# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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. 
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#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1442682'
_audit_update_record             
;
2015-12-15 deposited with the CCDC.
2016-01-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C66 H69 Cl5 Cu2 F12 N6 O8 P2'
_chemical_formula_weight         1668.54

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   14.590(3)
_cell_length_b                   17.504(4)
_cell_length_c                   28.499(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.456(3)
_cell_angle_gamma                90
_cell_volume                     7133(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    14477
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      27.6

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_F_000             3408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.069
_exptl_crystal_size_mid          0.054
_exptl_crystal_size_min          0.024
_exptl_absorpt_coefficient_mu    0.918
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.412
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            70413
_diffrn_reflns_av_unetI/netI     0.0665
_diffrn_reflns_av_R_equivalents  0.0795
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.232
_diffrn_reflns_theta_max         27.566
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             16433
_reflns_number_gt                9992
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         16433
_refine_ls_number_parameters     957
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1628
_refine_ls_R_factor_gt           0.1095
_refine_ls_wR_factor_ref         0.3630
_refine_ls_wR_factor_gt          0.3244
_refine_ls_goodness_of_fit_ref   1.267
_refine_ls_restrained_S_all      1.268
_refine_ls_shift/su_max          0.047
_refine_ls_shift/su_mean         0.002

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
C1 C 0.6711(4) 0.2835(4) 0.1634(2) 0.0379(14) Uani 1 1 d . . . . .
C2 C 0.6203(6) 0.2251(5) 0.1801(3) 0.057(2) Uani 1 1 d . . . . .
H2 H 0.6007 0.1827 0.1611 0.069 Uiso 1 1 calc R U . . .
C3 C 0.5998(6) 0.2312(5) 0.2247(3) 0.060(2) Uani 1 1 d . . . . .
H3 H 0.5664 0.1923 0.2359 0.072 Uiso 1 1 calc R U . . .
C4 C 0.6266(5) 0.2917(5) 0.2522(3) 0.0531(19) Uani 1 1 d . . . . .
H4 H 0.6112 0.2961 0.2822 0.064 Uiso 1 1 calc R U . . .
C5 C 0.6791(4) 0.3490(4) 0.2348(2) 0.0388(14) Uani 1 1 d . . . . .
C6 C 0.6980(5) 0.4201(5) 0.3075(2) 0.0466(17) Uani 1 1 d . . . . .
H6A H 0.7248 0.3765 0.3263 0.056 Uiso 1 1 calc R U . . .
H6B H 0.6318 0.4224 0.3080 0.056 Uiso 1 1 calc R U . . .
C7 C 0.7456(5) 0.4923(5) 0.3276(3) 0.0505(18) Uani 1 1 d . . . . .
H7A H 0.7179 0.5353 0.3084 0.061 Uiso 1 1 calc R U . . .
H7B H 0.7354 0.4997 0.3599 0.061 Uiso 1 1 calc R U . . .
C8 C 0.8479(5) 0.4905(4) 0.3285(2) 0.0436(16) Uani 1 1 d . . . . .
C9 C 0.8861(5) 0.5229(5) 0.2910(3) 0.057(2) Uani 1 1 d . . . . .
H9 H 0.8467 0.5476 0.2659 0.069 Uiso 1 1 calc R U . . .
C10 C 0.9787(6) 0.5187(7) 0.2910(3) 0.079(3) Uani 1 1 d . . . . .
H10 H 1.0029 0.5399 0.2661 0.094 Uiso 1 1 calc R U . . .
C11 C 1.0381(6) 0.4815(7) 0.3296(3) 0.075(3) Uani 1 1 d . . . . .
C12 C 1.0027(6) 0.4477(5) 0.3645(3) 0.060(2) Uani 1 1 d . . . . .
H12 H 1.0417 0.4208 0.3887 0.072 Uiso 1 1 calc R U . . .
C13 C 0.9097(6) 0.4532(5) 0.3641(3) 0.0540(19) Uani 1 1 d . . . . .
H13 H 0.8865 0.4309 0.3890 0.065 Uiso 1 1 calc R U . . .
C14 C 1.1699(7) 0.4964(14) 0.2934(4) 0.162(10) Uani 1 1 d D . . . .
H14A H 1.1743 0.5516 0.2913 0.195 Uiso 1 1 calc R U . . .
H14B H 1.1341 0.4767 0.2635 0.195 Uiso 1 1 calc R U . . .
C15 C 1.2700(8) 0.4579(15) 0.3066(5) 0.181(10) Uani 1 1 d D . . . .
H15A H 1.3037 0.4788 0.3366 0.218 Uiso 1 1 calc R U . . .
H15B H 1.2628 0.4034 0.3108 0.218 Uiso 1 1 calc R U . . .
C16 C 1.3230(9) 0.4706(15) 0.2701(5) 0.179(10) Uani 1 1 d D . . . .
H16A H 1.3835 0.4463 0.2800 0.215 Uiso 1 1 calc R U . . .
H16B H 1.3339 0.5251 0.2681 0.215 Uiso 1 1 calc R U . . .
C17 C 1.2800(11) 0.4422(13) 0.2204(5) 0.157(8) Uani 1 1 d D . . . .
H17A H 1.3286 0.4347 0.2020 0.189 Uiso 1 1 calc R U . . .
H17B H 1.2494 0.3935 0.2226 0.189 Uiso 1 1 calc R U . . .
C18 C 1.1558(6) 0.4728(6) 0.1577(3) 0.056(2) Uani 1 1 d . . . . .
C25 C 0.8821(6) 0.4066(10) 0.0233(3) 0.110(6) Uani 0.5 1 d . . P A 1
H25A H 0.9108 0.3569 0.0219 0.132 Uiso 0.5 1 calc R U P A 1
H25B H 0.8375 0.4134 -0.0065 0.132 Uiso 0.5 1 calc R U P A 1
C23 C 1.0880(6) 0.5288(6) 0.1410(3) 0.064(2) Uani 0.5 1 d . . P A 1
C24 C 0.9449(9) 0.4561(11) 0.0246(5) 0.048(4) Uani 0.5 1 d . . P A 1
H24 H 0.9458 0.4869 -0.0018 0.058 Uiso 0.5 1 calc R U P A 1
H24A H 0.9142 0.5051 0.0179 0.058 Uiso 0.5 1 calc R U P A 1
H24B H 0.9767 0.4453 -0.0014 0.058 Uiso 0.5 1 calc R U P A 1
C21 C 1.0205(10) 0.4653(13) 0.0705(6) 0.041(4) Uani 0.5 1 d . . P A 1
C19 C 1.152(2) 0.4142(15) 0.1274(10) 0.052(6) Uani 0.5 1 d . . P A 1
H19 H 1.1974 0.3763 0.1345 0.063 Uiso 0.5 1 calc R U P A 1
C20 C 1.0828(19) 0.4066(12) 0.0847(7) 0.050(4) Uani 0.5 1 d . . P A 1
H20 H 1.0796 0.3622 0.0666 0.060 Uiso 0.5 1 calc R U P A 1
C22 C 1.0224(17) 0.5287(15) 0.0989(12) 0.057(7) Uani 0.5 1 d . . P A 1
H22 H 0.9816 0.5694 0.0902 0.068 Uiso 0.5 1 calc R U P A 1
C85 C 0.8821(6) 0.4066(10) 0.0233(3) 0.110(6) Uani 0.5 1 d . . P A 2
H85A H 0.8542 0.3712 -0.0016 0.132 Uiso 0.5 1 calc R U P A 2
