442(4) 0.06826(2) 0.0770(2) Uani 1.000000 .
Se2 Se 0.63725(5) 0.84625(4) 0.20339(3) 0.0796(2) Uani 1.000000 .
Se3 Se 0.56334(4) 0.61341(5) 0.21477(3) 0.0892(2) Uani 1.000000 .
Cu1 Cu 0.56970(5) 0.73623(5) 0.16039(3) 0.0650(2) Uani 1.000000 .
N4 N 0.6166(3) 0.8232(3) 0.33149(18) 0.0648(10) Uani 1.000000 .
C1 C 0.5316(3) 0.8332(3) 0.0341(2) 0.0652(12) Uani 1.000000 .
N2 N 0.5135(3) 0.9085(3) 0.05266(18) 0.0630(9) Uani 1.000000 .
C8 C 0.6567(4) 0.8043(3) 0.2807(2) 0.0691(13) Uani 1.000000 .
N1 N 0.5761(3) 0.8422(3) -0.01694(19) 0.0769(12) Uani 1.000000 .
C9 C 0.7120(4) 0.7371(4) 0.3575(2) 0.0849(17) Uani 1.000000 .
H9 H 0.7462(4) 0.7031(4) 0.3795(2) 0.102(2) Uiso 1.000000 R
N3 N 0.7150(3) 0.7510(3) 0.29672(19) 0.0781(13) Uani 1.000000 .
N6 N 0.3959(6) 0.5959(9) 0.1828(6) 0.182(7) Uani 1.000000 .
C3 C 0.5464(4) 0.9663(4) 0.0141(3) 0.0776(15) Uani 1.000000 .
H3 H 0.5432(4) 1.0227(4) 0.0178(3) 0.0931(18) Uiso 1.000000 R
C7 C 0.4640(3) 0.9303(4) 0.1046(2) 0.0707(13) Uani 1.000000 .
H7a H 0.4630(3) 0.8849(4) 0.1325(2) 0.0849(16) Uiso 1.000000 R
H7b H 0.4889(3) 0.9762(4) 0.1251(2) 0.0849(16) Uiso 1.000000 R
C2 C 0.5839(4) 0.9235(4) -0.0299(3) 0.0817(16) Uani 1.000000 .
H2 H 0.6104(4) 0.9454(4) -0.0633(3) 0.0981(19) Uiso 1.000000 R
C10 C 0.6500(4) 0.7819(4) 0.3797(2) 0.0780(15) Uani 1.000000 .
H10 H 0.6331(4) 0.7846(4) 0.4197(2) 0.0936(18) Uiso 1.000000 R
C15 C 0.4731(6) 0.5688(7) 0.1780(4) 0.121(3) Uani 1.000000 .
N5 N 0.4743(9) 0.5048(10) 0.1412(4) 0.198(6) Uani 1.000000 .
C4 C 0.6062(5) 0.7765(5) -0.0550(3) 0.102(2) Uani 1.000000 .
H4 H 0.6037(5) 0.7258(5) -0.0318(3) 0.122(3) Uiso 1.000000 R
F3 F 0.0161(4) 0.6435(4) 0.1643(2) 0.159(2) Uani 1.000000 .
F4 F 0.0505(4) 0.6369(5) 0.2575(2) 0.176(3) Uani 1.000000 .
F2 F 0.1452(4) 0.6463(4) 0.1875(4) 0.172(3) Uani 1.000000 .
C13 C 0.7903(6) 0.6274(6) 0.2690(4) 0.141(4) Uani 1.000000 .
H13a H 0.815(5) 0.6226(7) 0.3080(17) 0.211(6) Uiso 1.000000 GR
H13b H 0.7393(8) 0.5986(12) 0.269(4) 0.211(6) Uiso 1.000000 GR
H13c H 0.826(4) 0.6045(14) 0.239(2) 0.211(6) Uiso 1.000000 GR
C14 C 0.5475(3) 0.8768(3) 0.3375(3) 0.0742(14) Uani 1.000000 .
H14a H 0.5180(3) 0.8777(3) 0.2996(3) 0.0890(16) Uiso 1.000000 R
H14b H 0.5112(3) 0.8549(3) 0.3679(3) 0.0890(16) Uiso 1.000000 R
C11 C 0.7755(5) 0.7153(5) 0.2551(3) 0.104(2) Uani 1.000000 .
H11 H 0.7554(5) 0.7201(5) 0.2137(3) 0.125(3) Uiso 1.000000 R
C6 C 0.5506(8) 0.7671(7) -0.1106(4) 0.157(4) Uani 1.000000 .
H6a H 0.4950(10) 0.762(6) -0.0977(5) 0.236(6) Uiso 1.000000 GR
H6b H 0.556(5) 0.814(3) -0.136(2) 0.236(6) Uiso 1.000000 GR
H6c H 0.566(4) 0.719(4) -0.133(3) 0.236(6) Uiso 1.000000 GR
C5 C 0.6923(6) 0.7889(7) -0.0748(5) 0.158(4) Uani 1.000000 .
H5a H 0.6934(8) 0.825(5) -0.109(3) 0.238(7) Uiso 1.000000 GR
H5b H 0.7233(15) 0.812(5) -0.0423(15) 0.238(7) Uiso 1.000000 GR
H5c H 0.7155(19) 0.7375(11) -0.086(4) 0.238(7) Uiso 1.000000 GR
C16 C 0.3908(16) 0.4923(17) 0.1245(9) 0.354(19) Uani 1.000000 .
H16 H 0.3711(16) 0.4518(17) 0.0991(9) 0.42(2) Uiso 1.000000 R
C12 C 0.8537(7) 0.7630(8) 0.2611(7) 0.196(6) Uani 1.000000 .
H12a H 0.8413(7) 0.8186(19) 0.271(6) 0.294(9) Uiso 1.000000 GR
H12b H 0.887(4) 0.740(5) 0.292(4) 0.294(9) Uiso 1.000000 GR
H12c H 0.883(4) 0.761(7) 0.224(2) 0.294(9) Uiso 1.000000 GR
C18 C 0.5457(17) 0.4559(16) 0.1281(11) 0.343(19) Uani 1.000000 .
H18 H 0.5915(17) 0.4825(16) 0.1485(11) 0.41(2) Uiso 1.000000 R
B1 B 0.0702(6) 0.6705(5) 0.2042(4) 0.092(2) Uani 1.000000 .
F1 F 0.0718(4) 0.7521(3) 0.2079(4) 0.178(3) Uani 1.000000 .
C17 C 0.3533(16) 0.5408(17) 0.1478(11) 0.341(17) Uani 1.000000 .
H17 H 0.2969(16) 0.5434(17) 0.1436(11) 0.41(2) Uiso 1.000000 R
C21 C 0.3689(8) 0.6622(9) 0.2203(10) 0.267(14) Uani 1.000000 .
H21a H 0.4137(8) 0.6995(9) 0.2271(10) 0.321(17) Uiso 1.000000 R
H21b H 0.3258(8) 0.6918(9) 0.1998(10) 0.321(17) Uiso 1.000000 R
C20 C 0.5395(18) 0.3746(14) 0.1538(13) 0.42(2) Uani 1.000000 .
H20a H 0.51(2) 0.376(5) 0.189(11) 0.63(3) Uiso 1.000000 GR
H20b H 0.52(2) 0.338(6) 0.125(7) 0.63(3) Uiso 1.000000 GR
H20c H 0.593(3) 0.356(10) 0.165(17) 0.63(3) Uiso 1.000000 GR
C19 C 0.5643(16) 0.4606(17) 0.0598(8) 0.45(2) Uani 1.000000 .
H19a H 0.55(3) 0.512(13) 0.044(5) 0.68(3) Uiso 1.000000 GR
H19b H 0.622(3) 0.46(3) 0.0535(17) 0.68(3) Uiso 1.000000 GR
H19c H 0.54(2) 0.417(19) 0.039(3) 0.68(3) Uiso 1.000000 GR


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
Se1 Cu1 2.3361(9) . ?
Se1 C1 1.860(5) . ?
Se2 Cu1 2.3242(10) . ?
Se2 C8 1.875(5) . ?
Se3 Cu1 2.3518(10) . ?
Se3 C15 1.843(10) . ?
N4 C8 1.341(7) . ?
N4 C10 1.379(7) . ?
N4 C14 1.443(7) . ?
C1 N2 1.336(7) . ?
C1 N1 1.355(7) . ?
N2 C3 1.387(7) . ?
N2 C7 1.455(7) . ?
C8 N3 1.345(7) . ?
N1 C2 1.372(8) . ?
N1 C4 1.456(8) . ?
C9 N3 1.369(7) . ?
C9 C10 1.348(9) . ?
N3 C11 1.478(8) . ?
N6 C15 1.348(15) . ?
N6 C17 1.38(3) . ?
N6 C21 1.44(2) . ?
C3 C2 1.352(9) . ?
C7 C14 1.526(8) 3_464 ?
C15 N5 1.331(16) . ?
N5 C16 1.44(3) . ?
N5 C18 1.45(3) . ?
C4 C6 1.543(13) . ?
C4 C5 1.494(12) . ?
F3 B1 1.331(10) . ?
F4 B1 1.344(9) . ?
F2 B1 1.346(10) . ?
C13 C11 1.495(12) . ?
C11 C12 1.510(14) . ?
C16 C17 1.13(4) . ?
C18 C20 1.46(3) . ?
C18 C19 1.55(2) . ?
B1 F1 1.342(10) . ?
C21 C21 1.50(3) 8_665 ?

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
C1 Se1 Cu1 102.33(15) . . ?
C8 Se2 Cu1 99.83(16) . . ?
C15 Se3 Cu1 98.6(3) . . ?
Se2 Cu1 Se1 126.86(4) . . ?
Se3 Cu1 Se1 114.60(4) . . ?
Se3 Cu1 Se2 118.49(4) . . ?
C10 N4 C8 110.1(4) . . ?
C14 N4 C8 127.1(4) . . ?
C14 N4 C10 122.8(5) . . ?
N2 C1 Se1 128.4(4) . . ?
N1 C1 Se1 125.6(4) . . ?
N1 C1 N2 106.0(5) . . ?
C3 N2 C1 110.9(5) . . ?
C7 N2 C1 126.6(4) . . ?
C7 N2 C3 122.5(5) . . ?
N4 C8 Se2 126.9(4) . . ?
N3 C8 Se2 127.0(4) . . ?
N3 C8 N4 106.0(4) . . ?
C2 N1 C1 109.4(5) . . ?
C4 N1 C1 125.9(5) . . ?
C4 N1 C2 124.5(5) . . ?
C10 C9 N3 107.2(5) . . ?
C9 N3 C8 110.1(5) . . ?
C11 N3 C8 124.9(5) . . ?
C11 N3 C9 125.0(5) . . ?
C17 N6 C15 102.4(19) . . ?
C21 N6 C15 125.9(13) . . ?
C21 N6 C17 131.5(17) . . ?
C2 C3 N2 105.5(5) . . ?
C14 C7 N2 112.7(4) 3_464 . ?
C3 C2 N1 108.2(5) . . ?
C9 C10 N4 106.6(5) . . ?
N6 C15 Se3 126.1(11) . . ?
N5 C15 Se3 125.0(10) . . ?
N5 C15 N6 108.9(12) . . ?
C16 N5 C15 104.9(18) . . ?
C18 N5 C15 124.9(13) . . ?
C18 N5 C16 129.9(19) . . ?
C6 C4 N1 109.6(7) . . ?
C5 C4 N1 113.0(8) . . ?
C5 C4 C6 109.8(7) . . ?
C7 C14 N4 114.0(5) 2_655 . ?
C13 C11 N3 111.3(8) . . ?
C12 C11 N3 108.1(7) . . ?
C12 C11 C13 110.2(8) . . ?
C17 C16 N5 108(3) . . ?
C20 C18 N5 111.8(16) . . ?
C19 C18 N5 109(3) . . ?
C19 C18 C20 116.3(19) . . ?
F4 B1 F3 106.7(6) . . ?
F2 B1 F3 109.2(8) . . ?
F2 B1 F4 109.9(8) . . ?
F1 B1 F3 112.7(8) . . ?
F1 B1 F4 111.2(9) . . ?
F1 B1 F2 107.1(7) . . ?
C16 C17 N6 116(3) . . ?
C21 C21 N6 110.8(9) 8_665 . ?

_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_7
_database_code_depnum_ccdc_archive 'CCDC 1855124'
_audit_update_record             
;
2018-07-11 deposited with the CCDC.
2018-09-03 downloaded from the CCDC.
;
_audit_creation_date             2017-09-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_formula_moiety         'C42 H48 Cu N4 Se2, Cl2 Cu'
_chemical_formula_sum            'C42 H48 Cl2 Cu2 N4 Se2'
_chemical_formula_weight         964.79
_chemical_oxdiff_formula         'C21 H24 N2 Se Cu Cl'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.36843 0.69943 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cu -1.96878 0.60861 13.33800 7.16760 5.61580 1.67350 3.58280 0.24700 11.39660
64.81260 1.19099998474
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Se -0.79210 1.18296 17.00060 5.81960 3.97310 4.35430 2.40980 0.27260 15.23720
43.81630 2.84089994431
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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 2ybc (x-z,y,z)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   8.3465(2)
_cell_length_b                   19.3330(5)
_cell_length_c                   13.4761(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.742(2)
_cell_angle_gamma                90
_cell_volume                     2159.51(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3798
_cell_measurement_temperature    298
_cell_measurement_theta_max      70.7820
_cell_measurement_theta_min      3.2950
_exptl_absorpt_coefficient_mu    4.531
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.4836
_exptl_crystal_description       block
_exptl_crystal_F_000             968.1501
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8771
_diffrn_reflns_theta_full        70.9529
_diffrn_reflns_theta_max         70.95
_diffrn_reflns_theta_min         4.02
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1293
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 1.0000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   30.00   67.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -120.0000 37

#__ type_ start__ end____ width___ exp.time_
  2 omega  -19.00   16.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -120.0000 35

#__ type_ start__ end____ width___ exp.time_
  3 omega -100.00  -54.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000   60.0000 46

#__ type_ start__ end____ width___ exp.time_
  4 omega   26.00  109.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000   60.0000 83

#__ type_ start__ end____ width___ exp.time_
  5 omega  -17.00  125.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000    0.0000   30.0000 142

#__ type_ start__ end____ width___ exp.time_
  6 omega   29.00   55.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
  7 omega   47.00   73.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
  8 omega   52.00   92.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000   90.0000 40

#__ type_ start__ end____ width___ exp.time_
  9 omega   51.00   78.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000    0.0000 27

#__ type_ start__ end____ width___ exp.time_
 10 omega   39.00   92.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000   60.0000 53

#__ type_ start__ end____ width___ exp.time_
 11 omega   47.00  111.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   90.0000 64

#__ type_ start__ end____ width___ exp.time_
 12 omega   38.00   91.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -180.0000 53

#__ type_ start__ end____ width___ exp.time_
 13 omega  153.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
 14 omega   40.00  170.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   12.0000 -180.0000 130

#__ type_ start__ end____ width___ exp.time_
 15 omega   40.00   89.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -60.0000 49

#__ type_ start__ end____ width___ exp.time_
 16 omega   47.00  104.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000 -120.0000 57

