# 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_sad2
_database_code_depnum_ccdc_archive 'CCDC 1520303'
_audit_update_record             
;
2017-01-04 deposited with the CCDC.
2018-06-27 downloaded from the CCDC.
;
_audit_creation_date             2016-12-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H26 N6 O S'
_chemical_formula_sum            'C23 H26 N6 O S'
_chemical_formula_weight         434.56
_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'
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           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                   9.911(2)
_cell_length_b                   18.212(4)
_cell_length_c                   12.793(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.92(3)
_cell_angle_gamma                90
_cell_volume                     2300.8(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    28560
_cell_measurement_temperature    200
_cell_measurement_theta_max      27.00
_cell_measurement_theta_min      1.95
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.167
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.373067
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2004/1 (Bruker,2004) was used for absorption correction.
R(int) was 0.2585 before and 0.0491 after correction.
The Ratio of minimum to maximum transmission is 0.3731.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.68
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.26
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            28560
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.998
_diffrn_reflns_theta_min         1.950
_diffrn_ambient_temperature      200.0
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            KappaCCD
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker-AXS-enraf-nonius KappaCCD'
_diffrn_measurement_method       'Phi and omega scans'
_diffrn_radiation_collimation    'Montel optic'
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Multilayer mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec ISG250'
_diffrn_source_target            Mo
_diffrn_source_type              'Microfocus sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3224
_reflns_number_total             5022
_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       EvalCCD
_computing_data_collection       Collect
_computing_data_reduction        EvalCCD
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    ?
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     487
_refine_ls_number_reflns         5022
_refine_ls_number_restraints     844
_refine_ls_R_factor_all          0.0866
_refine_ls_R_factor_gt           0.0441
_refine_ls_restrained_S_all      1.010
_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)+(0.0448P)²+0.8940P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1036
_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, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All S(H) groups
2. Restrained distances
 C2-C8
 1.4 with sigma of 0.02
 C3-C2
 1.4 with sigma of 0.02
 C2'-C8
 1.4 with sigma of 0.02
 C1-C2'
 1.4 with sigma of 0.02
 C10-N6
 1.35 with sigma of 0.02
 C10'-N6'
 1.35 with sigma of 0.02
 N3-C10
 1.3 with sigma of 0.02
 N3'-C10'
 1.3 with sigma of 0.02
3. Rigid bond restraints
 C5', C18, C9, C11, N4, C21, C16', C16, C15', C12, N6', C22, C1, C13, C4', N2',
  N3, C21', C7', N6, C19, O1, C2', C11', C9', N5', C15, C3, C4, N2, C20', C6,
 C7, C2, N4', C23', C6', C14, C10, N1, C20, C3', C17', C23, C17, S1, S1', C5,
 N5, C8, N3', C10', C14'
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C5' \\sim C18 \\sim C9 \\sim C11 \\sim N4 \\sim C21 \\sim C16' \\sim C16 \\sim
C15' \\sim C12 \\sim N6' \\sim C22 \\sim C1 \\sim C13 \\sim C4' \\sim N2' \\sim
N3 \\sim C21' \\sim C7' \\sim N6 \\sim C19 \\sim O1 \\sim C2' \\sim C11' \\sim
C9' \\sim N5' \\sim C15 \\sim C3 \\sim C4 \\sim N2 \\sim C20' \\sim C6 \\sim C7
\\sim C2 \\sim N4' \\sim C23' \\sim C6' \\sim C14 \\sim C10 \\sim N1 \\sim C20
\\sim C3' \\sim C17' \\sim C23 \\sim C17 \\sim S1 \\sim S1' \\sim C5 \\sim N5
\\sim C8 \\sim N3' \\sim C10' \\sim C14': within 1.7A with sigma of 0.04 and
sigma for terminal atoms of 0.08
Uanis(C11') \\sim Ueq: with sigma of 0.05 and sigma for terminal atoms of 0.1
Uanis(C11) \\sim Ueq: with sigma of 0.05 and sigma for terminal atoms of 0.1
Uanis(C21) \\sim Ueq, Uanis(C20) \\sim Ueq: with sigma of 0.05 and sigma for
terminal atoms of 0.1
5. Others
 Sof(S1')=Sof(N3')=Sof(H3')=Sof(N6')=Sof(H6')=Sof(C4')=Sof(C2')=Sof(C6')=
 Sof(C3')=Sof(H3'A)=Sof(H8BC)=Sof(H8BD)=Sof(C5')=Sof(H5')=Sof(C9')=Sof(H9'A)=
 Sof(H9'B)=Sof(H9'C)=Sof(C11')=Sof(H11D)=Sof(H11E)=Sof(H11F)=Sof(N2')=Sof(C7')=
 Sof(H7')=Sof(C10')=1-FVAR(1)
 Sof(C10)=Sof(N2)=Sof(H8AA)=Sof(H8AB)=Sof(C7)=Sof(H7)=Sof(C11)=Sof(H11A)=
 Sof(H11B)=Sof(H11C)=Sof(C5)=Sof(H5)=Sof(C3)=Sof(H3)=Sof(C9)=Sof(H9A)=Sof(H9B)=
 Sof(H9C)=Sof(C6)=Sof(C4)=Sof(N6)=Sof(H6)=Sof(N3)=Sof(C2)=Sof(S1)=Sof(H1A)=
 FVAR(1)
 Sof(H22A)=Sof(C20')=Sof(H20')=Sof(C21')=Sof(H21')=Sof(N5')=Sof(C23')=
 Sof(H23')=1-FVAR(2)
 Sof(H22)=Sof(N5)=Sof(C23)=Sof(H23)=Sof(C20)=Sof(H20)=Sof(C21)=Sof(H21)=FVAR(2)
 Sof(C14')=Sof(H14')=Sof(C16')=Sof(H16')=Sof(C17')=Sof(H17')=Sof(N4')=
 Sof(C15')=Sof(H15')=1-FVAR(3)
 Sof(N4)=Sof(C17)=Sof(H17)=Sof(C16)=Sof(H16)=Sof(C15)=Sof(H15)=Sof(C14)=
 Sof(H14)=FVAR(3)
6.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C8(H8BC,H8BD), C8(H8AA,H8AB), C18(H18A,H18B)
6.b Aromatic/amide H refined with riding coordinates:
 N3'(H3'), N6'(H6'), C3'(H3'A), C7(H7), C5'(H5'), C14'(H14'), C17(H17),
 C22(H22A), C22(H22), C16(H16), C15(H15), C20'(H20'), C21'(H21'), C23(H23),
 C20(H20), C23'(H23'), C21(H21), C5(H5), C3(H3), N6(H6), C7'(H7'), C16'(H16'),
 C14(H14), C17'(H17'), C15'(H15')
6.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C9'(H9'A,H9'B,H9'C), C9(H9A,H9B,H9C), C11'(H11D,H11E,H11F)
6.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), S1(H1A)
;
_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
S1' S -0.2211(4) -0.01086(19) 0.4923(5) 0.0595(11) Uani 0.651(14) 1 d . U P A 2
C10 C -0.191(2) 0.0829(14) 0.534(2) 0.048(3) Uani 0.349(14) 1 d D U P A 1
N1 N 0.54087(14) 0.34264(8) 0.72057(11) 0.0413(4) Uani 1 1 d . U . . .
N3' N -0.0599(12) 0.0947(8) 0.5626(13) 0.060(3) Uani 0.651(14) 1 d D U P A 2
H3' H 0.0093 0.0657 0.5539 0.072 Uiso 0.651(14) 1 calc R . P A 2
N2 N -0.037(2) 0.1667(12) 0.5755(14) 0.039(2) Uani 0.349(14) 1 d . U P A 1
N6' N -0.2905(8) 0.1234(4) 0.5359(7) 0.0551(16) Uani 0.651(14) 1 d D U P A 2
H6' H -0.2662 0.1694 0.5472 0.066 Uiso 0.651(14) 1 calc R . P A 2
C1 C 0.26042(18) 0.27251(10) 0.69379(17) 0.0504(5) Uani 1 1 d D U . . .
N4 N 0.6536(17) 0.4531(7) 0.5091(13) 0.070(2) Uani 0.54(3) 1 d . U P B 1
C4' C 0.0705(8) 0.3839(5) 0.7174(8) 0.0619(19) Uani 0.651(14) 1 d . U P A 2
C2' C 0.2934(11) 0.3362(8) 0.7447(17) 0.050(3) Uani 0.651(14) 1 d D U P A 2
C12 C 0.54169(19) 0.40594(10) 0.65105(15) 0.0470(5) Uani 1 1 d . U . . .
H12A H 0.5834 0.4481 0.6905 0.056 Uiso 1 1 calc R . . . .
H12B H 0.4472 0.4194 0.6274 0.056 Uiso 1 1 calc R . . . .
C6' C 0.1267(12) 0.2599(6) 0.6667(7) 0.051(2) Uani 0.651(14) 1 d . U P A 2
C19 C 0.6950(2) 0.25503(12) 0.81585(17) 0.0557(5) Uani 1 1 d . U . . .
C13 C 0.6181(2) 0.39158(11) 0.55686(16) 0.0533(5) Uani 1 1 d . U . . .
