# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

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

data_fdd-20180312
_database_code_depnum_ccdc_archive 'CCDC 1837871'
_audit_update_record             
;
2018-04-17 deposited with the CCDC.
2019-02-08 downloaded from the CCDC.
;
_audit_creation_date             2018-03-13
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.02.02 svn.r3481 for OlexSys, GUI svn.r5470)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H22 Cl N5 O8'
_chemical_formula_sum            'C21 H22 Cl N5 O8'
_chemical_formula_weight         507.89
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 Cl1 N1 O1 '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   25.9456(5)
_cell_length_b                   8.8451(3)
_cell_length_c                   23.3704(7)
_cell_angle_alpha                90
_cell_angle_beta                 101.146(3)
_cell_angle_gamma                90
_cell_volume                     5262.1(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    54083
_cell_measurement_temperature    293.0(10)
_cell_measurement_theta_max      72.5090
_cell_measurement_theta_min      4.2110
_shelx_estimated_absorpt_T_max   0.859
_shelx_estimated_absorpt_T_min   0.489
_exptl_absorpt_coefficient_mu    1.739
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.05273
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'rect. Prism'
_exptl_crystal_F_000             2112
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1610
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            98174
_diffrn_reflns_point_group_measured_fraction_full 0.942
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        67.063
_diffrn_reflns_theta_max         67.063
_diffrn_reflns_theta_min         3.631
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.0(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0528
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):
  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -31.00  53.00   1.00    1.00    --   36.36 -57.00-150.00   84
  2  ω     10.00 104.00   1.00    1.00    --   36.36  77.00  90.00   94
  3  ω    -31.00  53.00   1.00    1.00    --   36.36 -57.00 150.00   84
  4  ω      7.00 108.00   1.00    1.00    --   36.36  19.00  90.00  101
  5  ω     23.00  90.00   1.00    1.00    --   36.36-125.00 -30.00   67
  6  ω    -33.00 106.00   1.00    1.00    --   36.36   0.00  30.00  139
  7  ω     20.00 104.00   1.00    1.00    --   36.36  57.00-150.00   84
  8  ω    -31.00  53.00   1.00    1.00    --   36.36 -57.00  90.00   84
  9  ω     23.00  90.00   1.00    1.00    --   36.36-125.00   0.00   67
 10  ω     23.00  90.00   1.00    1.00    --   36.36-125.00  30.00   67
 11  ω      1.00  75.00   1.00    1.00    --   36.36 -99.00 -30.00   74
 12  ω     20.00 104.00   1.00    1.00    --   36.36  57.00 150.00   84
 13  ω     17.00 105.00   1.00    1.00    --   36.36  38.00  90.00   88
 14  ω     20.00 104.00   1.00    1.00    --   36.36  57.00 -30.00   84
 15  ω     17.00 105.00   1.00    1.00    --   36.36  38.00-120.00   88
 16  ω    -33.00  55.00   1.00    1.00    --   36.36 -38.00 150.00   88
 17  ω     10.00 104.00   1.00    1.00    --   36.36  77.00 -30.00   94
 18  ω     23.00  90.00   1.00    1.00    --   36.36-125.00 150.00   67
 19  ω     10.00 104.00   1.00    1.00    --   36.36  77.00  60.00   94
 20  ω    -33.00  55.00   1.00    1.00    --   36.36 -38.00  30.00   88
 21  ω     20.00 104.00   1.00    1.00    --   36.36  57.00 120.00   84
 22  ω      7.00 108.00   1.00    1.00    --   36.36  19.00 120.00  101
 23  ω     71.00 178.00   1.00    4.00    --  109.31  15.00 120.00  107
 24  ω     88.00 178.00   1.00    4.00    --  109.31  30.00  30.00   90
 25  ω     42.00 136.00   1.00    4.00    --  109.31 -77.00-120.00   94
 26  ω     91.00 176.00   1.00    4.00    --  109.31  61.00  30.00   85
 27  ω     92.00 178.00   1.00    4.00    --  109.31  45.00   0.00   86
 28  ω     83.00 177.00   1.00    4.00    --  109.31  77.00   0.00   94
 29  ω     92.00 178.00   1.00    4.00    --  109.31  45.00  60.00   86
 30  ω     92.00 178.00   1.00    4.00    --  109.31  45.00  30.00   86
 31  ω     71.00 178.00   1.00    4.00    --  109.31  15.00  60.00  107
 32  ω    100.00 178.00   1.00    4.00    --  109.31 111.00-120.00   78
 33  ω     83.00 177.00   1.00    4.00    --  109.31  77.00  60.00   94
 34  ω     88.00 178.00   1.00    4.00    --  109.31  30.00  60.00   90
 35  ω     91.00 176.00   1.00    4.00    --  109.31  61.00  90.00   85
 36  ω     91.00 176.00   1.00    4.00    --  109.31  61.00   0.00   85
 37  ω     42.00 136.00   1.00    4.00    --  109.31 -77.00  30.00   94
 38  ω     88.00 178.00   1.00    4.00    --  109.31  30.00  90.00   90
 39  ω     83.00 177.00   1.00    4.00    --  109.31  77.00  30.00   94
 40  ω     88.00 178.00   1.00    4.00    --  109.31  30.00 -30.00   90
 41  ω     83.00 177.00   1.00    4.00    --  109.31  77.00 -30.00   94
 42  ω    100.00 178.00   1.00    4.00    --  109.31 111.00-180.00   78
 43  ω     92.00 178.00   1.00    4.00    --  109.31  45.00 -30.00   86
 44  ω     91.00 176.00   1.00    4.00    --  109.31  61.00  60.00   85
 45  ω     88.00 178.00   1.00    4.00    --  109.31  30.00 120.00   90
 46  ω     92.00 178.00   1.00    4.00    --  109.31  45.00  90.00   86
 47  ω     91.00 176.00   1.00    4.00    --  109.31  61.00 -30.00   85
 48  ω     88.00 178.00   1.00    4.00    --  109.31  30.00   0.00   90
 49  ω     71.00 178.00   1.00    4.00    --  109.31  15.00  30.00  107
 50  ω     83.00 177.00   1.00    4.00    --  109.31  77.00 150.00   94
 51  ω    100.00 178.00   1.00    4.00    --  109.31 111.00 -30.00   78
 52  ω     23.00  90.00   1.00    1.00    --   36.36-125.00-180.00   67
 53  ω    -33.00  55.00   1.00    1.00    --   36.36 -38.00  90.00   88
 54  ω     17.00 105.00   1.00    1.00    --   36.36  38.00 -90.00   88
 55  ω     20.00 104.00   1.00    1.00    --   36.36  57.00 -90.00   84
 56  ω     10.00 104.00   1.00    1.00    --   36.36  77.00-150.00   94
 57  ω     17.00 105.00   1.00    1.00    --   36.36  38.00 120.00   88
 58  ω     23.00  90.00   1.00    1.00    --   36.36-125.00  90.00   67
 59  ω     20.00 104.00   1.00    1.00    --   36.36  57.00 -60.00   84
 60  ω      7.00 108.00   1.00    1.00    --   36.36  19.00-150.00  101
 61  ω     23.00  90.00   1.00    1.00    --   36.36-125.00 -90.00   67
 62  ω    -31.00  53.00   1.00    1.00    --   36.36 -57.00   0.00   84
 63  ω    -33.00  55.00   1.00    1.00    --   36.36 -38.00 -90.00   88
 64  ω     17.00 105.00   1.00    1.00    --   36.36  38.00 -68.00   88
 65  ω    -31.00  53.00   1.00    1.00    --   36.36 -57.00-120.00   84
 66  ω    -18.00  66.00   1.00    1.00    --   36.36 -83.00 -28.00   84
 67  ω     10.00 104.00   1.00    1.00    --   36.36  77.00-120.00   94
 68  ω      7.00 108.00   1.00    1.00    --   36.36  19.00 -90.00  101
 69  ω    -33.00  55.00   1.00    1.00    --   36.36 -38.00 120.00   88
 70  ω     10.00 104.00   1.00    1.00    --   36.36  77.00 -90.00   94
 71  ω    -31.00  53.00   1.00    1.00    --   36.36 -57.00 120.00   84
 72  ω     20.00 104.00   1.00    1.00    --   36.36  57.00-180.00   84
 73  ω     23.00  90.00   1.00    1.00    --   36.36-125.00-120.00   67
 74  ω     10.00 104.00   1.00    1.00    --   36.36  77.00  30.00   94
 75  ω     10.00 104.00   1.00    1.00    --   36.36  77.00 150.00   94
 76  ω      1.00  75.00   1.00    1.00    --   36.36 -99.00 150.00   74
 77  ω    -31.00  53.00   1.00    1.00    --   36.36 -57.00-180.00   84
 78  ω     88.00 178.00   1.00    4.00    --  109.31  30.00-150.00   90
 79  ω     39.00 116.00   1.00    4.00    --  109.31-111.00-180.00   77
 80  ω     90.00 178.00   1.00    4.00    --  109.31  38.00 -68.00   88
 81  ω     88.00 178.00   1.00    4.00    --  109.31  30.00 -90.00   90
 82  ω     88.00 178.00   1.00    4.00    --  109.31  30.00-120.00   90
 83  ω     88.00 178.00   1.00    4.00    --  109.31  30.00 150.00   90
 84  ω     91.00 176.00   1.00    4.00    --  109.31  61.00-180.00   85
 85  ω     39.00 116.00   1.00    4.00    --  109.31-111.00  30.00   77
 86  ω     91.00 176.00   1.00    4.00    --  109.31  61.00-120.00   85
 87  ω     71.00 178.00   1.00    4.00    --  109.31  15.00 -30.00  107
 88  ω     83.00 177.00   1.00    4.00    --  109.31  77.00 -60.00   94
 89  ω     91.00 176.00   1.00    4.00    --  109.31  61.00 120.00   85
 90  ω     91.00 176.00   1.00    4.00    --  109.31  61.00 -60.00   85
 91  ω     40.00 109.00   1.00    4.00    --  109.31 -95.00-150.00   69
 92  ω     83.00 177.00   1.00    4.00    --  109.31  77.00 -90.00   94
 93  ω     91.00 176.00   1.00    4.00    --  109.31  61.00-150.00   85
 94  ω     88.00 178.00   1.00    4.00    --  109.31  30.00-180.00   90
 95  ω     83.00 177.00   1.00    4.00    --  109.31  77.00-120.00   94
 96  ω     83.00 177.00   1.00    4.00    --  109.31  77.00-180.00   94
 97  ω     91.00 176.00   1.00    4.00    --  109.31  61.00 150.00   85
 98  ω     92.00 178.00   1.00    4.00    --  109.31  45.00 120.00   86
 99  ω     83.00 177.00   1.00    4.00    --  109.31  77.00-150.00   94
100  ω     40.00 109.00   1.00    4.00    --  109.31 -95.00 -30.00   69
101  ω     83.00 177.00   1.00    4.00    --  109.31  77.00 120.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0454283000
_diffrn_orient_matrix_UB_12      -0.0667024000
_diffrn_orient_matrix_UB_13      0.0255131000
_diffrn_orient_matrix_UB_21      -0.0290525000
_diffrn_orient_matrix_UB_22      -0.0460550000
_diffrn_orient_matrix_UB_23      -0.0618476000
_diffrn_orient_matrix_UB_31      0.0277883000
_diffrn_orient_matrix_UB_32      -0.1543560000
_diffrn_orient_matrix_UB_33      0.0066944000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.761
_reflns_Friedel_fraction_full    0.877
_reflns_Friedel_fraction_max     0.877
_reflns_number_gt                8381
_reflns_number_total             8872
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.511
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details 
;
 Flack x determined using 3330 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.003(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     637
_refine_ls_number_reflns         8872
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0641
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1148P)²+4.4232P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1749
_refine_ls_wR_factor_ref         0.1781
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C1(H1), C45(H45), C36(H36)
2.b Secondary CH2 refined with riding coordinates:
 C47(H47A,H47B), C2(H2A,H2B), C50(H50A,H50B), C16(H16A,H16B), C51(H51A,H51B),
 C15(H15A,H15B), C25(H25A,H25B), C60(H60A,H60B)
2.c Aromatic/amide H refined with riding coordinates:
 C22(H22), C57(H57), C41(H41), C21(H21), C56(H56), C8(H8)
2.d Idealised Me refined as rotating group:
 C34(H34A,H34B,H34C), C30(H30A,H30B,H30C), C65(H65A,H65B,H65C), C61(H61A,H61B,
 H61C), C69(H69A,H69B,H69C), C26(H26A,H26B,H26C)
;
_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
Cl20 Cl 0.33604(4) 0.02628(17) 0.98988(6) 0.0538(3) Uani 1 1 d . . . . .
