# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_CuOTf_2_3a_2
_database_code_depnum_ccdc_archive 'CCDC 1913662'
loop_
_audit_author_name
_audit_author_address
'Pascal Retailleau'
;ICSN CNRS University Paris Saclay
France
;
_audit_update_record             
;
2019-07-09 deposited with the CCDC.	2019-07-11 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT910_CuOTf_2_3a_2        
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         12 Note  
RESPONSE: Indeed 12 Bragg reflections  as listed below were omitted due 
to a theta(min) limit set too high  (From CIF: Theta(Min) =  3.80). 
The very low-order reflections are essentially hidden by the beamstop 
which has a finite size and a fixed setting and the strategy software does not 
readily allow us to set up additional images with the detector at a larger 
distance from the crystal with the beamstop setting changed accordingly. 
These very few missing reflections do not preclude at all the structure 
solution and refinement meeting the iUCR & Chemistry criteria.  
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H18 Cu F6 N6 O10 S2'
_chemical_formula_sum            'C28 H18 Cu F6 N6 O10 S2'
_chemical_formula_weight         840.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'

_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                   7.9107(4)
_cell_length_b                   7.9633(4)
_cell_length_c                   13.4394(8)
_cell_angle_alpha                81.297(4)
_cell_angle_beta                 82.418(5)
_cell_angle_gamma                84.920(4)
_cell_volume                     827.53(8)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4322
_cell_measurement_theta_max      28.9560
_cell_measurement_theta_min      4.6140

_exptl_crystal_description       platelet
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.686
_exptl_crystal_F_000             423
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.886
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56630
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_ambient_environment      air
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) mm003 X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Rigaku MaxFlux double bounce layer optics'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_detector                 'HPAD Dectris Pilatus3R-200K-A'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -25.00  89.00   0.50   45.00    --    0.00  57.00 -30.00  228
  2  ω    -23.00  89.00   0.50   45.00    --    0.00  38.00-180.00  224
  3  ω     -1.00  81.00   0.50   45.00    --    0.00  38.00  60.00  164
;
_diffrn_reflns_number            11808
_diffrn_reflns_av_unetI/netI     0.0659
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.803
_diffrn_reflns_theta_max         30.724
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.863
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.863
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.863
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             4461
_reflns_number_gt                3655
_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_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0576P)²+0.9162P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4448
_refine_ls_number_parameters     241
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0542
_refine_ls_wR_factor_ref         0.1480
_refine_ls_wR_factor_gt          0.1401
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_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 0.500000 0.500000 0.500000 0.02907(14) Uani 1 2 d S . P . .
S1 S 0.36409(10) 0.16066(9) 0.71503(6) 0.04103(19) Uani 1 1 d . . . . .
F1 F 0.4937(4) 0.0008(4) 0.8739(2) 0.0855(8) Uani 1 1 d . . . . .
N1 N 0.6361(3) 0.3510(4) 0.15844(19) 0.0427(6) Uani 1 1 d . . . . .
C1 C 0.5400(3) 0.3695(3) 0.3213(2) 0.0303(5) Uani 1 1 d . . . . .
O1 O 0.4294(2) 0.3836(3) 0.39474(15) 0.0357(4) Uani 1 1 d . . . . .
O2 O 0.4936(3) 0.3657(3) 0.22799(16) 0.0410(5) Uani 1 1 d . . . . .
F2 F 0.6642(4) 0.0096(5) 0.7369(3) 0.1043(11) Uani 1 1 d . . . . .
N2 N 0.7640(3) 0.3446(3) 0.21111(17) 0.0326(5) Uani 1 1 d . . . . .
C2 C 0.7189(3) 0.3549(3) 0.31095(19) 0.0278(5) Uani 1 1 d . . . . .
C5 C 1.0678(4) 0.2146(4) 0.4745(3) 0.0424(7) Uani 1 1 d . . . . .
H5 H 1.176892 0.160129 0.472134 0.051 Uiso 1 1 calc R U . . .
O5 O 0.3113(5) 0.0061(3) 0.6939(3) 0.0796(10) Uani 1 1 d . . . . .
C4 C 0.9843(4) 0.2464(4) 0.3890(2) 0.0376(6) Uani 1 1 d . . . . .
H4 H 1.036273 0.212256 0.328392 0.045 Uiso 1 1 calc R U . . .
O4 O 0.2450(5) 0.2446(5) 0.7835(3) 0.0945(12) Uani 1 1 d . . . . .
C3 C 0.8228(3) 0.3294(3) 0.39384(19) 0.0282(5) Uani 1 1 d . . . . .
N3 N 0.7428(3) 0.3820(3) 0.48105(16) 0.0293(4) Uani 1 1 d . . . . .
O3 O 0.4334(3) 0.2731(3) 0.6295(2) 0.0569(6) Uani 1 1 d . . . . .
F3 F 0.6090(5) 0.2302(4) 0.8099(3) 0.1137(13) Uani 1 1 d . . . . .
C6 C 0.9865(4) 0.2649(4) 0.5634(2) 0.0437(7) Uani 1 1 d . . . . .
H6 H 1.038735 0.242847 0.622521 0.052 Uiso 1 1 calc R U . . .
C7 C 0.8267(4) 0.3483(4) 0.5630(2) 0.0383(6) Uani 1 1 d . . . . .
H7 H 0.773750 0.383419 0.623073 0.046 Uiso 1 1 calc R U . . .
C8 C 0.9324(4) 0.3320(4) 0.1542(2) 0.0356(6) Uani 1 1 d . . . . .
C9 C 0.9808(5) 0.1857(4) 0.1111(3) 0.0498(8) Uani 1 1 d . . . . .
H9 H 0.910546 0.095558 0.120696 0.060 Uiso 1 1 calc R U . . .
C10 C 1.1387(5) 0.1792(6) 0.0528(3) 0.0604(10) Uani 1 1 d . . . . .
H10 H 1.175325 0.082982 0.022275 0.073 Uiso 1 1 calc R U . . .
C11 C 1.2411(5) 0.3115(6) 0.0396(3) 0.0561(9) Uani 1 1 d . . . . .
H11 H 1.346498 0.304467 0.000093 0.067 Uiso 1 1 calc R U . . .
C12 C 1.1905(4) 0.4558(5) 0.0841(3) 0.0513(8) Uani 1 1 d . . . . .
H12 H 1.261994 0.544899 0.075148 0.062 Uiso 1 1 calc R U . . .
C13 C 1.0319(4) 0.4677(4) 0.1423(2) 0.0420(6) Uani 1 1 d . . . . .
H13 H 0.994663 0.564547 0.172236 0.050 Uiso 1 1 calc R U . . .
C14 C 0.5417(5) 0.0971(5) 0.7883(3) 0.0602(9) 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 O1 1.967(2) 2_666 ?
Cu1 O1 1.9669(19) . ?
Cu1 N3 2.064(2) . ?
Cu1 N3 2.064(2) 2_666 ?
Cu1 O3 2.355(2) . ?
Cu1 O3 2.355(2) 2_666 ?
S1 O5 1.413(3) . ?
S1 O4 1.424(3) . ?
S1 O3 1.426(2) . ?
S1 C14 1.813(4) . ?
F1 C14 1.314(5) . ?
N1 N2 1.303(4) . ?
N1 O2 1.375(3) . ?
C1 O1 1.241(3) . ?
C1 O2 1.357(3) . ?
C1 C2 1.400(4) . ?
F2 C14 1.323(5) . ?
N2 C2 1.355(3) . ?
N2 C8 1.449(3) . ?
C2 C3 1.450(4) . ?
C5 C6 1.377(5) . ?
C5 C4 1.379(4) . ?
C4 C3 1.384(4) . ?
C3 N3 1.362(3) . ?
N3 C7 1.340(4) . ?
F3 C14 1.313(5) . ?
C6 C7 1.375(4) . ?
C8 C13 1.371(4) . ?
C8 C9 1.380(4) . ?
C9 C10 1.385(5) . ?
C10 C11 1.362(6) . ?
C11 C12 1.379(5) . ?
C12 C13 1.392(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O1 180.0 2_666 . ?
O1 Cu1 N3 89.21(8) 2_666 . ?
O1 Cu1 N3 90.79(8) . . ?
O1 Cu1 N3 90.79(8) 2_666 2_666 ?
O1 Cu1 N3 89.21(8) . 2_666 ?
N3 Cu1 N3 180.0 . 2_666 ?
O1 Cu1 O3 86.93(9) 2_666 . ?
O1 Cu1 O3 93.07(9) . . ?
N3 Cu1 O3 86.93(9) . . ?
N3 Cu1 O3 93.07(9) 2_666 . ?
O1 Cu1 O3 93.07(9) 2_666 2_666 ?
O1 Cu1 O3 86.93(9) . 2_666 ?
N3 Cu1 O3 93.07(9) . 2_666 ?
N3 Cu1 O3 86.92(9) 2_666 2_666 ?
O3 Cu1 O3 180.0 . 2_666 ?
O5 S1 O4 114.3(3) . . ?
O5 S1 O3 115.9(2) . . ?
O4 S1 O3 113.2(2) . . ?
O5 S1 C14 104.61(19) . . ?
O4 S1 C14 102.4(2) . . ?
O3 S1 C14 104.50(18) . . ?
N2 N1 O2 104.4(2) . . ?
O1 C1 O2 120.3(2) . . ?
O1 C1 C2 133.0(2) . . ?
O2 C1 C2 106.7(2) . . ?
C1 O1 Cu1 114.65(17) . . ?
C1 O2 N1 110.3(2) . . ?
N1 N2 C2 114.7(2) . . ?
N1 N2 C8 115.5(2) . . ?
C2 N2 C8 129.8(2) . . ?
N2 C2 C1 103.9(2) . . ?
N2 C2 C3 130.0(2) . . ?
C1 C2 C3 125.4(2) . . ?
C6 C5 C4 118.8(3) . . ?
C5 C4 C3 119.6(3) . . ?
N3 C3 C4 121.9(3) . . ?
N3 C3 C2 114.2(2) . . ?
C4 C3 C2 123.7(2) . . ?
C7 N3 C3 117.0(2) . . ?
C7 N3 Cu1 117.02(18) . . ?
C3 N3 Cu1 125.91(18) . . ?
S1 O3 Cu1 167.70(18) . . ?
C7 C6 C5 118.7(3) . . ?
N3 C7 C6 123.9(3) . . ?
C13 C8 C9 123.5(3) . . ?
C13 C8 N2 118.6(3) . . ?
C9 C8 N2 117.8(3) . . ?
C8 C9 C10 117.0(3) . . ?
C11 C10 C9 121.1(3) . . ?
C10 C11 C12 120.9(3) . . ?
C11 C12 C13 119.7(3) . . ?
C8 C13 C12 117.8(3) . . ?
F3 C14 F1 108.1(4) . . ?
F3 C14 F2 107.4(4) . . ?
F1 C14 F2 107.7(4) . . ?
F3 C14 S1 111.3(3) . . ?
F1 C14 S1 111.4(3) . . ?
F2 C14 S1 110.8(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 O1 Cu1 -150.3(2) . . . . ?
C2 C1 O1 Cu1 29.8(4) . . . . ?
O1 C1 O2 N1 179.5(2) . . . . ?
C2 C1 O2 N1 -0.6(3) . . . . ?
N2 N1 O2 C1 0.6(3) . . . . ?
O2 N1 N2 C2 -0.4(3) . . . . ?
O2 N1 N2 C8 -178.9(2) . . . . ?
N1 N2 C2 C1 0.0(3) . . . . ?
C8 N2 C2 C1 178.3(3) . . . . ?
N1 N2 C2 C3 170.7(3) . . . . ?
C8 N2 C2 C3 -11.1(4) . . . . ?
O1 C1 C2 N2 -179.7(3) . . . . ?
O2 C1 C2 N2 0.3(3) . . . . ?
O1 C1 C2 C3 9.1(5) . . . . ?
O2 C1 C2 C3 -170.9(2) . . . . ?
C6 C5 C4 C3 0.8(5) . . . . ?
C5 C4 C3 N3 0.3(4) . . . . ?
C5 C4 C3 C2 -174.2(3) . . . . ?
N2 C2 C3 N3 167.8(2) . . . . ?
C1 C2 C3 N3 -23.4(3) . . . . ?
N2 C2 C3 C4 -17.3(4) . . . . ?
C1 C2 C3 C4 151.5(3) . . . . ?
C4 C3 N3 C7 -0.7(4) . . . . ?
C2 C3 N3 C7 174.3(2) . . . . ?
C4 C3 N3 Cu1 -178.0(2) . . . . ?
C2 C3 N3 Cu1 -3.0(3) . . . . ?
O5 S1 O3 Cu1 121.4(9) . . . . ?
O4 S1 O3 Cu1 -13.4(10) . . . . ?
C14 S1 O3 Cu1 -124.0(9) . . . . ?
C4 C5 C6 C7 -1.4(5) . . . . ?
C3 N3 C7 C6 0.0(4) . . . . ?
Cu1 N3 C7 C6 177.5(2) . . . . ?
C5 C6 C7 N3 1.1(5) . . . . ?
N1 N2 C8 C13 111.7(3) . . . . ?
C2 N2 C8 C13 -66.5(4) . . . . ?
N1 N2 C8 C9 -65.6(4) . . . . ?
C2 N2 C8 C9 116.1(3) . . . . ?
C13 C8 C9 C10 -0.2(5) . . . . ?
N2 C8 C9 C10 177.0(3) . . . . ?
C8 C9 C10 C11 0.4(6) . . . . ?
C9 C10 C11 C12 0.1(6) . . . . ?
C10 C11 C12 C13 -0.7(6) . . . . ?
C9 C8 C13 C12 -0.4(5) . . . . ?
N2 C8 C13 C12 -177.5(3) . . . . ?
C11 C12 C13 C8 0.8(5) . . . . ?
O5 S1 C14 F3 177.4(3) . . . . ?
O4 S1 C14 F3 -63.1(4) . . . . ?
O3 S1 C14 F3 55.1(4) . . . . ?
O5 S1 C14 F1 -61.9(4) . . . . ?
O4 S1 C14 F1 57.6(4) . . . . ?
O3 S1 C14 F1 175.8(3) . . . . ?
O5 S1 C14 F2 58.0(4) . . . . ?
O4 S1 C14 F2 177.5(3) . . . . ?
O3 S1 C14 F2 -64.2(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
_geom_hbond_publ_flag
C6 H6 S1 0.93 2.98 3.797(3) 147.1 1_655 yes
C7 H7 O1 0.93 2.35 2.878(4) 115.7 2_666 yes
C13 H13 O4 0.93 2.39 3.204(4) 145.7 2_666 yes

