# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_el1397
_database_code_depnum_ccdc_archive 'CCDC 1831783'
_audit_update_record             
;
2018-03-22 deposited with the CCDC.
2018-05-01 downloaded from the CCDC.
;
_audit_creation_date             2018-03-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H22 Cu F6 N8 O6 S2'
_chemical_formula_sum            'C26 H22 Cu F6 N8 O6 S2'
_chemical_formula_weight         784.17
_chemical_melting_point          ?
_chemical_oxdiff_formula         C50H50N20CuF6S2O8
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'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.3801(5)
_cell_length_b                   13.3284(8)
_cell_length_c                   16.0985(8)
_cell_angle_alpha                107.132(5)
_cell_angle_beta                 103.696(5)
_cell_angle_gamma                100.131(5)
_cell_volume                     1802.08(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3427
_cell_measurement_temperature    173
_cell_measurement_theta_max      71.0810
_cell_measurement_theta_min      5.0250
_shelx_estimated_absorpt_T_max   0.836
_shelx_estimated_absorpt_T_min   0.707
_exptl_absorpt_coefficient_mu    2.659
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53128
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.44a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             794
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_unetI/netI     0.0730
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.936
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9434
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.100
_diffrn_reflns_theta_min         5.012
_diffrn_ambient_temperature      173.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1033
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      7.00 108.00   1.00    1.00    --   36.75  19.00  30.00  101
  2  ω     48.00 122.00   1.00    4.25    --  107.00 -45.00 120.00   74
  3  ω     56.00 142.00   1.00    4.25    --  107.00 -93.00  -6.01   86
  4  ω     64.00 112.00   1.00    4.25    --  107.00 -93.00-102.77   48
  5  ω     55.00 126.00   1.00    4.25    --  107.00 -30.00   0.00   71
  6  ω    102.00 165.00   1.00    4.25    --  107.00  61.00 -60.00   63
  7  ω     42.00 124.00   1.00    4.25    --  107.00 -45.00 -60.00   82
  8  ω     40.00 124.00   1.00    4.25    --  107.00 -45.00-150.00   84
  9  ω     21.00 104.00   1.00    1.00    --   36.75  57.00  90.00   83
 10  ω     38.00 172.00   1.00    4.25    --  107.00   0.00  90.00  134
 11  ω     38.00 118.00   1.00    4.25    --  107.00 -92.00 148.23   80
 12  ω    -28.00  63.00   1.00    1.00    --   36.75 -77.00-120.00   91
 13  ω   -109.00 -77.00   1.00    1.00    --  -36.75 178.00-120.00   32
 14  ω   -108.00 -53.00   1.00    1.00    --  -36.75 178.00  60.00   55
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1590154000
_diffrn_orient_matrix_UB_12      0.0292802000
_diffrn_orient_matrix_UB_13      -0.0111844000
_diffrn_orient_matrix_UB_21      0.0371605000
_diffrn_orient_matrix_UB_22      0.1123935000
_diffrn_orient_matrix_UB_23      0.0749335000
_diffrn_orient_matrix_UB_31      0.0637146000
_diffrn_orient_matrix_UB_32      -0.0473370000
_diffrn_orient_matrix_UB_33      0.0730027000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4909
_reflns_number_total             6550
_reflns_odcompleteness_completeness 98.05
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.44a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.44a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.44a (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.658
_refine_diff_density_min         -0.650
_refine_diff_density_rms         0.089
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     444
_refine_ls_number_reflns         6550
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0890
_refine_ls_R_factor_gt           0.0657
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0950P)²+1.5960P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1742
_refine_ls_wR_factor_ref         0.1921
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C2(H2), C19(H19), C3(H3), C5(H5), C9(H9), C16(H16), C4(H4),
 C18(H18), C17(H17), C11(H11), C10(H10)
2.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C26(H26A,H26B,H26C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.08875(7) 0.72579(5) 0.32608(4) 0.03242(19) Uani 1 1 d . . . . .
S1 S 0.44877(11) 0.75500(9) 0.49552(7) 0.0347(2) Uani 1 1 d . . . . .
S2 S -0.15701(13) 0.81111(9) 0.18278(8) 0.0408(3) Uani 1 1 d . . . . .
O3 O 0.5111(5) 0.6710(3) 0.5151(3) 0.0532(9) Uani 1 1 d . . . . .
O4 O -0.1347(4) 0.7646(3) 0.2530(2) 0.0493(8) Uani 1 1 d . . . . .
O1 O 0.3334(4) 0.7183(3) 0.4090(2) 0.0505(9) Uani 1 1 d . . . . .
N4 N 0.7977(4) 0.5133(3) 0.3844(2) 0.0292(7) Uani 1 1 d . . . . .
N6 N 0.9853(4) 0.6069(3) 0.3610(2) 0.0298(7) Uani 1 1 d . . . . .
O2 O 0.4141(4) 0.8271(3) 0.5691(2) 0.0535(9) Uani 1 1 d . . . . .
N5 N 0.8493(4) 0.6057(3) 0.3713(2) 0.0303(7) Uani 1 1 d . . . . .
N3 N 0.1735(4) 0.5095(3) 0.1214(2) 0.0317(7) Uani 1 1 d . . . . .
N1 N 0.0800(4) 0.6111(3) 0.2111(2) 0.0318(7) Uani 1 1 d . . . . .
F3 F 0.6506(5) 0.7827(3) 0.4116(3) 0.0799(12) Uani 1 1 d . . . . .
N2 N 0.2056(4) 0.6017(3) 0.1913(2) 0.0316(7) Uani 1 1 d . . . . .
O6 O -0.1043(5) 0.9275(3) 0.2122(3) 0.0659(11) Uani 1 1 d . . . . .
N7 N 0.0943(5) 0.8370(3) 0.4425(3) 0.0424(9) Uani 1 1 d . . . . .
O5 O -0.1249(5) 0.7528(4) 0.1032(3) 0.0639(11) Uani 1 1 d . . . . .
N8 N 0.2045(5) 0.8410(3) 0.2933(3) 0.0431(9) Uani 1 1 d . . . . .
F1 F 0.5676(6) 0.9216(3) 0.4560(4) 0.1011(17) Uani 1 1 d . . . . .
C20 C 1.0218(4) 0.5129(3) 0.3667(3) 0.0279(8) Uani 1 1 d . . . . .
F5 F -0.4100(5) 0.8223(4) 0.0791(3) 0.0901(14) Uani 1 1 d . . . . .
C13 C 0.4692(4) 0.4729(3) 0.2384(3) 0.0307(8) Uani 1 1 d . . . . .
H13 H 0.4963 0.5502 0.2595 0.037 Uiso 1 1 calc R . . . .
C6 C 0.0234(4) 0.4543(3) 0.0952(3) 0.0296(8) Uani 1 1 d . . . . .
C1 C -0.0378(4) 0.5219(3) 0.1533(3) 0.0285(8) Uani 1 1 d . . . . .
C15 C 0.9005(4) 0.4516(3) 0.3822(3) 0.0307(8) Uani 1 1 d . . . . .
C12 C 0.5305(4) 0.4197(4) 0.2946(3) 0.0317(8) Uani 1 1 d . . . . .
C8 C 0.3683(4) 0.4140(4) 0.1516(3) 0.0330(9) Uani 1 1 d . . . . .
F2 F 0.7245(5) 0.8806(4) 0.5526(4) 0.1122(19) Uani 1 1 d . . . . .
C14 C 0.6418(5) 0.4853(4) 0.3891(3) 0.0362(9) Uani 1 1 d . . . . .
H14A H 0.6127 0.5528 0.4154 0.043 Uiso 1 1 calc R . . . .
H14B H 0.6374 0.4423 0.4297 0.043 Uiso 1 1 calc R . . . .
C2 C -0.1922(5) 0.4924(4) 0.1462(3) 0.0372(9) Uani 1 1 d . . . . .
H2 H -0.2357 0.5383 0.1843 0.045 Uiso 1 1 calc R . . . .
F6 F -0.4132(5) 0.8307(6) 0.2131(4) 0.121(2) Uani 1 1 d . . . . .
C19 C 1.1519(5) 0.4756(4) 0.3611(3) 0.0367(9) Uani 1 1 d . . . . .
H19 H 1.2347 0.5161 0.3499 0.044 Uiso 1 1 calc R . . . .
F4 F -0.4245(5) 0.6785(4) 0.1109(4) 0.119(2) Uani 1 1 d . . . . .
C7 C 0.2972(5) 0.4710(4) 0.0916(3) 0.0368(9) Uani 1 1 d . . . . .
H7A H 0.3754 0.5336 0.0946 0.044 Uiso 1 1 calc R . . . .
H7B H 0.2564 0.4202 0.0274 0.044 Uiso 1 1 calc R . . . .
C3 C -0.2774(5) 0.3938(4) 0.0812(3) 0.0452(11) Uani 1 1 d . . . . .
H3 H -0.3818 0.3694 0.0757 0.054 Uiso 1 1 calc R . . . .
C5 C -0.0643(5) 0.3546(4) 0.0270(3) 0.0378(9) Uani 1 1 d . . . . .
H5 H -0.0223 0.3094 -0.0126 0.045 Uiso 1 1 calc R . . . .
C9 C 0.3317(5) 0.3008(4) 0.1200(3) 0.0420(10) Uani 1 1 d . . . . .
H9 H 0.2649 0.2600 0.0601 0.050 Uiso 1 1 calc R . . . .
C16 C 0.9012(5) 0.3517(4) 0.3946(3) 0.0377(9) Uani 1 1 d . . . . .
H16 H 0.8186 0.3105 0.4054 0.045 Uiso 1 1 calc R . . . .
C4 C -0.2131(5) 0.3274(4) 0.0219(3) 0.0438(11) Uani 1 1 d . . . . .
H4 H -0.2774 0.2610 -0.0234 0.053 Uiso 1 1 calc R . . . .
C18 C 1.1526(5) 0.3778(4) 0.3726(3) 0.0431(10) Uani 1 1 d . . . . .
H18 H 1.2379 0.3495 0.3688 0.052 Uiso 1 1 calc R . . . .
C17 C 1.0306(6) 0.3180(4) 0.3900(4) 0.0463(11) Uani 1 1 d . . . . .
H17 H 1.0379 0.2515 0.3988 0.056 Uiso 1 1 calc R . . . .
C25 C 0.2585(6) 0.9065(4) 0.2712(3) 0.0503(12) Uani 1 1 d . . . . .
C23 C 0.1176(6) 0.8963(4) 0.5131(3) 0.0458(11) Uani 1 1 d . . . . .
C11 C 0.4918(6) 0.3068(4) 0.2633(3) 0.0440(11) Uani 1 1 d . . . . .
H11 H 0.5329 0.2701 0.3017 0.053 Uiso 1 1 calc R . . . .
C10 C 0.3934(6) 0.2476(4) 0.1764(4) 0.0508(12) Uani 1 1 d . . . . .
H10 H 0.3678 0.1703 0.1552 0.061 Uiso 1 1 calc R . . . .
C21 C 0.6045(6) 0.8389(4) 0.4777(5) 0.0566(14) Uani 1 1 d . . . . .
C24 C 0.1489(9) 0.9703(5) 0.6055(4) 0.0700(18) Uani 1 1 d . . . . .
H24A H 0.1836 1.0454 0.6083 0.105 Uiso 1 1 calc GR . . . .
H24B H 0.2283 0.9537 0.6471 0.105 Uiso 1 1 calc GR . . . .
H24C H 0.0560 0.9618 0.6235 0.105 Uiso 1 1 calc GR . . . .
C26 C 0.3230(11) 0.9904(6) 0.2421(5) 0.090(3) Uani 1 1 d . . . . .
H26A H 0.3531 0.9579 0.1881 0.134 Uiso 1 1 calc GR . . . .
H26B H 0.4125 1.0410 0.2914 0.134 Uiso 1 1 calc GR . . . .
H26C H 0.2475 1.0297 0.2269 0.134 Uiso 1 1 calc GR . . . .
C22 C -0.3615(6) 0.7843(6) 0.1452(5) 0.0651(16) 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 O4 2.370(4) . ?
Cu1 O1 2.402(4) . ?
Cu1 N6 2.003(3) 1_455 ?
Cu1 N1 1.996(4) . ?
Cu1 N7 2.001(4) . ?
Cu1 N8 1.994(4) . ?
S1 O3 1.430(4) . ?
S1 O1 1.432(3) . ?
S1 O2 1.433(4) . ?
S1 C21 1.811(5) . ?
S2 O4 1.432(4) . ?
S2 O6 1.436(4) . ?
S2 O5 1.420(4) . ?
S2 C22 1.804(6) . ?
N4 N5 1.337(5) . ?
N4 C15 1.373(5) . ?
N4 C14 1.470(5) . ?
N6 Cu1 2.003(3) 1_655 ?
N6 N5 1.323(5) . ?
N6 C20 1.378(5) . ?
N3 N2 1.327(5) . ?
N3 C6 1.368(5) . ?
N3 C7 1.474(5) . ?
N1 N2 1.309(5) . ?
N1 C1 1.378(5) . ?
F3 C21 1.320(7) . ?
N7 C23 1.121(6) . ?
N8 C25 1.121(7) . ?
F1 C21 1.327(7) . ?
C20 C15 1.397(5) . ?
C20 C19 1.408(6) . ?
F5 C22 1.328(8) . ?
C13 H13 0.9500 . ?
C13 C12 1.388(6) . ?
C13 C8 1.390(6) . ?
C6 C1 1.398(6) . ?
C6 C5 1.406(6) . ?
C1 C2 1.400(6) . ?
C15 C16 1.404(6) . ?
C12 C14 1.521(6) . ?
C12 C11 1.387(7) . ?
C8 C7 1.503(6) . ?
C8 C9 1.391(6) . ?
F2 C21 1.331(8) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C2 H2 0.9500 . ?
C2 C3 1.374(7) . ?
F6 C22 1.331(8) . ?
C19 H19 0.9500 . ?
C19 C18 1.370(7) . ?
F4 C22 1.319(9) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C3 H3 0.9500 . ?
C3 C4 1.421(7) . ?
C5 H5 0.9500 . ?
C5 C4 1.355(7) . ?
C9 H9 0.9500 . ?
C9 C10 1.393(7) . ?
C16 H16 0.9500 . ?
C16 C17 1.376(7) . ?
C4 H4 0.9500 . ?
C18 H18 0.9500 . ?
C18 C17 1.409(7) . ?
C17 H17 0.9500 . ?
C25 C26 1.428(8) . ?
C23 C24 1.448(7) . ?
C11 H11 0.9500 . ?
C11 C10 1.383(7) . ?
C10 H10 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 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
O4 Cu1 O1 170.53(13) . . ?
N6 Cu1 O4 96.90(13) 1_455 . ?
N6 Cu1 O1 90.65(14) 1_455 . ?
N1 Cu1 O4 92.26(13) . . ?
N1 Cu1 O1 93.73(13) . . ?
N1 Cu1 N6 87.80(14) . 1_455 ?
N1 Cu1 N7 178.17(16) . . ?
N7 Cu1 O4 87.98(16) . . ?
N7 Cu1 O1 86.26(15) . . ?
N7 Cu1 N6 90.37(15) . 1_455 ?
N8 Cu1 O4 86.84(16) . . ?
N8 Cu1 O1 85.72(16) . . ?
N8 Cu1 N6 176.16(16) . 1_455 ?
N8 Cu1 N1 91.17(15) . . ?
N8 Cu1 N7 90.66(17) . . ?
O3 S1 O1 113.8(2) . . ?
O3 S1 O2 115.9(2) . . ?
O3 S1 C21 103.0(3) . . ?
O1 S1 O2 114.5(2) . . ?
O1 S1 C21 102.5(3) . . ?
O2 S1 C21 104.8(3) . . ?
O4 S2 O6 116.3(3) . . ?
O4 S2 C22 101.3(3) . . ?
O6 S2 C22 103.9(3) . . ?
O5 S2 O4 114.2(3) . . ?
O5 S2 O6 115.2(3) . . ?
O5 S2 C22 103.1(3) . . ?
S2 O4 Cu1 128.3(2) . . ?
S1 O1 Cu1 146.4(2) . . ?
N5 N4 C15 111.2(3) . . ?
N5 N4 C14 119.5(3) . . ?
C15 N4 C14 128.9(4) . . ?
N5 N6 Cu1 119.0(3) . 1_655 ?
N5 N6 C20 109.4(3) . . ?
C20 N6 Cu1 131.0(3) . 1_655 ?
N6 N5 N4 107.7(3) . . ?
N2 N3 C6 111.2(3) . . ?
N2 N3 C7 120.0(3) . . ?
C6 N3 C7 128.0(4) . . ?
N2 N1 Cu1 119.8(3) . . ?
N2 N1 C1 109.5(3) . . ?
C1 N1 Cu1 129.5(3) . . ?
N1 N2 N3 108.1(3) . . ?
C23 N7 Cu1 169.5(5) . . ?
C25 N8 Cu1 174.4(5) . . ?
N6 C20 C15 107.3(4) . . ?
N6 C20 C19 131.7(4) . . ?
C15 C20 C19 121.0(4) . . ?
C12 C13 H13 119.7 . . ?
C12 C13 C8 120.5(4) . . ?
C8 C13 H13 119.7 . . ?
N3 C6 C1 104.2(3) . . ?
N3 C6 C5 133.1(4) . . ?
C1 C6 C5 122.8(4) . . ?
N1 C1 C6 106.9(3) . . ?
N1 C1 C2 132.2(4) . . ?
C6 C1 C2 120.9(4) . . ?
N4 C15 C20 104.4(4) . . ?
N4 C15 C16 132.8(4) . . ?
C20 C15 C16 122.8(4) . . ?
C13 C12 C14 119.9(4) . . ?
C11 C12 C13 119.7(4) . . ?
C11 C12 C14 120.4(4) . . ?
C13 C8 C7 120.9(4) . . ?
C13 C8 C9 119.6(4) . . ?
C9 C8 C7 119.5(4) . . ?
N4 C14 C12 110.6(3) . . ?
N4 C14 H14A 109.5 . . ?
N4 C14 H14B 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
C1 C2 H2 121.8 . . ?
C3 C2 C1 116.5(4) . . ?
C3 C2 H2 121.8 . . ?
C20 C19 H19 121.8 . . ?
C18 C19 C20 116.4(4) . . ?
C18 C19 H19 121.8 . . ?
N3 C7 C8 110.2(3) . . ?
N3 C7 H7A 109.6 . . ?
N3 C7 H7B 109.6 . . ?
C8 C7 H7A 109.6 . . ?
C8 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
C2 C3 H3 119.2 . . ?
C2 C3 C4 121.5(4) . . ?
C4 C3 H3 119.2 . . ?
C6 C5 H5 122.3 . . ?
C4 C5 C6 115.3(4) . . ?
C4 C5 H5 122.3 . . ?
C8 C9 H9 120.1 . . ?
C8 C9 C10 119.7(4) . . ?
C10 C9 H9 120.1 . . ?
C15 C16 H16 122.5 . . ?
C17 C16 C15 115.0(4) . . ?
C17 C16 H16 122.5 . . ?
C3 C4 H4 118.5 . . ?
C5 C4 C3 123.0(4) . . ?
C5 C4 H4 118.5 . . ?
C19 C18 H18 119.0 . . ?
C19 C18 C17 122.0(4) . . ?
C17 C18 H18 119.0 . . ?
C16 C17 C18 122.9(5) . . ?
C16 C17 H17 118.5 . . ?
C18 C17 H17 118.5 . . ?
N8 C25 C26 178.3(8) . . ?
N7 C23 C24 178.1(6) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 C12 120.2(5) . . ?
C10 C11 H11 119.9 . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.3(5) . . ?
C11 C10 H10 119.9 . . ?
F3 C21 S1 111.9(4) . . ?
F3 C21 F1 107.2(5) . . ?
F3 C21 F2 106.7(5) . . ?
F1 C21 S1 112.4(4) . . ?
F1 C21 F2 107.2(5) . . ?
F2 C21 S1 111.1(5) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
F5 C22 S2 112.3(5) . . ?
F5 C22 F6 106.8(6) . . ?
F6 C22 S2 111.5(5) . . ?
F4 C22 S2 110.0(5) . . ?
F4 C22 F5 106.1(6) . . ?
F4 C22 F6 110.0(6) . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.023 0.000 0.000 299.6 54.7 C2H3N

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.475
_oxdiff_exptl_absorpt_empirical_full_min 0.397
####################################################################### 
# 
# 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_2017ncs0284za
_database_code_depnum_ccdc_archive 'CCDC 1831786'
_audit_update_record             
;
2018-03-22 deposited with the CCDC.
2018-05-01 downloaded from the CCDC.
;
_audit_creation_date             2017-09-06
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'C28 H28 Cu N8, 2(C3 H6 O), 2(C F3 O3 S), 1.33(H2 O)'
_chemical_formula_sum            'C36 H42.67 Cu F6 N8 O9.33 S2'
_chemical_formula_weight         978.43
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Cu2 (C14 H12 N4)2 (C F3 S O3)2'
_chemical_oxdiff_usercomment     EL1464
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'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   20.8910(7)
_cell_length_b                   9.2748(2)
_cell_length_c                   25.1344(9)
_cell_angle_alpha                90
_cell_angle_beta                 114.487(4)
_cell_angle_gamma                90
_cell_volume                     4432.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11676
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.9860
_cell_measurement_theta_min      3.8860
_shelx_estimated_absorpt_T_max   0.933
_shelx_estimated_absorpt_T_min   0.800
_exptl_absorpt_coefficient_mu    2.336
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87179
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             2017
_exptl_crystal_recrystallization_method 
'The material was recrystallised from a mixture of acetone and water'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0843
_diffrn_reflns_av_unetI/netI     0.0564
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            41244
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.240
_diffrn_reflns_theta_min         3.586
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'hybrid pixel detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_dtime           0.000
_diffrn_detector_type            'Rigaku, HyPix 6000'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -19.00   6.00   0.50    5.00    --    5.00  53.00 -93.00   50
  2  ω    -83.00 -58.00   0.50    5.00    --    0.00  14.00 150.00   50
  3  ω     39.00  88.00   0.50    5.00    --    0.00  14.00 150.00   98
  4  ω     -4.00  85.00   0.50    5.00    --    0.00  43.00   0.00  178
  5  ω    -89.00 -31.00   0.50    5.00    --    0.00  43.00   0.00  116
  6  ω    -89.00  10.00   0.50    5.00    --    0.00  53.00 -93.00  198
  7  ω    -39.00 -14.00   0.50   20.00    --  -90.00  14.00   0.00   50
  8  ω   -124.00 -47.00   0.50   20.00    --  -90.00  14.00   0.00  154
  9  ω   -168.00-142.00   0.50   20.00    --  -90.00  14.00   0.00   52
 10  ω   -173.00  -2.00   0.50   20.00    --  -90.00  29.00 -90.00  342
 11  ω   -164.00-107.00   0.50   20.00    --  -90.00  43.00-120.00  114
 12  ω    -83.00  -5.00   0.50   20.00    --  -90.00  43.00-120.00  156
 13  ω   -130.00 -92.00   0.50   20.00    --  -90.00  43.00 -30.00   76
 14  ω    -71.00 -41.00   0.50   20.00    --  -90.00  43.00 -30.00   60
 15  ω    -27.00  -2.00   0.50   20.00    --  -90.00  43.00 -30.00   50
 16  ω    -90.00 -42.00   0.50   20.00    --  -90.00  53.00 -93.00   96
 17  ω    -40.00 -12.00   0.50   20.00    --  -90.00  60.00-180.00   56
 18  ω    -26.00  -1.00   0.50   20.00    --  -90.00  60.00 -90.00   50
 19  ω   -153.00-115.00   0.50   20.00    --  -90.00  60.00 -90.00   76
 20  ω   -147.00 -75.00   0.50   20.00    --  -90.00  60.00  30.00  144
 21  ω   -179.00 -46.00   0.50   20.00    --  -90.00  60.00-180.00  266
 22  ω   -179.00 -76.00   0.50   20.00    --  -90.00  60.00 -30.00  206
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_details 'Rigaku, AFC11 quarter χ goniometer'
_diffrn_measurement_device_type  
'Rigaku 007HF equipped with Varimax confocal mirrors and an AFC11 goniometer and HyPix 6000 detector'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroLoop'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0272858000
_diffrn_orient_matrix_UB_12      -0.1311662000
_diffrn_orient_matrix_UB_13      0.0220005000
_diffrn_orient_matrix_UB_21      -0.0720012000
_diffrn_orient_matrix_UB_22      0.0143706000
_diffrn_orient_matrix_UB_23      -0.0523824000
_diffrn_orient_matrix_UB_31      0.0251589000
_diffrn_orient_matrix_UB_32      -0.1009300000
_diffrn_orient_matrix_UB_33      -0.0361852000
_diffrn_radiation_collimation    'Varimax focusing mirrors'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating anode'
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_target            Cu
_diffrn_source_type              'Rigaku 007 HF'
_diffrn_source_voltage           40.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6316
_reflns_number_total             8098
_reflns_odcompleteness_completeness 99.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.478
_refine_diff_density_min         -1.017
_refine_diff_density_rms         0.115
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     616
_refine_ls_number_reflns         8098
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0606
_refine_ls_restrained_S_all      1.007
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1259P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1638
_refine_ls_wR_factor_ref         0.1744
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Others
 Fixed Sof: O61B(0.33333) C61B(0.33333) C62B(0.33333) H62A(0.33333)
 H62B(0.33333) H62C(0.33333) C63B(0.33333) H63A(0.33333) H63B(0.33333)
 H63C(0.33333) O61A(0.66667) C61A(0.66667) C62A(0.66667) H62D(0.66667)
 H62E(0.66667) H62F(0.66667) C63A(0.66667) H63D(0.66667) H63E(0.66667)
 H63F(0.66667) O62B(0.33333) H62G(0.33333) H62H(0.33333)
3.a Free rotating group:
 O62B(H62G,H62H), O101(H10A,H10B)
3.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C11(H11A,H11B), C18(H18A,H18B), C25(H25A,H25B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C6(H6), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13),
 C14(H14), C15(H15), C16(H16), C17(H17), C20(H20), C21(H21), C22(H22), C23(H23),
  C26(H26), C27(H27), C28(H28)
3.d Idealised Me refined as rotating group:
 C62B(H62A,H62B,H62C), C63B(H63A,H63B,H63C), C62A(H62D,H62E,H62F), C63A(H63D,
 H63E,H63F), C52(H52A,H52B,H52C), C53(H53A,H53B,H53C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.59777(2) 0.46459(5) 0.36627(2) 0.02656(16) Uani 1 1 d . . . . .
N1 N 0.63123(14) 0.5314(3) 0.30656(12) 0.0274(6) Uani 1 1 d . . . . .
N2 N 0.68251(14) 0.6633(3) 0.26288(12) 0.0292(6) Uani 1 1 d . . . . .
N3 N 0.58296(14) 1.0652(3) 0.28938(12) 0.0274(6) Uani 1 1 d . . . . .
N4 N 0.57216(14) 1.2737(3) 0.32613(11) 0.0282(6) Uani 1 1 d . . . . .
N5 N 0.62161(14) 0.6542(3) 0.40725(11) 0.0272(6) Uani 1 1 d . . . . .
N6 N 0.66792(13) 0.8132(3) 0.47749(11) 0.0262(6) Uani 1 1 d . . . . .
N7 N 0.51403(14) 0.6837(3) 0.54096(12) 0.0311(6) Uani 1 1 d . . . . .
N8 N 0.44050(14) 0.6050(3) 0.57674(12) 0.0307(6) Uani 1 1 d . . . . .
C1 C 0.67817(17) 0.6342(3) 0.31377(14) 0.0274(7) Uani 1 1 d . . . . .
H1 H 0.705046 0.680840 0.349843 0.033 Uiso 1 1 calc R . . . .
C2 C 0.60545(19) 0.4935(4) 0.24838(15) 0.0337(8) Uani 1 1 d . . . . .
H2 H 0.570811 0.421619 0.230195 0.040 Uiso 1 1 calc R . . . .
C3 C 0.63669(19) 0.5735(4) 0.22113(15) 0.0346(8) Uani 1 1 d . . . . .
H3 H 0.628595 0.568561 0.181084 0.042 Uiso 1 1 calc R . . . .
C4 C 0.72542(18) 0.7786(4) 0.25323(16) 0.0337(8) Uani 1 1 d . . . . .
H4A H 0.758209 0.735028 0.238499 0.040 Uiso 1 1 calc R . . . .
H4B H 0.753894 0.825830 0.291040 0.040 Uiso 1 1 calc R . . . .
C5 C 0.68146(18) 0.8908(4) 0.21041(15) 0.0311(7) Uani 1 1 d . . . . .
C6 C 0.6918(2) 0.9158(4) 0.15956(17) 0.0394(8) Uani 1 1 d . . . . .
H6 H 0.724507 0.858015 0.151872 0.047 Uiso 1 1 calc R . . . .
C7 C 0.6557(2) 1.0216(4) 0.12065(17) 0.0430(9) Uani 1 1 d . . . . .
H7 H 0.663725 1.036360 0.086495 0.052 Uiso 1 1 calc R . . . .
C8 C 0.6074(2) 1.1076(4) 0.13093(16) 0.0409(9) Uani 1 1 d . . . . .
H8 H 0.583258 1.182715 0.104542 0.049 Uiso 1 1 calc R . . . .
C9 C 0.59501(19) 1.0819(4) 0.18057(16) 0.0364(8) Uani 1 1 d . . . . .
H9 H 0.561211 1.138781 0.187219 0.044 Uiso 1 1 calc R . . . .
C10 C 0.63101(18) 0.9752(4) 0.22036(15) 0.0300(7) Uani 1 1 d . . . . .
C11 C 0.61594(18) 0.9443(3) 0.27321(14) 0.0283(7) Uani 1 1 d . . . . .
H11A H 0.584664 0.859172 0.264901 0.034 Uiso 1 1 calc R . . . .
H11B H 0.660609 0.919969 0.306755 0.034 Uiso 1 1 calc R . . . .
C12 C 0.51222(17) 1.0834(4) 0.27510(15) 0.0325(7) Uani 1 1 d . . . . .
H12 H 0.475204 1.018867 0.253549 0.039 Uiso 1 1 calc R . . . .
C13 C 0.50631(17) 1.2127(4) 0.29819(14) 0.0295(7) Uani 1 1 d . . . . .
H13 H 0.463562 1.254535 0.295499 0.035 Uiso 1 1 calc R . . . .
C14 C 0.61677(17) 1.1812(3) 0.31966(14) 0.0282(7) Uani 1 1 d . . . . .
H14 H 0.666176 1.195316 0.334540 0.034 Uiso 1 1 calc R . . . .
C15 C 0.66865(16) 0.6762(4) 0.46099(14) 0.0269(7) Uani 1 1 d . . . . .
H15 H 0.699249 0.603999 0.485045 0.032 Uiso 1 1 calc R . . . .
C16 C 0.58914(16) 0.7866(3) 0.38785(13) 0.0263(6) Uani 1 1 d . . . . .
H16 H 0.552880 0.805206 0.350269 0.032 Uiso 1 1 calc R . . . .
C17 C 0.61775(16) 0.8853(4) 0.43146(14) 0.0278(7) Uani 1 1 d . . . . .