H85B H 0.8779 0.4575 0.0095 0.132 Uiso 0.5 1 calc R U P A 2
C83 C 1.0880(6) 0.5288(6) 0.1410(3) 0.064(2) Uani 0.5 1 d . . P A 2
C84 C 0.9718(12) 0.3886(12) 0.0384(6) 0.064(5) Uani 0.5 1 d . . P A 2
H84 H 0.9976 0.3537 0.0202 0.077 Uiso 0.5 1 calc R U P A 2
H84A H 1.0024 0.4000 0.0120 0.077 Uiso 0.5 1 calc R U P A 2
H84B H 0.9736 0.3335 0.0420 0.077 Uiso 0.5 1 calc R U P A 2
C81 C 1.0326(15) 0.4186(16) 0.0808(6) 0.047(4) Uani 0.5 1 d . . P A 2
C80 C 1.1102(17) 0.3720(15) 0.1045(9) 0.066(6) Uani 0.5 1 d . . P A 2
H80 H 1.1189 0.3240 0.0920 0.079 Uiso 0.5 1 calc R U P A 2
C79 C 1.170(2) 0.396(2) 0.1436(10) 0.075(10) Uani 0.5 1 d . . P A 2
H79 H 1.2163 0.3643 0.1604 0.090 Uiso 0.5 1 calc R U P A 2
C82 C 1.028(2) 0.490(2) 0.1009(10) 0.076(10) Uani 0.5 1 d . . P A 2
H82 H 0.9764 0.5187 0.0862 0.091 Uiso 0.5 1 calc R U P A 2
C26 C 0.7756(5) 0.3463(5) 0.0649(3) 0.0482(18) Uani 1 1 d . . . . .
C27 C 0.7420(7) 0.2923(6) 0.0290(3) 0.064(3) Uani 1 1 d . . . . .
H27 H 0.7599 0.2952 -0.0005 0.077 Uiso 1 1 calc R U . . .
C28 C 0.6848(7) 0.2371(5) 0.0372(3) 0.068(3) Uani 1 1 d . . . . .
H28 H 0.6611 0.2024 0.0132 0.082 Uiso 1 1 calc R U . . .
C29 C 0.6602(6) 0.2311(5) 0.0817(3) 0.058(2) Uani 1 1 d . . . . .
H29 H 0.6214 0.1919 0.0881 0.069 Uiso 1 1 calc R U . . .
C30 C 0.6950(5) 0.2847(4) 0.1161(3) 0.0441(16) Uani 1 1 d . . . . .
C31 C 0.8494(4) 0.5807(4) 0.1747(2) 0.0409(15) Uani 1 1 d . . . . .
C32 C 0.8859(6) 0.6573(5) 0.1861(3) 0.056(2) Uani 1 1 d . . . . .
H32A H 0.9161 0.6595 0.2193 0.084 Uiso 1 1 calc R U . . .
H32B H 0.8355 0.6934 0.1801 0.084 Uiso 1 1 calc R U . . .
H32C H 0.9304 0.6693 0.1665 0.084 Uiso 1 1 calc R U . . .
C41 C 0.5688(5) 0.4640(4) 1.0741(3) 0.059(2) Uani 1 1 d . . . . .
C42 C 0.5731(6) 0.5019(5) 1.1171(3) 0.060(2) Uani 1 1 d . . . . .
H42 H 0.6056 0.5477 1.1231 0.072 Uiso 1 1 calc R U . . .
C43 C 0.5288(6) 0.4708(5) 1.1507(3) 0.068(3) Uani 1 1 d . . . . .
H43 H 0.5333 0.4950 1.1802 0.082 Uiso 1 1 calc R U . . .
C44 C 0.4768(6) 0.4033(6) 1.1416(3) 0.064(2) Uani 1 1 d . . . . .
H44 H 0.4449 0.3827 1.1638 0.077 Uiso 1 1 calc R U . . .
C45 C 0.4755(5) 0.3686(5) 1.0973(3) 0.055(2) Uani 1 1 d . . . . .
C46 C 0.3739(6) 0.2675(6) 1.1132(3) 0.064(2) Uani 1 1 d . . . . .
H46A H 0.3253 0.3021 1.1189 0.077 Uiso 1 1 calc R U . . .
H46B H 0.4137 0.2551 1.1437 0.077 Uiso 1 1 calc R U . . .
C47 C 0.3307(5) 0.1954(5) 1.0888(3) 0.056(2) Uani 1 1 d . . . . .
H47A H 0.2923 0.2088 1.0580 0.067 Uiso 1 1 calc R U . . .
H47B H 0.2902 0.1727 1.1082 0.067 Uiso 1 1 calc R U . . .
C48 C 0.4037(5) 0.1369(5) 1.0812(3) 0.0464(17) Uani 1 1 d . . . . .
C49 C 0.4434(5) 0.0852(5) 1.1162(3) 0.053(2) Uani 1 1 d . . . . .
H49 H 0.4204 0.0821 1.1443 0.063 Uiso 1 1 calc R U . . .
C50 C 0.5150(5) 0.0391(4) 1.1105(3) 0.0502(18) Uani 1 1 d . . . . .
H50 H 0.5405 0.0059 1.1351 0.060 Uiso 1 1 calc R U . . .
C51 C 0.5518(5) 0.0401(4) 1.0684(3) 0.0428(16) Uani 1 1 d . . . . .
C52 C 0.5098(5) 0.0910(4) 1.0319(3) 0.0455(16) Uani 1 1 d . . . . .
H52 H 0.5307 0.0929 1.0032 0.055 Uiso 1 1 calc R U . . .
C53 C 0.4375(5) 0.1380(4) 1.0391(3) 0.0483(17) Uani 1 1 d . . . . .
H53 H 0.4107 0.1713 1.0148 0.058 Uiso 1 1 calc R U . . .
C54 C 0.6813(5) 0.0144(4) 1.0306(3) 0.0487(17) Uani 1 1 d . . . . .
H54A H 0.6846 0.0693 1.0267 0.058 Uiso 1 1 calc R U . . .
H54B H 0.6523 -0.0077 1.0001 0.058 Uiso 1 1 calc R U . . .
C55 C 0.7777(6) -0.0178(6) 1.0470(3) 0.065(2) Uani 1 1 d . . . . .
H55A H 0.7723 -0.0705 1.0567 0.078 Uiso 1 1 calc R U . . .
H55B H 0.8090 0.0105 1.0749 0.078 Uiso 1 1 calc R U . . .
C56 C 0.8378(7) -0.0154(6) 1.0095(4) 0.072(3) Uani 1 1 d . . . . .
H56A H 0.8130 -0.0515 0.9844 0.086 Uiso 1 1 calc R U . . .
H56B H 0.9005 -0.0319 1.0240 0.086 Uiso 1 1 calc R U . . .
C57 C 0.8438(5) 0.0627(5) 0.9871(3) 0.058(2) Uani 1 1 d . . . . .
H57A H 0.8536 0.1019 1.0117 0.069 Uiso 1 1 calc R U . . .
H57B H 0.8956 0.0642 0.9704 0.069 Uiso 1 1 calc R U . . .
C58 C 0.7424(5) 0.1441(4) 0.9325(2) 0.0391(15) Uani 1 1 d . . . . .
C59 C 0.8114(5) 0.1981(4) 0.9284(2) 0.0413(15) Uani 1 1 d . . . . .
H59 H 0.8737 0.1888 0.9422 0.050 Uiso 1 1 calc R U . . .
C60 C 0.7866(4) 0.2641(4) 0.9039(2) 0.0413(15) Uani 1 1 d . . . . .
H60 H 0.8330 0.2992 0.9011 0.050 Uiso 1 1 calc R U . . .
C61 C 0.6947(5) 0.2808(5) 0.8829(2) 0.0444(16) Uani 1 1 d . . . . .
C62 C 0.6266(4) 0.2284(4) 0.8872(2) 0.0422(16) Uani 1 1 d . . . . .
H62 H 0.5644 0.2387 0.8736 0.051 Uiso 1 1 calc R U . . .
C63 C 0.6495(4) 0.1604(4) 0.9114(2) 0.0394(14) Uani 1 1 d . . . . .
H63 H 0.6028 0.1252 0.9136 0.047 Uiso 1 1 calc R U . . .
C64 C 0.6684(5) 0.3547(5) 0.8571(3) 0.054(2) Uani 1 1 d . . . . .
H64A H 0.6024 0.3536 0.8426 0.065 Uiso 1 1 calc R U . . .
H64B H 0.7032 0.3598 0.8316 0.065 Uiso 1 1 calc R U . . .
C65 C 0.6878(5) 0.4228(5) 0.8897(3) 0.056(2) Uani 1 1 d . . . . .
H65A H 0.7541 0.4262 0.9032 0.067 Uiso 1 1 calc R U . . .
H65B H 0.6687 0.4694 0.8720 0.067 Uiso 1 1 calc R U . . .
C66 C 0.6500(5) 0.4631(4) 0.9627(3) 0.0503(18) Uani 1 1 d . . . . .
C67 C 0.7041(5) 0.5296(5) 0.9645(4) 0.060(2) Uani 1 1 d . . . . .
H67 H 0.7327 0.5420 0.9391 0.072 Uiso 1 1 calc R U . . .
C68 C 0.7144(6) 0.5751(5) 1.0026(4) 0.066(2) Uani 1 1 d . . . . .
H68 H 0.7502 0.6193 1.0038 0.079 Uiso 1 1 calc R U . . .
C69 C 0.6722(6) 0.5569(4) 1.0406(3) 0.061(2) Uani 1 1 d . . . . .
H69 H 0.6802 0.5878 1.0676 0.073 Uiso 1 1 calc R U . . .
C70 C 0.6167(5) 0.4903(4) 1.0373(3) 0.0484(18) Uani 1 1 d . . . . .
C71 C 0.4154(4) 0.2415(3) 0.9291(2) 0.0356(14) Uani 1 1 d . . . . .