Cl55 Cl 0.66235(4) 0.44886(17) 0.50268(6) 0.0562(4) Uani 1 1 d . . . . .
O54 O 0.55682(11) 0.9639(4) 0.47812(14) 0.0451(8) Uani 1 1 d . . . . .
O19 O 0.44152(11) 0.5372(4) 1.01576(13) 0.0439(7) Uani 1 1 d . . . . .
O33 O 0.43720(15) 0.2697(5) 0.77672(15) 0.0555(9) Uani 1 1 d . . . . .
N37 N 0.58142(12) 0.6960(4) 0.54647(14) 0.0304(7) Uani 1 1 d . . . . .
N5 N 0.48930(12) 0.1961(5) 0.90812(14) 0.0330(7) Uani 1 1 d . . . . .
N42 N 0.51955(14) 0.3547(5) 0.57811(17) 0.0407(9) Uani 1 1 d . . . . .
N12 N 0.41879(12) 0.2685(4) 0.94791(14) 0.0296(7) Uani 1 1 d . . . . .
N44 N 0.51407(12) 0.6240(5) 0.59215(15) 0.0335(8) Uani 1 1 d . . . . .
O68 O 0.57713(17) 0.7020(6) 0.72307(16) 0.0690(13) Uani 1 1 d . . . . .
O66 O 0.50693(14) 0.9621(6) 0.65972(17) 0.0627(11) Uani 1 1 d . . . . .
O31 O 0.50240(14) 0.5398(6) 0.84714(17) 0.0630(11) Uani 1 1 d . . . . .
O24 O 0.64449(14) 0.0093(6) 0.85469(19) 0.0675(12) Uani 1 1 d . . . . .
O29 O 0.42323(16) 0.6148(5) 0.79976(17) 0.0587(10) Uani 1 1 d . . . . .
N7 N 0.48250(15) -0.0716(5) 0.92189(17) 0.0421(9) Uani 1 1 d . . . . .
O64 O 0.58859(16) 1.0488(5) 0.69265(17) 0.0636(11) Uani 1 1 d . . . . .
N48 N 0.63911(13) 0.8628(5) 0.50637(15) 0.0377(8) Uani 1 1 d . . . . .
O59 O 0.35949(13) 0.4454(5) 0.64941(19) 0.0633(11) Uani 1 1 d . . . . .
O27 O 0.63713(16) 0.2603(6) 0.8654(2) 0.0776(14) Uani 1 1 d . . . . .
N13 N 0.35934(13) 0.4391(5) 0.98363(16) 0.0373(8) Uani 1 1 d . . . . .
N9 N 0.40858(15) -0.1480(5) 0.96173(19) 0.0460(9) Uani 1 1 d . . . . .
O62 O 0.36839(16) 0.6931(6) 0.6394(2) 0.0760(14) Uani 1 1 d . . . . .
N40 N 0.59092(15) 0.2747(5) 0.53382(19) 0.0482(10) Uani 1 1 d . . . . .
O35 O 0.36895(19) 0.2047(7) 0.81622(19) 0.0830(16) Uani 1 1 d . . . . .
O53 O 0.72693(14) 0.8073(7) 0.5180(2) 0.0880(17) Uani 1 1 d . . . . .
O18 O 0.27145(14) 0.3809(7) 0.9700(2) 0.0846(17) Uani 1 1 d . . . . .
C47 C 0.62540(15) 0.8927(6) 0.60708(18) 0.0390(10) Uani 1 1 d . . . . .
H47A H 0.616557 0.992781 0.591260 0.047 Uiso 1 1 calc R . . . .
H47B H 0.658008 0.898664 0.635431 0.047 Uiso 1 1 calc R . . . .
C28 C 0.45528(18) 0.5245(6) 0.83525(18) 0.0399(9) Uani 1 1 d . . . . .
C6 C 0.46615(14) 0.0670(5) 0.92463(17) 0.0314(9) Uani 1 1 d . . . . .
O70 O 0.6385(2) 0.6278(8) 0.6749(2) 0.096(2) Uani 1 1 d . . . . .
C38 C 0.57926(14) 0.5389(5) 0.54879(16) 0.0294(8) Uani 1 1 d . . . . .
C63 C 0.55361(18) 0.9528(6) 0.66376(18) 0.0430(10) Uani 1 1 d . . . . .
C32 C 0.40655(18) 0.2819(6) 0.81539(18) 0.0414(10) Uani 1 1 d . . . . .
C11 C 0.42094(14) 0.1118(6) 0.94671(16) 0.0319(9) Uani 1 1 d . . . . .
C4 C 0.45810(14) 0.3289(5) 0.91625(16) 0.0283(8) Uani 1 1 d . . . . .
H4 H 0.480067 0.404745 0.939964 0.034 Uiso 1 1 calc R . . . .
C67 C 0.60290(19) 0.7068(7) 0.67985(18) 0.0488(12) Uani 1 1 d . . . . .
C43 C 0.53598(15) 0.4953(6) 0.57379(17) 0.0342(10) Uani 1 1 d . . . . .
C10 C 0.39280(16) -0.0039(6) 0.96383(18) 0.0361(9) Uani 1 1 d . . . . .
C17 C 0.39580(16) 0.5269(6) 1.02014(18) 0.0373(9) Uani 1 1 d . . . . .
C22 C 0.56932(16) 0.0970(6) 0.8830(2) 0.0431(11) Uani 1 1 d . . . . .
H22 H 0.559599 -0.003404 0.886221 0.052 Uiso 1 1 calc R . . . .
C1 C 0.37017(14) 0.3564(5) 0.93350(17) 0.0343(9) Uani 1 1 d . . . . .
H1 H 0.340759 0.288494 0.918764 0.041 Uiso 1 1 calc R . . . .
C45 C 0.54459(14) 0.7553(5) 0.58179(16) 0.0296(8) Uani 1 1 d . . . . .
H45 H 0.521615 0.831665 0.559652 0.036 Uiso 1 1 calc R . . . .
C57 C 0.43539(16) 0.5273(6) 0.6211(2) 0.0415(10) Uani 1 1 d . . . . .
H57 H 0.445065 0.426730 0.618354 0.050 Uiso 1 1 calc R . . . .
C52 C 0.60208(16) 0.9520(6) 0.47172(18) 0.0391(10) Uani 1 1 d . . . . .
C58 C 0.38521(17) 0.5674(7) 0.6374(2) 0.0481(12) Uani 1 1 d . . . . .
C36 C 0.63070(14) 0.7810(5) 0.55816(17) 0.0326(9) Uani 1 1 d . . . . .
H36 H 0.660148 0.712094 0.571499 0.039 Uiso 1 1 calc R . . . .
C41 C 0.54824(18) 0.2518(6) 0.5559(2) 0.0486(11) Uani 1 1 d . . . . .
H41 H 0.536736 0.152209 0.555973 0.058 Uiso 1 1 calc R . . . .
C21 C 0.53834(15) 0.2092(6) 0.89242(17) 0.0375(10) Uani 1 1 d . . . . .
H21 H 0.550460 0.306679 0.888143 0.045 Uiso 1 1 calc R . . . .
C23 C 0.61974(19) 0.1372(8) 0.8672(2) 0.0525(13) Uani 1 1 d . . . . .
C56 C 0.46644(14) 0.6381(6) 0.61042(17) 0.0343(9) Uani 1 1 d . . . . .
H56 H 0.455165 0.735983 0.615713 0.041 Uiso 1 1 calc R . . . .
C2 C 0.37806(16) 0.4663(6) 0.88480(18) 0.0375(9) Uani 1 1 d . . . . .
H2A H 0.385602 0.567367 0.900285 0.045 Uiso 1 1 calc R . . . .
H2B H 0.346815 0.470103 0.854380 0.045 Uiso 1 1 calc R . . . .
C39 C 0.60658(16) 0.4210(6) 0.53052(19) 0.0414(11) Uani 1 1 d . . . . .
C3 C 0.42519(15) 0.4033(5) 0.86058(17) 0.0348(9) Uani 1 1 d . . . . .
C46 C 0.58103(15) 0.8300(6) 0.63549(16) 0.0362(10) Uani 1 1 d . . . . .
C8 C 0.45232(18) -0.1732(6) 0.9419(2) 0.0482(12) Uani 1 1 d . . . . .
H8 H 0.463251 -0.273333 0.941872 0.058 Uiso 1 1 calc R . . . .
C49 C 0.68881(18) 0.8737(7) 0.4922(2) 0.0547(14) Uani 1 1 d . . . . .
C14 C 0.30906(19) 0.4474(7) 0.9965(2) 0.0526(13) Uani 1 1 d . . . . .
C50 C 0.6846(2) 0.9803(9) 0.4419(3) 0.0698(19) Uani 1 1 d . . . . .
H50A H 0.695272 0.930945 0.409018 0.084 Uiso 1 1 calc R . . . .
H50B H 0.706723 1.068085 0.452716 0.084 Uiso 1 1 calc R . . . .
C16 C 0.3687(2) 0.6010(8) 1.0644(2) 0.0564(14) Uani 1 1 d . . . . .
H16A H 0.370864 0.710227 1.062155 0.068 Uiso 1 1 calc R . . . .
H16B H 0.384359 0.569038 1.103620 0.068 Uiso 1 1 calc R . . . .
C51 C 0.6280(2) 1.0256(7) 0.4268(2) 0.0542(13) Uani 1 1 d . . . . .
H51A H 0.612281 0.990850 0.387988 0.065 Uiso 1 1 calc R . . . .
H51B H 0.624548 1.134719 0.428156 0.065 Uiso 1 1 calc R . . . .
C15 C 0.3123(2) 0.5489(10) 1.0484(3) 0.0697(18) Uani 1 1 d . . . . .
H15A H 0.302381 0.494407 1.080629 0.084 Uiso 1 1 calc R . . . .
H15B H 0.288991 0.634811 1.038902 0.084 Uiso 1 1 calc R . . . .
C34 C 0.4234(3) 0.1571(9) 0.7318(3) 0.080(2) Uani 1 1 d . . . . .
H34A H 0.389554 0.180487 0.708667 0.120 Uiso 1 1 calc GR . . . .
H34B H 0.422139 0.059448 0.749443 0.120 Uiso 1 1 calc GR . . . .
H34C H 0.449183 0.156313 0.707415 0.120 Uiso 1 1 calc GR . . . .
