# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_wuyatong_1207
_database_code_depnum_ccdc_archive 'CCDC 2107861'
loop_
_audit_author_name
_audit_author_address
'Jing Qi'
;Hebei University
China
;
_audit_update_record             
;
2021-09-06 deposited with the CCDC.	2022-03-28 downloaded from the CCDC.
;
_audit_creation_date             2020-12-09
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C36 H34 Br2 N2 O7'
_chemical_formula_sum            'C36 H34 Br2 N2 O7'
_chemical_formula_weight         766.47
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
Br Br -0.6763 1.2805 '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                   12.10511(17)
_cell_length_b                   23.4016(3)
_cell_length_c                   12.13354(15)
_cell_angle_alpha                90
_cell_angle_beta                 95.0522(13)
_cell_angle_gamma                90
_cell_volume                     3423.82(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9798
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.0200
_cell_measurement_theta_min      1.9180
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.427
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.10275
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
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    1.487
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1560
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.918
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            20689
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.918
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.893
_diffrn_reflns_theta_min         3.666
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -18.00  35.00   1.00    0.40    --  -43.18  19.00   0.00   53
  2  ω     44.00 116.00   1.00    0.40    --   43.18  49.00-145.00   72
  3  ω    -58.00 -25.00   1.00    1.00    -- -100.00  49.00-145.00   33
  4  ω    -50.00 -24.00   1.00    1.00    -- -100.00  45.00 -60.00   26
  5  ω    -72.00 -44.00   1.00    1.00    -- -100.00  61.00   0.00   28
  6  ω    -54.00 -27.00   1.00    1.00    -- -100.00  45.00  60.00   27
  7  ω    -54.00 -29.00   1.00    1.00    -- -100.00  45.00  90.00   25
  8  ω   -101.00 -24.00   1.00    1.00    -- -100.00 102.00  78.00   77
  9  ω    -13.00  12.00   1.00    0.40    --   43.18 -19.00  60.00   25
 10  ω     40.00  67.00   1.00    1.00    --  109.26 -61.00   0.00   27
 11  ω     40.00  65.00   1.00    1.00    --  109.26 -61.00 -60.00   25
 12  ω     35.00  60.00   1.00    1.00    --  109.26 -61.00 -90.00   25
 13  ω     37.00  87.00   1.00    1.00    --  109.26 -78.00-136.00   50
 14  ω     41.00  67.00   1.00    1.00    --  109.26 -61.00  30.00   26
 15  ω     91.00 117.00   1.00    1.00    --  109.26  49.00-145.00   26
 16  ω    146.00 175.00   1.00    1.00    --  109.26  49.00-145.00   29
 17  ω    -78.00 -53.00   1.00    0.40    --  -43.18-179.00-120.00   25
 18  ω    -32.00   4.00   1.00    0.40    --   42.93 -49.00  66.00   36
 19  ω     27.00  52.00   1.00    0.40    --   42.93 -49.00  66.00   25
 20  ω    -21.00   5.00   1.00    0.40    --   42.93 -19.00 -60.00   26
 21  ω     95.00 121.00   1.00    0.40    --   42.93 179.00-180.00   26
 22  ω    -31.00  18.00   1.00    0.40    --   42.93 -19.00 120.00   49
 23  ω   -115.00 -89.00   1.00    1.00    -- -100.00 -30.00  90.00   26
 24  ω   -112.00 -70.00   1.00    1.00    -- -100.00 125.00-180.00   42
 25  ω    -54.00 -28.00   1.00    1.00    -- -100.00  45.00-180.00   26
 26  ω   -159.00 -87.00   1.00    1.00    -- -100.00 -94.00-180.00   72
 27  ω   -176.00-129.00   1.00    1.00    -- -100.00 -30.00  90.00   47
 28  ω    -60.00 -27.00   1.00    1.00    -- -100.00 125.00-180.00   33
 29  ω   -103.00 -77.00   1.00    1.00    -- -100.00  77.00-120.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1010684000
_diffrn_orient_matrix_UB_12      -0.0303615000
_diffrn_orient_matrix_UB_13      -0.0599140000
_diffrn_orient_matrix_UB_21      0.0298594000
_diffrn_orient_matrix_UB_22      0.0250150000
_diffrn_orient_matrix_UB_23      -0.1110424000
_diffrn_orient_matrix_UB_31      0.0721981000
_diffrn_orient_matrix_UB_32      -0.0527961000
_diffrn_orient_matrix_UB_33      -0.0180939000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5429
_reflns_number_total             6562
_reflns_odcompleteness_completeness 98.59
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.474
_refine_diff_density_min         -0.610
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     431
_refine_ls_number_reflns         6562
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0422
_refine_ls_restrained_S_all      1.031
_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)+(0.0467P)²+2.1834P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1033
_refine_ls_wR_factor_ref         0.1084
_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:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C20(H20), C21(H21), C23(H23), C26(H26), C27(H27),
 C29(H29), C30(H30)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C31(H31A,H31B,
 H31C), C34(H34A,H34B,H34C), C35(H35A,H35B,H35C), C36(H36A,H36B,H36C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.16243(3) 0.38331(2) 0.33242(3) 0.07324(14) Uani 1 1 d . . . . .
Br2 Br 0.43999(5) 0.33190(2) 0.66396(4) 0.10126(19) Uani 1 1 d . . . . .
O1 O 0.61711(16) 0.51448(8) 0.47738(16) 0.0540(5) Uani 1 1 d . . . . .
O2 O 0.65108(17) 0.48167(10) 0.69515(16) 0.0658(6) Uani 1 1 d . . . . .
O3 O 0.83056(15) 0.46067(8) 0.74279(14) 0.0519(4) Uani 1 1 d . . . . .
O4 O 0.7997(2) 0.53802(9) 0.25640(19) 0.0704(6) Uani 1 1 d . . . . .
O5 O 0.76023(16) 0.39583(8) 0.16159(14) 0.0495(4) Uani 1 1 d . . . . .
O6 O 0.7663(3) 0.22645(9) 0.2628(3) 0.1103(12) Uani 1 1 d . . . . .
O7 O 0.85782(17) 0.29361(8) 0.17662(17) 0.0588(5) Uani 1 1 d . . . . .
N1 N 0.77349(16) 0.47001(8) 0.56332(16) 0.0396(4) Uani 1 1 d . . . . .
N2 N 0.71708(18) 0.31945(8) 0.27410(18) 0.0441(5) Uani 1 1 d . . . . .
C1 C 0.6988(2) 0.48545(10) 0.4737(2) 0.0397(5) Uani 1 1 d . . . . .
C2 C 0.7410(2) 0.45951(10) 0.36865(19) 0.0383(5) Uani 1 1 d . . . . .
C3 C 0.8559(2) 0.44056(10) 0.40938(19) 0.0378(5) Uani 1 1 d . . . . .
C4 C 0.9423(2) 0.42167(11) 0.3507(2) 0.0450(6) Uani 1 1 d . . . . .
H4 H 0.933374 0.417917 0.274101 0.054 Uiso 1 1 calc R . . . .
C5 C 1.0414(2) 0.40871(11) 0.4094(2) 0.0472(6) Uani 1 1 d . . . . .
C6 C 1.0583(2) 0.41483(11) 0.5228(2) 0.0488(6) Uani 1 1 d . . . . .
H6 H 1.126602 0.405627 0.559671 0.059 Uiso 1 1 calc R . . . .
C7 C 0.9725(2) 0.43486(11) 0.5817(2) 0.0450(6) Uani 1 1 d . . . . .
H7 H 0.982805 0.439929 0.657939 0.054 Uiso 1 1 calc R . . . .
C8 C 0.87190(19) 0.44698(9) 0.52408(19) 0.0375(5) Uani 1 1 d . . . . .
C9 C 0.7285(2) 0.50523(11) 0.2759(2) 0.0469(6) Uani 1 1 d . . . . .
C10 C 0.6145(2) 0.50083(12) 0.2177(2) 0.0525(6) Uani 1 1 d . . . . .
H10A H 0.618760 0.498745 0.138388 0.063 Uiso 1 1 calc R . . . .
H10B H 0.571044 0.534169 0.233735 0.063 Uiso 1 1 calc R . . . .
C11 C 0.5601(2) 0.44667(11) 0.2589(2) 0.0432(5) Uani 1 1 d . . . . .
H11 H 0.510560 0.458615 0.314309 0.052 Uiso 1 1 calc R . . . .
C12 C 0.65792(19) 0.41232(10) 0.32158(18) 0.0375(5) Uani 1 1 d . . . . .
C13 C 0.7433(2) 0.47188(11) 0.6735(2) 0.0445(6) Uani 1 1 d . . . . .
C14 C 0.8183(3) 0.45156(13) 0.8630(2) 0.0571(7) Uani 1 1 d . . . . .
C15 C 0.7406(4) 0.40256(17) 0.8758(3) 0.0881(12) Uani 1 1 d . . . . .
H15A H 0.666692 0.413577 0.848854 0.132 Uiso 1 1 calc GR . . . .
H15B H 0.741923 0.392360 0.952566 0.132 Uiso 1 1 calc GR . . . .
H15C H 0.763304 0.370377 0.834261 0.132 Uiso 1 1 calc GR . . . .
C16 C 0.7824(4) 0.50610(16) 0.9154(3) 0.0803(11) Uani 1 1 d . . . . .
H16A H 0.828246 0.537074 0.894640 0.120 Uiso 1 1 calc GR . . . .
H16B H 0.789597 0.502034 0.994446 0.120 Uiso 1 1 calc GR . . . .
H16C H 0.706411 0.513945 0.890539 0.120 Uiso 1 1 calc GR . . . .
C17 C 0.9360(3) 0.4362(2) 0.9056(3) 0.0927(13) Uani 1 1 d . . . . .
H17A H 0.958510 0.402390 0.868596 0.139 Uiso 1 1 calc GR . . . .
H17B H 0.939252 0.429170 0.983777 0.139 Uiso 1 1 calc GR . . . .
H17C H 0.984748 0.467135 0.891403 0.139 Uiso 1 1 calc GR . . . .
C18 C 0.7190(2) 0.37681(10) 0.23984(19) 0.0391(5) Uani 1 1 d . . . . .
C19 C 0.6520(2) 0.31411(11) 0.3663(2) 0.0441(5) Uani 1 1 d . . . . .
C20 C 0.6193(3) 0.26528(12) 0.4189(3) 0.0625(8) Uani 1 1 d . . . . .
H20 H 0.638072 0.229185 0.394450 0.075 Uiso 1 1 calc R . . . .
C21 C 0.5580(3) 0.27179(14) 0.5087(3) 0.0684(9) Uani 1 1 d . . . . .
H21 H 0.537185 0.239733 0.547198 0.082 Uiso 1 1 calc R . . . .
C22 C 0.5274(3) 0.32532(13) 0.5419(2) 0.0583(7) Uani 1 1 d . . . . .
C23 C 0.5568(2) 0.37429(12) 0.4884(2) 0.0488(6) Uani 1 1 d . . . . .
H23 H 0.534392 0.410179 0.510751 0.059 Uiso 1 1 calc R . . . .
C24 C 0.6208(2) 0.36791(10) 0.40024(19) 0.0392(5) Uani 1 1 d . . . . .
C25 C 0.4919(2) 0.41087(11) 0.1741(2) 0.0449(6) Uani 1 1 d . . . . .
C26 C 0.4131(2) 0.37321(14) 0.2088(2) 0.0567(7) Uani 1 1 d . . . . .
H26 H 0.402689 0.370785 0.283671 0.068 Uiso 1 1 calc R . . . .
C27 C 0.3503(3) 0.33950(16) 0.1347(3) 0.0680(8) Uani 1 1 d . . . . .
H27 H 0.298929 0.314394 0.160666 0.082 Uiso 1 1 calc R . . . .
C28 C 0.3619(3) 0.34213(15) 0.0219(3) 0.0654(8) Uani 1 1 d . . . . .
C29 C 0.4408(3) 0.37914(15) -0.0125(3) 0.0661(8) Uani 1 1 d . . . . .
