# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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 1468756'
_audit_update_record             
;
2017-08-22 deposited with the CCDC.
2017-10-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H19 Cu N6 O4, N O3'
_chemical_formula_sum            'C16 H19 Cu N7 O7'
_chemical_formula_weight         484.92

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.6735(9)
_cell_length_b                   17.4644(11)
_cell_length_c                   12.1452(13)
_cell_angle_alpha                90
_cell_angle_beta                 103.407(10)
_cell_angle_gamma                90
_cell_volume                     1995.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(1)
_cell_measurement_reflns_used    2571
_cell_measurement_theta_min      3.2480
_cell_measurement_theta_max      26.9290

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.614
_exptl_crystal_F_000             996
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    1.150
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.66044
_exptl_absorpt_correction_T_max  1.00000
_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_absorpt_special_details   ?

_diffrn_ambient_temperature      200(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.1544
_diffrn_measurement_method       ω-scan
_diffrn_reflns_number            7123
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.064
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3514
_reflns_number_gt                2618
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_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_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_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'



_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0658P)²+2.5163P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3514
_refine_ls_number_parameters     284
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_gt           0.0551
_refine_ls_wR_factor_ref         0.1424
_refine_ls_wR_factor_gt          0.1325
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.72670(6) 0.20149(3) 0.72281(5) 0.0432(2) Uani 1 1 d . . . . .
N1A N 0.8950(4) 0.22189(19) 0.6642(3) 0.0431(8) Uani 1 1 d . . . . .
C2A C 0.9276(5) 0.2952(2) 0.6644(3) 0.0408(10) Uani 1 1 d . . . . .
N3A N 1.0462(4) 0.3084(2) 0.6283(3) 0.0463(9) Uani 1 1 d . . . . .
H3A H 1.0850 0.3533 0.6226 0.056 Uiso 1 1 calc R U . . .
C4A C 1.0965(5) 0.2382(3) 0.6017(3) 0.0430(10) Uani 1 1 d . . . . .
C5A C 1.2141(5) 0.2164(3) 0.5617(4) 0.0514(12) Uani 1 1 d . . . . .
H5A H 1.2783 0.2533 0.5449 0.062 Uiso 1 1 calc R U . . .
C6A C 1.2343(5) 0.1394(3) 0.5473(4) 0.0584(13) Uani 1 1 d . . . . .
H6A H 1.3141 0.1229 0.5205 0.070 Uiso 1 1 calc R U . . .
C7A C 1.1401(5) 0.0852(3) 0.5713(4) 0.0580(13) Uani 1 1 d . . . . .
H7A H 1.1564 0.0324 0.5599 0.070 Uiso 1 1 calc R U . . .
C8A C 1.0234(5) 0.1064(3) 0.6114(4) 0.0520(12) Uani 1 1 d . . . . .
H8A H 0.9601 0.0691 0.6285 0.062 Uiso 1 1 calc R U . . .
C9A C 1.0013(5) 0.1835(2) 0.6259(3) 0.0411(10) Uani 1 1 d . . . . .
N10A N 0.8425(4) 0.35056(19) 0.6969(3) 0.0464(9) Uani 1 1 d . . . . .
C11A C 0.9084(6) 0.4214(3) 0.7490(5) 0.0634(14) Uani 1 1 d . . . . .
H11C H 0.8706 0.4650 0.7006 0.095 Uiso 1 1 calc R U . . .
H11B H 1.0115 0.4185 0.7576 0.095 Uiso 1 1 calc R U . . .
H11A H 0.8871 0.4279 0.8235 0.095 Uiso 1 1 calc R U . . .
N12A N 0.7311(4) 0.31544(19) 0.7310(3) 0.0437(8) Uani 1 1 d . . . . .
C13A C 0.6219(5) 0.3499(2) 0.7495(3) 0.0431(10) Uani 1 1 d . . . . .
C14A C 0.5894(6) 0.4331(3) 0.7357(5) 0.0623(14) Uani 1 1 d . . . . .
H14C H 0.6384 0.4604 0.8041 0.093 Uiso 1 1 calc R U . . .
H14B H 0.4866 0.4409 0.7236 0.093 Uiso 1 1 calc R U . . .
H14A H 0.6217 0.4527 0.6704 0.093 Uiso 1 1 calc R U . . .
C15A C 0.5205(5) 0.2962(2) 0.7842(3) 0.0427(10) Uani 1 1 d . . . . .
N16A N 0.5502(4) 0.2207(2) 0.7767(3) 0.0420(8) Uani 1 1 d . . . . .
C17A C 0.4687(5) 0.1684(3) 0.8086(4) 0.0501(11) Uani 1 1 d . . . . .
H17A H 0.4902 0.1158 0.8015 0.060 Uiso 1 1 calc R U . . .
C18A C 0.3519(5) 0.1878(3) 0.8524(4) 0.0560(13) Uani 1 1 d . . . . .
H18A H 0.2965 0.1493 0.8769 0.067 Uiso 1 1 calc R U . . .
C19A C 0.3198(5) 0.2635(3) 0.8589(4) 0.0598(13) Uani 1 1 d . . . . .
H19A H 0.2399 0.2786 0.8867 0.072 Uiso 1 1 calc R U . . .
C20A C 0.4057(5) 0.3189(3) 0.8243(4) 0.0503(11) Uani 1 1 d . . . . .
H20A H 0.3844 0.3717 0.8287 0.060 Uiso 1 1 calc R U . . .
N1B N 0.6420(4) 0.0969(2) 0.5587(4) 0.0564(10) Uani 1 1 d . . . . .
O1B O 0.6900(4) 0.09556(17) 0.6661(3) 0.0548(8) Uani 1 1 d . . . . .
O2B O 0.5949(4) 0.1578(2) 0.5134(3) 0.0713(10) Uani 1 1 d . . . . .
O3B O 0.6450(5) 0.0375(3) 0.5062(4) 0.0987(15) Uani 1 1 d . . . . .
O1C O 0.8421(4) 0.1533(2) 0.8869(3) 0.0704(10) Uani 1 1 d . . . . .
H1C H 0.8002 0.1252 0.9249 0.085 Uiso 1 1 calc R U . . .
C1C C 0.9862(7) 0.1457(4) 0.9261(5) 0.093(2) Uani 1 1 d . . . . .
H1C3 H 1.0346 0.1672 0.8707 0.140 Uiso 1 1 calc R U . . .
H1C2 H 1.0103 0.0913 0.9376 0.140 Uiso 1 1 calc R U . . .
H1C1 H 1.0166 0.1731 0.9981 0.140 Uiso 1 1 calc R U . . .
N1D N 0.7115(5) 0.0236(3) 0.0607(4) 0.0658(12) Uani 1 1 d . . . . .
O1D O 0.6669(9) 0.0085(4) 0.1434(6) 0.181(3) Uani 1 1 d . . . . .
O2D O 0.7074(6) 0.0902(2) 0.0376(5) 0.127(2) Uani 1 1 d . . . . .
O3D O 0.7611(6) -0.0223(3) 0.0109(5) 0.1218(19) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N1A 1.956(3) . ?
Cu1 O1B 1.977(3) . ?
Cu1 N12A 1.993(3) . ?
Cu1 N16A 1.994(3) . ?
Cu1 O1C 2.212(3) . ?
N1A C2A 1.319(5) . ?
N1A C9A 1.395(5) . ?
C2A N3A 1.340(5) . ?
C2A N10A 1.385(5) . ?
N3A C4A 1.384(6) . ?
N3A H3A 0.8800 . ?
C4A C5A 1.390(6) . ?
C4A C9A 1.404(6) . ?
C5A C6A 1.376(7) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.391(7) . ?
C6A H6A 0.9500 . ?
C7A C8A 1.380(6) . ?
C7A H7A 0.9500 . ?
C8A C9A 1.379(6) . ?
C8A H8A 0.9500 . ?
N10A N12A 1.384(5) . ?
N10A C11A 1.466(5) . ?
C11A H11C 0.9800 . ?
C11A H11B 0.9800 . ?
C11A H11A 0.9800 . ?
N12A C13A 1.281(5) . ?
C13A C14A 1.486(6) . ?
C13A C15A 1.487(6) . ?
C14A H14C 0.9800 . ?
C14A H14B 0.9800 . ?
C14A H14A 0.9800 . ?
C15A N16A 1.357(5) . ?
C15A C20A 1.371(6) . ?
N16A C17A 1.322(6) . ?
C17A C18A 1.396(6) . ?
C17A H17A 0.9500 . ?
C18A C19A 1.366(7) . ?
C18A H18A 0.9500 . ?
C19A C20A 1.401(7) . ?
C19A H19A 0.9500 . ?
C20A H20A 0.9500 . ?
N1B O3B 1.221(5) . ?
N1B O2B 1.235(5) . ?
N1B O1B 1.279(5) . ?
O1C C1C 1.371(6) . ?
O1C H1C 0.8400 . ?
C1C H1C3 0.9800 . ?
C1C H1C2 0.9800 . ?
C1C H1C1 0.9800 . ?
N1D O3D 1.172(5) . ?
N1D O2D 1.195(6) . ?
N1D O1D 1.210(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
N1A Cu1 O1B 98.10(14) . . ?
N1A Cu1 N12A 79.99(14) . . ?
O1B Cu1 N12A 162.16(15) . . ?
N1A Cu1 N16A 159.68(15) . . ?
O1B Cu1 N16A 100.02(14) . . ?
N12A Cu1 N16A 79.94(14) . . ?
N1A Cu1 O1C 96.23(14) . . ?
O1B Cu1 O1C 88.30(15) . . ?
N12A Cu1 O1C 109.54(16) . . ?
N16A Cu1 O1C 93.43(13) . . ?
C2A N1A C9A 105.9(3) . . ?
C2A N1A Cu1 113.2(3) . . ?
C9A N1A Cu1 140.7(3) . . ?
N1A C2A N3A 112.8(4) . . ?
N1A C2A N10A 121.4(4) . . ?
N3A C2A N10A 125.8(4) . . ?
C2A N3A C4A 107.4(3) . . ?
C2A N3A H3A 126.3 . . ?
C4A N3A H3A 126.3 . . ?
N3A C4A C5A 133.2(4) . . ?
N3A C4A C9A 105.7(4) . . ?
C5A C4A C9A 121.1(4) . . ?
C6A C5A C4A 117.6(4) . . ?
C6A C5A H5A 121.2 . . ?
C4A C5A H5A 121.2 . . ?
C5A C6A C7A 121.3(4) . . ?
C5A C6A H6A 119.3 . . ?
C7A C6A H6A 119.3 . . ?
C8A C7A C6A 121.3(5) . . ?
C8A C7A H7A 119.3 . . ?
C6A C7A H7A 119.3 . . ?
C9A C8A C7A 118.1(4) . . ?
C9A C8A H8A 120.9 . . ?
C7A C8A H8A 120.9 . . ?
C8A C9A N1A 131.3(4) . . ?
C8A C9A C4A 120.6(4) . . ?
N1A C9A C4A 108.2(4) . . ?
N12A N10A C2A 109.4(3) . . ?
N12A N10A C11A 122.4(4) . . ?
C2A N10A C11A 118.9(4) . . ?
N10A C11A H11C 109.5 . . ?
N10A C11A H11B 109.5 . . ?
H11C C11A H11B 109.5 . . ?
N10A C11A H11A 109.5 . . ?
H11C C11A H11A 109.5 . . ?
H11B C11A H11A 109.5 . . ?
C13A N12A N10A 125.1(4) . . ?
C13A N12A Cu1 118.0(3) . . ?
N10A N12A Cu1 115.9(3) . . ?
N12A C13A C14A 127.0(4) . . ?
N12A C13A C15A 112.2(4) . . ?
C14A C13A C15A 120.8(4) . . ?
C13A C14A H14C 109.5 . . ?
C13A C14A H14B 109.5 . . ?
H14C C14A H14B 109.5 . . ?
C13A C14A H14A 109.5 . . ?
H14C C14A H14A 109.5 . . ?
H14B C14A H14A 109.5 . . ?
N16A C15A C20A 120.4(4) . . ?
N16A C15A C13A 115.5(4) . . ?
C20A C15A C13A 124.1(4) . . ?
C17A N16A C15A 120.1(4) . . ?
C17A N16A Cu1 126.5(3) . . ?
C15A N16A Cu1 113.3(3) . . ?
N16A C17A C18A 122.3(5) . . ?
N16A C17A H17A 118.9 . . ?
C18A C17A H17A 118.9 . . ?
C19A C18A C17A 118.1(5) . . ?
C19A C18A H18A 120.9 . . ?
C17A C18A H18A 120.9 . . ?
C18A C19A C20A 119.5(4) . . ?
C18A C19A H19A 120.3 . . ?
C20A C19A H19A 120.3 . . ?
C15A C20A C19A 119.6(4) . . ?
C15A C20A H20A 120.2 . . ?
C19A C20A H20A 120.2 . . ?
O3B N1B O2B 123.3(5) . . ?
O3B N1B O1B 118.0(5) . . ?
O2B N1B O1B 118.6(4) . . ?
N1B O1B Cu1 109.4(3) . . ?
C1C O1C Cu1 127.6(3) . . ?
C1C O1C H1C 109.5 . . ?
Cu1 O1C H1C 120.7 . . ?
O1C C1C H1C3 109.5 . . ?
O1C C1C H1C2 109.5 . . ?
H1C3 C1C H1C2 109.5 . . ?
O1C C1C H1C1 109.5 . . ?
H1C3 C1C H1C1 109.5 . . ?
H1C2 C1C H1C1 109.5 . . ?
O3D N1D O2D 122.7(5) . . ?
O3D N1D O1D 123.1(6) . . ?
O2D N1D O1D 114.1(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9A N1A C2A N3A 0.6(5) . . . . ?
Cu1 N1A C2A N3A 177.5(3) . . . . ?
C9A N1A C2A N10A 179.2(4) . . . . ?
Cu1 N1A C2A N10A -3.9(5) . . . . ?
N1A C2A N3A C4A 0.1(5) . . . . ?
N10A C2A N3A C4A -178.4(4) . . . . ?
C2A N3A C4A C5A -179.4(5) . . . . ?
C2A N3A C4A C9A -0.8(5) . . . . ?
N3A C4A C5A C6A 178.1(4) . . . . ?
C9A C4A C5A C6A -0.4(7) . . . . ?
C4A C5A C6A C7A 0.3(7) . . . . ?
C5A C6A C7A C8A -0.6(8) . . . . ?
C6A C7A C8A C9A 0.8(8) . . . . ?
C7A C8A C9A N1A 180.0(5) . . . . ?
C7A C8A C9A C4A -0.8(7) . . . . ?
C2A N1A C9A C8A 178.2(5) . . . . ?
Cu1 N1A C9A C8A 2.7(8) . . . . ?
C2A N1A C9A C4A -1.1(5) . . . . ?
Cu1 N1A C9A C4A -176.6(3) . . . . ?
N3A C4A C9A C8A -178.2(4) . . . . ?
C5A C4A C9A C8A 0.6(7) . . . . ?
N3A C4A C9A N1A 1.2(5) . . . . ?
C5A C4A C9A N1A 180.0(4) . . . . ?
N1A C2A N10A N12A 2.8(6) . . . . ?
N3A C2A N10A N12A -178.9(4) . . . . ?
N1A C2A N10A C11A 150.2(4) . . . . ?
N3A C2A N10A C11A -31.5(6) . . . . ?
C2A N10A N12A C13A -168.7(4) . . . . ?
C11A N10A N12A C13A 45.2(6) . . . . ?
C2A N10A N12A Cu1 -0.3(4) . . . . ?
C11A N10A N12A Cu1 -146.3(4) . . . . ?
N10A N12A C13A C14A 1.7(7) . . . . ?
Cu1 N12A C13A C14A -166.5(4) . . . . ?
N10A N12A C13A C15A 179.5(4) . . . . ?
Cu1 N12A C13A C15A 11.3(5) . . . . ?
N12A C13A C15A N16A -8.0(5) . . . . ?
C14A C13A C15A N16A 170.0(4) . . . . ?
N12A C13A C15A C20A 170.4(4) . . . . ?
C14A C13A C15A C20A -11.7(6) . . . . ?
C20A C15A N16A C17A -0.2(6) . . . . ?
C13A C15A N16A C17A 178.2(4) . . . . ?
C20A C15A N16A Cu1 -177.4(3) . . . . ?
C13A C15A N16A Cu1 1.0(4) . . . . ?
C15A N16A C17A C18A -1.1(7) . . . . ?
Cu1 N16A C17A C18A 175.6(3) . . . . ?
N16A C17A C18A C19A 1.9(7) . . . . ?
C17A C18A C19A C20A -1.4(7) . . . . ?
N16A C15A C20A C19A 0.7(6) . . . . ?
C13A C15A C20A C19A -177.5(4) . . . . ?
C18A C19A C20A C15A 0.1(7) . . . . ?
O3B N1B O1B Cu1 163.0(4) . . . . ?
O2B N1B O1B Cu1 -17.1(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3A H3A O2D 0.88 2.00 2.753(6) 142.6 4_666
C11A H11C O3D 0.98 2.60 3.349(8) 133.4 2_655
C11A H11B O1D 0.98 2.60 3.299(8) 128.1 4_666
O1C H1C O2D 0.84 1.90 2.715(6) 162.0 1_556
C1C H1C2 O3D 0.98 2.47 3.215(8) 132.7 3_756