C25 C 0.6958(2) 0.0307(11) 0.8401(3) 0.085(2) Uani 1 1 d . . . . .
H25A H 0.720399 0.066891 0.873957 0.102 Uiso 1 1 calc R . . . .
H25B H 0.693702 0.105019 0.809258 0.102 Uiso 1 1 calc R . . . .
C30 C 0.4481(3) 0.7350(8) 0.7737(3) 0.079(2) Uani 1 1 d . . . . .
H30A H 0.422003 0.789482 0.746724 0.118 Uiso 1 1 calc GR . . . .
H30B H 0.473541 0.693178 0.753335 0.118 Uiso 1 1 calc GR . . . .
H30C H 0.465180 0.802428 0.803570 0.118 Uiso 1 1 calc GR . . . .
C65 C 0.5673(4) 1.1686(11) 0.7217(3) 0.091(3) Uani 1 1 d . . . . .
H65A H 0.541969 1.223452 0.694046 0.137 Uiso 1 1 calc GR . . . .
H65B H 0.595058 1.235561 0.739125 0.137 Uiso 1 1 calc GR . . . .
H65C H 0.550618 1.127341 0.751470 0.137 Uiso 1 1 calc GR . . . .
C61 C 0.2844(3) 0.3233(15) 0.6725(4) 0.115(4) Uani 1 1 d . . . . .
H61A H 0.282627 0.260515 0.638685 0.172 Uiso 1 1 calc GR . . . .
H61B H 0.249596 0.339176 0.679750 0.172 Uiso 1 1 calc GR . . . .
H61C H 0.305489 0.274478 0.705652 0.172 Uiso 1 1 calc GR . . . .
C60 C 0.3078(2) 0.4684(11) 0.6626(4) 0.093(3) Uani 1 1 d . . . . .
H60A H 0.285587 0.520281 0.630448 0.111 Uiso 1 1 calc R . . . .
H60B H 0.310502 0.531010 0.697169 0.111 Uiso 1 1 calc R . . . .
C69 C 0.5954(3) 0.5905(13) 0.7678(3) 0.107(3) Uani 1 1 d . . . . .
H69A H 0.575258 0.499396 0.759234 0.161 Uiso 1 1 calc GR . . . .
H69B H 0.591160 0.629040 0.804979 0.161 Uiso 1 1 calc GR . . . .
H69C H 0.631808 0.569216 0.768685 0.161 Uiso 1 1 calc GR . . . .
C26 C 0.7137(3) -0.1155(13) 0.8208(5) 0.112(4) Uani 1 1 d . . . . .
H26A H 0.688240 -0.153051 0.788597 0.168 Uiso 1 1 calc GR . . . .
H26B H 0.717820 -0.186564 0.852396 0.168 Uiso 1 1 calc GR . . . .
H26C H 0.746788 -0.101965 0.808825 0.168 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl20 C10 1.720(4) . ?
Cl55 C39 1.715(4) . ?
O54 C52 1.217(5) . ?
O19 C17 1.214(5) . ?
O33 C32 1.318(6) . ?
O33 C34 1.441(7) . ?
N37 C38 1.392(6) . ?
N37 C45 1.475(4) . ?
N37 C36 1.463(5) . ?
N5 C6 1.380(6) . ?
N5 C4 1.459(5) . ?
N5 C21 1.396(5) . ?
N42 C43 1.325(6) . ?
N42 C41 1.343(6) . ?
N12 C11 1.388(6) . ?
N12 C4 1.471(4) . ?
N12 C1 1.465(5) . ?
N44 C43 1.378(6) . ?
N44 C45 1.452(5) . ?
N44 C56 1.389(4) . ?
O68 C67 1.315(6) . ?
O68 C69 1.448(9) . ?
O66 C63 1.199(6) . ?
O31 C28 1.208(6) . ?
O24 C23 1.360(8) . ?
O24 C25 1.448(6) . ?
O29 C28 1.323(6) . ?
O29 C30 1.438(7) . ?
N7 C6 1.303(6) . ?
N7 C8 1.334(7) . ?
O64 C63 1.328(6) . ?
O64 C65 1.426(9) . ?
N48 C52 1.379(6) . ?
N48 C36 1.462(5) . ?
N48 C49 1.395(5) . ?
O59 C58 1.327(7) . ?
O59 C60 1.448(6) . ?
O27 C23 1.183(8) . ?
N13 C17 1.384(6) . ?
N13 C1 1.453(5) . ?
N13 C14 1.397(5) . ?
N9 C10 1.343(7) . ?
N9 C8 1.325(6) . ?
O62 C58 1.199(8) . ?
N40 C41 1.324(6) . ?
N40 C39 1.363(7) . ?
O35 C32 1.194(7) . ?
O53 C49 1.206(7) . ?
O18 C14 1.204(8) . ?
C47 H47A 0.9700 . ?
C47 H47B 0.9700 . ?
C47 C36 1.537(6) . ?
C47 C46 1.539(5) . ?
C28 C3 1.513(6) . ?
C6 C11 1.426(5) . ?
O70 C67 1.180(7) . ?
C38 C43 1.416(5) . ?
C38 C39 1.374(6) . ?
C63 C46 1.517(6) . ?
C32 C3 1.518(6) . ?
C11 C10 1.361(6) . ?
C4 H4 0.9800 . ?
C4 C3 1.557(5) . ?
C67 C46 1.536(7) . ?
C17 C16 1.509(6) . ?
C22 H22 0.9300 . ?
C22 C21 1.322(7) . ?
C22 C23 1.470(6) . ?
C1 H1 0.9800 . ?
C1 C2 1.540(6) . ?
C45 H45 0.9800 . ?
C45 C46 1.564(6) . ?
C57 H57 0.9300 . ?
C57 C58 1.469(5) . ?
C57 C56 1.322(7) . ?
C52 C51 1.501(6) . ?
C36 H36 0.9800 . ?
C41 H41 0.9300 . ?
C21 H21 0.9300 . ?
C56 H56 0.9300 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.547(5) . ?
C8 H8 0.9300 . ?
C49 C50 1.494(9) . ?
C14 C15 1.498(9) . ?
C50 H50A 0.9700 . ?
C50 H50B 0.9700 . ?
C50 C51 1.497(8) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C15 1.510(9) . ?
C51 H51A 0.9700 . ?
C51 H51B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 C26 1.474(13) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C65 H65A 0.9600 . ?
C65 H65B 0.9600 . ?
C65 H65C 0.9600 . ?
C61 H61A 0.9600 . ?
C61 H61B 0.9600 . ?
C61 H61C 0.9600 . ?
C61 C60 1.458(14) . ?
C60 H60A 0.9700 . ?
C60 H60B 0.9700 . ?
C69 H69A 0.9600 . ?
C69 H69B 0.9600 . ?
C69 H69C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?

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
C32 O33 C34 117.2(5) . . ?
C38 N37 C45 107.3(3) . . ?
C38 N37 C36 123.1(3) . . ?
C36 N37 C45 110.5(3) . . ?
C6 N5 C4 110.3(3) . . ?
C6 N5 C21 127.6(4) . . ?
C21 N5 C4 121.6(4) . . ?
C43 N42 C41 113.3(4) . . ?
C11 N12 C4 108.5(3) . . ?
C11 N12 C1 124.2(3) . . ?
C1 N12 C4 110.0(3) . . ?
C43 N44 C45 109.7(3) . . ?
C43 N44 C56 128.0(4) . . ?
C56 N44 C45 121.7(4) . . ?
C67 O68 C69 115.6(6) . . ?
C23 O24 C25 115.8(6) . . ?
C28 O29 C30 115.7(5) . . ?
C6 N7 C8 113.4(4) . . ?
C63 O64 C65 115.3(5) . . ?
C52 N48 C36 124.8(3) . . ?
C52 N48 C49 113.1(4) . . ?
C49 N48 C36 121.5(4) . . ?
C58 O59 C60 117.1(5) . . ?
C17 N13 C1 124.3(3) . . ?
C17 N13 C14 113.1(4) . . ?
C14 N13 C1 122.3(4) . . ?
C8 N9 C10 117.4(4) . . ?
C41 N40 C39 116.6(4) . . ?
H47A C47 H47B 108.7 . . ?
C36 C47 H47A 110.6 . . ?
C36 C47 H47B 110.6 . . ?
C36 C47 C46 105.8(4) . . ?
C46 C47 H47A 110.6 . . ?
C46 C47 H47B 110.6 . . ?
O31 C28 O29 124.2(5) . . ?
O31 C28 C3 124.4(4) . . ?
O29 C28 C3 111.3(4) . . ?
N5 C6 C11 107.7(4) . . ?
N7 C6 N5 127.0(4) . . ?
N7 C6 C11 125.3(4) . . ?
N37 C38 C43 109.2(4) . . ?
C39 C38 N37 135.9(4) . . ?
C39 C38 C43 114.8(4) . . ?
O66 C63 O64 125.2(5) . . ?
O66 C63 C46 124.5(5) . . ?
O64 C63 C46 110.3(4) . . ?
O33 C32 C3 112.4(4) . . ?
O35 C32 O33 124.5(5) . . ?
O35 C32 C3 123.0(4) . . ?
N12 C11 C6 108.9(4) . . ?
C10 C11 N12 136.0(4) . . ?
C10 C11 C6 115.0(4) . . ?
N5 C4 N12 103.3(3) . . ?
N5 C4 H4 110.4 . . ?
N5 C4 C3 117.4(3) . . ?
N12 C4 H4 110.4 . . ?
N12 C4 C3 104.6(3) . . ?
C3 C4 H4 110.4 . . ?
O68 C67 C46 111.4(5) . . ?
O70 C67 O68 125.4(5) . . ?
O70 C67 C46 123.2(4) . . ?
N42 C43 N44 126.4(4) . . ?
N42 C43 C38 125.4(4) . . ?
N44 C43 C38 108.2(4) . . ?
N9 C10 Cl20 116.6(3) . . ?
N9 C10 C11 121.2(4) . . ?
C11 C10 Cl20 122.2(4) . . ?
O19 C17 N13 123.6(4) . . ?
O19 C17 C16 128.2(5) . . ?
N13 C17 C16 108.2(4) . . ?
C21 C22 H22 121.3 . . ?
C21 C22 C23 117.4(5) . . ?
C23 C22 H22 121.3 . . ?
N12 C1 H1 109.4 . . ?
N12 C1 C2 105.9(3) . . ?
N13 C1 N12 112.0(3) . . ?
N13 C1 H1 109.4 . . ?
N13 C1 C2 110.6(4) . . ?
C2 C1 H1 109.4 . . ?
N37 C45 H45 110.1 . . ?
N37 C45 C46 104.1(3) . . ?
N44 C45 N37 104.0(3) . . ?
N44 C45 H45 110.1 . . ?
N44 C45 C46 118.0(3) . . ?
C46 C45 H45 110.1 . . ?
C58 C57 H57 120.9 . . ?
C56 C57 H57 120.9 . . ?
C56 C57 C58 118.2(5) . . ?
O54 C52 N48 123.8(4) . . ?
O54 C52 C51 128.5(5) . . ?
N48 C52 C51 107.7(4) . . ?
O59 C58 C57 111.4(5) . . ?
O62 C58 O59 123.0(4) . . ?
O62 C58 C57 125.5(5) . . ?
N37 C36 C47 105.6(3) . . ?
N37 C36 H36 109.8 . . ?
N48 C36 N37 111.4(3) . . ?
N48 C36 C47 110.3(4) . . ?
