# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_acetone_BrC2
_database_code_depnum_ccdc_archive 'CCDC 1551401'
_audit_update_record             
;
2017-05-22 deposited with the CCDC.
2017-06-15 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT431_acetone_BrC2        
;
PROBLEM: Short Inter HL..A  Contact Br2    ..  O4      ..       2.94 Ang.  
RESPONSE: Halogen bond
;
# end Validation Reply Form
_audit_creation_date             2017-05-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C36 H36 Br4 O8, C3 H6 O, 0.25(C8 H12 O4)'
_chemical_formula_sum            'C41 H45 Br4 O10'
_chemical_formula_weight         1017.41
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N1 O9 Br4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           59
_space_group_name_H-M_alt        'P m m n'
_space_group_name_Hall           '-P 2ab 2a'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z'
'x+1/2, -y, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z'
'-x-1/2, y, z'

_cell_length_a                   16.2181(9)
_cell_length_b                   16.1822(8)
_cell_length_c                   7.9215(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2078.96(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3516
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      75.8570
_cell_measurement_theta_min      3.8400
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.191
_exptl_absorpt_correction_T_max  0.941
_exptl_absorpt_correction_T_min  0.803
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.625
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1022
_exptl_crystal_size_max          0.1601
_exptl_crystal_size_mid          0.0413
_exptl_crystal_size_min          0.0259
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0646
_diffrn_reflns_av_unetI/netI     0.0488
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            9568
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        66.742
_diffrn_reflns_theta_max         66.742
_diffrn_reflns_theta_min         5.585
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -57.00   32.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8676   57.0000    0.0000 89

#__ type_ start__ end____ width___ exp.time_
  2 omega -116.00  -10.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8676  -77.0000 -120.0000 106

#__ type_ start__ end____ width___ exp.time_
  3 omega   24.00   95.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8676 -125.0000   90.0000 71

#__ type_ start__ end____ width___ exp.time_
  4 omega  -31.00   69.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8676  -57.0000   90.0000 100

#__ type_ start__ end____ width___ exp.time_
  5 omega   41.00   94.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000   90.0000 53

#__ type_ start__ end____ width___ exp.time_
  6 omega   36.00   91.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -60.0000 55

#__ type_ start__ end____ width___ exp.time_
  7 omega   43.00   75.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -126.0000  -41.0000 32

#__ type_ start__ end____ width___ exp.time_
  8 omega   86.00  175.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000 -150.0000 89

#__ type_ start__ end____ width___ exp.time_
  9 omega   49.00  114.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  120.0000 65

#__ type_ start__ end____ width___ exp.time_
 10 omega   38.00   91.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000   30.0000 53

#__ type_ start__ end____ width___ exp.time_
 11 omega   31.00  164.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -15.0000 -180.0000 133

#__ type_ start__ end____ width___ exp.time_
 12 omega   39.00   98.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000 -180.0000 59

#__ type_ start__ end____ width___ exp.time_
 13 omega   36.00   58.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000  -60.0000 22
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0945187000
_diffrn_orient_matrix_UB_12      0.0006706000
_diffrn_orient_matrix_UB_13      0.0180418000
_diffrn_orient_matrix_UB_21      0.0056794000
_diffrn_orient_matrix_UB_22      -0.0672065000
_diffrn_orient_matrix_UB_23      0.1371111000
_diffrn_orient_matrix_UB_31      0.0065283000
_diffrn_orient_matrix_UB_32      0.0674594000
_diffrn_orient_matrix_UB_33      0.1368834000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1706
_reflns_number_total             1981
_reflns_odcompleteness_completeness 99.54
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.657
_refine_diff_density_min         -0.669
_refine_diff_density_rms         0.114
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     153
_refine_ls_number_reflns         1981
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0408
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0610P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1006
_refine_ls_wR_factor_ref         0.1057
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C12) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Others
 Fixed Sof: H15A(0.5) H15B(0.5) H15C(0.5) C12(0.25) H12C(0.25) H12A(0.25)
 H12B(0.25)
4.a Riding coordinates:
 O1(H1)
4.b Ternary CH refined with riding coordinates:
 C5(H5)
4.c Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
4.d Aromatic/amide H refined with riding coordinates:
 C1(H1A), C6(H6)
4.e Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C15(H15A,H15B,H15C), C12(H12C,H12A,H12B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.45556(3) 0.7500 1.12381(7) 0.02326(18) Uani 1 2 d S T P . .
Br2 Br 0.7500 0.37700(3) 1.00448(7) 0.02457(19) Uani 1 2 d S T P . .
O1 O 0.60049(17) 0.46583(16) 0.8375(4) 0.0245(6) Uani 1 1 d . . . . .
H1 H 0.5916 0.4380 0.9265 0.029 Uiso 1 1 d R . . . .
O2 O 0.50791(17) 0.60512(18) 0.9224(3) 0.0230(6) Uani 1 1 d . . . . .
H2 H 0.528(3) 0.568(3) 0.889(6) 0.018(12) Uiso 1 1 d . . . . .
C1 C 0.5896(3) 0.7500 0.6081(6) 0.0180(10) Uani 1 2 d S T P . .
H1A H 0.6173 0.7500 0.5052 0.022 Uiso 1 2 calc RS T P . .
C2 C 0.5702(2) 0.6740(2) 0.6806(4) 0.0172(7) Uani 1 1 d . . . . .
C3 C 0.5299(2) 0.6745(2) 0.8372(4) 0.0175(7) Uani 1 1 d . . . . .
C4 C 0.5100(3) 0.7500 0.9112(6) 0.0177(10) Uani 1 2 d S T P . .
C5 C 0.5936(2) 0.5923(2) 0.5970(4) 0.0176(7) Uani 1 1 d . . . . .
H5 H 0.5509 0.5523 0.6281 0.021 Uiso 1 1 calc R . . . .
C6 C 0.7500 0.5910(3) 0.6127(6) 0.0156(9) Uani 1 2 d S T P . .
H6 H 0.7500 0.6346 0.5363 0.019 Uiso 1 2 calc RS T P . .
C7 C 0.6744(2) 0.5596(2) 0.6674(4) 0.0174(7) Uani 1 1 d . . . . .
C8 C 0.6754(2) 0.4955(2) 0.7844(5) 0.0197(7) Uani 1 1 d . . . . .
C9 C 0.7500 0.4639(3) 0.8421(7) 0.0201(10) Uani 1 2 d S T P . .
C10 C 0.5946(2) 0.5964(2) 0.4032(5) 0.0219(8) Uani 1 1 d . . . . .
H10A H 0.5403 0.6125 0.3637 0.026 Uiso 1 1 calc R . . . .
H10B H 0.6334 0.6386 0.3679 0.026 Uiso 1 1 calc R . . . .
C11 C 0.6183(2) 0.5146(3) 0.3211(5) 0.0283(9) Uani 1 1 d . . . . .
H11A H 0.6105 0.5184 0.2012 0.043 Uiso 1 1 calc GR . . . .
H11B H 0.5844 0.4712 0.3656 0.043 Uiso 1 1 calc GR . . . .
H11C H 0.6752 0.5028 0.3447 0.043 Uiso 1 1 calc GR . . . .
O3 O 0.7500 0.7500 0.2953(7) 0.0263(12) Uani 1 4 d S T P . .
C14 C 0.7500 0.7500 0.1411(10) 0.0281(17) Uani 1 4 d S T P . .
C15 C 0.7500 0.6717(6) 0.0453(10) 0.059(2) Uani 1 2 d S T P . .
H15A H 0.7861 0.6767 -0.0502 0.088 Uiso 0.5 1 calc GR . . A -1
H15B H 0.6951 0.6599 0.0070 0.088 Uiso 0.5 1 calc GR . . A -1
H15C H 0.7688 0.6277 0.1169 0.088 Uiso 0.5 1 calc GR . . A -1
O4 O 0.7500 0.2500 1.2701(9) 0.071(3) Uani 1 4 d S T P . .
C12 C 0.8289(17) 0.2500 1.512(3) 0.110(9) Uani 0.5 2 d S TU P . .
H12C H 0.8525 0.1956 1.5093 0.165 Uiso 0.25 1 calc GR . . B -1
H12A H 0.8186 0.2660 1.6263 0.165 Uiso 0.25 1 calc GR . . B -1
H12B H 0.8666 0.2884 1.4608 0.165 Uiso 0.25 1 calc GR . . B -1
C13 C 0.7500 0.2500 1.4157(14) 0.066(4) Uani 1 4 d S T P . .


_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 C4 1.901(5) . ?
Br2 C9 1.906(5) . ?
O1 H1 0.8485 . ?
O1 C8 1.372(4) . ?
O2 H2 0.73(5) . ?
O2 C3 1.358(5) . ?
C1 H1A 0.9300 . ?
C1 C2 1.393(4) 7_575 ?
C1 C2 1.393(4) . ?
C2 C3 1.402(5) . ?
C2 C5 1.527(5) . ?
C3 C4 1.393(4) . ?
C4 C3 1.393(4) 7_575 ?
C5 H5 0.9800 . ?
C5 C7 1.520(5) . ?
C5 C10 1.536(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.395(4) 8_755 ?
C6 C7 1.395(4) . ?
C7 C8 1.392(5) . ?
C8 C9 1.391(5) . ?
C9 C8 1.391(5) 8_755 ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.524(5) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
O3 C14 1.222(10) . ?
C14 C15 1.477(9) . ?
C14 C15 1.477(9) 2_665 ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
O4 C13 1.154(14) . ?
C12 H12C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 C13 1.49(2) . ?
C13 C12 1.49(2) 2_655 ?

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
C8 O1 H1 126.2 . . ?
C3 O2 H2 113(4) . . ?
C2 C1 H1A 118.1 7_575 . ?
C2 C1 H1A 118.1 . . ?
C2 C1 C2 123.9(5) 7_575 . ?
C1 C2 C3 117.8(3) . . ?
C1 C2 C5 121.9(3) . . ?
C3 C2 C5 120.3(3) . . ?
O2 C3 C2 123.9(3) . . ?
O2 C3 C4 117.1(3) . . ?
C4 C3 C2 119.0(3) . . ?
C3 C4 Br1 118.7(2) . . ?
C3 C4 Br1 118.7(2) 7_575 . ?
C3 C4 C3 122.6(4) . 7_575 ?
C2 C5 H5 106.7 . . ?
C2 C5 C10 113.5(3) . . ?
C7 C5 C2 110.9(3) . . ?
C7 C5 H5 106.7 . . ?
C7 C5 C10 111.9(3) . . ?
C10 C5 H5 106.7 . . ?
C7 C6 H6 118.6 . . ?
C7 C6 H6 118.6 8_755 . ?
C7 C6 C7 122.9(5) 8_755 . ?
C6 C7 C5 121.1(3) . . ?
C8 C7 C5 120.9(3) . . ?
C8 C7 C6 117.9(3) . . ?
O1 C8 C7 117.1(3) . . ?
O1 C8 C9 122.8(3) . . ?
C9 C8 C7 120.2(3) . . ?
C8 C9 Br2 119.5(2) . . ?
C8 C9 Br2 119.5(2) 8_755 . ?
C8 C9 C8 120.9(5) 8_755 . ?
C5 C10 H10A 109.0 . . ?
C5 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C11 C10 C5 113.1(3) . . ?
C11 C10 H10A 109.0 . . ?
C11 C10 H10B 109.0 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O3 C14 C15 120.9(5) . . ?
O3 C14 C15 120.9(5) . 2_665 ?
C15 C14 C15 118.2(10) . 2_665 ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
H12C C12 H12A 109.5 . . ?
H12C C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C13 C12 H12C 109.5 . . ?
C13 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
O4 C13 C12 120.7(13) . 2_655 ?
O4 C13 C12 120.7(13) . . ?
C12 C13 C12 119(3) . 2_655 ?

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
O1 C8 C9 Br2 -1.0(6) . . . . ?
O1 C8 C9 C8 179.7(3) . . . 8_755 ?
O2 C3 C4 Br1 0.8(5) . . . . ?
O2 C3 C4 C3 179.4(3) . . . 7_575 ?
C1 C2 C3 O2 -179.6(4) . . . . ?
C1 C2 C3 C4 1.2(5) . . . . ?
C1 C2 C5 C7 95.4(4) . . . . ?
C1 C2 C5 C10 -31.6(5) . . . . ?
C2 C1 C2 C3 -1.2(7) 7_575 . . . ?
C2 C1 C2 C5 -179.4(3) 7_575 . . . ?
C2 C3 C4 Br1 -179.9(3) . . . . ?
C2 C3 C4 C3 -1.4(7) . . . 7_575 ?
C2 C5 C7 C6 -79.5(4) . . . . ?
C2 C5 C7 C8 102.7(4) . . . . ?
C2 C5 C10 C11 179.8(3) . . . . ?
C3 C2 C5 C7 -82.8(4) . . . . ?
C3 C2 C5 C10 150.3(3) . . . . ?
C5 C2 C3 O2 -1.3(5) . . . . ?
C5 C2 C3 C4 179.4(3) . . . . ?
C5 C7 C8 O1 -2.6(5) . . . . ?
C5 C7 C8 C9 177.2(4) . . . . ?
C6 C7 C8 O1 179.6(3) . . . . ?
C6 C7 C8 C9 -0.6(6) . . . . ?
C7 C5 C10 C11 53.4(4) . . . . ?
C7 C6 C7 C5 -176.5(3) 8_755 . . . ?
C7 C6 C7 C8 1.3(7) 8_755 . . . ?
C7 C8 C9 Br2 179.2(3) . . . . ?
C7 C8 C9 C8 -0.1(7) . . . 8_755 ?
C10 C5 C7 C6 48.3(5) . . . . ?
C10 C5 C7 C8 -129.4(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
3 10 -1 0.0164 3.0000 9.9934 -1.0047 -0.2950 -0.7923 0.5562
-9 5 0 0.0119 -9.0064 4.9808 -0.0010 0.8546 -0.3860 0.2771
10 -4 0 0.0235 10.0073 -3.9804 0.0007 -0.9485 0.3244 -0.2031
-3 -10 1 0.0096 -3.0000 -9.9934 1.0047 0.2950 0.7923 -0.5562
1 -1 -5 0.0847 0.9845 -0.9962 -5.0076 -0.1841 -0.6141 -0.7462
-1 1 5 0.0626 -0.9845 0.9962 5.0076 0.1841 0.6141 0.7462

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_2_BrC2
_database_code_depnum_ccdc_archive 'CCDC 1551403'
_audit_update_record             
;
2017-05-22 deposited with the CCDC.
2017-06-15 downloaded from the CCDC.
;
_audit_creation_date             2017-05-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C36 H36 Br4 O8, 2(C6 H7 N O), C3 H6 O'
_chemical_formula_sum            'C51 H56 Br4 N2 O11'
_chemical_formula_weight         1192.61
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C5 H5 N1 O3 Br1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   13.8485(6)
_cell_length_b                   13.9210(4)
_cell_length_c                   14.3337(4)
_cell_angle_alpha                90.848(2)
_cell_angle_beta                 115.869(4)
_cell_angle_gamma                90.012(3)
_cell_volume                     2486.07(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9561
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      73.2450
_cell_measurement_theta_min      3.3870
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.466
_exptl_absorpt_correction_T_max  0.744
_exptl_absorpt_correction_T_min  0.547
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1208
_exptl_crystal_size_max          0.1148
_exptl_crystal_size_mid          0.0906
_exptl_crystal_size_min          0.0545
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16207
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        66.749
_diffrn_reflns_theta_max         66.749
_diffrn_reflns_theta_min         3.427
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -45.00  -19.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676   37.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega   -8.00   25.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676   37.0000  -60.0000 33

#__ type_ start__ end____ width___ exp.time_
  3 omega  -44.00   26.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676   37.0000 -180.0000 70

#__ type_ start__ end____ width___ exp.time_
  4 omega  -95.00  -13.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676  125.0000 -120.0000 82

#__ type_ start__ end____ width___ exp.time_
  5 omega   61.00   98.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -45.0000  120.0000 37

#__ type_ start__ end____ width___ exp.time_
  6 omega   32.00  109.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -94.0000   90.0000 77

#__ type_ start__ end____ width___ exp.time_
  7 omega   40.00   89.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -30.0000  -90.0000 49

#__ type_ start__ end____ width___ exp.time_
  8 omega   89.00  147.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154   45.0000 -180.0000 58

#__ type_ start__ end____ width___ exp.time_
  9 omega   85.00  163.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154   77.0000 -150.0000 78

#__ type_ start__ end____ width___ exp.time_
 10 omega  104.00  175.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  125.0000  150.0000 71

#__ type_ start__ end____ width___ exp.time_
 11 omega  -47.00    5.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6176   37.0000  120.0000 52

#__ type_ start__ end____ width___ exp.time_
 12 omega  -45.00   24.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6176   37.0000   60.0000 69

#__ type_ start__ end____ width___ exp.time_
 13 omega   33.00   83.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -45.0000   90.0000 50

#__ type_ start__ end____ width___ exp.time_
 14 omega   26.00  107.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -94.0000  -30.0000 81

#__ type_ start__ end____ width___ exp.time_
 15 omega   36.00   62.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154 -125.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 16 omega   71.00  118.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154 -125.0000 -120.0000 47

#__ type_ start__ end____ width___ exp.time_
 17 omega   95.00  177.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  125.0000   30.0000 82

#__ type_ start__ end____ width___ exp.time_
 18 omega   80.00  146.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154   77.0000   90.0000 66

#__ type_ start__ end____ width___ exp.time_
 19 omega   13.00   99.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6176   57.0000  150.0000 86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0048314000
_diffrn_orient_matrix_UB_12      -0.0906534000
_diffrn_orient_matrix_UB_13      -0.0648989000
_diffrn_orient_matrix_UB_21      0.1144811000
_diffrn_orient_matrix_UB_22      0.0213226000
_diffrn_orient_matrix_UB_23      0.0132289000
_diffrn_orient_matrix_UB_31      0.0464409000
_diffrn_orient_matrix_UB_32      -0.0598101000
_diffrn_orient_matrix_UB_33      0.0994228000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7754
_reflns_number_total             8742
_reflns_odcompleteness_completeness 99.13
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.802
_refine_diff_density_min         -0.568
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     641
_refine_ls_number_reflns         8742
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0381
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0326P)²+3.1574P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0931
_refine_ls_wR_factor_ref         0.0966
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O7-H7
 0.85 with sigma of 0.02
 H5-O5
 0.85 with sigma of 0.02
 H3-O3
 0.85 with sigma of 0.02
 O1-H1
 0.85 with sigma of 0.02
 O6-H6
 0.85 with sigma of 0.02
 O4-H4
 0.85 with sigma of 0.02
 H2-O2
 0.85 with sigma of 0.02
 H8-O8
 0.85 with sigma of 0.02
3.a Riding coordinates:
 O8(H8), O4(H4), O6(H6), O2(H2)
3.b Ternary CH refined with riding coordinates:
 C7(H7A), C25(H25), C34(H34), C16(H16)
3.c Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C8(H8A,H8B), C35(H35A,H35B), C26(H26A,H26B)
3.d Aromatic/amide H refined with riding coordinates:
 C15(H15), C33(H33), C24(H24), C42(H42), C46(H46), C40(H40), C49(H49), C6(H6A),
  C43(H43), C48(H48), C41(H41), C47(H47)
3.e Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C27(H27A,H27B,H27C), C18(H18A,H18B,H18C), C36(H36A,H36B,
 H36C), C39(H39A,H39B,H39C), C51(H51A,H51B,H51C), C37(H37A,H37B,H37C), C45(H45A,
 H45B,H45C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br4 Br 0.10467(3) 1.07579(2) 0.40257(3) 0.02408(9) Uani 1 1 d . . . . .
Br3 Br 0.12896(3) 0.56342(3) 0.26633(3) 0.02408(9) Uani 1 1 d . . . . .
Br2 Br 0.13619(3) 0.41026(3) 0.76154(3) 0.02676(10) Uani 1 1 d . . . . .
Br1 Br 0.11087(3) 0.91012(3) 0.91678(3) 0.03444(11) Uani 1 1 d . . . . .
O8 O 0.2268(2) 1.09284(17) 0.64340(17) 0.0231(5) Uani 1 1 d D . . . .
H8 H 0.1963 1.1435 0.6193 0.041(13) Uiso 1 1 d DR . . . .
O3 O 0.2527(2) 0.55287(18) 0.92645(19) 0.0262(5) Uani 1 1 d D . . . .
O4 O 0.2739(2) 0.39499(17) 0.63889(17) 0.0239(5) Uani 1 1 d D . . . .
H4 H 0.2302 0.3496 0.6186 0.061(17) Uiso 1 1 d DR . . . .
O7 O 0.2362(2) 0.94036(17) 0.34708(17) 0.0223(5) Uani 1 1 d D . . . .
O6 O 0.2525(2) 0.75654(16) 0.30339(17) 0.0256(5) Uani 1 1 d D . . . .
H6 H 0.2173 0.7534 0.2382 0.09(2) Uiso 1 1 d DR . . . .
O5 O 0.2551(2) 0.45415(17) 0.45623(17) 0.0235(5) Uani 1 1 d D . . . .
O1 O 0.2140(2) 1.02924(18) 0.8141(2) 0.0281(5) Uani 1 1 d D . . . .
O2 O 0.2615(2) 0.73463(16) 0.99537(19) 0.0248(5) Uani 1 1 d D . . . .
H2 H 0.2255 0.7382 1.0316 0.12(3) Uiso 1 1 d DR . . . .
O9 O -0.13574(18) 0.74435(16) 0.42570(18) 0.0231(5) Uani 1 1 d . . . . .
O10 O 0.1566(2) 0.74336(18) 0.10528(17) 0.0262(5) Uani 1 1 d . . . . .
N2 N 0.0524(2) 0.7430(2) 0.0775(2) 0.0270(6) Uani 1 1 d . . . . .
C10 C 0.3917(3) 0.6033(2) 0.8762(2) 0.0164(6) Uani 1 1 d . . . . .
O11 O 0.6557(2) 0.7698(2) 0.7995(2) 0.0359(6) Uani 1 1 d . . . . .
C3 C 0.2381(3) 0.8834(2) 0.9023(3) 0.0219(7) Uani 1 1 d . . . . .
C7 C 0.4382(3) 0.6782(2) 0.9630(2) 0.0174(6) Uani 1 1 d . . . . .
H7A H 0.4204 0.6571 1.0185 0.021 Uiso 1 1 calc R . . . .
N1 N -0.0358(2) 0.73095(19) 0.4976(2) 0.0213(6) Uani 1 1 d . . . . .
C28 C 0.3728(3) 0.9001(2) 0.5186(2) 0.0159(6) Uani 1 1 d . . . . .
C9 C 0.6063(3) 0.7492(3) 1.1067(3) 0.0286(8) Uani 1 1 d . . . . .
H9A H 0.5828 0.8140 1.0884 0.043 Uiso 1 1 calc GR . . . .
H9B H 0.6833 0.7473 1.1374 0.043 Uiso 1 1 calc GR . . . .
H9C H 0.5814 0.7265 1.1554 0.043 Uiso 1 1 calc GR . . . .
C17 C 0.5672(3) 0.5163(2) 0.7014(2) 0.0196(6) Uani 1 1 d . . . . .
H17A H 0.5941 0.5101 0.6494 0.024 Uiso 1 1 calc R . . . .
H17B H 0.5877 0.5794 0.7338 0.024 Uiso 1 1 calc R . . . .
C50 C -0.0093(3) 0.6745(3) 0.0130(3) 0.0346(9) Uani 1 1 d . . . . .
C25 C 0.4273(3) 0.8293(2) 0.4741(2) 0.0162(6) Uani 1 1 d . . . . .
H25 H 0.4040 0.8467 0.4015 0.019 Uiso 1 1 calc R . . . .
C27 C 0.6002(3) 0.7750(3) 0.4705(3) 0.0252(7) Uani 1 1 d . . . . .
H27A H 0.5705 0.7918 0.3987 0.038 Uiso 1 1 calc GR . . . .
H27B H 0.5851 0.7086 0.4761 0.038 Uiso 1 1 calc GR . . . .
H27C H 0.6765 0.7852 0.5018 0.038 Uiso 1 1 calc GR . . . .
C29 C 0.2811(3) 0.9494(2) 0.4527(2) 0.0170(6) Uani 1 1 d . . . . .
C23 C 0.3856(3) 0.7285(2) 0.4723(2) 0.0158(6) Uani 1 1 d . . . . .
C30 C 0.2323(3) 1.0135(2) 0.4948(2) 0.0183(6) Uani 1 1 d . . . . .
C22 C 0.2970(3) 0.6953(2) 0.3840(2) 0.0171(6) Uani 1 1 d . . . . .
C15 C 0.4337(3) 0.5894(2) 0.8045(2) 0.0170(6) Uani 1 1 d . . . . .
H15 H 0.4907 0.6283 0.8102 0.020 Uiso 1 1 calc R . . . .
C8 C 0.5608(3) 0.6852(2) 1.0096(2) 0.0199(6) Uani 1 1 d . . . . .
H8A H 0.5909 0.6214 1.0270 0.024 Uiso 1 1 calc R . . . .
H8B H 0.5816 0.7110 0.9585 0.024 Uiso 1 1 calc R . . . .
C11 C 0.3028(3) 0.5465(2) 0.8632(2) 0.0185(6) Uani 1 1 d . . . . .
C21 C 0.2545(2) 0.6043(2) 0.3833(2) 0.0183(6) Uani 1 1 d . . . . .
C1 C 0.3649(3) 0.9266(2) 0.8357(2) 0.0167(6) Uani 1 1 d . . . . .
C5 C 0.3820(3) 0.7746(2) 0.9258(2) 0.0171(6) Uani 1 1 d . . . . .
C33 C 0.4110(3) 0.9163(2) 0.6252(2) 0.0172(6) Uani 1 1 d . . . . .
H33 H 0.4706 0.8821 0.6697 0.021 Uiso 1 1 calc R . . . .
C18 C 0.6183(3) 0.4394(3) 0.7834(3) 0.0286(8) Uani 1 1 d . . . . .
H18A H 0.5947 0.3770 0.7524 0.043 Uiso 1 1 calc GR . . . .
H18B H 0.5973 0.4493 0.8384 0.043 Uiso 1 1 calc GR . . . .
H18C H 0.6950 0.4438 0.8109 0.043 Uiso 1 1 calc GR . . . .
C36 C 0.5787(3) 1.0846(3) 0.8004(3) 0.0261(7) Uani 1 1 d . . . . .
H36A H 0.5599 1.0735 0.7282 0.039 Uiso 1 1 calc GR . . . .
H36B H 0.6554 1.0862 0.8389 0.039 Uiso 1 1 calc GR . . . .
H36C H 0.5497 1.1449 0.8090 0.039 Uiso 1 1 calc GR . . . .
C24 C 0.4299(2) 0.6668(2) 0.5570(2) 0.0163(6) Uani 1 1 d . . . . .
H24 H 0.4881 0.6887 0.6167 0.020 Uiso 1 1 calc R . . . .
C35 C 0.5328(3) 1.0038(2) 0.8401(2) 0.0197(6) Uani 1 1 d . . . . .
H35A H 0.5558 1.0133 0.9139 0.024 Uiso 1 1 calc R . . . .
H35B H 0.5614 0.9430 0.8300 0.024 Uiso 1 1 calc R . . . .
C19 C 0.3908(3) 0.5739(2) 0.5559(2) 0.0155(6) Uani 1 1 d . . . . .
C42 C 0.1669(3) 0.7052(3) 0.6507(3) 0.0430(10) Uani 1 1 d . . . . .
H42 H 0.2360 0.6971 0.7028 0.052 Uiso 1 1 calc R . . . .
C32 C 0.3646(3) 0.9807(2) 0.6679(2) 0.0171(6) Uani 1 1 d . . . . .
C39 C 0.7901(4) 0.8892(3) 0.8321(3) 0.0399(10) Uani 1 1 d . . . . .
H39A H 0.7609 0.9178 0.8755 0.060 Uiso 1 1 calc GR . . . .
H39B H 0.7780 0.9308 0.7752 0.060 Uiso 1 1 calc GR . . . .
H39C H 0.8658 0.8799 0.8718 0.060 Uiso 1 1 calc GR . . . .
C26 C 0.5504(3) 0.8374(2) 0.5260(2) 0.0199(6) Uani 1 1 d . . . . .
H26A H 0.5713 0.9038 0.5257 0.024 Uiso 1 1 calc R . . . .
H26B H 0.5777 0.8179 0.5976 0.024 Uiso 1 1 calc R . . . .
C34 C 0.4092(3) 0.9989(2) 0.7850(2) 0.0171(6) Uani 1 1 d . . . . .
H34 H 0.3834 1.0622 0.7943 0.020 Uiso 1 1 calc R . . . .
C12 C 0.2622(3) 0.4785(2) 0.7831(2) 0.0188(6) Uani 1 1 d . . . . .
C31 C 0.2733(3) 1.0309(2) 0.6003(2) 0.0182(6) Uani 1 1 d . . . . .
C46 C 0.0138(4) 0.8139(3) 0.1207(3) 0.0400(10) Uani 1 1 d . . . . .
H46 H 0.0594 0.8617 0.1632 0.048 Uiso 1 1 calc R . . . .
C14 C 0.3952(2) 0.5209(2) 0.7250(2) 0.0149(6) Uani 1 1 d . . . . .
C51 C 0.0411(4) 0.6093(3) -0.0336(3) 0.0422(10) Uani 1 1 d . . . . .
H51A H 0.0649 0.6451 -0.0765 0.063 Uiso 1 1 calc GR . . . .
H51B H -0.0100 0.5613 -0.0750 0.063 Uiso 1 1 calc GR . . . .
H51C H 0.1014 0.5788 0.0202 0.063 Uiso 1 1 calc GR . . . .
C40 C -0.0212(3) 0.6828(3) 0.5846(3) 0.0286(8) Uani 1 1 d . . . . .
H40 H -0.0804 0.6587 0.5916 0.034 Uiso 1 1 calc R . . . .
C13 C 0.3089(3) 0.4632(2) 0.7157(2) 0.0175(6) Uani 1 1 d . . . . .
C49 C -0.1179(4) 0.6726(4) -0.0072(3) 0.0437(10) Uani 1 1 d . . . . .
H49 H -0.1633 0.6249 -0.0499 0.052 Uiso 1 1 calc R . . . .
C2 C 0.2715(3) 0.9471(2) 0.8486(2) 0.0199(7) Uani 1 1 d . . . . .
C6 C 0.4150(3) 0.8392(2) 0.8723(2) 0.0173(6) Uani 1 1 d . . . . .
H6A H 0.4738 0.8232 0.8603 0.021 Uiso 1 1 calc R . . . .
C37 C 0.7855(4) 0.7316(4) 0.7373(3) 0.0433(10) Uani 1 1 d . . . . .
H37A H 0.7393 0.6774 0.7057 0.065 Uiso 1 1 calc GR . . . .
H37B H 0.8543 0.7097 0.7869 0.065 Uiso 1 1 calc GR . . . .
H37C H 0.7942 0.7677 0.6848 0.065 Uiso 1 1 calc GR . . . .
C16 C 0.4446(3) 0.5078(2) 0.6486(2) 0.0161(6) Uani 1 1 d . . . . .
H16 H 0.4277 0.4418 0.6213 0.019 Uiso 1 1 calc R . . . .
C4 C 0.2932(3) 0.7981(2) 0.9427(2) 0.0191(6) Uani 1 1 d . . . . .
C43 C 0.1507(3) 0.7529(3) 0.5613(3) 0.0351(9) Uani 1 1 d . . . . .
H43 H 0.2094 0.7770 0.5536 0.042 Uiso 1 1 calc R . . . .
C20 C 0.3003(3) 0.5433(2) 0.4672(2) 0.0179(6) Uani 1 1 d . . . . .
C44 C 0.0482(3) 0.7653(3) 0.4831(3) 0.0260(7) Uani 1 1 d . . . . .
C48 C -0.1565(4) 0.7414(4) 0.0363(3) 0.0419(10) Uani 1 1 d . . . . .
H48 H -0.2287 0.7397 0.0223 0.050 Uiso 1 1 calc R . . . .
C41 C 0.0795(4) 0.6696(3) 0.6619(3) 0.0388(10) Uani 1 1 d . . . . .
H41 H 0.0892 0.6369 0.7214 0.047 Uiso 1 1 calc R . . . .
C45 C 0.0232(3) 0.8160(3) 0.3847(3) 0.0339(8) Uani 1 1 d . . . . .
H45A H -0.0108 0.8760 0.3850 0.051 Uiso 1 1 calc GR . . . .
H45B H -0.0241 0.7769 0.3271 0.051 Uiso 1 1 calc GR . . . .
H45C H 0.0885 0.8278 0.3785 0.051 Uiso 1 1 calc GR . . . .
C38 C 0.7366(3) 0.7945(3) 0.7911(3) 0.0325(8) Uani 1 1 d . . . . .
C47 C -0.0923(4) 0.8128(4) 0.1000(3) 0.0497(13) Uani 1 1 d . . . . .
H47 H -0.1202 0.8593 0.1284 0.060 Uiso 1 1 calc R . . . .
H3 H 0.261(4) 0.6078(19) 0.953(3) 0.043(14) Uiso 1 1 d D . . . .
H5 H 0.271(4) 0.433(3) 0.515(2) 0.045(14) Uiso 1 1 d D . . . .
H7 H 0.245(4) 0.8837(18) 0.332(4) 0.042(13) Uiso 1 1 d D . . . .
H1 H 0.219(4) 1.044(4) 0.759(3) 0.057(16) Uiso 1 1 d 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
Br4 C30 1.902(3) . ?
Br3 C21 1.893(3) . ?
Br2 C12 1.888(3) . ?
Br1 C3 1.898(3) . ?
O8 H8 0.8221 . ?
O8 C31 1.368(4) . ?
O3 C11 1.364(4) . ?
O3 H3 0.835(19) . ?
O4 H4 0.8307 . ?
O4 C13 1.361(4) . ?
O7 C29 1.366(4) . ?
O7 H7 0.840(19) . ?
O6 H6 0.8454 . ?
O6 C22 1.360(4) . ?
O5 C20 1.366(4) . ?
O5 H5 0.834(19) . ?
O1 C2 1.364(4) . ?
O1 H1 0.84(2) . ?
O2 H2 0.8640 . ?
O2 C4 1.361(4) . ?
O9 N1 1.331(4) . ?
O10 N2 1.319(4) . ?
N2 C50 1.335(5) . ?
N2 C46 1.383(5) . ?
C10 C7 1.521(4) . ?
C10 C15 1.395(4) . ?
C10 C11 1.404(5) . ?
O11 C38 1.227(5) . ?
C3 C2 1.386(5) . ?
C3 C4 1.403(5) . ?
C7 H7A 0.9800 . ?
C7 C8 1.531(4) . ?
C7 C5 1.533(4) . ?
N1 C40 1.361(5) . ?
N1 C44 1.356(5) . ?
C28 C25 1.534(4) . ?
C28 C29 1.396(4) . ?
C28 C33 1.396(4) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C9 C8 1.525(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.530(4) . ?
C17 C16 1.531(4) . ?
C50 C51 1.464(6) . ?
C50 C49 1.402(6) . ?
C25 H25 0.9800 . ?
C25 C23 1.514(4) . ?
C25 C26 1.537(4) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C27 C26 1.523(5) . ?
C29 C30 1.399(5) . ?
C23 C22 1.396(4) . ?
C23 C24 1.402(4) . ?
C30 C31 1.382(5) . ?
C22 C21 1.395(5) . ?
C15 H15 0.9300 . ?
C15 C14 1.389(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C11 C12 1.391(5) . ?
C21 C20 1.390(5) . ?
C1 C34 1.526(4) . ?
C1 C2 1.413(5) . ?
C1 C6 1.392(5) . ?
C5 C6 1.390(5) . ?
C5 C4 1.392(5) . ?
C33 H33 0.9300 . ?
C33 C32 1.386(5) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C36 C35 1.525(4) . ?
C24 H24 0.9300 . ?
C24 C19 1.400(4) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C35 C34 1.541(4) . ?
C19 C16 1.531(4) . ?
C19 C20 1.401(5) . ?
C42 H42 0.9300 . ?
C42 C43 1.381(6) . ?
C42 C41 1.381(6) . ?
C32 C34 1.531(4) . ?
C32 C31 1.406(5) . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?
C39 C38 1.492(6) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C34 H34 0.9800 . ?
C12 C13 1.393(5) . ?
C46 H46 0.9300 . ?
C46 C47 1.366(7) . ?
C14 C13 1.395(5) . ?
C14 C16 1.532(4) . ?
C51 H51A 0.9600 . ?
C51 H51B 0.9600 . ?
C51 H51C 0.9600 . ?
C40 H40 0.9300 . ?
C40 C41 1.366(6) . ?
C49 H49 0.9300 . ?
C49 C48 1.365(7) . ?
C6 H6A 0.9300 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C37 C38 1.503(6) . ?
C16 H16 0.9800 . ?
C43 H43 0.9300 . ?
C43 C44 1.385(5) . ?
C44 C45 1.487(5) . ?
C48 H48 0.9300 . ?
C48 C47 1.369(7) . ?
C41 H41 0.9300 . ?
C45 H45A 0.9600 . ?
C45 H45B 0.9600 . ?
C45 H45C 0.9600 . ?
C47 H47 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
C31 O8 H8 127.3 . . ?
C11 O3 H3 110(3) . . ?
C13 O4 H4 138.5 . . ?
C29 O7 H7 108(3) . . ?
C22 O6 H6 138.2 . . ?
C20 O5 H5 108(4) . . ?
C2 O1 H1 107(4) . . ?
C4 O2 H2 135.4 . . ?
O10 N2 C50 119.6(3) . . ?
O10 N2 C46 116.9(3) . . ?
C50 N2 C46 123.5(4) . . ?
C15 C10 C7 121.7(3) . . ?
C15 C10 C11 117.0(3) . . ?
C11 C10 C7 121.3(3) . . ?
C2 C3 Br1 119.1(2) . . ?
C2 C3 C4 121.9(3) . . ?
C4 C3 Br1 119.0(3) . . ?
C10 C7 H7A 106.7 . . ?
C10 C7 C8 112.9(3) . . ?
C10 C7 C5 109.8(2) . . ?
C8 C7 H7A 106.7 . . ?
C8 C7 C5 113.5(3) . . ?
C5 C7 H7A 106.7 . . ?
O9 N1 C40 118.3(3) . . ?
O9 N1 C44 120.0(3) . . ?
C44 N1 C40 121.7(3) . . ?
C29 C28 C25 120.4(3) . . ?
C33 C28 C25 121.8(3) . . ?
C33 C28 C29 117.8(3) . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H17A C17 H17B 107.9 . . ?
C18 C17 H17A 109.3 . . ?
C18 C17 H17B 109.3 . . ?
C18 C17 C16 111.8(3) . . ?
C16 C17 H17A 109.3 . . ?
C16 C17 H17B 109.3 . . ?
N2 C50 C51 117.3(4) . . ?
N2 C50 C49 117.3(4) . . ?
C49 C50 C51 125.4(4) . . ?
C28 C25 H25 106.2 . . ?
C28 C25 C26 113.6(3) . . ?
C23 C25 C28 110.1(2) . . ?
C23 C25 H25 106.2 . . ?
C23 C25 C26 113.8(3) . . ?
C26 C25 H25 106.2 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
O7 C29 C28 123.5(3) . . ?
O7 C29 C30 117.0(3) . . ?
C28 C29 C30 119.5(3) . . ?
C22 C23 C25 119.2(3) . . ?
C22 C23 C24 117.8(3) . . ?
C24 C23 C25 123.0(3) . . ?
C29 C30 Br4 118.2(2) . . ?
C31 C30 Br4 120.0(2) . . ?
C31 C30 C29 121.8(3) . . ?
O6 C22 C23 117.4(3) . . ?
O6 C22 C21 122.8(3) . . ?
C21 C22 C23 119.7(3) . . ?
C10 C15 H15 118.1 . . ?
C14 C15 C10 123.8(3) . . ?
C14 C15 H15 118.1 . . ?
C7 C8 H8A 109.3 . . ?
C7 C8 H8B 109.3 . . ?
C9 C8 C7 111.6(3) . . ?
C9 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
O3 C11 C10 123.6(3) . . ?
O3 C11 C12 116.4(3) . . ?
C12 C11 C10 120.0(3) . . ?
C22 C21 Br3 119.3(2) . . ?
C20 C21 Br3 118.8(2) . . ?
C20 C21 C22 121.9(3) . . ?
C2 C1 C34 120.7(3) . . ?
C6 C1 C34 121.8(3) . . ?
C6 C1 C2 117.4(3) . . ?
C6 C5 C7 122.0(3) . . ?
C6 C5 C4 118.2(3) . . ?
C4 C5 C7 119.8(3) . . ?
C28 C33 H33 118.4 . . ?
C32 C33 C28 123.3(3) . . ?
C32 C33 H33 118.4 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
C23 C24 H24 118.4 . . ?
C19 C24 C23 123.1(3) . . ?
C19 C24 H24 118.4 . . ?
C36 C35 H35A 109.0 . . ?
C36 C35 H35B 109.0 . . ?
C36 C35 C34 112.7(3) . . ?
H35A C35 H35B 107.8 . . ?
C34 C35 H35A 109.0 . . ?
C34 C35 H35B 109.0 . . ?
C24 C19 C16 121.2(3) . . ?
C24 C19 C20 117.9(3) . . ?
C20 C19 C16 120.9(3) . . ?
C43 C42 H42 120.3 . . ?
C43 C42 C41 119.3(4) . . ?
C41 C42 H42 120.3 . . ?
C33 C32 C34 122.5(3) . . ?
C33 C32 C31 118.1(3) . . ?
C31 C32 C34 119.4(3) . . ?
H39A C39 H39B 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C38 C39 H39A 109.5 . . ?
C38 C39 H39B 109.5 . . ?
C38 C39 H39C 109.5 . . ?
C25 C26 H26A 109.3 . . ?
C25 C26 H26B 109.3 . . ?
C27 C26 C25 111.7(3) . . ?
C27 C26 H26A 109.3 . . ?
C27 C26 H26B 109.3 . . ?
H26A C26 H26B 107.9 . . ?
C1 C34 C35 111.6(2) . . ?
C1 C34 C32 111.6(3) . . ?
C1 C34 H34 106.6 . . ?
C35 C34 H34 106.6 . . ?
C32 C34 C35 113.2(3) . . ?
C32 C34 H34 106.6 . . ?
C11 C12 Br2 118.8(2) . . ?
C11 C12 C13 121.7(3) . . ?
C13 C12 Br2 119.4(2) . . ?
O8 C31 C30 122.9(3) . . ?
O8 C31 C32 117.7(3) . . ?
C30 C31 C32 119.4(3) . . ?
N2 C46 H46 120.4 . . ?
C47 C46 N2 119.1(5) . . ?
C47 C46 H46 120.4 . . ?
C15 C14 C13 118.1(3) . . ?
C15 C14 C16 121.9(3) . . ?
C13 C14 C16 120.0(3) . . ?
C50 C51 H51A 109.5 . . ?
C50 C51 H51B 109.5 . . ?
C50 C51 H51C 109.5 . . ?
H51A C51 H51B 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
N1 C40 H40 119.7 . . ?
N1 C40 C41 120.5(4) . . ?
C41 C40 H40 119.7 . . ?
O4 C13 C12 123.3(3) . . ?
O4 C13 C14 117.3(3) . . ?
C12 C13 C14 119.3(3) . . ?
C50 C49 H49 120.2 . . ?
C48 C49 C50 119.6(5) . . ?
C48 C49 H49 120.2 . . ?
O1 C2 C3 117.6(3) . . ?
O1 C2 C1 123.0(3) . . ?
C3 C2 C1 119.3(3) . . ?
C1 C6 H6A 118.2 . . ?
C5 C6 C1 123.7(3) . . ?
C5 C6 H6A 118.2 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C38 C37 H37A 109.5 . . ?
C38 C37 H37B 109.5 . . ?
C38 C37 H37C 109.5 . . ?
C17 C16 C19 113.6(3) . . ?
C17 C16 C14 112.6(3) . . ?
C17 C16 H16 106.5 . . ?
C19 C16 C14 110.7(2) . . ?
C19 C16 H16 106.5 . . ?
C14 C16 H16 106.5 . . ?
O2 C4 C3 122.7(3) . . ?
O2 C4 C5 117.9(3) . . ?
C5 C4 C3 119.3(3) . . ?
C42 C43 H43 119.6 . . ?
C42 C43 C44 120.9(4) . . ?
C44 C43 H43 119.6 . . ?
O5 C20 C21 116.9(3) . . ?
O5 C20 C19 123.5(3) . . ?
C21 C20 C19 119.6(3) . . ?
N1 C44 C43 118.2(3) . . ?
N1 C44 C45 117.3(3) . . ?
C43 C44 C45 124.5(3) . . ?
C49 C48 H48 119.0 . . ?
C49 C48 C47 122.1(4) . . ?
C47 C48 H48 119.0 . . ?
C42 C41 H41 120.3 . . ?
C40 C41 C42 119.3(4) . . ?
C40 C41 H41 120.3 . . ?
C44 C45 H45A 109.5 . . ?
C44 C45 H45B 109.5 . . ?
C44 C45 H45C 109.5 . . ?
H45A C45 H45B 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
O11 C38 C39 121.8(4) . . ?
O11 C38 C37 121.5(4) . . ?
C39 C38 C37 116.7(4) . . ?
C46 C47 C48 118.3(4) . . ?
C46 C47 H47 120.8 . . ?
C48 C47 H47 120.8 . . ?

