# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_20230209-pydmadf1-hbr2
_database_code_depnum_ccdc_archive 'CCDC 2246246'
loop_
_audit_author_name
_audit_author_address
'Ryo Inoue'
;Kwansei Gakuin University
Japan
;
_audit_update_record             
;
2023-03-04 deposited with the CCDC.	2023-04-11 downloaded from the CCDC.
;
_audit_creation_date             2023-02-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'Br, 0.5(C29 H20.978 N O4), 0.5(C29 H22 N O4), 0.5(C4 O)'
_chemical_formula_sum            'C33 H22 Br N O6'
_chemical_formula_weight         608.42
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C26H30NO4Br
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_H-M_alt        'C 2 2 21'
_space_group_name_Hall           'C 2c 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x, -y, -z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z+1/2'

_cell_length_a                   12.3684(14)
_cell_length_b                   14.0492(13)
_cell_length_c                   60.098(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     10443(2)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    3216
_cell_measurement_temperature    150
_cell_measurement_theta_max      30.7780
_cell_measurement_theta_min      2.2390
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.923
_exptl_absorpt_coefficient_mu    1.625
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.28376
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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    1.548
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             4960
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0920
_diffrn_reflns_av_unetI/netI     0.1646
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.901
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       86
_diffrn_reflns_limit_l_min       -81
_diffrn_reflns_number            23524
_diffrn_reflns_point_group_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.856
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.213
_diffrn_reflns_theta_min         2.033
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.901
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00  70.00   0.50   60.00    --  -20.00  45.00   0.00  360
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0269672000
_diffrn_orient_matrix_UB_12      0.0375669000
_diffrn_orient_matrix_UB_13      0.0055993000
_diffrn_orient_matrix_UB_21      0.0115454000
_diffrn_orient_matrix_UB_22      0.0216793000
_diffrn_orient_matrix_UB_23      -0.0103819000
_diffrn_orient_matrix_UB_31      -0.0492765000
_diffrn_orient_matrix_UB_32      0.0257718000
_diffrn_orient_matrix_UB_33      0.0006040000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.752
_reflns_Friedel_fraction_full    0.933
_reflns_Friedel_fraction_max     0.802
_reflns_number_gt                9237
_reflns_number_total             14515
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         1.408
_refine_diff_density_min         -1.527
_refine_diff_density_rms         0.228
_refine_ls_abs_structure_details 
;
 Flack x determined using 2035 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.095(18)
_refine_ls_extinction_coef       0.0152(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     691
_refine_ls_number_reflns         14515
_refine_ls_number_restraints     664
_refine_ls_R_factor_all          0.2190
_refine_ls_R_factor_gt           0.1719
_refine_ls_restrained_S_all      1.041
_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)+(0.1696P)²+258.7294P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3799
_refine_ls_wR_factor_ref         0.4118
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C45-C61 \\sim C45-C61A
 with sigma of 0.02
 O4-O8 \\sim O4A-O8A
 with sigma of 0.04
 C61-O4 \\sim C61A-O4A
 with sigma of 0.02
 C61-O8 \\sim C61A-O8A
 with sigma of 0.02
 C61-C12 \\sim C61A-C12A
 with sigma of 0.04
 C45-O8 \\sim C45-O8A
 with sigma of 0.04
 O8-C12 \\sim O8A-C12A
 with sigma of 0.02
 C45-O4 \\sim C45-O4A
 with sigma of 0.04
 C56-C7 \\sim C56A-C7A
 with sigma of 0.04
 C60-O7 \\sim C60-O7A
 with sigma of 0.04
 C56-C60 \\sim C56A-C60
 with sigma of 0.02
 C60-O5 \\sim C60-O5A
 with sigma of 0.04
 C56-O5 \\sim C56A-O5A
 with sigma of 0.02
 O5-O7 \\sim O5A-O7A
 with sigma of 0.04
 C56-O7 \\sim C56A-O7A
 with sigma of 0.02
 O5-C7 \\sim O5A-C7A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C56 \\sim O7 \\sim O5 \\sim C60: within 1.7A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 1.7A
C14 \\sim C20 \\sim C1 \\sim C38: within 1.7A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 1.7A
Uanis(C12) \\sim Ueq, Uanis(O8) \\sim Ueq, : with sigma of 0.1 and sigma for
terminal atoms of 0.2
Uanis(O8) \\sim Ueq, Uanis(C12) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C41) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C14) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C56) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C12, O8, C61, O4, C45
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C56, C60, O5, C7
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
5. Others
 Sof(C12A)=Sof(H12D)=Sof(H12E)=Sof(H12F)=Sof(O8A)=Sof(C61A)=Sof(O4A)=1-FVAR(1)
 Sof(C61)=Sof(O4)=Sof(O8)=Sof(C12)=Sof(H12A)=Sof(H12B)=Sof(H12C)=FVAR(1)
 Sof(O7A)=Sof(C56A)=Sof(O5A)=Sof(C7A)=1-FVAR(2)
 Sof(C56)=Sof(O5)=Sof(O7)=Sof(C7)=Sof(H7A)=Sof(H7B)=Sof(H7C)=FVAR(2)
6.a Ternary CH refined with riding coordinates:
 C2(H2), C9(H9), C24(H24), C38(H38)
6.b Aromatic/amide H refined with riding coordinates:
 N7(H7), C8(H8), C10(H10), N12(H12), C17(H17), C18(H18), C20(H20), C22(H22),
 C29(H29), C26(H26), C27(H27), C30(H30), C31(H31), C32(H32), C33(H33), C34(H34),
  C39(H39), C43(H43), C44(H44), C47(H47), C48(H48), C51(H51), C52(H52),
 C62(H62), C63(H63), C65(H65), C66(H66), C21(H21)
6.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C7(H7A,H7B,H7C), C12(H12A,H12B,H12C), C12A(H12D,H12E,
 H12F), C67(H67A,H67B,H67C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.3959(2) -0.68732(16) -0.21634(4) 0.0503(7) Uani 1 1 d . . . . .
Br2 Br -0.01324(16) -0.57611(15) -0.46523(4) 0.0462(6) Uani 1 1 d . . . . .
C1 C 0.2973(13) -0.7082(10) -0.4232(3) 0.025(3) Uani 1 1 d . U . . .
C2 C 0.2047(14) -0.7254(10) -0.4410(3) 0.027(3) Uani 1 1 d . . . . .
H2 H 0.149885 -0.673145 -0.441412 0.033 Uiso 1 1 calc R U . . .
C3 C 0.2190(16) -0.4811(13) -0.3258(3) 0.037(4) Uani 1 1 d . . . . .
C4 C 0.2479(19) -0.4521(14) -0.2866(4) 0.043(4) Uani 1 1 d . . . . .
C5 C 0.3380(12) -0.8150(12) -0.4629(3) 0.027(3) Uani 1 1 d . . . . .
C6 C 0.2935(15) -0.5520(11) -0.3248(3) 0.032(3) Uani 1 1 d . . . . .
N7 N 0.3611(10) -0.7985(9) -0.5009(2) 0.026(2) Uani 1 1 d . . . . .
H7 H 0.394581 -0.815846 -0.513179 0.031 Uiso 1 1 calc R U . . .
C8 C 0.1392(15) -0.4776(12) -0.3421(3) 0.035(4) Uani 1 1 d . . . . .
H8 H 0.096473 -0.421958 -0.343963 0.042 Uiso 1 1 calc R U . . .
C9 C 0.3837(15) -0.5375(12) -0.3085(3) 0.033(3) Uani 1 1 d . . . . .
H9 H 0.437871 -0.590322 -0.308436 0.040 Uiso 1 1 calc R U . . .
C10 C 0.1984(15) -0.9902(12) -0.4330(3) 0.030(3) Uani 1 1 d . . . . .
H10 H 0.247139 -1.042455 -0.432792 0.036 Uiso 1 1 calc R U . . .
N12 N 0.2937(15) -0.5465(11) -0.2497(3) 0.041(3) Uani 1 1 d . . . . .
H12 H 0.309913 -0.576560 -0.237313 0.049 Uiso 1 1 calc R U . . .
C13 C 0.4322(15) -0.4408(13) -0.3131(3) 0.033(3) Uani 1 1 d . . . . .
C14 C 0.3713(13) -0.7842(10) -0.4233(3) 0.024(3) Uani 1 1 d . U . . .
C15 C 0.3285(14) -0.5225(10) -0.2866(3) 0.028(3) Uani 1 1 d . . . . .
C16 C 0.3579(15) -0.3661(13) -0.3131(3) 0.030(3) Uani 1 1 d . . . . .
C17 C 0.5374(16) -0.4183(14) -0.3155(3) 0.039(4) Uani 1 1 d . . . . .
H17 H 0.588698 -0.468460 -0.314687 0.047 Uiso 1 1 calc R U . . .
C18 C 0.2786(16) -0.6306(12) -0.3393(4) 0.040(4) Uani 1 1 d . . . . .
H18 H 0.328793 -0.681794 -0.339097 0.048 Uiso 1 1 calc R U . . .
C19 C 0.1572(14) -0.8204(12) -0.4357(3) 0.031(3) Uani 1 1 d . . . . .
C20 C 0.4554(16) -0.7825(12) -0.4088(3) 0.037(4) Uani 1 1 d . U . . .
H20 H 0.507061 -0.832490 -0.408935 0.044 Uiso 1 1 calc R U . . .
C22 C 0.0122(18) -0.9391(14) -0.4308(4) 0.047(5) Uani 1 1 d . . . . .
H22 H -0.062043 -0.954940 -0.429255 0.057 Uiso 1 1 calc R U . . .
C23 C 0.2596(12) -0.7421(12) -0.4634(3) 0.028(3) Uani 1 1 d . . . . .
C24 C 0.2381(16) -0.4004(12) -0.3095(3) 0.034(3) Uani 1 1 d . . . . .
H24 H 0.182681 -0.348613 -0.309958 0.041 Uiso 1 1 calc R U . . .
C29 C 0.178(2) -0.5132(13) -0.2079(4) 0.047(5) Uani 1 1 d . . . . .
H29 H 0.207909 -0.574630 -0.210399 0.057 Uiso 1 1 calc R U . . .
C26 C 0.3969(18) -0.2766(14) -0.3167(4) 0.043(4) Uani 1 1 d . . . . .
H26 H 0.343291 -0.228436 -0.317922 0.052 Uiso 1 1 calc R U . . .
C27 C 0.1128(18) -0.3955(14) -0.1838(4) 0.046(4) Uani 1 1 d . . . . .
H27 H 0.085132 -0.373673 -0.170006 0.055 Uiso 1 1 calc R U . . .
C28 C 0.4169(16) -0.5404(13) -0.3829(3) 0.037(4) Uani 1 1 d . . . . .
C30 C 0.3060(14) -0.6313(10) -0.4107(3) 0.026(3) Uani 1 1 d . . . . .
H30 H 0.257125 -0.579487 -0.412015 0.031 Uiso 1 1 calc R U . . .
C31 C 0.3433(15) -0.5705(11) -0.2674(3) 0.033(3) Uani 1 1 d . . . . .
H31 H 0.391458 -0.623176 -0.267132 0.040 Uiso 1 1 calc R U . . .
C32 C 0.2340(17) -0.6985(15) -0.4835(3) 0.041(4) Uani 1 1 d . . . . .
H32 H 0.183572 -0.647556 -0.484006 0.049 Uiso 1 1 calc R U . . .
C33 C 0.3910(15) -0.8416(12) -0.4819(3) 0.031(3) Uani 1 1 d . . . . .
H33 H 0.446551 -0.888266 -0.481625 0.038 Uiso 1 1 calc R U . . .
C34 C 0.1927(18) -0.4259(15) -0.2675(3) 0.042(4) Uani 1 1 d . . . . .
H34 H 0.141762 -0.375374 -0.267756 0.050 Uiso 1 1 calc R U . . .
C35 C 0.2126(16) -0.4730(12) -0.2488(4) 0.036(3) Uani 1 1 d . . . . .