H17 H 0.605413 0.984169 0.430247 0.033 Uiso 1 1 calc R . . . .
C18 C 0.71029(17) 0.8697(4) 0.53607(14) 0.0306(7) Uani 1 1 d . . . . .
H18A H 0.742938 0.943509 0.533150 0.037 Uiso 1 1 calc R . . . .
H18B H 0.739064 0.790328 0.560776 0.037 Uiso 1 1 calc R . . . .
C19 C 0.66759(17) 0.9362(4) 0.56599(14) 0.0296(7) Uani 1 1 d . . . . .
C20 C 0.69245(18) 1.0649(4) 0.59609(14) 0.0332(7) Uani 1 1 d . . . . .
H20 H 0.732000 1.110500 0.593905 0.040 Uiso 1 1 calc R . . . .
C21 C 0.66086(19) 1.1280(4) 0.62921(15) 0.0370(8) Uani 1 1 d . . . . .
H21 H 0.679240 1.214830 0.650028 0.044 Uiso 1 1 calc R . . . .
C22 C 0.60229(19) 1.0635(4) 0.63166(15) 0.0368(8) Uani 1 1 d . . . . .
H22 H 0.580381 1.105527 0.654339 0.044 Uiso 1 1 calc R . . . .
C23 C 0.57584(18) 0.9370(4) 0.60074(15) 0.0344(8) Uani 1 1 d . . . . .
H23 H 0.534927 0.894866 0.601785 0.041 Uiso 1 1 calc R . . . .
C24 C 0.60765(17) 0.8700(4) 0.56820(14) 0.0302(7) Uani 1 1 d . . . . .
C25 C 0.58028(17) 0.7270(4) 0.53777(15) 0.0342(8) Uani 1 1 d . . . . .
H25A H 0.572424 0.735047 0.496235 0.041 Uiso 1 1 calc R . . . .
H25B H 0.616189 0.651465 0.556135 0.041 Uiso 1 1 calc R . . . .
C26 C 0.44934(18) 0.7355(5) 0.50502(16) 0.0413(9) Uani 1 1 d . . . . .
H26 H 0.438220 0.794597 0.471497 0.050 Uiso 1 1 calc R . . . .
C27 C 0.40374(19) 0.6850(4) 0.52702(15) 0.0401(9) Uani 1 1 d . . . . .
H27 H 0.354498 0.702291 0.510663 0.048 Uiso 1 1 calc R . . . .
C28 C 0.50712(18) 0.6062(4) 0.58373(15) 0.0314(7) Uani 1 1 d . . . . .
H28 H 0.544676 0.559149 0.614549 0.038 Uiso 1 1 calc R . . . .
O61B O 0.9152(8) 0.5345(16) 0.6189(6) 0.065(4) Uani 0.3333 1 d . . P A 2
C61B C 0.9427(10) 0.613(3) 0.5914(9) 0.052(5) Uani 0.3333 1 d . . P A 2
C62B C 0.9291(9) 0.589(2) 0.5306(6) 0.073(4) Uani 0.3333 1 d . . P A 2
H62A H 0.911588 0.490441 0.519396 0.109 Uiso 0.3333 1 calc GR . P A 2
H62B H 0.972736 0.601879 0.525507 0.109 Uiso 0.3333 1 calc GR . P A 2
H62C H 0.893771 0.657916 0.505966 0.109 Uiso 0.3333 1 calc GR . P A 2
C63B C 0.9917(6) 0.7250(14) 0.6233(5) 0.049(3) Uani 0.3333 1 d . . P A 2
H63A H 0.997988 0.724499 0.664156 0.074 Uiso 0.3333 1 calc GR . P A 2
H63B H 0.973325 0.818830 0.605717 0.074 Uiso 0.3333 1 calc GR . P A 2
H63C H 1.037120 0.707474 0.621616 0.074 Uiso 0.3333 1 calc GR . P A 2
O61A O 0.8242(3) 0.5317(6) 0.5162(2) 0.0637(13) Uani 0.6667 1 d . . P B 1
C61A C 0.8701(4) 0.5016(9) 0.5628(3) 0.064(2) Uani 0.6667 1 d . . P B 1
C62A C 0.9153(8) 0.6094(19) 0.6027(6) 0.083(5) Uani 0.6667 1 d . . P B 1
H62D H 0.906899 0.703228 0.583010 0.124 Uiso 0.6667 1 calc GR . P B 1
H62E H 0.964648 0.581859 0.614740 0.124 Uiso 0.6667 1 calc GR . P B 1
H62F H 0.904922 0.615941 0.637231 0.124 Uiso 0.6667 1 calc GR . P B 1
C63A C 0.8844(6) 0.3477(10) 0.5840(4) 0.095(3) Uani 0.6667 1 d . . P B 1
H63D H 0.842433 0.288996 0.563010 0.142 Uiso 0.6667 1 calc GR . P B 1
H63E H 0.896158 0.344569 0.626039 0.142 Uiso 0.6667 1 calc GR . P B 1
H63F H 0.923855 0.309761 0.576843 0.142 Uiso 0.6667 1 calc GR . P B 1
O51 O 0.7275(2) 0.5402(4) 0.61487(17) 0.0935(14) Uani 1 1 d . . . . .
C51 C 0.7502(2) 0.5473(5) 0.6680(2) 0.0537(11) Uani 1 1 d . . . . .
C52 C 0.7220(2) 0.6537(5) 0.6973(2) 0.0601(12) Uani 1 1 d . . . . .
H52A H 0.687648 0.716293 0.667812 0.090 Uiso 1 1 calc GR . . . .
H52B H 0.760641 0.712400 0.724636 0.090 Uiso 1 1 calc GR . . . .
H52C H 0.699065 0.602360 0.718775 0.090 Uiso 1 1 calc GR . . . .
C53 C 0.8073(3) 0.4524(6) 0.7063(2) 0.0711(14) Uani 1 1 d . . . . .
H53A H 0.816282 0.377630 0.682659 0.107 Uiso 1 1 calc GR . . . .
H53B H 0.793582 0.407019 0.735184 0.107 Uiso 1 1 calc GR . . . .
H53C H 0.850127 0.509450 0.726451 0.107 Uiso 1 1 calc GR . . . .
S201 S 0.79146(5) -0.00119(10) 0.42149(4) 0.0352(2) Uani 1 1 d . . . . .
F201 F 0.90008(14) 0.1688(3) 0.46426(14) 0.0730(8) Uani 1 1 d . . . . .
F202 F 0.90658(16) -0.0153(4) 0.51740(13) 0.0842(10) Uani 1 1 d . . . . .
F203 F 0.92247(13) -0.0390(3) 0.43856(14) 0.0735(8) Uani 1 1 d . . . . .
O201 O 0.75985(15) 0.0812(3) 0.45325(12) 0.0469(7) Uani 1 1 d . . . . .
O202 O 0.78372(15) -0.1542(3) 0.42351(13) 0.0499(7) Uani 1 1 d . . . . .
O203 O 0.77787(14) 0.0555(3) 0.36446(12) 0.0502(7) Uani 1 1 d . . . . .
C201 C 0.8852(2) 0.0296(5) 0.4631(2) 0.0500(10) Uani 1 1 d . . . . .
S211 S 0.42193(4) 0.63200(9) 0.26559(4) 0.0331(2) Uani 1 1 d . . . . .
F211 F 0.35966(13) 0.4139(3) 0.19761(10) 0.0557(6) Uani 1 1 d . . . . .
F212 F 0.33615(14) 0.6206(3) 0.15505(11) 0.0669(8) Uani 1 1 d . . . . .
F213 F 0.43601(15) 0.5215(4) 0.17539(12) 0.0751(9) Uani 1 1 d . . . . .
O211 O 0.47616(13) 0.5363(3) 0.30172(10) 0.0376(6) Uani 1 1 d . . . . .
O212 O 0.36253(14) 0.6388(3) 0.28036(14) 0.0584(8) Uani 1 1 d . . . . .
O213 O 0.44607(17) 0.7680(3) 0.25432(13) 0.0583(8) Uani 1 1 d . . . . .
C211 C 0.3871(2) 0.5420(4) 0.19497(17) 0.0428(9) Uani 1 1 d . . . . .
O62B O 0.7783(4) 0.4227(13) 0.5500(4) 0.058(2) Uani 0.3333 1 d . . P C 2
H62G H 0.806347 0.489083 0.550075 0.087 Uiso 0.3333 1 d G . P C 2
H62H H 0.803586 0.365501 0.576979 0.087 Uiso 0.3333 1 d G . P C 2
O101 O 0.71739(13) 0.3708(3) 0.43061(11) 0.0385(6) Uani 1 1 d . . . . .
H10A H 0.748990 0.412082 0.459919 0.058 Uiso 1 1 d G . . . .
H10B H 0.731390 0.284135 0.432577 0.058 Uiso 1 1 d G . . . .


_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 N1 1.999(3) . ?
Cu1 N4 1.998(3) 1_545 ?
Cu1 N5 1.994(3) . ?
Cu1 N8 2.014(3) 3_666 ?
N1 C1 1.325(4) . ?
N1 C2 1.378(4) . ?
N2 C1 1.347(4) . ?
N2 C3 1.371(4) . ?
N2 C4 1.479(4) . ?
N3 C11 1.460(4) . ?
N3 C12 1.379(4) . ?
N3 C14 1.338(4) . ?
N4 C13 1.380(4) . ?
N4 C14 1.326(4) . ?
N5 C15 1.316(4) . ?
N5 C16 1.390(4) . ?
N6 C15 1.338(4) . ?
N6 C17 1.371(4) . ?
N6 C18 1.465(4) . ?
N7 C25 1.475(4) . ?
N7 C26 1.364(4) . ?
N7 C28 1.350(4) . ?
N8 C27 1.381(5) . ?
N8 C28 1.329(4) . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?
C2 C3 1.348(5) . ?
C3 H3 0.9500 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.505(5) . ?
C5 C6 1.401(5) . ?
C5 C10 1.416(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.370(6) . ?
C7 H7 0.9500 . ?
C7 C8 1.392(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.396(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.387(5) . ?
C10 C11 1.514(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12 0.9500 . ?
C12 C13 1.360(5) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C16 C17 1.361(5) . ?
C17 H17 0.9500 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.516(4) . ?
C19 C20 1.393(5) . ?
C19 C24 1.417(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.388(5) . ?
C21 H21 0.9500 . ?
C21 C22 1.386(5) . ?
C22 H22 0.9500 . ?
C22 C23 1.389(5) . ?
C23 H23 0.9500 . ?
C23 C24 1.395(4) . ?
C24 C25 1.519(5) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 H26 0.9500 . ?
C26 C27 1.367(5) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
O61B C61B 1.29(3) . ?
C61B C62B 1.45(2) . ?
C61B C63B 1.45(3) . ?
C62B H62A 0.9800 . ?
C62B H62B 0.9800 . ?
C62B H62C 0.9800 . ?
C63B H63A 0.9800 . ?
C63B H63B 0.9800 . ?
C63B H63C 0.9800 . ?
O61A C61A 1.200(8) . ?
C61A C62A 1.453(16) . ?
C61A C63A 1.509(11) . ?
C62A H62D 0.9800 . ?
C62A H62E 0.9800 . ?
C62A H62F 0.9800 . ?
C63A H63D 0.9800 . ?
C63A H63E 0.9800 . ?
C63A H63F 0.9800 . ?
O51 C51 1.220(6) . ?
C51 C52 1.492(7) . ?
C51 C53 1.474(7) . ?
C52 H52A 0.9800 . ?
C52 H52B 0.9800 . ?
C52 H52C 0.9800 . ?
C53 H53A 0.9800 . ?
C53 H53B 0.9800 . ?
C53 H53C 0.9800 . ?
S201 O201 1.447(3) . ?
S201 O202 1.431(3) . ?
S201 O203 1.440(3) . ?
S201 C201 1.821(4) . ?
F201 C201 1.325(5) . ?
F202 C201 1.316(5) . ?
F203 C201 1.337(5) . ?
S211 O211 1.430(3) . ?
S211 O212 1.436(3) . ?
S211 O213 1.429(3) . ?
S211 C211 1.818(4) . ?
F211 C211 1.333(5) . ?
F212 C211 1.336(5) . ?
F213 C211 1.319(5) . ?
O62B H62G 0.8498 . ?
O62B H62H 0.8498 . ?
O101 H10A 0.8498 . ?
O101 H10B 0.8495 . ?

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
N1 Cu1 N8 177.22(11) . 3_666 ?
N4 Cu1 N1 89.96(10) 1_545 . ?
N4 Cu1 N8 88.47(11) 1_545 3_666 ?
N5 Cu1 N1 91.38(10) . . ?
N5 Cu1 N4 178.55(10) . 1_545 ?
N5 Cu1 N8 90.17(11) . 3_666 ?
C1 N1 Cu1 126.1(2) . . ?
C1 N1 C2 105.7(3) . . ?
C2 N1 Cu1 127.8(2) . . ?
C1 N2 C3 107.7(3) . . ?
C1 N2 C4 125.8(3) . . ?
C3 N2 C4 126.3(3) . . ?
C12 N3 C11 126.9(3) . . ?
C14 N3 C11 125.3(3) . . ?
C14 N3 C12 107.8(3) . . ?
C13 N4 Cu1 128.5(2) . 1_565 ?
C14 N4 Cu1 125.5(2) . 1_565 ?
C14 N4 C13 106.0(3) . . ?
C15 N5 Cu1 126.0(2) . . ?
C15 N5 C16 105.8(3) . . ?
C16 N5 Cu1 128.1(2) . . ?
C15 N6 C17 107.7(3) . . ?
C15 N6 C18 124.9(3) . . ?
C17 N6 C18 127.3(3) . . ?
C26 N7 C25 124.2(3) . . ?
C28 N7 C25 126.9(3) . . ?
C28 N7 C26 108.1(3) . . ?
C27 N8 Cu1 125.5(2) . 3_666 ?
C28 N8 Cu1 127.7(2) . 3_666 ?
C28 N8 C27 105.9(3) . . ?
N1 C1 N2 110.6(3) . . ?
N1 C1 H1 124.7 . . ?
N2 C1 H1 124.7 . . ?
N1 C2 H2 125.1 . . ?
C3 C2 N1 109.9(3) . . ?
C3 C2 H2 125.1 . . ?
N2 C3 H3 127.0 . . ?
C2 C3 N2 106.1(3) . . ?
C2 C3 H3 127.0 . . ?
N2 C4 H4A 109.1 . . ?
N2 C4 H4B 109.1 . . ?
N2 C4 C5 112.7(3) . . ?
H4A C4 H4B 107.8 . . ?
C5 C4 H4A 109.1 . . ?
C5 C4 H4B 109.1 . . ?
C6 C5 C4 119.2(3) . . ?
C6 C5 C10 118.5(3) . . ?
C10 C5 C4 122.3(3) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 C5 121.6(3) . . ?
C7 C6 H6 119.2 . . ?
C6 C7 H7 119.9 . . ?
C6 C7 C8 120.3(3) . . ?
C8 C7 H7 119.9 . . ?
C7 C8 H8 120.5 . . ?
C7 C8 C9 119.1(4) . . ?
C9 C8 H8 120.5 . . ?
C8 C9 H9 119.3 . . ?
C10 C9 C8 121.4(3) . . ?
C10 C9 H9 119.3 . . ?
C5 C10 C11 119.4(3) . . ?
C9 C10 C5 119.2(3) . . ?
C9 C10 C11 121.4(3) . . ?
N3 C11 C10 113.1(3) . . ?
N3 C11 H11A 109.0 . . ?
N3 C11 H11B 109.0 . . ?
C10 C11 H11A 109.0 . . ?
C10 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
N3 C12 H12 127.0 . . ?
C13 C12 N3 105.9(3) . . ?
C13 C12 H12 127.0 . . ?
N4 C13 H13 125.3 . . ?
C12 C13 N4 109.3(3) . . ?
C12 C13 H13 125.3 . . ?
N3 C14 H14 124.5 . . ?
N4 C14 N3 111.0(3) . . ?
N4 C14 H14 124.5 . . ?
N5 C15 N6 111.4(3) . . ?
N5 C15 H15 124.3 . . ?
N6 C15 H15 124.3 . . ?
N5 C16 H16 125.6 . . ?
C17 C16 N5 108.9(3) . . ?
C17 C16 H16 125.6 . . ?
N6 C17 H17 126.9 . . ?
C16 C17 N6 106.2(3) . . ?
C16 C17 H17 126.9 . . ?
N6 C18 H18A 108.7 . . ?
N6 C18 H18B 108.7 . . ?
N6 C18 C19 114.2(3) . . ?
H18A C18 H18B 107.6 . . ?
C19 C18 H18A 108.7 . . ?
C19 C18 H18B 108.7 . . ?
C20 C19 C18 117.0(3) . . ?
C20 C19 C24 119.1(3) . . ?
C24 C19 C18 123.7(3) . . ?
C19 C20 H20 119.2 . . ?
C21 C20 C19 121.6(3) . . ?
C21 C20 H20 119.2 . . ?
C20 C21 H21 120.3 . . ?
C22 C21 C20 119.5(3) . . ?
C22 C21 H21 120.3 . . ?
C21 C22 H22 120.2 . . ?
C21 C22 C23 119.6(3) . . ?
C23 C22 H22 120.2 . . ?
C22 C23 H23 119.0 . . ?
C22 C23 C24 121.9(3) . . ?
C24 C23 H23 119.0 . . ?
C19 C24 C25 120.9(3) . . ?
C23 C24 C19 118.2(3) . . ?
C23 C24 C25 120.8(3) . . ?
N7 C25 C24 112.1(3) . . ?
N7 C25 H25A 109.2 . . ?
N7 C25 H25B 109.2 . . ?
C24 C25 H25A 109.2 . . ?
C24 C25 H25B 109.2 . . ?
H25A C25 H25B 107.9 . . ?
N7 C26 H26 127.0 . . ?
N7 C26 C27 106.1(3) . . ?
C27 C26 H26 127.0 . . ?
N8 C27 H27 125.3 . . ?
C26 C27 N8 109.3(3) . . ?
C26 C27 H27 125.3 . . ?
N7 C28 H28 124.7 . . ?
N8 C28 N7 110.6(3) . . ?
N8 C28 H28 124.7 . . ?
O61B C61B C62B 123(2) . . ?
O61B C61B C63B 118.6(17) . . ?
C63B C61B C62B 118.5(18) . . ?
C61B C62B H62A 109.5 . . ?
C61B C62B H62B 109.5 . . ?
C61B C62B H62C 109.5 . . ?
H62A C62B H62B 109.5 . . ?
H62A C62B H62C 109.5 . . ?
H62B C62B H62C 109.5 . . ?
C61B C63B H63A 109.5 . . ?
C61B C63B H63B 109.5 . . ?
C61B C63B H63C 109.5 . . ?
H63A C63B H63B 109.5 . . ?
H63A C63B H63C 109.5 . . ?
H63B C63B H63C 109.5 . . ?
O61A C61A C62A 122.8(10) . . ?
O61A C61A C63A 121.7(8) . . ?
C62A C61A C63A 115.5(9) . . ?
C61A C62A H62D 109.5 . . ?
C61A C62A H62E 109.5 . . ?
C61A C62A H62F 109.5 . . ?
H62D C62A H62E 109.5 . . ?
H62D C62A H62F 109.5 . . ?
H62E C62A H62F 109.5 . . ?
C61A C63A H63D 109.5 . . ?
C61A C63A H63E 109.5 . . ?
C61A C63A H63F 109.5 . . ?
H63D C63A H63E 109.5 . . ?
H63D C63A H63F 109.5 . . ?
H63E C63A H63F 109.5 . . ?
O51 C51 C52 121.5(4) . . ?
O51 C51 C53 121.6(5) . . ?
C53 C51 C52 116.9(4) . . ?
C51 C52 H52A 109.5 . . ?
C51 C52 H52B 109.5 . . ?
C51 C52 H52C 109.5 . . ?
H52A C52 H52B 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
C51 C53 H53A 109.5 . . ?
C51 C53 H53B 109.5 . . ?
C51 C53 H53C 109.5 . . ?
H53A C53 H53B 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?
O201 S201 C201 103.24(19) . . ?
O202 S201 O201 114.80(16) . . ?
O202 S201 O203 114.76(19) . . ?
O202 S201 C201 104.22(19) . . ?
O203 S201 O201 114.17(17) . . ?
O203 S201 C201 103.62(19) . . ?
F201 C201 S201 110.6(3) . . ?
F201 C201 F203 107.4(4) . . ?
F202 C201 S201 111.6(3) . . ?
F202 C201 F201 108.0(4) . . ?
F202 C201 F203 108.4(4) . . ?
F203 C201 S201 110.7(3) . . ?
O211 S211 O212 113.91(18) . . ?
O211 S211 C211 103.06(17) . . ?
O212 S211 C211 103.49(18) . . ?
O213 S211 O211 114.96(17) . . ?
O213 S211 O212 115.2(2) . . ?
O213 S211 C211 104.06(18) . . ?
F211 C211 S211 111.5(3) . . ?
F211 C211 F212 107.4(3) . . ?
F212 C211 S211 110.8(3) . . ?
F213 C211 S211 111.8(3) . . ?
F213 C211 F211 107.8(4) . . ?
F213 C211 F212 107.3(3) . . ?
H62G O62B H62H 104.5 . . ?
H10A O101 H10B 104.5 . . ?

_olex2_date_sample_completion    2017-05-24
_olex2_date_sample_data_collection 2017-05-08
_olex2_date_sample_submission    2017-05-04
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id EL1464
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.439
_oxdiff_exptl_absorpt_empirical_full_min 0.757
####################################################################### 
# 
# 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_el1145hex
_database_code_depnum_ccdc_archive 'CCDC 1831784'
_audit_update_record             
;
2018-03-22 deposited with the CCDC.
2018-05-01 downloaded from the CCDC.
;
_audit_creation_date             2017-11-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C44 H36 Cu N8, 2(C F3 O3 S)'
_chemical_formula_sum            'C46 H36 Cu F6 N8 O6 S2'
_chemical_formula_weight         1038.49
_chemical_melting_point          ?
_chemical_oxdiff_formula         C45H45N10CuCl2O8
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'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.0686(6)
_cell_length_b                   11.2199(6)
_cell_length_c                   12.0883(8)
_cell_angle_alpha                115.102(6)
_cell_angle_beta                 104.812(6)
_cell_angle_gamma                93.484(5)
_cell_volume                     1056.48(13)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2396
_cell_measurement_temperature    173
_cell_measurement_theta_max      70.8790
_cell_measurement_theta_min      4.2110
_shelx_estimated_absorpt_T_max   0.726
_shelx_estimated_absorpt_T_min   0.616
_exptl_absorpt_coefficient_mu    2.439
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.44a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.632
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             531
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0921
_diffrn_reflns_av_unetI/netI     0.0976
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5327
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.133
_diffrn_reflns_theta_min         4.250
_diffrn_ambient_temperature      173.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1033
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     12.00  90.00   1.00    2.00    --   36.63  77.00 -90.00   78
  2  ω     39.00  93.00   1.00    2.00    --   36.63 178.00 -90.00   54
  3  ω     36.00 109.00   1.00    2.00    --   36.63 178.00-180.00   73
  4  ω     13.00 103.00   1.00    2.00    --   36.63  77.00   0.00   90
  5  ω    100.00 151.00   1.00    5.35    --  107.00  61.00  30.00   51
  6  ω     40.00 120.00   1.00    5.35    --  107.00 -45.00 -30.00   80
  7  ω     74.00 121.00   1.00    5.35    --  107.00 -92.00-153.62   47
  8  ω     53.00 126.00   1.00    5.35    --  107.00 -92.00 -14.83   73
  9  ω     59.00 113.00   1.00    5.35    --  107.00 -93.00 122.07   54
 10  ω     46.00  76.00   1.00    2.00    --   36.63 -99.00 150.00   30
 11  ω     38.00 172.00   1.00    5.35    --  107.00   0.00   0.00  134
 12  ω     43.00 123.00   1.00    5.35    --  107.00 -45.00-120.00   80
 13  ω     39.00 122.00   1.00    5.35    --  107.00 -45.00  60.00   83
 14  ω     40.00 124.00   1.00    5.35    --  107.00 -45.00 150.00   84
 15  ω    -24.00  19.00   1.00    2.00    --   36.63 -99.00 150.00   43
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1492474000
_diffrn_orient_matrix_UB_12      -0.0077593000
_diffrn_orient_matrix_UB_13      -0.1006374000
_diffrn_orient_matrix_UB_21      0.0771805000
_diffrn_orient_matrix_UB_22      0.1259654000
_diffrn_orient_matrix_UB_23      -0.0003295000
_diffrn_orient_matrix_UB_31      0.0619988000
_diffrn_orient_matrix_UB_32      -0.0891947000
_diffrn_orient_matrix_UB_33      -0.1086484000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2966
_reflns_number_total             3844
_reflns_odcompleteness_completeness 97.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.44a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.44a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.44a (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.065
_refine_diff_density_min         -0.812
_refine_diff_density_rms         0.125
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         3844
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0883
_refine_ls_R_factor_gt           0.0682
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1150P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1736
_refine_ls_wR_factor_ref         0.1948
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 H22-H3_$1
 2.02 with sigma of 0.001
3.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C8(H8A,H8B)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C22(H22), C20(H20), C6(H6), C3(H3), C4(H4), C17(H17), C13(H13),
 C5(H5), C10(H10), C11(H11), C19(H19), C18(H18), C12(H12)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 1.0000 0.5000 0.5000 0.0233(2) Uani 1 2 d S T P . .
S1 S 1.03559(11) 0.86696(9) 0.72789(10) 0.0275(3) Uani 1 1 d . . . . .
F1 F 1.1561(4) 1.0846(3) 0.9466(3) 0.0462(7) Uani 1 1 d . . . . .
F2 F 1.3097(3) 0.9449(3) 0.9035(3) 0.0475(7) Uani 1 1 d . . . . .
O1 O 1.0510(3) 0.7291(3) 0.6937(3) 0.0301(6) Uani 1 1 d . . . . .
F3 F 1.1212(4) 0.9042(3) 0.9661(3) 0.0508(8) Uani 1 1 d . . . . .
O3 O 0.8879(4) 0.8986(3) 0.7397(4) 0.0470(9) Uani 1 1 d . . . . .
N2 N 0.6044(4) 0.6393(3) 0.4410(3) 0.0236(7) Uani 1 1 d . . . . .
N1 N 0.7759(4) 0.5170(3) 0.4423(3) 0.0246(7) Uani 1 1 d . . . . .
N3 N 0.0472(4) 0.5846(3) 0.3917(3) 0.0233(7) Uani 1 1 d . . . . .
N4 N 0.1477(4) 0.7458(3) 0.3673(4) 0.0270(7) Uani 1 1 d . . . . .
C1 C 0.7558(4) 0.6404(3) 0.4831(3) 0.0174(7) Uani 1 1 d . . . . .
H1 H 0.8354 0.7182 0.5344 0.021 Uiso 1 1 calc R . . . .
C22 C 0.1540(4) 0.6906(3) 0.4437(3) 0.0162(6) Uani 1 1 d . . . . .
H22 H 0.2277 0.7242 0.5268 0.019 Uiso 1 1 calc DR . . . .
O2 O 1.1055(5) 0.9275(4) 0.6651(4) 0.0516(10) Uani 1 1 d . . . . .
C7 C 0.5220(4) 0.5104(4) 0.3661(4) 0.0208(7) Uani 1 1 d . . . . .
C2 C 0.6340(4) 0.4307(4) 0.3685(4) 0.0220(7) Uani 1 1 d . . . . .
C16 C 0.0296(5) 0.6734(4) 0.2559(4) 0.0274(8) Uani 1 1 d . . . . .
C21 C -0.0350(4) 0.5664(4) 0.2696(4) 0.0252(8) Uani 1 1 d . . . . .
C20 C -0.1592(5) 0.4679(4) 0.1728(4) 0.0311(9) Uani 1 1 d . . . . .
H20 H -0.2017 0.3941 0.1816 0.037 Uiso 1 1 calc R . . . .
C6 C 0.3644(5) 0.4592(4) 0.3004(4) 0.0278(8) Uani 1 1 d . . . . .
H6 H 0.2905 0.5157 0.3004 0.033 Uiso 1 1 calc R . . . .
C3 C 0.5856(4) 0.2889(4) 0.2956(3) 0.0293(8) Uani 1 1 d . . . . .
H3 H 0.6591 0.2314 0.2895 0.035 Uiso 1 1 calc DR . . . .
C14 C 0.3734(4) 0.8525(4) 0.3355(4) 0.0258(8) Uani 1 1 d . . . . .
C9 C 0.5072(5) 0.8001(4) 0.3655(4) 0.0254(8) Uani 1 1 d . . . . .
C15 C 0.2547(5) 0.8723(4) 0.4092(4) 0.0287(8) Uani 1 1 d . . . . .
H15A H 0.3109 0.9096 0.5022 0.034 Uiso 1 1 calc R . . . .
H15B H 0.1936 0.9381 0.3964 0.034 Uiso 1 1 calc R . . . .
C4 C 0.4354(5) 0.2397(4) 0.2365(5) 0.0333(9) Uani 1 1 d . . . . .
H4 H 0.4017 0.1451 0.1928 0.040 Uiso 1 1 calc R . . . .
C8 C 0.5468(5) 0.7656(4) 0.4758(4) 0.0282(8) Uani 1 1 d . . . . .
H8A H 0.6271 0.8389 0.5502 0.034 Uiso 1 1 calc R . . . .
H8B H 0.4530 0.7576 0.5018 0.034 Uiso 1 1 calc R . . . .
C17 C -0.0294(5) 0.6889(5) 0.1444(5) 0.0368(10) Uani 1 1 d . . . . .
H17 H 0.0140 0.7616 0.1343 0.044 Uiso 1 1 calc R . . . .
C13 C 0.3482(5) 0.8888(4) 0.2368(5) 0.0308(9) Uani 1 1 d . . . . .
H13 H 0.2587 0.9247 0.2165 0.037 Uiso 1 1 calc R . . . .
C5 C 0.3223(5) 0.3212(4) 0.2353(4) 0.0316(9) Uani 1 1 d . . . . .
H5 H 0.2162 0.2803 0.1891 0.038 Uiso 1 1 calc R . . . .
C10 C 0.6101(5) 0.7857(4) 0.2947(5) 0.0348(10) Uani 1 1 d . . . . .
H10 H 0.7011 0.7518 0.3153 0.042 Uiso 1 1 calc R . . . .
C23 C 1.1620(5) 0.9548(5) 0.8943(4) 0.0339(9) Uani 1 1 d . . . . .
C11 C 0.5822(6) 0.8199(5) 0.1951(5) 0.0402(11) Uani 1 1 d . . . . .
H11 H 0.6519 0.8068 0.1460 0.048 Uiso 1 1 calc R . . . .
C19 C -0.2173(6) 0.4831(5) 0.0637(5) 0.0413(11) Uani 1 1 d . . . . .
H19 H -0.3023 0.4184 -0.0048 0.050 Uiso 1 1 calc R . . . .
C18 C -0.1531(6) 0.5929(5) 0.0514(5) 0.0434(11) Uani 1 1 d . . . . .