H29 H 0.451211 0.381475 -0.087433 0.079 Uiso 1 1 calc R . . . .
C30 C 0.5043(3) 0.41258(13) 0.0614(2) 0.0570(7) Uani 1 1 d . . . . .
H30 H 0.556934 0.436942 0.035458 0.068 Uiso 1 1 calc R . . . .
C31 C 0.2921(4) 0.3049(2) -0.0598(4) 0.1066(16) Uani 1 1 d . . . . .
H31A H 0.264386 0.272733 -0.021744 0.160 Uiso 1 1 calc GR . . . .
H31B H 0.336852 0.291738 -0.116191 0.160 Uiso 1 1 calc GR . . . .
H31C H 0.230979 0.326839 -0.093246 0.160 Uiso 1 1 calc GR . . . .
C32 C 0.7823(3) 0.27453(12) 0.2372(3) 0.0569(7) Uani 1 1 d . . . . .
C33 C 0.9395(3) 0.25408(13) 0.1326(3) 0.0602(8) Uani 1 1 d . . . . .
C34 C 0.8795(4) 0.21163(19) 0.0570(4) 0.1102(17) Uani 1 1 d . . . . .
H34A H 0.840832 0.184949 0.099819 0.165 Uiso 1 1 calc GR . . . .
H34B H 0.931883 0.191478 0.016457 0.165 Uiso 1 1 calc GR . . . .
H34C H 0.827249 0.231234 0.006203 0.165 Uiso 1 1 calc GR . . . .
C35 C 1.0095(4) 0.2273(2) 0.2261(4) 0.1034(15) Uani 1 1 d . . . . .
H35A H 1.039048 0.256607 0.275791 0.155 Uiso 1 1 calc GR . . . .
H35B H 1.069364 0.206710 0.197681 0.155 Uiso 1 1 calc GR . . . .
H35C H 0.965140 0.201537 0.265111 0.155 Uiso 1 1 calc GR . . . .
C36 C 1.0073(4) 0.29440(19) 0.0695(4) 0.1003(14) Uani 1 1 d . . . . .
H36A H 0.961014 0.311371 0.010034 0.150 Uiso 1 1 calc GR . . . .
H36B H 1.066547 0.273735 0.039922 0.150 Uiso 1 1 calc GR . . . .
H36C H 1.037764 0.323834 0.118254 0.150 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
Br1 C5 1.901(2) . ?
Br2 C22 1.901(3) . ?
O1 C1 1.203(3) . ?
O2 C13 1.191(3) . ?
O3 C13 1.317(3) . ?
O3 C14 1.494(3) . ?
O4 C9 1.193(3) . ?
O5 C18 1.197(3) . ?
O6 C32 1.188(4) . ?
O7 C32 1.301(3) . ?
O7 C33 1.487(3) . ?
N1 C1 1.400(3) . ?
N1 C8 1.427(3) . ?
N1 C13 1.417(3) . ?
N2 C18 1.406(3) . ?
N2 C19 1.429(3) . ?
N2 C32 1.411(3) . ?
C1 C2 1.539(3) . ?
C2 C3 1.502(3) . ?
C2 C9 1.550(3) . ?
C2 C12 1.567(3) . ?
C3 C4 1.388(3) . ?
C3 C8 1.396(3) . ?
C4 C5 1.374(4) . ?
C5 C6 1.381(4) . ?
C6 C7 1.393(4) . ?
C7 C8 1.379(3) . ?
C9 C10 1.498(4) . ?
C10 C11 1.532(4) . ?
C11 C12 1.571(3) . ?
C11 C25 1.514(4) . ?
C12 C18 1.533(3) . ?
C12 C24 1.506(3) . ?
C14 C15 1.501(5) . ?
C14 C16 1.507(4) . ?
C14 C17 1.515(5) . ?
C19 C20 1.383(4) . ?
C19 C24 1.387(3) . ?
C20 C21 1.380(5) . ?
C21 C22 1.376(4) . ?
C22 C23 1.379(4) . ?
C23 C24 1.384(3) . ?
C25 C26 1.391(4) . ?
C25 C30 1.389(4) . ?
C26 C27 1.374(4) . ?
C27 C28 1.390(5) . ?
C28 C29 1.382(5) . ?
C28 C31 1.519(5) . ?
C29 C30 1.374(4) . ?
C33 C34 1.496(5) . ?
C33 C35 1.492(5) . ?
C33 C36 1.504(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 O3 C14 120.6(2) . . ?
C32 O7 C33 120.8(2) . . ?
C1 N1 C8 109.86(18) . . ?
C1 N1 C13 121.5(2) . . ?
C13 N1 C8 128.2(2) . . ?
C18 N2 C19 109.86(19) . . ?
C18 N2 C32 126.4(2) . . ?
C32 N2 C19 123.1(2) . . ?
O1 C1 N1 126.4(2) . . ?
O1 C1 C2 126.0(2) . . ?
N1 C1 C2 107.61(18) . . ?
C1 C2 C9 108.08(18) . . ?
C1 C2 C12 109.30(19) . . ?
C3 C2 C1 102.10(18) . . ?
C3 C2 C9 118.1(2) . . ?
C3 C2 C12 117.25(19) . . ?
C9 C2 C12 101.75(19) . . ?
C4 C3 C2 130.0(2) . . ?
C4 C3 C8 120.1(2) . . ?
C8 C3 C2 109.85(19) . . ?
C5 C4 C3 117.8(2) . . ?
C4 C5 Br1 119.3(2) . . ?
C4 C5 C6 122.7(2) . . ?
C6 C5 Br1 118.0(2) . . ?
C5 C6 C7 119.7(3) . . ?
C8 C7 C6 118.3(2) . . ?
C3 C8 N1 109.1(2) . . ?
C7 C8 N1 129.4(2) . . ?
C7 C8 C3 121.5(2) . . ?
O4 C9 C2 124.2(3) . . ?
O4 C9 C10 127.0(2) . . ?
C10 C9 C2 108.7(2) . . ?
C9 C10 C11 108.0(2) . . ?
C10 C11 C12 104.7(2) . . ?
C25 C11 C10 117.4(2) . . ?
C25 C11 C12 112.85(19) . . ?
C2 C12 C11 104.36(18) . . ?
C18 C12 C2 106.69(18) . . ?
C18 C12 C11 110.50(18) . . ?
C24 C12 C2 118.23(19) . . ?
C24 C12 C11 113.93(19) . . ?
C24 C12 C18 102.93(19) . . ?
O2 C13 O3 127.7(2) . . ?
O2 C13 N1 122.6(2) . . ?
O3 C13 N1 109.7(2) . . ?
O3 C14 C15 109.1(2) . . ?
O3 C14 C16 110.4(2) . . ?
O3 C14 C17 101.3(2) . . ?
C15 C14 C16 113.3(3) . . ?
C15 C14 C17 111.2(3) . . ?
C16 C14 C17 110.8(3) . . ?
O5 C18 N2 127.5(2) . . ?
O5 C18 C12 124.8(2) . . ?
N2 C18 C12 107.74(19) . . ?
C20 C19 N2 129.3(2) . . ?
C20 C19 C24 121.1(2) . . ?
C24 C19 N2 109.6(2) . . ?
C21 C20 C19 118.0(3) . . ?
C22 C21 C20 120.6(3) . . ?
C21 C22 Br2 118.9(2) . . ?
C21 C22 C23 122.2(3) . . ?
C23 C22 Br2 118.9(2) . . ?
C22 C23 C24 117.3(3) . . ?
C19 C24 C12 109.5(2) . . ?
C23 C24 C12 129.4(2) . . ?
C23 C24 C19 120.9(2) . . ?
C26 C25 C11 119.5(2) . . ?
C30 C25 C11 123.6(3) . . ?
C30 C25 C26 116.9(3) . . ?
C27 C26 C25 121.4(3) . . ?
C26 C27 C28 121.4(3) . . ?
C27 C28 C31 121.3(3) . . ?
C29 C28 C27 117.3(3) . . ?
C29 C28 C31 121.4(3) . . ?
C30 C29 C28 121.5(3) . . ?
C29 C30 C25 121.6(3) . . ?
O6 C32 O7 127.8(3) . . ?
O6 C32 N2 120.9(3) . . ?
O7 C32 N2 111.4(2) . . ?
O7 C33 C34 109.3(3) . . ?
O7 C33 C35 109.8(3) . . ?
O7 C33 C36 101.7(2) . . ?
C34 C33 C36 111.2(4) . . ?
C35 C33 C34 113.6(4) . . ?
C35 C33 C36 110.6(4) . . ?

_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 8.296
_oxdiff_exptl_absorpt_empirical_full_min 0.555
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cu_210519_2F_Cu_0m
_database_code_depnum_ccdc_archive 'CCDC 2107864'
loop_
_audit_author_name
_audit_author_address
'Jing Qi'
;Hebei University
China
;
_audit_update_record             
;
2021-09-06 deposited with the CCDC.	2022-03-28 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            'C35 H32 F2 N2 O7'
_chemical_formula_weight         630.62

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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   19.564(4)
_cell_length_b                   15.658(3)
_cell_length_c                   21.549(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.928(14)
_cell_angle_gamma                90
_cell_volume                     6481(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    6938
_cell_measurement_theta_min      3.64
_cell_measurement_theta_max      68.44

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_F_000             2640
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.490
_exptl_crystal_size_mid          0.420
_exptl_crystal_size_min          0.350
_exptl_absorpt_coefficient_mu    0.819
_shelx_estimated_absorpt_T_min   0.690
_shelx_estimated_absorpt_T_max   0.762
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27462
_diffrn_reflns_av_unetI/netI     0.1030
_diffrn_reflns_av_R_equivalents  0.0960
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.642
_diffrn_reflns_theta_max         68.994
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             9454
_reflns_number_gt                7987
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.998
_reflns_Friedel_fraction_max     0.982
_reflns_Friedel_fraction_full    0.998

_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          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1716P)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_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.5(3)
_chemical_absolute_configuration UNK
_refine_ls_number_reflns         9454
_refine_ls_number_parameters     842
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0955
_refine_ls_R_factor_gt           0.0874
_refine_ls_wR_factor_ref         0.2386
_refine_ls_wR_factor_gt          0.2307
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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 0.7028(3) 0.0141(4) 0.4626(4) 0.0462(14) Uani 1 1 d . . . . .
H1 H 0.7206 0.0646 0.4842 0.055 Uiso 1 1 calc R U . . .
C2 C 0.7258(4) -0.0656(4) 0.4879(4) 0.0510(16) Uani 1 1 d . . . . .
H2 H 0.7593 -0.0691 0.5260 0.061 Uiso 1 1 calc R U . . .
C3 C 0.6992(4) -0.1392(4) 0.4568(4) 0.0482(15) Uani 1 1 d . . . . .
H3 H 0.7139 -0.1936 0.4738 0.058 Uiso 1 1 calc R U . . .
C4 C 0.6511(4) -0.1332(4) 0.4009(4) 0.0513(17) Uani 1 1 d . . . . .
H4 H 0.6334 -0.1837 0.3792 0.062 Uiso 1 1 calc R U . . .
C5 C 0.6285(3) -0.0534(4) 0.3762(3) 0.0414(13) Uani 1 1 d . . . . .
H5 H 0.5948 -0.0502 0.3382 0.050 Uiso 1 1 calc R U . . .
C6 C 0.6543(3) 0.0207(4) 0.4062(3) 0.0395(13) Uani 1 1 d . . . . .
C7 C 0.6299(3) 0.1092(3) 0.3832(3) 0.0385(13) Uani 1 1 d . . . . .
H7 H 0.6695 0.1495 0.3971 0.046 Uiso 1 1 calc R U . . .
C8 C 0.6060(4) 0.1202(4) 0.3114(3) 0.0447(14) Uani 1 1 d . . . . .
H8A H 0.6435 0.1458 0.2924 0.054 Uiso 1 1 calc R U . . .
H8B H 0.5927 0.0646 0.2909 0.054 Uiso 1 1 calc R U . . .
C9 C 0.5429(3) 0.1802(3) 0.3046(3) 0.0403(13) Uani 1 1 d . . . . .