C72 C 0.3647(5) 0.1875(4) 0.8956(2) 0.0409(15) Uani 1 1 d . . . . .
H72A H 0.3852 0.1914 0.8657 0.061 Uiso 1 1 calc R U . . .
H72B H 0.2990 0.1985 0.8907 0.061 Uiso 1 1 calc R U . . .
H72C H 0.3761 0.1368 0.9081 0.061 Uiso 1 1 calc R U . . .
C95 C 0.9282(9) 0.3092(10) 0.2739(6) 0.137(7) Uani 1 1 d . . . . .
H95A H 0.9809 0.3073 0.3007 0.165 Uiso 1 1 calc R U . . .
H95B H 0.8877 0.3504 0.2800 0.165 Uiso 1 1 calc R U . . .
C97 C 1.0285(7) 0.1568(6) 0.1209(4) 0.073(3) Uani 1 1 d . . . . .
H97 H 1.0336 0.1023 0.1288 0.088 Uiso 1 1 calc R U . . .
N1 N 0.7007(3) 0.3451(3) 0.19147(19) 0.0337(11) Uani 1 1 d . . . . .
N2 N 0.7506(4) 0.3425(3) 0.10730(19) 0.0384(12) Uani 1 1 d . . . . .
N31 N 0.8213(4) 0.5213(4) 0.1679(2) 0.0418(13) Uani 1 1 d . . . . .
N41 N 0.5189(4) 0.3973(3) 1.0647(2) 0.0428(13) Uani 1 1 d . . . . .
N42 N 0.6066(4) 0.4458(3) 0.9984(2) 0.0460(15) Uani 1 1 d . . . . .
N71 N 0.4563(4) 0.2839(3) 0.9556(2) 0.0381(12) Uani 1 1 d . . . . .
O1 O 0.7117(3) 0.4128(3) 0.25852(16) 0.0397(10) Uani 1 1 d . . . . .
O2 O 1.1316(5) 0.4744(7) 0.3319(3) 0.121(4) Uani 1 1 d . . . . .
O3 O 1.2187(4) 0.4925(4) 0.1987(2) 0.0702(17) Uani 1 1 d . . . . .
O4 O 0.8298(4) 0.4046(5) 0.06182(19) 0.0715(19) Uani 1 1 d . . . . .
O41 O 0.4274(3) 0.3026(3) 1.08267(18) 0.0503(12) Uani 1 1 d . . . . .
O42 O 0.6263(4) -0.0035(3) 1.06660(19) 0.0527(13) Uani 1 1 d . . . . .
O43 O 0.7580(3) 0.0758(3) 0.95436(17) 0.0465(12) Uani 1 1 d . . . . .
O44 O 0.6359(3) 0.4132(3) 0.9269(2) 0.0471(12) Uani 1 1 d . . . . .
F1 F 0.7074(5) 0.6263(5) 0.2370(3) 0.127(3) Uani 1 1 d . . . . .
F2 F 0.7135(4) 0.7546(4) 0.2200(2) 0.0785(16) Uani 1 1 d . . . . .
F3 F 0.6287(6) 0.6700(4) 0.1696(2) 0.100(2) Uani 1 1 d . . . . .
F4 F 0.5539(5) 0.6308(4) 0.2293(3) 0.109(2) Uani 1 1 d . . . . .
F5 F 0.5591(4) 0.7531(4) 0.2076(2) 0.0792(16) Uani 1 1 d . . . . .
F6 F 0.6340(6) 0.7111(8) 0.2787(2) 0.164(5) Uani 1 1 d . . . . .
F7 F 0.8849(10) 0.7085(6) 0.0132(4) 0.184(6) Uani 1 1 d . . . . .
F8 F 0.9832(4) 0.7248(4) 0.0972(3) 0.102(2) Uani 1 1 d . . . . .
F9 F 0.9423(4) 0.8195(3) 0.04423(19) 0.0672(13) Uani 1 1 d . . . . .
F10 F 0.8683(4) 0.7967(4) 0.1052(2) 0.0895(18) Uani 1 1 d . . . . .
F11 F 0.7928(6) 0.7790(7) 0.0320(3) 0.146(4) Uani 1 1 d . . . . .
F12 F 0.8373(6) 0.6771(5) 0.0783(2) 0.125(3) Uani 1 1 d . . . . .
P1 P 0.63511(16) 0.69202(14) 0.22570(9) 0.0608(6) Uani 1 1 d . . . . .
P2 P 0.8928(2) 0.74602(16) 0.06053(10) 0.0791(9) Uani 1 1 d . . . . .
Cu1 Cu 0.77377(5) 0.42210(5) 0.16008(3) 0.0384(2) Uani 1 1 d . . . . .
Cu2 Cu 0.51696(6) 0.35572(4) 0.99889(3) 0.0415(3) Uani 1 1 d . . . . .
Cl95 Cl 0.8697(2) 0.2277(2) 0.27197(16) 0.1256(15) Uani 1 1 d . . . . .
Cl96 Cl 0.9714(3) 0.3313(4) 0.2203(2) 0.186(3) Uani 1 1 d . . . . .
Cl97 Cl 1.0529(2) 0.1670(2) 0.06392(10) 0.0899(8) Uani 1 1 d . . . . .
Cl98 Cl 1.1186(3) 0.2042(2) 0.16184(15) 0.1212(13) Uani 1 1 d . . . . .
Cl99 Cl 0.9120(2) 0.1837(2) 0.12009(12) 0.1061(11) 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
C1 N1 1.360(8) . ?
C1 C2 1.401(11) . ?
C1 C30 1.458(10) . ?
C2 C3 1.364(13) . ?
C3 C4 1.330(12) . ?
C4 C5 1.411(10) . ?
C5 N1 1.335(9) . ?
C5 O1 1.343(8) . ?
C6 O1 1.454(8) . ?
C6 C7 1.500(11) . ?
C7 C8 1.488(11) . ?
C8 C13 1.381(10) . ?
C8 C9 1.417(11) . ?
C9 C10 1.353(12) . ?
C10 C11 1.416(13) . ?
C11 O2 1.358(11) . ?
C11 C12 1.346(14) . ?
C12 C13 1.359(12) . ?
C14 O2 1.382(16) . ?
C14 C15 1.584(14) . ?
C15 C16 1.432(15) . ?
C16 C17 1.515(15) . ?
C17 O3 1.319(17) . ?
C18 C19 1.33(3) . ?
C18 O3 1.379(10) . ?
C18 C23 1.407(13) . ?
C18 C83 1.407(13) . ?
C18 C79 1.44(4) . ?
C25 C24 1.25(2) . ?
C25 O4 1.457(10) . ?
C23 C22 1.38(3) . ?
C24 C21 1.54(2) . ?
C21 C22 1.37(4) . ?
C21 C20 1.38(2) . ?
C19 C20 1.42(3) . ?
C85 C84 1.33(2) . ?
C85 O4 1.457(10) . ?
C83 C82 1.46(3) . ?
C84 C81 1.45(3) . ?
C81 C82 1.38(4) . ?
C81 C80 1.45(3) . ?
C80 C79 1.33(4) . ?
C26 O4 1.304(11) . ?
C26 N2 1.330(9) . ?
C26 C27 1.409(12) . ?
C27 C28 1.327(15) . ?
C28 C29 1.386(14) . ?
C29 C30 1.381(10) . ?
C30 N2 1.351(10) . ?
C31 N31 1.122(9) . ?
C31 C32 1.454(10) . ?
C41 N41 1.373(10) . ?
C41 C42 1.384(12) . ?
C41 C70 1.448(13) . ?
C42 C43 1.371(15) . ?
C43 C44 1.400(14) . ?
C44 C45 1.398(12) . ?
C45 N41 1.323(11) . ?
C45 O41 1.374(10) . ?
C46 O41 1.418(11) . ?
C46 C47 1.516(13) . ?
C47 C48 1.525(12) . ?
C48 C53 1.385(11) . ?
C48 C49 1.386(11) . ?
C49 C50 1.354(12) . ?
C50 C51 1.408(11) . ?
C51 O42 1.338(9) . ?
C51 C52 1.414(10) . ?
C52 C53 1.384(11) . ?
C54 O42 1.455(10) . ?
C54 C55 1.503(11) . ?
C55 C56 1.511(14) . ?
C56 C57 1.519(13) . ?
C57 O43 1.422(9) . ?
C58 O43 1.346(8) . ?
C58 C63 1.399(9) . ?
C58 C59 1.404(10) . ?
C59 C60 1.361(10) . ?
C60 C61 1.387(9) . ?
C61 C62 1.376(10) . ?
C61 C64 1.500(11) . ?
C62 C63 1.382(10) . ?
C64 C65 1.504(13) . ?
C65 O44 1.429(10) . ?
C66 N42 1.336(11) . ?
C66 O44 1.329(10) . ?
C66 C67 1.402(11) . ?
C67 C68 1.331(14) . ?
C68 C69 1.383(14) . ?
C69 C70 1.411(11) . ?
C70 N42 1.337(10) . ?
C71 N71 1.138(8) . ?
C71 C72 1.439(9) . ?
C95 Cl95 1.657(19) . ?
C95 Cl96 1.80(2) . ?
C97 Cl97 1.739(11) . ?
C97 Cl99 1.759(11) . ?
C97 Cl98 1.779(11) . ?
N1 Cu1 2.033(5) . ?
N2 Cu1 2.029(5) . ?
N31 Cu1 1.866(6) . ?
N41 Cu2 2.007(6) . ?
N42 Cu2 2.051(6) . ?
N71 Cu2 1.859(5) . ?
F1 P1 1.551(7) . ?
F2 P1 1.615(6) . ?
F3 P1 1.629(6) . ?
F4 P1 1.615(7) . ?
F5 P1 1.552(6) . ?
F6 P1 1.550(7) . ?
F7 P2 1.484(9) . ?
F8 P2 1.557(7) . ?
F9 P2 1.588(5) . ?
F10 P2 1.647(7) . ?
F11 P2 1.630(9) . ?
F12 P2 1.591(7) . ?

