# Electronic Supplementary Material (ESI) for Chemical Science.
# 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).
# 
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# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
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data_mo_dm16701_0m
_database_code_depnum_ccdc_archive 'CCDC 1517578'
_audit_update_record             
;
2016-11-16 deposited with the CCDC.
2017-05-16 downloaded from the CCDC.
;
_audit_creation_date             2016-10-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H18 Cl N3 O'
_chemical_formula_sum            'C18 H18 Cl N3 O'
_chemical_formula_weight         327.80
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   11.6963(15)
_cell_length_b                   7.8375(10)
_cell_length_c                   18.213(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.443(2)
_cell_angle_gamma                90
_cell_volume                     1659.0(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3855
_cell_measurement_temperature    130
_cell_measurement_theta_max      25.822
_cell_measurement_theta_min      2.69
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.965
_exptl_absorpt_coefficient_mu    0.238
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6819
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1200 before and 0.0445 after correction.
The Ratio of minimum to maximum transmission is 0.9140.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0603
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            16974
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.618
_diffrn_reflns_theta_min         1.125
_diffrn_ambient_temperature      130
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.799
_reflns_Friedel_fraction_full    0.945
_reflns_Friedel_fraction_max     0.908
_reflns_number_gt                7532
_reflns_number_total             9757
_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       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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         0.240
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 
;
 Flack x determined using 2613 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     419
_refine_ls_number_reflns         9757
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0464
_refine_ls_restrained_S_all      1.014
_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)+(0.0368P)²+0.1709P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0871
_refine_ls_wR_factor_ref         0.0972
_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 Ternary CH refined with riding coordinates:
 C2(H2), C20(H20)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C24(H24A,H24B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C8(H8), C9(H9), C11(H11), C12(H12), C14(H14), C15(H15),
 C16(H16), C17(H17), C18(H18), C22(H22), C23(H23), C26(H26), C27(H27), C29(H29),
  C30(H30), C32(H32), C33(H33), C34(H34), C35(H35), C36(H36)
2.d Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C21(H21A,H21B,H21C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.33217(7) 0.28456(10) 0.38654(4) 0.03702(18) Uani 1 1 d . . . . .
O1 O 0.54128(16) 0.3713(3) 0.85742(11) 0.0292(4) Uani 1 1 d . . . . .
H1 H 0.563191 0.278326 0.840764 0.044 Uiso 1 1 calc GR . . . .
N1 N 0.40174(19) 0.1817(3) 0.73850(12) 0.0220(5) Uani 1 1 d . . . . .
N2 N 0.50758(19) 0.1078(3) 0.75324(13) 0.0292(5) Uani 1 1 d . . . . .
N3 N 0.3760(2) -0.0853(3) 0.70548(16) 0.0411(7) Uani 1 1 d . . . . .
C1 C 0.4194(2) 0.3856(3) 0.84154(14) 0.0217(5) Uani 1 1 d . . . . .
C2 C 0.3844(2) 0.3613(3) 0.75685(14) 0.0208(5) Uani 1 1 d . . . . .
H2 H 0.300388 0.386983 0.746326 0.025 Uiso 1 1 calc R . . . .
C3 C 0.3887(2) 0.5656(4) 0.86599(15) 0.0288(6) Uani 1 1 d . . . . .
H3A H 0.414634 0.580031 0.918684 0.043 Uiso 1 1 calc GR . . . .
H3B H 0.305174 0.581680 0.857493 0.043 Uiso 1 1 calc GR . . . .
H3C H 0.426742 0.650236 0.837406 0.043 Uiso 1 1 calc GR . . . .
C4 C 0.3263(3) 0.0657(4) 0.71051(16) 0.0314(6) Uani 1 1 d . . . . .
H4 H 0.247114 0.088016 0.696007 0.038 Uiso 1 1 calc R . . . .
C5 C 0.4865(3) -0.0513(4) 0.73290(18) 0.0358(7) Uani 1 1 d . . . . .
H5 H 0.544559 -0.136603 0.737116 0.043 Uiso 1 1 calc R . . . .
C6 C 0.4490(3) 0.4758(4) 0.70706(14) 0.0264(6) Uani 1 1 d . . . . .
H6A H 0.428292 0.596429 0.714882 0.032 Uiso 1 1 calc R . . . .
H6B H 0.532808 0.463415 0.721114 0.032 Uiso 1 1 calc R . . . .
C7 C 0.4210(2) 0.4316(3) 0.62616(14) 0.0239(5) Uani 1 1 d . . . . .
C8 C 0.4887(2) 0.3173(4) 0.59156(15) 0.0267(6) Uani 1 1 d . . . . .
H8 H 0.554979 0.269430 0.618918 0.032 Uiso 1 1 calc R . . . .
C9 C 0.4618(2) 0.2718(4) 0.51816(14) 0.0272(6) Uani 1 1 d . . . . .
H9 H 0.508792 0.194000 0.495099 0.033 Uiso 1 1 calc R . . . .
C10 C 0.3652(2) 0.3419(4) 0.47937(15) 0.0250(6) Uani 1 1 d . . . . .
C11 C 0.2957(2) 0.4551(4) 0.51144(16) 0.0296(6) Uani 1 1 d . . . . .
H11 H 0.229489 0.501871 0.483651 0.036 Uiso 1 1 calc R . . . .
C12 C 0.3240(3) 0.5000(4) 0.58522(15) 0.0295(6) Uani 1 1 d . . . . .
H12 H 0.276628 0.578133 0.607866 0.035 Uiso 1 1 calc R . . . .
C13 C 0.3568(2) 0.2500(3) 0.88271(13) 0.0218(5) Uani 1 1 d . . . . .
C14 C 0.4157(2) 0.1327(4) 0.92983(15) 0.0288(6) Uani 1 1 d . . . . .
H14 H 0.497167 0.139173 0.939067 0.035 Uiso 1 1 calc R . . . .
C15 C 0.3571(3) 0.0056(4) 0.96380(16) 0.0339(7) Uani 1 1 d . . . . .
H15 H 0.398490 -0.073191 0.996320 0.041 Uiso 1 1 calc R . . . .
C16 C 0.2389(3) -0.0057(4) 0.95020(16) 0.0332(7) Uani 1 1 d . . . . .
H16 H 0.198796 -0.093230 0.972757 0.040 Uiso 1 1 calc R . . . .
C17 C 0.1790(2) 0.1111(4) 0.90347(16) 0.0314(6) Uani 1 1 d . . . . .
H17 H 0.097645 0.103749 0.894067 0.038 Uiso 1 1 calc R . . . .
C18 C 0.2372(2) 0.2384(4) 0.87050(15) 0.0276(6) Uani 1 1 d . . . . .
H18 H 0.195180 0.318866 0.839136 0.033 Uiso 1 1 calc R . . . .