C3' C 0.2036(9) 0.3933(5) 0.7578(7) 0.0506(18) Uani 0.651(14) 1 d . U P A 2
H3'A H 0.2323 0.4373 0.7931 0.061 Uiso 0.651(14) 1 calc R . P A 2
C8 C 0.4363(2) 0.35071(11) 0.79460(16) 0.0503(5) Uani 1 1 d D U . . .
H8BC H 0.4405 0.4012 0.8236 0.060 Uiso 0.651(14) 1 calc R . P A 2
H8BD H 0.4560 0.3162 0.8537 0.060 Uiso 0.651(14) 1 calc R . P A 2
H8AA H 0.4480 0.3121 0.8491 0.060 Uiso 0.349(14) 1 calc R . P A 1
H8AB H 0.4460 0.3991 0.8298 0.060 Uiso 0.349(14) 1 calc R . P A 1
C18 C 0.6749(2) 0.33144(11) 0.77616(18) 0.0565(5) Uani 1 1 d . U . . .
H18A H 0.6865 0.3660 0.8360 0.068 Uiso 1 1 calc R . . . .
H18B H 0.7453 0.3428 0.7281 0.068 Uiso 1 1 calc R . . . .
C7 C 0.087(2) 0.1851(11) 0.5953(12) 0.040(3) Uani 0.349(14) 1 d . U P A 1
H7 H 0.1563 0.1501 0.5856 0.048 Uiso 0.349(14) 1 calc R . P A 1
C11 C -0.430(3) 0.1116(16) 0.554(2) 0.089(7) Uani 0.349(14) 1 d . U P A 1
H11A H -0.4804 0.1417 0.6006 0.134 Uiso 0.349(14) 1 calc GR . P A 1
H11B H -0.4487 0.0596 0.5655 0.134 Uiso 0.349(14) 1 calc GR . P A 1
H11C H -0.4565 0.1245 0.4809 0.134 Uiso 0.349(14) 1 calc GR . P A 1
C5' C 0.0339(8) 0.3172(4) 0.6743(8) 0.0635(19) Uani 0.651(14) 1 d . U P A 2
H5' H -0.0578 0.3096 0.6486 0.076 Uiso 0.651(14) 1 calc R . P A 2
C14' C 0.652(2) 0.3239(10) 0.5209(16) 0.061(3) Uani 0.46(3) 1 d . U P B 2
H14' H 0.6170 0.2822 0.5539 0.073 Uiso 0.46(3) 1 calc R . P B 2
C9' C -0.0325(9) 0.4459(5) 0.7235(10) 0.095(3) Uani 0.651(14) 1 d . U P A 2
H9'A H -0.0842 0.4384 0.7845 0.142 Uiso 0.651(14) 1 calc GR . P A 2
H9'B H -0.0944 0.4461 0.6594 0.142 Uiso 0.651(14) 1 calc GR . P A 2
H9'C H 0.0151 0.4931 0.7303 0.142 Uiso 0.651(14) 1 calc GR . P A 2
C17 C 0.7064(15) 0.4436(7) 0.4166(12) 0.083(3) Uani 0.54(3) 1 d . U P B 1
H17 H 0.7356 0.4860 0.3816 0.099 Uiso 0.54(3) 1 calc R . P B 1
C22 C 0.7323(3) 0.11409(17) 0.8813(3) 0.0940(9) Uani 1 1 d . U . . .
H22A H 0.7303 0.0651 0.9067 0.113 Uiso 0.484(8) 1 calc R . P C 2
H22 H 0.7418 0.0653 0.9070 0.113 Uiso 0.516(8) 1 calc R . P C 1
C16 C 0.7208(17) 0.3773(7) 0.3701(10) 0.089(3) Uani 0.54(3) 1 d . U P B 1
H16 H 0.7586 0.3739 0.3046 0.107 Uiso 0.54(3) 1 calc R . P B 1
C15 C 0.679(2) 0.3153(9) 0.4197(13) 0.092(4) Uani 0.54(3) 1 d . U P B 1
H15 H 0.6890 0.2686 0.3882 0.111 Uiso 0.54(3) 1 calc R . P B 1
C20' C 0.7548(8) 0.2458(4) 0.9136(5) 0.080(2) Uani 0.484(8) 1 d . U P C 2
H20' H 0.7800 0.2868 0.9568 0.097 Uiso 0.484(8) 1 calc R . P C 2
N5 N 0.5892(5) 0.2071(2) 0.7964(5) 0.0700(18) Uani 0.516(8) 1 d . U P C 1
C21' C 0.7779(10) 0.1760(5) 0.9484(6) 0.099(3) Uani 0.484(8) 1 d . U P C 2
H21' H 0.8232 0.1674 1.0157 0.119 Uiso 0.484(8) 1 calc R . P C 2
C23 C 0.6093(7) 0.1380(3) 0.8272(7) 0.092(3) Uani 0.516(8) 1 d . U P C 1
H23 H 0.5386 0.1033 0.8124 0.111 Uiso 0.516(8) 1 calc R . P C 1
N5' N 0.6731(9) 0.1999(2) 0.7485(4) 0.079(2) Uani 0.484(8) 1 d . U P C 2
C20 C 0.8069(8) 0.2297(4) 0.8674(9) 0.114(3) Uani 0.516(8) 1 d . U P C 1
H20 H 0.8784 0.2630 0.8870 0.137 Uiso 0.516(8) 1 calc R . P C 1
C23' C 0.6947(11) 0.1312(3) 0.7840(5) 0.091(3) Uani 0.484(8) 1 d . U P C 2
H23' H 0.6818 0.0922 0.7349 0.109 Uiso 0.484(8) 1 calc R . P C 2
C21 C 0.8232(9) 0.1565(5) 0.8938(10) 0.137(4) Uani 0.516(8) 1 d . U P C 1
H21 H 0.9092 0.1397 0.9226 0.165 Uiso 0.516(8) 1 calc R . P C 1
C5 C 0.0310(14) 0.3157(8) 0.6287(9) 0.046(2) Uani 0.349(14) 1 d . U P A 1
H5 H -0.0573 0.3072 0.5958 0.055 Uiso 0.349(14) 1 calc R . P A 1
C3 C 0.1913(17) 0.3934(9) 0.7220(11) 0.042(3) Uani 0.349(14) 1 d D U P A 1
H3 H 0.2075 0.4411 0.7502 0.051 Uiso 0.349(14) 1 calc R . P A 1
C9 C -0.0320(15) 0.4476(9) 0.6646(14) 0.077(4) Uani 0.349(14) 1 d . U P A 1
H9A H -0.1256 0.4300 0.6551 0.115 Uiso 0.349(14) 1 calc GR . P A 1
H9B H -0.0132 0.4786 0.6049 0.115 Uiso 0.349(14) 1 calc GR . P A 1
H9C H -0.0191 0.4763 0.7295 0.115 Uiso 0.349(14) 1 calc GR . P A 1
C6 C 0.125(2) 0.2591(12) 0.6327(11) 0.037(2) Uani 0.349(14) 1 d . U P A 1
C4 C 0.0621(15) 0.3839(9) 0.6710(11) 0.050(3) Uani 0.349(14) 1 d . U P A 1
N6 N -0.2828(15) 0.1253(8) 0.5771(11) 0.059(3) Uani 0.349(14) 1 d D U P A 1
H6 H -0.2551 0.1614 0.6194 0.070 Uiso 0.349(14) 1 calc R . P A 1
C11' C -0.4336(11) 0.1074(8) 0.5153(10) 0.072(2) Uani 0.651(14) 1 d . U P A 2
H11D H -0.4530 0.0939 0.4414 0.108 Uiso 0.651(14) 1 calc GR . P A 2
H11E H -0.4865 0.1509 0.5307 0.108 Uiso 0.651(14) 1 calc GR . P A 2
H11F H -0.4580 0.0666 0.5599 0.108 Uiso 0.651(14) 1 calc GR . P A 2
N2' N -0.0385(14) 0.1719(7) 0.6041(9) 0.055(2) Uani 0.651(14) 1 d . U P A 2
N3 N -0.0651(19) 0.1054(15) 0.558(2) 0.044(3) Uani 0.349(14) 1 d D U P A 1
C7' C 0.0862(13) 0.1880(7) 0.6266(8) 0.054(2) Uani 0.651(14) 1 d . U P A 2
H7' H 0.1536 0.1522 0.6168 0.064 Uiso 0.651(14) 1 calc R . P A 2
O1 O 0.35126(13) 0.21780(7) 0.68538(12) 0.0569(4) Uani 1 1 d . U . . .
H1 H 0.4296 0.2336 0.7029 0.085 Uiso 1 1 calc GR . . . .