#__ type_ start__ end____ width___ exp.time_
 17 omega   38.00   64.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000    0.0000 26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0253395000
_diffrn_orient_matrix_UB_12      -0.0190533000
_diffrn_orient_matrix_UB_13      0.1080833000
_diffrn_orient_matrix_UB_21      -0.0893152000
_diffrn_orient_matrix_UB_22      0.0689114000
_diffrn_orient_matrix_UB_23      0.0104474000
_diffrn_orient_matrix_UB_31      -0.1609139000
_diffrn_orient_matrix_UB_32      -0.0351693000
_diffrn_orient_matrix_UB_33      -0.0383873000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -10
_reflns_limit_k_max              23
_reflns_limit_k_min              0
_reflns_limit_l_max              16
_reflns_limit_l_min              -7
_reflns_number_gt                3476
_reflns_number_total             4092
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.7770
_refine_diff_density_min         -1.1643
_refine_diff_density_rms         0.1302
_refine_ls_d_res_high            0.8156
_refine_ls_d_res_low             11.0037
_refine_ls_goodness_of_fit_ref   1.0365
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    36
_refine_ls_number_parameters     243
_refine_ls_number_reflns         4092
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0462
_refine_ls_restrained_S_all      1.0365
_refine_ls_shift/su_max          0.0023
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0918P)²+0.1867P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1341
_refine_ls_wR_factor_ref         0.1519
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C8(H8), C15(H15), C17(H17)
2.b Idealised Me refined as rotating group:
 C10(H10a,H10b,H10c), C11(H11a,H11b,H11c), C12(H12a,H12b,H12c), C19(H19a,H19b,
 H19c), C20(H20a,H20b,H20c), C21(H21a,H21b,H21c)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
C1 C 0.7367(4) 0.06464(16) 0.3463(2) 0.0503(7) Uani 1.000000 1 . . .
C2 C 0.7614(5) 0.0279(2) 0.1918(3) 0.0683(10) Uani 1.000000 1 . . .
H2 H 0.7539(5) 0.0001(2) 0.1351(3) 0.0820(11) Uiso 1.000000 1 R . .
C3 C 0.8282(5) 0.0907(2) 0.2011(3) 0.0678(10) Uani 1.000000 1 . . .
H3 H 0.8770(5) 0.1144(2) 0.1527(3) 0.0813(11) Uiso 1.000000 1 R . .
C4 C 0.8608(4) 0.17998(17) 0.3385(2) 0.0530(7) Uani 1.000000 1 . . .
C5 C 0.7455(4) 0.23130(19) 0.3420(3) 0.0602(8) Uani 1.000000 1 . . .
C6 C 0.7941(5) 0.29341(19) 0.3880(3) 0.0656(9) Uani 1.000000 1 . . .
H6 H 0.7181(5) 0.32813(19) 0.3925(3) 0.0787(10) Uiso 1.000000 1 R . .
C7 C 0.9514(5) 0.30482(19) 0.4270(3) 0.0626(8) Uani 1.000000 1 . . .
C8 C 1.0630(5) 0.2537(2) 0.4196(3) 0.0632(9) Uani 1.000000 1 . . .
H8 H 1.1700(5) 0.2619(2) 0.4445(3) 0.0758(11) Uiso 1.000000 1 R . .
C9 C 1.0220(4) 0.18979(18) 0.3761(2) 0.0564(7) Uani 1.000000 1 . . .
C10 C 0.5708(5) 0.2208(3) 0.2984(4) 0.0905(14) Uani 1.000000 1 . . .
H10a H 0.5672(5) 0.1960(19) 0.2365(16) 0.136(2) Uiso 1.000000 1 GR . .
H10b H 0.5153(14) 0.1948(19) 0.3446(14) 0.136(2) Uiso 1.000000 1 GR . .
H10c H 0.5195(15) 0.2650(3) 0.287(3) 0.136(2) Uiso 1.000000 1 GR . .
C11 C 0.9979(6) 0.3725(2) 0.4791(3) 0.0863(13) Uani 1.000000 1 . . .
H11a H 1.041(4) 0.3635(3) 0.5472(8) 0.129(2) Uiso 1.000000 1 GR . .
H11b H 1.078(3) 0.3953(9) 0.4454(16) 0.129(2) Uiso 1.000000 1 GR . .
H11c H 0.9045(10) 0.4015(8) 0.478(2) 0.129(2) Uiso 1.000000 1 GR . .
C12 C 1.1441(5) 0.1346(2) 0.3697(3) 0.0773(11) Uani 1.000000 1 . . .
H12a H 1.1012(16) 0.0912(4) 0.389(2) 0.1159(16) Uiso 1.000000 1 GR . .
H12b H 1.171(3) 0.1316(12) 0.3024(7) 0.1159(16) Uiso 1.000000 1 GR . .
H12c H 1.2395(16) 0.1454(9) 0.414(2) 0.1159(16) Uiso 1.000000 1 GR . .
C13 C 0.6223(4) -0.05162(17) 0.3012(2) 0.0508(7) Uani 1.000000 1 . . .
C14 C 0.4557(4) -0.05433(18) 0.2753(2) 0.0531(7) Uani 1.000000 1 . . .
C15 C 0.3790(4) -0.11611(19) 0.2942(2) 0.0580(8) Uani 1.000000 1 . . .
H15 H 0.2681(4) -0.11957(19) 0.2768(2) 0.0696(10) Uiso 1.000000 1 R . .
C16 C 0.4607(4) -0.17203(19) 0.3376(2) 0.0605(8) Uani 1.000000 1 . . .
C17 C 0.6257(5) -0.16724(19) 0.3592(3) 0.0633(9) Uani 1.000000 1 . . .
H17 H 0.6824(5) -0.20537(19) 0.3868(3) 0.0760(10) Uiso 1.000000 1 R . .
C18 C 0.7105(4) -0.10772(19) 0.3413(2) 0.0583(8) Uani 1.000000 1 . . .
C19 C 0.3639(5) 0.0066(2) 0.2294(4) 0.0782(11) Uani 1.000000 1 . . .
H19a H 0.390(3) 0.0469(4) 0.2697(15) 0.1173(17) Uiso 1.000000 1 GR . .
H19b H 0.393(3) 0.0143(12) 0.1633(11) 0.1173(17) Uiso 1.000000 1 GR . .
H19c H 0.2502(5) -0.0024(8) 0.226(2) 0.1173(17) Uiso 1.000000 1 GR . .
C20 C 0.3715(6) -0.2369(2) 0.3618(4) 0.0816(12) Uani 1.000000 1 . . .
H20a H 0.321(4) -0.2574(10) 0.3010(4) 0.1224(18) Uiso 1.000000 1 GR . .
H20b H 0.4462(9) -0.2692(7) 0.396(2) 0.1224(18) Uiso 1.000000 1 GR . .
H20c H 0.290(3) -0.2254(3) 0.404(2) 0.1224(18) Uiso 1.000000 1 GR . .
C21 C 0.8922(5) -0.1040(3) 0.3616(4) 0.0840(12) Uani 1.000000 1 . . .
H21a H 0.9374(5) -0.101(2) 0.2995(4) 0.1259(19) Uiso 1.000000 1 GR . .
H21b H 0.9226(5) -0.0640(11) 0.402(2) 0.1259(19) Uiso 1.000000 1 GR . .
H21c H 0.9321(6) -0.1449(9) 0.397(2) 0.1259(19) Uiso 1.000000 1 GR . .
Cl1 Cl 0.9522(2) 0.10162(10) 0.95263(12) 0.1205(5) Uani 1.000000 1 . . .
Cu1 Cu 0.5 0.0 0.5 0.0592(2) Uani 1.000000 2 S T P
Cu2 Cu 1.0 0.0 1.0 0.0975(4) Uani 1.000000 2 S T P
N1 N 0.7053(3) 0.01161(14) 0.2815(2) 0.0537(6) Uani 1.000000 1 . . .
N2 N 0.8112(3) 0.11372(15) 0.2966(2) 0.0554(6) Uani 1.000000 1 . . .
Se1 Se 0.70092(5) 0.07445(2) 0.47886(3) 0.06504(18) Uani 1.000000 1 . . .


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 N1 1.352(4) . ?
C1 N2 1.354(4) . ?
C1 Se1 1.856(3) . ?
C2 C3 1.336(5) . ?
C2 N1 1.383(4) . ?
C3 N2 1.384(4) . ?
C4 C5 1.387(5) . ?
C4 C9 1.394(4) . ?
C4 N2 1.441(4) . ?
C5 C6 1.390(5) . ?
C5 C10 1.520(5) . ?
C6 C7 1.374(5) . ?
C7 C8 1.370(5) . ?
C7 C11 1.513(5) . ?
C8 C9 1.393(5) . ?
C9 C12 1.484(5) . ?
C13 C14 1.394(4) . ?
C13 C18 1.384(5) . ?
C13 N1 1.445(4) . ?
C14 C15 1.393(5) . ?
C14 C19 1.499(5) . ?
C15 C16 1.372(5) . ?
C16 C17 1.377(5) . ?
C16 C20 1.514(5) . ?
C17 C18 1.387(5) . ?
C18 C21 1.511(5) . ?
Cl1 Cu2 2.090(2) . ?
Cu1 Se1 2.2532(3) . ?
Cu1 Se1 2.2532(3) 3_656 ?

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
N2 C1 N1 106.2(3) . . ?
Se1 C1 N1 131.1(2) . . ?
Se1 C1 N2 122.7(2) . . ?
N1 C2 C3 107.8(3) . . ?
N2 C3 C2 107.0(3) . . ?
C9 C4 C5 122.3(3) . . ?
N2 C4 C5 118.7(3) . . ?
N2 C4 C9 118.9(3) . . ?
C6 C5 C4 117.8(3) . . ?
C10 C5 C4 121.9(3) . . ?
C10 C5 C6 120.3(4) . . ?
C7 C6 C5 121.7(4) . . ?
C8 C7 C6 118.9(3) . . ?
C11 C7 C6 119.9(4) . . ?
C11 C7 C8 121.2(4) . . ?
C9 C8 C7 122.4(3) . . ?
C8 C9 C4 116.9(3) . . ?
C12 C9 C4 121.4(3) . . ?
C12 C9 C8 121.7(3) . . ?
C18 C13 C14 122.5(3) . . ?
N1 C13 C14 118.1(3) . . ?
N1 C13 C18 119.3(3) . . ?
C15 C14 C13 116.9(3) . . ?
C19 C14 C13 121.4(3) . . ?
C19 C14 C15 121.7(3) . . ?
C16 C15 C14 122.5(3) . . ?
C17 C16 C15 118.2(3) . . ?
C20 C16 C15 120.8(4) . . ?
C20 C16 C17 121.0(4) . . ?
C18 C17 C16 122.5(3) . . ?
C17 C18 C13 117.3(3) . . ?
C21 C18 C13 120.7(3) . . ?
C21 C18 C17 122.0(4) . . ?
Se1 Cu1 Se1 180.0 3_656 . ?
Cl1 Cu2 Cl1 180.0 3_757 . ?
C2 N1 C1 109.4(3) . . ?
C13 N1 C1 125.8(3) . . ?
C13 N1 C2 124.8(3) . . ?
C3 N2 C1 109.7(3) . . ?
C4 N2 C1 123.9(3) . . ?
C4 N2 C3 126.4(3) . . ?
Cu1 Se1 C1 105.24(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_11
_database_code_depnum_ccdc_archive 'CCDC 1855119'
_audit_update_record             
;
2018-07-11 deposited with the CCDC.
2018-09-03 downloaded from the CCDC.
;
_audit_creation_date             2017-09-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C54 H72 Cu N4 Se2, F6 P'
_chemical_formula_sum            'C54 H72 Cu F6 N4 P Se2'
_chemical_formula_weight         1143.63
_chemical_oxdiff_formula         'C21 H24 N2 Se Cu P'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.07537 0.05506 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
P 0.30360 0.43703 6.43450 4.17910 1.78000 1.49080 1.90670 27.15700 0.52600
68.16450 1.11489999294
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cu -1.96878 0.60861 13.33800 7.16760 5.61580 1.67350 3.58280 0.24700 11.39660
64.81260 1.19099998474
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Se -0.79210 1.18296 17.00060 5.81960 3.97310 4.35430 2.40980 0.27260 15.23720
43.81630 2.84089994431
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y,-z+1/2
3 -x,-y,-z
4 x,-y,z-1/2
5 x+1/2,y+1/2,z
6 -x+1/2,y+1/2,-z+1/2
7 -x+1/2,-y+1/2,-z
8 x+1/2,-y+1/2,z-1/2

_symmetry_Int_Tables_number      15
_cell_length_a                   19.5751(8)
_cell_length_b                   16.3426(4)
_cell_length_c                   20.4314(10)
_cell_angle_alpha                90
_cell_angle_beta                 113.637(5)
_cell_angle_gamma                90
_cell_volume                     5987.8(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4398
_cell_measurement_temperature    298
_cell_measurement_theta_max      71.6238
_cell_measurement_theta_min      3.6562
_exptl_absorpt_coefficient_mu    2.601
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76929
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.2685
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2353.1034
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10607
_diffrn_reflns_theta_full        71.7674
_diffrn_reflns_theta_max         71.77
_diffrn_reflns_theta_min         3.66
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean 16.1293
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 1.0000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -56.00  -29.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  124.0000   -5.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega  -15.00   11.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega  -48.00   23.00   1.0000    2.9000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   38.0000 -180.0000 71

#__ type_ start__ end____ width___ exp.time_
  4 omega  -80.00  -23.00   1.0000    2.9000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -57.0000 -120.0000 57

#__ type_ start__ end____ width___ exp.time_
  5 omega -115.00  -59.00   1.0000    2.9000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  178.0000 -120.0000 56

#__ type_ start__ end____ width___ exp.time_
  6 omega  -84.00   29.00   1.0000    2.9000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   19.0000  -60.0000 113

#__ type_ start__ end____ width___ exp.time_
  7 omega   50.00   86.00   1.0000    2.9000
omega____ theta____ kappa____ phi______ frames
    -      110.2786  -25.0000  120.0000 36

#__ type_ start__ end____ width___ exp.time_
  8 omega   41.00  114.00   1.0000    2.9000
omega____ theta____ kappa____ phi______ frames
    -      110.2786 -111.0000  120.0000 73

#__ type_ start__ end____ width___ exp.time_
  9 omega   43.00  107.00   1.0000    2.9000
omega____ theta____ kappa____ phi______ frames
    -      110.2786 -111.0000   30.0000 64

#__ type_ start__ end____ width___ exp.time_
 10 omega   39.00   86.00   1.0000    2.9000
omega____ theta____ kappa____ phi______ frames
    -      110.2786  -38.0000 -180.0000 47

#__ type_ start__ end____ width___ exp.time_
 11 omega   39.00   83.00   1.0000    2.9000
omega____ theta____ kappa____ phi______ frames
    -      110.2786  -38.0000   60.0000 44

#__ type_ start__ end____ width___ exp.time_
 12 omega   80.00  116.00   1.0000    2.9000
omega____ theta____ kappa____ phi______ frames
    -      110.2786 -111.0000 -150.0000 36

#__ type_ start__ end____ width___ exp.time_
 13 omega   42.00   68.00   1.0000    2.9000
omega____ theta____ kappa____ phi______ frames
    -      110.2786 -111.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 14 omega   96.00  178.00   1.0000    2.9000
omega____ theta____ kappa____ phi______ frames
    -      110.2786   25.0000 -120.0000 82

#__ type_ start__ end____ width___ exp.time_
 15 omega   39.00   82.00   1.0000    2.9000
omega____ theta____ kappa____ phi______ frames
    -      110.2786  -25.0000   90.0000 43