Cl2 Cl 0.76319(7) 1.08508(10) 0.95917(4) 0.04075(19) Uani 1 1 d . . . . .
O2 O 1.03269(16) 0.2019(2) 0.73221(11) 0.0287(4) Uani 1 1 d . . . . .
H2A H 1.035562 0.099547 0.718922 0.043 Uiso 1 1 calc GR . . . .
N4 N 0.98687(18) 0.5739(3) 0.73423(11) 0.0208(4) Uani 1 1 d . . . . .
N5 N 1.10129(19) 0.5723(3) 0.75822(14) 0.0318(5) Uani 1 1 d . . . . .
N6 N 1.0479(2) 0.8316(3) 0.71271(14) 0.0304(5) Uani 1 1 d . . . . .
C19 C 0.9225(2) 0.2705(3) 0.70733(14) 0.0229(5) Uani 1 1 d . . . . .
C20 C 0.9080(2) 0.4369(3) 0.75106(15) 0.0221(5) Uani 1 1 d . . . . .
H20 H 0.828674 0.479367 0.734563 0.027 Uiso 1 1 calc R . . . .
C21 C 0.8276(2) 0.1446(4) 0.72322(17) 0.0303(6) Uani 1 1 d . . . . .
H21A H 0.825756 0.048943 0.688438 0.045 Uiso 1 1 calc GR . . . .
H21B H 0.753007 0.202888 0.717503 0.045 Uiso 1 1 calc GR . . . .
H21C H 0.843504 0.101542 0.773863 0.045 Uiso 1 1 calc GR . . . .
C22 C 0.9582(3) 0.7288(3) 0.70837(16) 0.0291(6) Uani 1 1 d . . . . .
H22 H 0.882408 0.761166 0.689158 0.035 Uiso 1 1 calc R . . . .
C23 C 1.1330(2) 0.7281(3) 0.74308(17) 0.0316(7) Uani 1 1 d . . . . .
H23 H 1.210432 0.765557 0.752798 0.038 Uiso 1 1 calc R . . . .
C24 C 0.9152(3) 0.4178(3) 0.83567(15) 0.0264(6) Uani 1 1 d . . . . .
H24A H 0.864748 0.323102 0.848141 0.032 Uiso 1 1 calc R . . . .
H24B H 0.995120 0.389806 0.855839 0.032 Uiso 1 1 calc R . . . .
C25 C 0.8782(2) 0.5819(4) 0.87022(14) 0.0241(5) Uani 1 1 d . . . . .
C26 C 0.7623(2) 0.6272(4) 0.86363(16) 0.0316(7) Uani 1 1 d . . . . .
H26 H 0.706709 0.551129 0.839839 0.038 Uiso 1 1 calc R . . . .
C27 C 0.7263(2) 0.7802(4) 0.89088(16) 0.0332(6) Uani 1 1 d . . . . .
H27 H 0.647043 0.809942 0.885527 0.040 Uiso 1 1 calc R . . . .
C28 C 0.8079(2) 0.8894(4) 0.92615(15) 0.0271(6) Uani 1 1 d . . . . .
C29 C 0.9229(2) 0.8464(4) 0.93548(15) 0.0288(6) Uani 1 1 d . . . . .
H29 H 0.977761 0.920955 0.961068 0.035 Uiso 1 1 calc R . . . .
C30 C 0.9576(2) 0.6933(4) 0.90706(15) 0.0276(6) Uani 1 1 d . . . . .
H30 H 1.036862 0.663808 0.912848 0.033 Uiso 1 1 calc R . . . .
C31 C 0.9102(2) 0.3086(3) 0.62411(14) 0.0231(5) Uani 1 1 d . . . . .
C32 C 0.9964(3) 0.2680(4) 0.58051(16) 0.0350(7) Uani 1 1 d . . . . .
H32 H 1.067225 0.222835 0.603000 0.042 Uiso 1 1 calc R . . . .
C33 C 0.9807(3) 0.2922(5) 0.50475(18) 0.0417(8) Uani 1 1 d . . . . .
H33 H 1.039749 0.260243 0.475648 0.050 Uiso 1 1 calc R . . . .
C34 C 0.8801(3) 0.3623(4) 0.47126(18) 0.0391(8) Uani 1 1 d . . . . .
H34 H 0.870015 0.379717 0.419318 0.047 Uiso 1 1 calc R . . . .
C35 C 0.7940(3) 0.4071(4) 0.51377(17) 0.0360(7) Uani 1 1 d . . . . .
H35 H 0.724669 0.456444 0.491062 0.043 Uiso 1 1 calc R . . . .
C36 C 0.8086(3) 0.3800(4) 0.58946(16) 0.0298(6) Uani 1 1 d . . . . .
H36 H 0.748722 0.410325 0.618186 0.036 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C10 1.750(3) . ?
O1 H1 0.8400 . ?
O1 C1 1.427(3) . ?
N1 N2 1.366(3) . ?
N1 C2 1.466(3) . ?
N1 C4 1.328(3) . ?
N2 C5 1.317(4) . ?
N3 C4 1.327(4) . ?
N3 C5 1.358(4) . ?
C1 C2 1.562(4) . ?
C1 C3 1.534(4) . ?
C1 C13 1.533(4) . ?
C2 H2 1.0000 . ?
C2 C6 1.534(4) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.513(4) . ?
C7 C8 1.393(4) . ?
C7 C12 1.393(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.385(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.377(4) . ?
C10 C11 1.377(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.393(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.387(4) . ?
C13 C18 1.394(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.393(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.380(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.386(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.382(4) . ?
C18 H18 0.9500 . ?
Cl2 C28 1.749(3) . ?
O2 H2A 0.8400 . ?
O2 C19 1.423(3) . ?
N4 N5 1.361(3) . ?
N4 C20 1.470(3) . ?
N4 C22 1.331(3) . ?
N5 C23 1.314(4) . ?
N6 C22 1.318(4) . ?
N6 C23 1.353(4) . ?
C19 C20 1.547(4) . ?
C19 C21 1.537(4) . ?
C19 C31 1.536(4) . ?
C20 H20 1.0000 . ?
C20 C24 1.541(4) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.516(4) . ?
C25 C26 1.394(4) . ?
C25 C30 1.391(4) . ?
C26 H26 0.9500 . ?
C26 C27 1.381(4) . ?
C27 H27 0.9500 . ?
C27 C28 1.385(4) . ?
C28 C29 1.379(4) . ?
C29 H29 0.9500 . ?
C29 C30 1.386(4) . ?
C30 H30 0.9500 . ?
C31 C32 1.389(4) . ?
C31 C36 1.399(4) . ?
C32 H32 0.9500 . ?
C32 C33 1.384(4) . ?
C33 H33 0.9500 . ?
C33 C34 1.377(5) . ?
C34 H34 0.9500 . ?
C34 C35 1.384(5) . ?
