# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

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

data_cd17020
_database_code_depnum_ccdc_archive 'CCDC 1870646'
_audit_update_record             
;
2018-09-30 deposited with the CCDC.
2018-10-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H20 Br N O2'
_chemical_formula_weight         386.28

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'

_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                   10.901(2)
_cell_length_b                   6.2481(11)
_cell_length_c                   13.318(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.052(4)
_cell_angle_gamma                90
_cell_volume                     898.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1621
_cell_measurement_theta_min      4.530
_cell_measurement_theta_max      43.937

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_F_000             396
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    2.300
_shelx_estimated_absorpt_T_min   0.656
_shelx_estimated_absorpt_T_max   0.894
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6170
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5164
_diffrn_reflns_av_unetI/netI     0.0764
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.887
_diffrn_reflns_theta_max         25.496
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             3261
_reflns_number_gt                2644
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.774
_reflns_Friedel_fraction_max     0.944
_reflns_Friedel_fraction_full    0.947

_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0231P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 938 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.031(10)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3261
_refine_ls_number_parameters     222
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0436
_refine_ls_wR_factor_ref         0.0945
_refine_ls_wR_factor_gt          0.0895
_refine_ls_goodness_of_fit_ref   0.976
_refine_ls_restrained_S_all      0.976
_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
Br1 Br 0.16721(6) -0.28895(10) 0.36721(4) 0.0650(3) Uani 1 1 d . . . . .
N1 N 0.3045(4) 0.4528(7) 0.7441(3) 0.0347(11) Uani 1 1 d . . . . .
O1 O 0.3221(3) 1.0007(6) 0.8179(3) 0.0484(10) Uani 1 1 d . . . . .
O2 O 0.3829(4) 0.6230(7) 0.6168(3) 0.0474(10) Uani 1 1 d . . . . .
C1 C 0.4457(5) 0.9366(10) 0.8088(5) 0.0540(17) Uani 1 1 d . . . . .
H1A H 0.5056 1.0293 0.8483 0.065 Uiso 1 1 calc R U . . .
H1B H 0.4600 0.9394 0.7386 0.065 Uiso 1 1 calc R U . . .
C2 C 0.4543(4) 0.7077(13) 0.8507(4) 0.0424(11) Uani 1 1 d . . . . .
H2 H 0.4689 0.7200 0.9248 0.051 Uiso 1 1 calc R U . . .
C3 C 0.3192(5) 0.6207(8) 0.8222(4) 0.0336(12) Uani 1 1 d . . . . .
C4 C 0.2461(5) 0.8250(8) 0.7810(4) 0.0373(12) Uani 1 1 d . . . . .
H4 H 0.2388 0.8240 0.7069 0.045 Uiso 1 1 calc R U . . .
C5 C 0.1186(5) 0.8513(8) 0.8103(4) 0.0358(12) Uani 1 1 d . . . . .
C6 C 0.0946(5) 0.9855(9) 0.8875(4) 0.0455(14) Uani 1 1 d . . . . .
H6 H 0.1590 1.0636 0.9233 0.055 Uiso 1 1 calc R U . . .
C7 C -0.0237(5) 1.0054(10) 0.9124(5) 0.0524(16) Uani 1 1 d . . . . .
H7 H -0.0384 1.0979 0.9642 0.063 Uiso 1 1 calc R U . . .
C8 C -0.1190(6) 0.8903(11) 0.8616(5) 0.0543(16) Uani 1 1 d . . . . .
H8 H -0.1985 0.9028 0.8789 0.065 Uiso 1 1 calc R U . . .
C9 C -0.0967(6) 0.7545(12) 0.7838(5) 0.062(2) Uani 1 1 d . . . . .
H9 H -0.1609 0.6743 0.7490 0.074 Uiso 1 1 calc R U . . .
C10 C 0.0214(5) 0.7392(12) 0.7585(4) 0.0478(15) Uani 1 1 d . . . . .
H10 H 0.0354 0.6510 0.7050 0.057 Uiso 1 1 calc R U . . .
C11 C 0.2746(5) 0.5251(9) 0.9153(4) 0.0417(14) Uani 1 1 d . . . . .
H11A H 0.1921 0.4704 0.8974 0.063 Uiso 1 1 calc R U . . .
H11B H 0.2745 0.6336 0.9663 0.063 Uiso 1 1 calc R U . . .
H11C H 0.3289 0.4108 0.9411 0.063 Uiso 1 1 calc R U . . .
C12 C 0.5564(5) 0.5768(11) 0.8216(5) 0.0514(16) Uani 1 1 d . . . . .
H12 H 0.5622 0.5633 0.7529 0.062 Uiso 1 1 calc R U . . .
C13 C 0.6388(6) 0.4792(12) 0.8855(6) 0.0670(19) Uani 1 1 d . . . . .
H13A H 0.6358 0.4894 0.9548 0.080 Uiso 1 1 calc R U . . .
H13B H 0.7009 0.3991 0.8619 0.080 Uiso 1 1 calc R U . . .
C14 C 0.3300(5) 0.4698(9) 0.6483(4) 0.0380(13) Uani 1 1 d . . . . .
C15 C 0.2893(5) 0.2823(9) 0.5814(4) 0.0374(13) Uani 1 1 d . . . . .
C16 C 0.1760(4) 0.1826(10) 0.5845(3) 0.0401(13) Uani 1 1 d . . . . .
H16 H 0.1251 0.2294 0.6305 0.048 Uiso 1 1 calc R U . . .
C17 C 0.1381(5) 0.0154(9) 0.5204(4) 0.0436(14) Uani 1 1 d . . . . .
H17 H 0.0614 -0.0489 0.5217 0.052 Uiso 1 1 calc R U . . .
C18 C 0.2149(5) -0.0544(9) 0.4547(4) 0.0400(13) Uani 1 1 d . . . . .
C19 C 0.3263(5) 0.0424(10) 0.4493(4) 0.0495(16) Uani 1 1 d . . . . .
H19 H 0.3775 -0.0069 0.4040 0.059 Uiso 1 1 calc R U . . .
C20 C 0.3620(4) 0.2137(14) 0.5118(3) 0.0458(12) Uani 1 1 d . . . . .
H20 H 0.4363 0.2834 0.5067 0.055 Uiso 1 1 calc R U . . .
H1 H 0.290(5) 0.329(9) 0.768(4) 0.031(15) Uiso 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
Br1 C18 1.899(5) . ?
N1 C14 1.347(6) . ?
N1 C3 1.470(7) . ?
N1 H1 0.86(5) . ?
O1 C4 1.421(6) . ?
O1 C1 1.427(7) . ?
O2 C14 1.222(7) . ?
C1 C2 1.533(10) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C12 1.476(8) . ?
C2 C3 1.566(7) . ?
C2 H2 0.9800 . ?
C3 C11 1.517(7) . ?
C3 C4 1.562(7) . ?
C4 C5 1.504(7) . ?
C4 H4 0.9800 . ?
C5 C10 1.373(7) . ?
C5 C6 1.380(8) . ?
C6 C7 1.381(8) . ?
C6 H6 0.9300 . ?
C7 C8 1.364(9) . ?
C7 H7 0.9300 . ?
C8 C9 1.387(9) . ?
C8 H8 0.9300 . ?
C9 C10 1.378(8) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.300(8) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9300 . ?
C13 H13B 0.9300 . ?
C14 C15 1.501(8) . ?
C15 C20 1.371(7) . ?
C15 C16 1.388(7) . ?
C16 C17 1.376(8) . ?
C16 H16 0.9300 . ?
C17 C18 1.364(7) . ?
C17 H17 0.9300 . ?
C18 C19 1.367(8) . ?
C19 C20 1.378(9) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?

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 N1 C3 126.7(5) . . ?
C14 N1 H1 119(4) . . ?
C3 N1 H1 113(3) . . ?
C4 O1 C1 105.4(4) . . ?
O1 C1 C2 104.0(4) . . ?
O1 C1 H1A 111.0 . . ?
C2 C1 H1A 111.0 . . ?
O1 C1 H1B 111.0 . . ?
C2 C1 H1B 111.0 . . ?
H1A C1 H1B 109.0 . . ?
C12 C2 C1 115.5(5) . . ?
C12 C2 C3 117.5(6) . . ?
C1 C2 C3 103.2(4) . . ?
C12 C2 H2 106.6 . . ?
C1 C2 H2 106.6 . . ?
C3 C2 H2 106.6 . . ?
N1 C3 C11 106.4(4) . . ?
N1 C3 C4 109.6(4) . . ?
C11 C3 C4 113.7(4) . . ?
N1 C3 C2 115.2(4) . . ?
C11 C3 C2 109.7(4) . . ?
C4 C3 C2 102.6(4) . . ?
O1 C4 C5 110.0(4) . . ?
O1 C4 C3 105.4(4) . . ?
C5 C4 C3 116.3(4) . . ?
O1 C4 H4 108.3 . . ?
C5 C4 H4 108.3 . . ?
C3 C4 H4 108.3 . . ?
C10 C5 C6 118.1(5) . . ?
C10 C5 C4 119.4(5) . . ?
C6 C5 C4 122.5(5) . . ?
C5 C6 C7 121.0(5) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C8 C7 C6 120.4(6) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C9 119.5(6) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C10 C9 C8 119.5(6) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C5 C10 C9 121.5(6) . . ?
C5 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C3 C11 H11A 109.5 . . ?
C3 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C3 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C2 124.4(6) . . ?
C13 C12 H12 117.8 . . ?
C2 C12 H12 117.8 . . ?
C12 C13 H13A 120.0 . . ?
C12 C13 H13B 120.0 . . ?
H13A C13 H13B 120.0 . . ?
O2 C14 N1 123.8(5) . . ?
O2 C14 C15 121.5(5) . . ?
N1 C14 C15 114.7(5) . . ?
C20 C15 C16 118.7(5) . . ?
C20 C15 C14 119.6(5) . . ?
C16 C15 C14 121.5(5) . . ?
C17 C16 C15 120.9(5) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C18 C17 C16 118.9(5) . . ?
C18 C17 H17 120.6 . . ?
C16 C17 H17 120.6 . . ?
C17 C18 C19 121.4(5) . . ?
C17 C18 Br1 120.0(4) . . ?
C19 C18 Br1 118.6(4) . . ?
C18 C19 C20 119.3(5) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C15 C20 C19 120.7(5) . . ?
C15 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?

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
C4 O1 C1 C2 -45.4(5) . . . . ?
O1 C1 C2 C12 161.3(5) . . . . ?
O1 C1 C2 C3 31.7(6) . . . . ?
C14 N1 C3 C11 178.3(5) . . . . ?
C14 N1 C3 C4 55.0(6) . . . . ?
C14 N1 C3 C2 -60.0(7) . . . . ?
C12 C2 C3 N1 -17.4(7) . . . . ?
C1 C2 C3 N1 111.0(5) . . . . ?
C12 C2 C3 C11 102.5(5) . . . . ?
C1 C2 C3 C11 -129.1(5) . . . . ?
C12 C2 C3 C4 -136.3(5) . . . . ?
C1 C2 C3 C4 -7.9(5) . . . . ?
C1 O1 C4 C5 166.1(4) . . . . ?
C1 O1 C4 C3 40.0(5) . . . . ?
N1 C3 C4 O1 -141.1(4) . . . . ?
C11 C3 C4 O1 100.0(5) . . . . ?
C2 C3 C4 O1 -18.3(5) . . . . ?
N1 C3 C4 C5 96.8(5) . . . . ?
C11 C3 C4 C5 -22.1(6) . . . . ?
C2 C3 C4 C5 -140.4(4) . . . . ?
O1 C4 C5 C10 160.4(5) . . . . ?
C3 C4 C5 C10 -79.8(6) . . . . ?
O1 C4 C5 C6 -19.2(7) . . . . ?
C3 C4 C5 C6 100.5(6) . . . . ?
C10 C5 C6 C7 0.4(8) . . . . ?
C4 C5 C6 C7 -179.9(5) . . . . ?
C5 C6 C7 C8 0.7(9) . . . . ?
C6 C7 C8 C9 -0.7(10) . . . . ?
C7 C8 C9 C10 -0.6(10) . . . . ?
C6 C5 C10 C9 -1.7(9) . . . . ?
C4 C5 C10 C9 178.6(6) . . . . ?
C8 C9 C10 C5 1.8(10) . . . . ?
C1 C2 C12 C13 125.6(7) . . . . ?
C3 C2 C12 C13 -112.1(7) . . . . ?
C3 N1 C14 O2 8.7(9) . . . . ?
C3 N1 C14 C15 -171.9(5) . . . . ?
O2 C14 C15 C20 37.1(8) . . . . ?
N1 C14 C15 C20 -142.3(5) . . . . ?
O2 C14 C15 C16 -139.5(6) . . . . ?
N1 C14 C15 C16 41.0(7) . . . . ?
C20 C15 C16 C17 1.2(8) . . . . ?
C14 C15 C16 C17 177.8(5) . . . . ?
C15 C16 C17 C18 1.3(8) . . . . ?
C16 C17 C18 C19 -2.0(9) . . . . ?
C16 C17 C18 Br1 178.6(4) . . . . ?
C17 C18 C19 C20 0.2(9) . . . . ?
Br1 C18 C19 C20 179.6(5) . . . . ?
C16 C15 C20 C19 -3.0(9) . . . . ?
C14 C15 C20 C19 -179.8(5) . . . . ?
C18 C19 C20 C15 2.4(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.86(5) 2.17(5) 2.988(6) 159(5) 1_545
C4 H4 O2 0.98 2.45 3.084(7) 121.9 .
C1 H1B O2 0.97 2.62 3.218(8) 120.2 .
N1 H1 O1 0.86(5) 2.17(5) 2.988(6) 159(5) 1_545
C4 H4 O2 0.98 2.45 3.084(7) 121.9 .
C1 H1B O2 0.97 2.62 3.218(8) 120.2 .
C1 H1B O2 0.97 2.62 3.218(8) 120.2 .
C4 H4 O2 0.98 2.45 3.084(7) 121.9 .
N1 H1 O1 0.86(5) 2.17(5) 2.988(6) 159(5) 1_545

_refine_diff_density_max         0.641
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.053

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_mo_d8v18616_0m
_database_code_depnum_ccdc_archive 'CCDC 1870647'
_audit_update_record             
;
2018-09-30 deposited with the CCDC.
2018-10-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H21 Cl N2 O4'
_chemical_formula_weight         388.84

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   10.4038(4)
_cell_length_b                   20.5233(6)
_cell_length_c                   37.6117(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     8030.9(5)
_cell_formula_units_Z            16
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9795
_cell_measurement_theta_min      4.474
_cell_measurement_theta_max      43.820

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_F_000             3264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.217
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6473
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\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            43420
_diffrn_reflns_av_unetI/netI     0.0634
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         2.383
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             14873
_reflns_number_gt                8904
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.814
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    0.994