C36 C 0.2600(15) -0.6980(12) -0.5253(3) 0.032(3) Uani 1 1 d . . . . .
C37 C 0.3892(17) -0.6306(12) -0.3959(3) 0.037(4) Uani 1 1 d . . . . .
C38 C 0.3457(13) -0.8647(12) -0.4401(3) 0.030(3) Uani 1 1 d . U . . .
H38 H 0.399534 -0.917793 -0.439800 0.036 Uiso 1 1 calc R U . . .
C39 C 0.0471(15) -0.8402(14) -0.4341(4) 0.037(4) Uani 1 1 d . . . . .
H39 H -0.004610 -0.790403 -0.435109 0.045 Uiso 1 1 calc R U . . .
C40 C 0.2361(14) -0.8959(11) -0.4361(3) 0.028(3) Uani 1 1 d . . . . .
C41 C 0.2830(12) -0.7303(9) -0.5028(3) 0.022(2) Uani 1 1 d . U . . .
C43 C 0.257(2) -0.7585(14) -0.5421(4) 0.047(5) Uani 1 1 d . . . . .
H43 H 0.270988 -0.824107 -0.539533 0.056 Uiso 1 1 calc R U . . .
C44 C 0.148(2) -0.3503(15) -0.2224(4) 0.050(5) Uani 1 1 d . . . . .
H44 H 0.144935 -0.303182 -0.233682 0.061 Uiso 1 1 calc R U . . .
C45 C 0.1222(15) -0.5594(13) -0.3563(3) 0.038(4) Uani 1 1 d D . . . .
C47 C 0.234(2) -0.7267(14) -0.5638(4) 0.046(5) Uani 1 1 d . . . . .
H47 H 0.229465 -0.770733 -0.575733 0.055 Uiso 1 1 calc R U . . .
C48 C 0.0866(15) -1.0041(13) -0.4302(4) 0.040(4) Uani 1 1 d . . . . .
H48 H 0.063169 -1.067524 -0.427630 0.047 Uiso 1 1 calc R U . . .
C49 C 0.1703(15) -0.7202(13) -0.3669(4) 0.036(3) Uani 1 1 d . . . . .
C51 C 0.4960(17) -0.2468(15) -0.3188(4) 0.044(4) Uani 1 1 d . . . . .
H51 H 0.516690 -0.181891 -0.320079 0.053 Uiso 1 1 calc R U . . .
C52 C 0.1425(17) -0.4922(14) -0.1879(4) 0.043(4) Uani 1 1 d . . . . .
H52 H 0.136765 -0.539332 -0.176597 0.051 Uiso 1 1 calc R U . . .
C55 C 0.1925(15) -0.6334(13) -0.3536(3) 0.035(4) Uani 1 1 d . . . . .
C56 C 0.556(3) -0.708(3) -0.3799(7) 0.036(5) Uani 0.66(4) 1 d D U P A 1
C57 C 0.1741(16) -0.4483(11) -0.2261(3) 0.035(3) Uani 1 1 d . . . . .
C60 C 0.4662(14) -0.7096(10) -0.3940(3) 0.032(3) Uani 1 1 d D U . . .
C61 C 0.023(2) -0.552(2) -0.3690(5) 0.035(5) Uani 0.57(4) 1 d D . P B 1
C62 C 0.2345(19) -0.6007(14) -0.5292(4) 0.043(4) Uani 1 1 d . . . . .
H62 H 0.233006 -0.557716 -0.516998 0.052 Uiso 1 1 calc R U . . .
C63 C 0.2175(14) -0.6294(12) -0.5675(3) 0.030(3) Uani 1 1 d . . . . .
H63 H 0.210135 -0.606404 -0.582250 0.036 Uiso 1 1 calc R U . . .
C65 C 0.212(2) -0.5679(15) -0.5502(4) 0.052(5) Uani 1 1 d . . . . .
H65 H 0.192808 -0.503162 -0.552524 0.063 Uiso 1 1 calc R U . . .
C66 C 0.5743(16) -0.3305(12) -0.3189(4) 0.040(4) Uani 1 1 d . . . . .
H66 H 0.649281 -0.320086 -0.321288 0.048 Uiso 1 1 calc R U . . .
O1 O 0.3434(11) -0.4728(8) -0.3862(2) 0.036(3) Uani 1 1 d . . . . .
O5 O 0.537(2) -0.720(3) -0.3599(5) 0.057(7) Uani 0.66(4) 1 d D U P A 1
C11 C 0.3742(18) -0.3828(12) -0.3765(4) 0.043(5) Uani 1 1 d . . . . .
H11A H 0.426796 -0.351159 -0.386251 0.065 Uiso 1 1 calc R U . . .
H11B H 0.406746 -0.393545 -0.361881 0.065 Uiso 1 1 calc R U . . .
H11C H 0.310099 -0.342375 -0.374934 0.065 Uiso 1 1 calc R U . . .
O7 O 0.6576(19) -0.701(2) -0.3872(5) 0.053(7) Uani 0.66(4) 1 d D U P A 1
C7 C 0.623(3) -0.703(2) -0.3440(6) 0.056(8) Uani 0.66(4) 1 d D . P A 1
H7A H 0.682995 -0.747746 -0.346924 0.083 Uiso 0.66(4) 1 calc R U P A 1
H7B H 0.596284 -0.713522 -0.328851 0.083 Uiso 0.66(4) 1 calc R U P A 1
H7C H 0.649554 -0.637883 -0.345471 0.083 Uiso 0.66(4) 1 calc R U P A 1
C21 C 0.129(2) -0.3348(15) -0.2025(4) 0.053(5) Uani 1 1 d . . . . .
H21 H 0.124018 -0.269051 -0.199018 0.064 Uiso 1 1 calc R U . . .
O24 O 0.4947(15) -0.5329(10) -0.3703(3) 0.061(5) Uani 1 1 d . . . . .
O3 O 0.2418(12) -0.7919(10) -0.3632(2) 0.039(3) Uani 1 1 d . . . . .
O2 O 0.091(2) -0.7309(14) -0.3786(5) 0.099(9) Uani 1 1 d . . . . .
O4 O -0.0704(19) -0.552(2) -0.3610(5) 0.051(8) Uani 0.57(4) 1 d D . P B 1
O8 O 0.0451(18) -0.5507(19) -0.3900(4) 0.040(5) Uani 0.57(4) 1 d D U P B 1
C12 C -0.040(2) -0.577(3) -0.4044(6) 0.040(7) Uani 0.57(4) 1 d D U P B 1
H12A H -0.034151 -0.540783 -0.418265 0.061 Uiso 0.57(4) 1 calc R U P B 1
H12B H -0.109158 -0.563939 -0.397253 0.061 Uiso 0.57(4) 1 calc R U P B 1
H12C H -0.034278 -0.645359 -0.407709 0.061 Uiso 0.57(4) 1 calc R U P B 1
C12A C -0.122(6) -0.572(11) -0.3873(15) 0.16(5) Uiso 0.43(4) 1 d D . P B 2
H12D H -0.113434 -0.625253 -0.397712 0.236 Uiso 0.43(4) 1 calc R U P B 2
H12E H -0.112436 -0.511839 -0.395239 0.236 Uiso 0.43(4) 1 calc R U P B 2
H12F H -0.194972 -0.574230 -0.380823 0.236 Uiso 0.43(4) 1 calc R U P B 2
O8A O -0.044(2) -0.580(3) -0.3701(6) 0.037(8) Uiso 0.43(4) 1 d D . P B 2
C61A C 0.052(2) -0.553(3) -0.3760(5) 0.028(9) Uiso 0.43(4) 1 d D . P B 2
O4A O 0.074(3) -0.508(3) -0.3935(5) 0.037(8) Uiso 0.43(4) 1 d D . P B 2
O7A O 0.514(4) -0.750(3) -0.3556(6) 0.035(10) Uiso 0.34(4) 1 d D . P A 2
C56A C 0.538(4) -0.713(7) -0.3757(9) 0.05(3) Uiso 0.34(4) 1 d D . P A 2
O5A O 0.635(3) -0.691(3) -0.3782(7) 0.032(10) Uiso 0.34(4) 1 d D . P A 2
C7A C 0.702(4) -0.667(3) -0.3593(7) 0.029(12) Uiso 0.34(4) 1 d D . P A 2
C67 C 0.2190(16) -0.8812(12) -0.3733(4) 0.038(4) Uani 1 1 d . . . . .
H67A H 0.223197 -0.874578 -0.389545 0.058 Uiso 1 1 calc R U . . .
H67B H 0.146181 -0.901944 -0.369125 0.058 Uiso 1 1 calc R U . . .
H67C H 0.271954 -0.928473 -0.368339 0.058 Uiso 1 1 calc R U . . .
O29 O -0.015(11) -1.000000 -0.500000 0.33(6) Uiso 1 2 d S . P . .
C25 C 0.155(5) -0.938(4) -0.5025(9) 0.122(16) Uiso 1 1 d . . . . .
C42 C 0.069(7) -0.906(7) -0.5002(14) 0.20(3) Uiso 1 1 d . . . . .
C70 C -0.107(3) -0.746(3) -0.2483(6) 0.087(9) Uiso 1 1 d . . . C 1
O30 O 0.000000 -0.661(6) -0.250000 0.22(3) Uiso 1 2 d S . P C 1
C68 C -0.031(6) -0.827(4) -0.2477(14) 0.15(2) Uiso 1 1 d . . . C 1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.59(2) . ?
C1 C14 1.41(2) . ?
C1 C30 1.32(2) . ?
C2 H2 1.0000 . ?
C2 C19 1.49(2) . ?
C2 C23 1.52(2) . ?
C3 C6 1.36(2) . ?
C3 C8 1.39(3) . ?
C3 C24 1.52(3) . ?
C4 C15 1.40(2) . ?
C4 C24 1.56(3) . ?
C4 C34 1.39(3) . ?
C5 C23 1.41(2) . ?
C5 C33 1.37(2) . ?
C5 C38 1.54(3) . ?
C6 C9 1.50(2) . ?
C6 C18 1.42(2) . ?
N7 H7 0.8800 . ?
N7 C33 1.35(2) . ?
N7 C41 1.365(19) . ?
C8 H8 0.9500 . ?
C8 C45 1.45(2) . ?
C9 H9 1.0000 . ?
C9 C13 1.51(2) . ?
C9 C15 1.50(3) . ?
C10 H10 0.9500 . ?
C10 C40 1.42(2) . ?
C10 C48 1.41(3) . ?
N12 H12 0.8800 . ?
N12 C31 1.27(3) . ?
N12 C35 1.44(2) . ?
C13 C16 1.39(3) . ?
C13 C17 1.35(2) . ?
C14 C20 1.36(2) . ?
C14 C38 1.55(2) . ?
C15 C31 1.35(2) . ?
C16 C24 1.57(3) . ?
C16 C26 1.36(3) . ?
C17 H17 0.9500 . ?
C17 C66 1.33(3) . ?
C18 H18 0.9500 . ?
C18 C55 1.37(3) . ?
C19 C39 1.39(2) . ?
C19 C40 1.44(2) . ?
C20 H20 0.9500 . ?
C20 C60 1.36(2) . ?
C22 H22 0.9500 . ?
C22 C39 1.47(3) . ?
C22 C48 1.30(3) . ?
C23 C32 1.39(3) . ?
C24 H24 1.0000 . ?
C29 H29 0.9500 . ?
C29 C52 1.32(3) . ?
C29 C57 1.42(3) . ?
C26 H26 0.9500 . ?
C26 C51 1.30(3) . ?
C27 H27 0.9500 . ?
C27 C52 1.43(3) . ?
C27 C21 1.42(3) . ?
C28 C37 1.53(2) . ?
C28 O1 1.33(2) . ?
C28 O24 1.23(2) . ?
C30 H30 0.9500 . ?
C30 C37 1.36(3) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C32 C41 1.38(2) . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?
C34 C35 1.33(3) . ?
C35 C57 1.48(3) . ?
C36 C41 1.46(2) . ?
C36 C43 1.32(3) . ?
C36 C62 1.42(2) . ?