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
O8 H8 O9 0.82 1.76 2.586(3) 176.7 2_576
O4 H4 O9 0.83 1.75 2.585(3) 178.7 2_566
O6 H6 O10 0.85 1.72 2.560(3) 174.6 .
O2 H2 O10 0.86 1.70 2.569(3) 178.6 1_556
O3 H3 O2 0.835(19) 1.86(2) 2.686(3) 171(5) .
O5 H5 O4 0.834(19) 1.84(2) 2.659(3) 167(5) .
O7 H7 O6 0.840(19) 1.82(2) 2.659(3) 173(5) .
O1 H1 O8 0.84(2) 1.85(2) 2.692(3) 173(5) .

_shelx_SHELXL_version_number     2014/7
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1 0 8 0.0446 1.0000 0.0000 8.0000 -0.5240 0.2203 0.8418
-1 0 -8 0.0391 -1.0000 -0.0000 -8.0000 0.5240 -0.2203 -0.8418
-1 -9 -2 0.0415 -1.0000 -9.0000 -2.0000 0.9505 -0.3328 0.2930
1 9 -1 0.0571 1.0000 9.0000 -1.0000 -0.7558 0.2932 -0.5913
-9 0 6 0.0354 -9.0000 0.0000 6.0000 -0.3459 -0.9510 0.1786
8 1 -7 0.0317 8.0000 1.0000 -7.0000 0.3250 0.8446 -0.3842
4 -5 4 0.0433 4.0000 -5.0000 4.0000 0.1743 0.4042 0.8825
-5 5 -4 0.0500 -5.0000 5.0000 -4.0000 -0.1695 -0.5187 -0.9289
0 -2 -8 0.0278 -0.0000 -2.0000 -8.0000 0.7005 -0.1485 -0.6758
4 2 6 0.0397 4.0000 2.0000 6.0000 -0.5900 0.5799 0.6627
7 0 2 0.0191 7.0000 0.0000 2.0000 -0.1636 0.8278 0.5239
-7 -1 -1 0.0293 -7.0000 -1.0000 -1.0000 0.1894 -0.8359 -0.3647

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_3_BrC2
_database_code_depnum_ccdc_archive 'CCDC 1551404'
_audit_update_record             
;
2017-05-22 deposited with the CCDC.
2017-06-15 downloaded from the CCDC.
;
_audit_creation_date             2017-04-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C36 H36 Br4 O8, 2(C6 H7 N O), C3 H6 O'
_chemical_formula_sum            'C51 H56 Br4 N2 O11'
_chemical_formula_weight         1192.61
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N1 O9 Br1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   13.6699(3)
_cell_length_b                   13.7198(4)
_cell_length_c                   14.7020(5)
_cell_angle_alpha                114.673(3)
_cell_angle_beta                 90.898(2)
_cell_angle_gamma                92.597(2)
_cell_volume                     2501.22(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9484
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      73.1490
_cell_measurement_theta_min      3.6730
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.439
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79071
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1208
_exptl_crystal_size_max          0.2063
_exptl_crystal_size_mid          0.1074
_exptl_crystal_size_min          0.0476
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14656
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        66.750
_diffrn_reflns_theta_max         66.750
_diffrn_reflns_theta_min         3.239
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -44.00   29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676   37.0000    0.0000 73

#__ type_ start__ end____ width___ exp.time_
  2 omega  -41.00   -4.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676   37.0000  -30.0000 37

#__ type_ start__ end____ width___ exp.time_
  3 omega  -96.00   -7.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676  125.0000   60.0000 89

#__ type_ start__ end____ width___ exp.time_
  4 omega -108.00  -20.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676  -37.0000 -180.0000 88

#__ type_ start__ end____ width___ exp.time_
  5 omega   78.00  175.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      105.6154   30.0000   30.0000 97

#__ type_ start__ end____ width___ exp.time_
  6 omega   96.00  173.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  125.0000  -60.0000 77

#__ type_ start__ end____ width___ exp.time_
  7 omega   80.00  172.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      105.6154   30.0000  120.0000 92

#__ type_ start__ end____ width___ exp.time_
  8 omega   84.00  138.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -77.0000  -30.0000 54

#__ type_ start__ end____ width___ exp.time_
  9 omega   47.00  138.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -77.0000  -90.0000 91

#__ type_ start__ end____ width___ exp.time_
 10 omega   34.00  122.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      105.6154 -125.0000 -180.0000 88

#__ type_ start__ end____ width___ exp.time_
 11 omega   30.00   91.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -30.0000 -150.0000 61

#__ type_ start__ end____ width___ exp.time_
 12 omega   29.00   56.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -77.0000  -30.0000 27

#__ type_ start__ end____ width___ exp.time_
 13 omega   29.00   61.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -30.0000    0.0000 32

#__ type_ start__ end____ width___ exp.time_
 14 omega   23.00  109.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -94.0000 -120.0000 86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0769138000
_diffrn_orient_matrix_UB_12      0.0833265000
_diffrn_orient_matrix_UB_13      0.0485837000
_diffrn_orient_matrix_UB_21      0.0643149000
_diffrn_orient_matrix_UB_22      0.0504183000
_diffrn_orient_matrix_UB_23      0.0971854000
_diffrn_orient_matrix_UB_31      0.0518960000
_diffrn_orient_matrix_UB_32      0.0763795000
_diffrn_orient_matrix_UB_33      -0.0388724000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7850
_reflns_number_total             8799
_reflns_odcompleteness_completeness 99.04
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     641
_refine_ls_number_reflns         8799
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0289
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0310P)²+0.4881P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0705
_refine_ls_wR_factor_ref         0.0741
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O7-H7
 0.85 with sigma of 0.02
 O5-H5
 0.85 with sigma of 0.02
 O6-H6
 0.85 with sigma of 0.02
 O4-H4
 0.85 with sigma of 0.02
3.a Riding coordinates:
 O2(H2), O4(H4), O6(H6), O8(H8)
3.b Ternary CH refined with riding coordinates:
 C7(H7A), C16(H16), C25(H25), C34(H34)
3.c Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C17(H17A,H17B), C26(H26A,H26B), C35(H35A,H35B)
3.d Aromatic/amide H refined with riding coordinates:
 C1(H1A), C10(H10), C19(H19), C28(H28), C43(H43), C44(H44), C45(H45), C47(H47),
  C37(H37), C39(H39), C40(H40), C41(H41)
3.e Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C18(H18A,H18B,H18C), C27(H27A,H27B,H27C), C36(H36A,H36B,
 H36C), C48(H48A,H48B,H48C), C42(H42A,H42B,H42C), C49(H49A,H49B,H49C), C51(H51A,
 H51B,H51C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.60578(2) 0.88428(2) 0.06398(2) 0.02593(7) Uani 1 1 d . . . . .
Br2 Br 1.11545(2) 0.86316(2) 0.22823(2) 0.02630(7) Uani 1 1 d . . . . .
Br3 Br 0.94442(2) 0.86550(2) 0.72648(2) 0.02611(7) Uani 1 1 d . . . . .
Br4 Br 0.45984(2) 0.91238(2) 0.58169(2) 0.02604(7) Uani 1 1 d . . . . .
O1 O 0.47910(12) 0.78932(14) 0.17171(13) 0.0233(3) Uani 1 1 d . . . . .
H1 H 0.459(3) 0.786(3) 0.227(3) 0.050(10) Uiso 1 1 d . . . . .
O2 O 0.78015(12) 0.73453(14) 0.00022(13) 0.0231(3) Uani 1 1 d . . . . .
H2 H 0.7816 0.7674 -0.0382 0.095(18) Uiso 1 1 d R . . . .
O3 O 0.96370(13) 0.74329(14) 0.07082(13) 0.0235(3) Uani 1 1 d . . . . .
H3 H 0.907(3) 0.738(3) 0.046(3) 0.038(9) Uiso 1 1 d . . . . .
O4 O 1.11676(12) 0.73881(14) 0.36291(12) 0.0231(3) Uani 1 1 d D . . . .
H4 H 1.1709 0.7758 0.3763 0.102(19) Uiso 1 1 d DR . . . .
O5 O 1.05347(12) 0.75294(14) 0.54148(13) 0.0240(3) Uani 1 1 d D . . . .
H5 H 1.076(3) 0.748(3) 0.4874(18) 0.039(9) Uiso 1 1 d D . . . .
O6 O 0.74798(12) 0.73062(14) 0.68657(12) 0.0244(3) Uani 1 1 d D . . . .
H6 H 0.7576 0.7610 0.7488 0.079(15) Uiso 1 1 d DR . . . .
O7 O 0.57257(13) 0.76533(14) 0.63606(12) 0.0253(4) Uani 1 1 d D . . . .
H7 H 0.6257(16) 0.751(2) 0.654(2) 0.028(8) Uiso 1 1 d D . . . .
O8 O 0.43314(13) 0.79410(14) 0.35020(12) 0.0248(4) Uani 1 1 d . . . . .
H8 H 0.3795 0.8237 0.3716 0.060(12) Uiso 1 1 d R . . . .
C1 C 0.66285(16) 0.58975(16) 0.13003(16) 0.0154(4) Uani 1 1 d . . . . .
H1A H 0.6758 0.5329 0.1464 0.018 Uiso 1 1 calc R . . . .
C2 C 0.57606(16) 0.64049(17) 0.16134(16) 0.0167(4) Uani 1 1 d . . . . .
C3 C 0.55929(16) 0.73053(18) 0.14161(16) 0.0181(4) Uani 1 1 d . . . . .
C4 C 0.62746(17) 0.76081(17) 0.08734(17) 0.0175(4) Uani 1 1 d . . . . .
C5 C 0.71185(16) 0.70504(18) 0.05219(16) 0.0173(4) Uani 1 1 d . . . . .
C6 C 0.73169(16) 0.61880(17) 0.07563(16) 0.0158(4) Uani 1 1 d . . . . .
C7 C 0.82693(16) 0.56152(18) 0.04404(16) 0.0177(4) Uani 1 1 d . . . . .
H7A H 0.8508 0.5768 -0.0114 0.021 Uiso 1 1 calc R . . . .
C8 C 0.81225(17) 0.43886(18) 0.00407(17) 0.0197(4) Uani 1 1 d . . . . .
H8A H 0.8753 0.4072 -0.0110 0.024 Uiso 1 1 calc R . . . .
H8B H 0.7836 0.4204 0.0552 0.024 Uiso 1 1 calc R . . . .
C9 C 0.7456(2) 0.3929(2) -0.09009(19) 0.0291(5) Uani 1 1 d . . . . .
H9A H 0.7721 0.4144 -0.1394 0.044 Uiso 1 1 calc GR . . . .
H9B H 0.6814 0.4194 -0.0739 0.044 Uiso 1 1 calc GR . . . .
H9C H 0.7413 0.3159 -0.1162 0.044 Uiso 1 1 calc GR . . . .
C10 C 0.91483(16) 0.57178(17) 0.20258(16) 0.0159(4) Uani 1 1 d . . . . .
H10 H 0.8721 0.5156 0.1995 0.019 Uiso 1 1 calc R . . . .
C11 C 0.98593(16) 0.61273(17) 0.28038(16) 0.0161(4) Uani 1 1 d . . . . .
C12 C 1.04804(16) 0.69930(18) 0.28651(17) 0.0174(4) Uani 1 1 d . . . . .
C13 C 1.03635(16) 0.74139(17) 0.21589(17) 0.0179(4) Uani 1 1 d . . . . .
C14 C 0.96626(16) 0.69833(18) 0.13787(17) 0.0177(4) Uani 1 1 d . . . . .
C15 C 0.90434(16) 0.61043(17) 0.12935(16) 0.0168(4) Uani 1 1 d . . . . .
C16 C 0.99817(16) 0.56451(17) 0.35609(16) 0.0165(4) Uani 1 1 d . . . . .
H16 H 1.0652 0.5855 0.3846 0.020 Uiso 1 1 calc R . . . .
C17 C 0.99057(17) 0.44094(18) 0.30596(17) 0.0202(4) Uani 1 1 d . . . . .
H17A H 0.9972 0.4138 0.3569 0.024 Uiso 1 1 calc R . . . .
H17B H 0.9265 0.4164 0.2729 0.024 Uiso 1 1 calc R . . . .
C18 C 1.06946(19) 0.39630(19) 0.22956(19) 0.0251(5) Uani 1 1 d . . . . .
H18A H 1.0586 0.4164 0.1752 0.038 Uiso 1 1 calc GR . . . .
H18B H 1.0667 0.3194 0.2044 0.038 Uiso 1 1 calc GR . . . .
H18C H 1.1327 0.4250 0.2610 0.038 Uiso 1 1 calc GR . . . .
C19 C 0.83476(17) 0.57058(17) 0.43978(16) 0.0168(4) Uani 1 1 d . . . . .
H19 H 0.8114 0.5136 0.3810 0.020 Uiso 1 1 calc R . . . .
C20 C 0.77266(16) 0.60929(17) 0.51985(16) 0.0162(4) Uani 1 1 d . . . . .
C21 C 0.80939(17) 0.69450(18) 0.60825(16) 0.0180(4) Uani 1 1 d . . . . .
C22 C 0.90177(17) 0.74147(17) 0.61112(17) 0.0185(4) Uani 1 1 d . . . . .
C23 C 0.96290(16) 0.70267(18) 0.53051(17) 0.0177(4) Uani 1 1 d . . . . .
C24 C 0.93032(16) 0.61293(17) 0.44316(16) 0.0166(4) Uani 1 1 d . . . . .
C25 C 0.66623(16) 0.56648(17) 0.51364(16) 0.0168(4) Uani 1 1 d . . . . .
H25 H 0.6467 0.5858 0.5826 0.020 Uiso 1 1 calc R . . . .
C26 C 0.65384(17) 0.44338(18) 0.45871(17) 0.0202(4) Uani 1 1 d . . . . .
H26A H 0.5848 0.4211 0.4531 0.024 Uiso 1 1 calc R . . . .
H26B H 0.6777 0.4205 0.3915 0.024 Uiso 1 1 calc R . . . .
C27 C 0.70969(19) 0.38915(19) 0.51401(19) 0.0257(5) Uani 1 1 d . . . . .
H27A H 0.6959 0.3128 0.4814 0.039 Uiso 1 1 calc GR . . . .
H27B H 0.6895 0.4156 0.5820 0.039 Uiso 1 1 calc GR . . . .
H27C H 0.7788 0.4049 0.5134 0.039 Uiso 1 1 calc GR . . . .
C28 C 0.58160(16) 0.58931(17) 0.36760(17) 0.0164(4) Uani 1 1 d . . . . .
H28 H 0.6088 0.5263 0.3246 0.020 Uiso 1 1 calc R . . . .
C29 C 0.52370(16) 0.64239(18) 0.32628(17) 0.0166(4) Uani 1 1 d . . . . .
C30 C 0.48558(16) 0.73922(18) 0.39081(17) 0.0183(4) Uani 1 1 d . . . . .
C31 C 0.50528(17) 0.77850(18) 0.49397(17) 0.0192(4) Uani 1 1 d . . . . .
C32 C 0.56116(16) 0.72238(18) 0.53414(17) 0.0184(4) Uani 1 1 d . . . . .
C33 C 0.60095(15) 0.62594(17) 0.47034(16) 0.0161(4) Uani 1 1 d . . . . .
C34 C 0.50011(16) 0.59949(17) 0.21420(17) 0.0173(4) Uani 1 1 d . . . . .
H34 H 0.4379 0.6289 0.2070 0.021 Uiso 1 1 calc R . . . .
C35 C 0.48394(17) 0.47622(18) 0.16147(17) 0.0195(4) Uani 1 1 d . . . . .
H35A H 0.4706 0.4551 0.0906 0.023 Uiso 1 1 calc R . . . .
H35B H 0.5437 0.4440 0.1684 0.023 Uiso 1 1 calc R . . . .
C36 C 0.39960(18) 0.4328(2) 0.20348(19) 0.0254(5) Uani 1 1 d . . . . .
H36A H 0.3918 0.3562 0.1670 0.038 Uiso 1 1 calc GR . . . .
H36B H 0.3402 0.4645 0.1970 0.038 Uiso 1 1 calc GR . . . .
H36C H 0.4138 0.4504 0.2729 0.038 Uiso 1 1 calc GR . . . .
O10 O 0.76891(14) 0.82309(13) -0.12314(12) 0.0262(4) Uani 1 1 d . . . . .
N2 N 0.75779(15) 0.92737(16) -0.09474(14) 0.0213(4) Uani 1 1 d . . . . .
C43 C 0.67989(18) 0.9599(2) -0.13074(18) 0.0245(5) Uani 1 1 d . . . . .
H43 H 0.6341 0.9097 -0.1752 0.029 Uiso 1 1 calc R . . . .
C44 C 0.6695(2) 1.0678(2) -0.1008(2) 0.0274(5) Uani 1 1 d . . . . .
H44 H 0.6167 1.0911 -0.1255 0.033 Uiso 1 1 calc R . . . .
C45 C 0.7376(2) 1.1421(2) -0.0337(2) 0.0307(6) Uani 1 1 d . . . . .
H45 H 0.7296 1.2152 -0.0125 0.037 Uiso 1 1 calc R . . . .
C46 C 0.8174(2) 1.1080(2) 0.00197(19) 0.0281(5) Uani 1 1 d . . . . .
C47 C 0.82454(19) 0.9984(2) -0.03003(19) 0.0266(5) Uani 1 1 d . . . . .
H47 H 0.8767 0.9734 -0.0062 0.032 Uiso 1 1 calc R . . . .
C48 C 0.8960(2) 1.1853(3) 0.0700(2) 0.0411(7) Uani 1 1 d . . . . .
H48A H 0.9276 1.1530 0.1086 0.062 Uiso 1 1 calc GR . . . .
H48B H 0.8673 1.2498 0.1143 0.062 Uiso 1 1 calc GR . . . .
H48C H 0.9435 1.2023 0.0306 0.062 Uiso 1 1 calc GR . . . .
O9 O 0.73121(12) 1.12239(14) 0.59038(13) 0.0257(4) Uani 1 1 d . . . . .
N1 N 0.75006(14) 1.03032(16) 0.51414(16) 0.0228(4) Uani 1 1 d . . . . .
C37 C 0.78477(17) 1.03296(19) 0.42968(19) 0.0228(5) Uani 1 1 d . . . . .
H37 H 0.7959 1.0988 0.4264 0.027 Uiso 1 1 calc R . . . .
C38 C 0.80392(17) 0.9397(2) 0.3482(2) 0.0254(5) Uani 1 1 d . . . . .
C39 C 0.7882(2) 0.8423(2) 0.3560(2) 0.0336(6) Uani 1 1 d . . . . .
H39 H 0.8006 0.7780 0.3024 0.040 Uiso 1 1 calc R . . . .
C40 C 0.7543(2) 0.8418(2) 0.4438(3) 0.0395(7) Uani 1 1 d . . . . .
H40 H 0.7450 0.7771 0.4496 0.047 Uiso 1 1 calc R . . . .
C41 C 0.7343(2) 0.9364(2) 0.5225(2) 0.0324(6) Uani 1 1 d . . . . .
H41 H 0.7102 0.9359 0.5811 0.039 Uiso 1 1 calc R . . . .
C42 C 0.8398(2) 0.9454(2) 0.2547(2) 0.0329(6) Uani 1 1 d . . . . .
H42A H 0.8973 0.9051 0.2341 0.049 Uiso 1 1 calc GR . . . .
H42B H 0.8555 1.0190 0.2674 0.049 Uiso 1 1 calc GR . . . .
H42C H 0.7897 0.9157 0.2025 0.049 Uiso 1 1 calc GR . . . .
O11 O 0.71130(16) 0.33866(15) 0.19908(15) 0.0359(4) Uani 1 1 d . . . . .
C49 C 0.5749(2) 0.2141(3) 0.1650(3) 0.0453(7) Uani 1 1 d . . . . .
H49A H 0.5319 0.2288 0.2197 0.068 Uiso 1 1 calc GR . . . .
H49B H 0.5759 0.1378 0.1267 0.068 Uiso 1 1 calc GR . . . .
H49C H 0.5520 0.2468 0.1229 0.068 Uiso 1 1 calc GR . . . .
C50 C 0.6761(2) 0.2588(2) 0.2052(2) 0.0329(6) Uani 1 1 d . . . . .
C51 C 0.7309(3) 0.2000(3) 0.2547(2) 0.0452(7) Uani 1 1 d . . . . .
H51A H 0.7483 0.1319 0.2047 0.068 Uiso 1 1 calc GR . . . .
H51B H 0.6900 0.1886 0.3023 0.068 Uiso 1 1 calc GR . . . .
H51C H 0.7892 0.2419 0.2885 0.068 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C4 1.898(2) . ?
Br2 C13 1.889(2) . ?
Br3 C22 1.892(2) . ?
Br4 C31 1.890(2) . ?
O1 H1 0.88(4) . ?
O1 C3 1.358(3) . ?
O2 H2 0.8577 . ?
O2 C5 1.366(3) . ?
O3 H3 0.84(4) . ?
O3 C14 1.365(3) . ?
O4 H4 0.8500 . ?
O4 C12 1.360(3) . ?
O5 H5 0.836(18) . ?
O5 C23 1.363(3) . ?
O6 H6 0.8376 . ?
O6 C21 1.367(3) . ?
O7 H7 0.829(18) . ?
O7 C32 1.365(3) . ?
O8 H8 0.8544 . ?
O8 C30 1.360(3) . ?
C1 H1A 0.9300 . ?
C1 C2 1.389(3) . ?
C1 C6 1.393(3) . ?
C2 C3 1.409(3) . ?
C2 C34 1.528(3) . ?
C3 C4 1.394(3) . ?
C4 C5 1.397(3) . ?
C5 C6 1.400(3) . ?
C6 C7 1.528(3) . ?
C7 H7A 0.9800 . ?
C7 C8 1.535(3) . ?
C7 C15 1.528(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.525(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10 0.9300 . ?
C10 C11 1.396(3) . ?
C10 C15 1.393(3) . ?
C11 C12 1.399(3) . ?
C11 C16 1.524(3) . ?
C12 C13 1.393(3) . ?
C13 C14 1.390(3) . ?
C14 C15 1.402(3) . ?
C16 H16 0.9800 . ?
C16 C17 1.538(3) . ?
C16 C24 1.524(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.524(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19 0.9300 . ?
C19 C20 1.392(3) . ?
C19 C24 1.397(3) . ?
C20 C21 1.402(3) . ?
C20 C25 1.531(3) . ?
C21 C22 1.383(3) . ?
C22 C23 1.390(3) . ?
C23 C24 1.406(3) . ?
C25 H25 0.9800 . ?
C25 C26 1.538(3) . ?
C25 C33 1.533(3) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C26 C27 1.528(3) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28 0.9300 . ?
C28 C29 1.390(3) . ?
C28 C33 1.395(3) . ?
C29 C30 1.401(3) . ?
C29 C34 1.524(3) . ?
C30 C31 1.398(3) . ?
C31 C32 1.394(3) . ?
C32 C33 1.404(3) . ?
C34 H34 0.9800 . ?
C34 C35 1.542(3) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C35 C36 1.527(3) . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
O10 N2 1.329(3) . ?
N2 C43 1.355(3) . ?
N2 C47 1.344(3) . ?
C43 H43 0.9300 . ?
C43 C44 1.372(4) . ?
C44 H44 0.9300 . ?
C44 C45 1.388(4) . ?
C45 H45 0.9300 . ?
C45 C46 1.384(4) . ?
C46 C47 1.385(4) . ?
C46 C48 1.502(4) . ?
C47 H47 0.9300 . ?
C48 H48A 0.9600 . ?
C48 H48B 0.9600 . ?
C48 H48C 0.9600 . ?
O9 N1 1.332(3) . ?
N1 C37 1.350(3) . ?
N1 C41 1.352(3) . ?
C37 H37 0.9300 . ?
C37 C38 1.379(4) . ?
C38 C39 1.396(4) . ?
C38 C42 1.499(4) . ?
C39 H39 0.9300 . ?
C39 C40 1.380(4) . ?
C40 H40 0.9300 . ?
C40 C41 1.374(4) . ?
C41 H41 0.9300 . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?
O11 C50 1.215(4) . ?
C49 H49A 0.9600 . ?
C49 H49B 0.9600 . ?
C49 H49C 0.9600 . ?
C49 C50 1.494(5) . ?
C50 C51 1.506(4) . ?
C51 H51A 0.9600 . ?
C51 H51B 0.9600 . ?
C51 H51C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 H1 109(3) . . ?
C5 O2 H2 137.3 . . ?
C14 O3 H3 112(2) . . ?
C12 O4 H4 137.6 . . ?
C23 O5 H5 113(2) . . ?
C21 O6 H6 133.2 . . ?
C32 O7 H7 112(2) . . ?
C30 O8 H8 125.9 . . ?
C2 C1 H1A 118.0 . . ?
C2 C1 C6 123.99(19) . . ?
C6 C1 H1A 118.0 . . ?
C1 C2 C3 117.9(2) . . ?
C1 C2 C34 121.37(19) . . ?
C3 C2 C34 120.7(2) . . ?
O1 C3 C2 123.4(2) . . ?
O1 C3 C4 117.74(19) . . ?
C4 C3 C2 118.8(2) . . ?
C3 C4 Br1 118.46(17) . . ?
C3 C4 C5 122.17(19) . . ?
C5 C4 Br1 119.35(16) . . ?
O2 C5 C4 122.96(19) . . ?
O2 C5 C6 117.5(2) . . ?
C4 C5 C6 119.5(2) . . ?
C1 C6 C5 117.5(2) . . ?
C1 C6 C7 122.11(19) . . ?
C5 C6 C7 120.35(19) . . ?
C6 C7 H7A 106.7 . . ?
C6 C7 C8 113.03(18) . . ?
C8 C7 H7A 106.7 . . ?
C15 C7 C6 109.76(18) . . ?
C15 C7 H7A 106.7 . . ?
C15 C7 C8 113.42(18) . . ?
C7 C8 H8A 109.4 . . ?
C7 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C9 C8 C7 111.10(18) . . ?
C9 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 H10 118.2 . . ?
C15 C10 H10 118.2 . . ?
C15 C10 C11 123.6(2) . . ?
C10 C11 C12 118.01(19) . . ?
C10 C11 C16 121.89(19) . . ?
C12 C11 C16 120.1(2) . . ?
O4 C12 C11 117.46(19) . . ?
O4 C12 C13 123.3(2) . . ?
C13 C12 C11 119.2(2) . . ?
C12 C13 Br2 119.24(17) . . ?
C14 C13 Br2 118.75(16) . . ?
C14 C13 C12 122.0(2) . . ?
O3 C14 C13 117.1(2) . . ?
O3 C14 C15 123.2(2) . . ?
C13 C14 C15 119.8(2) . . ?
C10 C15 C7 121.8(2) . . ?
C10 C15 C14 117.4(2) . . ?
C14 C15 C7 120.70(19) . . ?
C11 C16 H16 106.3 . . ?
C11 C16 C17 112.08(18) . . ?
C17 C16 H16 106.3 . . ?
C24 C16 C11 111.59(17) . . ?
C24 C16 H16 106.3 . . ?
C24 C16 C17 113.63(18) . . ?
C16 C17 H17A 109.3 . . ?
C16 C17 H17B 109.3 . . ?
H17A C17 H17B 108.0 . . ?
C18 C17 C16 111.55(18) . . ?
C18 C17 H17A 109.3 . . ?
C18 C17 H17B 109.3 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 H19 118.3 . . ?
C20 C19 C24 123.4(2) . . ?
C24 C19 H19 118.3 . . ?
C19 C20 C21 117.6(2) . . ?
C19 C20 C25 123.1(2) . . ?
C21 C20 C25 119.3(2) . . ?
O6 C21 C20 116.8(2) . . ?
O6 C21 C22 123.3(2) . . ?
C22 C21 C20 119.8(2) . . ?
C21 C22 Br3 119.02(17) . . ?
C21 C22 C23 122.0(2) . . ?
C23 C22 Br3 118.92(17) . . ?
O5 C23 C22 117.6(2) . . ?
O5 C23 C24 123.1(2) . . ?
C22 C23 C24 119.3(2) . . ?
C19 C24 C16 121.9(2) . . ?
C19 C24 C23 117.7(2) . . ?
C23 C24 C16 120.4(2) . . ?
C20 C25 H25 106.8 . . ?
C20 C25 C26 112.88(19) . . ?
C20 C25 C33 109.07(17) . . ?
C26 C25 H25 106.8 . . ?
C33 C25 H25 106.8 . . ?
C33 C25 C26 114.07(18) . . ?
C25 C26 H26A 109.3 . . ?
C25 C26 H26B 109.3 . . ?
H26A C26 H26B 108.0 . . ?
C27 C26 C25 111.41(19) . . ?
C27 C26 H26A 109.3 . . ?
C27 C26 H26B 109.3 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C29 C28 H28 118.4 . . ?
C29 C28 C33 123.2(2) . . ?
C33 C28 H28 118.4 . . ?
C28 C29 C30 118.3(2) . . ?
C28 C29 C34 122.7(2) . . ?
C30 C29 C34 118.95(19) . . ?
O8 C30 C29 118.4(2) . . ?
O8 C30 C31 122.0(2) . . ?
C31 C30 C29 119.5(2) . . ?
C30 C31 Br4 120.15(17) . . ?
C32 C31 Br4 118.57(17) . . ?
C32 C31 C30 121.2(2) . . ?
O7 C32 C31 116.6(2) . . ?
O7 C32 C33 123.5(2) . . ?
C31 C32 C33 119.9(2) . . ?
C28 C33 C25 122.0(2) . . ?
C28 C33 C32 117.8(2) . . ?
C32 C33 C25 120.16(19) . . ?
C2 C34 H34 106.5 . . ?
C2 C34 C35 111.14(18) . . ?
C29 C34 C2 111.92(18) . . ?
C29 C34 H34 106.5 . . ?
C29 C34 C35 113.86(17) . . ?
C35 C34 H34 106.5 . . ?
C34 C35 H35A 109.0 . . ?
C34 C35 H35B 109.0 . . ?
H35A C35 H35B 107.8 . . ?
C36 C35 C34 113.02(19) . . ?
C36 C35 H35A 109.0 . . ?
C36 C35 H35B 109.0 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
O10 N2 C43 119.8(2) . . ?
O10 N2 C47 118.7(2) . . ?
C47 N2 C43 121.5(2) . . ?
N2 C43 H43 120.4 . . ?
N2 C43 C44 119.1(2) . . ?
C44 C43 H43 120.4 . . ?
C43 C44 H44 120.0 . . ?
C43 C44 C45 120.1(2) . . ?
C45 C44 H44 120.0 . . ?
C44 C45 H45 119.8 . . ?
C46 C45 C44 120.3(2) . . ?
C46 C45 H45 119.8 . . ?
C45 C46 C47 117.5(2) . . ?
C45 C46 C48 122.2(3) . . ?
C47 C46 C48 120.2(3) . . ?
N2 C47 C46 121.5(2) . . ?
N2 C47 H47 119.2 . . ?
C46 C47 H47 119.2 . . ?
C46 C48 H48A 109.5 . . ?
C46 C48 H48B 109.5 . . ?
C46 C48 H48C 109.5 . . ?
H48A C48 H48B 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
O9 N1 C37 119.0(2) . . ?
O9 N1 C41 119.8(2) . . ?
C37 N1 C41 121.3(2) . . ?
N1 C37 H37 119.5 . . ?
N1 C37 C38 121.1(2) . . ?
C38 C37 H37 119.5 . . ?
C37 C38 C39 118.2(2) . . ?
C37 C38 C42 119.6(2) . . ?
C39 C38 C42 122.2(2) . . ?
C38 C39 H39 120.2 . . ?
C40 C39 C38 119.7(3) . . ?
C40 C39 H39 120.2 . . ?
C39 C40 H40 119.8 . . ?
C41 C40 C39 120.3(3) . . ?
C41 C40 H40 119.8 . . ?
N1 C41 C40 119.5(3) . . ?
N1 C41 H41 120.3 . . ?
C40 C41 H41 120.3 . . ?
C38 C42 H42A 109.5 . . ?
C38 C42 H42B 109.5 . . ?
C38 C42 H42C 109.5 . . ?
H42A C42 H42B 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
H49A C49 H49B 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
C50 C49 H49A 109.5 . . ?
C50 C49 H49B 109.5 . . ?
C50 C49 H49C 109.5 . . ?
O11 C50 C49 121.7(3) . . ?
O11 C50 C51 122.2(3) . . ?
C49 C50 C51 116.1(3) . . ?
C50 C51 H51A 109.5 . . ?
C50 C51 H51B 109.5 . . ?
C50 C51 H51C 109.5 . . ?
H51A C51 H51B 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?