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0763P)²+0.0643P] 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     SHELXL
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 3104 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.01(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         14873
_refine_ls_number_parameters     982
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0995
_refine_ls_R_factor_gt           0.0494
_refine_ls_wR_factor_ref         0.1509
_refine_ls_wR_factor_gt          0.1215
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.001
_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 0.9537(2) 0.52746(12) 0.86338(6) 0.1445(8) Uani 1 1 d . . . . .
Cl1A Cl 0.48031(15) 0.66010(7) 0.76249(4) 0.0942(5) Uani 1 1 d . . . . .
Cl1B Cl 0.8884(2) 0.43882(8) 0.61955(5) 0.1114(6) Uani 1 1 d . . . . .
Cl1C Cl 0.8027(2) 0.66531(7) 0.51825(5) 0.1189(6) Uani 1 1 d . . . . .
N1 N 0.6115(4) 0.56221(16) 0.90657(8) 0.0597(9) Uani 1 1 d . . . . .
H1 H 0.6279 0.5497 0.9279 0.072 Uiso 1 1 calc R U . . .
N2 N 0.6751(11) 0.3089(3) 0.93174(18) 0.130(3) Uani 1 1 d . . . . .
N1A N 0.6722(4) 0.50021(15) 0.77717(8) 0.0568(9) Uani 1 1 d . . . . .
H1A H 0.6825 0.5092 0.7993 0.068 Uiso 1 1 calc R U . . .
N2A N 1.0197(5) 0.6849(2) 0.80960(14) 0.0905(14) Uani 1 1 d . . . . .
N1B N 0.7094(4) 0.59886(15) 0.65296(8) 0.0632(10) Uani 1 1 d . . . . .
H1B H 0.6890 0.5846 0.6737 0.076 Uiso 1 1 calc R U . . .
N2B N 0.3453(6) 0.4153(3) 0.66424(13) 0.0981(16) Uani 1 1 d . . . . .
N1C N 0.7285(5) 0.50185(19) 0.52721(9) 0.0727(12) Uani 1 1 d . . . . .
H1C H 0.7205 0.5193 0.5479 0.087 Uiso 1 1 calc R U . . .
N2C N 1.2278(7) 0.5185(3) 0.58371(17) 0.1123(17) Uani 1 1 d . . . . .
O1 O 0.4712(5) 0.71380(19) 0.87325(12) 0.1123(15) Uani 1 1 d . . . . .
O2 O 0.6609(4) 0.54497(16) 0.84870(7) 0.0830(11) Uani 1 1 d . . . . .
O3 O 0.5637(9) 0.3176(3) 0.94057(19) 0.146(2) Uani 1 1 d . . . . .
O4 O 0.7356(9) 0.2593(2) 0.93847(15) 0.186(3) Uani 1 1 d . . . . .
O1A O 0.5428(4) 0.35446(14) 0.73305(8) 0.0751(10) Uani 1 1 d . . . . .
O2A O 0.6613(4) 0.54650(14) 0.72252(7) 0.0797(11) Uani 1 1 d . . . . .
O3A O 1.0839(5) 0.6360(2) 0.81102(18) 0.140(2) Uani 1 1 d . . . . .
O4A O 1.0590(5) 0.7368(2) 0.81883(19) 0.147(2) Uani 1 1 d . . . . .
O1B O 0.8894(6) 0.7424(2) 0.62437(11) 0.1129(16) Uani 1 1 d . . . . .
O2B O 0.7345(4) 0.56778(16) 0.59553(7) 0.0890(12) Uani 1 1 d . . . . .
O3B O 0.2910(6) 0.4635(3) 0.67393(19) 0.154(2) Uani 1 1 d . . . . .
O4B O 0.2963(6) 0.3617(2) 0.66418(15) 0.1345(18) Uani 1 1 d . . . . .
O1C O 0.5001(7) 0.4243(4) 0.46734(15) 0.170(3) Uani 1 1 d . . . . .
O2C O 0.8645(4) 0.49701(17) 0.47950(8) 0.0865(11) Uani 1 1 d . . . . .
O3C O 1.2227(6) 0.4597(3) 0.5840(2) 0.158(2) Uani 1 1 d . . . . .
O4C O 1.3154(6) 0.5493(3) 0.59701(18) 0.154(2) Uani 1 1 d . . . . .
C1 C 0.3646(8) 0.6722(4) 0.8686(2) 0.116(2) Uani 1 1 d . . . . .
H1X H 0.3355 0.6737 0.8441 0.140 Uiso 1 1 calc R U . . .
H1Y H 0.2943 0.6858 0.8838 0.140 Uiso 1 1 calc R U . . .
C2 C 0.4064(6) 0.6033(3) 0.87809(15) 0.0879(16) Uani 1 1 d . . . . .
H2 H 0.4399 0.5830 0.8564 0.105 Uiso 1 1 calc R U . . .
C3 C 0.5217(5) 0.6173(2) 0.90261(11) 0.0692(13) Uani 1 1 d . . . . .
C4 C 0.5816(6) 0.6751(2) 0.88134(14) 0.0811(16) Uani 1 1 d . . . . .
H4A H 0.6163 0.6580 0.8590 0.097 Uiso 1 1 calc R U . . .
C5 C 0.6816(9) 0.7152(3) 0.89842(15) 0.0928(19) Uani 1 1 d . . . . .
C6 C 0.8062(10) 0.7016(4) 0.89225(17) 0.106(2) Uani 1 1 d . . . . .
H6 H 0.8277 0.6658 0.8783 0.127 Uiso 1 1 calc R U . . .
C7 C 0.9053(11) 0.7411(6) 0.9066(2) 0.148(3) Uani 1 1 d . . . . .
H7 H 0.9911 0.7303 0.9030 0.178 Uiso 1 1 calc R U . . .
C8 C 0.8734(16) 0.7946(6) 0.9257(3) 0.162(4) Uani 1 1 d . . . . .
H8 H 0.9373 0.8225 0.9338 0.194 Uiso 1 1 calc R U . . .
C9 C 0.7503(16) 0.8073(4) 0.9328(3) 0.167(5) Uani 1 1 d . . . . .
H9 H 0.7301 0.8423 0.9475 0.201 Uiso 1 1 calc R U . . .
C10 C 0.6521(10) 0.7698(3) 0.9189(2) 0.134(3) Uani 1 1 d . . . . .
H10 H 0.5669 0.7808 0.9232 0.161 Uiso 1 1 calc R U . . .
C11 C 0.4837(7) 0.6363(3) 0.94032(13) 0.098(2) Uani 1 1 d . . . . .
H11A H 0.4469 0.5994 0.9522 0.146 Uiso 1 1 calc R U . . .
H11B H 0.4218 0.6710 0.9395 0.146 Uiso 1 1 calc R U . . .
H11C H 0.5585 0.6507 0.9531 0.146 Uiso 1 1 calc R U . . .
C12 C 0.2948(8) 0.5607(4) 0.8915(2) 0.124(2) Uani 1 1 d . . . . .
H12A H 0.2687 0.5759 0.9149 0.148 Uiso 1 1 calc R U . . .
H12B H 0.2220 0.5658 0.8756 0.148 Uiso 1 1 calc R U . . .
C13 C 0.3288(10) 0.4893(4) 0.8939(2) 0.147(3) Uani 1 1 d . . . . .
H13A H 0.3692 0.4757 0.8722 0.221 Uiso 1 1 calc R U . . .
H13B H 0.2520 0.4643 0.8977 0.221 Uiso 1 1 calc R U . . .
H13C H 0.3868 0.4826 0.9134 0.221 Uiso 1 1 calc R U . . .
C14 C 0.6699(5) 0.5298(2) 0.88041(11) 0.0643(12) Uani 1 1 d . . . . .
C15 C 0.7417(6) 0.4704(2) 0.89115(11) 0.0708(14) Uani 1 1 d . . . . .
C16 C 0.8711(8) 0.4642(3) 0.88234(15) 0.101(2) Uani 1 1 d . . . . .
C17 C 0.9361(9) 0.4050(5) 0.8888(2) 0.138(3) Uani 1 1 d . . . . .
H17 H 1.0220 0.4003 0.8825 0.166 Uiso 1 1 calc R U . . .
C18 C 0.8716(11) 0.3552(4) 0.90436(19) 0.129(3) Uani 1 1 d . . . . .
H18 H 0.9135 0.3159 0.9086 0.154 Uiso 1 1 calc R U . . .
C19 C 0.7449(9) 0.3621(3) 0.91396(14) 0.099(2) Uani 1 1 d . . . . .
C20 C 0.6801(6) 0.4193(2) 0.90750(12) 0.0776(15) Uani 1 1 d . . . . .
H20 H 0.5944 0.4234 0.9142 0.093 Uiso 1 1 calc R U . . .
C1A C 0.6776(6) 0.3418(2) 0.73026(13) 0.0754(14) Uani 1 1 d . . . . .
H1A1 H 0.7002 0.3310 0.7059 0.090 Uiso 1 1 calc R U . . .
H1A2 H 0.7016 0.3057 0.7455 0.090 Uiso 1 1 calc R U . . .
C2A C 0.7464(5) 0.4040(2) 0.74195(12) 0.0692(13) Uani 1 1 d . . . . .
H2A H 0.7474 0.4335 0.7215 0.083 Uiso 1 1 calc R U . . .
C3A C 0.6487(5) 0.43111(17) 0.76848(10) 0.0573(11) Uani 1 1 d . . . . .
C4A C 0.5244(5) 0.41903(19) 0.74686(11) 0.0615(12) Uani 1 1 d . . . . .
H4A1 H 0.5225 0.4497 0.7269 0.074 Uiso 1 1 calc R U . . .
C5A C 0.4000(5) 0.4242(2) 0.76654(11) 0.0643(12) Uani 1 1 d . . . . .
C6A C 0.3466(6) 0.4850(2) 0.77135(17) 0.0933(18) Uani 1 1 d . . . . .
H6A H 0.3859 0.5213 0.7613 0.112 Uiso 1 1 calc R U . . .
C7A C 0.2354(8) 0.4927(3) 0.7909(2) 0.111(2) Uani 1 1 d . . . . .
H7A H 0.2025 0.5342 0.7950 0.134 Uiso 1 1 calc R U . . .
C8A C 0.1740(7) 0.4395(3) 0.80410(18) 0.1035(19) Uani 1 1 d . . . . .
H8A H 0.0972 0.4444 0.8165 0.124 Uiso 1 1 calc R U . . .
C9A C 0.2237(7) 0.3807(3) 0.7994(2) 0.112(2) Uani 1 1 d . . . . .
H9A H 0.1820 0.3447 0.8091 0.134 Uiso 1 1 calc R U . . .
C10A C 0.3351(6) 0.3716(2) 0.78053(16) 0.0885(17) Uani 1 1 d . . . . .
H10A H 0.3670 0.3298 0.7772 0.106 Uiso 1 1 calc R U . . .
C11A C 0.6481(6) 0.3950(2) 0.80374(12) 0.0747(15) Uani 1 1 d . . . . .
H11D H 0.7314 0.3983 0.8146 0.112 Uiso 1 1 calc R U . . .
H11E H 0.6277 0.3500 0.7997 0.112 Uiso 1 1 calc R U . . .
H11F H 0.5848 0.4140 0.8192 0.112 Uiso 1 1 calc R U . . .
C12A C 0.8849(6) 0.3962(3) 0.75437(18) 0.0970(18) Uani 1 1 d . . . . .
H12C H 0.8903 0.3587 0.7700 0.116 Uiso 1 1 calc R U . . .
H12D H 0.9091 0.4343 0.7680 0.116 Uiso 1 1 calc R U . . .
C13A C 0.9801(9) 0.3874(5) 0.7241(3) 0.164(4) Uani 1 1 d . . . . .
H13D H 0.9674 0.3455 0.7133 0.246 Uiso 1 1 calc R U . . .
H13E H 1.0662 0.3902 0.7332 0.246 Uiso 1 1 calc R U . . .
H13F H 0.9670 0.4209 0.7067 0.246 Uiso 1 1 calc R U . . .
C14A C 0.6792(5) 0.55018(18) 0.75478(10) 0.0561(11) Uani 1 1 d . . . . .
C15A C 0.7201(5) 0.61342(17) 0.77180(10) 0.0523(11) Uani 1 1 d . . . . .
C16A C 0.8452(6) 0.62049(19) 0.78274(11) 0.0649(13) Uani 1 1 d . . . . .
H16A H 0.9021 0.5858 0.7807 0.078 Uiso 1 1 calc R U . . .
C17A C 0.8867(5) 0.6791(2) 0.79674(12) 0.0659(12) Uani 1 1 d . . . . .
C18A C 0.8072(6) 0.7321(2) 0.79974(13) 0.0672(13) Uani 1 1 d . . . . .
H18A H 0.8373 0.7713 0.8089 0.081 Uiso 1 1 calc R U . . .
C19A C 0.6826(6) 0.7256(2) 0.78896(12) 0.0667(13) Uani 1 1 d . . . . .
H19A H 0.6264 0.7606 0.7910 0.080 Uiso 1 1 calc R U . . .
C20A C 0.6393(5) 0.66644(19) 0.77490(11) 0.0590(11) Uani 1 1 d . . . . .
C1B C 0.7663(11) 0.7614(3) 0.61329(18) 0.124(3) Uani 1 1 d . . . . .
H1B1 H 0.7659 0.7686 0.5878 0.149 Uiso 1 1 calc R U . . .
H1B2 H 0.7420 0.8017 0.6249 0.149 Uiso 1 1 calc R U . . .
C2B C 0.6707(8) 0.7077(3) 0.62284(15) 0.098(2) Uani 1 1 d . . . . .
H2B H 0.6584 0.6803 0.6018 0.118 Uiso 1 1 calc R U . . .
C3B C 0.7461(5) 0.6682(2) 0.65053(11) 0.0664(13) Uani 1 1 d . . . . .
C4B C 0.8841(7) 0.6765(2) 0.63653(14) 0.0858(17) Uani 1 1 d . . . . .
H4B H 0.8964 0.6474 0.6162 0.103 Uiso 1 1 calc R U . . .
C5B C 0.9888(6) 0.6643(3) 0.66287(17) 0.0910(17) Uani 1 1 d . . . . .
C6B C 1.0248(8) 0.6010(3) 0.6706(2) 0.113(2) Uani 1 1 d . . . . .
H6B H 0.9888 0.5671 0.6575 0.136 Uiso 1 1 calc R U . . .
C7B C 1.1135(9) 0.5862(4) 0.6973(3) 0.155(3) Uani 1 1 d . . . . .
H7B H 1.1369 0.5431 0.7015 0.186 Uiso 1 1 calc R U . . .
C8B C 1.1658(10) 0.6352(6) 0.7173(4) 0.184(5) Uani 1 1 d . . . . .
H8B H 1.2208 0.6257 0.7361 0.221 Uiso 1 1 calc R U . . .
C9B C 1.1360(11) 0.6979(5) 0.7094(4) 0.181(5) Uani 1 1 d . . . . .
H9B H 1.1751 0.7316 0.7220 0.218 Uiso 1 1 calc R U . . .
C10B C 1.0473(9) 0.7129(3) 0.6825(2) 0.133(3) Uani 1 1 d . . . . .
H10B H 1.0276 0.7562 0.6778 0.159 Uiso 1 1 calc R U . . .
C11B C 0.7332(6) 0.6959(2) 0.68807(12) 0.0738(15) Uani 1 1 d . . . . .
H11G H 0.6444 0.6956 0.6950 0.111 Uiso 1 1 calc R U . . .
H11H H 0.7648 0.7399 0.6884 0.111 Uiso 1 1 calc R U . . .
H11I H 0.7821 0.6698 0.7043 0.111 Uiso 1 1 calc R U . . .
C12B C 0.5401(10) 0.7347(4) 0.6337(3) 0.147(3) Uani 1 1 d . . . . .
H12E H 0.5494 0.7583 0.6560 0.177 Uiso 1 1 calc R U . . .
H12F H 0.5113 0.7654 0.6158 0.177 Uiso 1 1 calc R U . . .
C13B C 0.4394(11) 0.6828(6) 0.6383(4) 0.209(6) Uani 1 1 d . . . . .
H13G H 0.4389 0.6550 0.6178 0.314 Uiso 1 1 calc R U . . .
H13H H 0.3566 0.7029 0.6409 0.314 Uiso 1 1 calc R U . . .
H13I H 0.4584 0.6575 0.6591 0.314 Uiso 1 1 calc R U . . .
C14B C 0.7047(5) 0.5563(2) 0.62644(10) 0.0674(13) Uani 1 1 d . . . . .
C15B C 0.6551(6) 0.4896(2) 0.63630(10) 0.0677(14) Uani 1 1 d . . . . .
C16B C 0.5298(6) 0.4829(2) 0.64733(11) 0.0718(15) Uani 1 1 d . . . . .
H16B H 0.4797 0.5196 0.6517 0.086 Uiso 1 1 calc R U . . .
C17B C 0.4790(6) 0.4214(2) 0.65184(12) 0.0766(15) Uani 1 1 d . . . . .
C18B C 0.5491(8) 0.3662(2) 0.64569(13) 0.0862(18) Uani 1 1 d . . . . .
H18B H 0.5122 0.3252 0.6484 0.103 Uiso 1 1 calc R U . . .
C19B C 0.6748(8) 0.3725(2) 0.63549(14) 0.0888(18) Uani 1 1 d . . . . .
H19B H 0.7240 0.3354 0.6314 0.107 Uiso 1 1 calc R U . . .
C20B C 0.7294(6) 0.4333(2) 0.63129(11) 0.0789(15) Uani 1 1 d . . . . .
C1C C 0.5594(11) 0.3698(5) 0.4819(2) 0.151(3) Uani 1 1 d . . . . .
H1C1 H 0.5923 0.3422 0.4630 0.181 Uiso 1 1 calc R U . . .
H1C2 H 0.4978 0.3449 0.4956 0.181 Uiso 1 1 calc R U . . .
C2C C 0.6672(7) 0.3916(3) 0.50522(15) 0.098(2) Uani 1 1 d . . . . .
H2C H 0.7437 0.3962 0.4902 0.117 Uiso 1 1 calc R U . . .
C3C C 0.6219(6) 0.4614(3) 0.51551(12) 0.0808(15) Uani 1 1 d . . . . .
C4C C 0.5597(7) 0.4829(4) 0.48019(14) 0.107(2) Uani 1 1 d . . . . .
H4C H 0.6282 0.4952 0.4636 0.129 Uiso 1 1 calc R U . . .
C5C C 0.4649(9) 0.5373(4) 0.48192(14) 0.104(2) Uani 1 1 d . . . . .
C6C C 0.5031(10) 0.6013(6) 0.4878(3) 0.152(3) Uani 1 1 d . . . . .
H6C H 0.5904 0.6099 0.4902 0.182 Uiso 1 1 calc R U . . .
C7C C 0.4190(14) 0.6523(6) 0.4900(3) 0.174(4) Uani 1 1 d . . . . .
H7C H 0.4499 0.6940 0.4946 0.209 Uiso 1 1 calc R U . . .
C8C C 0.2938(14) 0.6429(6) 0.4858(3) 0.151(3) Uani 1 1 d . . . . .
H8C H 0.2377 0.6781 0.4870 0.181 Uiso 1 1 calc R U . . .
C9C C 0.2475(10) 0.5826(7) 0.4797(2) 0.137(3) Uani 1 1 d . . . . .
H9C H 0.1596 0.5765 0.4767 0.164 Uiso 1 1 calc R U . . .
C10C C 0.3332(11) 0.5272(5) 0.47784(18) 0.133(3) Uani 1 1 d . . . . .
H10C H 0.3010 0.4856 0.4740 0.160 Uiso 1 1 calc R U . . .
C11C C 0.5251(6) 0.4607(3) 0.54537(13) 0.0934(18) Uani 1 1 d . . . . .
H11J H 0.5610 0.4387 0.5656 0.140 Uiso 1 1 calc R U . . .
H11K H 0.4488 0.4384 0.5377 0.140 Uiso 1 1 calc R U . . .
H11L H 0.5038 0.5047 0.5518 0.140 Uiso 1 1 calc R U . . .
C12C C 0.7028(9) 0.3456(3) 0.53612(18) 0.123(3) Uani 1 1 d . . . . .
H12G H 0.7631 0.3678 0.5517 0.147 Uiso 1 1 calc R U . . .
H12H H 0.6260 0.3363 0.5498 0.147 Uiso 1 1 calc R U . . .
C13C C 0.7620(12) 0.2818(4) 0.5240(2) 0.161(4) Uani 1 1 d . . . . .
H13J H 0.7009 0.2582 0.5099 0.242 Uiso 1 1 calc R U . . .
H13K H 0.7851 0.2563 0.5444 0.242 Uiso 1 1 calc R U . . .
H13L H 0.8374 0.2906 0.5101 0.242 Uiso 1 1 calc R U . . .
C14C C 0.8374(6) 0.5153(2) 0.50995(12) 0.0700(14) Uani 1 1 d . . . . .
C15C C 0.9345(6) 0.5537(2) 0.53093(11) 0.0685(13) Uani 1 1 d . . . . .
C16C C 1.0342(6) 0.5204(2) 0.54695(14) 0.0775(15) Uani 1 1 d . . . . .
H16C H 1.0404 0.4753 0.5449 0.093 Uiso 1 1 calc R U . . .
C17C C 1.1248(6) 0.5551(3) 0.56609(14) 0.0816(15) Uani 1 1 d . . . . .
C18C C 1.1226(7) 0.6217(3) 0.56927(15) 0.0887(17) Uani 1 1 d . . . . .
H18C H 1.1862 0.6437 0.5818 0.106 Uiso 1 1 calc R U . . .
C19C C 1.0246(7) 0.6542(3) 0.55354(15) 0.0892(17) Uani 1 1 d . . . . .
H19C H 1.0212 0.6994 0.5550 0.107 Uiso 1 1 calc R U . . .
C20C C 0.9295(6) 0.6211(2) 0.53531(13) 0.0807(16) 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
Cl1 C16 1.712(8) . ?
Cl1A C20A 1.723(5) . ?
Cl1B C20B 1.716(7) . ?
Cl1C C20C 1.725(7) . ?
N1 C14 1.334(5) . ?
N1 C3 1.473(5) . ?
N1 H1 0.8600 . ?
N2 O3 1.219(10) . ?
N2 O4 1.223(8) . ?
N2 C19 1.471(11) . ?
N1A C14A 1.329(5) . ?
N1A C3A 1.476(5) . ?
N1A H1A 0.8600 . ?
N2A O4A 1.193(6) . ?
N2A O3A 1.207(6) . ?
N2A C17A 1.470(7) . ?
N1B C14B 1.327(5) . ?
N1B C3B 1.476(5) . ?
N1B H1B 0.8600 . ?
N2B O3B 1.195(7) . ?
N2B O4B 1.214(6) . ?
N2B C17B 1.473(8) . ?
N1C C14C 1.334(7) . ?
N1C C3C 1.454(7) . ?
N1C H1C 0.8600 . ?
N2C O3C 1.208(7) . ?
N2C O4C 1.216(7) . ?
N2C C17C 1.467(8) . ?
O1 C1 1.411(9) . ?
O1 C4 1.428(7) . ?
O2 C14 1.236(5) . ?
O1A C1A 1.430(7) . ?
O1A C4A 1.436(5) . ?
O2A C14A 1.230(5) . ?
O1B C1B 1.402(10) . ?
O1B C4B 1.430(6) . ?
O2B C14B 1.226(5) . ?
O1C C1C 1.388(11) . ?
O1C C4C 1.436(9) . ?
O2C C14C 1.238(5) . ?
C1 C2 1.522(8) . ?
C1 H1X 0.9700 . ?
C1 H1Y 0.9700 . ?
C2 C12 1.540(10) . ?
C2 C3 1.540(8) . ?
C2 H2 0.9800 . ?
C3 C11 1.524(7) . ?
C3 C4 1.561(7) . ?
C4 C5 1.473(9) . ?
C4 H4A 0.9800 . ?
C5 C6 1.347(10) . ?
C5 C10 1.394(10) . ?
C6 C7 1.418(12) . ?
C6 H6 0.9300 . ?
C7 C8 1.352(14) . ?
C7 H7 0.9300 . ?
C8 C9 1.335(16) . ?
C8 H8 0.9300 . ?
C9 C10 1.382(14) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.509(11) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.485(6) . ?
C15 C20 1.375(8) . ?
C15 C16 1.392(9) . ?
C16 C17 1.411(9) . ?
C17 C18 1.356(12) . ?
C17 H17 0.9300 . ?
C18 C19 1.374(12) . ?
C18 H18 0.9300 . ?
C19 C20 1.376(8) . ?
C20 H20 0.9300 . ?
C1A C2A 1.527(7) . ?
C1A H1A1 0.9700 . ?
C1A H1A2 0.9700 . ?
C2A C12A 1.524(8) . ?
C2A C3A 1.529(7) . ?
C2A H2A 0.9800 . ?
C3A C11A 1.519(6) . ?
C3A C4A 1.548(7) . ?
C4A C5A 1.494(7) . ?
C4A H4A1 0.9800 . ?
C5A C10A 1.377(7) . ?
C5A C6A 1.379(7) . ?
C6A C7A 1.379(9) . ?
C6A H6A 0.9300 . ?
C7A C8A 1.360(9) . ?
C7A H7A 0.9300 . ?
C8A C9A 1.325(9) . ?
C8A H8A 0.9300 . ?
C9A C10A 1.372(9) . ?
C9A H9A 0.9300 . ?
C10A H10A 0.9300 . ?
C11A H11D 0.9600 . ?
C11A H11E 0.9600 . ?
C11A H11F 0.9600 . ?
C12A C13A 1.520(10) . ?
C12A H12C 0.9700 . ?
C12A H12D 0.9700 . ?
C13A H13D 0.9600 . ?
C13A H13E 0.9600 . ?
C13A H13F 0.9600 . ?
C14A C15A 1.508(6) . ?
C15A C16A 1.373(7) . ?
C15A C20A 1.380(6) . ?
C16A C17A 1.383(6) . ?
C16A H16A 0.9300 . ?
C17A C18A 1.370(7) . ?
C18A C19A 1.365(7) . ?
C18A H18A 0.9300 . ?
C19A C20A 1.399(6) . ?
C19A H19A 0.9300 . ?
C1B C2B 1.526(10) . ?
C1B H1B1 0.9700 . ?
C1B H1B2 0.9700 . ?
C2B C12B 1.524(12) . ?
C2B C3B 1.536(8) . ?
C2B H2B 0.9800 . ?
C3B C11B 1.528(6) . ?
C3B C4B 1.538(8) . ?
C4B C5B 1.493(9) . ?
C4B H4B 0.9800 . ?
C5B C10B 1.381(9) . ?
C5B C6B 1.382(9) . ?
C6B C7B 1.400(12) . ?
C6B H6B 0.9300 . ?
C7B C8B 1.369(13) . ?
C7B H7B 0.9300 . ?
C8B C9B 1.358(14) . ?
C8B H8B 0.9300 . ?
C9B C10B 1.404(13) . ?
C9B H9B 0.9300 . ?
C10B H10B 0.9300 . ?
C11B H11G 0.9600 . ?
C11B H11H 0.9600 . ?
C11B H11I 0.9600 . ?
C12B C13B 1.503(14) . ?
C12B H12E 0.9700 . ?
C12B H12F 0.9700 . ?
C13B H13G 0.9600 . ?
C13B H13H 0.9600 . ?
C13B H13I 0.9600 . ?
C14B C15B 1.510(6) . ?
C15B C16B 1.375(8) . ?
C15B C20B 1.402(7) . ?
C16B C17B 1.378(6) . ?
C16B H16B 0.9300 . ?
C17B C18B 1.368(8) . ?
C18B C19B 1.369(9) . ?
C18B H18B 0.9300 . ?
C19B C20B 1.381(7) . ?
C19B H19B 0.9300 . ?
C1C C2C 1.493(11) . ?
C1C H1C1 0.9700 . ?
C1C H1C2 0.9700 . ?
C2C C12C 1.542(10) . ?
C2C C3C 1.558(8) . ?
C2C H2C 0.9800 . ?
C3C C11C 1.509(8) . ?
C3C C4C 1.541(8) . ?
C4C C5C 1.491(10) . ?
C4C H4C 0.9800 . ?
C5C C10C 1.394(11) . ?
C5C C6C 1.391(12) . ?
C6C C7C 1.366(13) . ?
C6C H6C 0.9300 . ?
C7C C8C 1.327(14) . ?
C7C H7C 0.9300 . ?
C8C C9C 1.347(13) . ?
C8C H8C 0.9300 . ?
C9C C10C 1.446(12) . ?
C9C H9C 0.9300 . ?
C10C H10C 0.9300 . ?
C11C H11J 0.9600 . ?
C11C H11K 0.9600 . ?
C11C H11L 0.9600 . ?
C12C C13C 1.517(10) . ?
C12C H12G 0.9700 . ?
C12C H12H 0.9700 . ?
C13C H13J 0.9600 . ?
C13C H13K 0.9600 . ?
C13C H13L 0.9600 . ?
C14C C15C 1.504(7) . ?
C15C C16C 1.381(8) . ?
C15C C20C 1.393(7) . ?
C16C C17C 1.383(8) . ?
C16C H16C 0.9300 . ?
C17C C18C 1.372(8) . ?
C18C C19C 1.355(9) . ?
C18C H18C 0.9300 . ?
C19C C20C 1.383(8) . ?
C19C H19C 0.9300 . ?