C10 C 0.5381(3) 0.2181(3) 0.3696(3) 0.0376(13) Uani 1 1 d . . . . .
C11 C 0.5662(3) 0.1415(3) 0.4133(3) 0.0358(13) Uani 1 1 d . . . . .
C70 C 0.4179(3) 0.4643(3) 0.6163(3) 0.0359(12) Uani 1 1 d . . . . .
C12 C 0.5889(3) 0.1633(3) 0.4830(3) 0.0391(13) Uani 1 1 d . . . . .
C13 C 0.5105(3) 0.0525(3) 0.4773(3) 0.0412(14) Uani 1 1 d . . . . .
C14 C 0.5123(3) 0.0722(3) 0.4152(3) 0.0367(13) Uani 1 1 d . . . . .
C15 C 0.4726(4) 0.0282(4) 0.3651(4) 0.0461(15) Uani 1 1 d . . . . .
H15 H 0.4746 0.0408 0.3224 0.055 Uiso 1 1 calc R U . . .
C16 C 0.4292(3) -0.0360(4) 0.3816(4) 0.0501(17) Uani 1 1 d . . . . .
C17 C 0.4279(4) -0.0566(4) 0.4426(4) 0.0544(18) Uani 1 1 d . . . . .
H17 H 0.3995 -0.1027 0.4512 0.065 Uiso 1 1 calc R U . . .
C18 C 0.4670(4) -0.0119(4) 0.4929(4) 0.0512(17) Uani 1 1 d . . . . .
H18 H 0.4644 -0.0244 0.5355 0.061 Uiso 1 1 calc R U . . .
C19 C 0.5690(4) 0.0987(4) 0.5863(4) 0.0503(16) Uani 1 1 d . . . . .
C20 C 0.6465(5) 0.1488(6) 0.6820(4) 0.063(2) Uani 1 1 d . . . . .
C21 C 0.7030(5) 0.2134(9) 0.6901(5) 0.083(3) Uani 1 1 d . . . . .
H21A H 0.7397 0.1943 0.6680 0.124 Uiso 1 1 calc R U . . .
H21B H 0.7223 0.2204 0.7352 0.124 Uiso 1 1 calc R U . . .
H21C H 0.6841 0.2680 0.6724 0.124 Uiso 1 1 calc R U . . .
C22 C 0.5878(5) 0.1795(7) 0.7153(4) 0.074(2) Uani 1 1 d . . . . .
H22A H 0.6076 0.1954 0.7590 0.111 Uiso 1 1 calc R U . . .
H22B H 0.5539 0.1333 0.7153 0.111 Uiso 1 1 calc R U . . .
H22C H 0.5646 0.2291 0.6929 0.111 Uiso 1 1 calc R U . . .
C23 C 0.6738(7) 0.0619(7) 0.7040(6) 0.088(3) Uani 1 1 d . . . . .
H23A H 0.7065 0.0423 0.6777 0.132 Uiso 1 1 calc R U . . .
H23B H 0.6350 0.0216 0.7003 0.132 Uiso 1 1 calc R U . . .
H23C H 0.6978 0.0653 0.7482 0.132 Uiso 1 1 calc R U . . .
C24 C 0.5886(3) 0.2960(3) 0.3787(3) 0.0404(13) Uani 1 1 d . . . . .
C25 C 0.4698(3) 0.2568(4) 0.3767(3) 0.0386(12) Uani 1 1 d . . . . .
C26 C 0.4044(3) 0.2216(4) 0.3687(4) 0.0465(15) Uani 1 1 d . . . . .
H26 H 0.3968 0.1632 0.3575 0.056 Uiso 1 1 calc R U . . .
C27 C 0.3505(3) 0.2735(4) 0.3773(4) 0.0531(18) Uani 1 1 d . . . . .
C28 C 0.3591(4) 0.3580(4) 0.3956(5) 0.060(2) Uani 1 1 d . . . . .
H28 H 0.3207 0.3911 0.4031 0.072 Uiso 1 1 calc R U . . .
C29 C 0.4258(4) 0.3936(4) 0.4026(4) 0.0558(18) Uani 1 1 d . . . . .
H29 H 0.4336 0.4518 0.4144 0.067 Uiso 1 1 calc R U . . .
C30 C 0.4795(3) 0.3429(4) 0.3923(3) 0.0412(13) Uani 1 1 d . . . . .
C31 C 0.5717(4) 0.4532(4) 0.3954(4) 0.0524(17) Uani 1 1 d . . . . .
C32 C 0.6640(4) 0.5459(4) 0.3770(6) 0.077(3) Uani 1 1 d . . . . .
C33 C 0.7349(6) 0.5218(6) 0.3646(10) 0.131(7) Uani 1 1 d . . . . .
H33A H 0.7592 0.4866 0.3996 0.196 Uiso 1 1 calc R U . . .
H33B H 0.7619 0.5737 0.3612 0.196 Uiso 1 1 calc R U . . .
H33C H 0.7295 0.4894 0.3251 0.196 Uiso 1 1 calc R U . . .
C34 C 0.6210(6) 0.5944(6) 0.3202(6) 0.088(3) Uani 1 1 d . . . . .
H34A H 0.6217 0.5625 0.2812 0.132 Uiso 1 1 calc R U . . .
H34B H 0.6412 0.6512 0.3172 0.132 Uiso 1 1 calc R U . . .
H34C H 0.5728 0.6003 0.3263 0.132 Uiso 1 1 calc R U . . .
C35 C 0.6704(7) 0.5927(6) 0.4383(7) 0.101(4) Uani 1 1 d . . . . .
H35A H 0.6239 0.6068 0.4459 0.151 Uiso 1 1 calc R U . . .
H35B H 0.6970 0.6454 0.4365 0.151 Uiso 1 1 calc R U . . .
H35C H 0.6946 0.5566 0.4727 0.151 Uiso 1 1 calc R U . . .
C36 C 0.3070(3) 0.7457(4) 0.5341(4) 0.0476(15) Uani 1 1 d . . . . .
H36 H 0.2907 0.6949 0.5121 0.057 Uiso 1 1 calc R U . . .
C37 C 0.2839(4) 0.8247(4) 0.5081(4) 0.0506(16) Uani 1 1 d . . . . .
H37 H 0.2522 0.8278 0.4689 0.061 Uiso 1 1 calc R U . . .
C38 C 0.3083(4) 0.8991(4) 0.5407(4) 0.0544(18) Uani 1 1 d . . . . .
H38 H 0.2930 0.9534 0.5239 0.065 Uiso 1 1 calc R U . . .
C39 C 0.3539(4) 0.8937(4) 0.5964(4) 0.0526(17) Uani 1 1 d . . . . .
H39 H 0.3707 0.9446 0.6181 0.063 Uiso 1 1 calc R U . . .
C40 C 0.3765(4) 0.8152(4) 0.6225(4) 0.0476(15) Uani 1 1 d . . . . .
H40 H 0.4082 0.8130 0.6618 0.057 Uiso 1 1 calc R U . . .
C41 C 0.3532(3) 0.7400(3) 0.5915(3) 0.0373(13) Uani 1 1 d . . . . .
C42 C 0.3791(3) 0.6522(3) 0.6162(3) 0.0376(13) Uani 1 1 d . . . . .
H42 H 0.3400 0.6112 0.6021 0.045 Uiso 1 1 calc R U . . .
C43 C 0.4023(3) 0.6398(3) 0.6873(3) 0.0423(14) Uani 1 1 d . . . . .
H43A H 0.4177 0.6946 0.7081 0.051 Uiso 1 1 calc R U . . .
H43B H 0.3636 0.6168 0.7061 0.051 Uiso 1 1 calc R U . . .
C44 C 0.4620(3) 0.5768(4) 0.6951(3) 0.0408(14) Uani 1 1 d . . . . .
C45 C 0.4688(3) 0.5421(3) 0.6286(3) 0.0382(13) Uani 1 1 d . . . . .
C46 C 0.4426(3) 0.6207(3) 0.5857(3) 0.0365(12) Uani 1 1 d . . . . .
C47 C 0.4201(3) 0.5992(3) 0.5158(3) 0.0387(13) Uani 1 1 d . . . . .
C48 C 0.4983(3) 0.7111(3) 0.5231(3) 0.0382(13) Uani 1 1 d . . . . .
C49 C 0.4966(3) 0.6889(3) 0.5852(3) 0.0354(12) Uani 1 1 d . . . . .
C50 C 0.5381(3) 0.7304(3) 0.6354(3) 0.0395(13) Uani 1 1 d . . . . .
H50 H 0.5371 0.7158 0.6780 0.047 Uiso 1 1 calc R U . . .
C51 C 0.5812(3) 0.7944(4) 0.6204(3) 0.0431(14) Uani 1 1 d . . . . .
C52 C 0.5829(3) 0.8177(4) 0.5590(4) 0.0469(15) Uani 1 1 d . . . . .
H52 H 0.6126 0.8628 0.5512 0.056 Uiso 1 1 calc R U . . .
C53 C 0.5407(3) 0.7754(4) 0.5077(4) 0.0455(14) Uani 1 1 d . . . . .
H53 H 0.5414 0.7901 0.4650 0.055 Uiso 1 1 calc R U . . .
C54 C 0.4349(3) 0.6739(4) 0.4147(3) 0.0440(14) Uani 1 1 d . . . . .
C55 C 0.3547(4) 0.6366(4) 0.3186(3) 0.0501(16) Uani 1 1 d . . . . .
C56 C 0.4089(5) 0.6352(6) 0.2754(4) 0.069(2) Uani 1 1 d . . . . .
H56A H 0.4389 0.6857 0.2838 0.104 Uiso 1 1 calc R U . . .
H56B H 0.3851 0.6356 0.2311 0.104 Uiso 1 1 calc R U . . .
H56C H 0.4374 0.5835 0.2838 0.104 Uiso 1 1 calc R U . . .
C57 C 0.3042(6) 0.5620(6) 0.3056(5) 0.076(3) Uani 1 1 d . . . . .
H57A H 0.3303 0.5083 0.3087 0.114 Uiso 1 1 calc R U . . .
H57B H 0.2761 0.5676 0.2630 0.114 Uiso 1 1 calc R U . . .
H57C H 0.2736 0.5620 0.3367 0.114 Uiso 1 1 calc R U . . .
C58 C 0.3132(5) 0.7203(5) 0.3143(4) 0.064(2) Uani 1 1 d . . . . .
H58A H 0.2873 0.7228 0.3490 0.097 Uiso 1 1 calc R U . . .
H58B H 0.2806 0.7226 0.2738 0.097 Uiso 1 1 calc R U . . .
H58C H 0.3453 0.7688 0.3175 0.097 Uiso 1 1 calc R U . . .
C59 C 0.5352(3) 0.5043(3) 0.6194(3) 0.0399(13) Uani 1 1 d . . . . .
C60 C 0.6022(4) 0.5388(4) 0.6275(4) 0.0536(18) Uani 1 1 d . . . . .
H60 H 0.6111 0.5953 0.6430 0.064 Uiso 1 1 calc R U . . .
C61 C 0.6541(4) 0.4901(5) 0.6130(5) 0.070(3) Uani 1 1 d . . . . .
C62 C 0.6454(5) 0.4078(5) 0.5904(6) 0.074(3) Uani 1 1 d . . . . .
H62 H 0.6834 0.3767 0.5800 0.089 Uiso 1 1 calc R U . . .
C63 C 0.5792(4) 0.3712(4) 0.5834(5) 0.067(2) Uani 1 1 d . . . . .
H63 H 0.5710 0.3142 0.5688 0.081 Uiso 1 1 calc R U . . .
C64 C 0.5264(4) 0.4198(4) 0.5981(4) 0.0470(15) Uani 1 1 d . . . . .
C65 C 0.4325(3) 0.3089(4) 0.5892(4) 0.0452(15) Uani 1 1 d . . . . .
C66 C 0.3386(3) 0.2139(4) 0.6016(4) 0.0470(16) Uani 1 1 d . . . . .
C67 C 0.3350(4) 0.1708(5) 0.5384(5) 0.061(2) Uani 1 1 d . . . . .