C37 C60 1.47(2) . ?
C38 H38 1.0000 . ?
C38 C40 1.44(2) . ?
C39 H39 0.9500 . ?
C43 H43 0.9500 . ?
C43 C47 1.41(3) . ?
C44 H44 0.9500 . ?
C44 C57 1.43(2) . ?
C44 C21 1.23(3) . ?
C45 C55 1.36(2) . ?
C45 C61 1.45(3) . ?
C45 C61A 1.47(3) . ?
C47 H47 0.9500 . ?
C47 C63 1.40(3) . ?
C48 H48 0.9500 . ?
C49 C55 1.48(2) . ?
C49 O3 1.36(2) . ?
C49 O2 1.21(3) . ?
C51 H51 0.9500 . ?
C51 C66 1.52(3) . ?
C52 H52 0.9500 . ?
C56 C60 1.40(3) . ?
C56 O5 1.24(5) . ?
C56 O7 1.33(5) . ?
C60 C56A 1.41(3) . ?
C61 O4 1.25(3) . ?
C61 O8 1.29(3) . ?
C62 H62 0.9500 . ?
C62 C65 1.37(3) . ?
C63 H63 0.9500 . ?
C63 C65 1.35(3) . ?
C65 H65 0.9500 . ?
C66 H66 0.9500 . ?
O1 C11 1.44(2) . ?
O5 C7 1.46(4) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C21 H21 0.9500 . ?
O3 C67 1.423(19) . ?
O8 C12 1.41(4) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C12A H12D 0.9800 . ?
C12A H12E 0.9800 . ?
C12A H12F 0.9800 . ?
C12A O8A 1.42(4) . ?
O8A C61A 1.29(3) . ?
C61A O4A 1.25(4) . ?
O7A C56A 1.35(5) . ?
C56A O5A 1.24(5) . ?
O5A C7A 1.45(4) . ?
C67 H67A 0.9800 . ?
C67 H67B 0.9800 . ?
C67 H67C 0.9800 . ?
O29 C42 1.68(11) . ?
O29 C42 1.68(11) 3_534 ?
C25 C25 1.77(11) 3_534 ?
C25 C42 1.17(9) . ?
C70 O30 1.79(7) . ?
C70 C68 1.47(7) . ?
C68 C68 0.82(13) 4_554 ?

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
C14 C1 C2 110.6(13) . . ?
C30 C1 C2 124.6(14) . . ?
C30 C1 C14 124.7(16) . . ?
C1 C2 H2 113.2 . . ?
C19 C2 C1 106.1(14) . . ?
C19 C2 H2 113.2 . . ?
C19 C2 C23 103.0(13) . . ?
C23 C2 C1 107.3(13) . . ?
C23 C2 H2 113.2 . . ?
C6 C3 C8 122.6(17) . . ?
C6 C3 C24 114.4(16) . . ?
C8 C3 C24 122.6(16) . . ?
C15 C4 C24 112.8(18) . . ?
C34 C4 C15 122.1(19) . . ?
C34 C4 C24 124.7(17) . . ?
C23 C5 C38 112.8(14) . . ?
C33 C5 C23 120.8(17) . . ?
C33 C5 C38 126.0(15) . . ?
C3 C6 C9 115.8(16) . . ?
C3 C6 C18 117.0(17) . . ?
C18 C6 C9 127.2(16) . . ?
C33 N7 H7 117.3 . . ?
C33 N7 C41 125.5(15) . . ?
C41 N7 H7 117.3 . . ?
C3 C8 H8 120.3 . . ?
C3 C8 C45 119.3(16) . . ?
C45 C8 H8 120.3 . . ?
C6 C9 H9 113.8 . . ?
C6 C9 C13 107.4(15) . . ?
C6 C9 C15 104.7(15) . . ?
C13 C9 H9 113.8 . . ?
C15 C9 H9 113.8 . . ?
C15 C9 C13 102.4(14) . . ?
C40 C10 H10 121.0 . . ?
C48 C10 H10 121.0 . . ?
C48 C10 C40 118.0(16) . . ?
C31 N12 H12 118.0 . . ?
C31 N12 C35 123.9(18) . . ?
C35 N12 H12 118.0 . . ?
C16 C13 C9 114.5(16) . . ?
C17 C13 C9 127.9(18) . . ?
C17 C13 C16 117.4(18) . . ?
C1 C14 C38 115.0(14) . . ?
C20 C14 C1 118.9(14) . . ?
C20 C14 C38 126.1(14) . . ?
C4 C15 C9 114.7(16) . . ?
C31 C15 C4 117.0(18) . . ?
C31 C15 C9 128.3(16) . . ?
C13 C16 C24 113.0(15) . . ?
C26 C16 C13 117.4(18) . . ?
C26 C16 C24 129.6(18) . . ?
C13 C17 H17 117.8 . . ?
C66 C17 C13 124(2) . . ?
C66 C17 H17 117.8 . . ?
C6 C18 H18 119.7 . . ?
C55 C18 C6 120.6(17) . . ?
C55 C18 H18 119.7 . . ?
C39 C19 C2 125.4(16) . . ?
C39 C19 C40 121.1(16) . . ?
C40 C19 C2 112.8(15) . . ?
C14 C20 H20 119.7 . . ?
C14 C20 C60 120.6(16) . . ?
C60 C20 H20 119.7 . . ?
C39 C22 H22 121.3 . . ?
C48 C22 H22 121.3 . . ?
C48 C22 C39 117(2) . . ?
C5 C23 C2 113.7(15) . . ?
C32 C23 C2 126.7(15) . . ?
C32 C23 C5 119.4(16) . . ?
C3 C24 C4 103.5(15) . . ?
C3 C24 C16 106.6(16) . . ?
C3 C24 H24 114.7 . . ?
C4 C24 C16 101.1(15) . . ?
C4 C24 H24 114.7 . . ?
C16 C24 H24 114.7 . . ?
C52 C29 H29 118.4 . . ?
C52 C29 C57 123.2(18) . . ?
C57 C29 H29 118.4 . . ?
C16 C26 H26 114.9 . . ?
C51 C26 C16 130(2) . . ?
C51 C26 H26 114.9 . . ?
C52 C27 H27 123.2 . . ?
C21 C27 H27 123.2 . . ?
C21 C27 C52 114(2) . . ?
O1 C28 C37 111.2(15) . . ?
O24 C28 C37 124.2(16) . . ?
O24 C28 O1 124.5(17) . . ?
C1 C30 H30 121.9 . . ?
C1 C30 C37 116.1(15) . . ?
C37 C30 H30 121.9 . . ?
N12 C31 C15 121.0(18) . . ?
N12 C31 H31 119.5 . . ?
C15 C31 H31 119.5 . . ?
C23 C32 H32 120.4 . . ?
C41 C32 C23 119.1(16) . . ?
C41 C32 H32 120.4 . . ?
C5 C33 H33 121.5 . . ?
N7 C33 C5 117.0(15) . . ?
N7 C33 H33 121.5 . . ?
C4 C34 H34 120.6 . . ?
C35 C34 C4 118.7(19) . . ?
C35 C34 H34 120.6 . . ?
N12 C35 C57 115.3(16) . . ?
C34 C35 N12 117(2) . . ?
C34 C35 C57 127.0(17) . . ?
C43 C36 C41 120.9(16) . . ?
C43 C36 C62 119.3(19) . . ?
C62 C36 C41 119.6(16) . . ?
C30 C37 C28 120.7(15) . . ?
C30 C37 C60 122.5(16) . . ?
C60 C37 C28 116.2(16) . . ?
C5 C38 C14 105.2(13) . . ?
C5 C38 H38 113.3 . . ?
C14 C38 H38 113.3 . . ?
C40 C38 C5 103.3(14) . . ?
C40 C38 C14 107.6(14) . . ?
C40 C38 H38 113.3 . . ?
C19 C39 C22 119.0(17) . . ?
C19 C39 H39 120.5 . . ?
C22 C39 H39 120.5 . . ?
C10 C40 C19 117.6(16) . . ?
C10 C40 C38 127.9(15) . . ?
C19 C40 C38 114.5(15) . . ?
N7 C41 C32 117.9(15) . . ?
N7 C41 C36 115.7(14) . . ?
C32 C41 C36 126.4(15) . . ?
C36 C43 H43 119.7 . . ?
C36 C43 C47 120.5(19) . . ?
C47 C43 H43 119.7 . . ?
C57 C44 H44 124.3 . . ?
C21 C44 H44 124.3 . . ?
C21 C44 C57 111(2) . . ?
C8 C45 C61 112.1(18) . . ?
C8 C45 C61A 121(2) . . ?
C55 C45 C8 116.4(17) . . ?
C55 C45 C61 131.0(19) . . ?
C55 C45 C61A 121(2) . . ?
C43 C47 H47 120.4 . . ?
C63 C47 C43 119.2(19) . . ?
C63 C47 H47 120.4 . . ?
C10 C48 H48 116.7 . . ?
C22 C48 C10 126.6(19) . . ?
C22 C48 H48 116.7 . . ?
O3 C49 C55 113.6(16) . . ?
O2 C49 C55 124.1(19) . . ?
O2 C49 O3 121.9(17) . . ?
C26 C51 H51 124.7 . . ?
C26 C51 C66 110.5(18) . . ?
C66 C51 H51 124.7 . . ?
C29 C52 C27 117(2) . . ?
C29 C52 H52 121.5 . . ?
C27 C52 H52 121.5 . . ?
C18 C55 C49 120.3(17) . . ?
C45 C55 C18 123.2(17) . . ?
C45 C55 C49 116.5(17) . . ?
O5 C56 C60 116(3) . . ?
O5 C56 O7 121(2) . . ?
O7 C56 C60 123(3) . . ?
C29 C57 C35 122.9(16) . . ?
C29 C57 C44 120(2) . . ?
C44 C57 C35 116.3(17) . . ?
C20 C60 C37 117.0(16) . . ?
C20 C60 C56 119(2) . . ?
C20 C60 C56A 123(4) . . ?
C56 C60 C37 123.4(19) . . ?
C56A C60 C37 120(4) . . ?
O4 C61 C45 126(2) . . ?
O4 C61 O8 125(2) . . ?
O8 C61 C45 109(2) . . ?
C36 C62 H62 119.4 . . ?
C65 C62 C36 121.2(19) . . ?
C65 C62 H62 119.4 . . ?
C47 C63 H63 119.7 . . ?
C65 C63 C47 120.6(19) . . ?
C65 C63 H63 119.7 . . ?
C62 C65 H65 120.6 . . ?
C63 C65 C62 118.7(19) . . ?
C63 C65 H65 120.6 . . ?
C17 C66 C51 119.8(19) . . ?
C17 C66 H66 120.1 . . ?
C51 C66 H66 120.1 . . ?
C28 O1 C11 112.7(15) . . ?
C56 O5 C7 118(3) . . ?
O1 C11 H11A 109.5 . . ?
O1 C11 H11B 109.5 . . ?
O1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O5 C7 H7A 109.5 . . ?
O5 C7 H7B 109.5 . . ?
O5 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C27 C21 H21 113.4 . . ?
C44 C21 C27 133(2) . . ?
C44 C21 H21 113.4 . . ?
C49 O3 C67 117.0(15) . . ?
C61 O8 C12 116(3) . . ?
O8 C12 H12A 109.5 . . ?
O8 C12 H12B 109.5 . . ?
O8 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
H12D C12A H12E 109.5 . . ?
H12D C12A H12F 109.5 . . ?
H12E C12A H12F 109.5 . . ?
O8A C12A H12D 109.5 . . ?
O8A C12A H12E 109.5 . . ?
O8A C12A H12F 109.5 . . ?
C61A O8A C12A 114(4) . . ?
O8A C61A C45 108(2) . . ?
O4A C61A C45 125(3) . . ?
O4A C61A O8A 125(3) . . ?
O7A C56A C60 125(4) . . ?
O5A C56A C60 120(4) . . ?
O5A C56A O7A 115(3) . . ?
C56A O5A C7A 121(4) . . ?