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 N1 C3 126.6(3) . . ?
C14 N1 H1 116.7 . . ?
C3 N1 H1 116.7 . . ?
O3 N2 O4 123.7(10) . . ?
O3 N2 C19 119.0(7) . . ?
O4 N2 C19 117.2(10) . . ?
C14A N1A C3A 127.6(3) . . ?
C14A N1A H1A 116.2 . . ?
C3A N1A H1A 116.2 . . ?
O4A N2A O3A 122.7(6) . . ?
O4A N2A C17A 119.4(5) . . ?
O3A N2A C17A 117.9(4) . . ?
C14B N1B C3B 126.7(3) . . ?
C14B N1B H1B 116.7 . . ?
C3B N1B H1B 116.7 . . ?
O3B N2B O4B 123.6(7) . . ?
O3B N2B C17B 118.2(5) . . ?
O4B N2B C17B 118.2(6) . . ?
C14C N1C C3C 128.2(4) . . ?
C14C N1C H1C 115.9 . . ?
C3C N1C H1C 115.9 . . ?
O3C N2C O4C 123.3(7) . . ?
O3C N2C C17C 118.8(7) . . ?
O4C N2C C17C 117.9(6) . . ?
C1 O1 C4 108.8(4) . . ?
C1A O1A C4A 108.9(4) . . ?
C1B O1B C4B 108.8(5) . . ?
C1C O1C C4C 110.5(6) . . ?
O1 C1 C2 107.9(5) . . ?
O1 C1 H1X 110.1 . . ?
C2 C1 H1X 110.1 . . ?
O1 C1 H1Y 110.1 . . ?
C2 C1 H1Y 110.1 . . ?
H1X C1 H1Y 108.4 . . ?
C1 C2 C12 112.9(6) . . ?
C1 C2 C3 101.0(5) . . ?
C12 C2 C3 119.8(5) . . ?
C1 C2 H2 107.5 . . ?
C12 C2 H2 107.5 . . ?
C3 C2 H2 107.5 . . ?
N1 C3 C11 105.5(3) . . ?
N1 C3 C2 114.3(4) . . ?
C11 C3 C2 113.8(5) . . ?
N1 C3 C4 112.5(4) . . ?
C11 C3 C4 112.6(4) . . ?
C2 C3 C4 98.4(4) . . ?
O1 C4 C5 110.5(5) . . ?
O1 C4 C3 102.2(5) . . ?
C5 C4 C3 118.9(4) . . ?
O1 C4 H4A 108.3 . . ?
C5 C4 H4A 108.3 . . ?
C3 C4 H4A 108.3 . . ?
C6 C5 C10 118.2(8) . . ?
C6 C5 C4 119.3(6) . . ?
C10 C5 C4 122.3(8) . . ?
C5 C6 C7 121.1(8) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C8 C7 C6 119.2(11) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C9 C8 C7 120.1(12) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C10 121.5(12) . . ?
C8 C9 H9 119.2 . . ?
C10 C9 H9 119.2 . . ?
C9 C10 C5 119.7(10) . . ?
C9 C10 H10 120.2 . . ?
C5 C10 H10 120.2 . . ?
C3 C11 H11A 109.5 . . ?
C3 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C3 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C2 113.2(7) . . ?
C13 C12 H12A 108.9 . . ?
C2 C12 H12A 108.9 . . ?
C13 C12 H12B 108.9 . . ?
C2 C12 H12B 108.9 . . ?
H12A C12 H12B 107.8 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O2 C14 N1 123.5(4) . . ?
O2 C14 C15 120.5(4) . . ?
N1 C14 C15 115.9(4) . . ?
C20 C15 C16 119.1(5) . . ?
C20 C15 C14 120.9(5) . . ?
C16 C15 C14 119.8(5) . . ?
C15 C16 C17 120.1(7) . . ?
C15 C16 Cl1 121.0(5) . . ?
C17 C16 Cl1 118.9(7) . . ?
C18 C17 C16 119.0(8) . . ?
C18 C17 H17 120.5 . . ?
C16 C17 H17 120.5 . . ?
C17 C18 C19 120.7(6) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C20 C19 C18 120.8(7) . . ?
C20 C19 N2 118.1(8) . . ?
C18 C19 N2 121.1(7) . . ?
C19 C20 C15 120.2(7) . . ?
C19 C20 H20 119.9 . . ?
C15 C20 H20 119.9 . . ?
O1A C1A C2A 106.7(4) . . ?
O1A C1A H1A1 110.4 . . ?
C2A C1A H1A1 110.4 . . ?
O1A C1A H1A2 110.4 . . ?
C2A C1A H1A2 110.4 . . ?
H1A1 C1A H1A2 108.6 . . ?
C1A C2A C12A 116.4(4) . . ?
C1A C2A C3A 100.4(4) . . ?
C12A C2A C3A 117.8(4) . . ?
C1A C2A H2A 107.2 . . ?
C12A C2A H2A 107.2 . . ?
C3A C2A H2A 107.2 . . ?
N1A C3A C11A 106.0(3) . . ?
N1A C3A C2A 112.6(4) . . ?
C11A C3A C2A 113.3(4) . . ?
N1A C3A C4A 114.1(3) . . ?
C11A C3A C4A 112.1(4) . . ?
C2A C3A C4A 98.9(3) . . ?
O1A C4A C5A 111.1(4) . . ?
O1A C4A C3A 103.1(4) . . ?
C5A C4A C3A 116.9(3) . . ?
O1A C4A H4A1 108.5 . . ?
C5A C4A H4A1 108.5 . . ?
C3A C4A H4A1 108.5 . . ?
C10A C5A C6A 117.4(5) . . ?
C10A C5A C4A 124.0(4) . . ?
C6A C5A C4A 118.6(4) . . ?
C7A C6A C5A 120.8(6) . . ?
C7A C6A H6A 119.6 . . ?
C5A C6A H6A 119.6 . . ?
C8A C7A C6A 119.8(6) . . ?
C8A C7A H7A 120.1 . . ?
C6A C7A H7A 120.1 . . ?
C9A C8A C7A 120.0(6) . . ?
C9A C8A H8A 120.0 . . ?
C7A C8A H8A 120.0 . . ?
C8A C9A C10A 121.5(6) . . ?
C8A C9A H9A 119.3 . . ?
C10A C9A H9A 119.3 . . ?
C9A C10A C5A 120.4(5) . . ?
C9A C10A H10A 119.8 . . ?
C5A C10A H10A 119.8 . . ?
C3A C11A H11D 109.5 . . ?
C3A C11A H11E 109.5 . . ?
H11D C11A H11E 109.5 . . ?
C3A C11A H11F 109.5 . . ?
H11D C11A H11F 109.5 . . ?
H11E C11A H11F 109.5 . . ?
C2A C12A C13A 113.5(6) . . ?
C2A C12A H12C 108.9 . . ?
C13A C12A H12C 108.9 . . ?
C2A C12A H12D 108.9 . . ?
C13A C12A H12D 108.9 . . ?
H12C C12A H12D 107.7 . . ?
C12A C13A H13D 109.5 . . ?
C12A C13A H13E 109.5 . . ?
H13D C13A H13E 109.5 . . ?
C12A C13A H13F 109.5 . . ?
H13D C13A H13F 109.5 . . ?
H13E C13A H13F 109.5 . . ?
O2A C14A N1A 124.7(4) . . ?
O2A C14A C15A 120.9(3) . . ?
N1A C14A C15A 114.2(3) . . ?
C16A C15A C20A 118.0(4) . . ?
C16A C15A C14A 119.0(4) . . ?
C20A C15A C14A 122.9(4) . . ?
C15A C16A C17A 120.2(4) . . ?
C15A C16A H16A 119.9 . . ?
C17A C16A H16A 119.9 . . ?
C18A C17A C16A 122.2(5) . . ?
C18A C17A N2A 118.5(4) . . ?
C16A C17A N2A 119.3(4) . . ?
C19A C18A C17A 118.2(4) . . ?
C19A C18A H18A 120.9 . . ?
C17A C18A H18A 120.9 . . ?
C18A C19A C20A 120.2(4) . . ?
C18A C19A H19A 119.9 . . ?
C20A C19A H19A 119.9 . . ?
C15A C20A C19A 121.3(4) . . ?
C15A C20A Cl1A 120.1(3) . . ?
C19A C20A Cl1A 118.5(4) . . ?
O1B C1B C2B 109.0(5) . . ?
O1B C1B H1B1 109.9 . . ?
C2B C1B H1B1 109.9 . . ?
O1B C1B H1B2 109.9 . . ?
C2B C1B H1B2 109.9 . . ?
H1B1 C1B H1B2 108.3 . . ?
C12B C2B C1B 112.5(6) . . ?
C12B C2B C3B 117.7(6) . . ?
C1B C2B C3B 102.0(6) . . ?
C12B C2B H2B 108.1 . . ?
C1B C2B H2B 108.1 . . ?
C3B C2B H2B 108.1 . . ?
N1B C3B C11B 106.2(3) . . ?
N1B C3B C2B 114.8(4) . . ?
C11B C3B C2B 112.6(4) . . ?
N1B C3B C4B 111.7(4) . . ?
C11B C3B C4B 110.9(4) . . ?
C2B C3B C4B 100.7(4) . . ?
O1B C4B C5B 110.0(5) . . ?
O1B C4B C3B 104.5(5) . . ?
C5B C4B C3B 115.8(4) . . ?
O1B C4B H4B 108.8 . . ?
C5B C4B H4B 108.8 . . ?
C3B C4B H4B 108.8 . . ?
C10B C5B C6B 116.5(7) . . ?
C10B C5B C4B 123.7(6) . . ?
C6B C5B C4B 119.6(6) . . ?
C5B C6B C7B 122.3(7) . . ?
C5B C6B H6B 118.9 . . ?
C7B C6B H6B 118.9 . . ?
C8B C7B C6B 119.8(8) . . ?
C8B C7B H7B 120.1 . . ?
C6B C7B H7B 120.1 . . ?
C9B C8B C7B 119.1(10) . . ?
C9B C8B H8B 120.5 . . ?
C7B C8B H8B 120.5 . . ?
C8B C9B C10B 121.0(8) . . ?
C8B C9B H9B 119.5 . . ?
C10B C9B H9B 119.5 . . ?
C5B C10B C9B 121.2(8) . . ?
C5B C10B H10B 119.4 . . ?
C9B C10B H10B 119.4 . . ?
C3B C11B H11G 109.5 . . ?
C3B C11B H11H 109.5 . . ?
H11G C11B H11H 109.5 . . ?
C3B C11B H11I 109.5 . . ?
H11G C11B H11I 109.5 . . ?
H11H C11B H11I 109.5 . . ?
C13B C12B C2B 113.2(8) . . ?
C13B C12B H12E 108.9 . . ?
C2B C12B H12E 108.9 . . ?
C13B C12B H12F 108.9 . . ?
C2B C12B H12F 108.9 . . ?
H12E C12B H12F 107.7 . . ?
C12B C13B H13G 109.5 . . ?
C12B C13B H13H 109.5 . . ?
H13G C13B H13H 109.5 . . ?
C12B C13B H13I 109.5 . . ?
H13G C13B H13I 109.5 . . ?
H13H C13B H13I 109.5 . . ?
O2B C14B N1B 125.3(4) . . ?
O2B C14B C15B 119.6(3) . . ?
N1B C14B C15B 115.2(3) . . ?
C16B C15B C20B 118.8(4) . . ?
C16B C15B C14B 119.2(5) . . ?
C20B C15B C14B 121.7(5) . . ?
C15B C16B C17B 119.4(5) . . ?
C15B C16B H16B 120.3 . . ?
C17B C16B H16B 120.3 . . ?
C18B C17B C16B 122.2(6) . . ?
C18B C17B N2B 119.1(5) . . ?
C16B C17B N2B 118.6(5) . . ?
C19B C18B C17B 118.6(5) . . ?
C19B C18B H18B 120.7 . . ?
C17B C18B H18B 120.7 . . ?
C18B C19B C20B 120.7(6) . . ?
C18B C19B H19B 119.7 . . ?
C20B C19B H19B 119.7 . . ?
C19B C20B C15B 120.2(6) . . ?
C19B C20B Cl1B 119.0(5) . . ?
C15B C20B Cl1B 120.8(4) . . ?
O1C C1C C2C 108.9(7) . . ?
O1C C1C H1C1 109.9 . . ?
C2C C1C H1C1 109.9 . . ?
O1C C1C H1C2 109.9 . . ?
C2C C1C H1C2 109.9 . . ?
H1C1 C1C H1C2 108.3 . . ?
C1C C2C C12C 116.2(6) . . ?
C1C C2C C3C 101.2(7) . . ?
C12C C2C C3C 116.7(4) . . ?
C1C C2C H2C 107.4 . . ?
C12C C2C H2C 107.4 . . ?
C3C C2C H2C 107.4 . . ?
N1C C3C C11C 106.8(4) . . ?
N1C C3C C4C 114.7(5) . . ?
C11C C3C C4C 111.4(5) . . ?
N1C C3C C2C 111.6(5) . . ?
C11C C3C C2C 112.2(5) . . ?
C4C C3C C2C 100.1(4) . . ?
O1C C4C C5C 110.8(7) . . ?
O1C C4C C3C 103.4(6) . . ?
C5C C4C C3C 117.0(5) . . ?
O1C C4C H4C 108.4 . . ?
C5C C4C H4C 108.4 . . ?
C3C C4C H4C 108.4 . . ?
C10C C5C C6C 116.0(8) . . ?
C10C C5C C4C 122.3(8) . . ?
C6C C5C C4C 121.7(8) . . ?
C7C C6C C5C 123.4(10) . . ?
C7C C6C H6C 118.3 . . ?
C5C C6C H6C 118.3 . . ?
C8C C7C C6C 120.7(12) . . ?
C8C C7C H7C 119.7 . . ?
C6C C7C H7C 119.7 . . ?
C7C C8C C9C 120.3(12) . . ?
C7C C8C H8C 119.8 . . ?
C9C C8C H8C 119.8 . . ?
C8C C9C C10C 120.6(10) . . ?
C8C C9C H9C 119.7 . . ?
C10C C9C H9C 119.7 . . ?
C5C C10C C9C 119.0(9) . . ?
C5C C10C H10C 120.5 . . ?
C9C C10C H10C 120.5 . . ?
C3C C11C H11J 109.5 . . ?
C3C C11C H11K 109.5 . . ?
H11J C11C H11K 109.5 . . ?
C3C C11C H11L 109.5 . . ?
H11J C11C H11L 109.5 . . ?
H11K C11C H11L 109.5 . . ?
C13C C12C C2C 113.6(6) . . ?
C13C C12C H12G 108.9 . . ?
C2C C12C H12G 108.9 . . ?
C13C C12C H12H 108.9 . . ?
C2C C12C H12H 108.9 . . ?
H12G C12C H12H 107.7 . . ?
C12C C13C H13J 109.5 . . ?
C12C C13C H13K 109.5 . . ?
H13J C13C H13K 109.5 . . ?
C12C C13C H13L 109.5 . . ?
H13J C13C H13L 109.5 . . ?
H13K C13C H13L 109.5 . . ?
O2C C14C N1C 125.5(5) . . ?
O2C C14C C15C 119.4(5) . . ?
N1C C14C C15C 115.0(4) . . ?