_refine_diff_density_max         1.309
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.085

####################################################################### 
# 
# 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_NIP350
_database_code_depnum_ccdc_archive 'CCDC 1913665'
loop_
_audit_author_name
_audit_author_address
'Pascal Retailleau'
;CNRS
France
;
_audit_update_record             
;
2019-05-02 deposited with the CCDC.	2019-07-11 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT910_NIP350              
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         11 Note  
RESPONSE: Indeed 11 Bragg reflections  as listed below were omitted due 
to a theta(min) limit set too high  (From CIF: Theta(Min) =  3.92). 
The very low-order reflections are essentially hidden by the beamstop 
which has a finite size and a fixed setting and the strategy software does not 
readily allow us to set up additional images with the detector at a larger 
distance from the crystal with the beamstop setting changed accordingly. 
These very few missing reflections do not preclude at all the structure 
solution and refinement meeting the iUCR & Chemistry criteria.  
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H9 Cl2 N3 O2 Zn'
_chemical_formula_sum            'C13 H9 Cl2 N3 O2 Zn'
_chemical_formula_weight         375.50

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'
Cl Cl 0.1484 0.1585 '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'
Zn Zn 0.2839 1.4301 '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                   8.5206(4)
_cell_length_b                   8.9361(3)
_cell_length_c                   9.9810(3)
_cell_angle_alpha                94.269(3)
_cell_angle_beta                 99.231(3)
_cell_angle_gamma                94.285(3)
_cell_volume                     745.13(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8579
_cell_measurement_theta_min      4.1400
_cell_measurement_theta_max      30.5890