H67A H 0.3139 0.2098 0.5046 0.091 Uiso 1 1 calc R U . . .
H67B H 0.3066 0.1189 0.5367 0.091 Uiso 1 1 calc R U . . .
H67C H 0.3821 0.1556 0.5328 0.091 Uiso 1 1 calc R U . . .
C68 C 0.3797(4) 0.1629(5) 0.6551(5) 0.063(2) Uani 1 1 d . . . . .
H68A H 0.4247 0.1471 0.6447 0.095 Uiso 1 1 calc R U . . .
H68B H 0.3538 0.1111 0.6616 0.095 Uiso 1 1 calc R U . . .
H68C H 0.3874 0.1973 0.6938 0.095 Uiso 1 1 calc R U . . .
C69 C 0.2667(4) 0.2353(4) 0.6148(4) 0.0552(18) Uani 1 1 d . . . . .
H69A H 0.2716 0.2633 0.6561 0.083 Uiso 1 1 calc R U . . .
H69B H 0.2397 0.1826 0.6151 0.083 Uiso 1 1 calc R U . . .
H69C H 0.2426 0.2736 0.5819 0.083 Uiso 1 1 calc R U . . .
F1 F 0.3904(3) -0.0792(3) 0.3331(3) 0.0715(14) Uani 1 1 d . . . . .
F2 F 0.2855(2) 0.2396(3) 0.3684(3) 0.0706(14) Uani 1 1 d . . . . .
F3 F 0.7195(2) 0.5231(3) 0.6218(4) 0.105(3) Uani 1 1 d . . . . .
F4 F 0.6228(2) 0.8343(3) 0.6687(2) 0.0560(10) Uani 1 1 d . . . . .
N1 N 0.5566(3) 0.1061(3) 0.5195(3) 0.0395(11) Uani 1 1 d . . . . .
N2 N 0.5494(3) 0.3672(3) 0.3930(3) 0.0448(12) Uani 1 1 d . . . . .
N3 N 0.4555(3) 0.3957(3) 0.5978(3) 0.0407(12) Uani 1 1 d . . . . .
N4 N 0.4507(3) 0.6594(3) 0.4792(3) 0.0389(11) Uani 1 1 d . . . . .
O1 O 0.5343(3) 0.0525(4) 0.6132(3) 0.0670(15) Uani 1 1 d . . . . .
O2 O 0.6208(3) 0.1487(3) 0.6125(2) 0.0526(11) Uani 1 1 d . . . . .
O3 O 0.6281(3) 0.2201(3) 0.5025(2) 0.0483(11) Uani 1 1 d . . . . .
O4 O 0.5026(3) 0.1934(3) 0.2565(3) 0.0542(12) Uani 1 1 d . . . . .
O5 O 0.6472(2) 0.2955(3) 0.3708(3) 0.0499(12) Uani 1 1 d . . . . .
O6 O 0.6332(3) 0.4603(3) 0.3817(4) 0.0700(17) Uani 1 1 d . . . . .
O7 O 0.5343(3) 0.5096(3) 0.4070(4) 0.0741(18) Uani 1 1 d . . . . .
O8 O 0.4705(3) 0.2547(3) 0.5754(3) 0.0638(15) Uani 1 1 d . . . . .
O9 O 0.3693(2) 0.3004(2) 0.6009(3) 0.0494(12) Uani 1 1 d . . . . .
O10 O 0.3590(2) 0.4638(2) 0.6253(2) 0.0425(10) Uani 1 1 d . . . . .
O11 O 0.5002(3) 0.5582(3) 0.7441(3) 0.0543(12) Uani 1 1 d . . . . .
O12 O 0.3810(2) 0.5417(3) 0.4944(2) 0.0474(11) Uani 1 1 d . . . . .
O13 O 0.3864(3) 0.6222(3) 0.3861(2) 0.0484(11) Uani 1 1 d . . . . .
O14 O 0.4623(3) 0.7317(4) 0.3889(3) 0.0648(15) 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 C6 1.396(10) . ?
C1 C2 1.401(9) . ?
C1 H1 0.9500 . ?
C2 C3 1.384(11) . ?
C2 H2 0.9500 . ?
C3 C4 1.383(11) . ?
C3 H3 0.9500 . ?
C4 C5 1.397(9) . ?
C4 H4 0.9500 . ?
C5 C6 1.377(9) . ?
C5 H5 0.9500 . ?
C6 C7 1.518(7) . ?
C7 C8 1.539(10) . ?
C7 C11 1.590(8) . ?
C7 H7 1.0000 . ?
C8 C9 1.536(8) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 O4 1.196(9) . ?
C9 C10 1.540(9) . ?
C10 C25 1.502(8) . ?
C10 C11 1.559(8) . ?
C10 C24 1.560(8) . ?
C11 C14 1.520(7) . ?
C11 C12 1.524(10) . ?
C70 O10 1.205(8) . ?
C70 N3 1.402(7) . ?
C70 C45 1.564(8) . ?
C12 O3 1.197(8) . ?
C12 N1 1.417(8) . ?
C13 C14 1.380(10) . ?
C13 C18 1.401(9) . ?
C13 N1 1.425(9) . ?
C14 C15 1.387(9) . ?
C15 C16 1.404(9) . ?
C15 H15 0.9500 . ?
C16 F1 1.351(9) . ?
C16 C17 1.359(12) . ?
C17 C18 1.391(12) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 O1 1.212(9) . ?
C19 O2 1.319(9) . ?
C19 N1 1.420(10) . ?
C20 C21 1.482(14) . ?
C20 O2 1.487(10) . ?
C20 C23 1.505(13) . ?
C20 C22 1.543(13) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 O5 1.190(8) . ?
C24 N2 1.419(8) . ?
C25 C26 1.374(9) . ?
C25 C30 1.393(8) . ?
C26 C27 1.371(9) . ?
C26 H26 0.9500 . ?
C27 F2 1.359(8) . ?
C27 C28 1.382(10) . ?
C28 C29 1.401(11) . ?
C28 H28 0.9500 . ?
C29 C30 1.370(9) . ?
C29 H29 0.9500 . ?
C30 N2 1.417(9) . ?
C31 O7 1.202(9) . ?
C31 O6 1.297(10) . ?
C31 N2 1.413(8) . ?
C32 O6 1.481(7) . ?
C32 C35 1.50(2) . ?
C32 C33 1.508(17) . ?
C32 C34 1.546(15) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 C41 1.390(10) . ?
C36 C37 1.396(9) . ?
C36 H36 0.9500 . ?
C37 C38 1.397(10) . ?
C37 H37 0.9500 . ?
C38 C39 1.355(12) . ?
C38 H38 0.9500 . ?
C39 C40 1.388(9) . ?
C39 H39 0.9500 . ?
C40 C41 1.389(9) . ?
C40 H40 0.9500 . ?
C41 C42 1.525(7) . ?
C42 C43 1.526(10) . ?
C42 C46 1.590(8) . ?
C42 H42 1.0000 . ?
C43 C44 1.514(8) . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C44 O11 1.209(9) . ?
C44 C45 1.562(10) . ?
C45 C59 1.474(8) . ?
C45 C46 1.566(7) . ?
C46 C49 1.504(7) . ?
C46 C47 1.524(10) . ?
C47 O12 1.214(7) . ?
C47 N4 1.430(8) . ?
C48 C53 1.385(8) . ?
C48 C49 1.388(9) . ?
C48 N4 1.444(8) . ?
C49 C50 1.385(9) . ?
C50 C51 1.386(9) . ?
C50 H50 0.9500 . ?
C51 F4 1.348(8) . ?
C51 C52 1.378(10) . ?
C52 C53 1.414(10) . ?
C52 H52 0.9500 . ?
C53 H53 0.9500 . ?
C54 O14 1.236(9) . ?
C54 O13 1.309(8) . ?
C54 N4 1.384(9) . ?
C55 O13 1.486(9) . ?
C55 C57 1.522(11) . ?
C55 C58 1.535(10) . ?
C55 C56 1.538(12) . ?
C56 H56A 0.9800 . ?
C56 H56B 0.9800 . ?
C56 H56C 0.9800 . ?
C57 H57A 0.9800 . ?
C57 H57B 0.9800 . ?
C57 H57C 0.9800 . ?
C58 H58A 0.9800 . ?
C58 H58B 0.9800 . ?
C58 H58C 0.9800 . ?
C59 C60 1.397(9) . ?
C59 C64 1.400(8) . ?
C60 C61 1.353(10) . ?
C60 H60 0.9500 . ?
C61 F3 1.360(8) . ?
C61 C62 1.376(11) . ?
C62 C63 1.399(11) . ?
C62 H62 0.9500 . ?
C63 C64 1.368(10) . ?
C63 H63 0.9500 . ?
C64 N3 1.437(8) . ?
C65 O8 1.202(8) . ?
C65 O9 1.315(8) . ?
C65 N3 1.432(7) . ?
C66 O9 1.483(7) . ?
C66 C68 1.503(11) . ?
C66 C67 1.511(12) . ?
C66 C69 1.524(10) . ?
C67 H67A 0.9800 . ?
C67 H67B 0.9800 . ?
C67 H67C 0.9800 . ?
C68 H68A 0.9800 . ?
C68 H68B 0.9800 . ?
C68 H68C 0.9800 . ?
C69 H69A 0.9800 . ?
C69 H69B 0.9800 . ?
C69 H69C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 121.3(6) . . ?
C6 C1 H1 119.4 . . ?
C2 C1 H1 119.4 . . ?
C3 C2 C1 119.3(7) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C4 C3 C2 119.7(6) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 120.4(6) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 120.8(7) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C1 118.4(6) . . ?
C5 C6 C7 123.4(6) . . ?
C1 C6 C7 118.1(6) . . ?
C6 C7 C8 116.5(5) . . ?
C6 C7 C11 112.4(5) . . ?
C8 C7 C11 105.2(5) . . ?
C6 C7 H7 107.4 . . ?
C8 C7 H7 107.4 . . ?
C11 C7 H7 107.4 . . ?
C9 C8 C7 104.5(5) . . ?
C9 C8 H8A 110.9 . . ?
C7 C8 H8A 110.9 . . ?
C9 C8 H8B 110.9 . . ?
C7 C8 H8B 110.9 . . ?
H8A C8 H8B 108.9 . . ?
O4 C9 C8 125.1(6) . . ?
O4 C9 C10 125.3(6) . . ?
C8 C9 C10 109.6(5) . . ?
C25 C10 C9 117.3(5) . . ?
C25 C10 C11 117.9(5) . . ?
C9 C10 C11 100.2(4) . . ?
C25 C10 C24 103.0(4) . . ?
C9 C10 C24 105.6(5) . . ?
C11 C10 C24 112.5(5) . . ?
C14 C11 C12 101.9(5) . . ?
C14 C11 C10 113.5(5) . . ?
C12 C11 C10 115.3(4) . . ?
C14 C11 C7 112.7(4) . . ?
C12 C11 C7 111.7(5) . . ?
C10 C11 C7 102.3(5) . . ?
O10 C70 N3 127.6(5) . . ?
O10 C70 C45 125.2(5) . . ?
N3 C70 C45 107.1(5) . . ?
O3 C12 N1 126.9(6) . . ?
O3 C12 C11 124.0(6) . . ?
N1 C12 C11 109.1(5) . . ?
C14 C13 C18 121.4(7) . . ?
C14 C13 N1 111.0(5) . . ?
C18 C13 N1 127.6(7) . . ?
C13 C14 C15 122.0(6) . . ?
C13 C14 C11 109.4(5) . . ?
C15 C14 C11 128.5(6) . . ?
C14 C15 C16 115.8(7) . . ?
C14 C15 H15 122.1 . . ?
C16 C15 H15 122.1 . . ?
F1 C16 C17 121.2(6) . . ?
F1 C16 C15 116.2(7) . . ?
C17 C16 C15 122.5(6) . . ?
C16 C17 C18 121.7(6) . . ?
C16 C17 H17 119.1 . . ?
C18 C17 H17 119.1 . . ?
C17 C18 C13 116.4(7) . . ?
C17 C18 H18 121.8 . . ?