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
O1 H1 O8 0.88(4) 1.81(4) 2.683(2) 172(4) .
O2 H2 O10 0.86 1.72 2.576(2) 171.7 .
O3 H3 O2 0.84(4) 1.84(4) 2.678(2) 175(4) .
O4 H4 O9 0.85 1.79 2.631(2) 167.6 2_776
O5 H5 O4 0.836(18) 1.875(19) 2.709(2) 176(4) .
O6 H6 O10 0.84 1.71 2.549(2) 176.2 1_556
O7 H7 O6 0.829(18) 1.797(19) 2.621(2) 173(3) .
O8 H8 O9 0.85 1.71 2.566(2) 177.1 2_676

_shelx_SHELXL_version_number     2014/7
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1 0 9 0.0306 0.9974 -0.0001 8.9974 0.3604 0.9386 -0.2980
-1 1 -9 0.0514 -0.9969 1.0005 -8.9978 -0.2771 -0.8881 0.3744
4 7 -1 0.0879 4.0025 7.0051 -1.0000 0.2273 0.5134 0.7816
-5 -7 2 0.0924 -5.0026 -7.0057 1.9991 -0.1019 -0.4807 -0.8724
-7 6 -2 0.0354 -6.9951 5.9992 -2.0053 0.9405 -0.3423 0.1732
7 -6 2 0.0354 6.9951 -5.9992 2.0053 -0.9405 0.3423 -0.1732
-6 6 2 0.0214 -5.9964 5.9995 1.9938 1.0580 0.1106 0.0695
6 -6 -2 0.0263 5.9964 -5.9995 -1.9938 -1.0580 -0.1106 -0.0695
7 0 -5 0.0696 6.9997 0.0038 -4.9944 -0.7807 -0.0350 0.5577
-5 -6 7 0.0965 -5.0034 -6.0056 6.9970 0.2244 0.0554 -0.9904

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_acetone_BrC2_10
_database_code_depnum_ccdc_archive 'CCDC 1551411'
_audit_update_record             
;
2017-05-22 deposited with the CCDC.
2017-06-15 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT094_acetone_BrC2_10     
;
PROBLEM: Ratio of Maximum / Minimum Residual Density ....       4.02 Report
RESPONSE: Due to unresolved disorder
;
# end Validation Reply Form
_audit_creation_date             2017-05-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C36 H36 Br4 O8, 3(C10 H8 N2 O2), 3(C3 H6 O)'
_chemical_formula_sum            'C75 H78 Br4 N6 O17'
_chemical_formula_weight         1655.07
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C10 H20 N4 O4 Br1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   37.615(8)
_cell_length_b                   7.8003(16)
_cell_length_c                   27.830(6)
_cell_angle_alpha                90
_cell_angle_beta                 120.42(3)
_cell_angle_gamma                90
_cell_volume                     7042(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10353
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      73.1380
_cell_measurement_theta_min      3.6550
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.362
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85341
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             3384
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.1712
_exptl_crystal_size_mid          0.0805
_exptl_crystal_size_min          0.0549
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            21198
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.249
_diffrn_reflns_theta_min         1.516
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -46.00   33.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676   37.0000  -90.0000 79

#__ type_ start__ end____ width___ exp.time_
  2 omega  -49.00   -4.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676   37.0000 -120.0000 45

#__ type_ start__ end____ width___ exp.time_
  3 omega  -96.00   -7.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676  125.0000  -30.0000 89

#__ type_ start__ end____ width___ exp.time_
  4 omega -114.00  -25.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676  -37.0000   90.0000 89

#__ type_ start__ end____ width___ exp.time_
  5 omega   33.00   91.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -30.0000  -60.0000 58

#__ type_ start__ end____ width___ exp.time_
  6 omega   53.00  121.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154   15.0000  -60.0000 68

#__ type_ start__ end____ width___ exp.time_
  7 omega   61.00  173.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154   15.0000 -180.0000 112

#__ type_ start__ end____ width___ exp.time_
  8 omega   98.00  173.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  125.0000 -150.0000 75

#__ type_ start__ end____ width___ exp.time_
  9 omega   41.00   99.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -45.0000  120.0000 58

#__ type_ start__ end____ width___ exp.time_
 10 omega   32.00  122.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154 -125.0000   90.0000 90

#__ type_ start__ end____ width___ exp.time_
 11 omega   26.00  109.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -94.0000  150.0000 83

#__ type_ start__ end____ width___ exp.time_
 12 omega   30.00   89.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -30.0000 -120.0000 59

#__ type_ start__ end____ width___ exp.time_
 13 omega   31.00  136.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -73.0000 -122.0000 105
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0201194000
_diffrn_orient_matrix_UB_12      -0.1232074000
_diffrn_orient_matrix_UB_13      -0.0099238000
_diffrn_orient_matrix_UB_21      -0.0327794000
_diffrn_orient_matrix_UB_22      -0.1366391000
_diffrn_orient_matrix_UB_23      -0.0314106000
_diffrn_orient_matrix_UB_31      -0.0278506000
_diffrn_orient_matrix_UB_32      0.0718906000
_diffrn_orient_matrix_UB_33      -0.0766715000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5827
_reflns_number_total             6382
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         3.166
_refine_diff_density_min         -0.787
_refine_diff_density_rms         0.141
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     466
_refine_ls_number_reflns         6382
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0566
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0993P)²+33.2637P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1443
_refine_ls_wR_factor_ref         0.1499
_refine_special_details          
;
 Refined as a 2-component perfect twin.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Riding coordinates:
 O1(H1), O2(H2), O3(H3), O4(H4)
2.b Ternary CH refined with riding coordinates:
 C13(H13), C16(H16)
2.c Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C17(H17A,H17B)
2.d Aromatic/amide H refined with riding coordinates:
 C6(H6), C12(H12), C19(H19), C20(H20), C21(H21), C22(H22), C25(H25), C26(H26),
 C27(H27), C28(H28), C29(H29), C30(H30), C32(H32), C33(H33)
2.e Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C18(H18A,H18B,H18C), C35(H35A,H35B,H35C), C36(H36A,H36B,
 H36C), C38(H38A,H38B,H38C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.66976(2) 0.60542(5) 0.77296(2) 0.02083(14) Uani 1 1 d . . . . .
Br2 Br 0.44013(2) 0.74056(5) 0.56495(2) 0.01793(14) Uani 1 1 d . . . . .
O1 O 0.66213(8) 0.4381(3) 0.86616(10) 0.0161(5) Uani 1 1 d . . . . .
H1 H 0.6806 0.3670 0.8852 0.024 Uiso 1 1 d R . . . .
O2 O 0.60006(8) 0.4570(4) 0.66837(11) 0.0191(5) Uani 1 1 d . . . . .
H2 H 0.5751 0.4772 0.6478 0.029 Uiso 1 1 d R . . . .
O3 O 0.51581(7) 0.5153(3) 0.59985(11) 0.0171(5) Uani 1 1 d . . . . .
H3 H 0.5163 0.5926 0.5780 0.026 Uiso 1 1 d R . . . .
O4 O 0.38615(8) 0.5283(3) 0.59106(11) 0.0190(6) Uani 1 1 d . . . . .
H4 H 0.3712 0.4994 0.6036 0.029 Uiso 1 1 d R . . . .
O5 O 0.72011(8) 0.2226(4) 0.92343(12) 0.0231(6) Uani 1 1 d . . . . .
O6 O 0.99620(8) 0.2353(3) 0.98148(12) 0.0195(6) Uani 1 1 d . . . . .
O7 O 0.33102(9) 0.7819(4) 0.40952(13) 0.0254(6) Uani 1 1 d . . . . .
O8 O 0.72760(13) 0.9285(5) 0.78529(14) 0.0445(9) Uani 1 1 d . . . . .
O9 O 0.5000 0.8927(5) 0.7500 0.0244(9) Uani 1 2 d S T P . .
N1 N 0.75779(10) 0.2256(4) 0.93082(14) 0.0178(7) Uani 1 1 d . . . . .
N2 N 0.95873(10) 0.2330(4) 0.97470(13) 0.0160(6) Uani 1 1 d . . . . .
N3 N 0.30877(10) 0.7706(4) 0.43317(14) 0.0184(7) Uani 1 1 d . . . . .
C1 C 0.57049(11) 0.2675(5) 0.70820(15) 0.0136(7) Uani 1 1 d . . . . .
C2 C 0.59959(11) 0.3895(5) 0.71327(15) 0.0152(7) Uani 1 1 d . . . . .
C3 C 0.63041(11) 0.4422(5) 0.76646(15) 0.0150(7) Uani 1 1 d . . . . .
C4 C 0.63200(11) 0.3776(5) 0.81416(15) 0.0144(7) Uani 1 1 d . . . . .
C5 C 0.60220(11) 0.2613(4) 0.80957(15) 0.0135(7) Uani 1 1 d . . . . .
C6 C 0.57178(10) 0.2121(5) 0.75639(15) 0.0120(7) Uani 1 1 d . . . . .
H6 H 0.5512 0.1381 0.7530 0.014 Uiso 1 1 calc R . . . .
C7 C 0.42890(11) 0.2729(5) 0.62848(15) 0.0155(7) Uani 1 1 d . . . . .
C8 C 0.42115(11) 0.4375(5) 0.60524(14) 0.0148(7) Uani 1 1 d . . . . .
C9 C 0.45007(11) 0.5171(5) 0.59507(14) 0.0149(7) Uani 1 1 d . . . . .
C10 C 0.48695(11) 0.4375(5) 0.60839(14) 0.0147(7) Uani 1 1 d . . . . .
C11 C 0.49602(11) 0.2744(5) 0.63338(15) 0.0151(7) Uani 1 1 d . . . . .
C12 C 0.46677(11) 0.1979(5) 0.64260(14) 0.0136(7) Uani 1 1 d . . . . .
H12 H 0.4727 0.0902 0.6592 0.016 Uiso 1 1 calc R . . . .
C13 C 0.53798(10) 0.1979(5) 0.65131(14) 0.0128(7) Uani 1 1 d . . . . .
H13 H 0.5457 0.2371 0.6244 0.015 Uiso 1 1 calc R . . . .
C14 C 0.53824(11) 0.0007(5) 0.65022(15) 0.0185(7) Uani 1 1 d . . . . .
H14A H 0.5308 -0.0427 0.6766 0.022 Uiso 1 1 calc R . . . .
H14B H 0.5176 -0.0386 0.6134 0.022 Uiso 1 1 calc R . . . .
C15 C 0.58012(13) -0.0722(5) 0.66455(18) 0.0248(8) Uani 1 1 d . . . . .
H15A H 0.5886 -0.0231 0.6403 0.037 Uiso 1 1 calc GR . . . .
H15B H 0.5781 -0.1945 0.6599 0.037 Uiso 1 1 calc GR . . . .
H15C H 0.6001 -0.0450 0.7025 0.037 Uiso 1 1 calc GR . . . .
C16 C 0.39670(11) 0.1902(5) 0.63863(14) 0.0141(7) Uani 1 1 d . . . . .
H16 H 0.3698 0.2214 0.6068 0.017 Uiso 1 1 calc R . . . .
C17 C 0.39831(11) -0.0070(5) 0.64042(15) 0.0157(7) Uani 1 1 d . . . . .
H17A H 0.3956 -0.0495 0.6059 0.019 Uiso 1 1 calc R . . . .
H17B H 0.4250 -0.0434 0.6707 0.019 Uiso 1 1 calc R . . . .
C18 C 0.36428(13) -0.0865(5) 0.64844(17) 0.0226(8) Uani 1 1 d . . . . .
H18A H 0.3380 -0.0405 0.6211 0.034 Uiso 1 1 calc GR . . . .
H18B H 0.3694 -0.0600 0.6851 0.034 Uiso 1 1 calc GR . . . .
H18C H 0.3641 -0.2086 0.6441 0.034 Uiso 1 1 calc GR . . . .
C19 C 0.76639(12) 0.1300(5) 0.89729(16) 0.0210(8) Uani 1 1 d . . . . .
H19 H 0.7456 0.0655 0.8688 0.025 Uiso 1 1 calc R . . . .
C20 C 0.80556(12) 0.1274(5) 0.90512(16) 0.0192(8) Uani 1 1 d . . . . .
H20 H 0.8112 0.0592 0.8824 0.023 Uiso 1 1 calc R . . . .
C21 C 0.78772(12) 0.3194(5) 0.97298(16) 0.0204(8) Uani 1 1 d . . . . .
H21 H 0.7817 0.3820 0.9964 0.024 Uiso 1 1 calc R . . . .
C22 C 0.82682(11) 0.3221(5) 0.98109(15) 0.0173(7) Uani 1 1 d . . . . .
H22 H 0.8470 0.3884 1.0097 0.021 Uiso 1 1 calc R . . . .
C23 C 0.83699(12) 0.2267(5) 0.94707(16) 0.0157(7) Uani 1 1 d . . . . .
C24 C 0.87922(12) 0.2290(5) 0.95628(16) 0.0165(7) Uani 1 1 d . . . . .
C25 C 0.90215(12) 0.3807(5) 0.97000(16) 0.0185(8) Uani 1 1 d . . . . .
H25 H 0.8906 0.4824 0.9732 0.022 Uiso 1 1 calc R . . . .
C26 C 0.94153(12) 0.3807(5) 0.97879(15) 0.0186(8) Uani 1 1 d . . . . .
H26 H 0.9564 0.4825 0.9876 0.022 Uiso 1 1 calc R . . . .
C27 C 0.93765(11) 0.0824(5) 0.96237(15) 0.0166(7) Uani 1 1 d . . . . .
H27 H 0.9501 -0.0186 0.9607 0.020 Uiso 1 1 calc R . . . .
C28 C 0.89772(11) 0.0792(5) 0.95232(15) 0.0164(7) Uani 1 1 d . . . . .
H28 H 0.8831 -0.0234 0.9429 0.020 Uiso 1 1 calc R . . . .
C29 C 0.32652(12) 0.7239(5) 0.48750(17) 0.0200(8) Uani 1 1 d . . . . .
H29 H 0.3545 0.6978 0.5073 0.024 Uiso 1 1 calc R . . . .
C30 C 0.30415(12) 0.7147(5) 0.51350(16) 0.0206(8) Uani 1 1 d . . . . .
H30 H 0.3173 0.6824 0.5508 0.025 Uiso 1 1 calc R . . . .
C31 C 0.26193(12) 0.7522(4) 0.48572(16) 0.0154(7) Uani 1 1 d . . . . .
C32 C 0.24414(12) 0.7946(5) 0.42900(16) 0.0200(8) Uani 1 1 d . . . . .
H32 H 0.2160 0.8169 0.4081 0.024 Uiso 1 1 calc R . . . .
C33 C 0.26763(12) 0.8035(5) 0.40389(16) 0.0203(8) Uani 1 1 d . . . . .
H33 H 0.2551 0.8324 0.3664 0.024 Uiso 1 1 calc R . . . .
C34 C 0.5000 0.7369(7) 0.7500 0.0246(13) Uani 1 2 d S T P . .
C35 C 0.5341(2) 0.6395(8) 0.7509(2) 0.0582(18) Uani 1 1 d . . . . .
H35A H 0.5531 0.7179 0.7490 0.087 Uiso 1 1 calc GR . . . .
H35B H 0.5232 0.5633 0.7195 0.087 Uiso 1 1 calc GR . . . .
H35C H 0.5483 0.5742 0.7847 0.087 Uiso 1 1 calc GR . . . .
C36 C 0.69387(19) 0.8910(7) 0.6878(2) 0.0401(12) Uani 1 1 d . . . . .
H36A H 0.7101 0.7883 0.6970 0.060 Uiso 1 1 calc GR . . . .
H36B H 0.6978 0.9575 0.6618 0.060 Uiso 1 1 calc GR . . . .
H36C H 0.6653 0.8614 0.6713 0.060 Uiso 1 1 calc GR . . . .
C37 C 0.70705(14) 0.9941(6) 0.73965(19) 0.0299(9) Uani 1 1 d . . . . .
C38 C 0.69367(18) 1.1767(7) 0.7322(2) 0.0450(13) Uani 1 1 d . . . . .
H38A H 0.6981 1.2215 0.7669 0.068 Uiso 1 1 calc GR . . . .
H38B H 0.6649 1.1841 0.7046 0.068 Uiso 1 1 calc GR . . . .
H38C H 0.7094 1.2422 0.7202 0.068 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C3 1.891(4) . ?
Br2 C9 1.888(4) . ?
O1 H1 0.8366 . ?
O1 C4 1.393(4) . ?
O2 H2 0.8294 . ?
O2 C2 1.364(4) . ?
O3 H3 0.8621 . ?
O3 C10 1.365(4) . ?
O4 H4 0.8277 . ?
O4 C8 1.365(4) . ?
O5 N1 1.325(4) . ?
O6 N2 1.324(4) . ?
O7 N3 1.304(5) . ?
O8 C37 1.216(6) . ?
O9 C34 1.215(7) . ?
N1 C19 1.355(5) . ?
N1 C21 1.357(5) . ?
N2 C26 1.354(5) . ?
N2 C27 1.361(5) . ?
N3 C29 1.357(5) . ?
N3 C33 1.359(5) . ?
C1 C2 1.403(5) . ?
C1 C6 1.386(5) . ?
C1 C13 1.528(5) . ?
C2 C3 1.402(5) . ?
C3 C4 1.393(5) . ?
C4 C5 1.397(5) . ?
C5 C6 1.390(5) . ?
C5 C16 1.526(5) 2_656 ?
C6 H6 0.9300 . ?
C7 C8 1.400(5) . ?
C7 C12 1.400(5) . ?
C7 C16 1.520(5) . ?
C8 C9 1.400(5) . ?
C9 C10 1.388(5) . ?
C10 C11 1.407(5) . ?
C11 C12 1.385(5) . ?
C11 C13 1.516(5) . ?
C12 H12 0.9300 . ?
C13 H13 0.9800 . ?
C13 C14 1.539(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.526(5) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C5 1.526(5) 2_656 ?
C16 H16 0.9800 . ?
C16 C17 1.539(5) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.537(5) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19 0.9300 . ?
C19 C20 1.376(5) . ?
C20 H20 0.9300 . ?
C20 C23 1.401(6) . ?
C21 H21 0.9300 . ?
C21 C22 1.371(5) . ?
C22 H22 0.9300 . ?
C22 C23 1.401(5) . ?
C23 C24 1.476(5) . ?
C24 C25 1.398(5) . ?
C24 C28 1.393(5) . ?
C25 H25 0.9300 . ?
C25 C26 1.374(5) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C27 C28 1.382(5) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
C29 C30 1.362(6) . ?
C30 H30 0.9300 . ?
C30 C31 1.401(6) . ?
C31 C31 1.470(8) 7_566 ?
C31 C32 1.407(5) . ?
C32 H32 0.9300 . ?
C32 C33 1.378(6) . ?
C33 H33 0.9300 . ?
C34 C35 1.482(6) 2_656 ?
C34 C35 1.482(6) . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C36 C37 1.501(6) . ?
C37 C38 1.490(7) . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O1 H1 114.4 . . ?
C2 O2 H2 99.9 . . ?
C10 O3 H3 137.3 . . ?
C8 O4 H4 119.8 . . ?
O5 N1 C19 119.5(3) . . ?
O5 N1 C21 119.8(3) . . ?
C19 N1 C21 120.6(3) . . ?
O6 N2 C26 119.7(3) . . ?
O6 N2 C27 119.3(3) . . ?
C26 N2 C27 120.9(3) . . ?
O7 N3 C29 120.1(3) . . ?
O7 N3 C33 120.8(3) . . ?
C29 N3 C33 119.1(3) . . ?
C2 C1 C13 121.3(3) . . ?
C6 C1 C2 118.1(3) . . ?
C6 C1 C13 120.6(3) . . ?
O2 C2 C1 122.7(3) . . ?
O2 C2 C3 117.8(3) . . ?
C3 C2 C1 119.4(3) . . ?
C2 C3 Br1 119.1(3) . . ?
C4 C3 Br1 119.9(3) . . ?
C4 C3 C2 120.9(3) . . ?
O1 C4 C5 120.5(3) . . ?
C3 C4 O1 119.2(3) . . ?
C3 C4 C5 120.2(3) . . ?
C4 C5 C16 120.9(3) . 2_656 ?
C6 C5 C4 117.8(3) . . ?
C6 C5 C16 121.3(3) . 2_656 ?
C1 C6 C5 123.4(3) . . ?
C1 C6 H6 118.3 . . ?
C5 C6 H6 118.3 . . ?
C8 C7 C16 118.4(3) . . ?
C12 C7 C8 117.2(3) . . ?
C12 C7 C16 124.3(3) . . ?
O4 C8 C7 123.7(3) . . ?
O4 C8 C9 116.5(3) . . ?
C9 C8 C7 119.9(3) . . ?
C8 C9 Br2 120.0(3) . . ?
C10 C9 Br2 118.5(3) . . ?
C10 C9 C8 121.4(3) . . ?
O3 C10 C9 122.0(3) . . ?
O3 C10 C11 118.2(3) . . ?
C9 C10 C11 119.7(3) . . ?
C10 C11 C13 118.0(3) . . ?
C12 C11 C10 117.7(3) . . ?
C12 C11 C13 124.2(3) . . ?
C7 C12 H12 118.0 . . ?
C11 C12 C7 124.0(4) . . ?
C11 C12 H12 118.0 . . ?
C1 C13 H13 106.8 . . ?
C1 C13 C14 111.4(3) . . ?
C11 C13 C1 110.8(3) . . ?
C11 C13 H13 106.8 . . ?
C11 C13 C14 113.8(3) . . ?
C14 C13 H13 106.8 . . ?
C13 C14 H14A 109.1 . . ?
C13 C14 H14B 109.1 . . ?
H14A C14 H14B 107.8 . . ?
C15 C14 C13 112.6(3) . . ?
C15 C14 H14A 109.1 . . ?
C15 C14 H14B 109.1 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C5 C16 H16 106.5 2_656 . ?
C5 C16 C17 110.6(3) 2_656 . ?
C7 C16 C5 112.2(3) . 2_656 ?
C7 C16 H16 106.5 . . ?
C7 C16 C17 114.1(3) . . ?
C17 C16 H16 106.5 . . ?
C16 C17 H17A 109.1 . . ?
C16 C17 H17B 109.1 . . ?
H17A C17 H17B 107.8 . . ?
C18 C17 C16 112.7(3) . . ?
C18 C17 H17A 109.1 . . ?
C18 C17 H17B 109.1 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 C19 H19 119.7 . . ?
N1 C19 C20 120.6(4) . . ?
C20 C19 H19 119.7 . . ?
C19 C20 H20 119.7 . . ?
C19 C20 C23 120.5(4) . . ?
C23 C20 H20 119.7 . . ?
N1 C21 H21 119.9 . . ?
N1 C21 C22 120.1(4) . . ?
C22 C21 H21 119.9 . . ?
C21 C22 H22 119.4 . . ?
C21 C22 C23 121.2(4) . . ?
C23 C22 H22 119.4 . . ?
C20 C23 C22 116.9(3) . . ?
C20 C23 C24 122.1(3) . . ?
C22 C23 C24 120.9(3) . . ?
C25 C24 C23 121.2(3) . . ?
C28 C24 C23 120.9(3) . . ?
C28 C24 C25 117.9(4) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 C24 120.6(4) . . ?
C26 C25 H25 119.7 . . ?
N2 C26 C25 120.2(4) . . ?
N2 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
N2 C27 H27 120.0 . . ?
N2 C27 C28 120.1(3) . . ?
C28 C27 H27 120.0 . . ?
C24 C28 H28 119.9 . . ?
C27 C28 C24 120.3(4) . . ?
C27 C28 H28 119.9 . . ?
N3 C29 H29 119.4 . . ?
N3 C29 C30 121.2(4) . . ?
C30 C29 H29 119.4 . . ?
C29 C30 H30 119.0 . . ?
C29 C30 C31 121.9(4) . . ?
C31 C30 H30 119.0 . . ?
C30 C31 C31 121.9(4) . 7_566 ?
C30 C31 C32 115.5(4) . . ?
C32 C31 C31 122.6(4) . 7_566 ?
C31 C32 H32 119.4 . . ?
C33 C32 C31 121.2(4) . . ?
C33 C32 H32 119.4 . . ?
N3 C33 C32 120.9(4) . . ?
N3 C33 H33 119.5 . . ?
C32 C33 H33 119.5 . . ?
O9 C34 C35 120.8(4) . . ?
O9 C34 C35 120.8(4) . 2_656 ?
C35 C34 C35 118.3(7) . 2_656 ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C37 C36 H36A 109.5 . . ?
C37 C36 H36B 109.5 . . ?
C37 C36 H36C 109.5 . . ?
O8 C37 C36 120.4(5) . . ?
O8 C37 C38 122.6(4) . . ?
C38 C37 C36 117.0(4) . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?

_shelx_SHELXL_version_number     2014/7
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 0 -12 0.0345 -0.0038 0.0001 -11.9989 0.1190 0.3770 0.9201
0 0 12 0.0323 0.0038 -0.0001 11.9989 -0.1190 -0.3770 -0.9201
-11 -5 5 0.0726 -10.9993 -5.0000 4.9997 0.3451 0.8867 -0.4365
12 5 -5 0.1096 11.9994 5.0000 -4.9998 -0.3250 -0.9195 0.4086
28 -1 -18 0.0355 27.9969 -0.9999 -17.9993 0.8651 -0.2157 0.5284
-27 0 18 0.0282 -26.9968 -0.0001 17.9992 -0.7218 0.3196 -0.6282
28 1 -6 0.0441 28.0006 0.9999 -6.0003 0.4997 -0.8660 -0.2479
-24 0 2 0.0132 -24.0015 0.0001 2.0006 -0.5028 0.7239 0.5151
-30 -2 14 0.0088 -29.9983 -2.0000 13.9996 -0.4961 0.8169 -0.3817
19 2 -16 0.0647 18.9967 2.0001 -15.9991 0.2945 -0.3934 0.8414
-11 -4 9 0.0464 -10.9981 -4.0000 8.9994 0.1823 0.6244 -0.6713
-6 5 1 0.0931 -6.0003 5.0000 1.0003 -0.7467 -0.5179 0.4499
29 -1 -8 0.0306 29.0001 -1.0000 -8.0002 0.7861 -0.5627 -0.2662

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_1_BrC2
_database_code_depnum_ccdc_archive 'CCDC 1551402'
_audit_update_record             
;
2017-05-22 deposited with the CCDC.
2017-06-15 downloaded from the CCDC.
;
_audit_creation_date             2017-05-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C36 H36 Br4 O8, 2(C5 H5 N O), C3 H6 O'
_chemical_formula_sum            'C49 H52 Br4 N2 O11'
_chemical_formula_weight         1164.56
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C5 H5 N1 O3 Br1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   13.7077(4)
_cell_length_b                   13.9155(4)
_cell_length_c                   13.9398(4)
_cell_angle_alpha                90.621(2)
_cell_angle_beta                 116.716(3)
_cell_angle_gamma                96.052(2)
_cell_volume                     2356.84(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9555
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      73.1510
_cell_measurement_theta_min      3.5350
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.695
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87460
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.641
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1176
_exptl_crystal_size_max          0.2084
_exptl_crystal_size_mid          0.1175
_exptl_crystal_size_min          0.0517
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13651
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        66.746
_diffrn_reflns_theta_max         66.746
_diffrn_reflns_theta_min         3.201
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -49.00   33.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676   37.0000 -120.0000 82

#__ type_ start__ end____ width___ exp.time_
  2 omega  -96.00   -2.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676  125.0000  -90.0000 94

#__ type_ start__ end____ width___ exp.time_
  3 omega -115.00  -13.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676  -57.0000   90.0000 102

#__ type_ start__ end____ width___ exp.time_
  4 omega  111.00  178.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  125.0000  150.0000 67

#__ type_ start__ end____ width___ exp.time_
  5 omega   90.00  169.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      105.6154   30.0000  120.0000 79

#__ type_ start__ end____ width___ exp.time_
  6 omega   77.00  160.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      105.6154   61.0000  150.0000 83

#__ type_ start__ end____ width___ exp.time_
  7 omega   72.00   99.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -45.0000   30.0000 27

#__ type_ start__ end____ width___ exp.time_
  8 omega   44.00  122.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      105.6154 -125.0000    0.0000 78

#__ type_ start__ end____ width___ exp.time_
  9 omega   63.00   93.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -45.0000  -90.0000 30

#__ type_ start__ end____ width___ exp.time_
 10 omega   51.00   81.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -30.0000 -150.0000 30

#__ type_ start__ end____ width___ exp.time_
 11 omega   32.00   77.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -30.0000 -180.0000 45

#__ type_ start__ end____ width___ exp.time_
 12 omega   80.00  174.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      105.6154   45.0000 -150.0000 94

#__ type_ start__ end____ width___ exp.time_
 13 omega   31.00  109.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -94.0000   90.0000 78

#__ type_ start__ end____ width___ exp.time_
 14 omega   43.00  137.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -77.0000  150.0000 94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0937908000
_diffrn_orient_matrix_UB_12      0.0629408000
_diffrn_orient_matrix_UB_13      -0.0549570000
_diffrn_orient_matrix_UB_21      0.0701098000
_diffrn_orient_matrix_UB_22      0.0857147000
_diffrn_orient_matrix_UB_23      0.0809319000
_diffrn_orient_matrix_UB_31      0.0486117000
_diffrn_orient_matrix_UB_32      0.0337509000
_diffrn_orient_matrix_UB_33      -0.0761786000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7560
_reflns_number_total             8284
_reflns_odcompleteness_completeness 99.04
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         1.379
_refine_diff_density_min         -0.739
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     621
_refine_ls_number_reflns         8284
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0294
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0337P)²+1.7564P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0733
_refine_ls_wR_factor_ref         0.0760
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O2-H2
 0.85 with sigma of 0.02
 O3-H3
 0.85 with sigma of 0.02
3.a Riding coordinates:
 O1(H1), O3(H3), O5(H5), O7(H7)
3.b Ternary CH refined with riding coordinates:
 C7(H7A), C16(H16), C25(H25), C34(H34)
3.c Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C17(H17A,H17B), C26(H26A,H26B), C35(H35A,H35B)
3.d Aromatic/amide H refined with riding coordinates:
 C3(H3A), C11(H11), C20(H20), C29(H29), C42(H42), C43(H43), C44(H44), C45(H45),
  C46(H46), C37(H37), C38(H38), C39(H39), C40(H40), C41(H41)
3.e Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C18(H18A,H18B,H18C), C27(H27A,H27B,H27C), C36(H36A,H36B,
 H36C), C47(H47A,H47B,H47C), C49(H49A,H49B,H49C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.37604(2) 0.48966(2) 0.75548(2) 0.02257(7) Uani 1 1 d . . . . .
Br2 Br 0.39501(2) 0.62758(2) 0.27374(2) 0.02910(8) Uani 1 1 d . . . . .
Br3 Br 0.40823(2) 0.12017(2) 0.08839(2) 0.02554(8) Uani 1 1 d . . . . .
Br4 Br 0.41655(2) -0.02576(2) 0.61940(2) 0.02377(7) Uani 1 1 d . . . . .
O1 O 0.25715(15) 0.27897(12) 0.71992(14) 0.0228(4) Uani 1 1 d . . . . .
H1 H 0.3032 0.2895 0.7852 0.069(15) Uiso 1 1 d R . . . .
O2 O 0.24178(15) 0.57830(12) 0.55393(14) 0.0229(4) Uani 1 1 d D . . . .
H2 H 0.227(3) 0.600(3) 0.4930(19) 0.038(10) Uiso 1 1 d D . . . .
O3 O 0.23044(16) 0.63250(13) 0.36981(14) 0.0238(4) Uani 1 1 d D . . . .
H3 H 0.2770 0.6817 0.3941 0.074(16) Uiso 1 1 d DR . . . .
O4 O 0.28638(15) 0.47162(14) 0.09764(15) 0.0227(4) Uani 1 1 d . . . . .
H4 H 0.276(3) 0.423(3) 0.063(3) 0.035(10) Uiso 1 1 d . . . . .
O5 O 0.26674(15) 0.28962(13) 0.01194(15) 0.0227(4) Uani 1 1 d . . . . .
H5 H 0.3119 0.2983 -0.0140 0.10(2) Uiso 1 1 d R . . . .
O6 O 0.29705(15) -0.00554(13) 0.18884(16) 0.0229(4) Uani 1 1 d . . . . .
H6 H 0.288(3) -0.028(3) 0.234(3) 0.032(10) Uiso 1 1 d . . . . .
O7 O 0.28813(14) -0.06034(12) 0.36998(14) 0.0205(4) Uani 1 1 d . . . . .
H7 H 0.3195 -0.1082 0.3961 0.042(10) Uiso 1 1 d R . . . .
O8 O 0.28264(16) 0.09841(14) 0.67218(14) 0.0253(4) Uani 1 1 d . . . . .
H8 H 0.270(3) 0.153(3) 0.684(3) 0.039(10) Uiso 1 1 d . . . . .
C1 C 0.2119(2) 0.33295(17) 0.63287(19) 0.0174(5) Uani 1 1 d . . . . .
C2 C 0.1232(2) 0.28751(17) 0.53966(19) 0.0166(5) Uani 1 1 d . . . . .
C3 C 0.0767(2) 0.34131(17) 0.44985(19) 0.0169(5) Uani 1 1 d . . . . .
H3A H 0.0192 0.3107 0.3874 0.020 Uiso 1 1 calc R . . . .
C4 C 0.1121(2) 0.43914(17) 0.44888(19) 0.0168(5) Uani 1 1 d . . . . .
C5 C 0.2018(2) 0.48288(17) 0.54348(19) 0.0175(5) Uani 1 1 d . . . . .
C6 C 0.25136(19) 0.42951(17) 0.63252(18) 0.0167(5) Uani 1 1 d . . . . .
C7 C 0.0568(2) 0.49676(17) 0.34997(19) 0.0170(5) Uani 1 1 d . . . . .
H7A H 0.0689 0.5647 0.3761 0.020 Uiso 1 1 calc R . . . .
C8 C -0.0686(2) 0.46871(18) 0.28808(19) 0.0191(5) Uani 1 1 d . . . . .
H8A H -0.0841 0.4028 0.2571 0.023 Uiso 1 1 calc R . . . .
H8B H -0.1002 0.4711 0.3378 0.023 Uiso 1 1 calc R . . . .
C9 C -0.1221(2) 0.5363(2) 0.1987(2) 0.0255(5) Uani 1 1 d . . . . .
H9A H -0.0952 0.5303 0.1464 0.038 Uiso 1 1 calc GR . . . .
H9B H -0.1043 0.6019 0.2288 0.038 Uiso 1 1 calc GR . . . .
H9C H -0.2005 0.5193 0.1647 0.038 Uiso 1 1 calc GR . . . .
C10 C 0.11339(19) 0.49111(16) 0.27777(18) 0.0154(4) Uani 1 1 d . . . . .
C11 C 0.07985(19) 0.41887(16) 0.19565(18) 0.0149(4) Uani 1 1 d . . . . .
H11 H 0.0202 0.3735 0.1843 0.018 Uiso 1 1 calc R . . . .
C12 C 0.13072(19) 0.41063(16) 0.12936(18) 0.0142(4) Uani 1 1 d . . . . .
C13 C 0.22534(19) 0.47485(17) 0.15212(19) 0.0170(5) Uani 1 1 d . . . . .
C14 C 0.26064(19) 0.54741(17) 0.23465(19) 0.0180(5) Uani 1 1 d . . . . .
C15 C 0.2034(2) 0.55859(17) 0.29372(19) 0.0171(5) Uani 1 1 d . . . . .
C16 C 0.08590(19) 0.33264(16) 0.03732(18) 0.0148(4) Uani 1 1 d . . . . .
H16 H 0.1095 0.3563 -0.0158 0.018 Uiso 1 1 calc R . . . .
C17 C -0.04031(19) 0.31687(17) -0.01993(19) 0.0174(5) Uani 1 1 d . . . . .
H17A H -0.0667 0.2877 0.0283 0.021 Uiso 1 1 calc R . . . .
H17B H -0.0678 0.3791 -0.0368 0.021 Uiso 1 1 calc R . . . .
C18 C -0.0856(2) 0.25215(19) -0.1232(2) 0.0251(5) Uani 1 1 d . . . . .
H18A H -0.0571 0.2792 -0.1699 0.038 Uiso 1 1 calc GR . . . .
H18B H -0.1645 0.2477 -0.1586 0.038 Uiso 1 1 calc GR . . . .
H18C H -0.0638 0.1887 -0.1062 0.038 Uiso 1 1 calc GR . . . .
C19 C 0.13839(19) 0.23964(16) 0.07660(18) 0.0151(4) Uani 1 1 d . . . . .
C20 C 0.10084(18) 0.17258(16) 0.12953(18) 0.0144(4) Uani 1 1 d . . . . .
H20 H 0.0407 0.1845 0.1400 0.017 Uiso 1 1 calc R . . . .
C21 C 0.14867(18) 0.08822(16) 0.16784(18) 0.0144(4) Uani 1 1 d . . . . .
C22 C 0.24201(19) 0.07324(17) 0.15508(19) 0.0168(5) Uani 1 1 d . . . . .
C23 C 0.28049(19) 0.14006(17) 0.10241(19) 0.0170(5) Uani 1 1 d . . . . .
C24 C 0.2298(2) 0.22254(17) 0.06248(18) 0.0165(5) Uani 1 1 d . . . . .
C25 C 0.09959(19) 0.01325(16) 0.21886(18) 0.0149(4) Uani 1 1 d . . . . .
H25 H 0.1240 -0.0485 0.2102 0.018 Uiso 1 1 calc R . . . .
C26 C -0.02697(19) -0.00167(17) 0.15803(19) 0.0170(5) Uani 1 1 d . . . . .
H26A H -0.0545 0.0583 0.1640 0.020 Uiso 1 1 calc R . . . .
H26B H -0.0496 -0.0169 0.0824 0.020 Uiso 1 1 calc R . . . .
C27 C -0.0786(2) -0.08235(18) 0.2002(2) 0.0222(5) Uani 1 1 d . . . . .
H27A H -0.1568 -0.0920 0.1558 0.033 Uiso 1 1 calc GR . . . .
H27B H -0.0631 -0.0646 0.2729 0.033 Uiso 1 1 calc GR . . . .
H27C H -0.0485 -0.1412 0.1985 0.033 Uiso 1 1 calc GR . . . .
C28 C 0.14551(19) 0.03584(16) 0.33997(19) 0.0157(4) Uani 1 1 d . . . . .
C29 C 0.09689(19) 0.09487(16) 0.38317(19) 0.0153(4) Uani 1 1 d . . . . .
H29 H 0.0343 0.1211 0.3361 0.018 Uiso 1 1 calc R . . . .
C30 C 0.13716(19) 0.11660(16) 0.49328(19) 0.0158(4) Uani 1 1 d . . . . .
C31 C 0.2340(2) 0.07888(17) 0.56353(19) 0.0177(5) Uani 1 1 d . . . . .
C32 C 0.28322(19) 0.01919(16) 0.52211(19) 0.0170(5) Uani 1 1 d . . . . .
C33 C 0.23964(19) -0.00356(16) 0.41191(19) 0.0163(4) Uani 1 1 d . . . . .
C34 C 0.0820(2) 0.18087(17) 0.53869(19) 0.0175(5) Uani 1 1 d . . . . .
H34 H 0.1069 0.1661 0.6141 0.021 Uiso 1 1 calc R . . . .
C35 C -0.0437(2) 0.15801(17) 0.4832(2) 0.0193(5) Uani 1 1 d . . . . .
H35A H -0.0719 0.1728 0.4083 0.023 Uiso 1 1 calc R . . . .
H35B H -0.0635 0.0893 0.4852 0.023 Uiso 1 1 calc R . . . .
C36 C -0.0977(2) 0.2153(2) 0.5363(2) 0.0253(5) Uani 1 1 d . . . . .
H36A H -0.1756 0.1954 0.5021 0.038 Uiso 1 1 calc GR . . . .
H36B H -0.0838 0.2832 0.5288 0.038 Uiso 1 1 calc GR . . . .
H36C H -0.0675 0.2033 0.6112 0.038 Uiso 1 1 calc GR . . . .
O10 O 0.39972(15) 0.31204(14) 0.92456(15) 0.0269(4) Uani 1 1 d . . . . .
N2 N 0.49106(18) 0.28160(17) 0.93209(17) 0.0244(5) Uani 1 1 d . . . . .
C42 C 0.5872(2) 0.3407(2) 0.9817(2) 0.0286(6) Uani 1 1 d . . . . .
H42 H 0.5885 0.4022 1.0093 0.034 Uiso 1 1 calc R . . . .
C43 C 0.6833(2) 0.3096(2) 0.9912(2) 0.0329(6) Uani 1 1 d . . . . .
H43 H 0.7496 0.3496 1.0267 0.040 Uiso 1 1 calc R . . . .
C44 C 0.6807(2) 0.2189(2) 0.9481(2) 0.0314(6) Uani 1 1 d . . . . .
H44 H 0.7453 0.1974 0.9546 0.038 Uiso 1 1 calc R . . . .
C45 C 0.5816(2) 0.1608(2) 0.8952(2) 0.0281(6) Uani 1 1 d . . . . .
H45 H 0.5784 0.1003 0.8642 0.034 Uiso 1 1 calc R . . . .
C46 C 0.4872(2) 0.1927(2) 0.8886(2) 0.0266(6) Uani 1 1 d . . . . .
H46 H 0.4204 0.1531 0.8542 0.032 Uiso 1 1 calc R . . . .
O9 O 0.62972(16) 0.21697(13) 0.55188(17) 0.0310(4) Uani 1 1 d . . . . .
N1 N 0.53189(18) 0.24292(15) 0.48467(18) 0.0233(5) Uani 1 1 d . . . . .
C37 C 0.4446(2) 0.2182(2) 0.5029(2) 0.0307(6) Uani 1 1 d . . . . .
H37 H 0.4512 0.1790 0.5586 0.037 Uiso 1 1 calc R . . . .
C38 C 0.3454(2) 0.2509(2) 0.4393(3) 0.0342(7) Uani 1 1 d . . . . .
H38 H 0.2852 0.2342 0.4524 0.041 Uiso 1 1 calc R . . . .
C39 C 0.3355(2) 0.3081(2) 0.3568(2) 0.0325(6) Uani 1 1 d . . . . .
H39 H 0.2690 0.3311 0.3139 0.039 Uiso 1 1 calc R . . . .
C40 C 0.4263(3) 0.3311(2) 0.3383(2) 0.0365(7) Uani 1 1 d . . . . .
H40 H 0.4212 0.3694 0.2824 0.044 Uiso 1 1 calc R . . . .
C41 C 0.5239(2) 0.2968(2) 0.4031(2) 0.0311(6) Uani 1 1 d . . . . .
H41 H 0.5846 0.3112 0.3902 0.037 Uiso 1 1 calc R . . . .
O11 O -0.14290(16) 0.21126(15) 0.20134(16) 0.0299(4) Uani 1 1 d . . . . .
C47 C -0.2866(3) 0.0815(2) 0.1600(2) 0.0330(6) Uani 1 1 d . . . . .
H47A H -0.2578 0.0556 0.1153 0.049 Uiso 1 1 calc GR . . . .
H47B H -0.3640 0.0846 0.1181 0.049 Uiso 1 1 calc GR . . . .
H47C H -0.2750 0.0405 0.2182 0.049 Uiso 1 1 calc GR . . . .
C48 C -0.2288(2) 0.1814(2) 0.2046(2) 0.0265(6) Uani 1 1 d . . . . .
C49 C -0.2808(3) 0.2415(2) 0.2542(3) 0.0349(6) Uani 1 1 d . . . . .
H49A H -0.2308 0.2982 0.2920 0.052 Uiso 1 1 calc GR . . . .
H49B H -0.2976 0.2043 0.3036 0.052 Uiso 1 1 calc GR . . . .
H49C H -0.3473 0.2606 0.1987 0.052 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C6 1.895(2) . ?
Br2 C14 1.894(2) . ?
Br3 C23 1.895(2) . ?
Br4 C32 1.898(2) . ?
O1 H1 0.8425 . ?
O1 C1 1.365(3) . ?
O2 H2 0.847(18) . ?
O2 C5 1.362(3) . ?
O3 H3 0.8362 . ?
O3 C15 1.365(3) . ?
O4 H4 0.79(4) . ?
O4 C13 1.363(3) . ?
O5 H5 0.8450 . ?
O5 C24 1.363(3) . ?
O6 H6 0.76(4) . ?
O6 C22 1.363(3) . ?
O7 H7 0.8284 . ?
O7 C33 1.363(3) . ?
O8 H8 0.82(4) . ?
O8 C31 1.363(3) . ?
C1 C2 1.402(4) . ?
C1 C6 1.395(3) . ?
C2 C3 1.392(3) . ?
C2 C34 1.529(3) . ?
C3 H3A 0.9300 . ?
C3 C4 1.398(3) . ?
C4 C5 1.410(4) . ?
C4 C7 1.527(3) . ?
C5 C6 1.386(3) . ?
C7 H7A 0.9800 . ?
C7 C8 1.540(3) . ?
C7 C10 1.527(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.524(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.392(3) . ?
C10 C15 1.399(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.395(3) . ?
C12 C13 1.400(3) . ?
C12 C16 1.524(3) . ?
C13 C14 1.396(4) . ?
C14 C15 1.386(4) . ?
C16 H16 0.9800 . ?
C16 C17 1.534(3) . ?
C16 C19 1.533(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.523(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.391(3) . ?
C19 C24 1.397(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.398(3) . ?
C21 C22 1.404(3) . ?
C21 C25 1.531(3) . ?
C22 C23 1.393(3) . ?
C23 C24 1.394(3) . ?
C25 H25 0.9800 . ?
C25 C26 1.539(3) . ?
C25 C28 1.529(3) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C26 C27 1.526(3) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 C29 1.395(3) . ?
C28 C33 1.403(3) . ?
C29 H29 0.9300 . ?
C29 C30 1.395(3) . ?
C30 C31 1.409(3) . ?
C30 C34 1.528(3) . ?
C31 C32 1.392(4) . ?
C32 C33 1.393(3) . ?
C34 H34 0.9800 . ?
C34 C35 1.533(3) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C35 C36 1.527(3) . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
O10 N2 1.324(3) . ?
N2 C42 1.353(4) . ?
N2 C46 1.357(4) . ?
C42 H42 0.9300 . ?
C42 C43 1.380(4) . ?
C43 H43 0.9300 . ?
C43 C44 1.382(5) . ?
C44 H44 0.9300 . ?
C44 C45 1.378(4) . ?
C45 H45 0.9300 . ?
C45 C46 1.376(4) . ?
C46 H46 0.9300 . ?
O9 N1 1.337(3) . ?
N1 C37 1.343(4) . ?
N1 C41 1.338(4) . ?
C37 H37 0.9300 . ?
C37 C38 1.378(4) . ?
C38 H38 0.9300 . ?
C38 C39 1.370(4) . ?
C39 H39 0.9300 . ?
C39 C40 1.387(4) . ?
C40 H40 0.9300 . ?
C40 C41 1.375(4) . ?
C41 H41 0.9300 . ?
O11 C48 1.228(4) . ?
C47 H47A 0.9600 . ?
C47 H47B 0.9600 . ?
C47 H47C 0.9600 . ?
C47 C48 1.501(4) . ?
C48 C49 1.496(4) . ?
C49 H49A 0.9600 . ?
C49 H49B 0.9600 . ?
C49 H49C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 136.5 . . ?
C5 O2 H2 111(3) . . ?
C15 O3 H3 136.8 . . ?
C13 O4 H4 115(3) . . ?
C24 O5 H5 141.0 . . ?
C22 O6 H6 111(3) . . ?
C33 O7 H7 127.3 . . ?
C31 O8 H8 108(3) . . ?
O1 C1 C2 117.6(2) . . ?
O1 C1 C6 123.0(2) . . ?
C6 C1 C2 119.4(2) . . ?
C1 C2 C34 119.5(2) . . ?
C3 C2 C1 118.4(2) . . ?
C3 C2 C34 122.1(2) . . ?
C2 C3 H3A 118.4 . . ?
C2 C3 C4 123.2(2) . . ?
C4 C3 H3A 118.4 . . ?
C3 C4 C5 117.2(2) . . ?
C3 C4 C7 121.9(2) . . ?
C5 C4 C7 121.0(2) . . ?
O2 C5 C4 122.8(2) . . ?
O2 C5 C6 116.8(2) . . ?
C6 C5 C4 120.3(2) . . ?
C1 C6 Br1 119.76(18) . . ?
C5 C6 Br1 118.82(18) . . ?
C5 C6 C1 121.4(2) . . ?
C4 C7 H7A 106.7 . . ?
C4 C7 C8 113.45(19) . . ?
C4 C7 C10 110.35(19) . . ?
C8 C7 H7A 106.7 . . ?
C10 C7 H7A 106.7 . . ?
C10 C7 C8 112.47(19) . . ?
C7 C8 H8A 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
C9 C8 C7 111.6(2) . . ?
C9 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C7 122.2(2) . . ?
C11 C10 C15 117.3(2) . . ?
C15 C10 C7 120.5(2) . . ?
C10 C11 H11 118.2 . . ?
C10 C11 C12 123.7(2) . . ?
C12 C11 H11 118.2 . . ?
C11 C12 C13 117.7(2) . . ?
C11 C12 C16 120.8(2) . . ?
C13 C12 C16 121.5(2) . . ?
O4 C13 C12 123.8(2) . . ?
O4 C13 C14 116.9(2) . . ?
C14 C13 C12 119.3(2) . . ?
C13 C14 Br2 119.48(18) . . ?
C15 C14 Br2 118.73(18) . . ?
C15 C14 C13 121.7(2) . . ?
O3 C15 C10 116.4(2) . . ?
O3 C15 C14 123.6(2) . . ?
C14 C15 C10 120.0(2) . . ?
C12 C16 H16 106.7 . . ?
C12 C16 C17 112.17(19) . . ?
C12 C16 C19 110.37(19) . . ?
C17 C16 H16 106.7 . . ?
C19 C16 H16 106.7 . . ?
C19 C16 C17 113.64(19) . . ?
C16 C17 H17A 109.1 . . ?
C16 C17 H17B 109.1 . . ?
H17A C17 H17B 107.9 . . ?
C18 C17 C16 112.4(2) . . ?
C18 C17 H17A 109.1 . . ?
C18 C17 H17B 109.1 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C16 122.5(2) . . ?
C20 C19 C24 118.2(2) . . ?
C24 C19 C16 119.2(2) . . ?
C19 C20 H20 118.2 . . ?
C19 C20 C21 123.5(2) . . ?
C21 C20 H20 118.2 . . ?
C20 C21 C22 117.5(2) . . ?
C20 C21 C25 121.5(2) . . ?
C22 C21 C25 121.0(2) . . ?
O6 C22 C21 123.7(2) . . ?
O6 C22 C23 116.8(2) . . ?
C23 C22 C21 119.5(2) . . ?
C22 C23 Br3 118.94(17) . . ?
C22 C23 C24 122.1(2) . . ?
C24 C23 Br3 118.95(18) . . ?
O5 C24 C19 117.6(2) . . ?
O5 C24 C23 123.2(2) . . ?
C23 C24 C19 119.2(2) . . ?
C21 C25 H25 106.4 . . ?
C21 C25 C26 111.54(18) . . ?
C26 C25 H25 106.4 . . ?
C28 C25 C21 111.73(18) . . ?
C28 C25 H25 106.4 . . ?
C28 C25 C26 113.92(19) . . ?
C25 C26 H26A 109.0 . . ?
C25 C26 H26B 109.0 . . ?
H26A C26 H26B 107.8 . . ?
C27 C26 C25 113.12(19) . . ?
C27 C26 H26A 109.0 . . ?
C27 C26 H26B 109.0 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C29 C28 C25 122.4(2) . . ?
C29 C28 C33 117.7(2) . . ?
C33 C28 C25 119.9(2) . . ?
C28 C29 H29 118.3 . . ?
C30 C29 C28 123.5(2) . . ?
C30 C29 H29 118.3 . . ?
C29 C30 C31 117.7(2) . . ?
C29 C30 C34 122.5(2) . . ?
C31 C30 C34 119.8(2) . . ?
O8 C31 C30 122.6(2) . . ?
O8 C31 C32 117.7(2) . . ?
C32 C31 C30 119.7(2) . . ?
C31 C32 Br4 118.15(18) . . ?
C31 C32 C33 121.5(2) . . ?
C33 C32 Br4 120.32(18) . . ?
O7 C33 C28 117.9(2) . . ?
O7 C33 C32 122.1(2) . . ?
C32 C33 C28 119.9(2) . . ?
C2 C34 H34 106.5 . . ?
C2 C34 C35 113.9(2) . . ?
C30 C34 C2 110.18(19) . . ?
C30 C34 H34 106.5 . . ?
C30 C34 C35 112.7(2) . . ?
C35 C34 H34 106.5 . . ?
C34 C35 H35A 109.1 . . ?
C34 C35 H35B 109.1 . . ?
H35A C35 H35B 107.8 . . ?
C36 C35 C34 112.4(2) . . ?
C36 C35 H35A 109.1 . . ?
C36 C35 H35B 109.1 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
O10 N2 C42 119.2(2) . . ?
O10 N2 C46 120.0(2) . . ?
C42 N2 C46 120.8(2) . . ?
N2 C42 H42 120.1 . . ?
N2 C42 C43 119.9(3) . . ?
C43 C42 H42 120.1 . . ?
C42 C43 H43 120.0 . . ?
C42 C43 C44 119.9(3) . . ?
C44 C43 H43 120.0 . . ?
C43 C44 H44 120.3 . . ?
C45 C44 C43 119.3(3) . . ?
C45 C44 H44 120.3 . . ?
C44 C45 H45 120.2 . . ?
C46 C45 C44 119.7(3) . . ?
C46 C45 H45 120.2 . . ?
N2 C46 C45 120.4(3) . . ?
N2 C46 H46 119.8 . . ?
C45 C46 H46 119.8 . . ?
O9 N1 C37 119.5(2) . . ?
O9 N1 C41 119.3(2) . . ?
C41 N1 C37 121.2(2) . . ?
N1 C37 H37 120.0 . . ?
N1 C37 C38 120.1(3) . . ?
C38 C37 H37 120.0 . . ?
C37 C38 H38 120.0 . . ?
C39 C38 C37 120.0(3) . . ?
C39 C38 H38 120.0 . . ?
C38 C39 H39 120.6 . . ?
C38 C39 C40 118.8(3) . . ?
C40 C39 H39 120.6 . . ?
C39 C40 H40 120.2 . . ?
C41 C40 C39 119.6(3) . . ?
C41 C40 H40 120.2 . . ?
N1 C41 C40 120.3(3) . . ?
N1 C41 H41 119.9 . . ?
C40 C41 H41 119.9 . . ?
H47A C47 H47B 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
C48 C47 H47A 109.5 . . ?
C48 C47 H47B 109.5 . . ?
C48 C47 H47C 109.5 . . ?
O11 C48 C47 121.4(3) . . ?
O11 C48 C49 122.2(3) . . ?
C49 C48 C47 116.4(3) . . ?
C48 C49 H49A 109.5 . . ?
C48 C49 H49B 109.5 . . ?
C48 C49 H49C 109.5 . . ?
H49A C49 H49B 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?