_exptl_crystal_description       tab
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.674
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    2.012
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.46733
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_ambient_environment      air
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) mm003 X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Rigaku MaxFlux double bounce layer optics'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_detector                 'HPAD Dectris Pilatus3R-200K-A'
_diffrn_reflns_number            19751
_diffrn_reflns_av_unetI/netI     0.0526
_diffrn_reflns_av_R_equivalents  0.0616
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.920
_diffrn_reflns_theta_max         31.002
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.907
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.907
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.907
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4322
_reflns_number_gt                3627
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0288P)²+0.1190P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.024(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4319
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0305
_refine_ls_wR_factor_ref         0.0773
_refine_ls_wR_factor_gt          0.0742
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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
Zn1 Zn 0.58096(2) 0.67975(2) 0.80782(2) 0.03569(8) Uani 1 1 d . . . . .
Cl1 Cl 0.71531(5) 0.83954(5) 0.97185(5) 0.04866(12) Uani 1 1 d . . . . .
C1 C 0.33819(18) 0.39118(17) 0.76341(15) 0.0311(3) Uani 1 1 d . . . . .
N1 N 0.37369(19) 0.15232(17) 0.69813(16) 0.0451(3) Uani 1 1 d . . . . .
O1 O 0.62043(13) 0.46061(14) 0.84424(14) 0.0447(3) Uani 1 1 d . . . . .
O2 O 0.51888(15) 0.22631(14) 0.75491(14) 0.0452(3) Uani 1 1 d . . . . .
Cl2 Cl 0.59626(8) 0.69981(8) 0.59464(5) 0.06905(17) Uani 1 1 d . . . . .
C2 C 0.50207(19) 0.37450(19) 0.79346(17) 0.0360(3) Uani 1 1 d . . . . .
N2 N 0.27250(16) 0.25402(15) 0.70520(14) 0.0346(3) Uani 1 1 d . . . . .
N3 N 0.34794(15) 0.64995(15) 0.83934(13) 0.0320(3) Uani 1 1 d . . . . .
C3 C 0.25631(17) 0.51815(17) 0.80930(14) 0.0294(3) Uani 1 1 d . . . . .
C4 C 0.2856(2) 0.77018(19) 0.89265(19) 0.0403(4) Uani 1 1 d . . . . .
H4 H 0.349876 0.860171 0.914935 0.048 Uiso 1 1 calc R U . . .
C5 C 0.1300(2) 0.7651(2) 0.9155(2) 0.0458(4) Uani 1 1 d . . . . .
H5 H 0.089722 0.850007 0.952084 0.055 Uiso 1 1 calc R U . . .
C6 C 0.0358(2) 0.6312(2) 0.8829(2) 0.0451(4) Uani 1 1 d . . . . .
H6 H -0.069976 0.625195 0.896107 0.054 Uiso 1 1 calc R U . . .
C7 C 0.09864(19) 0.5059(2) 0.83042(18) 0.0388(3) Uani 1 1 d . . . . .
H7 H 0.036389 0.414586 0.809529 0.047 Uiso 1 1 calc R U . . .
C8 C 0.1067(2) 0.20975(18) 0.64817(16) 0.0363(3) Uani 1 1 d . . . . .
C9 C 0.0341(2) 0.2894(2) 0.5465(2) 0.0505(4) Uani 1 1 d . . . . .
H9 H 0.090770 0.365403 0.510714 0.061 Uiso 1 1 calc R U . . .
C10 C -0.1272(3) 0.2517(3) 0.4996(2) 0.0628(6) Uani 1 1 d . . . . .
H10 H -0.180413 0.303898 0.431583 0.075 Uiso 1 1 calc R U . . .
C11 C -0.2095(3) 0.1381(3) 0.5523(2) 0.0606(6) Uani 1 1 d . . . . .
H11 H -0.318016 0.115162 0.520767 0.073 Uiso 1 1 calc R U . . .
C12 C -0.1324(3) 0.0588(3) 0.6508(3) 0.0658(6) Uani 1 1 d . . . . .
H12 H -0.188008 -0.019772 0.684197 0.079 Uiso 1 1 calc R U . . .
C13 C 0.0284(3) 0.0950(2) 0.7011(2) 0.0520(5) Uani 1 1 d . . . . .
H13 H 0.081457 0.042629 0.769024 0.062 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
Zn1 O1 2.0603(13) . ?
Zn1 N3 2.0605(13) . ?
Zn1 Cl2 2.1723(5) . ?
Zn1 Cl1 2.1991(5) . ?
C1 N2 1.357(2) . ?
C1 C2 1.402(2) . ?
C1 C3 1.458(2) . ?
N1 N2 1.304(2) . ?
N1 O2 1.373(2) . ?
O1 C2 1.236(2) . ?
O2 C2 1.376(2) . ?
N2 C8 1.449(2) . ?
N3 C4 1.346(2) . ?
N3 C3 1.350(2) . ?
C3 C7 1.391(2) . ?
C4 C5 1.378(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.377(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.381(2) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C13 1.366(3) . ?
C8 C9 1.375(3) . ?
C9 C10 1.386(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.375(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.366(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.387(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Zn1 N3 92.21(5) . . ?
O1 Zn1 Cl2 106.53(4) . . ?
N3 Zn1 Cl2 112.01(4) . . ?
O1 Zn1 Cl1 111.22(4) . . ?
N3 Zn1 Cl1 108.54(4) . . ?
Cl2 Zn1 Cl1 122.22(2) . . ?
N2 C1 C2 104.42(13) . . ?
N2 C1 C3 127.91(13) . . ?
C2 C1 C3 126.68(14) . . ?
N2 N1 O2 104.37(13) . . ?
C2 O1 Zn1 110.41(10) . . ?
N1 O2 C2 110.55(12) . . ?
O1 C2 O2 120.20(14) . . ?
O1 C2 C1 133.96(15) . . ?
O2 C2 C1 105.84(14) . . ?
N1 N2 C1 114.77(14) . . ?
N1 N2 C8 117.28(14) . . ?
C1 N2 C8 127.93(13) . . ?
C4 N3 C3 119.07(13) . . ?
C4 N3 Zn1 117.19(11) . . ?
C3 N3 Zn1 123.74(10) . . ?
N3 C3 C7 121.05(14) . . ?
N3 C3 C1 115.10(13) . . ?
C7 C3 C1 123.72(14) . . ?
N3 C4 C5 122.54(16) . . ?
N3 C4 H4 118.7 . . ?
C5 C4 H4 118.7 . . ?
C6 C5 C4 118.37(16) . . ?
C6 C5 H5 120.8 . . ?
C4 C5 H5 120.8 . . ?
C5 C6 C7 119.90(16) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C6 C7 C3 119.05(16) . . ?
C6 C7 H7 120.5 . . ?
C3 C7 H7 120.5 . . ?
C13 C8 C9 123.06(17) . . ?
C13 C8 N2 118.71(16) . . ?
C9 C8 N2 118.18(16) . . ?
C8 C9 C10 117.2(2) . . ?
C8 C9 H9 121.4 . . ?
C10 C9 H9 121.4 . . ?
C11 C10 C9 120.9(2) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C12 C11 C10 120.2(2) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C13 120.3(2) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C8 C13 C12 118.3(2) . . ?
C8 C13 H13 120.9 . . ?
C12 C13 H13 120.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 N1 O2 C2 -1.10(18) . . . . ?
Zn1 O1 C2 O2 153.28(13) . . . . ?
Zn1 O1 C2 C1 -27.5(2) . . . . ?
N1 O2 C2 O1 -178.49(16) . . . . ?
N1 O2 C2 C1 2.12(18) . . . . ?
N2 C1 C2 O1 178.51(19) . . . . ?
C3 C1 C2 O1 -12.2(3) . . . . ?
N2 C1 C2 O2 -2.22(17) . . . . ?
C3 C1 C2 O2 167.05(14) . . . . ?
O2 N1 N2 C1 -0.43(19) . . . . ?
O2 N1 N2 C8 178.11(13) . . . . ?
C2 C1 N2 N1 1.71(19) . . . . ?
C3 C1 N2 N1 -167.38(15) . . . . ?
C2 C1 N2 C8 -176.64(15) . . . . ?
C3 C1 N2 C8 14.3(3) . . . . ?
C4 N3 C3 C7 1.1(2) . . . . ?
Zn1 N3 C3 C7 -178.70(12) . . . . ?
C4 N3 C3 C1 -174.80(14) . . . . ?
Zn1 N3 C3 C1 5.39(18) . . . . ?
N2 C1 C3 N3 -167.87(15) . . . . ?
C2 C1 C3 N3 25.3(2) . . . . ?
N2 C1 C3 C7 16.3(3) . . . . ?
C2 C1 C3 C7 -150.45(17) . . . . ?
C3 N3 C4 C5 -1.3(3) . . . . ?
Zn1 N3 C4 C5 178.50(14) . . . . ?
N3 C4 C5 C6 0.3(3) . . . . ?
C4 C5 C6 C7 0.9(3) . . . . ?
C5 C6 C7 C3 -1.1(3) . . . . ?
N3 C3 C7 C6 0.1(3) . . . . ?
C1 C3 C7 C6 175.62(16) . . . . ?
N1 N2 C8 C13 60.6(2) . . . . ?
C1 N2 C8 C13 -121.0(2) . . . . ?
N1 N2 C8 C9 -121.78(19) . . . . ?
C1 N2 C8 C9 56.5(2) . . . . ?
C13 C8 C9 C10 1.6(3) . . . . ?
N2 C8 C9 C10 -175.88(18) . . . . ?
C8 C9 C10 C11 -0.7(3) . . . . ?
C9 C10 C11 C12 -1.0(4) . . . . ?
C10 C11 C12 C13 1.8(4) . . . . ?
C9 C8 C13 C12 -0.8(3) . . . . ?
N2 C8 C13 C12 176.64(19) . . . . ?
C11 C12 C13 C8 -0.9(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C4 H4 Cl1 0.93 2.96 3.6465(18) 131.9 2_677 yes
C13 H13 Cl1 0.93 2.95 3.607(2) 129.2 2_667 yes