_refine_diff_density_max         0.801
_refine_diff_density_min         -0.462
_refine_diff_density_rms         0.072

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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 1468758'
_audit_update_record             
;
2017-08-22 deposited with the CCDC.
2017-10-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H15 Br2 Cu N5, C H4 O'
_chemical_formula_sum            'C16 H19 Br2 Cu N5 O'
_chemical_formula_weight         520.72

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.6841(12)
_cell_length_b                   10.0927(9)
_cell_length_c                   10.4709(9)
_cell_angle_alpha                91.231(7)
_cell_angle_beta                 92.328(8)
_cell_angle_gamma                117.823(11)
_cell_volume                     903.40(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(1)
_cell_measurement_reflns_used    1268
_cell_measurement_theta_min      3.8940
_cell_measurement_theta_max      28.0250

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.914
_exptl_crystal_F_000             514
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    5.647
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.66151
_exptl_absorpt_correction_T_max  1.00000
_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_absorpt_special_details   ?

_diffrn_ambient_temperature      120(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.1544
_diffrn_measurement_method       ω-scan
_diffrn_reflns_number            5979
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_av_R_equivalents  0.0167
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.934
_diffrn_reflns_theta_max         28.030
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.839
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.839
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.839
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3675
_reflns_number_gt                3322
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;


_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_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_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'



_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0314P)²+1.9240P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3675
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0283
_refine_ls_wR_factor_ref         0.0741
_refine_ls_wR_factor_gt          0.0713
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.34331(4) 0.29963(4) 0.39344(3) 0.01093(10) Uani 1 1 d . . . . .
N1A N 0.4493(3) 0.4548(3) 0.2705(2) 0.0114(5) Uani 1 1 d . . . . .
C2A C 0.5949(4) 0.4809(3) 0.2556(3) 0.0113(6) Uani 1 1 d . . . . .
N3A N 0.6693(3) 0.5834(3) 0.1691(2) 0.0126(5) Uani 1 1 d . . . . .
H3A H 0.7660 0.6154 0.1469 0.015 Uiso 1 1 calc R U . . .
C4A C 0.5619(4) 0.6289(4) 0.1213(3) 0.0127(6) Uani 1 1 d . . . . .
C5A C 0.5753(4) 0.7307(4) 0.0299(3) 0.0167(7) Uani 1 1 d . . . . .
H5A H 0.6687 0.7832 -0.0136 0.020 Uiso 1 1 calc R U . . .
C6A C 0.4463(4) 0.7520(4) 0.0052(3) 0.0192(7) Uani 1 1 d . . . . .
H6A H 0.4508 0.8213 -0.0565 0.023 Uiso 1 1 calc R U . . .
C7A C 0.3077(4) 0.6731(4) 0.0695(3) 0.0196(7) Uani 1 1 d . . . . .
H7A H 0.2211 0.6909 0.0507 0.023 Uiso 1 1 calc R U . . .
C8A C 0.2955(4) 0.5701(4) 0.1597(3) 0.0162(7) Uani 1 1 d . . . . .
H8A H 0.2015 0.5161 0.2020 0.019 Uiso 1 1 calc R U . . .
C9A C 0.4247(4) 0.5486(3) 0.1860(3) 0.0127(6) Uani 1 1 d . . . . .
N10A N 0.6608(3) 0.4080(3) 0.3240(2) 0.0128(5) Uani 1 1 d . . . . .
C11A C 0.8112(4) 0.4188(4) 0.2932(3) 0.0151(7) Uani 1 1 d . . . . .
H11C H 0.8943 0.4956 0.3499 0.023 Uiso 1 1 calc R U . . .
H11B H 0.8312 0.4461 0.2041 0.023 Uiso 1 1 calc R U . . .
H11A H 0.8092 0.3218 0.3050 0.023 Uiso 1 1 calc R U . . .
N12A N 0.5623(3) 0.3203(3) 0.4128(2) 0.0105(5) Uani 1 1 d . . . . .
C13A C 0.5943(3) 0.2548(3) 0.5052(3) 0.0108(6) Uani 1 1 d . . . . .
C14A C 0.7462(4) 0.2581(4) 0.5456(3) 0.0146(6) Uani 1 1 d . . . . .
H14C H 0.7452 0.1653 0.5147 0.022 Uiso 1 1 calc R U . . .
H14B H 0.7601 0.2670 0.6392 0.022 Uiso 1 1 calc R U . . .
H14A H 0.8326 0.3442 0.5093 0.022 Uiso 1 1 calc R U . . .
C15A C 0.4549(4) 0.1677(3) 0.5810(3) 0.0115(6) Uani 1 1 d . . . . .
N16A N 0.3255(3) 0.1815(3) 0.5484(2) 0.0124(5) Uani 1 1 d . . . . .
C17A C 0.1962(4) 0.1064(4) 0.6123(3) 0.0159(7) Uani 1 1 d . . . . .
H17A H 0.1055 0.1160 0.5888 0.019 Uiso 1 1 calc R U . . .
C18A C 0.1900(4) 0.0154(4) 0.7112(3) 0.0161(7) Uani 1 1 d . . . . .
H18A H 0.0969 -0.0364 0.7553 0.019 Uiso 1 1 calc R U . . .
C19A C 0.3219(4) 0.0014(4) 0.7447(3) 0.0169(7) Uani 1 1 d . . . . .
H19A H 0.3208 -0.0597 0.8128 0.020 Uiso 1 1 calc R U . . .
C20A C 0.4555(4) 0.0772(4) 0.6783(3) 0.0137(6) Uani 1 1 d . . . . .
H20A H 0.5465 0.0672 0.6992 0.016 Uiso 1 1 calc R U . . .
Br1B Br 0.12046(4) 0.33462(4) 0.42060(3) 0.02056(10) Uani 1 1 d . . . . .
Br1C Br 0.23259(4) 0.04477(4) 0.24422(3) 0.01580(9) Uani 1 1 d . . . . .
C1D C 0.9965(4) 0.7898(4) -0.0211(3) 0.0262(8) Uani 1 1 d . . . . .
H1D3 H 0.8946 0.7669 -0.0620 0.039 Uiso 1 1 calc R U . . .
H1D2 H 1.0457 0.7425 -0.0720 0.039 Uiso 1 1 calc R U . . .
H1D1 H 1.0637 0.8986 -0.0154 0.039 Uiso 1 1 calc R U . . .
O1D O 0.9757(3) 0.7335(3) 0.1044(2) 0.0204(5) Uani 1 1 d . . . . .
H1D H 1.0245 0.8048 0.1585 0.031 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N1A 1.964(3) . ?
Cu1 N16A 1.999(3) . ?
Cu1 N12A 2.032(3) . ?
Cu1 Br1B 2.3706(6) . ?
Cu1 Br1C 2.7063(6) . ?
N1A C2A 1.325(4) . ?
N1A C9A 1.402(4) . ?
C2A N3A 1.344(4) . ?
C2A N10A 1.374(4) . ?
N3A C4A 1.398(4) . ?
N3A H3A 0.8800 . ?
C4A C5A 1.385(4) . ?
C4A C9A 1.405(4) . ?
C5A C6A 1.379(5) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.409(5) . ?
C6A H6A 0.9500 . ?
C7A C8A 1.387(5) . ?
C7A H7A 0.9500 . ?
C8A C9A 1.384(4) . ?
C8A H8A 0.9500 . ?
N10A N12A 1.370(3) . ?
N10A C11A 1.459(4) . ?
C11A H11C 0.9800 . ?
C11A H11B 0.9800 . ?
C11A H11A 0.9800 . ?
N12A C13A 1.291(4) . ?
C13A C15A 1.495(4) . ?
C13A C14A 1.499(4) . ?
C14A H14C 0.9800 . ?
C14A H14B 0.9800 . ?
C14A H14A 0.9800 . ?
C15A N16A 1.355(4) . ?
C15A C20A 1.385(4) . ?
N16A C17A 1.339(4) . ?
C17A C18A 1.384(5) . ?
C17A H17A 0.9500 . ?
C18A C19A 1.381(5) . ?
C18A H18A 0.9500 . ?
C19A C20A 1.384(5) . ?
C19A H19A 0.9500 . ?
C20A H20A 0.9500 . ?
C1D O1D 1.427(4) . ?
C1D H1D3 0.9800 . ?
C1D H1D2 0.9800 . ?
C1D H1D1 0.9800 . ?
O1D H1D 0.8400 . ?

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
N1A Cu1 N16A 156.46(11) . . ?
N1A Cu1 N12A 79.97(10) . . ?
N16A Cu1 N12A 79.09(10) . . ?
N1A Cu1 Br1B 99.21(8) . . ?
N16A Cu1 Br1B 97.51(8) . . ?
N12A Cu1 Br1B 162.43(7) . . ?
N1A Cu1 Br1C 102.06(8) . . ?
N16A Cu1 Br1C 89.78(8) . . ?
N12A Cu1 Br1C 93.29(7) . . ?
Br1B Cu1 Br1C 103.98(2) . . ?
C2A N1A C9A 105.1(3) . . ?
C2A N1A Cu1 112.6(2) . . ?
C9A N1A Cu1 142.3(2) . . ?
N1A C2A N3A 114.0(3) . . ?
N1A C2A N10A 121.7(3) . . ?
N3A C2A N10A 124.2(3) . . ?
C2A N3A C4A 106.2(3) . . ?
C2A N3A H3A 126.9 . . ?
C4A N3A H3A 126.9 . . ?
C5A C4A N3A 130.9(3) . . ?
C5A C4A C9A 122.8(3) . . ?
N3A C4A C9A 106.2(3) . . ?
C6A C5A C4A 116.6(3) . . ?
C6A C5A H5A 121.7 . . ?
C4A C5A H5A 121.7 . . ?
C5A C6A C7A 121.5(3) . . ?
C5A C6A H6A 119.3 . . ?
C7A C6A H6A 119.3 . . ?
C8A C7A C6A 121.2(3) . . ?
C8A C7A H7A 119.4 . . ?
C6A C7A H7A 119.4 . . ?
C9A C8A C7A 117.8(3) . . ?
C9A C8A H8A 121.1 . . ?
C7A C8A H8A 121.1 . . ?
C8A C9A N1A 131.5(3) . . ?
C8A C9A C4A 120.0(3) . . ?
N1A C9A C4A 108.4(3) . . ?
N12A N10A C2A 111.0(2) . . ?
N12A N10A C11A 127.3(3) . . ?
C2A N10A C11A 121.5(3) . . ?
N10A C11A H11C 109.5 . . ?
N10A C11A H11B 109.5 . . ?
H11C C11A H11B 109.5 . . ?
N10A C11A H11A 109.5 . . ?
H11C C11A H11A 109.5 . . ?
H11B C11A H11A 109.5 . . ?
C13A N12A N10A 127.6(3) . . ?
C13A N12A Cu1 118.5(2) . . ?
N10A N12A Cu1 113.83(19) . . ?
N12A C13A C15A 111.7(3) . . ?
N12A C13A C14A 129.7(3) . . ?
C15A C13A C14A 118.6(3) . . ?
C13A C14A H14C 109.5 . . ?
C13A C14A H14B 109.5 . . ?
H14C C14A H14B 109.5 . . ?
C13A C14A H14A 109.5 . . ?
H14C C14A H14A 109.5 . . ?
H14B C14A H14A 109.5 . . ?
N16A C15A C20A 121.3(3) . . ?
N16A C15A C13A 116.0(3) . . ?
C20A C15A C13A 122.8(3) . . ?
C17A N16A C15A 119.1(3) . . ?
C17A N16A Cu1 126.1(2) . . ?
C15A N16A Cu1 114.5(2) . . ?
N16A C17A C18A 122.3(3) . . ?
N16A C17A H17A 118.9 . . ?
C18A C17A H17A 118.9 . . ?
C19A C18A C17A 118.7(3) . . ?
C19A C18A H18A 120.7 . . ?
C17A C18A H18A 120.7 . . ?
C18A C19A C20A 119.5(3) . . ?
C18A C19A H19A 120.3 . . ?
C20A C19A H19A 120.3 . . ?
C19A C20A C15A 119.1(3) . . ?
C19A C20A H20A 120.4 . . ?
C15A C20A H20A 120.4 . . ?
O1D C1D H1D3 109.5 . . ?
O1D C1D H1D2 109.5 . . ?
H1D3 C1D H1D2 109.5 . . ?
O1D C1D H1D1 109.5 . . ?
H1D3 C1D H1D1 109.5 . . ?
H1D2 C1D H1D1 109.5 . . ?
C1D O1D H1D 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9A N1A C2A N3A 0.0(3) . . . . ?
Cu1 N1A C2A N3A 178.1(2) . . . . ?
C9A N1A C2A N10A 180.0(3) . . . . ?
Cu1 N1A C2A N10A -1.9(4) . . . . ?
N1A C2A N3A C4A -0.4(4) . . . . ?
N10A C2A N3A C4A 179.6(3) . . . . ?
C2A N3A C4A C5A -179.4(3) . . . . ?
C2A N3A C4A C9A 0.7(3) . . . . ?
N3A C4A C5A C6A -179.2(3) . . . . ?
C9A C4A C5A C6A 0.7(5) . . . . ?
C4A C5A C6A C7A -0.4(5) . . . . ?
C5A C6A C7A C8A -0.4(5) . . . . ?
C6A C7A C8A C9A 0.9(5) . . . . ?
C7A C8A C9A N1A 179.9(3) . . . . ?
C7A C8A C9A C4A -0.6(5) . . . . ?
C2A N1A C9A C8A -180.0(3) . . . . ?
Cu1 N1A C9A C8A 2.9(6) . . . . ?
C2A N1A C9A C4A 0.4(3) . . . . ?
Cu1 N1A C9A C4A -176.7(3) . . . . ?
C5A C4A C9A C8A -0.2(5) . . . . ?
N3A C4A C9A C8A 179.7(3) . . . . ?
C5A C4A C9A N1A 179.4(3) . . . . ?
N3A C4A C9A N1A -0.7(3) . . . . ?
N1A C2A N10A N12A -5.4(4) . . . . ?
N3A C2A N10A N12A 174.6(3) . . . . ?
N1A C2A N10A C11A 170.1(3) . . . . ?
N3A C2A N10A C11A -9.9(5) . . . . ?
C2A N10A N12A C13A -168.7(3) . . . . ?
C11A N10A N12A C13A 16.1(5) . . . . ?
C2A N10A N12A Cu1 9.8(3) . . . . ?
C11A N10A N12A Cu1 -165.3(2) . . . . ?
N10A N12A C13A C15A -179.4(3) . . . . ?
Cu1 N12A C13A C15A 2.1(3) . . . . ?
N10A N12A C13A C14A 2.1(5) . . . . ?
Cu1 N12A C13A C14A -176.3(3) . . . . ?
N12A C13A C15A N16A -5.3(4) . . . . ?
C14A C13A C15A N16A 173.3(3) . . . . ?
N12A C13A C15A C20A 174.3(3) . . . . ?
C14A C13A C15A C20A -7.0(4) . . . . ?
C20A C15A N16A C17A 0.3(4) . . . . ?
C13A C15A N16A C17A 179.9(3) . . . . ?
C20A C15A N16A Cu1 -173.6(2) . . . . ?
C13A C15A N16A Cu1 6.0(3) . . . . ?
C15A N16A C17A C18A 0.4(5) . . . . ?
Cu1 N16A C17A C18A 173.5(2) . . . . ?
N16A C17A C18A C19A -0.2(5) . . . . ?
C17A C18A C19A C20A -0.5(5) . . . . ?
C18A C19A C20A C15A 1.1(5) . . . . ?
N16A C15A C20A C19A -1.0(5) . . . . ?
C13A C15A C20A C19A 179.3(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3A H3A O1D 0.88 1.89 2.752(4) 165.1 .
C5A H5A Br1C 0.95 2.93 3.689(3) 138.0 2_665
C8A H8A Br1B 0.95 2.86 3.589(3) 134.1 .
C17A H17A Br1B 0.95 2.81 3.395(3) 120.9 .
C20A H20A Br1C 0.95 2.90 3.823(3) 165.2 2_656
O1D H1D Br1C 0.84 2.44 3.227(2) 157.1 1_665