O3 C67 H67A 109.5 . . ?
O3 C67 H67B 109.5 . . ?
O3 C67 H67C 109.5 . . ?
H67A C67 H67B 109.5 . . ?
H67A C67 H67C 109.5 . . ?
H67B C67 H67C 109.5 . . ?
C42 O29 C42 104(10) . 3_534 ?
C42 C25 C25 111(6) . 3_534 ?
C25 C42 O29 105(9) . . ?
C68 C70 O30 93(4) . . ?
C70 O30 C70 95(5) 4_554 . ?
C68 C68 C70 126(5) 4_554 . ?

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
C1 C2 C19 C39 132(2) . . . . ?
C1 C2 C19 C40 -57.5(18) . . . . ?
C1 C2 C23 C5 53.7(17) . . . . ?
C1 C2 C23 C32 -131.4(19) . . . . ?
C1 C14 C20 C60 2(3) . . . . ?
C1 C14 C38 C5 55.8(18) . . . . ?
C1 C14 C38 C40 -54(2) . . . . ?
C1 C30 C37 C28 171.6(18) . . . . ?
C1 C30 C37 C60 1(3) . . . . ?
C2 C1 C14 C20 -178.9(16) . . . . ?
C2 C1 C14 C38 0(2) . . . . ?
C2 C1 C30 C37 178.2(17) . . . . ?
C2 C19 C39 C22 174.4(18) . . . . ?
C2 C19 C40 C10 -175.2(16) . . . . ?
C2 C19 C40 C38 3(2) . . . . ?
C2 C23 C32 C41 -172.1(17) . . . . ?
C3 C6 C9 C13 -52(2) . . . . ?
C3 C6 C9 C15 56(2) . . . . ?
C3 C6 C18 C55 0(3) . . . . ?
C3 C8 C45 C55 -5(3) . . . . ?
C3 C8 C45 C61 168(2) . . . . ?
C3 C8 C45 C61A -170(2) . . . . ?
C4 C15 C31 N12 -7(2) . . . . ?
C4 C34 C35 N12 2(3) . . . . ?
C4 C34 C35 C57 171(2) . . . . ?
C5 C23 C32 C41 3(3) . . . . ?
C5 C38 C40 C10 120(2) . . . . ?
C5 C38 C40 C19 -58.9(18) . . . . ?
C6 C3 C8 C45 11(3) . . . . ?
C6 C3 C24 C4 -53(2) . . . . ?
C6 C3 C24 C16 53(2) . . . . ?
C6 C9 C13 C16 54(2) . . . . ?
C6 C9 C13 C17 -132(2) . . . . ?
C6 C9 C15 C4 -51.9(19) . . . . ?
C6 C9 C15 C31 124.7(18) . . . . ?
C6 C18 C55 C45 6(3) . . . . ?
C6 C18 C55 C49 -173.0(19) . . . . ?
C8 C3 C6 C9 170.7(19) . . . . ?
C8 C3 C6 C18 -8(3) . . . . ?
C8 C3 C24 C4 134(2) . . . . ?
C8 C3 C24 C16 -120(2) . . . . ?
C8 C45 C55 C18 -3(3) . . . . ?
C8 C45 C55 C49 175.5(18) . . . . ?
C8 C45 C61 O4 -65(4) . . . . ?
C8 C45 C61 O8 118(3) . . . . ?
C8 C45 C61A O8A -93(4) . . . . ?
C8 C45 C61A O4A 71(5) . . . . ?
C9 C6 C18 C55 -179(2) . . . . ?
C9 C13 C16 C24 -3(2) . . . . ?
C9 C13 C16 C26 178.7(17) . . . . ?
C9 C13 C17 C66 -177.8(19) . . . . ?
C9 C15 C31 N12 176.7(17) . . . . ?
N12 C35 C57 C29 -25(3) . . . . ?
N12 C35 C57 C44 145.0(18) . . . . ?
C13 C9 C15 C4 60.1(19) . . . . ?
C13 C9 C15 C31 -123.2(18) . . . . ?
C13 C16 C24 C3 -49.7(19) . . . . ?
C13 C16 C24 C4 58.2(18) . . . . ?
C13 C16 C26 C51 -5(4) . . . . ?
C13 C17 C66 C51 4(3) . . . . ?
C14 C1 C2 C19 54.8(18) . . . . ?
C14 C1 C2 C23 -54.8(18) . . . . ?
C14 C1 C30 C37 -5(3) . . . . ?
C14 C20 C60 C37 -5(3) . . . . ?
C14 C20 C60 C56 -177(3) . . . . ?
C14 C20 C60 C56A 167(3) . . . . ?
C14 C38 C40 C10 -129.5(19) . . . . ?
C14 C38 C40 C19 52(2) . . . . ?
C15 C4 C24 C3 56(2) . . . . ?
C15 C4 C24 C16 -54(2) . . . . ?
C15 C4 C34 C35 -4(3) . . . . ?
C15 C9 C13 C16 -56.2(19) . . . . ?
C15 C9 C13 C17 118(2) . . . . ?
C16 C13 C17 C66 -3(3) . . . . ?
C16 C26 C51 C66 5(4) . . . . ?
C17 C13 C16 C24 -178.0(17) . . . . ?
C17 C13 C16 C26 4(3) . . . . ?
C18 C6 C9 C13 127(2) . . . . ?
C18 C6 C9 C15 -125(2) . . . . ?
C19 C2 C23 C5 -58.0(18) . . . . ?
C19 C2 C23 C32 117(2) . . . . ?
C20 C14 C38 C5 -125.8(19) . . . . ?
C20 C14 C38 C40 125(2) . . . . ?
C20 C60 C56A O7A -87(9) . . . . ?
C20 C60 C56A O5A 85(8) . . . . ?
C23 C2 C19 C39 -115(2) . . . . ?
C23 C2 C19 C40 55.1(19) . . . . ?
C23 C5 C33 N7 -3(2) . . . . ?
C23 C5 C38 C14 -57.5(17) . . . . ?
C23 C5 C38 C40 55.3(17) . . . . ?
C23 C32 C41 N7 -5(3) . . . . ?
C23 C32 C41 C36 175.1(17) . . . . ?
C24 C3 C6 C9 -2(3) . . . . ?
C24 C3 C6 C18 178.6(18) . . . . ?
C24 C3 C8 C45 -176.7(19) . . . . ?
C24 C4 C15 C9 -3(2) . . . . ?
C24 C4 C15 C31 179.6(15) . . . . ?
C24 C4 C34 C35 -176.5(19) . . . . ?
C24 C16 C26 C51 177(2) . . . . ?
C26 C16 C24 C3 128(2) . . . . ?
C26 C16 C24 C4 -124(2) . . . . ?
C26 C51 C66 C17 -4(3) . . . . ?
C28 C37 C60 C20 -167.0(19) . . . . ?
C28 C37 C60 C56 5(4) . . . . ?
C28 C37 C60 C56A 21(4) . . . . ?
C30 C1 C2 C19 -127.9(17) . . . . ?
C30 C1 C2 C23 122.5(18) . . . . ?
C30 C1 C14 C20 4(3) . . . . ?
C30 C1 C14 C38 -177.6(17) . . . . ?
C30 C37 C60 C20 4(3) . . . . ?
C30 C37 C60 C56 176(3) . . . . ?
C30 C37 C60 C56A -168(3) . . . . ?
C31 N12 C35 C34 -3(3) . . . . ?
C31 N12 C35 C57 -173.1(17) . . . . ?
C33 C5 C23 C2 177.0(15) . . . . ?
C33 C5 C23 C32 2(3) . . . . ?
C33 C5 C38 C14 129.0(17) . . . . ?
C33 C5 C38 C40 -118.3(18) . . . . ?
C33 N7 C41 C32 4(2) . . . . ?
C33 N7 C41 C36 -176.5(16) . . . . ?
C34 C4 C15 C9 -176.7(19) . . . . ?
C34 C4 C15 C31 6(3) . . . . ?
C34 C4 C24 C3 -131(2) . . . . ?
C34 C4 C24 C16 119(2) . . . . ?
C34 C35 C57 C29 165(2) . . . . ?
C34 C35 C57 C44 -24(3) . . . . ?
C35 N12 C31 C15 5(3) . . . . ?
C36 C43 C47 C63 2(4) . . . . ?
C36 C62 C65 C63 -2(4) . . . . ?
C37 C28 O1 C11 -172.2(17) . . . . ?
C37 C60 C56A O7A 84(9) . . . . ?
C37 C60 C56A O5A -103(8) . . . . ?
C38 C5 C23 C2 3.1(19) . . . . ?
C38 C5 C23 C32 -172.2(17) . . . . ?
C38 C5 C33 N7 169.9(15) . . . . ?
C38 C14 C20 C60 -176.7(18) . . . . ?
C39 C19 C40 C10 -5(3) . . . . ?
C39 C19 C40 C38 173.9(19) . . . . ?
C39 C22 C48 C10 -2(4) . . . . ?
C40 C10 C48 C22 2(3) . . . . ?
C40 C19 C39 C22 5(3) . . . . ?
C41 N7 C33 C5 1(3) . . . . ?
C41 C36 C43 C47 179(2) . . . . ?
C41 C36 C62 C65 -180(2) . . . . ?
C43 C36 C41 N7 40(3) . . . . ?
C43 C36 C41 C32 -140(2) . . . . ?
C43 C36 C62 C65 -3(4) . . . . ?
C43 C47 C63 C65 -7(4) . . . . ?
C45 C61 O8 C12 158(3) . . . . ?
C47 C63 C65 C62 7(4) . . . . ?
C48 C10 C40 C19 1(3) . . . . ?
C48 C10 C40 C38 -177.3(19) . . . . ?
C48 C22 C39 C19 -2(3) . . . . ?
C52 C29 C57 C35 -179(2) . . . . ?
C52 C29 C57 C44 11(4) . . . . ?
C52 C27 C21 C44 13(4) . . . . ?
C55 C45 C61 O4 106(4) . . . . ?
C55 C45 C61 O8 -71(4) . . . . ?
C55 C45 C61A O8A 102(3) . . . . ?
C55 C45 C61A O4A -94(5) . . . . ?
C55 C49 O3 C67 173.1(17) . . . . ?
C57 C29 C52 C27 -9(4) . . . . ?
C57 C44 C21 C27 -11(4) . . . . ?
C60 C56 O5 C7 -170(3) . . . . ?
C60 C56A O5A C7A 162(6) . . . . ?
C61 C45 C55 C18 -174(2) . . . . ?
C61 C45 C55 C49 5(4) . . . . ?
C62 C36 C41 N7 -143.7(18) . . . . ?
C62 C36 C41 C32 36(3) . . . . ?
C62 C36 C43 C47 3(4) . . . . ?
O1 C28 C37 C30 7(3) . . . . ?
O1 C28 C37 C60 178.6(17) . . . . ?
O5 C56 C60 C20 -112(3) . . . . ?
O5 C56 C60 C37 76(4) . . . . ?
O7 C56 C60 C20 63(4) . . . . ?
O7 C56 C60 C37 -109(4) . . . . ?
O7 C56 O5 C7 15(5) . . . . ?
C21 C27 C52 C29 -1(3) . . . . ?
C21 C44 C57 C29 -1(3) . . . . ?
C21 C44 C57 C35 -172(2) . . . . ?
O24 C28 C37 C30 -175(2) . . . . ?
O24 C28 C37 C60 -4(3) . . . . ?
O24 C28 O1 C11 10(3) . . . . ?
O3 C49 C55 C18 0(3) . . . . ?
O3 C49 C55 C45 -178.8(18) . . . . ?
O2 C49 C55 C18 174(3) . . . . ?
O2 C49 C55 C45 -5(4) . . . . ?
O2 C49 O3 C67 -1(3) . . . . ?
O4 C61 O8 C12 -19(5) . . . . ?
C12A O8A C61A C45 177(8) . . . . ?
C12A O8A C61A O4A 13(10) . . . . ?
C61A C45 C55 C18 162(2) . . . . ?
C61A C45 C55 C49 -19(3) . . . . ?