H18 H -0.1980 0.6003 -0.0250 0.052 Uiso 1 1 calc R . . . .
C12 C 0.4524(6) 0.8734(5) 0.1673(5) 0.0408(11) Uani 1 1 d . . . . .
H12 H 0.4344 0.8996 0.1006 0.049 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N1 2.022(3) 2_766 ?
Cu1 N1 2.022(3) . ?
Cu1 N3 2.022(3) 1_655 ?
Cu1 N3 2.022(3) 2_666 ?
S1 O1 1.448(3) . ?
S1 O3 1.433(3) . ?
S1 O2 1.439(4) . ?
S1 C23 1.826(5) . ?
F1 C23 1.330(5) . ?
F2 C23 1.331(5) . ?
F3 C23 1.331(6) . ?
N2 C1 1.334(5) . ?
N2 C7 1.371(5) . ?
N2 C8 1.468(4) . ?
N1 C1 1.300(5) . ?
N1 C2 1.385(5) . ?
N3 Cu1 2.022(3) 1_455 ?
N3 C22 1.289(5) . ?
N3 C21 1.392(5) . ?
N4 C22 1.305(5) . ?
N4 C16 1.360(6) . ?
N4 C15 1.477(5) . ?
C1 H1 0.9500 . ?
C22 H22 0.9500 . ?
C7 C2 1.396(5) . ?
C7 C6 1.392(5) . ?
C2 C3 1.424(5) . ?
C16 C21 1.395(5) . ?
C16 C17 1.406(6) . ?
C21 C20 1.392(6) . ?
C20 H20 0.9500 . ?
C20 C19 1.376(7) . ?
C6 H6 0.9500 . ?
C6 C5 1.380(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.322(6) . ?
C14 C9 1.411(5) . ?
C14 C15 1.534(5) . ?
C14 C13 1.388(6) . ?
C9 C8 1.506(6) . ?
C9 C10 1.392(6) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C4 H4 0.9500 . ?
C4 C5 1.416(6) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C17 H17 0.9500 . ?
C17 C18 1.365(7) . ?
C13 H13 0.9500 . ?
C13 C12 1.389(6) . ?
C5 H5 0.9500 . ?
C10 H10 0.9500 . ?
C10 C11 1.382(7) . ?
C11 H11 0.9500 . ?
C11 C12 1.383(7) . ?
C19 H19 0.9500 . ?
C19 C18 1.411(7) . ?
C18 H18 0.9500 . ?
C12 H12 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
N1 Cu1 N1 180.0 2_766 . ?
N1 Cu1 N3 91.66(13) . 2_666 ?
N1 Cu1 N3 88.34(13) 2_766 2_666 ?
N1 Cu1 N3 91.66(13) 2_766 1_655 ?
N1 Cu1 N3 88.34(13) . 1_655 ?
N3 Cu1 N3 180.0 2_666 1_655 ?
O1 S1 C23 102.08(19) . . ?
O3 S1 O1 116.2(2) . . ?
O3 S1 O2 115.4(3) . . ?
O3 S1 C23 102.3(2) . . ?
O2 S1 O1 115.0(2) . . ?
O2 S1 C23 102.8(2) . . ?
C1 N2 C7 110.9(3) . . ?
C1 N2 C8 120.4(3) . . ?
C7 N2 C8 128.7(3) . . ?
C1 N1 Cu1 113.7(2) . . ?
C1 N1 C2 109.5(3) . . ?
C2 N1 Cu1 136.7(3) . . ?
C22 N3 Cu1 119.8(2) . 1_455 ?
C22 N3 C21 107.6(3) . . ?
C21 N3 Cu1 131.3(3) . 1_455 ?
C22 N4 C16 109.9(3) . . ?
C22 N4 C15 120.6(3) . . ?
C16 N4 C15 129.5(4) . . ?
N2 C1 H1 125.8 . . ?
N1 C1 N2 108.4(3) . . ?
N1 C1 H1 125.8 . . ?
N3 C22 N4 111.1(3) . . ?
N3 C22 H22 124.4 . . ?
N4 C22 H22 124.4 . . ?
N2 C7 C2 104.3(3) . . ?
N2 C7 C6 131.9(3) . . ?
C6 C7 C2 123.8(3) . . ?
N1 C2 C7 106.9(3) . . ?
N1 C2 C3 134.7(3) . . ?
C7 C2 C3 118.3(3) . . ?
N4 C16 C21 104.9(4) . . ?
N4 C16 C17 133.4(4) . . ?
C21 C16 C17 121.7(4) . . ?
N3 C21 C16 106.5(3) . . ?
C20 C21 N3 131.7(4) . . ?
C20 C21 C16 121.8(4) . . ?
C21 C20 H20 121.7 . . ?
C19 C20 C21 116.5(4) . . ?
C19 C20 H20 121.7 . . ?
C7 C6 H6 122.1 . . ?
C5 C6 C7 115.7(4) . . ?
C5 C6 H6 122.1 . . ?
C2 C3 H3 121.0 . . ?
C4 C3 C2 118.0(4) . . ?
C4 C3 H3 121.0 . . ?
C9 C14 C15 122.3(4) . . ?
C13 C14 C9 119.2(4) . . ?
C13 C14 C15 118.5(4) . . ?
C14 C9 C8 122.2(4) . . ?
C10 C9 C14 119.0(4) . . ?
C10 C9 C8 118.7(4) . . ?
N4 C15 C14 112.4(3) . . ?
N4 C15 H15A 109.1 . . ?
N4 C15 H15B 109.1 . . ?
C14 C15 H15A 109.1 . . ?
C14 C15 H15B 109.1 . . ?
H15A C15 H15B 107.9 . . ?
C3 C4 H4 118.4 . . ?
C3 C4 C5 123.2(4) . . ?
C5 C4 H4 118.4 . . ?
N2 C8 C9 111.5(3) . . ?
N2 C8 H8A 109.3 . . ?
N2 C8 H8B 109.3 . . ?
C9 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
C16 C17 H17 122.2 . . ?
C18 C17 C16 115.6(4) . . ?
C18 C17 H17 122.2 . . ?
C14 C13 H13 119.6 . . ?
C14 C13 C12 120.8(4) . . ?
C12 C13 H13 119.6 . . ?
C6 C5 C4 120.8(4) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C9 C10 H10 119.4 . . ?
C11 C10 C9 121.2(4) . . ?
C11 C10 H10 119.4 . . ?
F1 C23 S1 111.3(3) . . ?
F1 C23 F2 107.6(4) . . ?
F1 C23 F3 107.8(4) . . ?
F2 C23 S1 111.9(3) . . ?
F3 C23 S1 111.3(3) . . ?
F3 C23 F2 106.8(4) . . ?
C10 C11 H11 120.2 . . ?
C10 C11 C12 119.7(4) . . ?
C12 C11 H11 120.2 . . ?
C20 C19 H19 119.3 . . ?
C20 C19 C18 121.3(4) . . ?
C18 C19 H19 119.3 . . ?
C17 C18 C19 123.0(5) . . ?
C17 C18 H18 118.5 . . ?
C19 C18 H18 118.5 . . ?
C13 C12 H12 120.0 . . ?
C11 C12 C13 120.1(4) . . ?
C11 C12 H12 120.0 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 7.966
_oxdiff_exptl_absorpt_empirical_full_min 0.555
####################################################################### 
# 
# 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_2017ncs0036z
_database_code_depnum_ccdc_archive 'CCDC 1831788'
_audit_update_record             
;
2018-03-22 deposited with the CCDC.
2018-05-01 downloaded from the CCDC.
;
_audit_creation_date             2017-02-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H16 N6'
_chemical_formula_sum            'C20 H16 N6'
_chemical_formula_weight         340.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C42 H32 N12 O6 F6 S2 Zn2'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.3881(4)
_cell_length_b                   7.6794(9)
_cell_length_c                   17.8944(12)
_cell_angle_alpha                87.348(7)
_cell_angle_beta                 89.529(5)
_cell_angle_gamma                67.155(8)
_cell_volume                     808.07(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5145
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.5930
_cell_measurement_theta_min      2.8660
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86147
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.9g (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13024
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_min         2.279
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -94.00  41.00   1.00   10.00    --  -17.00   0.00-180.00  135
  2  ω   -107.00  22.00   1.00   10.00    --  -17.00 -72.00-180.00  129
  3  ω    -69.00  22.00   1.00   10.00    --  -17.00 -72.00   0.00   91
  4  ω    -25.00  -2.00   1.00   10.00    --  -17.00  72.00 -90.00   23
  5  ω    -41.00 -26.00   1.00   10.00    --  -17.00  36.00-180.00   15
  6  ω   -107.00  73.00   1.00   10.00    --  -17.00   0.00 150.00  180
  7  ω    -64.00  22.00   1.00   10.00    --  -17.00 -72.00  90.00   86
  8  ω    -49.00  22.00   1.00   10.00    --  -17.00 -72.00 -90.00   71
  9  ω    -26.00 -10.00   1.00   10.00    --  -17.00  72.00-150.00   16
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0430693000
_diffrn_orient_matrix_UB_12      0.0085586000
_diffrn_orient_matrix_UB_13      0.0369044000
_diffrn_orient_matrix_UB_21      -0.0139057000
_diffrn_orient_matrix_UB_22      0.0963270000
_diffrn_orient_matrix_UB_23      -0.0011745000
_diffrn_orient_matrix_UB_31      -0.1116701000
_diffrn_orient_matrix_UB_32      0.0267413000
_diffrn_orient_matrix_UB_33      -0.0145401000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2785
_reflns_number_total             3650
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.9g (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.9g (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.9g (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.677
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.131
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3650
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1229
_refine_ls_R_factor_gt           0.0994
_refine_ls_restrained_S_all      1.118
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1380P)²+1.5630P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2643
_refine_ls_wR_factor_ref         0.2788
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C11(H11), C4(H4), C19(H19), C6(H6), C18(H18), C17(H17), C9(H9),
 C5(H5), C12(H12), C10(H10), C20(H20)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.0097(5) 0.8657(4) 0.36059(17) 0.0222(6) Uani 1 1 d . . . . .
N2 N -0.2129(5) 0.9081(4) 0.34464(18) 0.0270(7) Uani 1 1 d . . . . .
N4 N 0.6713(5) 0.8466(4) 0.13550(18) 0.0254(7) Uani 1 1 d . . . . .
N5 N 0.8603(5) 0.8809(5) 0.14924(19) 0.0289(7) Uani 1 1 d . . . . .
N3 N -0.3138(5) 0.8797(4) 0.40478(19) 0.0276(7) Uani 1 1 d . . . . .
N6 N 0.9832(5) 0.8523(5) 0.08955(19) 0.0303(7) Uani 1 1 d . . . . .
C15 C 0.6734(6) 0.7935(5) 0.0642(2) 0.0227(7) Uani 1 1 d . . . . .
C13 C 0.4913(6) 0.6860(5) 0.2247(2) 0.0225(7) Uani 1 1 d . . . . .
C16 C 0.8756(6) 0.7963(5) 0.0350(2) 0.0258(8) Uani 1 1 d . . . . .
C1 C 0.0559(6) 0.8046(4) 0.4334(2) 0.0209(7) Uani 1 1 d . . . . .
C14 C 0.5022(6) 0.8701(5) 0.1934(2) 0.0251(8) Uani 1 1 d . . . . .
H14A H 0.3541 0.9504 0.1730 0.030 Uiso 1 1 calc R . . . .
H14B H 0.5350 0.9348 0.2342 0.030 Uiso 1 1 calc R . . . .
C2 C -0.1531(6) 0.8137(5) 0.4616(2) 0.0244(8) Uani 1 1 d . . . . .
C8 C 0.3218(5) 0.6921(5) 0.27507(19) 0.0207(7) Uani 1 1 d . . . . .
C3 C -0.1711(6) 0.7611(5) 0.5367(2) 0.0277(8) Uani 1 1 d . . . . .
H3 H -0.3092 0.7685 0.5566 0.033 Uiso 1 1 calc R . . . .
C11 C 0.6259(7) 0.3442(5) 0.2303(2) 0.0292(8) Uani 1 1 d . . . . .
H11 H 0.7313 0.2277 0.2165 0.035 Uiso 1 1 calc R . . . .
C4 C 0.0245(6) 0.6981(5) 0.5801(2) 0.0267(8) Uani 1 1 d . . . . .
H4 H 0.0191 0.6612 0.6301 0.032 Uiso 1 1 calc R . . . .
C19 C 0.5893(6) 0.6919(5) -0.0486(2) 0.0288(8) Uani 1 1 d . . . . .
H19 H 0.4958 0.6552 -0.0781 0.035 Uiso 1 1 calc R . . . .
C6 C 0.2558(6) 0.7404(5) 0.4767(2) 0.0260(8) Uani 1 1 d . . . . .
H6 H 0.3941 0.7334 0.4571 0.031 Uiso 1 1 calc R . . . .
C18 C 0.7915(6) 0.6952(5) -0.0797(2) 0.0272(8) Uani 1 1 d . . . . .
H18 H 0.8270 0.6613 -0.1289 0.033 Uiso 1 1 calc R . . . .
C17 C 0.9362(6) 0.7474(5) -0.0391(2) 0.0269(8) Uani 1 1 d . . . . .
H17 H 1.0691 0.7503 -0.0596 0.032 Uiso 1 1 calc R . . . .
C9 C 0.3008(6) 0.5254(5) 0.3002(2) 0.0260(8) Uani 1 1 d . . . . .
H9 H 0.1843 0.5304 0.3327 0.031 Uiso 1 1 calc R . . . .
C7 C 0.1634(6) 0.8819(5) 0.3025(2) 0.0249(8) Uani 1 1 d . . . . .
H7A H 0.2534 0.9467 0.3219 0.030 Uiso 1 1 calc R . . . .
H7B H 0.0744 0.9585 0.2605 0.030 Uiso 1 1 calc R . . . .
C5 C 0.2340(6) 0.6889(5) 0.5491(2) 0.0275(8) Uani 1 1 d . . . . .
H5 H 0.3623 0.6455 0.5798 0.033 Uiso 1 1 calc R . . . .
C12 C 0.6452(6) 0.5112(5) 0.2031(2) 0.0259(8) Uani 1 1 d . . . . .
H12 H 0.7615 0.5052 0.1704 0.031 Uiso 1 1 calc R . . . .
C10 C 0.4525(7) 0.3520(5) 0.2772(2) 0.0301(8) Uani 1 1 d . . . . .
H10 H 0.4364 0.2412 0.2936 0.036 Uiso 1 1 calc R . . . .
C20 C 0.5250(6) 0.7403(5) 0.0229(2) 0.0279(8) Uani 1 1 d . . . . .
H20 H 0.3912 0.7380 0.0429 0.034 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N2 1.359(4) . ?
N1 C1 1.360(5) . ?
N1 C7 1.458(5) . ?
N2 N3 1.303(5) . ?
N4 N5 1.359(4) . ?
N4 C15 1.356(5) . ?
N4 C14 1.456(5) . ?
N5 N6 1.296(5) . ?
N3 C2 1.382(5) . ?
N6 C16 1.375(5) . ?
C15 C16 1.396(5) . ?
C15 C20 1.397(5) . ?
C13 C14 1.523(5) . ?
C13 C8 1.391(5) . ?
C13 C12 1.391(5) . ?
C16 C17 1.405(6) . ?
C1 C2 1.400(5) . ?
C1 C6 1.402(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C2 C3 1.403(5) . ?
C8 C9 1.392(5) . ?
C8 C7 1.517(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.382(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.400(5) . ?
C11 C10 1.368(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.422(5) . ?
C19 H19 0.9300 . ?
C19 C18 1.411(5) . ?
C19 C20 1.365(6) . ?
C6 H6 0.9300 . ?
C6 C5 1.359(5) . ?
C18 H18 0.9300 . ?
C18 C17 1.367(5) . ?
C17 H17 0.9300 . ?
C9 H9 0.9300 . ?
C9 C10 1.387(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C5 H5 0.9300 . ?
C12 H12 0.9300 . ?
C10 H10 0.9300 . ?
C20 H20 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
N2 N1 C1 110.2(3) . . ?
N2 N1 C7 120.7(3) . . ?
C1 N1 C7 129.1(3) . . ?
N3 N2 N1 109.3(3) . . ?
N5 N4 C14 120.5(3) . . ?
C15 N4 N5 109.9(3) . . ?
C15 N4 C14 129.6(3) . . ?
N6 N5 N4 109.2(3) . . ?
N2 N3 C2 107.8(3) . . ?
N5 N6 C16 108.2(3) . . ?
N4 C15 C16 104.3(3) . . ?
N4 C15 C20 133.0(3) . . ?
C16 C15 C20 122.7(3) . . ?
C8 C13 C14 119.5(3) . . ?
C12 C13 C14 121.4(3) . . ?
C12 C13 C8 119.1(3) . . ?
N6 C16 C15 108.4(3) . . ?
N6 C16 C17 131.2(3) . . ?
C15 C16 C17 120.4(3) . . ?
N1 C1 C2 104.0(3) . . ?
N1 C1 C6 132.9(3) . . ?
C2 C1 C6 123.1(3) . . ?
N4 C14 C13 114.5(3) . . ?
N4 C14 H14A 108.6 . . ?
N4 C14 H14B 108.6 . . ?
C13 C14 H14A 108.6 . . ?
C13 C14 H14B 108.6 . . ?
H14A C14 H14B 107.6 . . ?
N3 C2 C1 108.7(3) . . ?
N3 C2 C3 131.1(3) . . ?
C1 C2 C3 120.2(3) . . ?
C13 C8 C9 120.0(3) . . ?
C13 C8 C7 119.1(3) . . ?
C9 C8 C7 120.9(3) . . ?
C2 C3 H3 121.4 . . ?
C4 C3 C2 117.3(3) . . ?
C4 C3 H3 121.4 . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.2(3) . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.7(4) . . ?
C5 C4 H4 119.7 . . ?
C18 C19 H19 118.6 . . ?
C20 C19 H19 118.6 . . ?
C20 C19 C18 122.9(4) . . ?
C1 C6 H6 122.3 . . ?
C5 C6 C1 115.5(3) . . ?
C5 C6 H6 122.3 . . ?
C19 C18 H18 119.3 . . ?
C17 C18 C19 121.3(4) . . ?
C17 C18 H18 119.3 . . ?
C16 C17 H17 121.4 . . ?
C18 C17 C16 117.1(3) . . ?
C18 C17 H17 121.4 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.4(3) . . ?
C10 C9 H9 119.8 . . ?
N1 C7 C8 113.2(3) . . ?
N1 C7 H7A 108.9 . . ?
N1 C7 H7B 108.9 . . ?
C8 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
H7A C7 H7B 107.8 . . ?
C4 C5 H5 118.4 . . ?
C6 C5 C4 123.2(3) . . ?
C6 C5 H5 118.4 . . ?
C13 C12 C11 120.3(3) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C11 C10 C9 119.9(3) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C15 C20 H20 122.2 . . ?
C19 C20 C15 115.6(3) . . ?
C19 C20 H20 122.2 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.029
_oxdiff_exptl_absorpt_empirical_full_min 0.351
####################################################################### 
# 
# 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_2017ncs0287xa
_database_code_depnum_ccdc_archive 'CCDC 1831787'
_audit_update_record             
;
2018-03-22 deposited with the CCDC.
2018-05-01 downloaded from the CCDC.
;
_audit_creation_date             2018-01-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'2(C41 H32 Cu2 F3 N12 O3 S), 2(C F3 O3 S), 4(C3 H6 O)'
_chemical_formula_sum            'C96 H88 Cu4 F12 N24 O16 S4'
_chemical_formula_weight         2444.30
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Cu (C20 H16 N3)2 C F3 S O3'
_chemical_oxdiff_usercomment     EL1460A
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'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   16.6451(3)
_cell_length_b                   17.1433(2)
_cell_length_c                   19.1060(3)
_cell_angle_alpha                90.7040(10)
_cell_angle_beta                 90.0420(10)
_cell_angle_gamma                97.2670(10)
_cell_volume                     5407.72(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    18045
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.7290
_cell_measurement_theta_min      3.4820
_shelx_estimated_absorpt_T_max   0.976
_shelx_estimated_absorpt_T_min   0.760
_exptl_absorpt_coefficient_mu    2.420
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75321
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.31c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             2496
_exptl_crystal_recrystallization_method 
'The material was recrystallised from a mixture of acetone and Et2O'
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0517
_diffrn_reflns_av_unetI/netI     0.0552
_diffrn_reflns_Laue_measured_fraction_full 0.956
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            50455
_diffrn_reflns_point_group_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        66.590
_diffrn_reflns_theta_max         66.590
_diffrn_reflns_theta_min         3.458
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'hybrid pixel detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_dtime           0.000
_diffrn_detector_type            'Rigaku, HyPix 6000'
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -84.00  70.00   0.50    5.00    --    5.00  29.00 -30.00  308
  2  ω    -19.00   6.00   0.50    5.00    --    5.00  41.00-157.00   50
  3  ω    -89.00  80.00   0.50    5.00    --    0.00  41.00-157.00  338
  4  ω    -82.00 -56.00   0.50    5.00    --    0.00  60.00-120.00   52
  5  ω   -153.00-127.00   0.50   20.00    --  -90.00   0.00-180.00   52
  6  ω   -108.00 -82.00   0.50   20.00    --  -90.00   0.00-180.00   52
  7  ω   -178.00 -85.00   0.50   20.00    --  -90.00  14.00-150.00  186
  8  ω    -68.00 -37.00   0.50   20.00    --  -90.00  14.00-150.00   62
  9  ω   -179.00-148.00   0.50   20.00    --  -90.00  29.00   0.00   62
 10  ω   -142.00  -1.00   0.50   20.00    --  -90.00  29.00   0.00  282
 11  ω   -114.00 -89.00   0.50   20.00    --  -90.00  41.00-157.00   50
 12  ω   -124.00 -98.00   0.50   20.00    --  -90.00  43.00 120.00   52
 13  ω   -110.00 -85.00   0.50   20.00    --  -90.00  60.00-180.00   50
 14  ω   -179.00 -96.00   0.50   20.00    --  -90.00  60.00 -60.00  166
 15  ω    -77.00 -17.00   0.50   20.00    --  -90.00  60.00 -60.00  120
 16  ω   -149.00-116.00   0.50   20.00    --  -90.00  60.00-180.00   66
 17  ω    -71.00 -17.00   0.50   20.00    --  -90.00  60.00-180.00  108
 18  ω   -178.00  -1.00   0.50   20.00    --  -90.00  60.00  90.00  354
 19  ω    -52.00  -4.00   0.50   20.00    --  -90.00  60.00 -90.00   96
 20  ω   -135.00 -95.00   0.50   20.00    --  -90.00  60.00 -90.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_details 'Rigaku, AFC11 quarter χ goniometer'
_diffrn_measurement_device_type  
'Rigaku 007HF equipped with Varimax confocal mirrors and an AFC11 goniometer and HyPix 6000 detector'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroLoop'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0217552000
_diffrn_orient_matrix_UB_12      0.0867059000
_diffrn_orient_matrix_UB_13      -0.0205630000
_diffrn_orient_matrix_UB_21      0.0748202000
_diffrn_orient_matrix_UB_22      0.0065364000
_diffrn_orient_matrix_UB_23      0.0482350000
_diffrn_orient_matrix_UB_31      0.0513243000
_diffrn_orient_matrix_UB_32      -0.0254447000
_diffrn_orient_matrix_UB_33      -0.0612628000
_diffrn_radiation_collimation    'Varimax focusing mirrors'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Rotating anode'
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_target            Cu
_diffrn_source_type              'Rigaku 007 HF'
_diffrn_source_voltage           40.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                13560
_reflns_number_total             18266
_reflns_odcompleteness_completeness 95.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.31c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.31c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.31c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.063
_refine_diff_density_min         -0.546
_refine_diff_density_rms         0.108
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1442
_refine_ls_number_reflns         18266
_refine_ls_number_restraints     1296
_refine_ls_R_factor_all          0.0818
_refine_ls_R_factor_gt           0.0609
_refine_ls_restrained_S_all      0.979
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1242P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1626
_refine_ls_wR_factor_ref         0.1769
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Sof: C243(0.5) H24D(0.5) H24E(0.5) H24F(0.5) C253(0.5) H25A(0.5)
 H25B(0.5) H25C(0.5)
 Fixed Uiso: H29(0.041) H7A(0.043) H7B(0.043) H22(0.047) H30(0.045)
 H27A(0.041) H27B(0.041) H57A(0.044) H57B(0.044) H16(0.049) H59(0.051)
 H32(0.047) H9(0.049) H12(0.05) H31(0.046) H25(0.053) H34A(0.048) H34B(0.048)
 H14A(0.041) H14B(0.041) H17(0.053) H77A(0.044) H77B(0.044) H5(0.055)
 H64A(0.046) H64B(0.046) H10(0.056) H66(0.052) H52(0.057) H79(0.049) H69(0.047)
 H19(0.051) H89(0.055) H67(0.057) H68(0.056) H24(0.061) H18(0.054) H36(0.059)
 H2(0.057) H80(0.057) H11(0.055) H23(0.059) H62(0.055) H84A(0.048) H84B(0.048)
 H81(0.061) H82(0.055) H86(0.06) H72(0.058) H87(0.065) H60(0.063) H4(0.064)
 H3(0.064) H55(0.053) H61(0.064) H88(0.063) H54(0.063) H39(0.065) H53(0.066)
 H37(0.065) H38(0.071) H75(0.07) H73(0.077) H74(0.084) H26A(0.108) H26B(0.108)
 H26C(0.108) H22A(0.104) H22B(0.104) H22C(0.104) H26D(0.211) H26E(0.211)
 H26F(0.211) H20A(0.224) H20B(0.224) H20C(0.224) H22D(0.144) H22E(0.144)
 H22F(0.144) H20D(0.277) H20E(0.277) H20F(0.277) H23A(0.138) H23B(0.138)
 H23C(0.138) H23D(0.161) H23E(0.161) H23F(0.161) H24A(0.217) H24B(0.217)
 H24C(0.217) H24D(0.216) H24E(0.216) H24F(0.216) H25A(0.295) H25B(0.295)
 H25C(0.295)
 Fixed X: H29(0.138859) H7A(-0.094438) H7B(-0.13968) H22(0.234299)
 H30(0.14362) H27A(0.091915) H27B(0.005455) H57A(0.377336) H57B(0.431668)
 H16(0.020819) H59(0.262314) H32(0.007057) H9(-0.025473) H12(0.128143)
 H31(0.076069) H25(0.235539) H34A(-0.032045) H34B(0.028414) H14A(-0.046521)
 H14B(-0.043058) H17(0.079332) H77A(0.369436) H77B(0.300725) H5(-0.206266)
 H64A(0.408701) H64B(0.333984) H10(0.099119) H66(0.252058) H52(0.368212)
 H79(0.450654) H69(0.382611) H19(0.200721) H89(0.528812) H67(0.224536)
 H68(0.287755) H24(0.344166) H18(0.16753) H36(-0.136008) H2(-0.265697)
 H80(0.53853) H11(0.173847) H23(0.342508) H62(0.225481) H84A(0.31145)
 H84B(0.353105) H81(0.552945) H82(0.477467) H86(0.418906) H72(0.352377)
 H87(0.494003) H60(0.152752) H4(-0.284512) H3(-0.315463) H55(0.287237)
 H61(0.1337) H88(0.548661) H54(0.245857) H39(-0.308972) H53(0.284664) H37(-
 0.267943) H38(-0.35194) H75(0.226126) H73(0.235099) H74(0.171434) H26A(-
 0.349429) H26B(-0.408095) H26C(-0.399091) H22A(0.647731) H22B(0.615564)
 H22C(0.592689) H26D(-0.318712) H26E(-0.376376) H26F(-0.282479) H20A(0.882346)
 H20B(0.859383) H20C(0.934854) H22D(0.444191) H22E(0.476875) H22F(0.411746)
 H20D(1.033204) H20E(0.944015) H20F(1.004468) H23A(0.455772) H23B(0.540786)
 H23C(0.536876) H23D(0.561854) H23E(0.465805) H23F(0.511733) H24A(0.112694)
 H24B(0.114391) H24C(0.072227) H24D(-0.055098) H24E(-0.107918) H24F(-0.079068)
 H25A(-0.020186) H25B(-0.005208) H25C(-0.089724)
 Fixed Y: H29(0.720596) H7A(0.446434) H7B(0.407698) H22(0.437245)
 H30(0.827679) H27A(0.710625) H27B(0.677116) H57A(0.875041) H57B(0.916999)
 H16(0.176713) H59(0.828851) H32(0.936039) H9(0.559491) H12(0.35356)
 H31(0.934669) H25(0.680222) H34A(0.776654) H34B(0.853432) H14A(0.290781)
 H14B(0.350812) H17(0.059388) H77A(0.835599) H77B(0.863752) H5(0.448141)
 H64A(1.008145) H64B(1.011065) H10(0.557176) H66(1.104552) H52(0.563712)
 H79(0.990121) H69(1.358325) H19(0.122678) H89(0.501848) H67(1.219009)
 H68(1.342776) H24(0.606868) H18(0.033975) H36(1.091483) H2(0.708259)
 H80(0.982056) H11(0.452913) H23(0.487144) H62(1.07732) H84A(0.723695)
 H84B(0.732863) H81(0.859265) H82(0.746408) H86(0.485716) H72(1.183896)
 H87(0.391163) H60(0.888351) H4(0.512849) H3(0.639116) H55(0.744557)
 H61(1.012757) H88(0.398765) H54(0.609197) H39(0.880175) H53(0.521932)
 H37(1.105176) H38(1.001269) H75(0.979195) H73(1.198249) H74(1.096414)
 H26A(0.437503) H26B(0.376525) H26C(0.362129) H22A(0.817296) H22B(0.765741)
 H22C(0.734651) H26D(0.219697) H26E(0.240607) H26F(0.235617) H20A(0.766859)
 H20B(0.815577) H20C(0.766379) H22D(0.727546) H22E(0.778328) H22F(0.80975)
 H20D(0.919789) H20E(0.94514) H20F(0.978122) H23A(0.831979) H23B(0.802294)
 H23C(0.893054) H23D(0.720601) H23E(0.719749) H23F(0.745311) H24A(0.794148)
 H24B(0.703486) H24C(0.759156) H24D(0.736634) H24E(0.735783) H24F(0.656027)
 H25A(0.833116) H25B(0.849099) H25C(0.803824)
 Fixed Z: H29(0.000147) H7A(0.096478) H7B(0.16379) H22(0.051104) H30(-
 0.074719) H27A(0.167812) H27B(0.135846) H57A(0.349304) H57B(0.411352)
 H16(0.19873) H59(0.492598) H32(0.06015) H9(0.239811) H12(0.198928) H31(-
 0.044408) H25(0.176412) H34A(0.177198) H34B(0.198207) H14A(0.151262)
 H14B(0.087708) H17(0.193218) H77A(0.608725) H77B(0.658024) H5(0.28084)
 H64A(0.353647) H64B(0.301593) H10(0.297777) H66(0.241696) H52(0.485847)
 H79(0.715613) H69(0.309992) H19(0.014545) H89(0.627395) H67(0.185862)
 H68(0.220044) H24(0.182157) H18(0.10483) H36(0.208613) H2(0.236749)
 H80(0.809606) H11(0.278734) H23(0.12341) H62(0.41131) H84A(0.735736)
 H84B(0.660383) H81(0.85692) H82(0.811901) H86(0.859128) H72(0.537824)
 H87(0.815354) H60(0.530553) H4(0.357543) H3(0.335814) H55(0.318378)
 H61(0.488871) H88(0.702236) H54(0.308967) H39(0.100899) H53(0.391019)
 H37(0.174654) H38(0.125024) H75(0.68247) H73(0.600493) H74(0.669288)
 H26A(0.031663) H26B(0.076975) H26C(-0.005409) H22A(0.276031) H22B(0.208967)
 H22C(0.285949) H26D(0.02327) H26E(0.085927) H26F(0.100472) H20A(0.571633)
 H20B(0.639117) H20C(0.641791) H22D(0.228561) H22E(0.162377) H22F(0.213642)
 H20D(0.65862) H20E(0.662562) H20F(0.601639) H23A(0.168154) H23B(0.14994)
 H23C(0.168349) H23D(0.261123) H23E(0.255617) H23F(0.32749) H24A(0.355615)
 H24B(0.373767) H24C(0.426389) H24D(0.425621) H24E(0.355531) H24F(0.383105)
 H25A(0.396042) H25B(0.314452) H25C(0.340377)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu2 Cu 0.06354(3) 0.41612(3) -0.02118(3) 0.03250(15) Uani 1 1 d . U . . .