#__ type_ start__ end____ width___ exp.time_
 16 omega  120.00  161.00   1.0000    2.9000
omega____ theta____ kappa____ phi______ frames
    -      110.2786  111.0000   90.0000 41
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0302178000
_diffrn_orient_matrix_UB_12      0.0081720000
_diffrn_orient_matrix_UB_13      0.0586446000
_diffrn_orient_matrix_UB_21      0.0782119000
_diffrn_orient_matrix_UB_22      -0.0189954000
_diffrn_orient_matrix_UB_23      0.0573840000
_diffrn_orient_matrix_UB_31      0.0188276000
_diffrn_orient_matrix_UB_32      0.0919558000
_diffrn_orient_matrix_UB_33      0.0066642000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              21
_reflns_limit_h_min              -24
_reflns_limit_k_max              19
_reflns_limit_k_min              0
_reflns_limit_l_max              24
_reflns_limit_l_min              0
_reflns_number_gt                4504
_reflns_number_total             5722
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.9039
_refine_diff_density_min         -1.0294
_refine_diff_density_rms         0.0865
_refine_ls_d_res_high            0.8117
_refine_ls_d_res_low             12.0791
_refine_ls_goodness_of_fit_ref   1.0450
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    56
_refine_ls_number_parameters     317
_refine_ls_number_reflns         5722
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0542
_refine_ls_restrained_S_all      1.0450
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1036P)²+3.2468P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1516
_refine_ls_wR_factor_ref         0.1697
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C13(H13), C22(H22), C25(H25)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C7(H7), C8(H8), C18(H18), C19(H19), C20(H20)
2.c Idealised Me refined as rotating group:
 C11(H11a,H11b,H11c), C12(H12a,H12b,H12c), C14(H14a,H14b,H14c), C15(H15a,H15b,
 H15c), C23(H23a,H23b,H23c), C24(H24a,H24b,H24c), C26(H26a,H26b,H26c), C27(H27a,
 H27b,H27c)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Se1 Se 0.20768(2) 0.61958(2) 0.47654(2) 0.06441(18) Uani 1.000000 1 . . .
Cu1 Cu 0.25 0.75 0.5 0.0545(2) Uani 1.000000 2 S T P
N1 N 0.27646(15) 0.47272(15) 0.54309(14) 0.0461(6) Uani 1.000000 1 . . .
N2 N 0.35662(14) 0.57128(15) 0.57875(14) 0.0450(6) Uani 1.000000 1 . . .
C1 C 0.28455(17) 0.55402(18) 0.53585(16) 0.0440(6) Uani 1.000000 1 . . .
C2 C 0.34277(19) 0.4387(2) 0.59018(18) 0.0522(7) Uani 1.000000 1 . . .
H2 H 0.35126(19) 0.3842(2) 0.60404(18) 0.0626(9) Uiso 1.000000 1 R . .
C3 C 0.39252(19) 0.5004(2) 0.61190(18) 0.0541(8) Uani 1.000000 1 . . .
H3 H 0.44220(19) 0.4960(2) 0.64356(18) 0.0649(9) Uiso 1.000000 1 R . .
C4 C 0.20656(18) 0.42945(18) 0.50867(18) 0.0483(7) Uani 1.000000 1 . . .
C5 C 0.1561(2) 0.4319(2) 0.5408(2) 0.0594(9) Uani 1.000000 1 . . .
C6 C 0.0887(3) 0.3914(3) 0.5054(3) 0.0794(12) Uani 1.000000 1 . . .
H6 H 0.0530(3) 0.3921(3) 0.5247(3) 0.0952(15) Uiso 1.000000 1 R . .
C7 C 0.0743(3) 0.3508(3) 0.4430(3) 0.0844(13) Uani 1.000000 1 . . .
H7 H 0.0288(3) 0.3242(3) 0.4202(3) 0.1013(16) Uiso 1.000000 1 R . .
C8 C 0.1256(3) 0.3486(3) 0.4135(2) 0.0756(12) Uani 1.000000 1 . . .
H8 H 0.1148(3) 0.3200(3) 0.3712(2) 0.0908(14) Uiso 1.000000 1 R . .
C9 C 0.1934(2) 0.3881(2) 0.4455(2) 0.0572(8) Uani 1.000000 1 . . .
C10 C 0.1734(3) 0.4750(3) 0.6121(3) 0.0748(11) Uani 1.000000 1 . . .
H10 H 0.2187(3) 0.5076(3) 0.6233(3) 0.0898(14) Uiso 1.000000 1 R . .
C11 C 0.1106(4) 0.5334(4) 0.6074(4) 0.129(2) Uani 1.000000 1 . . .
H11a H 0.102(2) 0.572(2) 0.569(2) 0.194(4) Uiso 1.000000 1 GR . .
H11b H 0.0659(10) 0.5027(6) 0.598(3) 0.194(4) Uiso 1.000000 1 GR . .
H11c H 0.1244(15) 0.562(3) 0.6517(12) 0.194(4) Uiso 1.000000 1 GR . .
C12 C 0.1892(5) 0.4123(4) 0.6710(3) 0.130(3) Uani 1.000000 1 . . .
H12a H 0.1488(16) 0.374(2) 0.6575(15) 0.195(4) Uiso 1.000000 1 GR . .
H12b H 0.2347(18) 0.384(3) 0.678(2) 0.195(4) Uiso 1.000000 1 GR . .
H12c H 0.194(4) 0.4394(6) 0.7143(9) 0.195(4) Uiso 1.000000 1 GR . .
C13 C 0.2500(3) 0.3859(3) 0.4117(2) 0.0728(11) Uani 1.000000 1 . . .
H13 H 0.2950(3) 0.4144(3) 0.4439(2) 0.0874(13) Uiso 1.000000 1 R . .
C14 C 0.2208(5) 0.4305(5) 0.3409(4) 0.139(3) Uani 1.000000 1 . . .
H14a H 0.181(3) 0.400(2) 0.3064(11) 0.209(5) Uiso 1.000000 1 GR . .
H14b H 0.203(4) 0.4836(17) 0.3467(9) 0.209(5) Uiso 1.000000 1 GR . .
H14c H 0.2603(10) 0.436(4) 0.3246(18) 0.209(5) Uiso 1.000000 1 GR . .
C15 C 0.2717(4) 0.3001(3) 0.4023(3) 0.1019(17) Uani 1.000000 1 . . .
H15a H 0.289(2) 0.2721(9) 0.4474(6) 0.153(3) Uiso 1.000000 1 GR . .
H15b H 0.2292(7) 0.2718(9) 0.3685(18) 0.153(3) Uiso 1.000000 1 GR . .
H15c H 0.3107(18) 0.3014(3) 0.385(2) 0.153(3) Uiso 1.000000 1 GR . .
C16 C 0.39019(17) 0.6510(2) 0.59298(18) 0.0498(7) Uani 1.000000 1 . . .
C17 C 0.42919(19) 0.6776(2) 0.5529(2) 0.0616(9) Uani 1.000000 1 . . .
C18 C 0.4637(2) 0.7541(3) 0.5709(3) 0.0795(13) Uani 1.000000 1 . . .
H18 H 0.4904(2) 0.7740(3) 0.5455(3) 0.0954(16) Uiso 1.000000 1 R . .
C19 C 0.4595(2) 0.7996(3) 0.6242(3) 0.0839(14) Uani 1.000000 1 . . .
H19 H 0.4829(2) 0.8503(3) 0.6346(3) 0.1007(17) Uiso 1.000000 1 R . .
C20 C 0.4211(2) 0.7722(2) 0.6633(2) 0.0742(12) Uani 1.000000 1 . . .
H20 H 0.4188(2) 0.8046(2) 0.6998(2) 0.0890(15) Uiso 1.000000 1 R . .
C21 C 0.38521(18) 0.6960(2) 0.64890(19) 0.0562(8) Uani 1.000000 1 . . .
C22 C 0.4348(3) 0.6282(3) 0.4934(3) 0.0811(13) Uani 1.000000 1 . . .
H22 H 0.4124(3) 0.5745(3) 0.4934(3) 0.0974(15) Uiso 1.000000 1 R . .
C23 C 0.3913(4) 0.6681(6) 0.4203(3) 0.144(3) Uani 1.000000 1 . . .
H23a H 0.3388(4) 0.665(4) 0.4091(17) 0.215(5) Uiso 1.000000 1 GR . .
H23b H 0.406(3) 0.7244(13) 0.4218(12) 0.215(5) Uiso 1.000000 1 GR . .
H23c H 0.402(3) 0.640(3) 0.3843(7) 0.215(5) Uiso 1.000000 1 GR . .
C24 C 0.5159(4) 0.6142(5) 0.5041(4) 0.119(2) Uani 1.000000 1 . . .
H24a H 0.5411(9) 0.6659(5) 0.511(3) 0.179(3) Uiso 1.000000 1 GR . .
H24b H 0.5404(10) 0.581(3) 0.5455(19) 0.179(3) Uiso 1.000000 1 GR . .
H24c H 0.5172(4) 0.587(3) 0.4628(14) 0.179(3) Uiso 1.000000 1 GR . .
C25 C 0.3447(2) 0.6635(3) 0.6930(2) 0.0675(10) Uani 1.000000 1 . . .
H25 H 0.3112(2) 0.6201(3) 0.6650(2) 0.0810(12) Uiso 1.000000 1 R . .
C26 C 0.3978(3) 0.6254(4) 0.7620(3) 0.108(2) Uani 1.000000 1 . . .
H26a H 0.425(2) 0.582(2) 0.7516(3) 0.162(3) Uiso 1.000000 1 GR . .
H26b H 0.4320(18) 0.6662(8) 0.7907(12) 0.162(3) Uiso 1.000000 1 GR . .
H26c H 0.3701(4) 0.604(3) 0.7876(13) 0.162(3) Uiso 1.000000 1 GR . .
C27 C 0.2967(5) 0.7278(5) 0.7077(4) 0.146(3) Uani 1.000000 1 . . .
H27a H 0.3281(5) 0.767(2) 0.742(3) 0.219(5) Uiso 1.000000 1 GR . .
H27b H 0.267(3) 0.756(3) 0.6641(8) 0.219(5) Uiso 1.000000 1 GR . .
H27c H 0.264(3) 0.7018(6) 0.727(3) 0.219(5) Uiso 1.000000 1 GR . .
P1 P 0.5 0.31678(10) 0.75 0.0838(6) Uani 1.000000 2 S T P
F1 F 0.5 0.4115(3) 0.75 0.180(3) Uani 1.000000 2 S T P
F2 F 0.4787(2) 0.3185(2) 0.66736(16) 0.1359(15) Uani 1.000000 1 . . .
F3 F 0.4153(2) 0.3167(4) 0.7297(3) 0.181(2) Uani 1.000000 1 . . .
F4 F 0.5 0.2232(4) 0.75 0.219(5) Uani 1.000000 2 S T P


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
Se1 Cu1 2.2672(3) 7_566 ?
Se1 C1 1.849(3) . ?
N1 C1 1.353(4) . ?
N1 C2 1.385(4) . ?
N1 C4 1.448(4) . ?
N2 C1 1.359(4) . ?
N2 C3 1.384(4) . ?
N2 C16 1.436(4) . ?
C2 C3 1.347(5) . ?
C4 C5 1.388(5) . ?
C4 C9 1.387(5) . ?
C5 C6 1.391(6) . ?
C5 C10 1.529(6) . ?
C6 C7 1.363(7) . ?
C7 C8 1.363(7) . ?
C8 C9 1.382(5) . ?
C9 C13 1.523(6) . ?
C10 C11 1.529(8) . ?
C10 C12 1.515(8) . ?
C13 C14 1.513(7) . ?
C13 C15 1.500(7) . ?
C16 C17 1.395(5) . ?
C16 C21 1.394(5) . ?
C17 C18 1.398(5) . ?
C17 C22 1.499(6) . ?
C18 C19 1.349(7) . ?
C19 C20 1.374(7) . ?
C20 C21 1.402(5) . ?
C21 C25 1.515(6) . ?
C22 C23 1.538(8) . ?
C22 C24 1.531(7) . ?
C25 C26 1.511(6) . ?
C25 C27 1.517(7) . ?
P1 F1 1.549(5) . ?
P1 F2 1.569(3) 2_656 ?
P1 F2 1.569(3) . ?
P1 F3 1.539(4) 2_656 ?
P1 F3 1.539(4) . ?
P1 F4 1.530(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Se1 Cu1 105.89(9) . 7_566 ?
Se1 Cu1 Se1 180.0 . 7_566 ?
C2 N1 C1 110.6(3) . . ?
C4 N1 C1 123.8(3) . . ?
C4 N1 C2 125.6(3) . . ?
C3 N2 C1 109.5(3) . . ?
C16 N2 C1 126.3(3) . . ?
C16 N2 C3 124.0(3) . . ?
N1 C1 Se1 122.7(2) . . ?
N2 C1 Se1 131.6(2) . . ?
N2 C1 N1 105.7(2) . . ?
C3 C2 N1 106.4(3) . . ?
C2 C3 N2 107.9(3) . . ?
C5 C4 N1 118.0(3) . . ?
C9 C4 N1 118.5(3) . . ?
C9 C4 C5 123.5(3) . . ?
C6 C5 C4 116.5(4) . . ?
C10 C5 C4 122.4(3) . . ?
C10 C5 C6 121.0(4) . . ?
C7 C6 C5 121.1(4) . . ?
C8 C7 C6 120.8(4) . . ?
C9 C8 C7 121.2(4) . . ?
C8 C9 C4 116.9(4) . . ?
C13 C9 C4 122.4(3) . . ?
C13 C9 C8 120.7(4) . . ?
C11 C10 C5 111.3(5) . . ?
C12 C10 C5 110.0(4) . . ?
C12 C10 C11 112.0(5) . . ?
C14 C13 C9 111.0(5) . . ?
C15 C13 C9 112.0(4) . . ?
C15 C13 C14 110.3(5) . . ?
C17 C16 N2 118.5(3) . . ?
C21 C16 N2 117.9(3) . . ?
C21 C16 C17 123.5(3) . . ?
C18 C17 C16 116.4(4) . . ?
C22 C17 C16 122.9(3) . . ?
C22 C17 C18 120.7(4) . . ?
C19 C18 C17 121.7(4) . . ?
C20 C19 C18 121.0(4) . . ?
C21 C20 C19 120.9(4) . . ?
C20 C21 C16 116.5(4) . . ?
C25 C21 C16 121.9(3) . . ?
C25 C21 C20 121.6(4) . . ?
C23 C22 C17 111.4(5) . . ?
C24 C22 C17 112.0(5) . . ?
C24 C22 C23 110.0(5) . . ?
C26 C25 C21 111.7(4) . . ?
C27 C25 C21 112.9(5) . . ?
C27 C25 C26 110.5(5) . . ?
F2 P1 F1 89.00(15) . . ?
F2 P1 F1 89.00(15) 2_656 . ?
F2 P1 F2 178.0(3) 2_656 . ?
F3 P1 F1 90.0(2) 2_656 . ?
F3 P1 F1 90.0(2) . . ?
F3 P1 F2 94.8(3) . 2_656 ?
F3 P1 F2 94.8(3) 2_656 . ?
F3 P1 F2 85.2(3) . . ?
F3 P1 F2 85.2(3) 2_656 2_656 ?
F3 P1 F3 179.9(5) 2_656 . ?
F4 P1 F1 180.0 . . ?
F4 P1 F2 91.00(15) . 2_656 ?
F4 P1 F2 91.00(15) . . ?
F4 P1 F3 90.0(2) . . ?
F4 P1 F3 90.0(2) . 2_656 ?

_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_4
_database_code_depnum_ccdc_archive 'CCDC 1855117'
_audit_update_record             
;
2018-07-11 deposited with the CCDC.
2018-09-03 downloaded from the CCDC.
;
_audit_creation_date             2017-09-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_formula_moiety         'C21 H24 Cu I N2 S'
_chemical_formula_sum            'C21 H24 Cu I N2 S'
_chemical_formula_weight         526.95
_chemical_oxdiff_formula         'C21 H28 N2 S Cu I'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
I -0.19206 6.94430 20.14720 18.99490 7.51380 2.27350 4.34700 0.38140 27.76600
66.87760 4.07119989395
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.33537 0.55136 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cu -1.96878 0.60861 13.33800 7.16760 5.61580 1.67350 3.58280 0.24700 11.39660
64.81260 1.19099998474
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   11.5024(12)
_cell_length_b                   15.4127(14)
_cell_length_c                   13.6155(16)
_cell_angle_alpha                90
_cell_angle_beta                 112.632(13)
_cell_angle_gamma                90
_cell_volume                     2227.9(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2859
_cell_measurement_temperature    298.0
_cell_measurement_theta_max      71.1585
_cell_measurement_theta_min      3.5141
_exptl_absorpt_coefficient_mu    13.179
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32807
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.5709
_exptl_crystal_description       needle
_exptl_crystal_F_000             1042.9361
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_unetI/netI     0.0598
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8950
_diffrn_reflns_theta_full        71.2983
_diffrn_reflns_theta_max         71.30
_diffrn_reflns_theta_min         4.16
_diffrn_ambient_temperature      298.0
_diffrn_detector_area_resol_mean 16.1293
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 1.0000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   29.00   54.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
  2 omega  -37.00   30.00   1.0000    3.4200
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   38.0000  120.0000 67

#__ type_ start__ end____ width___ exp.time_
  3 omega  -70.00  -39.00   1.0000    3.4200
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000   90.0000 31

#__ type_ start__ end____ width___ exp.time_
  4 omega  -98.00  -72.00   1.0000    3.4200
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega   35.00  121.00   1.0000    3.4200
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000   30.0000 86

#__ type_ start__ end____ width___ exp.time_
  6 omega   23.00  107.00   1.0000    3.4200
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000 -120.0000 84

#__ type_ start__ end____ width___ exp.time_
  7 omega  -14.00   73.00   1.0000    3.4200
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000   60.0000 87

#__ type_ start__ end____ width___ exp.time_
  8 omega   75.00  101.00   1.0000    3.4200
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
  9 omega   58.00   93.00   1.0000    3.4200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   30.0000 35