O7A C56A O5A C7A -25(11) . . . . ?
C25 C25 C42 O29 -14(9) 3_534 . . . ?
C42 O29 C42 C25 7(4) 3_534 . . . ?
O30 C70 C68 C68 -23(18) . . . 4_554 ?
C68 C70 O30 C70 4(3) . . . 4_554 ?

_olex2_exptl_crystal_mounting_method fiber
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.198
_oxdiff_exptl_absorpt_empirical_full_min 0.576
####################################################################### 
# 
# 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_20230209-pydmadff2-hbr
_database_code_depnum_ccdc_archive 'CCDC 2246247'
loop_
_audit_author_name
_audit_author_address
'Ryo Inoue'
;Kwansei Gakuin University
Japan
;
_audit_update_record             
;
2023-03-04 deposited with the CCDC.	2023-04-11 downloaded from the CCDC.
;
_audit_creation_date             2023-02-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br, C29 H21 F N O4'
_chemical_formula_sum            'C29 H21 Br F N O4'
_chemical_formula_weight         546.38
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C29H21NO4BrF
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_H-M_alt        'C 2 2 21'
_space_group_name_Hall           'C 2c 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y, -z+1/2'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   12.0615(7)
_cell_length_b                   14.3870(9)
_cell_length_c                   61.506(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     10673.1(11)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    7019
_cell_measurement_temperature    150
_cell_measurement_theta_max      29.8200
_cell_measurement_theta_min      2.2050
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.925
_exptl_absorpt_coefficient_mu    1.581
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.34604
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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    1.360
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             4448
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1571
_diffrn_reflns_av_unetI/netI     0.2802
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       84
_diffrn_reflns_limit_l_min       -63
_diffrn_reflns_number            39313
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.900
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.150
_diffrn_reflns_theta_min         1.987
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00  70.00   0.50   40.00    --  -20.00  45.00   0.00  360
  2  ω   -110.00  -9.00   0.50   40.00    --  -20.00  45.00  90.00  202
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0074390000
_diffrn_orient_matrix_UB_12      -0.0023097000
_diffrn_orient_matrix_UB_13      0.0114249000
_diffrn_orient_matrix_UB_21      0.0499765000
_diffrn_orient_matrix_UB_22      -0.0251577000
_diffrn_orient_matrix_UB_23      -0.0015460000
_diffrn_orient_matrix_UB_31      0.0301256000
_diffrn_orient_matrix_UB_32      0.0423054000
_diffrn_orient_matrix_UB_33      -0.0002721000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.765
_reflns_Friedel_fraction_full    0.975
_reflns_Friedel_fraction_max     0.852
_reflns_number_gt                7382
_reflns_number_total             15536
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.685
_refine_diff_density_min         -1.091
_refine_diff_density_rms         0.158
_refine_ls_abs_structure_details 
;
 Flack x determined using 1703 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.062(11)
_refine_ls_extinction_coef       0.00056(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     654
_refine_ls_number_reflns         15536
_refine_ls_number_restraints     864
_refine_ls_R_factor_all          0.2175
_refine_ls_R_factor_gt           0.1201
_refine_ls_restrained_S_all      1.005
_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)+(0.1023P)²+7.6460P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2296
_refine_ls_wR_factor_ref         0.2761
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C01M \\sim C01P \\sim C016 \\sim C01K \\sim C01Z \\sim C01A: within 1.7A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 1.7A
C00I \\sim C011 \\sim C01J \\sim C01S \\sim C01T \\sim C01U: within 1.7A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 1.7A
O005 \\sim O00C \\sim C018 \\sim C01H: within 1.7A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 1.7A
N00F \\sim C00K \\sim C00Q \\sim C00T \\sim C014 \\sim C00L: within 1.7A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 1.7A
N00A \\sim C00D \\sim C00M \\sim C7 \\sim C01L \\sim C11: within 1.7A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 1.7A
C12 \\sim C00M: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08 within 1.7A
N00F \\sim C00K \\sim C00L \\sim C00Q \\sim C00T \\sim C014: within 1.7A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 1.7A
C01D \\sim O006 \\sim C01E: within 1.7A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 1.7A
C01J \\sim C8 \\sim C7: within 1.7A with sigma of 0.04 and sigma for terminal
atoms of 0.08 within 1.7A
C12 \\sim C2 \\sim C1 \\sim C15 \\sim C00O \\sim C00R: within 1.7A with sigma
of 0.04 and sigma for terminal atoms of 0.08 within 1.7A
Uanis(C01U) \\sim Ueq: with sigma of 0.05 and sigma for terminal atoms of 0.05
Uanis(O007) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(C01H) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C00K) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C01D) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(C017) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Rigid body (RIGU) restrains
 C00H, C00J, C00X, C013, C01I, C01N
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N00F, C00Q, C00T, C014, C00L, C00K
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C01A, C01P, C01Z, C01K, C01M, C016
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C016, C01A, C01K, C01M, C01P, C01Z
 with sigma for 1-2 distances of 0.008 and sigma for 1-3 distances of 0.008
 C00T, C00X, C013, C014, C019, C01M, C01P, C01V
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C017, C01U
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C00S, C9, C10, C00P, C00N, C6
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C01K, C01M, C01P, C01Z, C01A, C016
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C00I, C011, C01J, C01S, C01T, C01U
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 O007, O008, C017
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C010, C020, C01C, C00G, C01Q, C01R
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C01H, O005
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 O00C, C018, C01H
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C00K, C00L, C00G, N00F
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N00A, C00D, C00M, C7, C11, C01L
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C00M, N00A, C00D, C7, C01L, C11
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C12, C00M
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N00F, C00K, C00Q, C014, C00L, C00T
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C00K, C00L, C00Q, N00F, C00T, C014
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 N00A, C00D, C00M, C7, C01L, C11
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C01D, O006, C01E
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C00K, C00L, N00F, C00Q, C014, C00T
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C00K, C00G
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C00G, C00K, N00F, C00L
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C8, C01J, C7
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C7, C8, C01J, C9
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C2, C12, C00R, C15, C00O, C1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 Br01, Br02, F003, F004, O005, O006, O007, O008, O009, N00A, H00A, O00B, O00C,
 C00D, H00D, O00E, N00F, H00F, C00G, C00H, H00H, C00I, H00I, C00J, C00K, C00L,
 H00L, C00M, C00N, H00N, C00O, C00P, H00P, C00Q, H00Q, C00R, H00R, C00S, C00T,
 C5, H5, C6, H6, C7, C00X, C8, H8, C00Z, C010, H010, C011, H011, C9, C013, C014,
  C1, H1, C016, H016, C017, C018, C019, H019, C01A, H01G, C2, H2, C01C, C01D,
 H01H, H01I, H01J, C01E, C12, C10, H10, C01H, H01K, H01M, H01N, C01I, H01O,
 C01J, C01K, H01P, C01L, H01L, C01M, C01N, C11, C01P, C01Q, H01Q, C01R, H01R,
 C01S, C01T, C01U, C01V, H01V, C01W, H01A, H01B, H01C, C15, H15, C01Y, H01D,
 H01E, H01F, C01Z, H01Z, C020, H020
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C017, O008, C01U, O007
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Ternary CH refined with riding coordinates:
 C5(H5), C8(H8), C019(H019), C01V(H01V)
4.b Aromatic/amide H refined with riding coordinates:
 N00A(H00A), C00D(H00D), N00F(H00F), C00H(H00H), C00I(H00I), C00L(H00L),
 C00N(H00N), C00P(H00P), C00Q(H00Q), C00R(H00R), C6(H6), C010(H010), C011(H011),
  C1(H1), C016(H016), C01A(H01G), C2(H2), C10(H10), C01I(H01O), C01K(H01P),
 C01L(H01L), C01Q(H01Q), C01R(H01R), C15(H15), C01Z(H01Z), C020(H020)
4.c Idealised Me refined as rotating group:
 C01D(H01H,H01I,H01J), C01H(H01K,H01M,H01N), C01W(H01A,H01B,H01C), C01Y(H01D,
 H01E,H01F)
;
_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
Br01 Br 1.11963(11) 0.77281(11) 0.28316(2) 0.0317(4) Uani 1 1 d . . . A 1
Br02 Br 0.47744(11) 0.91635(11) 0.46459(2) 0.0330(4) Uani 1 1 d . . . . .
F003 F 0.5797(7) 1.1048(7) 0.16878(14) 0.046(2) Uani 1 1 d . . . . .
F004 F 0.6855(7) 0.9191(7) 0.58072(15) 0.049(2) Uani 1 1 d . . . . .
O005 O 1.0562(7) 0.7680(8) 0.36046(14) 0.029(2) Uani 1 1 d . U . . .
O006 O 0.8374(7) 1.0028(7) 0.38453(15) 0.027(2) Uani 1 1 d . U . . .
O007 O 0.5933(7) 0.7271(8) 0.37656(17) 0.041(3) Uani 1 1 d . U . . .
O008 O 0.7535(7) 0.6768(7) 0.36358(16) 0.030(2) Uani 1 1 d . . . . .
O009 O 0.9998(8) 0.9520(7) 0.37257(17) 0.038(3) Uani 1 1 d . . . . .
N00A N 0.7911(8) 0.9165(8) 0.25123(18) 0.024(2) Uani 1 1 d . U . . .
H00A H 0.804266 0.885899 0.239111 0.029 Uiso 1 1 calc R U . . .
O00B O 0.5360(7) 0.9115(9) 0.38778(16) 0.042(3) Uani 1 1 d . . . . .
O00C O 1.1657(7) 0.7944(9) 0.39007(16) 0.044(3) Uani 1 1 d . U . . .
C00D C 0.8500(9) 0.8911(8) 0.2691(2) 0.018(2) Uani 1 1 d . U . . .
H00D H 0.901147 0.841041 0.268345 0.022 Uiso 1 1 calc R U . . .
O00E O 0.4261(8) 0.8860(8) 0.35949(17) 0.043(3) Uani 1 1 d . . . . .
N00F N 0.8527(8) 0.6924(7) 0.49899(18) 0.023(2) Uani 1 1 d . U . . .
H00F H 0.883735 0.673995 0.511202 0.028 Uiso 1 1 calc R U . . .
C00G C 0.7527(10) 0.8039(10) 0.5211(2) 0.026(3) Uani 1 1 d . . . . .
C00H C 0.9583(10) 0.7041(10) 0.4094(2) 0.028(3) Uani 1 1 d . . . . .
H00H H 1.010515 0.654685 0.409272 0.033 Uiso 1 1 calc R U . . .
C00I C 0.7943(10) 0.8308(10) 0.3394(2) 0.027(3) Uani 1 1 d . U . . .
H00I H 0.848523 0.782930 0.338984 0.032 Uiso 1 1 calc R U . . .
C00J C 0.9727(10) 0.7804(9) 0.3955(2) 0.022(2) Uani 1 1 d . . . . .
C00K C 0.7787(10) 0.7632(10) 0.4998(2) 0.027(2) Uani 1 1 d . U . . .
C00L C 0.7245(11) 0.7885(10) 0.4804(2) 0.027(3) Uani 1 1 d . U . . .
H00L H 0.668204 0.834605 0.480459 0.032 Uiso 1 1 calc R U . . .
C00M C 0.7146(11) 0.9843(10) 0.2505(2) 0.028(3) Uani 1 1 d . U . . .
C00N C 1.0055(10) 1.2019(10) 0.3194(2) 0.029(3) Uani 1 1 d . . . . .
H00N H 1.025632 1.264966 0.321686 0.035 Uiso 1 1 calc R U . . .
C00O C 0.6036(10) 1.0757(11) 0.1888(2) 0.031(3) Uani 1 1 d . U . . .
C00P C 1.0907(11) 1.1336(11) 0.3192(2) 0.035(4) Uani 1 1 d . . . . .
H00P H 1.166880 1.149446 0.320561 0.042 Uiso 1 1 calc R U . . .
C00Q C 0.8810(11) 0.6486(10) 0.4803(2) 0.028(3) Uani 1 1 d . U . . .