Cu51 Cu 0.48135(3) 0.68346(3) 0.58686(3) 0.03588(15) Uani 1 1 d . U . . .
Cu52 Cu 0.49256(3) 1.10443(3) 0.46662(3) 0.03420(15) Uani 1 1 d . U . . .
Cu1 Cu -0.17602(4) 0.74353(3) 0.09147(3) 0.03991(16) Uani 1 1 d . U . . .
S151 S 0.13224(6) 0.74447(6) 0.70491(6) 0.0419(2) Uani 1 1 d . U . . .
S1 S -0.36501(6) 0.67792(6) 0.04972(6) 0.0448(3) Uani 1 1 d . U . . .
S51 S 0.61469(7) 0.61800(6) 0.48427(6) 0.0466(3) Uani 1 1 d . U . . .
S101 S 0.23689(8) 0.88571(6) 0.21070(7) 0.0610(4) Uani 1 1 d . U . . .
F1 F -0.30106(16) 0.69718(17) -0.07476(14) 0.0634(7) Uani 1 1 d . U . . .
F52 F 0.71920(16) 0.72890(15) 0.54242(15) 0.0604(7) Uani 1 1 d . U . . .
F103 F 0.23162(18) 0.91052(16) 0.07550(15) 0.0671(8) Uani 1 1 d . U . . .
N7 N 0.09648(18) 0.51481(16) 0.03777(16) 0.0310(7) Uani 1 1 d . U . . .
O51 O 0.56825(18) 0.60998(16) 0.54808(16) 0.0494(7) Uani 1 1 d . U . . .
N5 N 0.08438(18) 0.31448(16) 0.02904(16) 0.0320(7) Uani 1 1 d . U . . .
N8 N 0.05337(18) 0.57356(16) 0.05146(16) 0.0323(7) Uani 1 1 d . U . . .
O1 O -0.30541(17) 0.74169(16) 0.07487(16) 0.0490(7) Uani 1 1 d . U . . .
N4 N 0.05045(18) 0.28872(16) 0.09032(16) 0.0323(7) Uani 1 1 d . U . . .
O3 O -0.3370(2) 0.60218(16) 0.04868(17) 0.0544(8) Uani 1 1 d . U . . .
N9 N 0.09723(18) 0.62513(16) 0.09535(16) 0.0323(7) Uani 1 1 d . U . . .
O153 O 0.05112(19) 0.75532(19) 0.72234(17) 0.0584(8) Uani 1 1 d . U . . .
N2 N -0.12953(18) 0.58525(16) 0.11352(17) 0.0338(7) Uani 1 1 d . U . . .
N59 N 0.36819(18) 0.95296(18) 0.60958(17) 0.0361(7) Uani 1 1 d . U . . .
F53 F 0.74286(18) 0.61148(17) 0.56504(17) 0.0746(9) Uani 1 1 d . U . . .
N52 N 0.43382(19) 0.79826(17) 0.48855(16) 0.0343(7) Uani 1 1 d . U . . .
O261 O -0.23289(19) 0.36630(19) 0.05050(17) 0.0567(8) Uani 1 1 d . U . . .
O53 O 0.59430(19) 0.67841(17) 0.43847(16) 0.0520(8) Uani 1 1 d . U . . .
N6 N 0.13141(18) 0.26358(16) 0.00582(17) 0.0333(7) Uani 1 1 d . U . . .
F51 F 0.77011(18) 0.66099(18) 0.46296(17) 0.0729(8) Uani 1 1 d . U . . .
O151 O 0.17057(18) 0.69636(19) 0.75311(17) 0.0566(8) Uani 1 1 d . U . . .
N55 N 0.42609(18) 1.15293(17) 0.39319(16) 0.0334(7) Uani 1 1 d . U . . .
N54 N 0.36896(19) 1.11409(17) 0.35093(17) 0.0352(7) Uani 1 1 d . U . . .
O2 O -0.44444(19) 0.6818(2) 0.07571(18) 0.0608(8) Uani 1 1 d . U . . .
N53 N 0.39068(19) 0.80474(17) 0.42976(17) 0.0365(7) Uani 1 1 d . U . . .
N56 N 0.43061(19) 1.22847(17) 0.38039(16) 0.0342(7) Uani 1 1 d . U . . .
N1 N -0.16773(19) 0.64258(18) 0.13865(17) 0.0362(7) Uani 1 1 d . U . . .
N3 N -0.14235(19) 0.52455(17) 0.15823(17) 0.0349(7) Uani 1 1 d . U . . .
N58 N 0.42898(18) 0.97268(17) 0.56497(16) 0.0328(7) Uani 1 1 d . U . . .
N61 N 0.3984(2) 0.65409(18) 0.72099(18) 0.0413(8) Uani 1 1 d . U . . .
O152 O 0.1815(2) 0.81464(18) 0.6838(2) 0.0651(9) Uani 1 1 d . U . . .
O52 O 0.6272(2) 0.54521(17) 0.45158(17) 0.0582(8) Uani 1 1 d . U . . .
N51 N 0.42647(19) 0.72364(17) 0.50650(17) 0.0357(7) Uani 1 1 d . U . . .
N11 N -0.0792(2) 0.87745(17) 0.16255(17) 0.0395(7) Uani 1 1 d . U . . .
N12 N -0.1509(2) 0.85036(18) 0.13550(18) 0.0406(8) Uani 1 1 d . U . . .
N57 N 0.42397(18) 1.04468(17) 0.54186(16) 0.0343(7) Uani 1 1 d . U . . .
N62 N 0.44198(19) 0.62400(18) 0.67102(17) 0.0368(7) Uani 1 1 d . U . . .
F151 F 0.0881(2) 0.7227(2) 0.57437(17) 0.0915(10) Uani 1 1 d . U . . .
N10 N -0.0706(2) 0.95124(18) 0.18627(18) 0.0437(8) Uani 1 1 d . U . . .
F3 F -0.42635(19) 0.6486(2) -0.07605(17) 0.0929(11) Uani 1 1 d . U . . .
N60 N 0.3888(2) 0.61480(19) 0.78052(18) 0.0450(8) Uani 1 1 d . U . . .
F2 F -0.3933(2) 0.7705(2) -0.05177(19) 0.1048(13) Uani 1 1 d . U . . .
C21 C 0.1681(2) 0.5288(2) 0.07375(19) 0.0328(8) Uani 1 1 d . U . . .
O103 O 0.3033(3) 0.8757(2) 0.2550(2) 0.0911(14) Uani 1 1 d . U . . .
F153 F 0.1942(3) 0.6715(2) 0.60246(19) 0.1043(12) Uani 1 1 d . U . . .
O102 O 0.1783(3) 0.8179(2) 0.2051(2) 0.0853(13) Uani 1 1 d . U . . .
C15 C 0.0758(2) 0.2181(2) 0.1064(2) 0.0359(8) Uani 1 1 d . U . . .
F152 F 0.0777(3) 0.61775(19) 0.6358(2) 0.1094(13) Uani 1 1 d . U . . .
C28 C 0.0680(2) 0.76276(19) 0.0742(2) 0.0321(8) Uani 1 1 d . U . . .
O221 O 0.5208(2) 0.8758(2) 0.2967(2) 0.0700(10) Uani 1 1 d . U . . .
C26 C 0.1693(2) 0.6001(2) 0.1103(2) 0.0349(8) Uani 1 1 d . U . . .
C1 C -0.2053(2) 0.6181(2) 0.2002(2) 0.0372(8) Uani 1 1 d . U . . .
C29 C 0.1111(2) 0.7639(2) 0.0124(2) 0.0343(8) Uani 1 1 d . U . . .
H29 H 0.138859 0.720596 0.000147 0.041 Uiso 1 1 calc R . . . .
C8 C -0.0224(2) 0.4570(2) 0.18491(19) 0.0344(8) Uani 1 1 d . U . . .
C6 C -0.1890(2) 0.5426(2) 0.2124(2) 0.0375(8) Uani 1 1 d . U . . .
C20 C 0.1276(2) 0.2033(2) 0.0530(2) 0.0347(8) Uani 1 1 d . U . . .
C40 C -0.1943(3) 0.9129(2) 0.1416(2) 0.0429(9) Uani 1 1 d . U . . .
C7 C -0.1031(2) 0.4538(2) 0.1473(2) 0.0357(8) Uani 1 1 d . U . . .
H7A H -0.094438 0.446434 0.096478 0.043 Uiso 1 1 calc R . . . .
H7B H -0.139680 0.407698 0.163790 0.043 Uiso 1 1 calc R . . . .
C13 C 0.0238(2) 0.3956(2) 0.1727(2) 0.0350(8) Uani 1 1 d . U . . .
C22 C 0.2338(2) 0.4851(2) 0.0766(2) 0.0395(9) Uani 1 1 d . U . . .
H22 H 0.234299 0.437245 0.051104 0.047 Uiso 1 1 calc R . . . .
C76 C 0.3216(2) 1.0124(2) 0.6159(2) 0.0412(9) Uani 1 1 d . U . . .
C63 C 0.2990(2) 0.9916(2) 0.4033(2) 0.0371(8) Uani 1 1 d . U . . .
C30 C 0.1143(2) 0.8276(2) -0.0321(2) 0.0378(9) Uani 1 1 d . U . . .
H30 H 0.143620 0.827679 -0.074719 0.045 Uiso 1 1 calc R . . . .
C58 C 0.3103(2) 0.9163(2) 0.4279(2) 0.0367(8) Uani 1 1 d . U . . .
C51 C 0.3779(2) 0.6812(2) 0.4578(2) 0.0375(9) Uani 1 1 d . U . . .
C33 C 0.0292(2) 0.8279(2) 0.0931(2) 0.0361(8) Uani 1 1 d . U . . .
C65 C 0.3357(2) 1.1652(2) 0.3094(2) 0.0361(8) Uani 1 1 d . U . . .
C27 C 0.0630(2) 0.69330(19) 0.1239(2) 0.0344(8) Uani 1 1 d . U . . .
H27A H 0.091915 0.710625 0.167812 0.041 Uiso 1 1 calc R . . . .
H27B H 0.005455 0.677116 0.135846 0.041 Uiso 1 1 calc R . . . .
C70 C 0.3752(2) 1.2387(2) 0.3287(2) 0.0348(8) Uani 1 1 d . U . . .
C57 C 0.3820(2) 0.8806(2) 0.4008(2) 0.0363(8) Uani 1 1 d . U . . .
H57A H 0.377336 0.875041 0.349304 0.044 Uiso 1 1 calc R . . . .
H57B H 0.431668 0.916999 0.411352 0.044 Uiso 1 1 calc R . . . .
O101 O 0.2052(3) 0.9587(2) 0.2214(2) 0.0918(14) Uani 1 1 d . U . . .
C90 C 0.4625(2) 0.5569(2) 0.7005(2) 0.0403(9) Uani 1 1 d . U . . .
C71 C 0.3584(2) 1.0709(2) 0.5729(2) 0.0374(8) Uani 1 1 d . U . . .
C16 C 0.0559(2) 0.1658(2) 0.1617(2) 0.0407(9) Uani 1 1 d . U . . .
H16 H 0.020819 0.176713 0.198730 0.049 Uiso 1 1 calc R . . . .
C59 C 0.2548(2) 0.8793(2) 0.4756(2) 0.0424(9) Uani 1 1 d . U . . .
H59 H 0.262314 0.828851 0.492598 0.051 Uiso 1 1 calc R . . . .
C32 C 0.0333(2) 0.8918(2) 0.0478(2) 0.0394(9) Uani 1 1 d . U . . .
H32 H 0.007057 0.936039 0.060150 0.047 Uiso 1 1 calc R . . . .
C78 C 0.4120(2) 0.8727(2) 0.7060(2) 0.0354(8) Uani 1 1 d . U . . .
C9 C 0.0055(2) 0.5174(2) 0.2315(2) 0.0404(9) Uani 1 1 d . U . . .
H9 H -0.025473 0.559491 0.239811 0.049 Uiso 1 1 calc R . . . .
C12 C 0.0966(2) 0.3952(2) 0.2075(2) 0.0413(9) Uani 1 1 d . U . . .
H12 H 0.128143 0.353560 0.198928 0.050 Uiso 1 1 calc R . . . .
C31 C 0.0746(2) 0.8912(2) -0.0138(2) 0.0386(9) Uani 1 1 d . U . . .
H31 H 0.076069 0.934669 -0.044408 0.046 Uiso 1 1 calc R . . . .
C85 C 0.4293(3) 0.5519(2) 0.7690(2) 0.0429(9) Uani 1 1 d . U . . .
C56 C 0.3547(2) 0.7329(2) 0.4081(2) 0.0370(9) Uani 1 1 d . U . . .
C25 C 0.2348(3) 0.6316(2) 0.1518(2) 0.0441(10) Uani 1 1 d . U . . .
H25 H 0.235539 0.680222 0.176412 0.053 Uiso 1 1 calc R . . . .
C34 C -0.0119(2) 0.8309(2) 0.1629(2) 0.0400(9) Uani 1 1 d . U . . .
H34A H -0.032045 0.776654 0.177198 0.048 Uiso 1 1 calc R . . . .
H34B H 0.028414 0.853432 0.198207 0.048 Uiso 1 1 calc R . . . .
C14 C -0.0101(2) 0.3293(2) 0.1242(2) 0.0341(8) Uani 1 1 d . U . . .
H14A H -0.046521 0.290781 0.151262 0.041 Uiso 1 1 calc R . . . .
H14B H -0.043058 0.350812 0.087708 0.041 Uiso 1 1 calc R . . . .
F102 F 0.3445(3) 0.9473(3) 0.1226(2) 0.1389(19) Uani 1 1 d . U . . .
C17 C 0.0914(3) 0.0976(2) 0.1579(2) 0.0444(10) Uani 1 1 d . U . . .
H17 H 0.079332 0.059388 0.193218 0.053 Uiso 1 1 calc R . . . .
C77 C 0.3579(2) 0.8762(2) 0.6432(2) 0.0365(9) Uani 1 1 d . U . . .
H77A H 0.369436 0.835599 0.608725 0.044 Uiso 1 1 calc R . . . .
H77B H 0.300725 0.863752 0.658024 0.044 Uiso 1 1 calc R . . . .
C5 C -0.2180(3) 0.5000(2) 0.2722(2) 0.0455(10) Uani 1 1 d . U . . .
H5 H -0.206266 0.448141 0.280840 0.055 Uiso 1 1 calc R . . . .
C64 C 0.3558(2) 1.0282(2) 0.3483(2) 0.0384(9) Uani 1 1 d . U . . .
H64A H 0.408701 1.008145 0.353647 0.046 Uiso 1 1 calc R . . . .
H64B H 0.333984 1.011065 0.301593 0.046 Uiso 1 1 calc R . . . .
C10 C 0.0796(3) 0.5158(2) 0.2662(2) 0.0470(10) Uani 1 1 d . U . . .
H10 H 0.099119 0.557176 0.297777 0.056 Uiso 1 1 calc R . . . .
C35 C -0.1428(3) 0.9749(2) 0.1729(2) 0.0418(9) Uani 1 1 d . U . . .
C83 C 0.4186(2) 0.7994(2) 0.7371(2) 0.0384(9) Uani 1 1 d . U . . .
F101 F 0.3067(3) 0.8256(3) 0.1043(2) 0.1151(14) Uani 1 1 d . U . . .
C66 C 0.2783(2) 1.1549(2) 0.2552(2) 0.0433(10) Uani 1 1 d . U . . .
H66 H 0.252058 1.104552 0.241696 0.052 Uiso 1 1 calc R . . . .
C52 C 0.3525(3) 0.5998(2) 0.4527(2) 0.0476(11) Uani 1 1 d . U . . .
H52 H 0.368212 0.563712 0.485847 0.057 Uiso 1 1 calc R . . . .
C79 C 0.4564(2) 0.9402(2) 0.7348(2) 0.0411(9) Uani 1 1 d . U . . .
H79 H 0.450654 0.990121 0.715613 0.049 Uiso 1 1 calc R . . . .
C69 C 0.3572(2) 1.3077(2) 0.2961(2) 0.0390(9) Uani 1 1 d . U . . .
H69 H 0.382611 1.358325 0.309992 0.047 Uiso 1 1 calc R . . . .
C19 C 0.1644(3) 0.1333(2) 0.0508(2) 0.0425(9) Uani 1 1 d . U . . .
H19 H 0.200721 0.122678 0.014545 0.051 Uiso 1 1 calc R . . . .
C89 C 0.5073(3) 0.4993(2) 0.6735(2) 0.0456(10) Uani 1 1 d . U . . .
H89 H 0.528812 0.501848 0.627395 0.055 Uiso 1 1 calc R . . . .
C67 C 0.2627(3) 1.2227(2) 0.2232(2) 0.0477(11) Uani 1 1 d . U . . .
H67 H 0.224536 1.219009 0.185862 0.057 Uiso 1 1 calc R . . . .
C68 C 0.3013(3) 1.2978(2) 0.2437(2) 0.0464(10) Uani 1 1 d . U . . .
H68 H 0.287755 1.342776 0.220044 0.056 Uiso 1 1 calc R . . . .
C24 C 0.2981(3) 0.5878(3) 0.1547(2) 0.0504(11) Uani 1 1 d . U . . .
H24 H 0.344166 0.606868 0.182157 0.061 Uiso 1 1 calc R . . . .
C18 C 0.1445(3) 0.0819(2) 0.1042(2) 0.0453(10) Uani 1 1 d . U . . .
H18 H 0.167530 0.033975 0.104830 0.054 Uiso 1 1 calc R . . . .
C36 C -0.1700(3) 1.0493(2) 0.1869(2) 0.0491(10) Uani 1 1 d . U . . .
H36 H -0.136008 1.091483 0.208613 0.059 Uiso 1 1 calc R . . . .
C2 C -0.2535(3) 0.6566(3) 0.2455(2) 0.0478(10) Uani 1 1 d . U . . .
H2 H -0.265697 0.708259 0.236749 0.057 Uiso 1 1 calc R . . . .
C80 C 0.5085(3) 0.9357(3) 0.7908(2) 0.0479(10) Uani 1 1 d . U . . .
H80 H 0.538530 0.982056 0.809606 0.057 Uiso 1 1 calc R . . . .
C11 C 0.1242(3) 0.4545(2) 0.2545(2) 0.0462(10) Uani 1 1 d . U . . .
H11 H 0.173847 0.452913 0.278734 0.055 Uiso 1 1 calc R . . . .
C23 C 0.2975(3) 0.5156(3) 0.1186(2) 0.0490(11) Uani 1 1 d . U . . .
H23 H 0.342508 0.487144 0.123410 0.059 Uiso 1 1 calc R . . . .
C62 C 0.2332(3) 1.0265(2) 0.4272(2) 0.0459(10) Uani 1 1 d . U . . .
H62 H 0.225481 1.077320 0.411310 0.055 Uiso 1 1 calc R . . . .
C84 C 0.3639(2) 0.7269(2) 0.7109(2) 0.0400(9) Uani 1 1 d . U . . .
H84A H 0.311450 0.723695 0.735736 0.048 Uiso 1 1 calc R . . . .
H84B H 0.353105 0.732863 0.660383 0.048 Uiso 1 1 calc R . . . .
C81 C 0.5166(3) 0.8630(3) 0.8191(2) 0.0508(11) Uani 1 1 d . U . . .
H81 H 0.552945 0.859265 0.856920 0.061 Uiso 1 1 calc R . . . .
C82 C 0.4717(3) 0.7959(2) 0.7921(2) 0.0457(10) Uani 1 1 d . U . . .
H82 H 0.477467 0.746408 0.811901 0.055 Uiso 1 1 calc R . . . .
C86 C 0.4408(3) 0.4893(2) 0.8132(2) 0.0499(11) Uani 1 1 d . U . . .
H86 H 0.418906 0.485716 0.859128 0.060 Uiso 1 1 calc R . . . .
C72 C 0.3271(3) 1.1429(2) 0.5663(2) 0.0486(10) Uani 1 1 d . U . . .
H72 H 0.352377 1.183896 0.537824 0.058 Uiso 1 1 calc R . . . .
C87 C 0.4849(3) 0.4342(3) 0.7869(3) 0.0538(11) Uani 1 1 d . U . . .
H87 H 0.494003 0.391163 0.815354 0.065 Uiso 1 1 calc R . . . .
C261 C -0.3024(3) 0.3361(3) 0.0507(2) 0.0534(11) Uani 1 1 d . U . . .
C60 C 0.1900(3) 0.9144(3) 0.4982(3) 0.0523(11) Uani 1 1 d . U . . .
H60 H 0.152752 0.888351 0.530553 0.063 Uiso 1 1 calc R . . . .
C4 C -0.2639(3) 0.5386(3) 0.3163(3) 0.0530(11) Uani 1 1 d . U . . .
H4 H -0.284512 0.512849 0.357543 0.064 Uiso 1 1 calc R . . . .
C3 C -0.2823(3) 0.6153(3) 0.3035(2) 0.0535(11) Uani 1 1 d . U . . .
H3 H -0.315463 0.639116 0.335814 0.064 Uiso 1 1 calc R . . . .
C55 C 0.3038(3) 0.7086(2) 0.3513(2) 0.0443(10) Uani 1 1 d . U . . .
H55 H 0.287237 0.744557 0.318378 0.053 Uiso 1 1 calc R . . . .
C61 C 0.1789(3) 0.9884(3) 0.4736(3) 0.0532(11) Uani 1 1 d . U . . .
H61 H 0.133700 1.012757 0.488871 0.064 Uiso 1 1 calc R . . . .
C88 C 0.5181(3) 0.4388(3) 0.7180(3) 0.0525(11) Uani 1 1 d . U . . .
H88 H 0.548661 0.398765 0.702236 0.063 Uiso 1 1 calc R . . . .
C54 C 0.2797(3) 0.6293(2) 0.3468(2) 0.0522(11) Uani 1 1 d . U . . .
H54 H 0.245857 0.609197 0.308967 0.063 Uiso 1 1 calc R . . . .
C39 C -0.2739(3) 0.9216(3) 0.1224(3) 0.0544(11) Uani 1 1 d . U . . .
H39 H -0.308972 0.880175 0.100899 0.065 Uiso 1 1 calc R . . . .
C91 C 0.7160(3) 0.6564(3) 0.5148(3) 0.0554(11) Uani 1 1 d . U . . .
C53 C 0.3035(3) 0.5763(2) 0.3966(3) 0.0553(12) Uani 1 1 d . U . . .
H53 H 0.284664 0.521932 0.391019 0.066 Uiso 1 1 calc R . . . .
C37 C -0.2476(3) 1.0564(3) 0.1673(2) 0.0538(11) Uani 1 1 d . U . . .
H37 H -0.267943 1.105176 0.174654 0.065 Uiso 1 1 calc R . . . .
C41 C -0.3717(3) 0.7008(3) -0.0419(3) 0.0604(12) Uani 1 1 d . U . . .
C221 C 0.5266(3) 0.8228(3) 0.2553(3) 0.0588(12) Uani 1 1 d . U . . .
C38 C -0.2980(3) 0.9935(3) 0.1366(3) 0.0594(12) Uani 1 1 d . U . . .
H38 H -0.351940 1.001269 0.125024 0.071 Uiso 1 1 calc R . . . .
C75 C 0.2510(3) 1.0198(3) 0.6534(3) 0.0584(13) Uani 1 1 d . U . . .
H75 H 0.226126 0.979195 0.682470 0.070 Uiso 1 1 calc R . . . .
C101 C 0.2814(4) 0.8946(3) 0.1247(3) 0.0710(14) Uani 1 1 d . U . . .
C151 C 0.1221(4) 0.6865(3) 0.6246(3) 0.0662(13) Uani 1 1 d . U . . .
C73 C 0.2582(3) 1.1505(3) 0.6032(3) 0.0639(14) Uani 1 1 d . U . . .
H73 H 0.235099 1.198249 0.600493 0.077 Uiso 1 1 calc R . . . .
C74 C 0.2201(3) 1.0890(3) 0.6456(3) 0.0703(16) Uani 1 1 d . U . . .
H74 H 0.171434 1.096414 0.669288 0.084 Uiso 1 1 calc R . . . .
C262 C -0.3705(3) 0.3819(4) 0.0373(3) 0.0718(15) Uani 1 1 d . U . . .
H26A H -0.349429 0.437503 0.031663 0.108 Uiso 1 1 calc GR . . . .
H26B H -0.408095 0.376525 0.076975 0.108 Uiso 1 1 calc GR . . . .
H26C H -0.399091 0.362129 -0.005409 0.108 Uiso 1 1 calc GR . . . .
C222 C 0.6024(5) 0.7814(4) 0.2567(4) 0.069(2) Uani 0.729(11) 1 d . U P A 1
H22A H 0.647731 0.817296 0.276031 0.104 Uiso 0.729(11) 1 calc GR . P A 1
H22B H 0.615564 0.765741 0.208967 0.104 Uiso 0.729(11) 1 calc GR . P A 1
H22C H 0.592689 0.734651 0.285949 0.104 Uiso 0.729(11) 1 calc GR . P A 1
C201 C 0.9577(5) 0.8674(7) 0.5879(5) 0.120(3) Uani 1 1 d . U . . .
C263 C -0.3217(5) 0.2507(4) 0.0664(6) 0.141(4) Uani 1 1 d . U . . .
H26D H -0.318712 0.219697 0.023270 0.211 Uiso 1 1 calc GR . . . .
H26E H -0.376376 0.240607 0.085927 0.211 Uiso 1 1 calc GR . . . .
H26F H -0.282479 0.235617 0.100472 0.211 Uiso 1 1 calc GR . . . .
O201 O 0.9679(5) 0.8699(6) 0.5223(4) 0.182(3) Uani 1 1 d . U . . .
C202 C 0.9041(5) 0.7983(7) 0.6121(6) 0.150(4) Uani 1 1 d . U . . .
H20A H 0.882346 0.766859 0.571633 0.224 Uiso 1 1 calc GR . . . .
H20B H 0.859383 0.815577 0.639117 0.224 Uiso 1 1 calc GR . . . .
H20C H 0.934854 0.766379 0.641791 0.224 Uiso 1 1 calc GR . . . .
C223 C 0.4589(6) 0.7809(6) 0.2111(6) 0.096(4) Uani 0.729(11) 1 d . U P A 1
H22D H 0.444191 0.727546 0.228561 0.144 Uiso 0.729(11) 1 calc GR . P A 1
H22E H 0.476875 0.778328 0.162377 0.144 Uiso 0.729(11) 1 calc GR . P A 1
H22F H 0.411746 0.809750 0.213642 0.144 Uiso 0.729(11) 1 calc GR . P A 1
C203 C 0.9871(9) 0.9326(8) 0.6310(6) 0.185(5) Uani 1 1 d . U . . .
H20D H 1.033204 0.919789 0.658620 0.277 Uiso 1 1 calc GR . . . .
H20E H 0.944015 0.945140 0.662562 0.277 Uiso 1 1 calc GR . . . .
H20F H 1.004468 0.978122 0.601639 0.277 Uiso 1 1 calc GR . . . .
C233 C 0.5139(19) 0.8390(18) 0.1787(13) 0.092(8) Uani 0.271(11) 1 d . U P A 2
H23A H 0.455772 0.831979 0.168154 0.138 Uiso 0.271(11) 1 calc GR . P A 2
H23B H 0.540786 0.802294 0.149940 0.138 Uiso 0.271(11) 1 calc GR . P A 2
H23C H 0.536876 0.893054 0.168349 0.138 Uiso 0.271(11) 1 calc GR . P A 2
C232 C 0.516(2) 0.7468(13) 0.2763(16) 0.108(11) Uani 0.271(11) 1 d . U P A 2
H23D H 0.561854 0.720601 0.261123 0.161 Uiso 0.271(11) 1 calc GR . P A 2
H23E H 0.465805 0.719749 0.255617 0.161 Uiso 0.271(11) 1 calc GR . P A 2
H23F H 0.511733 0.745311 0.327490 0.161 Uiso 0.271(11) 1 calc GR . P A 2
O241 O -0.0057(3) 0.6991(2) 0.2850(2) 0.0849(12) Uani 1 1 d . U . . .
C241 C 0.0054(5) 0.7274(5) 0.3403(3) 0.101(2) Uani 1 1 d . U . . .
C242 C 0.0826(5) 0.7477(7) 0.3771(5) 0.144(4) Uani 1 1 d . U . . .
H24A H 0.112694 0.794148 0.355615 0.217 Uiso 1 1 calc GR . . . .
H24B H 0.114391 0.703486 0.373767 0.217 Uiso 1 1 calc GR . . . .
H24C H 0.072227 0.759156 0.426389 0.217 Uiso 1 1 calc GR . . . .
C243 C -0.0641(8) 0.7129(13) 0.3789(10) 0.144(7) Uani 0.5 1 d . U P B 1
H24D H -0.055098 0.736634 0.425621 0.216 Uiso 0.5 1 calc R . P B 1
H24E H -0.107918 0.735783 0.355531 0.216 Uiso 0.5 1 calc R . P B 1
H24F H -0.079068 0.656027 0.383105 0.216 Uiso 0.5 1 calc R . P B 1
C253 C -0.0311(19) 0.8119(14) 0.3486(9) 0.197(12) Uani 0.5 1 d . U P B 2
H25A H -0.020186 0.833116 0.396042 0.295 Uiso 0.5 1 calc R . P B 2
H25B H -0.005208 0.849099 0.314452 0.295 Uiso 0.5 1 calc R . P B 2
H25C H -0.089724 0.803824 0.340377 0.295 Uiso 0.5 1 calc R . P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu2 N7 2.037(3) . ?
Cu2 N5 2.067(3) . ?
Cu2 N8 2.059(3) 2_565 ?
Cu2 N2 2.080(3) 2_565 ?
Cu51 O51 2.161(3) . ?