C35 H35 0.9500 . ?
C35 C36 1.386(4) . ?
C36 H36 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
N2 N1 C2 120.5(2) . . ?
C4 N1 N2 109.5(2) . . ?
C4 N1 C2 129.9(2) . . ?
C5 N2 N1 102.1(2) . . ?
C4 N3 C5 101.9(2) . . ?
O1 C1 C2 109.6(2) . . ?
O1 C1 C3 105.9(2) . . ?
O1 C1 C13 111.6(2) . . ?
C3 C1 C2 110.8(2) . . ?
C13 C1 C2 108.2(2) . . ?
C13 C1 C3 110.8(2) . . ?
N1 C2 C1 108.3(2) . . ?
N1 C2 H2 107.9 . . ?
N1 C2 C6 109.7(2) . . ?
C1 C2 H2 107.9 . . ?
C6 C2 C1 114.9(2) . . ?
C6 C2 H2 107.9 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N1 C4 H4 124.5 . . ?
N3 C4 N1 111.1(3) . . ?
N3 C4 H4 124.5 . . ?
N2 C5 N3 115.5(3) . . ?
N2 C5 H5 122.3 . . ?
N3 C5 H5 122.3 . . ?
C2 C6 H6A 109.2 . . ?
C2 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C7 C6 C2 112.0(2) . . ?
C7 C6 H6A 109.2 . . ?
C7 C6 H6B 109.2 . . ?
C8 C7 C6 121.0(2) . . ?
C12 C7 C6 120.5(2) . . ?
C12 C7 C8 118.4(2) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 C7 121.5(3) . . ?
C9 C8 H8 119.3 . . ?
C8 C9 H9 120.7 . . ?
C10 C9 C8 118.5(3) . . ?
C10 C9 H9 120.7 . . ?
C9 C10 Cl1 118.2(2) . . ?
C11 C10 Cl1 119.9(2) . . ?
C11 C10 C9 121.9(3) . . ?
C10 C11 H11 120.5 . . ?
C10 C11 C12 119.0(3) . . ?
C12 C11 H11 120.5 . . ?
C7 C12 H12 119.7 . . ?
C11 C12 C7 120.6(3) . . ?
C11 C12 H12 119.7 . . ?
C14 C13 C1 122.0(2) . . ?
C14 C13 C18 118.4(2) . . ?
C18 C13 C1 119.5(2) . . ?
C13 C14 H14 119.6 . . ?
C13 C14 C15 120.9(3) . . ?
C15 C14 H14 119.6 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.0(3) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 120.2 . . ?
C15 C16 C17 119.7(3) . . ?
C17 C16 H16 120.2 . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.3(3) . . ?
C18 C17 H17 119.8 . . ?
C13 C18 H18 119.6 . . ?
C17 C18 C13 120.8(2) . . ?
C17 C18 H18 119.6 . . ?
C19 O2 H2A 109.5 . . ?
N5 N4 C20 122.9(2) . . ?
C22 N4 N5 108.8(2) . . ?
C22 N4 C20 126.9(2) . . ?
C23 N5 N4 102.4(2) . . ?
C22 N6 C23 101.6(2) . . ?
O2 C19 C20 107.6(2) . . ?
O2 C19 C21 110.2(2) . . ?
O2 C19 C31 111.6(2) . . ?
C21 C19 C20 108.8(2) . . ?
C31 C19 C20 109.9(2) . . ?
C31 C19 C21 108.7(2) . . ?
N4 C20 C19 113.6(2) . . ?
N4 C20 H20 106.1 . . ?
N4 C20 C24 108.3(2) . . ?
C19 C20 H20 106.1 . . ?
C24 C20 C19 115.8(2) . . ?
C24 C20 H20 106.1 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N4 C22 H22 124.2 . . ?
N6 C22 N4 111.6(2) . . ?
N6 C22 H22 124.2 . . ?
N5 C23 N6 115.5(3) . . ?
N5 C23 H23 122.2 . . ?
N6 C23 H23 122.2 . . ?
C20 C24 H24A 109.6 . . ?
C20 C24 H24B 109.6 . . ?
H24A C24 H24B 108.1 . . ?
C25 C24 C20 110.3(2) . . ?
C25 C24 H24A 109.6 . . ?
C25 C24 H24B 109.6 . . ?
C26 C25 C24 120.0(2) . . ?
C30 C25 C24 121.8(2) . . ?
C30 C25 C26 118.2(3) . . ?
C25 C26 H26 119.2 . . ?
C27 C26 C25 121.5(3) . . ?
C27 C26 H26 119.2 . . ?
C26 C27 H27 120.6 . . ?
C26 C27 C28 118.8(3) . . ?
C28 C27 H27 120.6 . . ?
C27 C28 Cl2 119.0(2) . . ?
C29 C28 Cl2 119.8(2) . . ?
C29 C28 C27 121.2(3) . . ?
C28 C29 H29 120.4 . . ?
C28 C29 C30 119.2(3) . . ?
C30 C29 H29 120.4 . . ?
C25 C30 H30 119.5 . . ?
C29 C30 C25 121.1(3) . . ?
C29 C30 H30 119.5 . . ?
C32 C31 C19 121.8(2) . . ?
C32 C31 C36 118.0(3) . . ?
C36 C31 C19 120.2(2) . . ?
C31 C32 H32 119.5 . . ?
C33 C32 C31 121.0(3) . . ?
C33 C32 H32 119.5 . . ?
C32 C33 H33 119.8 . . ?
C34 C33 C32 120.5(3) . . ?
C34 C33 H33 119.8 . . ?
C33 C34 H34 120.2 . . ?
C33 C34 C35 119.5(3) . . ?
C35 C34 H34 120.2 . . ?
C34 C35 H35 120.0 . . ?
C34 C35 C36 120.1(3) . . ?
C36 C35 H35 120.0 . . ?
C31 C36 H36 119.5 . . ?
C35 C36 C31 120.9(3) . . ?
C35 C36 H36 119.5 . . ?

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 N2 0.84 2.13 2.802(3) 137.4 .

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
Cl1 C10 C11 C12 -179.5(2) . . . . ?
O1 C1 C2 N1 70.7(3) . . . . ?
O1 C1 C2 C6 -52.3(3) . . . . ?
O1 C1 C13 C14 0.9(3) . . . . ?
O1 C1 C13 C18 -176.3(2) . . . . ?
N1 N2 C5 N3 0.7(3) . . . . ?
N1 C2 C6 C7 51.1(3) . . . . ?
N2 N1 C2 C1 -58.0(3) . . . . ?
N2 N1 C2 C6 68.1(3) . . . . ?
N2 N1 C4 N3 0.1(3) . . . . ?
C1 C2 C6 C7 173.4(2) . . . . ?
C1 C13 C14 C15 -176.9(3) . . . . ?
C1 C13 C18 C17 176.2(3) . . . . ?