_refine_diff_density_max         0.495
_refine_diff_density_min         -1.021
_refine_diff_density_rms         0.113

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1570189'
_audit_update_record             
;
2017-08-21 deposited with the CCDC.
2017-10-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H15 Br2 Mn N5'
_chemical_formula_sum            'C15 H15 Br2 Mn N5'
_chemical_formula_weight         480.08

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.6305(5)
_cell_length_b                   8.9863(5)
_cell_length_c                   13.5352(8)
_cell_angle_alpha                83.946(5)
_cell_angle_beta                 75.427(6)
_cell_angle_gamma                67.854(6)
_cell_volume                     831.92(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(1)
_cell_measurement_reflns_used    2571
_cell_measurement_theta_min      3.2480
_cell_measurement_theta_max      26.9290

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.916
_exptl_crystal_F_000             470
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    5.601
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.66044
_exptl_absorpt_correction_T_max  1.00000
_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_absorpt_special_details   ?

_diffrn_ambient_temperature      120(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.1544
_diffrn_measurement_method       ω-scan
_diffrn_reflns_number            5914
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.962
_diffrn_reflns_theta_max         28.315
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.823
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.823
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.823
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3403
_reflns_number_gt                3123
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_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_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_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0221P)²+0.5230P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3403
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0245
_refine_ls_wR_factor_ref         0.0587
_refine_ls_wR_factor_gt          0.0566
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.56217(5) 0.30248(4) 0.77416(3) 0.01238(9) Uani 1 1 d . . . . .
N1A N 0.7352(3) 0.3857(2) 0.64273(16) 0.0144(4) Uani 1 1 d . . . . .
C2A C 0.6413(4) 0.5304(3) 0.60760(19) 0.0139(5) Uani 1 1 d . . . . .
N3A N 0.7100(3) 0.5533(3) 0.50794(16) 0.0159(5) Uani 1 1 d . . . . .
H3A H 0.6645 0.6400 0.4713 0.019 Uiso 1 1 calc R U . . .
C4A C 0.8672(4) 0.4136(3) 0.47375(19) 0.0144(5) Uani 1 1 d . . . . .
C5A C 0.9934(4) 0.3711(3) 0.3788(2) 0.0186(6) Uani 1 1 d . . . . .
H5A H 0.9811 0.4419 0.3215 0.022 Uiso 1 1 calc R U . . .
C6A C 1.1380(4) 0.2202(3) 0.3721(2) 0.0193(6) Uani 1 1 d . . . . .
H6A H 1.2273 0.1860 0.3085 0.023 Uiso 1 1 calc R U . . .
C7A C 1.1557(4) 0.1173(3) 0.4564(2) 0.0186(6) Uani 1 1 d . . . . .
H7A H 1.2580 0.0151 0.4491 0.022 Uiso 1 1 calc R U . . .
C8A C 1.0280(4) 0.1598(3) 0.5509(2) 0.0173(5) Uani 1 1 d . . . . .
H8A H 1.0409 0.0889 0.6082 0.021 Uiso 1 1 calc R U . . .
C9A C 0.8817(3) 0.3092(3) 0.55827(19) 0.0140(5) Uani 1 1 d . . . . .
N10A N 0.4943(3) 0.6451(2) 0.66969(16) 0.0160(5) Uani 1 1 d . . . . .
C11A C 0.3641(4) 0.7892(3) 0.6266(2) 0.0184(6) Uani 1 1 d . . . . .
H11C H 0.4107 0.8778 0.6235 0.028 Uiso 1 1 calc R U . . .
H11B H 0.2323 0.8194 0.6699 0.028 Uiso 1 1 calc R U . . .
H11A H 0.3627 0.7664 0.5576 0.028 Uiso 1 1 calc R U . . .
N12A N 0.4321(3) 0.5772(2) 0.76243(16) 0.0146(5) Uani 1 1 d . . . . .
C13A C 0.3454(3) 0.6630(3) 0.8433(2) 0.0149(5) Uani 1 1 d . . . . .
C14A C 0.3102(4) 0.8370(3) 0.8523(2) 0.0190(6) Uani 1 1 d . . . . .
H14C H 0.4089 0.8655 0.8009 0.028 Uiso 1 1 calc R U . . .
H14B H 0.3178 0.8571 0.9206 0.028 Uiso 1 1 calc R U . . .
H14A H 0.1808 0.9025 0.8413 0.028 Uiso 1 1 calc R U . . .
C15A C 0.2895(3) 0.5686(3) 0.93381(19) 0.0147(5) Uani 1 1 d . . . . .
N16A N 0.3678(3) 0.4069(2) 0.92461(16) 0.0150(5) Uani 1 1 d . . . . .
C17A C 0.3172(4) 0.3172(3) 1.0038(2) 0.0182(6) Uani 1 1 d . . . . .
H17A H 0.3726 0.2036 0.9977 0.022 Uiso 1 1 calc R U . . .
C18A C 0.1880(4) 0.3819(3) 1.0943(2) 0.0217(6) Uani 1 1 d . . . . .
H18A H 0.1544 0.3143 1.1486 0.026 Uiso 1 1 calc R U . . .
C19A C 0.1093(4) 0.5472(3) 1.1037(2) 0.0229(6) Uani 1 1 d . . . . .
H19A H 0.0214 0.5955 1.1650 0.028 Uiso 1 1 calc R U . . .
C20A C 0.1609(4) 0.6411(3) 1.0224(2) 0.0190(6) Uani 1 1 d . . . . .
H20A H 0.1081 0.7549 1.0273 0.023 Uiso 1 1 calc R U . . .
Br1B Br 0.78214(4) 0.05240(3) 0.84660(2) 0.02074(8) Uani 1 1 d . . . . .
Br1C Br 0.35636(4) 0.20794(3) 0.69539(2) 0.01852(8) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn1 N1A 2.179(2) . ?
Mn1 N16A 2.250(2) . ?
Mn1 N12A 2.292(2) . ?
Mn1 Br1B 2.5196(5) . ?
Mn1 Br1C 2.5227(5) . ?
N1A C2A 1.330(3) . ?
N1A C9A 1.404(3) . ?
C2A N3A 1.343(3) . ?
C2A N10A 1.365(3) . ?
N3A C4A 1.391(3) . ?
N3A H3A 0.8800 . ?
C4A C5A 1.389(3) . ?
C4A C9A 1.400(4) . ?
C5A C6A 1.382(4) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.392(4) . ?
C6A H6A 0.9500 . ?
C7A C8A 1.388(4) . ?
C7A H7A 0.9500 . ?
C8A C9A 1.378(3) . ?
C8A H8A 0.9500 . ?
N10A N12A 1.389(3) . ?
N10A C11A 1.472(3) . ?
C11A H11C 0.9800 . ?
C11A H11B 0.9800 . ?
C11A H11A 0.9800 . ?
N12A C13A 1.288(3) . ?
C13A C15A 1.481(4) . ?
C13A C14A 1.497(4) . ?
C14A H14C 0.9800 . ?
C14A H14B 0.9800 . ?
C14A H14A 0.9800 . ?
C15A N16A 1.353(3) . ?
C15A C20A 1.384(3) . ?
N16A C17A 1.339(3) . ?
C17A C18A 1.386(4) . ?
C17A H17A 0.9500 . ?
C18A C19A 1.383(4) . ?
C18A H18A 0.9500 . ?
C19A C20A 1.385(4) . ?
C19A H19A 0.9500 . ?
C20A H20A 0.9500 . ?

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
N1A Mn1 N16A 135.65(8) . . ?
N1A Mn1 N12A 70.31(8) . . ?
N16A Mn1 N12A 69.58(8) . . ?
N1A Mn1 Br1B 108.92(5) . . ?
N16A Mn1 Br1B 96.51(5) . . ?
N12A Mn1 Br1B 149.68(6) . . ?
N1A Mn1 Br1C 103.18(6) . . ?
N16A Mn1 Br1C 104.42(6) . . ?
N12A Mn1 Br1C 104.50(6) . . ?
Br1B Mn1 Br1C 105.067(17) . . ?
C2A N1A C9A 104.5(2) . . ?
C2A N1A Mn1 114.43(16) . . ?
C9A N1A Mn1 134.02(17) . . ?
N1A C2A N3A 113.8(2) . . ?
N1A C2A N10A 122.0(2) . . ?
N3A C2A N10A 124.2(2) . . ?
C2A N3A C4A 106.8(2) . . ?
C2A N3A H3A 126.6 . . ?
C4A N3A H3A 126.6 . . ?
C5A C4A N3A 131.9(2) . . ?
C5A C4A C9A 122.3(2) . . ?
N3A C4A C9A 105.8(2) . . ?
C6A C5A C4A 116.4(2) . . ?
C6A C5A H5A 121.8 . . ?
C4A C5A H5A 121.8 . . ?
C5A C6A C7A 121.5(2) . . ?
C5A C6A H6A 119.3 . . ?
C7A C6A H6A 119.3 . . ?
C8A C7A C6A 121.8(2) . . ?
C8A C7A H7A 119.1 . . ?
C6A C7A H7A 119.1 . . ?
C9A C8A C7A 117.2(2) . . ?
C9A C8A H8A 121.4 . . ?
C7A C8A H8A 121.4 . . ?
C8A C9A C4A 120.7(2) . . ?
C8A C9A N1A 130.2(2) . . ?
C4A C9A N1A 109.1(2) . . ?
C2A N10A N12A 110.4(2) . . ?
C2A N10A C11A 120.9(2) . . ?
N12A N10A C11A 122.2(2) . . ?
N10A C11A H11C 109.5 . . ?
N10A C11A H11B 109.5 . . ?
H11C C11A H11B 109.5 . . ?
N10A C11A H11A 109.5 . . ?
H11C C11A H11A 109.5 . . ?
H11B C11A H11A 109.5 . . ?
C13A N12A N10A 121.1(2) . . ?
C13A N12A Mn1 120.70(18) . . ?
N10A N12A Mn1 116.18(14) . . ?
N12A C13A C15A 112.7(2) . . ?
N12A C13A C14A 126.5(3) . . ?
C15A C13A C14A 120.7(2) . . ?
C13A C14A H14C 109.5 . . ?
C13A C14A H14B 109.5 . . ?
H14C C14A H14B 109.5 . . ?
C13A C14A H14A 109.5 . . ?
H14C C14A H14A 109.5 . . ?
H14B C14A H14A 109.5 . . ?
N16A C15A C20A 121.6(2) . . ?
N16A C15A C13A 116.3(2) . . ?
C20A C15A C13A 122.1(2) . . ?
C17A N16A C15A 118.2(2) . . ?
C17A N16A Mn1 123.17(17) . . ?
C15A N16A Mn1 118.48(17) . . ?
N16A C17A C18A 123.2(2) . . ?
N16A C17A H17A 118.4 . . ?
C18A C17A H17A 118.4 . . ?
C19A C18A C17A 118.4(3) . . ?
C19A C18A H18A 120.8 . . ?
C17A C18A H18A 120.8 . . ?
C18A C19A C20A 118.9(2) . . ?
C18A C19A H19A 120.6 . . ?
C20A C19A H19A 120.6 . . ?
C15A C20A C19A 119.7(3) . . ?
C15A C20A H20A 120.1 . . ?
C19A C20A H20A 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9A N1A C2A N3A 1.5(3) . . . . ?
Mn1 N1A C2A N3A -153.41(18) . . . . ?
C9A N1A C2A N10A -175.9(2) . . . . ?
Mn1 N1A C2A N10A 29.1(3) . . . . ?
N1A C2A N3A C4A -1.8(3) . . . . ?
N10A C2A N3A C4A 175.6(2) . . . . ?
C2A N3A C4A C5A -179.1(3) . . . . ?
C2A N3A C4A C9A 1.2(3) . . . . ?
N3A C4A C5A C6A 179.1(3) . . . . ?
C9A C4A C5A C6A -1.2(4) . . . . ?
C4A C5A C6A C7A -0.2(4) . . . . ?
C5A C6A C7A C8A 0.8(4) . . . . ?
C6A C7A C8A C9A 0.0(4) . . . . ?
C7A C8A C9A C4A -1.4(4) . . . . ?
C7A C8A C9A N1A -178.7(3) . . . . ?
C5A C4A C9A C8A 2.1(4) . . . . ?
N3A C4A C9A C8A -178.1(2) . . . . ?
C5A C4A C9A N1A 179.9(2) . . . . ?
N3A C4A C9A N1A -0.3(3) . . . . ?
C2A N1A C9A C8A 176.9(3) . . . . ?
Mn1 N1A C9A C8A -35.6(4) . . . . ?
C2A N1A C9A C4A -0.7(3) . . . . ?
Mn1 N1A C9A C4A 146.87(19) . . . . ?
N1A C2A N10A N12A -14.0(3) . . . . ?
N3A C2A N10A N12A 168.8(2) . . . . ?
N1A C2A N10A C11A -166.1(2) . . . . ?
N3A C2A N10A C11A 16.7(4) . . . . ?
C2A N10A N12A C13A 156.7(2) . . . . ?
C11A N10A N12A C13A -51.7(3) . . . . ?
C2A N10A N12A Mn1 -7.2(3) . . . . ?
C11A N10A N12A Mn1 144.47(19) . . . . ?
N10A N12A C13A C15A 179.5(2) . . . . ?
Mn1 N12A C13A C15A -17.3(3) . . . . ?
N10A N12A C13A C14A -3.9(4) . . . . ?
Mn1 N12A C13A C14A 159.23(19) . . . . ?
N12A C13A C15A N16A 12.3(3) . . . . ?
C14A C13A C15A N16A -164.4(2) . . . . ?
N12A C13A C15A C20A -166.2(2) . . . . ?
C14A C13A C15A C20A 17.0(4) . . . . ?
C20A C15A N16A C17A 0.2(4) . . . . ?
C13A C15A N16A C17A -178.4(2) . . . . ?
C20A C15A N16A Mn1 176.65(19) . . . . ?
C13A C15A N16A Mn1 -1.9(3) . . . . ?
C15A N16A C17A C18A 0.4(4) . . . . ?
Mn1 N16A C17A C18A -175.9(2) . . . . ?
N16A C17A C18A C19A -0.8(4) . . . . ?
C17A C18A C19A C20A 0.7(4) . . . . ?
N16A C15A C20A C19A -0.3(4) . . . . ?
C13A C15A C20A C19A 178.2(2) . . . . ?
C18A C19A C20A C15A -0.1(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3A H3A Br1C 0.88 2.52 3.327(2) 152.8 2_666
C14A H14A Br1B 0.98 2.81 3.773(3) 167.5 1_465