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 C1 C2 120.4(6) . . ?
N1 C1 C30 115.1(6) . . ?
C2 C1 C30 124.4(6) . . ?
C3 C2 C1 119.2(7) . . ?
C4 C3 C2 121.2(7) . . ?
C3 C4 C5 118.3(7) . . ?
N1 C5 O1 112.5(5) . . ?
N1 C5 C4 122.3(6) . . ?
O1 C5 C4 125.2(6) . . ?
O1 C6 C7 107.4(6) . . ?
C8 C7 C6 112.0(6) . . ?
C13 C8 C9 116.5(7) . . ?
C13 C8 C7 121.9(7) . . ?
C9 C8 C7 121.5(7) . . ?
C10 C9 C8 121.3(8) . . ?
C9 C10 C11 118.9(8) . . ?
O2 C11 C12 116.9(9) . . ?
O2 C11 C10 122.3(10) . . ?
C12 C11 C10 120.7(8) . . ?
C13 C12 C11 119.4(8) . . ?
C12 C13 C8 123.0(8) . . ?
O2 C14 C15 101.1(11) . . ?
C16 C15 C14 111.6(12) . . ?
C15 C16 C17 116.4(17) . . ?
O3 C17 C16 109.5(14) . . ?
C19 C18 O3 132.5(13) . . ?
C19 C18 C23 112.5(12) . . ?
O3 C18 C23 114.6(8) . . ?
O3 C18 C83 114.6(8) . . ?
O3 C18 C79 111.5(13) . . ?
C83 C18 C79 133.6(13) . . ?
C24 C25 O4 118.9(13) . . ?
C22 C23 C18 127.8(14) . . ?
C25 C24 C21 119.6(13) . . ?
C22 C21 C20 119.7(18) . . ?
C22 C21 C24 120.8(18) . . ?
C20 C21 C24 119.3(19) . . ?
C18 C19 C20 123.7(19) . . ?
C21 C20 C19 119.7(17) . . ?
C21 C22 C23 116.4(19) . . ?
C84 C85 O4 112.2(10) . . ?
C18 C83 C82 102.3(15) . . ?
C85 C84 C81 125.8(17) . . ?
C82 C81 C80 114(2) . . ?
C82 C81 C84 127(3) . . ?
C80 C81 C84 119(2) . . ?
C79 C80 C81 122(2) . . ?
C80 C79 C18 115(2) . . ?
C81 C82 C83 132(2) . . ?
O4 C26 N2 112.3(7) . . ?
O4 C26 C27 127.1(8) . . ?
N2 C26 C27 120.6(8) . . ?
C28 C27 C26 119.9(8) . . ?
C27 C28 C29 120.2(7) . . ?
C30 C29 C28 118.2(9) . . ?
N2 C30 C29 121.8(8) . . ?
N2 C30 C1 116.5(6) . . ?
C29 C30 C1 121.7(7) . . ?
N31 C31 C32 177.1(8) . . ?
N41 C41 C42 120.6(10) . . ?
N41 C41 C70 116.3(7) . . ?
C42 C41 C70 123.1(8) . . ?
C43 C42 C41 119.0(9) . . ?
C42 C43 C44 121.2(8) . . ?
C45 C44 C43 116.3(10) . . ?
N41 C45 O41 113.2(6) . . ?
N41 C45 C44 123.2(9) . . ?
O41 C45 C44 123.6(9) . . ?
O41 C46 C47 108.0(7) . . ?
C46 C47 C48 112.7(6) . . ?
C53 C48 C49 117.6(7) . . ?
C53 C48 C47 119.6(7) . . ?
C49 C48 C47 122.7(7) . . ?
C50 C49 C48 121.6(7) . . ?
C49 C50 C51 121.9(7) . . ?
O42 C51 C50 118.5(6) . . ?
O42 C51 C52 124.5(7) . . ?
C50 C51 C52 116.9(7) . . ?
C53 C52 C51 119.8(7) . . ?
C48 C53 C52 122.2(7) . . ?
O42 C54 C55 108.2(6) . . ?
C54 C55 C56 114.1(7) . . ?
C55 C56 C57 114.4(8) . . ?
O43 C57 C56 107.7(7) . . ?
O43 C58 C63 116.2(7) . . ?
O43 C58 C59 125.3(6) . . ?
C63 C58 C59 118.4(6) . . ?
C60 C59 C58 119.5(6) . . ?
C59 C60 C61 122.4(7) . . ?
C62 C61 C60 118.3(7) . . ?
C62 C61 C64 120.0(6) . . ?
C60 C61 C64 121.7(7) . . ?
C61 C62 C63 120.7(6) . . ?
C62 C63 C58 120.6(7) . . ?
C61 C64 C65 112.4(7) . . ?
O44 C65 C64 107.6(6) . . ?
N42 C66 O44 114.3(6) . . ?
N42 C66 C67 120.6(8) . . ?
O44 C66 C67 125.1(8) . . ?
C68 C67 C66 119.8(9) . . ?
C67 C68 C69 120.3(8) . . ?
C68 C69 C70 118.4(8) . . ?
N42 C70 C69 120.2(8) . . ?
N42 C70 C41 115.2(6) . . ?
C69 C70 C41 124.6(8) . . ?
N71 C71 C72 179.3(7) . . ?
Cl95 C95 Cl96 114.8(7) . . ?
Cl97 C97 Cl99 109.6(5) . . ?
Cl97 C97 Cl98 107.6(6) . . ?
Cl99 C97 Cl98 118.0(6) . . ?
C5 N1 C1 118.5(6) . . ?
C5 N1 Cu1 127.9(4) . . ?
C1 N1 Cu1 113.6(4) . . ?
C26 N2 C30 119.2(6) . . ?
C26 N2 Cu1 127.2(5) . . ?
C30 N2 Cu1 113.2(4) . . ?
C31 N31 Cu1 176.9(6) . . ?
C45 N41 C41 119.7(7) . . ?
C45 N41 Cu2 126.7(5) . . ?
C41 N41 Cu2 113.5(6) . . ?
C66 N42 C70 120.5(7) . . ?
C66 N42 Cu2 125.4(5) . . ?
C70 N42 Cu2 114.1(6) . . ?
C71 N71 Cu2 176.8(5) . . ?
C5 O1 C6 117.0(5) . . ?
C11 O2 C14 119.7(9) . . ?
C17 O3 C18 120.3(10) . . ?
C26 O4 C25 119.1(9) . . ?
C26 O4 C85 119.1(9) . . ?
C45 O41 C46 119.2(6) . . ?
C51 O42 C54 118.1(5) . . ?
C58 O43 C57 119.5(6) . . ?
C66 O44 C65 117.9(6) . . ?
F6 P1 F1 95.5(5) . . ?
F6 P1 F5 91.7(5) . . ?
F1 P1 F5 172.3(5) . . ?
F6 P1 F4 86.0(6) . . ?
F1 P1 F4 88.4(4) . . ?
F5 P1 F4 89.6(4) . . ?
F6 P1 F2 95.5(5) . . ?
F1 P1 F2 93.4(4) . . ?
F5 P1 F2 88.4(3) . . ?
F4 P1 F2 177.5(4) . . ?
F6 P1 F3 176.0(5) . . ?
F1 P1 F3 86.1(4) . . ?
F5 P1 F3 86.5(4) . . ?
F4 P1 F3 90.3(4) . . ?
F2 P1 F3 88.1(4) . . ?
F7 P2 F8 114.1(7) . . ?
F7 P2 F9 92.8(4) . . ?
F8 P2 F9 90.9(3) . . ?
F7 P2 F12 90.0(4) . . ?
F8 P2 F12 91.3(4) . . ?
F9 P2 F12 175.3(5) . . ?
F7 P2 F11 78.6(7) . . ?
F8 P2 F11 167.3(5) . . ?
F9 P2 F11 88.9(4) . . ?
F12 P2 F11 88.0(5) . . ?
F7 P2 F10 161.9(7) . . ?
F8 P2 F10 84.0(4) . . ?
F9 P2 F10 88.4(3) . . ?
F12 P2 F10 87.7(4) . . ?
F11 P2 F10 83.4(5) . . ?
N31 Cu1 N2 137.0(2) . . ?
N31 Cu1 N1 141.2(2) . . ?
N2 Cu1 N1 81.2(2) . . ?
N71 Cu2 N41 141.5(3) . . ?
N71 Cu2 N42 137.4(3) . . ?
N41 Cu2 N42 80.6(3) . . ?