C2 N1 N2 C5 176.8(2) . . . . ?
C2 N1 C4 N3 -176.9(3) . . . . ?
C2 C1 C13 C14 121.6(3) . . . . ?
C2 C1 C13 C18 -55.7(3) . . . . ?
C2 C6 C7 C8 -93.0(3) . . . . ?
C2 C6 C7 C12 84.7(3) . . . . ?
C3 C1 C2 N1 -172.8(2) . . . . ?
C3 C1 C2 C6 64.2(3) . . . . ?
C3 C1 C13 C14 -116.8(3) . . . . ?
C3 C1 C13 C18 65.9(3) . . . . ?
C4 N1 N2 C5 -0.5(3) . . . . ?
C4 N1 C2 C1 118.7(3) . . . . ?
C4 N1 C2 C6 -115.2(3) . . . . ?
C4 N3 C5 N2 -0.7(4) . . . . ?
C5 N3 C4 N1 0.3(3) . . . . ?
C6 C7 C8 C9 177.9(3) . . . . ?
C6 C7 C12 C11 -177.8(3) . . . . ?
C7 C8 C9 C10 -0.2(4) . . . . ?
C8 C7 C12 C11 0.0(4) . . . . ?
C8 C9 C10 Cl1 179.7(2) . . . . ?
C8 C9 C10 C11 0.1(4) . . . . ?
C9 C10 C11 C12 0.0(4) . . . . ?
C10 C11 C12 C7 -0.1(4) . . . . ?
C12 C7 C8 C9 0.2(4) . . . . ?
C13 C1 C2 N1 -51.1(3) . . . . ?
C13 C1 C2 C6 -174.1(2) . . . . ?
C13 C14 C15 C16 0.6(5) . . . . ?
C14 C13 C18 C17 -1.2(4) . . . . ?
C14 C15 C16 C17 -0.9(5) . . . . ?
C15 C16 C17 C18 0.1(5) . . . . ?
C16 C17 C18 C13 0.9(4) . . . . ?
C18 C13 C14 C15 0.4(4) . . . . ?
Cl2 C28 C29 C30 -178.1(2) . . . . ?
O2 C19 C20 N4 66.7(3) . . . . ?
O2 C19 C20 C24 -59.7(3) . . . . ?
O2 C19 C31 C32 3.8(3) . . . . ?
O2 C19 C31 C36 -178.7(2) . . . . ?
N4 N5 C23 N6 1.4(4) . . . . ?
N4 C20 C24 C25 61.3(3) . . . . ?
N5 N4 C20 C19 -73.3(3) . . . . ?
N5 N4 C20 C24 57.0(3) . . . . ?
N5 N4 C22 N6 0.9(3) . . . . ?
C19 C20 C24 C25 -169.6(2) . . . . ?
C19 C31 C32 C33 175.4(3) . . . . ?
C19 C31 C36 C35 -176.7(3) . . . . ?
C20 N4 N5 C23 -168.8(2) . . . . ?
C20 N4 C22 N6 167.7(2) . . . . ?
C20 C19 C31 C32 123.1(3) . . . . ?
C20 C19 C31 C36 -59.4(3) . . . . ?
C20 C24 C25 C26 73.7(3) . . . . ?
C20 C24 C25 C30 -104.3(3) . . . . ?
C21 C19 C20 N4 -174.0(2) . . . . ?
C21 C19 C20 C24 59.6(3) . . . . ?
C21 C19 C31 C32 -117.9(3) . . . . ?
C21 C19 C31 C36 59.5(3) . . . . ?
C22 N4 N5 C23 -1.3(3) . . . . ?
C22 N4 C20 C19 121.5(3) . . . . ?
C22 N4 C20 C24 -108.2(3) . . . . ?
C22 N6 C23 N5 -0.9(4) . . . . ?
C23 N6 C22 N4 0.0(3) . . . . ?
C24 C25 C26 C27 -176.4(3) . . . . ?
C24 C25 C30 C29 177.1(2) . . . . ?
C25 C26 C27 C28 -0.7(4) . . . . ?
C26 C25 C30 C29 -1.0(4) . . . . ?
C26 C27 C28 Cl2 178.8(2) . . . . ?
C26 C27 C28 C29 -1.2(4) . . . . ?
C27 C28 C29 C30 1.9(4) . . . . ?
C28 C29 C30 C25 -0.8(4) . . . . ?
C30 C25 C26 C27 1.8(4) . . . . ?
C31 C19 C20 N4 -55.1(3) . . . . ?
C31 C19 C20 C24 178.5(2) . . . . ?
C31 C32 C33 C34 2.0(5) . . . . ?
C32 C31 C36 C35 0.8(4) . . . . ?
C32 C33 C34 C35 -0.6(5) . . . . ?
C33 C34 C35 C36 -0.6(5) . . . . ?
C34 C35 C36 C31 0.5(5) . . . . ?
C36 C31 C32 C33 -2.1(4) . . . . ?

_shelx_SHELXL_version_number     2016/6
_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_mo_dm16225_0m
_database_code_depnum_ccdc_archive 'CCDC 1517472'
_audit_update_record             
;
2016-11-15 deposited with the CCDC.
2017-05-16 downloaded from the CCDC.
;
_audit_creation_date             2016-04-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H31 B2 Br O4'
_chemical_formula_sum            'C22 H31 B2 Br O4'
_chemical_formula_weight         461.00
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
B B 0.0013 0.0007 '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'
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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   11.1006(17)
_cell_length_b                   6.9951(10)
_cell_length_c                   30.827(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.930(3)
_cell_angle_gamma                90
_cell_volume                     2384.8(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4389
_cell_measurement_temperature    130
_cell_measurement_theta_max      25.820
_cell_measurement_theta_min      2.36
_shelx_estimated_absorpt_T_max   0.744
_shelx_estimated_absorpt_T_min   0.622
_exptl_absorpt_coefficient_mu    1.747
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6136
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0786 before and 0.0645 after correction.
The Ratio of minimum to maximum transmission is 0.8224.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_unetI/netI     0.1178
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            24139
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.591
_diffrn_reflns_theta_min         1.841
_diffrn_ambient_temperature      130
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.849
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                9343
_reflns_number_total             14501
_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       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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         0.544
_refine_diff_density_min         -0.461
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details 
;
 Flack x determined using 3064 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.020(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.944
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     541
_refine_ls_number_reflns         14501
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0995
_refine_ls_R_factor_gt           0.0494
_refine_ls_restrained_S_all      0.944
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w=1/[σ²(Fo²)] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.1093
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10), C28(H28), C29(H29), C31(H31), C32(H32)
2.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C), C16(H16A,H16B,H16C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,
 H21B,H21C), C22(H22A,H22B,H22C), C26(H26A,H26B,H26C), C35(H35A,H35B,H35C),
 C36(H36A,H36B,H36C), C37(H37A,H37B,H37C), C38(H38A,H38B,H38C), C41(H41A,H41B,
 H41C), C42(H42A,H42B,H42C), C43(H43A,H43B,H43C), C44(H44A,H44B,H44C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.60334(4) 0.23567(8) 0.33605(2) 0.03829(15) Uani 1 1 d . . . . .