_refine_diff_density_max         0.589
_refine_diff_density_min         -0.636
_refine_diff_density_rms         0.139

####################################################################### 
# 
# 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_NIP321b
_database_code_depnum_ccdc_archive 'CCDC 1913664'
loop_
_audit_author_name
_audit_author_address
'Pascal Retailleau'
;CNRS
France
;
_audit_update_record             
;
2019-05-02 deposited with the CCDC.	2019-07-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        3-Phenyl-4-(2-pyridinyl)-sydnone
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H9 N3 O2'
_chemical_formula_sum            'C13 H9 N3 O2'
_chemical_formula_weight         239.23

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'

_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                   8.7441(8)
_cell_length_b                   13.0971(15)
_cell_length_c                   10.0411(10)
_cell_angle_alpha                90
_cell_angle_beta                 100.651(10)
_cell_angle_gamma                90
_cell_volume                     1130.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1411
_cell_measurement_theta_min      3.9060
_cell_measurement_theta_max      25.7890

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_F_000             496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.099
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.46092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_ambient_environment      air
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) mm003 X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Rigaku MaxFlux double bounce layer optics'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_detector                 'HPAD Dectris Pilatus3R-200K-A'
_diffrn_reflns_number            12373
_diffrn_reflns_av_unetI/netI     0.0672
_diffrn_reflns_av_R_equivalents  0.0951
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.912
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2212
_reflns_number_gt                1337
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0479P)²+0.2214P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2212
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0960
_refine_ls_R_factor_gt           0.0513
_refine_ls_wR_factor_ref         0.1412
_refine_ls_wR_factor_gt          0.1181
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.000
_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
O1 O 0.6203(2) 0.46740(15) 0.3330(2) 0.0851(6) Uani 1 1 d . . . . .
N1 N 0.3295(2) 0.63807(19) 0.3573(2) 0.0716(6) Uani 1 1 d . . . . .
C1 C 0.5498(3) 0.5422(2) 0.3583(3) 0.0645(7) Uani 1 1 d . . . . .
O2 O 0.3871(2) 0.54851(15) 0.31592(19) 0.0772(6) Uani 1 1 d . . . . .
N2 N 0.4545(2) 0.68592(15) 0.42042(18) 0.0538(5) Uani 1 1 d . . . . .
C2 C 0.5904(3) 0.63582(17) 0.4251(2) 0.0512(6) Uani 1 1 d . . . . .
N3 N 0.7692(2) 0.77498(16) 0.4607(3) 0.0747(7) Uani 1 1 d . . . . .
C3 C 0.7456(2) 0.67568(19) 0.4786(2) 0.0515(6) Uani 1 1 d . . . . .
C6 C 1.0086(3) 0.6496(3) 0.5856(3) 0.0745(8) Uani 1 1 d . . . . .
H6 H 1.089055 0.607332 0.626790 0.089 Uiso 1 1 calc R U . . .
C5 C 1.0337(3) 0.7518(3) 0.5696(3) 0.0805(9) Uani 1 1 d . . . . .
H5 H 1.130874 0.780590 0.601122 0.097 Uiso 1 1 calc R U . . .
C4 C 0.9130(3) 0.8101(2) 0.5065(4) 0.0895(10) Uani 1 1 d . . . . .
H4 H 0.931711 0.879097 0.494411 0.107 Uiso 1 1 calc R U . . .
C9 C 0.4759(3) 0.7909(2) 0.6213(2) 0.0583(6) Uani 1 1 d . . . . .
H9 H 0.532347 0.739118 0.671467 0.070 Uiso 1 1 calc R U . . .
C8 C 0.4252(2) 0.78106(18) 0.4842(2) 0.0504(6) Uani 1 1 d . . . . .
C7 C 0.8615(3) 0.6107(2) 0.5393(2) 0.0627(7) Uani 1 1 d . . . . .
H7 H 0.841062 0.541632 0.548979 0.075 Uiso 1 1 calc R U . . .
C10 C 0.4405(3) 0.8800(2) 0.6824(3) 0.0658(7) Uani 1 1 d . . . . .
H10 H 0.474070 0.888829 0.775102 0.079 Uiso 1 1 calc R U . . .
C11 C 0.3572(3) 0.9550(2) 0.6086(3) 0.0705(7) Uani 1 1 d . . . . .
H11 H 0.333491 1.014443 0.651189 0.085 Uiso 1 1 calc R U . . .
C12 C 0.3078(3) 0.9437(2) 0.4720(3) 0.0736(8) Uani 1 1 d . . . . .
H12 H 0.251789 0.995662 0.422051 0.088 Uiso 1 1 calc R U . . .
C13 C 0.3408(3) 0.8558(2) 0.4086(3) 0.0640(7) Uani 1 1 d . . . . .
H13 H 0.306440 0.847237 0.316002 0.077 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
O1 C1 1.209(3) . ?
N1 N2 1.316(3) . ?
N1 O2 1.371(3) . ?
C1 O2 1.410(3) . ?
C1 C2 1.412(3) . ?
N2 C2 1.351(3) . ?
N2 C8 1.445(3) . ?
C2 C3 1.460(3) . ?
N3 C3 1.334(3) . ?
N3 C4 1.338(3) . ?
C3 C7 1.376(3) . ?
C6 C5 1.370(4) . ?
C6 C7 1.383(4) . ?
C5 C4 1.361(4) . ?
C9 C8 1.372(3) . ?
C9 C10 1.380(3) . ?
C8 C13 1.368(3) . ?
C10 C11 1.359(4) . ?
C11 C12 1.367(4) . ?
C12 C13 1.371(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 O2 103.57(18) . . ?
O1 C1 O2 120.7(2) . . ?
O1 C1 C2 135.2(3) . . ?
O2 C1 C2 104.1(2) . . ?
N1 O2 C1 111.45(18) . . ?
N1 N2 C2 115.6(2) . . ?
N1 N2 C8 115.12(18) . . ?
C2 N2 C8 129.06(18) . . ?
N2 C2 C1 105.2(2) . . ?
N2 C2 C3 126.2(2) . . ?
C1 C2 C3 128.4(2) . . ?
C3 N3 C4 116.6(2) . . ?
N3 C3 C7 122.9(2) . . ?
N3 C3 C2 117.1(2) . . ?
C7 C3 C2 120.0(2) . . ?
C5 C6 C7 118.7(3) . . ?
C4 C5 C6 118.4(3) . . ?
N3 C4 C5 124.4(3) . . ?
C8 C9 C10 117.9(2) . . ?
C13 C8 C9 122.0(2) . . ?
C13 C8 N2 119.5(2) . . ?
C9 C8 N2 118.3(2) . . ?
C3 C7 C6 118.9(3) . . ?
C11 C10 C9 120.7(2) . . ?
C10 C11 C12 120.5(3) . . ?
C11 C12 C13 120.2(3) . . ?
C8 C13 C12 118.8(2) . . ?

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
N2 N1 O2 C1 1.4(3) . . . . ?
O1 C1 O2 N1 178.6(2) . . . . ?
C2 C1 O2 N1 -1.9(3) . . . . ?
O2 N1 N2 C2 -0.2(3) . . . . ?
O2 N1 N2 C8 -175.50(18) . . . . ?
N1 N2 C2 C1 -1.0(3) . . . . ?
C8 N2 C2 C1 173.5(2) . . . . ?
N1 N2 C2 C3 174.5(2) . . . . ?
C8 N2 C2 C3 -11.0(4) . . . . ?
O1 C1 C2 N2 -179.0(3) . . . . ?
O2 C1 C2 N2 1.7(2) . . . . ?
O1 C1 C2 C3 5.7(5) . . . . ?
O2 C1 C2 C3 -173.6(2) . . . . ?
C4 N3 C3 C7 -0.7(4) . . . . ?
C4 N3 C3 C2 -178.1(2) . . . . ?
N2 C2 C3 N3 -34.7(3) . . . . ?
C1 C2 C3 N3 139.7(3) . . . . ?
N2 C2 C3 C7 147.8(2) . . . . ?
C1 C2 C3 C7 -37.8(3) . . . . ?
C7 C6 C5 C4 -1.2(4) . . . . ?
C3 N3 C4 C5 -0.4(5) . . . . ?
C6 C5 C4 N3 1.4(5) . . . . ?
C10 C9 C8 C13 -0.6(3) . . . . ?
C10 C9 C8 N2 -176.8(2) . . . . ?
N1 N2 C8 C13 -55.2(3) . . . . ?
C2 N2 C8 C13 130.3(2) . . . . ?
N1 N2 C8 C9 121.1(2) . . . . ?
C2 N2 C8 C9 -53.4(3) . . . . ?
N3 C3 C7 C6 0.8(4) . . . . ?
C2 C3 C7 C6 178.1(2) . . . . ?
C5 C6 C7 C3 0.1(4) . . . . ?
C8 C9 C10 C11 0.4(4) . . . . ?
C9 C10 C11 C12 -0.5(4) . . . . ?
C10 C11 C12 C13 0.7(4) . . . . ?
C9 C8 C13 C12 0.8(4) . . . . ?
N2 C8 C13 C12 177.0(2) . . . . ?
C11 C12 C13 C8 -0.8(4) . . . . ?