C13 C18 H18 121.8 . . ?
O1 C19 O2 127.2(8) . . ?
O1 C19 N1 121.9(7) . . ?
O2 C19 N1 110.8(6) . . ?
C21 C20 O2 102.8(7) . . ?
C21 C20 C23 111.6(9) . . ?
O2 C20 C23 110.4(8) . . ?
C21 C20 C22 109.7(9) . . ?
O2 C20 C22 109.3(7) . . ?
C23 C20 C22 112.7(9) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O5 C24 N2 127.6(5) . . ?
O5 C24 C10 125.6(5) . . ?
N2 C24 C10 106.7(5) . . ?
C26 C25 C30 120.1(6) . . ?
C26 C25 C10 130.5(5) . . ?
C30 C25 C10 109.4(5) . . ?
C27 C26 C25 117.8(6) . . ?
C27 C26 H26 121.1 . . ?
C25 C26 H26 121.1 . . ?
F2 C27 C26 118.2(6) . . ?
F2 C27 C28 118.3(6) . . ?
C26 C27 C28 123.5(6) . . ?
C27 C28 C29 118.2(6) . . ?
C27 C28 H28 120.9 . . ?
C29 C28 H28 120.9 . . ?
C30 C29 C28 118.6(6) . . ?
C30 C29 H29 120.7 . . ?
C28 C29 H29 120.7 . . ?
C29 C30 C25 121.8(6) . . ?
C29 C30 N2 127.7(6) . . ?
C25 C30 N2 110.5(5) . . ?
O7 C31 O6 127.8(6) . . ?
O7 C31 N2 120.7(7) . . ?
O6 C31 N2 111.4(6) . . ?
O6 C32 C35 110.5(9) . . ?
O6 C32 C33 100.7(6) . . ?
C35 C32 C33 110.7(11) . . ?
O6 C32 C34 109.3(7) . . ?
C35 C32 C34 113.5(8) . . ?
C33 C32 C34 111.4(12) . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C32 C34 H34A 109.5 . . ?
C32 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C32 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C32 C35 H35A 109.5 . . ?
C32 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C32 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C41 C36 C37 121.3(6) . . ?
C41 C36 H36 119.3 . . ?
C37 C36 H36 119.3 . . ?
C36 C37 C38 118.9(7) . . ?
C36 C37 H37 120.5 . . ?
C38 C37 H37 120.5 . . ?
C39 C38 C37 119.9(6) . . ?
C39 C38 H38 120.1 . . ?
C37 C38 H38 120.1 . . ?
C38 C39 C40 121.3(6) . . ?
C38 C39 H39 119.4 . . ?
C40 C39 H39 119.4 . . ?
C39 C40 C41 120.4(7) . . ?
C39 C40 H40 119.8 . . ?
C41 C40 H40 119.8 . . ?
C40 C41 C36 118.2(6) . . ?
C40 C41 C42 122.7(6) . . ?
C36 C41 C42 119.0(5) . . ?
C41 C42 C43 118.7(5) . . ?
C41 C42 C46 111.7(5) . . ?
C43 C42 C46 105.6(5) . . ?
C41 C42 H42 106.7 . . ?
C43 C42 H42 106.7 . . ?
C46 C42 H42 106.7 . . ?
C44 C43 C42 105.7(5) . . ?
C44 C43 H43A 110.6 . . ?
C42 C43 H43A 110.6 . . ?
C44 C43 H43B 110.6 . . ?
C42 C43 H43B 110.6 . . ?
H43A C43 H43B 108.7 . . ?
O11 C44 C43 126.1(6) . . ?
O11 C44 C45 124.9(6) . . ?
C43 C44 C45 108.9(5) . . ?
C59 C45 C44 119.6(6) . . ?
C59 C45 C70 102.3(4) . . ?
C44 C45 C70 105.3(5) . . ?
C59 C45 C46 115.8(5) . . ?
C44 C45 C46 101.1(4) . . ?
C70 C45 C46 112.6(5) . . ?
C49 C46 C47 102.7(5) . . ?
C49 C46 C45 114.2(5) . . ?
C47 C46 C45 114.3(4) . . ?
C49 C46 C42 112.8(4) . . ?
C47 C46 C42 112.1(5) . . ?
C45 C46 C42 101.2(5) . . ?
O12 C47 N4 125.4(6) . . ?
O12 C47 C46 125.5(6) . . ?
N4 C47 C46 109.1(5) . . ?
C53 C48 C49 122.6(6) . . ?
C53 C48 N4 126.3(6) . . ?
C49 C48 N4 111.2(5) . . ?
C50 C49 C48 121.1(5) . . ?
C50 C49 C46 129.6(6) . . ?
C48 C49 C46 109.2(5) . . ?
C49 C50 C51 116.7(6) . . ?
C49 C50 H50 121.6 . . ?
C51 C50 H50 121.6 . . ?
F4 C51 C52 119.8(6) . . ?
F4 C51 C50 117.4(6) . . ?
C52 C51 C50 122.8(6) . . ?
C51 C52 C53 120.7(5) . . ?
C51 C52 H52 119.7 . . ?
C53 C52 H52 119.7 . . ?
C48 C53 C52 116.1(6) . . ?
C48 C53 H53 121.9 . . ?
C52 C53 H53 121.9 . . ?
O14 C54 O13 125.4(7) . . ?
O14 C54 N4 122.5(6) . . ?
O13 C54 N4 112.1(5) . . ?
O13 C55 C57 101.5(6) . . ?
O13 C55 C58 107.7(6) . . ?
C57 C55 C58 109.1(7) . . ?
O13 C55 C56 112.5(6) . . ?
C57 C55 C56 112.1(8) . . ?
C58 C55 C56 113.2(7) . . ?
C55 C56 H56A 109.5 . . ?
C55 C56 H56B 109.5 . . ?
H56A C56 H56B 109.5 . . ?
C55 C56 H56C 109.5 . . ?
H56A C56 H56C 109.5 . . ?
H56B C56 H56C 109.5 . . ?
C55 C57 H57A 109.5 . . ?
C55 C57 H57B 109.5 . . ?
H57A C57 H57B 109.5 . . ?
C55 C57 H57C 109.5 . . ?
H57A C57 H57C 109.5 . . ?
H57B C57 H57C 109.5 . . ?
C55 C58 H58A 109.5 . . ?
C55 C58 H58B 109.5 . . ?
H58A C58 H58B 109.5 . . ?
C55 C58 H58C 109.5 . . ?
H58A C58 H58C 109.5 . . ?
H58B C58 H58C 109.5 . . ?
C60 C59 C64 117.4(6) . . ?
C60 C59 C45 131.1(5) . . ?
C64 C59 C45 111.5(5) . . ?
C61 C60 C59 118.7(6) . . ?
C61 C60 H60 120.6 . . ?
C59 C60 H60 120.6 . . ?
C60 C61 F3 118.8(7) . . ?
C60 C61 C62 124.2(7) . . ?
F3 C61 C62 117.0(7) . . ?
C61 C62 C63 118.1(7) . . ?
C61 C62 H62 120.9 . . ?
C63 C62 H62 120.9 . . ?
C64 C63 C62 118.1(6) . . ?
C64 C63 H63 120.9 . . ?
C62 C63 H63 120.9 . . ?
C63 C64 C59 123.4(6) . . ?
C63 C64 N3 128.5(6) . . ?
C59 C64 N3 108.0(5) . . ?
O8 C65 O9 128.7(5) . . ?
O8 C65 N3 120.5(6) . . ?
O9 C65 N3 110.8(5) . . ?
O9 C66 C68 109.6(6) . . ?
O9 C66 C67 110.4(6) . . ?
C68 C66 C67 112.4(6) . . ?
O9 C66 C69 101.0(5) . . ?
C68 C66 C69 110.6(7) . . ?
C67 C66 C69 112.3(6) . . ?
C66 C67 H67A 109.5 . . ?
C66 C67 H67B 109.5 . . ?
H67A C67 H67B 109.5 . . ?
C66 C67 H67C 109.5 . . ?
H67A C67 H67C 109.5 . . ?
H67B C67 H67C 109.5 . . ?
C66 C68 H68A 109.5 . . ?
C66 C68 H68B 109.5 . . ?
H68A C68 H68B 109.5 . . ?
C66 C68 H68C 109.5 . . ?
H68A C68 H68C 109.5 . . ?
H68B C68 H68C 109.5 . . ?
C66 C69 H69A 109.5 . . ?
C66 C69 H69B 109.5 . . ?
H69A C69 H69B 109.5 . . ?
C66 C69 H69C 109.5 . . ?
H69A C69 H69C 109.5 . . ?
H69B C69 H69C 109.5 . . ?
C12 N1 C19 127.2(6) . . ?
C12 N1 C13 108.3(5) . . ?
C19 N1 C13 124.5(5) . . ?
C31 N2 C30 123.2(5) . . ?
C31 N2 C24 125.5(6) . . ?
C30 N2 C24 110.2(5) . . ?
C70 N3 C65 126.6(5) . . ?
C70 N3 C64 110.7(4) . . ?
C65 N3 C64 122.0(5) . . ?
C54 N4 C47 128.6(5) . . ?
C54 N4 C48 124.1(5) . . ?
C47 N4 C48 107.0(5) . . ?
C19 O2 C20 121.1(6) . . ?
C31 O6 C32 120.0(6) . . ?
C65 O9 C66 119.4(5) . . ?
C54 O13 C55 119.9(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
C6 C1 C2 C3 -0.9(11) . . . . ?
C1 C2 C3 C4 0.9(10) . . . . ?
C2 C3 C4 C5 -1.1(11) . . . . ?
C3 C4 C5 C6 1.2(10) . . . . ?
C4 C5 C6 C1 -1.2(10) . . . . ?
C4 C5 C6 C7 -177.6(6) . . . . ?
C2 C1 C6 C5 1.1(10) . . . . ?
C2 C1 C6 C7 177.6(6) . . . . ?
C5 C6 C7 C8 -31.3(8) . . . . ?
C1 C6 C7 C8 152.4(6) . . . . ?
C5 C6 C7 C11 90.2(7) . . . . ?
C1 C6 C7 C11 -86.2(7) . . . . ?
C6 C7 C8 C9 141.3(5) . . . . ?
C11 C7 C8 C9 16.1(6) . . . . ?
C7 C8 C9 O4 -167.0(6) . . . . ?
C7 C8 C9 C10 10.9(6) . . . . ?
O4 C9 C10 C25 15.5(8) . . . . ?
C8 C9 C10 C25 -162.4(5) . . . . ?
O4 C9 C10 C11 144.5(6) . . . . ?
C8 C9 C10 C11 -33.5(6) . . . . ?
O4 C9 C10 C24 -98.5(7) . . . . ?
C8 C9 C10 C24 83.5(5) . . . . ?
C25 C10 C11 C14 48.6(7) . . . . ?
C9 C10 C11 C14 -80.0(6) . . . . ?
C24 C10 C11 C14 168.3(5) . . . . ?
C25 C10 C11 C12 -68.4(7) . . . . ?
C9 C10 C11 C12 163.1(5) . . . . ?
C24 C10 C11 C12 51.3(7) . . . . ?
C25 C10 C11 C7 170.2(5) . . . . ?
C9 C10 C11 C7 41.7(5) . . . . ?
C24 C10 C11 C7 -70.1(6) . . . . ?
C6 C7 C11 C14 -42.4(7) . . . . ?
C8 C7 C11 C14 85.3(6) . . . . ?
C6 C7 C11 C12 71.5(6) . . . . ?
C8 C7 C11 C12 -160.7(4) . . . . ?
C6 C7 C11 C10 -164.6(5) . . . . ?
C8 C7 C11 C10 -36.9(5) . . . . ?
C14 C11 C12 O3 -174.6(5) . . . . ?
C10 C11 C12 O3 -51.3(7) . . . . ?
C7 C11 C12 O3 64.9(7) . . . . ?
C14 C11 C12 N1 5.6(5) . . . . ?
C10 C11 C12 N1 129.0(5) . . . . ?
C7 C11 C12 N1 -114.8(5) . . . . ?