Cu51 N56 2.058(3) 2_676 ?
Cu51 N51 1.962(3) . ?
Cu51 N62 1.982(3) . ?
Cu52 N52 2.113(3) 2_676 ?
Cu52 N55 2.036(3) . ?
Cu52 N58 2.058(3) 2_676 ?
Cu52 N57 2.040(3) . ?
Cu1 O1 2.173(3) . ?
Cu1 N6 2.010(3) 2_565 ?
Cu1 N1 1.981(3) . ?
Cu1 N12 2.001(3) . ?
S151 O153 1.425(3) . ?
S151 O151 1.444(3) . ?
S151 O152 1.430(3) . ?
S151 C151 1.813(5) . ?
S1 O1 1.457(3) . ?
S1 O3 1.434(3) . ?
S1 O2 1.422(3) . ?
S1 C41 1.806(5) . ?
S51 O51 1.443(3) . ?
S51 O53 1.437(3) . ?
S51 O52 1.427(3) . ?
S51 C91 1.824(5) . ?
S101 O103 1.420(4) . ?
S101 O102 1.422(4) . ?
S101 O101 1.431(4) . ?
S101 C101 1.803(7) . ?
F1 C41 1.341(6) . ?
F52 C91 1.340(5) . ?
F103 C101 1.306(5) . ?
N7 N8 1.332(4) . ?
N7 C21 1.369(4) . ?
N5 N4 1.355(4) . ?
N5 N6 1.317(4) . ?
N8 N9 1.355(4) . ?
N4 C15 1.370(4) . ?
N4 C14 1.444(5) . ?
N9 C26 1.356(5) . ?
N9 C27 1.464(5) . ?
N2 N1 1.322(4) . ?
N2 N3 1.351(4) . ?
N59 N58 1.337(4) . ?
N59 C76 1.361(5) . ?
N59 C77 1.462(4) . ?
F53 C91 1.349(5) . ?
N52 N53 1.346(4) . ?
N52 N51 1.319(4) . ?
O261 C261 1.207(5) . ?
N6 C20 1.375(5) . ?
F51 C91 1.335(6) . ?
N55 N54 1.351(4) . ?
N55 N56 1.314(4) . ?
N54 C65 1.358(4) . ?
N54 C64 1.462(4) . ?
N53 C57 1.443(4) . ?
N53 C56 1.360(5) . ?
N56 C70 1.378(4) . ?
N1 C1 1.378(5) . ?
N3 C6 1.351(5) . ?
N3 C7 1.461(5) . ?
N58 N57 1.328(4) . ?
N61 N62 1.337(5) . ?
N61 N60 1.328(5) . ?
N61 C84 1.454(5) . ?
N51 C51 1.372(5) . ?
N11 N12 1.326(5) . ?
N11 N10 1.329(4) . ?
N11 C34 1.456(5) . ?
N12 C40 1.370(5) . ?
N57 C71 1.365(5) . ?
N62 C90 1.368(5) . ?
F151 C151 1.315(6) . ?
N10 C35 1.341(5) . ?
F3 C41 1.354(6) . ?
N60 C85 1.358(5) . ?
F2 C41 1.306(6) . ?
C21 C26 1.399(5) . ?
C21 C22 1.404(5) . ?
F153 C151 1.329(7) . ?
C15 C20 1.379(6) . ?
C15 C16 1.406(5) . ?
F152 C151 1.330(6) . ?
C28 C29 1.382(5) . ?
C28 C33 1.402(5) . ?
C28 C27 1.526(5) . ?
O221 C221 1.211(6) . ?
C26 C25 1.396(5) . ?
C1 C6 1.379(5) . ?
C1 C2 1.395(6) . ?
C29 H29 0.9500 . ?
C29 C30 1.387(5) . ?
C8 C7 1.518(5) . ?
C8 C13 1.397(5) . ?
C8 C9 1.392(5) . ?
C6 C5 1.415(6) . ?
C20 C19 1.415(5) . ?
C40 C35 1.406(6) . ?
C40 C39 1.401(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C13 C12 1.383(5) . ?
C13 C14 1.510(5) . ?
C22 H22 0.9500 . ?
C22 C23 1.373(6) . ?
C76 C71 1.386(5) . ?
C76 C75 1.394(6) . ?
C63 C58 1.414(5) . ?
C63 C64 1.502(6) . ?
C63 C62 1.388(6) . ?
C30 H30 0.9500 . ?
C30 C31 1.386(5) . ?
C58 C57 1.499(6) . ?
C58 C59 1.397(6) . ?
C51 C56 1.394(5) . ?
C51 C52 1.408(5) . ?
C33 C32 1.399(5) . ?
C33 C34 1.502(6) . ?
C65 C70 1.390(5) . ?
C65 C66 1.402(5) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C70 C69 1.409(5) . ?
C57 H57A 0.9900 . ?
C57 H57B 0.9900 . ?
C90 C85 1.422(6) . ?
C90 C89 1.405(6) . ?
C71 C72 1.407(5) . ?
C16 H16 0.9500 . ?
C16 C17 1.377(6) . ?
C59 H59 0.9500 . ?
C59 C60 1.368(6) . ?
C32 H32 0.9500 . ?
C32 C31 1.365(6) . ?
C78 C77 1.505(5) . ?
C78 C83 1.413(5) . ?
C78 C79 1.398(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.404(6) . ?
C12 H12 0.9500 . ?
C12 C11 1.382(6) . ?
C31 H31 0.9500 . ?
C85 C86 1.405(5) . ?
C56 C55 1.402(5) . ?
C25 H25 0.9500 . ?
C25 C24 1.370(6) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
F102 C101 1.296(6) . ?
C17 H17 0.9500 . ?
C17 C18 1.399(6) . ?
C77 H77A 0.9900 . ?
C77 H77B 0.9900 . ?
C5 H5 0.9500 . ?
C5 C4 1.360(6) . ?
C64 H64A 0.9900 . ?
C64 H64B 0.9900 . ?
C10 H10 0.9500 . ?
C10 C11 1.379(6) . ?
C35 C36 1.430(5) . ?
C83 C84 1.524(5) . ?
C83 C82 1.379(5) . ?
F101 C101 1.359(7) . ?
C66 H66 0.9500 . ?
C66 C67 1.374(5) . ?
C52 H52 0.9500 . ?
C52 C53 1.371(6) . ?
C79 H79 0.9500 . ?
C79 C80 1.387(6) . ?
C69 H69 0.9500 . ?
C69 C68 1.362(5) . ?
C19 H19 0.9500 . ?
C19 C18 1.370(6) . ?
C89 H89 0.9500 . ?
C89 C88 1.378(6) . ?
C67 H67 0.9500 . ?
C67 C68 1.415(6) . ?
C68 H68 0.9500 . ?
C24 H24 0.9500 . ?
C24 C23 1.408(6) . ?
C18 H18 0.9500 . ?
C36 H36 0.9500 . ?
C36 C37 1.365(7) . ?
C2 H2 0.9500 . ?
C2 C3 1.376(6) . ?
C80 H80 0.9500 . ?
C80 C81 1.386(6) . ?
C11 H11 0.9500 . ?
C23 H23 0.9500 . ?
C62 H62 0.9500 . ?
C62 C61 1.376(6) . ?
C84 H84A 0.9900 . ?
C84 H84B 0.9900 . ?
C81 H81 0.9500 . ?
C81 C82 1.384(6) . ?
C82 H82 0.9500 . ?
C86 H86 0.9500 . ?
C86 C87 1.360(6) . ?
C72 H72 0.9500 . ?
C72 C73 1.365(6) . ?
C87 H87 0.9500 . ?
C87 C88 1.427(7) . ?
C261 C262 1.483(7) . ?
C261 C263 1.493(8) . ?
C60 H60 0.9500 . ?
C60 C61 1.394(6) . ?
C4 H4 0.9500 . ?
C4 C3 1.412(6) . ?
C3 H3 0.9500 . ?
C55 H55 0.9500 . ?
C55 C54 1.370(6) . ?
C61 H61 0.9500 . ?
C88 H88 0.9500 . ?
C54 H54 0.9500 . ?
C54 C53 1.414(6) . ?
C39 H39 0.9500 . ?
C39 C38 1.368(6) . ?
C53 H53 0.9500 . ?
C37 H37 0.9500 . ?
C37 C38 1.402(7) . ?
C221 C222 1.525(8) . ?
C221 C223 1.508(10) . ?
C221 C233 1.51(2) . ?
C221 C232 1.36(2) . ?
C38 H38 0.9500 . ?
C75 H75 0.9500 . ?
C75 C74 1.360(6) . ?
C73 H73 0.9500 . ?
C73 C74 1.423(7) . ?
C74 H74 0.9500 . ?
C262 H26A 0.9800 . ?
C262 H26B 0.9800 . ?
C262 H26C 0.9800 . ?
C222 H22A 0.9800 . ?
C222 H22B 0.9800 . ?
C222 H22C 0.9800 . ?
C201 O201 1.267(10) . ?
C201 C202 1.469(14) . ?
C201 C203 1.417(15) . ?
C263 H26D 0.9800 . ?
C263 H26E 0.9800 . ?
C263 H26F 0.9800 . ?
C202 H20A 0.9800 . ?
C202 H20B 0.9800 . ?
C202 H20C 0.9800 . ?
C223 H22D 0.9800 . ?
C223 H22E 0.9800 . ?
C223 H22F 0.9800 . ?
C203 H20D 0.9800 . ?
C203 H20E 0.9800 . ?
C203 H20F 0.9800 . ?
C233 H23A 0.9800 . ?
C233 H23B 0.9800 . ?
C233 H23C 0.9800 . ?
C232 H23D 0.9800 . ?
C232 H23E 0.9800 . ?
C232 H23F 0.9800 . ?
O241 C241 1.163(7) . ?
C241 C242 1.464(10) . ?
C241 C243 1.370(17) . ?
C241 C253 1.647(19) . ?
C242 H24A 0.9800 . ?
C242 H24B 0.9800 . ?
C242 H24C 0.9800 . ?
C243 H24D 0.9800 . ?
C243 H24E 0.9800 . ?
C243 H24F 0.9800 . ?
C253 H25A 0.9800 . ?
C253 H25B 0.9800 . ?
C253 H25C 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
N7 Cu2 N5 112.74(11) . . ?
N7 Cu2 N8 103.84(11) . 2_565 ?
N7 Cu2 N2 112.50(12) . 2_565 ?
N5 Cu2 N2 104.35(12) . 2_565 ?
N8 Cu2 N5 117.85(12) 2_565 . ?
N8 Cu2 N2 105.57(12) 2_565 2_565 ?
N56 Cu51 O51 93.42(12) 2_676 . ?
N51 Cu51 O51 108.42(12) . . ?
N51 Cu51 N56 107.10(12) . 2_676 ?
N51 Cu51 N62 133.28(13) . . ?
N62 Cu51 O51 100.22(12) . . ?
N62 Cu51 N56 107.15(13) . 2_676 ?
N55 Cu52 N52 104.04(11) . 2_676 ?
N55 Cu52 N58 119.07(12) . 2_676 ?
N55 Cu52 N57 113.58(12) . . ?
N58 Cu52 N52 105.56(12) 2_676 2_676 ?
N57 Cu52 N52 110.31(12) . 2_676 ?
N57 Cu52 N58 103.96(12) . 2_676 ?
N6 Cu1 O1 103.78(12) 2_565 . ?
N1 Cu1 O1 103.49(12) . . ?
N1 Cu1 N6 108.08(12) . 2_565 ?
N1 Cu1 N12 125.39(13) . . ?
N12 Cu1 O1 99.49(12) . . ?
N12 Cu1 N6 113.41(13) . 2_565 ?
O153 S151 O151 114.75(19) . . ?
O153 S151 O152 114.2(2) . . ?
O153 S151 C151 104.0(2) . . ?
O151 S151 C151 104.2(2) . . ?
O152 S151 O151 114.9(2) . . ?
O152 S151 C151 102.7(3) . . ?
O1 S1 C41 101.7(2) . . ?
O3 S1 O1 114.32(18) . . ?
O3 S1 C41 103.3(2) . . ?
O2 S1 O1 113.7(2) . . ?
O2 S1 O3 117.0(2) . . ?
O2 S1 C41 104.3(2) . . ?
O51 S51 C91 103.2(2) . . ?
O53 S51 O51 114.77(18) . . ?
O53 S51 C91 103.1(2) . . ?
O52 S51 O51 114.45(18) . . ?
O52 S51 O53 116.12(19) . . ?
O52 S51 C91 102.6(2) . . ?
O103 S101 O102 113.8(2) . . ?
O103 S101 O101 113.9(3) . . ?
O103 S101 C101 103.8(3) . . ?
O102 S101 O101 115.6(3) . . ?
O102 S101 C101 104.0(3) . . ?
O101 S101 C101 103.8(3) . . ?
N8 N7 Cu2 128.0(2) . . ?
N8 N7 C21 108.3(3) . . ?
C21 N7 Cu2 123.6(2) . . ?
S51 O51 Cu51 128.27(17) . . ?
N4 N5 Cu2 125.4(2) . . ?
N6 N5 Cu2 125.4(2) . . ?
N6 N5 N4 109.2(3) . . ?
N7 N8 Cu2 128.1(2) . 2_565 ?
N7 N8 N9 108.1(3) . . ?
N9 N8 Cu2 123.6(2) . 2_565 ?
S1 O1 Cu1 129.56(17) . . ?
N5 N4 C15 109.3(3) . . ?
N5 N4 C14 121.0(3) . . ?
C15 N4 C14 129.3(3) . . ?
N8 N9 C26 110.5(3) . . ?
N8 N9 C27 120.7(3) . . ?
C26 N9 C27 128.6(3) . . ?
N1 N2 Cu2 127.8(2) . 2_565 ?
N1 N2 N3 107.5(3) . . ?
N3 N2 Cu2 124.6(2) . 2_565 ?
N58 N59 C76 110.3(3) . . ?
N58 N59 C77 121.1(3) . . ?
C76 N59 C77 128.6(3) . . ?
N53 N52 Cu52 121.8(2) . 2_676 ?
N51 N52 Cu52 129.2(2) . 2_676 ?
N51 N52 N53 108.8(3) . . ?
N5 N6 Cu1 126.8(2) . 2_565 ?
N5 N6 C20 107.7(3) . . ?
C20 N6 Cu1 123.4(2) . 2_565 ?
N54 N55 Cu52 126.4(2) . . ?
N56 N55 Cu52 125.0(2) . . ?
N56 N55 N54 108.5(3) . . ?
N55 N54 C65 110.5(3) . . ?
N55 N54 C64 121.1(3) . . ?
C65 N54 C64 128.0(3) . . ?
N52 N53 C57 121.3(3) . . ?
N52 N53 C56 110.4(3) . . ?
C56 N53 C57 128.2(3) . . ?
N55 N56 Cu51 127.7(2) . 2_676 ?
N55 N56 C70 108.1(3) . . ?
C70 N56 Cu51 123.0(2) . 2_676 ?
N2 N1 Cu1 125.3(3) . . ?
N2 N1 C1 108.7(3) . . ?
C1 N1 Cu1 125.9(3) . . ?
N2 N3 C6 110.7(3) . . ?
N2 N3 C7 120.7(3) . . ?
C6 N3 C7 128.5(3) . . ?
N59 N58 Cu52 122.9(2) . 2_676 ?
N57 N58 Cu52 128.2(3) . 2_676 ?
N57 N58 N59 108.7(3) . . ?
N62 N61 C84 121.5(3) . . ?
N60 N61 N62 117.0(3) . . ?
N60 N61 C84 121.5(3) . . ?
N52 N51 Cu51 124.3(2) . . ?
N52 N51 C51 107.9(3) . . ?
C51 N51 Cu51 127.7(2) . . ?
N12 N11 N10 116.4(3) . . ?
N12 N11 C34 122.2(3) . . ?
N10 N11 C34 121.3(3) . . ?
N11 N12 Cu1 123.6(2) . . ?
N11 N12 C40 103.7(3) . . ?
C40 N12 Cu1 132.6(3) . . ?
N58 N57 Cu52 127.9(3) . . ?
N58 N57 C71 107.7(3) . . ?
C71 N57 Cu52 124.2(2) . . ?
N61 N62 Cu51 122.8(2) . . ?
N61 N62 C90 103.3(3) . . ?
C90 N62 Cu51 132.5(3) . . ?
N11 N10 C35 103.3(3) . . ?
N61 N60 C85 103.3(3) . . ?
N7 C21 C26 108.3(3) . . ?
N7 C21 C22 130.5(3) . . ?
C26 C21 C22 121.2(3) . . ?
N4 C15 C20 105.0(3) . . ?
N4 C15 C16 131.9(4) . . ?
C20 C15 C16 123.1(3) . . ?
C29 C28 C33 119.4(3) . . ?
C29 C28 C27 121.9(3) . . ?
C33 C28 C27 118.6(3) . . ?
N9 C26 C21 104.8(3) . . ?
N9 C26 C25 132.7(3) . . ?
C25 C26 C21 122.5(3) . . ?
N1 C1 C6 107.7(3) . . ?
N1 C1 C2 130.5(4) . . ?
C6 C1 C2 121.8(4) . . ?
C28 C29 H29 119.6 . . ?
C28 C29 C30 120.8(3) . . ?
C30 C29 H29 119.6 . . ?
C13 C8 C7 117.9(3) . . ?
C9 C8 C7 122.4(3) . . ?
C9 C8 C13 119.8(3) . . ?
N3 C6 C1 105.3(3) . . ?
N3 C6 C5 132.2(4) . . ?
C1 C6 C5 122.4(4) . . ?
N6 C20 C15 108.9(3) . . ?
N6 C20 C19 129.8(4) . . ?
C15 C20 C19 121.2(3) . . ?
N12 C40 C35 106.9(4) . . ?
N12 C40 C39 131.6(4) . . ?
C39 C40 C35 121.5(4) . . ?
N3 C7 C8 113.2(3) . . ?
N3 C7 H7A 108.9 . . ?
N3 C7 H7B 108.9 . . ?
C8 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
H7A C7 H7B 107.8 . . ?
C8 C13 C14 118.3(3) . . ?
C12 C13 C8 119.7(4) . . ?
C12 C13 C14 122.0(3) . . ?
C21 C22 H22 122.0 . . ?
C23 C22 C21 116.0(4) . . ?
C23 C22 H22 122.0 . . ?
N59 C76 C71 104.5(3) . . ?
N59 C76 C75 132.6(4) . . ?
C71 C76 C75 122.9(4) . . ?
C58 C63 C64 118.3(3) . . ?
C62 C63 C58 119.0(4) . . ?
C62 C63 C64 122.6(3) . . ?
C29 C30 H30 120.2 . . ?
C31 C30 C29 119.6(4) . . ?
C31 C30 H30 120.2 . . ?
C63 C58 C57 117.5(3) . . ?
C59 C58 C63 119.0(4) . . ?
C59 C58 C57 123.5(3) . . ?
N51 C51 C56 108.6(3) . . ?
N51 C51 C52 130.2(3) . . ?
C56 C51 C52 121.2(3) . . ?
C28 C33 C34 120.3(3) . . ?
C32 C33 C28 119.0(4) . . ?
C32 C33 C34 120.5(3) . . ?
N54 C65 C70 104.4(3) . . ?
N54 C65 C66 132.9(3) . . ?
C70 C65 C66 122.5(3) . . ?
N9 C27 C28 113.9(3) . . ?
N9 C27 H27A 108.8 . . ?
N9 C27 H27B 108.8 . . ?
C28 C27 H27A 108.8 . . ?
C28 C27 H27B 108.8 . . ?
H27A C27 H27B 107.7 . . ?
N56 C70 C65 108.4(3) . . ?
N56 C70 C69 130.3(3) . . ?
C65 C70 C69 121.3(3) . . ?
N53 C57 C58 114.2(3) . . ?
N53 C57 H57A 108.7 . . ?
N53 C57 H57B 108.7 . . ?
C58 C57 H57A 108.7 . . ?
C58 C57 H57B 108.7 . . ?
H57A C57 H57B 107.6 . . ?
N62 C90 C85 107.6(4) . . ?
N62 C90 C89 130.6(4) . . ?
C89 C90 C85 121.7(4) . . ?
N57 C71 C76 108.7(3) . . ?
N57 C71 C72 130.2(4) . . ?
C76 C71 C72 121.1(4) . . ?
C15 C16 H16 122.7 . . ?
C17 C16 C15 114.7(4) . . ?
C17 C16 H16 122.7 . . ?
C58 C59 H59 119.4 . . ?
C60 C59 C58 121.2(4) . . ?
C60 C59 H59 119.4 . . ?
C33 C32 H32 119.6 . . ?
C31 C32 C33 120.8(4) . . ?
C31 C32 H32 119.6 . . ?
C83 C78 C77 119.6(3) . . ?
C79 C78 C77 121.9(3) . . ?
C79 C78 C83 118.6(3) . . ?
C8 C9 H9 120.2 . . ?
C8 C9 C10 119.6(4) . . ?
C10 C9 H9 120.2 . . ?
C13 C12 H12 119.6 . . ?
C11 C12 C13 120.9(4) . . ?
C11 C12 H12 119.6 . . ?
C30 C31 H31 119.8 . . ?
C32 C31 C30 120.3(4) . . ?
C32 C31 H31 119.8 . . ?
N60 C85 C90 108.7(3) . . ?
N60 C85 C86 130.0(4) . . ?
C86 C85 C90 121.3(4) . . ?
N53 C56 C51 104.3(3) . . ?
N53 C56 C55 132.4(3) . . ?
C51 C56 C55 123.2(3) . . ?
C26 C25 H25 122.2 . . ?
C24 C25 C26 115.5(4) . . ?
C24 C25 H25 122.2 . . ?
N11 C34 C33 113.2(3) . . ?
N11 C34 H34A 108.9 . . ?
N11 C34 H34B 108.9 . . ?
C33 C34 H34A 108.9 . . ?
C33 C34 H34B 108.9 . . ?
H34A C34 H34B 107.7 . . ?
N4 C14 C13 114.4(3) . . ?
N4 C14 H14A 108.6 . . ?
N4 C14 H14B 108.6 . . ?
C13 C14 H14A 108.6 . . ?
C13 C14 H14B 108.6 . . ?
H14A C14 H14B 107.6 . . ?
C16 C17 H17 118.6 . . ?
C16 C17 C18 122.9(4) . . ?
C18 C17 H17 118.6 . . ?
N59 C77 C78 113.1(3) . . ?
N59 C77 H77A 109.0 . . ?
N59 C77 H77B 109.0 . . ?
C78 C77 H77A 109.0 . . ?
C78 C77 H77B 109.0 . . ?
H77A C77 H77B 107.8 . . ?
C6 C5 H5 122.4 . . ?
C4 C5 C6 115.2(4) . . ?
C4 C5 H5 122.4 . . ?
N54 C64 C63 114.2(3) . . ?
N54 C64 H64A 108.7 . . ?
N54 C64 H64B 108.7 . . ?
C63 C64 H64A 108.7 . . ?
C63 C64 H64B 108.7 . . ?
H64A C64 H64B 107.6 . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.1(4) . . ?
C11 C10 H10 119.9 . . ?
N10 C35 C40 109.6(3) . . ?
N10 C35 C36 129.3(4) . . ?
C40 C35 C36 121.1(4) . . ?
C78 C83 C84 118.8(3) . . ?
C82 C83 C78 119.3(4) . . ?
C82 C83 C84 121.8(3) . . ?
C65 C66 H66 122.3 . . ?
C67 C66 C65 115.4(4) . . ?
C67 C66 H66 122.3 . . ?
C51 C52 H52 122.3 . . ?
C53 C52 C51 115.3(4) . . ?
C53 C52 H52 122.3 . . ?
C78 C79 H79 119.4 . . ?
C80 C79 C78 121.2(4) . . ?
C80 C79 H79 119.4 . . ?
C70 C69 H69 121.9 . . ?
C68 C69 C70 116.1(3) . . ?
C68 C69 H69 121.9 . . ?
C20 C19 H19 122.1 . . ?
C18 C19 C20 115.8(4) . . ?
C18 C19 H19 122.1 . . ?
C90 C89 H89 122.1 . . ?
C88 C89 C90 115.9(4) . . ?
C88 C89 H89 122.1 . . ?
C66 C67 H67 118.8 . . ?
C66 C67 C68 122.3(4) . . ?
C68 C67 H67 118.8 . . ?
C69 C68 C67 122.3(3) . . ?
C69 C68 H68 118.9 . . ?
C67 C68 H68 118.9 . . ?
C25 C24 H24 118.7 . . ?
C25 C24 C23 122.6(4) . . ?
C23 C24 H24 118.7 . . ?
C17 C18 H18 118.8 . . ?
C19 C18 C17 122.3(4) . . ?
C19 C18 H18 118.8 . . ?
C35 C36 H36 121.9 . . ?
C37 C36 C35 116.2(4) . . ?
C37 C36 H36 121.9 . . ?
C1 C2 H2 122.0 . . ?
C3 C2 C1 116.1(4) . . ?
C3 C2 H2 122.0 . . ?
C79 C80 H80 120.2 . . ?
C81 C80 C79 119.5(4) . . ?
C81 C80 H80 120.2 . . ?
C12 C11 H11 120.0 . . ?
C10 C11 C12 119.9(4) . . ?
C10 C11 H11 120.0 . . ?
C22 C23 C24 122.1(4) . . ?
C22 C23 H23 119.0 . . ?
C24 C23 H23 119.0 . . ?
C63 C62 H62 119.5 . . ?
C61 C62 C63 120.9(4) . . ?
C61 C62 H62 119.5 . . ?
N61 C84 C83 113.2(3) . . ?
N61 C84 H84A 108.9 . . ?
N61 C84 H84B 108.9 . . ?
C83 C84 H84A 108.9 . . ?
C83 C84 H84B 108.9 . . ?
H84A C84 H84B 107.7 . . ?
C80 C81 H81 120.1 . . ?
C82 C81 C80 119.8(4) . . ?
C82 C81 H81 120.1 . . ?
C83 C82 C81 121.5(4) . . ?
C83 C82 H82 119.3 . . ?
C81 C82 H82 119.3 . . ?
C85 C86 H86 121.7 . . ?
C87 C86 C85 116.6(4) . . ?
C87 C86 H86 121.7 . . ?
C71 C72 H72 121.9 . . ?
C73 C72 C71 116.1(4) . . ?
C73 C72 H72 121.9 . . ?
C86 C87 H87 118.8 . . ?
C86 C87 C88 122.4(4) . . ?
C88 C87 H87 118.8 . . ?
O261 C261 C262 121.8(5) . . ?
O261 C261 C263 119.9(5) . . ?
C262 C261 C263 118.4(5) . . ?
C59 C60 H60 120.2 . . ?
C59 C60 C61 119.6(4) . . ?
C61 C60 H60 120.2 . . ?
C5 C4 H4 118.6 . . ?
C5 C4 C3 122.8(4) . . ?
C3 C4 H4 118.6 . . ?
C2 C3 C4 121.8(4) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C56 C55 H55 122.5 . . ?
C54 C55 C56 115.0(4) . . ?
C54 C55 H55 122.5 . . ?
C62 C61 C60 120.3(4) . . ?
C62 C61 H61 119.9 . . ?
C60 C61 H61 119.9 . . ?
C89 C88 C87 122.2(4) . . ?
C89 C88 H88 118.9 . . ?
C87 C88 H88 118.9 . . ?
C55 C54 H54 118.9 . . ?
C55 C54 C53 122.2(4) . . ?
C53 C54 H54 118.9 . . ?
C40 C39 H39 122.1 . . ?
C38 C39 C40 115.9(4) . . ?
C38 C39 H39 122.1 . . ?
F52 C91 S51 112.4(3) . . ?
F52 C91 F53 106.1(4) . . ?
F53 C91 S51 112.2(3) . . ?
F51 C91 S51 112.0(4) . . ?
F51 C91 F52 106.4(4) . . ?
F51 C91 F53 107.3(4) . . ?
C52 C53 C54 123.0(4) . . ?
C52 C53 H53 118.5 . . ?
C54 C53 H53 118.5 . . ?
C36 C37 H37 119.2 . . ?
C36 C37 C38 121.7(4) . . ?
C38 C37 H37 119.2 . . ?
F1 C41 S1 111.5(3) . . ?
F1 C41 F3 105.6(4) . . ?
F3 C41 S1 111.8(3) . . ?
F2 C41 S1 112.4(4) . . ?
F2 C41 F1 108.3(4) . . ?
F2 C41 F3 107.0(4) . . ?
O221 C221 C222 118.9(5) . . ?
O221 C221 C223 126.0(5) . . ?
O221 C221 C233 117.5(11) . . ?
O221 C221 C232 120.4(13) . . ?
C223 C221 C222 113.8(5) . . ?
C232 C221 C233 118.0(18) . . ?
C39 C38 C37 123.6(5) . . ?
C39 C38 H38 118.2 . . ?
C37 C38 H38 118.2 . . ?
C76 C75 H75 122.1 . . ?
C74 C75 C76 115.7(4) . . ?
C74 C75 H75 122.1 . . ?
F103 C101 S101 114.3(4) . . ?
F103 C101 F101 104.9(4) . . ?
F102 C101 S101 112.5(4) . . ?
F102 C101 F103 107.8(5) . . ?
F102 C101 F101 106.4(6) . . ?
F101 C101 S101 110.3(4) . . ?
F151 C151 S151 112.0(4) . . ?
F151 C151 F153 108.2(5) . . ?
F151 C151 F152 108.7(5) . . ?
F153 C151 S151 110.4(4) . . ?
F153 C151 F152 107.2(4) . . ?
F152 C151 S151 110.1(4) . . ?
C72 C73 H73 119.0 . . ?
C72 C73 C74 122.0(4) . . ?
C74 C73 H73 119.0 . . ?
C75 C74 C73 122.2(5) . . ?
C75 C74 H74 118.9 . . ?
C73 C74 H74 118.9 . . ?
C261 C262 H26A 109.5 . . ?
C261 C262 H26B 109.5 . . ?
C261 C262 H26C 109.5 . . ?
H26A C262 H26B 109.5 . . ?
H26A C262 H26C 109.5 . . ?
H26B C262 H26C 109.5 . . ?
C221 C222 H22A 109.5 . . ?
C221 C222 H22B 109.5 . . ?
C221 C222 H22C 109.5 . . ?
H22A C222 H22B 109.5 . . ?
H22A C222 H22C 109.5 . . ?
H22B C222 H22C 109.5 . . ?
O201 C201 C202 114.5(12) . . ?
O201 C201 C203 120.5(12) . . ?
C203 C201 C202 124.4(11) . . ?
C261 C263 H26D 109.5 . . ?
C261 C263 H26E 109.5 . . ?
C261 C263 H26F 109.5 . . ?
H26D C263 H26E 109.5 . . ?
H26D C263 H26F 109.5 . . ?
H26E C263 H26F 109.5 . . ?
C201 C202 H20A 109.5 . . ?
C201 C202 H20B 109.5 . . ?
C201 C202 H20C 109.5 . . ?
H20A C202 H20B 109.5 . . ?
H20A C202 H20C 109.5 . . ?
H20B C202 H20C 109.5 . . ?
C221 C223 H22D 109.5 . . ?