O1 O 0.9440(3) 0.4373(4) 0.15453(9) 0.0255(7) Uani 1 1 d . . . . .
O2 O 0.8628(3) 0.1439(4) 0.13768(9) 0.0237(7) Uani 1 1 d . . . . .
O3 O 0.7739(2) 0.3486(5) 0.05277(8) 0.0235(6) Uani 1 1 d . . . . .
O4 O 0.5841(2) 0.2469(4) 0.02918(8) 0.0222(6) Uani 1 1 d . . . . .
C1 C 0.7092(4) 0.4216(6) 0.14573(13) 0.0227(9) Uani 1 1 d . . . . .
C2 C 0.6196(4) 0.3333(7) 0.11063(12) 0.0220(9) Uani 1 1 d . . . . .
C3 C 0.5061(4) 0.2885(7) 0.11824(14) 0.0328(12) Uani 1 1 d . . . . .
C4 C 0.7155(4) 0.6390(6) 0.13583(14) 0.0293(10) Uani 1 1 d . . . . .
H4A H 0.7365 0.6576 0.1059 0.044 Uiso 1 1 calc GR . . . .
H4B H 0.7773 0.6988 0.1561 0.044 Uiso 1 1 calc GR . . . .
H4C H 0.6368 0.6978 0.1393 0.044 Uiso 1 1 calc GR . . . .
C5 C 0.6753(4) 0.3810(7) 0.19173(12) 0.0218(9) Uani 1 1 d . . . . .
C6 C 0.6745(4) 0.1915(7) 0.20662(13) 0.0257(10) Uani 1 1 d . . . . .
H6 H 0.6902 0.0907 0.1873 0.031 Uiso 1 1 calc R . . . .
C7 C 0.6513(4) 0.1483(7) 0.24880(14) 0.0284(11) Uani 1 1 d . . . . .
H7 H 0.6510 0.0190 0.2582 0.034 Uiso 1 1 calc R . . . .
C8 C 0.6286(4) 0.2931(7) 0.27725(13) 0.0256(11) Uani 1 1 d . . . . .
C9 C 0.6256(4) 0.4804(7) 0.26333(14) 0.0293(11) Uani 1 1 d . . . . .
H9 H 0.6074 0.5797 0.2827 0.035 Uiso 1 1 calc R . . . .
C10 C 0.6493(4) 0.5240(7) 0.22095(13) 0.0260(10) Uani 1 1 d . . . . .
H10 H 0.6478 0.6536 0.2117 0.031 Uiso 1 1 calc R . . . .
C11 C 1.0459(4) 0.3128(6) 0.14776(14) 0.0253(10) Uani 1 1 d . . . . .
C12 C 0.9902(4) 0.1097(6) 0.14997(14) 0.0243(9) Uani 1 1 d . . . . .
C13 C 1.0354(4) -0.0352(7) 0.11825(17) 0.0377(12) Uani 1 1 d . . . . .
H13A H 0.9972 -0.1593 0.1225 0.056 Uiso 1 1 calc GR . . . .
H13B H 1.1234 -0.0481 0.1235 0.056 Uiso 1 1 calc GR . . . .
H13C H 1.0147 0.0085 0.0883 0.056 Uiso 1 1 calc GR . . . .
C14 C 0.9995(5) 0.0260(8) 0.19577(15) 0.0401(13) Uani 1 1 d . . . . .
H14A H 0.9660 0.1169 0.2157 0.060 Uiso 1 1 calc GR . . . .
H14B H 1.0845 0.0012 0.2053 0.060 Uiso 1 1 calc GR . . . .
H14C H 0.9539 -0.0939 0.1957 0.060 Uiso 1 1 calc GR . . . .
C15 C 1.1473(4) 0.3582(8) 0.18189(14) 0.0383(11) Uani 1 1 d . . . . .
H15A H 1.1768 0.4881 0.1773 0.057 Uiso 1 1 calc GR . . . .
H15B H 1.2134 0.2668 0.1797 0.057 Uiso 1 1 calc GR . . . .
H15C H 1.1177 0.3494 0.2109 0.057 Uiso 1 1 calc GR . . . .
C16 C 1.0851(4) 0.3666(8) 0.10275(13) 0.0338(10) Uani 1 1 d . . . . .
H16A H 1.0198 0.3365 0.0804 0.051 Uiso 1 1 calc GR . . . .
H16B H 1.1576 0.2938 0.0971 0.051 Uiso 1 1 calc GR . . . .
H16C H 1.1030 0.5037 0.1020 0.051 Uiso 1 1 calc GR . . . .
C17 C 0.7711(4) 0.3375(6) 0.00507(12) 0.0220(9) Uani 1 1 d . . . . .
C18 C 0.6590(4) 0.2086(6) -0.00652(12) 0.0211(9) Uani 1 1 d . . . . .
C19 C 0.5873(4) 0.2598(8) -0.04949(13) 0.0372(12) Uani 1 1 d . . . . .
H19A H 0.5180 0.1735 -0.0544 0.056 Uiso 1 1 calc GR . . . .
H19B H 0.6395 0.2468 -0.0734 0.056 Uiso 1 1 calc GR . . . .
H19C H 0.5586 0.3920 -0.0482 0.056 Uiso 1 1 calc GR . . . .
C20 C 0.6873(4) -0.0015(6) -0.00521(15) 0.0318(11) Uani 1 1 d . . . . .
H20A H 0.7336 -0.0326 0.0224 0.048 Uiso 1 1 calc GR . . . .
H20B H 0.7350 -0.0342 -0.0295 0.048 Uiso 1 1 calc GR . . . .
H20C H 0.6118 -0.0748 -0.0077 0.048 Uiso 1 1 calc GR . . . .
C21 C 0.7570(5) 0.5408(7) -0.01125(17) 0.0389(12) Uani 1 1 d . . . . .
H21A H 0.6791 0.5918 -0.0039 0.058 Uiso 1 1 calc GR . . . .
H21B H 0.7602 0.5428 -0.0429 0.058 Uiso 1 1 calc GR . . . .
H21C H 0.8226 0.6196 0.0025 0.058 Uiso 1 1 calc GR . . . .
C22 C 0.8907(4) 0.2556(7) -0.00662(13) 0.0272(9) Uani 1 1 d . . . . .
H22A H 0.9559 0.3461 0.0019 0.041 Uiso 1 1 calc GR . . . .
H22B H 0.8872 0.2333 -0.0381 0.041 Uiso 1 1 calc GR . . . .