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
O2 H2 O3 0.847(18) 1.80(2) 2.625(2) 163(4) .
O3 H3 O9 0.84 1.71 2.545(3) 177.4 2_666
O4 H4 O5 0.79(4) 1.95(4) 2.723(3) 166(4) .
O6 H6 O7 0.76(4) 1.95(4) 2.697(3) 167(4) .
O7 H7 O9 0.83 1.76 2.583(2) 173.1 2_656
O8 H8 O1 0.82(4) 1.87(4) 2.690(3) 174(4) .

_shelx_SHELXL_version_number     2014/7
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-2 6 6 0.0399 -2.0000 6.0000 6.0000 0.2355 0.8597 -0.3518
5 -2 -9 0.0537 5.0000 -2.0000 -9.0000 -0.1002 -0.5493 0.8612
-4 -8 2 0.0882 -4.0000 -8.0000 2.0000 -0.2383 -0.8043 -0.6168
-8 3 1 0.0286 -8.0000 3.0000 1.0000 0.8842 -0.2228 -0.3638
9 -3 -2 0.0169 9.0000 -3.0000 -2.0000 -0.9230 0.2120 0.4886
5 3 -8 0.0814 5.0000 3.0000 -8.0000 0.1595 -0.0398 0.9537
-5 -2 9 0.0682 -5.0000 -2.0000 9.0000 -0.1515 0.2064 -0.9962
-7 -3 0 0.0506 -7.0000 -3.0000 -0.0000 0.4677 -0.7479 -0.4415
0 -1 -8 0.0538 0.0000 -1.0000 -8.0000 0.3767 -0.7332 0.5757
5 3 4 0.0213 5.0000 3.0000 4.0000 -0.5000 0.9314 0.0396

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_acetone_BrC2_11
_database_code_depnum_ccdc_archive 'CCDC 1551412'
_audit_update_record             
;
2017-05-22 deposited with the CCDC.
2017-06-15 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT420_acetone_BrC2_11     
;
PROBLEM: D-H Without Acceptor      *O9     -- *H9E    ...     Please Check 
RESPONSE: Disorderd solvent surrounded by carbon atoms
;
# end Validation Reply Form
_audit_creation_date             2017-04-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'C36 H36 Br4 O8, C13 H14 N2 O2, 4(C H4 O), C3 H6 O, H2 O'
_chemical_formula_sum            'C56 H74 Br4 N2 O16'
_chemical_formula_weight         1350.81
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N6 O10'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 1 2/c 1'
_space_group_name_Hall           '-P 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   14.85237(16)
_cell_length_b                   7.94141(8)
_cell_length_c                   24.9573(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.3906(9)
_cell_angle_gamma                90
_cell_volume                     2942.81(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10685
_cell_measurement_temperature    123
_cell_measurement_theta_max      73.1160
_cell_measurement_theta_min      4.5580
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.907
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92714
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1384
_exptl_crystal_size_max          0.1912
_exptl_crystal_size_mid          0.133
_exptl_crystal_size_min          0.1185
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            15504
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.740
_diffrn_reflns_theta_max         66.740
_diffrn_reflns_theta_min         2.976
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -70.00   30.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676   57.0000  -30.0000 100

#__ type_ start__ end____ width___ exp.time_
  2 omega  -74.00   26.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676   77.0000   90.0000 100

#__ type_ start__ end____ width___ exp.time_
  3 omega -108.00  -19.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676  -57.0000 -180.0000 89

#__ type_ start__ end____ width___ exp.time_
  4 omega   30.00   91.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -30.0000  -60.0000 61

#__ type_ start__ end____ width___ exp.time_
  5 omega   80.00  171.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154   30.0000 -150.0000 91

#__ type_ start__ end____ width___ exp.time_
  6 omega   96.00  178.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  125.0000   30.0000 82

#__ type_ start__ end____ width___ exp.time_
  7 omega   78.00  176.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154   30.0000  120.0000 98

#__ type_ start__ end____ width___ exp.time_
  8 omega   36.00  122.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154 -125.0000  -90.0000 86

#__ type_ start__ end____ width___ exp.time_
  9 omega   23.00  109.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -94.0000  -30.0000 86

#__ type_ start__ end____ width___ exp.time_
 10 omega   29.00   61.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -30.0000   90.0000 32

#__ type_ start__ end____ width___ exp.time_
 11 omega   29.00  138.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -77.0000   60.0000 109
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0440278000
_diffrn_orient_matrix_UB_12      0.0863457000
_diffrn_orient_matrix_UB_13      -0.0480384000
_diffrn_orient_matrix_UB_21      -0.0748439000
_diffrn_orient_matrix_UB_22      -0.0699160000
_diffrn_orient_matrix_UB_23      -0.0375965000
_diffrn_orient_matrix_UB_31      -0.0567677000
_diffrn_orient_matrix_UB_32      0.1590448000
_diffrn_orient_matrix_UB_33      0.0095735000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4901
_reflns_number_total             5219
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.658
_refine_diff_density_min         -0.690
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     436
_refine_ls_number_reflns         5219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0288
_refine_ls_R_factor_gt           0.0269
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0316P)²+2.7779P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0664
_refine_ls_wR_factor_ref         0.0679
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, H4 of O4, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, H6A of O6, H3 of O3, H1 of O1, All O(H,H) groups
2. Others
 Fixed Sof: H27A(0.5) H27B(0.5) O9(0.5) H9D(0.5) H9E(0.5)
 Fixed U11: O9(0.14268)
 Fixed U33: O9(0.06501)
3.a Riding coordinates:
 O2(H2), O4(H4), O6(H6A), O5(H5)
3.b Free rotating group:
 O9(H9D,H9E)
3.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C19(H19A,H19B,H19C), C28(H28A,H28B,H28C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.69926(2) 0.76044(3) 0.46040(2) 0.01866(7) Uani 1 1 d . . . . .
Br2 Br 0.20984(2) 0.86230(3) 0.33630(2) 0.02057(7) Uani 1 1 d . . . . .
O1 O 0.19297(10) 0.66252(19) 0.23668(6) 0.0181(3) Uani 1 1 d . . . . .
H1 H 0.195(2) 0.629(4) 0.2065(13) 0.027 Uiso 1 1 d R . . . .
O2 O 0.34305(10) 0.65514(19) 0.40776(6) 0.0196(3) Uani 1 1 d . . . . .
H2 H 0.3105 0.7124 0.4278 0.091(16) Uiso 1 1 d R . . . .
O3 O 0.51433(11) 0.62557(19) 0.45441(6) 0.0168(3) Uani 1 1 d . . . . .
H3 H 0.466(2) 0.628(4) 0.4475(12) 0.025 Uiso 1 1 d R . . . .
O4 O 0.79679(9) 0.57084(19) 0.36849(6) 0.0173(3) Uani 1 1 d . . . . .
H4 H 0.8321 0.6257 0.3886 0.021 Uiso 1 1 d R . . . .
C1 C 0.29095(13) 0.4259(3) 0.25932(8) 0.0131(4) Uani 1 1 d . . . . .
C2 C 0.25074(13) 0.5804(3) 0.27098(8) 0.0139(4) Uani 1 1 d . . . . .
C3 C 0.26751(13) 0.6559(3) 0.32084(8) 0.0145(4) Uani 1 1 d . . . . .
C4 C 0.32492(13) 0.5828(3) 0.35931(8) 0.0142(4) Uani 1 1 d . . . . .
C5 C 0.36831(13) 0.4306(2) 0.34758(8) 0.0128(4) Uani 1 1 d . . . . .
C6 C 0.35057(13) 0.3574(3) 0.29781(8) 0.0131(4) Uani 1 1 d . . . . .
H6 H 0.3790(17) 0.257(3) 0.2895(10) 0.016 Uiso 1 1 d R . . . .
C7 C 0.43278(13) 0.3513(2) 0.38887(8) 0.0130(4) Uani 1 1 d . . . . .
H7 H 0.4121(16) 0.385(3) 0.4228(10) 0.016 Uiso 1 1 d R . . . .
C8 C 0.43051(14) 0.1575(3) 0.38747(8) 0.0152(4) Uani 1 1 d . . . . .
H8A H 0.3670(18) 0.125(3) 0.3888(10) 0.018 Uiso 1 1 d R . . . .
H8B H 0.4518(17) 0.115(3) 0.3521(11) 0.018 Uiso 1 1 d R . . . .
C9 C 0.48657(16) 0.0785(3) 0.43275(9) 0.0220(5) Uani 1 1 d . . . . .
H9A H 0.470(2) 0.125(4) 0.4670(13) 0.033 Uiso 1 1 d R . . . .
H9B H 0.551(2) 0.104(4) 0.4284(12) 0.033 Uiso 1 1 d R . . . .
H9C H 0.480(2) -0.050(4) 0.4332(12) 0.033 Uiso 1 1 d R . . . .
C10 C 0.58427(13) 0.3559(2) 0.34374(8) 0.0127(4) Uani 1 1 d . . . . .
H10 H 0.5592(17) 0.272(3) 0.3200(10) 0.015 Uiso 1 1 d R . . . .
C11 C 0.52844(13) 0.4200(2) 0.38284(8) 0.0121(4) Uani 1 1 d . . . . .
C12 C 0.56319(13) 0.5461(2) 0.41665(8) 0.0135(4) Uani 1 1 d . . . . .
C13 C 0.65297(14) 0.5950(3) 0.41244(8) 0.0139(4) Uani 1 1 d . . . . .
C14 C 0.70852(13) 0.5251(3) 0.37444(8) 0.0132(4) Uani 1 1 d . . . . .
C15 C 0.67344(13) 0.4056(2) 0.33823(8) 0.0122(4) Uani 1 1 d . . . . .
C16 C 0.73084(13) 0.3352(3) 0.29354(8) 0.0132(4) Uani 1 1 d . . . . .
H16 H 0.7936(18) 0.360(3) 0.3027(10) 0.016 Uiso 1 1 d R . . . .
C17 C 0.72440(14) 0.1425(3) 0.28799(8) 0.0159(4) Uani 1 1 d . . . . .
H17A H 0.6615(18) 0.105(3) 0.2803(10) 0.019 Uiso 1 1 d R . . . .
H17B H 0.7577(18) 0.113(3) 0.2590(11) 0.019 Uiso 1 1 d R . . . .
C18 C 0.75634(19) 0.0484(3) 0.33788(10) 0.0266(5) Uani 1 1 d . . . . .
H18A H 0.722(2) 0.079(4) 0.3669(13) 0.040 Uiso 1 1 d R . . . .
H18B H 0.818(2) 0.080(4) 0.3481(13) 0.040 Uiso 1 1 d R . . . .
H18C H 0.755(2) -0.068(4) 0.3323(13) 0.040 Uiso 1 1 d R . . . .
O7 O 0.11488(10) 1.06620(19) 0.48410(6) 0.0187(3) Uani 1 1 d . . . . .
N1 N 0.09138(12) 1.1546(2) 0.44047(7) 0.0154(4) Uani 1 1 d . . . . .
C21 C 0.00366(15) 1.1913(3) 0.43052(9) 0.0217(5) Uani 1 1 d . . . . .
H21 H -0.0362(19) 1.145(3) 0.4567(11) 0.026 Uiso 1 1 d R . . . .
C22 C -0.02134(15) 1.2828(3) 0.38565(9) 0.0221(5) Uani 1 1 d . . . . .
H22 H -0.081(2) 1.305(4) 0.3788(11) 0.027 Uiso 1 1 d R . . . .
C23 C 0.04225(14) 1.3368(3) 0.34937(8) 0.0171(4) Uani 1 1 d . . . . .
C24 C 0.13209(15) 1.2967(3) 0.36130(9) 0.0196(4) Uani 1 1 d . . . . .
H24 H 0.1786(19) 1.331(3) 0.3379(11) 0.023 Uiso 1 1 d R . . . .
C25 C 0.15498(14) 1.2081(3) 0.40697(9) 0.0183(4) Uani 1 1 d . . . . .
H25 H 0.2136(19) 1.182(3) 0.4169(11) 0.022 Uiso 1 1 d R . . . .
C26 C 0.01658(15) 1.4362(3) 0.29997(9) 0.0198(4) Uani 1 1 d . . . . .
H26A H 0.0655(19) 1.513(4) 0.2937(11) 0.024 Uiso 1 1 d R . . . .
H26B H -0.0377(19) 1.498(3) 0.3063(11) 0.024 Uiso 1 1 d R . . . .
C27 C 0.0000 1.3265(5) 0.2500 0.0216(7) Uani 1 2 d S T P . .
H27A H 0.038(5) 1.266(11) 0.247(4) 0.026 Uiso 0.5 1 d R . . . .
H27B H -0.061(5) 1.244(10) 0.255(3) 0.026 Uiso 0.5 1 d R . . . .
O6 O 0.91152(13) 0.7227(4) 0.43215(9) 0.0600(8) Uani 1 1 d . . . . .
H6A H 0.9040 0.7870 0.4591 0.090 Uiso 1 1 d R . . . .
C20 C 0.9967(2) 0.7429(5) 0.41396(17) 0.0608(11) Uani 1 1 d . . . . .
H20A H 1.0307 0.8177 0.4383 0.091 Uiso 1 1 calc GR . . . .
H20B H 0.9939 0.7924 0.3780 0.091 Uiso 1 1 calc GR . . . .
H20C H 1.0267 0.6331 0.4126 0.091 Uiso 1 1 calc GR . . . .
O5 O 0.24129(17) 0.8271(3) 0.46983(7) 0.0610(8) Uani 1 1 d . . . . .
H5 H 0.2054 0.9047 0.4741 0.054(10) Uiso 1 1 d R . . . .
C19 C 0.2518(2) 0.7438(4) 0.51861(11) 0.0449(8) Uani 1 1 d . . . . .
H19A H 0.2079 0.6520 0.5204 0.067 Uiso 1 1 calc GR . . . .
H19B H 0.2420 0.8231 0.5480 0.067 Uiso 1 1 calc GR . . . .
H19C H 0.3128 0.6976 0.5218 0.067 Uiso 1 1 calc GR . . . .
O8 O 0.5000 1.0390(3) 0.2500 0.0220(5) Uani 1 2 d S T P . .
C28 C 0.5354(2) 0.7888(4) 0.29723(14) 0.0470(8) Uani 1 1 d . . . . .
H28A H 0.5554 0.8670 0.3255 0.070 Uiso 1 1 calc GR . . . .
H28B H 0.5863 0.7191 0.2864 0.070 Uiso 1 1 calc GR . . . .
H28C H 0.4877 0.7163 0.3108 0.070 Uiso 1 1 calc GR . . . .
C29 C 0.5000 0.8862(4) 0.2500 0.0210(6) Uani 1 2 d S T P . .
O9 O 0.9597(5) -0.0771(8) 0.2708(3) 0.0951(13) Uani 0.5 1 d . . . A -1
H9D H 0.9478 -0.1825 0.2642 0.143 Uiso 0.5 1 d G . . A -1
H9E H 1.0088 -0.0699 0.2904 0.143 Uiso 0.5 1 d G . . A -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C13 1.895(2) . ?
Br2 C3 1.893(2) . ?
O1 H1 0.80(3) . ?
O1 C2 1.363(2) . ?
O2 H2 0.8388 . ?
O2 C4 1.360(2) . ?
O3 H3 0.74(3) . ?
O3 C12 1.359(2) . ?
O4 H4 0.8396 . ?
O4 C14 1.372(2) . ?
C1 C2 1.398(3) . ?
C1 C6 1.400(3) . ?
C1 C16 1.531(3) 2_655 ?
C2 C3 1.398(3) . ?
C3 C4 1.395(3) . ?
C4 C5 1.404(3) . ?
C5 C6 1.391(3) . ?
C5 C7 1.526(3) . ?
C6 H6 0.93(3) . ?
C7 H7 0.94(3) . ?
C7 C8 1.540(3) . ?
C7 C11 1.533(3) . ?
C8 H8A 0.98(3) . ?
C8 H8B 1.00(3) . ?
C8 C9 1.523(3) . ?
C9 H9A 0.97(3) . ?
C9 H9B 0.99(3) . ?
C9 H9C 1.02(3) . ?
C10 H10 0.96(3) . ?
C10 C11 1.392(3) . ?
C10 C15 1.392(3) . ?
C11 C12 1.400(3) . ?
C12 C13 1.395(3) . ?
C13 C14 1.388(3) . ?
C14 C15 1.402(3) . ?
C15 C16 1.526(3) . ?
C16 C1 1.531(3) 2_655 ?
C16 H16 0.97(3) . ?
C16 C17 1.539(3) . ?
C17 H17A 0.99(3) . ?
C17 H17B 0.92(3) . ?
C17 C18 1.518(3) . ?
C18 H18A 0.93(3) . ?
C18 H18B 0.98(3) . ?
C18 H18C 0.94(3) . ?
O7 N1 1.335(2) . ?
N1 C21 1.352(3) . ?
N1 C25 1.345(3) . ?
C21 H21 0.97(3) . ?
C21 C22 1.378(3) . ?
C22 H22 0.91(3) . ?
C22 C23 1.392(3) . ?
C23 C24 1.397(3) . ?
C23 C26 1.505(3) . ?
C24 H24 0.96(3) . ?
C24 C25 1.375(3) . ?
C25 H25 0.92(3) . ?
C26 H26A 0.96(3) . ?
C26 H26B 0.96(3) . ?
C26 C27 1.536(3) . ?
C27 C26 1.536(3) 2 ?
C27 H27A 0.75(6) . ?
C27 H27B 1.13(6) . ?
O6 H6A 0.8532 . ?
O6 C20 1.364(4) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
O5 H5 0.8238 . ?
O5 C19 1.391(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
O8 C29 1.213(4) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C28 C29 1.495(3) . ?
C29 C28 1.495(3) 2_655 ?
O9 H9D 0.8704 . ?
O9 H9E 0.8694 . ?

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
C2 O1 H1 114(2) . . ?
C4 O2 H2 130.9 . . ?
C12 O3 H3 113(2) . . ?
C14 O4 H4 131.1 . . ?
C2 C1 C6 117.66(18) . . ?
C2 C1 C16 120.66(18) . 2_655 ?
C6 C1 C16 121.68(18) . 2_655 ?
O1 C2 C1 123.68(18) . . ?
O1 C2 C3 116.72(18) . . ?
C3 C2 C1 119.58(18) . . ?
C2 C3 Br2 118.74(15) . . ?
C4 C3 Br2 119.47(15) . . ?
C4 C3 C2 121.79(18) . . ?
O2 C4 C3 122.74(18) . . ?
O2 C4 C5 117.85(18) . . ?
C3 C4 C5 119.39(18) . . ?
C4 C5 C7 119.89(18) . . ?
C6 C5 C4 117.90(18) . . ?
C6 C5 C7 122.21(18) . . ?
C1 C6 H6 117.7(16) . . ?
C5 C6 C1 123.59(19) . . ?
C5 C6 H6 118.7(16) . . ?
C5 C7 H7 106.1(15) . . ?
C5 C7 C8 112.60(16) . . ?
C5 C7 C11 110.78(16) . . ?
C8 C7 H7 107.0(15) . . ?
C11 C7 H7 108.1(15) . . ?
C11 C7 C8 111.93(16) . . ?
C7 C8 H8A 106.6(15) . . ?
C7 C8 H8B 110.3(14) . . ?
H8A C8 H8B 105(2) . . ?
C9 C8 C7 112.56(17) . . ?
C9 C8 H8A 112.0(15) . . ?
C9 C8 H8B 109.7(14) . . ?
C8 C9 H9A 110.9(18) . . ?
C8 C9 H9B 110.4(17) . . ?
C8 C9 H9C 111.5(17) . . ?
H9A C9 H9B 106(2) . . ?
H9A C9 H9C 110(2) . . ?
H9B C9 H9C 108(2) . . ?
C11 C10 H10 117.2(15) . . ?
C15 C10 H10 119.4(15) . . ?
C15 C10 C11 123.34(19) . . ?
C10 C11 C7 120.52(18) . . ?
C10 C11 C12 117.84(18) . . ?
C12 C11 C7 121.63(17) . . ?
O3 C12 C11 123.72(18) . . ?
O3 C12 C13 116.76(18) . . ?
C13 C12 C11 119.52(18) . . ?
C12 C13 Br1 118.56(15) . . ?
C14 C13 Br1 119.76(15) . . ?
C14 C13 C12 121.68(18) . . ?
O4 C14 C13 123.60(18) . . ?
O4 C14 C15 116.79(17) . . ?
C13 C14 C15 119.56(18) . . ?
C10 C15 C14 117.91(18) . . ?
C10 C15 C16 121.17(18) . . ?
C14 C15 C16 120.91(18) . . ?
C1 C16 H16 106.9(15) 2_655 . ?
C1 C16 C17 112.28(16) 2_655 . ?
C15 C16 C1 110.30(16) . 2_655 ?
C15 C16 H16 107.6(15) . . ?
C15 C16 C17 113.30(17) . . ?
C17 C16 H16 106.0(14) . . ?
C16 C17 H17A 111.7(15) . . ?
C16 C17 H17B 106.8(16) . . ?
H17A C17 H17B 107(2) . . ?
C18 C17 C16 113.46(18) . . ?
C18 C17 H17A 106.6(15) . . ?
C18 C17 H17B 111.1(16) . . ?
C17 C18 H18A 110(2) . . ?
C17 C18 H18B 111.1(19) . . ?
C17 C18 H18C 111(2) . . ?
H18A C18 H18B 105(3) . . ?
H18A C18 H18C 111(3) . . ?
H18B C18 H18C 108(3) . . ?
O7 N1 C21 119.66(17) . . ?
O7 N1 C25 119.96(17) . . ?
C25 N1 C21 120.38(19) . . ?
N1 C21 H21 113.4(16) . . ?
N1 C21 C22 120.2(2) . . ?
C22 C21 H21 126.5(17) . . ?
C21 C22 H22 119.6(18) . . ?
C21 C22 C23 121.1(2) . . ?
C23 C22 H22 119.2(18) . . ?
C22 C23 C24 116.8(2) . . ?
C22 C23 C26 122.1(2) . . ?
C24 C23 C26 121.06(19) . . ?
C23 C24 H24 120.4(16) . . ?
C25 C24 C23 120.6(2) . . ?
C25 C24 H24 119.0(17) . . ?
N1 C25 C24 120.9(2) . . ?
N1 C25 H25 115.8(17) . . ?
C24 C25 H25 123.3(17) . . ?
C23 C26 H26A 106.7(16) . . ?
C23 C26 H26B 109.3(16) . . ?
C23 C26 C27 113.6(2) . . ?
H26A C26 H26B 110(2) . . ?
C27 C26 H26A 109.4(16) . . ?
C27 C26 H26B 107.9(16) . . ?
C26 C27 C26 110.9(3) . 2 ?
C26 C27 H27A 109(7) . . ?
C26 C27 H27A 114(7) 2 . ?
C26 C27 H27B 111(4) . . ?
C26 C27 H27B 108(4) 2 . ?
H27A C27 H27B 105(4) . . ?
C20 O6 H6A 109.3 . . ?
O6 C20 H20A 109.5 . . ?
O6 C20 H20B 109.5 . . ?
O6 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 O5 H5 107.5 . . ?
O5 C19 H19A 109.5 . . ?
O5 C19 H19B 109.5 . . ?
O5 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C29 C28 H28A 109.5 . . ?
C29 C28 H28B 109.5 . . ?
C29 C28 H28C 109.5 . . ?
O8 C29 C28 121.18(18) . 2_655 ?
O8 C29 C28 121.18(18) . . ?
C28 C29 C28 117.6(4) . 2_655 ?
H9D O9 H9E 109.5 . . ?

_shelx_SHELXL_version_number     2014/7
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-7 1 -10 0.0641 -7.0000 1.0000 -10.0000 0.2585 0.8300 0.4607
-7 4 -1 0.0768 -7.0000 4.0000 -1.0000 0.0852 0.2818 1.0240
3 3 13 0.0794 3.0000 3.0000 12.9999 -0.2334 -0.9230 0.4313
7 -2 7 0.0545 7.0000 -2.0000 7.0000 -0.2008 -0.6473 -0.6485
-4 -2 -14 0.0644 -4.0000 -2.0000 -13.9999 0.3237 0.9656 -0.2250
8 1 -9 0.0721 8.0000 1.0000 -9.0000 0.8709 -0.3303 -0.3813
0 -5 3 0.0633 0.0000 -5.0000 3.0000 -0.5758 0.2368 -0.7665
-8 0 9 0.0455 -8.0000 0.0000 9.0000 -0.7846 0.2604 0.5403
0 5 -3 0.0829 -0.0000 5.0000 -3.0000 0.5758 -0.2368 0.7665
8 -1 -8 0.0837 8.0000 -1.0000 -8.0000 0.6502 -0.2281 -0.6898
10 0 -1 0.0624 10.0000 0.0000 -1.0000 0.4883 -0.7108 -0.5773
-1 1 -16 0.0639 -1.0000 1.0000 -16.0000 0.8109 0.6065 0.0626
5 2 -13 0.0677 5.0000 2.0000 -13.0000 1.0173 -0.0253 -0.0902
-5 -2 13 0.0508 -5.0000 -2.0000 13.0000 -1.0173 0.0253 0.0902
3 -3 11 0.0456 3.0000 -3.0000 11.0000 -0.6554 -0.4283 -0.5421

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_acetone_BrC2_6
_database_code_depnum_ccdc_archive 'CCDC 1551407'
_audit_update_record             
;
2017-05-22 deposited with the CCDC.
2017-06-15 downloaded from the CCDC.
;
_audit_creation_date             2017-05-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'C36 H36 Br4 O8, 0.5(C16 H22 N2 O2), H2 O, 2(C3 H6 O)'
_chemical_formula_sum            'C50 H61 Br4 N O12'
_chemical_formula_weight         1187.63
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C30 H30 N1 O9 Br4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 1 2/c 1'
_space_group_name_Hall           '-P 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   15.3678(8)
_cell_length_b                   7.9991(3)
_cell_length_c                   22.9088(11)
_cell_angle_alpha                90
_cell_angle_beta                 104.628(5)
_cell_angle_gamma                90
_cell_volume                     2724.8(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3314
_cell_measurement_temperature    120
_cell_measurement_theta_max      28.2360
_cell_measurement_theta_min      3.6070
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.011
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84080
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1208
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
12 0 21 0.0301
-12 1 -21 0.0332
-21 -1 14 0.0389
20 0 -18 0.0155
2 5 27 0.0947
-3 -5 -26 0.0850
-7 -10 9 0.1232
8 10 -7 0.1164
-1 1 -31 0.0233
-2 -1 32 0.0328
21 1 2 0.0151
-18 -1 24 0.0264
16 1 -26 0.0082
-3 11 4 0.1372

_exptl_crystal_size_max          0.281
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_min          0.036
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
11.9998 0.0000 20.9981 -0.4516 0.1745 0.8602
-11.9998 1.0000 -20.9979 0.5276 -0.1902 -0.8172
-20.9999 -1.0000 14.0009 0.3179 0.8302 -0.4400
20.0000 0.0000 -18.0007 -0.3387 -0.8786 0.2763
1.9996 5.0000 26.9992 0.1211 0.4687 0.8711
-2.9996 -5.0000 -25.9992 -0.1050 -0.4226 -0.8828
-6.9997 -10.0000 8.9988 -0.6625 0.5247 -0.4670
7.9996 10.0000 -6.9990 0.6229 -0.5047 0.5441
-0.9998 1.0000 -30.9983 0.3421 -0.6756 -0.6674
-2.0002 -1.0000 31.9985 -0.2780 0.7699 0.5889
20.9998 1.0000 1.9984 -0.4429 -0.4772 0.7894
-18.0000 -1.0000 24.0001 0.1679 0.9786 -0.1213
16.0001 1.0000 -25.9999 -0.1044 -0.9746 0.0107
-3.0004 11.0000 4.0015 0.8766 -0.0130 0.4591