C16C C15C C20C 117.9(5) . . ?
C16C C15C C14C 118.3(4) . . ?
C20C C15C C14C 123.8(5) . . ?
C15C C16C C17C 119.0(5) . . ?
C15C C16C H16C 120.5 . . ?
C17C C16C H16C 120.5 . . ?
C18C C17C C16C 123.1(6) . . ?
C18C C17C N2C 118.8(6) . . ?
C16C C17C N2C 118.0(5) . . ?
C19C C18C C17C 117.8(6) . . ?
C19C C18C H18C 121.1 . . ?
C17C C18C H18C 121.1 . . ?
C18C C19C C20C 120.8(5) . . ?
C18C C19C H19C 119.6 . . ?
C20C C19C H19C 119.6 . . ?
C19C C20C C15C 121.4(6) . . ?
C19C C20C Cl1C 118.2(4) . . ?
C15C C20C Cl1C 120.5(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
C4 O1 C1 C2 6.3(7) . . . . ?
O1 C1 C2 C12 152.3(6) . . . . ?
O1 C1 C2 C3 23.1(7) . . . . ?
C14 N1 C3 C11 -179.8(5) . . . . ?
C14 N1 C3 C2 54.5(6) . . . . ?
C14 N1 C3 C4 -56.6(6) . . . . ?
C1 C2 C3 N1 -159.7(5) . . . . ?
C12 C2 C3 N1 75.7(7) . . . . ?
C1 C2 C3 C11 79.1(6) . . . . ?
C12 C2 C3 C11 -45.6(7) . . . . ?
C1 C2 C3 C4 -40.3(5) . . . . ?
C12 C2 C3 C4 -164.9(6) . . . . ?
C1 O1 C4 C5 -160.3(6) . . . . ?
C1 O1 C4 C3 -32.8(6) . . . . ?
N1 C3 C4 O1 166.0(4) . . . . ?
C11 C3 C4 O1 -74.9(5) . . . . ?
C2 C3 C4 O1 45.2(5) . . . . ?
N1 C3 C4 C5 -72.1(6) . . . . ?
C11 C3 C4 C5 47.0(7) . . . . ?
C2 C3 C4 C5 167.1(5) . . . . ?
O1 C4 C5 C6 -146.5(5) . . . . ?
C3 C4 C5 C6 95.9(7) . . . . ?
O1 C4 C5 C10 29.0(8) . . . . ?
C3 C4 C5 C10 -88.6(7) . . . . ?
C10 C5 C6 C7 0.9(9) . . . . ?
C4 C5 C6 C7 176.6(5) . . . . ?
C5 C6 C7 C8 -2.6(11) . . . . ?
C6 C7 C8 C9 4.6(16) . . . . ?
C7 C8 C9 C10 -5.1(19) . . . . ?
C8 C9 C10 C5 3.4(16) . . . . ?
C6 C5 C10 C9 -1.3(11) . . . . ?
C4 C5 C10 C9 -176.8(7) . . . . ?
C1 C2 C12 C13 168.3(7) . . . . ?
C3 C2 C12 C13 -73.0(8) . . . . ?
C3 N1 C14 O2 4.4(8) . . . . ?
C3 N1 C14 C15 -171.9(5) . . . . ?
O2 C14 C15 C20 -116.3(5) . . . . ?
N1 C14 C15 C20 60.0(6) . . . . ?
O2 C14 C15 C16 59.0(7) . . . . ?
N1 C14 C15 C16 -124.7(5) . . . . ?
C20 C15 C16 C17 2.7(8) . . . . ?
C14 C15 C16 C17 -172.7(5) . . . . ?
C20 C15 C16 Cl1 -177.7(4) . . . . ?
C14 C15 C16 Cl1 6.9(7) . . . . ?
C15 C16 C17 C18 -1.5(11) . . . . ?
Cl1 C16 C17 C18 178.9(6) . . . . ?
C16 C17 C18 C19 -0.4(12) . . . . ?
C17 C18 C19 C20 1.0(11) . . . . ?
C17 C18 C19 N2 -178.3(7) . . . . ?
O3 N2 C19 C20 -1.1(10) . . . . ?
O4 N2 C19 C20 -177.3(6) . . . . ?
O3 N2 C19 C18 178.2(7) . . . . ?
O4 N2 C19 C18 2.1(9) . . . . ?
C18 C19 C20 C15 0.2(8) . . . . ?
N2 C19 C20 C15 179.6(5) . . . . ?
C16 C15 C20 C19 -2.1(7) . . . . ?
C14 C15 C20 C19 173.3(4) . . . . ?
C4A O1A C1A C2A -2.1(5) . . . . ?
O1A C1A C2A C12A 158.2(4) . . . . ?
O1A C1A C2A C3A 29.8(5) . . . . ?
C14A N1A C3A C11A -179.1(5) . . . . ?
C14A N1A C3A C2A 56.5(6) . . . . ?
C14A N1A C3A C4A -55.2(6) . . . . ?
C1A C2A C3A N1A -164.4(3) . . . . ?
C12A C2A C3A N1A 68.2(5) . . . . ?
C1A C2A C3A C11A 75.3(5) . . . . ?
C12A C2A C3A C11A -52.1(6) . . . . ?
C1A C2A C3A C4A -43.5(4) . . . . ?
C12A C2A C3A C4A -171.0(4) . . . . ?
C1A O1A C4A C5A -152.3(4) . . . . ?
C1A O1A C4A C3A -26.4(4) . . . . ?
N1A C3A C4A O1A 163.5(3) . . . . ?
C11A C3A C4A O1A -76.0(4) . . . . ?
C2A C3A C4A O1A 43.7(4) . . . . ?
N1A C3A C4A C5A -74.4(4) . . . . ?
C11A C3A C4A C5A 46.2(5) . . . . ?
C2A C3A C4A C5A 165.8(3) . . . . ?
O1A C4A C5A C10A 21.5(6) . . . . ?
C3A C4A C5A C10A -96.4(5) . . . . ?
O1A C4A C5A C6A -159.0(4) . . . . ?
C3A C4A C5A C6A 83.2(5) . . . . ?
C10A C5A C6A C7A 2.9(9) . . . . ?
C4A C5A C6A C7A -176.7(6) . . . . ?
C5A C6A C7A C8A -3.3(10) . . . . ?
C6A C7A C8A C9A 2.6(11) . . . . ?
C7A C8A C9A C10A -1.7(12) . . . . ?
C8A C9A C10A C5A 1.4(11) . . . . ?
C6A C5A C10A C9A -2.0(9) . . . . ?
C4A C5A C10A C9A 177.6(6) . . . . ?
C1A C2A C12A C13A 76.9(7) . . . . ?
C3A C2A C12A C13A -163.8(6) . . . . ?
C3A N1A C14A O2A 3.3(8) . . . . ?
C3A N1A C14A C15A -173.0(4) . . . . ?
O2A C14A C15A C16A -105.2(5) . . . . ?
N1A C14A C15A C16A 71.3(5) . . . . ?
O2A C14A C15A C20A 70.6(6) . . . . ?
N1A C14A C15A C20A -113.0(5) . . . . ?
C20A C15A C16A C17A 0.7(6) . . . . ?
C14A C15A C16A C17A 176.7(4) . . . . ?
C15A C16A C17A C18A -1.0(7) . . . . ?
C15A C16A C17A N2A 177.6(4) . . . . ?
O4A N2A C17A C18A -7.7(8) . . . . ?
O3A N2A C17A C18A 170.8(6) . . . . ?
O4A N2A C17A C16A 173.6(6) . . . . ?
O3A N2A C17A C16A -7.9(8) . . . . ?
C16A C17A C18A C19A 1.1(7) . . . . ?
N2A C17A C18A C19A -177.6(4) . . . . ?
C17A C18A C19A C20A -0.8(7) . . . . ?
C16A C15A C20A C19A -0.4(6) . . . . ?
C14A C15A C20A C19A -176.2(4) . . . . ?
C16A C15A C20A Cl1A -178.6(3) . . . . ?
C14A C15A C20A Cl1A 5.6(5) . . . . ?
C18A C19A C20A C15A 0.5(7) . . . . ?
C18A C19A C20A Cl1A 178.7(4) . . . . ?
C4B O1B C1B C2B 7.2(7) . . . . ?
O1B C1B C2B C12B 144.5(6) . . . . ?
O1B C1B C2B C3B 17.4(7) . . . . ?
C14B N1B C3B C11B 178.8(5) . . . . ?
C14B N1B C3B C2B 53.7(7) . . . . ?
C14B N1B C3B C4B -60.2(6) . . . . ?
C12B C2B C3B N1B 83.4(6) . . . . ?
C1B C2B C3B N1B -153.0(5) . . . . ?
C12B C2B C3B C11B -38.3(7) . . . . ?
C1B C2B C3B C11B 85.3(6) . . . . ?
C12B C2B C3B C4B -156.5(6) . . . . ?
C1B C2B C3B C4B -32.9(5) . . . . ?
C1B O1B C4B C5B -154.0(5) . . . . ?
C1B O1B C4B C3B -29.1(6) . . . . ?
N1B C3B C4B O1B 160.9(4) . . . . ?
C11B C3B C4B O1B -80.8(5) . . . . ?
C2B C3B C4B O1B 38.6(5) . . . . ?
N1B C3B C4B C5B -78.0(5) . . . . ?
C11B C3B C4B C5B 40.3(6) . . . . ?
C2B C3B C4B C5B 159.7(4) . . . . ?
O1B C4B C5B C10B 23.0(9) . . . . ?
C3B C4B C5B C10B -95.1(7) . . . . ?
O1B C4B C5B C6B -162.0(6) . . . . ?
C3B C4B C5B C6B 79.9(7) . . . . ?
C10B C5B C6B C7B 1.5(11) . . . . ?
C4B C5B C6B C7B -173.9(7) . . . . ?
C5B C6B C7B C8B 1.2(15) . . . . ?
C6B C7B C8B C9B -3.8(19) . . . . ?
C7B C8B C9B C10B 4(2) . . . . ?
C6B C5B C10B C9B -1.6(12) . . . . ?
C4B C5B C10B C9B 173.5(9) . . . . ?
C8B C9B C10B C5B -1.0(18) . . . . ?
C1B C2B C12B C13B 171.9(8) . . . . ?
C3B C2B C12B C13B -69.9(10) . . . . ?
C3B N1B C14B O2B 2.4(9) . . . . ?
C3B N1B C14B C15B -176.0(5) . . . . ?
O2B C14B C15B C16B -113.6(6) . . . . ?
N1B C14B C15B C16B 65.0(6) . . . . ?
O2B C14B C15B C20B 60.2(7) . . . . ?
N1B C14B C15B C20B -121.2(5) . . . . ?
C20B C15B C16B C17B -2.5(6) . . . . ?
C14B C15B C16B C17B 171.5(4) . . . . ?
C15B C16B C17B C18B 0.0(7) . . . . ?
C15B C16B C17B N2B 179.0(4) . . . . ?
O3B N2B C17B C18B 170.3(6) . . . . ?
O4B N2B C17B C18B -9.4(7) . . . . ?
O3B N2B C17B C16B -8.8(8) . . . . ?
O4B N2B C17B C16B 171.5(5) . . . . ?
C16B C17B C18B C19B 1.5(7) . . . . ?
N2B C17B C18B C19B -177.5(5) . . . . ?
C17B C18B C19B C20B -0.4(8) . . . . ?
C18B C19B C20B C15B -2.1(7) . . . . ?
C18B C19B C20B Cl1B 178.4(4) . . . . ?
C16B C15B C20B C19B 3.6(6) . . . . ?
C14B C15B C20B C19B -170.2(4) . . . . ?
C16B C15B C20B Cl1B -177.0(3) . . . . ?
C14B C15B C20B Cl1B 9.2(6) . . . . ?
C4C O1C C1C C2C -1.4(10) . . . . ?
O1C C1C C2C C12C 152.4(7) . . . . ?
O1C C1C C2C C3C 25.1(8) . . . . ?
C14C N1C C3C C11C 178.4(5) . . . . ?
C14C N1C C3C C4C -57.7(7) . . . . ?
C14C N1C C3C C2C 55.3(7) . . . . ?
C1C C2C C3C N1C -158.9(5) . . . . ?
C12C C2C C3C N1C 74.1(7) . . . . ?
C1C C2C C3C C11C 81.2(6) . . . . ?
C12C C2C C3C C11C -45.9(8) . . . . ?
C1C C2C C3C C4C -37.0(7) . . . . ?
C12C C2C C3C C4C -164.1(6) . . . . ?
C1C O1C C4C C5C -149.6(7) . . . . ?
C1C O1C C4C C3C -23.4(8) . . . . ?
N1C C3C C4C O1C 156.8(5) . . . . ?
C11C C3C C4C O1C -81.8(6) . . . . ?
C2C C3C C4C O1C 37.1(6) . . . . ?
N1C C3C C4C C5C -81.1(8) . . . . ?
C11C C3C C4C C5C 40.4(8) . . . . ?
C2C C3C C4C C5C 159.2(7) . . . . ?
O1C C4C C5C C10C 11.0(8) . . . . ?
C3C C4C C5C C10C -107.2(7) . . . . ?
O1C C4C C5C C6C -169.0(7) . . . . ?
C3C C4C C5C C6C 72.8(9) . . . . ?
C10C C5C C6C C7C 0.9(14) . . . . ?
C4C C5C C6C C7C -179.0(9) . . . . ?
C5C C6C C7C C8C -1.7(18) . . . . ?
C6C C7C C8C C9C 1.1(18) . . . . ?
C7C C8C C9C C10C 0.1(15) . . . . ?
C6C C5C C10C C9C 0.3(10) . . . . ?
C4C C5C C10C C9C -179.8(6) . . . . ?
C8C C9C C10C C5C -0.8(12) . . . . ?
C1C C2C C12C C13C 68.1(10) . . . . ?
C3C C2C C12C C13C -172.6(7) . . . . ?
C3C N1C C14C O2C 3.0(8) . . . . ?
C3C N1C C14C C15C -174.3(5) . . . . ?
O2C C14C C15C C16C -78.6(6) . . . . ?
N1C C14C C15C C16C 98.8(5) . . . . ?
O2C C14C C15C C20C 101.6(6) . . . . ?
N1C C14C C15C C20C -80.9(6) . . . . ?
C20C C15C C16C C17C -0.8(7) . . . . ?
C14C C15C C16C C17C 179.5(4) . . . . ?
C15C C16C C17C C18C -1.7(8) . . . . ?
C15C C16C C17C N2C 178.3(5) . . . . ?
O3C N2C C17C C18C 172.6(7) . . . . ?
O4C N2C C17C C18C -8.3(9) . . . . ?
O3C N2C C17C C16C -7.4(9) . . . . ?
O4C N2C C17C C16C 171.6(6) . . . . ?
C16C C17C C18C C19C 1.7(8) . . . . ?
N2C C17C C18C C19C -178.3(5) . . . . ?
C17C C18C C19C C20C 0.8(8) . . . . ?
C18C C19C C20C C15C -3.3(8) . . . . ?
C18C C19C C20C Cl1C 176.2(4) . . . . ?
C16C C15C C20C C19C 3.2(7) . . . . ?
C14C C15C C20C C19C -177.0(5) . . . . ?
C16C C15C C20C Cl1C -176.2(4) . . . . ?
C14C C15C C20C Cl1C 3.5(7) . . . . ?