H22C H 0.9064 0.1344 0.0088 0.041 Uiso 1 1 calc GR . . . .
B1 B 0.8409(5) 0.3323(8) 0.14466(14) 0.0214(10) Uani 1 1 d . . . . .
B2 B 0.6605(4) 0.3089(7) 0.06352(15) 0.0190(10) Uani 1 1 d . . . . .
Br2 Br 0.39087(4) 0.86043(9) 0.16948(2) 0.04337(17) Uani 1 1 d . . . . .
O5 O 0.4077(2) 0.5968(4) 0.47125(8) 0.0214(6) Uani 1 1 d . . . . .
O6 O 0.2126(3) 0.6854(4) 0.45097(9) 0.0245(7) Uani 1 1 d . . . . .
O7 O 0.0367(3) 0.8314(4) 0.35806(9) 0.0270(7) Uani 1 1 d . . . . .
O8 O 0.1280(3) 0.5414(4) 0.35134(9) 0.0243(7) Uani 1 1 d . . . . .
C23 C 0.2715(4) 0.8342(6) 0.36304(12) 0.0194(8) Uani 1 1 d . . . . .
C24 C 0.3644(4) 0.7182(6) 0.39247(11) 0.0185(8) Uani 1 1 d . . . . .
C25 C 0.4758(4) 0.6786(7) 0.38201(14) 0.0278(10) Uani 1 1 d . . . . .
C26 C 0.2624(4) 1.0332(6) 0.38374(14) 0.0281(10) Uani 1 1 d . . . . .
H26A H 0.2444 1.0194 0.4142 0.042 Uiso 1 1 calc GR . . . .
H26B H 0.1976 1.1061 0.3677 0.042 Uiso 1 1 calc GR . . . .
H26C H 0.3393 1.1009 0.3825 0.042 Uiso 1 1 calc GR . . . .
C27 C 0.3050(3) 0.8461(7) 0.31562(12) 0.0208(8) Uani 1 1 d . . . . .
C28 C 0.3197(4) 1.0172(7) 0.29419(14) 0.0287(10) Uani 1 1 d . . . . .
H28 H 0.3115 1.1342 0.3093 0.034 Uiso 1 1 calc R . . . .
C29 C 0.3459(4) 1.0212(8) 0.25134(15) 0.0312(11) Uani 1 1 d . . . . .
H29 H 0.3563 1.1400 0.2372 0.037 Uiso 1 1 calc R . . . .
C30 C 0.3570(4) 0.8529(8) 0.22916(12) 0.0282(10) Uani 1 1 d . . . . .
C31 C 0.3444(4) 0.6801(7) 0.24908(14) 0.0268(11) Uani 1 1 d . . . . .
H31 H 0.3534 0.5644 0.2336 0.032 Uiso 1 1 calc R . . . .
C32 C 0.3181(4) 0.6768(7) 0.29227(14) 0.0241(10) Uani 1 1 d . . . . .
H32 H 0.3089 0.5573 0.3063 0.029 Uiso 1 1 calc R . . . .
C33 C 0.3370(4) 0.5453(6) 0.50763(13) 0.0218(9) Uani 1 1 d . . . . .
C34 C 0.2217(4) 0.6683(6) 0.49851(13) 0.0230(10) Uani 1 1 d . . . . .
C35 C 0.2355(5) 0.8702(7) 0.51600(15) 0.0359(11) Uani 1 1 d . . . . .
H35A H 0.3124 0.9237 0.5083 0.054 Uiso 1 1 calc GR . . . .
H35B H 0.2344 0.8683 0.5478 0.054 Uiso 1 1 calc GR . . . .
H35C H 0.1686 0.9492 0.5033 0.054 Uiso 1 1 calc GR . . . .
C36 C 0.1048(4) 0.5804(7) 0.51145(15) 0.0314(11) Uani 1 1 d . . . . .
H36A H 0.0373 0.6670 0.5032 0.047 Uiso 1 1 calc GR . . . .
H36B H 0.1109 0.5597 0.5430 0.047 Uiso 1 1 calc GR . . . .
H36C H 0.0910 0.4578 0.4965 0.047 Uiso 1 1 calc GR . . . .
C37 C 0.3131(4) 0.3319(6) 0.50402(15) 0.0308(10) Uani 1 1 d . . . . .
H37A H 0.2667 0.3043 0.4762 0.046 Uiso 1 1 calc GR . . . .
H37B H 0.2669 0.2907 0.5281 0.046 Uiso 1 1 calc GR . . . .
H37C H 0.3902 0.2630 0.5054 0.046 Uiso 1 1 calc GR . . . .
C38 C 0.4118(4) 0.5895(7) 0.54975(14) 0.0344(11) Uani 1 1 d . . . . .
H38A H 0.4844 0.5093 0.5521 0.052 Uiso 1 1 calc GR . . . .
H38B H 0.3640 0.5632 0.5744 0.052 Uiso 1 1 calc GR . . . .
H38C H 0.4353 0.7245 0.5501 0.052 Uiso 1 1 calc GR . . . .
C39 C -0.0017(4) 0.5007(7) 0.34804(14) 0.0258(9) Uani 1 1 d . . . . .
C40 C -0.0575(4) 0.7035(7) 0.34005(15) 0.0284(10) Uani 1 1 d . . . . .
C41 C -0.1710(4) 0.7392(9) 0.36172(18) 0.0469(13) Uani 1 1 d . . . . .
H41A H -0.1540 0.7286 0.3933 0.070 Uiso 1 1 calc GR . . . .
H41B H -0.2322 0.6446 0.3516 0.070 Uiso 1 1 calc GR . . . .
H41C H -0.2012 0.8679 0.3543 0.070 Uiso 1 1 calc GR . . . .
C42 C -0.0758(5) 0.7547(9) 0.29153(16) 0.0471(14) Uani 1 1 d . . . . .
H42A H -0.0933 0.8916 0.2884 0.071 Uiso 1 1 calc GR . . . .
H42B H -0.1437 0.6809 0.2777 0.071 Uiso 1 1 calc GR . . . .
H42C H -0.0022 0.7243 0.2775 0.071 Uiso 1 1 calc GR . . . .
C43 C -0.0282(4) 0.4141(8) 0.39144(16) 0.0401(13) Uani 1 1 d . . . . .
H43A H 0.0227 0.3010 0.3973 0.060 Uiso 1 1 calc GR . . . .
H43B H -0.1136 0.3771 0.3903 0.060 Uiso 1 1 calc GR . . . .
H43C H -0.0108 0.5084 0.4146 0.060 Uiso 1 1 calc GR . . . .
C44 C -0.0290(4) 0.3571(8) 0.31168(16) 0.0399(12) Uani 1 1 d . . . . .
H44A H 0.0018 0.4052 0.2849 0.060 Uiso 1 1 calc GR . . . .