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_unetI/netI     0.0559
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            11117
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.250
_diffrn_reflns_theta_max         25.250
_diffrn_reflns_theta_min         3.137
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      120
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0053
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -94.00 -35.00   1.00   30.00    --  -18.14-178.00 -60.00   59
  2  ω      4.00  55.00   1.00   30.00    --   19.23  57.00 120.00   51
  3  ω      3.00  91.00   1.00   30.00    --   19.23  37.00-120.00   88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0239675000
_diffrn_orient_matrix_UB_12      0.0759945000
_diffrn_orient_matrix_UB_13      -0.0078118000
_diffrn_orient_matrix_UB_21      -0.0240704000
_diffrn_orient_matrix_UB_22      -0.0157713000
_diffrn_orient_matrix_UB_23      0.0220638000
_diffrn_orient_matrix_UB_31      0.0334688000
_diffrn_orient_matrix_UB_32      0.0429231000
_diffrn_orient_matrix_UB_33      0.0218370000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4052
_reflns_number_total             4906
_reflns_odcompleteness_completeness 98.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.525
_refine_diff_density_min         -1.223
_refine_diff_density_rms         0.124
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         4906
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0467
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0832P)²+5.5762P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1334
_refine_ls_wR_factor_ref         0.1434
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Restrained distances
 C31-C29
 2.5 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C26) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
Uanis(C31) = Uanis(C30) = Uanis(O30) = Uanis(C29)
Uanis(C21) = Uanis(C26)
4. Others
 Fixed Sof: O1(0.5) O1W(0.5) H1WA(0.5) H1WB(0.5) O30(0.5) C22(0.5) H22(0.5)
 C21(0.5) C20(0.5) H20(0.5) C19(0.5) N1(0.5) C23(0.5) C24(0.5) H24A(0.5)
 H24B(0.5) H24C(0.5) C25(0.5) H25A(0.5) H25B(0.5) H25C(0.5) C26(0.5) H26A(0.5)
 H26B(0.5) H26C(0.5) C29(0.5) H29A(0.5) H29B(0.5) H29C(0.5) C30(0.5) C31(0.5)
 H31A(0.5) H31B(0.5) H31C(0.5)
5.a Riding coordinates:
 O1W(H1WA,H1WB), O11(H11), O13(H13)
5.b Ternary CH refined with riding coordinates:
 C7(H7), C14(H14)
5.c Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C17(H17A,H17B)
5.d Aromatic/amide H refined with riding coordinates:
 C2(H2), C9(H9), C22(H22), C20(H20)
5.e Fitted hexagon refined as free rotating group:
 C22(C21,C20,C19,N1,C23)
5.f Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C18(H18A,H18B,H18C), C24(H24A,H24B,H24C), C25(H25A,H25B,
 H25C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C29(H29A,H29B,H29C), C31(H31A,
 H31B,H31C)
5.g Idealised tetrahedral OH refined as rotating group:
 O4(H4), O6(H6)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.22462(3) 1.11954(6) 0.14405(2) 0.02108(16) Uani 1 1 d . . . . .
Br2 Br 0.27507(3) 1.00877(6) 0.48513(2) 0.01980(16) Uani 1 1 d . . . . .
O1 O 0.4668(7) 0.9278(13) 0.4545(5) 0.035(3) Uani 0.5 1 d . . . A 1
O1W O 0.5322(6) 1.1683(13) 0.5357(4) 0.032(2) Uani 0.5 1 d . . . B -1
H1WA H 0.4871 1.2163 0.5442 0.049 Uiso 0.5 1 d R . . B -1
H1WB H 0.5116 1.0903 0.5119 0.049 Uiso 0.5 1 d R . . B -1
O4 O 0.2984(2) 0.9210(4) 0.25455(14) 0.0219(8) Uani 1 1 d . . . . .
H4 H 0.3069 0.8883 0.2904 0.033 Uiso 1 1 calc GR . . . .
O6 O 0.0769(2) 0.9137(4) 0.07068(14) 0.0181(7) Uani 1 1 d . . . . .
H6 H 0.0234 0.8832 0.0568 0.027 Uiso 1 1 calc GR . . . .
O11 O 0.0980(2) 0.8268(4) 0.48491(13) 0.0189(7) Uani 1 1 d . . . . .
H11 H 0.0932 0.9002 0.5108 0.028 Uiso 1 1 d R . . . .
O13 O 0.3290(2) 0.8494(4) 0.37476(14) 0.0202(7) Uani 1 1 d . . . . .
H13 H 0.3732 0.8703 0.4025 0.030 Uiso 1 1 d R . . . .
O28 O 0.0000 0.2872(6) 0.2500 0.0261(11) Uani 1 2 d S T P . .
O30 O 0.3787(8) 1.298(2) 0.5660(8) 0.104(4) Uani 0.5 1 d . . . C -1
C1 C 0.0819(3) 0.6748(6) 0.13799(19) 0.0129(9) Uani 1 1 d . . . . .
C2 C 0.1254(3) 0.6052(6) 0.19342(19) 0.0131(9) Uani 1 1 d . . . . .
H2 H 0.1040 0.5013 0.2043 0.016 Uiso 1 1 calc R . . . .
C3 C 0.1990(3) 0.6794(6) 0.23415(19) 0.0133(9) Uani 1 1 d . . . . .
C4 C 0.2277(3) 0.8349(6) 0.21876(19) 0.0145(9) Uani 1 1 d . . . . .
C5 C 0.1855(3) 0.9076(6) 0.1639(2) 0.0143(9) Uani 1 1 d . . . . .
C6 C 0.1131(3) 0.8301(6) 0.12328(19) 0.0136(9) Uani 1 1 d . . . . .
C7 C 0.2444(3) 0.5962(6) 0.2938(2) 0.0150(9) Uani 1 1 d . . . . .
H7 H 0.3089 0.6314 0.3036 0.018 Uiso 1 1 calc R . . . .
C8 C 0.2060(3) 0.6627(6) 0.34451(19) 0.0132(9) Uani 1 1 d . . . . .
C9 C 0.1238(3) 0.6059(5) 0.35149(19) 0.0135(9) Uani 1 1 d . . . . .
H9 H 0.0911 0.5274 0.3232 0.016 Uiso 1 1 calc R . . . .
C10 C 0.0871(3) 0.6588(5) 0.39809(19) 0.0130(9) Uani 1 1 d . . . . .
C11 C 0.1351(3) 0.7758(6) 0.43869(19) 0.0155(9) Uani 1 1 d . . . . .
C12 C 0.2166(3) 0.8398(6) 0.43156(19) 0.0143(9) Uani 1 1 d . . . . .
C13 C 0.2520(3) 0.7830(6) 0.38501(19) 0.0152(9) Uani 1 1 d . . . . .
C14 C 0.0023(3) 0.5890(5) 0.09458(19) 0.0132(9) Uani 1 1 d . . . . .
H14 H 0.0059 0.6178 0.0528 0.016 Uiso 1 1 calc R . . . .
C15 C 0.0057(3) 0.3968(6) 0.0995(2) 0.0182(10) Uani 1 1 d . . . . .
H15A H 0.0615 0.3566 0.0901 0.022 Uiso 1 1 calc R . . . .
H15B H 0.0082 0.3645 0.1416 0.022 Uiso 1 1 calc R . . . .
C16 C -0.0742(3) 0.3110(6) 0.0578(2) 0.0236(11) Uani 1 1 d . . . . .
H16A H -0.0814 0.3521 0.0165 0.035 Uiso 1 1 calc GR . . . .
H16B H -0.1287 0.3355 0.0710 0.035 Uiso 1 1 calc GR . . . .
H16C H -0.0640 0.1900 0.0588 0.035 Uiso 1 1 calc GR . . . .
C17 C 0.2442(3) 0.4039(6) 0.2914(2) 0.0202(10) Uani 1 1 d . . . . .
H17A H 0.1819 0.3628 0.2862 0.024 Uiso 1 1 calc R . . . .
H17B H 0.2652 0.3670 0.2561 0.024 Uiso 1 1 calc R . . . .
C18 C 0.3049(4) 0.3272(7) 0.3490(2) 0.0334(13) Uani 1 1 d . . . . .
H18A H 0.3044 0.2051 0.3453 0.050 Uiso 1 1 calc GR . . . .
H18B H 0.2825 0.3590 0.3839 0.050 Uiso 1 1 calc GR . . . .
H18C H 0.3665 0.3685 0.3545 0.050 Uiso 1 1 calc GR . . . .
C22 C 0.6389(5) 0.7280(9) 0.3973(3) 0.032(3) Uani 0.5 1 d . . . A 1
H22 H 0.6716 0.7470 0.3678 0.038 Uiso 0.5 1 calc R . . A 1
C21 C 0.6565(4) 0.5869(8) 0.4338(3) 0.041(2) Uani 0.5 1 d G . . A 1
C20 C 0.6087(5) 0.5590(7) 0.4769(3) 0.032(3) Uani 0.5 1 d G . . A 1
H20 H 0.6208 0.4626 0.5019 0.038 Uiso 0.5 1 calc R . . A 1
C19 C 0.5433(4) 0.6723(8) 0.4835(3) 0.031(3) Uani 0.5 1 d G . . A 1
N1 N 0.5256(4) 0.8134(7) 0.4470(3) 0.0239(19) Uani 0.5 1 d G . . A 1
C23 C 0.5735(4) 0.8412(7) 0.4039(3) 0.026(2) Uani 0.5 1 d G . . A 1
C24 C 0.5455(8) 0.9935(14) 0.3644(7) 0.042(3) Uani 0.5 1 d . . . A 1
H24A H 0.5880 1.0110 0.3395 0.063 Uiso 0.5 1 calc GR . . A 1
H24B H 0.5454 1.0919 0.3898 0.063 Uiso 0.5 1 calc GR . . A 1
H24C H 0.4850 0.9761 0.3383 0.063 Uiso 0.5 1 calc GR . . A 1
C25 C 0.4836(9) 0.652(2) 0.5257(6) 0.055(4) Uani 0.5 1 d . . . A 1
H25A H 0.5062 0.5607 0.5540 0.082 Uiso 0.5 1 calc GR . . A 1
H25B H 0.4223 0.6261 0.5024 0.082 Uiso 0.5 1 calc GR . . A 1
H25C H 0.4832 0.7561 0.5482 0.082 Uiso 0.5 1 calc GR . . A 1
C26 C 0.7342(10) 0.489(2) 0.4317(7) 0.041(2) Uani 0.5 1 d . U . A 1
H26A H 0.7839 0.5160 0.4666 0.061 Uiso 0.5 1 calc GR . . A 1
H26B H 0.7520 0.5138 0.3945 0.061 Uiso 0.5 1 calc GR . . A 1
H26C H 0.7197 0.3697 0.4327 0.061 Uiso 0.5 1 calc GR . . A 1
C27 C 0.0621(5) 0.0381(9) 0.2983(3) 0.0522(19) Uani 1 1 d . . . . .
H27A H 0.1010 0.1146 0.3267 0.078 Uiso 1 1 calc GR . . . .
H27B H 0.0990 -0.0354 0.2802 0.078 Uiso 1 1 calc GR . . . .
H27C H 0.0269 -0.0295 0.3198 0.078 Uiso 1 1 calc GR . . . .
C28 C 0.0000 0.1363(9) 0.2500 0.0246(16) Uani 1 2 d S T P . .
C29 C 0.2849(14) 1.507(3) 0.5910(11) 0.104(4) Uani 0.5 1 d D . . C -1
H29A H 0.2255 1.4543 0.5828 0.156 Uiso 0.5 1 calc GR . . C -1
H29B H 0.2889 1.5754 0.5563 0.156 Uiso 0.5 1 calc GR . . C -1
H29C H 0.2935 1.5784 0.6268 0.156 Uiso 0.5 1 calc GR . . C -1
C30 C 0.3562(15) 1.375(3) 0.6018(13) 0.104(4) Uani 0.5 1 d . . . C -1
C31 C 0.3977(11) 1.376(3) 0.6717(9) 0.104(4) Uani 0.5 1 d D . . C -1
H31A H 0.3613 1.3051 0.6913 0.156 Uiso 0.5 1 calc GR . . C -1
H31B H 0.3987 1.4902 0.6870 0.156 Uiso 0.5 1 calc GR . . C -1
H31C H 0.4593 1.3319 0.6805 0.156 Uiso 0.5 1 calc GR . . C -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C5 1.892(4) . ?
Br2 C12 1.893(4) . ?
O1 N1 1.327(10) . ?
O1W H1WA 0.8578 . ?
O1W H1WB 0.8374 . ?
O4 H4 0.8400 . ?
O4 C4 1.370(5) . ?
O6 H6 0.8400 . ?
O6 C6 1.368(5) . ?
O11 H11 0.8510 . ?
O11 C11 1.384(5) . ?
O13 H13 0.8214 . ?
O13 C13 1.371(5) . ?
O28 C28 1.207(9) . ?
O30 C30 1.15(2) . ?
C1 C2 1.393(6) . ?
C1 C6 1.403(6) . ?
C1 C14 1.531(6) . ?
C2 H2 0.9500 . ?
C2 C3 1.403(6) . ?
C3 C4 1.395(6) . ?
C3 C7 1.522(6) . ?
C4 C5 1.388(6) . ?
C5 C6 1.401(6) . ?
C7 H7 1.0000 . ?
C7 C8 1.525(6) . ?
C7 C17 1.539(7) . ?
C8 C9 1.390(6) . ?
C8 C13 1.399(6) . ?
C9 H9 0.9500 . ?
C9 C10 1.393(6) . ?
C10 C11 1.392(6) . ?
C10 C14 1.530(6) 2 ?
C11 C12 1.401(6) . ?
C12 C13 1.390(6) . ?
C14 C10 1.530(6) 2 ?
C14 H14 1.0000 . ?
C14 C15 1.542(6) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.516(7) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.539(7) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C22 H22 0.9500 . ?
C22 C21 1.3900 . ?
C22 C23 1.3900 . ?
C21 C20 1.3900 . ?
C21 C26 1.440(15) . ?
C20 H20 0.9500 . ?
C20 C19 1.3900 . ?
C19 N1 1.3900 . ?
C19 C25 1.500(12) . ?
N1 C23 1.3900 . ?
C23 C24 1.514(14) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C27 C28 1.489(7) . ?
C28 C27 1.489(7) 2 ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C29 C30 1.50(3) . ?
C30 C31 1.57(3) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1WA O1W H1WB 106.7 . . ?
C4 O4 H4 109.5 . . ?
C6 O6 H6 109.5 . . ?
C11 O11 H11 149.5 . . ?
C13 O13 H13 121.8 . . ?
C2 C1 C6 117.3(4) . . ?
C2 C1 C14 122.3(4) . . ?
C6 C1 C14 120.5(4) . . ?
C1 C2 H2 118.1 . . ?
C1 C2 C3 123.9(4) . . ?
C3 C2 H2 118.1 . . ?
C2 C3 C7 121.5(4) . . ?
C4 C3 C2 117.5(4) . . ?
C4 C3 C7 121.0(4) . . ?
O4 C4 C3 123.4(4) . . ?
O4 C4 C5 116.8(4) . . ?
C5 C4 C3 119.8(4) . . ?
C4 C5 Br1 119.2(3) . . ?
C4 C5 C6 121.8(4) . . ?
C6 C5 Br1 119.0(3) . . ?
O6 C6 C1 123.8(4) . . ?
O6 C6 C5 116.5(4) . . ?
C5 C6 C1 119.7(4) . . ?
C3 C7 H7 106.4 . . ?
C3 C7 C8 110.7(4) . . ?
C3 C7 C17 114.1(4) . . ?
C8 C7 H7 106.4 . . ?
C8 C7 C17 112.2(4) . . ?
C17 C7 H7 106.4 . . ?
C9 C8 C7 120.8(4) . . ?
C9 C8 C13 118.1(4) . . ?
C13 C8 C7 121.2(4) . . ?
C8 C9 H9 118.5 . . ?
C8 C9 C10 123.0(4) . . ?
C10 C9 H9 118.5 . . ?
C9 C10 C14 121.4(4) . 2 ?
C11 C10 C9 117.9(4) . . ?
C11 C10 C14 120.7(4) . 2 ?
O11 C11 C10 117.3(4) . . ?
O11 C11 C12 122.3(4) . . ?
C10 C11 C12 120.4(4) . . ?
C11 C12 Br2 118.5(3) . . ?
C13 C12 Br2 121.1(3) . . ?
C13 C12 C11 120.3(4) . . ?
O13 C13 C8 117.8(4) . . ?
O13 C13 C12 121.8(4) . . ?
C12 C13 C8 120.2(4) . . ?
C1 C14 H14 106.9 . . ?
C1 C14 C15 113.1(4) . . ?
C10 C14 C1 110.9(3) 2 . ?
C10 C14 H14 106.9 2 . ?
C10 C14 C15 111.8(4) 2 . ?
C15 C14 H14 106.9 . . ?
C14 C15 H15A 108.9 . . ?
C14 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
C16 C15 C14 113.4(4) . . ?
C16 C15 H15A 108.9 . . ?
C16 C15 H15B 108.9 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C7 C17 H17A 109.2 . . ?
C7 C17 H17B 109.2 . . ?
H17A C17 H17B 107.9 . . ?
C18 C17 C7 111.9(4) . . ?
C18 C17 H17A 109.2 . . ?
C18 C17 H17B 109.2 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C21 C22 H22 120.0 . . ?
C21 C22 C23 120.0 . . ?
C23 C22 H22 120.0 . . ?
C22 C21 C26 117.4(9) . . ?
C20 C21 C22 120.0 . . ?
C20 C21 C26 121.9(8) . . ?
C21 C20 H20 120.0 . . ?
C21 C20 C19 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C19 N1 120.0 . . ?
C20 C19 C25 125.3(8) . . ?
N1 C19 C25 114.7(7) . . ?
O1 N1 C19 121.2(7) . . ?
O1 N1 C23 118.7(7) . . ?
C23 N1 C19 120.0 . . ?
C22 C23 C24 124.3(6) . . ?
N1 C23 C22 120.0 . . ?
N1 C23 C24 115.7(6) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C19 C25 H25A 109.5 . . ?
C19 C25 H25B 109.5 . . ?
C19 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C21 C26 H26A 109.5 . . ?
C21 C26 H26B 109.5 . . ?
C21 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C28 C27 H27A 109.5 . . ?
C28 C27 H27B 109.5 . . ?
C28 C27 H27C 109.5 . . ?
O28 C28 C27 121.8(4) . 2 ?
O28 C28 C27 121.8(4) . . ?
C27 C28 C27 116.3(8) . 2 ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C30 C29 H29A 109.5 . . ?
C30 C29 H29B 109.5 . . ?
C30 C29 H29C 109.5 . . ?
O30 C30 C29 127(3) . . ?
O30 C30 C31 128(3) . . ?
C29 C30 C31 105.0(17) . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C5 C6 O6 1.4(5) . . . . ?
Br1 C5 C6 C1 -178.4(3) . . . . ?
Br2 C12 C13 O13 -1.8(6) . . . . ?
Br2 C12 C13 C8 -177.5(3) . . . . ?
O1 N1 C23 C22 176.6(7) . . . . ?
O1 N1 C23 C24 -6.6(9) . . . . ?
O4 C4 C5 Br1 -2.3(5) . . . . ?
O4 C4 C5 C6 179.2(4) . . . . ?
O11 C11 C12 Br2 -2.7(6) . . . . ?
O11 C11 C12 C13 179.0(4) . . . . ?
C1 C2 C3 C4 2.4(6) . . . . ?
C1 C2 C3 C7 -179.4(4) . . . . ?
C1 C14 C15 C16 178.6(4) . . . . ?
C2 C1 C6 O6 -179.8(4) . . . . ?
C2 C1 C6 C5 0.1(6) . . . . ?
C2 C1 C14 C10 96.7(5) . . . 2 ?
C2 C1 C14 C15 -29.8(6) . . . . ?
C2 C3 C4 O4 179.8(4) . . . . ?
C2 C3 C4 C5 -2.1(6) . . . . ?
C2 C3 C7 C8 -94.9(5) . . . . ?
C2 C3 C7 C17 32.9(6) . . . . ?
C3 C4 C5 Br1 179.5(3) . . . . ?
C3 C4 C5 C6 1.0(7) . . . . ?
C3 C7 C8 C9 78.6(5) . . . . ?
C3 C7 C8 C13 -100.9(5) . . . . ?
C3 C7 C17 C18 169.8(4) . . . . ?
C4 C3 C7 C8 83.3(5) . . . . ?
C4 C3 C7 C17 -148.9(4) . . . . ?
C4 C5 C6 O6 179.9(4) . . . . ?
C4 C5 C6 C1 0.1(6) . . . . ?
C6 C1 C2 C3 -1.4(6) . . . . ?
C6 C1 C14 C10 -82.4(5) . . . 2 ?
C6 C1 C14 C15 151.1(4) . . . . ?
C7 C3 C4 O4 1.5(6) . . . . ?
C7 C3 C4 C5 179.6(4) . . . . ?
C7 C8 C9 C10 178.0(4) . . . . ?
C7 C8 C13 O13 5.2(6) . . . . ?
C7 C8 C13 C12 -178.9(4) . . . . ?
C8 C7 C17 C18 -63.2(5) . . . . ?
C8 C9 C10 C11 1.0(7) . . . . ?
C8 C9 C10 C14 -178.0(4) . . . 2 ?
C9 C8 C13 O13 -174.3(4) . . . . ?
C9 C8 C13 C12 1.6(6) . . . . ?
C9 C10 C11 O11 -179.8(4) . . . . ?
C9 C10 C11 C12 1.4(6) . . . . ?
C10 C11 C12 Br2 176.1(3) . . . . ?
C10 C11 C12 C13 -2.2(7) . . . . ?
C10 C14 C15 C16 52.5(5) 2 . . . ?
C11 C12 C13 O13 176.4(4) . . . . ?
C11 C12 C13 C8 0.7(7) . . . . ?
C13 C8 C9 C10 -2.4(6) . . . . ?
C14 C1 C2 C3 179.5(4) . . . . ?
C14 C1 C6 O6 -0.6(6) . . . . ?
C14 C1 C6 C5 179.3(4) . . . . ?
C14 C10 C11 O11 -0.8(6) 2 . . . ?
C14 C10 C11 C12 -179.7(4) 2 . . . ?
C17 C7 C8 C9 -50.2(6) . . . . ?
C17 C7 C8 C13 130.3(4) . . . . ?
C22 C21 C20 C19 0.0 . . . . ?
C21 C22 C23 N1 0.0 . . . . ?
C21 C22 C23 C24 -176.5(8) . . . . ?
C21 C20 C19 N1 0.0 . . . . ?
C21 C20 C19 C25 176.3(10) . . . . ?
C20 C19 N1 O1 -176.5(7) . . . . ?
C20 C19 N1 C23 0.0 . . . . ?
C19 N1 C23 C22 0.0 . . . . ?
C19 N1 C23 C24 176.8(8) . . . . ?
C23 C22 C21 C20 0.0 . . . . ?
C23 C22 C21 C26 -170.2(8) . . . . ?
C25 C19 N1 O1 6.8(10) . . . . ?
C25 C19 N1 C23 -176.7(9) . . . . ?
C26 C21 C20 C19 169.8(9) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.157
_oxdiff_exptl_absorpt_empirical_full_min 0.878
####################################################################### 
# 
# 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_acetone_BrC2_5
_database_code_depnum_ccdc_archive 'CCDC 1551406'
_audit_update_record             
;
2017-05-22 deposited with the CCDC.
2017-06-15 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT431_acetone_BrC2_5      
;
PROBLEM: Short Inter HL..A  Contact Br2    ..  O8      ..       3.00 Ang.  
RESPONSE: Halogen bond
;
_vrf_PLAT971_acetone_BrC2_5      
;
PROBLEM: Check Calcd Residual Density  1.65A From      O3       2.85 eA-3  
RESPONSE: Due to unresolved disorder
;
# end Validation Reply Form
_audit_creation_date             2017-04-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C36 H36 Br4 O8, 3(C3 H6 O), 2(C6 H7 N O2)'
_chemical_formula_sum            'C57 H68 Br4 N2 O15'
_chemical_formula_weight         1340.77
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 O8 Br1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   31.3059(19)
_cell_length_b                   8.0079(5)
_cell_length_c                   23.0375(17)
_cell_angle_alpha                90
_cell_angle_beta                 96.653(7)
_cell_angle_gamma                90
_cell_volume                     5736.5(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2463
_cell_measurement_temperature    120
_cell_measurement_theta_max      26.1420
_cell_measurement_theta_min      3.3660
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.875
_exptl_absorpt_correction_T_max  0.921
_exptl_absorpt_correction_T_min  0.679
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             2736
_exptl_crystal_size_max          0.1695
_exptl_crystal_size_mid          0.0442
_exptl_crystal_size_min          0.0231
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0650
_diffrn_reflns_av_unetI/netI     0.0911
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            14479
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.250
_diffrn_reflns_theta_max         25.250
_diffrn_reflns_theta_min         2.798
_diffrn_ambient_temperature      120
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0053
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -78.00  -36.00   1.0000  125.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.1368 -178.0000 -180.0000 42

#__ type_ start__ end____ width___ exp.time_
  2 omega  -83.00   -3.00   1.0000  125.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.1368  -57.0000 -180.0000 80

#__ type_ start__ end____ width___ exp.time_
  3 omega  -35.00   -3.00   1.0000  125.0000
omega____ theta____ kappa____ phi______ frames
    -       19.3087  -57.0000   90.0000 32

#__ type_ start__ end____ width___ exp.time_
  4 omega  -19.00    8.00   1.0000  125.0000
omega____ theta____ kappa____ phi______ frames
    -       19.3087  -99.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
  5 omega   46.00   94.00   1.0000  125.0000
omega____ theta____ kappa____ phi______ frames
    -       19.3087  178.0000 -120.0000 48

#__ type_ start__ end____ width___ exp.time_
  6 omega  -16.00   59.00   1.0000  125.0000
omega____ theta____ kappa____ phi______ frames
    -       19.3087  -99.0000    0.0000 75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0192179000
_diffrn_orient_matrix_UB_12      0.0083790000
_diffrn_orient_matrix_UB_13      0.0133044000
_diffrn_orient_matrix_UB_21      -0.0102596500
_diffrn_orient_matrix_UB_22      -0.0588995500
_diffrn_orient_matrix_UB_23      -0.0199599000
_diffrn_orient_matrix_UB_31      0.0067768500
_diffrn_orient_matrix_UB_32      -0.0656104500
_diffrn_orient_matrix_UB_33      0.0196299000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3895
_reflns_number_total             5192
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.681
_refine_diff_density_min         -0.944
_refine_diff_density_rms         0.180
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     354
_refine_ls_number_reflns         5192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1101
_refine_ls_R_factor_gt           0.0818
_refine_ls_restrained_S_all      1.146
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0488P)²+229.6943P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2002
_refine_ls_wR_factor_ref         0.2131
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C14) = Uanis(C15)
3.a Riding coordinates:
 O1(H1), O2(H2), O4(H4)
3.b Ternary CH refined with riding coordinates:
 C3(H3A), C10(H10)
3.c Secondary CH2 refined with riding coordinates:
 C1AA(H1AA,H1AB), C11(H11A,H11B)
3.d Aromatic/amide H refined with riding coordinates:
 C9(H9), C13(H13), C17(H17), C18(H18), C20(H20), C21(H21)
3.e Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C32(H32A,H32B,H32C), C23(H23A,H23B,H23C), C22(H22A,H22B,
 H22C), C25(H25A,H25B,H25C), C27(H27A,H27B,H27C)
3.f Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.11167(3) 0.11812(12) 0.12269(4) 0.0186(3) Uani 1 1 d . . . . .
Br2 Br 0.12977(3) 0.01447(12) 0.45764(4) 0.0159(3) Uani 1 1 d . . . . .
O1 O -0.0398(2) -0.0818(8) 0.4370(3) 0.0169(15) Uani 1 1 d . . . . .
H1 H -0.0160 -0.1115 0.4484 0.025 Uiso 1 1 d R . . . .
O2 O 0.0450(2) -0.1670(9) 0.4746(3) 0.0171(15) Uani 1 1 d . . . . .
H2 H 0.0427 -0.1011 0.5006 0.026 Uiso 1 1 d R . . . .
O3 O 0.1539(2) -0.1295(9) 0.3458(3) 0.0172(15) Uani 1 1 d . . . . .
H3 H 0.1525 -0.1145 0.3096 0.026 Uiso 1 1 calc GR . . . .
O4 O 0.1442(2) -0.0863(9) 0.2310(3) 0.0183(15) Uani 1 1 d . . . . .
H4 H 0.1680 -0.1014 0.2176 0.027 Uiso 1 1 d R . . . .
C1 C -0.0405(3) -0.3179(12) 0.3695(4) 0.015(2) Uani 1 1 d . . . . .
C1AA C -0.0050(3) -0.5983(12) 0.4008(4) 0.017(2) Uani 1 1 d . . . . .
H1AA H -0.0316 -0.6373 0.4158 0.020 Uiso 1 1 calc R . . . .
H1AB H -0.0063 -0.6322 0.3593 0.020 Uiso 1 1 calc R . . . .
C2 C -0.0563(3) -0.1673(12) 0.3869(4) 0.013(2) Uani 1 1 d . . . . .
C3 C -0.0026(3) -0.4066(11) 0.4049(4) 0.0111(19) Uani 1 1 d . . . . .
H3A H -0.0044 -0.3778 0.4468 0.013 Uiso 1 1 calc R . . . .
C4 C 0.0401(3) -0.3371(11) 0.3898(4) 0.0102(19) Uani 1 1 d . . . . .
C5 C 0.0619(3) -0.2151(12) 0.4252(4) 0.013(2) Uani 1 1 d . . . . .
C6 C 0.1000(3) -0.1484(11) 0.4095(4) 0.0115(19) Uani 1 1 d . . . . .
C7 C 0.1169(3) -0.2019(12) 0.3588(4) 0.013(2) Uani 1 1 d . . . . .
C8 C 0.0966(3) -0.3300(11) 0.3248(4) 0.0109(19) Uani 1 1 d . . . . .
C9 C 0.0581(3) -0.3910(11) 0.3403(4) 0.0114(19) Uani 1 1 d . . . . .
H9 H 0.0433 -0.4733 0.3161 0.014 Uiso 1 1 calc R . . . .
C10 C 0.1157(3) -0.3980(12) 0.2718(4) 0.014(2) Uani 1 1 d . . . . .
H10 H 0.1465 -0.3623 0.2764 0.017 Uiso 1 1 calc R . . . .
C11 C 0.1161(3) -0.5892(12) 0.2686(4) 0.016(2) Uani 1 1 d . . . . .
H11A H 0.0864 -0.6309 0.2692 0.019 Uiso 1 1 calc R . . . .
H11B H 0.1258 -0.6235 0.2309 0.019 Uiso 1 1 calc R . . . .
C12 C 0.1450(4) -0.6703(14) 0.3181(5) 0.035(3) Uani 1 1 d . . . . .
H12A H 0.1748 -0.6343 0.3165 0.052 Uiso 1 1 calc GR . . . .
H12B H 0.1432 -0.7920 0.3142 0.052 Uiso 1 1 calc GR . . . .
H12C H 0.1357 -0.6368 0.3556 0.052 Uiso 1 1 calc GR . . . .
C13 C 0.0604(3) -0.3887(12) 0.1824(4) 0.0115(19) Uani 1 1 d . . . . .
H13 H 0.0496 -0.4915 0.1952 0.014 Uiso 1 1 calc R . . . .
C14 C 0.0950(3) -0.3160(12) 0.2159(4) 0.0113(14) Uani 1 1 d . . . . .
C15 C 0.1113(3) -0.1626(12) 0.1975(4) 0.0113(14) Uani 1 1 d . . . . .
C16 C 0.0911(3) -0.0915(12) 0.1466(4) 0.014(2) Uani 1 1 d . . . . .
C32 C 0.0339(3) -0.6820(13) 0.4358(5) 0.022(2) Uani 1 1 d . . . . .
H32A H 0.0594 -0.6666 0.4154 0.032 Uiso 1 1 calc GR . . . .
H32B H 0.0282 -0.8016 0.4396 0.032 Uiso 1 1 calc GR . . . .
H32C H 0.0389 -0.6314 0.4747 0.032 Uiso 1 1 calc GR . . . .
O7 O 0.0000 0.2917(13) 0.2500 0.023(2) Uani 1 2 d S T P . .
C23 C 0.0300(4) 0.0429(17) 0.2926(6) 0.045(4) Uani 1 1 d . . . . .
H23A H 0.0520 -0.0107 0.2720 0.067 Uiso 1 1 calc GR . . . .
H23B H 0.0138 -0.0427 0.3112 0.067 Uiso 1 1 calc GR . . . .
H23C H 0.0439 0.1184 0.3226 0.067 Uiso 1 1 calc GR . . . .
C24 C 0.0000 0.1404(18) 0.2500 0.020(3) Uani 1 2 d S T P . .
O5 O 0.2170(2) -0.1049(9) 0.1965(3) 0.0261(17) Uani 1 1 d . . . . .
O6 O 0.2524(2) 0.4387(9) 0.0682(3) 0.0205(16) Uani 1 1 d . . . . .
N1 N 0.2256(2) 0.0319(11) 0.1661(4) 0.0189(19) Uani 1 1 d . . . . .
C17 C 0.2391(3) 0.1738(14) 0.1947(5) 0.022(2) Uani 1 1 d . . . . .
H17 H 0.2422 0.1766 0.2362 0.027 Uiso 1 1 calc R . . . .
C18 C 0.2483(3) 0.3131(13) 0.1640(5) 0.020(2) Uani 1 1 d . . . . .
H18 H 0.2573 0.4125 0.1844 0.024 Uiso 1 1 calc R . . . .
C19 C 0.2446(3) 0.3102(12) 0.1031(4) 0.015(2) Uani 1 1 d . . . . .
C20 C 0.2313(3) 0.1611(13) 0.0752(4) 0.019(2) Uani 1 1 d . . . . .
H20 H 0.2292 0.1545 0.0338 0.023 Uiso 1 1 calc R . . . .
C21 C 0.2212(3) 0.0244(13) 0.1066(4) 0.019(2) Uani 1 1 d . . . . .
H21 H 0.2112 -0.0750 0.0870 0.023 Uiso 1 1 calc R . . . .
C22 C 0.2667(3) 0.5952(13) 0.0963(5) 0.024(2) Uani 1 1 d . . . . .
H22A H 0.2956 0.5806 0.1171 0.036 Uiso 1 1 calc GR . . . .
H22B H 0.2468 0.6277 0.1241 0.036 Uiso 1 1 calc GR . . . .
H22C H 0.2674 0.6825 0.0666 0.036 Uiso 1 1 calc GR . . . .
O8 O 0.1825(2) 0.2811(9) 0.5235(3) 0.0304(19) Uani 1 1 d . . . . .
C25 C 0.1445(5) 0.456(2) 0.5815(8) 0.073(6) Uani 1 1 d . . . . .
H25A H 0.1147 0.4177 0.5791 0.109 Uiso 1 1 calc GR . . . .
H25B H 0.1453 0.5783 0.5853 0.109 Uiso 1 1 calc GR . . . .
H25C H 0.1613 0.4062 0.6157 0.109 Uiso 1 1 calc GR . . . .
C26 C 0.1630(3) 0.4074(14) 0.5287(5) 0.027(3) Uani 1 1 d . . . . .
C27 C 0.1579(5) 0.5300(19) 0.4789(8) 0.074(6) Uani 1 1 d . . . . .
H27A H 0.1798 0.5084 0.4527 0.110 Uiso 1 1 calc GR . . . .
H27B H 0.1613 0.6439 0.4943 0.110 Uiso 1 1 calc GR . . . .
H27C H 0.1292 0.5177 0.4572 0.110 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C16 1.902(9) . ?
Br2 C6 1.887(9) . ?
O1 H1 0.7994 . ?
O1 C2 1.389(11) . ?
O2 H2 0.8081 . ?
O2 C5 1.365(11) . ?
O3 H3 0.8400 . ?
O3 C7 1.359(11) . ?
O4 H4 0.8473 . ?
O4 C15 1.359(11) . ?
C1 C2 1.380(13) . ?
C1 C3 1.534(13) . ?
C1 C13 1.402(13) 2 ?
C1AA H1AA 0.9900 . ?
C1AA H1AB 0.9900 . ?
C1AA C3 1.539(13) . ?
C1AA C32 1.533(13) . ?
C2 C16 1.398(13) 2 ?
C3 H3A 1.0000 . ?
C3 C4 1.527(11) . ?
C4 C5 1.398(13) . ?
C4 C9 1.399(13) . ?
C5 C6 1.394(13) . ?
C6 C7 1.402(13) . ?
C7 C8 1.398(13) . ?
C8 C9 1.383(12) . ?
C8 C10 1.522(13) . ?
C9 H9 0.9500 . ?
C10 H10 1.0000 . ?
C10 C11 1.533(14) . ?
C10 C14 1.521(13) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.518(14) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C1 1.402(13) 2 ?
C13 H13 0.9500 . ?
C13 C14 1.384(13) . ?
C14 C15 1.414(13) . ?
C15 C16 1.388(13) . ?
C16 C2 1.398(13) 2 ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
O7 C24 1.211(18) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C23 C24 1.497(14) . ?
C24 C23 1.497(14) 2 ?
O5 N1 1.344(11) . ?
O6 C19 1.346(12) . ?
O6 C22 1.457(12) . ?
N1 C17 1.356(13) . ?
N1 C21 1.364(13) . ?
C17 H17 0.9500 . ?
C17 C18 1.368(15) . ?
C18 H18 0.9500 . ?
C18 C19 1.395(14) . ?
C19 C20 1.397(14) . ?
C20 H20 0.9500 . ?
C20 C21 1.369(14) . ?
C21 H21 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
O8 C26 1.194(13) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C25 C26 1.461(19) . ?
C26 C27 1.504(18) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 H1 111.7 . . ?
C5 O2 H2 151.7 . . ?
C7 O3 H3 109.5 . . ?
C15 O4 H4 111.7 . . ?
C2 C1 C3 122.1(8) . . ?
C2 C1 C13 117.5(9) . 2 ?
C13 C1 C3 120.4(8) 2 . ?
H1AA C1AA H1AB 107.9 . . ?
C3 C1AA H1AA 109.2 . . ?
C3 C1AA H1AB 109.2 . . ?
C32 C1AA H1AA 109.2 . . ?
C32 C1AA H1AB 109.2 . . ?
C32 C1AA C3 112.0(8) . . ?
O1 C2 C16 115.8(8) . 2 ?
C1 C2 O1 124.1(8) . . ?
C1 C2 C16 120.1(9) . 2 ?
C1 C3 C1AA 113.7(8) . . ?
C1 C3 H3A 106.4 . . ?
C1AA C3 H3A 106.4 . . ?
C4 C3 C1 110.7(7) . . ?
C4 C3 C1AA 112.7(7) . . ?
C4 C3 H3A 106.4 . . ?
C5 C4 C3 120.1(8) . . ?
C5 C4 C9 118.5(8) . . ?
C9 C4 C3 121.4(8) . . ?
O2 C5 C4 118.4(8) . . ?
O2 C5 C6 122.3(8) . . ?
C6 C5 C4 119.3(9) . . ?
C5 C6 Br2 119.4(7) . . ?
C5 C6 C7 121.0(8) . . ?
C7 C6 Br2 119.6(7) . . ?
O3 C7 C6 117.7(8) . . ?
O3 C7 C8 122.2(8) . . ?
C8 C7 C6 120.0(8) . . ?
C7 C8 C10 121.1(8) . . ?
C9 C8 C7 117.8(9) . . ?
C9 C8 C10 121.1(8) . . ?
C4 C9 H9 118.4 . . ?
C8 C9 C4 123.1(9) . . ?
C8 C9 H9 118.4 . . ?
C8 C10 H10 106.1 . . ?
C8 C10 C11 113.7(8) . . ?
C11 C10 H10 106.1 . . ?
C14 C10 C8 110.8(8) . . ?
C14 C10 H10 106.1 . . ?
C14 C10 C11 113.3(8) . . ?
C10 C11 H11A 108.9 . . ?
C10 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C12 C11 C10 113.4(8) . . ?
C12 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C1 C13 H13 118.4 2 . ?
C14 C13 C1 123.2(9) . 2 ?
C14 C13 H13 118.4 . . ?
C13 C14 C10 121.3(8) . . ?
C13 C14 C15 118.9(9) . . ?
C15 C14 C10 119.8(8) . . ?
O4 C15 C14 119.7(8) . . ?
O4 C15 C16 122.5(9) . . ?
C16 C15 C14 117.8(8) . . ?
C2 C16 Br1 119.5(7) 2 . ?
C15 C16 Br1 118.1(7) . . ?
C15 C16 C2 122.5(9) . 2 ?
C1AA C32 H32A 109.5 . . ?
C1AA C32 H32B 109.5 . . ?
C1AA C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C24 C23 H23A 109.5 . . ?
C24 C23 H23B 109.5 . . ?
C24 C23 H23C 109.5 . . ?
O7 C24 C23 121.4(8) . . ?
O7 C24 C23 121.4(7) . 2 ?
C23 C24 C23 117.2(15) . 2 ?
C19 O6 C22 117.3(8) . . ?
O5 N1 C17 120.1(8) . . ?
O5 N1 C21 119.0(8) . . ?
C17 N1 C21 120.9(9) . . ?
N1 C17 H17 119.8 . . ?
N1 C17 C18 120.4(9) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 119.7 . . ?
C17 C18 C19 120.5(10) . . ?
C19 C18 H18 119.7 . . ?
O6 C19 C18 126.1(9) . . ?
O6 C19 C20 116.3(9) . . ?
C18 C19 C20 117.6(9) . . ?
C19 C20 H20 119.5 . . ?
C21 C20 C19 121.0(9) . . ?
C21 C20 H20 119.5 . . ?
N1 C21 C20 119.6(9) . . ?
N1 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
O6 C22 H22A 109.5 . . ?
O6 C22 H22B 109.5 . . ?
O6 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C26 C25 H25A 109.5 . . ?
C26 C25 H25B 109.5 . . ?
C26 C25 H25C 109.5 . . ?
O8 C26 C25 124.4(13) . . ?
O8 C26 C27 119.3(13) . . ?
C25 C26 C27 116.3(13) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br2 C6 C7 O3 -1.6(12) . . . . ?
Br2 C6 C7 C8 175.9(7) . . . . ?
O2 C5 C6 Br2 -0.1(12) . . . . ?
O2 C5 C6 C7 179.2(8) . . . . ?
O3 C7 C8 C9 -177.5(8) . . . . ?
O3 C7 C8 C10 1.4(13) . . . . ?
O4 C15 C16 Br1 1.5(12) . . . . ?
O4 C15 C16 C2 -177.8(9) . . . 2 ?
C1 C3 C4 C5 97.3(10) . . . . ?
C1 C3 C4 C9 -81.6(10) . . . . ?
C1 C13 C14 C10 -179.7(9) 2 . . . ?
C1 C13 C14 C15 0.2(14) 2 . . . ?
C1AA C3 C4 C5 -134.1(9) . . . . ?
C1AA C3 C4 C9 46.9(12) . . . . ?
C2 C1 C3 C1AA 148.3(9) . . . . ?
C2 C1 C3 C4 -83.7(11) . . . . ?
C3 C1 C2 O1 0.3(14) . . . . ?
C3 C1 C2 C16 -179.5(9) . . . 2 ?
C3 C4 C5 O2 3.3(13) . . . . ?
C3 C4 C5 C6 -177.5(8) . . . . ?
C3 C4 C9 C8 179.4(8) . . . . ?
C4 C5 C6 Br2 -179.3(7) . . . . ?
C4 C5 C6 C7 0.0(13) . . . . ?
C5 C4 C9 C8 0.4(14) . . . . ?
C5 C6 C7 O3 179.1(8) . . . . ?
C5 C6 C7 C8 -3.3(14) . . . . ?
C6 C7 C8 C9 5.1(13) . . . . ?
C6 C7 C8 C10 -176.1(8) . . . . ?
C7 C8 C9 C4 -3.7(13) . . . . ?
C7 C8 C10 C11 134.2(9) . . . . ?
C7 C8 C10 C14 -96.8(10) . . . . ?
C8 C10 C11 C12 -65.0(11) . . . . ?
C8 C10 C14 C13 -94.1(10) . . . . ?
C8 C10 C14 C15 85.9(10) . . . . ?
C9 C4 C5 O2 -177.8(8) . . . . ?
C9 C4 C5 C6 1.5(13) . . . . ?
C9 C8 C10 C11 -47.0(12) . . . . ?
C9 C8 C10 C14 82.0(11) . . . . ?
C10 C8 C9 C4 177.4(8) . . . . ?
C10 C14 C15 O4 -2.5(12) . . . . ?
C10 C14 C15 C16 -179.3(8) . . . . ?
C11 C10 C14 C13 35.0(12) . . . . ?
C11 C10 C14 C15 -144.9(9) . . . . ?
C13 C1 C2 O1 -179.7(8) 2 . . . ?
C13 C1 C2 C16 0.5(14) 2 . . 2 ?
C13 C1 C3 C1AA -31.7(12) 2 . . . ?
C13 C1 C3 C4 96.3(10) 2 . . . ?
C13 C14 C15 O4 177.5(8) . . . . ?
C13 C14 C15 C16 0.7(13) . . . . ?
C14 C10 C11 C12 167.2(9) . . . . ?
C14 C15 C16 Br1 178.2(6) . . . . ?
C14 C15 C16 C2 -1.1(14) . . . 2 ?
C32 C1AA C3 C1 178.8(8) . . . . ?
C32 C1AA C3 C4 51.8(11) . . . . ?
O5 N1 C17 C18 179.4(9) . . . . ?
O5 N1 C21 C20 -177.8(8) . . . . ?
O6 C19 C20 C21 -178.0(9) . . . . ?
N1 C17 C18 C19 -1.0(15) . . . . ?
C17 N1 C21 C20 1.2(14) . . . . ?
C17 C18 C19 O6 179.6(9) . . . . ?
C17 C18 C19 C20 0.0(14) . . . . ?
C18 C19 C20 C21 1.7(14) . . . . ?
C19 C20 C21 N1 -2.3(15) . . . . ?
C21 N1 C17 C18 0.5(14) . . . . ?
C22 O6 C19 C18 0.9(13) . . . . ?
C22 O6 C19 C20 -179.5(8) . . . . ?