_refine_diff_density_max         2.927
_refine_diff_density_min         -1.731
_refine_diff_density_rms         0.154



####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1442683'
_audit_update_record             
;
2015-12-15 deposited with the CCDC.
2016-01-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C60 H60 N4 O8'
_chemical_formula_weight         965.12

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

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

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

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

_cell_length_a                   9.688(2)
_cell_length_b                   11.374(2)
_cell_length_c                   13.628(3)
_cell_angle_alpha                100.5350(10)
_cell_angle_beta                 110.1260(10)
_cell_angle_gamma                109.435(2)
_cell_volume                     1252.4(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3861
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      27.6

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.161
_exptl_crystal_size_mid          0.131
_exptl_crystal_size_min          0.042
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4852
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24806
_diffrn_reflns_av_unetI/netI     0.0610
_diffrn_reflns_av_R_equivalents  0.0721
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.311
_diffrn_reflns_theta_max         27.630
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5778
_reflns_number_gt                4291
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0912P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5778
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0515
_refine_ls_wR_factor_ref         0.1645
_refine_ls_wR_factor_gt          0.1451
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.41975(12) 0.65134(10) 0.02071(9) 0.0285(3) Uani 1 1 d . . . . .
O2 O 1.30881(13) 1.11041(11) 0.55034(10) 0.0433(3) Uani 1 1 d . . . . .
O3 O 1.11326(12) 1.20215(11) 0.26617(9) 0.0351(3) Uani 1 1 d . . . . .
O4 O -0.21642(13) 0.52660(11) 0.30158(10) 0.0355(3) Uani 1 1 d . . . . .
N2 N 0.23596(13) 0.62435(12) 0.09521(10) 0.0246(3) Uani 1 1 d . . . . .
N1 N -0.03385(14) 0.54469(12) 0.22568(10) 0.0263(3) Uani 1 1 d . . . . .
C21 C 0.65186(17) 0.91799(14) 0.03048(13) 0.0277(3) Uani 1 1 d . . . . .
C7 C -0.3041(2) 0.36844(17) 0.38261(15) 0.0358(4) Uani 1 1 d . . . . .
H7A H -0.2665 0.4353 0.4531 0.043 Uiso 1 1 calc R U . . .
H7B H -0.4126 0.3555 0.3350 0.043 Uiso 1 1 calc R U . . .
C18 C 0.95929(17) 1.10977(15) 0.19272(13) 0.0305(3) Uani 1 1 d . . . . .
C4 C -0.17162(17) 0.68618(15) 0.21543(13) 0.0301(3) Uani 1 1 d . . . . .
H4 H -0.2464 0.7103 0.2314 0.036 Uiso 1 1 calc R U . . .
C17 C 1.15929(18) 1.22045(16) 0.38095(13) 0.0341(4) Uani 1 1 d . . . . .
H17A H 1.1402 1.1363 0.3932 0.041 Uiso 1 1 calc R U . . .
H17B H 1.0957 1.2575 0.4062 0.041 Uiso 1 1 calc R U . . .
C19 C 0.92317(18) 1.08127(16) 0.08099(14) 0.0343(4) Uani 1 1 d . . . . .
H19 H 1.0010 1.1261 0.0595 0.041 Uiso 1 1 calc R U . . .
C22 C 0.69009(17) 0.94888(15) 0.14276(13) 0.0298(3) Uani 1 1 d . . . . .
H22 H 0.6122 0.9043 0.1643 0.036 Uiso 1 1 calc R U . . .
C8 C -0.31113(19) 0.24001(16) 0.40146(14) 0.0328(4) Uani 1 1 d . . . . .
C26 C 0.33959(16) 0.58671(14) 0.07289(12) 0.0250(3) Uani 1 1 d . . . . .
C28 C 0.29422(17) 0.41805(14) 0.15327(13) 0.0278(3) Uani 1 1 d . . . . .
H28 H 0.3130 0.3485 0.1723 0.033 Uiso 1 1 calc R U . . .
C16 C 1.33736(18) 1.31358(15) 0.44368(14) 0.0329(4) Uani 1 1 d . . . . .
H16A H 1.3535 1.3978 0.4319 0.040 Uiso 1 1 calc R U . . .
H16B H 1.3980 1.2777 0.4138 0.040 Uiso 1 1 calc R U . . .
C1 C 0.04365(16) 0.60662(14) 0.17127(12) 0.0248(3) Uani 1 1 d . . . . .
C24 C 0.48733(17) 0.81819(15) -0.05992(13) 0.0282(3) Uani 1 1 d . . . . .
H24A H 0.5029 0.7536 -0.1069 0.034 Uiso 1 1 calc R U . . .
H24B H 0.4398 0.8636 -0.1054 0.034 Uiso 1 1 calc R U . . .
C11 C -0.32096(19) 0.00090(16) 0.43132(14) 0.0351(4) Uani 1 1 d . . . . .
C23 C 0.84048(18) 1.04385(15) 0.22369(13) 0.0315(3) Uani 1 1 d . . . . .
H23 H 0.8620 1.0635 0.2982 0.038 Uiso 1 1 calc R U . . .
C25 C 0.36723(17) 0.74522(15) -0.01994(13) 0.0277(3) Uani 1 1 d . . . . .
H25A H 0.3660 0.8069 0.0389 0.033 Uiso 1 1 calc R U . . .
H25B H 0.2585 0.6995 -0.0804 0.033 Uiso 1 1 calc R U . . .
C13 C -0.44916(19) 0.12203(16) 0.33988(13) 0.0332(4) Uani 1 1 d . . . . .
H13 H -0.5400 0.1228 0.2870 0.040 Uiso 1 1 calc R U . . .
C27 C 0.37604(17) 0.48450(15) 0.10127(13) 0.0280(3) Uani 1 1 d . . . . .
H27 H 0.4523 0.4627 0.0855 0.034 Uiso 1 1 calc R U . . .
C30 C 0.15776(15) 0.55893(14) 0.14747(12) 0.0245(3) Uani 1 1 d . . . . .
C29 C 0.18249(16) 0.45519(15) 0.17760(13) 0.0270(3) Uani 1 1 d . . . . .
H29 H 0.1264 0.4114 0.2130 0.032 Uiso 1 1 calc R U . . .
C14 C 1.45291(18) 1.23282(15) 0.60292(14) 0.0354(4) Uani 1 1 d . . . . .
H14A H 1.5348 1.2252 0.5799 0.042 Uiso 1 1 calc R U . . .
H14B H 1.4972 1.2556 0.6829 0.042 Uiso 1 1 calc R U . . .
C20 C 0.77295(19) 0.98717(16) 0.00196(14) 0.0335(4) Uani 1 1 d . . . . .
H20 H 0.7511 0.9689 -0.0726 0.040 Uiso 1 1 calc R U . . .
C5 C -0.13699(17) 0.58554(15) 0.24586(13) 0.0286(3) Uani 1 1 d . . . . .
C6 C -0.19123(19) 0.41715(15) 0.32969(14) 0.0302(3) Uani 1 1 d . . . . .
H6A H -0.0788 0.4456 0.3813 0.036 Uiso 1 1 calc R U . . .
H6B H -0.2182 0.3477 0.2638 0.036 Uiso 1 1 calc R U . . .
C9 C -0.1777(2) 0.23590(17) 0.48106(14) 0.0379(4) Uani 1 1 d . . . . .
H9 H -0.0845 0.3141 0.5253 0.046 Uiso 1 1 calc R U . . .
C2 C 0.01855(17) 0.70877(15) 0.13764(13) 0.0291(3) Uani 1 1 d . . . . .
H2 H 0.0737 0.7495 0.1005 0.035 Uiso 1 1 calc R U . . .
C3 C -0.09141(18) 0.74886(16) 0.16092(14) 0.0324(3) Uani 1 1 d . . . . .
H3 H -0.1102 0.8174 0.1397 0.039 Uiso 1 1 calc R U . . .
C12 C -0.45706(19) 0.00268(16) 0.35419(13) 0.0337(4) Uani 1 1 d . . . . .
H12 H -0.5522 -0.0748 0.3127 0.040 Uiso 1 1 calc R U . . .
C10 C -0.1811(2) 0.11839(17) 0.49567(15) 0.0408(4) Uani 1 1 d . . . . .
H10 H -0.0901 0.1176 0.5484 0.049 Uiso 1 1 calc R U . . .
C15 C 1.40574(19) 1.33735(16) 0.56842(14) 0.0355(4) Uani 1 1 d . . . . .
H15A H 1.5007 1.4219 0.6062 0.043 Uiso 1 1 calc R U . . .
H15B H 1.3250 1.3436 0.5932 0.043 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C26 1.3566(16) . ?
O1 C25 1.4456(16) . ?
O2 C11 1.3689(18) 2_666 ?
O2 C14 1.4331(18) . ?
O3 C18 1.3696(18) . ?
O3 C17 1.424(2) . ?
O4 C5 1.3649(17) . ?
O4 C6 1.4382(17) . ?
N2 C26 1.3162(17) . ?
N2 C30 1.3508(17) . ?
N1 C5 1.3197(18) . ?
N1 C1 1.3535(18) . ?
C21 C22 1.389(2) . ?
C21 C20 1.399(2) . ?
C21 C24 1.510(2) . ?
C7 C8 1.512(2) . ?
C7 C6 1.519(2) . ?
C18 C19 1.387(2) . ?
C18 C23 1.393(2) . ?
C4 C3 1.373(2) . ?
C4 C5 1.389(2) . ?
C17 C16 1.506(2) . ?
C19 C20 1.374(2) . ?
C22 C23 1.385(2) . ?
C8 C13 1.384(2) . ?
C8 C9 1.394(2) . ?
C26 C27 1.4034(19) . ?
C28 C27 1.3731(19) . ?
C28 C29 1.4000(19) . ?
C16 C15 1.529(2) . ?
C1 C2 1.3874(19) . ?
C1 C30 1.4843(19) . ?
C24 C25 1.5161(18) . ?
C11 O2 1.3689(18) 2_666 ?
C11 C12 1.384(2) . ?
C11 C10 1.393(2) . ?
C13 C12 1.387(2) . ?
C30 C29 1.3841(19) . ?
C14 C15 1.504(2) . ?
C9 C10 1.378(2) . ?
C2 C3 1.3952(19) . ?

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
C26 O1 C25 116.30(10) . . ?
C11 O2 C14 118.38(12) 2_666 . ?
C18 O3 C17 117.33(11) . . ?
C5 O4 C6 118.30(11) . . ?
C26 N2 C30 117.79(12) . . ?
C5 N1 C1 116.87(12) . . ?
C22 C21 C20 116.97(14) . . ?
C22 C21 C24 123.42(12) . . ?
C20 C21 C24 119.58(14) . . ?
C8 C7 C6 111.91(12) . . ?
O3 C18 C19 116.57(13) . . ?
O3 C18 C23 124.17(14) . . ?
C19 C18 C23 119.25(14) . . ?
C3 C4 C5 117.54(13) . . ?
O3 C17 C16 107.80(12) . . ?
C20 C19 C18 120.29(14) . . ?
C23 C22 C21 122.13(13) . . ?
C13 C8 C9 117.42(14) . . ?
C13 C8 C7 121.48(14) . . ?
C9 C8 C7 121.10(15) . . ?
N2 C26 O1 118.74(12) . . ?
N2 C26 C27 124.35(13) . . ?
O1 C26 C27 116.90(12) . . ?
C27 C28 C29 119.90(13) . . ?
C17 C16 C15 113.51(12) . . ?
N1 C1 C2 122.73(12) . . ?
N1 C1 C30 116.58(12) . . ?
C2 C1 C30 120.69(13) . . ?
C21 C24 C25 115.28(13) . . ?
O2 C11 C12 125.05(14) 2_666 . ?
O2 C11 C10 114.97(14) 2_666 . ?
C12 C11 C10 119.97(15) . . ?
C22 C23 C18 119.54(15) . . ?
O1 C25 C24 106.98(11) . . ?
C8 C13 C12 122.42(14) . . ?
C28 C27 C26 117.12(12) . . ?
N2 C30 C29 122.65(12) . . ?
N2 C30 C1 115.29(12) . . ?
C29 C30 C1 122.06(13) . . ?
C30 C29 C28 118.17(13) . . ?
O2 C14 C15 107.34(12) . . ?
C19 C20 C21 121.81(15) . . ?
N1 C5 O4 118.72(13) . . ?
N1 C5 C4 125.05(13) . . ?
O4 C5 C4 116.23(12) . . ?
O4 C6 C7 105.33(11) . . ?
C10 C9 C8 121.40(15) . . ?
C1 C2 C3 118.43(13) . . ?
C4 C3 C2 119.39(13) . . ?
C11 C12 C13 118.88(15) . . ?
C9 C10 C11 119.85(15) . . ?
C14 C15 C16 115.03(14) . . ?