N48 C36 H36 109.8 . . ?
C47 C36 H36 109.8 . . ?
N42 C41 H41 116.0 . . ?
N40 C41 N42 127.9(5) . . ?
N40 C41 H41 116.0 . . ?
N5 C21 H21 116.7 . . ?
C22 C21 N5 126.6(5) . . ?
C22 C21 H21 116.7 . . ?
O24 C23 C22 109.4(5) . . ?
O27 C23 O24 124.0(4) . . ?
O27 C23 C22 126.6(5) . . ?
N44 C56 H56 116.5 . . ?
C57 C56 N44 127.0(4) . . ?
C57 C56 H56 116.5 . . ?
C1 C2 H2A 110.6 . . ?
C1 C2 H2B 110.6 . . ?
C1 C2 C3 105.7(3) . . ?
H2A C2 H2B 108.7 . . ?
C3 C2 H2A 110.6 . . ?
C3 C2 H2B 110.6 . . ?
N40 C39 Cl55 116.1(3) . . ?
N40 C39 C38 121.7(4) . . ?
C38 C39 Cl55 122.2(4) . . ?
C28 C3 C32 110.4(3) . . ?
C28 C3 C4 112.7(3) . . ?
C28 C3 C2 113.1(4) . . ?
C32 C3 C4 109.4(4) . . ?
C32 C3 C2 110.0(4) . . ?
C2 C3 C4 101.0(3) . . ?
C47 C46 C45 101.1(3) . . ?
C63 C46 C47 112.5(4) . . ?
C63 C46 C67 110.9(4) . . ?
C63 C46 C45 113.0(3) . . ?
C67 C46 C47 109.7(4) . . ?
C67 C46 C45 109.2(4) . . ?
N7 C8 H8 116.2 . . ?
N9 C8 N7 127.6(5) . . ?
N9 C8 H8 116.2 . . ?
N48 C49 C50 107.4(5) . . ?
O53 C49 N48 123.6(5) . . ?
O53 C49 C50 128.9(4) . . ?
N13 C14 C15 107.3(5) . . ?
O18 C14 N13 124.1(5) . . ?
O18 C14 C15 128.5(5) . . ?
C49 C50 H50A 110.5 . . ?
C49 C50 H50B 110.5 . . ?
C49 C50 C51 105.9(4) . . ?
H50A C50 H50B 108.7 . . ?
C51 C50 H50A 110.5 . . ?
C51 C50 H50B 110.5 . . ?
C17 C16 H16A 110.8 . . ?
C17 C16 H16B 110.8 . . ?
C17 C16 C15 104.8(5) . . ?
H16A C16 H16B 108.9 . . ?
C15 C16 H16A 110.8 . . ?
C15 C16 H16B 110.8 . . ?
C52 C51 H51A 110.6 . . ?
C52 C51 H51B 110.6 . . ?
C50 C51 C52 105.7(4) . . ?
C50 C51 H51A 110.6 . . ?
C50 C51 H51B 110.6 . . ?
H51A C51 H51B 108.7 . . ?
C14 C15 C16 106.5(4) . . ?
C14 C15 H15A 110.4 . . ?
C14 C15 H15B 110.4 . . ?
C16 C15 H15A 110.4 . . ?
C16 C15 H15B 110.4 . . ?
H15A C15 H15B 108.6 . . ?
O33 C34 H34A 109.5 . . ?
O33 C34 H34B 109.5 . . ?
O33 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
O24 C25 H25A 110.0 . . ?
O24 C25 H25B 110.0 . . ?
O24 C25 C26 108.5(7) . . ?
H25A C25 H25B 108.4 . . ?
C26 C25 H25A 110.0 . . ?
C26 C25 H25B 110.0 . . ?
O29 C30 H30A 109.5 . . ?
O29 C30 H30B 109.5 . . ?
O29 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
O64 C65 H65A 109.5 . . ?
O64 C65 H65B 109.5 . . ?
O64 C65 H65C 109.5 . . ?
H65A C65 H65B 109.5 . . ?
H65A C65 H65C 109.5 . . ?
H65B C65 H65C 109.5 . . ?
H61A C61 H61B 109.5 . . ?
H61A C61 H61C 109.5 . . ?
H61B C61 H61C 109.5 . . ?
C60 C61 H61A 109.5 . . ?
C60 C61 H61B 109.5 . . ?
C60 C61 H61C 109.5 . . ?
O59 C60 C61 110.0(7) . . ?
O59 C60 H60A 109.7 . . ?
O59 C60 H60B 109.7 . . ?
C61 C60 H60A 109.7 . . ?
C61 C60 H60B 109.7 . . ?
H60A C60 H60B 108.2 . . ?
O68 C69 H69A 109.5 . . ?
O68 C69 H69B 109.5 . . ?
O68 C69 H69C 109.5 . . ?
H69A C69 H69B 109.5 . . ?
H69A C69 H69C 109.5 . . ?
H69B C69 H69C 109.5 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O54 C52 C51 C50 176.0(5) . . . . ?
O19 C17 C16 C15 179.5(5) . . . . ?
O33 C32 C3 C28 27.6(5) . . . . ?
O33 C32 C3 C4 -96.9(4) . . . . ?
O33 C32 C3 C2 153.0(4) . . . . ?
N37 C38 C43 N42 173.9(4) . . . . ?
N37 C38 C43 N44 -5.6(4) . . . . ?
N37 C38 C39 Cl55 7.7(7) . . . . ?
N37 C38 C39 N40 -172.6(4) . . . . ?
N37 C45 C46 C47 35.0(4) . . . . ?
N37 C45 C46 C63 155.5(4) . . . . ?
N37 C45 C46 C67 -80.6(4) . . . . ?
N5 C6 C11 N12 -4.6(4) . . . . ?
N5 C6 C11 C10 178.6(3) . . . . ?
N5 C4 C3 C28 -90.1(4) . . . . ?
N5 C4 C3 C32 33.1(4) . . . . ?
N5 C4 C3 C2 149.0(4) . . . . ?
N12 C11 C10 Cl20 6.1(7) . . . . ?
N12 C11 C10 N9 -173.1(4) . . . . ?
N12 C4 C3 C28 156.2(4) . . . . ?
N12 C4 C3 C32 -80.6(4) . . . . ?
N12 C4 C3 C2 35.3(4) . . . . ?
N12 C1 C2 C3 16.6(5) . . . . ?
N44 C45 C46 C47 149.5(4) . . . . ?
N44 C45 C46 C63 -90.0(5) . . . . ?
N44 C45 C46 C67 33.9(5) . . . . ?
O68 C67 C46 C47 149.3(5) . . . . ?
O68 C67 C46 C63 24.4(6) . . . . ?
O68 C67 C46 C45 -100.8(5) . . . . ?
O66 C63 C46 C47 136.5(5) . . . . ?
O66 C63 C46 C67 -100.2(6) . . . . ?
O66 C63 C46 C45 22.8(7) . . . . ?
O31 C28 C3 C32 -106.1(5) . . . . ?
O31 C28 C3 C4 16.5(7) . . . . ?
O31 C28 C3 C2 130.2(5) . . . . ?
O29 C28 C3 C32 75.9(5) . . . . ?
O29 C28 C3 C4 -161.5(4) . . . . ?
O29 C28 C3 C2 -47.8(5) . . . . ?
N7 C6 C11 N12 174.3(4) . . . . ?
N7 C6 C11 C10 -2.5(6) . . . . ?
O64 C63 C46 C47 -42.5(5) . . . . ?
O64 C63 C46 C67 80.8(5) . . . . ?
O64 C63 C46 C45 -156.2(4) . . . . ?
N48 C52 C51 C50 -4.5(6) . . . . ?
N48 C49 C50 C51 -2.0(7) . . . . ?
N13 C17 C16 C15 -1.3(6) . . . . ?
N13 C1 C2 C3 138.1(3) . . . . ?
N13 C14 C15 C16 0.7(7) . . . . ?
O35 C32 C3 C28 -154.1(6) . . . . ?
O35 C32 C3 C4 81.4(6) . . . . ?
O35 C32 C3 C2 -28.7(7) . . . . ?
O53 C49 C50 C51 178.7(7) . . . . ?
O18 C14 C15 C16 179.5(7) . . . . ?
C6 N5 C4 N12 8.7(4) . . . . ?
C6 N5 C4 C3 -105.7(4) . . . . ?
C6 N5 C21 C22 9.5(7) . . . . ?
C6 N7 C8 N9 2.0(8) . . . . ?
C6 C11 C10 Cl20 -178.2(3) . . . . ?
C6 C11 C10 N9 2.5(6) . . . . ?
O70 C67 C46 C47 -30.6(8) . . . . ?
O70 C67 C46 C63 -155.5(6) . . . . ?
O70 C67 C46 C45 79.3(7) . . . . ?
C38 N37 C45 N44 -12.5(4) . . . . ?
C38 N37 C45 C46 111.6(4) . . . . ?
C38 N37 C36 N48 115.9(4) . . . . ?
C38 N37 C36 C47 -124.4(4) . . . . ?
C11 N12 C4 N5 -11.4(4) . . . . ?
C11 N12 C4 C3 111.9(4) . . . . ?
C11 N12 C1 N13 114.9(4) . . . . ?
C11 N12 C1 C2 -124.5(4) . . . . ?
C4 N5 C6 N7 178.2(4) . . . . ?
C4 N5 C6 C11 -2.9(4) . . . . ?
C4 N5 C21 C22 -178.8(4) . . . . ?
C4 N12 C11 C6 10.2(4) . . . . ?
C4 N12 C11 C10 -174.0(4) . . . . ?
C4 N12 C1 N13 -114.1(4) . . . . ?
C4 N12 C1 C2 6.5(4) . . . . ?
C43 N42 C41 N40 3.6(8) . . . . ?
C43 N44 C45 N37 9.3(4) . . . . ?
C43 N44 C45 C46 -105.3(4) . . . . ?
C43 N44 C56 C57 9.5(7) . . . . ?
C43 C38 C39 Cl55 -176.4(3) . . . . ?
C43 C38 C39 N40 3.3(6) . . . . ?
C10 N9 C8 N7 -2.0(8) . . . . ?
C17 N13 C1 N12 48.3(6) . . . . ?
C17 N13 C1 C2 -69.6(5) . . . . ?
C17 N13 C14 O18 179.5(6) . . . . ?
C17 N13 C14 C15 -1.6(6) . . . . ?
C17 C16 C15 C14 0.4(7) . . . . ?
C1 N12 C11 C6 141.7(3) . . . . ?
C1 N12 C11 C10 -42.4(7) . . . . ?
C1 N12 C4 N5 -150.2(3) . . . . ?
C1 N12 C4 C3 -26.9(4) . . . . ?
C1 N13 C17 O19 -4.2(7) . . . . ?
C1 N13 C17 C16 176.6(4) . . . . ?
C1 N13 C14 O18 4.6(9) . . . . ?
C1 N13 C14 C15 -176.5(5) . . . . ?
C1 C2 C3 C28 -152.1(3) . . . . ?
C1 C2 C3 C32 84.0(4) . . . . ?
C1 C2 C3 C4 -31.5(4) . . . . ?
C45 N37 C38 C43 11.4(4) . . . . ?
C45 N37 C38 C39 -172.5(4) . . . . ?
C45 N37 C36 N48 -115.5(4) . . . . ?
C45 N37 C36 C47 4.2(4) . . . . ?
C45 N44 C43 N42 177.8(4) . . . . ?
C45 N44 C43 C38 -2.7(4) . . . . ?