H00Q H 0.936263 0.601538 0.480516 0.034 Uiso 1 1 calc R U . . .
C00R C 0.6625(11) 0.9530(11) 0.2118(2) 0.031(3) Uani 1 1 d . U . . .
H00R H 0.685236 0.890335 0.213798 0.038 Uiso 1 1 calc R U . . .
C00S C 0.8673(10) 1.0878(10) 0.3141(2) 0.028(3) Uani 1 1 d . . . . .
C00T C 0.7551(10) 0.7445(10) 0.4613(2) 0.025(2) Uani 1 1 d . U . . .
C5 C 0.7453(9) 1.0581(9) 0.31057(19) 0.019(2) Uani 1 1 d . . . . .
H5 H 0.690122 1.109926 0.311227 0.023 Uiso 1 1 calc R U . . .
C6 C 0.8985(11) 1.1814(10) 0.3165(2) 0.028(3) Uani 1 1 d . . . . .
H6 H 0.844291 1.229272 0.316155 0.033 Uiso 1 1 calc R U . . .
C7 C 0.8358(10) 0.9366(9) 0.2879(2) 0.023(2) Uani 1 1 d . U . . .
C00X C 0.7858(10) 0.7761(10) 0.4232(2) 0.023(3) Uani 1 1 d . . . . .
C8 C 0.8918(10) 0.9251(10) 0.3100(2) 0.024(2) Uani 1 1 d . U . . .
H8 H 0.948054 0.874006 0.310129 0.028 Uiso 1 1 calc R U . . .
C00Z C 0.5209(11) 0.8935(11) 0.3670(2) 0.033(3) Uani 1 1 d . . . . .
C010 C 0.7470(12) 0.7477(10) 0.5400(2) 0.034(3) Uani 1 1 d . . . . .
H010 H 0.760684 0.682856 0.538760 0.041 Uiso 1 1 calc R U . . .
C011 C 0.6386(10) 0.9760(10) 0.3409(2) 0.027(3) Uani 1 1 d . U . . .
H011 H 0.588591 1.026773 0.341891 0.032 Uiso 1 1 calc R U . . .
C9 C 0.9440(10) 1.0213(10) 0.3131(2) 0.027(3) Uani 1 1 d . . . . .
C013 C 0.8691(10) 0.7011(9) 0.4230(2) 0.021(2) Uani 1 1 d . . . . .
C014 C 0.8300(10) 0.6717(10) 0.4609(2) 0.027(2) Uani 1 1 d . U . . .
C1 C 0.6142(10) 1.1337(11) 0.2057(2) 0.032(3) Uani 1 1 d . U . . .
H1 H 0.599255 1.197879 0.203505 0.038 Uiso 1 1 calc R U . . .
C016 C 0.6975(10) 0.5005(10) 0.4315(2) 0.023(2) Uani 1 1 d . U . . .
H016 H 0.751574 0.452500 0.431250 0.028 Uiso 1 1 calc R U . . .
C017 C 0.6768(10) 0.7413(10) 0.3658(2) 0.025(3) Uani 1 1 d . U . . .
C018 C 1.0750(9) 0.7817(9) 0.3816(2) 0.018(2) Uani 1 1 d . U . . .
C019 C 0.6950(9) 0.7589(9) 0.43936(19) 0.017(2) Uani 1 1 d . . . . .
H019 H 0.638215 0.809527 0.439783 0.021 Uiso 1 1 calc R U . . .
C01A C 0.5814(11) 0.4790(11) 0.4285(3) 0.035(3) Uani 1 1 d . U . . .
H01G H 0.558733 0.416434 0.426362 0.042 Uiso 1 1 calc R U . . .
C2 C 0.6443(11) 1.1063(10) 0.2255(2) 0.032(3) Uani 1 1 d . U . . .
H2 H 0.649002 1.149707 0.237074 0.038 Uiso 1 1 calc R U . . .
C01C C 0.7026(13) 0.8801(12) 0.5613(3) 0.039(3) Uani 1 1 d . . . . .
C01D C 0.8630(10) 1.0972(10) 0.3755(2) 0.033(3) Uani 1 1 d . U . . .
H01H H 0.882885 1.091721 0.360148 0.050 Uiso 1 1 calc R U . . .
H01I H 0.925053 1.124498 0.383597 0.050 Uiso 1 1 calc R U . . .
H01J H 0.797610 1.137237 0.377000 0.050 Uiso 1 1 calc R U . . .
C01E C 0.9179(11) 0.9375(10) 0.3826(2) 0.030(3) Uani 1 1 d . U . . .
C12 C 0.6695(11) 1.0108(10) 0.2290(2) 0.031(3) Uani 1 1 d . U . . .
C10 C 1.0544(11) 1.0397(11) 0.3167(2) 0.030(3) Uani 1 1 d . . . . .
H10 H 1.106248 0.990091 0.317635 0.036 Uiso 1 1 calc R U . . .
C01H C 1.1536(11) 0.7786(14) 0.3464(2) 0.048(4) Uani 1 1 d . U . . .
H01K H 1.131858 0.769417 0.331235 0.072 Uiso 1 1 calc R U . . .
H01M H 1.209535 0.732262 0.350456 0.072 Uiso 1 1 calc R U . . .
H01N H 1.184516 0.841091 0.348244 0.072 Uiso 1 1 calc R U . . .
C01I C 0.8038(10) 0.8486(9) 0.4094(2) 0.020(2) Uani 1 1 d . . . . .
H01O H 0.750856 0.897509 0.409269 0.024 Uiso 1 1 calc R U . . .
C01J C 0.8018(10) 0.9102(10) 0.3262(2) 0.024(2) Uani 1 1 d . U . . .
C01K C 0.5370(10) 0.6439(10) 0.4318(2) 0.031(3) Uani 1 1 d . U . . .
H01P H 0.482864 0.691873 0.431894 0.037 Uiso 1 1 calc R U . . .
C01L C 0.6931(11) 1.0326(10) 0.2699(2) 0.027(3) Uani 1 1 d . U . . .
H01L H 0.638094 1.079838 0.270499 0.032 Uiso 1 1 calc R U . . .
C01M C 0.6468(9) 0.6642(9) 0.43452(19) 0.017(2) Uani 1 1 d . U . . .
C01N C 0.8939(10) 0.8557(9) 0.3957(2) 0.023(3) Uani 1 1 d . . . . .
C11 C 0.7545(9) 1.0095(9) 0.2882(2) 0.021(2) Uani 1 1 d . U . . .
C01P C 0.7285(10) 0.5909(10) 0.4347(2) 0.023(2) Uani 1 1 d . U . . .
C01Q C 0.7268(12) 0.8994(11) 0.5242(3) 0.042(3) Uani 1 1 d . . . . .
H01Q H 0.722639 0.937842 0.511723 0.051 Uiso 1 1 calc R U . . .
C01R C 0.7223(10) 0.7846(12) 0.5601(2) 0.030(3) Uani 1 1 d . . . . .
H01R H 0.718669 0.746440 0.572700 0.036 Uiso 1 1 calc R U . . .
C01S C 0.7259(10) 0.9794(10) 0.3271(2) 0.024(2) Uani 1 1 d . U . . .
C01T C 0.6233(10) 0.8980(10) 0.3535(2) 0.026(2) Uani 1 1 d . U . . .
C01U C 0.7011(10) 0.8266(10) 0.3532(2) 0.027(3) Uani 1 1 d . U . . .
C01V C 0.8431(10) 0.6263(10) 0.4389(2) 0.027(3) Uani 1 1 d . . . . .
H01V H 0.899787 0.575598 0.438975 0.032 Uiso 1 1 calc R U . . .
C01W C 0.7312(14) 0.5872(12) 0.3734(3) 0.055(5) Uani 1 1 d . . . . .
H01A H 0.789044 0.543007 0.369162 0.082 Uiso 1 1 calc R U . . .
H01B H 0.658893 0.564431 0.368478 0.082 Uiso 1 1 calc R U . . .
H01C H 0.730532 0.593675 0.389283 0.082 Uiso 1 1 calc R U . . .
C15 C 0.6252(11) 0.9785(12) 0.1919(2) 0.035(3) Uani 1 1 d . U . . .
H15 H 0.613952 0.934299 0.180671 0.043 Uiso 1 1 calc R U . . .
C01Y C 0.4422(13) 0.9022(14) 0.4012(3) 0.055(5) Uani 1 1 d . . . . .
H01D H 0.393763 0.956263 0.399260 0.082 Uiso 1 1 calc R U . . .
H01E H 0.465586 0.898108 0.416394 0.082 Uiso 1 1 calc R U . . .
H01F H 0.401743 0.845588 0.397176 0.082 Uiso 1 1 calc R U . . .
C01Z C 0.5050(12) 0.5480(11) 0.4288(3) 0.051(5) Uani 1 1 d . U . . .
H01Z H 0.428855 0.532997 0.426971 0.061 Uiso 1 1 calc R U . . .
C020 C 0.7081(16) 0.9384(15) 0.5432(3) 0.063(5) Uani 1 1 d . . . . .
H020 H 0.698655 1.003673 0.544603 0.075 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
F003 C00O 1.330(16) . ?
F004 C01C 1.337(17) . ?
O005 C018 1.336(14) . ?
O005 C01H 1.465(15) . ?
O006 C01D 1.499(16) . ?
O006 C01E 1.356(16) . ?
O007 C017 1.223(13) . ?
O008 C017 1.317(16) . ?
O008 C01W 1.449(18) . ?
O009 C01E 1.183(15) . ?
N00A H00A 0.8800 . ?
N00A C00D 1.360(15) . ?
N00A C00M 1.344(15) . ?
O00B C00Z 1.315(17) . ?
O00B C01Y 1.406(16) . ?
O00C C018 1.225(14) . ?
C00D H00D 0.9500 . ?
C00D C7 1.335(17) . ?
O00E C00Z 1.239(17) . ?
N00F H00F 0.8800 . ?
N00F C00K 1.355(16) . ?
N00F C00Q 1.355(16) . ?
C00G C00K 1.469(19) . ?
C00G C010 1.419(18) . ?
C00G C01Q 1.42(2) . ?
C00H H00H 0.9500 . ?
C00H C00J 1.399(17) . ?
C00H C013 1.364(17) . ?
C00I H00I 0.9500 . ?
C00I C01J 1.402(19) . ?
C00I C01U 1.411(17) . ?
C00J C018 1.501(16) . ?
C00J C01N 1.441(17) . ?
C00K C00L 1.406(18) . ?
C00L H00L 0.9500 . ?
C00L C00T 1.388(18) . ?
C00M C12 1.478(19) . ?
C00M C01L 1.406(18) . ?
C00N H00N 0.9500 . ?
C00N C00P 1.421(19) . ?
C00N C6 1.336(18) . ?
C00O C1 1.34(2) . ?
C00O C15 1.44(2) . ?
C00P H00P 0.9500 . ?
C00P C10 1.43(2) . ?
C00Q H00Q 0.9500 . ?
C00Q C014 1.381(17) . ?
C00R H00R 0.9500 . ?
C00R C12 1.349(19) . ?
C00R C15 1.354(19) . ?
C00S C5 1.547(17) . ?
C00S C6 1.406(19) . ?
C00S C9 1.333(19) . ?
C00T C014 1.383(18) . ?
C00T C019 1.544(17) . ?
C5 H5 1.0000 . ?
C5 C11 1.545(17) . ?
C5 C01S 1.539(18) . ?
C6 H6 0.9500 . ?
C7 C8 1.531(17) . ?
C7 C11 1.436(17) . ?
C00X C013 1.475(18) . ?
C00X C019 1.499(16) . ?
C00X C01I 1.360(18) . ?
C8 H8 1.0000 . ?
C8 C9 1.532(19) . ?
C8 C01J 1.490(17) . ?
C00Z C01T 1.490(18) . ?
C010 H010 0.9500 . ?
C010 C01R 1.380(19) . ?
C011 H011 0.9500 . ?
C011 C01S 1.354(17) . ?
C011 C01T 1.376(18) . ?