C10' C -0.1909(10) 0.0713(7) 0.5389(15) 0.056(3) Uani 0.651(14) 1 d D U P A 2
C16' C 0.784(2) 0.3701(10) 0.3992(14) 0.105(4) Uani 0.46(3) 1 d . U P B 2
H16' H 0.8389 0.3651 0.3423 0.126 Uiso 0.46(3) 1 calc R . P B 2
C14 C 0.623(2) 0.3206(10) 0.5176(14) 0.083(4) Uani 0.54(3) 1 d . U P B 1
H14 H 0.5905 0.2792 0.5532 0.100 Uiso 0.54(3) 1 calc R . P B 1
C17' C 0.757(2) 0.4346(12) 0.4374(17) 0.109(5) Uani 0.46(3) 1 d . U P B 2
H17' H 0.7966 0.4761 0.4072 0.130 Uiso 0.46(3) 1 calc R . P B 2
N4' N 0.678(2) 0.4473(9) 0.5155(16) 0.086(4) Uani 0.46(3) 1 d . U P B 2
C15' C 0.7312(19) 0.3118(13) 0.4435(16) 0.089(3) Uani 0.46(3) 1 d . U P B 2
H15' H 0.7491 0.2634 0.4207 0.107 Uiso 0.46(3) 1 calc R . P B 2
C2 C 0.302(2) 0.3448(15) 0.739(3) 0.042(3) Uani 0.349(14) 1 d D U P A 1
S1 S -0.2183(8) -0.0108(4) 0.5010(9) 0.067(2) Uani 0.349(14) 1 d . U P A 1
H1A H -0.3221 -0.0169 0.4461 0.101 Uiso 0.349(14) 1 calc GR . P A 1


_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
S1' C10' 1.628(12) . ?
C10 N6 1.346(17) . ?
C10 N3 1.327(17) . ?
C10 S1 1.77(2) . ?
N1 C12 1.456(2) . ?
N1 C8 1.470(2) . ?
N1 C18 1.467(2) . ?
N3' H3' 0.8800 . ?
N3' N2' 1.51(2) . ?
N3' C10' 1.376(9) . ?
N2 C7 1.28(3) . ?
N2 N3 1.17(4) . ?
N6' H6' 0.8800 . ?
N6' C11' 1.450(13) . ?
N6' C10' 1.367(11) . ?
C1 C2' 1.357(12) . ?
C1 C6' 1.360(12) . ?
C1 C6 1.511(18) . ?
C1 O1 1.353(2) . ?
C1 C2 1.48(2) . ?
N4 C13 1.337(14) . ?
N4 C17 1.34(2) . ?
C4' C3' 1.385(11) . ?
C4' C5' 1.370(10) . ?
C4' C9' 1.529(12) . ?
C2' C3' 1.389(12) . ?
C2' C8 1.526(9) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.500(3) . ?
C6' C5' 1.401(14) . ?
C6' C7' 1.451(15) . ?
C19 C18 1.489(3) . ?
C19 C20' 1.347(7) . ?
C19 N5 1.371(4) . ?
C19 N5' 1.328(5) . ?
C19 C20 1.324(7) . ?
C13 C14' 1.37(2) . ?
C13 C14 1.389(18) . ?
C13 N4' 1.309(17) . ?
C3' H3'A 0.9500 . ?
C8 H8BC 0.9900 . ?
C8 H8BD 0.9900 . ?
C8 H8AA 0.9900 . ?
C8 H8AB 0.9900 . ?
C8 C2 1.454(16) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C7 H7 0.9500 . ?
C7 C6 1.47(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C11 N6 1.48(3) . ?
C5' H5' 0.9500 . ?
C14' H14' 0.9500 . ?
C14' C15' 1.33(3) . ?
C9' H9'A 0.9800 . ?
C9' H9'B 0.9800 . ?
C9' H9'C 0.9800 . ?
C17 H17 0.9500 . ?
C17 C16 1.359(17) . ?
C22 H22A 0.9500 . ?
C22 H22 0.9500 . ?
C22 C21' 1.464(9) . ?
C22 C23 1.418(6) . ?
C22 C23' 1.305(7) . ?
C22 C21 1.187(8) . ?
C16 H16 0.9500 . ?
C16 C15 1.375(19) . ?
C15 H15 0.9500 . ?
C15 C14 1.42(2) . ?
C20' H20' 0.9500 . ?
C20' C21' 1.360(11) . ?
N5 C23 1.329(6) . ?
C21' H21' 0.9500 . ?
C23 H23 0.9500 . ?
N5' C23' 1.343(7) . ?
C20 H20 0.9500 . ?
C20 C21 1.381(10) . ?
C23' H23' 0.9500 . ?
C21 H21 0.9500 . ?
C5 H5 0.9500 . ?
C5 C6 1.39(3) . ?
C5 C4 1.38(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.397(19) . ?
C3 C2 1.415(18) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C9 C4 1.49(2) . ?
N6 H6 0.8800 . ?
C11' H11D 0.9800 . ?
C11' H11E 0.9800 . ?
C11' H11F 0.9800 . ?
N2' C7' 1.279(17) . ?
C7' H7' 0.9500 . ?
O1 H1 0.8400 . ?
C16' H16' 0.9500 . ?
C16' C17' 1.31(2) . ?
C16' C15' 1.33(2) . ?
C14 H14 0.9500 . ?
C17' H17' 0.9500 . ?
C17' N4' 1.34(3) . ?
C15' H15' 0.9500 . ?
S1 H1A 1.2000 . ?

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
N6 C10 S1 123.8(17) . . ?
N3 C10 N6 112.4(18) . . ?
N3 C10 S1 118.2(18) . . ?
C12 N1 C8 110.82(15) . . ?
C12 N1 C18 110.73(14) . . ?
C18 N1 C8 111.16(16) . . ?
N2' N3' H3' 121.1 . . ?
C10' N3' H3' 121.1 . . ?
C10' N3' N2' 117.8(12) . . ?
N3 N2 C7 120(2) . . ?
C11' N6' H6' 118.0 . . ?
C10' N6' H6' 118.0 . . ?
C10' N6' C11' 123.9(8) . . ?
C2' C1 C6' 117.1(7) . . ?
O1 C1 C2' 122.2(4) . . ?
O1 C1 C6' 119.7(5) . . ?
O1 C1 C6 113.9(8) . . ?
O1 C1 C2 121.2(7) . . ?
C2 C1 C6 123.5(11) . . ?
C13 N4 C17 115.6(12) . . ?
C3' C4' C9' 120.5(7) . . ?
C5' C4' C3' 118.1(8) . . ?
C5' C4' C9' 121.4(7) . . ?
C1 C2' C3' 124.6(7) . . ?
C1 C2' C8 121.7(8) . . ?
C3' C2' C8 113.7(9) . . ?
N1 C12 H12A 109.1 . . ?
N1 C12 H12B 109.1 . . ?
N1 C12 C13 112.47(16) . . ?
H12A C12 H12B 107.8 . . ?
C13 C12 H12A 109.1 . . ?
C13 C12 H12B 109.1 . . ?
C1 C6' C5' 119.2(8) . . ?
C1 C6' C7' 118.5(10) . . ?
C5' C6' C7' 122.3(10) . . ?
C20' C19 C18 117.9(4) . . ?
N5 C19 C18 117.1(2) . . ?
N5' C19 C18 118.4(2) . . ?
N5' C19 C20' 122.8(4) . . ?
C20 C19 C18 125.3(3) . . ?
C20 C19 N5 117.6(4) . . ?
N4 C13 C12 113.1(8) . . ?
N4 C13 C14 126.6(11) . . ?
C14' C13 C12 125.7(8) . . ?
C14 C13 C12 119.1(8) . . ?
N4' C13 C12 117.8(9) . . ?
N4' C13 C14' 115.4(13) . . ?
C4' C3' C2' 117.5(8) . . ?
C4' C3' H3'A 121.2 . . ?
C2' C3' H3'A 121.2 . . ?
N1 C8 C2' 113.2(9) . . ?
N1 C8 H8BC 108.9 . . ?
N1 C8 H8BD 108.9 . . ?
N1 C8 H8AA 109.6 . . ?
N1 C8 H8AB 109.6 . . ?
C2' C8 H8BC 108.9 . . ?
C2' C8 H8BD 108.9 . . ?
H8BC C8 H8BD 107.8 . . ?
H8AA C8 H8AB 108.1 . . ?
C2 C8 N1 110.1(16) . . ?
C2 C8 H8AA 109.6 . . ?
C2 C8 H8AB 109.6 . . ?
N1 C18 C19 112.61(15) . . ?
N1 C18 H18A 109.1 . . ?
N1 C18 H18B 109.1 . . ?
C19 C18 H18A 109.1 . . ?
C19 C18 H18B 109.1 . . ?
H18A C18 H18B 107.8 . . ?
N2 C7 H7 119.4 . . ?
N2 C7 C6 121(2) . . ?
C6 C7 H7 119.4 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N6 C11 H11A 109.5 . . ?
N6 C11 H11B 109.5 . . ?
N6 C11 H11C 109.5 . . ?
C4' C5' C6' 122.4(7) . . ?
C4' C5' H5' 118.8 . . ?
C6' C5' H5' 118.8 . . ?
C13 C14' H14' 117.3 . . ?
C15' C14' C13 125.3(16) . . ?
C15' C14' H14' 117.3 . . ?
C4' C9' H9'A 109.5 . . ?
C4' C9' H9'B 109.5 . . ?
C4' C9' H9'C 109.5 . . ?
H9'A C9' H9'B 109.5 . . ?
H9'A C9' H9'C 109.5 . . ?
H9'B C9' H9'C 109.5 . . ?
N4 C17 H17 117.9 . . ?
N4 C17 C16 124.2(12) . . ?
C16 C17 H17 117.9 . . ?
C21' C22 H22A 122.5 . . ?
C23 C22 H22 120.8 . . ?
C23' C22 H22A 122.5 . . ?
C23' C22 C21' 115.1(5) . . ?