_refine_diff_density_max         0.143
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.040

####################################################################### 
# 
# 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_NIP318A
_database_code_depnum_ccdc_archive 'CCDC 1913667'
loop_
_audit_author_name
_audit_author_address
'Pascal Retailleau'
;ICSN CNRS University Paris Saclay
France
;
_audit_update_record             
;
2019-07-09 deposited with the CCDC.	2019-07-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H18 Cl2 Cu N6 O4'
_chemical_formula_sum            'C26 H18 Cl2 Cu N6 O4'
_chemical_formula_weight         612.90

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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                   8.0661(3)
_cell_length_b                   8.8517(4)
_cell_length_c                   10.0437(4)
_cell_angle_alpha                108.745(4)
_cell_angle_beta                 104.613(3)
_cell_angle_gamma                96.672(4)
_cell_volume                     641.70(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7697
_cell_measurement_theta_min      3.9370
_cell_measurement_theta_max      31.0550

_exptl_crystal_description       cobbledstone
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.586
_exptl_crystal_F_000             311
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    1.105
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.66254
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_ambient_environment      air
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) mm003 X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Rigaku MaxFlux double bounce layer optics'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_detector                 'HPAD Dectris Pilatus3R-200K-A'
_diffrn_reflns_number            17478
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.671
_diffrn_reflns_theta_max         31.036
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.902
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.902
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.902
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3711
_reflns_number_gt                3195
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0357P)²+0.1256P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3708
_refine_ls_number_parameters     178
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0301
_refine_ls_wR_factor_ref         0.0822
_refine_ls_wR_factor_gt          0.0789
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_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 0.500000 0.500000 0.500000 0.02875(8) Uani 1 2 d S . P . .
O1 O 0.71811(17) 0.72346(13) 0.47899(14) 0.0430(3) Uani 1 1 d . . . . .
N1 N 0.7619(2) 0.59679(18) 0.13233(18) 0.0525(4) Uani 1 1 d . . . . .
Cl1 Cl 0.64778(5) 0.58259(5) 0.74485(4) 0.04421(11) Uani 1 1 d . . . . .
C1 C 0.7407(2) 0.64397(17) 0.36473(18) 0.0348(3) Uani 1 1 d . . . . .
C2 C 0.76110(19) 0.48252(16) 0.30176(16) 0.0305(3) Uani 1 1 d . . . . .
N2 N 0.76894(17) 0.46580(15) 0.16508(14) 0.0345(3) Uani 1 1 d . . . . .
O2 O 0.7497(2) 0.71160(14) 0.25788(15) 0.0515(3) Uani 1 1 d . . . . .
C3 C 0.76789(18) 0.35496(15) 0.36471(15) 0.0292(3) Uani 1 1 d . . . . .
N3 N 0.66726(16) 0.35109(14) 0.45304(13) 0.0302(2) Uani 1 1 d . . . . .
C4 C 0.8758(2) 0.24454(18) 0.33753(18) 0.0375(3) Uani 1 1 d . . . . .
H4 H 0.949324 0.252643 0.281012 0.045 Uiso 1 1 calc R U . . .
C5 C 0.8725(2) 0.12261(19) 0.3956(2) 0.0429(4) Uani 1 1 d . . . . .
H5 H 0.940955 0.045556 0.375789 0.052 Uiso 1 1 calc R U . . .
C6 C 0.7669(2) 0.11638(19) 0.4830(2) 0.0427(4) Uani 1 1 d . . . . .
H6 H 0.760671 0.033979 0.521330 0.051 Uiso 1 1 calc R U . . .
C9 C 0.6118(3) 0.2032(2) -0.0205(2) 0.0537(5) Uani 1 1 d . . . . .
H9 H 0.510748 0.222215 0.004630 0.064 Uiso 1 1 calc R U . . .
C8 C 0.7668(2) 0.31737(18) 0.04756(16) 0.0357(3) Uani 1 1 d . . . . .
C7 C 0.6705(2) 0.23507(18) 0.51227(19) 0.0389(3) Uani 1 1 d . . . . .
H7 H 0.604748 0.234701 0.576072 0.047 Uiso 1 1 calc R U . . .
C10 C 0.6119(3) 0.0581(3) -0.1285(2) 0.0684(6) Uani 1 1 d . . . . .
H10 H 0.509164 -0.022091 -0.176509 0.082 Uiso 1 1 calc R U . . .
C11 C 0.7611(4) 0.0317(2) -0.1652(2) 0.0639(6) Uani 1 1 d . . . . .
H11 H 0.759086 -0.066187 -0.237498 0.077 Uiso 1 1 calc R U . . .
C12 C 0.9141(3) 0.1494(2) -0.0956(2) 0.0576(5) Uani 1 1 d . . . . .
H12 H 1.015136 0.130559 -0.120819 0.069 Uiso 1 1 calc R U . . .
C13 C 0.9181(2) 0.2959(2) 0.0122(2) 0.0446(4) Uani 1 1 d . . . . .
H13 H 1.020183 0.377009 0.058935 0.054 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 N3 2.0285(11) 2_666 ?
Cu1 N3 2.0285(11) . ?
Cu1 Cl1 2.2729(4) . ?
Cu1 Cl1 2.2729(4) 2_666 ?
O1 C1 1.2089(19) . ?
N1 N2 1.3065(18) . ?
N1 O2 1.376(2) . ?
C1 O2 1.3991(19) . ?
C1 C2 1.4128(19) . ?
C2 N2 1.3512(19) . ?
C2 C3 1.4606(18) . ?
N2 C8 1.4517(19) . ?
C3 N3 1.3503(18) . ?
C3 C4 1.3907(19) . ?
N3 C7 1.3417(18) . ?
C4 C5 1.382(2) . ?
C5 C6 1.378(2) . ?
C6 C7 1.379(2) . ?
C9 C8 1.372(2) . ?
C9 C10 1.390(3) . ?
C8 C13 1.371(2) . ?
C10 C11 1.368(3) . ?
C11 C12 1.376(3) . ?
C12 C13 1.387(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 Cu1 N3 180.0 2_666 . ?
N3 Cu1 Cl1 90.12(4) 2_666 . ?
N3 Cu1 Cl1 89.88(4) . . ?
N3 Cu1 Cl1 89.88(4) 2_666 2_666 ?
N3 Cu1 Cl1 90.12(4) . 2_666 ?
Cl1 Cu1 Cl1 180.0 . 2_666 ?
N2 N1 O2 104.05(12) . . ?
O1 C1 O2 120.78(13) . . ?
O1 C1 C2 135.19(14) . . ?
O2 C1 C2 104.03(13) . . ?
N2 C2 C1 105.50(12) . . ?
N2 C2 C3 125.55(12) . . ?
C1 C2 C3 128.94(13) . . ?
N1 N2 C2 115.08(13) . . ?
N1 N2 C8 116.89(13) . . ?
C2 N2 C8 127.72(12) . . ?
N1 O2 C1 111.18(11) . . ?
N3 C3 C4 121.43(13) . . ?
N3 C3 C2 116.99(12) . . ?
C4 C3 C2 121.57(13) . . ?
C7 N3 C3 118.34(12) . . ?
C7 N3 Cu1 115.48(10) . . ?
C3 N3 Cu1 126.13(9) . . ?
C5 C4 C3 119.18(14) . . ?
C6 C5 C4 119.33(14) . . ?
C5 C6 C7 118.49(14) . . ?
C8 C9 C10 117.33(18) . . ?
C13 C8 C9 123.33(16) . . ?
C13 C8 N2 119.29(14) . . ?
C9 C8 N2 117.37(15) . . ?
N3 C7 C6 123.08(15) . . ?
C11 C10 C9 120.89(19) . . ?
C10 C11 C12 120.30(18) . . ?
C11 C12 C13 120.22(19) . . ?
C8 C13 C12 117.92(16) . . ?