C18 C13 C14 C15 -1.5(9) . . . . ?
N1 C13 C14 C15 179.2(5) . . . . ?
C18 C13 C14 C11 -177.6(5) . . . . ?
N1 C13 C14 C11 3.1(6) . . . . ?
C12 C11 C14 C13 -5.2(6) . . . . ?
C10 C11 C14 C13 -129.8(5) . . . . ?
C7 C11 C14 C13 114.5(6) . . . . ?
C12 C11 C14 C15 179.0(5) . . . . ?
C10 C11 C14 C15 54.4(8) . . . . ?
C7 C11 C14 C15 -61.2(8) . . . . ?
C13 C14 C15 C16 1.5(8) . . . . ?
C11 C14 C15 C16 176.8(5) . . . . ?
C14 C15 C16 F1 -179.9(5) . . . . ?
C14 C15 C16 C17 -2.5(9) . . . . ?
F1 C16 C17 C18 -179.2(6) . . . . ?
C15 C16 C17 C18 3.5(10) . . . . ?
C16 C17 C18 C13 -3.2(10) . . . . ?
C14 C13 C18 C17 2.2(9) . . . . ?
N1 C13 C18 C17 -178.6(5) . . . . ?
C25 C10 C24 O5 -172.4(7) . . . . ?
C9 C10 C24 O5 -48.8(8) . . . . ?
C11 C10 C24 O5 59.6(9) . . . . ?
C25 C10 C24 N2 3.1(7) . . . . ?
C9 C10 C24 N2 126.7(5) . . . . ?
C11 C10 C24 N2 -125.0(5) . . . . ?
C9 C10 C25 C26 58.7(9) . . . . ?
C11 C10 C25 C26 -61.2(10) . . . . ?
C24 C10 C25 C26 174.2(7) . . . . ?
C9 C10 C25 C30 -119.3(6) . . . . ?
C11 C10 C25 C30 120.8(6) . . . . ?
C24 C10 C25 C30 -3.8(7) . . . . ?
C30 C25 C26 C27 -0.9(11) . . . . ?
C10 C25 C26 C27 -178.7(7) . . . . ?
C25 C26 C27 F2 178.9(7) . . . . ?
C25 C26 C27 C28 -2.1(13) . . . . ?
F2 C27 C28 C29 -177.9(8) . . . . ?
C26 C27 C28 C29 3.2(14) . . . . ?
C27 C28 C29 C30 -1.2(13) . . . . ?
C28 C29 C30 C25 -1.7(12) . . . . ?
C28 C29 C30 N2 175.7(7) . . . . ?
C26 C25 C30 C29 2.8(11) . . . . ?
C10 C25 C30 C29 -179.0(7) . . . . ?
C26 C25 C30 N2 -175.0(6) . . . . ?
C10 C25 C30 N2 3.2(8) . . . . ?
C41 C36 C37 C38 0.3(11) . . . . ?
C36 C37 C38 C39 0.4(11) . . . . ?
C37 C38 C39 C40 -0.8(12) . . . . ?
C38 C39 C40 C41 0.5(11) . . . . ?
C39 C40 C41 C36 0.1(10) . . . . ?
C39 C40 C41 C42 176.8(6) . . . . ?
C37 C36 C41 C40 -0.5(10) . . . . ?
C37 C36 C41 C42 -177.3(6) . . . . ?
C40 C41 C42 C43 29.5(8) . . . . ?
C36 C41 C42 C43 -153.8(6) . . . . ?
C40 C41 C42 C46 -93.7(7) . . . . ?
C36 C41 C42 C46 82.9(7) . . . . ?
C41 C42 C43 C44 -145.3(5) . . . . ?
C46 C42 C43 C44 -19.1(5) . . . . ?
C42 C43 C44 O11 170.3(6) . . . . ?
C42 C43 C44 C45 -7.2(6) . . . . ?
O11 C44 C45 C59 -18.6(8) . . . . ?
C43 C44 C45 C59 159.0(5) . . . . ?
O11 C44 C45 C70 95.6(7) . . . . ?
C43 C44 C45 C70 -86.8(5) . . . . ?
O11 C44 C45 C46 -147.0(6) . . . . ?
C43 C44 C45 C46 30.5(5) . . . . ?
O10 C70 C45 C59 171.6(6) . . . . ?
N3 C70 C45 C59 -4.2(7) . . . . ?
O10 C70 C45 C44 45.9(8) . . . . ?
N3 C70 C45 C44 -129.9(5) . . . . ?
O10 C70 C45 C46 -63.4(8) . . . . ?
N3 C70 C45 C46 120.9(5) . . . . ?
C59 C45 C46 C49 -49.6(7) . . . . ?
C44 C45 C46 C49 81.2(6) . . . . ?
C70 C45 C46 C49 -166.9(5) . . . . ?
C59 C45 C46 C47 68.3(7) . . . . ?
C44 C45 C46 C47 -160.9(5) . . . . ?
C70 C45 C46 C47 -49.0(7) . . . . ?
C59 C45 C46 C42 -171.1(5) . . . . ?
C44 C45 C46 C42 -40.3(5) . . . . ?
C70 C45 C46 C42 71.6(6) . . . . ?
C41 C42 C46 C49 45.7(7) . . . . ?
C43 C42 C46 C49 -84.7(6) . . . . ?
C41 C42 C46 C47 -69.7(6) . . . . ?
C43 C42 C46 C47 159.9(4) . . . . ?
C41 C42 C46 C45 168.1(5) . . . . ?
C43 C42 C46 C45 37.7(5) . . . . ?
C49 C46 C47 O12 173.4(6) . . . . ?
C45 C46 C47 O12 49.2(8) . . . . ?
C42 C46 C47 O12 -65.2(7) . . . . ?
C49 C46 C47 N4 -8.4(6) . . . . ?
C45 C46 C47 N4 -132.6(5) . . . . ?
C42 C46 C47 N4 113.0(5) . . . . ?
C53 C48 C49 C50 -0.2(8) . . . . ?
N4 C48 C49 C50 -179.9(5) . . . . ?
C53 C48 C49 C46 176.8(5) . . . . ?
N4 C48 C49 C46 -2.8(6) . . . . ?
C47 C46 C49 C50 -176.5(5) . . . . ?
C45 C46 C49 C50 -52.2(8) . . . . ?
C42 C46 C49 C50 62.6(8) . . . . ?
C47 C46 C49 C48 6.7(6) . . . . ?
C45 C46 C49 C48 131.0(5) . . . . ?
C42 C46 C49 C48 -114.1(5) . . . . ?
C48 C49 C50 C51 -0.3(8) . . . . ?
C46 C49 C50 C51 -176.7(5) . . . . ?
C49 C50 C51 F4 -178.8(5) . . . . ?
C49 C50 C51 C52 1.0(9) . . . . ?
F4 C51 C52 C53 178.6(6) . . . . ?
C50 C51 C52 C53 -1.2(9) . . . . ?
C49 C48 C53 C52 0.1(9) . . . . ?
N4 C48 C53 C52 179.7(5) . . . . ?
C51 C52 C53 C48 0.6(9) . . . . ?
C44 C45 C59 C60 -59.6(10) . . . . ?
C70 C45 C59 C60 -175.3(8) . . . . ?
C46 C45 C59 C60 61.8(10) . . . . ?
C44 C45 C59 C64 121.4(6) . . . . ?
C70 C45 C59 C64 5.7(7) . . . . ?
C46 C45 C59 C64 -117.2(6) . . . . ?
C64 C59 C60 C61 1.7(12) . . . . ?
C45 C59 C60 C61 -177.3(8) . . . . ?
C59 C60 C61 F3 -179.0(8) . . . . ?
C59 C60 C61 C62 0.0(16) . . . . ?
C60 C61 C62 C63 -1.5(17) . . . . ?
F3 C61 C62 C63 177.5(10) . . . . ?
C61 C62 C63 C64 1.2(16) . . . . ?
C62 C63 C64 C59 0.5(15) . . . . ?
C62 C63 C64 N3 -176.7(8) . . . . ?
C60 C59 C64 C63 -2.0(12) . . . . ?
C45 C59 C64 C63 177.2(8) . . . . ?
C60 C59 C64 N3 175.7(6) . . . . ?
C45 C59 C64 N3 -5.1(8) . . . . ?
O3 C12 N1 C19 -6.6(9) . . . . ?
C11 C12 N1 C19 173.1(5) . . . . ?
O3 C12 N1 C13 176.1(6) . . . . ?
C11 C12 N1 C13 -4.2(6) . . . . ?
O1 C19 N1 C12 173.7(6) . . . . ?
O2 C19 N1 C12 -5.4(8) . . . . ?
O1 C19 N1 C13 -9.5(10) . . . . ?
O2 C19 N1 C13 171.4(5) . . . . ?
C14 C13 N1 C12 0.7(6) . . . . ?
C18 C13 N1 C12 -178.6(6) . . . . ?
C14 C13 N1 C19 -176.7(5) . . . . ?
C18 C13 N1 C19 4.0(9) . . . . ?
O7 C31 N2 C30 11.8(12) . . . . ?
O6 C31 N2 C30 -165.9(7) . . . . ?
O7 C31 N2 C24 178.9(8) . . . . ?
O6 C31 N2 C24 1.1(11) . . . . ?
C29 C30 N2 C31 -10.0(12) . . . . ?
C25 C30 N2 C31 167.7(7) . . . . ?
C29 C30 N2 C24 -178.8(7) . . . . ?
C25 C30 N2 C24 -1.1(8) . . . . ?
O5 C24 N2 C31 5.5(12) . . . . ?
C10 C24 N2 C31 -169.8(7) . . . . ?
O5 C24 N2 C30 174.0(7) . . . . ?
C10 C24 N2 C30 -1.4(7) . . . . ?
O10 C70 N3 C65 -3.9(11) . . . . ?
C45 C70 N3 C65 171.8(6) . . . . ?
O10 C70 N3 C64 -174.2(7) . . . . ?
C45 C70 N3 C64 1.4(7) . . . . ?
O8 C65 N3 C70 -177.3(7) . . . . ?
O9 C65 N3 C70 0.3(10) . . . . ?
O8 C65 N3 C64 -7.9(11) . . . . ?
O9 C65 N3 C64 169.7(6) . . . . ?
C63 C64 N3 C70 179.7(9) . . . . ?
C59 C64 N3 C70 2.2(8) . . . . ?
C63 C64 N3 C65 8.8(13) . . . . ?
C59 C64 N3 C65 -168.7(6) . . . . ?
O14 C54 N4 C47 175.5(7) . . . . ?
O13 C54 N4 C47 -1.8(8) . . . . ?
O14 C54 N4 C48 2.3(10) . . . . ?
O13 C54 N4 C48 -175.0(5) . . . . ?
O12 C47 N4 C54 11.2(10) . . . . ?
C46 C47 N4 C54 -167.0(5) . . . . ?
O12 C47 N4 C48 -174.8(6) . . . . ?
C46 C47 N4 C48 7.0(6) . . . . ?
C53 C48 N4 C54 -7.9(9) . . . . ?
C49 C48 N4 C54 171.7(5) . . . . ?
C53 C48 N4 C47 177.7(6) . . . . ?
C49 C48 N4 C47 -2.7(6) . . . . ?
O1 C19 O2 C20 4.4(11) . . . . ?
N1 C19 O2 C20 -176.5(6) . . . . ?
C21 C20 O2 C19 -179.5(8) . . . . ?
C23 C20 O2 C19 61.4(10) . . . . ?
C22 C20 O2 C19 -63.0(10) . . . . ?
O7 C31 O6 C32 -2.0(14) . . . . ?
N2 C31 O6 C32 175.6(8) . . . . ?
C35 C32 O6 C31 59.7(10) . . . . ?
C33 C32 O6 C31 176.7(11) . . . . ?
C34 C32 O6 C31 -66.0(13) . . . . ?
O8 C65 O9 C66 4.0(12) . . . . ?
N3 C65 O9 C66 -173.3(6) . . . . ?
C68 C66 O9 C65 64.7(9) . . . . ?
C67 C66 O9 C65 -59.6(8) . . . . ?