_refine_diff_density_max         0.195
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.031

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_cd17129
_database_code_depnum_ccdc_archive 'CCDC 1870648'
_audit_update_record             
;
2018-09-30 deposited with the CCDC.
2018-10-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H23.40 Br N O2'
_chemical_formula_weight         353.68

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   10.2614(10)
_cell_length_b                   21.747(2)
_cell_length_c                   40.341(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     9002.2(15)
_cell_formula_units_Z            20
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3971
_cell_measurement_theta_min      4.389
_cell_measurement_theta_max      39.757

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_F_000             3668
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    2.287
_shelx_estimated_absorpt_T_min   0.684
_shelx_estimated_absorpt_T_max   0.838
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5713
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            50143
_diffrn_reflns_av_unetI/netI     0.1602
_diffrn_reflns_av_R_equivalents  0.1163
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_theta_min         1.781
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             15865
_reflns_number_gt                6133
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.813
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    0.973

_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0540P)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 
; 
 Flack x determined using 2040 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.010(7)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         15865
_refine_ls_number_parameters     964
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1936
_refine_ls_R_factor_gt           0.0558
_refine_ls_wR_factor_ref         0.1641
_refine_ls_wR_factor_gt          0.1170
_refine_ls_goodness_of_fit_ref   0.939
_refine_ls_restrained_S_all      0.939
_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
Br1 Br 0.4749(2) 0.76533(6) 1.01083(4) 0.1313(7) Uani 1 1 d . . . . .
Br2 Br 1.49117(14) 0.92598(10) 0.24689(3) 0.1385(7) Uani 1 1 d . . . . .
Br3 Br -0.45263(15) 0.93461(8) 0.03643(4) 0.1224(6) Uani 1 1 d . . . . .
Br4 Br 0.7630(2) 1.10709(7) 0.17994(5) 0.1595(9) Uani 1 1 d . . . . .
Br5 Br 0.1643(3) -0.28169(7) 0.37913(6) 0.1809(10) Uani 1 1 d . . . . .
N1 N 0.5481(10) 0.4541(4) 0.9916(2) 0.081(3) Uani 1 1 d . . . . .
H1 H 0.5305 0.4663 1.0113 0.098 Uiso 1 1 calc R U . . .
N2 N 0.9112(9) 0.9196(4) 0.32885(19) 0.061(2) Uani 1 1 d . . . . .
H2A H 0.9239 0.8900 0.3151 0.073 Uiso 1 1 calc R U . . .
N3 N 0.1165(9) 0.9436(4) 0.1236(2) 0.066(2) Uani 1 1 d . . . . .
H3D H 0.1082 0.9695 0.1076 0.080 Uiso 1 1 calc R U . . .
N4 N 0.9093(9) 0.8079(4) 0.2086(2) 0.070(3) Uani 1 1 d . . . . .
H4A H 0.8969 0.8207 0.1887 0.084 Uiso 1 1 calc R U . . .
N5 N 0.1848(9) 0.0269(4) 0.41422(18) 0.057(2) Uani 1 1 d . . . . .
H5D H 0.1195 0.0163 0.4022 0.069 Uiso 1 1 calc R U . . .
O1 O 0.5652(18) 0.2971(4) 1.0164(2) 0.161(6) Uani 1 1 d . . . . .
O2 O 0.6044(8) 0.4866(3) 0.94077(19) 0.080(2) Uani 1 1 d . . . . .
O3 O 0.5617(8) 0.9085(4) 0.33462(17) 0.081(2) Uani 1 1 d . . . . .
O4 O 1.0064(8) 0.9980(3) 0.35632(18) 0.075(2) Uani 1 1 d . . . . .
O5 O 0.4531(11) 0.9774(5) 0.1391(2) 0.115(3) Uani 1 1 d . . . . .
O6 O 0.0224(8) 0.8619(4) 0.14848(17) 0.081(2) Uani 1 1 d . . . . .
O7 O 0.932(2) 0.6712(6) 0.2555(4) 0.187(6) Uani 1 1 d . . . . .
O8 O 0.9205(7) 0.8427(3) 0.26166(18) 0.067(2) Uani 1 1 d . . . . .
O9 O 0.1334(9) 0.1910(3) 0.4097(2) 0.083(2) Uani 1 1 d . . . . .
O10 O 0.3738(9) -0.0059(3) 0.43672(18) 0.075(2) Uani 1 1 d . . . . .
C1 C 0.5534(16) 0.3876(5) 0.9862(3) 0.088(4) Uani 1 1 d . . . . .
C2 C 0.505(2) 0.3550(6) 1.0179(3) 0.104(5) Uani 1 1 d . . . . .
H2 H 0.5433 0.3769 1.0368 0.125 Uiso 1 1 calc R U . . .
C3 C 0.689(3) 0.3065(8) 1.0059(5) 0.207(13) Uani 1 1 d . . . . .
H3A H 0.7206 0.2702 0.9944 0.249 Uiso 1 1 calc R U . . .
H3B H 0.7456 0.3137 1.0248 0.249 Uiso 1 1 calc R U . . .
C4 C 0.695(2) 0.3633(6) 0.9820(3) 0.115(6) Uani 1 1 d . . . . .
H4 H 0.7061 0.3485 0.9592 0.138 Uiso 1 1 calc R U . . .
C5 C 0.805(2) 0.4061(7) 0.9901(4) 0.128(6) Uani 1 1 d . . . . .
H5A H 0.7946 0.4202 1.0127 0.153 Uiso 1 1 calc R U . . .
H5B H 0.7992 0.4417 0.9757 0.153 Uiso 1 1 calc R U . . .
C6 C 0.942(2) 0.3787(10) 0.9865(5) 0.198(10) Uani 1 1 d . . . . .
H6A H 0.9521 0.3623 0.9646 0.296 Uiso 1 1 calc R U . . .
H6B H 0.9529 0.3464 1.0025 0.296 Uiso 1 1 calc R U . . .
H6C H 1.0056 0.4102 0.9903 0.296 Uiso 1 1 calc R U . . .
C7 C 0.4687(18) 0.3702(6) 0.9557(3) 0.130(6) Uani 1 1 d . . . . .
H7A H 0.3799 0.3820 0.9596 0.195 Uiso 1 1 calc R U . . .
H7B H 0.4731 0.3266 0.9521 0.195 Uiso 1 1 calc R U . . .
H7C H 0.5008 0.3913 0.9364 0.195 Uiso 1 1 calc R U . . .
C8 C 0.358(2) 0.3473(7) 1.0249(3) 0.125(6) Uani 1 1 d . . . . .
H8 H 0.3184 0.3257 1.0061 0.150 Uiso 1 1 calc R U . . .
C9 C 0.346(2) 0.3058(6) 1.0556(3) 0.171(9) Uani 1 1 d . . . . .
H9A H 0.3881 0.2672 1.0513 0.257 Uiso 1 1 calc R U . . .
H9B H 0.2554 0.2987 1.0604 0.257 Uiso 1 1 calc R U . . .
H9C H 0.3865 0.3255 1.0742 0.257 Uiso 1 1 calc R U . . .
C10 C 0.2929(16) 0.4082(8) 1.0281(4) 0.138(6) Uani 1 1 d . . . . .
H10A H 0.2015 0.4024 1.0321 0.207 Uiso 1 1 calc R U . . .
H10B H 0.3048 0.4312 1.0080 0.207 Uiso 1 1 calc R U . . .
H10C H 0.3307 0.4304 1.0463 0.207 Uiso 1 1 calc R U . . .
C11 C 0.5679(12) 0.4974(5) 0.9688(3) 0.070(3) Uani 1 1 d . . . . .
C12 C 0.5379(11) 0.5613(5) 0.9794(2) 0.061(3) Uani 1 1 d . . . . .
C13 C 0.4452(13) 0.5768(5) 1.0023(3) 0.081(3) Uani 1 1 d . . . . .
H13 H 0.3944 0.5462 1.0120 0.097 Uiso 1 1 calc R U . . .
C14 C 0.4265(14) 0.6378(6) 1.0112(3) 0.094(4) Uani 1 1 d . . . . .
H14 H 0.3627 0.6477 1.0267 0.113 Uiso 1 1 calc R U . . .
C15 C 0.5000(15) 0.6831(5) 0.9975(3) 0.076(3) Uani 1 1 d . . . . .
C16 C 0.5896(14) 0.6692(6) 0.9749(3) 0.081(4) Uani 1 1 d . . . . .
H16 H 0.6378 0.7004 0.9651 0.097 Uiso 1 1 calc R U . . .
C17 C 0.6119(12) 0.6089(6) 0.9660(3) 0.076(3) Uani 1 1 d . . . . .
H17 H 0.6772 0.5998 0.9508 0.092 Uiso 1 1 calc R U . . .
C18 C 0.7806(11) 0.9265(5) 0.3436(2) 0.061(3) Uani 1 1 d . . . . .
C19 C 0.6829(11) 0.8812(5) 0.3279(3) 0.061(3) Uani 1 1 d . . . . .
H19 H 0.6963 0.8812 0.3038 0.074 Uiso 1 1 calc R U . . .
C20 C 0.5750(13) 0.9735(5) 0.3387(3) 0.081(4) Uani 1 1 d . . . . .
H20A H 0.5424 0.9858 0.3603 0.097 Uiso 1 1 calc R U . . .
H20B H 0.5255 0.9950 0.3218 0.097 Uiso 1 1 calc R U . . .
C21 C 0.7173(11) 0.9891(5) 0.3358(3) 0.067(3) Uani 1 1 d . . . . .
H21 H 0.7411 1.0190 0.3529 0.081 Uiso 1 1 calc R U . . .
C22 C 0.7534(12) 1.0142(5) 0.3018(3) 0.077(3) Uani 1 1 d . . . . .
H22A H 0.7291 0.9842 0.2852 0.092 Uiso 1 1 calc R U . . .
H22B H 0.8473 1.0192 0.3008 0.092 Uiso 1 1 calc R U . . .
C23 C 0.6896(14) 1.0755(6) 0.2932(3) 0.120(5) Uani 1 1 d . . . . .
H23A H 0.5977 1.0696 0.2901 0.179 Uiso 1 1 calc R U . . .
H23B H 0.7273 1.0913 0.2731 0.179 Uiso 1 1 calc R U . . .
H23C H 0.7038 1.1043 0.3109 0.179 Uiso 1 1 calc R U . . .
C24 C 0.7867(11) 0.9181(5) 0.3813(2) 0.077(3) Uani 1 1 d . . . . .
H24A H 0.8265 0.8793 0.3864 0.115 Uiso 1 1 calc R U . . .
H24B H 0.7001 0.9191 0.3903 0.115 Uiso 1 1 calc R U . . .
H24C H 0.8374 0.9507 0.3909 0.115 Uiso 1 1 calc R U . . .
C25 C 0.6765(15) 0.8156(5) 0.3395(3) 0.082(4) Uani 1 1 d . . . . .
H25 H 0.6528 0.8158 0.3630 0.099 Uiso 1 1 calc R U . . .
C26 C 0.8078(15) 0.7818(5) 0.3359(3) 0.100(4) Uani 1 1 d . . . . .
H26A H 0.8348 0.7826 0.3132 0.149 Uiso 1 1 calc R U . . .
H26B H 0.7981 0.7400 0.3431 0.149 Uiso 1 1 calc R U . . .
H26C H 0.8723 0.8019 0.3494 0.149 Uiso 1 1 calc R U . . .
C27 C 0.5709(15) 0.7807(6) 0.3207(3) 0.110(5) Uani 1 1 d . . . . .
H27A H 0.5946 0.7777 0.2977 0.164 Uiso 1 1 calc R U . . .
H27B H 0.4896 0.8023 0.3226 0.164 Uiso 1 1 calc R U . . .
H27C H 0.5619 0.7402 0.3298 0.164 Uiso 1 1 calc R U . . .
C28 C 1.0120(13) 0.9575(6) 0.3358(3) 0.068(3) Uani 1 1 d . . . . .
C29 C 1.1273(12) 0.9480(6) 0.3153(3) 0.063(3) Uani 1 1 d . . . . .
C30 C 1.1913(14) 0.9984(6) 0.3027(3) 0.087(4) Uani 1 1 d . . . . .
H30 H 1.1620 1.0377 0.3079 0.105 Uiso 1 1 calc R U . . .
C31 C 1.3002(15) 0.9909(7) 0.2823(4) 0.095(4) Uani 1 1 d . . . . .
H31 H 1.3433 1.0253 0.2741 0.114 Uiso 1 1 calc R U . . .
C32 C 1.3431(12) 0.9345(10) 0.2745(3) 0.090(4) Uani 1 1 d . . . . .
C33 C 1.2815(15) 0.8835(7) 0.2870(3) 0.094(4) Uani 1 1 d . . . . .
H33 H 1.3133 0.8444 0.2823 0.112 Uiso 1 1 calc R U . . .
C34 C 1.1712(12) 0.8906(6) 0.3067(3) 0.075(3) Uani 1 1 d . . . . .
H34 H 1.1266 0.8560 0.3141 0.090 Uiso 1 1 calc R U . . .
C35 C 0.2360(12) 0.9468(5) 0.1434(2) 0.067(3) Uani 1 1 d . . . . .
C36 C 0.3253(15) 0.9961(6) 0.1289(3) 0.083(4) Uani 1 1 d . . . . .
H36 H 0.3208 0.9936 0.1046 0.099 Uiso 1 1 calc R U . . .
C37 C 0.4545(15) 0.9137(7) 0.1448(3) 0.103(4) Uani 1 1 d . . . . .
H37A H 0.4848 0.9053 0.1671 0.124 Uiso 1 1 calc R U . . .
H37B H 0.5136 0.8939 0.1293 0.124 Uiso 1 1 calc R U . . .
C38 C 0.3209(12) 0.8887(6) 0.1404(3) 0.069(3) Uani 1 1 d . . . . .
H38 H 0.3012 0.8615 0.1591 0.083 Uiso 1 1 calc R U . . .
C39 C 0.3102(12) 0.8522(5) 0.1089(3) 0.078(3) Uani 1 1 d . . . . .
H39A H 0.3377 0.8777 0.0904 0.094 Uiso 1 1 calc R U . . .
H39B H 0.2196 0.8412 0.1053 0.094 Uiso 1 1 calc R U . . .
C40 C 0.3935(13) 0.7930(6) 0.1095(3) 0.109(5) Uani 1 1 d . . . . .
H40A H 0.4842 0.8037 0.1086 0.164 Uiso 1 1 calc R U . . .
H40B H 0.3719 0.7679 0.0907 0.164 Uiso 1 1 calc R U . . .
H40C H 0.3761 0.7705 0.1295 0.164 Uiso 1 1 calc R U . . .
C41 C 0.2013(13) 0.9589(6) 0.1793(3) 0.104(5) Uani 1 1 d . . . . .
H41A H 0.1345 0.9898 0.1804 0.155 Uiso 1 1 calc R U . . .
H41B H 0.2772 0.9730 0.1910 0.155 Uiso 1 1 calc R U . . .
H41C H 0.1702 0.9216 0.1893 0.155 Uiso 1 1 calc R U . . .
C42 C 0.3080(18) 1.0641(6) 0.1391(3) 0.114(5) Uani 1 1 d . . . . .
H42 H 0.3207 1.0672 0.1632 0.137 Uiso 1 1 calc R U . . .
C43 C 0.416(2) 1.1016(7) 0.1218(5) 0.175(8) Uani 1 1 d . . . . .
H43A H 0.4189 1.0911 0.0987 0.263 Uiso 1 1 calc R U . . .