C21 C22 H22 120.8 . . ?
C21 C22 C23 118.5(5) . . ?
C17 C16 H16 120.6 . . ?
C17 C16 C15 118.8(11) . . ?
C15 C16 H16 120.6 . . ?
C16 C15 H15 119.8 . . ?
C16 C15 C14 120.5(14) . . ?
C14 C15 H15 119.8 . . ?
C19 C20' H20' 121.0 . . ?
C19 C20' C21' 117.9(6) . . ?
C21' C20' H20' 121.0 . . ?
C23 N5 C19 117.2(4) . . ?
C22 C21' H21' 120.2 . . ?
C20' C21' C22 119.5(6) . . ?
C20' C21' H21' 120.2 . . ?
C22 C23 H23 118.8 . . ?
N5 C23 C22 122.4(5) . . ?
N5 C23 H23 118.8 . . ?
C19 N5' C23' 118.2(4) . . ?
C19 C20 H20 118.9 . . ?
C19 C20 C21 122.2(6) . . ?
C21 C20 H20 118.9 . . ?
C22 C23' N5' 124.7(6) . . ?
C22 C23' H23' 117.7 . . ?
N5' C23' H23' 117.7 . . ?
C22 C21 C20 121.6(6) . . ?
C22 C21 H21 119.2 . . ?
C20 C21 H21 119.2 . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C4 C5 C6 121.8(13) . . ?
C4 C3 H3 114.1 . . ?
C4 C3 C2 131.8(15) . . ?
C2 C3 H3 114.1 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
C7 C6 C1 120.6(17) . . ?
C5 C6 C1 117.6(14) . . ?
C5 C6 C7 121.0(17) . . ?
C5 C4 C3 117.3(14) . . ?
C5 C4 C9 124.3(12) . . ?
C3 C4 C9 118.4(13) . . ?
C10 N6 C11 120.4(15) . . ?
C10 N6 H6 119.8 . . ?
C11 N6 H6 119.8 . . ?
N6' C11' H11D 109.5 . . ?
N6' C11' H11E 109.5 . . ?
N6' C11' H11F 109.5 . . ?
H11D C11' H11E 109.5 . . ?
H11D C11' H11F 109.5 . . ?
H11E C11' H11F 109.5 . . ?
C7' N2' N3' 113.3(12) . . ?
N2 N3 C10 123(2) . . ?
C6' C7' H7' 119.4 . . ?
N2' C7' C6' 121.3(12) . . ?
N2' C7' H7' 119.4 . . ?
C1 O1 H1 109.5 . . ?
N3' C10' S1' 120.4(9) . . ?
N6' C10' S1' 121.2(8) . . ?
N6' C10' N3' 117.2(11) . . ?
C17' C16' H16' 121.5 . . ?
C17' C16' C15' 117.1(15) . . ?
C15' C16' H16' 121.5 . . ?
C13 C14 C15 114.2(14) . . ?
C13 C14 H14 122.9 . . ?
C15 C14 H14 122.9 . . ?
C16' C17' H17' 117.1 . . ?
C16' C17' N4' 125.8(16) . . ?
N4' C17' H17' 117.1 . . ?
C13 N4' C17' 118.7(14) . . ?
C14' C15' H15' 121.3 . . ?
C16' C15' C14' 117.5(18) . . ?
C16' C15' H15' 121.3 . . ?
C8 C2 C1 118.1(14) . . ?
C3 C2 C1 107.8(13) . . ?
C3 C2 C8 134.1(18) . . ?
C10 S1 H1A 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N1 0.84 2.27 2.960(2) 139.0 .
O1 H1 N5 0.84 1.96 2.654(4) 139.3 .
O1 H1 N5' 0.84 2.51 3.239(8) 145.8 .

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_sad
_database_code_depnum_ccdc_archive 'CCDC 1520306'
_audit_update_record             
;
2016-12-01 deposited with the CCDC.
2018-06-27 downloaded from the CCDC.
;
_audit_creation_date             2016-11-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H27 Cu2 N6 O2 S, C F3 O3 S, H2 O'
_chemical_formula_sum            'C25 H29 Cu2 F3 N6 O6 S2'
_chemical_formula_weight         757.74
_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      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                   8.7438(17)
_cell_length_b                   10.771(2)
_cell_length_c                   15.739(3)
_cell_angle_alpha                95.74(3)
_cell_angle_beta                 95.74(3)
_cell_angle_gamma                92.90(3)
_cell_volume                     1464.7(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    36785
_cell_measurement_temperature    200
_cell_measurement_theta_max      29.998
_cell_measurement_theta_min      2.421
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.665
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.600376
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2004/1 (Bruker,2004) was used for absorption correction.
R(int) was 0.3587 before and 0.0671 after correction.
The Ratio of minimum to maximum transmission is 0.6004.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.718
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             772
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.32
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0676
_diffrn_reflns_av_unetI/netI     0.0855
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            36785
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.998
_diffrn_reflns_theta_min         2.421
_diffrn_ambient_temperature      200
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            KappaCCD
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_collimation    'Montel optic'
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec ISG250'
_diffrn_source_target            Mo
_diffrn_source_type              'Microfocus sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5712
_reflns_number_total             8473
_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       EvalCCD
_computing_data_collection       Collect
_computing_data_reduction        EvalCCD
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL-2016 (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_refine_diff_density_max         0.809
_refine_diff_density_min         -0.783
_refine_diff_density_rms         0.147
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     404
_refine_ls_number_reflns         8473
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0947
_refine_ls_R_factor_gt           0.0440
_refine_ls_restrained_S_all      1.044
_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)+(0.0776P)²+0.5783P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1198
_refine_ls_wR_factor_ref         0.1432
_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) groups, All O(H,H) groups
2.a Free rotating group:
 O6(H6A,H6B)
2.b Rotating group:
 O2(H2)
2.c Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C19(H19A,H19B), C8(H8A,H8B)
2.d Aromatic/amide H refined with riding coordinates:
 C18(H18), C3(H3), C22(H22), C24(H24), C5(H5), C15(H15), C16(H16), C17(H17),
 C21(H21), C7(H7), C23(H23)
2.e Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.32449(4) 0.57942(3) 0.38925(2) 0.01883(11) Uani 1 1 d . . . . .
Cu2 Cu 0.12415(4) 0.52242(3) 0.22351(2) 0.01800(11) Uani 1 1 d . . . . .
S1 S 0.48728(9) 0.73502(7) 0.44863(5) 0.02353(17) Uani 1 1 d . . . . .
S2 S 0.34714(11) 0.86516(9) 0.12709(5) 0.0341(2) Uani 1 1 d . . . . .
O2 O 0.3086(2) 0.61627(19) 0.27128(13) 0.0217(4) Uani 1 1 d . . . . .
H2 H 0.3242 0.6869 0.2616 0.033 Uiso 1 1 d GR . . . .
O1 O 0.1795(2) 0.4454(2) 0.33629(13) 0.0242(5) Uani 1 1 d . . . . .
O3 O 0.3448(3) 0.8699(2) 0.21796(15) 0.0379(6) Uani 1 1 d . . . . .
N1 N -0.0610(3) 0.4006(2) 0.19268(15) 0.0194(5) Uani 1 1 d . . . . .
N5 N -0.0416(3) 0.6466(2) 0.24060(16) 0.0219(5) Uani 1 1 d . . . . .
N4 N 0.1913(3) 0.4426(2) 0.11325(15) 0.0231(5) Uani 1 1 d . . . . .
N2 N 0.3034(3) 0.5342(2) 0.50302(15) 0.0198(5) Uani 1 1 d . . . . .
C10 C 0.4722(4) 0.6985(3) 0.55339(19) 0.0233(6) Uani 1 1 d . . . . .
N3 N 0.3884(3) 0.6020(2) 0.57362(15) 0.0230(5) Uani 1 1 d . . . . .
C13 C -0.0783(4) 0.3835(3) 0.09690(18) 0.0245(7) Uani 1 1 d . . . . .
H13A H -0.1286 0.4556 0.0744 0.029 Uiso 1 1 calc R . . . .
H13B H -0.1442 0.3069 0.0761 0.029 Uiso 1 1 calc R . . . .
C18 C 0.3343(4) 0.4409(3) 0.0896(2) 0.0292(7) Uani 1 1 d . . . . .
H18 H 0.4147 0.4919 0.1231 0.035 Uiso 1 1 calc R . . . .
C6 C 0.1120(3) 0.3599(3) 0.46250(18) 0.0209(6) Uani 1 1 d . . . . .
C19 C -0.1997(3) 0.4526(3) 0.2256(2) 0.0233(6) Uani 1 1 d . . . . .
H19A H -0.2156 0.4196 0.2808 0.028 Uiso 1 1 calc R . . . .
H19B H -0.2909 0.4253 0.1843 0.028 Uiso 1 1 calc R . . . .
N6 N 0.5494(3) 0.7733(3) 0.61896(17) 0.0324(7) Uani 1 1 d . . . . .
C3 C -0.0991(4) 0.1941(3) 0.3596(2) 0.0232(6) Uani 1 1 d . . . . .
H3 H -0.1738 0.1396 0.3243 0.028 Uiso 1 1 calc R . . . .
C9 C -0.1726(4) 0.0845(3) 0.4850(2) 0.0310(7) Uani 1 1 d . . . . .