_shelx_SHELXL_version_number     2014/7
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
20 0 27 0.0128 20.0015 -0.0002 26.9940 -0.0252 -0.7440 0.6654
-20 -2 -26 0.0155 -20.0033 -1.9997 -25.9934 0.0218 0.8418 -0.5146
-4 -11 2 0.0894 -4.0103 -10.9992 2.0044 0.0116 0.6490 0.7338
5 11 -1 0.0638 5.0104 10.9992 -1.0047 -0.0175 -0.6792 -0.7074
-34 -1 23 0.0207 -34.0097 -1.0021 22.9989 0.9512 -0.0511 0.2867
34 1 -23 0.0024 34.0097 1.0021 -22.9989 -0.9512 0.0511 -0.2867

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_acetone_BrC2_8
_database_code_depnum_ccdc_archive 'CCDC 1551409'
_audit_update_record             
;
2017-05-22 deposited with the CCDC.
2017-06-15 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT094_acetone_BrC2_8      
;
PROBLEM: Ratio of Maximum / Minimum Residual Density ....       4.14 Report
RESPONSE: Due to unresolved disorder
;
# end Validation Reply Form
_audit_creation_date             2017-05-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C36 H36 Br4 O8, 2(C9 H7 N O), 2(C3 H6 O)'
_chemical_formula_sum            'C60 H62 Br4 N2 O12'
_chemical_formula_weight         1322.75
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 O9 N1 Br2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   25.3967(6)
_cell_length_b                   7.78520(18)
_cell_length_c                   27.8052(8)
_cell_angle_alpha                90
_cell_angle_beta                 96.897(2)
_cell_angle_gamma                90
_cell_volume                     5457.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4884
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      73.9580
_cell_measurement_theta_min      4.4450
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.150
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92465
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.610
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             2688
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-15 0 9 0.0165
15 0 -9 0.0183
0 -5 -1 0.0509
0 5 1 0.0543
4 0 17 0.0114
-3 0 -17 0.0100

_exptl_crystal_size_max          0.107
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.022
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-15.0001 0.0000 8.9990 -0.0151 0.1012 0.9850
15.0001 -0.0000 -8.9990 0.0151 -0.1012 -0.9850
-0.0002 -5.0000 -0.9974 0.3826 -0.9098 0.0772
0.0002 5.0000 0.9974 -0.3826 0.9098 -0.0772
3.9996 0.0000 17.0000 0.8952 0.4464 0.1327
-2.9996 -0.0000 -17.0000 -0.8666 -0.4385 -0.1861

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            9196
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        66.730
_diffrn_reflns_theta_max         66.730
_diffrn_reflns_theta_min         3.675
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -66.00  33.00   1.00    6.00    --  -41.90  37.00 120.00   99
  2  ω      1.00  83.00   1.00    6.00    --   41.90 -99.00-120.00   82
  3  ω     77.00 153.00   1.00   24.00    --  106.66  77.00 -60.00   76
  4  ω     24.00 103.00   1.00   24.00    --  106.66 -94.00  60.00   79
  5  ω     36.00 117.00   1.00   24.00    --  106.66-125.00 -90.00   81
  6  ω     37.00 134.00   1.00   24.00    --  106.66 -61.00-120.00   97
  7  ω     92.00 144.00   1.00   24.00    --  106.66  61.00   0.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0285643000
_diffrn_orient_matrix_UB_12      -0.0856828000
_diffrn_orient_matrix_UB_13      0.0459380000
_diffrn_orient_matrix_UB_21      0.0078944000
_diffrn_orient_matrix_UB_22      0.1771019000
_diffrn_orient_matrix_UB_23      0.0244003000
_diffrn_orient_matrix_UB_31      -0.0534428000
_diffrn_orient_matrix_UB_32      -0.0194956000
_diffrn_orient_matrix_UB_33      0.0203794000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4424
_reflns_number_total             4865
_reflns_odcompleteness_completeness 98.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         3.507
_refine_diff_density_min         -0.848
_refine_diff_density_rms         0.196
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     378
_refine_ls_number_reflns         4865
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0549
_refine_ls_restrained_S_all      1.123
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0451P)²+140.8365P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1512
_refine_ls_wR_factor_ref         0.1626
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.9363(11) 0.0637(11)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3. Restrained distances
 C30-C31
 1.54 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(C32) \\sim Ueq, Uanis(C30) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.01
Uanis(C13) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
5. Others
 Fixed Sof: O6(0.5) C30(0.5) H30A(0.5) H30B(0.5) H30C(0.5) C31(0.5) C32(0.5)
 H32A(0.5) H32B(0.5) H32C(0.5)
6.a Riding coordinates:
 O1(H1), O2(H2), O3(H3)
6.b Ternary CH refined with riding coordinates:
 C7(H7), C16(H16)
6.c Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C17(H17A,H17B)
6.d Aromatic/amide H refined with riding coordinates:
 C2(H2A), C9(H9), C19(H19), C20(H20), C23(H23), C24(H24), C25(H25), C26(H26),
 C27(H27)
6.e Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C18(H18A,H18B,H18C), C29(H29A,H29B,H29C), C30(H30A,H30B,
 H30C), C32(H32A,H32B,H32C)
6.f Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.48480(3) 0.94051(10) 0.07459(3) 0.0198(2) Uani 1 1 d . . . . .
Br2 Br 0.26262(2) 0.82675(9) 0.24927(2) 0.01330(19) Uani 1 1 d . . . . .
O1 O 0.58007(18) 0.7307(7) 0.10957(17) 0.0180(11) Uani 1 1 d . . . . .
H1 H 0.6088 0.7087 0.1277 0.027 Uiso 1 1 d R . . . .
O2 O 0.39399(18) 0.7459(7) 0.10670(18) 0.0181(10) Uani 1 1 d . . . . .
H2 H 0.3686 0.7290 0.1229 0.027 Uiso 1 1 d R . . . .
O3 O 0.31085(18) 0.6717(7) 0.16117(16) 0.0159(10) Uani 1 1 d . . . . .
H3 H 0.2861 0.7422 0.1514 0.024 Uiso 1 1 d R . . . .
O4 O 0.32319(18) 0.6439(6) 0.33569(16) 0.0128(10) Uani 1 1 d . . . . .
H4 H 0.3086 0.5637 0.3479 0.019 Uiso 1 1 calc GR . . . .
O5 O 0.2294(2) 0.8948(7) 0.12731(17) 0.0217(11) Uani 1 1 d . . . . .
O6 O 0.4333(5) 0.617(2) -0.0284(6) 0.051(4) Uani 0.5 1 d . . . . .
O7 O 0.5000 1.1104(9) 0.2500 0.0199(15) Uani 1 2 d S T P . .
N1 N 0.2331(2) 0.9308(8) 0.0805(2) 0.0160(12) Uani 1 1 d . . . . .
C1 C 0.4408(3) 0.4999(9) 0.1448(2) 0.0117(13) Uani 1 1 d . . . . .
C2 C 0.4898(3) 0.4231(9) 0.1572(2) 0.0136(13) Uani 1 1 d . . . . .
H2A H 0.4910 0.3195 0.1739 0.016 Uiso 1 1 calc R . . . .
C3 C 0.5377(3) 0.4921(9) 0.1459(2) 0.0118(13) Uani 1 1 d . . . . .
C4 C 0.5360(3) 0.6495(10) 0.1224(2) 0.0137(14) Uani 1 1 d . . . . .
C5 C 0.4869(3) 0.7297(9) 0.1089(2) 0.0156(14) Uani 1 1 d . . . . .
C6 C 0.4402(3) 0.6596(10) 0.1205(2) 0.0151(14) Uani 1 1 d . . . . .
C7 C 0.3896(2) 0.4189(9) 0.1569(2) 0.0121(13) Uani 1 1 d . . . . .
H7 H 0.3617 0.4528 0.1312 0.015 Uiso 1 1 calc R . . . .
C8 C 0.3733(2) 0.4881(9) 0.2046(2) 0.0104(13) Uani 1 1 d . . . . .
C9 C 0.3979(2) 0.4256(9) 0.2488(2) 0.0117(13) Uani 1 1 d . . . . .
H9 H 0.4259 0.3486 0.2487 0.014 Uiso 1 1 calc R . . . .
C10 C 0.3819(2) 0.4747(8) 0.2931(2) 0.0106(13) Uani 1 1 d . . . . .
C11 C 0.3404(2) 0.5905(9) 0.2926(2) 0.0104(12) Uani 1 1 d . . . . .
C12 C 0.3169(2) 0.6604(8) 0.2490(2) 0.0115(13) Uani 1 1 d . . . . .
C13 C 0.3329(2) 0.6081(9) 0.2050(2) 0.0114(13) Uani 1 1 d . U . . .
C14 C 0.3915(3) 0.2210(9) 0.1569(2) 0.0148(14) Uani 1 1 d . . . . .
H14A H 0.3986 0.1816 0.1252 0.018 Uiso 1 1 calc R . . . .
H14B H 0.4205 0.1830 0.1804 0.018 Uiso 1 1 calc R . . . .
C15 C 0.3399(3) 0.1398(10) 0.1690(3) 0.0217(16) Uani 1 1 d . . . . .
H15A H 0.3110 0.1776 0.1460 0.033 Uiso 1 1 calc GR . . . .
H15B H 0.3336 0.1737 0.2010 0.033 Uiso 1 1 calc GR . . . .
H15C H 0.3428 0.0169 0.1676 0.033 Uiso 1 1 calc GR . . . .
C16 C 0.5903(3) 0.3999(9) 0.1596(2) 0.0116(13) Uani 1 1 d . . . . .
H16 H 0.6128 0.4269 0.1343 0.014 Uiso 1 1 calc R . . . .
C17 C 0.5853(3) 0.2035(9) 0.1609(2) 0.0147(14) Uani 1 1 d . . . . .
H17A H 0.5627 0.1720 0.1852 0.018 Uiso 1 1 calc R . . . .
H17B H 0.5684 0.1636 0.1298 0.018 Uiso 1 1 calc R . . . .
C18 C 0.6387(3) 0.1144(10) 0.1723(3) 0.0215(16) Uani 1 1 d . . . . .
H18A H 0.6622 0.1519 0.1498 0.032 Uiso 1 1 calc GR . . . .
H18B H 0.6339 -0.0077 0.1696 0.032 Uiso 1 1 calc GR . . . .
H18C H 0.6537 0.1428 0.2046 0.032 Uiso 1 1 calc GR . . . .
C19 C 0.1897(3) 0.9500(13) 0.0493(3) 0.0296(19) Uani 1 1 d . . . . .
H19 H 0.1566 0.9335 0.0597 0.036 Uiso 1 1 calc R . . . .
C20 C 0.1929(3) 0.9936(14) 0.0022(3) 0.037(2) Uani 1 1 d . . . . .
H20 H 0.1620 1.0105 -0.0188 0.044 Uiso 1 1 calc R . . . .
C21 C 0.2425(3) 1.0133(11) -0.0151(3) 0.0213(16) Uani 1 1 d . . . . .
C22 C 0.2883(3) 0.9812(9) 0.0179(2) 0.0163(14) Uani 1 1 d . . . . .
C23 C 0.2821(3) 0.9400(10) 0.0663(3) 0.0199(15) Uani 1 1 d . . . . .
H23 H 0.3118 0.9193 0.0885 0.024 Uiso 1 1 calc R . . . .
C24 C 0.3395(3) 0.9965(12) 0.0027(3) 0.0282(18) Uani 1 1 d . . . . .
H24 H 0.3698 0.9749 0.0242 0.034 Uiso 1 1 calc R . . . .
C25 C 0.3436(3) 1.0434(12) -0.0440(3) 0.0308(19) Uani 1 1 d . . . . .
H25 H 0.3770 1.0548 -0.0541 0.037 Uiso 1 1 calc R . . . .
C26 C 0.2984(4) 1.0748(12) -0.0771(3) 0.033(2) Uani 1 1 d . . . . .
H26 H 0.3026 1.1056 -0.1088 0.040 Uiso 1 1 calc R . . . .
C27 C 0.2494(3) 1.0616(11) -0.0643(3) 0.0243(17) Uani 1 1 d . . . . .
H27 H 0.2201 1.0832 -0.0868 0.029 Uiso 1 1 calc R . . . .
C28 C 0.5000 0.9544(14) 0.2500 0.022(2) Uani 1 2 d S T P . .
C29 C 0.4528(5) 0.8524(12) 0.2485(3) 0.052(3) Uani 1 1 d . . . . .
H29A H 0.4532 0.7896 0.2783 0.079 Uiso 1 1 calc GR . . . .
H29B H 0.4513 0.7733 0.2219 0.079 Uiso 1 1 calc GR . . . .
H29C H 0.4223 0.9260 0.2444 0.079 Uiso 1 1 calc GR . . . .
C30 C 0.5288(10) 0.589(5) -0.0145(15) 0.043(9) Uani 0.5 1 d D U . A -1
H30A H 0.5334 0.7080 -0.0058 0.064 Uiso 0.5 1 calc GR . . A -1
H30B H 0.5368 0.5727 -0.0471 0.064 Uiso 0.5 1 calc GR . . A -1
H30C H 0.5523 0.5202 0.0072 0.064 Uiso 0.5 1 calc GR . . A -1
C31 C 0.4711(6) 0.536(2) -0.0111(6) 0.026(4) Uani 0.5 1 d D . . A -1
C32 C 0.4689(13) 0.372(4) 0.0190(15) 0.040(8) Uani 0.5 1 d . U . A -1
H32A H 0.4337 0.3256 0.0142 0.059 Uiso 0.5 1 calc GR . . A -1
H32B H 0.4782 0.3987 0.0526 0.059 Uiso 0.5 1 calc GR . . A -1
H32C H 0.4934 0.2894 0.0090 0.059 Uiso 0.5 1 calc GR . . A -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C5 1.896(7) . ?
Br2 C12 1.891(6) . ?
O1 H1 0.8536 . ?
O1 C4 1.370(8) . ?
O2 H2 0.8413 . ?
O2 C6 1.366(8) . ?
O3 H3 0.8533 . ?
O3 C13 1.372(8) . ?
O4 H4 0.8200 . ?
O4 C11 1.388(8) . ?
O5 N1 1.347(7) . ?
O6 C31 1.20(2) . ?
O7 C28 1.214(13) . ?
N1 C19 1.327(10) . ?
N1 C23 1.351(9) . ?
C1 C2 1.387(10) . ?
C1 C6 1.414(10) . ?
C1 C7 1.520(9) . ?
C2 H2A 0.9300 . ?
C2 C3 1.397(10) . ?
C3 C4 1.387(10) . ?
C3 C16 1.526(9) . ?
C4 C5 1.405(10) . ?
C5 C6 1.379(10) . ?
C7 H7 0.9800 . ?
C7 C8 1.534(9) . ?
C7 C14 1.541(9) . ?
C8 C9 1.397(9) . ?
C8 C13 1.388(9) . ?
C9 H9 0.9300 . ?
C9 C10 1.395(9) . ?
C10 C11 1.385(9) . ?
C10 C16 1.531(9) 2_655 ?
C11 C12 1.398(10) . ?
C12 C13 1.395(9) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.529(10) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C10 1.531(9) 2_655 ?
C16 H16 0.9800 . ?
C16 C17 1.535(9) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.523(10) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19 0.9300 . ?
C19 C20 1.366(12) . ?
C20 H20 0.9300 . ?
C20 C21 1.408(11) . ?
C21 C22 1.413(10) . ?
C21 C27 1.451(10) . ?
C22 C23 1.411(10) . ?
C22 C24 1.421(10) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C24 C25 1.363(11) . ?
C25 H25 0.9300 . ?
C25 C26 1.405(13) . ?
C26 H26 0.9300 . ?
C26 C27 1.337(12) . ?
C27 H27 0.9300 . ?
C28 C29 1.435(11) 2_655 ?
C28 C29 1.435(11) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C30 C31 1.537(19) . ?
C31 C32 1.53(4) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O1 H1 114.9 . . ?
C6 O2 H2 117.4 . . ?
C13 O3 H3 136.3 . . ?
C11 O4 H4 109.5 . . ?
O5 N1 C23 117.8(6) . . ?
C19 N1 O5 120.4(6) . . ?
C19 N1 C23 121.7(6) . . ?
C2 C1 C6 117.1(6) . . ?
C2 C1 C7 122.2(6) . . ?
C6 C1 C7 120.6(6) . . ?
C1 C2 H2A 118.1 . . ?
C1 C2 C3 123.9(6) . . ?
C3 C2 H2A 118.1 . . ?
C2 C3 C16 121.5(6) . . ?
C4 C3 C2 117.9(6) . . ?
C4 C3 C16 120.6(6) . . ?
O1 C4 C3 123.5(6) . . ?
O1 C4 C5 116.8(6) . . ?
C3 C4 C5 119.6(6) . . ?
C4 C5 Br1 119.3(5) . . ?
C6 C5 Br1 119.2(5) . . ?
C6 C5 C4 121.5(7) . . ?
O2 C6 C1 121.8(6) . . ?
O2 C6 C5 118.2(6) . . ?
C5 C6 C1 120.0(6) . . ?
C1 C7 H7 106.9 . . ?
C1 C7 C8 111.8(5) . . ?
C1 C7 C14 112.7(6) . . ?
C8 C7 H7 106.9 . . ?
C8 C7 C14 111.3(6) . . ?
C14 C7 H7 106.9 . . ?
C9 C8 C7 120.0(6) . . ?
C13 C8 C7 121.3(6) . . ?
C13 C8 C9 118.7(6) . . ?
C8 C9 H9 118.9 . . ?
C10 C9 C8 122.3(6) . . ?
C10 C9 H9 118.9 . . ?
C9 C10 C16 120.1(6) . 2_655 ?
C11 C10 C9 118.1(6) . . ?
C11 C10 C16 121.8(6) . 2_655 ?
O4 C11 C12 119.1(6) . . ?
C10 C11 O4 120.3(6) . . ?
C10 C11 C12 120.5(6) . . ?
C11 C12 Br2 119.9(5) . . ?
C13 C12 Br2 119.6(5) . . ?
C13 C12 C11 120.5(6) . . ?
O3 C13 C8 117.4(6) . . ?
O3 C13 C12 122.8(6) . . ?
C8 C13 C12 119.9(6) . . ?
C7 C14 H14A 109.1 . . ?
C7 C14 H14B 109.1 . . ?
H14A C14 H14B 107.8 . . ?
C15 C14 C7 112.6(6) . . ?
C15 C14 H14A 109.1 . . ?
C15 C14 H14B 109.1 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C3 C16 C10 109.5(5) . 2_655 ?
C3 C16 H16 106.7 . . ?
C3 C16 C17 113.7(6) . . ?
C10 C16 H16 106.7 2_655 . ?
C10 C16 C17 112.9(6) 2_655 . ?
C17 C16 H16 106.7 . . ?
C16 C17 H17A 109.1 . . ?
C16 C17 H17B 109.1 . . ?
H17A C17 H17B 107.8 . . ?
C18 C17 C16 112.6(6) . . ?
C18 C17 H17A 109.1 . . ?
C18 C17 H17B 109.1 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 C19 H19 119.5 . . ?
N1 C19 C20 120.9(7) . . ?
C20 C19 H19 119.5 . . ?
C19 C20 H20 119.6 . . ?
C19 C20 C21 120.9(8) . . ?
C21 C20 H20 119.6 . . ?
C20 C21 C22 117.4(7) . . ?
C20 C21 C27 124.3(7) . . ?
C22 C21 C27 118.3(7) . . ?
C21 C22 C24 120.3(7) . . ?
C23 C22 C21 118.8(6) . . ?
C23 C22 C24 120.9(7) . . ?
N1 C23 C22 120.1(7) . . ?
N1 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C22 C24 H24 120.6 . . ?
C25 C24 C22 118.8(8) . . ?
C25 C24 H24 120.6 . . ?
C24 C25 H25 119.3 . . ?
C24 C25 C26 121.5(8) . . ?
C26 C25 H25 119.3 . . ?
C25 C26 H26 119.2 . . ?
C27 C26 C25 121.6(8) . . ?
C27 C26 H26 119.2 . . ?
C21 C27 H27 120.2 . . ?
C26 C27 C21 119.6(7) . . ?
C26 C27 H27 120.2 . . ?
O7 C28 C29 123.6(6) . 2_655 ?
O7 C28 C29 123.6(6) . . ?
C29 C28 C29 112.8(13) 2_655 . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C31 C30 H30A 109.5 . . ?
C31 C30 H30B 109.5 . . ?
C31 C30 H30C 109.5 . . ?
O6 C31 C30 124(2) . . ?
O6 C31 C32 125.4(16) . . ?
C32 C31 C30 111(2) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C5 C6 O2 0.1(9) . . . . ?
Br1 C5 C6 C1 178.1(5) . . . . ?
Br2 C12 C13 O3 -0.3(9) . . . . ?
Br2 C12 C13 C8 179.0(5) . . . . ?
O1 C4 C5 Br1 -0.1(8) . . . . ?
O1 C4 C5 C6 -179.2(6) . . . . ?
O4 C11 C12 Br2 0.5(8) . . . . ?
O4 C11 C12 C13 -179.3(6) . . . . ?
O5 N1 C19 C20 177.2(8) . . . . ?
O5 N1 C23 C22 -178.6(6) . . . . ?
N1 C19 C20 C21 2.3(16) . . . . ?
C1 C2 C3 C4 2.2(10) . . . . ?
C1 C2 C3 C16 -178.8(6) . . . . ?
C1 C7 C8 C9 -79.2(8) . . . . ?
C1 C7 C8 C13 103.3(7) . . . . ?
C1 C7 C14 C15 -179.9(6) . . . . ?
C2 C1 C6 O2 179.9(6) . . . . ?
C2 C1 C6 C5 2.0(9) . . . . ?
C2 C1 C7 C8 94.8(7) . . . . ?
C2 C1 C7 C14 -31.6(9) . . . . ?
C2 C3 C4 O1 179.8(6) . . . . ?
C2 C3 C4 C5 -2.9(9) . . . . ?
C2 C3 C16 C10 -97.3(7) . . . 2_655 ?
C2 C3 C16 C17 30.1(9) . . . . ?
C3 C4 C5 Br1 -177.6(5) . . . . ?
C3 C4 C5 C6 3.3(10) . . . . ?
C3 C16 C17 C18 177.2(6) . . . . ?
C4 C3 C16 C10 81.7(7) . . . 2_655 ?
C4 C3 C16 C17 -150.9(6) . . . . ?
C4 C5 C6 O2 179.2(6) . . . . ?
C4 C5 C6 C1 -2.8(10) . . . . ?
C6 C1 C2 C3 -1.8(10) . . . . ?
C6 C1 C7 C8 -84.6(7) . . . . ?
C6 C1 C7 C14 149.1(6) . . . . ?
C7 C1 C2 C3 178.8(6) . . . . ?
C7 C1 C6 O2 -0.7(9) . . . . ?
C7 C1 C6 C5 -178.6(6) . . . . ?
C7 C8 C9 C10 -175.1(6) . . . . ?
C7 C8 C13 O3 -4.7(9) . . . . ?
C7 C8 C13 C12 176.0(6) . . . . ?
C8 C7 C14 C15 53.5(8) . . . . ?
C8 C9 C10 C11 -0.5(10) . . . . ?
C8 C9 C10 C16 179.0(6) . . . 2_655 ?
C9 C8 C13 O3 177.7(6) . . . . ?
C9 C8 C13 C12 -1.6(9) . . . . ?
C9 C10 C11 O4 -179.8(6) . . . . ?
C9 C10 C11 C12 -2.4(9) . . . . ?
C10 C11 C12 Br2 -176.9(5) . . . . ?
C10 C11 C12 C13 3.2(10) . . . . ?
C10 C16 C17 C18 -57.2(8) 2_655 . . . ?
C11 C12 C13 O3 179.5(6) . . . . ?
C11 C12 C13 C8 -1.2(9) . . . . ?
C13 C8 C9 C10 2.5(10) . . . . ?
C14 C7 C8 C9 47.9(8) . . . . ?
C14 C7 C8 C13 -129.7(7) . . . . ?
C16 C3 C4 O1 0.8(9) . . . . ?
C16 C3 C4 C5 178.1(6) . . . . ?
C16 C10 C11 O4 0.8(10) 2_655 . . . ?
C16 C10 C11 C12 178.2(6) 2_655 . . . ?
C19 N1 C23 C22 3.9(12) . . . . ?
C19 C20 C21 C22 1.8(14) . . . . ?
C19 C20 C21 C27 -179.1(9) . . . . ?
C20 C21 C22 C23 -3.1(12) . . . . ?
C20 C21 C22 C24 179.2(8) . . . . ?
C20 C21 C27 C26 -179.2(9) . . . . ?
C21 C22 C23 N1 0.4(11) . . . . ?
C21 C22 C24 C25 0.4(13) . . . . ?
C22 C21 C27 C26 -0.2(12) . . . . ?
C22 C24 C25 C26 -0.7(14) . . . . ?
C23 N1 C19 C20 -5.3(14) . . . . ?
C23 C22 C24 C25 -177.3(8) . . . . ?
C24 C22 C23 N1 178.1(7) . . . . ?
C24 C25 C26 C27 0.6(15) . . . . ?
C25 C26 C27 C21 -0.1(14) . . . . ?
C27 C21 C22 C23 177.8(7) . . . . ?
C27 C21 C22 C24 0.1(12) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.128
_oxdiff_exptl_absorpt_empirical_full_min 0.882
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.9363(11)
2 0.0637(11)

####################################################################### 
# 
# 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_acetone_BrC2_7
_database_code_depnum_ccdc_archive 'CCDC 1551408'
_audit_update_record             
;
2017-05-22 deposited with the CCDC.
2017-06-15 downloaded from the CCDC.
;
_audit_creation_date             2017-05-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C36 H36 Br4 O8, 3(C11 H9 N O), C3 H6 O'
_chemical_formula_sum            'C72 H69 Br4 N3 O12'
_chemical_formula_weight         1487.94
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N1 O9'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 1 2/n 1'
_space_group_name_Hall           '-P 2yac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z-1/2'

_cell_length_a                   19.2354(5)
_cell_length_b                   7.84234(14)
_cell_length_c                   22.8722(6)
_cell_angle_alpha                90
_cell_angle_beta                 114.269(3)
_cell_angle_gamma                90
_cell_volume                     3145.36(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7405
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      73.1800
_cell_measurement_theta_min      3.8720
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.681
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89626
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1516
_exptl_crystal_size_max          0.0696
_exptl_crystal_size_mid          0.0559
_exptl_crystal_size_min          0.0277
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0611
_diffrn_reflns_av_unetI/netI     0.0598
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            17556
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.736
_diffrn_reflns_theta_max         66.736
_diffrn_reflns_theta_min         3.904
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -115.00  -19.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676  -37.0000   30.0000 96

#__ type_ start__ end____ width___ exp.time_
  2 omega  -72.00   29.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676   77.0000 -150.0000 101

#__ type_ start__ end____ width___ exp.time_
  3 omega   77.00  173.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154   61.0000  120.0000 96

#__ type_ start__ end____ width___ exp.time_
  4 omega   82.00  175.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154   61.0000 -180.0000 93

#__ type_ start__ end____ width___ exp.time_
  5 omega   50.00   94.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -45.0000 -180.0000 44

#__ type_ start__ end____ width___ exp.time_
  6 omega   33.00  135.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -61.0000   30.0000 102

#__ type_ start__ end____ width___ exp.time_
  7 omega   39.00   90.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -94.0000  -60.0000 51

#__ type_ start__ end____ width___ exp.time_
  8 omega  -23.00   19.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.6176   37.0000  150.0000 42

#__ type_ start__ end____ width___ exp.time_
  9 omega  -64.00   33.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.6176   77.0000  -30.0000 97

#__ type_ start__ end____ width___ exp.time_
 10 omega  118.00  178.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154   45.0000   60.0000 60

#__ type_ start__ end____ width___ exp.time_
 11 omega   85.00  111.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154   45.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 12 omega   25.00   51.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -94.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 13 omega   72.00  109.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -94.0000  120.0000 37

#__ type_ start__ end____ width___ exp.time_
 14 omega   24.00  109.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -94.0000    0.0000 85

#__ type_ start__ end____ width___ exp.time_
 15 omega  128.00  154.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154   45.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 16 omega   34.00   76.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154 -125.0000  -90.0000 42
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0050365000
_diffrn_orient_matrix_UB_12      -0.0070742000
_diffrn_orient_matrix_UB_13      0.0689557000
_diffrn_orient_matrix_UB_21      -0.0386546000
_diffrn_orient_matrix_UB_22      0.1760782000
_diffrn_orient_matrix_UB_23      -0.0094667000
_diffrn_orient_matrix_UB_31      -0.0787209000
_diffrn_orient_matrix_UB_32      -0.0867675000
_diffrn_orient_matrix_UB_33      -0.0248337000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4769
_reflns_number_total             5578
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.435
_refine_diff_density_min         -0.499
_refine_diff_density_rms         0.115
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     450
_refine_ls_number_reflns         5578
_refine_ls_number_restraints     41
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0451
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0696P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1081
_refine_ls_wR_factor_ref         0.1147
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 H4-O4
 0.85 with sigma of 0.02
 O7-N2
 1.34 with sigma of 0.02
 O3-H3
 0.85 with sigma of 0.02
 O2-H2
 0.85 with sigma of 0.02
 H5-O5
 0.85 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C32) \\sim Ueq, Uanis(C34) \\sim Ueq, Uanis(C31) \\sim Ueq, Uanis(C30)
\\sim Ueq, Uanis(N2) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms
of 0.02
Uanis(C37) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Fixed Sof: O7(0.5) C30(0.5) H30(0.5) C31(0.5) H31(0.5) C32(0.5) C33(0.5)
 H33(0.5) C34(0.5) H34(0.5) N2(0.5) C38(0.5) H38(0.5) C37(0.5) H37(0.5)
 C36(0.5) H36(0.5) C35(0.5) C40(0.5) H40(0.5) C39(0.5) H39(0.5)
 Fixed U11: O7(0.104627) C34(0.078601) C37(0.086901)
 Fixed U22: C37(0.0962)
 Fixed U33: C39(0.09185)
5.a Riding coordinates:
 O2(H2), O3(H3), O5(H5)
5.b Ternary CH refined with riding coordinates:
 C7(H7), C16(H16)
5.c Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C17(H17A,H17B)
5.d Aromatic/amide H refined with riding coordinates:
 C1(H1), C10(H10), C19(H19), C20(H20), C22(H22), C23(H23), C25(H25), C26(H26),
 C27(H27), C28(H28), C29(H29), C30(H30), C31(H31), C33(H33), C34(H34), C38(H38),
  C37(H37), C36(H36), C40(H40), C39(H39)
5.e Fitted hexagon refined as free rotating group:
 C30(C31,C32,C33,C34,N2), C38(C37,C36,C35,C40,C39)
5.f Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C18(H18A,H18B,H18C), C41(H41A,H41B,H41C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.26906(2) 0.36485(4) 0.46788(2) 0.02347(12) Uani 1 1 d . . . . .
Br2 Br -0.08747(2) 0.46720(4) 0.14589(2) 0.02283(12) Uani 1 1 d . . . . .
O2 O 0.00061(13) 0.6241(3) 0.28023(11) 0.0229(5) Uani 1 1 d D . . . .
H2 H -0.0426 0.6563 0.2779 0.12(3) Uiso 1 1 d DR . . A 1
O3 O 0.13106(13) 0.5584(3) 0.38561(12) 0.0254(5) Uani 1 1 d D . . . .
H3 H 0.0918 0.5859 0.3524 0.051(15) Uiso 1 1 d DR . . . .
O4 O 0.39860(13) 0.5714(3) 0.46689(11) 0.0221(5) Uani 1 1 d D . . . .
H4 H 0.435(2) 0.604(6) 0.460(3) 0.038(13) Uiso 1 1 d D . . . .
O5 O -0.01971(13) 0.6543(3) 0.06290(11) 0.0234(5) Uani 1 1 d D . . . .
H5 H -0.0487 0.5958 0.0318 0.035 Uiso 1 1 d DR . . . .
C1 C 0.10223(17) 0.8796(4) 0.20742(16) 0.0185(6) Uani 1 1 d . . . . .
H1 H 0.1416 0.9590 0.2199 0.022 Uiso 1 1 calc R . . . .
C2 C 0.07058(17) 0.8255(4) 0.14407(15) 0.0180(6) Uani 1 1 d . . . . .
C3 C 0.01187(18) 0.7048(4) 0.12596(15) 0.0199(6) Uani 1 1 d . . . . .
C4 C -0.01140(17) 0.6388(4) 0.17140(16) 0.0195(6) Uani 1 1 d . . . . .
C5 C 0.02066(18) 0.6958(4) 0.23470(16) 0.0204(6) Uani 1 1 d . . . . .
C6 C 0.07766(17) 0.8204(4) 0.25305(15) 0.0169(6) Uani 1 1 d . . . . .
C7 C 0.11230(17) 0.8873(4) 0.32184(15) 0.0187(6) Uani 1 1 d . . . . .
H7 H 0.0787 0.8502 0.3420 0.022 Uiso 1 1 calc R . . . .
C8 C 0.11465(19) 1.0827(4) 0.32464(16) 0.0217(6) Uani 1 1 d . . . . .
H8A H 0.1406 1.1189 0.3689 0.026 Uiso 1 1 calc R . . . .
H8B H 0.1435 1.1247 0.3014 0.026 Uiso 1 1 calc R . . . .
C9 C 0.0345(2) 1.1602(5) 0.2957(2) 0.0330(8) Uani 1 1 d . . . . .
H9A H 0.0099 1.1305 0.2511 0.050 Uiso 1 1 calc GR . . . .
H9B H 0.0381 1.2820 0.3000 0.050 Uiso 1 1 calc GR . . . .
H9C H 0.0054 1.1167 0.3178 0.050 Uiso 1 1 calc GR . . . .
C10 C 0.25745(19) 0.8795(4) 0.36448(15) 0.0189(6) Uani 1 1 d . . . . .
H10 H 0.2550 0.9825 0.3436 0.023 Uiso 1 1 calc R . . . .
C11 C 0.18955(18) 0.8046(4) 0.35908(14) 0.0186(6) Uani 1 1 d . . . . .
C12 C 0.19340(18) 0.6454(4) 0.38900(15) 0.0183(6) Uani 1 1 d . . . . .
C13 C 0.26466(18) 0.5736(4) 0.42468(15) 0.0199(6) Uani 1 1 d . . . . .
C14 C 0.33154(18) 0.6517(4) 0.43029(15) 0.0191(6) Uani 1 1 d . . . . .
C15 C 0.32947(18) 0.8078(4) 0.39986(14) 0.0173(6) Uani 1 1 d . . . . .
C16 C 0.40283(18) 0.8960(4) 0.40551(15) 0.0187(6) Uani 1 1 d . . . . .
H16 H 0.4422 0.8661 0.4478 0.022 Uiso 1 1 calc R . . . .
C17 C 0.39708(19) 1.0914(4) 0.40321(16) 0.0219(6) Uani 1 1 d . . . . .
H17A H 0.3558 1.1254 0.3632 0.026 Uiso 1 1 calc R . . . .
H17B H 0.3848 1.1306 0.4381 0.026 Uiso 1 1 calc R . . . .
C18 C 0.4705(2) 1.1776(4) 0.40849(17) 0.0260(7) Uani 1 1 d . . . . .
H18A H 0.4777 1.1576 0.3699 0.039 Uiso 1 1 calc GR . . . .
H18B H 0.5129 1.1313 0.4445 0.039 Uiso 1 1 calc GR . . . .
H18C H 0.4671 1.2980 0.4144 0.039 Uiso 1 1 calc GR . . . .
O6 O -0.12666(19) 0.7058(4) 0.27508(17) 0.0475(8) Uani 1 1 d . . . . .
N1 N -0.15061(18) 0.5822(5) 0.30340(17) 0.0352(7) Uani 1 1 d . . . . .
C19 C -0.1376(2) 0.4172(6) 0.2967(2) 0.0370(9) Uani 1 1 d . . . . .
H19 H -0.1086 0.3866 0.2743 0.044 Uiso 1 1 calc R . . . .
C20 C -0.1667(2) 0.2928(6) 0.3225(2) 0.0370(9) Uani 1 1 d . . . . .
H20 H -0.1574 0.1787 0.3172 0.044 Uiso 1 1 calc R . . . .
C21 C -0.2101(2) 0.3353(5) 0.35665(19) 0.0312(8) Uani 1 1 d . . . . .
C22 C -0.2187(2) 0.5082(5) 0.36521(19) 0.0331(8) Uani 1 1 d . . . . .
H22 H -0.2445 0.5423 0.3898 0.040 Uiso 1 1 calc R . . . .
C23 C -0.1899(2) 0.6296(5) 0.3381(2) 0.0373(9) Uani 1 1 d . . . . .
H23 H -0.1973 0.7446 0.3436 0.045 Uiso 1 1 calc R . . . .
C24 C -0.2488(2) 0.2037(5) 0.37886(18) 0.0279(7) Uani 1 1 d . . . . .
C25 C -0.2531(2) 0.2180(5) 0.43835(18) 0.0313(8) Uani 1 1 d . . . . .
H25 H -0.2292 0.3084 0.4655 0.038 Uiso 1 1 calc R . . . .
C26 C -0.2927(2) 0.0979(5) 0.45664(19) 0.0337(8) Uani 1 1 d . . . . .
H26 H -0.2943 0.1068 0.4966 0.040 Uiso 1 1 calc R . . . .
C27 C -0.3301(2) -0.0356(5) 0.41648(19) 0.0317(8) Uani 1 1 d . . . . .
H27 H -0.3578 -0.1138 0.4289 0.038 Uiso 1 1 calc R . . . .
C28 C -0.3261(2) -0.0520(5) 0.3577(2) 0.0370(9) Uani 1 1 d . . . . .
H28 H -0.3506 -0.1421 0.3306 0.044 Uiso 1 1 calc R . . . .
C29 C -0.2853(3) 0.0664(5) 0.33916(19) 0.0360(8) Uani 1 1 d . . . . .
H29 H -0.2822 0.0541 0.2998 0.043 Uiso 1 1 calc R . . . .
O7 O 0.0939(9) -0.0091(18) 0.5781(7) 0.095(4) Uani 0.5 1 d D . . B -1
C30 C 0.0880(5) 0.2128(11) 0.5075(4) 0.063(4) Uani 0.5 1 d . U . B -1
H30 H 0.1229 0.1633 0.4940 0.075 Uiso 0.5 1 calc R . . B -1
C31 C 0.0583(6) 0.3733(11) 0.4850(4) 0.070(4) Uani 0.5 1 d G U . B -1
H31 H 0.0732 0.4311 0.4566 0.083 Uiso 0.5 1 calc R . . B -1
C32 C 0.0061(6) 0.4473(9) 0.5051(5) 0.064(4) Uani 0.5 1 d G U . B -1
C33 C -0.0163(6) 0.3610(12) 0.5476(5) 0.076(4) Uani 0.5 1 d G . . B -1
H33 H -0.0512 0.4105 0.5610 0.091 Uiso 0.5 1 calc R . . B -1
C34 C 0.0134(6) 0.2005(12) 0.5700(5) 0.088(4) Uani 0.5 1 d G U . B -1
H34 H -0.0016 0.1428 0.5984 0.106 Uiso 0.5 1 calc R . . B -1
N2 N 0.0656(5) 0.1265(9) 0.5499(4) 0.060(3) Uani 0.5 1 d DG U . B -1
C38 C -0.0863(6) 0.9603(11) 0.4428(5) 0.068(5) Uani 0.5 1 d . . . B -1
H38 H -0.1062 1.0678 0.4281 0.081 Uiso 0.5 1 calc R . . B -1
C37 C -0.0359(7) 0.8850(12) 0.4210(5) 0.090(3) Uani 0.5 1 d G U . B -1
H37 H -0.0222 0.9421 0.3917 0.108 Uiso 0.5 1 calc R . . B -1
C36 C -0.0062(6) 0.7243(12) 0.4430(5) 0.063(4) Uani 0.5 1 d G . . B -1
H36 H 0.0275 0.6739 0.4284 0.076 Uiso 0.5 1 calc R . . B -1
C35 C -0.0267(6) 0.6389(11) 0.4867(5) 0.074(4) Uani 0.5 1 d G . . B -1
C40 C -0.0771(6) 0.7142(14) 0.5085(5) 0.077(5) Uani 0.5 1 d G . . B -1
H40 H -0.0908 0.6571 0.5378 0.092 Uiso 0.5 1 calc R . . B -1
C39 C -0.1069(6) 0.8749(15) 0.4865(5) 0.090(5) Uani 0.5 1 d G . . B -1
H39 H -0.1405 0.9253 0.5011 0.108 Uiso 0.5 1 calc R . . B -1
O1 O 0.2500 0.1934(4) 0.2500 0.0263(7) Uani 1 2 d S T P . .
C41 C 0.1778(3) 0.4476(6) 0.2304(3) 0.0553(13) Uani 1 1 d . . . . .
H41A H 0.1356 0.3709 0.2201 0.083 Uiso 1 1 calc GR . . . .
H41B H 0.1708 0.5155 0.1934 0.083 Uiso 1 1 calc GR . . . .
H41C H 0.1808 0.5208 0.2649 0.083 Uiso 1 1 calc GR . . . .
C42 C 0.2500 0.3476(6) 0.2500 0.0286(11) Uani 1 2 d S T P . .


_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 C13 1.896(3) . ?
Br2 C4 1.895(3) . ?
O2 H2 0.8484 . ?
O2 C5 1.371(4) . ?
O3 H3 0.8501 . ?
O3 C12 1.354(4) . ?
O4 H4 0.82(2) . ?
O4 C14 1.369(4) . ?
O5 H5 0.8384 . ?
O5 C3 1.373(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.387(5) . ?
C1 C6 1.391(5) . ?
C2 C3 1.400(5) . ?
C2 C16 1.526(4) 2 ?
C3 C4 1.389(5) . ?
C4 C5 1.394(5) . ?
C5 C6 1.398(5) . ?
C6 C7 1.527(4) . ?
C7 H7 0.9800 . ?
C7 C8 1.534(4) . ?
C7 C11 1.521(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.531(5) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10 0.9300 . ?
C10 C11 1.391(5) . ?
C10 C15 1.403(5) . ?
C11 C12 1.411(4) . ?
C12 C13 1.394(5) . ?
C13 C14 1.382(5) . ?
C14 C15 1.401(4) . ?
C15 C16 1.529(4) . ?
C16 C2 1.526(4) 2 ?
C16 H16 0.9800 . ?
C16 C17 1.536(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.525(5) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
O6 N1 1.347(5) . ?
N1 C19 1.339(6) . ?
N1 C23 1.353(6) . ?
C19 H19 0.9300 . ?
C19 C20 1.373(6) . ?
C20 H20 0.9300 . ?
C20 C21 1.399(6) . ?
C21 C22 1.389(6) . ?
C21 C24 1.479(5) . ?
C22 H22 0.9300 . ?
C22 C23 1.372(6) . ?
C23 H23 0.9300 . ?
C24 C25 1.401(5) . ?
C24 C29 1.398(6) . ?
C25 H25 0.9300 . ?
C25 C26 1.380(6) . ?
C26 H26 0.9300 . ?
C26 C27 1.383(6) . ?
C27 H27 0.9300 . ?
C27 C28 1.385(6) . ?
C28 H28 0.9300 . ?
C28 C29 1.389(6) . ?
C29 H29 0.9300 . ?
O7 N2 1.247(11) . ?
C30 H30 0.9300 . ?
C30 C31 1.3900 . ?
C30 N2 1.3900 . ?
C31 H31 0.9300 . ?
C31 C32 1.3900 . ?
C32 C33 1.3900 . ?
C32 C35 1.617(13) . ?
C33 H33 0.9300 . ?
C33 C34 1.3900 . ?
C34 H34 0.9300 . ?
C34 N2 1.3900 . ?
C38 H38 0.9300 . ?
C38 C37 1.3900 . ?
C38 C39 1.3900 . ?
C37 H37 0.9300 . ?
C37 C36 1.3900 . ?
C36 H36 0.9300 . ?
C36 C35 1.3900 . ?
C35 C40 1.3900 . ?
C40 H40 0.9300 . ?
C40 C39 1.3900 . ?
C39 H39 0.9300 . ?
O1 C42 1.209(6) . ?
C41 H41A 0.9600 . ?
C41 H41B 0.9600 . ?
C41 H41C 0.9600 . ?
C41 C42 1.494(6) . ?
C42 C41 1.494(6) 2 ?