_refine_diff_density_max         0.528
_refine_diff_density_min         -0.492
_refine_diff_density_rms         0.079

####################################################################### 
# 
# 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 1468757'
_audit_update_record             
;
2017-08-21 deposited with the CCDC.
2017-10-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H19 Cu F6 N5 O7 S2'
_chemical_formula_sum            'C18 H19 Cu F6 N5 O7 S2'
_chemical_formula_weight         659.04

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0767(3)
_cell_length_b                   11.3717(5)
_cell_length_c                   13.9815(8)
_cell_angle_alpha                76.300(4)
_cell_angle_beta                 82.265(4)
_cell_angle_gamma                85.663(3)
_cell_volume                     1234.98(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(1)
_cell_measurement_reflns_used    4277
_cell_measurement_theta_min      3.1190
_cell_measurement_theta_max      27.9800

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.772
_exptl_crystal_F_000             666
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    1.149
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.89510
_exptl_absorpt_correction_T_max  1.00000
_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_absorpt_special_details   ?

_diffrn_ambient_temperature      120(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.1544
_diffrn_measurement_method       ω-scan
_diffrn_reflns_number            8888
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_av_R_equivalents  0.0149
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.078
_diffrn_reflns_theta_max         28.209
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.834
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.834
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.834
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5079
_reflns_number_gt                4552
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_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_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_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0347P)²+0.5690P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5079
_refine_ls_number_parameters     363
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0273
_refine_ls_wR_factor_ref         0.0709
_refine_ls_wR_factor_gt          0.0685
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.23316(3) 0.77188(2) 0.24000(2) 0.01241(7) Uani 1 1 d . . . . .
N1A N 0.19882(18) 0.62307(14) 0.34375(11) 0.0129(3) Uani 1 1 d . . . . .
C2A C 0.2568(2) 0.63101(17) 0.42636(14) 0.0134(4) Uani 1 1 d . . . . .
N3A N 0.25043(19) 0.52697(15) 0.49604(13) 0.0153(3) Uani 1 1 d . . . . .
H3A H 0.272(3) 0.516(2) 0.5484(17) 0.014(6) Uiso 1 1 d . . . . .
C4A C 0.1781(2) 0.44364(17) 0.45712(14) 0.0154(4) Uani 1 1 d . . . . .
C5A C 0.1368(2) 0.32507(17) 0.49886(15) 0.0190(4) Uani 1 1 d . . . . .
H5A H 0.1586 0.2855 0.5641 0.023 Uiso 1 1 calc R U . . .
C6A C 0.0617(2) 0.26682(17) 0.44010(16) 0.0209(4) Uani 1 1 d . . . . .
H6A H 0.0312 0.1853 0.4657 0.025 Uiso 1 1 calc R U . . .
C7A C 0.0302(2) 0.32579(18) 0.34430(16) 0.0209(4) Uani 1 1 d . . . . .
H7A H -0.0201 0.2830 0.3059 0.025 Uiso 1 1 calc R U . . .
C8A C 0.0706(2) 0.44570(17) 0.30357(15) 0.0175(4) Uani 1 1 d . . . . .
H8A H 0.0473 0.4857 0.2387 0.021 Uiso 1 1 calc R U . . .
C9A C 0.1464(2) 0.50471(16) 0.36155(14) 0.0144(4) Uani 1 1 d . . . . .
N10A N 0.31117(18) 0.73765(14) 0.43801(11) 0.0143(3) Uani 1 1 d . . . . .
C11A C 0.4218(2) 0.7387(2) 0.51265(15) 0.0222(4) Uani 1 1 d . . . . .
H11C H 0.3578 0.7666 0.5684 0.033 Uiso 1 1 calc R U . . .
H11B H 0.5124 0.7936 0.4831 0.033 Uiso 1 1 calc R U . . .
H11A H 0.4693 0.6567 0.5363 0.033 Uiso 1 1 calc R U . . .
N12A N 0.30975(18) 0.82489(14) 0.35073(11) 0.0124(3) Uani 1 1 d . . . . .
C13A C 0.3183(2) 0.93956(17) 0.34192(14) 0.0142(4) Uani 1 1 d . . . . .
C14A C 0.3230(2) 1.00428(19) 0.42242(15) 0.0200(4) Uani 1 1 d . . . . .
H14C H 0.2726 0.9550 0.4855 0.030 Uiso 1 1 calc R U . . .
H14B H 0.2600 1.0822 0.4071 0.030 Uiso 1 1 calc R U . . .
H14A H 0.4393 1.0183 0.4277 0.030 Uiso 1 1 calc R U . . .
C15A C 0.3162(2) 1.00835(17) 0.23744(14) 0.0146(4) Uani 1 1 d . . . . .
N16A N 0.28904(18) 0.94182(14) 0.17291(12) 0.0146(3) Uani 1 1 d . . . . .
C17A C 0.2892(2) 0.99503(18) 0.07720(15) 0.0200(4) Uani 1 1 d . . . . .
H17A H 0.2694 0.9477 0.0326 0.024 Uiso 1 1 calc R U . . .
C18A C 0.3172(3) 1.11763(19) 0.04023(16) 0.0254(5) Uani 1 1 d . . . . .
H18A H 0.3197 1.1533 -0.0286 0.030 Uiso 1 1 calc R U . . .
C19A C 0.3413(2) 1.18597(19) 0.10613(17) 0.0263(5) Uani 1 1 d . . . . .
H19A H 0.3585 1.2702 0.0832 0.032 Uiso 1 1 calc R U . . .
C20A C 0.3403(2) 1.13129(18) 0.20631(16) 0.0213(4) Uani 1 1 d . . . . .
H20A H 0.3559 1.1776 0.2525 0.026 Uiso 1 1 calc R U . . .
C1B C 0.6195(3) 0.4858(2) 0.16803(19) 0.0282(5) Uani 1 1 d . . . . .
F1B F 0.47769(19) 0.43261(14) 0.20876(14) 0.0537(5) Uani 1 1 d . . . . .
F2B F 0.74527(19) 0.40650(13) 0.18910(14) 0.0528(5) Uani 1 1 d . . . . .
F3B F 0.61837(19) 0.51147(15) 0.07029(12) 0.0474(4) Uani 1 1 d . . . . .
S1B S 0.64050(5) 0.62221(4) 0.21173(3) 0.01504(10) Uani 1 1 d . . . . .
O1B O 0.50250(15) 0.70048(12) 0.17458(10) 0.0189(3) Uani 1 1 d . . . . .
O2B O 0.80244(16) 0.66114(13) 0.16302(11) 0.0241(3) Uani 1 1 d . . . . .
O3B O 0.62683(18) 0.58001(14) 0.31788(11) 0.0285(3) Uani 1 1 d . . . . .
C1C C 0.1915(3) 0.6687(2) 0.06064(15) 0.0228(4) Uani 1 1 d . . . . .
H1C3 H 0.2964 0.7029 0.0252 0.034 Uiso 1 1 calc R U . . .
H1C2 H 0.1119 0.6709 0.0131 0.034 Uiso 1 1 calc R U . . .
H1C1 H 0.2133 0.5846 0.0956 0.034 Uiso 1 1 calc R U . . .
O1C O 0.12240(17) 0.73857(12) 0.13118(10) 0.0166(3) Uani 1 1 d . . . . .
H1C H 0.031(3) 0.729(2) 0.1460(18) 0.025(7) Uiso 1 1 d . . . . .
C1D C -0.1962(3) 1.0611(2) 0.19535(18) 0.0330(5) Uani 1 1 d . . . . .
F1D F -0.06060(18) 1.09826(19) 0.13314(14) 0.0776(7) Uani 1 1 d . . . . .
F2D F -0.28152(17) 1.15938(12) 0.21497(14) 0.0501(4) Uani 1 1 d . . . . .
F3D F -0.29191(18) 1.00860(16) 0.14829(11) 0.0479(4) Uani 1 1 d . . . . .
S1D S -0.14272(5) 0.95802(4) 0.30837(3) 0.01492(11) Uani 1 1 d . . . . .
O1D O -0.04461(18) 1.02879(15) 0.35026(13) 0.0323(4) Uani 1 1 d . . . . .
O2D O -0.05141(16) 0.85939(12) 0.27318(11) 0.0212(3) Uani 1 1 d . . . . .
O3D O -0.30421(16) 0.92837(13) 0.36247(11) 0.0233(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N1A 1.9608(16) . ?
Cu1 N12A 1.9745(15) . ?
Cu1 O1C 1.9873(13) . ?
Cu1 N16A 1.9943(16) . ?
Cu1 O1B 2.4036(12) . ?
N1A C2A 1.328(2) . ?
N1A C9A 1.397(2) . ?
C2A N3A 1.342(2) . ?
C2A N10A 1.372(2) . ?
N3A C4A 1.396(2) . ?
N3A H3A 0.76(2) . ?
C4A C5A 1.383(3) . ?
C4A C9A 1.400(3) . ?
C5A C6A 1.391(3) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.396(3) . ?
C6A H6A 0.9500 . ?
C7A C8A 1.393(3) . ?
C7A H7A 0.9500 . ?
C8A C9A 1.391(3) . ?
C8A H8A 0.9500 . ?
N10A N12A 1.379(2) . ?
N10A C11A 1.465(2) . ?
C11A H11C 0.9800 . ?
C11A H11B 0.9800 . ?
C11A H11A 0.9800 . ?
N12A C13A 1.287(2) . ?
C13A C15A 1.486(3) . ?
C13A C14A 1.489(2) . ?
C14A H14C 0.9800 . ?
C14A H14B 0.9800 . ?
C14A H14A 0.9800 . ?
C15A N16A 1.355(2) . ?
C15A C20A 1.383(3) . ?
N16A C17A 1.332(3) . ?
C17A C18A 1.392(3) . ?
C17A H17A 0.9500 . ?
C18A C19A 1.379(3) . ?
C18A H18A 0.9500 . ?
C19A C20A 1.391(3) . ?
C19A H19A 0.9500 . ?
C20A H20A 0.9500 . ?
C1B F2B 1.322(3) . ?
C1B F3B 1.329(3) . ?
C1B F1B 1.330(3) . ?
C1B S1B 1.824(2) . ?
S1B O3B 1.4393(15) . ?
S1B O2B 1.4407(14) . ?
S1B O1B 1.4460(14) . ?
C1C O1C 1.439(2) . ?
C1C H1C3 0.9800 . ?
C1C H1C2 0.9800 . ?
C1C H1C1 0.9800 . ?
O1C H1C 0.75(2) . ?
C1D F1D 1.332(3) . ?
C1D F2D 1.333(3) . ?
C1D F3D 1.334(3) . ?
C1D S1D 1.813(2) . ?
S1D O1D 1.4364(15) . ?
S1D O3D 1.4378(14) . ?
S1D O2D 1.4431(13) . ?