H43B H 0.4990 1.0921 0.1318 0.263 Uiso 1 1 calc R U . . .
H43C H 0.3988 1.1447 0.1242 0.263 Uiso 1 1 calc R U . . .
C44 C 0.1765(19) 1.0888(6) 0.1310(4) 0.147(7) Uani 1 1 d . . . . .
H44A H 0.1706 1.1308 0.1381 0.220 Uiso 1 1 calc R U . . .
H44B H 0.1112 1.0648 0.1420 0.220 Uiso 1 1 calc R U . . .
H44C H 0.1630 1.0867 0.1075 0.220 Uiso 1 1 calc R U . . .
C45 C 0.0202(12) 0.9041(6) 0.1284(3) 0.064(3) Uani 1 1 d . . . . .
C46 C -0.0967(11) 0.9134(6) 0.1062(3) 0.064(3) Uani 1 1 d . . . . .
C47 C -0.1463(13) 0.9708(5) 0.0998(3) 0.072(3) Uani 1 1 d . . . . .
H47 H -0.1083 1.0052 0.1094 0.086 Uiso 1 1 calc R U . . .
C48 C -0.2550(13) 0.9777(6) 0.0786(3) 0.078(3) Uani 1 1 d . . . . .
H48 H -0.2881 1.0164 0.0736 0.093 Uiso 1 1 calc R U . . .
C49 C -0.3106(11) 0.9250(6) 0.0654(2) 0.069(3) Uani 1 1 d . . . . .
C50 C -0.2620(14) 0.8684(6) 0.0726(3) 0.086(4) Uani 1 1 d . . . . .
H50 H -0.3002 0.8336 0.0634 0.103 Uiso 1 1 calc R U . . .
C51 C -0.1575(13) 0.8624(6) 0.0932(3) 0.076(3) Uani 1 1 d . . . . .
H51 H -0.1269 0.8234 0.0985 0.092 Uiso 1 1 calc R U . . .
C52 C 0.9343(13) 0.7417(5) 0.2119(3) 0.072(3) Uani 1 1 d . . . . .
C53 C 0.8488(16) 0.7125(6) 0.2385(4) 0.101(4) Uani 1 1 d . . . . .
H53 H 0.8241 0.7449 0.2541 0.121 Uiso 1 1 calc R U . . .
C54 C 1.055(3) 0.7029(10) 0.2563(6) 0.188(10) Uani 1 1 d . . . . .
H54A H 1.1248 0.6747 0.2617 0.225 Uiso 1 1 calc R U . . .
H54B H 1.0530 0.7354 0.2728 0.225 Uiso 1 1 calc R U . . .
C55 C 1.0739(15) 0.7286(6) 0.2231(5) 0.114(5) Uani 1 1 d . . . . .
H55 H 1.1050 0.6946 0.2093 0.136 Uiso 1 1 calc R U . . .
C56 C 1.1727(16) 0.7798(8) 0.2193(6) 0.167(9) Uani 1 1 d . . . . .
H56 H 1.1476 0.8206 0.2166 0.201 Uiso 1 1 calc R U . . .
C57 C 1.299(2) 0.7629(9) 0.2199(5) 0.190(9) Uani 1 1 d . . . . .
H57A H 1.3211 0.7218 0.2227 0.228 Uiso 1 1 calc R U . . .
H57B H 1.3638 0.7925 0.2177 0.228 Uiso 1 1 calc R U . . .
C58 C 0.9147(16) 0.7149(5) 0.1768(3) 0.112(5) Uani 1 1 d . . . . .
H58A H 0.8361 0.7312 0.1674 0.168 Uiso 1 1 calc R U . . .
H58B H 0.9082 0.6709 0.1782 0.168 Uiso 1 1 calc R U . . .
H58C H 0.9875 0.7258 0.1631 0.168 Uiso 1 1 calc R U . . .
C59 C 0.728(2) 0.6795(8) 0.2288(5) 0.157(9) Uani 1 1 d . . . . .
H59 H 0.7484 0.6503 0.2111 0.189 Uiso 1 1 calc R U . . .
C60 C 0.680(3) 0.6423(9) 0.2603(6) 0.282(18) Uani 1 1 d . . . . .
H60A H 0.6760 0.6695 0.2791 0.423 Uiso 1 1 calc R U . . .
H60B H 0.7403 0.6096 0.2649 0.423 Uiso 1 1 calc R U . . .
H60C H 0.5953 0.6255 0.2562 0.423 Uiso 1 1 calc R U . . .
C61 C 0.638(2) 0.7227(12) 0.2168(7) 0.248(17) Uani 1 1 d . . . . .
H61A H 0.6600 0.7641 0.2160 0.298 Uiso 1 1 calc R U . . .
H61B H 0.5561 0.7099 0.2096 0.298 Uiso 1 1 calc R U . . .
C62 C 0.9030(11) 0.8513(5) 0.2322(3) 0.062(3) Uani 1 1 d . . . . .
C63 C 0.8689(10) 0.9134(5) 0.2193(2) 0.053(3) Uani 1 1 d . . . . .
C64 C 0.7746(11) 0.9213(5) 0.1952(3) 0.066(3) Uani 1 1 d . . . . .
H64 H 0.7331 0.8871 0.1863 0.079 Uiso 1 1 calc R U . . .
C65 C 0.7412(12) 0.9794(6) 0.1843(3) 0.077(4) Uani 1 1 d . . . . .
H65 H 0.6751 0.9847 0.1688 0.092 Uiso 1 1 calc R U . . .
C66 C 0.8060(15) 1.0282(5) 0.1965(3) 0.085(4) Uani 1 1 d . . . . .
C67 C 0.9005(13) 1.0221(5) 0.2203(3) 0.076(4) Uani 1 1 d . . . . .
H67 H 0.9435 1.0566 0.2285 0.092 Uiso 1 1 calc R U . . .
C68 C 0.9301(12) 0.9654(5) 0.2317(2) 0.069(3) Uani 1 1 d . . . . .
H68 H 0.9928 0.9612 0.2482 0.083 Uiso 1 1 calc R U . . .
C69 C 0.1914(11) 0.0907(4) 0.4256(2) 0.057(3) Uani 1 1 d . . . . .
C70 C 0.0829(11) 0.1296(5) 0.4094(3) 0.062(3) Uani 1 1 d . . . . .
H70 H 0.0720 0.1164 0.3863 0.074 Uiso 1 1 calc R U . . .
C71 C 0.2672(15) 0.1905(5) 0.4145(4) 0.100(4) Uani 1 1 d . . . . .
H71A H 0.2882 0.2081 0.4359 0.120 Uiso 1 1 calc R U . . .
H71B H 0.3096 0.2148 0.3975 0.120 Uiso 1 1 calc R U . . .
C72 C 0.3143(12) 0.1247(5) 0.4129(3) 0.071(3) Uani 1 1 d . . . . .
H72 H 0.3865 0.1187 0.4285 0.086 Uiso 1 1 calc R U . . .
C73 C 0.3572(13) 0.1066(5) 0.3780(3) 0.091(4) Uani 1 1 d . . . . .
H73A H 0.3614 0.0621 0.3766 0.109 Uiso 1 1 calc R U . . .
H73B H 0.2918 0.1204 0.3623 0.109 Uiso 1 1 calc R U . . .
C74 C 0.4884(16) 0.1328(7) 0.3678(5) 0.170(8) Uani 1 1 d . . . . .
H74A H 0.4821 0.1768 0.3662 0.255 Uiso 1 1 calc R U . . .
H74B H 0.5134 0.1162 0.3467 0.255 Uiso 1 1 calc R U . . .
H74C H 0.5526 0.1221 0.3841 0.255 Uiso 1 1 calc R U . . .
C75 C 0.1863(13) 0.0932(5) 0.4629(2) 0.089(4) Uani 1 1 d . . . . .
H75A H 0.1075 0.0741 0.4705 0.133 Uiso 1 1 calc R U . . .
H75B H 0.1881 0.1353 0.4701 0.133 Uiso 1 1 calc R U . . .
H75C H 0.2601 0.0718 0.4719 0.133 Uiso 1 1 calc R U . . .
C76 C -0.0491(13) 0.1313(5) 0.4259(3) 0.081(4) Uani 1 1 d . . . . .
H76 H -0.0370 0.1452 0.4488 0.097 Uiso 1 1 calc R U . . .
C77 C -0.1389(14) 0.1780(6) 0.4081(4) 0.115(5) Uani 1 1 d . . . . .
H77A H -0.0983 0.2178 0.4080 0.173 Uiso 1 1 calc R U . . .
H77B H -0.2208 0.1804 0.4195 0.173 Uiso 1 1 calc R U . . .
H77C H -0.1533 0.1648 0.3857 0.173 Uiso 1 1 calc R U . . .
C78 C -0.1137(13) 0.0683(6) 0.4268(3) 0.108(4) Uani 1 1 d . . . . .
H78A H -0.1080 0.0496 0.4053 0.162 Uiso 1 1 calc R U . . .
H78B H -0.2037 0.0728 0.4329 0.162 Uiso 1 1 calc R U . . .
H78C H -0.0703 0.0428 0.4428 0.162 Uiso 1 1 calc R U . . .
C79 C 0.2732(15) -0.0156(5) 0.4213(3) 0.061(3) Uani 1 1 d . . . . .
C80 C 0.2454(15) -0.0797(5) 0.4095(2) 0.065(3) Uani 1 1 d . . . . .
C81 C 0.1229(14) -0.1057(6) 0.4124(3) 0.076(3) Uani 1 1 d . . . . .
H81 H 0.0544 -0.0818 0.4203 0.091 Uiso 1 1 calc R U . . .
C82 C 0.0997(16) -0.1658(6) 0.4038(3) 0.096(4) Uani 1 1 d . . . . .
H82 H 0.0171 -0.1828 0.4062 0.115 Uiso 1 1 calc R U . . .
C83 C 0.1993(19) -0.1994(5) 0.3919(3) 0.090(4) Uani 1 1 d . . . . .
C84 C 0.3221(18) -0.1751(7) 0.3881(3) 0.105(5) Uani 1 1 d . . . . .
H84 H 0.3895 -0.1985 0.3793 0.126 Uiso 1 1 calc R U . . .
C85 C 0.3423(14) -0.1149(5) 0.3977(3) 0.082(4) Uani 1 1 d . . . . .
H85 H 0.4255 -0.0983 0.3960 0.098 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
Br1 C15 1.884(11) . ?
Br2 C32 1.892(13) . ?
Br3 C49 1.880(10) . ?
Br4 C66 1.893(11) . ?
Br5 C83 1.898(12) . ?
N1 C11 1.332(12) . ?
N1 C1 1.464(13) . ?
N1 H1 0.8600 . ?
N2 C28 1.351(14) . ?
N2 C18 1.475(13) . ?
N2 H2A 0.8600 . ?
N3 C45 1.323(13) . ?
N3 C35 1.465(13) . ?
N3 H3D 0.8600 . ?
N4 C62 1.341(12) . ?
N4 C52 1.469(13) . ?
N4 H4A 0.8600 . ?
N5 C79 1.326(13) . ?
N5 C69 1.463(11) . ?
N5 H5D 0.8600 . ?
O1 C3 1.36(2) . ?
O1 C2 1.403(16) . ?
O2 C11 1.213(12) . ?
O3 C19 1.405(12) . ?
O3 C20 1.430(12) . ?
O4 C28 1.209(12) . ?
O5 C37 1.406(14) . ?
O5 C36 1.434(15) . ?
O6 C45 1.226(11) . ?
O7 C53 1.420(18) . ?
O7 C54 1.43(2) . ?
O8 C62 1.216(11) . ?
O9 C71 1.386(14) . ?
O9 C70 1.432(12) . ?
O10 C79 1.222(13) . ?
C1 C2 1.542(17) . ?
C1 C7 1.553(17) . ?
C1 C4 1.56(2) . ?
C2 C8 1.55(2) . ?
C2 H2 0.9800 . ?
C3 C4 1.57(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.50(2) . ?
C4 H4 0.9800 . ?
C5 C6 1.53(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C10 1.49(2) . ?
C8 C9 1.536(18) . ?
C8 H8 0.9800 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.486(14) . ?
C12 C13 1.368(14) . ?
C12 C17 1.393(14) . ?
C13 C14 1.387(15) . ?
C13 H13 0.9300 . ?
C14 C15 1.359(16) . ?
C14 H14 0.9300 . ?
C15 C16 1.329(16) . ?
C16 C17 1.380(15) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C24 1.533(13) . ?
C18 C21 1.541(14) . ?
C18 C19 1.543(13) . ?
C19 C25 1.502(14) . ?
C19 H19 0.9800 . ?
C20 C21 1.504(15) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.520(14) . ?
C21 H21 0.9800 . ?
C22 C23 1.526(15) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C27 1.525(16) . ?
C25 C26 1.542(17) . ?
C25 H25 0.9800 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 C29 1.459(15) . ?
C29 C34 1.371(15) . ?
C29 C30 1.374(16) . ?
C30 C31 1.398(17) . ?
C30 H30 0.9300 . ?
C31 C32 1.341(17) . ?
C31 H31 0.9300 . ?
C32 C33 1.372(18) . ?
C33 C34 1.391(16) . ?
C33 H33 0.9300 . ?
C34 H34 0.9300 . ?
C35 C41 1.518(14) . ?
C35 C36 1.526(15) . ?
C35 C38 1.539(15) . ?
C36 C42 1.547(17) . ?
C36 H36 0.9800 . ?
C37 C38 1.485(16) . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C38 C39 1.502(13) . ?
C38 H38 0.9800 . ?
C39 C40 1.547(15) . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
C41 H41A 0.9600 . ?
C41 H41B 0.9600 . ?
C41 H41C 0.9600 . ?
C42 C44 1.49(2) . ?
C42 C43 1.55(2) . ?
C42 H42 0.9800 . ?
C43 H43A 0.9600 . ?
C43 H43B 0.9600 . ?
C43 H43C 0.9600 . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 0.9600 . ?
C45 C46 1.510(15) . ?
C46 C47 1.372(14) . ?
C46 C51 1.375(14) . ?
C47 C48 1.414(16) . ?
C47 H47 0.9300 . ?
C48 C49 1.386(14) . ?
C48 H48 0.9300 . ?
C49 C50 1.358(14) . ?
C50 C51 1.364(15) . ?
C50 H50 0.9300 . ?
C51 H51 0.9300 . ?
C52 C53 1.524(17) . ?
C52 C55 1.528(18) . ?
C52 C58 1.544(14) . ?
C53 C59 1.49(2) . ?
C53 H53 0.9800 . ?
C54 C55 1.46(2) . ?
C54 H54A 0.9700 . ?
C54 H54B 0.9700 . ?
C55 C56 1.51(2) . ?
C55 H55 0.9800 . ?
C56 C57 1.35(2) . ?
C56 H56 0.9300 . ?
C57 H57A 0.9300 . ?
C57 H57B 0.9300 . ?
C58 H58A 0.9600 . ?
C58 H58B 0.9600 . ?
C58 H58C 0.9600 . ?
C59 C61 1.40(3) . ?
C59 C60 1.58(3) . ?
C59 H59 0.9800 . ?
C60 H60A 0.9600 . ?
C60 H60B 0.9600 . ?
C60 H60C 0.9600 . ?
C61 H61A 0.9300 . ?
C61 H61B 0.9300 . ?
C62 C63 1.489(14) . ?
C63 C64 1.382(13) . ?
C63 C68 1.388(13) . ?
C64 C65 1.380(14) . ?
C64 H64 0.9300 . ?
C65 C66 1.346(15) . ?
C65 H65 0.9300 . ?
C66 C67 1.372(16) . ?
C67 C68 1.350(13) . ?
C67 H67 0.9300 . ?
C68 H68 0.9300 . ?
C69 C75 1.507(13) . ?
C69 C70 1.544(13) . ?
C69 C72 1.548(15) . ?
C70 C76 1.510(15) . ?
C70 H70 0.9800 . ?
C71 C72 1.512(15) . ?
C71 H71A 0.9700 . ?
C71 H71B 0.9700 . ?
C72 C73 1.529(15) . ?
C72 H72 0.9800 . ?
C73 C74 1.518(17) . ?
C73 H73A 0.9700 . ?
C73 H73B 0.9700 . ?
C74 H74A 0.9600 . ?
C74 H74B 0.9600 . ?
C74 H74C 0.9600 . ?
C75 H75A 0.9600 . ?
C75 H75B 0.9600 . ?
C75 H75C 0.9600 . ?
C76 C78 1.523(16) . ?
C76 C77 1.548(16) . ?
C76 H76 0.9800 . ?
C77 H77A 0.9600 . ?
C77 H77B 0.9600 . ?
C77 H77C 0.9600 . ?
C78 H78A 0.9600 . ?
C78 H78B 0.9600 . ?
C78 H78C 0.9600 . ?
C79 C80 1.501(15) . ?
C80 C85 1.342(15) . ?
C80 C81 1.383(15) . ?
C81 C82 1.372(15) . ?
C81 H81 0.9300 . ?
C82 C83 1.344(18) . ?
C82 H82 0.9300 . ?
C83 C84 1.375(18) . ?
C84 C85 1.381(16) . ?
C84 H84 0.9300 . ?
C85 H85 0.9300 . ?