C221 C223 H22E 109.5 . . ?
C221 C223 H22F 109.5 . . ?
H22D C223 H22E 109.5 . . ?
H22D C223 H22F 109.5 . . ?
H22E C223 H22F 109.5 . . ?
C201 C203 H20D 109.5 . . ?
C201 C203 H20E 109.5 . . ?
C201 C203 H20F 109.5 . . ?
H20D C203 H20E 109.5 . . ?
H20D C203 H20F 109.5 . . ?
H20E C203 H20F 109.5 . . ?
C221 C233 H23A 109.5 . . ?
C221 C233 H23B 109.5 . . ?
C221 C233 H23C 109.5 . . ?
H23A C233 H23B 109.5 . . ?
H23A C233 H23C 109.5 . . ?
H23B C233 H23C 109.5 . . ?
C221 C232 H23D 109.5 . . ?
C221 C232 H23E 109.5 . . ?
C221 C232 H23F 109.5 . . ?
H23D C232 H23E 109.5 . . ?
H23D C232 H23F 109.5 . . ?
H23E C232 H23F 109.5 . . ?
O241 C241 C242 128.2(8) . . ?
O241 C241 C243 109.1(10) . . ?
O241 C241 C253 112.8(9) . . ?
C242 C241 C253 99.2(13) . . ?
C243 C241 C242 118.8(9) . . ?
C241 C242 H24A 109.5 . . ?
C241 C242 H24B 109.5 . . ?
C241 C242 H24C 109.5 . . ?
H24A C242 H24B 109.5 . . ?
H24A C242 H24C 109.5 . . ?
H24B C242 H24C 109.5 . . ?
C241 C243 H24D 109.5 . . ?
C241 C243 H24E 109.5 . . ?
C241 C243 H24F 109.5 . . ?
H24D C243 H24E 109.5 . . ?
H24D C243 H24F 109.5 . . ?
H24E C243 H24F 109.5 . . ?
C241 C253 H25A 109.5 . . ?
C241 C253 H25B 109.5 . . ?
C241 C253 H25C 109.5 . . ?
H25A C253 H25B 109.5 . . ?
H25A C253 H25C 109.5 . . ?
H25B C253 H25C 109.5 . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.500 0.500 197.5 21.7 ?
2 0.313 0.469 0.271 7.3 0.0 ?
3 0.500 0.000 0.000 143.0 3.1 ?
4 0.500 0.500 0.000 30.8 0.0 ?
5 0.687 0.531 0.729 7.3 0.0 ?

_olex2_date_sample_data_collection 2017-05-10
_olex2_date_sample_submission    2017-05-04
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id EL1460A
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.587
_oxdiff_exptl_absorpt_empirical_full_min 0.773
####################################################################### 
# 
# 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_cu231
_database_code_depnum_ccdc_archive 'CCDC 1831793'
_audit_update_record             
;
2018-03-22 deposited with the CCDC.
2018-05-01 downloaded from the CCDC.
;
_audit_creation_date             2018-03-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H17 N3'
_chemical_formula_sum            'C13 H17 N3'
_chemical_formula_weight         215.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N3
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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.0813(10)
_cell_length_b                   5.4875(3)
_cell_length_c                   17.7677(16)
_cell_angle_alpha                90
_cell_angle_beta                 108.906(9)
_cell_angle_gamma                90
_cell_volume                     1206.62(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1073
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.2900
_cell_measurement_theta_min      5.3420
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.563
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82654
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            3667
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.336
_diffrn_reflns_theta_min         5.318
_diffrn_ambient_temperature      173.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1033
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -18.00  86.00   1.00    5.45    --   54.75 -38.00 -30.00  104
  2  ω     40.00  82.00   1.00    5.47    --  109.50-111.00   0.00   42
  3  ω     46.00 125.00   1.00    5.47    --  109.50 -92.00  60.00   79
  4  ω     47.00 137.00   1.00    5.47    --  109.50 -38.00 -30.00   90
  5  ω     78.00 173.00   1.00    5.47    --  109.50  25.00 -30.00   95
  6  ω     80.00 168.00   1.00    5.47    --  109.50  25.00  60.00   88
  7  ω     32.00 120.00   1.00    5.45    --   54.75  57.00 -60.00   88
  8  ω     16.00  45.00   1.00    1.03    --    0.00 -99.00   0.00   29
  9  ω    -24.00   5.00   1.00    1.03    --    0.00 -99.00   0.00   29
 10  ω     36.00  84.00   1.00    5.47    --  109.50-111.00-150.00   48
 11  ω     14.00  90.00   1.00    5.45    --   54.75-125.00-150.00   76
 12  ω     36.00  74.00   1.00    5.47    --  109.50-111.00 150.00   38
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1150300000
_diffrn_orient_matrix_UB_12      -0.0432399000
_diffrn_orient_matrix_UB_13      0.0029209000
_diffrn_orient_matrix_UB_21      0.0428803000
_diffrn_orient_matrix_UB_22      0.0175155000
_diffrn_orient_matrix_UB_23      0.0914341000
_diffrn_orient_matrix_UB_31      -0.0207791000
_diffrn_orient_matrix_UB_32      0.2768140000
_diffrn_orient_matrix_UB_33      -0.0053043000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1638
_reflns_number_total             2234
_reflns_odcompleteness_completeness 98.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2234
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0469
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0603P)²+0.0129P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1150
_refine_ls_wR_factor_ref         0.1336
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C10(H10A,H10B), C12(H12A,H12B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C5(H5), C1(H1), C3(H3), C2(H2), C4(H4)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.70990(11) 0.2881(3) 0.44945(9) 0.0391(4) Uani 1 1 d . . . . .
N2 N 0.71834(13) 0.0449(3) 0.45315(10) 0.0452(4) Uani 1 1 d . . . . .
N3 N 0.80447(12) -0.0124(3) 0.43327(9) 0.0426(4) Uani 1 1 d . . . . .
C8 C 0.78996(14) 0.3872(3) 0.42714(10) 0.0375(4) Uani 1 1 d . . . . .
H8 H 0.8018 0.5552 0.4200 0.045 Uiso 1 1 calc R . . . .
C9 C 0.85027(14) 0.1950(3) 0.41704(10) 0.0361(4) Uani 1 1 d . . . . .
C11 C 0.98867(14) 0.4410(3) 0.37805(11) 0.0408(4) Uani 1 1 d . . . . .
H11A H 0.9971 0.5471 0.4247 0.049 Uiso 1 1 calc R . . . .
H11B H 0.9328 0.5144 0.3319 0.049 Uiso 1 1 calc R . . . .
C6 C 0.51720(14) 0.3958(3) 0.39750(11) 0.0394(4) Uani 1 1 d . . . . .
C10 C 0.95078(15) 0.1905(3) 0.39434(12) 0.0427(4) Uani 1 1 d . . . . .
H10A H 0.9377 0.0886 0.3462 0.051 Uiso 1 1 calc R . . . .
H10B H 1.0092 0.1126 0.4378 0.051 Uiso 1 1 calc R . . . .
C12 C 1.09535(15) 0.4315(4) 0.36092(12) 0.0476(5) Uani 1 1 d . . . . .
H12A H 1.1506 0.3530 0.4063 0.057 Uiso 1 1 calc R . . . .
H12B H 1.0862 0.3296 0.3132 0.057 Uiso 1 1 calc R . . . .
C7 C 0.62047(15) 0.4100(4) 0.46668(12) 0.0470(5) Uani 1 1 d . . . . .
H7A H 0.6394 0.5831 0.4796 0.056 Uiso 1 1 calc R . . . .
H7B H 0.6093 0.3332 0.5138 0.056 Uiso 1 1 calc R . . . .
C5 C 0.44549(16) 0.2059(3) 0.39058(13) 0.0508(5) Uani 1 1 d . . . . .
H5 H 0.4607 0.0844 0.4308 0.061 Uiso 1 1 calc R . . . .
C13 C 1.13540(17) 0.6825(4) 0.34718(13) 0.0526(5) Uani 1 1 d . . . . .
H13A H 1.0817 0.7600 0.3017 0.079 Uiso 1 1 calc GR . . . .
H13B H 1.2039 0.6662 0.3363 0.079 Uiso 1 1 calc GR . . . .
H13C H 1.1464 0.7830 0.3947 0.079 Uiso 1 1 calc GR . . . .
C1 C 0.49288(17) 0.5700(4) 0.33779(13) 0.0514(5) Uani 1 1 d . . . . .
H1 H 0.5408 0.7030 0.3415 0.062 Uiso 1 1 calc R . . . .
C3 C 0.33003(17) 0.3622(4) 0.26743(13) 0.0574(6) Uani 1 1 d . . . . .
H3 H 0.2662 0.3496 0.2228 0.069 Uiso 1 1 calc R . . . .
C2 C 0.39971(19) 0.5524(4) 0.27295(13) 0.0604(6) Uani 1 1 d . . . . .
H2 H 0.3841 0.6723 0.2322 0.073 Uiso 1 1 calc R . . . .
C4 C 0.35231(18) 0.1897(4) 0.32636(14) 0.0591(6) Uani 1 1 d . . . . .
H4 H 0.3034 0.0589 0.3229 0.071 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N2 1.339(2) . ?
N1 C8 1.349(2) . ?
N1 C7 1.464(2) . ?
N2 N3 1.323(2) . ?
N3 C9 1.360(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.363(2) . ?
C9 C10 1.495(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C10 1.520(2) . ?
C11 C12 1.522(3) . ?
C6 C7 1.505(3) . ?
C6 C5 1.381(2) . ?
C6 C1 1.386(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.521(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C5 H5 0.9500 . ?
C5 C4 1.376(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C1 H1 0.9500 . ?
C1 C2 1.383(3) . ?
C3 H3 0.9500 . ?
C3 C2 1.368(3) . ?
C3 C4 1.371(3) . ?
C2 H2 0.9500 . ?
C4 H4 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
N2 N1 C8 110.91(15) . . ?
N2 N1 C7 120.27(15) . . ?
C8 N1 C7 128.80(16) . . ?
N3 N2 N1 106.71(14) . . ?
N2 N3 C9 109.25(14) . . ?
N1 C8 H8 127.3 . . ?
N1 C8 C9 105.32(15) . . ?
C9 C8 H8 127.3 . . ?
N3 C9 C8 107.81(15) . . ?
N3 C9 C10 122.00(15) . . ?
C8 C9 C10 130.17(15) . . ?
H11A C11 H11B 107.8 . . ?
C10 C11 H11A 109.1 . . ?
C10 C11 H11B 109.1 . . ?
C10 C11 C12 112.57(15) . . ?
C12 C11 H11A 109.1 . . ?
C12 C11 H11B 109.1 . . ?
C5 C6 C7 121.04(17) . . ?
C5 C6 C1 118.13(19) . . ?
C1 C6 C7 120.81(17) . . ?
C9 C10 C11 113.96(14) . . ?
C9 C10 H10A 108.8 . . ?
C9 C10 H10B 108.8 . . ?
C11 C10 H10A 108.8 . . ?
C11 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C11 C12 H12A 109.0 . . ?
C11 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C13 C12 C11 112.76(16) . . ?
C13 C12 H12A 109.0 . . ?
C13 C12 H12B 109.0 . . ?
N1 C7 C6 111.86(15) . . ?
N1 C7 H7A 109.2 . . ?
N1 C7 H7B 109.2 . . ?
C6 C7 H7A 109.2 . . ?
C6 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C6 C5 H5 119.5 . . ?
C4 C5 C6 121.07(19) . . ?
C4 C5 H5 119.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C6 C1 H1 119.6 . . ?
C2 C1 C6 120.74(19) . . ?
C2 C1 H1 119.6 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.0(2) . . ?
C4 C3 H3 120.0 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.00(19) . . ?
C3 C2 H2 120.0 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 C5 120.0(2) . . ?
C3 C4 H4 120.0 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.141
_oxdiff_exptl_absorpt_empirical_full_min 0.858
####################################################################### 
# 
# 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_cu229
_database_code_depnum_ccdc_archive 'CCDC 1831794'
_audit_update_record             
;
2018-03-22 deposited with the CCDC.
2018-05-01 downloaded from the CCDC.
;
_audit_creation_date             2017-11-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H11 N3 O'
_chemical_formula_sum            'C10 H11 N3 O'
_chemical_formula_weight         189.22
_chemical_melting_point          ?
_chemical_oxdiff_formula         C50H50N6O2
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'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2035(12)
_cell_length_b                   11.0403(11)
_cell_length_c                   11.2020(11)
_cell_angle_alpha                93.064(8)
_cell_angle_beta                 106.687(11)
_cell_angle_gamma                104.934(10)
_cell_volume                     930.1(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1595
_cell_measurement_temperature    173
_cell_measurement_theta_max      71.1270
_cell_measurement_theta_min      4.1800
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.744
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94611
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0545
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5011
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.194
_diffrn_reflns_theta_min         4.160
_diffrn_ambient_temperature      173.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1033
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     10.00 104.00   1.00    4.89    --   36.75  77.00 120.00   94
  2  ω    -30.00  63.00   1.00    4.89    --   36.75 -77.00 -90.00   93
  3  ω     10.00 101.00   1.00    4.89    --   36.75  77.00  30.00   91
  4  ω    -23.00  75.00   1.00    4.89    --   36.75 -99.00-150.00   98
  5  ω     41.00 121.00   1.00   24.00    --  107.00 -45.00   0.00   80
  6  ω     69.00 142.00   1.00   24.00    --  107.00 -92.00-109.27   73
  7  ω     40.00 124.00   1.00   24.00    --  107.00 -45.00-180.00   84
  8  ω     85.00 123.00   1.00   24.00    --  107.00 -45.00 -90.00   38
  9  ω     42.00 123.00   1.00   24.00    --  107.00 -45.00  90.00   81
 10  ω     41.00  82.00   1.00   24.00    --  107.00 -45.00 -90.00   41
 11  ω    110.00 166.00   1.00   24.00    --  107.00  45.00 150.00   56
 12  ω     43.00 169.00   1.00   24.00    --  107.00   0.00 120.00  126
 13  ω     46.00 115.00   1.00   24.00    --  107.00 -92.00 153.56   69
 14  ω     77.00 142.00   1.00   24.00    --  107.00 -93.00 -18.64   65
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1146424000
_diffrn_orient_matrix_UB_12      0.0121848000
_diffrn_orient_matrix_UB_13      0.0849400000
_diffrn_orient_matrix_UB_21      0.1350748000
_diffrn_orient_matrix_UB_22      0.1269214000
_diffrn_orient_matrix_UB_23      0.0681026000
_diffrn_orient_matrix_UB_31      -0.1022625000
_diffrn_orient_matrix_UB_32      0.0707256000
_diffrn_orient_matrix_UB_33      -0.0956994000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2383
_reflns_number_total             3462
_reflns_odcompleteness_completeness 98.15
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3462
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0451
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0417P)²+0.0128P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1216
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H1(0.052) H2A(0.05) H18(0.032) H8(0.034) H17A(0.037) H17B(0.037)
 H20A(0.038) H20B(0.038) H4(0.041) H10A(0.039) H10B(0.039) H7A(0.039)
 H7B(0.039) H6(0.044) H13(0.045) H2(0.049) H15(0.05) H1A(0.052) H12(0.054)
 H3(0.047) H11(0.054) H16(0.059)
 Fixed X: H1(0.3276) H2A(0.1736) H18(-0.3086) H8(0.8117) H17A(-0.3635) H17B(-
 0.1897) H20A(0.0541) H20B(-0.1317) H4(0.9593) H10A(0.6352) H10B(0.4484)
 H7A(0.6903) H7B(0.8658) H6(0.5577) H13(-0.2609) H2(0.7841) H15(-0.2416)
 H1A(0.574) H12(-0.2814) H3(0.9761) H11(-0.2751) H16(-0.2553)
 Fixed Y: H1(0.3931) H2A(0.613) H18(0.3656) H8(0.6435) H17A(0.2826)
 H17B(0.3218) H20A(0.4233) H20B(0.4553) H4(0.9303) H10A(0.5522) H10B(0.5829)
 H7A(0.687) H7B(0.7212) H6(0.8514) H13(0.1353) H2(1.213) H15(0.0982)
 H1A(1.0656) H12(-0.0788) H3(1.1446) H11(-0.2038) H16(-0.1149)
 Fixed Z: H1(0.332) H2A(0.1628) H18(0.2505) H8(0.2495) H17A(0.4567)
 H17B(0.5774) H20A(0.1147) H20B(0.0874) H4(0.1733) H10A(0.4123) H10B(0.3845)
 H7A(-0.0794) H7B(0.04) H6(-0.1544) H13(0.6727) H2(0.0165) H15(0.3172) H1A(-
 0.1496) H12(0.6794) H3(0.1774) H11(0.5071) H16(0.3266)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.42740(19) 0.40591(12) 0.32099(14) 0.0346(3) Uani 1 1 d . . . . .
H1 H 0.3276 0.3931 0.3320 0.052 Uiso 1 1 calc GR . . . .
O2 O 0.07704(18) 0.60014(12) 0.17872(13) 0.0336(3) Uani 1 1 d . . . . .
H2A H 0.1736 0.6130 0.1628 0.050 Uiso 1 1 calc GR . . . .
N4 N -0.1352(2) 0.33576(13) 0.41319(15) 0.0274(3) Uani 1 1 d . . . . .
N1 N 0.6383(2) 0.67110(13) 0.08635(15) 0.0283(3) Uani 1 1 d . . . . .
N6 N 0.0996(2) 0.40233(15) 0.36124(16) 0.0324(4) Uani 1 1 d . . . . .
N5 N 0.0410(2) 0.35482(15) 0.45160(16) 0.0331(4) Uani 1 1 d . . . . .
N2 N 0.4622(2) 0.64955(16) 0.04706(16) 0.0358(4) Uani 1 1 d . . . . .
N3 N 0.4037(2) 0.60184(15) 0.13717(16) 0.0343(4) Uani 1 1 d . . . . .
C9 C 0.5421(2) 0.59255(16) 0.23372(17) 0.0274(4) Uani 1 1 d . . . . .
C18 C -0.1905(2) 0.37039(16) 0.29846(17) 0.0270(4) Uani 1 1 d . . . . .
H18 H -0.3086 0.3656 0.2505 0.032 Uiso 1 1 calc R . . . .
C8 C 0.6933(2) 0.63750(16) 0.20113(17) 0.0283(4) Uani 1 1 d . . . . .
H8 H 0.8117 0.6435 0.2495 0.034 Uiso 1 1 calc R . . . .
C5 C 0.7558(2) 0.86960(17) 0.00932(17) 0.0281(4) Uani 1 1 d . . . . .
C17 C -0.2411(3) 0.27587(17) 0.49073(18) 0.0308(4) Uani 1 1 d . . . . .
H17A H -0.3635 0.2826 0.4567 0.037 Uiso 1 1 calc R . . . .
H17B H -0.1897 0.3218 0.5774 0.037 Uiso 1 1 calc R . . . .
C14 C -0.2482(2) 0.13783(17) 0.49488(17) 0.0287(4) Uani 1 1 d . . . . .
C19 C -0.0392(2) 0.41409(15) 0.26578(17) 0.0266(4) Uani 1 1 d . . . . .
C20 C -0.0143(3) 0.46836(17) 0.15095(17) 0.0319(4) Uani 1 1 d . . . . .
H20A H 0.0541 0.4233 0.1147 0.038 Uiso 1 1 calc R . . . .
H20B H -0.1317 0.4553 0.0874 0.038 Uiso 1 1 calc R . . . .
C4 C 0.8805(3) 0.95752(18) 0.10747(18) 0.0342(4) Uani 1 1 d . . . . .
H4 H 0.9593 0.9303 0.1733 0.041 Uiso 1 1 calc R . . . .
C10 C 0.5176(3) 0.53840(17) 0.34852(18) 0.0326(4) Uani 1 1 d . . . . .
H10A H 0.6352 0.5522 0.4123 0.039 Uiso 1 1 calc R . . . .
H10B H 0.4484 0.5829 0.3845 0.039 Uiso 1 1 calc R . . . .
C7 C 0.7446(3) 0.73063(17) 0.00812(19) 0.0328(4) Uani 1 1 d . . . . .
H7A H 0.6903 0.6870 -0.0794 0.039 Uiso 1 1 calc R . . . .
H7B H 0.8658 0.7212 0.0400 0.039 Uiso 1 1 calc R . . . .
C6 C 0.6427(3) 0.91082(19) -0.08641(19) 0.0371(4) Uani 1 1 d . . . . .
H6 H 0.5577 0.8514 -0.1544 0.044 Uiso 1 1 calc R . . . .
C13 C -0.2603(3) 0.08463(19) 0.60160(19) 0.0379(4) Uani 1 1 d . . . . .
H13 H -0.2609 0.1353 0.6727 0.045 Uiso 1 1 calc R . . . .
C2 C 0.7770(3) 1.12562(18) 0.0146(2) 0.0408(5) Uani 1 1 d . . . . .
H2 H 0.7841 1.2130 0.0165 0.049 Uiso 1 1 calc R . . . .
C15 C -0.2480(3) 0.06278(19) 0.3917(2) 0.0417(5) Uani 1 1 d . . . . .
H15 H -0.2416 0.0982 0.3172 0.050 Uiso 1 1 calc R . . . .
C1 C 0.6527(3) 1.0382(2) -0.0838(2) 0.0434(5) Uani 1 1 d . . . . .
H1A H 0.5740 1.0656 -0.1496 0.052 Uiso 1 1 calc R . . . .
C12 C -0.2716(3) -0.0426(2) 0.6058(2) 0.0450(5) Uani 1 1 d . . . . .
H12 H -0.2814 -0.0788 0.6794 0.054 Uiso 1 1 calc R . . . .
C3 C 0.8905(3) 1.08497(19) 0.1098(2) 0.0394(5) Uani 1 1 d . . . . .
H3 H 0.9761 1.1446 0.1774 0.047 Uiso 1 1 calc R . . . .
C11 C -0.2689(3) -0.11696(19) 0.5037(2) 0.0453(5) Uani 1 1 d . . . . .
H11 H -0.2751 -0.2038 0.5071 0.054 Uiso 1 1 calc R . . . .
C16 C -0.2572(4) -0.0642(2) 0.3971(2) 0.0488(6) Uani 1 1 d . . . . .
H16 H -0.2553 -0.1149 0.3266 0.059 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8400 . ?
O1 C10 1.430(2) . ?
O2 H2A 0.8400 . ?
O2 C20 1.425(2) . ?
N4 N5 1.340(2) . ?
N4 C18 1.346(2) . ?
N4 C17 1.465(2) . ?
N1 N2 1.336(2) . ?
N1 C8 1.341(2) . ?
N1 C7 1.472(2) . ?
N6 N5 1.318(2) . ?
N6 C19 1.360(2) . ?
N2 N3 1.316(2) . ?
N3 C9 1.355(3) . ?
C9 C8 1.371(3) . ?
C9 C10 1.490(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.371(3) . ?
C8 H8 0.9500 . ?
C5 C4 1.388(3) . ?
C5 C7 1.512(2) . ?
C5 C6 1.384(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C14 1.514(2) . ?
C14 C13 1.377(3) . ?
C14 C15 1.386(3) . ?
C19 C20 1.492(2) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C4 H4 0.9500 . ?
C4 C3 1.387(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C6 H6 0.9500 . ?
C6 C1 1.385(3) . ?
C13 H13 0.9500 . ?
C13 C12 1.388(3) . ?
C2 H2 0.9500 . ?
C2 C1 1.386(3) . ?
C2 C3 1.379(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.390(3) . ?
C1 H1A 0.9500 . ?
C12 H12 0.9500 . ?
C12 C11 1.381(3) . ?
C3 H3 0.9500 . ?
C11 H11 0.9500 . ?
C11 C16 1.372(3) . ?
C16 H16 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
C10 O1 H1 109.5 . . ?
C20 O2 H2A 109.5 . . ?
N5 N4 C18 111.14(16) . . ?
N5 N4 C17 119.81(16) . . ?
C18 N4 C17 128.91(16) . . ?
N2 N1 C8 111.00(16) . . ?
N2 N1 C7 119.96(16) . . ?
C8 N1 C7 128.96(16) . . ?
N5 N6 C19 109.37(15) . . ?
N6 N5 N4 106.74(15) . . ?
N3 N2 N1 106.77(15) . . ?
N2 N3 C9 109.63(15) . . ?
N3 C9 C8 107.31(17) . . ?
N3 C9 C10 122.32(16) . . ?
C8 C9 C10 130.35(18) . . ?
N4 C18 H18 127.5 . . ?
N4 C18 C19 105.01(16) . . ?
C19 C18 H18 127.5 . . ?
N1 C8 C9 105.29(17) . . ?
N1 C8 H8 127.4 . . ?
C9 C8 H8 127.4 . . ?
C4 C5 C7 119.93(18) . . ?
C6 C5 C4 119.21(18) . . ?
C6 C5 C7 120.86(17) . . ?
N4 C17 H17A 109.1 . . ?
N4 C17 H17B 109.1 . . ?
N4 C17 C14 112.42(15) . . ?
H17A C17 H17B 107.9 . . ?
C14 C17 H17A 109.1 . . ?
C14 C17 H17B 109.1 . . ?
C13 C14 C17 119.56(17) . . ?
C13 C14 C15 119.25(18) . . ?
C15 C14 C17 121.16(17) . . ?
N6 C19 C18 107.73(16) . . ?
N6 C19 C20 122.02(16) . . ?
C18 C19 C20 130.25(17) . . ?
O2 C20 C19 111.55(15) . . ?
O2 C20 H20A 109.3 . . ?
O2 C20 H20B 109.3 . . ?
C19 C20 H20A 109.3 . . ?
C19 C20 H20B 109.3 . . ?
H20A C20 H20B 108.0 . . ?
C5 C4 H4 119.9 . . ?
C3 C4 C5 120.3(2) . . ?
C3 C4 H4 119.9 . . ?
O1 C10 C9 111.55(15) . . ?
O1 C10 H10A 109.3 . . ?
O1 C10 H10B 109.3 . . ?
C9 C10 H10A 109.3 . . ?
C9 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
N1 C7 C5 111.27(15) . . ?
N1 C7 H7A 109.4 . . ?
N1 C7 H7B 109.4 . . ?
C5 C7 H7A 109.4 . . ?
C5 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C5 C6 H6 119.8 . . ?
C5 C6 C1 120.45(19) . . ?
C1 C6 H6 119.8 . . ?
C14 C13 H13 119.8 . . ?
C14 C13 C12 120.32(19) . . ?
C12 C13 H13 119.8 . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C3 C2 C1 119.55(19) . . ?
C14 C15 H15 120.0 . . ?
C14 C15 C16 120.1(2) . . ?
C16 C15 H15 120.0 . . ?
C6 C1 C2 120.1(2) . . ?
C6 C1 H1A 119.9 . . ?
C2 C1 H1A 119.9 . . ?
C13 C12 H12 119.8 . . ?
C11 C12 C13 120.4(2) . . ?
C11 C12 H12 119.8 . . ?
C4 C3 H3 119.8 . . ?
C2 C3 C4 120.4(2) . . ?
C2 C3 H3 119.8 . . ?
C12 C11 H11 120.3 . . ?
C16 C11 C12 119.34(19) . . ?
C16 C11 H11 120.3 . . ?
C15 C16 H16 119.7 . . ?
C11 C16 C15 120.5(2) . . ?
C11 C16 H16 119.7 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.238
_oxdiff_exptl_absorpt_empirical_full_min 0.874





#===END
####################################################################### 
# 
# 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_o-il
_database_code_depnum_ccdc_archive 'CCDC 1831789'
_audit_update_record             
;
2018-03-22 deposited with the CCDC.
2018-05-01 downloaded from the CCDC.
;
_audit_creation_date             2017-01-09
_audit_creation_method           
;
Olex2 1.2-ac21
(compiled 2015.09.16 svn.r134, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(H2 O), C14 H14 N4'
_chemical_formula_sum            'C14 H18 N4 O2'
_chemical_formula_weight         274.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N6O2
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'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1128(8)
_cell_length_b                   8.7716(11)
_cell_length_c                   10.9028(11)
_cell_angle_alpha                80.648(10)
_cell_angle_beta                 69.951(9)
_cell_angle_gamma                84.374(10)
_cell_volume                     718.41(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1142
_cell_measurement_temperature    173
_cell_measurement_theta_max      70.5740
_cell_measurement_theta_min      5.1170
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.716
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91060
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.44a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0721
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3676
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.949
_diffrn_reflns_theta_min         4.358
_diffrn_ambient_temperature      173
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1033
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     23.00 101.00   1.00    1.00    --   36.75  57.00 -30.00   78
  2  ω     41.00 124.00   1.00    2.67    --  107.00 -45.00 -90.00   83
  3  ω     72.00 130.00   1.00    2.67    --  107.00 -93.00 -30.02   58
  4  ω     63.00 105.00   1.00    2.67    --  107.00 -91.00-111.65   42
  5  ω     57.00 120.00   1.00    2.67    --  107.00 -45.00-180.00   63
  6  ω    102.00 172.00   1.00    2.67    --  107.00  61.00-180.00   70
  7  ω     36.00  89.00   1.00    1.00    --   36.75 178.00 -30.00   53
  8  ω     25.00  99.00   1.00    1.00    --   36.75  57.00 120.00   74
  9  ω     39.00 123.00   1.00    2.67    --  107.00 -45.00  30.00   84
 10  ω     50.00 121.00   1.00    2.67    --  107.00 -92.00 121.31   71
 11  ω     44.00 112.00   1.00    2.67    --  107.00 -45.00 120.00   68
 12  ω     41.00 174.00   1.00    2.67    --  107.00   0.00 150.00  133
 13  ω     21.00 101.00   1.00    1.00    --   36.75  57.00  60.00   80
 14  ω    -25.00  76.00   1.00    1.00    --   36.75 -99.00-150.00  101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1144370000
_diffrn_orient_matrix_UB_12      0.1035579000
_diffrn_orient_matrix_UB_13      -0.1215230000
_diffrn_orient_matrix_UB_21      0.0347830000
_diffrn_orient_matrix_UB_22      -0.1345625000
_diffrn_orient_matrix_UB_23      -0.0818406000
_diffrn_orient_matrix_UB_31      -0.1632219000
_diffrn_orient_matrix_UB_32      0.0540161000
_diffrn_orient_matrix_UB_33      -0.0399647000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1828
_reflns_number_total             2629
_reflns_odcompleteness_completeness 97.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.44a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.44a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.44a (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         2629
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0730
_refine_ls_R_factor_gt           0.0484
_refine_ls_restrained_S_all      0.986
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0460P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1108
_refine_ls_wR_factor_ref         0.1284
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O2(H2A,H2B), O1(H1A,H1B)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C6(H6), C7(H7), C1(H1), C14(H14), C12(H12), C8(H8), C13(H13), C2(H2),
 C3(H3)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O -0.1630(3) 0.9463(3) 0.91840(17) 0.0468(5) Uani 1 1 d . . . . .
H2A H -0.1928 0.9871 0.8524 0.070 Uiso 1 1 d G . . . .
H2B H -0.0520 0.9324 0.8945 0.070 Uiso 1 1 d G . . . .