C69 C66 O9 C65 -178.5(6) . . . . ?
O14 C54 O13 C55 -6.6(10) . . . . ?
N4 C54 O13 C55 170.7(5) . . . . ?
C57 C55 O13 C54 178.5(7) . . . . ?
C58 C55 O13 C54 -67.0(8) . . . . ?
C56 C55 O13 C54 58.5(8) . . . . ?

_refine_diff_density_max         0.591
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.084

####################################################################### 
# 
# 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_cu_220228_OCF_7_0m
_database_code_depnum_ccdc_archive 'CCDC 2158074'
loop_
_audit_author_name
_audit_author_address
'Jing Qi'
;Hebei University
China
;
_audit_update_record             
;
2022-03-12 deposited with the CCDC.	2022-03-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C55 H50 Cl2 F0 N4 O6'
_chemical_formula_weight         933.89

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   13.2632(4)
_cell_length_b                   9.2221(3)
_cell_length_c                   19.4715(6)
_cell_angle_alpha                90
_cell_angle_beta                 97.7280(10)
_cell_angle_gamma                90
_cell_volume                     2360.02(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    9698
_cell_measurement_theta_min      3.36
_cell_measurement_theta_max      68.26
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_F_000             980
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    1.693
_shelx_estimated_absorpt_T_min   0.497
_shelx_estimated_absorpt_T_max   0.773
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            39406
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.290
_diffrn_reflns_theta_max         68.319
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             8486
_reflns_number_gt                8226
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.838
_reflns_Friedel_fraction_max     0.958
_reflns_Friedel_fraction_full    0.964

_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 3599 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.044(5)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         8486
_refine_ls_number_parameters     608
_refine_ls_number_restraints     32
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_ref         0.1299
_refine_ls_wR_factor_gt          0.1275
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_restrained_S_all      1.262
_refine_ls_shift/su_max          0.003
_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
Cl1 Cl 1.10518(10) 0.66684(15) 0.84135(7) 0.0776(3) Uani 1 1 d . . . . .
H1D H 0.477061 -0.046650 0.521260 0.093 Uiso 1 1 d R U . . .
Cl2 Cl 1.10804(9) 0.40128(16) 0.76085(6) 0.0766(3) Uani 1 1 d . . . . .
O1 O 0.46182(16) 0.0116(3) 0.55283(10) 0.0419(5) Uani 1 1 d . . . . .
O2 O 0.50511(17) 0.3500(3) 0.56123(12) 0.0495(6) Uani 1 1 d . . . . .
O3 O 0.14125(15) 0.1089(2) 0.52064(11) 0.0337(4) Uani 1 1 d . . . . .
O4 O 0.72434(15) 0.9409(2) 0.84416(11) 0.0341(4) Uani 1 1 d . . . . .
O5 O 0.56023(14) 0.9897(2) 0.93658(11) 0.0348(4) Uani 1 1 d . . . . .
H5D H 0.496810 1.000515 0.945247 0.042 Uiso 1 1 d R U . . .
O6 O 0.62310(14) 0.5626(2) 1.02248(10) 0.0355(4) Uani 1 1 d . . . . .
N1 N 0.10209(17) 0.3341(2) 0.55958(12) 0.0296(4) Uani 1 1 d . . . . .
N2 N 0.4849(2) 0.2791(3) 0.67041(13) 0.0405(6) Uani 1 1 d . . . . .
N3 N 0.58940(16) 0.8310(2) 0.77828(11) 0.0281(4) Uani 1 1 d . . . . .
N4 N 0.69769(19) 0.4088(2) 0.95209(14) 0.0379(5) Uani 1 1 d . . . . .
C1 C 0.2198(4) 0.5017(5) 0.39487(18) 0.0622(11) Uani 1 1 d . U . . .
H1 H 0.268813 0.565649 0.418583 0.075 Uiso 1 1 calc R U . . .
C2 C 0.1454(5) 0.5548(8) 0.3459(2) 0.0900(18) Uani 1 1 d . U . . .
H2 H 0.143584 0.655638 0.335912 0.108 Uiso 1 1 calc R U . . .
C3 C 0.0750(5) 0.4676(10) 0.3118(3) 0.1031(17) Uani 1 1 d . U . . .
H3 H 0.022972 0.507356 0.278892 0.124 Uiso 1 1 calc R U . . .
C4 C 0.0776(4) 0.3159(10) 0.3246(2) 0.0914(14) Uani 1 1 d . U . . .
H4 H 0.029041 0.253648 0.299321 0.110 Uiso 1 1 calc R U . . .
C5 C 0.1523(3) 0.2593(7) 0.37479(18) 0.0636(11) Uani 1 1 d . U . . .
H5 H 0.154144 0.158328 0.384616 0.076 Uiso 1 1 calc R U . . .
C6 C 0.2241(2) 0.3518(4) 0.41027(14) 0.0418(7) Uani 1 1 d . . . . .
C7 C 0.3062(2) 0.3013(3) 0.46598(13) 0.0293(5) Uani 1 1 d . . . . .
H7 H 0.362353 0.373973 0.467423 0.035 Uiso 1 1 calc R U . . .
C8 C 0.3555(2) 0.1528(4) 0.45962(14) 0.0392(6) Uani 1 1 d . . . . .
H8A H 0.422678 0.163969 0.443446 0.047 Uiso 1 1 calc R U . . .
H8B H 0.311967 0.091770 0.425818 0.047 Uiso 1 1 calc R U . . .
C9 C 0.3678(2) 0.0816(3) 0.53172(12) 0.0286(5) Uani 1 1 d . . . . .
H9 H 0.311565 0.009893 0.533253 0.034 Uiso 1 1 calc R U . . .
C10 C 0.35429(18) 0.2065(3) 0.58294(12) 0.0255(5) Uani 1 1 d . . . . .
C11 C 0.27190(18) 0.3021(3) 0.54027(12) 0.0232(5) Uani 1 1 d . . . . .
C12 C 0.16566(18) 0.2324(3) 0.53863(12) 0.0243(5) Uani 1 1 d . . . . .
C13 C 0.1513(2) 0.4673(3) 0.57381(13) 0.0303(5) Uani 1 1 d . . . . .
C14 C 0.2530(2) 0.4538(3) 0.56489(12) 0.0273(5) Uani 1 1 d . . . . .
C15 C 0.3145(2) 0.5767(3) 0.57165(15) 0.0383(6) Uani 1 1 d . . . . .
H15 H 0.384003 0.571586 0.564810 0.046 Uiso 1 1 calc R U . . .
C16 C 0.2714(3) 0.7075(3) 0.58871(18) 0.0503(9) Uani 1 1 d . . . . .
H16 H 0.312378 0.792317 0.593765 0.060 Uiso 1 1 calc R U . . .
C17 C 0.1699(3) 0.7164(3) 0.5985(2) 0.0549(9) Uani 1 1 d . . . . .
H17 H 0.142717 0.806434 0.611031 0.066 Uiso 1 1 calc R U . . .
C18 C 0.1082(3) 0.5959(4) 0.59009(19) 0.0467(7) Uani 1 1 d . . . . .
H18 H 0.038141 0.601600 0.595401 0.056 Uiso 1 1 calc R U . . .
C19 C -0.0055(2) 0.3097(4) 0.5627(2) 0.0472(7) Uani 1 1 d . . . . .
H19A H -0.023634 0.210720 0.547368 0.071 Uiso 1 1 calc R U . . .
H19B H -0.045899 0.379132 0.532409 0.071 Uiso 1 1 calc R U . . .
H19C H -0.019537 0.322680 0.610477 0.071 Uiso 1 1 calc R U . . .
C20 C 0.4561(2) 0.2879(3) 0.60129(15) 0.0337(6) Uani 1 1 d . . . . .
C21 C 0.4154(2) 0.1966(3) 0.70272(14) 0.0356(6) Uani 1 1 d . . . . .
C22 C 0.4242(3) 0.1538(5) 0.77155(16) 0.0524(9) Uani 1 1 d . . . . .
H22 H 0.480001 0.183915 0.804220 0.063 Uiso 1 1 calc R U . . .
C23 C 0.3480(3) 0.0650(5) 0.79079(16) 0.0558(9) Uani 1 1 d . . . . .
H23 H 0.351766 0.033508 0.837529 0.067 Uiso 1 1 calc R U . . .
C24 C 0.2672(3) 0.0218(4) 0.74327(17) 0.0488(8) Uani 1 1 d . . . . .
H24 H 0.216292 -0.039498 0.757520 0.059 Uiso 1 1 calc R U . . .
C25 C 0.2593(2) 0.0672(3) 0.67446(15) 0.0353(6) Uani 1 1 d . . . . .
H25 H 0.202860 0.038561 0.642017 0.042 Uiso 1 1 calc R U . . .
C26 C 0.3347(2) 0.1545(3) 0.65399(12) 0.0275(5) Uani 1 1 d . . . . .
C27 C 0.5790(3) 0.3362(5) 0.7056(2) 0.0614(10) Uani 1 1 d . . . . .
H27A H 0.565354 0.392370 0.746032 0.092 Uiso 1 1 calc R U . . .
H27B H 0.610481 0.399192 0.673898 0.092 Uiso 1 1 calc R U . . .
H27C H 0.625217 0.256049 0.720633 0.092 Uiso 1 1 calc R U . . .
C28 C 0.9544(2) 0.6541(3) 0.99538(15) 0.0351(6) Uani 1 1 d . . . . .
H28 H 0.965407 0.685504 0.950524 0.042 Uiso 1 1 calc R U . . .
C29 C 1.0307(2) 0.5798(4) 1.03657(18) 0.0439(7) Uani 1 1 d . . . . .
H29 H 1.092874 0.559994 1.019263 0.053 Uiso 1 1 calc R U . . .
C30 C 1.0180(2) 0.5346(4) 1.10140(17) 0.0431(7) Uani 1 1 d . . . . .
H30 H 1.070690 0.483914 1.129484 0.052 Uiso 1 1 calc R U . . .
C31 C 0.9268(2) 0.5640(4) 1.12539(16) 0.0450(7) Uani 1 1 d . . . . .
H31 H 0.916993 0.532921 1.170525 0.054 Uiso 1 1 calc R U . . .
C32 C 0.8492(2) 0.6380(3) 1.08499(14) 0.0357(6) Uani 1 1 d . . . . .
H32 H 0.787326 0.657680 1.102731 0.043 Uiso 1 1 calc R U . . .
C33 C 0.86189(18) 0.6835(3) 1.01870(13) 0.0242(5) Uani 1 1 d . . . . .
C34 C 0.78001(17) 0.7608(2) 0.97051(12) 0.0224(5) Uani 1 1 d . . . . .
H34 H 0.815515 0.819660 0.937907 0.027 Uiso 1 1 calc R U . . .
C35 C 0.70734(19) 0.8650(3) 1.00244(14) 0.0293(5) Uani 1 1 d . . . . .
H35A H 0.732876 0.965839 1.001843 0.035 Uiso 1 1 calc R U . . .
H35B H 0.702782 0.837471 1.051066 0.035 Uiso 1 1 calc R U . . .
C36 C 0.60135(17) 0.8532(3) 0.95823(12) 0.0241(5) Uani 1 1 d . . . . .
H36 H 0.553492 0.802527 0.985746 0.029 Uiso 1 1 calc R U . . .
C37 C 0.61812(17) 0.7581(2) 0.89524(11) 0.0207(4) Uani 1 1 d . . . . .
C38 C 0.70618(17) 0.6556(2) 0.92500(11) 0.0213(4) Uani 1 1 d . . . . .
C39 C 0.66846(18) 0.5395(3) 0.97289(13) 0.0270(5) Uani 1 1 d . . . . .
C40 C 0.7455(2) 0.4192(3) 0.89261(17) 0.0374(6) Uani 1 1 d . . . . .
C41 C 0.75291(19) 0.5638(3) 0.87328(13) 0.0284(5) Uani 1 1 d . . . . .
C42 C 0.7985(2) 0.5996(4) 0.81560(15) 0.0438(7) Uani 1 1 d . . . . .