H9A H -0.2823 0.0885 0.4660 0.047 Uiso 1 1 calc GR . . . .
H9B H -0.1563 0.0985 0.5478 0.047 Uiso 1 1 calc GR . . . .
H9C H -0.1388 0.0020 0.4657 0.047 Uiso 1 1 calc GR . . . .
C22 C -0.2874(4) 0.7913(3) 0.2704(2) 0.0336(8) Uani 1 1 d . . . . .
H22 H -0.3713 0.8412 0.2810 0.040 Uiso 1 1 calc R . . . .
O5 O 0.4908(4) 0.9087(5) 0.1015(3) 0.0992(16) Uani 1 1 d . . . . .
C24 C -0.0213(4) 0.7711(3) 0.2560(2) 0.0284(7) Uani 1 1 d . . . . .
H24 H 0.0793 0.8090 0.2566 0.034 Uiso 1 1 calc R . . . .
C20 C -0.1848(3) 0.5935(3) 0.23908(17) 0.0206(6) Uani 1 1 d . . . . .
C4 C -0.0810(4) 0.1841(3) 0.4472(2) 0.0240(6) Uani 1 1 d . . . . .
C5 C 0.0233(4) 0.2671(3) 0.4971(2) 0.0245(6) Uani 1 1 d . . . . .
H5 H 0.0366 0.2623 0.5573 0.029 Uiso 1 1 calc R . . . .
C2 C -0.0125(3) 0.2804(3) 0.32148(19) 0.0219(6) Uani 1 1 d . . . . .
C15 C 0.1038(4) 0.2978(3) -0.0082(2) 0.0329(8) Uani 1 1 d . . . . .
H15 H 0.0215 0.2496 -0.0421 0.039 Uiso 1 1 calc R . . . .
C1 C 0.0943(3) 0.3639(3) 0.37305(18) 0.0203(6) Uani 1 1 d . . . . .
C8 C -0.0287(4) 0.2770(3) 0.22526(19) 0.0237(6) Uani 1 1 d . . . . .
H8A H -0.1134 0.2150 0.2012 0.028 Uiso 1 1 calc R . . . .
H8B H 0.0674 0.2481 0.2038 0.028 Uiso 1 1 calc R . . . .
C16 C 0.2509(5) 0.2945(3) -0.0306(2) 0.0375(9) Uani 1 1 d . . . . .
H16 H 0.2717 0.2418 -0.0796 0.045 Uiso 1 1 calc R . . . .
C11 C 0.5365(5) 0.7476(4) 0.7065(2) 0.0431(10) Uani 1 1 d . . . . .
H11A H 0.4304 0.7182 0.7120 0.065 Uiso 1 1 calc GR . . . .
H11B H 0.5638 0.8241 0.7453 0.065 Uiso 1 1 calc GR . . . .
H11C H 0.6065 0.6830 0.7214 0.065 Uiso 1 1 calc GR . . . .
C14 C 0.0776(4) 0.3729(3) 0.06472(18) 0.0235(6) Uani 1 1 d . . . . .
C17 C 0.3681(5) 0.3667(3) 0.0174(2) 0.0362(8) Uani 1 1 d . . . . .
H17 H 0.4702 0.3660 0.0016 0.043 Uiso 1 1 calc R . . . .
C25 C 0.2186(5) 0.9858(3) 0.0967(3) 0.0410(9) Uani 1 1 d . . . . .
C21 C -0.3088(4) 0.6636(3) 0.2540(2) 0.0274(7) Uani 1 1 d . . . . .
H21 H -0.4085 0.6238 0.2530 0.033 Uiso 1 1 calc R . . . .
C7 C 0.2153(3) 0.4437(3) 0.52164(18) 0.0214(6) Uani 1 1 d . . . . .
H7 H 0.2187 0.4307 0.5806 0.026 Uiso 1 1 calc R . . . .
O4 O 0.2775(5) 0.7539(3) 0.0804(2) 0.0958(16) Uani 1 1 d . . . . .
C12 C 0.6421(4) 0.8842(3) 0.6070(2) 0.0355(8) Uani 1 1 d . . . . .
H12A H 0.6759 0.8757 0.5493 0.053 Uiso 1 1 calc GR . . . .
H12B H 0.7323 0.8945 0.6499 0.053 Uiso 1 1 calc GR . . . .
H12C H 0.5807 0.9576 0.6137 0.053 Uiso 1 1 calc GR . . . .
C23 C -0.1387(4) 0.8458(3) 0.2709(2) 0.0364(8) Uani 1 1 d . . . . .
H23 H -0.1199 0.9339 0.2815 0.044 Uiso 1 1 calc R . . . .
F1 F 0.2717(4) 1.0975(2) 0.1260(2) 0.0755(9) Uani 1 1 d . . . . .
F2 F 0.1905(4) 0.9822(3) 0.01289(17) 0.0823(10) Uani 1 1 d . . . . .
F3 F 0.0817(3) 0.9669(3) 0.1241(2) 0.0804(10) Uani 1 1 d . . . . .
O6 O 0.6244(5) 1.1773(5) 0.1096(3) 0.0934(14) Uani 1 1 d . . . . .
H6A H 0.6005 1.1776 0.0559 0.140 Uiso 1 1 d G . . . .
H6B H 0.5794 1.1142 0.1269 0.140 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 Cu2 2.9842(11) . ?
Cu1 S1 2.2107(11) . ?
Cu1 O2 1.930(2) . ?
Cu1 O1 1.936(2) . ?
Cu1 N2 1.926(2) . ?
Cu2 O2 1.905(2) . ?
Cu2 O1 2.058(2) . ?
Cu2 N1 2.019(2) . ?
Cu2 N5 2.041(3) . ?
Cu2 N4 2.013(3) . ?
S1 C10 1.749(3) . ?
S2 O3 1.428(3) . ?
S2 O5 1.428(4) . ?
S2 C25 1.829(4) . ?
S2 O4 1.417(3) . ?
O2 H2 0.7981 . ?
O1 C1 1.335(3) . ?
N1 C13 1.492(4) . ?
N1 C19 1.479(4) . ?
N1 C8 1.504(4) . ?
N5 C24 1.339(4) . ?
N5 C20 1.347(4) . ?
N4 C18 1.341(4) . ?
N4 C14 1.339(4) . ?
N2 N3 1.392(3) . ?
N2 C7 1.288(4) . ?
C10 N3 1.325(4) . ?
C10 N6 1.345(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.507(5) . ?
C18 H18 0.9500 . ?
C18 C17 1.388(5) . ?
C6 C5 1.418(4) . ?
C6 C1 1.406(4) . ?
C6 C7 1.441(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.509(4) . ?
N6 C11 1.446(4) . ?
N6 C12 1.449(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.387(4) . ?
C3 C2 1.389(4) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C9 C4 1.511(4) . ?
C22 H22 0.9500 . ?
C22 C21 1.373(5) . ?
C22 C23 1.398(5) . ?
C24 H24 0.9500 . ?
C24 C23 1.359(5) . ?
C20 C21 1.378(4) . ?
C4 C5 1.372(4) . ?
C5 H5 0.9500 . ?
C2 C1 1.399(4) . ?
C2 C8 1.503(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.368(5) . ?
C15 C14 1.382(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C16 H16 0.9500 . ?
C16 C17 1.368(5) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C17 H17 0.9500 . ?
C25 F1 1.290(4) . ?
C25 F2 1.314(4) . ?
C25 F3 1.325(5) . ?
C21 H21 0.9500 . ?
C7 H7 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C23 H23 0.9500 . ?
O6 H6A 0.8501 . ?
O6 H6B 0.8498 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
S1 Cu1 Cu2 135.89(3) . . ?
O2 Cu1 Cu2 38.60(6) . . ?
O2 Cu1 S1 99.89(7) . . ?
O2 Cu1 O1 79.45(9) . . ?
O1 Cu1 Cu2 43.23(6) . . ?
O1 Cu1 S1 178.91(7) . . ?
N2 Cu1 Cu2 132.05(8) . . ?
N2 Cu1 S1 87.93(8) . . ?
N2 Cu1 O2 170.20(9) . . ?
N2 Cu1 O1 92.64(10) . . ?
O2 Cu2 Cu1 39.21(6) . . ?
O2 Cu2 O1 77.03(9) . . ?
O2 Cu2 N1 168.12(9) . . ?
O2 Cu2 N5 103.09(10) . . ?
O2 Cu2 N4 100.69(10) . . ?
O1 Cu2 Cu1 40.11(6) . . ?
N1 Cu2 Cu1 129.84(7) . . ?
N1 Cu2 O1 91.23(9) . . ?
N1 Cu2 N5 82.35(10) . . ?
N5 Cu2 Cu1 100.64(7) . . ?
N5 Cu2 O1 109.43(10) . . ?
N4 Cu2 Cu1 125.48(8) . . ?
N4 Cu2 O1 119.64(10) . . ?
N4 Cu2 N1 83.41(10) . . ?
N4 Cu2 N5 128.96(10) . . ?
C10 S1 Cu1 94.01(11) . . ?
O3 S2 O5 113.9(2) . . ?
O3 S2 C25 103.59(18) . . ?
O5 S2 C25 102.8(2) . . ?
O4 S2 O3 114.5(2) . . ?