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
O1 C1 C2 N2 175.63(19) . . . . ?
O2 C1 C2 N2 -3.64(16) . . . . ?
O1 C1 C2 C3 -2.7(3) . . . . ?
O2 C1 C2 C3 177.99(14) . . . . ?
O2 N1 N2 C2 0.5(2) . . . . ?
O2 N1 N2 C8 174.69(13) . . . . ?
C1 C2 N2 N1 2.08(19) . . . . ?
C3 C2 N2 N1 -179.47(15) . . . . ?
C1 C2 N2 C8 -171.37(14) . . . . ?
C3 C2 N2 C8 7.1(2) . . . . ?
N2 N1 O2 C1 -3.0(2) . . . . ?
O1 C1 O2 N1 -175.22(16) . . . . ?
C2 C1 O2 N1 4.18(18) . . . . ?
N2 C2 C3 N3 -143.59(14) . . . . ?
C1 C2 C3 N3 34.5(2) . . . . ?
N2 C2 C3 C4 37.7(2) . . . . ?
C1 C2 C3 C4 -144.19(16) . . . . ?
C4 C3 N3 C7 -1.4(2) . . . . ?
C2 C3 N3 C7 179.88(13) . . . . ?
C4 C3 N3 Cu1 -178.67(11) . . . . ?
C2 C3 N3 Cu1 2.65(18) . . . . ?
N3 C3 C4 C5 3.7(2) . . . . ?
C2 C3 C4 C5 -177.71(14) . . . . ?
C3 C4 C5 C6 -2.1(3) . . . . ?
C4 C5 C6 C7 -1.4(3) . . . . ?
C10 C9 C8 C13 1.2(3) . . . . ?
C10 C9 C8 N2 -177.24(19) . . . . ?
N1 N2 C8 C13 79.0(2) . . . . ?
C2 N2 C8 C13 -107.69(19) . . . . ?
N1 N2 C8 C9 -102.48(19) . . . . ?
C2 N2 C8 C9 70.9(2) . . . . ?
C3 N3 C7 C6 -2.4(2) . . . . ?
Cu1 N3 C7 C6 175.15(14) . . . . ?
C5 C6 C7 N3 3.8(3) . . . . ?
C8 C9 C10 C11 -0.3(4) . . . . ?
C9 C10 C11 C12 -0.2(4) . . . . ?
C10 C11 C12 C13 -0.2(4) . . . . ?
C9 C8 C13 C12 -1.6(3) . . . . ?
N2 C8 C13 C12 176.87(17) . . . . ?
C11 C12 C13 C8 1.0(3) . . . . ?

_refine_diff_density_max         0.325
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.060

####################################################################### 
# 
# 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_NIP358
_database_code_depnum_ccdc_archive 'CCDC 1913663'
loop_
_audit_author_name
_audit_author_address
'Pascal Retailleau'
;CNRS
France
;
_audit_update_record             
;
2019-05-02 deposited with the CCDC.	2019-07-11 downloaded from the CCDC.
;

_vrf_PLAT910_NIP358              
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         12 Note  
RESPONSE: Indeed 12 Bragg reflections  as listed below were omitted due 
to a theta(min) limit set too high  (From CIF: Theta(Min) =  3.44). 
The very low-order reflections are essentially hidden by the beamstop 
which has a finite size and a fixed setting and the strategy software does not 
readily allow us to set up additional images with the detector at a larger 
distance from the crystal with the beamstop setting changed accordingly. 
These very few missing reflections do not preclude at all the structure 
solution and refinement meeting the iUCR & Chemistry criteria.  
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C52 H36 Cl2 Co2 N12 O8, Cl4 Co'
_chemical_formula_sum            'C52 H36 Cl6 Co3 N12 O8'
_chemical_formula_weight         1346.42

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 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, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'

_cell_length_a                   17.0950(4)
_cell_length_b                   16.1670(3)
_cell_length_c                   10.0791(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2785.61(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    17674
_cell_measurement_theta_min      3.3910
_cell_measurement_theta_max      27.8100

_exptl_crystal_description       platelet
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_F_000             1358
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    1.236
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.46958
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_ambient_environment      air
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) mm003 X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Rigaku MaxFlux double bounce layer optics'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_detector                 'HPAD Dectris Pilatus3R-200K-A'
_diffrn_reflns_number            60346
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_av_R_equivalents  0.0786
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.444
_diffrn_reflns_theta_max         29.108
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6983
_reflns_number_gt                5417
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.745
_reflns_Friedel_fraction_max     0.902
_reflns_Friedel_fraction_full    0.999