#__ type_ start__ end____ width___ exp.time_
 10 omega   36.00   88.00   1.0000    3.4200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   90.0000 52

#__ type_ start__ end____ width___ exp.time_
 11 omega  134.00  169.00   1.0000    3.4200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 35

#__ type_ start__ end____ width___ exp.time_
 12 omega   40.00   89.00   1.0000    3.4200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -60.0000 49

#__ type_ start__ end____ width___ exp.time_
 13 omega   44.00   93.00   1.0000    3.4200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -120.0000 49

#__ type_ start__ end____ width___ exp.time_
 14 omega   50.00   90.00   1.0000    3.4200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -180.0000 40

#__ type_ start__ end____ width___ exp.time_
 15 omega   40.00  136.00   1.0000    3.4200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -120.0000 96

#__ type_ start__ end____ width___ exp.time_
 16 omega   44.00  169.00   1.0000    3.4200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -12.0000 -150.0000 125
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1136665000
_diffrn_orient_matrix_UB_12      0.0587482000
_diffrn_orient_matrix_UB_13      0.0142124000
_diffrn_orient_matrix_UB_21      0.0898607000
_diffrn_orient_matrix_UB_22      -0.0765279000
_diffrn_orient_matrix_UB_23      0.0483404000
_diffrn_orient_matrix_UB_31      -0.0076977000
_diffrn_orient_matrix_UB_32      -0.0256859000
_diffrn_orient_matrix_UB_33      -0.1118211000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -13
_reflns_limit_k_max              18
_reflns_limit_k_min              0
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                2630
_reflns_number_total             4192
_reflns_odcompleteness_completeness 99.03
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.8092
_refine_diff_density_min         -2.8690
_refine_diff_density_rms         0.1881
_refine_ls_d_res_high            0.8139
_refine_ls_d_res_low             10.6167
_refine_ls_goodness_of_fit_ref   1.0724
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    36
_refine_ls_number_parameters     240
_refine_ls_number_reflns         4192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1159
_refine_ls_R_factor_gt           0.0851
_refine_ls_restrained_S_all      1.0724
_refine_ls_shift/su_max          0.0002
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2421
_refine_ls_wR_factor_ref         0.3220
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C8(H8), C15(H15), C17(H17)
2.b Idealised Me refined as rotating group:
 C10(H10a,H10b,H10c), C11(H11a,H11b,H11c), C12(H12a,H12b,H12c), C19(H19a,H19b,
 H19c), C20(H20a,H20b,H20c), C21(H21a,H21b,H21c)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
C1 C 0.4047(8) 0.2508(5) -0.0544(6) 0.0554(17) Uani 1.000000 .
C2 C 0.3298(8) 0.2508(6) -0.2327(6) 0.063(2) Uani 1.000000 .
H2 H 0.3234(8) 0.2424(6) -0.3022(6) 0.075(2) Uiso 1.000000 R
C3 C 0.2442(9) 0.2885(5) -0.2031(6) 0.063(2) Uani 1.000000 .
H3 H 0.1665(9) 0.3101(5) -0.2485(6) 0.076(2) Uiso 1.000000 R
C4 C 0.2239(8) 0.3202(5) -0.0305(6) 0.0577(19) Uani 1.000000 .
C5 C 0.1350(9) 0.2660(6) -0.0174(7) 0.065(2) Uani 1.000000 .
C6 C 0.0635(10) 0.2990(7) 0.0365(8) 0.076(3) Uani 1.000000 .
H6 H 0.0014(10) 0.2641(7) 0.0438(8) 0.091(3) Uiso 1.000000 R
C7 C 0.0809(10) 0.3807(6) 0.0790(8) 0.072(2) Uani 1.000000 .
C8 C 0.1733(10) 0.4316(6) 0.0670(8) 0.074(3) Uani 1.000000 .
H8 H 0.1872(10) 0.4869(6) 0.0968(8) 0.089(3) Uiso 1.000000 R
C9 C 0.2459(10) 0.4037(6) 0.0124(8) 0.068(2) Uani 1.000000 .
C10 C 0.3481(14) 0.4600(7) 0.0017(13) 0.106(4) Uani 1.000000 .
H10a H 0.424(3) 0.453(5) 0.063(4) 0.160(7) Uiso 1.000000 GR
H10b H 0.362(8) 0.443(5) -0.061(5) 0.160(7) Uiso 1.000000 GR
H10c H 0.322(5) 0.5197(10) -0.004(9) 0.160(7) Uiso 1.000000 GR
C11 C 0.1157(13) 0.1750(7) -0.0600(11) 0.094(4) Uani 1.000000 .
H11a H 0.087(10) 0.1765(7) -0.1362(12) 0.141(5) Uiso 1.000000 GR
H11b H 0.194(3) 0.144(2) -0.031(7) 0.141(5) Uiso 1.000000 GR
H11c H 0.054(7) 0.147(2) -0.040(7) 0.141(5) Uiso 1.000000 GR
C12 C 0.0043(13) 0.4145(9) 0.1389(9) 0.102(4) Uani 1.000000 .
H12a H -0.079(3) 0.429(7) 0.0895(11) 0.154(6) Uiso 1.000000 GR
H12b H -0.002(9) 0.371(3) 0.187(7) 0.154(6) Uiso 1.000000 GR
H12c H 0.044(6) 0.465(4) 0.179(7) 0.154(6) Uiso 1.000000 GR
C13 C 0.5356(8) 0.1763(5) -0.1402(6) 0.0548(18) Uani 1.000000 .
C14 C 0.5223(10) 0.0863(5) -0.1450(8) 0.065(2) Uani 1.000000 .
C15 C 0.6176(10) 0.0383(6) -0.1536(8) 0.075(3) Uani 1.000000 .
H15 H 0.6110(10) -0.0219(6) -0.1557(8) 0.090(3) Uiso 1.000000 R
C16 C 0.7254(10) 0.0770(6) -0.1593(8) 0.071(2) Uani 1.000000 .
C17 C 0.7343(9) 0.1670(6) -0.1541(7) 0.065(2) Uani 1.000000 .
H17 H 0.8050(9) 0.1939(6) -0.1576(7) 0.078(2) Uiso 1.000000 R
C18 C 0.6403(9) 0.2174(5) -0.1437(7) 0.061(2) Uani 1.000000 .
C19 C 0.6576(11) 0.3145(6) -0.1361(9) 0.073(3) Uani 1.000000 .
H19a H 0.591(4) 0.3416(6) -0.194(4) 0.110(4) Uiso 1.000000 GR
H19b H 0.656(8) 0.3346(8) -0.070(3) 0.110(4) Uiso 1.000000 GR
H19c H 0.737(3) 0.3292(7) -0.139(6) 0.110(4) Uiso 1.000000 GR
C20 C 0.4052(12) 0.0429(7) -0.1408(12) 0.091(3) Uani 1.000000 .
H20a H 0.392(5) 0.063(5) -0.079(4) 0.137(5) Uiso 1.000000 GR
H20b H 0.3333(18) 0.058(5) -0.204(4) 0.137(5) Uiso 1.000000 GR
H20c H 0.416(4) -0.0189(8) -0.137(8) 0.137(5) Uiso 1.000000 GR
C21 C 0.8288(12) 0.0212(8) -0.1696(11) 0.100(4) Uani 1.000000 .
H21a H 0.886(6) 0.003(6) -0.1002(13) 0.149(6) Uiso 1.000000 GR
H21b H 0.7922(14) -0.029(4) -0.212(7) 0.149(6) Uiso 1.000000 GR
H21c H 0.874(6) 0.054(2) -0.204(8) 0.149(6) Uiso 1.000000 GR
Cu1 Cu 0.67270(14) 0.18449(9) 0.08896(12) 0.0775(5) Uani 1.000000 .
I1 I 0.88123(7) 0.12724(6) 0.16420(7) 0.0997(4) Uani 1.000000 .
N1 N 0.4287(7) 0.2268(4) -0.1422(6) 0.0591(16) Uani 1.000000 .
N2 N 0.2909(7) 0.2899(4) -0.0935(5) 0.0579(16) Uani 1.000000 .
S1 S 0.4962(3) 0.2386(2) 0.07680(18) 0.0871(9) Uani 1.000000 .


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 N1 1.377(9) . ?
C1 N2 1.350(10) . ?
C1 S1 1.699(8) . ?
C2 C3 1.332(12) . ?
C2 N1 1.368(11) . ?
C3 N2 1.379(10) . ?
C4 C5 1.384(13) . ?
C4 C9 1.396(12) . ?
C4 N2 1.434(10) . ?
C5 C6 1.393(13) . ?
C5 C11 1.501(13) . ?
C6 C7 1.367(14) . ?
C7 C8 1.380(15) . ?
C7 C12 1.506(14) . ?
C8 C9 1.383(13) . ?
C9 C10 1.512(15) . ?
C13 C14 1.395(12) . ?
C13 C18 1.378(12) . ?
C13 N1 1.446(11) . ?
C14 C15 1.364(13) . ?
C14 C20 1.524(14) . ?
C15 C16 1.405(14) . ?
C16 C17 1.391(13) . ?
C16 C21 1.517(13) . ?
C17 C18 1.381(12) . ?
C18 C19 1.508(11) . ?
Cu1 I1 2.3854(16) . ?
Cu1 S1 2.142(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
N2 C1 N1 105.4(7) . . ?
S1 C1 N1 129.3(6) . . ?
S1 C1 N2 125.3(6) . . ?
N1 C2 C3 107.6(7) . . ?
N2 C3 C2 108.0(8) . . ?
C9 C4 C5 121.8(8) . . ?
N2 C4 C5 118.2(7) . . ?
N2 C4 C9 120.0(8) . . ?
C6 C5 C4 117.5(8) . . ?
C11 C5 C4 121.4(8) . . ?
C11 C5 C6 121.1(9) . . ?
C7 C6 C5 122.7(10) . . ?
C8 C7 C6 117.9(9) . . ?
C12 C7 C6 121.8(10) . . ?
C12 C7 C8 120.3(10) . . ?
C9 C8 C7 122.5(9) . . ?
C8 C9 C4 117.6(9) . . ?
C10 C9 C4 120.6(9) . . ?
C10 C9 C8 121.8(9) . . ?
C18 C13 C14 122.5(8) . . ?
N1 C13 C14 117.2(7) . . ?
N1 C13 C18 120.0(7) . . ?
C15 C14 C13 117.8(8) . . ?
C20 C14 C13 121.1(8) . . ?
C20 C14 C15 121.1(8) . . ?
C16 C15 C14 122.0(9) . . ?
C17 C16 C15 118.0(8) . . ?
C21 C16 C15 120.3(9) . . ?
C21 C16 C17 121.7(9) . . ?
C18 C17 C16 121.4(8) . . ?
C17 C18 C13 118.3(8) . . ?
C19 C18 C13 123.2(8) . . ?
C19 C18 C17 118.5(8) . . ?
S1 Cu1 I1 160.72(10) . . ?
C2 N1 C1 109.5(7) . . ?
C13 N1 C1 125.5(7) . . ?
C13 N1 C2 124.7(7) . . ?
C3 N2 C1 109.6(7) . . ?
C4 N2 C1 125.0(7) . . ?
C4 N2 C3 125.2(7) . . ?
Cu1 S1 C1 108.0(3) . . ?

_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_5
_database_code_depnum_ccdc_archive 'CCDC 1855123'
_audit_update_record             
;
2018-07-11 deposited with the CCDC.
2018-09-03 downloaded from the CCDC.
;
_audit_creation_date             2017-09-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_formula_moiety         'C21 H24 Cu I N2 Se'
_chemical_formula_sum            'C21 H24 Cu I N2 Se'
_chemical_formula_weight         573.85
_chemical_oxdiff_formula         'C24 H28 N2 Se Cu I'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
I -0.19206 6.94430 20.14720 18.99490 7.51380 2.27350 4.34700 0.38140 27.76600
66.87760 4.07119989395
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cu -1.96878 0.60861 13.33800 7.16760 5.61580 1.67350 3.58280 0.24700 11.39660
64.81260 1.19099998474
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Se -0.79210 1.18296 17.00060 5.81960 3.97310 4.35430 2.40980 0.27260 15.23720
43.81630 2.84089994431
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   11.5428(5)
_cell_length_b                   15.3915(8)
_cell_length_c                   13.7448(7)
_cell_angle_alpha                90
_cell_angle_beta                 112.364(5)
_cell_angle_gamma                90
_cell_volume                     2258.3(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3815
_cell_measurement_temperature    298
_cell_measurement_theta_max      70.2140
_cell_measurement_theta_min      4.2600
_exptl_absorpt_coefficient_mu    13.981
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.26227
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.6877
_exptl_crystal_description       needle
_exptl_crystal_F_000             1110.4274
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.17
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9201
_diffrn_reflns_theta_full        71.2128
_diffrn_reflns_theta_max         71.21
_diffrn_reflns_theta_min         4.14
_diffrn_ambient_temperature      298.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1293
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 1.0000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   27.00   68.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   19.0000 -180.0000 41

#__ type_ start__ end____ width___ exp.time_
  2 omega   -4.00   27.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   25.0000 -150.0000 31

#__ type_ start__ end____ width___ exp.time_
  3 omega  -94.00  -18.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -63.0000  -90.0000 76

#__ type_ start__ end____ width___ exp.time_
  4 omega   26.00  123.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000 -120.0000 97

#__ type_ start__ end____ width___ exp.time_
  5 omega   91.00  117.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
  6 omega   -3.00   70.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000   90.0000 73

#__ type_ start__ end____ width___ exp.time_
  7 omega   35.00  107.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  -30.0000 72

#__ type_ start__ end____ width___ exp.time_
  8 omega   49.00   88.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000   90.0000 39

#__ type_ start__ end____ width___ exp.time_
  9 omega   44.00  109.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   60.0000 65

#__ type_ start__ end____ width___ exp.time_
 10 omega   52.00   86.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000    0.0000 34

#__ type_ start__ end____ width___ exp.time_
 11 omega   41.00   79.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000   60.0000 38

#__ type_ start__ end____ width___ exp.time_
 12 omega   68.00  100.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000 -120.0000 32

#__ type_ start__ end____ width___ exp.time_
 13 omega   56.00   87.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -90.0000 31

#__ type_ start__ end____ width___ exp.time_
 14 omega   99.00  157.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000 -150.0000 58

#__ type_ start__ end____ width___ exp.time_
 15 omega  107.00  176.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000  150.0000 69

#__ type_ start__ end____ width___ exp.time_
 16 omega   92.00  157.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000  -90.0000 65