H42 H 0.805323 0.697705 0.802039 0.053 Uiso 1 1 calc R U . . .
C43 C 0.8341(3) 0.4854(6) 0.77814(18) 0.0669(13) Uani 1 1 d . . . . .
H43 H 0.864149 0.506418 0.737651 0.080 Uiso 1 1 calc R U . . .
C44 C 0.8266(3) 0.3442(5) 0.7984(2) 0.0689(14) Uani 1 1 d . . . . .
H44 H 0.852932 0.270065 0.772028 0.083 Uiso 1 1 calc R U . . .
C45 C 0.7817(3) 0.3055(4) 0.8563(2) 0.0562(10) Uani 1 1 d . . . . .
H45 H 0.776277 0.207328 0.870140 0.067 Uiso 1 1 calc R U . . .
C46 C 0.65247(18) 0.8564(2) 0.83822(12) 0.0242(5) Uani 1 1 d . . . . .
C47 C 0.51435(19) 0.7292(3) 0.78801(13) 0.0267(5) Uani 1 1 d . . . . .
C48 C 0.52650(17) 0.6835(3) 0.85689(12) 0.0227(4) Uani 1 1 d . . . . .
C49 C 0.45861(19) 0.5837(3) 0.87769(13) 0.0293(5) Uani 1 1 d . . . . .
H49 H 0.465079 0.551094 0.924362 0.035 Uiso 1 1 calc R U . . .
C50 C 0.3802(2) 0.5319(4) 0.82835(15) 0.0391(6) Uani 1 1 d . . . . .
H50 H 0.332579 0.464333 0.841979 0.047 Uiso 1 1 calc R U . . .
C51 C 0.3711(2) 0.5774(4) 0.76018(16) 0.0445(7) Uani 1 1 d . . . . .
H51 H 0.318560 0.538540 0.727371 0.053 Uiso 1 1 calc R U . . .
C52 C 0.4372(2) 0.6788(4) 0.73905(14) 0.0374(6) Uani 1 1 d . . . . .
H52 H 0.429970 0.712512 0.692553 0.045 Uiso 1 1 calc R U . . .
C53 C 0.6024(3) 0.8975(4) 0.71211(15) 0.0423(7) Uani 1 1 d . . . . .
H53A H 0.538880 0.945042 0.692576 0.063 Uiso 1 1 calc R U . . .
H53B H 0.619992 0.822681 0.680030 0.063 Uiso 1 1 calc R U . . .
H53C H 0.657106 0.969627 0.719259 0.063 Uiso 1 1 calc R U . . .
C54 C 0.6855(4) 0.2773(4) 0.9920(3) 0.0702(13) Uani 1 1 d . . . . .
H54A H 0.655048 0.200890 0.960925 0.105 Uiso 1 1 calc R U . . .
H54B H 0.641069 0.297589 1.027235 0.105 Uiso 1 1 calc R U . . .
H54C H 0.752173 0.245119 1.014749 0.105 Uiso 1 1 calc R U . . .
C55 C 1.0910(3) 0.4783(5) 0.8404(2) 0.0599(10) Uani 1 1 d . . . . .
H55A H 1.141131 0.435699 0.877131 0.072 Uiso 1 1 calc R U . . .
H55B H 1.022172 0.453698 0.851042 0.072 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
Cl1 C55 1.749(5) . ?
Cl2 C55 1.745(5) . ?
O1 C9 1.415(3) . ?
O2 C20 1.223(4) . ?
O3 C12 1.222(3) . ?
O4 C46 1.225(3) . ?
O5 C36 1.414(3) . ?
O6 C39 1.223(3) . ?
N1 C12 1.360(3) . ?
N1 C13 1.400(4) . ?
N1 C19 1.454(4) . ?
N2 C20 1.351(4) . ?
N2 C21 1.407(4) . ?
N2 C27 1.440(4) . ?
N3 C46 1.362(3) . ?
N3 C47 1.399(3) . ?
N3 C53 1.458(3) . ?
N4 C39 1.345(4) . ?
N4 C40 1.396(5) . ?
N4 C54 1.462(4) . ?
C1 C2 1.367(6) . ?
C1 C6 1.414(6) . ?
C2 C3 1.339(11) . ?
C3 C4 1.420(12) . ?
C4 C5 1.396(7) . ?
C5 C6 1.391(6) . ?
C6 C7 1.503(4) . ?
C7 C8 1.530(4) . ?
C7 C11 1.573(3) . ?
C8 C9 1.538(4) . ?
C9 C10 1.549(3) . ?
C10 C26 1.519(3) . ?
C10 C20 1.544(4) . ?
C10 C11 1.555(3) . ?
C11 C14 1.510(3) . ?
C11 C12 1.546(3) . ?
C13 C18 1.372(4) . ?
C13 C14 1.389(4) . ?
C14 C15 1.393(4) . ?
C15 C16 1.394(5) . ?
C16 C17 1.387(6) . ?
C17 C18 1.377(5) . ?
C21 C22 1.387(4) . ?
C21 C26 1.387(4) . ?
C22 C23 1.391(6) . ?
C23 C24 1.377(6) . ?
C24 C25 1.394(4) . ?
C25 C26 1.383(4) . ?
C28 C29 1.385(4) . ?
C28 C33 1.391(4) . ?
C29 C30 1.361(5) . ?
C30 C31 1.381(5) . ?
C31 C32 1.388(4) . ?
C32 C33 1.389(4) . ?
C33 C34 1.515(3) . ?
C34 C35 1.550(3) . ?
C34 C38 1.566(3) . ?
C35 C36 1.550(3) . ?
C36 C37 1.548(3) . ?
C37 C48 1.505(3) . ?
C37 C46 1.549(3) . ?
C37 C38 1.553(3) . ?
C38 C41 1.511(3) . ?
C38 C39 1.546(3) . ?
C40 C45 1.386(4) . ?
C40 C41 1.393(4) . ?
C41 C42 1.385(4) . ?
C42 C43 1.399(5) . ?
C43 C44 1.369(8) . ?
C44 C45 1.390(7) . ?
C47 C52 1.382(4) . ?
C47 C48 1.394(3) . ?
C48 C49 1.386(3) . ?
C49 C50 1.401(4) . ?
C50 C51 1.382(5) . ?
C51 C52 1.382(5) . ?

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
C12 N1 C13 111.9(2) . . ?
C12 N1 C19 123.8(2) . . ?
C13 N1 C19 124.1(2) . . ?
C20 N2 C21 111.3(2) . . ?
C20 N2 C27 124.2(3) . . ?
C21 N2 C27 124.3(3) . . ?
C46 N3 C47 111.4(2) . . ?
C46 N3 C53 123.6(2) . . ?
C47 N3 C53 124.9(2) . . ?
C39 N4 C40 111.7(2) . . ?
C39 N4 C54 121.8(3) . . ?
C40 N4 C54 126.4(3) . . ?
C2 C1 C6 120.2(5) . . ?
C3 C2 C1 121.4(6) . . ?
C2 C3 C4 120.3(5) . . ?
C5 C4 C3 119.3(6) . . ?
C6 C5 C4 119.5(6) . . ?
C5 C6 C1 119.3(4) . . ?
C5 C6 C7 123.3(3) . . ?
C1 C6 C7 117.4(3) . . ?
C6 C7 C8 119.6(2) . . ?
C6 C7 C11 113.0(2) . . ?
C8 C7 C11 105.0(2) . . ?
C7 C8 C9 107.6(2) . . ?
O1 C9 C8 116.1(2) . . ?
O1 C9 C10 109.0(2) . . ?
C8 C9 C10 105.3(2) . . ?
C26 C10 C20 101.2(2) . . ?
C26 C10 C9 113.6(2) . . ?
C20 C10 C9 109.7(2) . . ?
C26 C10 C11 118.1(2) . . ?
C20 C10 C11 112.2(2) . . ?
C9 C10 C11 102.20(19) . . ?
C14 C11 C12 101.68(19) . . ?
C14 C11 C10 119.4(2) . . ?
C12 C11 C10 110.36(19) . . ?
C14 C11 C7 112.16(19) . . ?
C12 C11 C7 110.7(2) . . ?
C10 C11 C7 102.67(19) . . ?
O3 C12 N1 125.3(2) . . ?
O3 C12 C11 126.8(2) . . ?
N1 C12 C11 107.9(2) . . ?
C18 C13 C14 123.2(3) . . ?
C18 C13 N1 127.3(3) . . ?
C14 C13 N1 109.3(2) . . ?
C13 C14 C15 118.8(3) . . ?
C13 C14 C11 109.2(2) . . ?
C15 C14 C11 131.6(3) . . ?
C14 C15 C16 118.2(3) . . ?
C17 C16 C15 121.4(3) . . ?
C18 C17 C16 120.5(3) . . ?
C13 C18 C17 117.8(3) . . ?
O2 C20 N2 124.1(3) . . ?
O2 C20 C10 127.1(3) . . ?
N2 C20 C10 108.8(2) . . ?
C22 C21 C26 122.6(3) . . ?
C22 C21 N2 127.7(3) . . ?
C26 C21 N2 109.7(2) . . ?
C21 C22 C23 117.3(3) . . ?
C24 C23 C22 121.2(3) . . ?
C23 C24 C25 120.6(3) . . ?
C26 C25 C24 119.2(3) . . ?
C25 C26 C21 119.2(2) . . ?
C25 C26 C10 131.7(2) . . ?
C21 C26 C10 108.9(2) . . ?
C29 C28 C33 121.0(3) . . ?
C30 C29 C28 121.1(3) . . ?
C29 C30 C31 118.4(3) . . ?
C30 C31 C32 121.4(3) . . ?
C31 C32 C33 120.1(3) . . ?
C32 C33 C28 117.8(2) . . ?
C32 C33 C34 123.5(2) . . ?
C28 C33 C34 118.7(2) . . ?
C33 C34 C35 118.4(2) . . ?
C33 C34 C38 113.64(19) . . ?
C35 C34 C38 103.65(18) . . ?
C34 C35 C36 107.46(18) . . ?
O5 C36 C37 111.0(2) . . ?
O5 C36 C35 112.80(19) . . ?
C37 C36 C35 105.29(18) . . ?
C48 C37 C36 117.38(18) . . ?
C48 C37 C46 101.99(19) . . ?
C36 C37 C46 108.90(19) . . ?
C48 C37 C38 115.06(19) . . ?
C36 C37 C38 103.31(18) . . ?
C46 C37 C38 110.17(17) . . ?
C41 C38 C39 102.07(19) . . ?
C41 C38 C37 116.60(19) . . ?
C39 C38 C37 110.99(18) . . ?
C41 C38 C34 116.29(19) . . ?
C39 C38 C34 108.42(18) . . ?
C37 C38 C34 102.47(17) . . ?
O6 C39 N4 125.9(2) . . ?
O6 C39 C38 126.1(2) . . ?
N4 C39 C38 108.0(2) . . ?
C45 C40 C41 123.0(3) . . ?
C45 C40 N4 126.7(3) . . ?
C41 C40 N4 110.3(2) . . ?
C42 C41 C40 120.1(3) . . ?
C42 C41 C38 132.1(3) . . ?
C40 C41 C38 107.8(2) . . ?
C41 C42 C43 117.3(4) . . ?
C44 C43 C42 121.5(4) . . ?
C43 C44 C45 122.3(3) . . ?
C40 C45 C44 115.7(4) . . ?
O4 C46 N3 124.8(2) . . ?
O4 C46 C37 127.2(2) . . ?
N3 C46 C37 107.9(2) . . ?
C52 C47 C48 122.7(2) . . ?
C52 C47 N3 127.3(2) . . ?
C48 C47 N3 109.9(2) . . ?
C49 C48 C47 119.1(2) . . ?
C49 C48 C37 132.2(2) . . ?
C47 C48 C37 108.7(2) . . ?
C48 C49 C50 118.5(2) . . ?
C51 C50 C49 121.1(3) . . ?
C52 C51 C50 121.0(3) . . ?
C47 C52 C51 117.6(3) . . ?
Cl2 C55 Cl1 112.8(2) . . ?

_refine_diff_density_max         0.365
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.049