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
N1A Cu1 N12A 80.91(6) . . ?
N1A Cu1 O1C 102.35(6) . . ?
N12A Cu1 O1C 170.03(6) . . ?
N1A Cu1 N16A 160.73(6) . . ?
N12A Cu1 N16A 79.86(6) . . ?
O1C Cu1 N16A 96.43(6) . . ?
N1A Cu1 O1B 93.30(5) . . ?
N12A Cu1 O1B 96.65(5) . . ?
O1C Cu1 O1B 92.58(5) . . ?
N16A Cu1 O1B 90.09(5) . . ?
C2A N1A C9A 105.50(15) . . ?
C2A N1A Cu1 111.34(12) . . ?
C9A N1A Cu1 142.88(13) . . ?
N1A C2A N3A 113.21(16) . . ?
N1A C2A N10A 121.90(17) . . ?
N3A C2A N10A 124.85(17) . . ?
C2A N3A C4A 106.70(16) . . ?
C2A N3A H3A 127.5(17) . . ?
C4A N3A H3A 125.5(17) . . ?
C5A C4A N3A 130.74(19) . . ?
C5A C4A C9A 123.18(18) . . ?
N3A C4A C9A 106.06(16) . . ?
C4A C5A C6A 116.38(19) . . ?
C4A C5A H5A 121.8 . . ?
C6A C5A H5A 121.8 . . ?
C5A C6A C7A 121.33(18) . . ?
C5A C6A H6A 119.3 . . ?
C7A C6A H6A 119.3 . . ?
C8A C7A C6A 121.72(19) . . ?
C8A C7A H7A 119.1 . . ?
C6A C7A H7A 119.1 . . ?
C9A C8A C7A 117.44(19) . . ?
C9A C8A H8A 121.3 . . ?
C7A C8A H8A 121.3 . . ?
C8A C9A N1A 131.54(18) . . ?
C8A C9A C4A 119.94(17) . . ?
N1A C9A C4A 108.50(16) . . ?
C2A N10A N12A 109.98(14) . . ?
C2A N10A C11A 121.19(16) . . ?
N12A N10A C11A 123.36(15) . . ?
N10A C11A H11C 109.5 . . ?
N10A C11A H11B 109.5 . . ?
H11C C11A H11B 109.5 . . ?
N10A C11A H11A 109.5 . . ?
H11C C11A H11A 109.5 . . ?
H11B C11A H11A 109.5 . . ?
C13A N12A N10A 125.50(16) . . ?
C13A N12A Cu1 117.33(13) . . ?
N10A N12A Cu1 115.37(11) . . ?
N12A C13A C15A 111.93(16) . . ?
N12A C13A C14A 127.52(18) . . ?
C15A C13A C14A 120.51(17) . . ?
C13A C14A H14C 109.5 . . ?
C13A C14A H14B 109.5 . . ?
H14C C14A H14B 109.5 . . ?
C13A C14A H14A 109.5 . . ?
H14C C14A H14A 109.5 . . ?
H14B C14A H14A 109.5 . . ?
N16A C15A C20A 121.30(18) . . ?
N16A C15A C13A 115.19(16) . . ?
C20A C15A C13A 123.50(17) . . ?
C17A N16A C15A 119.52(17) . . ?
C17A N16A Cu1 127.53(13) . . ?
C15A N16A Cu1 112.74(13) . . ?
N16A C17A C18A 122.27(19) . . ?
N16A C17A H17A 118.9 . . ?
C18A C17A H17A 118.9 . . ?
C19A C18A C17A 118.3(2) . . ?
C19A C18A H18A 120.9 . . ?
C17A C18A H18A 120.9 . . ?
C18A C19A C20A 119.84(19) . . ?
C18A C19A H19A 120.1 . . ?
C20A C19A H19A 120.1 . . ?
C15A C20A C19A 118.77(19) . . ?
C15A C20A H20A 120.6 . . ?
C19A C20A H20A 120.6 . . ?
F2B C1B F3B 107.48(19) . . ?
F2B C1B F1B 108.3(2) . . ?
F3B C1B F1B 107.25(18) . . ?
F2B C1B S1B 111.18(15) . . ?
F3B C1B S1B 111.08(16) . . ?
F1B C1B S1B 111.41(15) . . ?
O3B S1B O2B 116.16(9) . . ?
O3B S1B O1B 115.16(8) . . ?
O2B S1B O1B 113.98(9) . . ?
O3B S1B C1B 103.77(11) . . ?
O2B S1B C1B 102.24(9) . . ?
O1B S1B C1B 102.93(9) . . ?
S1B O1B Cu1 137.56(8) . . ?
O1C C1C H1C3 109.5 . . ?
O1C C1C H1C2 109.5 . . ?
H1C3 C1C H1C2 109.5 . . ?
O1C C1C H1C1 109.5 . . ?
H1C3 C1C H1C1 109.5 . . ?
H1C2 C1C H1C1 109.5 . . ?
C1C O1C Cu1 126.94(12) . . ?
C1C O1C H1C 111.2(18) . . ?
Cu1 O1C H1C 112.3(19) . . ?
F1D C1D F2D 107.4(2) . . ?
F1D C1D F3D 108.0(2) . . ?
F2D C1D F3D 107.33(18) . . ?
F1D C1D S1D 111.83(15) . . ?
F2D C1D S1D 110.97(18) . . ?
F3D C1D S1D 111.05(16) . . ?
O1D S1D O3D 115.41(9) . . ?
O1D S1D O2D 114.89(9) . . ?
O3D S1D O2D 114.61(8) . . ?
O1D S1D C1D 103.82(11) . . ?
O3D S1D C1D 102.45(9) . . ?
O2D S1D C1D 103.23(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9A N1A C2A N3A 1.45(19) . . . . ?
Cu1 N1A C2A N3A -173.96(11) . . . . ?
C9A N1A C2A N10A -176.32(15) . . . . ?
Cu1 N1A C2A N10A 8.3(2) . . . . ?
N1A C2A N3A C4A -1.5(2) . . . . ?
N10A C2A N3A C4A 176.15(16) . . . . ?
C2A N3A C4A C5A -177.30(18) . . . . ?
C2A N3A C4A C9A 0.95(18) . . . . ?
N3A C4A C5A C6A 178.57(17) . . . . ?
C9A C4A C5A C6A 0.6(3) . . . . ?
C4A C5A C6A C7A 0.0(3) . . . . ?
C5A C6A C7A C8A -0.7(3) . . . . ?
C6A C7A C8A C9A 0.9(3) . . . . ?
C7A C8A C9A N1A -178.71(17) . . . . ?
C7A C8A C9A C4A -0.4(3) . . . . ?
C2A N1A C9A C8A 177.68(18) . . . . ?
Cu1 N1A C9A C8A -9.4(3) . . . . ?
C2A N1A C9A C4A -0.77(18) . . . . ?
Cu1 N1A C9A C4A 172.13(15) . . . . ?
C5A C4A C9A C8A -0.4(3) . . . . ?
N3A C4A C9A C8A -178.77(15) . . . . ?
C5A C4A C9A N1A 178.30(16) . . . . ?
N3A C4A C9A N1A -0.11(18) . . . . ?
N1A C2A N10A N12A -5.6(2) . . . . ?
N3A C2A N10A N12A 176.94(15) . . . . ?
N1A C2A N10A C11A -160.24(16) . . . . ?
N3A C2A N10A C11A 22.2(3) . . . . ?
C2A N10A N12A C13A 164.19(16) . . . . ?
C11A N10A N12A C13A -41.8(2) . . . . ?
C2A N10A N12A Cu1 -0.04(17) . . . . ?
C11A N10A N12A Cu1 153.99(14) . . . . ?
N10A N12A C13A C15A 179.15(14) . . . . ?
Cu1 N12A C13A C15A -16.90(19) . . . . ?
N10A N12A C13A C14A -3.3(3) . . . . ?
Cu1 N12A C13A C14A 160.70(14) . . . . ?
N12A C13A C15A N16A 6.4(2) . . . . ?
C14A C13A C15A N16A -171.39(15) . . . . ?
N12A C13A C15A C20A -173.49(17) . . . . ?
C14A C13A C15A C20A 8.7(3) . . . . ?
C20A C15A N16A C17A 1.5(3) . . . . ?
C13A C15A N16A C17A -178.36(15) . . . . ?
C20A C15A N16A Cu1 -173.55(14) . . . . ?
C13A C15A N16A Cu1 6.56(18) . . . . ?
C15A N16A C17A C18A 0.3(3) . . . . ?
Cu1 N16A C17A C18A 174.58(14) . . . . ?
N16A C17A C18A C19A -1.7(3) . . . . ?
C17A C18A C19A C20A 1.2(3) . . . . ?
N16A C15A C20A C19A -1.9(3) . . . . ?
C13A C15A C20A C19A 177.96(17) . . . . ?
C18A C19A C20A C15A 0.5(3) . . . . ?
F2B C1B S1B O3B -64.55(19) . . . . ?
F3B C1B S1B O3B 175.80(14) . . . . ?
F1B C1B S1B O3B 56.30(19) . . . . ?
F2B C1B S1B O2B 56.6(2) . . . . ?
F3B C1B S1B O2B -63.02(16) . . . . ?
F1B C1B S1B O2B 177.48(16) . . . . ?
F2B C1B S1B O1B 175.08(17) . . . . ?
F3B C1B S1B O1B 55.44(16) . . . . ?
F1B C1B S1B O1B -64.06(19) . . . . ?
O3B S1B O1B Cu1 -6.55(16) . . . . ?
O2B S1B O1B Cu1 -144.47(11) . . . . ?
C1B S1B O1B Cu1 105.64(13) . . . . ?
F1D C1D S1D O1D 60.6(2) . . . . ?
F2D C1D S1D O1D -59.34(17) . . . . ?
F3D C1D S1D O1D -178.64(14) . . . . ?
F1D C1D S1D O3D -178.96(19) . . . . ?
F2D C1D S1D O3D 61.11(17) . . . . ?
F3D C1D S1D O3D -58.19(17) . . . . ?
F1D C1D S1D O2D -59.6(2) . . . . ?
F2D C1D S1D O2D -179.55(15) . . . . ?
F3D C1D S1D O2D 61.15(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3A H3A O3B 0.76(2) 2.16(2) 2.871(2) 157(2) 2_666
C5A H5A O2D 0.95 2.56 3.390(2) 146.2 2_566
C11A H11B O3D 0.98 2.42 3.359(2) 161.4 1_655
C14A H14A O3D 0.98 2.40 3.128(2) 130.2 1_655
C17A H17A F3D 0.95 2.44 3.160(2) 132.0 2_575
O1C H1C O2B 0.75(2) 2.01(2) 2.7388(19) 162(2) 1_455

_refine_diff_density_max         0.385
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.061

####################################################################### 
# 
# 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 1570188'
_audit_update_record             
;
2017-08-21 deposited with the CCDC.
2017-10-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H15 Cl2 Co N5, C2 H6 O'
_chemical_formula_sum            'C17 H21 Cl2 Co N5 O'
_chemical_formula_weight         441.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co -2.3653 3.6143 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   11.59108(13)
_cell_length_b                   15.95415(19)
_cell_length_c                   20.3432(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3761.98(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    130(1)
_cell_measurement_reflns_used    11197
_cell_measurement_theta_min      4.3210
_cell_measurement_theta_max      75.1580

_exptl_crystal_description       plate
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_F_000             1816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    9.908
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.14751
_exptl_absorpt_correction_T_max  0.24532
_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_absorpt_special_details   ?

_diffrn_ambient_temperature      130(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.5357
_diffrn_measurement_method       ω-scan
_diffrn_reflns_number            18640
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_av_R_equivalents  0.0566
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         4.347
_diffrn_reflns_theta_max         75.515
_diffrn_reflns_theta_full        67.500
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3838
_reflns_number_gt                3622
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_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_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_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1095P)²+2.4417P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3838
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1520
_refine_ls_wR_factor_gt          0.1488
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.21119(4) 0.39314(3) 0.52766(2) 0.02318(17) Uani 1 1 d . . . . .
N1A N 0.3280(2) 0.45967(15) 0.58144(12) 0.0267(5) Uani 1 1 d . . . . .
C2A C 0.3713(2) 0.52705(17) 0.55169(14) 0.0264(5) Uani 1 1 d . . . . .
N3A N 0.4670(2) 0.55715(15) 0.58108(12) 0.0291(5) Uani 1 1 d . . . . .
H3A H 0.5065 0.6018 0.5694 0.035 Uiso 1 1 calc R U . . .
C4A C 0.4911(3) 0.50379(19) 0.63332(14) 0.0296(6) Uani 1 1 d . . . . .
C5A C 0.5823(3) 0.5027(2) 0.67774(15) 0.0337(6) Uani 1 1 d . . . . .
H5A H 0.6409 0.5444 0.6774 0.040 Uiso 1 1 calc R U . . .
C6A C 0.5825(3) 0.4365(2) 0.72306(15) 0.0363(7) Uani 1 1 d . . . . .
H6A H 0.6436 0.4327 0.7540 0.044 Uiso 1 1 calc R U . . .
C7A C 0.4955(3) 0.3760(2) 0.72402(15) 0.0365(7) Uani 1 1 d . . . . .
H7A H 0.4984 0.3327 0.7560 0.044 Uiso 1 1 calc R U . . .
C8A C 0.4043(3) 0.3778(2) 0.67903(15) 0.0321(6) Uani 1 1 d . . . . .
H8A H 0.3453 0.3365 0.6797 0.039 Uiso 1 1 calc R U . . .
C9A C 0.4039(2) 0.44279(18) 0.63315(14) 0.0277(6) Uani 1 1 d . . . . .
N10A N 0.3226(2) 0.56006(14) 0.49585(12) 0.0267(5) Uani 1 1 d . . . . .
C11A C 0.3689(3) 0.6360(2) 0.46516(17) 0.0342(7) Uani 1 1 d . . . . .
H11C H 0.3676 0.6297 0.4172 0.051 Uiso 1 1 calc R U . . .
H11B H 0.4485 0.6448 0.4799 0.051 Uiso 1 1 calc R U . . .
H11A H 0.3217 0.6843 0.4778 0.051 Uiso 1 1 calc R U . . .
N12A N 0.2303(2) 0.51326(14) 0.47580(11) 0.0240(5) Uani 1 1 d . . . . .
C13A C 0.1572(2) 0.53211(17) 0.43039(13) 0.0245(5) Uani 1 1 d . . . . .
C14A C 0.1513(3) 0.60662(19) 0.38559(17) 0.0340(7) Uani 1 1 d . . . . .
H14C H 0.1994 0.6518 0.4033 0.051 Uiso 1 1 calc R U . . .
H14B H 0.0712 0.6259 0.3823 0.051 Uiso 1 1 calc R U . . .
H14A H 0.1793 0.5909 0.3419 0.051 Uiso 1 1 calc R U . . .
C15A C 0.0650(2) 0.46769(17) 0.42428(13) 0.0252(5) Uani 1 1 d . . . . .
N16A N 0.0664(2) 0.40428(15) 0.46846(12) 0.0246(5) Uani 1 1 d . . . . .
C17A C -0.0156(3) 0.34497(18) 0.46507(14) 0.0280(6) Uani 1 1 d . . . . .
H17A H -0.0144 0.3007 0.4963 0.034 Uiso 1 1 calc R U . . .
C18A C -0.1019(3) 0.34568(19) 0.41794(15) 0.0308(6) Uani 1 1 d . . . . .
H18A H -0.1582 0.3024 0.4166 0.037 Uiso 1 1 calc R U . . .
C19A C -0.1046(3) 0.4104(2) 0.37295(16) 0.0352(6) Uani 1 1 d . . . . .
H19A H -0.1629 0.4124 0.3401 0.042 Uiso 1 1 calc R U . . .
C20A C -0.0205(3) 0.47273(19) 0.37651(15) 0.0321(6) Uani 1 1 d . . . . .
H20A H -0.0216 0.5183 0.3465 0.038 Uiso 1 1 calc R U . . .
Cl1B Cl 0.14311(6) 0.29873(4) 0.60364(3) 0.0316(2) Uani 1 1 d . . . . .
Cl1C Cl 0.33240(6) 0.32066(4) 0.45576(3) 0.02831(19) Uani 1 1 d . . . . .
O1D O 0.8202(3) 0.5673(2) 0.74359(17) 0.0608(8) Uani 1 1 d . . . . .
H1D H 0.8605 0.5354 0.7671 0.091 Uiso 1 1 calc R U . . .
C2D C 0.8605(4) 0.6506(3) 0.7499(2) 0.0514(9) Uani 1 1 d . . . . .
H2D2 H 0.9346 0.6574 0.7263 0.062 Uiso 1 1 calc R U . . .
H2D1 H 0.8728 0.6645 0.7968 0.062 Uiso 1 1 calc R U . . .
C3D C 0.7697(6) 0.7075(3) 0.7205(3) 0.0803(18) Uani 1 1 d . . . . .
H3D3 H 0.7856 0.7156 0.6736 0.120 Uiso 1 1 calc R U . . .
H3D2 H 0.7713 0.7618 0.7430 0.120 Uiso 1 1 calc R U . . .
H3D1 H 0.6935 0.6819 0.7259 0.120 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 N1A 2.039(2) . ?
Co1 N16A 2.074(3) . ?
Co1 N12A 2.199(2) . ?
Co1 Cl1B 2.2978(8) . ?
Co1 Cl1C 2.3347(8) . ?
N1A C2A 1.331(4) . ?
N1A C9A 1.397(4) . ?
C2A N3A 1.349(4) . ?
C2A N10A 1.374(4) . ?
N3A C4A 1.390(4) . ?
N3A H3A 0.8800 . ?
C4A C5A 1.391(4) . ?
C4A C9A 1.403(4) . ?
C5A C6A 1.402(5) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.395(5) . ?
C6A H6A 0.9500 . ?
C7A C8A 1.399(5) . ?
C7A H7A 0.9500 . ?
C8A C9A 1.396(4) . ?
C8A H8A 0.9500 . ?
N10A N12A 1.366(3) . ?
N10A C11A 1.465(4) . ?
C11A H11C 0.9800 . ?
C11A H11B 0.9800 . ?
C11A H11A 0.9800 . ?
N12A C13A 1.289(4) . ?
C13A C15A 1.488(4) . ?
C13A C14A 1.499(4) . ?
C14A H14C 0.9800 . ?
C14A H14B 0.9800 . ?
C14A H14A 0.9800 . ?
C15A N16A 1.353(4) . ?
C15A C20A 1.390(4) . ?
N16A C17A 1.343(4) . ?
C17A C18A 1.385(4) . ?
C17A H17A 0.9500 . ?
C18A C19A 1.380(5) . ?
C18A H18A 0.9500 . ?
C19A C20A 1.395(4) . ?
C19A H19A 0.9500 . ?
C20A H20A 0.9500 . ?
O1D C2D 1.415(5) . ?
O1D H1D 0.8400 . ?
C2D C3D 1.513(7) . ?
C2D H2D2 0.9900 . ?
C2D H2D1 0.9900 . ?
C3D H3D3 0.9800 . ?
C3D H3D2 0.9800 . ?
C3D H3D1 0.9800 . ?