#__ type_ start__ end____ width___ exp.time_
 17 omega   41.00  103.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000  150.0000 62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0570775000
_diffrn_orient_matrix_UB_12      0.0630104000
_diffrn_orient_matrix_UB_13      0.0567515000
_diffrn_orient_matrix_UB_21      0.0964148000
_diffrn_orient_matrix_UB_22      -0.0303874000
_diffrn_orient_matrix_UB_23      0.1069713000
_diffrn_orient_matrix_UB_31      0.0910225000
_diffrn_orient_matrix_UB_32      0.0715845000
_diffrn_orient_matrix_UB_33      -0.0045660000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -13
_reflns_limit_k_max              18
_reflns_limit_k_min              0
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                3284
_reflns_number_total             4262
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.5022
_refine_diff_density_min         -1.4140
_refine_diff_density_rms         0.1373
_refine_ls_d_res_high            0.8143
_refine_ls_d_res_low             10.6746
_refine_ls_goodness_of_fit_ref   1.0257
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    36
_refine_ls_number_parameters     240
_refine_ls_number_reflns         4262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0490
_refine_ls_restrained_S_all      1.0257
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0908P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1323
_refine_ls_wR_factor_ref         0.1511
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C17(H17), C15(H15), C3(H3), C6(H6), C8(H8), C2(H2)
2.b Idealised Me refined as rotating group:
 C19(H19a,H19b,H19c), C11(H11a,H11b,H11c), C20(H20a,H20b,H20c), C10(H10a,H10b,
 H10c), C21(H21a,H21b,H21c), C12(H12a,H12b,H12c)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
I1 I 0.88517(3) 0.12052(3) 0.65908(4) 0.0939(2) Uani 1.000000 .
Se1 Se 0.50312(5) 0.24775(6) 0.58318(4) 0.0834(3) Uani 1.000000 .
Cu1 Cu 0.68099(7) 0.18391(6) 0.58840(7) 0.0714(3) Uani 1.000000 .
C13 C 0.5337(4) 0.1783(3) 0.3596(3) 0.0484(10) Uani 1.000000 .
C18 C 0.6384(4) 0.2207(3) 0.3552(3) 0.0521(10) Uani 1.000000 .
N2 N 0.2880(3) 0.2911(3) 0.4032(3) 0.0506(8) Uani 1.000000 .
C4 C 0.2200(4) 0.3214(3) 0.4655(3) 0.0504(10) Uani 1.000000 .
C14 C 0.5199(5) 0.0882(3) 0.3547(4) 0.0569(11) Uani 1.000000 .
C17 C 0.7323(4) 0.1686(4) 0.3460(4) 0.0585(11) Uani 1.000000 .
H17 H 0.8035(4) 0.1950(4) 0.3433(4) 0.0703(14) Uiso 1.000000 R
C16 C 0.7235(5) 0.0798(4) 0.3408(4) 0.0638(13) Uani 1.000000 .
C5 C 0.1344(4) 0.2656(3) 0.4812(4) 0.0565(11) Uani 1.000000 .
C15 C 0.6187(4) 0.0406(4) 0.3452(4) 0.0663(13) Uani 1.000000 .
H15 H 0.6131(4) -0.0197(4) 0.3418(4) 0.0796(16) Uiso 1.000000 R
C3 C 0.2396(4) 0.2865(4) 0.2949(4) 0.0601(12) Uani 1.000000 .
H3 H 0.1619(4) 0.3070(4) 0.2499(4) 0.0721(14) Uiso 1.000000 R
C9 C 0.2405(5) 0.4053(3) 0.5054(4) 0.0613(12) Uani 1.000000 .
C19 C 0.6511(6) 0.3167(4) 0.3618(5) 0.0688(14) Uani 1.000000 .
H19a H 0.5719(11) 0.3430(4) 0.321(3) 0.103(2) Uiso 1.000000 GR
H19b H 0.677(4) 0.3346(4) 0.4339(6) 0.103(2) Uiso 1.000000 GR
H19c H 0.712(3) 0.3347(4) 0.335(3) 0.103(2) Uiso 1.000000 GR
C6 C 0.0654(5) 0.2979(4) 0.5370(4) 0.0657(13) Uani 1.000000 .
H6 H 0.0058(5) 0.2622(4) 0.5470(4) 0.0789(16) Uiso 1.000000 R
C11 C 0.1159(7) 0.1751(5) 0.4398(6) 0.093(2) Uani 1.000000 .
H11a H 0.090(5) 0.1764(5) 0.3646(7) 0.139(3) Uiso 1.000000 GR
H11b H 0.1932(16) 0.1436(12) 0.470(4) 0.139(3) Uiso 1.000000 GR
H11c H 0.053(4) 0.1471(14) 0.458(4) 0.139(3) Uiso 1.000000 GR
C20 C 0.4050(6) 0.0434(4) 0.3565(6) 0.0822(17) Uani 1.000000 .
H20a H 0.393(3) 0.059(2) 0.4198(19) 0.123(3) Uiso 1.000000 GR
H20b H 0.3333(9) 0.061(2) 0.297(2) 0.123(3) Uiso 1.000000 GR
H20c H 0.4153(19) -0.0183(4) 0.354(4) 0.123(3) Uiso 1.000000 GR
C8 C 0.1695(6) 0.4334(4) 0.5632(4) 0.0717(15) Uani 1.000000 .
H8 H 0.1823(6) 0.4889(4) 0.5919(4) 0.0861(18) Uiso 1.000000 R
C10 C 0.3374(7) 0.4643(4) 0.4913(6) 0.092(2) Uani 1.000000 .
H10a H 0.4194(8) 0.446(2) 0.538(3) 0.138(3) Uiso 1.000000 GR
H10b H 0.332(4) 0.461(3) 0.4199(12) 0.138(3) Uiso 1.000000 GR
H10c H 0.323(3) 0.5230(7) 0.507(4) 0.138(3) Uiso 1.000000 GR
C21 C 0.8277(6) 0.0252(5) 0.3305(7) 0.099(2) Uani 1.000000 .
H21a H 0.854(4) 0.050(2) 0.278(3) 0.148(3) Uiso 1.000000 GR
H21b H 0.897(2) 0.024(3) 0.3969(13) 0.148(3) Uiso 1.000000 GR
H21c H 0.7978(18) -0.0328(12) 0.310(5) 0.148(3) Uiso 1.000000 GR
C12 C 0.0065(7) 0.4130(5) 0.6402(5) 0.098(2) Uani 1.000000 .
H12a H -0.059(4) 0.451(3) 0.5969(16) 0.147(4) Uiso 1.000000 GR
H12b H -0.030(5) 0.3645(6) 0.662(4) 0.147(4) Uiso 1.000000 GR
H12c H 0.0607(13) 0.444(3) 0.701(3) 0.147(4) Uiso 1.000000 GR
C7 C 0.0818(5) 0.3804(4) 0.5779(4) 0.0664(14) Uani 1.000000 .
N1 N 0.4272(3) 0.2284(3) 0.3574(3) 0.0492(8) Uani 1.000000 .
C1 C 0.4034(4) 0.2548(3) 0.4422(3) 0.0501(10) Uani 1.000000 .
C2 C 0.3248(4) 0.2471(3) 0.2663(4) 0.0571(11) Uani 1.000000 .
H2 H 0.3169(4) 0.2346(3) 0.1979(4) 0.0685(14) Uiso 1.000000 R


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 2.3891(8) . ?
Se1 Cu1 2.2526(9) . ?
Se1 C1 1.842(4) . ?
C13 C18 1.395(6) . ?
C13 C14 1.395(7) . ?
C13 N1 1.441(5) . ?
C18 C17 1.391(6) . ?
C18 C19 1.485(7) . ?
N2 C4 1.441(5) . ?
N2 C3 1.380(6) . ?
N2 C1 1.353(5) . ?
C4 C5 1.386(7) . ?
C4 C9 1.388(7) . ?
C14 C15 1.403(7) . ?
C14 C20 1.502(7) . ?
C17 C16 1.370(8) . ?
C16 C15 1.373(7) . ?
C16 C21 1.519(7) . ?
C5 C6 1.391(7) . ?
C5 C11 1.489(8) . ?
C3 C2 1.334(6) . ?
C9 C8 1.407(7) . ?
C9 C10 1.509(8) . ?
C6 C7 1.372(8) . ?
C8 C7 1.374(8) . ?
C12 C7 1.519(7) . ?
N1 C1 1.358(5) . ?
N1 C2 1.387(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Se1 Cu1 104.86(13) . . ?
Se1 Cu1 I1 159.60(4) . . ?
C14 C13 C18 123.2(4) . . ?
N1 C13 C18 119.7(4) . . ?
N1 C13 C14 116.7(4) . . ?
C17 C18 C13 116.9(5) . . ?
C19 C18 C13 122.0(4) . . ?
C19 C18 C17 121.2(5) . . ?
C3 N2 C4 124.7(4) . . ?
C1 N2 C4 125.1(4) . . ?
C1 N2 C3 109.8(4) . . ?
C5 C4 N2 118.3(4) . . ?
C9 C4 N2 119.1(4) . . ?
C9 C4 C5 122.6(4) . . ?
C15 C14 C13 116.2(4) . . ?
C20 C14 C13 122.7(5) . . ?
C20 C14 C15 121.1(5) . . ?
C16 C17 C18 122.3(4) . . ?
C15 C16 C17 119.0(4) . . ?
C21 C16 C17 120.8(5) . . ?
C21 C16 C15 120.2(6) . . ?
C6 C5 C4 117.2(5) . . ?
C11 C5 C4 121.8(5) . . ?
C11 C5 C6 121.0(5) . . ?
C16 C15 C14 122.4(5) . . ?
C2 C3 N2 107.5(4) . . ?
C8 C9 C4 117.4(5) . . ?
C10 C9 C4 122.1(5) . . ?
C10 C9 C8 120.4(5) . . ?
C7 C6 C5 122.5(5) . . ?
C7 C8 C9 121.3(5) . . ?
C8 C7 C6 119.0(5) . . ?
C12 C7 C6 121.2(6) . . ?
C12 C7 C8 119.9(6) . . ?
C1 N1 C13 126.3(4) . . ?
C2 N1 C13 123.9(4) . . ?
C2 N1 C1 109.3(4) . . ?
N2 C1 Se1 124.6(3) . . ?
N1 C1 Se1 129.5(3) . . ?
N1 C1 N2 105.9(4) . . ?
N1 C2 C3 107.4(4) . . ?

_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_2
_database_code_depnum_ccdc_archive 'CCDC 1855116'
_audit_update_record             
;
2018-07-11 deposited with the CCDC.
2018-09-03 downloaded from the CCDC.
;
_audit_creation_date             2017-09-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_formula_moiety         'C21 H24 Br Cu N2 S'
_chemical_formula_sum            'C21 H24 Br Cu N2 S'
_chemical_formula_weight         479.95
_chemical_oxdiff_formula         'C21 H24 N2 S Cu Br'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.33537 0.55136 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.67402 1.33011 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cu -1.96878 0.60861 13.33800 7.16760 5.61580 1.67350 3.58280 0.24700 11.39660
64.81260 1.19099998474
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   11.2063(2)
_cell_length_b                   15.3800(3)
_cell_length_c                   13.6241(3)
_cell_angle_alpha                90
_cell_angle_beta                 112.809(2)
_cell_angle_gamma                90
_cell_volume                     2164.52(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4119
_cell_measurement_temperature    298
_cell_measurement_theta_max      70.3650
_cell_measurement_theta_min      4.2610
_exptl_absorpt_coefficient_mu    4.526
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76687
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.4727
_exptl_crystal_F_000             968.5061
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8986
_diffrn_reflns_theta_full        70.9312
_diffrn_reflns_theta_max         70.93
_diffrn_reflns_theta_min         4.28
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1293
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 1.0000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -12.00   15.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -83.0000    3.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega  -41.00    0.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   38.0000 -150.0000 41

#__ type_ start__ end____ width___ exp.time_
  3 omega  -94.00  -17.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -50.0000   30.0000 77

#__ type_ start__ end____ width___ exp.time_
  4 omega   30.00   74.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -38.0000  150.0000 44

#__ type_ start__ end____ width___ exp.time_
  5 omega   51.00   76.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -38.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
  6 omega   27.00   53.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
  7 omega  -13.00   26.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -38.0000    0.0000 39

#__ type_ start__ end____ width___ exp.time_
  8 omega  -11.00   19.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000  120.0000 30

#__ type_ start__ end____ width___ exp.time_
  9 omega  -13.00   67.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000  -90.0000 80

#__ type_ start__ end____ width___ exp.time_
 10 omega   44.00   89.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -60.0000 45

#__ type_ start__ end____ width___ exp.time_
 11 omega   36.00   80.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   30.0000 44

#__ type_ start__ end____ width___ exp.time_
 12 omega   90.00  174.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000 -150.0000 84

#__ type_ start__ end____ width___ exp.time_
 13 omega   49.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  120.0000 66

#__ type_ start__ end____ width___ exp.time_
 14 omega  139.00  172.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000    0.0000 33

#__ type_ start__ end____ width___ exp.time_
 15 omega  109.00  135.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 16 omega   46.00  125.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000 -120.0000 79

#__ type_ start__ end____ width___ exp.time_
 17 omega   57.00  135.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   90.0000 78

#__ type_ start__ end____ width___ exp.time_
 18 omega   72.00  148.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000  150.0000 76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1161131000
_diffrn_orient_matrix_UB_12      0.0400713000
_diffrn_orient_matrix_UB_13      -0.0916536000
_diffrn_orient_matrix_UB_21      -0.0014121000
_diffrn_orient_matrix_UB_22      -0.0779661000
_diffrn_orient_matrix_UB_23      -0.0715152000
_diffrn_orient_matrix_UB_31      -0.0934624000
_diffrn_orient_matrix_UB_32      -0.0485300000
_diffrn_orient_matrix_UB_33      0.0391648000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -13
_reflns_limit_k_max              18
_reflns_limit_k_min              0
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                3303
_reflns_number_total             4081
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.5895
_refine_diff_density_min         -0.7487
_refine_diff_density_rms         0.0648
_refine_ls_d_res_high            0.8157
_refine_ls_d_res_low             10.3299
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0347
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    36
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4081
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0429
_refine_ls_restrained_S_all      1.0347
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0634P)²+0.8072P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1159
_refine_ls_wR_factor_ref         0.1260
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Me refined with riding coordinates:
 C20(H20a,H20b,H20c), C19(H19a,H19b,H19c), C12(H12a,H12b,H12c), C11(H11a,H11b,
 H11c), C10(H10a,H10b,H10c), C21(H21a,H21b,H21c)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C8(H8), C17(H17), C6(H6), C15(H15)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
Cu1 Cu 0.82198(4) 0.68747(4) 0.40349(4) 0.0671(2) Uani 1.000000 .
Br1 Br 0.62057(4) 0.63658(4) 0.34012(4) 0.1004(2) Uani 1.000000 .
S1 S 1.00515(8) 0.73887(8) 0.41810(6) 0.0763(3) Uani 1.000000 .
C9 C 1.3746(3) 0.7731(2) 0.5100(2) 0.0545(7) Uani 1.000000 .
N2 N 1.2153(2) 0.79168(16) 0.58689(17) 0.0483(5) Uani 1.000000 .
C14 C 0.8616(3) 0.71418(19) 0.6421(2) 0.0491(6) Uani 1.000000 .
N1 N 1.0756(2) 0.72719(16) 0.63582(17) 0.0483(5) Uani 1.000000 .
C2 C 1.1790(3) 0.7505(2) 0.7268(2) 0.0565(7) Uani 1.000000 .
H2 H 1.1870(3) 0.7407(2) 0.7965(2) 0.0678(9) Uiso 1.000000 R
C1 C 1.0985(3) 0.75206(19) 0.5494(2) 0.0486(6) Uani 1.000000 .
C3 C 1.2660(3) 0.7900(2) 0.6967(2) 0.0552(7) Uani 1.000000 .
H3 H 1.3458(3) 0.8121(2) 0.7416(2) 0.0662(8) Uiso 1.000000 R
C4 C 1.2815(3) 0.82511(19) 0.5232(2) 0.0497(6) Uani 1.000000 .
C18 C 0.9858(3) 0.5842(2) 0.6400(2) 0.0543(7) Uani 1.000000 .
C8 C 1.4439(3) 0.8076(3) 0.4533(3) 0.0632(8) Uani 1.000000 .
H8 H 1.5080(3) 0.7741(3) 0.4442(3) 0.0758(10) Uiso 1.000000 R
C13 C 0.9697(3) 0.67450(19) 0.6360(2) 0.0475(6) Uani 1.000000 .
C16 C 0.7787(3) 0.5713(2) 0.6560(3) 0.0590(7) Uani 1.000000 .
C20 C 1.1050(3) 0.5433(3) 0.6337(3) 0.0750(10) Uani 1.000000 .
H20a H 1.1613(3) 0.5880(3) 0.6274(3) 0.1125(15) Uiso 1.000000 R
H20b H 1.1493(3) 0.5100(3) 0.6970(3) 0.1125(15) Uiso 1.000000 R
H20c H 1.0800(3) 0.5058(3) 0.5727(3) 0.1125(15) Uiso 1.000000 R
C5 C 1.2535(3) 0.9083(2) 0.4806(3) 0.0610(8) Uani 1.000000 .
C7 C 1.4196(3) 0.8902(3) 0.4103(3) 0.0669(9) Uani 1.000000 .
C17 C 0.8884(3) 0.5344(2) 0.6495(3) 0.0626(8) Uani 1.000000 .
H17 H 0.8965(3) 0.4742(2) 0.6515(3) 0.0751(9) Uiso 1.000000 R
C19 C 0.8447(4) 0.8113(2) 0.6360(3) 0.0656(8) Uani 1.000000 .
H19a H 0.7643(4) 0.8262(2) 0.6416(3) 0.0984(13) Uiso 1.000000 R
H19b H 0.9150(4) 0.8380(2) 0.6933(3) 0.0984(13) Uiso 1.000000 R
H19c H 0.8439(4) 0.8319(2) 0.5692(3) 0.0984(13) Uiso 1.000000 R
C6 C 1.3255(4) 0.9381(2) 0.4243(3) 0.0683(9) Uani 1.000000 .
H6 H 1.3084(4) 0.9935(2) 0.3947(3) 0.0820(11) Uiso 1.000000 R
C15 C 0.7672(3) 0.6607(2) 0.6531(2) 0.0569(7) Uani 1.000000 .
H15 H 0.6946(3) 0.6859(2) 0.6587(2) 0.0683(9) Uiso 1.000000 R
C12 C 1.3993(4) 0.6817(3) 0.5534(4) 0.0836(11) Uani 1.000000 .
H12a H 1.4670(4) 0.6559(3) 0.5365(4) 0.1255(17) Uiso 1.000000 R
H12b H 1.4249(4) 0.6832(3) 0.6292(4) 0.1255(17) Uiso 1.000000 R
H12c H 1.3216(4) 0.6479(3) 0.5220(4) 0.1255(17) Uiso 1.000000 R
C11 C 1.4962(4) 0.9241(3) 0.3478(3) 0.0958(14) Uani 1.000000 .
H11a H 1.5577(4) 0.8810(3) 0.3470(3) 0.144(2) Uiso 1.000000 R
H11b H 1.4382(4) 0.9366(3) 0.2761(3) 0.144(2) Uiso 1.000000 R
H11c H 1.5411(4) 0.9762(3) 0.3807(3) 0.144(2) Uiso 1.000000 R
C10 C 1.1492(4) 0.9623(3) 0.4938(4) 0.0904(13) Uani 1.000000 .
H10a H 1.1439(4) 1.0174(3) 0.4592(4) 0.1357(19) Uiso 1.000000 R
H10b H 1.0677(4) 0.9327(3) 0.4623(4) 0.1357(19) Uiso 1.000000 R
H10c H 1.1691(4) 0.9715(3) 0.5682(4) 0.1357(19) Uiso 1.000000 R
C21 C 0.6745(4) 0.5145(3) 0.6670(4) 0.0890(13) Uani 1.000000 .
H21a H 0.6983(4) 0.4545(3) 0.6676(4) 0.1335(19) Uiso 1.000000 R
H21b H 0.6649(4) 0.5282(3) 0.7323(4) 0.1335(19) Uiso 1.000000 R
H21c H 0.5940(4) 0.5248(3) 0.6081(4) 0.1335(19) Uiso 1.000000 R