H44B H -0.1166 0.3381 0.3069 0.060 Uiso 1 1 calc GR . . . .
H44C H 0.0102 0.2351 0.3197 0.060 Uiso 1 1 calc GR . . . .
B3 B 0.3280(4) 0.6636(7) 0.43840(15) 0.0199(10) Uani 1 1 d . . . . .
B4 B 0.1424(4) 0.7314(8) 0.35934(13) 0.0206(10) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C8 1.901(4) . ?
O1 C11 1.457(5) . ?
O1 B1 1.372(6) . ?
O2 C12 1.452(5) . ?
O2 B1 1.360(6) . ?
O3 C17 1.470(4) . ?
O3 B2 1.358(5) . ?
O4 C18 1.459(5) . ?
O4 B2 1.368(5) . ?
C1 C2 1.536(6) . ?
C1 C4 1.554(6) . ?
C1 C5 1.525(5) . ?
C1 B1 1.593(6) . ?
C2 C3 1.338(6) . ?
C2 B2 1.568(6) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.404(6) . ?
C5 C10 1.393(6) . ?
C6 H6 0.9500 . ?
C6 C7 1.380(6) . ?
C7 H7 0.9500 . ?
C7 C8 1.377(6) . ?
C8 C9 1.379(7) . ?
C9 H9 0.9500 . ?
C9 C10 1.388(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.553(6) . ?
C11 C15 1.508(6) . ?
C11 C16 1.536(6) . ?
C12 C13 1.523(6) . ?
C12 C14 1.524(6) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.553(6) . ?
C17 C21 1.512(6) . ?
C17 C22 1.519(6) . ?
C18 C19 1.528(5) . ?
C18 C20 1.503(6) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
Br2 C30 1.910(4) . ?
O5 C33 1.467(5) . ?
O5 B3 1.368(5) . ?
O6 C34 1.465(5) . ?
O6 B3 1.378(6) . ?
O7 C40 1.450(5) . ?
O7 B4 1.363(6) . ?
O8 C39 1.463(5) . ?
O8 B4 1.358(7) . ?
C23 C24 1.544(6) . ?
C23 C26 1.538(6) . ?
C23 C27 1.542(5) . ?
C23 B4 1.598(6) . ?
C24 C25 1.334(6) . ?
C24 B3 1.553(6) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 C28 1.383(6) . ?
C27 C32 1.401(6) . ?
C28 H28 0.9500 . ?
C28 C29 1.377(6) . ?
C29 H29 0.9500 . ?
C29 C30 1.372(7) . ?
C30 C31 1.368(7) . ?
C31 H31 0.9500 . ?
C31 C32 1.387(6) . ?
C32 H32 0.9500 . ?
C33 C34 1.548(6) . ?
C33 C37 1.519(6) . ?
C33 C38 1.512(6) . ?
C34 C35 1.515(7) . ?
C34 C36 1.520(6) . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 C40 1.559(7) . ?
C39 C43 1.520(6) . ?
C39 C44 1.516(6) . ?
C40 C41 1.497(6) . ?
C40 C42 1.534(6) . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 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
B1 O1 C11 106.9(3) . . ?
B1 O2 C12 107.6(3) . . ?
B2 O3 C17 107.0(3) . . ?
B2 O4 C18 106.6(3) . . ?
C2 C1 C4 107.0(3) . . ?
C2 C1 B1 111.6(3) . . ?
C4 C1 B1 108.8(4) . . ?
C5 C1 C2 112.5(4) . . ?
C5 C1 C4 112.6(4) . . ?
C5 C1 B1 104.3(3) . . ?
C1 C2 B2 118.3(4) . . ?
C3 C2 C1 122.2(4) . . ?
C3 C2 B2 119.3(4) . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C1 119.3(4) . . ?
C10 C5 C1 123.3(4) . . ?
C10 C5 C6 117.3(4) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 C5 121.4(4) . . ?
C7 C6 H6 119.3 . . ?
C6 C7 H7 120.1 . . ?
C8 C7 C6 119.9(4) . . ?
C8 C7 H7 120.1 . . ?
C7 C8 Br1 120.1(4) . . ?
C7 C8 C9 120.1(4) . . ?
C9 C8 Br1 119.7(3) . . ?
C8 C9 H9 120.0 . . ?
C8 C9 C10 120.0(4) . . ?
C10 C9 H9 120.0 . . ?
C5 C10 H10 119.4 . . ?
C9 C10 C5 121.2(4) . . ?
C9 C10 H10 119.4 . . ?
O1 C11 C12 102.9(3) . . ?
O1 C11 C15 108.4(4) . . ?
O1 C11 C16 105.5(4) . . ?
C15 C11 C12 116.0(4) . . ?
C15 C11 C16 109.0(4) . . ?
C16 C11 C12 114.1(4) . . ?
O2 C12 C11 102.7(3) . . ?
O2 C12 C13 108.0(3) . . ?
O2 C12 C14 107.0(4) . . ?
C13 C12 C11 115.2(4) . . ?
C13 C12 C14 109.8(4) . . ?
C14 C12 C11 113.4(4) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C11 C16 H16A 109.5 . . ?
C11 C16 H16B 109.5 . . ?
C11 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O3 C17 C18 102.0(3) . . ?
O3 C17 C21 106.0(4) . . ?
O3 C17 C22 108.2(3) . . ?
C21 C17 C18 114.3(4) . . ?
C21 C17 C22 110.1(4) . . ?
C22 C17 C18 115.2(4) . . ?
O4 C18 C17 102.5(3) . . ?
O4 C18 C19 108.9(3) . . ?
O4 C18 C20 106.9(3) . . ?
C19 C18 C17 114.2(4) . . ?
C20 C18 C17 113.6(4) . . ?
C20 C18 C19 110.2(4) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C17 C21 H21A 109.5 . . ?
C17 C21 H21B 109.5 . . ?
C17 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C17 C22 H22A 109.5 . . ?
C17 C22 H22B 109.5 . . ?
C17 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O1 B1 C1 122.3(4) . . ?
O2 B1 O1 113.4(4) . . ?
O2 B1 C1 124.1(4) . . ?
O3 B2 O4 113.7(4) . . ?
O3 B2 C2 123.5(4) . . ?
O4 B2 C2 122.8(4) . . ?
B3 O5 C33 107.2(3) . . ?
B3 O6 C34 106.7(3) . . ?
B4 O7 C40 106.5(4) . . ?
B4 O8 C39 107.6(3) . . ?
C24 C23 B4 110.8(4) . . ?
C26 C23 C24 107.2(3) . . ?
C26 C23 B4 110.3(4) . . ?
C27 C23 C24 112.5(3) . . ?
C27 C23 C26 112.0(4) . . ?
C27 C23 B4 104.2(3) . . ?
C23 C24 B3 116.8(3) . . ?