C45 N44 C56 C57 179.9(4) . . . . ?
C52 N48 C36 N37 48.3(6) . . . . ?
C52 N48 C36 C47 -68.6(5) . . . . ?
C52 N48 C49 O53 178.4(6) . . . . ?
C52 N48 C49 C50 -0.9(7) . . . . ?
C58 O59 C60 C61 177.9(7) . . . . ?
C58 C57 C56 N44 -177.1(4) . . . . ?
C36 N37 C38 C43 141.3(3) . . . . ?
C36 N37 C38 C39 -42.7(7) . . . . ?
C36 N37 C45 N44 -149.2(3) . . . . ?
C36 N37 C45 C46 -25.1(4) . . . . ?
C36 N48 C52 O54 -5.5(8) . . . . ?
C36 N48 C52 C51 175.0(4) . . . . ?
C36 N48 C49 O53 6.5(9) . . . . ?
C36 N48 C49 C50 -172.8(5) . . . . ?
C36 C47 C46 C63 -153.6(4) . . . . ?
C36 C47 C46 C67 82.4(4) . . . . ?
C36 C47 C46 C45 -32.8(4) . . . . ?
C41 N42 C43 N44 179.3(4) . . . . ?
C41 N42 C43 C38 -0.1(7) . . . . ?
C41 N40 C39 Cl55 179.3(4) . . . . ?
C41 N40 C39 C38 -0.4(7) . . . . ?
C21 N5 C6 N7 -9.3(7) . . . . ?
C21 N5 C6 C11 169.6(4) . . . . ?
C21 N5 C4 N12 -164.3(3) . . . . ?
C21 N5 C4 C3 81.2(5) . . . . ?
C21 C22 C23 O24 -175.2(4) . . . . ?
C21 C22 C23 O27 4.8(9) . . . . ?
C23 O24 C25 C26 -173.0(6) . . . . ?
C23 C22 C21 N5 -179.6(4) . . . . ?
C56 N44 C43 N42 -10.8(7) . . . . ?
C56 N44 C43 C38 168.7(4) . . . . ?
C56 N44 C45 N37 -162.7(3) . . . . ?
C56 N44 C45 C46 82.7(5) . . . . ?
C56 C57 C58 O59 -177.1(4) . . . . ?
C56 C57 C58 O62 3.7(8) . . . . ?
C39 N40 C41 N42 -3.4(8) . . . . ?
C39 C38 C43 N42 -3.0(6) . . . . ?
C39 C38 C43 N44 177.4(3) . . . . ?
C46 C47 C36 N37 18.9(4) . . . . ?
C46 C47 C36 N48 139.3(3) . . . . ?
C8 N7 C6 N5 179.0(4) . . . . ?
C8 N7 C6 C11 0.4(6) . . . . ?
C8 N9 C10 Cl20 -179.9(4) . . . . ?
C8 N9 C10 C11 -0.6(7) . . . . ?
C49 N48 C52 O54 -177.0(5) . . . . ?
C49 N48 C52 C51 3.4(6) . . . . ?
C49 N48 C36 N37 -140.8(5) . . . . ?
C49 N48 C36 C47 102.3(5) . . . . ?
C49 C50 C51 C52 3.9(7) . . . . ?
C14 N13 C17 O19 -178.9(5) . . . . ?
C14 N13 C17 C16 1.9(6) . . . . ?
C14 N13 C1 N12 -137.5(5) . . . . ?
C14 N13 C1 C2 104.7(5) . . . . ?
C34 O33 C32 O35 1.4(9) . . . . ?
C34 O33 C32 C3 179.7(5) . . . . ?
C25 O24 C23 O27 1.9(9) . . . . ?
C25 O24 C23 C22 -178.1(5) . . . . ?
C30 O29 C28 O31 1.5(8) . . . . ?
C30 O29 C28 C3 179.5(5) . . . . ?
C65 O64 C63 O66 1.6(8) . . . . ?
C65 O64 C63 C46 -179.3(5) . . . . ?
C60 O59 C58 O62 2.9(9) . . . . ?
C60 O59 C58 C57 -176.3(5) . . . . ?
C69 O68 C67 O70 0.8(11) . . . . ?
C69 O68 C67 C46 -179.1(6) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.244 0.343 0.251 219.7 54.8 ?
2 0.256 0.843 0.749 219.7 54.7 ?
3 0.744 0.843 0.251 219.7 54.8 ?
4 0.756 0.343 0.749 219.7 54.7 ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 8.545
_oxdiff_exptl_absorpt_empirical_full_min 0.343
####################################################################### 
# 
# 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_fdd-2-1-20180205
_database_code_depnum_ccdc_archive 'CCDC 1837938'
_audit_update_record             
;
2018-04-18 deposited with the CCDC.
2019-02-08 downloaded from the CCDC.
;
_audit_creation_date             2018-02-05
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.01.22 svn.r3481 for OlexSys, GUI svn.r5465)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H26 Cl N5 O9'
_chemical_formula_sum            'C22 H26 Cl N5 O9'
_chemical_formula_weight         539.93
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 O1 N1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   14.6444(2)
_cell_length_b                   19.0270(3)
_cell_length_c                   9.29920(10)
_cell_angle_alpha                90
_cell_angle_beta                 98.1150(10)
_cell_angle_gamma                90
_cell_volume                     2565.17(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10087
_cell_measurement_temperature    291.42(10)
_cell_measurement_theta_max      72.5720
_cell_measurement_theta_min      4.6390
_shelx_estimated_absorpt_T_max   0.947
_shelx_estimated_absorpt_T_min   0.581
_exptl_absorpt_coefficient_mu    1.846
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40303
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            20088
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.482
_diffrn_reflns_theta_min         3.833
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      291.42(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0528
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):
  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     23.00  90.00   1.00    1.00    --   36.21-125.00  90.00   67
  2  ω    -31.00  53.00   1.00    1.00    --   36.21 -57.00  90.00   84
  3  ω     23.00  90.00   1.00    1.00    --   36.21-125.00 -60.00   67
  4  ω    -31.00  63.00   1.00    1.00    --   36.21 -77.00  60.00   94
  5  ω     17.00 105.00   1.00    1.00    --   36.21  38.00-120.00   88
  6  ω     19.00 103.00   1.00    1.00    --   36.21  57.00 -30.00   84
  7  ω     19.00 103.00   1.00    1.00    --   36.21  57.00  60.00   84
  8  ω     19.00 103.00   1.00    1.00    --   36.21  57.00-120.00   84
  9  ω     23.00  90.00   1.00    1.00    --   36.21-125.00 -90.00   67
 10  ω     42.00 127.00   1.00    1.86    --  109.31 -61.00-150.00   85
 11  ω     39.00 116.00   1.00    1.86    --  109.31-111.00  60.00   77
 12  ω     83.00 177.00   1.00    1.86    --  109.31  77.00-180.00   94
 13  ω    100.00 178.00   1.00    1.86    --  109.31 111.00 150.00   78
 14  ω     92.00 178.00   1.00    1.86    --  109.31  45.00 120.00   86
 15  ω     42.00 136.00   1.00    1.86    --  109.31 -77.00  90.00   94
 16  ω     42.00 127.00   1.00    1.86    --  109.31 -61.00  60.00   85
 17  ω     83.00 177.00   1.00    1.86    --  109.31  77.00-150.00   94
 18  ω     83.00 177.00   1.00    1.86    --  109.31  77.00 -90.00   94
 19  ω    -31.00  53.00   1.00    1.00    --   36.21 -57.00-180.00   84
 20  ω    -33.00  55.00   1.00    1.00    --   36.21 -38.00 -90.00   88
 21  ω      9.00 104.00   1.00    1.00    --   36.21  77.00 150.00   95
 22  ω      9.00  69.00   1.00    1.00    --   36.21  77.00   0.00   60
 23  ω     17.00 105.00   1.00    1.00    --   36.21  38.00 150.00   88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0646719000
_diffrn_orient_matrix_UB_12      -0.0640654000
_diffrn_orient_matrix_UB_13      -0.0028380000
_diffrn_orient_matrix_UB_21      -0.0802044000
_diffrn_orient_matrix_UB_22      0.0444950000
_diffrn_orient_matrix_UB_23      -0.0771095000
_diffrn_orient_matrix_UB_31      0.0259941000
_diffrn_orient_matrix_UB_32      -0.0218548000
_diffrn_orient_matrix_UB_33      -0.1484089000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4205
_reflns_number_total             5015
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.489
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     338
_refine_ls_number_reflns         5015
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0747
_refine_ls_R_factor_gt           0.0664
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1211P)²+0.9016P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1850
_refine_ls_wR_factor_ref         0.1976
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15a,H15b), C11(H11a,H11b), C16(H16a,H16b), C33(H33a,H33b)
2.c Aromatic/amide H refined with riding coordinates:
 N13(H13), C29(H29), C30(H30), C5(H5)
2.d Idealised Me refined as rotating group:
 C23(H23a,H23b,H23c), C27(H27a,H27b,H27c), C34(H34a,H34b,H34c), C1(H1a,H1b,H1c)
;
_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
Cl36 Cl 0.33936(5) 0.40811(4) 0.84576(7) 0.0528(2) Uani 1 1 d . . . . .
O26 O 0.71921(13) 0.34388(10) 0.4350(2) 0.0511(5) Uani 1 1 d . . . . .
O22 O 0.75323(13) 0.43429(10) 0.82652(19) 0.0492(5) Uani 1 1 d . . . . .
N1 N 0.50880(13) 0.39892(10) 0.64559(19) 0.0327(4) Uani 1 1 d . . . . .
N13 N 0.42912(13) 0.28768(10) 0.63870(18) 0.0354(4) Uani 1 1 d . . . . .
H13 H 0.409924 0.292310 0.547444 0.043 Uiso 1 1 calc R . . . .
O20 O 0.40616(15) 0.23650(11) 0.84746(17) 0.0555(5) Uani 1 1 d . . . . .
N8 N 0.61090(14) 0.49002(10) 0.6277(2) 0.0370(4) Uani 1 1 d . . . . .
O24 O 0.69382(16) 0.33989(11) 0.9211(2) 0.0610(6) Uani 1 1 d . . . . .
O32 O 0.86614(15) 0.53614(11) 0.3846(3) 0.0641(6) Uani 1 1 d . . . . .
O28 O 0.81973(14) 0.32448(14) 0.6357(3) 0.0706(6) Uani 1 1 d . . . . .
N6 N 0.54408(16) 0.57430(11) 0.7729(2) 0.0473(5) Uani 1 1 d . . . . .
N4 N 0.41250(17) 0.53322(12) 0.8749(2) 0.0509(6) Uani 1 1 d . . . . .
O35 O 0.8130(2) 0.62579(13) 0.5053(3) 0.0879(9) Uani 1 1 d . . . . .
C21 C 0.70538(16) 0.37544(12) 0.8197(2) 0.0373(5) Uani 1 1 d . . . . .
C2 C 0.48664(15) 0.45598(12) 0.7298(2) 0.0327(5) Uani 1 1 d . . . . .
C9 C 0.59609(15) 0.41566(11) 0.5908(2) 0.0325(5) Uani 1 1 d . . . . .
H9 H 0.587639 0.410214 0.484957 0.039 Uiso 1 1 calc R . . . .
C7 C 0.54730(16) 0.51120(12) 0.7153(2) 0.0355(5) Uani 1 1 d . . . . .
C14 C 0.38273(16) 0.24551(12) 0.7167(2) 0.0352(5) Uani 1 1 d . . . . .