O4 S2 O5 116.0(3) . . ?
O4 S2 C25 103.94(19) . . ?
Cu1 O2 H2 118.7 . . ?
Cu2 O2 Cu1 102.19(9) . . ?
Cu2 O2 H2 120.8 . . ?
Cu1 O1 Cu2 96.65(9) . . ?
C1 O1 Cu1 129.39(18) . . ?
C1 O1 Cu2 128.04(18) . . ?
C13 N1 Cu2 104.12(17) . . ?
C13 N1 C8 108.7(2) . . ?
C19 N1 Cu2 110.84(18) . . ?
C19 N1 C13 111.0(2) . . ?
C19 N1 C8 111.7(2) . . ?
C8 N1 Cu2 110.23(18) . . ?
C24 N5 Cu2 127.2(2) . . ?
C24 N5 C20 118.4(3) . . ?
C20 N5 Cu2 114.4(2) . . ?
C18 N4 Cu2 127.8(2) . . ?
C14 N4 Cu2 112.8(2) . . ?
C14 N4 C18 119.0(3) . . ?
N3 N2 Cu1 119.85(18) . . ?
C7 N2 Cu1 125.7(2) . . ?
C7 N2 N3 114.5(2) . . ?
N3 C10 S1 124.7(2) . . ?
N3 C10 N6 116.8(3) . . ?
N6 C10 S1 118.5(2) . . ?
C10 N3 N2 113.4(2) . . ?
N1 C13 H13A 109.7 . . ?
N1 C13 H13B 109.7 . . ?
N1 C13 C14 109.8(2) . . ?
H13A C13 H13B 108.2 . . ?
C14 C13 H13A 109.7 . . ?
C14 C13 H13B 109.7 . . ?
N4 C18 H18 119.1 . . ?
N4 C18 C17 121.8(3) . . ?
C17 C18 H18 119.1 . . ?
C5 C6 C7 117.6(3) . . ?
C1 C6 C5 118.1(3) . . ?
C1 C6 C7 124.3(3) . . ?
N1 C19 H19A 109.3 . . ?
N1 C19 H19B 109.3 . . ?
N1 C19 C20 111.5(2) . . ?
H19A C19 H19B 108.0 . . ?
C20 C19 H19A 109.3 . . ?
C20 C19 H19B 109.3 . . ?
C10 N6 C11 120.0(3) . . ?
C10 N6 C12 123.1(3) . . ?
C11 N6 C12 116.9(3) . . ?
C4 C3 H3 118.7 . . ?
C4 C3 C2 122.6(3) . . ?
C2 C3 H3 118.7 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
C21 C22 H22 120.9 . . ?
C21 C22 C23 118.2(3) . . ?
C23 C22 H22 120.9 . . ?
N5 C24 H24 118.6 . . ?
N5 C24 C23 122.8(3) . . ?
C23 C24 H24 118.6 . . ?
N5 C20 C19 116.1(3) . . ?
N5 C20 C21 121.8(3) . . ?
C21 C20 C19 122.0(3) . . ?
C3 C4 C9 120.6(3) . . ?
C5 C4 C3 117.5(3) . . ?
C5 C4 C9 121.9(3) . . ?
C6 C5 H5 118.7 . . ?
C4 C5 C6 122.7(3) . . ?
C4 C5 H5 118.7 . . ?
C3 C2 C1 119.3(3) . . ?
C3 C2 C8 119.2(3) . . ?
C1 C2 C8 121.3(3) . . ?
C16 C15 H15 120.7 . . ?
C16 C15 C14 118.6(3) . . ?
C14 C15 H15 120.7 . . ?
O1 C1 C6 120.9(3) . . ?
O1 C1 C2 119.3(3) . . ?
C2 C1 C6 119.7(3) . . ?
N1 C8 H8A 108.7 . . ?
N1 C8 H8B 108.7 . . ?
C2 C8 N1 114.2(2) . . ?
C2 C8 H8A 108.7 . . ?
C2 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.3(3) . . ?
C17 C16 H16 119.8 . . ?
N6 C11 H11A 109.5 . . ?
N6 C11 H11B 109.5 . . ?
N6 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N4 C14 C13 114.3(3) . . ?
N4 C14 C15 121.9(3) . . ?
C15 C14 C13 123.8(3) . . ?
C18 C17 H17 120.8 . . ?
C16 C17 C18 118.4(3) . . ?
C16 C17 H17 120.8 . . ?
F1 C25 S2 113.2(3) . . ?
F1 C25 F2 107.9(3) . . ?
F1 C25 F3 108.2(4) . . ?
F2 C25 S2 111.5(3) . . ?
F2 C25 F3 104.8(3) . . ?
F3 C25 S2 110.9(3) . . ?
C22 C21 C20 119.6(3) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
N2 C7 C6 126.9(3) . . ?
N2 C7 H7 116.6 . . ?
C6 C7 H7 116.6 . . ?
N6 C12 H12A 109.5 . . ?
N6 C12 H12B 109.5 . . ?
N6 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C22 C23 H23 120.4 . . ?
C24 C23 C22 119.2(3) . . ?
C24 C23 H23 120.4 . . ?
H6A O6 H6B 109.6 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O3 0.80 2.16 2.948(3) 171.5 .
O6 H6A S2 0.85 2.96 3.743(4) 154.8 2_675
O6 H6A O5 0.85 2.59 3.397(7) 158.6 2_675
O6 H6A O4 0.85 2.64 3.335(6) 139.5 2_675
O6 H6B O5 0.85 2.29 3.051(7) 149.0 .
O6 H6B F1 0.85 2.69 3.201(5) 120.4 .

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_nanny
_database_code_depnum_ccdc_archive 'CCDC 1520304'
_audit_update_record             
;
2016-12-01 deposited with the CCDC.
2018-06-27 downloaded from the CCDC.
;
_audit_creation_date             2016-11-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'C46 H50 Cu4 N12 O4 S2, 2(C F3 O3 S), 3(C2 H3 N)'
_chemical_formula_sum            'C54 H59 Cu4 F6 N15 O10 S4'
_chemical_formula_weight         1574.56
_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                   32.964(7)
_cell_length_b                   14.683(3)
_cell_length_c                   14.437(3)
_cell_angle_alpha                90
_cell_angle_beta                 112.86(3)
_cell_angle_gamma                90
_cell_volume                     6439(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    47707
_cell_measurement_temperature    200
_cell_measurement_theta_max      29.999
_cell_measurement_theta_min      2.775
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.518
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.648116
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2004/1 (Bruker,2004) was used for absorption correction.
R(int) was 0.1829 before and 0.0548 after correction.
The Ratio of minimum to maximum transmission is 0.6481.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.624
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             3208
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.26
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0594
_diffrn_reflns_av_unetI/netI     0.0543
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            47707
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_min         2.775
_diffrn_ambient_temperature      200
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'APEX II'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  Incoatec-Bruker-AXS-enraf-noniusKappaAPEXII
_diffrn_measurement_method       'Phi and omega scans'
_diffrn_radiation_collimation    'Montel optic'
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Multilayer mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec ISG250'
_diffrn_source_target            Mo
_diffrn_source_type              'Microfocus sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6291
_reflns_number_total             9332
_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       EvalCCD
_computing_data_collection       Collect
_computing_data_reduction        EvalCCD
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.762
_refine_diff_density_min         -0.542
_refine_diff_density_rms         0.095
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     438
_refine_ls_number_reflns         9332
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0838
_refine_ls_R_factor_gt           0.0384
_refine_ls_restrained_S_all      1.085
_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)+(0.0355P)²+12.4887P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0822
_refine_ls_wR_factor_ref         0.1020
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C27-C28
 1.45 with sigma of 0.02
 N8-C27
 1.2 with sigma of 0.02
3. Rigid bond restraints
 C27, C28, N8
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C27 \\sim C28 \\sim N8: within 1.7A with sigma of 0.04 and sigma for terminal
atoms of 0.08
5. Others
 Fixed Sof: C28(0.5) H28A(0.5) H28B(0.5) H28C(0.5) N8(0.5) C27(0.5)
6.a Rotating group:
 O2(H2)
6.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C8(H8A,H8B), C12(H12A,H12B)
6.c Aromatic/amide H refined with riding coordinates:
 N6(H6), C7(H7), C14(H14), C17(H17), C5(H5), C22(H22), C3(H3), C20(H20),
 C15(H15), C16(H16), C21(H21), C23(H23)
6.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C11(H11A,H11B,H11C), C9(H9A,H9B,H9C), C28(H28A,H28B,H28C)
;
_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
Cu1 Cu 0.23947(2) 0.35418(2) 0.02554(2) 0.02104(8) Uani 1 1 d . . . . .
Cu2 Cu 0.32758(2) 0.29159(2) 0.16272(2) 0.02147(8) Uani 1 1 d . . . . .
S1 S 0.17070(2) 0.32949(5) 0.01489(5) 0.02524(14) Uani 1 1 d . . . . .
S2 S 0.46476(2) 0.76477(6) 0.49054(6) 0.03585(17) Uani 1 1 d . . . . .
O2 O 0.26736(5) 0.24876(12) 0.10965(12) 0.0223(4) Uani 1 1 d . . . . .
H2 H 0.2547 0.2354 0.1549 0.027 Uiso 1 1 d GR . . . .