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
N1A Co1 N16A 143.58(10) . . ?
N1A Co1 N12A 74.73(9) . . ?
N16A Co1 N12A 74.24(9) . . ?
N1A Co1 Cl1B 102.03(7) . . ?
N16A Co1 Cl1B 99.72(7) . . ?
N12A Co1 Cl1B 158.23(7) . . ?
N1A Co1 Cl1C 101.19(7) . . ?
N16A Co1 Cl1C 99.54(7) . . ?
N12A Co1 Cl1C 94.03(6) . . ?
Cl1B Co1 Cl1C 107.66(3) . . ?
C2A N1A C9A 105.1(2) . . ?
C2A N1A Co1 115.2(2) . . ?
C9A N1A Co1 136.19(19) . . ?
N1A C2A N3A 113.3(3) . . ?
N1A C2A N10A 122.1(3) . . ?
N3A C2A N10A 124.6(3) . . ?
C2A N3A C4A 106.6(2) . . ?
C2A N3A H3A 126.7 . . ?
C4A N3A H3A 126.7 . . ?
C5A C4A N3A 131.1(3) . . ?
C5A C4A C9A 122.7(3) . . ?
N3A C4A C9A 106.2(3) . . ?
C4A C5A C6A 115.9(3) . . ?
C4A C5A H5A 122.0 . . ?
C6A C5A H5A 122.0 . . ?
C7A C6A C5A 122.0(3) . . ?
C7A C6A H6A 119.0 . . ?
C5A C6A H6A 119.0 . . ?
C6A C7A C8A 121.5(3) . . ?
C6A C7A H7A 119.2 . . ?
C8A C7A H7A 119.2 . . ?
C9A C8A C7A 117.1(3) . . ?
C9A C8A H8A 121.5 . . ?
C7A C8A H8A 121.5 . . ?
C8A C9A N1A 130.5(3) . . ?
C8A C9A C4A 120.8(3) . . ?
N1A C9A C4A 108.8(3) . . ?
N12A N10A C2A 111.0(2) . . ?
N12A N10A C11A 127.7(2) . . ?
C2A N10A C11A 121.3(2) . . ?
N10A C11A H11C 109.5 . . ?
N10A C11A H11B 109.5 . . ?
H11C C11A H11B 109.5 . . ?
N10A C11A H11A 109.5 . . ?
H11C C11A H11A 109.5 . . ?
H11B C11A H11A 109.5 . . ?
C13A N12A N10A 126.9(2) . . ?
C13A N12A Co1 118.73(19) . . ?
N10A N12A Co1 114.33(17) . . ?
N12A C13A C15A 111.8(2) . . ?
N12A C13A C14A 130.6(3) . . ?
C15A C13A C14A 117.6(2) . . ?
C13A C14A H14C 109.5 . . ?
C13A C14A H14B 109.5 . . ?
H14C C14A H14B 109.5 . . ?
C13A C14A H14A 109.5 . . ?
H14C C14A H14A 109.5 . . ?
H14B C14A H14A 109.5 . . ?
N16A C15A C20A 121.0(3) . . ?
N16A C15A C13A 116.9(2) . . ?
C20A C15A C13A 122.0(3) . . ?
C17A N16A C15A 119.0(2) . . ?
C17A N16A Co1 122.8(2) . . ?
C15A N16A Co1 117.32(19) . . ?
N16A C17A C18A 122.7(3) . . ?
N16A C17A H17A 118.6 . . ?
C18A C17A H17A 118.6 . . ?
C19A C18A C17A 118.8(3) . . ?
C19A C18A H18A 120.6 . . ?
C17A C18A H18A 120.6 . . ?
C18A C19A C20A 118.9(3) . . ?
C18A C19A H19A 120.6 . . ?
C20A C19A H19A 120.6 . . ?
C15A C20A C19A 119.6(3) . . ?
C15A C20A H20A 120.2 . . ?
C19A C20A H20A 120.2 . . ?
C2D O1D H1D 109.5 . . ?
O1D C2D C3D 107.3(4) . . ?
O1D C2D H2D2 110.2 . . ?
C3D C2D H2D2 110.2 . . ?
O1D C2D H2D1 110.2 . . ?
C3D C2D H2D1 110.2 . . ?
H2D2 C2D H2D1 108.5 . . ?
C2D C3D H3D3 109.5 . . ?
C2D C3D H3D2 109.5 . . ?
H3D3 C3D H3D2 109.5 . . ?
C2D C3D H3D1 109.5 . . ?
H3D3 C3D H3D1 109.5 . . ?
H3D2 C3D H3D1 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9A N1A C2A N3A -2.1(3) . . . . ?
Co1 N1A C2A N3A -164.59(19) . . . . ?
C9A N1A C2A N10A 176.6(3) . . . . ?
Co1 N1A C2A N10A 14.1(3) . . . . ?
N1A C2A N3A C4A 1.9(3) . . . . ?
N10A C2A N3A C4A -176.7(3) . . . . ?
C2A N3A C4A C5A 176.4(3) . . . . ?
C2A N3A C4A C9A -1.0(3) . . . . ?
N3A C4A C5A C6A -177.0(3) . . . . ?
C9A C4A C5A C6A 0.0(4) . . . . ?
C4A C5A C6A C7A -0.8(4) . . . . ?
C5A C6A C7A C8A 0.9(5) . . . . ?
C6A C7A C8A C9A -0.1(5) . . . . ?
C7A C8A C9A N1A 177.6(3) . . . . ?
C7A C8A C9A C4A -0.7(4) . . . . ?
C2A N1A C9A C8A -177.1(3) . . . . ?
Co1 N1A C9A C8A -20.2(5) . . . . ?
C2A N1A C9A C4A 1.3(3) . . . . ?
Co1 N1A C9A C4A 158.2(2) . . . . ?
C5A C4A C9A C8A 0.8(4) . . . . ?
N3A C4A C9A C8A 178.4(3) . . . . ?
C5A C4A C9A N1A -177.8(3) . . . . ?
N3A C4A C9A N1A -0.2(3) . . . . ?
N1A C2A N10A N12A -2.0(4) . . . . ?
N3A C2A N10A N12A 176.5(3) . . . . ?
N1A C2A N10A C11A 177.8(3) . . . . ?
N3A C2A N10A C11A -3.7(4) . . . . ?
C2A N10A N12A C13A 170.8(3) . . . . ?
C11A N10A N12A C13A -9.0(5) . . . . ?
C2A N10A N12A Co1 -10.0(3) . . . . ?
C11A N10A N12A Co1 170.1(2) . . . . ?
N10A N12A C13A C15A -177.4(2) . . . . ?
Co1 N12A C13A C15A 3.6(3) . . . . ?
N10A N12A C13A C14A 1.8(5) . . . . ?
Co1 N12A C13A C14A -177.3(3) . . . . ?
N12A C13A C15A N16A 4.4(3) . . . . ?
C14A C13A C15A N16A -174.9(3) . . . . ?
N12A C13A C15A C20A -177.0(3) . . . . ?
C14A C13A C15A C20A 3.7(4) . . . . ?
C20A C15A N16A C17A 1.0(4) . . . . ?
C13A C15A N16A C17A 179.6(2) . . . . ?
C20A C15A N16A Co1 170.7(2) . . . . ?
C13A C15A N16A Co1 -10.7(3) . . . . ?
C15A N16A C17A C18A 0.2(4) . . . . ?
Co1 N16A C17A C18A -169.0(2) . . . . ?
N16A C17A C18A C19A -0.7(5) . . . . ?
C17A C18A C19A C20A 0.0(5) . . . . ?
N16A C15A C20A C19A -1.6(4) . . . . ?
C13A C15A C20A C19A 179.8(3) . . . . ?
C18A C19A C20A C15A 1.1(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3A H3A Cl1C 0.88 2.30 3.125(3) 156.8 5_666
C5A H5A O1D 0.95 2.50 3.234(4) 133.8 .
C14A H14B Cl1B 0.98 2.77 3.738(4) 167.7 5_566
C17A H17A Cl1C 0.95 2.80 3.561(3) 137.5 4_456
C18A H18A Cl1B 0.95 2.84 3.773(3) 166.6 4_456

_refine_diff_density_max         1.677
_refine_diff_density_min         -0.610
_refine_diff_density_rms         0.114

####################################################################### 
# 
# 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 1570187'
_audit_update_record             
;
2017-08-21 deposited with the CCDC.
2017-10-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H30 Fe N10, 2(C F3 O3 S), C2 H3 N'
_chemical_formula_sum            'C34 H33 F6 Fe N11 O6 S2'
_chemical_formula_weight         925.68

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.7491(3)
_cell_length_b                   16.1976(4)
_cell_length_c                   24.3248(6)
_cell_angle_alpha                90
_cell_angle_beta                 95.452(2)
_cell_angle_gamma                90
_cell_volume                     3823.80(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(1)
_cell_measurement_reflns_used    6656
_cell_measurement_theta_min      3.2696
_cell_measurement_theta_max      26.5279