O1 O 0.1957(3) 0.8956(2) 0.86988(19) 0.0512(5) Uani 1 1 d . . . . .
H1A H 0.1973 0.9357 0.9354 0.077 Uiso 1 1 d G . . . .
H1B H 0.2760 0.8244 0.8536 0.077 Uiso 1 1 d G . . . .
N3 N 1.1185(2) 0.8164(2) 0.52710(17) 0.0270(4) Uani 1 1 d . . . . .
N2 N 0.7048(2) 0.5473(2) 0.85937(16) 0.0270(4) Uani 1 1 d . . . . .
N4 N 1.2245(3) 0.9306(2) 0.32163(18) 0.0352(5) Uani 1 1 d . . . . .
N1 N 0.4694(3) 0.6716(2) 0.82790(19) 0.0364(5) Uani 1 1 d . . . . .
C10 C 1.0886(3) 0.5565(2) 0.6624(2) 0.0253(4) Uani 1 1 d . . . . .
C5 C 1.0202(3) 0.4626(3) 0.7838(2) 0.0259(4) Uani 1 1 d . . . . .
C9 C 1.2295(3) 0.4992(3) 0.5632(2) 0.0289(5) Uani 1 1 d . . . . .
H9 H 1.2759 0.5620 0.4806 0.035 Uiso 1 1 calc R . . . .
C4 C 0.8656(3) 0.5168(3) 0.8946(2) 0.0298(5) Uani 1 1 d . . . . .
H4A H 0.8436 0.4370 0.9731 0.036 Uiso 1 1 calc R . . . .
H4B H 0.8952 0.6125 0.9181 0.036 Uiso 1 1 calc R . . . .
C6 C 1.0964(3) 0.3151(3) 0.8024(2) 0.0300(5) Uani 1 1 d . . . . .
H6 H 1.0503 0.2510 0.8843 0.036 Uiso 1 1 calc R . . . .
C7 C 1.2382(3) 0.2600(3) 0.7039(2) 0.0337(5) Uani 1 1 d . . . . .
H7 H 1.2905 0.1602 0.7190 0.040 Uiso 1 1 calc R . . . .
C1 C 0.6030(3) 0.6785(3) 0.8687(2) 0.0335(5) Uani 1 1 d . . . . .
H1 H 0.6251 0.7659 0.9010 0.040 Uiso 1 1 calc R . . . .
C14 C 1.1050(3) 0.8403(3) 0.4059(2) 0.0319(5) Uani 1 1 d . . . . .
H14 H 1.0182 0.7965 0.3838 0.038 Uiso 1 1 calc R . . . .
C12 C 1.2574(3) 0.8979(3) 0.5211(2) 0.0350(5) Uani 1 1 d . . . . .
H12 H 1.3002 0.9044 0.5910 0.042 Uiso 1 1 calc R . . . .
C8 C 1.3028(3) 0.3515(3) 0.5835(2) 0.0318(5) Uani 1 1 d . . . . .
H8 H 1.3974 0.3132 0.5146 0.038 Uiso 1 1 calc R . . . .
C11 C 1.0082(3) 0.7183(3) 0.6406(2) 0.0324(5) Uani 1 1 d . . . . .
H11A H 0.8940 0.7100 0.6286 0.039 Uiso 1 1 calc R . . . .
H11B H 0.9851 0.7682 0.7204 0.039 Uiso 1 1 calc R . . . .
C13 C 1.3214(3) 0.9677(3) 0.3943(2) 0.0362(5) Uani 1 1 d . . . . .
H13 H 1.4186 1.0326 0.3605 0.043 Uiso 1 1 calc R . . . .
C2 C 0.4865(3) 0.5260(3) 0.7912(2) 0.0353(5) Uani 1 1 d . . . . .
H2 H 0.4085 0.4860 0.7575 0.042 Uiso 1 1 calc R . . . .
C3 C 0.6308(3) 0.4480(3) 0.8100(2) 0.0328(5) Uani 1 1 d . . . . .
H3 H 0.6719 0.3459 0.7927 0.039 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 H2A 0.8501 . ?
O2 H2B 0.8501 . ?
O1 H1A 0.8502 . ?
O1 H1B 0.8501 . ?
N3 C14 1.344(3) . ?
N3 C12 1.371(3) . ?
N3 C11 1.455(3) . ?
N2 C4 1.471(3) . ?
N2 C1 1.346(3) . ?
N2 C3 1.373(3) . ?
N4 C14 1.310(3) . ?
N4 C13 1.382(3) . ?
N1 C1 1.314(3) . ?
N1 C2 1.380(3) . ?
C10 C5 1.404(3) . ?
C10 C9 1.395(3) . ?
C10 C11 1.520(3) . ?
C5 C4 1.513(3) . ?
C5 C6 1.393(3) . ?
C9 H9 0.9500 . ?
C9 C8 1.389(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C6 H6 0.9500 . ?
C6 C7 1.387(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.381(3) . ?
C1 H1 0.9500 . ?
C14 H14 0.9500 . ?
C12 H12 0.9500 . ?
C12 C13 1.361(3) . ?
C8 H8 0.9500 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C13 H13 0.9500 . ?
C2 H2 0.9500 . ?
C2 C3 1.357(3) . ?
C3 H3 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
H2A O2 H2B 109.5 . . ?
H1A O1 H1B 109.5 . . ?
C14 N3 C12 106.89(19) . . ?
C14 N3 C11 125.7(2) . . ?
C12 N3 C11 127.41(19) . . ?
C1 N2 C4 126.3(2) . . ?
C1 N2 C3 107.07(19) . . ?
C3 N2 C4 126.59(19) . . ?
C14 N4 C13 104.47(19) . . ?
C1 N1 C2 104.8(2) . . ?
C5 C10 C11 119.79(18) . . ?
C9 C10 C5 119.20(19) . . ?
C9 C10 C11 121.00(19) . . ?
C10 C5 C4 121.83(19) . . ?
C6 C5 C10 119.03(19) . . ?
C6 C5 C4 119.14(19) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 C10 120.8(2) . . ?
C8 C9 H9 119.6 . . ?
N2 C4 C5 112.53(16) . . ?
N2 C4 H4A 109.1 . . ?
N2 C4 H4B 109.1 . . ?
C5 C4 H4A 109.1 . . ?
C5 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
C5 C6 H6 119.3 . . ?
C7 C6 C5 121.3(2) . . ?
C7 C6 H6 119.3 . . ?
C6 C7 H7 120.3 . . ?
C8 C7 C6 119.5(2) . . ?
C8 C7 H7 120.3 . . ?
N2 C1 H1 123.9 . . ?
N1 C1 N2 112.1(2) . . ?
N1 C1 H1 123.9 . . ?
N3 C14 H14 123.6 . . ?
N4 C14 N3 112.7(2) . . ?
N4 C14 H14 123.6 . . ?
N3 C12 H12 127.2 . . ?
C13 C12 N3 105.7(2) . . ?
C13 C12 H12 127.2 . . ?
C9 C8 H8 120.0 . . ?
C7 C8 C9 120.1(2) . . ?
C7 C8 H8 120.0 . . ?
N3 C11 C10 113.61(17) . . ?
N3 C11 H11A 108.8 . . ?
N3 C11 H11B 108.8 . . ?
C10 C11 H11A 108.8 . . ?
C10 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
N4 C13 H13 124.9 . . ?
C12 C13 N4 110.2(2) . . ?
C12 C13 H13 124.9 . . ?
N1 C2 H2 124.9 . . ?
C3 C2 N1 110.3(2) . . ?
C3 C2 H2 124.9 . . ?
N2 C3 H3 127.1 . . ?
C2 C3 N2 105.7(2) . . ?
C2 C3 H3 127.1 . . ?

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
N3 C12 C13 N4 -0.1(3) . . . . ?
N1 C2 C3 N2 0.0(3) . . . . ?
C10 C5 C4 N2 62.8(3) . . . . ?
C10 C5 C6 C7 0.2(3) . . . . ?
C10 C9 C8 C7 -1.0(4) . . . . ?
C5 C10 C9 C8 -0.4(3) . . . . ?
C5 C10 C11 N3 164.3(2) . . . . ?
C5 C6 C7 C8 -1.6(4) . . . . ?
C9 C10 C5 C4 -179.0(2) . . . . ?
C9 C10 C5 C6 0.8(3) . . . . ?
C9 C10 C11 N3 -16.0(3) . . . . ?
C4 N2 C1 N1 179.06(19) . . . . ?
C4 N2 C3 C2 -179.26(19) . . . . ?
C4 C5 C6 C7 180.0(2) . . . . ?
C6 C5 C4 N2 -117.0(2) . . . . ?
C6 C7 C8 C9 2.0(4) . . . . ?
C1 N2 C4 C5 -127.0(2) . . . . ?
C1 N2 C3 C2 0.3(2) . . . . ?
C1 N1 C2 C3 -0.3(3) . . . . ?
C14 N3 C12 C13 0.0(3) . . . . ?
C14 N3 C11 C10 96.4(3) . . . . ?
C14 N4 C13 C12 0.2(3) . . . . ?
C12 N3 C14 N4 0.2(3) . . . . ?
C12 N3 C11 C10 -81.6(3) . . . . ?
C11 N3 C14 N4 -178.17(19) . . . . ?
C11 N3 C12 C13 178.26(19) . . . . ?
C11 C10 C5 C4 0.7(3) . . . . ?
C11 C10 C5 C6 -179.5(2) . . . . ?
C11 C10 C9 C8 179.9(2) . . . . ?
C13 N4 C14 N3 -0.2(3) . . . . ?
C2 N1 C1 N2 0.5(3) . . . . ?
C3 N2 C4 C5 52.5(3) . . . . ?
C3 N2 C1 N1 -0.5(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2017-01-09
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.800
_oxdiff_exptl_absorpt_empirical_full_min 0.865
####################################################################### 
# 
# 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_cu230
_database_code_depnum_ccdc_archive 'CCDC 1831792'
_audit_update_record             
;
2018-03-22 deposited with the CCDC.
2018-05-01 downloaded from the CCDC.
;
_audit_creation_date             2018-03-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H15 N3 O'
_chemical_formula_sum            'C16 H15 N3 O'
_chemical_formula_weight         265.31
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16H15N3O
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'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.1339(8)
_cell_length_b                   5.6565(6)
_cell_length_c                   14.5299(16)
_cell_angle_alpha                90
_cell_angle_beta                 92.836(9)
_cell_angle_gamma                90
_cell_volume                     667.69(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    532
_cell_measurement_temperature    173
_cell_measurement_theta_max      69.0420
_cell_measurement_theta_min      5.4530
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.680
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70135
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0578
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            1972
_diffrn_reflns_point_group_measured_fraction_full 0.643
_diffrn_reflns_point_group_measured_fraction_max 0.632
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.243
_diffrn_reflns_theta_min         5.445
_diffrn_ambient_temperature      173.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1033
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -9.00  17.00   1.00    2.00    --    0.00 -77.00 -60.00   26
  2  ω    -64.00 -39.00   1.00    2.00    --    0.00 -77.00 -60.00   25
  3  ω   -127.00 -29.00   1.00    3.80    --  -54.75 -77.00  30.00   98
  4  ω    -72.00  16.00   1.00    3.80    --  -54.75  57.00 150.00   88
  5  ω     84.00 126.00   1.00    3.80    --   54.75 125.00   0.00   42
  6  ω     79.00 110.00   1.00    3.80    --   54.75  99.00  40.00   31
  7  ω     83.00 175.00   1.00    3.80    --  109.50  64.00 -90.00   92
  8  ω     64.00 133.00   1.00    3.80    --  109.50 -50.00 -30.00   69
  9  ω     62.00  90.00   1.00    3.80    --  109.50-111.00  30.00   28
 10  ω     55.00  87.00   1.00    3.80    --  109.50-111.00   0.00   32
 11  ω     39.00 139.00   1.00    3.80    --  109.50 -38.00 -90.00  100
 12  ω     39.00 133.00   1.00    3.80    --  109.50 -50.00 120.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0359961000
_diffrn_orient_matrix_UB_12      0.0968786000
_diffrn_orient_matrix_UB_13      0.0980139000
_diffrn_orient_matrix_UB_21      0.1808163000
_diffrn_orient_matrix_UB_22      0.0425617000
_diffrn_orient_matrix_UB_23      -0.0223163000
_diffrn_orient_matrix_UB_31      -0.0444742000
_diffrn_orient_matrix_UB_32      0.2509551000
_diffrn_orient_matrix_UB_33      -0.0341060000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_reflns_Friedel_coverage         0.176
_reflns_Friedel_fraction_full    0.219
_reflns_Friedel_fraction_max     0.212
_reflns_number_gt                1263
_reflns_number_total             1586
_reflns_odcompleteness_completeness 98.23
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.0069(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         1586
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0464
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0550P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1164
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C14(H14), C5(H5), C12(H12), C1(H1), C2(H2), C3(H3), C11(H11),
 C4(H4), C8(H8)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1441(3) 0.2386(6) 0.37224(18) 0.0468(8) Uani 1 1 d . . . . .
N3 N 0.4608(4) 0.2119(7) 0.7917(2) 0.0448(9) Uani 1 1 d . . . . .
N1 N 0.5789(4) 0.5258(6) 0.8445(2) 0.0393(8) Uani 1 1 d . . . . .
N2 N 0.5373(4) 0.3039(7) 0.8658(3) 0.0472(9) Uani 1 1 d . . . . .
C6 C 0.8421(4) 0.7215(8) 0.8920(2) 0.0340(9) Uani 1 1 d . . . . .
C15 C 0.2820(4) 0.1281(7) 0.6142(3) 0.0352(9) Uani 1 1 d . . . . .
H15 H 0.2732 0.0129 0.6613 0.042 Uiso 1 1 calc R . . . .
C14 C 0.2020(4) 0.0910(7) 0.5286(3) 0.0367(10) Uani 1 1 d . . . . .
H14 H 0.1388 -0.0482 0.5175 0.044 Uiso 1 1 calc R . . . .
C5 C 0.9625(4) 0.5570(8) 0.9174(2) 0.0381(9) Uani 1 1 d . . . . .
H5 H 0.9331 0.4148 0.9472 0.046 Uiso 1 1 calc R . . . .
C9 C 0.4563(4) 0.3765(7) 0.7231(3) 0.0355(9) Uani 1 1 d . . . . .
C10 C 0.3748(4) 0.3320(7) 0.6321(3) 0.0338(9) Uani 1 1 d . . . . .
C12 C 0.3068(4) 0.4602(8) 0.4763(3) 0.0395(10) Uani 1 1 d . . . . .
H12 H 0.3158 0.5750 0.4291 0.047 Uiso 1 1 calc R . . . .
C13 C 0.2152(4) 0.2586(7) 0.4592(3) 0.0362(10) Uani 1 1 d . . . . .
C1 C 0.8871(5) 0.9286(8) 0.8487(2) 0.0385(10) Uani 1 1 d . . . . .
H1 H 0.8055 1.0421 0.8309 0.046 Uiso 1 1 calc R . . . .
C2 C 1.0505(5) 0.9706(8) 0.8314(3) 0.0422(10) Uani 1 1 d . . . . .
H2 H 1.0802 1.1127 0.8016 0.051 Uiso 1 1 calc R . . . .
C3 C 1.1698(5) 0.8083(8) 0.8570(3) 0.0424(11) Uani 1 1 d . . . . .
H3 H 1.2818 0.8392 0.8457 0.051 Uiso 1 1 calc R . . . .
C11 C 0.3856(5) 0.4969(8) 0.5617(3) 0.0395(10) Uani 1 1 d . . . . .
H11 H 0.4482 0.6369 0.5723 0.047 Uiso 1 1 calc R . . . .
C4 C 1.1266(5) 0.6001(8) 0.8991(3) 0.0403(10) Uani 1 1 d . . . . .
H4 H 1.2086 0.4862 0.9157 0.048 Uiso 1 1 calc R . . . .
C8 C 0.5331(5) 0.5759(8) 0.7566(3) 0.0405(10) Uani 1 1 d . . . . .
H8 H 0.5504 0.7194 0.7246 0.049 Uiso 1 1 calc R . . . .
C7 C 0.6650(5) 0.6801(8) 0.9133(3) 0.0422(11) Uani 1 1 d . . . . .
H7A H 0.6608 0.6067 0.9750 0.051 Uiso 1 1 calc R . . . .
H7B H 0.6073 0.8340 0.9151 0.051 Uiso 1 1 calc R . . . .
C16 C 0.0546(5) 0.0285(9) 0.3496(3) 0.0507(12) Uani 1 1 d . . . . .
H16A H 0.0103 0.0379 0.2857 0.076 Uiso 1 1 calc GR . . . .
H16B H -0.0362 0.0112 0.3910 0.076 Uiso 1 1 calc GR . . . .
H16C H 0.1281 -0.1083 0.3564 0.076 Uiso 1 1 calc GR . . . .


_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 C13 1.368(4) . ?
O1 C16 1.424(5) . ?
N3 N2 1.323(4) . ?
N3 C9 1.364(5) . ?
N1 N2 1.340(5) . ?
N1 C8 1.342(5) . ?
N1 C7 1.478(5) . ?
C6 C5 1.387(5) . ?
C6 C1 1.387(6) . ?
C6 C7 1.507(5) . ?
C15 H15 0.9500 . ?
C15 C14 1.391(5) . ?
C15 C10 1.396(5) . ?
C14 H14 0.9500 . ?
C14 C13 1.392(5) . ?
C5 H5 0.9500 . ?
C5 C4 1.396(5) . ?
C9 C10 1.471(5) . ?
C9 C8 1.368(6) . ?
C10 C11 1.391(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.378(6) . ?
C12 C11 1.383(5) . ?
C1 H1 0.9500 . ?
C1 C2 1.385(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.374(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.381(6) . ?
C11 H11 0.9500 . ?
C4 H4 0.9500 . ?
C8 H8 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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
C13 O1 C16 118.0(3) . . ?
N2 N3 C9 108.8(3) . . ?
N2 N1 C8 110.9(4) . . ?
N2 N1 C7 120.9(4) . . ?
C8 N1 C7 128.2(4) . . ?
N3 N2 N1 107.1(3) . . ?
C5 C6 C1 119.2(3) . . ?
C5 C6 C7 120.7(4) . . ?
C1 C6 C7 120.0(4) . . ?
C14 C15 H15 119.5 . . ?
C14 C15 C10 121.0(4) . . ?
C10 C15 H15 119.5 . . ?
C15 C14 H14 120.1 . . ?
C15 C14 C13 119.7(4) . . ?
C13 C14 H14 120.1 . . ?
C6 C5 H5 120.0 . . ?
C6 C5 C4 120.1(4) . . ?
C4 C5 H5 120.0 . . ?
N3 C9 C10 122.4(3) . . ?
N3 C9 C8 107.8(3) . . ?
C8 C9 C10 129.7(4) . . ?
C15 C10 C9 121.6(4) . . ?
C11 C10 C15 118.1(4) . . ?
C11 C10 C9 120.3(4) . . ?
C13 C12 H12 119.7 . . ?
C13 C12 C11 120.5(4) . . ?
C11 C12 H12 119.7 . . ?
O1 C13 C14 124.7(4) . . ?
O1 C13 C12 115.8(4) . . ?
C12 C13 C14 119.6(4) . . ?
C6 C1 H1 119.9 . . ?
C2 C1 C6 120.3(4) . . ?
C2 C1 H1 119.9 . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.5(4) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.9(4) . . ?
C4 C3 H3 120.1 . . ?
C10 C11 H11 119.5 . . ?
C12 C11 C10 121.0(4) . . ?
C12 C11 H11 119.5 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 C5 120.0(4) . . ?
C3 C4 H4 120.0 . . ?
N1 C8 C9 105.4(4) . . ?
N1 C8 H8 127.3 . . ?
C9 C8 H8 127.3 . . ?
N1 C7 C6 112.3(3) . . ?
N1 C7 H7A 109.2 . . ?
N1 C7 H7B 109.2 . . ?
C6 C7 H7A 109.2 . . ?
C6 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
O1 C16 H16A 109.5 . . ?
O1 C16 H16B 109.5 . . ?
O1 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.485
_oxdiff_exptl_absorpt_empirical_full_min 0.673
####################################################################### 
# 
# 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_monomerbl
_database_code_depnum_ccdc_archive 'CCDC 1831790'
_audit_update_record             
;
2018-03-22 deposited with the CCDC.
2018-05-01 downloaded from the CCDC.
;
_audit_creation_date             2018-03-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H11 N3'
_chemical_formula_sum            'C13 H11 N3'
_chemical_formula_weight         209.25
_chemical_melting_point          ?
_chemical_oxdiff_formula         C13H11N3
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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.5768(16)
_cell_length_b                   5.9774(8)
_cell_length_c                   16.119(2)
_cell_angle_alpha                90
_cell_angle_beta                 106.541(14)
_cell_angle_gamma                90
_cell_volume                     1069.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1059
_cell_measurement_temperature    173
_cell_measurement_theta_max      69.8660
_cell_measurement_theta_min      3.9470
_shelx_estimated_absorpt_T_max   0.884
_shelx_estimated_absorpt_T_min   0.813
_exptl_absorpt_coefficient_mu    0.634
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84525
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            3132
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.115
_diffrn_reflns_theta_min         3.983
_diffrn_ambient_temperature      173.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1033
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     10.00 108.00   1.00    1.00    --   36.63  19.00 -30.00   98
  2  ω     41.00  66.00   1.00    1.00    --  107.00 -61.00  60.00   25
  3  ω     48.00  84.00   1.00    1.00    --  107.00 -95.00  30.00   36
  4  ω     46.00 128.00   1.00    1.00    --  107.00 -30.00 -60.00   82
  5  ω     80.00 175.00   1.00    1.00    --  107.00  77.00 -30.00   95
  6  ω     44.00 145.00   1.00    1.00    --  107.00 -15.00 150.00  101
  7  ω     43.00 124.00   1.00    1.00    --  107.00 -57.00-170.00   81
  8  ω    -28.00  53.00   1.00    1.00    --   36.63 -57.00 150.00   81
  9  ω   -103.00 -60.00   1.00    1.00    --  -36.63-178.00 -30.00   43
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0195214000
_diffrn_orient_matrix_UB_12      0.0277476000
_diffrn_orient_matrix_UB_13      0.0980613000
_diffrn_orient_matrix_UB_21      0.0996388000
_diffrn_orient_matrix_UB_22      0.1736895000
_diffrn_orient_matrix_UB_23      0.0035991000
_diffrn_orient_matrix_UB_31      -0.0947409000
_diffrn_orient_matrix_UB_32      0.1882853000
_diffrn_orient_matrix_UB_33      -0.0178749000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1500
_reflns_number_total             1981
_reflns_odcompleteness_completeness 98.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1981
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0606
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1034P)²+0.1198P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1614
_refine_ls_wR_factor_ref         0.1860
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C2(H2), C13(H13), C4(H4), C9(H9), C3(H3), C12(H12), C11(H11), C10(H10)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N3 N 0.14075(15) 0.4949(3) 0.68515(11) 0.0397(5) Uani 1 1 d . . . . .
N1 N 0.07690(18) 0.1763(3) 0.62614(13) 0.0485(5) Uani 1 1 d . . . . .
N2 N 0.09236(17) 0.2959(3) 0.69620(12) 0.0462(5) Uani 1 1 d . . . . .
C6 C 0.15840(17) 0.5048(4) 0.60514(13) 0.0372(5) Uani 1 1 d . . . . .
C1 C 0.11584(18) 0.3006(4) 0.56738(14) 0.0412(5) Uani 1 1 d . . . . .
C8 C 0.30070(19) 0.6857(4) 0.79652(13) 0.0410(5) Uani 1 1 d . . . . .
C5 C 0.20635(19) 0.6683(4) 0.56292(15) 0.0441(6) Uani 1 1 d . . . . .
H5 H 0.2356 0.8068 0.5897 0.053 Uiso 1 1 calc R . . . .
C2 C 0.1164(2) 0.2532(4) 0.48210(15) 0.0464(6) Uani 1 1 d . . . . .
H2 H 0.0859 0.1159 0.4549 0.056 Uiso 1 1 calc R . . . .
C7 C 0.1672(2) 0.6644(4) 0.75314(14) 0.0455(6) Uani 1 1 d . . . . .
H7A H 0.1258 0.6246 0.7970 0.055 Uiso 1 1 calc R . . . .
H7B H 0.1353 0.8106 0.7278 0.055 Uiso 1 1 calc R . . . .
C13 C 0.3637(2) 0.5127(4) 0.84684(14) 0.0457(6) Uani 1 1 d . . . . .
H13 H 0.3232 0.3782 0.8528 0.055 Uiso 1 1 calc R . . . .
C4 C 0.2089(2) 0.6174(4) 0.48017(15) 0.0487(6) Uani 1 1 d . . . . .
H4 H 0.2426 0.7223 0.4493 0.058 Uiso 1 1 calc R . . . .
C9 C 0.3613(2) 0.8799(4) 0.78844(15) 0.0506(6) Uani 1 1 d . . . . .
H9 H 0.3187 0.9995 0.7542 0.061 Uiso 1 1 calc R . . . .
C3 C 0.1629(2) 0.4137(5) 0.43990(15) 0.0502(6) Uani 1 1 d . . . . .
H3 H 0.1642 0.3870 0.3821 0.060 Uiso 1 1 calc R . . . .
C12 C 0.4855(2) 0.5350(5) 0.88834(16) 0.0545(7) Uani 1 1 d . . . . .
H12 H 0.5282 0.4157 0.9226 0.065 Uiso 1 1 calc R . . . .
C11 C 0.5448(2) 0.7303(5) 0.88015(17) 0.0591(7) Uani 1 1 d . . . . .
H11 H 0.6282 0.7459 0.9094 0.071 Uiso 1 1 calc R . . . .
C10 C 0.4835(2) 0.9027(5) 0.82963(17) 0.0580(7) Uani 1 1 d . . . . .
H10 H 0.5246 1.0362 0.8231 0.070 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N3 N2 1.348(3) . ?
N3 C6 1.363(3) . ?
N3 C7 1.460(3) . ?
N1 N2 1.305(3) . ?
N1 C1 1.377(3) . ?
C6 C1 1.390(3) . ?
C6 C5 1.394(3) . ?
C1 C2 1.405(3) . ?
C8 C7 1.509(3) . ?
C8 C13 1.387(3) . ?
C8 C9 1.382(3) . ?
C5 H5 0.9500 . ?
C5 C4 1.377(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.372(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C13 H13 0.9500 . ?
C13 C12 1.384(3) . ?
C4 H4 0.9500 . ?
C4 C3 1.411(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.388(3) . ?
C3 H3 0.9500 . ?
C12 H12 0.9500 . ?
C12 C11 1.380(4) . ?
C11 H11 0.9500 . ?
C11 C10 1.379(4) . ?
C10 H10 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
N2 N3 C6 110.06(18) . . ?
N2 N3 C7 121.31(19) . . ?
C6 N3 C7 128.62(19) . . ?
N2 N1 C1 107.98(19) . . ?
N1 N2 N3 109.20(19) . . ?
N3 C6 C1 104.26(19) . . ?
N3 C6 C5 132.9(2) . . ?
C1 C6 C5 122.9(2) . . ?
N1 C1 C6 108.5(2) . . ?
N1 C1 C2 131.1(2) . . ?
C6 C1 C2 120.4(2) . . ?
C13 C8 C7 120.5(2) . . ?
C9 C8 C7 120.5(2) . . ?
C9 C8 C13 119.0(2) . . ?
C6 C5 H5 122.0 . . ?
C4 C5 C6 116.1(2) . . ?
C4 C5 H5 122.0 . . ?
C1 C2 H2 121.4 . . ?
C3 C2 C1 117.1(2) . . ?
C3 C2 H2 121.4 . . ?
N3 C7 C8 112.01(18) . . ?
N3 C7 H7A 109.2 . . ?
N3 C7 H7B 109.2 . . ?
C8 C7 H7A 109.2 . . ?
C8 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C8 C13 H13 119.8 . . ?
C12 C13 C8 120.3(2) . . ?
C12 C13 H13 119.8 . . ?
C5 C4 H4 119.1 . . ?
C5 C4 C3 121.8(2) . . ?
C3 C4 H4 119.1 . . ?
C8 C9 H9 119.6 . . ?
C8 C9 C10 120.9(2) . . ?
C10 C9 H9 119.6 . . ?
C2 C3 C4 121.7(2) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C13 C12 H12 119.9 . . ?
C11 C12 C13 120.1(2) . . ?
C11 C12 H12 119.9 . . ?
C12 C11 H11 119.9 . . ?
C10 C11 C12 120.1(2) . . ?
C10 C11 H11 119.9 . . ?
C9 C10 H10 120.2 . . ?
C11 C10 C9 119.5(3) . . ?
C11 C10 H10 120.2 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.337
_oxdiff_exptl_absorpt_empirical_full_min 0.754
####################################################################### 
# 
# 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_cu165f
_database_code_depnum_ccdc_archive 'CCDC 1831791'
_audit_update_record             
;
2018-03-22 deposited with the CCDC.
2018-05-01 downloaded from the CCDC.
;
_audit_creation_date             2018-03-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H13 N3'
_chemical_formula_sum            'C15 H13 N3'
_chemical_formula_weight         235.28
_chemical_absolute_configuration .
_chemical_melting_point          ?
_chemical_oxdiff_formula         C40H40N3
_chemical_oxdiff_usercomment     'small blue/green block'
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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   11.2241(4)
_cell_length_b                   19.3350(6)
_cell_length_c                   5.5817(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1211.33(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1498
_cell_measurement_temperature    173
_cell_measurement_theta_max      70.9630
_cell_measurement_theta_min      4.5400
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.619
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99353
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            3555
_diffrn_reflns_point_group_measured_fraction_full 0.900
_diffrn_reflns_point_group_measured_fraction_max 0.874
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.123
_diffrn_reflns_theta_min         4.555
_diffrn_ambient_temperature      173.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1033
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     22.00 106.00   1.00    1.00    --   36.63  38.00 150.00   84
  2  ω     38.00 142.00   1.00    2.87    --  107.00 -15.00 120.00  104
  3  ω     90.00 170.00   1.00    2.87    --  107.00  61.00 -60.00   80
  4  ω     56.00 123.00   1.00    2.87    --  107.00 -61.00-180.00   67
  5  ω     44.00  80.00   1.00    2.87    --  107.00 -95.00-180.00   36
  6  ω     39.00 127.00   1.00    2.87    --  107.00 -30.00 -60.00   88
  7  ω   -101.00 -57.00   1.00    1.00    --  -36.63-178.00 150.00   44
  8  ω   -107.00 -63.00   1.00    1.00    --  -36.63-178.00  60.00   44
  9  ω   -107.00 -57.00   1.00    1.00    --  -36.63-178.00-150.00   50
 10  ω   -109.00 -54.00   1.00    1.00    --  -36.63 178.00 -30.00   55
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0779412000
_diffrn_orient_matrix_UB_12      -0.0574261000
_diffrn_orient_matrix_UB_13      0.1098558000
_diffrn_orient_matrix_UB_21      0.0828955000
_diffrn_orient_matrix_UB_22      -0.0029209000
_diffrn_orient_matrix_UB_23      0.2196936000
_diffrn_orient_matrix_UB_31      -0.0767507000
_diffrn_orient_matrix_UB_32      0.0551841000
_diffrn_orient_matrix_UB_33      0.1257560000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_reflns_Friedel_coverage         0.608
_reflns_Friedel_fraction_full    0.779
_reflns_Friedel_fraction_max     0.741
_reflns_number_gt                1874
_reflns_number_total             2053
_reflns_odcompleteness_completeness 99.01
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.097
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2053
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0373
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0380P)²+0.0220P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0855
_refine_ls_wR_factor_ref         0.0892
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C11(H11), C5(H5), C1(H1), C15(H15), C4(H4), C2(H2), C13(H13),
 C12(H12), C14(H14), C3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.64976(19) 0.29054(10) 0.4577(4) 0.0374(5) Uani 1 1 d . . . . .