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
C11 N1 C1 126.2(9) . . ?
C11 N1 H1 116.9 . . ?
C1 N1 H1 116.9 . . ?
C28 N2 C18 123.4(9) . . ?
C28 N2 H2A 118.3 . . ?
C18 N2 H2A 118.3 . . ?
C45 N3 C35 125.2(9) . . ?
C45 N3 H3D 117.4 . . ?
C35 N3 H3D 117.4 . . ?
C62 N4 C52 129.4(9) . . ?
C62 N4 H4A 115.3 . . ?
C52 N4 H4A 115.3 . . ?
C79 N5 C69 124.1(9) . . ?
C79 N5 H5D 117.9 . . ?
C69 N5 H5D 117.9 . . ?
C3 O1 C2 106.7(14) . . ?
C19 O3 C20 110.8(9) . . ?
C37 O5 C36 109.6(11) . . ?
C53 O7 C54 103.7(13) . . ?
C71 O9 C70 110.6(8) . . ?
N1 C1 C2 108.5(10) . . ?
N1 C1 C7 109.7(11) . . ?
C2 C1 C7 111.5(11) . . ?
N1 C1 C4 112.7(11) . . ?
C2 C1 C4 103.5(12) . . ?
C7 C1 C4 110.8(12) . . ?
O1 C2 C1 103.7(12) . . ?
O1 C2 C8 109.8(15) . . ?
C1 C2 C8 120.9(13) . . ?
O1 C2 H2 107.3 . . ?
C1 C2 H2 107.3 . . ?
C8 C2 H2 107.3 . . ?
O1 C3 C4 110.3(18) . . ?
O1 C3 H3A 109.6 . . ?
C4 C3 H3A 109.6 . . ?
O1 C3 H3B 109.6 . . ?
C4 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?
C5 C4 C1 118.1(12) . . ?
C5 C4 C3 112.5(17) . . ?
C1 C4 C3 99.5(15) . . ?
C5 C4 H4 108.7 . . ?
C1 C4 H4 108.7 . . ?
C3 C4 H4 108.7 . . ?
C4 C5 C6 115.4(16) . . ?
C4 C5 H5A 108.4 . . ?
C6 C5 H5A 108.4 . . ?
C4 C5 H5B 108.4 . . ?
C6 C5 H5B 108.4 . . ?
H5A C5 H5B 107.5 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C10 C8 C9 114.7(14) . . ?
C10 C8 C2 110.8(13) . . ?
C9 C8 C2 106.8(17) . . ?
C10 C8 H8 108.1 . . ?
C9 C8 H8 108.1 . . ?
C2 C8 H8 108.1 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 C11 N1 123.5(10) . . ?
O2 C11 C12 120.9(11) . . ?
N1 C11 C12 115.5(10) . . ?
C13 C12 C17 117.3(10) . . ?
C13 C12 C11 124.7(11) . . ?
C17 C12 C11 118.0(11) . . ?
C12 C13 C14 120.4(11) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C15 C14 C13 120.8(12) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C16 C15 C14 119.8(11) . . ?
C16 C15 Br1 120.4(11) . . ?
C14 C15 Br1 119.8(11) . . ?
C15 C16 C17 120.7(12) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C16 C17 C12 120.9(12) . . ?
C16 C17 H17 119.5 . . ?
C12 C17 H17 119.5 . . ?
N2 C18 C24 110.6(9) . . ?
N2 C18 C21 112.9(8) . . ?
C24 C18 C21 109.1(8) . . ?
N2 C18 C19 111.1(9) . . ?
C24 C18 C19 111.1(9) . . ?
C21 C18 C19 101.9(8) . . ?
O3 C19 C25 107.6(9) . . ?
O3 C19 C18 103.0(8) . . ?
C25 C19 C18 120.4(9) . . ?
O3 C19 H19 108.4 . . ?
C25 C19 H19 108.4 . . ?
C18 C19 H19 108.4 . . ?
O3 C20 C21 107.8(10) . . ?
O3 C20 H20A 110.1 . . ?
C21 C20 H20A 110.1 . . ?
O3 C20 H20B 110.1 . . ?
C21 C20 H20B 110.1 . . ?
H20A C20 H20B 108.5 . . ?
C20 C21 C22 112.9(10) . . ?
C20 C21 C18 101.2(9) . . ?
C22 C21 C18 113.6(9) . . ?
C20 C21 H21 109.6 . . ?
C22 C21 H21 109.6 . . ?
C18 C21 H21 109.6 . . ?
C21 C22 C23 114.6(10) . . ?
C21 C22 H22A 108.6 . . ?
C23 C22 H22A 108.6 . . ?
C21 C22 H22B 108.6 . . ?
C23 C22 H22B 108.6 . . ?
H22A C22 H22B 107.6 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C18 C24 H24A 109.5 . . ?
C18 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C18 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C19 C25 C27 110.4(10) . . ?
C19 C25 C26 112.6(10) . . ?
C27 C25 C26 109.7(10) . . ?
C19 C25 H25 108.0 . . ?
C27 C25 H25 108.0 . . ?
C26 C25 H25 108.0 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O4 C28 N2 123.3(11) . . ?
O4 C28 C29 122.0(12) . . ?
N2 C28 C29 114.6(11) . . ?
C34 C29 C30 118.4(12) . . ?
C34 C29 C28 122.6(12) . . ?
C30 C29 C28 118.9(12) . . ?
C29 C30 C31 120.4(13) . . ?
C29 C30 H30 119.8 . . ?
C31 C30 H30 119.8 . . ?
C32 C31 C30 120.5(13) . . ?
C32 C31 H31 119.7 . . ?
C30 C31 H31 119.7 . . ?
C31 C32 C33 120.0(12) . . ?
C31 C32 Br2 119.4(14) . . ?
C33 C32 Br2 120.5(14) . . ?
C32 C33 C34 119.7(13) . . ?
C32 C33 H33 120.1 . . ?
C34 C33 H33 120.1 . . ?
C29 C34 C33 120.8(12) . . ?
C29 C34 H34 119.6 . . ?
C33 C34 H34 119.6 . . ?
N3 C35 C41 109.4(10) . . ?
N3 C35 C36 109.1(10) . . ?
C41 C35 C36 112.7(10) . . ?
N3 C35 C38 113.1(9) . . ?
C41 C35 C38 110.5(9) . . ?
C36 C35 C38 102.0(9) . . ?
O5 C36 C35 103.8(10) . . ?
O5 C36 C42 107.3(11) . . ?
C35 C36 C42 120.0(12) . . ?
O5 C36 H36 108.4 . . ?
C35 C36 H36 108.4 . . ?
C42 C36 H36 108.4 . . ?
O5 C37 C38 109.3(12) . . ?
O5 C37 H37A 109.8 . . ?
C38 C37 H37A 109.8 . . ?
O5 C37 H37B 109.8 . . ?
C38 C37 H37B 109.8 . . ?
H37A C37 H37B 108.3 . . ?
C37 C38 C39 111.2(10) . . ?
C37 C38 C35 102.3(10) . . ?
C39 C38 C35 117.3(9) . . ?
C37 C38 H38 108.6 . . ?
C39 C38 H38 108.6 . . ?
C35 C38 H38 108.6 . . ?
C38 C39 C40 112.7(10) . . ?
C38 C39 H39A 109.0 . . ?
C40 C39 H39A 109.0 . . ?
C38 C39 H39B 109.0 . . ?
C40 C39 H39B 109.0 . . ?
H39A C39 H39B 107.8 . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C35 C41 H41A 109.5 . . ?
C35 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C35 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C44 C42 C43 111.3(13) . . ?
C44 C42 C36 112.9(12) . . ?
C43 C42 C36 107.5(14) . . ?
C44 C42 H42 108.4 . . ?
C43 C42 H42 108.4 . . ?
C36 C42 H42 108.4 . . ?
C42 C43 H43A 109.5 . . ?
C42 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
C42 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C42 C44 H44A 109.5 . . ?
C42 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C42 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
O6 C45 N3 124.7(11) . . ?
O6 C45 C46 120.5(12) . . ?
N3 C45 C46 114.8(10) . . ?
C47 C46 C51 119.6(11) . . ?
C47 C46 C45 121.8(12) . . ?
C51 C46 C45 118.5(12) . . ?
C46 C47 C48 120.2(11) . . ?
C46 C47 H47 119.9 . . ?
C48 C47 H47 119.9 . . ?
C49 C48 C47 117.9(11) . . ?
C49 C48 H48 121.0 . . ?
C47 C48 H48 121.0 . . ?
C50 C49 C48 121.1(10) . . ?
C50 C49 Br3 121.2(10) . . ?
C48 C49 Br3 117.7(10) . . ?
C49 C50 C51 120.4(12) . . ?
C49 C50 H50 119.8 . . ?
C51 C50 H50 119.8 . . ?
C50 C51 C46 120.7(12) . . ?
C50 C51 H51 119.6 . . ?
C46 C51 H51 119.6 . . ?
N4 C52 C53 111.8(10) . . ?
N4 C52 C55 111.9(10) . . ?
C53 C52 C55 104.7(11) . . ?
N4 C52 C58 105.4(9) . . ?
C53 C52 C58 114.3(11) . . ?
C55 C52 C58 108.9(11) . . ?
O7 C53 C59 109.1(15) . . ?
O7 C53 C52 104.8(13) . . ?
C59 C53 C52 119.9(14) . . ?
O7 C53 H53 107.5 . . ?
C59 C53 H53 107.5 . . ?
C52 C53 H53 107.5 . . ?
O7 C54 C55 106.3(18) . . ?
O7 C54 H54A 110.5 . . ?
C55 C54 H54A 110.5 . . ?
O7 C54 H54B 110.5 . . ?
C55 C54 H54B 110.5 . . ?
H54A C54 H54B 108.7 . . ?
C54 C55 C56 117.7(19) . . ?
C54 C55 C52 102.5(15) . . ?
C56 C55 C52 117.4(13) . . ?
C54 C55 H55 106.1 . . ?
C56 C55 H55 106.1 . . ?
C52 C55 H55 106.1 . . ?
C57 C56 C55 116.3(16) . . ?
C57 C56 H56 121.9 . . ?
C55 C56 H56 121.9 . . ?
C56 C57 H57A 120.0 . . ?
C56 C57 H57B 120.0 . . ?
H57A C57 H57B 120.0 . . ?
C52 C58 H58A 109.5 . . ?
C52 C58 H58B 109.5 . . ?
H58A C58 H58B 109.5 . . ?
C52 C58 H58C 109.5 . . ?
H58A C58 H58C 109.5 . . ?
H58B C58 H58C 109.5 . . ?
C61 C59 C53 108.4(16) . . ?
C61 C59 C60 115(2) . . ?
C53 C59 C60 107.0(19) . . ?
C61 C59 H59 108.9 . . ?
C53 C59 H59 108.9 . . ?
C60 C59 H59 108.9 . . ?
C59 C60 H60A 109.5 . . ?
C59 C60 H60B 109.5 . . ?
H60A C60 H60B 109.5 . . ?
C59 C60 H60C 109.5 . . ?
H60A C60 H60C 109.5 . . ?
H60B C60 H60C 109.5 . . ?
C59 C61 H61A 120.0 . . ?
C59 C61 H61B 120.0 . . ?
H61A C61 H61B 120.0 . . ?
O8 C62 N4 125.3(10) . . ?
O8 C62 C63 121.1(10) . . ?
N4 C62 C63 113.7(10) . . ?
C64 C63 C68 117.9(9) . . ?
C64 C63 C62 121.6(10) . . ?
C68 C63 C62 120.4(10) . . ?
C65 C64 C63 120.8(10) . . ?
C65 C64 H64 119.6 . . ?
C63 C64 H64 119.6 . . ?
C66 C65 C64 118.8(11) . . ?
C66 C65 H65 120.6 . . ?
C64 C65 H65 120.6 . . ?
C65 C66 C67 122.0(10) . . ?
C65 C66 Br4 118.1(11) . . ?
C67 C66 Br4 119.9(10) . . ?
C68 C67 C66 119.0(11) . . ?
C68 C67 H67 120.5 . . ?
C66 C67 H67 120.5 . . ?
C67 C68 C63 121.4(11) . . ?
C67 C68 H68 119.3 . . ?
C63 C68 H68 119.3 . . ?
N5 C69 C75 110.2(8) . . ?
N5 C69 C70 110.7(8) . . ?
C75 C69 C70 112.2(9) . . ?
N5 C69 C72 112.7(9) . . ?
C75 C69 C72 110.0(9) . . ?
C70 C69 C72 100.7(8) . . ?
O9 C70 C76 107.3(9) . . ?
O9 C70 C69 104.2(8) . . ?
C76 C70 C69 118.3(9) . . ?
O9 C70 H70 108.9 . . ?
C76 C70 H70 108.9 . . ?
C69 C70 H70 108.9 . . ?
O9 C71 C72 108.6(10) . . ?
O9 C71 H71A 110.0 . . ?
C72 C71 H71A 110.0 . . ?
O9 C71 H71B 110.0 . . ?
C72 C71 H71B 110.0 . . ?
H71A C71 H71B 108.4 . . ?
C71 C72 C73 112.1(10) . . ?
C71 C72 C69 100.2(10) . . ?
C73 C72 C69 114.6(9) . . ?
C71 C72 H72 109.9 . . ?
C73 C72 H72 109.9 . . ?
C69 C72 H72 109.9 . . ?
C74 C73 C72 114.0(12) . . ?
C74 C73 H73A 108.8 . . ?
C72 C73 H73A 108.8 . . ?
C74 C73 H73B 108.8 . . ?
C72 C73 H73B 108.8 . . ?
H73A C73 H73B 107.6 . . ?
C73 C74 H74A 109.5 . . ?
C73 C74 H74B 109.5 . . ?
H74A C74 H74B 109.5 . . ?
C73 C74 H74C 109.5 . . ?
H74A C74 H74C 109.5 . . ?
H74B C74 H74C 109.5 . . ?
C69 C75 H75A 109.5 . . ?
C69 C75 H75B 109.5 . . ?
H75A C75 H75B 109.5 . . ?
C69 C75 H75C 109.5 . . ?
H75A C75 H75C 109.5 . . ?
H75B C75 H75C 109.5 . . ?
C70 C76 C78 112.2(10) . . ?
C70 C76 C77 110.2(10) . . ?
C78 C76 C77 110.0(11) . . ?
C70 C76 H76 108.1 . . ?
C78 C76 H76 108.1 . . ?
C77 C76 H76 108.1 . . ?
C76 C77 H77A 109.5 . . ?
C76 C77 H77B 109.5 . . ?
H77A C77 H77B 109.5 . . ?
C76 C77 H77C 109.5 . . ?
H77A C77 H77C 109.5 . . ?
H77B C77 H77C 109.5 . . ?
C76 C78 H78A 109.5 . . ?
C76 C78 H78B 109.5 . . ?
H78A C78 H78B 109.5 . . ?
C76 C78 H78C 109.5 . . ?
H78A C78 H78C 109.5 . . ?
H78B C78 H78C 109.5 . . ?
O10 C79 N5 124.6(10) . . ?
O10 C79 C80 118.7(12) . . ?
N5 C79 C80 116.7(12) . . ?
C85 C80 C81 118.0(11) . . ?
C85 C80 C79 120.1(13) . . ?
C81 C80 C79 121.7(12) . . ?
C82 C81 C80 121.7(13) . . ?
C82 C81 H81 119.2 . . ?
C80 C81 H81 119.2 . . ?
C83 C82 C81 118.4(13) . . ?
C83 C82 H82 120.8 . . ?
C81 C82 H82 120.8 . . ?
C82 C83 C84 121.9(12) . . ?
C82 C83 Br5 117.8(13) . . ?
C84 C83 Br5 120.3(12) . . ?
C83 C84 C85 118.0(12) . . ?
C83 C84 H84 121.0 . . ?
C85 C84 H84 121.0 . . ?
C80 C85 C84 121.9(13) . . ?
C80 C85 H85 119.0 . . ?
C84 C85 H85 119.0 . . ?