_refine_diff_density_max         0.342
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.067



####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1442684'
_audit_update_record             
;
2015-12-15 deposited with the CCDC.
2016-01-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C61 H75 Cl2 N5 O5'
_chemical_formula_weight         1029.16

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   10.1938(16)
_cell_length_b                   25.558(4)
_cell_length_c                   21.504(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.243(2)
_cell_angle_gamma                90
_cell_volume                     5601.2(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    10287
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_F_000             2200
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.169
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.456
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            55328
_diffrn_reflns_av_unetI/netI     0.0865
_diffrn_reflns_av_R_equivalents  0.0938
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.368
_diffrn_reflns_theta_max         27.526
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             12877
_reflns_number_gt                7016
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1866P)²+10.1302P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         12877
_refine_ls_number_parameters     727
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1553
_refine_ls_R_factor_gt           0.0840
_refine_ls_wR_factor_ref         0.3066
_refine_ls_wR_factor_gt          0.2327
_refine_ls_goodness_of_fit_ref   0.865
_refine_ls_restrained_S_all      0.865
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6123(4) 0.63156(15) 0.21789(17) 0.0356(9) Uani 1 1 d . . . . .
C2 C 0.6706(5) 0.58214(18) 0.2130(2) 0.0482(11) Uani 1 1 d . . . . .
H2 H 0.6222 0.5535 0.1988 0.058 Uiso 1 1 calc R U . . .
C3 C 0.8028(5) 0.57690(19) 0.2298(2) 0.0548(13) Uani 1 1 d . . . . .
H3 H 0.8439 0.5446 0.2268 0.066 Uiso 1 1 calc R U . . .
C4 C 0.8712(5) 0.61937(18) 0.2505(2) 0.0491(11) Uani 1 1 d . . . . .
H4 H 0.9596 0.6164 0.2615 0.059 Uiso 1 1 calc R U . . .
C5 C 0.8072(4) 0.66777(16) 0.25517(17) 0.0369(9) Uani 1 1 d . . . . .
C6 C 0.8775(4) 0.71586(17) 0.27569(17) 0.0364(9) Uani 1 1 d . . . . .
C7 C 1.0036(5) 0.7270(2) 0.2551(2) 0.0507(12) Uani 1 1 d . . . . .
H7 H 1.0465 0.7024 0.2310 0.061 Uiso 1 1 calc R U . . .
C8 C 1.0665(4) 0.7736(2) 0.2697(2) 0.0516(12) Uani 1 1 d . . . . .
H8 H 1.1503 0.7800 0.2552 0.062 Uiso 1 1 calc R U . . .
C9 C 1.0048(4) 0.81070(17) 0.30583(19) 0.0402(10) Uani 1 1 d . . . . .
C10 C 0.8802(4) 0.79937(16) 0.32853(17) 0.0352(8) Uani 1 1 d . . . . .
H10 H 0.8390 0.8234 0.3541 0.042 Uiso 1 1 calc R U . . .
C11 C 0.8185(4) 0.75328(15) 0.31343(17) 0.0334(8) Uani 1 1 d . . . . .
H11 H 0.7353 0.7468 0.3287 0.040 Uiso 1 1 calc R U . . .
C12 C 1.1706(7) 0.8796(3) 0.3002(4) 0.0356(15) Uani 0.65 1 d . . P A 1
H12A H 1.2392 0.8533 0.2998 0.043 Uiso 0.65 1 calc R U P A 1
H12B H 1.1998 0.9082 0.3268 0.043 Uiso 0.65 1 calc R U P A 1
C13 C 1.1437(6) 0.8994(2) 0.2352(3) 0.0374(14) Uani 0.65 1 d . . P A 1
H13A H 1.2247 0.9080 0.2147 0.045 Uiso 0.65 1 calc R U P A 1
H13B H 1.0962 0.8736 0.2105 0.045 Uiso 0.65 1 calc R U P A 1
C92 C 1.1657(13) 0.8690(6) 0.2673(7) 0.041(3) Uani 0.35 1 d . . P A 2
H92A H 1.2463 0.8497 0.2749 0.050 Uiso 0.35 1 calc R U P A 2
H92B H 1.1302 0.8604 0.2264 0.050 Uiso 0.35 1 calc R U P A 2
C93 C 1.1850(11) 0.9248(5) 0.2747(6) 0.039(3) Uani 0.35 1 d . . P A 2
H93A H 1.2628 0.9365 0.2535 0.047 Uiso 0.35 1 calc R U P A 2
H93B H 1.1926 0.9344 0.3183 0.047 Uiso 0.35 1 calc R U P A 2
C14 C 1.0112(5) 0.95841(18) 0.1853(3) 0.0599(14) Uani 1 1 d . . . . .
H14A H 0.9776 0.9267 0.1659 0.072 Uiso 1 1 calc R U . . .
H14B H 1.0795 0.9726 0.1595 0.072 Uiso 1 1 calc R U . . .
C15 C 0.9036(5) 0.99732(16) 0.1920(2) 0.0459(11) Uani 1 1 d . . . . .
H15A H 0.8374 0.9839 0.2195 0.055 Uiso 1 1 calc R U . . .
H15B H 0.9380 1.0297 0.2092 0.055 Uiso 1 1 calc R U . . .
C16 C 0.7447(5) 1.04243(16) 0.1320(2) 0.0475(11) Uani 1 1 d . . . . .
H16A H 0.7371 1.0586 0.0913 0.057 Uiso 1 1 calc R U . . .
H16B H 0.7666 1.0698 0.1618 0.057 Uiso 1 1 calc R U . . .
C17 C 0.6138(4) 1.01976(15) 0.14815(19) 0.0409(10) Uani 1 1 d . . . . .
H17A H 0.6230 0.9975 0.1845 0.049 Uiso 1 1 calc R U . . .
H17B H 0.5528 1.0477 0.1576 0.049 Uiso 1 1 calc R U . . .
C18 C 0.4495(5) 0.96170(16) 0.11109(19) 0.0430(10) Uani 1 1 d . . . . .
H18A H 0.3859 0.9848 0.1298 0.052 Uiso 1 1 calc R U . . .
H18B H 0.4701 0.9337 0.1401 0.052 Uiso 1 1 calc R U . . .
C19 C 0.3953(5) 0.93964(16) 0.05045(19) 0.0436(10) Uani 1 1 d . . . . .
H19A H 0.3733 0.9681 0.0223 0.052 Uiso 1 1 calc R U . . .
H19B H 0.4617 0.9183 0.0312 0.052 Uiso 1 1 calc R U . . .
C20 C 0.2973(4) 0.85752(15) 0.08089(17) 0.0354(9) Uani 1 1 d . . . . .
C21 C 0.1843(4) 0.82942(16) 0.09419(17) 0.0359(9) Uani 1 1 d . . . . .
H21 H 0.1026 0.8453 0.0894 0.043 Uiso 1 1 calc R U . . .
C22 C 0.1920(4) 0.77813(15) 0.11450(17) 0.0326(8) Uani 1 1 d . . . . .
H22 H 0.1156 0.7600 0.1233 0.039 Uiso 1 1 calc R U . . .
C23 C 0.3142(4) 0.75323(15) 0.12190(16) 0.0305(8) Uani 1 1 d . . . . .
C24 C 0.4258(4) 0.78155(15) 0.10688(17) 0.0351(8) Uani 1 1 d . . . . .
H24 H 0.5074 0.7654 0.1101 0.042 Uiso 1 1 calc R U . . .
C25 C 0.4188(4) 0.83316(15) 0.08732(18) 0.0355(9) Uani 1 1 d . . . . .
H25 H 0.4951 0.8514 0.0785 0.043 Uiso 1 1 calc R U . . .
C26 C 0.3313(4) 0.69931(15) 0.14708(16) 0.0312(8) Uani 1 1 d . . . . .
C27 C 0.2301(4) 0.66170(15) 0.14620(17) 0.0342(8) Uani 1 1 d . . . . .
H27 H 0.1480 0.6695 0.1289 0.041 Uiso 1 1 calc R U . . .
C28 C 0.2554(4) 0.61290(16) 0.17156(19) 0.0393(9) Uani 1 1 d . . . . .
H28 H 0.1899 0.5876 0.1720 0.047 Uiso 1 1 calc R U . . .
C29 C 0.3791(4) 0.60207(16) 0.19624(18) 0.0387(9) Uani 1 1 d . . . . .
H29 H 0.3977 0.5695 0.2135 0.046 Uiso 1 1 calc R U . . .