C12 C 0.66560(15) 0.35865(12) 0.6616(2) 0.0346(5) Uani 1 1 d . . . . .
C10 C 0.51007(15) 0.32589(11) 0.7006(2) 0.0327(5) Uani 1 1 d . . . . .
H10 H 0.514261 0.326263 0.806709 0.039 Uiso 1 1 calc R . . . .
C15 C 0.29958(17) 0.20996(13) 0.6358(2) 0.0412(5) Uani 1 1 d . . . . .
H15A H 0.309507 0.159546 0.637021 0.049 Uiso 1 1 calc R . . . .
H15B H 0.291238 0.225340 0.535315 0.049 Uiso 1 1 calc R . . . .
C29 C 0.67752(17) 0.53284(13) 0.5846(3) 0.0410(5) Uani 1 1 d . . . . .
H29 H 0.679436 0.578945 0.618062 0.049 Uiso 1 1 calc R . . . .
C11 C 0.59916(16) 0.29599(12) 0.6566(3) 0.0386(5) Uani 1 1 d . . . . .
H11A H 0.587894 0.276219 0.559563 0.046 Uiso 1 1 calc R . . . .
H11B H 0.624319 0.259614 0.723840 0.046 Uiso 1 1 calc R . . . .
O19 O 0.05480(17) 0.21886(15) 0.6508(4) 0.1042(11) Uani 1 1 d . . . . .
C3 C 0.41897(17) 0.46987(13) 0.8133(2) 0.0402(5) Uani 1 1 d . . . . .
C25 C 0.74465(18) 0.34125(13) 0.5784(3) 0.0442(6) Uani 1 1 d . . . . .
C30 C 0.73910(18) 0.51497(14) 0.5003(3) 0.0461(6) Uani 1 1 d . . . . .
H30 H 0.738396 0.469825 0.461781 0.055 Uiso 1 1 calc R . . . .
C31 C 0.8084(2) 0.56540(15) 0.4668(3) 0.0535(7) Uani 1 1 d . . . . .
C5 C 0.4740(2) 0.58131(15) 0.8510(3) 0.0524(7) Uani 1 1 d . . . . .
H5 H 0.468077 0.625078 0.893271 0.063 Uiso 1 1 calc R . . . .
C16 C 0.2140(2) 0.22616(15) 0.7014(4) 0.0553(7) Uani 1 1 d . . . . .
H16A H 0.223281 0.212492 0.802874 0.066 Uiso 1 1 calc R . . . .
H16B H 0.202777 0.276412 0.696679 0.066 Uiso 1 1 calc R . . . .
C23 C 0.7949(2) 0.45830(17) 0.9683(3) 0.0570(7) Uani 1 1 d . . . . .
H23A H 0.821507 0.503958 0.959651 0.085 Uiso 1 1 calc GR . . . .
H23B H 0.842230 0.425916 1.007592 0.085 Uiso 1 1 calc GR . . . .
H23C H 0.748707 0.460952 1.031757 0.085 Uiso 1 1 calc GR . . . .
C17 C 0.1318(2) 0.18878(18) 0.6250(5) 0.0710(10) Uani 1 1 d . . . . .
C27 C 0.7902(2) 0.3299(2) 0.3456(4) 0.0722(10) Uani 1 1 d . . . . .
H27A H 0.765184 0.335145 0.245090 0.108 Uiso 1 1 calc GR . . . .
H27B H 0.812570 0.282729 0.362674 0.108 Uiso 1 1 calc GR . . . .
H27C H 0.840173 0.362390 0.369669 0.108 Uiso 1 1 calc GR . . . .
C34 C 0.9983(3) 0.5389(3) 0.2657(5) 0.0974(14) Uani 1 1 d . . . . .
H34A H 0.963487 0.522463 0.176874 0.146 Uiso 1 1 calc GR . . . .
H34B H 1.021590 0.499476 0.323962 0.146 Uiso 1 1 calc GR . . . .
H34C H 1.048960 0.567148 0.243866 0.146 Uiso 1 1 calc GR . . . .
C33 C 0.9388(3) 0.5812(2) 0.3454(5) 0.0932(14) Uani 1 1 d . . . . .
H33A H 0.974364 0.600636 0.432213 0.112 Uiso 1 1 calc R . . . .
H33B H 0.912240 0.619772 0.285299 0.112 Uiso 1 1 calc R . . . .
O18 O 0.1337(2) 0.13829(18) 0.5509(5) 0.1298(16) Uani 1 1 d . . . . .
C1 C -0.0295(3) 0.1863(4) 0.5804(11) 0.178(4) Uani 1 1 d . . . . .
H1A H -0.031774 0.189254 0.476941 0.267 Uiso 1 1 calc GR . . . .
H1B H -0.081772 0.210169 0.609048 0.267 Uiso 1 1 calc GR . . . .
H1C H -0.030636 0.137793 0.608838 0.267 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl36 C3 1.712(3) . ?
O26 C25 1.334(3) . ?
O26 C27 1.445(3) . ?
O22 C21 1.318(3) . ?
O22 C23 1.447(3) . ?
N1 C2 1.403(3) . ?
N1 C9 1.476(3) . ?
N1 C10 1.480(3) . ?
N13 H13 0.8600 . ?
N13 C14 1.331(3) . ?
N13 C10 1.440(3) . ?
O20 C14 1.228(3) . ?
N8 C9 1.465(3) . ?
N8 C7 1.381(3) . ?
N8 C29 1.374(3) . ?
O24 C21 1.192(3) . ?
O32 C31 1.339(3) . ?
O32 C33 1.452(4) . ?
O28 C25 1.196(3) . ?
N6 C7 1.318(3) . ?
N6 C5 1.345(4) . ?
N4 C3 1.344(3) . ?
N4 C5 1.325(4) . ?
O35 C31 1.203(4) . ?
C21 C12 1.537(3) . ?
C2 C7 1.395(3) . ?
C2 C3 1.368(3) . ?
C9 H9 0.9800 . ?
C9 C12 1.568(3) . ?
C14 C15 1.499(3) . ?
C12 C11 1.535(3) . ?
C12 C25 1.517(3) . ?
C10 H10 0.9800 . ?
C10 C11 1.531(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.502(3) . ?
C29 H29 0.9300 . ?
C29 C30 1.320(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
O19 C17 1.317(4) . ?
O19 C1 1.452(6) . ?
C30 H30 0.9300 . ?
C30 C31 1.461(3) . ?
C5 H5 0.9300 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.489(4) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C17 O18 1.185(4) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C34 C33 1.462(6) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?

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
C25 O26 C27 116.5(2) . . ?
C21 O22 C23 117.7(2) . . ?
C2 N1 C9 107.78(17) . . ?
C2 N1 C10 121.75(16) . . ?
C9 N1 C10 110.65(17) . . ?
C14 N13 H13 118.6 . . ?
C14 N13 C10 122.79(18) . . ?
C10 N13 H13 118.6 . . ?
C7 N8 C9 109.28(18) . . ?
C29 N8 C9 126.3(2) . . ?
C29 N8 C7 124.4(2) . . ?
C31 O32 C33 116.2(3) . . ?
C7 N6 C5 112.6(2) . . ?
C5 N4 C3 117.2(2) . . ?
O22 C21 C12 110.48(19) . . ?
O24 C21 O22 125.3(2) . . ?
O24 C21 C12 124.2(2) . . ?
C7 C2 N1 109.16(18) . . ?
C3 C2 N1 135.2(2) . . ?
C3 C2 C7 115.6(2) . . ?
N1 C9 H9 109.3 . . ?
N1 C9 C12 104.39(16) . . ?
N8 C9 N1 103.55(17) . . ?
N8 C9 H9 109.3 . . ?
N8 C9 C12 120.27(18) . . ?
C12 C9 H9 109.3 . . ?
N8 C7 C2 109.2(2) . . ?
N6 C7 N8 124.8(2) . . ?
N6 C7 C2 126.0(2) . . ?
N13 C14 C15 116.06(18) . . ?
O20 C14 N13 122.1(2) . . ?
O20 C14 C15 121.9(2) . . ?
C21 C12 C9 113.20(18) . . ?
C11 C12 C21 110.08(18) . . ?
C11 C12 C9 98.82(17) . . ?
C25 C12 C21 108.66(19) . . ?
C25 C12 C9 115.72(18) . . ?
C25 C12 C11 109.94(19) . . ?
N1 C10 H10 109.7 . . ?
N1 C10 C11 103.06(16) . . ?
N13 C10 N1 111.50(18) . . ?
N13 C10 H10 109.7 . . ?
N13 C10 C11 112.97(18) . . ?
C11 C10 H10 109.7 . . ?
C14 C15 H15A 109.3 . . ?
C14 C15 H15B 109.3 . . ?
C14 C15 C16 111.7(2) . . ?
H15A C15 H15B 108.0 . . ?
C16 C15 H15A 109.3 . . ?
C16 C15 H15B 109.3 . . ?
N8 C29 H29 116.8 . . ?
C30 C29 N8 126.4(2) . . ?
C30 C29 H29 116.8 . . ?
C12 C11 H11A 110.7 . . ?
C12 C11 H11B 110.7 . . ?
C10 C11 C12 105.29(18) . . ?
C10 C11 H11A 110.7 . . ?
C10 C11 H11B 110.7 . . ?
H11A C11 H11B 108.8 . . ?
C17 O19 C1 115.3(4) . . ?
N4 C3 Cl36 116.71(18) . . ?
N4 C3 C2 121.0(2) . . ?
C2 C3 Cl36 122.24(19) . . ?
O26 C25 C12 112.1(2) . . ?
O28 C25 O26 124.4(2) . . ?
O28 C25 C12 123.4(2) . . ?
C29 C30 H30 119.7 . . ?
C29 C30 C31 120.7(2) . . ?
C31 C30 H30 119.7 . . ?
O32 C31 C30 111.2(2) . . ?
O35 C31 O32 123.6(3) . . ?
O35 C31 C30 125.1(3) . . ?
N6 C5 H5 116.2 . . ?
N4 C5 N6 127.7(2) . . ?
N4 C5 H5 116.2 . . ?
C15 C16 H16A 109.2 . . ?
C15 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
C17 C16 C15 111.9(2) . . ?
C17 C16 H16A 109.2 . . ?
C17 C16 H16B 109.2 . . ?
O22 C23 H23A 109.5 . . ?
O22 C23 H23B 109.5 . . ?
O22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O19 C17 C16 111.1(3) . . ?
O18 C17 O19 123.3(3) . . ?
O18 C17 C16 125.6(3) . . ?
O26 C27 H27A 109.5 . . ?
O26 C27 H27B 109.5 . . ?
O26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
O32 C33 C34 108.2(3) . . ?
O32 C33 H33A 110.1 . . ?
O32 C33 H33B 110.1 . . ?
C34 C33 H33A 110.1 . . ?
C34 C33 H33B 110.1 . . ?
H33A C33 H33B 108.4 . . ?
O19 C1 H1A 109.5 . . ?
O19 C1 H1B 109.5 . . ?
O19 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.414
_oxdiff_exptl_absorpt_empirical_full_min 0.408
####################################################################### 
# 
# 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_fdd-1-20180205
_database_code_depnum_ccdc_archive 'CCDC 1837937'
_audit_update_record             
;
2018-04-18 deposited with the CCDC.
2019-02-08 downloaded from the CCDC.