_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0283P)²+0.3243P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2025 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.016(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         6976
_refine_ls_number_parameters     367
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0332
_refine_ls_wR_factor_ref         0.0689
_refine_ls_wR_factor_gt          0.0630
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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
Co1 Co 0.42890(2) 0.57570(2) 0.39175(4) 0.03101(10) Uani 1 1 d . . . . .
N1 N 0.61980(15) 0.7320(2) 0.1278(3) 0.0485(7) Uani 1 1 d . . . . .
C1 C 0.53735(17) 0.68713(19) 0.2854(3) 0.0336(7) Uani 1 1 d . . . . .
O1 O 0.51918(11) 0.66202(12) 0.39659(19) 0.0366(5) Uani 1 1 d . . . . .
Cl1 Cl 0.500000 0.500000 0.56559(9) 0.0391(2) Uani 1 2 d S T P . .
Co2 Co 0.500000 0.000000 0.42091(6) 0.04292(16) Uani 1 2 d S T P . .
N2 N 0.54843(13) 0.72922(15) 0.0821(2) 0.0340(6) Uani 1 1 d . . . . .
C2 C 0.49472(18) 0.70305(17) 0.1693(3) 0.0291(6) Uani 1 1 d . . . . .
O2 O 0.61340(13) 0.70480(16) 0.2570(2) 0.0471(6) Uani 1 1 d . . . . .
Cl2 Cl 0.500000 0.500000 0.21655(9) 0.0368(2) Uani 1 2 d S T P . .
C5 C 0.2504(2) 0.7032(2) 0.1632(4) 0.0476(8) Uani 1 1 d . . . . .
H5 H 0.196047 0.702716 0.167497 0.057 Uiso 1 1 calc R U . . .
C4 C 0.29398(18) 0.6543(2) 0.2468(3) 0.0405(8) Uani 1 1 d . . . . .
H4 H 0.267959 0.620824 0.307506 0.049 Uiso 1 1 calc R U . . .
Cl4 Cl 0.38985(7) -0.01136(7) 0.54655(11) 0.0720(3) Uani 1 1 d . . . . .
C3 C 0.40914(17) 0.70159(17) 0.1566(3) 0.0308(6) Uani 1 1 d . . . . .
N3 N 0.37255(14) 0.65284(15) 0.2447(2) 0.0314(5) Uani 1 1 d . . . . .
Cl3 Cl 0.48879(10) 0.11198(8) 0.28747(13) 0.0989(5) Uani 1 1 d . . . . .
C6 C 0.2879(2) 0.7521(2) 0.0744(4) 0.0491(9) Uani 1 1 d . . . . .
H6 H 0.259429 0.785822 0.017353 0.059 Uiso 1 1 calc R U . . .
O1B O 0.34044(12) 0.48758(13) 0.3840(2) 0.0403(5) Uani 1 1 d . . . . .
N1B N 0.2609(2) 0.38557(18) 0.6472(3) 0.0518(8) Uani 1 1 d . . . . .
C1B C 0.31314(18) 0.47026(19) 0.4939(3) 0.0361(7) Uani 1 1 d . . . . .
O2B O 0.28841(15) 0.39164(14) 0.5196(2) 0.0510(6) Uani 1 1 d . . . . .
N2B N 0.26991(16) 0.46033(17) 0.6953(2) 0.0404(6) Uani 1 1 d . . . . .
C3B C 0.31231(17) 0.60467(18) 0.6285(3) 0.0341(7) Uani 1 1 d . . . . .
N3B N 0.36226(14) 0.63977(14) 0.5404(2) 0.0329(6) Uani 1 1 d . . . . .
C4B C 0.37187(18) 0.72169(19) 0.5455(3) 0.0400(7) Uani 1 1 d . . . . .
H4B H 0.404884 0.746150 0.483513 0.048 Uiso 1 1 calc R U . . .
C5B C 0.33593(19) 0.7718(2) 0.6365(3) 0.0431(8) Uani 1 1 d . . . . .
H5B H 0.345388 0.828395 0.638084 0.052 Uiso 1 1 calc R U . . .
C6B C 0.2860(2) 0.7361(2) 0.7246(4) 0.0512(9) Uani 1 1 d . . . . .
H6B H 0.260770 0.768510 0.787735 0.061 Uiso 1 1 calc R U . . .
C7B C 0.2726(2) 0.6519(2) 0.7205(3) 0.0477(8) Uani 1 1 d . . . . .
H7B H 0.237380 0.627433 0.778871 0.057 Uiso 1 1 calc R U . . .
C8B C 0.2497(2) 0.4689(2) 0.8360(3) 0.0402(7) Uani 1 1 d . . . . .
C9B C 0.3094(2) 0.4769(2) 0.9247(3) 0.0513(9) Uani 1 1 d . . . . .
H9B H 0.360909 0.481267 0.896136 0.062 Uiso 1 1 calc R U . . .
C10B C 0.2913(3) 0.4782(2) 1.0585(4) 0.0641(11) Uani 1 1 d . . . . .
H10B H 0.331011 0.482613 1.121134 0.077 Uiso 1 1 calc R U . . .
C11B C 0.2157(3) 0.4732(2) 1.0984(4) 0.0662(11) Uani 1 1 d . . . . .
H11B H 0.204027 0.474232 1.188512 0.079 Uiso 1 1 calc R U . . .
C12B C 0.1562(3) 0.4666(2) 1.0075(4) 0.0671(12) Uani 1 1 d . . . . .
H12B H 0.104634 0.463624 1.036505 0.081 Uiso 1 1 calc R U . . .
C13B C 0.1726(2) 0.4642(2) 0.8718(4) 0.0533(9) Uani 1 1 d . . . . .
H13B H 0.133102 0.459632 0.808786 0.064 Uiso 1 1 calc R U . . .
C2B C 0.30080(17) 0.51558(18) 0.6102(3) 0.0351(7) Uani 1 1 d . . . . .
C8 C 0.54092(17) 0.75437(19) -0.0558(3) 0.0349(7) Uani 1 1 d . . . . .
C7 C 0.36877(19) 0.7517(2) 0.0690(3) 0.0434(8) Uani 1 1 d . . . . .
H7 H 0.395354 0.784307 0.007873 0.052 Uiso 1 1 calc R U . . .
C9 C 0.5379(2) 0.6944(2) -0.1516(3) 0.0472(8) Uani 1 1 d . . . . .
H9 H 0.535507 0.638725 -0.129098 0.057 Uiso 1 1 calc R U . . .
C10 C 0.5386(2) 0.7193(3) -0.2833(4) 0.0588(10) Uani 1 1 d . . . . .
H10 H 0.537948 0.679899 -0.350567 0.071 Uiso 1 1 calc R U . . .
C11 C 0.5401(2) 0.8018(3) -0.3143(4) 0.0595(11) Uani 1 1 d . . . . .
H11 H 0.540630 0.817975 -0.402834 0.071 Uiso 1 1 calc R U . . .
C13 C 0.54230(19) 0.8373(2) -0.0846(3) 0.0463(8) Uani 1 1 d . . . . .
H13 H 0.544112 0.876630 -0.017327 0.056 Uiso 1 1 calc R U . . .
C12 C 0.5409(2) 0.8607(3) -0.2168(4) 0.0570(10) Uani 1 1 d . . . . .
H12 H 0.540526 0.916516 -0.239273 0.068 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 O1B 2.079(2) . ?
Co1 O1 2.081(2) . ?
Co1 N3B 2.149(2) . ?
Co1 N3 2.164(2) . ?
Co1 Cl1 2.4587(7) . ?
Co1 Cl2 2.4685(7) . ?
N1 N2 1.305(4) . ?
N1 O2 1.379(3) . ?
C1 O1 1.232(3) . ?
C1 O2 1.362(4) . ?
C1 C2 1.403(4) . ?
Co2 Cl3 2.2634(11) . ?
Co2 Cl3 2.2635(11) 2_655 ?
Co2 Cl4 2.2766(11) 2_655 ?
Co2 Cl4 2.2767(11) . ?
N2 C2 1.339(4) . ?
N2 C8 1.454(4) . ?
C2 C3 1.469(4) . ?
C5 C6 1.356(5) . ?
C5 C4 1.375(5) . ?
C5 H5 0.9300 . ?
C4 N3 1.343(4) . ?
C4 H4 0.9300 . ?
C3 N3 1.342(4) . ?
C3 C7 1.382(4) . ?
C6 C7 1.383(5) . ?
C6 H6 0.9300 . ?
O1B C1B 1.234(4) . ?
N1B N2B 1.312(4) . ?
N1B O2B 1.374(4) . ?
C1B O2B 1.364(4) . ?
C1B C2B 1.398(4) . ?
N2B C2B 1.347(4) . ?
N2B C8B 1.465(4) . ?
C3B N3B 1.356(4) . ?
C3B C7B 1.380(4) . ?
C3B C2B 1.465(4) . ?
N3B C4B 1.335(4) . ?
C4B C5B 1.369(5) . ?
C4B H4B 0.9300 . ?
C5B C6B 1.360(5) . ?
C5B H5B 0.9300 . ?
C6B C7B 1.381(5) . ?
C6B H6B 0.9300 . ?
C7B H7B 0.9300 . ?
C8B C9B 1.362(5) . ?
C8B C13B 1.369(5) . ?
C9B C10B 1.383(5) . ?
C9B H9B 0.9300 . ?
C10B C11B 1.355(6) . ?
C10B H10B 0.9300 . ?
C11B C12B 1.373(6) . ?
C11B H11B 0.9300 . ?
C12B C13B 1.397(6) . ?
C12B H12B 0.9300 . ?
C13B H13B 0.9300 . ?
C8 C9 1.369(5) . ?
C8 C13 1.372(4) . ?
C7 H7 0.9300 . ?
C9 C10 1.386(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.371(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.369(6) . ?
C11 H11 0.9300 . ?
C13 C12 1.385(5) . ?
C13 H13 0.9300 . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1B Co1 O1 178.58(8) . . ?
O1B Co1 N3B 88.33(9) . . ?