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
C5 O2 H2 113.8 . . ?
C12 O3 H3 111.4 . . ?
C14 O4 H4 114(4) . . ?
C3 O5 H5 154.5 . . ?
C2 C1 H1 118.6 . . ?
C2 C1 C6 122.9(3) . . ?
C6 C1 H1 118.6 . . ?
C1 C2 C3 118.0(3) . . ?
C1 C2 C16 121.9(3) . 2 ?
C3 C2 C16 120.1(3) . 2 ?
O5 C3 C2 117.4(3) . . ?
O5 C3 C4 122.6(3) . . ?
C4 C3 C2 120.0(3) . . ?
C3 C4 Br2 118.7(2) . . ?
C3 C4 C5 121.1(3) . . ?
C5 C4 Br2 120.2(2) . . ?
O2 C5 C4 121.0(3) . . ?
O2 C5 C6 119.3(3) . . ?
C4 C5 C6 119.6(3) . . ?
C1 C6 C5 118.3(3) . . ?
C1 C6 C7 121.3(3) . . ?
C5 C6 C7 120.4(3) . . ?
C6 C7 H7 106.9 . . ?
C6 C7 C8 112.3(3) . . ?
C8 C7 H7 106.9 . . ?
C11 C7 C6 110.0(2) . . ?
C11 C7 H7 106.9 . . ?
C11 C7 C8 113.4(3) . . ?
C7 C8 H8A 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 107.9 . . ?
C9 C8 C7 111.8(3) . . ?
C9 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 H10 118.3 . . ?
C11 C10 C15 123.4(3) . . ?
C15 C10 H10 118.3 . . ?
C10 C11 C7 122.4(3) . . ?
C10 C11 C12 118.1(3) . . ?
C12 C11 C7 119.6(3) . . ?
O3 C12 C11 123.3(3) . . ?
O3 C12 C13 117.7(3) . . ?
C13 C12 C11 119.0(3) . . ?
C12 C13 Br1 118.5(2) . . ?
C14 C13 Br1 119.6(2) . . ?
C14 C13 C12 121.9(3) . . ?
O4 C14 C13 117.4(3) . . ?
O4 C14 C15 122.2(3) . . ?
C13 C14 C15 120.4(3) . . ?
C10 C15 C16 121.7(3) . . ?
C14 C15 C10 117.2(3) . . ?
C14 C15 C16 121.1(3) . . ?
C2 C16 C15 110.7(2) 2 . ?
C2 C16 H16 106.7 2 . ?
C2 C16 C17 112.1(3) 2 . ?
C15 C16 H16 106.7 . . ?
C15 C16 C17 113.4(3) . . ?
C17 C16 H16 106.7 . . ?
C16 C17 H17A 109.0 . . ?
C16 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
C18 C17 C16 112.8(3) . . ?
C18 C17 H17A 109.0 . . ?
C18 C17 H17B 109.0 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O6 N1 C23 117.9(4) . . ?
C19 N1 O6 121.5(3) . . ?
C19 N1 C23 120.6(4) . . ?
N1 C19 H19 119.7 . . ?
N1 C19 C20 120.6(4) . . ?
C20 C19 H19 119.7 . . ?
C19 C20 H20 119.5 . . ?
C19 C20 C21 120.9(4) . . ?
C21 C20 H20 119.5 . . ?
C20 C21 C24 121.7(4) . . ?
C22 C21 C20 116.3(4) . . ?
C22 C21 C24 121.8(3) . . ?
C21 C22 H22 119.3 . . ?
C23 C22 C21 121.4(4) . . ?
C23 C22 H22 119.3 . . ?
N1 C23 C22 120.1(4) . . ?
N1 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C25 C24 C21 121.1(3) . . ?
C29 C24 C21 120.3(3) . . ?
C29 C24 C25 118.6(3) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 C24 120.0(4) . . ?
C26 C25 H25 120.0 . . ?
C25 C26 H26 119.4 . . ?
C25 C26 C27 121.1(4) . . ?
C27 C26 H26 119.4 . . ?
C26 C27 H27 120.2 . . ?
C26 C27 C28 119.6(4) . . ?
C28 C27 H27 120.2 . . ?
C27 C28 H28 120.1 . . ?
C27 C28 C29 119.9(4) . . ?
C29 C28 H28 120.1 . . ?
C24 C29 H29 119.6 . . ?
C28 C29 C24 120.9(4) . . ?
C28 C29 H29 119.6 . . ?
C31 C30 H30 120.0 . . ?
C31 C30 N2 120.0 . . ?
N2 C30 H30 120.0 . . ?
C30 C31 H31 120.0 . . ?
C30 C31 C32 120.0 . . ?
C32 C31 H31 120.0 . . ?
C31 C32 C35 124.1(7) . . ?
C33 C32 C31 120.0 . . ?
C33 C32 C35 115.7(7) . . ?
C32 C33 H33 120.0 . . ?
C32 C33 C34 120.0 . . ?
C34 C33 H33 120.0 . . ?
C33 C34 H34 120.0 . . ?
N2 C34 C33 120.0 . . ?
N2 C34 H34 120.0 . . ?
O7 N2 C30 125.6(8) . . ?
O7 N2 C34 114.0(8) . . ?
C34 N2 C30 120.0 . . ?
C37 C38 H38 120.0 . . ?
C37 C38 C39 120.0 . . ?
C39 C38 H38 120.0 . . ?
C38 C37 H37 120.0 . . ?
C36 C37 C38 120.0 . . ?
C36 C37 H37 120.0 . . ?
C37 C36 H36 120.0 . . ?
C35 C36 C37 120.0 . . ?
C35 C36 H36 120.0 . . ?
C36 C35 C32 116.0(7) . . ?
C36 C35 C40 120.0 . . ?
C40 C35 C32 123.8(7) . . ?
C35 C40 H40 120.0 . . ?
C35 C40 C39 120.0 . . ?
C39 C40 H40 120.0 . . ?
C38 C39 H39 120.0 . . ?
C40 C39 C38 120.0 . . ?
C40 C39 H39 120.0 . . ?
H41A C41 H41B 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C42 C41 H41A 109.5 . . ?
C42 C41 H41B 109.5 . . ?
C42 C41 H41C 109.5 . . ?
O1 C42 C41 121.7(3) . . ?
O1 C42 C41 121.7(3) . 2 ?
C41 C42 C41 116.7(6) 2 . ?

_shelx_SHELXL_version_number     2014/7
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-12 1 2 0.0118 -12.0066 0.9966 2.0089 0.0710 0.6206 0.8088
12 0 -2 0.0228 12.0035 0.0032 -2.0094 -0.0781 -0.4444 -0.8953
-1 5 2 0.0235 -1.0138 4.9997 1.9975 0.0973 0.9006 -0.4036
0 -5 -2 0.0374 0.0134 -5.0000 -1.9966 -0.1022 -0.8620 0.4824
3 1 12 0.0059 3.0108 1.0059 11.9922 0.8350 -0.0528 -0.6221
-6 -1 -8 0.0141 -6.0080 -1.0052 -7.9912 -0.5742 0.1309 0.7586
-10 -2 10 0.0244 -9.9881 -1.9988 10.0056 0.6538 -0.0606 0.7112
9 2 -12 0.0305 8.9856 1.9976 -12.0039 -0.7966 0.1180 -0.5826
1 -5 5 0.0283 1.0211 -4.9967 4.9998 0.3853 -0.9666 0.2290

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_4_BrC2
_database_code_depnum_ccdc_archive 'CCDC 1551405'
_audit_update_record             
;
2017-05-22 deposited with the CCDC.
2017-06-15 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT971_4_BrC2              
;
PROBLEM: Check Calcd Residual Density  1.45A From     C40       4.91 eA-3  
RESPONSE: Due to unresolved disorder
;
_vrf_PLAT097_4_BrC2              
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       3.74 eA-3  
RESPONSE: Due to unresolved disorder
;
# end Validation Reply Form

_audit_creation_date             2017-04-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C36 H36 Br4 O8, 3(C6 H7 N O)'
_chemical_formula_sum            'C54 H57 Br4 N3 O11'
_chemical_formula_weight         1243.66
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N1 O9 Br4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   13.8438(4)
_cell_length_b                   26.2609(6)
_cell_length_c                   14.0294(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.720(2)
_cell_angle_gamma                90
_cell_volume                     5098.1(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7793
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      74.0530
_cell_measurement_theta_min      4.5310
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.390
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_T_min  0.933
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.620
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             2520
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -17 1 0.0171
1 17 -1 0.0068
-5 0 -7 0.0477
-1 5 9 0.0278
2 -5 -9 0.0372
-9 -1 0 0.0538
9 1 1 0.0313

_exptl_crystal_size_max          0.092
_exptl_crystal_size_mid          0.073
_exptl_crystal_size_min          0.024
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.9998 -17.0002 1.0002 0.2874 -0.9337 0.2496
0.9998 17.0002 -1.0002 -0.2874 0.9337 -0.2496
-4.9997 -0.0024 -6.9997 -0.0745 0.2477 0.9271
-1.0000 4.9998 8.9999 0.6704 0.1892 -0.7646
1.9999 -4.9993 -9.0000 -0.7531 -0.2198 0.6966
-8.9995 -1.0040 0.0005 0.7522 0.2202 0.6280
8.9995 1.0040 0.9995 -0.6825 -0.2337 -0.7118

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0458
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17258
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        66.737
_diffrn_reflns_theta_max         66.737
_diffrn_reflns_theta_min         3.573
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00  -5.00   1.00   10.00    --  -41.90 -19.00   0.00  110
  2  ω     23.00  98.00   1.00   10.00    --   41.90-125.00 -90.00   75
  3  ω     78.00 178.00   1.00   40.00    --  106.66  61.00 -60.00  100
  4  ω    100.00 178.00   1.00   40.00    --  106.66 125.00-150.00   78
  5  ω     48.00 139.00   1.00   40.00    --  106.66 -77.00 150.00   91
  6  ω     94.00 178.00   1.00   40.00    --  106.66 125.00 120.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0826890000
_diffrn_orient_matrix_UB_12      -0.0079415000
_diffrn_orient_matrix_UB_13      0.0697164000
_diffrn_orient_matrix_UB_21      -0.0307095000
_diffrn_orient_matrix_UB_22      0.0559388000
_diffrn_orient_matrix_UB_23      -0.0134708000
_diffrn_orient_matrix_UB_31      -0.0680432000
_diffrn_orient_matrix_UB_32      -0.0156117000
_diffrn_orient_matrix_UB_33      -0.0838481000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7747
_reflns_number_total             8948
_reflns_odcompleteness_completeness 98.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         3.745
_refine_diff_density_min         -1.002
_refine_diff_density_rms         0.172
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     658
_refine_ls_number_reflns         8948
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0757
_refine_ls_restrained_S_all      1.137
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0798P)²+65.1622P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2028
_refine_ls_wR_factor_ref         0.2078
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Riding coordinates:
 O18(H18), O27(H27), O20(H20), O6(H6), O11(H11), O13(H13)
2.b Ternary CH refined with riding coordinates:
 C28(H28), C21(H21), C14(H14), C7(H7)
2.c Secondary CH2 refined with riding coordinates:
 C29(H29A,H29B), C35(H35A,H35B), C33(H33A,H33B), C31(H31A,H31B)
2.d Aromatic/amide H refined with riding coordinates:
 C16(H16), C2(H2), C23(H23), C9(H9), C47(H47), C46(H46), C43(H43), C49(H49),
 C53(H53), C44(H44), C37(H37), C50(H50), C42(H42), C52(H52), C38(H38), C41(H41)
2.e Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C), C36(H36A,H36B,H36C), C30(H30A,H30B,H30C), C34(H34A,H34B,
 H34C), C40(H40A,H40B,H40C), C48(H48A,H48B,H48C), C54(H54A,H54B,H54C)
2.f Idealised tetrahedral OH refined as rotating group:
 O4(H4), O25(H25)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.93865(6) 0.42755(3) 0.98018(5) 0.0212(2) Uani 1 1 d . . . . .
Br3 Br 0.23074(5) 0.43011(3) 0.60106(5) 0.0199(2) Uani 1 1 d . . . . .
Br4 Br 0.74120(6) 0.44841(3) 0.48434(5) 0.0217(2) Uani 1 1 d . . . . .
Br2 Br 0.40412(6) 0.42776(3) 1.12351(7) 0.0314(2) Uani 1 1 d . . . . .
O18 O 0.3804(4) 0.37774(19) 0.4920(3) 0.0170(10) Uani 1 1 d . . . . .
H18 H 0.4386 0.3794 0.4771 0.026 Uiso 1 1 d R . . . .
O27 O 0.5646(4) 0.3791(2) 0.4461(4) 0.0195(11) Uani 1 1 d . . . . .
H27 H 0.5734 0.3939 0.3935 0.029 Uiso 1 1 d R . . . .
O4 O 0.7827(4) 0.3744(2) 1.0808(3) 0.0203(11) Uani 1 1 d . . . . .
H4 H 0.7293 0.3679 1.1013 0.031 Uiso 1 1 calc GR . . . .
O20 O 0.2235(4) 0.36830(19) 0.7897(3) 0.0179(10) Uani 1 1 d . . . . .
H20 H 0.1781 0.3897 0.7942 0.027 Uiso 1 1 d R . . . .
O6 O 0.9491(4) 0.3692(2) 0.7885(3) 0.0189(11) Uani 1 1 d . . . . .
H6 H 0.9936 0.3913 0.7874 0.028 Uiso 1 1 d R . . . .
O25 O 0.8666(4) 0.3873(2) 0.6174(4) 0.0205(11) Uani 1 1 d . . . . .
H25 H 0.8909 0.3780 0.6685 0.031 Uiso 1 1 calc GR . . . .
O11 O 0.2883(4) 0.3751(2) 0.9746(4) 0.0239(12) Uani 1 1 d . . . . .
H11 H 0.2617 0.3681 0.9220 0.036 Uiso 1 1 d R . . . .
O13 O 0.5986(4) 0.3682(2) 1.1321(4) 0.0249(12) Uani 1 1 d . . . . .
H13 H 0.6039 0.3862 1.1811 0.037 Uiso 1 1 d R . . . .
O1 O 0.3951(4) 0.5766(2) 0.7125(4) 0.0241(12) Uani 1 1 d . . . . .
O3 O 1.0891(4) 0.4380(2) 0.7969(4) 0.0260(12) Uani 1 1 d . . . . .
O2 O 0.6110(4) 0.1884(2) 0.7690(4) 0.0280(12) Uani 1 1 d . . . . .
N2 N 0.6422(5) 0.1418(3) 0.7570(4) 0.0236(14) Uani 1 1 d . . . . .
C16 C 0.4147(5) 0.2908(3) 0.6940(5) 0.0130(13) Uani 1 1 d . . . . .
H16 H 0.4527 0.2633 0.7133 0.016 Uiso 1 1 calc R . . . .
N1 N 0.4268(5) 0.5294(3) 0.7215(4) 0.0209(14) Uani 1 1 d . . . . .
C2 C 0.7514(5) 0.2920(3) 0.8710(5) 0.0109(13) Uani 1 1 d . . . . .
H2 H 0.7125 0.2655 0.8481 0.013 Uiso 1 1 calc R . . . .
N3 N 1.0710(5) 0.4808(2) 0.7484(5) 0.0214(13) Uani 1 1 d . . . . .
C23 C 0.6711(5) 0.2929(2) 0.6228(4) 0.0111(13) Uani 1 1 d . . . . .
H23 H 0.6549 0.2632 0.6546 0.013 Uiso 1 1 calc R . . . .
C9 C 0.4961(5) 0.2900(3) 0.9422(4) 0.0125(13) Uani 1 1 d . . . . .
H9 H 0.5151 0.2631 0.9040 0.015 Uiso 1 1 calc R . . . .
C18 C 0.3742(5) 0.3541(3) 0.5773(5) 0.0131(13) Uani 1 1 d . . . . .
C28 C 0.8356(5) 0.2901(3) 0.7120(4) 0.0120(13) Uani 1 1 d . . . . .
H28 H 0.8998 0.3011 0.6927 0.014 Uiso 1 1 calc R . . . .
C19 C 0.3050(5) 0.3727(3) 0.6399(5) 0.0135(13) Uani 1 1 d . . . . .
C10 C 0.4023(5) 0.3096(3) 0.9281(5) 0.0128(13) Uani 1 1 d . . . . .
C24 C 0.7625(5) 0.3147(3) 0.6425(5) 0.0121(13) Uani 1 1 d . . . . .
C29 C 0.8342(5) 0.2317(3) 0.7060(5) 0.0157(14) Uani 1 1 d . . . . .
H29A H 0.7726 0.2192 0.7277 0.019 Uiso 1 1 calc R . . . .
H29B H 0.8403 0.2214 0.6401 0.019 Uiso 1 1 calc R . . . .
C21 C 0.5050(5) 0.2898(3) 0.5384(5) 0.0134(14) Uani 1 1 d . . . . .
H21 H 0.4849 0.2997 0.4734 0.016 Uiso 1 1 calc R . . . .
C27 C 0.6300(5) 0.3584(3) 0.5109(5) 0.0148(14) Uani 1 1 d . . . . .
C13 C 0.5331(5) 0.3500(3) 1.0657(5) 0.0159(14) Uani 1 1 d . . . . .
C17 C 0.4301(5) 0.3119(3) 0.6050(5) 0.0120(13) Uani 1 1 d . . . . .
C1 C 0.8221(5) 0.3110(3) 0.8124(5) 0.0125(13) Uani 1 1 d . . . . .
C15 C 0.3456(5) 0.3086(3) 0.7562(5) 0.0138(14) Uani 1 1 d . . . . .
C22 C 0.6040(5) 0.3136(3) 0.5579(5) 0.0126(13) Uani 1 1 d . . . . .
C6 C 0.8797(5) 0.3512(3) 0.8466(5) 0.0140(14) Uani 1 1 d . . . . .
C3 C 0.7356(5) 0.3105(3) 0.9622(5) 0.0122(13) Uani 1 1 d . . . . .
C5 C 0.8626(5) 0.3718(3) 0.9356(5) 0.0157(14) Uani 1 1 d . . . . .
C26 C 0.7160(5) 0.3825(3) 0.5352(5) 0.0143(14) Uani 1 1 d . . . . .
C32 C 0.5954(5) 0.2036(3) 1.0937(5) 0.0182(15) Uani 1 1 d . . . . .
H32A H 0.5299 0.2139 1.0803 0.027 Uiso 1 1 calc GR . . . .
H32B H 0.6151 0.2149 1.1564 0.027 Uiso 1 1 calc GR . . . .
H32C H 0.5999 0.1672 1.0904 0.027 Uiso 1 1 calc GR . . . .
C20 C 0.2898(5) 0.3506(3) 0.7277(5) 0.0143(14) Uani 1 1 d . . . . .
C8 C 0.5619(5) 0.3088(3) 1.0102(5) 0.0138(13) Uani 1 1 d . . . . .
C25 C 0.7826(5) 0.3609(3) 0.5995(5) 0.0142(14) Uani 1 1 d . . . . .
C11 C 0.3773(5) 0.3517(3) 0.9820(5) 0.0160(14) Uani 1 1 d . . . . .
C4 C 0.7917(5) 0.3524(3) 0.9939(5) 0.0142(14) Uani 1 1 d . . . . .
C35 C 0.5071(5) 0.2314(3) 0.5404(5) 0.0133(13) Uani 1 1 d . . . . .
H35A H 0.4422 0.2186 0.5278 0.016 Uiso 1 1 calc R . . . .
H35B H 0.5276 0.2201 0.6037 0.016 Uiso 1 1 calc R . . . .
C14 C 0.3316(5) 0.2855(3) 0.8553(5) 0.0143(14) Uani 1 1 d . . . . .
H14 H 0.2667 0.2954 0.8742 0.017 Uiso 1 1 calc R . . . .
C7 C 0.6617(5) 0.2859(3) 1.0266(4) 0.0129(13) Uani 1 1 d . . . . .
H7 H 0.6818 0.2944 1.0923 0.015 Uiso 1 1 calc R . . . .
C36 C 0.5752(5) 0.2086(3) 0.4669(5) 0.0199(15) Uani 1 1 d . . . . .
H36A H 0.5564 0.2204 0.4043 0.030 Uiso 1 1 calc GR . . . .
H36B H 0.5715 0.1721 0.4689 0.030 Uiso 1 1 calc GR . . . .
H36C H 0.6404 0.2192 0.4817 0.030 Uiso 1 1 calc GR . . . .
C12 C 0.4418(5) 0.3709(3) 1.0507(5) 0.0177(15) Uani 1 1 d . . . . .
C33 C 0.3352(5) 0.2275(3) 0.8587(5) 0.0171(14) Uani 1 1 d . . . . .
H33A H 0.3332 0.2165 0.9246 0.021 Uiso 1 1 calc R . . . .
H33B H 0.3959 0.2160 0.8334 0.021 Uiso 1 1 calc R . . . .
C51 C 1.0371(6) 0.5699(3) 0.6448(6) 0.0247(17) Uani 1 1 d . . . . .
C31 C 0.6616(5) 0.2274(3) 1.0200(5) 0.0149(14) Uani 1 1 d . . . . .
H31A H 0.6398 0.2172 0.9564 0.018 Uiso 1 1 calc R . . . .
H31B H 0.7269 0.2149 1.0305 0.018 Uiso 1 1 calc R . . . .
C39 C 0.5133(6) 0.4360(3) 0.7575(6) 0.0234(16) Uani 1 1 d . . . . .
C47 C 0.7032(6) 0.1200(3) 0.8231(5) 0.0230(16) Uani 1 1 d . . . . .
H47 H 0.7272 0.1393 0.8740 0.028 Uiso 1 1 calc R . . . .
C46 C 0.7297(6) 0.0698(3) 0.8158(6) 0.0283(18) Uani 1 1 d . . . . .
H46 H 0.7691 0.0553 0.8633 0.034 Uiso 1 1 calc R . . . .
C43 C 0.6144(6) 0.1148(3) 0.6790(6) 0.0264(17) Uani 1 1 d . . . . .
H43 H 0.5770 0.1304 0.6312 0.032 Uiso 1 1 calc R . . . .
C30 C 0.9157(6) 0.2076(3) 0.7664(5) 0.0250(17) Uani 1 1 d . . . . .
H30A H 0.9766 0.2215 0.7482 0.038 Uiso 1 1 calc GR . . . .
H30B H 0.9159 0.1714 0.7563 0.038 Uiso 1 1 calc GR . . . .
H30C H 0.9060 0.2146 0.8325 0.038 Uiso 1 1 calc GR . . . .
C49 C 1.1115(6) 0.5248(3) 0.7783(6) 0.0258(17) Uani 1 1 d . . . . .
H49 H 1.1503 0.5254 0.8335 0.031 Uiso 1 1 calc R . . . .
C53 C 1.0130(6) 0.4806(3) 0.6709(6) 0.0238(16) Uani 1 1 d . . . . .
H53 H 0.9845 0.4502 0.6512 0.029 Uiso 1 1 calc R . . . .
C44 C 0.6408(6) 0.0645(3) 0.6696(6) 0.0280(18) Uani 1 1 d . . . . .
H44 H 0.6194 0.0464 0.6160 0.034 Uiso 1 1 calc R . . . .
C34 C 0.2518(6) 0.2028(3) 0.8021(6) 0.0246(17) Uani 1 1 d . . . . .
H34A H 0.2569 0.2110 0.7358 0.037 Uiso 1 1 calc GR . . . .
H34B H 0.1915 0.2154 0.8247 0.037 Uiso 1 1 calc GR . . . .
H34C H 0.2545 0.1665 0.8103 0.037 Uiso 1 1 calc GR . . . .
C40 C 0.5707(6) 0.3883(3) 0.7827(6) 0.0290(18) Uani 1 1 d . . . . .
H40A H 0.6133 0.3952 0.8364 0.043 Uiso 1 1 calc GR . . . .
H40B H 0.6079 0.3783 0.7291 0.043 Uiso 1 1 calc GR . . . .
H40C H 0.5271 0.3614 0.7984 0.043 Uiso 1 1 calc GR . . . .
C45 C 0.6988(6) 0.0402(3) 0.7385(6) 0.0263(17) Uani 1 1 d . . . . .
C37 C 0.4005(6) 0.5008(3) 0.7960(6) 0.0267(17) Uani 1 1 d . . . . .
H37 H 0.3521 0.5126 0.8350 0.032 Uiso 1 1 calc R . . . .
C50 C 1.0954(6) 0.5693(3) 0.7269(6) 0.0270(17) Uani 1 1 d . . . . .
H50 H 1.1244 0.5994 0.7479 0.032 Uiso 1 1 calc R . . . .
C42 C 0.4899(6) 0.5098(3) 0.6593(6) 0.0276(18) Uani 1 1 d . . . . .
H42 H 0.5043 0.5282 0.6049 0.033 Uiso 1 1 calc R . . . .
C52 C 0.9942(6) 0.5241(3) 0.6194(6) 0.0248(17) Uani 1 1 d . . . . .
H52 H 0.9519 0.5228 0.5667 0.030 Uiso 1 1 calc R . . . .
C38 C 0.4430(6) 0.4552(3) 0.8159(6) 0.0281(18) Uani 1 1 d . . . . .
H38 H 0.4248 0.4367 0.8690 0.034 Uiso 1 1 calc R . . . .
C41 C 0.5330(6) 0.4634(3) 0.6753(6) 0.0269(17) Uani 1 1 d . . . . .
H41 H 0.5754 0.4503 0.6313 0.032 Uiso 1 1 calc R . . . .
C48 C 0.7267(7) -0.0143(3) 0.7285(6) 0.0321(19) Uani 1 1 d . . . . .
H48A H 0.7778 -0.0171 0.6840 0.048 Uiso 1 1 calc GR . . . .
H48B H 0.6719 -0.0336 0.7056 0.048 Uiso 1 1 calc GR . . . .
H48C H 0.7485 -0.0273 0.7893 0.048 Uiso 1 1 calc GR . . . .
C54 C 1.0210(7) 0.6169(3) 0.5866(6) 0.034(2) Uani 1 1 d . . . . .
H54A H 0.9960 0.6433 0.6261 0.051 Uiso 1 1 calc GR . . . .
H54B H 0.9756 0.6098 0.5353 0.051 Uiso 1 1 calc GR . . . .
H54C H 1.0812 0.6277 0.5610 0.051 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C5 1.899(7) . ?
Br3 C19 1.896(7) . ?
Br4 C26 1.909(7) . ?
Br2 C12 1.891(7) . ?
O18 H18 0.8398 . ?
O18 C18 1.354(8) . ?
O27 H27 0.8461 . ?
O27 C27 1.375(8) . ?
O4 H4 0.8200 . ?
O4 C4 1.360(8) . ?
O20 H20 0.8470 . ?
O20 C20 1.364(9) . ?
O6 H6 0.8471 . ?
O6 C6 1.363(9) . ?
O25 H25 0.8200 . ?
O25 C25 1.370(8) . ?
O11 H11 0.8347 . ?
O11 C11 1.378(8) . ?
O13 H13 0.8354 . ?
O13 C13 1.366(9) . ?
O1 N1 1.321(9) . ?
O3 N3 1.334(9) . ?
O2 N2 1.311(9) . ?
N2 C47 1.361(10) . ?
N2 C43 1.349(11) . ?
C16 H16 0.9300 . ?
C16 C17 1.388(9) . ?
C16 C15 1.394(10) . ?
N1 C37 1.345(10) . ?
N1 C42 1.354(10) . ?
C2 H2 0.9300 . ?
C2 C1 1.389(9) . ?
C2 C3 1.392(9) . ?
N3 C49 1.345(11) . ?
N3 C53 1.332(11) . ?
C23 H23 0.9300 . ?
C23 C24 1.409(9) . ?
C23 C22 1.391(10) . ?
C9 H9 0.9300 . ?
C9 C10 1.405(10) . ?
C9 C8 1.390(10) . ?
C18 C19 1.405(10) . ?
C18 C17 1.400(10) . ?
C28 H28 0.9800 . ?
C28 C24 1.528(9) . ?
C28 C29 1.538(10) . ?
C28 C1 1.528(9) . ?
C19 C20 1.384(10) . ?
C10 C11 1.390(10) . ?
C10 C14 1.529(9) . ?
C24 C25 1.387(10) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C29 C30 1.528(10) . ?
C21 H21 0.9800 . ?
C21 C17 1.531(9) . ?
C21 C22 1.525(9) . ?
C21 C35 1.534(9) . ?
C27 C22 1.399(10) . ?
C27 C26 1.383(10) . ?
C13 C8 1.398(10) . ?
C13 C12 1.389(10) . ?
C1 C6 1.400(10) . ?
C15 C20 1.399(10) . ?
C15 C14 1.533(9) . ?
C6 C5 1.387(10) . ?
C3 C4 1.410(10) . ?
C3 C7 1.529(9) . ?
C5 C4 1.392(10) . ?
C26 C25 1.391(10) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C32 C31 1.535(9) . ?
C8 C7 1.517(9) . ?
C11 C12 1.389(10) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C35 C36 1.540(9) . ?
C14 H14 0.9800 . ?
C14 C33 1.525(10) . ?
C7 H7 0.9800 . ?
C7 C31 1.539(10) . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C33 C34 1.526(10) . ?
C51 C50 1.386(12) . ?
C51 C52 1.382(12) . ?
C51 C54 1.493(12) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C39 C40 1.518(11) . ?
C39 C38 1.385(12) . ?
C39 C41 1.394(12) . ?
C47 H47 0.9300 . ?
C47 C46 1.373(12) . ?
C46 H46 0.9300 . ?
C46 C45 1.390(12) . ?
C43 H43 0.9300 . ?
C43 C44 1.380(12) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C49 H49 0.9300 . ?
C49 C50 1.388(12) . ?
C53 H53 0.9300 . ?
C53 C52 1.372(12) . ?
C44 H44 0.9300 . ?
C44 C45 1.394(12) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
C45 C48 1.489(12) . ?
C37 H37 0.9300 . ?
C37 C38 1.361(12) . ?
C50 H50 0.9300 . ?
C42 H42 0.9300 . ?
C42 C41 1.373(12) . ?
C52 H52 0.9300 . ?
C38 H38 0.9300 . ?
C41 H41 0.9300 . ?
C48 H48A 0.9600 . ?
C48 H48B 0.9600 . ?
C48 H48C 0.9600 . ?
C54 H54A 0.9600 . ?
C54 H54B 0.9600 . ?
C54 H54C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C18 O18 H18 109.3 . . ?
C27 O27 H27 130.4 . . ?
C4 O4 H4 109.5 . . ?
C20 O20 H20 142.1 . . ?
C6 O6 H6 140.9 . . ?
C25 O25 H25 109.5 . . ?
C11 O11 H11 109.8 . . ?
C13 O13 H13 143.0 . . ?
O2 N2 C47 120.4(6) . . ?
O2 N2 C43 120.4(7) . . ?
C43 N2 C47 119.2(7) . . ?
C17 C16 H16 118.1 . . ?
C17 C16 C15 123.9(6) . . ?
C15 C16 H16 118.1 . . ?
O1 N1 C37 120.0(6) . . ?
O1 N1 C42 120.9(6) . . ?
C37 N1 C42 119.0(7) . . ?
C1 C2 H2 118.3 . . ?
C1 C2 C3 123.4(6) . . ?
C3 C2 H2 118.3 . . ?
O3 N3 C49 119.6(7) . . ?
C53 N3 O3 120.9(7) . . ?
C53 N3 C49 119.6(7) . . ?
C24 C23 H23 118.4 . . ?
C22 C23 H23 118.4 . . ?
C22 C23 C24 123.2(6) . . ?
C10 C9 H9 118.3 . . ?
C8 C9 H9 118.3 . . ?
C8 C9 C10 123.4(6) . . ?
O18 C18 C19 117.1(6) . . ?
O18 C18 C17 124.0(6) . . ?
C17 C18 C19 118.9(6) . . ?
C24 C28 H28 106.7 . . ?
C24 C28 C29 112.3(5) . . ?
C29 C28 H28 106.7 . . ?
C1 C28 H28 106.7 . . ?
C1 C28 C24 109.9(5) . . ?
C1 C28 C29 114.0(5) . . ?
C18 C19 Br3 118.1(5) . . ?
C20 C19 Br3 119.6(5) . . ?
C20 C19 C18 122.4(6) . . ?
C9 C10 C14 120.8(6) . . ?
C11 C10 C9 117.3(6) . . ?
C11 C10 C14 121.9(6) . . ?
C23 C24 C28 121.8(6) . . ?
C25 C24 C23 117.5(6) . . ?
C25 C24 C28 120.6(6) . . ?
C28 C29 H29A 109.2 . . ?
C28 C29 H29B 109.2 . . ?
H29A C29 H29B 107.9 . . ?
C30 C29 C28 112.1(6) . . ?
C30 C29 H29A 109.2 . . ?
C30 C29 H29B 109.2 . . ?
C17 C21 H21 106.7 . . ?
C17 C21 C35 112.4(6) . . ?
C22 C21 H21 106.7 . . ?
C22 C21 C17 110.8(5) . . ?
C22 C21 C35 113.1(6) . . ?
C35 C21 H21 106.7 . . ?
O27 C27 C22 118.1(6) . . ?
O27 C27 C26 121.7(6) . . ?
C26 C27 C22 120.0(6) . . ?
O13 C13 C8 117.1(6) . . ?
O13 C13 C12 123.2(6) . . ?
C12 C13 C8 119.7(6) . . ?
C16 C17 C18 117.8(6) . . ?
C16 C17 C21 121.5(6) . . ?
C18 C17 C21 120.7(6) . . ?
C2 C1 C28 121.7(6) . . ?
C2 C1 C6 118.2(6) . . ?
C6 C1 C28 120.1(6) . . ?
C16 C15 C20 117.9(6) . . ?
C16 C15 C14 122.9(6) . . ?
C20 C15 C14 119.1(6) . . ?
C23 C22 C21 122.4(6) . . ?
C23 C22 C27 117.4(6) . . ?
C27 C22 C21 120.1(6) . . ?
O6 C6 C1 117.5(6) . . ?
O6 C6 C5 123.0(6) . . ?
C5 C6 C1 119.4(6) . . ?
C2 C3 C4 117.5(6) . . ?
C2 C3 C7 121.5(6) . . ?
C4 C3 C7 121.0(6) . . ?
C6 C5 Br1 119.3(5) . . ?
C6 C5 C4 121.9(6) . . ?
C4 C5 Br1 118.8(5) . . ?
C27 C26 Br4 119.3(5) . . ?
C27 C26 C25 121.5(6) . . ?
C25 C26 Br4 119.1(5) . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
O20 C20 C19 123.2(6) . . ?
O20 C20 C15 117.6(6) . . ?
C19 C20 C15 119.2(6) . . ?
C9 C8 C13 117.7(6) . . ?
C9 C8 C7 122.7(6) . . ?
C13 C8 C7 119.6(6) . . ?
O25 C25 C24 122.9(6) . . ?
O25 C25 C26 117.1(6) . . ?
C24 C25 C26 120.0(6) . . ?
O11 C11 C10 123.4(6) . . ?
O11 C11 C12 116.4(6) . . ?
C12 C11 C10 120.1(6) . . ?
O4 C4 C3 123.4(6) . . ?
O4 C4 C5 117.2(6) . . ?
C5 C4 C3 119.4(6) . . ?
C21 C35 H35A 109.0 . . ?
C21 C35 H35B 109.0 . . ?
C21 C35 C36 112.8(6) . . ?
H35A C35 H35B 107.8 . . ?
C36 C35 H35A 109.0 . . ?
C36 C35 H35B 109.0 . . ?
C10 C14 C15 110.3(6) . . ?
C10 C14 H14 106.5 . . ?
C15 C14 H14 106.5 . . ?
C33 C14 C10 111.8(6) . . ?
C33 C14 C15 114.7(6) . . ?
C33 C14 H14 106.5 . . ?
C3 C7 H7 106.5 . . ?
C3 C7 C31 112.6(5) . . ?
C8 C7 C3 111.4(5) . . ?
C8 C7 H7 106.5 . . ?
C8 C7 C31 112.7(6) . . ?
C31 C7 H7 106.5 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C13 C12 Br2 119.7(5) . . ?
C11 C12 Br2 118.7(5) . . ?
C11 C12 C13 121.6(6) . . ?
C14 C33 H33A 109.1 . . ?
C14 C33 H33B 109.1 . . ?
C14 C33 C34 112.6(6) . . ?
H33A C33 H33B 107.8 . . ?
C34 C33 H33A 109.1 . . ?
C34 C33 H33B 109.1 . . ?
C50 C51 C54 122.4(8) . . ?
C52 C51 C50 116.1(8) . . ?
C52 C51 C54 121.5(8) . . ?
C32 C31 C7 111.4(6) . . ?
C32 C31 H31A 109.3 . . ?
C32 C31 H31B 109.3 . . ?
C7 C31 H31A 109.3 . . ?
C7 C31 H31B 109.3 . . ?
H31A C31 H31B 108.0 . . ?
C38 C39 C40 122.3(8) . . ?
C38 C39 C41 117.4(8) . . ?
C41 C39 C40 120.3(7) . . ?
N2 C47 H47 119.5 . . ?
N2 C47 C46 121.0(7) . . ?
C46 C47 H47 119.5 . . ?
C47 C46 H46 119.4 . . ?
C47 C46 C45 121.3(8) . . ?
C45 C46 H46 119.4 . . ?
N2 C43 H43 119.7 . . ?
N2 C43 C44 120.7(7) . . ?
C44 C43 H43 119.7 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
N3 C49 H49 119.9 . . ?
N3 C49 C50 120.2(8) . . ?
C50 C49 H49 119.9 . . ?
N3 C53 H53 119.1 . . ?
N3 C53 C52 121.8(7) . . ?
C52 C53 H53 119.1 . . ?
C43 C44 H44 119.3 . . ?
C43 C44 C45 121.4(8) . . ?
C45 C44 H44 119.3 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C46 C45 C44 116.2(8) . . ?
C46 C45 C48 122.5(8) . . ?
C44 C45 C48 121.3(8) . . ?
N1 C37 H37 119.2 . . ?
N1 C37 C38 121.6(8) . . ?
C38 C37 H37 119.2 . . ?
C51 C50 C49 121.3(8) . . ?
C51 C50 H50 119.3 . . ?
C49 C50 H50 119.3 . . ?
N1 C42 H42 119.4 . . ?
N1 C42 C41 121.2(7) . . ?
C41 C42 H42 119.4 . . ?
C51 C52 H52 119.5 . . ?
C53 C52 C51 121.0(8) . . ?
C53 C52 H52 119.5 . . ?
C39 C38 H38 119.8 . . ?
C37 C38 C39 120.4(8) . . ?
C37 C38 H38 119.8 . . ?
C39 C41 H41 120.1 . . ?
C42 C41 C39 119.9(8) . . ?
C42 C41 H41 120.1 . . ?
C45 C48 H48A 109.5 . . ?
C45 C48 H48B 109.5 . . ?
C45 C48 H48C 109.5 . . ?
H48A C48 H48B 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C51 C54 H54A 109.5 . . ?
C51 C54 H54B 109.5 . . ?
C51 C54 H54C 109.5 . . ?
H54A C54 H54B 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C5 C4 O4 -1.2(9) . . . . ?
Br1 C5 C4 C3 -179.2(5) . . . . ?
Br3 C19 C20 O20 -0.5(9) . . . . ?
Br3 C19 C20 C15 -179.4(5) . . . . ?
Br4 C26 C25 O25 -4.4(9) . . . . ?
Br4 C26 C25 C24 175.4(5) . . . . ?
O18 C18 C19 Br3 -2.2(8) . . . . ?
O18 C18 C19 C20 177.8(6) . . . . ?
O18 C18 C17 C16 -178.7(6) . . . . ?
O18 C18 C17 C21 0.9(10) . . . . ?
O27 C27 C22 C23 179.6(6) . . . . ?
O27 C27 C22 C21 -1.2(10) . . . . ?
O27 C27 C26 Br4 4.2(9) . . . . ?
O27 C27 C26 C25 -178.9(6) . . . . ?
O6 C6 C5 Br1 -0.2(9) . . . . ?
O6 C6 C5 C4 -179.5(6) . . . . ?
O11 C11 C12 Br2 -2.0(9) . . . . ?
O11 C11 C12 C13 179.1(7) . . . . ?
O13 C13 C8 C9 -179.8(6) . . . . ?
O13 C13 C8 C7 1.1(10) . . . . ?
O13 C13 C12 Br2 0.5(10) . . . . ?
O13 C13 C12 C11 179.4(7) . . . . ?
O1 N1 C37 C38 -169.7(7) . . . . ?
O1 N1 C42 C41 171.2(7) . . . . ?
O3 N3 C49 C50 178.1(7) . . . . ?
O3 N3 C53 C52 -179.3(7) . . . . ?
O2 N2 C47 C46 174.3(7) . . . . ?
O2 N2 C43 C44 -174.9(7) . . . . ?
N2 C47 C46 C45 2.9(13) . . . . ?
N2 C43 C44 C45 -1.7(13) . . . . ?
C16 C15 C20 O20 -178.8(6) . . . . ?
C16 C15 C20 C19 0.1(10) . . . . ?
C16 C15 C14 C10 84.9(8) . . . . ?
C16 C15 C14 C33 -42.5(9) . . . . ?
N1 C37 C38 C39 -1.9(13) . . . . ?
N1 C42 C41 C39 -1.1(13) . . . . ?
C2 C1 C6 O6 179.7(6) . . . . ?
C2 C1 C6 C5 -2.1(10) . . . . ?
C2 C3 C4 O4 179.3(6) . . . . ?
C2 C3 C4 C5 -2.8(10) . . . . ?
C2 C3 C7 C8 -88.2(8) . . . . ?
C2 C3 C7 C31 39.6(8) . . . . ?
N3 C49 C50 C51 0.7(12) . . . . ?
N3 C53 C52 C51 1.8(12) . . . . ?
C23 C24 C25 O25 176.1(6) . . . . ?
C23 C24 C25 C26 -3.8(10) . . . . ?
C9 C10 C11 O11 179.2(6) . . . . ?
C9 C10 C11 C12 -3.8(10) . . . . ?
C9 C10 C14 C15 -86.7(8) . . . . ?
C9 C10 C14 C33 42.3(9) . . . . ?
C9 C8 C7 C3 88.8(8) . . . . ?
C9 C8 C7 C31 -39.0(9) . . . . ?
C18 C19 C20 O20 179.5(6) . . . . ?
C18 C19 C20 C15 0.6(10) . . . . ?
C28 C24 C25 O25 -1.1(10) . . . . ?
C28 C24 C25 C26 179.0(6) . . . . ?
C28 C1 C6 O6 -2.2(9) . . . . ?
C28 C1 C6 C5 176.1(6) . . . . ?
C19 C18 C17 C16 -0.7(10) . . . . ?
C19 C18 C17 C21 178.8(6) . . . . ?
C10 C9 C8 C13 -1.3(10) . . . . ?
C10 C9 C8 C7 177.8(6) . . . . ?
C10 C11 C12 Br2 -179.2(5) . . . . ?
C10 C11 C12 C13 1.9(11) . . . . ?
C10 C14 C33 C34 168.2(6) . . . . ?
C24 C23 C22 C21 -179.3(6) . . . . ?
C24 C23 C22 C27 -0.1(10) . . . . ?
C24 C28 C29 C30 172.8(6) . . . . ?
C24 C28 C1 C2 81.8(8) . . . . ?
C24 C28 C1 C6 -96.3(7) . . . . ?
C29 C28 C24 C23 37.1(9) . . . . ?
C29 C28 C24 C25 -145.8(6) . . . . ?
C29 C28 C1 C2 -45.3(9) . . . . ?
C29 C28 C1 C6 136.7(6) . . . . ?
C27 C26 C25 O25 178.7(6) . . . . ?
C27 C26 C25 C24 -1.5(10) . . . . ?
C13 C8 C7 C3 -92.1(7) . . . . ?
C13 C8 C7 C31 140.1(6) . . . . ?
C17 C16 C15 C20 -1.2(10) . . . . ?
C17 C16 C15 C14 -178.4(6) . . . . ?
C17 C18 C19 Br3 179.7(5) . . . . ?
C17 C18 C19 C20 -0.3(10) . . . . ?
C17 C21 C22 C23 90.7(8) . . . . ?
C17 C21 C22 C27 -88.5(7) . . . . ?
C17 C21 C35 C36 174.6(6) . . . . ?
C1 C2 C3 C4 3.2(10) . . . . ?
C1 C2 C3 C7 -175.6(6) . . . . ?
C1 C28 C24 C23 -90.9(7) . . . . ?
C1 C28 C24 C25 86.2(7) . . . . ?
C1 C28 C29 C30 -61.4(8) . . . . ?
C1 C6 C5 Br1 -178.3(5) . . . . ?
C1 C6 C5 C4 2.3(10) . . . . ?
C15 C16 C17 C18 1.5(10) . . . . ?
C15 C16 C17 C21 -178.1(6) . . . . ?
C15 C14 C33 C34 -65.3(8) . . . . ?
C22 C23 C24 C28 -178.2(6) . . . . ?
C22 C23 C24 C25 4.6(10) . . . . ?
C22 C21 C17 C16 -88.4(8) . . . . ?
C22 C21 C17 C18 92.1(7) . . . . ?
C22 C21 C35 C36 -59.0(7) . . . . ?
C22 C27 C26 Br4 -170.7(5) . . . . ?
C22 C27 C26 C25 6.2(11) . . . . ?
C6 C5 C4 O4 178.2(6) . . . . ?
C6 C5 C4 C3 0.2(10) . . . . ?
C3 C2 C1 C28 -178.8(6) . . . . ?
C3 C2 C1 C6 -0.7(10) . . . . ?
C3 C7 C31 C32 173.4(6) . . . . ?
C26 C27 C22 C23 -5.3(10) . . . . ?
C26 C27 C22 C21 174.0(6) . . . . ?
C20 C15 C14 C10 -92.3(7) . . . . ?
C20 C15 C14 C33 140.4(7) . . . . ?
C8 C9 C10 C11 3.6(10) . . . . ?
C8 C9 C10 C14 -177.0(6) . . . . ?
C8 C13 C12 Br2 -178.3(5) . . . . ?
C8 C13 C12 C11 0.6(11) . . . . ?
C8 C7 C31 C32 -59.5(7) . . . . ?
C11 C10 C14 C15 92.7(8) . . . . ?
C11 C10 C14 C33 -138.4(7) . . . . ?
C4 C3 C7 C8 93.1(7) . . . . ?
C4 C3 C7 C31 -139.1(6) . . . . ?
C35 C21 C17 C16 39.2(9) . . . . ?
C35 C21 C17 C18 -140.3(6) . . . . ?
C35 C21 C22 C23 -36.5(9) . . . . ?
C35 C21 C22 C27 144.3(6) . . . . ?
C14 C10 C11 O11 -0.2(11) . . . . ?
C14 C10 C11 C12 176.8(7) . . . . ?
C14 C15 C20 O20 -1.5(9) . . . . ?
C14 C15 C20 C19 177.4(6) . . . . ?
C7 C3 C4 O4 -2.0(10) . . . . ?
C7 C3 C4 C5 176.0(6) . . . . ?
C12 C13 C8 C9 -0.8(10) . . . . ?
C12 C13 C8 C7 180.0(6) . . . . ?
C47 N2 C43 C44 5.2(12) . . . . ?
C47 C46 C45 C44 0.6(12) . . . . ?
C47 C46 C45 C48 179.8(8) . . . . ?
C43 N2 C47 C46 -5.8(12) . . . . ?
C43 C44 C45 C46 -1.2(12) . . . . ?
C43 C44 C45 C48 179.6(8) . . . . ?
C49 N3 C53 C52 0.9(12) . . . . ?
C53 N3 C49 C50 -2.1(12) . . . . ?
C40 C39 C38 C37 172.9(8) . . . . ?
C40 C39 C41 C42 -171.6(8) . . . . ?
C37 N1 C42 C41 -5.2(12) . . . . ?
C50 C51 C52 C53 -3.0(12) . . . . ?
C42 N1 C37 C38 6.8(12) . . . . ?
C52 C51 C50 C49 1.8(12) . . . . ?
C38 C39 C41 C42 5.9(12) . . . . ?
C41 C39 C38 C37 -4.4(12) . . . . ?
C54 C51 C50 C49 -178.1(8) . . . . ?
C54 C51 C52 C53 176.9(7) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.104
_oxdiff_exptl_absorpt_empirical_full_min 0.912
####################################################################### 
# 
# 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_9_BrC2
_database_code_depnum_ccdc_archive 'CCDC 1551410'
_audit_update_record             
;
2017-05-22 deposited with the CCDC.
2017-06-15 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT094_9_BrC2              
;
PROBLEM: Ratio of Maximum / Minimum Residual Density ....       5.84 Report
RESPONSE: Due to unresolved disorder
;
_vrf_PLAT097_9_BrC2              
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       4.55 eA-3  
RESPONSE: Due to unresolved disorder
;
# end Validation Reply Form
_audit_creation_date             2017-05-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C36 H36 Br4 O8, 2(C9 H7 N O), C3 H6 O'
_chemical_formula_sum            'C57 H56 Br4 N2 O11'
_chemical_formula_weight         1264.67
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C24 H28 N6 O4 Br1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   14.1188(3)
_cell_length_b                   26.2939(6)
_cell_length_c                   14.3240(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.644(2)
_cell_angle_gamma                90
_cell_volume                     5315.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10437
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      75.1490
_cell_measurement_theta_min      4.2990
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.218
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78164
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             2560
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -17 -2 0.0219
1 17 0 0.0301
4 -1 -8 0.1019
-4 3 8 0.0932
9 2 -1 0.0341
-9 -1 0 0.0279
4 -6 7 0.0891
-5 5 -7 0.0946
8 4 -3 0.0456