C30 C 0.4757(4) 0.64090(15) 0.19482(16) 0.0328(8) Uani 1 1 d . . . . .
C31 C 0.3437(7) 0.68749(17) 0.3336(2) 0.0704(18) Uani 1 1 d . . . . .
H31A H 0.2756 0.7041 0.3092 0.106 Uiso 1 1 calc R U . . .
H31B H 0.3180 0.6523 0.3431 0.106 Uiso 1 1 calc R U . . .
H31C H 0.4232 0.6869 0.3105 0.106 Uiso 1 1 calc R U . . .
C32 C 0.2461(5) 0.71304(16) 0.4342(2) 0.0506(12) Uani 1 1 d . . . . .
H32A H 0.2621 0.7305 0.4731 0.076 Uiso 1 1 calc R U . . .
H32B H 0.2283 0.6767 0.4417 0.076 Uiso 1 1 calc R U . . .
H32C H 0.1720 0.7288 0.4132 0.076 Uiso 1 1 calc R U . . .
C33 C 0.4834(5) 0.6924(2) 0.4283(3) 0.0699(17) Uani 1 1 d . . . . .
H33A H 0.5585 0.6930 0.4021 0.105 Uiso 1 1 calc R U . . .
H33B H 0.4620 0.6568 0.4382 0.105 Uiso 1 1 calc R U . . .
H33C H 0.5028 0.7113 0.4659 0.105 Uiso 1 1 calc R U . . .
C34 C 0.3663(4) 0.71796(13) 0.39403(16) 0.0310(8) Uani 1 1 d . . . . .
C35 C 0.2273(4) 0.90432(16) 0.4758(2) 0.0406(10) Uani 1 1 d . . . . .
H35A H 0.1752 0.9057 0.4381 0.061 Uiso 1 1 calc R U . . .
H35B H 0.2028 0.9325 0.5026 0.061 Uiso 1 1 calc R U . . .
H35C H 0.2130 0.8716 0.4964 0.061 Uiso 1 1 calc R U . . .
C36 C 0.4559(4) 0.90274(15) 0.52000(17) 0.0369(9) Uani 1 1 d . . . . .
H36A H 0.4462 0.8677 0.5352 0.055 Uiso 1 1 calc R U . . .
H36B H 0.4265 0.9270 0.5508 0.055 Uiso 1 1 calc R U . . .
H36C H 0.5466 0.9093 0.5116 0.055 Uiso 1 1 calc R U . . .
C37 C 0.3959(4) 0.96516(14) 0.43478(18) 0.0340(8) Uani 1 1 d . . . . .
H37A H 0.4875 0.9702 0.4273 0.051 Uiso 1 1 calc R U . . .
H37B H 0.3673 0.9904 0.4647 0.051 Uiso 1 1 calc R U . . .
H37C H 0.3466 0.9696 0.3966 0.051 Uiso 1 1 calc R U . . .
C38 C 0.3737(4) 0.90948(13) 0.46011(16) 0.0290(8) Uani 1 1 d . . . . .
C39 C 0.4119(3) 0.86746(13) 0.41299(16) 0.0252(7) Uani 1 1 d . . . . .
C40 C 0.3728(4) 0.81549(13) 0.42224(16) 0.0276(7) Uani 1 1 d . . . . .
H40 H 0.3247 0.8076 0.4573 0.033 Uiso 1 1 calc R U . . .
C41 C 0.4028(3) 0.77485(13) 0.38109(15) 0.0255(7) Uani 1 1 d . . . . .
C42 C 0.4760(3) 0.78742(13) 0.32899(15) 0.0251(7) Uani 1 1 d . . . . .
H42 H 0.4964 0.7615 0.3005 0.030 Uiso 1 1 calc R U . . .
C43 C 0.5187(3) 0.83868(13) 0.31937(15) 0.0241(7) Uani 1 1 d . . . . .
C44 C 0.4872(3) 0.87818(13) 0.36113(15) 0.0256(7) Uani 1 1 d . . . . .
H44 H 0.5167 0.9121 0.3543 0.031 Uiso 1 1 calc R U . . .
C45 C 0.5975(3) 0.84961(12) 0.26486(15) 0.0230(7) Uani 1 1 d . . . . .
C46 C 0.6331(3) 0.81634(13) 0.21834(15) 0.0245(7) Uani 1 1 d . . . . .
H46 H 0.6112 0.7812 0.2140 0.029 Uiso 1 1 calc R U . . .
C47 C 0.7615(3) 0.83124(13) 0.12062(15) 0.0248(7) Uani 1 1 d . . . . .
C48 C 0.7796(3) 0.77851(13) 0.10680(16) 0.0248(7) Uani 1 1 d . . . . .
H48 H 0.7651 0.7533 0.1371 0.030 Uiso 1 1 calc R U . . .
C49 C 0.8195(3) 0.76330(13) 0.04798(16) 0.0255(7) Uani 1 1 d . . . . .
C50 C 0.8441(3) 0.80277(13) 0.00461(16) 0.0272(7) Uani 1 1 d . . . . .
H50 H 0.8706 0.7931 -0.0349 0.033 Uiso 1 1 calc R U . . .
C51 C 0.8307(3) 0.85624(13) 0.01803(16) 0.0262(7) Uani 1 1 d . . . . .
C52 C 0.7865(3) 0.87004(13) 0.07696(16) 0.0276(7) Uani 1 1 d . . . . .
H52 H 0.7739 0.9051 0.0870 0.033 Uiso 1 1 calc R U . . .
C53 C 0.8286(3) 0.70559(13) 0.02845(16) 0.0270(7) Uani 1 1 d . . . . .
C54 C 0.8174(5) 0.66847(14) 0.08402(18) 0.0388(9) Uani 1 1 d . . . . .
H54A H 0.7331 0.6728 0.1024 0.058 Uiso 1 1 calc R U . . .
H54B H 0.8851 0.6764 0.1143 0.058 Uiso 1 1 calc R U . . .
H54C H 0.8267 0.6330 0.0702 0.058 Uiso 1 1 calc R U . . .
C55 C 0.7166(4) 0.69478(15) -0.01814(18) 0.0339(8) Uani 1 1 d . . . . .
H55A H 0.6342 0.7009 0.0013 0.051 Uiso 1 1 calc R U . . .
H55B H 0.7209 0.6590 -0.0317 0.051 Uiso 1 1 calc R U . . .
H55C H 0.7245 0.7176 -0.0533 0.051 Uiso 1 1 calc R U . . .
C56 C 0.9613(4) 0.69495(14) -0.00231(17) 0.0309(8) Uani 1 1 d . . . . .
H56A H 0.9669 0.6586 -0.0132 0.046 Uiso 1 1 calc R U . . .
H56B H 1.0315 0.7037 0.0263 0.046 Uiso 1 1 calc R U . . .
H56C H 0.9679 0.7159 -0.0391 0.046 Uiso 1 1 calc R U . . .
C57 C 0.8602(4) 0.89846(13) -0.03053(17) 0.0314(8) Uani 1 1 d . . . . .
C58 C 0.9941(9) 0.9267(3) -0.0050(4) 0.044(2) Uani 0.5 1 d . . P B 1
H58A H 1.0165 0.9548 -0.0324 0.066 Uiso 0.5 1 calc R U P B 1
H58B H 1.0642 0.9016 -0.0036 0.066 Uiso 0.5 1 calc R U P B 1
H58C H 0.9806 0.9403 0.0359 0.066 Uiso 0.5 1 calc R U P B 1
C59 C 0.8942(11) 0.8759(3) -0.0930(3) 0.0386(19) Uani 0.5 1 d . . P B 1
H59A H 0.8243 0.8535 -0.1075 0.058 Uiso 0.5 1 calc R U P B 1
H59B H 0.9738 0.8560 -0.0891 0.058 Uiso 0.5 1 calc R U P B 1
H59C H 0.9060 0.9038 -0.1222 0.058 Uiso 0.5 1 calc R U P B 1
C60 C 0.7568(10) 0.9380(4) -0.0341(5) 0.050(2) Uani 0.5 1 d . . P B 1
H60A H 0.6764 0.9221 -0.0485 0.075 Uiso 0.5 1 calc R U P B 1
H60B H 0.7815 0.9650 -0.0626 0.075 Uiso 0.5 1 calc R U P B 1
H60C H 0.7446 0.9529 0.0063 0.075 Uiso 0.5 1 calc R U P B 1
C61 C 0.8644(13) 0.9527(3) -0.0050(4) 0.061(3) Uani 0.5 1 d . . P B 2
H61A H 0.9321 0.9551 0.0266 0.092 Uiso 0.5 1 calc R U P B 2
H61B H 0.7812 0.9610 0.0127 0.092 Uiso 0.5 1 calc R U P B 2
H61C H 0.8824 0.9770 -0.0378 0.092 Uiso 0.5 1 calc R U P B 2
C62 C 0.9805(10) 0.8860(4) -0.0664(5) 0.050(2) Uani 0.5 1 d . . P B 2
H62A H 0.9905 0.9113 -0.0989 0.075 Uiso 0.5 1 calc R U P B 2
H62B H 0.9720 0.8517 -0.0843 0.075 Uiso 0.5 1 calc R U P B 2
H62C H 1.0560 0.8869 -0.0390 0.075 Uiso 0.5 1 calc R U P B 2
C63 C 0.7381(9) 0.8984(4) -0.0804(4) 0.050(2) Uani 0.5 1 d . . P B 2
H63A H 0.7551 0.9230 -0.1130 0.075 Uiso 0.5 1 calc R U P B 2
H63B H 0.6592 0.9081 -0.0598 0.075 Uiso 0.5 1 calc R U P B 2
H63C H 0.7280 0.8640 -0.0978 0.075 Uiso 0.5 1 calc R U P B 2
N1 N 0.4510(3) 0.68881(12) 0.17146(14) 0.0313(7) Uani 1 1 d . . . . .
N2 N 0.6789(3) 0.67372(13) 0.23966(14) 0.0338(7) Uani 1 1 d . . . . .
N3 N 0.7075(3) 0.84578(11) 0.17965(14) 0.0300(7) Uani 1 1 d . . . . .
N4 N 0.7171(4) 0.89534(12) 0.20207(16) 0.0416(9) Uani 1 1 d . . . . .
N5 N 0.6504(4) 0.89770(12) 0.25382(15) 0.0387(8) Uani 1 1 d . . . . .
O1 O 0.2794(3) 0.90829(11) 0.06078(13) 0.0424(7) Uani 1 1 d . . . . .