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 Br1 2.2229(6) . ?
Cu1 S1 2.1357(9) . ?
S1 C1 1.699(3) . ?
C9 C4 1.381(4) . ?
C9 C8 1.395(4) . ?
C9 C12 1.508(5) . ?
N2 C1 1.351(4) . ?
N2 C3 1.380(3) . ?
N2 C4 1.438(4) . ?
C14 C13 1.388(4) . ?
C14 C19 1.504(4) . ?
C14 C15 1.393(4) . ?
N1 C2 1.376(4) . ?
N1 C1 1.354(3) . ?
N1 C13 1.438(4) . ?
C2 C3 1.341(4) . ?
C4 C5 1.389(4) . ?
C18 C13 1.398(4) . ?
C18 C20 1.509(4) . ?
C18 C17 1.380(4) . ?
C8 C7 1.381(5) . ?
C16 C17 1.388(4) . ?
C16 C15 1.380(5) . ?
C16 C21 1.512(4) . ?
C5 C6 1.390(4) . ?
C5 C10 1.501(5) . ?
C7 C6 1.359(5) . ?
C7 C11 1.517(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
S1 Cu1 Br1 163.94(4) . . ?
C1 S1 Cu1 108.65(10) . . ?
C8 C9 C4 117.6(3) . . ?
C12 C9 C4 121.5(3) . . ?
C12 C9 C8 120.9(3) . . ?
C3 N2 C1 109.4(2) . . ?
C4 N2 C1 125.7(2) . . ?
C4 N2 C3 124.7(2) . . ?
C19 C14 C13 121.9(3) . . ?
C15 C14 C13 117.6(3) . . ?
C15 C14 C19 120.5(3) . . ?
C1 N1 C2 109.4(2) . . ?
C13 N1 C2 123.5(2) . . ?
C13 N1 C1 126.6(2) . . ?
C3 C2 N1 107.5(2) . . ?
N2 C1 S1 124.2(2) . . ?
N1 C1 S1 129.4(2) . . ?
N1 C1 N2 106.3(2) . . ?
C2 C3 N2 107.3(2) . . ?
N2 C4 C9 117.7(3) . . ?
C5 C4 C9 122.6(3) . . ?
C5 C4 N2 119.7(3) . . ?
C20 C18 C13 121.0(3) . . ?
C17 C18 C13 117.4(3) . . ?
C17 C18 C20 121.6(3) . . ?
C7 C8 C9 121.6(3) . . ?
N1 C13 C14 119.5(3) . . ?
C18 C13 C14 122.5(3) . . ?
C18 C13 N1 117.8(3) . . ?
C15 C16 C17 118.7(3) . . ?
C21 C16 C17 120.5(3) . . ?
C21 C16 C15 120.8(3) . . ?
C6 C5 C4 116.7(3) . . ?
C10 C5 C4 121.4(3) . . ?
C10 C5 C6 121.9(3) . . ?
C6 C7 C8 118.4(3) . . ?
C11 C7 C8 119.5(4) . . ?
C11 C7 C6 122.0(4) . . ?
C16 C17 C18 122.1(3) . . ?
C7 C6 C5 123.1(3) . . ?
C16 C15 C14 121.6(3) . . ?

_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_13
_database_code_depnum_ccdc_archive 'CCDC 1855118'
_audit_update_record             
;
2018-07-11 deposited with the CCDC.
2018-09-03 downloaded from the CCDC.
;
_audit_creation_date             2017-09-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C5 H7 Cu I N2 Se'
_chemical_formula_sum            'C5 H7 Cu I N2 Se'
_chemical_formula_weight         364.53
_chemical_oxdiff_formula         'C21 H24 N2 Se Cu I P'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
I -0.41187 1.83264 20.14720 18.99490 7.51380 2.27350 4.34700 0.38140 27.76600
66.87760 4.07119989395
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cu 0.34125 1.28947 13.33800 7.16760 5.61580 1.67350 3.58280 0.24700 11.39660
64.81260 1.19099998474
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Se -0.08110 2.30834 17.00060 5.81960 3.97310 4.35430 2.40980 0.27260 15.23720
43.81630 2.84089994431
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   9.8486(4)
_cell_length_b                   10.7720(3)
_cell_length_c                   8.0970(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.735(4)
_cell_angle_gamma                90
_cell_volume                     834.44(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1386
_cell_measurement_temperature    298
_cell_measurement_theta_max      27.6671
_cell_measurement_theta_min      3.2005
_exptl_absorpt_coefficient_mu    10.604
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80916
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.9015
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             667.7095
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0537
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3108
_diffrn_reflns_theta_full        27.7277
_diffrn_reflns_theta_max         27.73
_diffrn_reflns_theta_min         3.21
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean 16.1293
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 1.0000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   59.00   93.00   1.0000    3.4800
omega____ theta____ kappa____ phi______ frames
    -        0.8594  178.0000 -180.0000 34

#__ type_ start__ end____ width___ exp.time_
  2 omega -125.00  -60.00   1.0000   13.9100
omega____ theta____ kappa____ phi______ frames
    -      -28.9763  178.0000 -150.0000 65

#__ type_ start__ end____ width___ exp.time_
  3 omega   50.00  123.00   1.0000   13.9100
omega____ theta____ kappa____ phi______ frames
    -       30.6951  178.0000 -120.0000 73

#__ type_ start__ end____ width___ exp.time_
  4 omega  -41.00   96.00   1.0000   13.9100
omega____ theta____ kappa____ phi______ frames
    -       30.6951  -19.0000 -180.0000 137
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0571700000
_diffrn_orient_matrix_UB_12      0.0416514000
_diffrn_orient_matrix_UB_13      0.0092509000
_diffrn_orient_matrix_UB_21      -0.0302755000
_diffrn_orient_matrix_UB_22      0.0387722000
_diffrn_orient_matrix_UB_23      0.0522307000
_diffrn_orient_matrix_UB_31      0.0364440000
_diffrn_orient_matrix_UB_32      -0.0331933000
_diffrn_orient_matrix_UB_33      0.0727593000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              14
_reflns_limit_k_min              0
_reflns_limit_l_max              10
_reflns_limit_l_min              0
_reflns_number_gt                1490
_reflns_number_total             1813
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         2.2718
_refine_diff_density_min         -1.6529
_refine_diff_density_rms         0.3318
_refine_ls_d_res_high            0.7638
_refine_ls_d_res_low             6.3523
_refine_ls_goodness_of_fit_ref   1.0069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    11
_refine_ls_number_parameters     91
_refine_ls_number_reflns         1813
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0443
_refine_ls_restrained_S_all      1.0069
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0829P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1237
_refine_ls_wR_factor_ref         0.1395
_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:
 C5(H5a,H5b)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C2(H2)
2.c Idealised Me refined as rotating group:
 C4(H4a,H4b,H4c)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
I1 I 0.20581(6) 1.08953(4) 0.56385(6) 0.0338(2) Uani 1.000000 .
Se1 Se 0.13955(9) 0.74258(7) 0.31149(9) 0.0315(3) Uani 1.000000 .
Cu1 Cu 0.06886(12) 0.87594(10) 0.53809(14) 0.0424(3) Uani 1.000000 .
N1 N 0.1899(6) 0.5166(6) 0.5099(7) 0.0264(13) Uani 1.000000 .
N2 N 0.3711(7) 0.6351(6) 0.5501(7) 0.0267(13) Uani 1.000000 .
C1 C 0.2382(8) 0.6255(6) 0.4639(8) 0.0225(14) Uani 1.000000 .
C5 C 0.0476(8) 0.4715(7) 0.4480(9) 0.0287(17) Uani 1.000000 .
H5a H 0.0138(8) 0.4934(7) 0.3292(9) 0.034(2) Uiso 1.000000 R
H5b H 0.0463(8) 0.3817(7) 0.4573(9) 0.034(2) Uiso 1.000000 R
C3 C 0.2929(10) 0.4580(8) 0.6272(10) 0.0362(19) Uani 1.000000 .
H3 H 0.2859(10) 0.3817(8) 0.6783(10) 0.043(2) Uiso 1.000000 R
C2 C 0.4072(9) 0.5323(8) 0.6547(10) 0.039(2) Uani 1.000000 .
H2 H 0.4931(9) 0.5174(8) 0.7293(10) 0.047(2) Uiso 1.000000 R
C4 C 0.4614(10) 0.7428(9) 0.5473(12) 0.044(2) Uani 1.000000 .
H4a H 0.432(4) 0.810(2) 0.607(7) 0.066(3) Uiso 1.000000 GR
H4b H 0.5563(13) 0.7216(19) 0.601(7) 0.066(3) Uiso 1.000000 GR
H4c H 0.455(5) 0.767(4) 0.4317(12) 0.066(3) Uiso 1.000000 GR


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 2.6501(12) . ?
I1 Cu1 2.6603(13) 3_576 ?
Se1 Cu1 2.5067(13) 4_575 ?
Se1 Cu1 2.5537(14) . ?
Se1 C1 1.867(7) . ?
Cu1 Cu1 2.994(2) 3_576 ?
N1 C1 1.352(9) . ?
N1 C5 1.455(9) . ?
N1 C3 1.368(10) . ?
N2 C1 1.333(9) . ?
N2 C2 1.388(10) . ?
N2 C4 1.466(10) . ?
C5 C5 1.530(15) 3_566 ?
C5 H5a 0.9700 . ?
C5 H5b 0.9700 . ?
C3 H3 0.9300 . ?
C3 C2 1.356(12) . ?
C2 H2 0.9300 . ?
C4 H4a 0.9600 . ?
C4 H4b 0.9600 . ?
C4 H4c 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
C1 Se1 Cu1 103.4(2) . 4_575 ?
C1 Se1 Cu1 95.3(2) . . ?
Se1 Cu1 I1 108.93(5) . . ?
Se1 Cu1 I1 113.20(5) 4_576 3_576 ?
Se1 Cu1 I1 106.64(4) . 3_576 ?
Se1 Cu1 I1 110.07(4) 4_576 . ?
Cu1 Cu1 I1 55.84(4) 3_576 . ?
Cu1 Cu1 I1 55.51(4) 3_576 3_576 ?
Cu1 Cu1 Se1 130.82(7) 3_576 4_576 ?
Cu1 Cu1 Se1 122.79(6) 3_576 . ?
C5 N1 C1 124.6(6) . . ?
C3 N1 C1 109.9(6) . . ?
C3 N1 C5 125.4(6) . . ?
C2 N2 C1 109.6(7) . . ?
C4 N2 C1 125.2(7) . . ?
C4 N2 C2 124.9(7) . . ?
N1 C1 Se1 127.3(5) . . ?
N2 C1 Se1 125.9(5) . . ?
N2 C1 N1 106.8(6) . . ?
C5 C5 N1 110.0(7) 3_566 . ?
H5a C5 N1 109.7(4) . . ?
H5b C5 N1 109.7(4) . . ?
H5b C5 H5a 108.2 . . ?
H3 C3 N1 126.5(4) . . ?
C2 C3 N1 106.9(7) . . ?
C2 C3 H3 126.5(5) . . ?
C3 C2 N2 106.8(7) . . ?
H2 C2 N2 126.6(4) . . ?
H2 C2 C3 126.6(5) . . ?
H4a C4 N2 109.5 . . ?
H4b C4 N2 109.5 . . ?
H4b C4 H4a 109.5 . . ?
H4c C4 N2 109.5 . . ?
H4c C4 H4a 109.5 . . ?
H4c C4 H4b 109.5 . . ?

_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_12
_database_code_depnum_ccdc_archive 'CCDC 1855121'
_audit_update_record             
;
2018-07-11 deposited with the CCDC.
2018-09-03 downloaded from the CCDC.
;
_audit_creation_date             2017-09-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C72 H60 Cu4 I4 P4, 2(C2 N)'
_chemical_formula_sum            'C76 H60 Cu4 I4 N2 P4'
_chemical_formula_weight         1887.03
_chemical_oxdiff_formula         'C21 H24 N2 Se P Cu I'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
I -0.19206 6.94430 20.14720 18.99490 7.51380 2.27350 4.34700 0.38140 27.76600
66.87760 4.07119989395
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
P 0.30360 0.43703 6.43450 4.17910 1.78000 1.49080 1.90670 27.15700 0.52600
68.16450 1.11489999294
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cu -1.96878 0.60861 13.33800 7.16760 5.61580 1.67350 3.58280 0.24700 11.39660
64.81260 1.19099998474
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y,-z+1/2
3 -x,-y,-z
4 x,-y,z-1/2
5 x+1/2,y+1/2,z
6 -x+1/2,y+1/2,-z+1/2
7 -x+1/2,-y+1/2,-z
8 x+1/2,-y+1/2,z-1/2

_symmetry_Int_Tables_number      15
_cell_length_a                   26.6333(12)
_cell_length_b                   16.1396(6)
_cell_length_c                   18.2784(8)
_cell_angle_alpha                90
_cell_angle_beta                 110.048(5)
_cell_angle_gamma                90
_cell_volume                     7380.9(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5713
_cell_measurement_temperature    298
_cell_measurement_theta_max      71.4321
_cell_measurement_theta_min      3.2559
_exptl_absorpt_coefficient_mu    15.579
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.13326
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.6980
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             3650.2058
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0691
_diffrn_reflns_av_unetI/netI     0.0798
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            13446
_diffrn_reflns_theta_full        71.5742
_diffrn_reflns_theta_max         71.57
_diffrn_reflns_theta_min         3.26
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean 16.1293
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 1.0000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   28.00   55.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  -60.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega  -43.00    6.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  115.0000  168.0000 49

#__ type_ start__ end____ width___ exp.time_
  3 omega  -47.00  -21.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -57.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega  -27.00   25.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   38.0000    0.0000 52

#__ type_ start__ end____ width___ exp.time_
  5 omega  -22.00   28.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   25.0000  120.0000 50

#__ type_ start__ end____ width___ exp.time_
  6 omega -106.00  -80.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -57.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
  7 omega -104.00  -48.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000 -168.0000  -65.0000 56

#__ type_ start__ end____ width___ exp.time_
  8 omega  -13.00   85.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       55.1511  -77.0000 -180.0000 98