_exptl_crystal_size_max          0.228
_exptl_crystal_size_mid          0.072
_exptl_crystal_size_min          0.072
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0116 -16.9860 -1.9882 -0.2672 -0.9512 -0.2462
1.0151 16.9744 -0.0103 0.2513 0.8517 0.4623
4.0133 -1.0451 -7.9934 -0.0840 -0.4472 0.8403
-4.0114 3.0426 7.9919 0.1248 0.5457 -0.7919
8.9994 1.9544 -0.9851 -0.7760 0.1688 0.5941
-8.9965 -0.9592 -0.0158 0.8360 -0.1763 -0.4877
3.9784 -5.9848 7.0128 -0.7803 0.1584 -0.5151
-4.9788 4.9905 -7.0139 0.8550 -0.2218 0.4394
8.0058 3.9491 -2.9887 -0.5609 0.1396 0.7556

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            35634
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.747
_diffrn_reflns_theta_max         66.747
_diffrn_reflns_theta_min         4.335
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -65.00  31.00   1.00   10.00    --  -41.65  57.00-180.00   96
  2  ω   -110.00 -17.00   1.00   10.00    --  -41.65 -57.00  30.00   93
  3  ω    -66.00  33.00   1.00   10.00    --  -41.65  37.00 -30.00   99
  4  ω     43.00  98.00   1.00   10.00    --   41.65-125.00   0.00   55
  5  ω     29.00 109.00   1.00   42.50    --  112.00 -94.00 -90.00   80
  6  ω    100.00 178.00   1.00   42.50    --  112.00  61.00 120.00   78
  7  ω     79.00 177.00   1.00   42.50    --  112.00  77.00   0.00   98
  8  ω     45.00 138.00   1.00   42.50    --  112.00 -45.00  30.00   93
  9  ω     37.00 116.00   1.00   42.50    --  112.00-111.00-120.00   79
 10  ω     87.00 178.00   1.00   42.50    --  112.00  45.00  60.00   91
 11  ω     38.00 142.00   1.00   42.50    --  112.00 -77.00 -60.00  104
 12  ω     57.00 151.00   1.00   42.50    --  112.00 178.00 -90.00   94
 13  ω     65.00 116.00   1.00   42.50    --  112.00-111.00 120.00   51
 14  ω     89.00 178.00   1.00   42.50    --  112.00  61.00  90.00   89
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0950397000
_diffrn_orient_matrix_UB_12      0.0204655000
_diffrn_orient_matrix_UB_13      -0.0398795000
_diffrn_orient_matrix_UB_21      0.0142385000
_diffrn_orient_matrix_UB_22      0.0493600000
_diffrn_orient_matrix_UB_23      0.0566401000
_diffrn_orient_matrix_UB_31      0.0517803000
_diffrn_orient_matrix_UB_32      0.0240877000
_diffrn_orient_matrix_UB_33      -0.0822710000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7891
_reflns_number_total             9404
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         4.545
_refine_diff_density_min         -0.778
_refine_diff_density_rms         0.165
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.173
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     675
_refine_ls_number_reflns         9404
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1002
_refine_ls_R_factor_gt           0.0873
_refine_ls_restrained_S_all      1.173
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0832P)²+52.4304P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2170
_refine_ls_wR_factor_ref         0.2249
_refine_special_details          
;
 Refined as a 2-component perfect twin.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Riding coordinates:
 O4(H4), O6(H6), O13(H13), O18(H18), O20(H20), O27(H27)
2.b Ternary CH refined with riding coordinates:
 C7(H7), C14(H14), C21(H21), C28(H28)
2.c Secondary CH2 refined with riding coordinates:
 C29(H29A,H29B), C32(H32A,H32B), C34(H34A,H34B), C36(H36A,H36B)
2.d Aromatic/amide H refined with riding coordinates:
 C2(H2), C9(H9), C16(H16), C23(H23), C37(H37), C38(H38), C39(H39), C40(H40),
 C43(H43), C44(H44), C45(H45), C46(H46), C47(H47), C48(H48), C51(H51), C52(H52),
  C53(H53), C54(H54)
2.e Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C33(H33A,H33B,H33C), C35(H35A,H35B,
 H35C), C55(H55A,H55B,H55C), C57(H57A,H57B,H57C)
2.f Idealised tetrahedral OH refined as rotating group:
 O11(H11), O25(H25)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.06113(6) 0.57473(3) 0.62972(6) 0.0310(2) Uani 1 1 d . . . . .
Br2 Br 0.42485(6) 0.57307(3) 0.77903(6) 0.0304(2) Uani 1 1 d . . . . .
Br3 Br 0.60244(6) 0.56666(3) 0.28424(6) 0.0315(2) Uani 1 1 d . . . . .
Br4 Br 0.10990(7) 0.56144(4) 0.11861(7) 0.0423(3) Uani 1 1 d . . . . .
O1G O 0.2296(4) 0.4214(2) 0.5397(4) 0.0277(12) Uani 1 1 d . . . . .
O1S O 0.2848(5) 0.8200(3) 0.4327(4) 0.0436(16) Uani 1 1 d . . . . .
O2G O 0.2520(4) 0.5910(2) -0.0592(4) 0.0294(13) Uani 1 1 d . . . . .
O4 O 0.0703(4) 0.6409(2) 0.7388(4) 0.0257(11) Uani 1 1 d . . . . .
H4 H 0.1265 0.6424 0.7616 0.038 Uiso 1 1 d R . . . .
O6 O -0.0700(4) 0.6256(2) 0.4330(4) 0.0304(13) Uani 1 1 d . . . . .
H6 H -0.1216 0.6097 0.4404 0.046 Uiso 1 1 d R . . . .
O11 O 0.5440(4) 0.6234(2) 0.6399(4) 0.0287(12) Uani 1 1 d . . . . .
H11 H 0.5623 0.6243 0.5861 0.043 Uiso 1 1 calc GR . . . .
O13 O 0.2518(4) 0.6447(2) 0.7914(4) 0.0255(12) Uani 1 1 d . . . . .
H13 H 0.2489 0.6263 0.8389 0.038 Uiso 1 1 d R . . . .
O18 O 0.4702(4) 0.6263(2) 0.1620(4) 0.0287(12) Uani 1 1 d . . . . .
H18 H 0.4128 0.6246 0.1454 0.043 Uiso 1 1 d R . . . .
O20 O 0.6142(4) 0.6303(2) 0.4675(4) 0.0278(12) Uani 1 1 d . . . . .
H20 H 0.6662 0.6140 0.4687 0.042 Uiso 1 1 d R . . . .
O25 O -0.0048(4) 0.6151(2) 0.2587(4) 0.0326(13) Uani 1 1 d . . . . .
H25 H -0.0235 0.6195 0.3117 0.049 Uiso 1 1 calc GR . . . .
O27 O 0.2867(4) 0.6287(2) 0.1017(4) 0.0312(13) Uani 1 1 d . . . . .
H27 H 0.2732 0.6171 0.0476 0.047 Uiso 1 1 d R . . . .
N1G N 0.2302(5) 0.4720(3) 0.5363(5) 0.0268(14) Uani 1 1 d . . . . .
N2G N 0.2226(5) 0.5439(2) -0.0831(4) 0.0258(14) Uani 1 1 d . . . . .
C1 C 0.0436(5) 0.6902(3) 0.4619(5) 0.0200(15) Uani 1 1 d . . . . .
C2 C 0.1089(5) 0.7131(3) 0.5232(5) 0.0159(13) Uani 1 1 d . . . . .
H2 H 0.1471 0.7389 0.5009 0.019 Uiso 1 1 calc R . . . .
C3 C 0.1195(5) 0.6988(3) 0.6170(5) 0.0190(14) Uani 1 1 d . . . . .
C4 C 0.0656(5) 0.6579(3) 0.6489(5) 0.0183(14) Uani 1 1 d . . . . .
C5 C 0.0032(5) 0.6328(3) 0.5870(5) 0.0219(15) Uani 1 1 d . . . . .
C6 C -0.0088(5) 0.6490(3) 0.4945(5) 0.0218(15) Uani 1 1 d . . . . .
C7 C 0.1926(5) 0.7252(3) 0.6814(5) 0.0173(14) Uani 1 1 d . . . . .
H7 H 0.1739 0.7182 0.7455 0.021 Uiso 1 1 calc R . . . .
C8 C 0.2898(5) 0.7018(3) 0.6710(5) 0.0185(14) Uani 1 1 d . . . . .
C9 C 0.3545(5) 0.7165(3) 0.6051(4) 0.0173(14) Uani 1 1 d . . . . .
H9 H 0.3383 0.7439 0.5668 0.021 Uiso 1 1 calc R . . . .
C10 C 0.4405(5) 0.6937(3) 0.5919(5) 0.0181(14) Uani 1 1 d . . . . .
C11 C 0.4628(5) 0.6502(3) 0.6456(5) 0.0213(15) Uani 1 1 d . . . . .
C12 C 0.3986(5) 0.6338(3) 0.7115(5) 0.0200(14) Uani 1 1 d . . . . .
C13 C 0.3139(5) 0.6592(3) 0.7260(5) 0.0180(14) Uani 1 1 d . . . . .
C14 C 0.5125(5) 0.7147(3) 0.5245(5) 0.0181(14) Uani 1 1 d . . . . .
H14 H 0.5748 0.7033 0.5479 0.022 Uiso 1 1 calc R . . . .
C15 C 0.4981(5) 0.6914(3) 0.4270(5) 0.0193(14) Uani 1 1 d . . . . .
C16 C 0.4328(5) 0.7109(3) 0.3614(5) 0.0164(13) Uani 1 1 d . . . . .
H16 H 0.3954 0.7383 0.3785 0.020 Uiso 1 1 calc R . . . .
C17 C 0.4207(5) 0.6912(3) 0.2711(5) 0.0190(14) Uani 1 1 d . . . . .
C18 C 0.4751(5) 0.6493(3) 0.2478(5) 0.0245(16) Uani 1 1 d . . . . .
C19 C 0.5382(5) 0.6279(3) 0.3135(5) 0.0229(15) Uani 1 1 d . . . . .
C20 C 0.5525(5) 0.6493(3) 0.4016(5) 0.0212(15) Uani 1 1 d . . . . .
C21 C 0.3486(5) 0.7137(3) 0.2016(5) 0.0216(15) Uani 1 1 d . . . . .
H21 H 0.3678 0.7031 0.1393 0.026 Uiso 1 1 calc R . . . .
C22 C 0.2505(5) 0.6902(3) 0.2166(5) 0.0225(15) Uani 1 1 d . . . . .
C23 C 0.1879(6) 0.7086(3) 0.2802(5) 0.0234(15) Uani 1 1 d . . . . .
H23 H 0.2049 0.7374 0.3144 0.028 Uiso 1 1 calc R . . . .
C24 C 0.0999(5) 0.6863(3) 0.2960(5) 0.0224(15) Uani 1 1 d . . . . .
C25 C 0.0776(6) 0.6413(3) 0.2478(5) 0.0268(17) Uani 1 1 d . . . . .
C26 C 0.1401(6) 0.6228(3) 0.1823(5) 0.0266(17) Uani 1 1 d . . . . .
C27 C 0.2247(5) 0.6473(3) 0.1653(5) 0.0234(16) Uani 1 1 d . . . . .
C28 C 0.0283(5) 0.7093(3) 0.3625(5) 0.0251(16) Uani 1 1 d . . . . .
H28 H -0.0344 0.6973 0.3412 0.030 Uiso 1 1 calc R . . . .
C29 C 0.0254(6) 0.7682(3) 0.3582(5) 0.0270(17) Uani 1 1 d . . . . .
H29A H 0.0859 0.7816 0.3808 0.032 Uiso 1 1 calc R . . . .
H29B H 0.0162 0.7788 0.2937 0.032 Uiso 1 1 calc R . . . .
C30 C -0.0536(6) 0.7908(3) 0.4164(6) 0.0328(19) Uani 1 1 d . . . . .
H30A H -0.1127 0.7748 0.3992 0.049 Uiso 1 1 calc GR . . . .
H30B H -0.0581 0.8267 0.4049 0.049 Uiso 1 1 calc GR . . . .
H30C H -0.0395 0.7850 0.4815 0.049 Uiso 1 1 calc GR . . . .
C31 C 0.2554(6) 0.8089(3) 0.7463(6) 0.0300(18) Uani 1 1 d . . . . .
H31A H 0.3203 0.7991 0.7390 0.045 Uiso 1 1 calc GR . . . .
H31B H 0.2349 0.7983 0.8066 0.045 Uiso 1 1 calc GR . . . .
H31C H 0.2499 0.8452 0.7411 0.045 Uiso 1 1 calc GR . . . .
C32 C 0.5160(6) 0.7729(3) 0.5237(5) 0.0236(16) Uani 1 1 d . . . . .
H32A H 0.4561 0.7859 0.4987 0.028 Uiso 1 1 calc R . . . .
H32B H 0.5238 0.7851 0.5873 0.028 Uiso 1 1 calc R . . . .
C33 C 0.5961(6) 0.7939(3) 0.4658(6) 0.0307(18) Uani 1 1 d . . . . .
H33A H 0.5881 0.7826 0.4024 0.046 Uiso 1 1 calc GR . . . .
H33B H 0.6558 0.7819 0.4911 0.046 Uiso 1 1 calc GR . . . .
H33C H 0.5950 0.8304 0.4676 0.046 Uiso 1 1 calc GR . . . .
C34 C 0.3480(6) 0.7719(3) 0.2021(5) 0.0252(16) Uani 1 1 d . . . . .
H34A H 0.3229 0.7838 0.2605 0.030 Uiso 1 1 calc R . . . .
H34B H 0.4125 0.7842 0.1983 0.030 Uiso 1 1 calc R . . . .
C35 C 0.2889(7) 0.7936(4) 0.1215(6) 0.035(2) Uani 1 1 d . . . . .
H35A H 0.3128 0.7814 0.0635 0.052 Uiso 1 1 calc GR . . . .
H35B H 0.2924 0.8301 0.1229 0.052 Uiso 1 1 calc GR . . . .
H35C H 0.2242 0.7831 0.1270 0.052 Uiso 1 1 calc GR . . . .
C36 C 0.1936(5) 0.7837(3) 0.6703(5) 0.0198(14) Uani 1 1 d . . . . .
H36A H 0.2175 0.7924 0.6095 0.024 Uiso 1 1 calc R . . . .
H36B H 0.1294 0.7966 0.6734 0.024 Uiso 1 1 calc R . . . .
C37 C 0.3029(7) 0.5751(4) 0.3780(7) 0.040(2) Uani 1 1 d . . . . .
H37 H 0.3025 0.6104 0.3745 0.048 Uiso 1 1 calc R . . . .
C38 C 0.3380(8) 0.5473(4) 0.3059(7) 0.045(2) Uani 1 1 d . . . . .
H38 H 0.3614 0.5637 0.2540 0.053 Uiso 1 1 calc R . . . .
C39 C 0.3387(6) 0.4934(4) 0.3105(6) 0.036(2) Uani 1 1 d . . . . .
H39 H 0.3642 0.4748 0.2620 0.043 Uiso 1 1 calc R . . . .
C40 C 0.3024(6) 0.4685(3) 0.3852(6) 0.0279(17) Uani 1 1 d . . . . .
H40 H 0.3014 0.4331 0.3864 0.033 Uiso 1 1 calc R . . . .
C41 C 0.2664(6) 0.4963(3) 0.4601(6) 0.0272(17) Uani 1 1 d . . . . .
C42 C 0.2671(6) 0.5504(3) 0.4581(6) 0.0310(18) Uani 1 1 d . . . . .
C43 C 0.2318(7) 0.5775(4) 0.5350(7) 0.039(2) Uani 1 1 d . . . . .
H43 H 0.2312 0.6129 0.5354 0.047 Uiso 1 1 calc R . . . .
C44 C 0.1991(7) 0.5507(3) 0.6081(6) 0.036(2) Uani 1 1 d . . . . .
H44 H 0.1772 0.5681 0.6597 0.043 Uiso 1 1 calc R . . . .
C45 C 0.1973(6) 0.4980(3) 0.6078(6) 0.0334(19) Uani 1 1 d . . . . .
H45 H 0.1727 0.4807 0.6583 0.040 Uiso 1 1 calc R . . . .
C46 C 0.1440(6) 0.5380(4) -0.1346(6) 0.038(2) Uani 1 1 d . . . . .
H46 H 0.1086 0.5666 -0.1515 0.046 Uiso 1 1 calc R . . . .
C47 C 0.1129(8) 0.4904(5) -0.1644(6) 0.053(3) Uani 1 1 d . . . . .
H47 H 0.0581 0.4870 -0.2015 0.064 Uiso 1 1 calc R . . . .
C48 C 0.1640(10) 0.4492(5) -0.1381(7) 0.063(4) Uani 1 1 d . . . . .
H48 H 0.1447 0.4170 -0.1576 0.075 Uiso 1 1 calc R . . . .
C49 C 0.2457(9) 0.4546(4) -0.0820(7) 0.047(3) Uani 1 1 d . . . . .
C50 C 0.2750(6) 0.5033(3) -0.0532(6) 0.0309(18) Uani 1 1 d . . . . .
C51 C 0.3541(6) 0.5113(4) 0.0058(6) 0.039(2) Uani 1 1 d . . . . .
H51 H 0.3718 0.5438 0.0251 0.047 Uiso 1 1 calc R . . . .
C52 C 0.4044(8) 0.4695(5) 0.0338(9) 0.061(3) Uani 1 1 d . . . . .
H52 H 0.4550 0.4739 0.0760 0.073 Uiso 1 1 calc R . . . .
C53 C 0.3833(12) 0.4198(6) 0.0018(10) 0.080(5) Uani 1 1 d . . . . .
H53 H 0.4227 0.3926 0.0177 0.096 Uiso 1 1 calc R . . . .
C54 C 0.3035(13) 0.4126(4) -0.0530(9) 0.072(5) Uani 1 1 d . . . . .
H54 H 0.2866 0.3799 -0.0717 0.087 Uiso 1 1 calc R . . . .
C55 C 0.2405(10) 0.8789(5) 0.3135(8) 0.070(4) Uani 1 1 d . . . . .
H55A H 0.1905 0.8549 0.3013 0.105 Uiso 1 1 calc GR . . . .
H55B H 0.2757 0.8839 0.2579 0.105 Uiso 1 1 calc GR . . . .
H55C H 0.2139 0.9107 0.3326 0.105 Uiso 1 1 calc GR . . . .
C56 C 0.3051(8) 0.8591(4) 0.3896(7) 0.048(3) Uani 1 1 d . . . . .
C57 C 0.3955(9) 0.8875(5) 0.4092(9) 0.060(3) Uani 1 1 d . . . . .
H57A H 0.4028 0.8935 0.4751 0.091 Uiso 1 1 calc GR . . . .
H57B H 0.3935 0.9194 0.3768 0.091 Uiso 1 1 calc GR . . . .
H57C H 0.4480 0.8678 0.3883 0.091 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C5 1.888(8) . ?
Br2 C12 1.898(7) . ?
Br3 C19 1.902(7) . ?
Br4 C26 1.895(8) . ?
O1G N1G 1.330(9) . ?
O1S C56 1.237(13) . ?
O2G N2G 1.348(9) . ?
O4 H4 0.8500 . ?
O4 C4 1.363(9) . ?
O6 H6 0.8480 . ?
O6 C6 1.363(9) . ?
O11 H11 0.8200 . ?
O11 C11 1.351(9) . ?
O13 H13 0.8370 . ?
O13 C13 1.356(9) . ?
O18 H18 0.8398 . ?
O18 C18 1.369(9) . ?
O20 H20 0.8503 . ?
O20 C20 1.361(9) . ?
O25 H25 0.8200 . ?
O25 C25 1.366(9) . ?
O27 H27 0.8484 . ?
O27 C27 1.372(9) . ?
N1G C41 1.376(11) . ?
N1G C45 1.326(11) . ?
N2G C46 1.324(11) . ?
N2G C50 1.360(11) . ?
C1 C2 1.393(10) . ?
C1 C6 1.399(11) . ?
C1 C28 1.520(10) . ?
C2 H2 0.9300 . ?
C2 C3 1.399(10) . ?
C3 C4 1.400(10) . ?
C3 C7 1.530(10) . ?
C4 C5 1.398(11) . ?
C5 C6 1.397(10) . ?
C7 H7 0.9800 . ?
C7 C8 1.515(10) . ?
C7 C36 1.547(10) . ?
C8 C9 1.389(10) . ?
C8 C13 1.405(10) . ?
C9 H9 0.9300 . ?
C9 C10 1.371(10) . ?
C10 C11 1.409(10) . ?
C10 C14 1.525(10) . ?
C11 C12 1.395(11) . ?
C12 C13 1.391(10) . ?
C14 H14 0.9800 . ?
C14 C15 1.533(9) . ?
C14 C32 1.532(10) . ?
C15 C16 1.396(10) . ?
C15 C20 1.401(11) . ?
C16 H16 0.9300 . ?
C16 C17 1.398(10) . ?
C17 C18 1.389(11) . ?
C17 C21 1.523(10) . ?
C18 C19 1.394(12) . ?
C19 C20 1.391(11) . ?
C21 H21 0.9800 . ?
C21 C22 1.536(10) . ?
C21 C34 1.532(11) . ?
C22 C23 1.375(11) . ?
C22 C27 1.389(11) . ?
C23 H23 0.9300 . ?
C23 C24 1.397(11) . ?
C24 C25 1.401(12) . ?
C24 C28 1.533(10) . ?
C25 C26 1.394(11) . ?
C26 C27 1.386(11) . ?
C28 H28 0.9800 . ?
C28 C29 1.551(12) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C29 C30 1.531(11) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C31 C36 1.527(10) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C32 C33 1.524(11) . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C34 C35 1.516(10) . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C37 H37 0.9300 . ?
C37 C38 1.368(14) . ?
C37 C42 1.425(13) . ?
C38 H38 0.9300 . ?
C38 C39 1.418(14) . ?
C39 H39 0.9300 . ?
C39 C40 1.367(12) . ?
C40 H40 0.9300 . ?
C40 C41 1.405(11) . ?
C41 C42 1.424(12) . ?
C42 C43 1.414(12) . ?
C43 H43 0.9300 . ?
C43 C44 1.354(13) . ?
C44 H44 0.9300 . ?
C44 C45 1.387(13) . ?
C45 H45 0.9300 . ?
C46 H46 0.9300 . ?
C46 C47 1.390(15) . ?
C47 H47 0.9300 . ?
C47 C48 1.350(19) . ?
C48 H48 0.9300 . ?
C48 C49 1.394(18) . ?
C49 C50 1.404(13) . ?
C49 C54 1.429(18) . ?
C50 C51 1.396(13) . ?
C51 H51 0.9300 . ?
C51 C52 1.361(15) . ?
C52 H52 0.9300 . ?
C52 C53 1.41(2) . ?
C53 H53 0.9300 . ?
C53 C54 1.37(2) . ?
C54 H54 0.9300 . ?
C55 H55A 0.9600 . ?
C55 H55B 0.9600 . ?
C55 H55C 0.9600 . ?
C55 C56 1.494(16) . ?
C56 C57 1.499(18) . ?
C57 H57A 0.9600 . ?
C57 H57B 0.9600 . ?
C57 H57C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O4 H4 111.6 . . ?
C6 O6 H6 132.2 . . ?
C11 O11 H11 109.5 . . ?
C13 O13 H13 140.5 . . ?
C18 O18 H18 107.6 . . ?
C20 O20 H20 137.3 . . ?
C25 O25 H25 109.5 . . ?
C27 O27 H27 127.1 . . ?
O1G N1G C41 119.7(6) . . ?
C45 N1G O1G 118.9(7) . . ?
C45 N1G C41 121.3(7) . . ?
O2G N2G C50 118.7(7) . . ?
C46 N2G O2G 119.7(7) . . ?
C46 N2G C50 121.6(8) . . ?
C2 C1 C6 118.1(7) . . ?
C2 C1 C28 121.4(7) . . ?
C6 C1 C28 120.4(7) . . ?
C1 C2 H2 118.7 . . ?
C1 C2 C3 122.7(7) . . ?
C3 C2 H2 118.7 . . ?
C2 C3 C4 118.4(7) . . ?
C2 C3 C7 120.5(6) . . ?
C4 C3 C7 121.0(6) . . ?
O4 C4 C3 123.3(6) . . ?
O4 C4 C5 117.2(6) . . ?
C5 C4 C3 119.6(6) . . ?
C4 C5 Br1 118.5(5) . . ?
C6 C5 Br1 120.5(6) . . ?
C6 C5 C4 121.0(7) . . ?
O6 C6 C1 117.7(7) . . ?
O6 C6 C5 122.2(7) . . ?
C5 C6 C1 120.1(7) . . ?
C3 C7 H7 106.6 . . ?
C3 C7 C36 113.5(6) . . ?
C8 C7 C3 110.7(6) . . ?
C8 C7 H7 106.6 . . ?
C8 C7 C36 112.5(6) . . ?
C36 C7 H7 106.6 . . ?
C9 C8 C7 124.7(6) . . ?
C9 C8 C13 116.7(7) . . ?
C13 C8 C7 118.3(6) . . ?
C8 C9 H9 117.4 . . ?
C10 C9 C8 125.1(7) . . ?
C10 C9 H9 117.4 . . ?
C9 C10 C11 117.7(7) . . ?
C9 C10 C14 122.5(6) . . ?
C11 C10 C14 119.8(6) . . ?
O11 C11 C10 124.6(7) . . ?
O11 C11 C12 116.7(6) . . ?
C12 C11 C10 118.7(7) . . ?
C11 C12 Br2 119.0(5) . . ?
C13 C12 Br2 118.9(5) . . ?
C13 C12 C11 122.0(7) . . ?
O13 C13 C8 117.4(6) . . ?
O13 C13 C12 123.0(6) . . ?
C12 C13 C8 119.7(7) . . ?
C10 C14 H14 106.3 . . ?
C10 C14 C15 111.1(6) . . ?
C10 C14 C32 112.9(6) . . ?
C15 C14 H14 106.3 . . ?
C32 C14 H14 106.3 . . ?
C32 C14 C15 113.3(6) . . ?
C16 C15 C14 122.3(6) . . ?
C16 C15 C20 118.1(7) . . ?
C20 C15 C14 119.6(6) . . ?
C15 C16 H16 118.4 . . ?
C15 C16 C17 123.2(7) . . ?
C17 C16 H16 118.4 . . ?
C16 C17 C21 121.5(7) . . ?
C18 C17 C16 117.6(7) . . ?
C18 C17 C21 120.9(7) . . ?
O18 C18 C17 123.5(7) . . ?
O18 C18 C19 116.2(7) . . ?
C17 C18 C19 120.3(7) . . ?
C18 C19 Br3 119.5(6) . . ?
C20 C19 Br3 119.0(6) . . ?
C20 C19 C18 121.5(7) . . ?
O20 C20 C15 117.1(7) . . ?
O20 C20 C19 123.6(7) . . ?
C19 C20 C15 119.3(7) . . ?
C17 C21 H21 106.7 . . ?
C17 C21 C22 110.0(6) . . ?
C17 C21 C34 112.9(6) . . ?
C22 C21 H21 106.7 . . ?
C34 C21 H21 106.7 . . ?
C34 C21 C22 113.3(7) . . ?
C23 C22 C21 123.4(7) . . ?
C23 C22 C27 118.2(7) . . ?
C27 C22 C21 118.4(7) . . ?
C22 C23 H23 118.3 . . ?
C22 C23 C24 123.4(7) . . ?
C24 C23 H23 118.3 . . ?
C23 C24 C25 117.6(7) . . ?
C23 C24 C28 122.7(7) . . ?
C25 C24 C28 119.7(7) . . ?
O25 C25 C24 123.4(7) . . ?
O25 C25 C26 117.2(7) . . ?
C26 C25 C24 119.3(7) . . ?
C25 C26 Br4 118.9(6) . . ?
C27 C26 Br4 119.7(6) . . ?
C27 C26 C25 121.4(7) . . ?
O27 C27 C22 118.6(7) . . ?
O27 C27 C26 121.3(7) . . ?
C26 C27 C22 120.0(7) . . ?
C1 C28 C24 111.9(6) . . ?
C1 C28 H28 106.7 . . ?
C1 C28 C29 111.7(6) . . ?
C24 C28 H28 106.7 . . ?
C24 C28 C29 112.7(6) . . ?
C29 C28 H28 106.7 . . ?
C28 C29 H29A 109.1 . . ?
C28 C29 H29B 109.1 . . ?
H29A C29 H29B 107.8 . . ?
C30 C29 C28 112.6(7) . . ?
C30 C29 H29A 109.1 . . ?
C30 C29 H29B 109.1 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C36 C31 H31A 109.5 . . ?
C36 C31 H31B 109.5 . . ?
C36 C31 H31C 109.5 . . ?
C14 C32 H32A 109.0 . . ?
C14 C32 H32B 109.0 . . ?
H32A C32 H32B 107.8 . . ?
C33 C32 C14 113.0(6) . . ?
C33 C32 H32A 109.0 . . ?
C33 C32 H32B 109.0 . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C21 C34 H34A 109.2 . . ?
C21 C34 H34B 109.2 . . ?
H34A C34 H34B 107.9 . . ?
C35 C34 C21 112.1(7) . . ?
C35 C34 H34A 109.2 . . ?
C35 C34 H34B 109.2 . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C7 C36 H36A 109.3 . . ?
C7 C36 H36B 109.3 . . ?
C31 C36 C7 111.5(6) . . ?
C31 C36 H36A 109.3 . . ?
C31 C36 H36B 109.3 . . ?
H36A C36 H36B 108.0 . . ?
C38 C37 H37 119.7 . . ?
C38 C37 C42 120.6(9) . . ?
C42 C37 H37 119.7 . . ?
C37 C38 H38 120.0 . . ?
C37 C38 C39 120.1(8) . . ?
C39 C38 H38 120.0 . . ?
C38 C39 H39 119.6 . . ?
C40 C39 C38 120.8(8) . . ?
C40 C39 H39 119.6 . . ?
C39 C40 H40 120.0 . . ?
C39 C40 C41 120.1(8) . . ?
C41 C40 H40 120.0 . . ?
N1G C41 C40 121.1(8) . . ?
N1G C41 C42 118.9(7) . . ?
C40 C41 C42 120.1(8) . . ?
C41 C42 C37 118.3(8) . . ?
C43 C42 C37 122.6(8) . . ?
C43 C42 C41 119.1(8) . . ?
C42 C43 H43 120.8 . . ?
C44 C43 C42 118.4(8) . . ?
C44 C43 H43 120.8 . . ?
C43 C44 H44 119.2 . . ?
C43 C44 C45 121.6(8) . . ?
C45 C44 H44 119.2 . . ?
N1G C45 C44 120.7(8) . . ?
N1G C45 H45 119.6 . . ?
C44 C45 H45 119.6 . . ?
N2G C46 H46 119.0 . . ?
N2G C46 C47 121.9(10) . . ?
C47 C46 H46 119.0 . . ?
C46 C47 H47 120.8 . . ?
C48 C47 C46 118.4(9) . . ?
C48 C47 H47 120.8 . . ?
C47 C48 H48 119.8 . . ?
C47 C48 C49 120.4(10) . . ?
C49 C48 H48 119.8 . . ?
C48 C49 C50 119.7(11) . . ?
C48 C49 C54 123.0(12) . . ?
C50 C49 C54 117.3(12) . . ?
N2G C50 C49 117.9(9) . . ?
N2G C50 C51 119.5(8) . . ?
C51 C50 C49 122.6(10) . . ?
C50 C51 H51 121.4 . . ?
C52 C51 C50 117.3(11) . . ?
C52 C51 H51 121.4 . . ?
C51 C52 H52 118.4 . . ?
C51 C52 C53 123.2(12) . . ?
C53 C52 H52 118.4 . . ?
C52 C53 H53 120.8 . . ?
C54 C53 C52 118.5(11) . . ?
C54 C53 H53 120.8 . . ?
C49 C54 H54 119.5 . . ?
C53 C54 C49 120.9(12) . . ?
C53 C54 H54 119.5 . . ?
H55A C55 H55B 109.5 . . ?
H55A C55 H55C 109.5 . . ?
H55B C55 H55C 109.5 . . ?
C56 C55 H55A 109.5 . . ?
C56 C55 H55B 109.5 . . ?
C56 C55 H55C 109.5 . . ?
O1S C56 C55 120.6(12) . . ?
O1S C56 C57 121.9(10) . . ?
C55 C56 C57 117.4(11) . . ?
C56 C57 H57A 109.5 . . ?
C56 C57 H57B 109.5 . . ?
C56 C57 H57C 109.5 . . ?
H57A C57 H57B 109.5 . . ?
H57A C57 H57C 109.5 . . ?
H57B C57 H57C 109.5 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.206
_oxdiff_exptl_absorpt_empirical_full_min 0.797