C9 C10 1.376(18) . ?
C013 C01V 1.490(18) . ?
C014 C01V 1.511(19) . ?
C1 H1 0.9500 . ?
C1 C2 1.328(19) . ?
C016 H016 0.9500 . ?
C016 C01A 1.446(18) . ?
C016 C01P 1.367(18) . ?
C017 C01U 1.480(18) . ?
C019 H019 1.0000 . ?
C019 C01M 1.512(17) . ?
C01A H01G 0.9500 . ?
C01A C01Z 1.35(2) . ?
C2 H2 0.9500 . ?
C2 C12 1.423(19) . ?
C01C C01R 1.40(2) . ?
C01C C020 1.39(2) . ?
C01D H01H 0.9800 . ?
C01D H01I 0.9800 . ?
C01D H01J 0.9800 . ?
C01E C01N 1.455(18) . ?
C10 H10 0.9500 . ?
C01H H01K 0.9800 . ?
C01H H01M 0.9800 . ?
C01H H01N 0.9800 . ?
C01I H01O 0.9500 . ?
C01I C01N 1.381(17) . ?
C01J C01S 1.353(19) . ?
C01K H01P 0.9500 . ?
C01K C01M 1.366(17) . ?
C01K C01Z 1.45(2) . ?
C01L H01L 0.9500 . ?
C01L C11 1.389(17) . ?
C01M C01P 1.443(17) . ?
C01P C01V 1.495(18) . ?
C01Q H01Q 0.9500 . ?
C01Q C020 1.32(2) . ?
C01R H01R 0.9500 . ?
C01T C01U 1.391(19) . ?
C01V H01V 1.0000 . ?
C01W H01A 0.9800 . ?
C01W H01B 0.9800 . ?
C01W H01C 0.9800 . ?
C15 H15 0.9500 . ?
C01Y H01D 0.9800 . ?
C01Y H01E 0.9800 . ?
C01Y H01F 0.9800 . ?
C01Z H01Z 0.9500 . ?
C020 H020 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C018 O005 C01H 115.0(10) . . ?
C01E O006 C01D 116.7(10) . . ?
C017 O008 C01W 116.9(11) . . ?
C00D N00A H00A 117.3 . . ?
C00M N00A H00A 117.3 . . ?
C00M N00A C00D 125.4(11) . . ?
C00Z O00B C01Y 116.0(12) . . ?
N00A C00D H00D 120.0 . . ?
C7 C00D N00A 120.0(12) . . ?
C7 C00D H00D 120.0 . . ?
C00K N00F H00F 118.5 . . ?
C00K N00F C00Q 123.1(11) . . ?
C00Q N00F H00F 118.5 . . ?
C010 C00G C00K 120.9(13) . . ?
C010 C00G C01Q 115.3(13) . . ?
C01Q C00G C00K 123.7(13) . . ?
C00J C00H H00H 120.1 . . ?
C013 C00H H00H 120.1 . . ?
C013 C00H C00J 119.7(12) . . ?
C01J C00I H00I 122.2 . . ?
C01J C00I C01U 115.7(12) . . ?
C01U C00I H00I 122.2 . . ?
C00H C00J C018 117.2(11) . . ?
C00H C00J C01N 120.2(11) . . ?
C01N C00J C018 122.5(11) . . ?
N00F C00K C00G 118.2(12) . . ?
N00F C00K C00L 118.1(13) . . ?
C00L C00K C00G 123.6(13) . . ?
C00K C00L H00L 120.7 . . ?
C00T C00L C00K 118.5(13) . . ?
C00T C00L H00L 120.7 . . ?
N00A C00M C12 118.0(12) . . ?
N00A C00M C01L 117.2(12) . . ?
C01L C00M C12 124.3(12) . . ?
C00P C00N H00N 118.5 . . ?
C6 C00N H00N 118.5 . . ?
C6 C00N C00P 123.0(14) . . ?
F003 C00O C1 122.9(15) . . ?
F003 C00O C15 118.2(13) . . ?
C1 C00O C15 118.9(14) . . ?
C00N C00P H00P 122.2 . . ?
C00N C00P C10 115.6(12) . . ?
C10 C00P H00P 122.2 . . ?
N00F C00Q H00Q 119.8 . . ?
N00F C00Q C014 120.5(13) . . ?
C014 C00Q H00Q 119.8 . . ?
C12 C00R H00R 117.9 . . ?
C12 C00R C15 124.3(15) . . ?
C15 C00R H00R 117.9 . . ?
C6 C00S C5 122.3(12) . . ?
C9 C00S C5 117.1(13) . . ?
C9 C00S C6 120.4(12) . . ?
C00L C00T C019 123.7(11) . . ?
C014 C00T C00L 122.1(12) . . ?
C014 C00T C019 113.4(11) . . ?
C00S C5 H5 114.9 . . ?
C11 C5 C00S 100.4(9) . . ?
C11 C5 H5 114.9 . . ?
C01S C5 C00S 104.8(10) . . ?
C01S C5 H5 114.9 . . ?
C01S C5 C11 105.3(11) . . ?
C00N C6 C00S 119.0(13) . . ?
C00N C6 H6 120.5 . . ?
C00S C6 H6 120.5 . . ?
C00D C7 C8 131.1(12) . . ?
C00D C7 C11 117.4(11) . . ?
C11 C7 C8 111.5(11) . . ?
C013 C00X C019 112.5(11) . . ?
C01I C00X C013 116.5(11) . . ?
C01I C00X C019 131.0(12) . . ?
C7 C8 H8 112.6 . . ?
C7 C8 C9 101.2(10) . . ?
C9 C8 H8 112.6 . . ?
C01J C8 C7 106.8(10) . . ?
C01J C8 H8 112.6 . . ?
C01J C8 C9 110.2(11) . . ?
O00B C00Z C01T 114.7(12) . . ?
O00E C00Z O00B 120.6(12) . . ?
O00E C00Z C01T 124.1(13) . . ?
C00G C010 H010 119.1 . . ?
C01R C010 C00G 121.8(14) . . ?
C01R C010 H010 119.1 . . ?
C01S C011 H011 120.4 . . ?
C01S C011 C01T 119.2(13) . . ?
C01T C011 H011 120.4 . . ?
C00S C9 C8 111.7(12) . . ?
C00S C9 C10 121.8(14) . . ?
C10 C9 C8 126.2(13) . . ?
C00H C013 C00X 121.3(12) . . ?
C00H C013 C01V 126.4(12) . . ?
C00X C013 C01V 112.3(11) . . ?
C00Q C014 C00T 117.5(13) . . ?
C00Q C014 C01V 128.4(13) . . ?
C00T C014 C01V 114.1(11) . . ?
C00O C1 H1 118.3 . . ?
C2 C1 C00O 123.5(15) . . ?
C2 C1 H1 118.3 . . ?
C01A C016 H016 120.4 . . ?
C01P C016 H016 120.4 . . ?
C01P C016 C01A 119.1(12) . . ?
O007 C017 O008 121.2(12) . . ?
O007 C017 C01U 125.8(12) . . ?
O008 C017 C01U 113.0(10) . . ?
O005 C018 C00J 114.5(10) . . ?
O00C C018 O005 125.9(11) . . ?
O00C C018 C00J 119.6(11) . . ?
C00T C019 H019 113.4 . . ?
C00X C019 C00T 105.0(9) . . ?
C00X C019 H019 113.4 . . ?
C00X C019 C01M 107.4(10) . . ?
C01M C019 C00T 103.3(10) . . ?
C01M C019 H019 113.4 . . ?
C016 C01A H01G 120.0 . . ?
C01Z C01A C016 120.0(14) . . ?
C01Z C01A H01G 120.0 . . ?
C1 C2 H2 120.4 . . ?
C1 C2 C12 119.1(14) . . ?
C12 C2 H2 120.4 . . ?
F004 C01C C01R 119.0(15) . . ?
F004 C01C C020 117.9(16) . . ?
C020 C01C C01R 123.0(16) . . ?
O006 C01D H01H 109.5 . . ?
O006 C01D H01I 109.5 . . ?
O006 C01D H01J 109.5 . . ?
H01H C01D H01I 109.5 . . ?
H01H C01D H01J 109.5 . . ?
H01I C01D H01J 109.5 . . ?
O006 C01E C01N 111.7(11) . . ?
O009 C01E O006 121.4(13) . . ?
O009 C01E C01N 126.7(13) . . ?
C00R C12 C00M 124.4(13) . . ?
C00R C12 C2 117.4(13) . . ?
C2 C12 C00M 117.7(13) . . ?
C00P C10 H10 120.2 . . ?
C9 C10 C00P 119.7(13) . . ?
C9 C10 H10 120.2 . . ?
O005 C01H H01K 109.5 . . ?
O005 C01H H01M 109.5 . . ?
O005 C01H H01N 109.5 . . ?
H01K C01H H01M 109.5 . . ?
H01K C01H H01N 109.5 . . ?
H01M C01H H01N 109.5 . . ?
C00X C01I H01O 117.9 . . ?
C00X C01I C01N 124.3(12) . . ?
C01N C01I H01O 117.9 . . ?
C00I C01J C8 123.3(12) . . ?
C01S C01J C00I 122.2(12) . . ?
C01S C01J C8 114.4(12) . . ?
C01M C01K H01P 120.7 . . ?
C01M C01K C01Z 118.6(13) . . ?
C01Z C01K H01P 120.7 . . ?
C00M C01L H01L 120.9 . . ?
C11 C01L C00M 118.2(12) . . ?
C11 C01L H01L 120.9 . . ?
C01K C01M C019 126.1(12) . . ?
C01K C01M C01P 120.5(12) . . ?
C01P C01M C019 113.2(10) . . ?
C00J C01N C01E 118.2(11) . . ?
C01I C01N C00J 117.9(11) . . ?
C01I C01N C01E 123.7(12) . . ?
C7 C11 C5 113.2(11) . . ?
C01L C11 C5 125.0(11) . . ?
C01L C11 C7 121.7(12) . . ?
C016 C01P C01M 120.5(11) . . ?
C016 C01P C01V 127.0(12) . . ?
C01M C01P C01V 112.6(12) . . ?
C00G C01Q H01Q 117.6 . . ?
C020 C01Q C00G 124.9(17) . . ?
C020 C01Q H01Q 117.6 . . ?
C010 C01R C01C 117.5(15) . . ?
C010 C01R H01R 121.3 . . ?
C01C C01R H01R 121.3 . . ?
C011 C01S C5 124.0(12) . . ?
C01J C01S C5 114.4(11) . . ?
C01J C01S C011 121.6(13) . . ?
C011 C01T C00Z 117.4(12) . . ?
C011 C01T C01U 120.3(12) . . ?
C01U C01T C00Z 122.3(12) . . ?
C00I C01U C017 120.6(12) . . ?
C01T C01U C00I 120.9(13) . . ?
C01T C01U C017 118.1(11) . . ?
C013 C01V C014 107.4(12) . . ?
C013 C01V C01P 109.1(11) . . ?
C013 C01V H01V 112.6 . . ?
C014 C01V H01V 112.6 . . ?
C01P C01V C014 101.9(10) . . ?
C01P C01V H01V 112.6 . . ?
O008 C01W H01A 109.5 . . ?
O008 C01W H01B 109.5 . . ?
O008 C01W H01C 109.5 . . ?
H01A C01W H01B 109.5 . . ?
H01A C01W H01C 109.5 . . ?
H01B C01W H01C 109.5 . . ?
C00O C15 H15 121.7 . . ?
C00R C15 C00O 116.5(15) . . ?
C00R C15 H15 121.7 . . ?
O00B C01Y H01D 109.5 . . ?
O00B C01Y H01E 109.5 . . ?
O00B C01Y H01F 109.5 . . ?
H01D C01Y H01E 109.5 . . ?
H01D C01Y H01F 109.5 . . ?
H01E C01Y H01F 109.5 . . ?
C01A C01Z C01K 121.3(14) . . ?
C01A C01Z H01Z 119.3 . . ?
C01K C01Z H01Z 119.3 . . ?