O1 O 0.30102(5) 0.38182(12) 0.05093(12) 0.0224(4) Uani 1 1 d . . . . .
N1 N 0.38981(6) 0.33557(15) 0.19790(15) 0.0244(4) Uani 1 1 d . . . . .
N6 N 0.10756(7) 0.44761(16) -0.07529(17) 0.0288(5) Uani 1 1 d . . . . .
H6 H 0.0911 0.4042 -0.0660 0.035 Uiso 1 1 calc R . . . .
N4 N 0.35747(7) 0.18789(16) 0.25017(15) 0.0266(5) Uani 1 1 d . . . . .
N5 N 0.32777(7) 0.40624(16) 0.26660(16) 0.0283(5) Uani 1 1 d . . . . .
N2 N 0.21995(7) 0.47615(15) -0.02286(15) 0.0236(4) Uani 1 1 d . . . . .
C18 C 0.40357(9) 0.3924(2) 0.2902(2) 0.0313(6) Uani 1 1 d . . . . .
H18A H 0.4277 0.4334 0.2920 0.038 Uiso 1 1 calc R . . . .
H18B H 0.4151 0.3523 0.3499 0.038 Uiso 1 1 calc R . . . .
C7 C 0.24579(9) 0.54405(19) -0.01537(19) 0.0273(5) Uani 1 1 d . . . . .
H7 H 0.2321 0.6018 -0.0348 0.033 Uiso 1 1 calc R . . . .
O5 O 0.42542(9) 0.7137(2) 0.4434(2) 0.0707(9) Uani 1 1 d . . . . .
C6 C 0.29300(8) 0.54228(18) 0.01908(18) 0.0247(5) Uani 1 1 d . . . . .
C10 C 0.15127(8) 0.43375(19) -0.04386(18) 0.0243(5) Uani 1 1 d . . . . .
O3 O 0.45931(9) 0.8525(2) 0.5260(2) 0.0675(8) Uani 1 1 d . . . . .
C4 C 0.35851(9) 0.6326(2) 0.0451(2) 0.0316(6) Uani 1 1 d . . . . .
O4 O 0.50094(10) 0.7156(2) 0.5590(2) 0.0745(9) Uani 1 1 d . . . . .
C14 C 0.42660(10) 0.1148(2) 0.3304(2) 0.0369(7) Uani 1 1 d . . . . .
H14 H 0.4573 0.1128 0.3449 0.044 Uiso 1 1 calc R . . . .
C17 C 0.33899(10) 0.1252(2) 0.2896(2) 0.0347(6) Uani 1 1 d . . . . .
H17 H 0.3084 0.1293 0.2759 0.042 Uiso 1 1 calc R . . . .
C5 C 0.31377(9) 0.6251(2) 0.0161(2) 0.0303(6) Uani 1 1 d . . . . .
H5 H 0.2961 0.6781 -0.0070 0.036 Uiso 1 1 calc R . . . .
C8 C 0.39313(8) 0.3872(2) 0.1123(2) 0.0279(6) Uani 1 1 d . . . . .
H8A H 0.3847 0.3464 0.0532 0.033 Uiso 1 1 calc R . . . .
H8B H 0.4242 0.4052 0.1302 0.033 Uiso 1 1 calc R . . . .
C22 C 0.29730(10) 0.5394(2) 0.3078(2) 0.0381(7) Uani 1 1 d . . . . .
H22 H 0.2724 0.5701 0.3105 0.046 Uiso 1 1 calc R . . . .
C26 C 0.34015(12) 0.8067(3) 0.2320(3) 0.0562(10) Uani 1 1 d . . . . .
H26A H 0.3379 0.8614 0.1913 0.084 Uiso 1 1 calc GR . . . .
H26B H 0.3554 0.7587 0.2110 0.084 Uiso 1 1 calc GR . . . .
H26C H 0.3568 0.8211 0.3031 0.084 Uiso 1 1 calc GR . . . .
N3 N 0.17542(7) 0.49846(16) -0.05823(16) 0.0281(5) Uani 1 1 d . . . . .
C13 C 0.40065(8) 0.1825(2) 0.26976(19) 0.0280(6) Uani 1 1 d . . . . .
C1 C 0.31902(8) 0.46337(18) 0.05170(17) 0.0216(5) Uani 1 1 d . . . . .
C3 C 0.38349(9) 0.5546(2) 0.0799(2) 0.0304(6) Uani 1 1 d . . . . .
H3 H 0.4146 0.5589 0.1021 0.036 Uiso 1 1 calc R . . . .
F1 F 0.45095(11) 0.8344(3) 0.3162(2) 0.1120(12) Uani 1 1 d . . . . .
C11 C 0.08663(9) 0.5310(2) -0.1237(2) 0.0386(7) Uani 1 1 d . . . . .
H11A H 0.0931 0.5414 -0.1837 0.058 Uiso 1 1 calc GR . . . .
H11B H 0.0979 0.5821 -0.0770 0.058 Uiso 1 1 calc GR . . . .
H11C H 0.0547 0.5260 -0.1433 0.058 Uiso 1 1 calc GR . . . .
N7 N 0.26247(10) 0.7512(2) 0.2090(2) 0.0522(7) Uani 1 1 d . . . . .
C2 C 0.36506(8) 0.47046(19) 0.08358(18) 0.0241(5) Uani 1 1 d . . . . .
C19 C 0.36663(8) 0.4487(2) 0.29587(18) 0.0273(6) Uani 1 1 d . . . . .
F2 F 0.51771(10) 0.8363(3) 0.4186(3) 0.1270(14) Uani 1 1 d . . . . .
C20 C 0.37267(10) 0.5367(2) 0.3319(2) 0.0353(6) Uani 1 1 d . . . . .
H20 H 0.4006 0.5654 0.3512 0.042 Uiso 1 1 calc R . . . .
F3 F 0.48859(13) 0.7153(3) 0.3477(3) 0.1233(13) Uani 1 1 d . . . . .
C12 C 0.41745(8) 0.2529(2) 0.2178(2) 0.0294(6) Uani 1 1 d . . . . .
H12A H 0.4483 0.2686 0.2606 0.035 Uiso 1 1 calc R . . . .
H12B H 0.4169 0.2280 0.1536 0.035 Uiso 1 1 calc R . . . .
C15 C 0.40757(11) 0.0507(2) 0.3693(2) 0.0434(8) Uani 1 1 d . . . . .
H15 H 0.4249 0.0030 0.4101 0.052 Uiso 1 1 calc R . . . .
C25 C 0.29638(11) 0.7757(2) 0.2181(2) 0.0415(7) Uani 1 1 d . . . . .
C16 C 0.36307(11) 0.0557(2) 0.3489(2) 0.0424(7) Uani 1 1 d . . . . .
H16 H 0.3494 0.0117 0.3756 0.051 Uiso 1 1 calc R . . . .
C21 C 0.33755(11) 0.5823(2) 0.3394(2) 0.0387(7) Uani 1 1 d . . . . .
H21 H 0.3411 0.6423 0.3660 0.046 Uiso 1 1 calc R . . . .
C23 C 0.29361(10) 0.4520(2) 0.2722(2) 0.0340(6) Uani 1 1 d . . . . .
H23 H 0.2658 0.4226 0.2507 0.041 Uiso 1 1 calc R . . . .
C24 C 0.48141(12) 0.7894(3) 0.3887(3) 0.0584(10) Uani 1 1 d . . . . .
C9 C 0.37983(12) 0.7213(2) 0.0364(3) 0.0477(8) Uani 1 1 d . . . . .
H9A H 0.3930 0.7149 -0.0135 0.072 Uiso 1 1 calc GR . . . .
H9B H 0.4028 0.7369 0.1018 0.072 Uiso 1 1 calc GR . . . .
H9C H 0.3576 0.7695 0.0154 0.072 Uiso 1 1 calc GR . . . .
C28 C 0.5078(3) 0.5038(9) 0.4652(8) 0.104(4) Uani 0.5 1 d D U P A -1
H28A H 0.4790 0.5141 0.4683 0.156 Uiso 0.5 1 calc GR . P A -1
H28B H 0.5281 0.5525 0.5016 0.156 Uiso 0.5 1 calc GR . P A -1
H28C H 0.5196 0.4450 0.4960 0.156 Uiso 0.5 1 calc GR . P A -1
N8 N 0.4970(4) 0.5102(8) 0.2815(10) 0.121(5) Uani 0.5 1 d D U P A -1
C27 C 0.5036(3) 0.5037(10) 0.3712(10) 0.112(5) Uani 0.5 1 d D U P A -1


_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 Cu2 2.9551(11) . ?
Cu1 S1 2.2413(8) . ?
Cu1 O2 1.9616(18) . ?
Cu1 O2 2.4089(18) 7 ?
Cu1 O1 1.9589(17) . ?
Cu1 N2 1.939(2) . ?
Cu2 O2 1.9342(17) . ?
Cu2 O1 2.0072(18) . ?
Cu2 N1 2.018(2) . ?
Cu2 N4 1.979(2) . ?
Cu2 N5 2.253(2) . ?
S1 C10 1.747(3) . ?
S2 O5 1.421(2) . ?
S2 O3 1.423(3) . ?
S2 O4 1.416(3) . ?
S2 C24 1.794(4) . ?
O2 Cu1 2.4089(18) 7 ?