O1 Co1 N3B 93.07(9) . . ?
O1B Co1 N3 92.60(9) . . ?
O1 Co1 N3 87.69(9) . . ?
N3B Co1 N3 87.94(9) . . ?
O1B Co1 Cl1 92.59(6) . . ?
O1 Co1 Cl1 87.16(6) . . ?
N3B Co1 Cl1 90.29(7) . . ?
N3 Co1 Cl1 174.46(7) . . ?
O1B Co1 Cl2 89.52(6) . . ?
O1 Co1 Cl2 89.09(6) . . ?
N3B Co1 Cl2 177.48(7) . . ?
N3 Co1 Cl2 90.85(7) . . ?
Cl1 Co1 Cl2 91.12(2) . . ?
N2 N1 O2 104.4(2) . . ?
O1 C1 O2 120.1(3) . . ?
O1 C1 C2 133.5(3) . . ?
O2 C1 C2 106.4(3) . . ?
C1 O1 Co1 112.74(18) . . ?
Co1 Cl1 Co1 89.10(3) 2_665 . ?
Cl3 Co2 Cl3 107.09(8) . 2_655 ?
Cl3 Co2 Cl4 109.63(5) . 2_655 ?
Cl3 Co2 Cl4 108.96(5) 2_655 2_655 ?
Cl3 Co2 Cl4 108.97(5) . . ?
Cl3 Co2 Cl4 109.63(5) 2_655 . ?
Cl4 Co2 Cl4 112.41(6) 2_655 . ?
N1 N2 C2 114.9(2) . . ?
N1 N2 C8 114.2(2) . . ?
C2 N2 C8 130.9(2) . . ?
N2 C2 C1 104.4(3) . . ?
N2 C2 C3 129.1(2) . . ?
C1 C2 C3 126.0(3) . . ?
C1 O2 N1 110.0(2) . . ?
Co1 Cl2 Co1 88.65(3) . 2_665 ?
C6 C5 C4 118.9(3) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
N3 C4 C5 122.8(3) . . ?
N3 C4 H4 118.6 . . ?
C5 C4 H4 118.6 . . ?
N3 C3 C7 122.3(3) . . ?
N3 C3 C2 114.6(2) . . ?
C7 C3 C2 122.9(3) . . ?
C3 N3 C4 117.8(3) . . ?
C3 N3 Co1 125.76(19) . . ?
C4 N3 Co1 116.4(2) . . ?
C5 C6 C7 119.7(3) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C1B O1B Co1 113.37(18) . . ?
N2B N1B O2B 103.9(2) . . ?
O1B C1B O2B 119.9(3) . . ?
O1B C1B C2B 133.7(3) . . ?
O2B C1B C2B 106.4(3) . . ?
C1B O2B N1B 110.5(2) . . ?
N1B N2B C2B 114.9(3) . . ?
N1B N2B C8B 114.7(2) . . ?
C2B N2B C8B 130.3(3) . . ?
N3B C3B C7B 121.2(3) . . ?
N3B C3B C2B 114.4(3) . . ?
C7B C3B C2B 124.2(3) . . ?
C4B N3B C3B 117.9(3) . . ?
C4B N3B Co1 116.1(2) . . ?
C3B N3B Co1 126.06(19) . . ?
N3B C4B C5B 123.8(3) . . ?
N3B C4B H4B 118.1 . . ?
C5B C4B H4B 118.1 . . ?
C6B C5B C4B 118.0(3) . . ?
C6B C5B H5B 121.0 . . ?
C4B C5B H5B 121.0 . . ?
C5B C6B C7B 120.2(3) . . ?
C5B C6B H6B 119.9 . . ?
C7B C6B H6B 119.9 . . ?
C3B C7B C6B 119.0(3) . . ?
C3B C7B H7B 120.5 . . ?
C6B C7B H7B 120.5 . . ?
C9B C8B C13B 123.6(3) . . ?
C9B C8B N2B 117.9(3) . . ?
C13B C8B N2B 118.4(3) . . ?
C8B C9B C10B 118.3(4) . . ?
C8B C9B H9B 120.8 . . ?
C10B C9B H9B 120.8 . . ?
C11B C10B C9B 120.1(4) . . ?
C11B C10B H10B 120.0 . . ?
C9B C10B H10B 120.0 . . ?
C10B C11B C12B 120.8(4) . . ?
C10B C11B H11B 119.6 . . ?
C12B C11B H11B 119.6 . . ?
C11B C12B C13B 120.4(4) . . ?
C11B C12B H12B 119.8 . . ?
C13B C12B H12B 119.8 . . ?
C8B C13B C12B 116.7(4) . . ?
C8B C13B H13B 121.6 . . ?
C12B C13B H13B 121.6 . . ?
N2B C2B C1B 104.2(2) . . ?
N2B C2B C3B 128.6(3) . . ?
C1B C2B C3B 126.9(3) . . ?
C9 C8 C13 122.9(3) . . ?
C9 C8 N2 118.7(3) . . ?
C13 C8 N2 118.3(3) . . ?
C3 C7 C6 118.5(3) . . ?
C3 C7 H7 120.8 . . ?
C6 C7 H7 120.8 . . ?
C8 C9 C10 118.1(3) . . ?
C8 C9 H9 121.0 . . ?
C10 C9 H9 121.0 . . ?
C11 C10 C9 120.0(4) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C12 C11 C10 120.9(3) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C8 C13 C12 118.1(3) . . ?
C8 C13 H13 121.0 . . ?
C12 C13 H13 121.0 . . ?
C11 C12 C13 120.0(4) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 O1 Co1 -144.5(2) . . . . ?
C2 C1 O1 Co1 35.0(4) . . . . ?
O2 N1 N2 C2 0.4(4) . . . . ?
O2 N1 N2 C8 -179.0(2) . . . . ?
N1 N2 C2 C1 0.0(3) . . . . ?
C8 N2 C2 C1 179.3(3) . . . . ?
N1 N2 C2 C3 172.1(3) . . . . ?
C8 N2 C2 C3 -8.6(5) . . . . ?
O1 C1 C2 N2 -179.9(3) . . . . ?
O2 C1 C2 N2 -0.4(3) . . . . ?
O1 C1 C2 C3 7.6(6) . . . . ?
O2 C1 C2 C3 -172.9(3) . . . . ?
O1 C1 O2 N1 -179.7(3) . . . . ?
C2 C1 O2 N1 0.6(3) . . . . ?
N2 N1 O2 C1 -0.6(3) . . . . ?
C6 C5 C4 N3 0.1(5) . . . . ?
N2 C2 C3 N3 163.5(3) . . . . ?
C1 C2 C3 N3 -25.9(4) . . . . ?
N2 C2 C3 C7 -21.9(5) . . . . ?
C1 C2 C3 C7 148.7(3) . . . . ?
C7 C3 N3 C4 -0.6(4) . . . . ?
C2 C3 N3 C4 174.0(3) . . . . ?
C7 C3 N3 Co1 -177.4(2) . . . . ?
C2 C3 N3 Co1 -2.8(3) . . . . ?
C5 C4 N3 C3 0.0(5) . . . . ?
C5 C4 N3 Co1 177.1(3) . . . . ?
C4 C5 C6 C7 0.3(5) . . . . ?
Co1 O1B C1B O2B -145.9(2) . . . . ?
Co1 O1B C1B C2B 33.3(5) . . . . ?
O1B C1B O2B N1B 179.5(3) . . . . ?
C2B C1B O2B N1B 0.1(4) . . . . ?
N2B N1B O2B C1B -0.2(4) . . . . ?
O2B N1B N2B C2B 0.3(4) . . . . ?
O2B N1B N2B C8B -175.7(3) . . . . ?
C7B C3B N3B C4B 0.0(4) . . . . ?
C2B C3B N3B C4B 175.8(3) . . . . ?
C7B C3B N3B Co1 179.7(2) . . . . ?
C2B C3B N3B Co1 -4.4(4) . . . . ?
C3B N3B C4B C5B 1.9(5) . . . . ?
Co1 N3B C4B C5B -177.9(3) . . . . ?
N3B C4B C5B C6B -1.8(5) . . . . ?
C4B C5B C6B C7B -0.1(5) . . . . ?
N3B C3B C7B C6B -1.8(5) . . . . ?
C2B C3B C7B C6B -177.2(3) . . . . ?
C5B C6B C7B C3B 1.8(6) . . . . ?
N1B N2B C8B C9B 106.1(4) . . . . ?
C2B N2B C8B C9B -69.2(5) . . . . ?
N1B N2B C8B C13B -70.5(4) . . . . ?
C2B N2B C8B C13B 114.2(4) . . . . ?
C13B C8B C9B C10B 1.6(6) . . . . ?
N2B C8B C9B C10B -174.8(3) . . . . ?
C8B C9B C10B C11B -1.1(6) . . . . ?
C9B C10B C11B C12B 0.1(6) . . . . ?
C10B C11B C12B C13B 0.5(6) . . . . ?
C9B C8B C13B C12B -1.0(6) . . . . ?
N2B C8B C13B C12B 175.4(3) . . . . ?
C11B C12B C13B C8B -0.1(6) . . . . ?
N1B N2B C2B C1B -0.3(4) . . . . ?
C8B N2B C2B C1B 175.0(3) . . . . ?
N1B N2B C2B C3B 174.4(3) . . . . ?
C8B N2B C2B C3B -10.3(5) . . . . ?
O1B C1B C2B N2B -179.2(3) . . . . ?
O2B C1B C2B N2B 0.1(3) . . . . ?
O1B C1B C2B C3B 6.0(6) . . . . ?
O2B C1B C2B C3B -174.7(3) . . . . ?
N3B C3B C2B N2B 163.9(3) . . . . ?
C7B C3B C2B N2B -20.4(5) . . . . ?
N3B C3B C2B C1B -22.5(4) . . . . ?
C7B C3B C2B C1B 153.2(3) . . . . ?
N1 N2 C8 C9 98.0(3) . . . . ?
C2 N2 C8 C9 -81.3(4) . . . . ?
N1 N2 C8 C13 -77.8(4) . . . . ?
C2 N2 C8 C13 102.9(4) . . . . ?
N3 C3 C7 C6 1.0(5) . . . . ?
C2 C3 C7 C6 -173.2(3) . . . . ?
C5 C6 C7 C3 -0.9(5) . . . . ?
C13 C8 C9 C10 1.9(5) . . . . ?
N2 C8 C9 C10 -173.7(3) . . . . ?
C8 C9 C10 C11 -1.7(6) . . . . ?
C9 C10 C11 C12 -0.1(6) . . . . ?
C9 C8 C13 C12 -0.3(5) . . . . ?
N2 C8 C13 C12 175.3(3) . . . . ?
C10 C11 C12 C13 1.8(6) . . . . ?
C8 C13 C12 C11 -1.5(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
_geom_hbond_publ_flag
C4 H4 O1B 0.93 2.60 3.132(4) 116.7 . yes
C4B H4B O1 0.93 2.54 3.086(4) 118.1 . yes
C5B H5B Cl4 0.93 2.85 3.737(4) 159.2 1_565 yes
C13B H13B Cl3 0.93 2.89 3.737(4) 151.7 4_456 yes

_refine_diff_density_max         0.269
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.060