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
C11 N1 C1 C2 -172.1(13) . . . . ?
C11 N1 C1 C7 -50.0(18) . . . . ?
C11 N1 C1 C4 73.9(15) . . . . ?
C3 O1 C2 C1 41.6(19) . . . . ?
C3 O1 C2 C8 172.1(15) . . . . ?
N1 C1 C2 O1 -155.0(13) . . . . ?
C7 C1 C2 O1 84.0(17) . . . . ?
C4 C1 C2 O1 -35.1(15) . . . . ?
N1 C1 C2 C8 81.5(15) . . . . ?
C7 C1 C2 C8 -39.5(17) . . . . ?
C4 C1 C2 C8 -158.6(13) . . . . ?
C2 O1 C3 C4 -32(2) . . . . ?
N1 C1 C4 C5 11.2(16) . . . . ?
C2 C1 C4 C5 -105.9(13) . . . . ?
C7 C1 C4 C5 134.5(12) . . . . ?
N1 C1 C4 C3 133.1(13) . . . . ?
C2 C1 C4 C3 16.1(15) . . . . ?
C7 C1 C4 C3 -103.5(14) . . . . ?
O1 C3 C4 C5 133.8(19) . . . . ?
O1 C3 C4 C1 8(2) . . . . ?
C1 C4 C5 C6 178.0(13) . . . . ?
C3 C4 C5 C6 63.0(19) . . . . ?
O1 C2 C8 C10 177.5(11) . . . . ?
C1 C2 C8 C10 -61.9(16) . . . . ?
O1 C2 C8 C9 51.9(14) . . . . ?
C1 C2 C8 C9 172.5(10) . . . . ?
C1 N1 C11 O2 -7(2) . . . . ?
C1 N1 C11 C12 171.4(12) . . . . ?
O2 C11 C12 C13 148.0(12) . . . . ?
N1 C11 C12 C13 -30.0(16) . . . . ?
O2 C11 C12 C17 -34.0(16) . . . . ?
N1 C11 C12 C17 147.9(11) . . . . ?
C17 C12 C13 C14 0.6(16) . . . . ?
C11 C12 C13 C14 178.5(11) . . . . ?
C12 C13 C14 C15 -0.4(19) . . . . ?
C13 C14 C15 C16 1.2(19) . . . . ?
C13 C14 C15 Br1 -178.6(9) . . . . ?
C14 C15 C16 C17 -2.2(18) . . . . ?
Br1 C15 C16 C17 177.6(8) . . . . ?
C15 C16 C17 C12 2.4(17) . . . . ?
C13 C12 C17 C16 -1.6(15) . . . . ?
C11 C12 C17 C16 -179.6(10) . . . . ?
C28 N2 C18 C24 -62.7(12) . . . . ?
C28 N2 C18 C21 59.8(12) . . . . ?
C28 N2 C18 C19 173.5(8) . . . . ?
C20 O3 C19 C25 153.7(9) . . . . ?
C20 O3 C19 C18 25.6(10) . . . . ?
N2 C18 C19 O3 -158.3(8) . . . . ?
C24 C18 C19 O3 78.1(10) . . . . ?
C21 C18 C19 O3 -37.9(10) . . . . ?
N2 C18 C19 C25 82.0(12) . . . . ?
C24 C18 C19 C25 -41.5(14) . . . . ?
C21 C18 C19 C25 -157.5(10) . . . . ?
C19 O3 C20 C21 -2.5(12) . . . . ?
O3 C20 C21 C22 100.2(11) . . . . ?
O3 C20 C21 C18 -21.6(11) . . . . ?
N2 C18 C21 C20 154.6(9) . . . . ?
C24 C18 C21 C20 -82.0(10) . . . . ?
C19 C18 C21 C20 35.5(10) . . . . ?
N2 C18 C21 C22 33.3(12) . . . . ?
C24 C18 C21 C22 156.7(9) . . . . ?
C19 C18 C21 C22 -85.8(11) . . . . ?
C20 C21 C22 C23 64.3(13) . . . . ?
C18 C21 C22 C23 178.8(11) . . . . ?
O3 C19 C25 C27 61.5(12) . . . . ?
C18 C19 C25 C27 178.8(10) . . . . ?
O3 C19 C25 C26 -175.5(9) . . . . ?
C18 C19 C25 C26 -58.2(14) . . . . ?
C18 N2 C28 O4 4.8(16) . . . . ?
C18 N2 C28 C29 -172.1(9) . . . . ?
O4 C28 C29 C34 142.3(11) . . . . ?
N2 C28 C29 C34 -40.8(15) . . . . ?
O4 C28 C29 C30 -40.7(16) . . . . ?
N2 C28 C29 C30 136.2(11) . . . . ?
C34 C29 C30 C31 -1.4(17) . . . . ?
C28 C29 C30 C31 -178.5(11) . . . . ?
C29 C30 C31 C32 1(2) . . . . ?
C30 C31 C32 C33 -1(2) . . . . ?
C30 C31 C32 Br2 -179.8(10) . . . . ?
C31 C32 C33 C34 2.8(19) . . . . ?
Br2 C32 C33 C34 -178.7(9) . . . . ?
C30 C29 C34 C33 3.0(17) . . . . ?
C28 C29 C34 C33 179.9(11) . . . . ?
C32 C33 C34 C29 -3.7(18) . . . . ?
C45 N3 C35 C41 -59.3(14) . . . . ?
C45 N3 C35 C36 177.1(9) . . . . ?
C45 N3 C35 C38 64.4(13) . . . . ?
C37 O5 C36 C35 24.9(12) . . . . ?
C37 O5 C36 C42 153.0(11) . . . . ?
N3 C35 C36 O5 -155.0(9) . . . . ?
C41 C35 C36 O5 83.3(12) . . . . ?
C38 C35 C36 O5 -35.1(10) . . . . ?
N3 C35 C36 C42 85.2(13) . . . . ?
C41 C35 C36 C42 -36.5(16) . . . . ?
C38 C35 C36 C42 -154.9(11) . . . . ?
C36 O5 C37 C38 -3.8(14) . . . . ?
O5 C37 C38 C39 107.4(11) . . . . ?
O5 C37 C38 C35 -18.6(12) . . . . ?
N3 C35 C38 C37 149.2(10) . . . . ?
C41 C35 C38 C37 -87.8(12) . . . . ?
C36 C35 C38 C37 32.2(10) . . . . ?
N3 C35 C38 C39 27.3(14) . . . . ?
C41 C35 C38 C39 150.3(11) . . . . ?
C36 C35 C38 C39 -89.7(11) . . . . ?
C37 C38 C39 C40 66.1(13) . . . . ?
C35 C38 C39 C40 -176.7(11) . . . . ?
O5 C36 C42 C44 -177.9(13) . . . . ?
C35 C36 C42 C44 -59.9(17) . . . . ?
O5 C36 C42 C43 59.0(14) . . . . ?
C35 C36 C42 C43 177.1(12) . . . . ?
C35 N3 C45 O6 -5.6(16) . . . . ?
C35 N3 C45 C46 175.7(9) . . . . ?
O6 C45 C46 C47 138.1(11) . . . . ?
N3 C45 C46 C47 -43.2(14) . . . . ?
O6 C45 C46 C51 -39.3(14) . . . . ?
N3 C45 C46 C51 139.4(10) . . . . ?
C51 C46 C47 C48 -3.4(16) . . . . ?
C45 C46 C47 C48 179.3(10) . . . . ?
C46 C47 C48 C49 1.7(16) . . . . ?
C47 C48 C49 C50 -0.2(17) . . . . ?
C47 C48 C49 Br3 -178.6(8) . . . . ?
C48 C49 C50 C51 0.5(18) . . . . ?
Br3 C49 C50 C51 178.8(9) . . . . ?
C49 C50 C51 C46 -2.3(18) . . . . ?
C47 C46 C51 C50 3.7(17) . . . . ?
C45 C46 C51 C50 -178.9(10) . . . . ?
C62 N4 C52 C53 49.3(16) . . . . ?
C62 N4 C52 C55 -67.9(16) . . . . ?
C62 N4 C52 C58 174.0(12) . . . . ?
C54 O7 C53 C59 166.6(16) . . . . ?
C54 O7 C53 C52 37.0(18) . . . . ?
N4 C52 C53 O7 -138.7(12) . . . . ?
C55 C52 C53 O7 -17.4(14) . . . . ?
C58 C52 C53 O7 101.7(13) . . . . ?
N4 C52 C53 C59 98.5(15) . . . . ?
C55 C52 C53 C59 -140.2(15) . . . . ?
C58 C52 C53 C59 -21.1(19) . . . . ?
C53 O7 C54 C55 -44(2) . . . . ?
O7 C54 C55 C56 162.0(15) . . . . ?
O7 C54 C55 C52 31.5(19) . . . . ?
N4 C52 C55 C54 112.9(14) . . . . ?
C53 C52 C55 C54 -8.4(15) . . . . ?
C58 C52 C55 C54 -131.1(14) . . . . ?
N4 C52 C55 C56 -17.7(19) . . . . ?
C53 C52 C55 C56 -139.0(15) . . . . ?
C58 C52 C55 C56 98.3(16) . . . . ?
C54 C55 C56 C57 75(2) . . . . ?
C52 C55 C56 C57 -161.4(18) . . . . ?
O7 C53 C59 C61 170.8(18) . . . . ?
C52 C53 C59 C61 -69(2) . . . . ?
O7 C53 C59 C60 46.6(18) . . . . ?
C52 C53 C59 C60 167.3(14) . . . . ?
C52 N4 C62 O8 1.7(19) . . . . ?
C52 N4 C62 C63 -177.1(11) . . . . ?
O8 C62 C63 C64 -137.6(11) . . . . ?
N4 C62 C63 C64 41.2(14) . . . . ?
O8 C62 C63 C68 41.2(15) . . . . ?
N4 C62 C63 C68 -140.0(10) . . . . ?
C68 C63 C64 C65 -0.9(15) . . . . ?
C62 C63 C64 C65 177.9(10) . . . . ?
C63 C64 C65 C66 2.8(18) . . . . ?
C64 C65 C66 C67 -3(2) . . . . ?
C64 C65 C66 Br4 177.7(9) . . . . ?
C65 C66 C67 C68 1(2) . . . . ?
Br4 C66 C67 C68 -179.7(9) . . . . ?
C66 C67 C68 C63 1.3(18) . . . . ?
C64 C63 C68 C67 -1.1(16) . . . . ?
C62 C63 C68 C67 -180.0(10) . . . . ?
C79 N5 C69 C75 -62.3(13) . . . . ?
C79 N5 C69 C70 172.9(9) . . . . ?
C79 N5 C69 C72 61.0(12) . . . . ?
C71 O9 C70 C76 143.9(10) . . . . ?
C71 O9 C70 C69 17.7(12) . . . . ?
N5 C69 C70 O9 -154.3(8) . . . . ?
C75 C69 C70 O9 82.1(11) . . . . ?
C72 C69 C70 O9 -34.9(9) . . . . ?
N5 C69 C70 C76 86.8(11) . . . . ?
C75 C69 C70 C76 -36.8(13) . . . . ?
C72 C69 C70 C76 -153.8(10) . . . . ?
C70 O9 C71 C72 7.8(14) . . . . ?
O9 C71 C72 C73 92.5(13) . . . . ?
O9 C71 C72 C69 -29.4(13) . . . . ?
N5 C69 C72 C71 155.8(9) . . . . ?
C75 C69 C72 C71 -80.8(11) . . . . ?
C70 C69 C72 C71 37.8(10) . . . . ?
N5 C69 C72 C73 35.6(12) . . . . ?
C75 C69 C72 C73 159.1(9) . . . . ?
C70 C69 C72 C73 -82.3(10) . . . . ?
C71 C72 C73 C74 75.4(15) . . . . ?
C69 C72 C73 C74 -171.3(11) . . . . ?
O9 C70 C76 C78 179.5(9) . . . . ?
C69 C70 C76 C78 -63.2(13) . . . . ?
O9 C70 C76 C77 56.6(12) . . . . ?
C69 C70 C76 C77 173.9(9) . . . . ?
C69 N5 C79 O10 -3.9(17) . . . . ?
C69 N5 C79 C80 175.7(9) . . . . ?
O10 C79 C80 C85 -39.2(15) . . . . ?
N5 C79 C80 C85 141.2(11) . . . . ?
O10 C79 C80 C81 136.6(12) . . . . ?
N5 C79 C80 C81 -43.1(14) . . . . ?
C85 C80 C81 C82 0.6(17) . . . . ?
C79 C80 C81 C82 -175.2(10) . . . . ?
C80 C81 C82 C83 -1.0(18) . . . . ?
C81 C82 C83 C84 0(2) . . . . ?
C81 C82 C83 Br5 -178.4(9) . . . . ?
C82 C83 C84 C85 2(2) . . . . ?
Br5 C83 C84 C85 179.8(9) . . . . ?
C81 C80 C85 C84 1.0(17) . . . . ?
C79 C80 C85 C84 176.9(10) . . . . ?
C83 C84 C85 C80 -2.1(19) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O10 0.86 2.39 3.126(11) 143.5 3_656
N2 H2A O8 0.86 2.39 3.187(10) 154.5 .
N3 H3D O2 0.86 2.17 3.009(11) 164.3 4_466
N4 H4A O6 0.86 2.26 2.936(11) 135.7 1_655
N5 H5D O4 0.86 2.22 3.033(11) 158.0 1_445
C7 H7C O2 0.96 2.34 2.951(14) 121.2 .
C24 H24C O4 0.96 2.45 3.019(13) 117.7 .
C53 H53 O8 0.98 2.36 3.073(14) 128.5 .
C54 H54A Br4 0.97 3.00 3.801(18) 140.4 3_745
C65 H65 O5 0.93 2.58 3.473(16) 161.7 .
C75 H75A Br3 0.96 3.10 3.861(12) 137.0 2_465
C75 H75C O10 0.96 2.50 3.076(14) 118.8 .

_refine_diff_density_max         0.360
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.049

_shelxl_version_number           2013-4