;
_audit_creation_date             2018-02-05
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.01.22 svn.r3481 for OlexSys, GUI svn.r5465)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H22 Cl N5 O8'
_chemical_formula_sum            'C25 H22 Cl N5 O8'
_chemical_formula_weight         555.92
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 O1 N1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   8.9522(4)
_cell_length_b                   12.3288(5)
_cell_length_c                   12.6211(5)
_cell_angle_alpha                103.938(3)
_cell_angle_beta                 101.104(4)
_cell_angle_gamma                102.417(4)
_cell_volume                     1275.71(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6083
_cell_measurement_temperature    291.69(10)
_cell_measurement_theta_max      28.4420
_cell_measurement_theta_min      3.8950
_shelx_estimated_absorpt_T_max   0.949
_shelx_estimated_absorpt_T_min   0.912
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84509
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14063
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         3.376
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      291.69(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0528
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):
  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -1.00  83.00   1.00    3.71    --   16.13  57.00 -90.00   84
  2  ω    -14.00  59.00   1.00    3.71    --   16.13-106.00  36.00   73
  3  ω    -11.00  84.00   1.00    3.71    --   16.13  77.00 150.00   95
  4  ω    -11.00  84.00   1.00    3.71    --   16.13  77.00 -60.00   95
  5  ω    -51.00  33.00   1.00    3.71    --   16.13 -57.00  60.00   84
  6  ω    -51.00  33.00   1.00    3.71    --   16.13 -57.00   0.00   84
  7  ω    -51.00  31.00   1.00    3.71    --   16.13 -57.00-180.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0791666000
_diffrn_orient_matrix_UB_12      0.0146285000
_diffrn_orient_matrix_UB_13      -0.0044337000
_diffrn_orient_matrix_UB_21      -0.0278834000
_diffrn_orient_matrix_UB_22      -0.0042502000
_diffrn_orient_matrix_UB_23      -0.0578036000
_diffrn_orient_matrix_UB_31      0.0024139000
_diffrn_orient_matrix_UB_32      0.0597328000
_diffrn_orient_matrix_UB_33      0.0151905000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3674
_reflns_number_total             4475
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.084
_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     355
_refine_ls_number_reflns         4475
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0503
_refine_ls_restrained_S_all      1.058
_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)+(0.0665P)²+0.3673P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1244
_refine_ls_wR_factor_ref         0.1314
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12a,H12b), C(Ha,Hb)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C16(H16), C19(H19), C24(H24), C25(H25), C18(H18), C17(H17)
2.d Idealised Me refined as rotating group:
 C31(H31a,H31b,H31c), C35(H35a,H35b,H35c), C0AA(H0Aa,H0Ab,H0Ac)
;
_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
Cl37 Cl 0.50007(9) 0.71772(5) 0.75924(6) 0.0729(2) Uani 1 1 d . . . . .
O23 O 0.79120(18) 0.38575(13) 0.72552(12) 0.0515(4) Uani 1 1 d . . . . .
O30 O 0.09797(19) 0.14531(13) 0.60333(15) 0.0630(5) Uani 1 1 d . . . . .
O22 O 0.6514(2) 0.64931(15) 0.98093(13) 0.0643(5) Uani 1 1 d . . . . .
N2 N 0.47954(19) 0.44340(14) 0.65667(13) 0.0409(4) Uani 1 1 d . . . . .
O36 O 0.3989(3) 0.08222(15) 0.53745(15) 0.0745(5) Uani 1 1 d . . . . .
N13 N 0.68169(19) 0.51012(14) 0.83323(13) 0.0431(4) Uani 1 1 d . . . . .
O32 O 0.1589(2) 0.33123(14) 0.70171(17) 0.0720(5) Uani 1 1 d . . . . .
O34 O 0.4023(3) 0.08323(15) 0.71392(15) 0.0756(6) Uani 1 1 d . . . . .
N7 N 0.1659(2) 0.46035(15) 0.44557(15) 0.0487(4) Uani 1 1 d . . . . .
N9 N 0.3003(2) 0.32159(14) 0.49097(13) 0.0436(4) Uani 1 1 d . . . . .
N5 N 0.2654(2) 0.65136(16) 0.57675(16) 0.0549(5) Uani 1 1 d . . . . .
O28 O -0.0980(3) 0.08130(17) 0.16452(17) 0.0956(7) Uani 1 1 d . . . . .
O27 O 0.1048(3) 0.01530(19) 0.22542(18) 0.1012(8) Uani 1 1 d . . . . .
C21 C 0.8070(2) 0.47265(17) 0.79959(16) 0.0413(5) Uani 1 1 d . . . . .
C3 C 0.3811(2) 0.50298(17) 0.61124(16) 0.0402(5) Uani 1 1 d . . . . .
C8 C 0.2729(2) 0.43009(17) 0.51068(16) 0.0406(5) Uani 1 1 d . . . . .
C29 C 0.1971(2) 0.24707(17) 0.66081(17) 0.0436(5) Uani 1 1 d . . . . .
C14 C 0.7362(3) 0.60547(18) 0.93038(17) 0.0464(5) Uani 1 1 d . . . . .
C20 C 0.9538(2) 0.55879(18) 0.87612(17) 0.0434(5) Uani 1 1 d . . . . .
C15 C 0.9107(3) 0.63644(17) 0.95528(17) 0.0442(5) Uani 1 1 d . . . . .
C4 C 0.3723(3) 0.61521(17) 0.63977(18) 0.0483(5) Uani 1 1 d . . . . .
C11 C 0.3682(2) 0.25006(16) 0.66464(16) 0.0407(5) Uani 1 1 d . . . . .
C10 C 0.4239(2) 0.32149(17) 0.58598(16) 0.0405(5) Uani 1 1 d . . . . .
H10 H 0.510505 0.297190 0.558819 0.049 Uiso 1 1 calc R . . . .
C1 C 0.5163(2) 0.45081(17) 0.77764(16) 0.0429(5) Uani 1 1 d . . . . .
H1 H 0.449585 0.492510 0.814385 0.051 Uiso 1 1 calc R . . . .
C12 C 0.4741(3) 0.32474(18) 0.78175(17) 0.0480(5) Uani 1 1 d . . . . .
H12A H 0.418213 0.317786 0.839499 0.058 Uiso 1 1 calc R . . . .
H12B H 0.569299 0.299846 0.798907 0.058 Uiso 1 1 calc R . . . .
C33 C 0.3919(3) 0.12942(19) 0.63006(19) 0.0506(5) Uani 1 1 d . . . . .
C6 C 0.1702(3) 0.5734(2) 0.4852(2) 0.0539(6) Uani 1 1 d . . . . .
H6 H 0.096374 0.599015 0.442249 0.065 Uiso 1 1 calc R . . . .
C16 C 1.0240(3) 0.7250(2) 1.0401(2) 0.0584(6) Uani 1 1 d . . . . .
H16 H 0.995939 0.776997 1.094184 0.070 Uiso 1 1 calc R . . . .
C19 C 1.1097(3) 0.5662(2) 0.8773(2) 0.0549(6) Uani 1 1 d . . . . .
H19 H 1.137568 0.513288 0.823937 0.066 Uiso 1 1 calc R . . . .
C24 C 0.2258(3) 0.22331(19) 0.40044(17) 0.0495(5) Uani 1 1 d . . . . .
H24 H 0.270320 0.161382 0.396898 0.059 Uiso 1 1 calc R . . . .
C25 C 0.0988(3) 0.2065(2) 0.31804(19) 0.0598(6) Uani 1 1 d . . . . .
H25 H 0.048818 0.264742 0.314219 0.072 Uiso 1 1 calc R . . . .
C18 C 1.2232(3) 0.6559(2) 0.9613(2) 0.0656(7) Uani 1 1 d . . . . .
H18 H 1.329753 0.664203 0.963906 0.079 Uiso 1 1 calc R . . . .
C17 C 1.1810(3) 0.7333(2) 1.0412(2) 0.0655(7) Uani 1 1 d . . . . .
H17 H 1.259930 0.792242 1.097071 0.079 Uiso 1 1 calc R . . . .
C26 C 0.0406(4) 0.0923(2) 0.2334(2) 0.0700(7) Uani 1 1 d . . . . .
C31 C -0.0698(3) 0.1386(3) 0.5875(3) 0.0884(9) Uani 1 1 d . . . . .
H31A H -0.130112 0.058675 0.566025 0.133 Uiso 1 1 calc GR . . . .
H31B H -0.102785 0.172622 0.529309 0.133 Uiso 1 1 calc GR . . . .
H31C H -0.087067 0.180031 0.656898 0.133 Uiso 1 1 calc GR . . . .
C35 C 0.4294(5) -0.0316(3) 0.6909(3) 0.0996(12) Uani 1 1 d . . . . .
H35A H 0.349107 -0.084046 0.626216 0.149 Uiso 1 1 calc GR . . . .
H35B H 0.425451 -0.059720 0.755265 0.149 Uiso 1 1 calc GR . . . .
H35C H 0.531572 -0.026718 0.676225 0.149 Uiso 1 1 calc GR . . . .
C C -0.1769(5) -0.0343(3) 0.0848(3) 0.1193(14) Uani 1 1 d . . . . .
HA H -0.109266 -0.057049 0.037085 0.143 Uiso 1 1 calc R . . . .
HB H -0.197206 -0.090712 0.125881 0.143 Uiso 1 1 calc R . . . .
C0AA C -0.3186(6) -0.0320(4) 0.0188(4) 0.166(2) Uani 1 1 d . . . . .
H0AA H -0.297133 0.010166 -0.033908 0.248 Uiso 1 1 calc GR . . . .
H0AB H -0.375672 0.005542 0.066312 0.248 Uiso 1 1 calc GR . . . .
H0AC H -0.380904 -0.110049 -0.021803 0.248 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl37 C4 1.725(2) . ?
O23 C21 1.201(2) . ?
O30 C29 1.313(2) . ?
O30 C31 1.458(3) . ?
O22 C14 1.213(3) . ?
N2 C3 1.390(3) . ?
N2 C10 1.471(2) . ?
N2 C1 1.474(2) . ?
O36 C33 1.194(3) . ?
N13 C21 1.401(3) . ?
N13 C14 1.397(3) . ?
N13 C1 1.451(3) . ?
O32 C29 1.193(2) . ?
O34 C33 1.315(3) . ?
O34 C35 1.458(3) . ?
N7 C8 1.316(3) . ?
N7 C6 1.352(3) . ?
N9 C8 1.384(3) . ?
N9 C10 1.468(3) . ?
N9 C24 1.382(3) . ?
N5 C4 1.345(3) . ?
N5 C6 1.311(3) . ?
O28 C26 1.330(3) . ?
O28 C 1.464(3) . ?
O27 C26 1.206(3) . ?
C21 C20 1.485(3) . ?
C3 C8 1.400(3) . ?
C3 C4 1.367(3) . ?
C29 C11 1.515(3) . ?
C14 C15 1.477(3) . ?
C20 C15 1.382(3) . ?
C20 C19 1.375(3) . ?
C15 C16 1.382(3) . ?
C11 C10 1.560(3) . ?
C11 C12 1.536(3) . ?
C11 C33 1.519(3) . ?
C10 H10 0.9800 . ?
C1 H1 0.9800 . ?
C1 C12 1.535(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C6 H6 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.384(4) . ?
C19 H19 0.9300 . ?
C19 C18 1.384(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.325(3) . ?
C25 H25 0.9300 . ?
C25 C26 1.463(3) . ?
C18 H18 0.9300 . ?
C18 C17 1.382(4) . ?
C17 H17 0.9300 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C HA 0.9700 . ?
C HB 0.9700 . ?
C C0AA 1.387(6) . ?