#__ type_ start__ end____ width___ exp.time_
  9 omega   47.00  133.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.3022  -77.0000  -60.0000 86

#__ type_ start__ end____ width___ exp.time_
 10 omega   82.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.3022   77.0000   30.0000 96

#__ type_ start__ end____ width___ exp.time_
 11 omega   44.00   78.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.3022  -25.0000  120.0000 34

#__ type_ start__ end____ width___ exp.time_
 12 omega  101.00  151.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.3022  115.0000  -11.0000 50

#__ type_ start__ end____ width___ exp.time_
 13 omega   58.00   83.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.3022  -25.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
 14 omega   88.00  174.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.3022   63.0000   90.0000 86

#__ type_ start__ end____ width___ exp.time_
 15 omega  109.00  150.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.3022  178.0000   30.0000 41

#__ type_ start__ end____ width___ exp.time_
 16 omega   80.00  177.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.3022   77.0000   60.0000 97
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0344327000
_diffrn_orient_matrix_UB_12      0.0681044000
_diffrn_orient_matrix_UB_13      0.0529719000
_diffrn_orient_matrix_UB_21      -0.0501048000
_diffrn_orient_matrix_UB_22      0.0349965000
_diffrn_orient_matrix_UB_23      0.0129432000
_diffrn_orient_matrix_UB_31      0.0101800000
_diffrn_orient_matrix_UB_32      -0.0570095000
_diffrn_orient_matrix_UB_33      0.0711575000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              30
_reflns_limit_h_min              -32
_reflns_limit_k_max              19
_reflns_limit_k_min              0
_reflns_limit_l_max              22
_reflns_limit_l_min              0
_reflns_number_gt                5546
_reflns_number_total             7046
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         2.5340
_refine_diff_density_min         -3.1965
_refine_diff_density_rms         0.2671
_refine_ls_d_res_high            0.8126
_refine_ls_d_res_low             13.5625
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0268
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    60
_refine_ls_number_parameters     406
_refine_ls_number_reflns         7046
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0917
_refine_ls_R_factor_gt           0.0790
_refine_ls_restrained_S_all      1.0268
_refine_ls_shift/su_max          0.0005
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1672P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2104
_refine_ls_wR_factor_ref         0.2419
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C2aa(H2aa), C3(H3), C3aa(H3aa), C4(H4), C5(H5), C6(H6), C8(H8),
 C9(H9), C10(H10), C11(H11), C12(H12), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C26(H26), C27(H27),
  C28(H28), C29(H29), C30(H30), C32(H32), C35(H35), C36(H36)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
I1 I 0.22504(2) 0.24843(3) 0.09679(3) 0.0395(2) Uani 1.000000 .
I2 I 0.36695(2) 0.37862(4) 0.12073(3) 0.0487(2) Uani 1.000000 .
Cu1 Cu 0.26991(5) 0.35213(8) 0.01978(7) 0.0439(3) Uani 1.000000 .
Cu2 Cu 0.36641(5) 0.29462(9) 0.00340(7) 0.0458(4) Uani 1.000000 .
P1 P 0.22516(7) 0.47063(12) -0.02325(11) 0.0319(4) Uani 1.000000 .
P2 P 0.43571(9) 0.27034(15) -0.03538(13) 0.0427(5) Uani 1.000000 .
C1 C 0.2459(4) 0.5264(5) -0.0948(5) 0.0397(17) Uani 1.000000 .
C2 C 0.3002(4) 0.5303(7) -0.0831(7) 0.061(3) Uani 1.000000 .
H2 H 0.3246(4) 0.5028(7) -0.0411(7) 0.073(3) Uiso 1.000000 R
C2aa C 0.4365(5) 0.1130(9) -0.2118(7) 0.078(4) Uani 1.000000 .
H2aa H 0.4474(5) 0.1134(9) -0.2550(7) 0.093(5) Uiso 1.000000 R
C3 C 0.3182(5) 0.5754(8) -0.1344(8) 0.072(3) Uani 1.000000 .
H3 H 0.3546(5) 0.5780(8) -0.1260(8) 0.086(4) Uiso 1.000000 R
C3aa C 0.4157(4) 0.0429(9) -0.1937(8) 0.074(4) Uani 1.000000 .
H3aa H 0.4123(4) -0.0045(9) -0.2240(8) 0.089(5) Uiso 1.000000 R
C4 C 0.2835(6) 0.6152(6) -0.1960(7) 0.066(3) Uani 1.000000 .
H4 H 0.2960(6) 0.6451(6) -0.2298(7) 0.079(4) Uiso 1.000000 R
C5 C 0.2301(5) 0.6117(6) -0.2086(6) 0.057(3) Uani 1.000000 .
H5 H 0.2062(5) 0.6382(6) -0.2517(6) 0.068(3) Uiso 1.000000 R
C6 C 0.2111(4) 0.5687(6) -0.1574(5) 0.0444(19) Uani 1.000000 .
H6 H 0.1747(4) 0.5685(6) -0.1653(5) 0.053(2) Uiso 1.000000 R
C7 C 0.2319(3) 0.5476(5) 0.0526(5) 0.0367(16) Uani 1.000000 .
C8 C 0.2392(5) 0.5214(6) 0.1273(6) 0.055(2) Uani 1.000000 .
H8 H 0.2405(5) 0.4649(6) 0.1377(6) 0.066(3) Uiso 1.000000 R
C9 C 0.2446(5) 0.5769(7) 0.1872(6) 0.060(3) Uani 1.000000 .
H9 H 0.2495(5) 0.5578(7) 0.2371(6) 0.072(3) Uiso 1.000000 R
C10 C 0.2429(4) 0.6598(7) 0.1723(6) 0.057(2) Uani 1.000000 .
H10 H 0.2472(4) 0.6975(7) 0.2124(6) 0.069(3) Uiso 1.000000 R
C11 C 0.2348(6) 0.6874(6) 0.0992(7) 0.070(3) Uani 1.000000 .
H11 H 0.2331(6) 0.7440(6) 0.0893(7) 0.083(4) Uiso 1.000000 R
C12 C 0.2289(5) 0.6318(6) 0.0390(6) 0.053(2) Uani 1.000000 .
H12 H 0.2230(5) 0.6515(6) -0.0111(6) 0.064(3) Uiso 1.000000 R
C13 C 0.1534(3) 0.4576(5) -0.0696(5) 0.0368(16) Uani 1.000000 .
C14 C 0.1346(4) 0.3841(6) -0.1113(6) 0.045(2) Uani 1.000000 .
H14 H 0.1588(4) 0.3451(6) -0.1167(6) 0.053(2) Uiso 1.000000 R
C15 C 0.0803(4) 0.3694(7) -0.1441(6) 0.053(2) Uani 1.000000 .
H15 H 0.0682(4) 0.3195(7) -0.1695(6) 0.064(3) Uiso 1.000000 R
C16 C 0.0442(4) 0.4279(7) -0.1396(7) 0.060(3) Uani 1.000000 .
H16 H 0.0078(4) 0.4179(7) -0.1625(7) 0.072(3) Uiso 1.000000 R
C17 C 0.0618(4) 0.5007(7) -0.1015(6) 0.058(2) Uani 1.000000 .
H17 H 0.0369(4) 0.5401(7) -0.0993(6) 0.069(3) Uiso 1.000000 R
C18 C 0.1157(4) 0.5177(6) -0.0662(6) 0.049(2) Uani 1.000000 .
H18 H 0.1269(4) 0.5678(6) -0.0406(6) 0.059(2) Uiso 1.000000 R
C19 C 0.5008(4) 0.2513(5) 0.0405(6) 0.045(2) Uani 1.000000 .
C20 C 0.5403(4) 0.2073(7) 0.0273(7) 0.062(3) Uani 1.000000 .
H20 H 0.5353(4) 0.1854(7) -0.0217(7) 0.074(3) Uiso 1.000000 R
C21 C 0.5882(5) 0.1954(9) 0.0874(9) 0.083(4) Uani 1.000000 .
H21 H 0.6147(5) 0.1642(9) 0.0780(9) 0.099(5) Uiso 1.000000 R
C22 C 0.5979(5) 0.2273(9) 0.1589(8) 0.073(3) Uani 1.000000 .
H22 H 0.6307(5) 0.2197(9) 0.1982(8) 0.088(4) Uiso 1.000000 R
C23 C 0.5570(6) 0.2720(10) 0.1720(8) 0.081(4) Uani 1.000000 .
H23 H 0.5625(6) 0.2938(10) 0.2212(8) 0.097(4) Uiso 1.000000 R
C24 C 0.5092(4) 0.2845(7) 0.1145(6) 0.058(2) Uani 1.000000 .
H24 H 0.4824(4) 0.3147(7) 0.1242(6) 0.070(3) Uiso 1.000000 R
C25 C 0.4462(4) 0.3593(6) -0.0898(6) 0.052(2) Uani 1.000000 .
C26 C 0.4943(6) 0.4013(9) -0.0681(9) 0.084(4) Uani 1.000000 .
H26 H 0.5234(6) 0.3854(9) -0.0252(9) 0.100(5) Uiso 1.000000 R
C27 C 0.4969(10) 0.4710(12) -0.1154(14) 0.134(8) Uani 1.000000 .
H27 H 0.5288(10) 0.5004(12) -0.1020(14) 0.161(10) Uiso 1.000000 R
C28 C 0.4574(10) 0.4955(10) -0.1760(12) 0.117(7) Uani 1.000000 .
H28 H 0.4612(10) 0.5396(10) -0.2064(12) 0.140(8) Uiso 1.000000 R
C29 C 0.4108(9) 0.4547(13) -0.1930(13) 0.132(8) Uani 1.000000 .
H29 H 0.3817(9) 0.4736(13) -0.2344(13) 0.159(10) Uiso 1.000000 R
C30 C 0.4038(7) 0.3865(10) -0.1524(10) 0.095(5) Uani 1.000000 .
H30 H 0.3711(7) 0.3592(10) -0.1670(10) 0.114(6) Uiso 1.000000 R
C31 C 0.4280(3) 0.1840(6) -0.1013(5) 0.0405(18) Uani 1.000000 .
C32 C 0.4422(4) 0.1840(8) -0.1674(6) 0.063(3) Uani 1.000000 .
H32 H 0.4555(4) 0.2320(8) -0.1821(6) 0.076(3) Uiso 1.000000 R
C35 C 0.3996(5) 0.0425(8) -0.1300(9) 0.077(3) Uani 1.000000 .
H35 H 0.3843(5) -0.0052(8) -0.1182(9) 0.093(4) Uiso 1.000000 R
C36 C 0.4056(5) 0.1115(7) -0.0831(6) 0.059(3) Uani 1.000000 .
H36 H 0.3949(5) 0.1100(7) -0.0398(6) 0.070(3) Uiso 1.000000 R
N1 N 0.6098(17) 0.2244(17) -0.110(2) 0.29(2) Uani 1.000000 .
C33 C 0.6103(11) 0.2848(15) -0.1161(16) 0.131(8) Uani 1.000000 .
C34 C 0.6220(13) 0.3682(19) -0.115(3) 0.29(3) Uani 1.000000 .


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 2.7135(14) . ?
I1 Cu1 2.7182(14) 7 ?
I1 Cu2 2.5906(14) 7 ?
I2 Cu1 2.6452(14) . ?
I2 Cu2 2.5331(14) . ?
Cu1 Cu2 2.8435(19) . ?
Cu1 P1 2.248(2) . ?
Cu2 P2 2.227(2) . ?
P1 C1 1.822(8) . ?
P1 C7 1.824(8) . ?
P1 C13 1.818(8) . ?
P2 C19 1.837(9) . ?
P2 C25 1.821(10) . ?
P2 C31 1.807(9) . ?
C1 C2 1.388(13) . ?
C1 C6 1.382(12) . ?
C2 C3 1.396(14) . ?
C2aa C3aa 1.35(2) . ?
C2aa C32 1.382(17) . ?
C3 C4 1.351(18) . ?
C3aa C35 1.371(19) . ?
C4 C5 1.361(17) . ?
C5 C6 1.392(11) . ?
C7 C8 1.377(12) . ?
C7 C12 1.379(13) . ?
C8 C9 1.382(13) . ?
C9 C10 1.364(16) . ?
C10 C11 1.353(15) . ?
C11 C12 1.387(13) . ?
C13 C14 1.406(12) . ?
C13 C18 1.413(12) . ?
C14 C15 1.382(12) . ?
C15 C16 1.369(15) . ?
C16 C17 1.365(15) . ?
C17 C18 1.385(13) . ?
C19 C20 1.359(14) . ?
C19 C24 1.399(14) . ?
C20 C21 1.380(16) . ?
C21 C22 1.34(2) . ?
C22 C23 1.39(2) . ?
C23 C24 1.359(18) . ?
C25 C26 1.382(16) . ?
C25 C30 1.374(19) . ?
C26 C27 1.434(19) . ?
C27 C28 1.30(3) . ?
C28 C29 1.34(3) . ?
C29 C30 1.38(2) . ?
C31 C32 1.384(13) . ?
C31 C36 1.404(13) . ?
C35 C36 1.381(15) . ?
N1 C33 0.98(4) . ?
C33 C34 1.38(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
Cu2 I1 Cu1 105.86(4) 7 . ?
Cu2 I1 Cu1 64.72(4) 7 7 ?
Cu2 I2 Cu1 66.57(4) . . ?
I2 Cu1 I1 103.68(5) . . ?
I2 Cu1 I1 110.14(5) . 7 ?
Cu2 Cu1 I1 115.34(5) . . ?
Cu2 Cu1 I1 55.47(4) . 7 ?
Cu2 Cu1 I2 54.83(4) . . ?
P1 Cu1 I1 115.55(7) . . ?
P1 Cu1 I1 113.35(7) . 7 ?
P1 Cu1 I2 112.37(7) . . ?
P1 Cu1 Cu2 129.10(8) . . ?
I2 Cu2 I1 118.23(5) . 7 ?
Cu1 Cu2 I1 59.81(4) . 7 ?
Cu1 Cu2 I2 58.60(4) . . ?
P2 Cu2 I1 114.13(8) . 7 ?
P2 Cu2 I2 126.79(8) . . ?
P2 Cu2 Cu1 165.62(9) . . ?
C1 P1 Cu1 114.6(3) . . ?
C7 P1 Cu1 114.3(3) . . ?
C7 P1 C1 103.5(4) . . ?
C13 P1 Cu1 114.3(3) . . ?
C13 P1 C1 104.6(4) . . ?
C13 P1 C7 104.3(4) . . ?
C19 P2 Cu2 117.4(3) . . ?
C25 P2 Cu2 109.5(3) . . ?
C25 P2 C19 105.2(5) . . ?
C31 P2 Cu2 115.5(3) . . ?
C31 P2 C19 103.7(4) . . ?
C31 P2 C25 104.3(4) . . ?
C2 C1 P1 117.9(7) . . ?
C6 C1 P1 123.8(7) . . ?
C6 C1 C2 118.2(9) . . ?
C3 C2 C1 119.9(10) . . ?
C32 C2aa C3aa 121.5(12) . . ?
C4 C3 C2 121.0(11) . . ?
C35 C3aa C2aa 119.1(12) . . ?
C5 C4 C3 119.9(9) . . ?
C6 C5 C4 120.4(10) . . ?
C5 C6 C1 120.6(9) . . ?
C8 C7 P1 119.2(7) . . ?
C12 C7 P1 123.3(7) . . ?
C12 C7 C8 117.5(8) . . ?
C9 C8 C7 121.8(9) . . ?
C10 C9 C8 119.4(9) . . ?
C11 C10 C9 120.2(10) . . ?
C12 C11 C10 120.5(10) . . ?
C11 C12 C7 120.7(9) . . ?
C14 C13 P1 118.2(6) . . ?
C18 C13 P1 123.3(7) . . ?
C18 C13 C14 118.5(8) . . ?
C15 C14 C13 120.4(8) . . ?
C16 C15 C14 120.5(9) . . ?
C17 C16 C15 119.9(9) . . ?
C18 C17 C16 121.9(10) . . ?
C17 C18 C13 118.8(9) . . ?
C20 C19 P2 122.8(8) . . ?
C24 C19 P2 117.6(8) . . ?
C24 C19 C20 119.6(10) . . ?
C21 C20 C19 119.5(11) . . ?
C22 C21 C20 122.5(13) . . ?
C23 C22 C21 117.6(12) . . ?
C24 C23 C22 121.6(13) . . ?
C23 C24 C19 119.2(11) . . ?
C26 C25 P2 122.1(9) . . ?
C30 C25 P2 118.1(10) . . ?
C30 C25 C26 119.8(12) . . ?
C27 C26 C25 116.3(16) . . ?
C28 C27 C26 124.0(18) . . ?
C29 C28 C27 117.5(15) . . ?
C30 C29 C28 123(2) . . ?
C29 C30 C25 118.7(18) . . ?
C32 C31 P2 125.4(8) . . ?
C36 C31 P2 116.4(7) . . ?
C36 C31 C32 118.2(9) . . ?
C31 C32 C2aa 120.3(12) . . ?
C36 C35 C3aa 121.3(13) . . ?
C35 C36 C31 119.6(10) . . ?
C34 C33 N1 168(5) . . ?