O2 H2 0.9229 . ?
O1 C1 1.335(3) . ?
N1 C18 1.486(3) . ?
N1 C8 1.490(3) . ?
N1 C12 1.478(3) . ?
N6 H6 0.8800 . ?
N6 C10 1.348(3) . ?
N6 C11 1.445(4) . ?
N4 C17 1.345(4) . ?
N4 C13 1.342(3) . ?
N5 C19 1.337(3) . ?
N5 C23 1.340(4) . ?
N2 C7 1.288(3) . ?
N2 N3 1.393(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.499(4) . ?
C7 H7 0.9500 . ?
C7 C6 1.438(4) . ?
C6 C5 1.405(4) . ?
C6 C1 1.409(4) . ?
C10 N3 1.307(3) . ?
C4 C5 1.372(4) . ?
C4 C3 1.387(4) . ?
C4 C9 1.507(4) . ?
C14 H14 0.9500 . ?
C14 C13 1.380(4) . ?
C14 C15 1.366(5) . ?
C17 H17 0.9500 . ?
C17 C16 1.371(4) . ?
C5 H5 0.9500 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C2 1.492(4) . ?
C22 H22 0.9500 . ?
C22 C21 1.376(5) . ?
C22 C23 1.371(4) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C26 C25 1.451(5) . ?
C13 C12 1.504(4) . ?
C1 C2 1.408(3) . ?
C3 H3 0.9500 . ?
C3 C2 1.386(4) . ?
F1 C24 1.313(5) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
N7 C25 1.132(4) . ?
C19 C20 1.378(4) . ?
F2 C24 1.300(5) . ?
C20 H20 0.9500 . ?
C20 C21 1.378(4) . ?
F3 C24 1.303(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C15 H15 0.9500 . ?
C15 C16 1.382(5) . ?
C16 H16 0.9500 . ?
C21 H21 0.9500 . ?
C23 H23 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C28 C27 1.309(13) . ?
N8 C27 1.231(13) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
S1 Cu1 Cu2 134.44(2) . . ?
S1 Cu1 O2 93.97(5) . 7 ?
O2 Cu1 Cu2 96.09(5) 7 . ?
O2 Cu1 Cu2 40.32(5) . . ?
O2 Cu1 S1 97.65(5) . . ?
O2 Cu1 O2 83.12(7) . 7 ?
O1 Cu1 Cu2 42.46(5) . . ?
O1 Cu1 S1 173.10(5) . . ?
O1 Cu1 O2 81.11(7) . . ?
O1 Cu1 O2 92.62(7) . 7 ?
N2 Cu1 Cu2 129.12(6) . . ?
N2 Cu1 S1 86.53(6) . . ?
N2 Cu1 O2 164.14(8) . . ?
N2 Cu1 O2 111.96(8) . 7 ?
N2 Cu1 O1 92.90(8) . . ?
O2 Cu2 Cu1 41.01(5) . . ?
O2 Cu2 O1 80.57(7) . . ?
O2 Cu2 N1 171.91(8) . . ?
O2 Cu2 N4 100.52(9) . . ?
O2 Cu2 N5 104.11(8) . . ?
O1 Cu2 Cu1 41.21(5) . . ?
O1 Cu2 N1 94.26(8) . . ?
O1 Cu2 N5 85.96(8) . . ?
N1 Cu2 Cu1 135.02(7) . . ?
N1 Cu2 N5 81.58(9) . . ?
N4 Cu2 Cu1 141.53(7) . . ?
N4 Cu2 O1 166.99(8) . . ?
N4 Cu2 N1 83.12(9) . . ?
N4 Cu2 N5 106.16(9) . . ?
N5 Cu2 Cu1 87.80(6) . . ?
C10 S1 Cu1 93.55(9) . . ?
O5 S2 O3 115.47(19) . . ?
O5 S2 C24 103.12(18) . . ?
O3 S2 C24 103.5(2) . . ?
O4 S2 O5 115.5(2) . . ?
O4 S2 O3 113.56(18) . . ?
O4 S2 C24 103.4(2) . . ?
Cu1 O2 Cu1 96.88(7) . 7 ?
Cu1 O2 H2 111.9 . . ?
Cu1 O2 H2 121.0 7 . ?
Cu2 O2 Cu1 98.67(8) . . ?
Cu2 O2 Cu1 106.47(7) . 7 ?
Cu2 O2 H2 117.8 . . ?
Cu1 O1 Cu2 96.33(8) . . ?
C1 O1 Cu1 127.77(15) . . ?
C1 O1 Cu2 122.13(15) . . ?
C18 N1 Cu2 109.37(16) . . ?
C18 N1 C8 111.3(2) . . ?
C8 N1 Cu2 110.42(15) . . ?
C12 N1 Cu2 106.01(16) . . ?
C12 N1 C18 109.7(2) . . ?
C12 N1 C8 109.9(2) . . ?
C10 N6 H6 118.7 . . ?
C10 N6 C11 122.5(2) . . ?
C11 N6 H6 118.7 . . ?
C17 N4 Cu2 126.93(19) . . ?
C13 N4 Cu2 113.86(18) . . ?
C13 N4 C17 119.2(2) . . ?
C19 N5 Cu2 108.26(17) . . ?
C19 N5 C23 118.2(2) . . ?
C23 N5 Cu2 128.99(19) . . ?
C7 N2 Cu1 124.64(18) . . ?
C7 N2 N3 114.6(2) . . ?
N3 N2 Cu1 120.28(17) . . ?
N1 C18 H18A 109.0 . . ?
N1 C18 H18B 109.0 . . ?
N1 C18 C19 112.8(2) . . ?
H18A C18 H18B 107.8 . . ?
C19 C18 H18A 109.0 . . ?
C19 C18 H18B 109.0 . . ?
N2 C7 H7 116.3 . . ?
N2 C7 C6 127.3(2) . . ?
C6 C7 H7 116.3 . . ?
C5 C6 C7 116.6(2) . . ?
C5 C6 C1 118.8(2) . . ?
C1 C6 C7 124.5(2) . . ?
N6 C10 S1 116.0(2) . . ?
N3 C10 S1 125.68(19) . . ?
N3 C10 N6 118.3(2) . . ?
C5 C4 C3 117.4(3) . . ?
C5 C4 C9 121.6(3) . . ?
C3 C4 C9 120.9(3) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
C15 C14 C13 119.1(3) . . ?
N4 C17 H17 119.1 . . ?
N4 C17 C16 121.8(3) . . ?
C16 C17 H17 119.1 . . ?
C6 C5 H5 118.7 . . ?
C4 C5 C6 122.6(3) . . ?
C4 C5 H5 118.7 . . ?
N1 C8 H8A 108.7 . . ?
N1 C8 H8B 108.7 . . ?
N1 C8 C2 114.2(2) . . ?
H8A C8 H8B 107.6 . . ?
C2 C8 H8A 108.7 . . ?
C2 C8 H8B 108.7 . . ?
C21 C22 H22 120.4 . . ?
C23 C22 H22 120.4 . . ?
C23 C22 C21 119.1(3) . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
C10 N3 N2 113.0(2) . . ?
N4 C13 C14 121.5(3) . . ?
N4 C13 C12 114.9(2) . . ?
C14 C13 C12 123.6(2) . . ?
O1 C1 C6 121.6(2) . . ?
O1 C1 C2 119.2(2) . . ?
C2 C1 C6 119.2(2) . . ?
C4 C3 H3 118.6 . . ?
C2 C3 C4 122.9(2) . . ?
C2 C3 H3 118.6 . . ?
N6 C11 H11A 109.5 . . ?
N6 C11 H11B 109.5 . . ?
N6 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C1 C2 C8 120.2(2) . . ?
C3 C2 C8 120.5(2) . . ?
C3 C2 C1 119.1(2) . . ?
N5 C19 C18 115.1(2) . . ?
N5 C19 C20 122.4(3) . . ?
C20 C19 C18 122.4(2) . . ?
C19 C20 H20 120.6 . . ?
C21 C20 C19 118.9(3) . . ?
C21 C20 H20 120.6 . . ?
N1 C12 C13 110.0(2) . . ?
N1 C12 H12A 109.7 . . ?
N1 C12 H12B 109.7 . . ?
C13 C12 H12A 109.7 . . ?
C13 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
C14 C15 H15 120.2 . . ?
C14 C15 C16 119.7(3) . . ?
C16 C15 H15 120.2 . . ?
N7 C25 C26 178.8(4) . . ?
C17 C16 C15 118.8(3) . . ?
C17 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
C22 C21 C20 118.9(3) . . ?
C22 C21 H21 120.6 . . ?
C20 C21 H21 120.6 . . ?
N5 C23 C22 122.5(3) . . ?
N5 C23 H23 118.7 . . ?
C22 C23 H23 118.7 . . ?
F1 C24 S2 111.8(3) . . ?
F2 C24 S2 111.7(3) . . ?
F2 C24 F1 108.6(4) . . ?
F2 C24 F3 106.7(4) . . ?
F3 C24 S2 111.8(3) . . ?
F3 C24 F1 106.0(4) . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
N8 C27 C28 174.1(15) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 N7 0.92 2.26 3.135(4) 158.4 4_545
N6 H6 O3 0.88 2.10 2.922(3) 154.6 4_545

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