O2 O 0.5648(3) 0.98986(11) 0.09641(13) 0.0439(7) Uani 1 1 d . . . . .
O3 O 0.8485(3) 1.00607(11) 0.13149(14) 0.0469(8) Uani 1 1 d . . . . .
O4 O 1.0616(4) 0.94747(14) 0.2447(2) 0.0706(11) Uani 1 1 d . . . . .
O5 O 1.0564(3) 0.85815(12) 0.32292(17) 0.0541(9) Uani 1 1 d . . . . .
Cl99 Cl 0.98912(19) 0.51785(7) 0.10597(12) 0.1116(8) Uani 1 1 d . . . . .
Cl98 Cl 1.2339(4) 0.4719(2) 0.1008(3) 0.1054(16) Uani 0.45 1 d . . P C 1
Cl97 Cl 1.2003(4) 0.44679(15) 0.06701(18) 0.0947(12) Uani 0.55 1 d . . P C 2
C99 C 1.0954(9) 0.4621(4) 0.1198(5) 0.145(4) Uani 1 1 d . . . . .
H99A H 1.0951 0.4534 0.1637 0.174 Uiso 1 1 calc R U . C 1
H99B H 1.0609 0.4323 0.0968 0.174 Uiso 1 1 calc R U . C 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
C1 N2 1.351(5) . ?
C1 C2 1.401(6) . ?
C1 C30 1.488(6) . ?
C2 C3 1.394(7) . ?
C3 C4 1.361(7) . ?
C4 C5 1.403(6) . ?
C5 N2 1.351(5) . ?
C5 C6 1.485(6) . ?
C6 C7 1.397(6) . ?
C6 C11 1.399(5) . ?
C7 C8 1.386(7) . ?
C8 C9 1.385(6) . ?
C9 O5 1.369(5) . ?
C9 C10 1.400(5) . ?
C10 C11 1.371(6) . ?
C12 O5 1.385(7) . ?
C12 C13 1.506(9) . ?
C13 O4 1.503(7) . ?
C92 C93 1.45(2) . ?
C92 O5 1.675(13) . ?
C93 O4 1.516(12) . ?
C14 O4 1.396(7) . ?
C14 C15 1.490(7) . ?
C15 O3 1.423(6) . ?
C16 O3 1.408(5) . ?
C16 C17 1.503(6) . ?
C17 O2 1.431(5) . ?
C18 O2 1.420(5) . ?
C18 C19 1.514(6) . ?
C19 O1 1.449(5) . ?
C20 O1 1.379(5) . ?
C20 C25 1.390(6) . ?
C20 C21 1.393(6) . ?
C21 C22 1.383(5) . ?
C22 C23 1.405(5) . ?
C23 C24 1.392(5) . ?
C23 C26 1.489(5) . ?
C24 C25 1.386(6) . ?
C26 N1 1.344(5) . ?
C26 C27 1.410(5) . ?
C27 C28 1.383(6) . ?
C28 C29 1.386(6) . ?
C29 C30 1.398(6) . ?
C30 N1 1.345(5) . ?
C31 C34 1.528(6) . ?
C32 C34 1.519(5) . ?
C33 C34 1.535(6) . ?
C34 C41 1.528(5) . ?
C35 C38 1.543(5) . ?
C36 C38 1.531(5) . ?
C37 C38 1.542(5) . ?
C38 C39 1.533(5) . ?
C39 C44 1.395(5) . ?
C39 C40 1.402(5) . ?
C40 C41 1.403(5) . ?
C41 C42 1.397(4) . ?
C42 C43 1.397(5) . ?
C43 C44 1.393(5) . ?
C43 C45 1.463(4) . ?
C45 N5 1.365(4) . ?
C45 C46 1.368(5) . ?
C46 N3 1.364(4) . ?
C47 C52 1.393(5) . ?
C47 C48 1.393(5) . ?
C47 N3 1.443(4) . ?
C48 C49 1.392(5) . ?
C49 C50 1.400(5) . ?
C49 C53 1.537(5) . ?
C50 C51 1.404(5) . ?
C51 C52 1.399(5) . ?
C51 C57 1.536(5) . ?
C53 C55 1.528(5) . ?
C53 C54 1.532(5) . ?
C53 C56 1.542(5) . ?
C57 C60 1.461(9) . ?
C57 C61 1.492(9) . ?
C57 C62 1.497(9) . ?
C57 C59 1.509(8) . ?
C57 C63 1.625(10) . ?
C57 C58 1.628(9) . ?
N3 N4 1.358(4) . ?
N4 N5 1.318(4) . ?
Cl99 C99 1.811(11) . ?
Cl98 C99 1.500(8) . ?
Cl97 C99 1.624(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 C2 122.3(4) . . ?
N2 C1 C30 116.5(3) . . ?
C2 C1 C30 121.0(4) . . ?
C3 C2 C1 118.4(4) . . ?
C4 C3 C2 119.6(4) . . ?
C3 C4 C5 119.4(4) . . ?
N2 C5 C4 122.1(4) . . ?
N2 C5 C6 116.0(3) . . ?
C4 C5 C6 121.9(4) . . ?
C7 C6 C11 117.1(4) . . ?
C7 C6 C5 121.0(4) . . ?
C11 C6 C5 121.8(3) . . ?
C8 C7 C6 121.8(4) . . ?
C9 C8 C7 120.1(4) . . ?
O5 C9 C8 125.5(4) . . ?
O5 C9 C10 115.8(4) . . ?
C8 C9 C10 118.7(4) . . ?
C11 C10 C9 120.7(4) . . ?
C10 C11 C6 121.6(4) . . ?
O5 C12 C13 108.8(6) . . ?
O4 C13 C12 103.8(5) . . ?
C93 C92 O5 100.2(10) . . ?
C92 C93 O4 102.7(9) . . ?
O4 C14 C15 107.6(4) . . ?
O3 C15 C14 107.1(4) . . ?
O3 C16 C17 114.7(3) . . ?
O2 C17 C16 108.8(3) . . ?
O2 C18 C19 106.6(3) . . ?
O1 C19 C18 110.9(3) . . ?
O1 C20 C25 124.4(4) . . ?
O1 C20 C21 116.4(4) . . ?
C25 C20 C21 119.2(4) . . ?
C22 C21 C20 120.8(4) . . ?
C21 C22 C23 120.6(4) . . ?
C24 C23 C22 117.7(4) . . ?
C24 C23 C26 118.4(3) . . ?
C22 C23 C26 123.8(3) . . ?
C25 C24 C23 121.9(4) . . ?
C24 C25 C20 119.8(4) . . ?
N1 C26 C27 121.8(4) . . ?
N1 C26 C23 115.1(3) . . ?
C27 C26 C23 123.1(4) . . ?
C28 C27 C26 118.7(4) . . ?
C27 C28 C29 119.4(4) . . ?
C28 C29 C30 119.0(4) . . ?
N1 C30 C29 121.8(4) . . ?
N1 C30 C1 115.9(3) . . ?
C29 C30 C1 122.2(4) . . ?
C32 C34 C31 109.4(4) . . ?
C32 C34 C41 112.6(3) . . ?
C31 C34 C41 111.3(3) . . ?
C32 C34 C33 108.7(4) . . ?
C31 C34 C33 107.0(4) . . ?
C41 C34 C33 107.6(3) . . ?
C36 C38 C39 109.6(3) . . ?
C36 C38 C37 108.6(3) . . ?
C39 C38 C37 111.8(3) . . ?
C36 C38 C35 108.7(3) . . ?
C39 C38 C35 110.2(3) . . ?
C37 C38 C35 107.8(3) . . ?
C44 C39 C40 117.6(3) . . ?
C44 C39 C38 122.9(3) . . ?
C40 C39 C38 119.5(3) . . ?
C39 C40 C41 123.0(3) . . ?
C42 C41 C40 117.6(3) . . ?
C42 C41 C34 120.1(3) . . ?
C40 C41 C34 122.2(3) . . ?
C41 C42 C43 120.5(3) . . ?
C44 C43 C42 120.5(3) . . ?
C44 C43 C45 121.1(3) . . ?
C42 C43 C45 118.4(3) . . ?
C43 C44 C39 120.8(3) . . ?
N5 C45 C46 108.7(3) . . ?
N5 C45 C43 122.5(3) . . ?
C46 C45 C43 128.8(3) . . ?
N3 C46 C45 105.2(3) . . ?
C52 C47 C48 121.2(3) . . ?
C52 C47 N3 119.2(3) . . ?
C48 C47 N3 119.5(3) . . ?
C49 C48 C47 120.4(3) . . ?
C48 C49 C50 117.7(3) . . ?
C48 C49 C53 122.5(3) . . ?
C50 C49 C53 119.8(3) . . ?
C49 C50 C51 123.0(3) . . ?
C52 C51 C50 117.8(3) . . ?
C52 C51 C57 120.7(3) . . ?
C50 C51 C57 121.5(3) . . ?
C47 C52 C51 119.9(3) . . ?
C55 C53 C54 109.4(3) . . ?
C55 C53 C49 107.7(3) . . ?
C54 C53 C49 112.0(3) . . ?
C55 C53 C56 109.7(3) . . ?
C54 C53 C56 107.9(3) . . ?
C49 C53 C56 110.2(3) . . ?
C61 C57 C62 111.8(7) . . ?
C60 C57 C59 113.4(6) . . ?
C60 C57 C51 111.8(4) . . ?
C61 C57 C51 114.0(4) . . ?
C62 C57 C51 112.0(4) . . ?
C59 C57 C51 112.9(4) . . ?
C61 C57 C63 105.0(7) . . ?
C62 C57 C63 106.5(6) . . ?
C51 C57 C63 106.8(4) . . ?
C60 C57 C58 108.1(6) . . ?
C59 C57 C58 105.2(5) . . ?
C51 C57 C58 104.9(4) . . ?
C26 N1 C30 119.2(3) . . ?
C1 N2 C5 118.1(3) . . ?
N4 N3 C46 109.5(3) . . ?
N4 N3 C47 121.8(3) . . ?
C46 N3 C47 128.5(3) . . ?
N5 N4 N3 108.0(3) . . ?
N4 N5 C45 108.6(3) . . ?
C20 O1 C19 117.8(3) . . ?
C18 O2 C17 112.0(3) . . ?
C16 O3 C15 112.2(3) . . ?
C14 O4 C13 103.5(4) . . ?
C14 O4 C93 138.7(6) . . ?
C9 O5 C12 125.3(5) . . ?
C9 O5 C92 102.3(6) . . ?
Cl98 C99 Cl99 112.8(6) . . ?
Cl97 C99 Cl99 118.4(6) . . ?

_refine_diff_density_max         0.543
_refine_diff_density_min         -0.845
_refine_diff_density_rms         0.076