C01C C020 H020 121.3 . . ?
C01Q C020 C01C 117.3(19) . . ?
C01Q C020 H020 121.3 . . ?

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
F003 C00O C1 C2 -175.9(13) . . . . ?
F003 C00O C15 C00R 172.1(12) . . . . ?
F004 C01C C01R C010 -175.7(12) . . . . ?
F004 C01C C020 C01Q 178.9(15) . . . . ?
O006 C01E C01N C00J -179.3(12) . . . . ?
O006 C01E C01N C01I -4(2) . . . . ?
O007 C017 C01U C00I -172.7(14) . . . . ?
O007 C017 C01U C01T 0(2) . . . . ?
O008 C017 C01U C00I 4.2(19) . . . . ?
O008 C017 C01U C01T 177.2(12) . . . . ?
O009 C01E C01N C00J -5(2) . . . . ?
O009 C01E C01N C01I 170.4(15) . . . . ?
N00A C00D C7 C8 -178.2(12) . . . . ?
N00A C00D C7 C11 2.1(18) . . . . ?
N00A C00M C12 C00R 28(2) . . . . ?
N00A C00M C12 C2 -144.2(14) . . . . ?
N00A C00M C01L C11 2(2) . . . . ?
O00B C00Z C01T C011 -102.5(16) . . . . ?
O00B C00Z C01T C01U 78.2(18) . . . . ?
C00D N00A C00M C12 172.0(12) . . . . ?
C00D N00A C00M C01L 0(2) . . . . ?
C00D C7 C8 C9 120.0(15) . . . . ?
C00D C7 C8 C01J -124.6(15) . . . . ?
C00D C7 C11 C5 -179.5(11) . . . . ?
C00D C7 C11 C01L -0.4(19) . . . . ?
O00E C00Z C01T C011 68(2) . . . . ?
O00E C00Z C01T C01U -111.2(18) . . . . ?
N00F C00K C00L C00T -4.7(19) . . . . ?
N00F C00Q C014 C00T 4(2) . . . . ?
N00F C00Q C014 C01V -174.6(13) . . . . ?
C00G C00K C00L C00T -179.2(12) . . . . ?
C00G C010 C01R C01C 0(2) . . . . ?
C00G C01Q C020 C01C -7(3) . . . . ?
C00H C00J C018 O005 109.3(14) . . . . ?
C00H C00J C018 O00C -70.7(18) . . . . ?
C00H C00J C01N C01E 174.2(13) . . . . ?
C00H C00J C01N C01I -1.6(19) . . . . ?
C00H C013 C01V C014 124.9(14) . . . . ?
C00H C013 C01V C01P -125.4(14) . . . . ?
C00I C01J C01S C5 -176.9(12) . . . . ?
C00I C01J C01S C011 1(2) . . . . ?
C00J C00H C013 C00X 1(2) . . . . ?
C00J C00H C013 C01V -178.7(12) . . . . ?
C00K N00F C00Q C014 -3(2) . . . . ?
C00K C00G C010 C01R -179.7(13) . . . . ?
C00K C00G C01Q C020 -176.8(17) . . . . ?
C00K C00L C00T C014 6(2) . . . . ?
C00K C00L C00T C019 174.1(12) . . . . ?
C00L C00T C014 C00Q -5(2) . . . . ?
C00L C00T C014 C01V 173.6(12) . . . . ?
C00L C00T C019 C00X 132.1(13) . . . . ?
C00L C00T C019 C01M -115.5(13) . . . . ?
C00M N00A C00D C7 -1.8(19) . . . . ?
C00M C01L C11 C5 177.3(12) . . . . ?
C00M C01L C11 C7 -2(2) . . . . ?
C00N C00P C10 C9 5(2) . . . . ?
C00O C1 C2 C12 1(2) . . . . ?
C00P C00N C6 C00S 3(2) . . . . ?
C00Q N00F C00K C00G 178.6(12) . . . . ?
C00Q N00F C00K C00L 3.8(19) . . . . ?
C00Q C014 C01V C013 -128.2(15) . . . . ?
C00Q C014 C01V C01P 117.2(15) . . . . ?
C00S C5 C11 C7 55.1(13) . . . . ?
C00S C5 C11 C01L -124.0(13) . . . . ?
C00S C5 C01S C011 130.3(13) . . . . ?
C00S C5 C01S C01J -52.1(15) . . . . ?
C00S C9 C10 C00P -7(2) . . . . ?
C00T C014 C01V C013 53.2(14) . . . . ?
C00T C014 C01V C01P -61.4(15) . . . . ?
C00T C019 C01M C01K 120.4(14) . . . . ?
C00T C019 C01M C01P -54.6(12) . . . . ?
C5 C00S C6 C00N -179.7(13) . . . . ?
C5 C00S C9 C8 -3.7(18) . . . . ?
C5 C00S C9 C10 -177.7(13) . . . . ?
C6 C00N C00P C10 -3(2) . . . . ?
C6 C00S C5 C11 119.8(14) . . . . ?
C6 C00S C5 C01S -131.1(13) . . . . ?
C6 C00S C9 C8 -179.0(12) . . . . ?
C6 C00S C9 C10 7(2) . . . . ?
C7 C8 C9 C00S 62.8(14) . . . . ?
C7 C8 C9 C10 -123.5(15) . . . . ?
C7 C8 C01J C00I 121.2(14) . . . . ?
C7 C8 C01J C01S -57.8(15) . . . . ?
C00X C013 C01V C014 -54.7(13) . . . . ?
C00X C013 C01V C01P 54.9(15) . . . . ?
C00X C019 C01M C01K -129.0(14) . . . . ?
C00X C019 C01M C01P 56.0(13) . . . . ?
C00X C01I C01N C00J 2(2) . . . . ?
C00X C01I C01N C01E -173.9(13) . . . . ?
C8 C7 C11 C5 0.7(15) . . . . ?
C8 C7 C11 C01L 179.9(12) . . . . ?
C8 C9 C10 C00P 179.6(13) . . . . ?
C8 C01J C01S C5 2.0(17) . . . . ?
C8 C01J C01S C011 179.6(12) . . . . ?
C00Z C01T C01U C00I 176.7(13) . . . . ?
C00Z C01T C01U C017 4(2) . . . . ?
C010 C00G C00K N00F -36.1(19) . . . . ?
C010 C00G C00K C00L 138.5(14) . . . . ?
C010 C00G C01Q C020 6(2) . . . . ?
C011 C01T C01U C00I -3(2) . . . . ?
C011 C01T C01U C017 -175.6(13) . . . . ?
C9 C00S C5 C11 -55.5(15) . . . . ?
C9 C00S C5 C01S 53.6(16) . . . . ?
C9 C00S C6 C00N -5(2) . . . . ?
C9 C8 C01J C00I -129.7(14) . . . . ?
C9 C8 C01J C01S 51.3(15) . . . . ?
C013 C00H C00J C018 177.5(12) . . . . ?
C013 C00H C00J C01N 0(2) . . . . ?
C013 C00X C019 C00T 55.2(14) . . . . ?
C013 C00X C019 C01M -54.3(13) . . . . ?
C013 C00X C01I C01N 0(2) . . . . ?
C014 C00T C019 C00X -58.5(14) . . . . ?
C014 C00T C019 C01M 53.9(13) . . . . ?
C1 C00O C15 C00R -4(2) . . . . ?
C1 C2 C12 C00M 173.4(13) . . . . ?
C1 C2 C12 C00R 1(2) . . . . ?
C016 C01A C01Z C01K 1(3) . . . . ?
C016 C01P C01V C013 126.8(14) . . . . ?
C016 C01P C01V C014 -119.8(15) . . . . ?
C018 C00J C01N C01E -2.9(19) . . . . ?
C018 C00J C01N C01I -178.6(12) . . . . ?
C019 C00T C014 C00Q -174.7(11) . . . . ?
C019 C00T C014 C01V 4.0(16) . . . . ?
C019 C00X C013 C00H -179.8(12) . . . . ?
C019 C00X C013 C01V -0.1(15) . . . . ?
C019 C00X C01I C01N 178.2(13) . . . . ?
C019 C01M C01P C016 177.4(12) . . . . ?
C019 C01M C01P C01V -2.0(15) . . . . ?
C01A C016 C01P C01M -2(2) . . . . ?
C01A C016 C01P C01V 177.5(13) . . . . ?
C01D O006 C01E O009 -7(2) . . . . ?
C01D O006 C01E C01N 168.0(11) . . . . ?
C12 C00M C01L C11 -169.8(13) . . . . ?
C12 C00R C15 C00O 7(2) . . . . ?
C01H O005 C018 O00C -6(2) . . . . ?
C01H O005 C018 C00J 174.0(12) . . . . ?
C01I C00X C013 C00H -1.0(19) . . . . ?
C01I C00X C013 C01V 178.7(12) . . . . ?
C01I C00X C019 C00T -123.4(15) . . . . ?
C01I C00X C019 C01M 127.1(15) . . . . ?
C01J C00I C01U C017 172.4(13) . . . . ?
C01J C00I C01U C01T 0(2) . . . . ?
C01J C8 C9 C00S -50.0(16) . . . . ?
C01J C8 C9 C10 123.7(15) . . . . ?
C01K C01M C01P C016 2(2) . . . . ?
C01K C01M C01P C01V -177.3(12) . . . . ?
C01L C00M C12 C00R -160.2(15) . . . . ?
C01L C00M C12 C2 28(2) . . . . ?
C01M C01K C01Z C01A 0(3) . . . . ?
C01M C01P C01V C013 -53.9(15) . . . . ?
C01M C01P C01V C014 59.5(14) . . . . ?
C01N C00J C018 O005 -73.6(16) . . . . ?
C01N C00J C018 O00C 106.4(16) . . . . ?
C11 C5 C01S C011 -124.2(13) . . . . ?
C11 C5 C01S C01J 53.3(14) . . . . ?
C11 C7 C8 C9 -60.3(13) . . . . ?
C11 C7 C8 C01J 55.1(14) . . . . ?
C01P C016 C01A C01Z 0(2) . . . . ?
C01Q C00G C00K N00F 146.9(13) . . . . ?
C01Q C00G C00K C00L -39(2) . . . . ?
C01Q C00G C010 C01R -2(2) . . . . ?
C01R C01C C020 C01Q 4(3) . . . . ?
C01S C5 C11 C7 -53.5(13) . . . . ?
C01S C5 C11 C01L 127.4(13) . . . . ?
C01S C011 C01T C00Z -174.7(13) . . . . ?
C01S C011 C01T C01U 5(2) . . . . ?
C01T C011 C01S C5 173.7(12) . . . . ?
C01T C011 C01S C01J -4(2) . . . . ?
C01U C00I C01J C8 -177.5(12) . . . . ?
C01U C00I C01J C01S 1(2) . . . . ?
C01W O008 C017 O007 3(2) . . . . ?
C01W O008 C017 C01U -173.6(12) . . . . ?
C15 C00O C1 C2 0(2) . . . . ?
C15 C00R C12 C00M -177.3(14) . . . . ?
C15 C00R C12 C2 -5(2) . . . . ?
C01Y O00B C00Z O00E 13(2) . . . . ?
C01Y O00B C00Z C01T -176.2(14) . . . . ?
C01Z C01K C01M C019 -175.6(14) . . . . ?
C01Z C01K C01M C01P -1(2) . . . . ?
C020 C01C C01R C010 -1(2) . . . . ?

_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 -0.036 0.000 0.000 189.9 56.6 ?
2 0.000 0.223 0.250 175.8 56.5 ?
3 0.036 0.000 0.500 189.9 56.0 ?
4 0.000 -0.223 0.750 175.8 55.5 ?
5 0.464 0.500 0.000 189.9 56.6 ?
6 0.500 0.277 0.750 175.8 55.5 ?
7 0.500 0.723 0.250 175.8 56.5 ?
8 0.536 0.500 0.500 189.9 56.0 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_exptl_crystal_mounting_method fiber
_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 3.566
_oxdiff_exptl_absorpt_empirical_full_min 0.637