_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_9
_database_code_depnum_ccdc_archive 'CCDC 1855120'
_audit_update_record             
;
2018-07-11 deposited with the CCDC.
2018-09-03 downloaded from the CCDC.
;
_audit_creation_date             2017-09-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C42 H48 Cu N4 Se2, F6 P'
_chemical_formula_sum            'C42 H48 Cu F6 N4 P Se2'
_chemical_formula_weight         975.30
_chemical_oxdiff_formula         'C10 H19 N2 Se Cu P F'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.07537 0.05506 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
P 0.30360 0.43703 6.43450 4.17910 1.78000 1.49080 1.90670 27.15700 0.52600
68.16450 1.11489999294
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cu -1.96878 0.60861 13.33800 7.16760 5.61580 1.67350 3.58280 0.24700 11.39660
64.81260 1.19099998474
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Se -0.79210 1.18296 17.00060 5.81960 3.97310 4.35430 2.40980 0.27260 15.23720
43.81630 2.84089994431
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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 2ybc (x-z,y,z)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   8.4401(2)
_cell_length_b                   18.3180(4)
_cell_length_c                   14.4474(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.023(2)
_cell_angle_gamma                90
_cell_volume                     2211.79(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3336
_cell_measurement_temperature    298
_cell_measurement_theta_max      71.3210
_cell_measurement_theta_min      3.0640
_exptl_absorpt_coefficient_mu    3.421
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62506
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.4644
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             984.1165
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7598
_diffrn_reflns_theta_full        71.5335
_diffrn_reflns_theta_max         71.53
_diffrn_reflns_theta_min         3.92
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1293
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 1.0000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    8.00   34.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   38.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega   47.00   72.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   38.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
  3 omega -110.00  -12.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000  120.0000 98

#__ type_ start__ end____ width___ exp.time_
  4 omega  -49.00   30.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   38.0000   60.0000 79

#__ type_ start__ end____ width___ exp.time_
  5 omega  -50.00   -2.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   25.0000  -90.0000 48

#__ type_ start__ end____ width___ exp.time_
  6 omega  -68.00  -42.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -63.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
  7 omega  -10.00   25.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   38.0000  -90.0000 35

#__ type_ start__ end____ width___ exp.time_
  8 omega   57.00   92.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.2786  -38.0000   60.0000 35

#__ type_ start__ end____ width___ exp.time_
  9 omega   57.00   91.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.2786  -25.0000 -180.0000 34

#__ type_ start__ end____ width___ exp.time_
 10 omega   40.00   80.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.2786  -50.0000  -30.0000 40

#__ type_ start__ end____ width___ exp.time_
 11 omega   51.00   87.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.2786  -25.0000  -30.0000 36

#__ type_ start__ end____ width___ exp.time_
 12 omega   88.00  167.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.2786   50.0000 -120.0000 79

#__ type_ start__ end____ width___ exp.time_
 13 omega   57.00   87.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.2786  178.0000 -150.0000 30

#__ type_ start__ end____ width___ exp.time_
 14 omega  113.00  139.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.2786  178.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 15 omega   56.00   97.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.2786  -54.0000  -93.0000 41

#__ type_ start__ end____ width___ exp.time_
 16 omega   38.00   93.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.2786  -38.0000  120.0000 55

#__ type_ start__ end____ width___ exp.time_
 17 omega   61.00  165.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.2786   12.0000   30.0000 104
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0981693000
_diffrn_orient_matrix_UB_12      -0.0511412000
_diffrn_orient_matrix_UB_13      0.0708096000
_diffrn_orient_matrix_UB_21      -0.1529563000
_diffrn_orient_matrix_UB_22      -0.0198731000
_diffrn_orient_matrix_UB_23      0.0414784000
_diffrn_orient_matrix_UB_31      -0.0310326000
_diffrn_orient_matrix_UB_32      -0.0636722000
_diffrn_orient_matrix_UB_33      -0.0697858000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -10
_reflns_limit_k_max              22
_reflns_limit_k_min              0
_reflns_limit_l_max              17
_reflns_limit_l_min              -7
_reflns_number_gt                3357
_reflns_number_total             4227
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.6070
_refine_diff_density_min         -0.6238
_refine_diff_density_rms         0.1066
_refine_ls_d_res_high            0.8128
_refine_ls_d_res_low             11.2749
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0400
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    36
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0472
_refine_ls_restrained_S_all      1.0400
_refine_ls_shift/su_max          0.0005
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0945P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1319
_refine_ls_wR_factor_ref         0.1522
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C8(H8), C15(H15), C17(H17)
2.b Idealised Me refined as rotating group:
 C10(H10a,H10b,H10c), C11(H11a,H11b,H11c), C12(H12a,H12b,H12c), C19(H19a,H19b,
 H19c), C20(H20a,H20b,H20c), C21(H21a,H21b,H21c)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Se1 Se 0.80236(5) 0.07915(2) 0.51813(2) 0.0720(2) Uani 1.000000 1 . . .
Cu1 Cu 1.0 0.0 0.5 0.0662(2) Uani 1.000000 2 S T P
N1 N 0.7051(4) 0.12257(18) 0.6893(2) 0.0708(8) Uani 1.000000 1 . . .
N2 N 0.8094(4) 0.01473(16) 0.70385(19) 0.0644(7) Uani 1.000000 1 . . .
C1 C 0.7748(4) 0.07036(18) 0.6426(2) 0.0617(8) Uani 1.000000 1 . . .
C2 C 0.6941(6) 0.0988(3) 0.7788(3) 0.0911(13) Uani 1.000000 1 . . .
H2 H 0.6497(6) 0.1244(3) 0.8245(3) 0.1093(16) Uiso 1.000000 1 R . .
C3 C 0.7581(6) 0.0327(3) 0.7879(3) 0.0878(12) Uani 1.000000 1 . . .
H3 H 0.7669(6) 0.0037(3) 0.8411(3) 0.1054(15) Uiso 1.000000 1 R . .
C4 C 0.8895(4) -0.05205(19) 0.6866(2) 0.0605(7) Uani 1.000000 1 . . .
C5 C 1.0544(4) -0.0557(2) 0.7106(2) 0.0682(9) Uani 1.000000 1 . . .
C6 C 1.1269(5) -0.1216(2) 0.6955(3) 0.0760(10) Uani 1.000000 1 . . .
H6 H 1.2372(5) -0.1254(2) 0.7116(3) 0.0912(12) Uiso 1.000000 1 R . .
C7 C 1.0443(5) -0.1813(2) 0.6580(3) 0.0796(11) Uani 1.000000 1 . . .
C8 C 0.8803(5) -0.1754(2) 0.6371(3) 0.0794(10) Uani 1.000000 1 . . .
H8 H 0.8222(5) -0.2157(2) 0.6123(3) 0.0953(13) Uiso 1.000000 1 R . .
C9 C 0.7986(4) -0.1113(2) 0.6516(3) 0.0702(9) Uani 1.000000 1 . . .
C10 C 1.1493(6) 0.0089(2) 0.7517(4) 0.0986(14) Uani 1.000000 1 . . .
H10a H 1.133(4) 0.0153(13) 0.8155(9) 0.148(2) Uiso 1.000000 1 GR . .
H10b H 1.2609(7) 0.0008(9) 0.749(3) 0.148(2) Uiso 1.000000 1 GR . .
H10c H 1.115(3) 0.0520(4) 0.7166(17) 0.148(2) Uiso 1.000000 1 GR . .
C11 C 1.1309(7) -0.2506(2) 0.6371(4) 0.1166(19) Uani 1.000000 1 . . .
H11a H 1.204(4) -0.2400(6) 0.594(3) 0.175(3) Uiso 1.000000 1 GR . .
H11b H 1.189(4) -0.2696(14) 0.6939(7) 0.175(3) Uiso 1.000000 1 GR . .
H11c H 1.0545(9) -0.2862(9) 0.610(3) 0.175(3) Uiso 1.000000 1 GR . .
C12 C 0.6189(5) -0.1065(3) 0.6311(4) 0.1010(15) Uani 1.000000 1 . . .
H12a H 0.5766(6) -0.1525(7) 0.607(3) 0.152(2) Uiso 1.000000 1 GR . .
H12b H 0.5761(6) -0.095(2) 0.6875(6) 0.152(2) Uiso 1.000000 1 GR . .
H12c H 0.5894(5) -0.0690(14) 0.5855(19) 0.152(2) Uiso 1.000000 1 GR . .
C13 C 0.6486(4) 0.1915(2) 0.6498(2) 0.0661(8) Uani 1.000000 1 . . .
C14 C 0.7579(5) 0.2476(2) 0.6442(3) 0.0740(10) Uani 1.000000 1 . . .
C15 C 0.6997(5) 0.3125(2) 0.6024(3) 0.0807(10) Uani 1.000000 1 . . .
H15 H 0.7705(5) 0.3505(2) 0.5962(3) 0.0968(13) Uiso 1.000000 1 R . .
C16 C 0.5395(5) 0.3217(2) 0.5700(3) 0.0821(11) Uani 1.000000 1 . . .
C17 C 0.4361(5) 0.2652(2) 0.5791(3) 0.0819(11) Uani 1.000000 1 . . .
H17 H 0.3278(5) 0.2720(2) 0.5582(3) 0.0983(13) Uiso 1.000000 1 R . .
C18 C 0.4858(5) 0.1985(2) 0.6180(3) 0.0725(9) Uani 1.000000 1 . . .
C19 C 0.9335(5) 0.2393(3) 0.6784(4) 0.1115(18) Uani 1.000000 1 . . .
H19a H 0.9475(5) 0.214(2) 0.7373(15) 0.167(3) Uiso 1.000000 1 GR . .
H19b H 0.9830(11) 0.212(2) 0.6337(14) 0.167(3) Uiso 1.000000 1 GR . .
H19c H 0.9822(11) 0.2867(3) 0.686(3) 0.167(3) Uiso 1.000000 1 GR . .
C20 C 0.4803(7) 0.3921(3) 0.5242(4) 0.1161(18) Uani 1.000000 1 . . .
H20a H 0.522(5) 0.3975(13) 0.4661(16) 0.174(3) Uiso 1.000000 1 GR . .
H20b H 0.3656(7) 0.3916(11) 0.513(3) 0.174(3) Uiso 1.000000 1 GR . .
H20c H 0.515(5) 0.4323(3) 0.5647(14) 0.174(3) Uiso 1.000000 1 GR . .
C21 C 0.3708(6) 0.1378(3) 0.6246(4) 0.1011(15) Uani 1.000000 1 . . .
H21a H 0.406(3) 0.0950(7) 0.595(2) 0.152(2) Uiso 1.000000 1 GR . .
H21b H 0.365(4) 0.1274(15) 0.6892(4) 0.152(2) Uiso 1.000000 1 GR . .
H21c H 0.2670(12) 0.1517(9) 0.594(2) 0.152(2) Uiso 1.000000 1 GR . .
P1 P 0.5 0.0 0.0 0.0799(4) Uani 1.000000 2 S T P
F1 F 0.5023(7) 0.0704(2) -0.0565(3) 0.191(2) Uani 1.000000 1 . . .
F2 F 0.3166(3) 0.0088(3) -0.0005(3) 0.1620(18) Uani 1.000000 1 . . .
F3 F 0.5213(4) 0.0443(2) 0.0942(2) 0.1472(13) Uani 1.000000 1 . . .


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
Se1 Cu1 2.2528(3) . ?
Se1 C1 1.853(3) . ?
N1 C1 1.351(4) . ?
N1 C2 1.380(5) . ?
N1 C13 1.440(5) . ?
N2 C1 1.354(4) . ?
N2 C3 1.385(4) . ?
N2 C4 1.436(4) . ?
C2 C3 1.323(6) . ?
C4 C5 1.388(5) . ?
C4 C9 1.383(5) . ?
C5 C6 1.383(6) . ?
C5 C10 1.504(5) . ?
C6 C7 1.367(6) . ?
C7 C8 1.379(6) . ?
C7 C11 1.517(6) . ?
C8 C9 1.393(5) . ?
C9 C12 1.507(5) . ?
C13 C14 1.391(5) . ?
C13 C18 1.392(5) . ?
C14 C15 1.393(5) . ?
C14 C19 1.503(6) . ?
C15 C16 1.378(6) . ?
C16 C17 1.372(6) . ?
C16 C20 1.503(6) . ?
C17 C18 1.385(5) . ?
C18 C21 1.488(5) . ?
P1 F1 1.527(3) . ?
P1 F1 1.527(3) 3_655 ?
P1 F2 1.555(3) . ?
P1 F2 1.555(3) 3_655 ?
P1 F3 1.574(3) . ?
P1 F3 1.574(3) 3_655 ?

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
C1 Se1 Cu1 104.61(10) . . ?
Se1 Cu1 Se1 180.0 3_756 . ?
C2 N1 C1 109.6(3) . . ?
C13 N1 C1 124.5(3) . . ?
C13 N1 C2 126.0(3) . . ?
C3 N2 C1 109.1(3) . . ?
C4 N2 C1 126.3(3) . . ?
C4 N2 C3 124.6(3) . . ?
N1 C1 Se1 123.0(2) . . ?
N2 C1 Se1 130.9(2) . . ?
N2 C1 N1 106.0(3) . . ?
C3 C2 N1 107.6(3) . . ?
C2 C3 N2 107.7(3) . . ?
C5 C4 N2 118.5(3) . . ?
C9 C4 N2 118.7(3) . . ?
C9 C4 C5 122.6(3) . . ?
C6 C5 C4 116.9(4) . . ?
C10 C5 C4 121.3(4) . . ?
C10 C5 C6 121.7(4) . . ?
C7 C6 C5 123.2(4) . . ?
C8 C7 C6 117.7(4) . . ?
C11 C7 C6 121.0(4) . . ?
C11 C7 C8 121.2(4) . . ?
C9 C8 C7 122.4(4) . . ?
C8 C9 C4 117.1(3) . . ?
C12 C9 C4 121.2(4) . . ?
C12 C9 C8 121.7(4) . . ?
C14 C13 N1 119.0(3) . . ?
C18 C13 N1 118.0(3) . . ?
C18 C13 C14 123.0(3) . . ?
C15 C14 C13 117.3(4) . . ?
C19 C14 C13 122.6(4) . . ?
C19 C14 C15 120.0(4) . . ?
C16 C15 C14 121.5(4) . . ?
C17 C16 C15 118.8(4) . . ?
C20 C16 C15 120.3(4) . . ?
C20 C16 C17 120.9(4) . . ?
C18 C17 C16 122.9(4) . . ?
C17 C18 C13 116.4(4) . . ?
C21 C18 C13 122.1(4) . . ?
C21 C18 C17 121.5(4) . . ?
F1 P1 F1 180.0 3_655 . ?
F2 P1 F1 89.8(3) . . ?
F2 P1 F1 90.2(3) . 3_655 ?
F2 P1 F1 90.2(3) 3_655 . ?
F2 P1 F1 89.8(3) 3_655 3_655 ?
F2 P1 F2 180.0 3_655 . ?
F3 P1 F1 91.0(3) . . ?
F3 P1 F1 89.0(3) . 3_655 ?
F3 P1 F1 89.0(3) 3_655 . ?
F3 P1 F1 91.0(3) 3_655 3_655 ?
F3 P1 F2 86.8(2) . . ?
F3 P1 F2 93.2(2) 3_655 . ?
F3 P1 F2 86.8(2) 3_655 3_655 ?
F3 P1 F2 93.2(2) . 3_655 ?
F3 P1 F3 180.0 3_655 . ?

_olex2_submission_special_instructions 'No special instructions were received'