C0AA H0AA 0.9600 . ?
C0AA H0AB 0.9600 . ?
C0AA H0AC 0.9600 . ?

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
C29 O30 C31 116.12(18) . . ?
C3 N2 C10 107.54(15) . . ?
C3 N2 C1 122.31(16) . . ?
C10 N2 C1 110.85(15) . . ?
C21 N13 C1 123.35(16) . . ?
C14 N13 C21 111.58(17) . . ?
C14 N13 C1 124.93(17) . . ?
C33 O34 C35 116.6(2) . . ?
C8 N7 C6 112.66(19) . . ?
C8 N9 C10 109.43(16) . . ?
C24 N9 C8 128.68(18) . . ?
C24 N9 C10 121.87(17) . . ?
C6 N5 C4 116.50(19) . . ?
C26 O28 C 116.0(3) . . ?
O23 C21 N13 124.55(19) . . ?
O23 C21 C20 129.71(19) . . ?
N13 C21 C20 105.71(16) . . ?
N2 C3 C8 110.52(17) . . ?
C4 C3 N2 134.60(19) . . ?
C4 C3 C8 114.79(19) . . ?
N7 C8 N9 126.15(18) . . ?
N7 C8 C3 125.79(19) . . ?
N9 C8 C3 108.05(18) . . ?
O30 C29 C11 113.02(17) . . ?
O32 C29 O30 124.6(2) . . ?
O32 C29 C11 122.30(19) . . ?
O22 C14 N13 124.6(2) . . ?
O22 C14 C15 129.7(2) . . ?
N13 C14 C15 105.77(17) . . ?
C15 C20 C21 107.94(18) . . ?
C19 C20 C21 130.0(2) . . ?
C19 C20 C15 122.0(2) . . ?
C20 C15 C14 108.72(17) . . ?
C16 C15 C14 130.4(2) . . ?
C16 C15 C20 120.9(2) . . ?
N5 C4 Cl37 116.83(16) . . ?
N5 C4 C3 122.2(2) . . ?
C3 C4 Cl37 120.99(18) . . ?
C29 C11 C10 108.30(16) . . ?
C29 C11 C12 109.53(16) . . ?
C29 C11 C33 112.62(17) . . ?
C12 C11 C10 102.42(15) . . ?
C33 C11 C10 110.55(16) . . ?
C33 C11 C12 112.86(18) . . ?
N2 C10 C11 105.42(15) . . ?
N2 C10 H10 110.3 . . ?
N9 C10 N2 104.00(15) . . ?
N9 C10 C11 116.07(16) . . ?
N9 C10 H10 110.3 . . ?
C11 C10 H10 110.3 . . ?
N2 C1 H1 109.4 . . ?
N2 C1 C12 105.60(15) . . ?
N13 C1 N2 111.39(15) . . ?
N13 C1 H1 109.4 . . ?
N13 C1 C12 111.49(17) . . ?
C12 C1 H1 109.4 . . ?
C11 C12 H12A 110.4 . . ?
C11 C12 H12B 110.4 . . ?
C1 C12 C11 106.79(16) . . ?
C1 C12 H12A 110.4 . . ?
C1 C12 H12B 110.4 . . ?
H12A C12 H12B 108.6 . . ?
O36 C33 O34 124.3(2) . . ?
O36 C33 C11 123.8(2) . . ?
O34 C33 C11 111.89(18) . . ?
N7 C6 H6 116.0 . . ?
N5 C6 N7 128.1(2) . . ?
N5 C6 H6 116.0 . . ?
C15 C16 H16 121.3 . . ?
C15 C16 C17 117.3(2) . . ?
C17 C16 H16 121.3 . . ?
C20 C19 H19 121.4 . . ?
C20 C19 C18 117.1(2) . . ?
C18 C19 H19 121.4 . . ?
N9 C24 H24 116.0 . . ?
C25 C24 N9 128.0(2) . . ?
C25 C24 H24 116.0 . . ?
C24 C25 H25 121.4 . . ?
C24 C25 C26 117.1(2) . . ?
C26 C25 H25 121.4 . . ?
C19 C18 H18 119.4 . . ?
C17 C18 C19 121.1(2) . . ?
C17 C18 H18 119.4 . . ?
C16 C17 H17 119.2 . . ?
C18 C17 C16 121.5(2) . . ?
C18 C17 H17 119.2 . . ?
O28 C26 C25 111.2(2) . . ?
O27 C26 O28 122.6(2) . . ?
O27 C26 C25 126.2(3) . . ?
O30 C31 H31A 109.5 . . ?
O30 C31 H31B 109.5 . . ?
O30 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
O34 C35 H35A 109.5 . . ?
O34 C35 H35B 109.5 . . ?
O34 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
O28 C HA 109.8 . . ?
O28 C HB 109.8 . . ?
HA C HB 108.3 . . ?
C0AA C O28 109.3(3) . . ?
C0AA C HA 109.8 . . ?
C0AA C HB 109.8 . . ?
C C0AA H0AA 109.5 . . ?
C C0AA H0AB 109.5 . . ?
C C0AA H0AC 109.5 . . ?
H0AA C0AA H0AB 109.5 . . ?
H0AA C0AA H0AC 109.5 . . ?
H0AB C0AA H0AC 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O23 C21 C20 C15 -173.4(2) . . . . ?
O23 C21 C20 C19 5.1(4) . . . . ?
O30 C29 C11 C10 106.89(19) . . . . ?
O30 C29 C11 C12 -142.15(19) . . . . ?
O30 C29 C11 C33 -15.7(2) . . . . ?
O22 C14 C15 C20 177.7(2) . . . . ?
O22 C14 C15 C16 -2.2(4) . . . . ?
N2 C3 C8 N7 -178.43(18) . . . . ?
N2 C3 C8 N9 0.6(2) . . . . ?
N2 C3 C4 Cl37 -2.2(3) . . . . ?
N2 C3 C4 N5 177.5(2) . . . . ?
N2 C1 C12 C11 -16.6(2) . . . . ?
N13 C21 C20 C15 4.5(2) . . . . ?
N13 C21 C20 C19 -177.1(2) . . . . ?
N13 C14 C15 C20 -1.5(2) . . . . ?
N13 C14 C15 C16 178.5(2) . . . . ?
N13 C1 C12 C11 -137.76(16) . . . . ?
O32 C29 C11 C10 -69.6(3) . . . . ?
O32 C29 C11 C12 41.3(3) . . . . ?
O32 C29 C11 C33 167.8(2) . . . . ?
N9 C24 C25 C26 -178.3(2) . . . . ?
C21 N13 C14 O22 -174.8(2) . . . . ?
C21 N13 C14 C15 4.6(2) . . . . ?
C21 N13 C1 N2 -58.1(2) . . . . ?
C21 N13 C1 C12 59.6(2) . . . . ?
C21 C20 C15 C14 -1.8(2) . . . . ?
C21 C20 C15 C16 178.13(19) . . . . ?
C21 C20 C19 C18 -178.7(2) . . . . ?
C3 N2 C10 N9 6.57(19) . . . . ?
C3 N2 C10 C11 -116.02(16) . . . . ?
C3 N2 C1 N13 -112.69(19) . . . . ?
C3 N2 C1 C12 126.11(19) . . . . ?
C8 N7 C6 N5 0.2(3) . . . . ?
C8 N9 C10 N2 -6.4(2) . . . . ?
C8 N9 C10 C11 108.91(18) . . . . ?
C8 N9 C24 C25 -8.5(4) . . . . ?
C8 C3 C4 Cl37 -178.40(14) . . . . ?
C8 C3 C4 N5 1.3(3) . . . . ?
C29 C11 C10 N2 86.70(18) . . . . ?
C29 C11 C10 N9 -27.8(2) . . . . ?
C29 C11 C12 C1 -86.96(19) . . . . ?
C29 C11 C33 O36 97.6(3) . . . . ?
C29 C11 C33 O34 -81.8(2) . . . . ?
C14 N13 C21 O23 172.36(19) . . . . ?
C14 N13 C21 C20 -5.6(2) . . . . ?
C14 N13 C1 N2 126.5(2) . . . . ?
C14 N13 C1 C12 -115.8(2) . . . . ?
C14 C15 C16 C17 -179.3(2) . . . . ?
C20 C15 C16 C17 0.8(3) . . . . ?
C20 C19 C18 C17 0.9(4) . . . . ?
C15 C20 C19 C18 -0.4(3) . . . . ?
C15 C16 C17 C18 -0.3(4) . . . . ?
C4 N5 C6 N7 -0.2(3) . . . . ?
C4 C3 C8 N7 -1.3(3) . . . . ?
C4 C3 C8 N9 177.68(17) . . . . ?
C10 N2 C3 C8 -4.6(2) . . . . ?
C10 N2 C3 C4 179.0(2) . . . . ?
C10 N2 C1 N13 118.82(17) . . . . ?
C10 N2 C1 C12 -2.4(2) . . . . ?
C10 N9 C8 N7 -177.21(18) . . . . ?
C10 N9 C8 C3 3.8(2) . . . . ?
C10 N9 C24 C25 169.6(2) . . . . ?
C10 C11 C12 C1 27.8(2) . . . . ?
C10 C11 C33 O36 -23.7(3) . . . . ?
C10 C11 C33 O34 156.86(19) . . . . ?
C1 N2 C3 C8 -134.54(17) . . . . ?
C1 N2 C3 C4 49.1(3) . . . . ?
C1 N2 C10 N9 142.64(15) . . . . ?
C1 N2 C10 C11 20.0(2) . . . . ?
C1 N13 C21 O23 -3.5(3) . . . . ?
C1 N13 C21 C20 178.52(17) . . . . ?
C1 N13 C14 O22 1.0(3) . . . . ?
C1 N13 C14 C15 -179.66(17) . . . . ?
C12 C11 C10 N2 -28.99(19) . . . . ?
C12 C11 C10 N9 -143.47(17) . . . . ?
C12 C11 C33 O36 -137.7(2) . . . . ?
C12 C11 C33 O34 42.8(3) . . . . ?
C33 C11 C10 N2 -149.48(17) . . . . ?
C33 C11 C10 N9 96.0(2) . . . . ?
C33 C11 C12 C1 146.71(18) . . . . ?
C6 N7 C8 N9 -178.23(18) . . . . ?
C6 N7 C8 C3 0.6(3) . . . . ?
C6 N5 C4 Cl37 179.07(16) . . . . ?
C6 N5 C4 C3 -0.6(3) . . . . ?
C19 C20 C15 C14 179.59(19) . . . . ?
C19 C20 C15 C16 -0.5(3) . . . . ?
C19 C18 C17 C16 -0.6(4) . . . . ?
C24 N9 C8 N7 1.1(3) . . . . ?
C24 N9 C8 C3 -177.86(19) . . . . ?
C24 N9 C10 N2 175.16(17) . . . . ?
C24 N9 C10 C11 -69.6(2) . . . . ?
C24 C25 C26 O28 171.7(2) . . . . ?
C24 C25 C26 O27 -7.0(5) . . . . ?
C26 O28 C C0AA -179.6(4) . . . . ?
C31 O30 C29 O32 1.6(4) . . . . ?
C31 O30 C29 C11 -174.8(2) . . . . ?
C35 O34 C33 O36 2.1(4) . . . . ?
C35 O34 C33 C11 -178.4(3) . . . . ?
C O28 C26 O27 5.9(5) . . . . ?
C O28 C26 C25 -172.9(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.258
_oxdiff_exptl_absorpt_empirical_full_min 0.716