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_F_000             1896
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.595
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.96094
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector_area_resol_mean 16.2413
_diffrn_measurement_method       ω-scan
_diffrn_reflns_number            14830
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.369
_diffrn_reflns_theta_max         26.496
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.924
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             7317
_reflns_number_gt                6090
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_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_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_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0560P)²+7.1740P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7317
_refine_ls_number_parameters     554
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0495
_refine_ls_wR_factor_ref         0.1302
_refine_ls_wR_factor_gt          0.1221
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.37497(4) 0.18567(2) 0.32774(2) 0.01802(12) Uani 1 1 d . . . . .
N1A N 0.5298(2) 0.19186(14) 0.38603(9) 0.0211(5) Uani 1 1 d . . . . .
C2A C 0.5023(3) 0.24416(17) 0.42518(11) 0.0213(6) Uani 1 1 d . . . . .
N3A N 0.6051(3) 0.25243(16) 0.46570(10) 0.0254(5) Uani 1 1 d . . . . .
H3A H 0.604(4) 0.284(2) 0.4943(16) 0.041(10) Uiso 1 1 d . . . . .
C4A C 0.7100(3) 0.19959(18) 0.45258(12) 0.0229(6) Uani 1 1 d . . . . .
C5A C 0.8367(3) 0.18179(19) 0.47986(12) 0.0269(6) Uani 1 1 d . . . . .
H5A H 0.8680 0.2078 0.5138 0.032 Uiso 1 1 calc R U . . .
C6A C 0.9158(3) 0.1243(2) 0.45554(13) 0.0309(7) Uani 1 1 d . . . . .
H6A H 1.0039 0.1103 0.4731 0.037 Uiso 1 1 calc R U . . .
C7A C 0.8697(3) 0.0864(2) 0.40584(14) 0.0348(7) Uani 1 1 d . . . . .
H7A H 0.9274 0.0473 0.3902 0.042 Uiso 1 1 calc R U . . .
C8A C 0.7415(3) 0.1042(2) 0.37856(13) 0.0303(7) Uani 1 1 d . . . . .
H8A H 0.7102 0.0779 0.3448 0.036 Uiso 1 1 calc R U . . .
C9A C 0.6612(3) 0.16196(18) 0.40255(11) 0.0220(6) Uani 1 1 d . . . . .
N10A N 0.3771(2) 0.28312(15) 0.42371(9) 0.0235(5) Uani 1 1 d . . . . .
C11A C 0.3623(3) 0.36180(19) 0.45213(13) 0.0317(7) Uani 1 1 d . . . . .
H11C H 0.3079 0.3535 0.4835 0.048 Uiso 1 1 calc R U . . .
H11B H 0.3155 0.4016 0.4265 0.048 Uiso 1 1 calc R U . . .
H11A H 0.4536 0.3830 0.4654 0.048 Uiso 1 1 calc R U . . .
N12A N 0.2936(2) 0.25819(14) 0.37751(9) 0.0203(5) Uani 1 1 d . . . . .
C13A C 0.1629(3) 0.27520(17) 0.36926(11) 0.0216(6) Uani 1 1 d . . . . .
C14A C 0.0728(3) 0.3165(2) 0.40750(13) 0.0307(7) Uani 1 1 d . . . . .
H14C H 0.1121 0.3088 0.4458 0.046 Uiso 1 1 calc R U . . .
H14B H -0.0196 0.2922 0.4027 0.046 Uiso 1 1 calc R U . . .
H14A H 0.0669 0.3756 0.3991 0.046 Uiso 1 1 calc R U . . .
C15A C 0.1067(3) 0.24841(17) 0.31422(12) 0.0224(6) Uani 1 1 d . . . . .
N16A N 0.1982(2) 0.20712(14) 0.28522(10) 0.0214(5) Uani 1 1 d . . . . .
C17A C 0.1617(3) 0.19082(17) 0.23142(12) 0.0241(6) Uani 1 1 d . . . . .
H17A H 0.2254 0.1628 0.2108 0.029 Uiso 1 1 calc R U . . .
C18A C 0.0361(3) 0.21319(19) 0.20522(13) 0.0301(7) Uani 1 1 d . . . . .
H18A H 0.0150 0.2027 0.1669 0.036 Uiso 1 1 calc R U . . .
C19A C -0.0588(3) 0.25110(19) 0.23545(14) 0.0321(7) Uani 1 1 d . . . . .
H19A H -0.1477 0.2650 0.2185 0.039 Uiso 1 1 calc R U . . .
C20A C -0.0235(3) 0.26875(18) 0.29080(13) 0.0271(6) Uani 1 1 d . . . . .
H20A H -0.0879 0.2944 0.3123 0.033 Uiso 1 1 calc R U . . .
N1B N 0.4597(2) 0.26452(14) 0.28034(9) 0.0197(5) Uani 1 1 d . . . . .
C2B C 0.5155(3) 0.22792(17) 0.23936(11) 0.0206(6) Uani 1 1 d . . . . .
N3B N 0.5685(3) 0.28068(16) 0.20457(11) 0.0248(5) Uani 1 1 d . . . . .
H3B H 0.596(4) 0.270(3) 0.1769(17) 0.051(13) Uiso 1 1 d . . . . .
C4B C 0.5431(3) 0.35971(18) 0.22350(12) 0.0234(6) Uani 1 1 d . . . . .
C5B C 0.5737(3) 0.43696(19) 0.20409(13) 0.0291(7) Uani 1 1 d . . . . .
H5B H 0.6225 0.4438 0.1724 0.035 Uiso 1 1 calc R U . . .
C6B C 0.5301(3) 0.50367(19) 0.23292(13) 0.0301(7) Uani 1 1 d . . . . .
H6B H 0.5486 0.5578 0.2206 0.036 Uiso 1 1 calc R U . . .
C7B C 0.4593(3) 0.49380(19) 0.27998(13) 0.0288(7) Uani 1 1 d . . . . .
H7B H 0.4304 0.5413 0.2987 0.035 Uiso 1 1 calc R U . . .
C8B C 0.4306(3) 0.41623(18) 0.29972(12) 0.0249(6) Uani 1 1 d . . . . .
H8B H 0.3832 0.4095 0.3318 0.030 Uiso 1 1 calc R U . . .
C9B C 0.4735(3) 0.34880(17) 0.27095(11) 0.0210(6) Uani 1 1 d . . . . .
N10B N 0.5124(2) 0.14285(14) 0.23369(9) 0.0224(5) Uani 1 1 d . . . . .
C11B C 0.6343(4) 0.1027(2) 0.21535(17) 0.0462(10) Uani 1 1 d . . . . .
H11F H 0.6920 0.1439 0.1991 0.069 Uiso 1 1 calc R U . . .
H11E H 0.6058 0.0606 0.1876 0.069 Uiso 1 1 calc R U . . .
H11D H 0.6870 0.0765 0.2470 0.069 Uiso 1 1 calc R U . . .
N12B N 0.4430(2) 0.10996(14) 0.27668(9) 0.0194(5) Uani 1 1 d . . . . .
C13B C 0.4072(3) 0.03239(17) 0.27806(11) 0.0217(6) Uani 1 1 d . . . . .
C14B C 0.4282(4) -0.03194(19) 0.23572(14) 0.0327(7) Uani 1 1 d . . . . .
H14F H 0.4187 -0.0068 0.1989 0.049 Uiso 1 1 calc R U . . .
H14E H 0.3590 -0.0755 0.2375 0.049 Uiso 1 1 calc R U . . .
H14D H 0.5206 -0.0557 0.2430 0.049 Uiso 1 1 calc R U . . .
C15B C 0.3347(3) 0.01463(17) 0.32699(12) 0.0227(6) Uani 1 1 d . . . . .
N16B N 0.3121(2) 0.08180(15) 0.35841(10) 0.0223(5) Uani 1 1 d . . . . .
C17B C 0.2532(3) 0.0702(2) 0.40547(13) 0.0291(7) Uani 1 1 d . . . . .
H17B H 0.2383 0.1167 0.4280 0.035 Uiso 1 1 calc R U . . .
C18B C 0.2132(3) -0.0068(2) 0.42248(14) 0.0361(8) Uani 1 1 d . . . . .
H18B H 0.1731 -0.0130 0.4563 0.043 Uiso 1 1 calc R U . . .
C19B C 0.2322(3) -0.0744(2) 0.38981(15) 0.0363(8) Uani 1 1 d . . . . .
H19B H 0.2026 -0.1275 0.4002 0.044 Uiso 1 1 calc R U . . .
C20B C 0.2947(3) -0.06400(19) 0.34179(13) 0.0297(7) Uani 1 1 d . . . . .
H20B H 0.3102 -0.1101 0.3190 0.036 Uiso 1 1 calc R U . . .
C1C C 0.8665(4) 0.3657(2) 0.08421(16) 0.0447(9) Uani 1 1 d . . . . .
F1C F 0.8669(3) 0.42688(18) 0.04850(12) 0.0821(9) Uani 1 1 d . . . . .
F2C F 0.9781(2) 0.31995(17) 0.07956(12) 0.0659(7) Uani 1 1 d . . . . .
F3C F 0.8785(2) 0.39854(15) 0.13462(10) 0.0580(6) Uani 1 1 d . . . . .
S1C S 0.71162(8) 0.30351(6) 0.07307(3) 0.0347(2) Uani 1 1 d . . . . .
O1C O 0.6032(3) 0.3605(2) 0.08206(11) 0.0561(8) Uani 1 1 d . . . . .
O2C O 0.7151(3) 0.27558(19) 0.01759(10) 0.0538(7) Uani 1 1 d . . . . .
O3C O 0.7321(3) 0.24205(17) 0.11587(10) 0.0479(7) Uani 1 1 d . . . . .
C1D C 0.8937(4) 0.4165(3) 0.55128(18) 0.0489(10) Uani 1 1 d . . . . .
F1D F 1.0041(3) 0.4194(4) 0.58361(19) 0.1467(19) Uani 1 1 d . . . . .
F2D F 0.8795(4) 0.49427(17) 0.53353(15) 0.1005(12) Uani 1 1 d . . . . .
F3D F 0.9110(3) 0.37289(16) 0.50752(13) 0.0847(10) Uani 1 1 d . . . . .
S1D S 0.74498(10) 0.38659(6) 0.58435(4) 0.0436(2) Uani 1 1 d . . . . .
O1D O 0.7826(6) 0.3031(2) 0.6029(2) 0.1151(18) Uani 1 1 d . . . . .
O2D O 0.6390(3) 0.3877(3) 0.54260(15) 0.1075(17) Uani 1 1 d . . . . .
O3D O 0.7367(3) 0.44285(18) 0.62817(10) 0.0534(7) Uani 1 1 d . . . . .
N1E N 0.2229(4) 0.5871(3) 0.64359(18) 0.0744(12) Uani 1 1 d . . . . .
C2E C 0.2752(4) 0.5392(3) 0.61849(16) 0.0473(9) Uani 1 1 d . . . . .
C3E C 0.3394(5) 0.4768(3) 0.58767(18) 0.0559(11) Uani 1 1 d . . . . .
H3E3 H 0.4375 0.4733 0.6006 0.084 Uiso 1 1 calc R U . . .
H3E2 H 0.3291 0.4911 0.5484 0.084 Uiso 1 1 calc R U . . .
H3E1 H 0.2954 0.4234 0.5930 0.084 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 N12B 1.909(2) . ?
Fe1 N12A 1.912(2) . ?
Fe1 N16A 1.955(2) . ?
Fe1 N1B 1.955(2) . ?
Fe1 N16B 1.962(2) . ?
Fe1 N1A 1.973(2) . ?
N1A C2A 1.321(4) . ?
N1A C9A 1.393(4) . ?
C2A N3A 1.344(4) . ?
C2A N10A 1.372(4) . ?
N3A C4A 1.394(4) . ?
N3A H3A 0.86(4) . ?
C4A C5A 1.375(4) . ?
C4A C9A 1.403(4) . ?
C5A C6A 1.378(4) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.392(4) . ?
C6A H6A 0.9500 . ?
C7A C8A 1.389(4) . ?
C7A H7A 0.9500 . ?
C8A C9A 1.384(4) . ?
C8A H8A 0.9500 . ?
N10A N12A 1.384(3) . ?
N10A C11A 1.463(4) . ?
C11A H11C 0.9800 . ?
C11A H11B 0.9800 . ?
C11A H11A 0.9800 . ?
N12A C13A 1.300(4) . ?
C13A C15A 1.464(4) . ?
C13A C14A 1.497(4) . ?
C14A H14C 0.9800 . ?
C14A H14B 0.9800 . ?
C14A H14A 0.9800 . ?
C15A N16A 1.364(4) . ?
C15A C20A 1.380(4) . ?
N16A C17A 1.349(4) . ?
C17A C18A 1.374(4) . ?
C17A H17A 0.9500 . ?
C18A C19A 1.380(5) . ?
C18A H18A 0.9500 . ?
C19A C20A 1.387(4) . ?
C19A H19A 0.9500 . ?
C20A H20A 0.9500 . ?
N1B C2B 1.321(3) . ?
N1B C9B 1.393(4) . ?
C2B N3B 1.340(4) . ?
C2B N10B 1.385(4) . ?
N3B C4B 1.391(4) . ?
N3B H3B 0.77(4) . ?
C4B C5B 1.380(4) . ?
C4B C9B 1.404(4) . ?
C5B C6B 1.377(4) . ?
C5B H5B 0.9500 . ?
C6B C7B 1.401(4) . ?
C6B H6B 0.9500 . ?
C7B C8B 1.383(4) . ?
C7B H7B 0.9500 . ?
C8B C9B 1.383(4) . ?
C8B H8B 0.9500 . ?
N10B N12B 1.403(3) . ?
N10B C11B 1.461(4) . ?
C11B H11F 0.9800 . ?
C11B H11E 0.9800 . ?
C11B H11D 0.9800 . ?
N12B C13B 1.305(4) . ?
C13B C15B 1.470(4) . ?
C13B C14B 1.493(4) . ?
C14B H14F 0.9800 . ?
C14B H14E 0.9800 . ?
C14B H14D 0.9800 . ?
C15B N16B 1.360(4) . ?
C15B C20B 1.389(4) . ?
N16B C17B 1.342(4) . ?
C17B C18B 1.382(4) . ?
C17B H17B 0.9500 . ?
C18B C19B 1.376(5) . ?
C18B H18B 0.9500 . ?
C19B C20B 1.378(5) . ?
C19B H19B 0.9500 . ?
C20B H20B 0.9500 . ?
C1C F1C 1.318(4) . ?
C1C F2C 1.330(5) . ?
C1C F3C 1.332(4) . ?
C1C S1C 1.814(4) . ?
S1C O2C 1.427(2) . ?
S1C O1C 1.436(3) . ?
S1C O3C 1.441(3) . ?
C1D F1D 1.273(5) . ?
C1D F3D 1.301(5) . ?
C1D F2D 1.335(5) . ?
C1D S1D 1.790(4) . ?
S1D O2D 1.379(4) . ?
S1D O3D 1.410(3) . ?
S1D O1D 1.461(4) . ?
N1E C2E 1.137(5) . ?
C2E C3E 1.437(6) . ?
C3E H3E3 0.9800 . ?
C3E H3E2 0.9800 . ?
C3E H3E1 0.9800 . ?