N2 N 0.6250(2) 0.28267(12) 0.2236(4) 0.0456(6) Uani 1 1 d . . . . .
N3 N 0.5357(2) 0.32469(11) 0.1737(4) 0.0418(5) Uani 1 1 d . . . . .
C9 C 0.5045(2) 0.35946(12) 0.3766(5) 0.0323(5) Uani 1 1 d . . . . .
C10 C 0.4119(2) 0.41314(11) 0.3752(4) 0.0319(5) Uani 1 1 d . . . . .
C8 C 0.5774(2) 0.33738(12) 0.5581(5) 0.0352(5) Uani 1 1 d . . . . .
H8 H 0.5768 0.3521 0.7205 0.042 Uiso 1 1 calc R . . . .
C11 C 0.4058(2) 0.46080(12) 0.5637(5) 0.0358(5) Uani 1 1 d . . . . .
H11 H 0.4585 0.4568 0.6961 0.043 Uiso 1 1 calc R . . . .
C6 C 0.8567(2) 0.30534(12) 0.5931(5) 0.0349(5) Uani 1 1 d . . . . .
C5 C 0.8836(2) 0.35390(13) 0.4177(5) 0.0384(6) Uani 1 1 d . . . . .
H5 H 0.8355 0.3570 0.2780 0.046 Uiso 1 1 calc R . . . .
C1 C 0.9273(2) 0.30139(13) 0.7960(5) 0.0400(6) Uani 1 1 d . . . . .
H1 H 0.9092 0.2686 0.9174 0.048 Uiso 1 1 calc R . . . .
C15 C 0.3330(2) 0.41969(14) 0.1842(5) 0.0394(6) Uani 1 1 d . . . . .
H15 H 0.3352 0.3874 0.0561 0.047 Uiso 1 1 calc R . . . .
C4 C 0.9804(2) 0.39798(14) 0.4452(5) 0.0442(6) Uani 1 1 d . . . . .
H4 H 0.9978 0.4314 0.3254 0.053 Uiso 1 1 calc R . . . .
C2 C 1.0247(2) 0.34517(14) 0.8230(5) 0.0437(6) Uani 1 1 d . . . . .
H2 H 1.0731 0.3421 0.9623 0.052 Uiso 1 1 calc R . . . .
C13 C 0.2452(2) 0.52063(13) 0.3652(6) 0.0431(6) Uani 1 1 d . . . . .
H13 H 0.1889 0.5573 0.3608 0.052 Uiso 1 1 calc R . . . .
C12 C 0.3226(2) 0.51402(13) 0.5573(5) 0.0411(6) Uani 1 1 d . . . . .
H12 H 0.3188 0.5462 0.6858 0.049 Uiso 1 1 calc R . . . .
C14 C 0.2510(2) 0.47336(13) 0.1808(5) 0.0441(6) Uani 1 1 d . . . . .
H14 H 0.1980 0.4776 0.0490 0.053 Uiso 1 1 calc R . . . .
C3 C 1.0513(2) 0.39319(14) 0.6471(5) 0.0448(6) Uani 1 1 d . . . . .
H3 H 1.1181 0.4229 0.6650 0.054 Uiso 1 1 calc R . . . .
C7 C 0.7527(2) 0.25628(13) 0.5654(6) 0.0451(6) Uani 1 1 d . . . . .
H7A H 0.7770 0.2168 0.4636 0.054 Uiso 1 1 calc R . . . .
H7B H 0.7302 0.2379 0.7246 0.054 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N2 1.345(3) . ?
N1 C8 1.339(3) . ?
N1 C7 1.462(3) . ?
N2 N3 1.320(3) . ?
N3 C9 1.363(3) . ?
C9 C10 1.469(3) . ?
C9 C8 1.371(3) . ?
C10 C11 1.400(3) . ?
C10 C15 1.392(3) . ?
C8 H8 0.9500 . ?
C11 H11 0.9500 . ?
C11 C12 1.390(3) . ?
C6 C5 1.390(4) . ?
C6 C1 1.384(4) . ?
C6 C7 1.512(3) . ?
C5 H5 0.9500 . ?
C5 C4 1.389(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.391(4) . ?
C15 H15 0.9500 . ?
C15 C14 1.387(3) . ?
C4 H4 0.9500 . ?
C4 C3 1.383(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.384(4) . ?
C13 H13 0.9500 . ?
C13 C12 1.386(4) . ?
C13 C14 1.378(4) . ?
C12 H12 0.9500 . ?
C14 H14 0.9500 . ?
C3 H3 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C7 120.8(2) . . ?
C8 N1 N2 111.0(2) . . ?
C8 N1 C7 127.9(2) . . ?
N3 N2 N1 107.0(2) . . ?
N2 N3 C9 108.9(2) . . ?
N3 C9 C10 121.8(2) . . ?
N3 C9 C8 107.9(2) . . ?
C8 C9 C10 130.3(2) . . ?
C11 C10 C9 119.7(2) . . ?
C15 C10 C9 121.2(2) . . ?
C15 C10 C11 119.0(2) . . ?
N1 C8 C9 105.3(2) . . ?
N1 C8 H8 127.4 . . ?
C9 C8 H8 127.4 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 120.1(2) . . ?
C12 C11 H11 120.0 . . ?
C5 C6 C7 121.3(2) . . ?
C1 C6 C5 119.3(2) . . ?
C1 C6 C7 119.4(2) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 C6 120.4(2) . . ?
C4 C5 H5 119.8 . . ?
C6 C1 H1 119.8 . . ?
C6 C1 C2 120.4(2) . . ?
C2 C1 H1 119.8 . . ?
C10 C15 H15 120.0 . . ?
C14 C15 C10 120.0(2) . . ?
C14 C15 H15 120.0 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 C5 119.9(3) . . ?
C3 C4 H4 120.0 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.0(2) . . ?
C3 C2 H2 120.0 . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C14 C13 C12 119.2(2) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.6(3) . . ?
C13 C12 H12 119.7 . . ?
C15 C14 H14 119.4 . . ?
C13 C14 C15 121.2(3) . . ?
C13 C14 H14 119.4 . . ?
C4 C3 C2 120.0(2) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
N1 C7 C6 111.6(2) . . ?
N1 C7 H7A 109.3 . . ?
N1 C7 H7B 109.3 . . ?
C6 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.089
_oxdiff_exptl_absorpt_empirical_full_min 0.889
####################################################################### 
# 
# 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_2017ncs0030z
_database_code_depnum_ccdc_archive 'CCDC 1831785'
_audit_update_record             
;
2018-03-22 deposited with the CCDC.
2018-05-01 downloaded from the CCDC.
;
_audit_creation_date             2018-03-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C31 H31 Cu F3 N9 O3 S, C F3 O3 S'
_chemical_formula_sum            'C32 H31 Cu F6 N9 O6 S2'
_chemical_formula_weight         879.32
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   14.1878(5)
_cell_length_b                   13.3086(5)
_cell_length_c                   40.4807(13)
_cell_angle_alpha                90
_cell_angle_beta                 90.608(3)
_cell_angle_gamma                90
_cell_volume                     7643.1(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    14097
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.0210
_cell_measurement_theta_min      2.1230
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.765
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62372
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.9g (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             3592
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0735
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       50
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_number            42305
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.012
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -113.00  23.00   1.00   60.00    --  -23.00 -72.00 -60.00  136
  2  ω    -88.00  27.00   1.00   60.00    --  -23.00  18.00 -90.00  115
  3  ω    -96.00  23.00   1.00   60.00    --  -23.00 -72.00  90.00  119
  4  ω    -59.00 -14.00   1.00   60.00    --  -23.00  72.00 -90.00   45
  5  ω    -65.00  10.00   1.00   60.00    --  -23.00  72.00  30.00   75
  6  ω    -68.00 -51.00   1.00   60.00    --  -23.00  72.00 120.00   17
  7  ω    -69.00  67.00   1.00   60.00    --  -23.00  72.00-120.00  136
  8  ω    -90.00 -19.00   1.00   60.00    --  -23.00 -72.00 -30.00   71
;
_diffrn_measurement_device       'four-circle κ goniometer'
_diffrn_measurement_device_type  
;
Rigaku FRE+ equipped with VHF Varimax confocal mirrors and an AFC12 goniometer and HG Saturn 724+ detector
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroLoop'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5866
_reflns_number_total             7794
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.9g (Rigaku OD, 2015)'
_computing_data_collection       
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)
;
_computing_data_reduction        'CrysAlisPro 1.171.39.9g (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.591
_refine_diff_density_min         -0.887
_refine_diff_density_rms         0.134
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     506
_refine_ls_number_reflns         7794
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1173
_refine_ls_R_factor_gt           0.0938
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1360P)²+66.0630P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2448
_refine_ls_wR_factor_ref         0.2638
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C11(H11A,H11B), C18(H18A,H18B), C25(H25A,H25B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C8(H8), C6(H6), C14(H14), C9(H9), C7(H7), C2(H2), C15(H15),
 C20(H20), C13(H13), C12(H12), C17(H17), C26(H26), C23(H23), C27(H27), C22(H22),
  C16(H16), C21(H21), C28(H28)
2.c Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.72212(5) 0.24860(5) 0.38447(2) 0.0349(2) Uani 1 1 d . . . . .
S1 S 0.60320(13) 0.01243(14) 0.41680(4) 0.0515(4) Uani 1 1 d . . . . .
S2 S 0.63377(15) 0.64961(15) 0.32905(7) 0.0690(6) Uani 1 1 d . . . . .
N2 N 0.7825(3) 0.0949(3) 0.29874(10) 0.0281(9) Uani 1 1 d . . . . .
N3 N 0.9734(4) -0.1260(3) 0.34823(11) 0.0380(11) Uani 1 1 d . . . . .
N1 N 0.7286(3) 0.1627(3) 0.34411(10) 0.0295(9) Uani 1 1 d . . . . .
O1 O 0.6441(3) 0.1110(4) 0.41677(12) 0.0527(11) Uani 1 1 d . . . . .
N4 N 1.0915(3) -0.2048(3) 0.37166(10) 0.0339(10) Uani 1 1 d . . . . .
O3 O 0.6676(4) -0.0695(4) 0.41919(11) 0.0539(12) Uani 1 1 d . . . . .
F2 F 0.4768(4) 0.0802(4) 0.45655(14) 0.0811(15) Uani 1 1 d . . . . .
N7 N 0.4855(3) 0.6643(4) 0.41986(12) 0.0398(11) Uani 1 1 d . . . . .
F1 F 0.4916(4) -0.0782(4) 0.45799(12) 0.0846(16) Uani 1 1 d . . . . .
N6 N 0.7390(4) 0.4827(4) 0.45201(12) 0.0421(12) Uani 1 1 d . . . . .
F3 F 0.5980(4) 0.0169(5) 0.48028(11) 0.0877(16) Uani 1 1 d . . . . .
N8 N 0.3443(3) 0.6881(4) 0.40049(12) 0.0435(12) Uani 1 1 d . . . . .
N5 N 0.7252(4) 0.3452(4) 0.42236(12) 0.0416(12) Uani 1 1 d . . . . .
C5 C 0.8577(4) -0.0456(4) 0.26793(12) 0.0290(10) Uani 1 1 d . . . . .
C4 C 0.8490(4) 0.0673(4) 0.27216(12) 0.0308(11) Uani 1 1 d . . . . .
H4A H 0.9119 0.0957 0.2774 0.037 Uiso 1 1 calc R . . . .
H4B H 0.8269 0.0972 0.2511 0.037 Uiso 1 1 calc R . . . .
C10 C 0.8950(4) -0.1066(4) 0.29291(12) 0.0322(11) Uani 1 1 d . . . . .
C1 C 0.8024(4) 0.1549(4) 0.32459(12) 0.0287(10) Uani 1 1 d . . . . .
H1 H 0.8613 0.1872 0.3283 0.034 Uiso 1 1 calc R . . . .
C3 C 0.6920(4) 0.0624(4) 0.30187(12) 0.0319(11) Uani 1 1 d . . . . .
H3 H 0.6588 0.0185 0.2873 0.038 Uiso 1 1 calc R . . . .
C8 C 0.8758(4) -0.2501(4) 0.25777(14) 0.0389(13) Uani 1 1 d . . . . .
H8 H 0.8820 -0.3204 0.2542 0.047 Uiso 1 1 calc R . . . .
C6 C 0.8286(4) -0.0885(4) 0.23862(13) 0.0376(13) Uani 1 1 d . . . . .
H6 H 0.8020 -0.0474 0.2217 0.045 Uiso 1 1 calc R . . . .
C14 C 1.0681(4) -0.1371(4) 0.34987(13) 0.0345(12) Uani 1 1 d . . . . .
H14 H 1.1117 -0.1005 0.3369 0.041 Uiso 1 1 calc R . . . .
O2 O 0.5275(5) 0.0003(5) 0.39276(14) 0.0796(18) Uani 1 1 d . . . . .
C9 C 0.9053(4) -0.2083(4) 0.28746(14) 0.0394(13) Uani 1 1 d . . . . .
H9 H 0.9326 -0.2497 0.3041 0.047 Uiso 1 1 calc R . . . .
N9 N 0.8024(5) 0.3828(4) 0.35006(16) 0.0562(14) Uani 1 1 d . . . . .
C7 C 0.8378(4) -0.1905(5) 0.23352(13) 0.0395(13) Uani 1 1 d . . . . .
H7 H 0.8177 -0.2193 0.2132 0.047 Uiso 1 1 calc R . . . .
C2 C 0.6586(4) 0.1048(4) 0.32971(14) 0.0350(12) Uani 1 1 d . . . . .
H2 H 0.5967 0.0962 0.3381 0.042 Uiso 1 1 calc R . . . .
C15 C 0.7333(4) 0.4441(5) 0.42169(15) 0.0420(13) Uani 1 1 d . . . . .
H15 H 0.7349 0.4830 0.4020 0.050 Uiso 1 1 calc R . . . .
C20 C 0.6860(5) 0.6294(5) 0.51634(16) 0.0510(17) Uani 1 1 d . . . . .
H20 H 0.7441 0.6073 0.5257 0.061 Uiso 1 1 calc R . . . .
O6 O 0.6391(8) 0.6127(6) 0.3570(2) 0.128(3) Uani 1 1 d . . . . .
C11 C 0.9213(5) -0.0591(5) 0.32597(13) 0.0417(14) Uani 1 1 d . . . . .
H11A H 0.9600 0.0014 0.3219 0.050 Uiso 1 1 calc R . . . .
H11B H 0.8629 -0.0371 0.3370 0.050 Uiso 1 1 calc R . . . .
C19 C 0.6763(5) 0.6303(5) 0.48191(16) 0.0475(15) Uani 1 1 d . . . . .
F6 F 0.7106(6) 0.8108(5) 0.3504(3) 0.154(4) Uani 1 1 d . . . . .
C24 C 0.5955(4) 0.6718(5) 0.46827(15) 0.0429(14) Uani 1 1 d . . . . .
C13 C 1.0086(4) -0.2385(5) 0.38462(14) 0.0423(14) Uani 1 1 d . . . . .
H13 H 1.0035 -0.2884 0.4013 0.051 Uiso 1 1 calc R . . . .
C12 C 0.9347(5) -0.1900(5) 0.37009(15) 0.0467(15) Uani 1 1 d . . . . .
H12 H 0.8696 -0.1992 0.3744 0.056 Uiso 1 1 calc R . . . .
C18 C 0.7542(5) 0.5904(5) 0.46088(17) 0.0496(16) Uani 1 1 d . . . . .
H18A H 0.7580 0.6309 0.4404 0.059 Uiso 1 1 calc R . . . .
H18B H 0.8149 0.5973 0.4730 0.059 Uiso 1 1 calc R . . . .
C17 C 0.7339(6) 0.4042(5) 0.47361(16) 0.0582(19) Uani 1 1 d . . . . .
H17 H 0.7356 0.4082 0.4970 0.070 Uiso 1 1 calc R . . . .
C26 C 0.4231(4) 0.7326(5) 0.40848(15) 0.0468(15) Uani 1 1 d . . . . .
H26 H 0.4348 0.8026 0.4066 0.056 Uiso 1 1 calc R . . . .
C23 C 0.5247(5) 0.7003(6) 0.48978(17) 0.0528(16) Uani 1 1 d . . . . .
H23 H 0.4678 0.7268 0.4808 0.063 Uiso 1 1 calc R . . . .
C25 C 0.5827(5) 0.6883(6) 0.43107(15) 0.0493(16) Uani 1 1 d . . . . .
H25A H 0.5970 0.7592 0.4257 0.059 Uiso 1 1 calc R . . . .
H25B H 0.6279 0.6453 0.4191 0.059 Uiso 1 1 calc R . . . .
C29 C 0.8449(4) 0.4466(5) 0.34058(15) 0.0453(14) Uani 1 1 d . . . . .
C27 C 0.3582(5) 0.5863(5) 0.40727(18) 0.0527(16) Uani 1 1 d . . . . .
H27 H 0.3127 0.5347 0.4041 0.063 Uiso 1 1 calc R . . . .
C22 C 0.5339(6) 0.6917(6) 0.52381(17) 0.064(2) Uani 1 1 d . . . . .
H22 H 0.4830 0.7088 0.5378 0.077 Uiso 1 1 calc R . . . .
C16 C 0.7259(5) 0.3206(5) 0.45550(15) 0.0516(16) Uani 1 1 d . . . . .
H16 H 0.7214 0.2543 0.4641 0.062 Uiso 1 1 calc R . . . .
C21 C 0.6171(6) 0.6582(5) 0.53686(16) 0.0539(18) Uani 1 1 d . . . . .
H21 H 0.6263 0.6553 0.5601 0.065 Uiso 1 1 calc R . . . .
F5 F 0.5703(6) 0.8132(5) 0.3529(3) 0.157(4) Uani 1 1 d . . . . .
C28 C 0.4473(5) 0.5730(6) 0.4191(2) 0.0596(19) Uani 1 1 d . . . . .
H28 H 0.4762 0.5115 0.4255 0.071 Uiso 1 1 calc R . . . .
F4 F 0.6445(7) 0.8283(5) 0.3072(2) 0.154(3) Uani 1 1 d . . . . .
C32 C 0.6356(6) 0.7799(6) 0.3341(2) 0.066(2) Uani 1 1 d . . . . .
O4 O 0.7077(6) 0.6245(7) 0.30805(19) 0.121(3) Uani 1 1 d . . . . .
C31 C 0.5393(6) 0.0072(6) 0.45495(19) 0.0575(18) Uani 1 1 d . . . . .
O5 O 0.5453(7) 0.6378(7) 0.3105(3) 0.150(4) Uani 1 1 d . . . . .
C30 C 0.8987(7) 0.5317(8) 0.3292(2) 0.087(3) Uani 1 1 d . . . . .
H30A H 0.9628 0.5100 0.3239 0.130 Uiso 1 1 calc GR . . . .
H30B H 0.9014 0.5830 0.3465 0.130 Uiso 1 1 calc GR . . . .
H30C H 0.8685 0.5599 0.3094 0.130 Uiso 1 1 calc GR . . . .


_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 N1 1.997(4) . ?
Cu1 O1 2.513(5) . ?
Cu1 N4 2.017(4) 3_455 ?
Cu1 N8 2.012(5) 3_545 ?
Cu1 N5 2.001(5) . ?
Cu1 N9 2.542(6) . ?
S1 O1 1.435(5) . ?
S1 O3 1.426(5) . ?
S1 O2 1.450(6) . ?
S1 C31 1.801(8) . ?
S2 O6 1.234(9) . ?
S2 C32 1.747(8) . ?
S2 O4 1.398(8) . ?
S2 O5 1.465(8) . ?
N2 C4 1.484(7) . ?
N2 C1 1.343(6) . ?
N2 C3 1.363(7) . ?
N3 C14 1.353(7) . ?
N3 C11 1.461(7) . ?
N3 C12 1.349(8) . ?
N1 C1 1.322(7) . ?
N1 C2 1.382(7) . ?
N4 Cu1 2.017(4) 3_545 ?
N4 C14 1.301(7) . ?
N4 C13 1.368(8) . ?
F2 C31 1.318(9) . ?
N7 C26 1.347(8) . ?
N7 C25 1.482(8) . ?
N7 C28 1.331(9) . ?
F1 C31 1.329(9) . ?
N6 C15 1.332(8) . ?
N6 C18 1.493(8) . ?
N6 C17 1.365(9) . ?
F3 C31 1.321(9) . ?
N8 Cu1 2.012(5) 3_455 ?
N8 C26 1.304(8) . ?
N8 C27 1.396(9) . ?
N5 C15 1.323(8) . ?
N5 C16 1.381(8) . ?
C5 C4 1.517(7) . ?
C5 C10 1.397(7) . ?
C5 C6 1.376(7) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C10 C9 1.379(8) . ?
C10 C11 1.523(7) . ?
C1 H1 0.9500 . ?
C3 H3 0.9500 . ?
C3 C2 1.351(8) . ?
C8 H8 0.9500 . ?
C8 C9 1.385(8) . ?
C8 C7 1.369(8) . ?
C6 H6 0.9500 . ?
C6 C7 1.379(9) . ?
C14 H14 0.9500 . ?
C9 H9 0.9500 . ?
N9 C29 1.112(8) . ?
C7 H7 0.9500 . ?
C2 H2 0.9500 . ?
C15 H15 0.9500 . ?
C20 H20 0.9500 . ?
C20 C19 1.399(9) . ?
C20 C21 1.346(10) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C19 C24 1.383(9) . ?
C19 C18 1.499(9) . ?
F6 C32 1.312(10) . ?
C24 C23 1.389(10) . ?
C24 C25 1.530(8) . ?
C13 H13 0.9500 . ?
C13 C12 1.360(8) . ?
C12 H12 0.9500 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C17 H17 0.9500 . ?
C17 C16 1.337(10) . ?
C26 H26 0.9500 . ?
C23 H23 0.9500 . ?
C23 C22 1.387(10) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C29 C30 1.445(10) . ?
C27 H27 0.9500 . ?
C27 C28 1.360(9) . ?
C22 H22 0.9500 . ?
C22 C21 1.363(11) . ?
C16 H16 0.9500 . ?
C21 H21 0.9500 . ?
F5 C32 1.285(11) . ?
C28 H28 0.9500 . ?
F4 C32 1.271(11) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 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
N1 Cu1 O1 91.88(17) . . ?
N1 Cu1 N4 90.93(17) . 3_455 ?
N1 Cu1 N8 89.27(18) . 3_545 ?
N1 Cu1 N5 173.7(2) . . ?
N1 Cu1 N9 85.94(19) . . ?
O1 Cu1 N9 177.77(18) . . ?
N4 Cu1 O1 87.09(18) 3_455 . ?
N4 Cu1 N9 93.4(2) 3_455 . ?
N8 Cu1 O1 85.60(19) 3_545 . ?
N8 Cu1 N4 172.7(2) 3_545 3_455 ?
N8 Cu1 N9 93.9(2) 3_545 . ?
N5 Cu1 O1 94.3(2) . . ?
N5 Cu1 N4 90.68(18) . 3_455 ?
N5 Cu1 N8 89.90(19) . 3_545 ?
N5 Cu1 N9 87.9(2) . . ?
O1 S1 O2 113.5(3) . . ?
O1 S1 C31 104.1(3) . . ?
O3 S1 O1 116.1(3) . . ?
O3 S1 O2 115.5(3) . . ?
O3 S1 C31 103.9(3) . . ?
O2 S1 C31 101.2(4) . . ?
O6 S2 C32 106.7(5) . . ?
O6 S2 O4 115.0(6) . . ?
O6 S2 O5 118.1(7) . . ?
O4 S2 C32 107.3(5) . . ?
O4 S2 O5 107.8(7) . . ?
O5 S2 C32 100.3(5) . . ?
C1 N2 C4 125.6(4) . . ?
C1 N2 C3 107.8(4) . . ?
C3 N2 C4 126.5(4) . . ?
C14 N3 C11 126.3(6) . . ?
C12 N3 C14 108.0(5) . . ?
C12 N3 C11 125.6(5) . . ?
C1 N1 Cu1 125.3(4) . . ?
C1 N1 C2 106.0(4) . . ?
C2 N1 Cu1 128.7(4) . . ?
S1 O1 Cu1 147.9(3) . . ?
C14 N4 Cu1 127.9(4) . 3_545 ?
C14 N4 C13 105.9(5) . . ?
C13 N4 Cu1 126.3(4) . 3_545 ?
C26 N7 C25 124.4(6) . . ?
C28 N7 C26 110.0(5) . . ?
C28 N7 C25 125.5(5) . . ?
C15 N6 C18 126.8(6) . . ?
C15 N6 C17 107.0(5) . . ?
C17 N6 C18 126.1(5) . . ?
C26 N8 Cu1 129.2(5) . 3_455 ?
C26 N8 C27 105.8(5) . . ?
C27 N8 Cu1 124.8(4) . 3_455 ?
C15 N5 Cu1 128.7(4) . . ?
C15 N5 C16 104.9(5) . . ?
C16 N5 Cu1 126.3(5) . . ?
C10 C5 C4 121.6(4) . . ?
C6 C5 C4 118.9(5) . . ?
C6 C5 C10 119.4(5) . . ?
N2 C4 C5 112.4(4) . . ?
N2 C4 H4A 109.1 . . ?
N2 C4 H4B 109.1 . . ?
C5 C4 H4A 109.1 . . ?
C5 C4 H4B 109.1 . . ?
H4A C4 H4B 107.9 . . ?
C5 C10 C11 118.9(5) . . ?
C9 C10 C5 119.6(5) . . ?
C9 C10 C11 121.5(5) . . ?
N2 C1 H1 124.7 . . ?
N1 C1 N2 110.6(5) . . ?
N1 C1 H1 124.7 . . ?
N2 C3 H3 126.7 . . ?
C2 C3 N2 106.5(5) . . ?
C2 C3 H3 126.7 . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.1(5) . . ?
C5 C6 H6 119.7 . . ?
C5 C6 C7 120.6(5) . . ?
C7 C6 H6 119.7 . . ?
N3 C14 H14 124.6 . . ?
N4 C14 N3 110.8(5) . . ?
N4 C14 H14 124.6 . . ?
C10 C9 C8 120.1(5) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C29 N9 Cu1 166.7(6) . . ?
C8 C7 C6 120.0(5) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
N1 C2 H2 125.4 . . ?
C3 C2 N1 109.1(5) . . ?
C3 C2 H2 125.4 . . ?
N6 C15 H15 124.2 . . ?
N5 C15 N6 111.7(6) . . ?
N5 C15 H15 124.2 . . ?
C19 C20 H20 118.4 . . ?
C21 C20 H20 118.4 . . ?
C21 C20 C19 123.2(6) . . ?
N3 C11 C10 114.0(5) . . ?
N3 C11 H11A 108.8 . . ?
N3 C11 H11B 108.8 . . ?
C10 C11 H11A 108.8 . . ?
C10 C11 H11B 108.8 . . ?
H11A C11 H11B 107.6 . . ?
C20 C19 C18 119.8(6) . . ?
C24 C19 C20 118.3(6) . . ?
C24 C19 C18 121.9(6) . . ?
C19 C24 C23 117.4(6) . . ?
C19 C24 C25 122.6(6) . . ?
C23 C24 C25 119.9(5) . . ?
N4 C13 H13 125.1 . . ?
C12 C13 N4 109.9(5) . . ?
C12 C13 H13 125.1 . . ?
N3 C12 C13 105.4(6) . . ?
N3 C12 H12 127.3 . . ?
C13 C12 H12 127.3 . . ?
N6 C18 C19 111.8(6) . . ?
N6 C18 H18A 109.3 . . ?
N6 C18 H18B 109.3 . . ?
C19 C18 H18A 109.3 . . ?
C19 C18 H18B 109.3 . . ?
H18A C18 H18B 107.9 . . ?
N6 C17 H17 126.6 . . ?
C16 C17 N6 106.9(6) . . ?
C16 C17 H17 126.6 . . ?
N7 C26 H26 125.1 . . ?
N8 C26 N7 109.7(6) . . ?
N8 C26 H26 125.1 . . ?
C24 C23 H23 118.7 . . ?
C22 C23 C24 122.6(6) . . ?
C22 C23 H23 118.7 . . ?
N7 C25 C24 111.7(5) . . ?
N7 C25 H25A 109.3 . . ?
N7 C25 H25B 109.3 . . ?
C24 C25 H25A 109.3 . . ?
C24 C25 H25B 109.3 . . ?
H25A C25 H25B 107.9 . . ?
N9 C29 C30 178.0(9) . . ?
N8 C27 H27 125.5 . . ?
C28 C27 N8 109.0(6) . . ?
C28 C27 H27 125.5 . . ?
C23 C22 H22 120.5 . . ?
C21 C22 C23 118.9(7) . . ?
C21 C22 H22 120.5 . . ?
N5 C16 H16 125.2 . . ?
C17 C16 N5 109.6(6) . . ?
C17 C16 H16 125.2 . . ?
C20 C21 C22 119.1(6) . . ?
C20 C21 H21 120.5 . . ?
C22 C21 H21 120.5 . . ?
N7 C28 C27 105.4(6) . . ?
N7 C28 H28 127.3 . . ?
C27 C28 H28 127.3 . . ?
F6 C32 S2 112.4(6) . . ?
F5 C32 S2 113.7(7) . . ?
F5 C32 F6 100.4(9) . . ?
F4 C32 S2 113.9(7) . . ?
F4 C32 F6 100.7(9) . . ?
F4 C32 F5 114.2(9) . . ?
F2 C31 S1 111.0(5) . . ?
F2 C31 F1 106.4(6) . . ?
F2 C31 F3 108.0(7) . . ?
F1 C31 S1 112.0(5) . . ?
F3 C31 S1 110.0(6) . . ?
F3 C31 F1 109.2(6) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.387 0.250 104.7 20.5 ''
2 0.000 0.613 0.750 104.7 20.5 ''
3 0.189 0.335 0.602 18.9 0.0 ?
4 0.189 0.665 0.102 18.9 0.0 ?
5 0.311 0.165 0.398 18.9 0.0 ?
6 0.311 0.835 0.898 18.9 0.0 ?
7 0.500 0.113 0.750 104.7 20.5 ?
8 0.500 0.887 0.250 104.7 20.5 ?
9 0.689 0.165 0.102 18.9 0.0 ?
10 0.689 0.835 0.602 18.9 0.0 ?
11 0.811 0.335 0.898 18.9 0.0 ?
12 0.811 0.665 0.398 18.9 0.0 ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