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
N12B Fe1 N12A 175.78(10) . . ?
N12B Fe1 N16A 96.51(10) . . ?
N12A Fe1 N16A 80.08(10) . . ?
N12B Fe1 N1B 81.00(9) . . ?
N12A Fe1 N1B 101.30(10) . . ?
N16A Fe1 N1B 88.43(10) . . ?
N12B Fe1 N16B 80.62(10) . . ?
N12A Fe1 N16B 97.04(10) . . ?
N16A Fe1 N16B 93.54(10) . . ?
N1B Fe1 N16B 161.62(10) . . ?
N12B Fe1 N1A 102.17(10) . . ?
N12A Fe1 N1A 81.32(10) . . ?
N16A Fe1 N1A 161.27(10) . . ?
N1B Fe1 N1A 93.06(10) . . ?
N16B Fe1 N1A 90.90(10) . . ?
C2A N1A C9A 105.0(2) . . ?
C2A N1A Fe1 110.93(19) . . ?
C9A N1A Fe1 144.07(19) . . ?
N1A C2A N3A 113.9(3) . . ?
N1A C2A N10A 121.1(2) . . ?
N3A C2A N10A 124.9(3) . . ?
C2A N3A C4A 106.4(2) . . ?
C2A N3A H3A 126(3) . . ?
C4A N3A H3A 128(3) . . ?
C5A C4A N3A 131.5(3) . . ?
C5A C4A C9A 122.9(3) . . ?
N3A C4A C9A 105.6(2) . . ?
C4A C5A C6A 116.6(3) . . ?
C4A C5A H5A 121.7 . . ?
C6A C5A H5A 121.7 . . ?
C5A C6A C7A 121.6(3) . . ?
C5A C6A H6A 119.2 . . ?
C7A C6A H6A 119.2 . . ?
C8A C7A C6A 121.6(3) . . ?
C8A C7A H7A 119.2 . . ?
C6A C7A H7A 119.2 . . ?
C9A C8A C7A 117.3(3) . . ?
C9A C8A H8A 121.3 . . ?
C7A C8A H8A 121.3 . . ?
C8A C9A N1A 130.9(3) . . ?
C8A C9A C4A 120.0(3) . . ?
N1A C9A C4A 109.1(2) . . ?
C2A N10A N12A 109.9(2) . . ?
C2A N10A C11A 121.0(2) . . ?
N12A N10A C11A 124.1(2) . . ?
N10A C11A H11C 109.5 . . ?
N10A C11A H11B 109.5 . . ?
H11C C11A H11B 109.5 . . ?
N10A C11A H11A 109.5 . . ?
H11C C11A H11A 109.5 . . ?
H11B C11A H11A 109.5 . . ?
C13A N12A N10A 123.8(2) . . ?
C13A N12A Fe1 119.47(19) . . ?
N10A N12A Fe1 116.47(17) . . ?
N12A C13A C15A 110.8(2) . . ?
N12A C13A C14A 128.5(3) . . ?
C15A C13A C14A 120.7(2) . . ?
C13A C14A H14C 109.5 . . ?
C13A C14A H14B 109.5 . . ?
H14C C14A H14B 109.5 . . ?
C13A C14A H14A 109.5 . . ?
H14C C14A H14A 109.5 . . ?
H14B C14A H14A 109.5 . . ?
N16A C15A C20A 121.6(3) . . ?
N16A C15A C13A 114.3(2) . . ?
C20A C15A C13A 123.8(3) . . ?
C17A N16A C15A 118.2(2) . . ?
C17A N16A Fe1 128.0(2) . . ?
C15A N16A Fe1 113.62(19) . . ?
N16A C17A C18A 122.6(3) . . ?
N16A C17A H17A 118.7 . . ?
C18A C17A H17A 118.7 . . ?
C17A C18A C19A 118.9(3) . . ?
C17A C18A H18A 120.5 . . ?
C19A C18A H18A 120.5 . . ?
C18A C19A C20A 119.4(3) . . ?
C18A C19A H19A 120.3 . . ?
C20A C19A H19A 120.3 . . ?
C15A C20A C19A 119.0(3) . . ?
C15A C20A H20A 120.5 . . ?
C19A C20A H20A 120.5 . . ?
C2B N1B C9B 105.2(2) . . ?
C2B N1B Fe1 112.29(18) . . ?
C9B N1B Fe1 142.17(19) . . ?
N1B C2B N3B 113.7(2) . . ?
N1B C2B N10B 121.0(2) . . ?
N3B C2B N10B 125.3(2) . . ?
C2B N3B C4B 106.6(2) . . ?
C2B N3B H3B 126(3) . . ?
C4B N3B H3B 126(3) . . ?
C5B C4B N3B 132.1(3) . . ?
C5B C4B C9B 122.2(3) . . ?
N3B C4B C9B 105.8(2) . . ?
C6B C5B C4B 116.7(3) . . ?
C6B C5B H5B 121.6 . . ?
C4B C5B H5B 121.6 . . ?
C5B C6B C7B 121.8(3) . . ?
C5B C6B H6B 119.1 . . ?
C7B C6B H6B 119.1 . . ?
C8B C7B C6B 121.3(3) . . ?
C8B C7B H7B 119.4 . . ?
C6B C7B H7B 119.4 . . ?
C7B C8B C9B 117.4(3) . . ?
C7B C8B H8B 121.3 . . ?
C9B C8B H8B 121.3 . . ?
C8B C9B N1B 130.7(3) . . ?
C8B C9B C4B 120.6(3) . . ?
N1B C9B C4B 108.7(2) . . ?
C2B N10B N12B 108.1(2) . . ?
C2B N10B C11B 117.6(3) . . ?
N12B N10B C11B 121.5(2) . . ?
N10B C11B H11F 109.5 . . ?
N10B C11B H11E 109.5 . . ?
H11F C11B H11E 109.5 . . ?
N10B C11B H11D 109.5 . . ?
H11F C11B H11D 109.5 . . ?
H11E C11B H11D 109.5 . . ?
C13B N12B N10B 122.3(2) . . ?
C13B N12B Fe1 119.43(19) . . ?
N10B N12B Fe1 117.57(17) . . ?
N12B C13B C15B 111.1(2) . . ?
N12B C13B C14B 126.9(3) . . ?
C15B C13B C14B 122.0(3) . . ?
C13B C14B H14F 109.5 . . ?
C13B C14B H14E 109.5 . . ?
H14F C14B H14E 109.5 . . ?
C13B C14B H14D 109.5 . . ?
H14F C14B H14D 109.5 . . ?
H14E C14B H14D 109.5 . . ?
N16B C15B C20B 121.6(3) . . ?
N16B C15B C13B 114.5(2) . . ?
C20B C15B C13B 123.9(3) . . ?
C17B N16B C15B 118.2(3) . . ?
C17B N16B Fe1 128.2(2) . . ?
C15B N16B Fe1 113.53(19) . . ?
N16B C17B C18B 122.5(3) . . ?
N16B C17B H17B 118.7 . . ?
C18B C17B H17B 118.7 . . ?
C19B C18B C17B 119.2(3) . . ?
C19B C18B H18B 120.4 . . ?
C17B C18B H18B 120.4 . . ?
C18B C19B C20B 119.1(3) . . ?
C18B C19B H19B 120.4 . . ?
C20B C19B H19B 120.4 . . ?
C19B C20B C15B 119.3(3) . . ?
C19B C20B H20B 120.4 . . ?
C15B C20B H20B 120.4 . . ?
F1C C1C F2C 108.0(3) . . ?
F1C C1C F3C 107.5(3) . . ?
F2C C1C F3C 107.4(3) . . ?
F1C C1C S1C 111.9(3) . . ?
F2C C1C S1C 110.7(3) . . ?
F3C C1C S1C 111.0(3) . . ?
O2C S1C O1C 115.60(17) . . ?
O2C S1C O3C 116.76(18) . . ?
O1C S1C O3C 112.81(18) . . ?
O2C S1C C1C 102.90(18) . . ?
O1C S1C C1C 103.56(19) . . ?
O3C S1C C1C 102.70(17) . . ?
F1D C1D F3D 111.0(4) . . ?
F1D C1D F2D 102.7(4) . . ?
F3D C1D F2D 105.4(4) . . ?
F1D C1D S1D 114.0(4) . . ?
F3D C1D S1D 113.2(3) . . ?
F2D C1D S1D 109.7(3) . . ?
O2D S1D O3D 117.1(2) . . ?
O2D S1D O1D 112.8(3) . . ?
O3D S1D O1D 113.3(2) . . ?
O2D S1D C1D 104.4(2) . . ?
O3D S1D C1D 105.77(18) . . ?
O1D S1D C1D 101.4(2) . . ?
N1E C2E C3E 178.3(5) . . ?
C2E C3E H3E3 109.5 . . ?
C2E C3E H3E2 109.5 . . ?
H3E3 C3E H3E2 109.5 . . ?
C2E C3E H3E1 109.5 . . ?
H3E3 C3E H3E1 109.5 . . ?
H3E2 C3E H3E1 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9A N1A C2A N3A 1.0(3) . . . . ?
Fe1 N1A C2A N3A -178.8(2) . . . . ?
C9A N1A C2A N10A -177.1(3) . . . . ?
Fe1 N1A C2A N10A 3.1(3) . . . . ?
N1A C2A N3A C4A -0.9(3) . . . . ?
N10A C2A N3A C4A 177.1(3) . . . . ?
C2A N3A C4A C5A -178.3(3) . . . . ?
C2A N3A C4A C9A 0.4(3) . . . . ?
N3A C4A C5A C6A 178.7(3) . . . . ?
C9A C4A C5A C6A 0.2(4) . . . . ?
C4A C5A C6A C7A 0.1(5) . . . . ?
C5A C6A C7A C8A -0.4(5) . . . . ?
C6A C7A C8A C9A 0.4(5) . . . . ?
C7A C8A C9A N1A -179.1(3) . . . . ?
C7A C8A C9A C4A -0.2(5) . . . . ?
C2A N1A C9A C8A 178.3(3) . . . . ?
Fe1 N1A C9A C8A -2.0(6) . . . . ?
C2A N1A C9A C4A -0.7(3) . . . . ?
Fe1 N1A C9A C4A 179.0(2) . . . . ?
C5A C4A C9A C8A -0.1(5) . . . . ?
N3A C4A C9A C8A -179.0(3) . . . . ?
C5A C4A C9A N1A 179.1(3) . . . . ?
N3A C4A C9A N1A 0.2(3) . . . . ?
N1A C2A N10A N12A 0.4(4) . . . . ?
N3A C2A N10A N12A -177.5(3) . . . . ?
N1A C2A N10A C11A -155.7(3) . . . . ?
N3A C2A N10A C11A 26.5(4) . . . . ?
C2A N10A N12A C13A 169.6(3) . . . . ?
C11A N10A N12A C13A -35.2(4) . . . . ?
C2A N10A N12A Fe1 -4.0(3) . . . . ?
C11A N10A N12A Fe1 151.2(2) . . . . ?
N10A N12A C13A C15A 173.7(2) . . . . ?
Fe1 N12A C13A C15A -12.8(3) . . . . ?
N10A N12A C13A C14A -5.9(5) . . . . ?
Fe1 N12A C13A C14A 167.5(2) . . . . ?
N12A C13A C15A N16A 4.2(3) . . . . ?
C14A C13A C15A N16A -176.1(3) . . . . ?
N12A C13A C15A C20A -170.2(3) . . . . ?
C14A C13A C15A C20A 9.5(4) . . . . ?
C20A C15A N16A C17A 4.1(4) . . . . ?
C13A C15A N16A C17A -170.5(2) . . . . ?
C20A C15A N16A Fe1 -179.9(2) . . . . ?
C13A C15A N16A Fe1 5.5(3) . . . . ?
C15A N16A C17A C18A -0.9(4) . . . . ?
Fe1 N16A C17A C18A -176.2(2) . . . . ?
N16A C17A C18A C19A -2.5(5) . . . . ?
C17A C18A C19A C20A 2.6(5) . . . . ?
N16A C15A C20A C19A -3.9(4) . . . . ?
C13A C15A C20A C19A 170.1(3) . . . . ?
C18A C19A C20A C15A 0.5(5) . . . . ?
C9B N1B C2B N3B 1.8(3) . . . . ?
Fe1 N1B C2B N3B 176.89(19) . . . . ?
C9B N1B C2B N10B -176.1(2) . . . . ?
Fe1 N1B C2B N10B -0.9(3) . . . . ?
N1B C2B N3B C4B -1.3(3) . . . . ?
N10B C2B N3B C4B 176.4(3) . . . . ?
C2B N3B C4B C5B -179.8(3) . . . . ?
C2B N3B C4B C9B 0.3(3) . . . . ?
N3B C4B C5B C6B 178.8(3) . . . . ?
C9B C4B C5B C6B -1.3(4) . . . . ?
C4B C5B C6B C7B 0.6(5) . . . . ?
C5B C6B C7B C8B 0.3(5) . . . . ?
C6B C7B C8B C9B -0.5(5) . . . . ?
C7B C8B C9B N1B -179.8(3) . . . . ?
C7B C8B C9B C4B -0.2(4) . . . . ?
C2B N1B C9B C8B 178.1(3) . . . . ?
Fe1 N1B C9B C8B 5.5(5) . . . . ?
C2B N1B C9B C4B -1.5(3) . . . . ?
Fe1 N1B C9B C4B -174.1(2) . . . . ?
C5B C4B C9B C8B 1.2(4) . . . . ?
N3B C4B C9B C8B -178.9(3) . . . . ?
C5B C4B C9B N1B -179.2(3) . . . . ?
N3B C4B C9B N1B 0.8(3) . . . . ?
N1B C2B N10B N12B 0.4(3) . . . . ?
N3B C2B N10B N12B -177.2(3) . . . . ?
N1B C2B N10B C11B -141.8(3) . . . . ?
N3B C2B N10B C11B 40.6(4) . . . . ?
C2B N10B N12B C13B 170.4(2) . . . . ?
C11B N10B N12B C13B -49.1(4) . . . . ?
C2B N10B N12B Fe1 0.4(3) . . . . ?
C11B N10B N12B Fe1 140.8(3) . . . . ?
N10B N12B C13B C15B -179.3(2) . . . . ?
Fe1 N12B C13B C15B -9.4(3) . . . . ?
N10B N12B C13B C14B -1.9(4) . . . . ?
Fe1 N12B C13B C14B 167.9(2) . . . . ?
N12B C13B C15B N16B 3.9(3) . . . . ?
C14B C13B C15B N16B -173.6(3) . . . . ?
N12B C13B C15B C20B -174.4(3) . . . . ?
C14B C13B C15B C20B 8.1(4) . . . . ?
C20B C15B N16B C17B 2.0(4) . . . . ?
C13B C15B N16B C17B -176.4(3) . . . . ?
C20B C15B N16B Fe1 -178.9(2) . . . . ?
C13B C15B N16B Fe1 2.8(3) . . . . ?
C15B N16B C17B C18B -1.0(4) . . . . ?
Fe1 N16B C17B C18B 180.0(2) . . . . ?
N16B C17B C18B C19B -1.0(5) . . . . ?
C17B C18B C19B C20B 2.1(5) . . . . ?
C18B C19B C20B C15B -1.2(5) . . . . ?
N16B C15B C20B C19B -0.9(4) . . . . ?
C13B C15B C20B C19B 177.3(3) . . . . ?
F1C C1C S1C O2C 58.7(3) . . . . ?
F2C C1C S1C O2C -61.9(3) . . . . ?
F3C C1C S1C O2C 178.9(3) . . . . ?
F1C C1C S1C O1C -62.1(3) . . . . ?
F2C C1C S1C O1C 177.4(3) . . . . ?
F3C C1C S1C O1C 58.1(3) . . . . ?
F1C C1C S1C O3C -179.7(3) . . . . ?
F2C C1C S1C O3C 59.8(3) . . . . ?
F3C C1C S1C O3C -59.5(3) . . . . ?
F1D C1D S1D O2D 179.8(4) . . . . ?
F3D C1D S1D O2D -52.1(4) . . . . ?
F2D C1D S1D O2D 65.3(4) . . . . ?
F1D C1D S1D O3D 55.7(4) . . . . ?
F3D C1D S1D O3D -176.2(3) . . . . ?
F2D C1D S1D O3D -58.9(4) . . . . ?
F1D C1D S1D O1D -62.8(4) . . . . ?
F3D C1D S1D O1D 65.3(4) . . . . ?
F2D C1D S1D O1D -177.3(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3A H3A O2D 0.86(4) 2.06(4) 2.880(5) 158(4) .
C11A H11C O2C 0.98 2.45 3.159(4) 128.7 4_566
C11A H11A O2D 0.98 2.48 3.342(5) 146.5 .
C14A H14C O2C 0.98 2.37 3.258(4) 151.1 4_566
N3B H3B O3C 0.77(4) 2.13(4) 2.871(4) 162(4) .
C5B H5B O1C 0.95 2.57 3.254(4) 129.1 .
C14B H14F O3D 0.98 2.57 3.389(4) 141.1 4_565

_refine_diff_density_max         1.495
_refine_diff_density_min         -0.839
_refine_diff_density_rms         0.075