C25 C24 C23 123.6(4) . . ?
C25 C24 B3 119.3(4) . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C28 C27 C23 123.2(4) . . ?
C28 C27 C32 117.7(4) . . ?
C32 C27 C23 119.1(4) . . ?
C27 C28 H28 119.4 . . ?
C29 C28 C27 121.3(5) . . ?
C29 C28 H28 119.4 . . ?
C28 C29 H29 120.1 . . ?
C30 C29 C28 119.7(4) . . ?
C30 C29 H29 120.1 . . ?
C29 C30 Br2 119.3(4) . . ?
C29 C30 C31 121.1(4) . . ?
C31 C30 Br2 119.5(4) . . ?
C30 C31 H31 120.5 . . ?
C30 C31 C32 118.9(4) . . ?
C32 C31 H31 120.5 . . ?
C27 C32 H32 119.4 . . ?
C31 C32 C27 121.2(4) . . ?
C31 C32 H32 119.4 . . ?
O5 C33 C34 102.3(3) . . ?
O5 C33 C37 106.7(3) . . ?
O5 C33 C38 108.5(4) . . ?
C37 C33 C34 113.3(4) . . ?
C38 C33 C34 115.3(4) . . ?
C38 C33 C37 110.1(4) . . ?
O6 C34 C33 102.2(3) . . ?
O6 C34 C35 106.0(3) . . ?
O6 C34 C36 108.0(3) . . ?
C35 C34 C33 113.4(4) . . ?
C35 C34 C36 110.2(4) . . ?
C36 C34 C33 116.0(4) . . ?
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 . . ?
C34 C36 H36A 109.5 . . ?
C34 C36 H36B 109.5 . . ?
C34 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C33 C37 H37A 109.5 . . ?
C33 C37 H37B 109.5 . . ?
C33 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C33 C38 H38A 109.5 . . ?
C33 C38 H38B 109.5 . . ?
C33 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
O8 C39 C40 102.1(3) . . ?
O8 C39 C43 106.3(3) . . ?
O8 C39 C44 108.2(4) . . ?
C43 C39 C40 113.4(4) . . ?
C43 C39 C44 110.2(4) . . ?
C44 C39 C40 115.8(4) . . ?
O7 C40 C39 103.8(3) . . ?
O7 C40 C41 109.5(4) . . ?
O7 C40 C42 105.1(4) . . ?
C41 C40 C39 114.8(4) . . ?
C41 C40 C42 110.4(4) . . ?
C42 C40 C39 112.6(4) . . ?
C40 C41 H41A 109.5 . . ?
C40 C41 H41B 109.5 . . ?
C40 C41 H41C 109.5 . . ?
H41A C41 H41B 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C40 C42 H42A 109.5 . . ?
C40 C42 H42B 109.5 . . ?
C40 C42 H42C 109.5 . . ?
H42A C42 H42B 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C39 C43 H43A 109.5 . . ?
C39 C43 H43B 109.5 . . ?
C39 C43 H43C 109.5 . . ?
H43A C43 H43B 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C39 C44 H44A 109.5 . . ?
C39 C44 H44B 109.5 . . ?
C39 C44 H44C 109.5 . . ?
H44A C44 H44B 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
O5 B3 O6 112.8(4) . . ?
O5 B3 C24 123.8(4) . . ?
O6 B3 C24 123.4(4) . . ?
O7 B4 C23 122.3(4) . . ?
O8 B4 O7 114.2(4) . . ?
O8 B4 C23 122.9(4) . . ?

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 C8 C9 C10 177.1(3) . . . . ?
O1 C11 C12 O2 25.1(4) . . . . ?
O1 C11 C12 C13 142.3(4) . . . . ?
O1 C11 C12 C14 -90.0(4) . . . . ?
O3 C17 C18 O4 27.8(4) . . . . ?
O3 C17 C18 C19 145.4(4) . . . . ?
O3 C17 C18 C20 -87.1(4) . . . . ?
C1 C2 B2 O3 5.0(6) . . . . ?
C1 C2 B2 O4 -174.3(4) . . . . ?
C1 C5 C6 C7 176.2(4) . . . . ?
C1 C5 C10 C9 -176.2(4) . . . . ?
C2 C1 C5 C6 63.5(5) . . . . ?
C2 C1 C5 C10 -119.2(4) . . . . ?
C2 C1 B1 O1 146.2(4) . . . . ?
C2 C1 B1 O2 -39.6(5) . . . . ?
C3 C2 B2 O3 -179.3(4) . . . . ?
C3 C2 B2 O4 1.4(7) . . . . ?
C4 C1 C2 C3 -101.9(5) . . . . ?
C4 C1 C2 B2 73.7(5) . . . . ?
C4 C1 C5 C6 -175.4(4) . . . . ?
C4 C1 C5 C10 1.8(6) . . . . ?
C4 C1 B1 O1 28.3(5) . . . . ?
C4 C1 B1 O2 -157.5(4) . . . . ?
C5 C1 C2 C3 22.3(6) . . . . ?
C5 C1 C2 B2 -162.1(4) . . . . ?
C5 C1 B1 O1 -92.1(4) . . . . ?
C5 C1 B1 O2 82.1(5) . . . . ?
C5 C6 C7 C8 -0.1(7) . . . . ?
C6 C5 C10 C9 1.1(6) . . . . ?
C6 C7 C8 Br1 -177.3(3) . . . . ?
C6 C7 C8 C9 1.8(7) . . . . ?
C7 C8 C9 C10 -2.0(7) . . . . ?
C8 C9 C10 C5 0.5(7) . . . . ?
C10 C5 C6 C7 -1.3(6) . . . . ?
C11 O1 B1 O2 8.3(5) . . . . ?
C11 O1 B1 C1 -176.9(4) . . . . ?
C12 O2 B1 O1 9.0(5) . . . . ?
C12 O2 B1 C1 -165.7(4) . . . . ?
C15 C11 C12 O2 143.3(4) . . . . ?
C15 C11 C12 C13 -99.5(5) . . . . ?
C15 C11 C12 C14 28.3(5) . . . . ?
C16 C11 C12 O2 -88.7(4) . . . . ?
C16 C11 C12 C13 28.5(5) . . . . ?
C16 C11 C12 C14 156.3(4) . . . . ?
C17 O3 B2 O4 8.3(5) . . . . ?
C17 O3 B2 C2 -171.1(4) . . . . ?
C18 O4 B2 O3 11.0(5) . . . . ?
C18 O4 B2 C2 -169.7(4) . . . . ?
C21 C17 C18 O4 -86.1(4) . . . . ?
C21 C17 C18 C19 31.4(5) . . . . ?
C21 C17 C18 C20 158.9(4) . . . . ?
C22 C17 C18 O4 144.8(3) . . . . ?
C22 C17 C18 C19 -97.6(4) . . . . ?
C22 C17 C18 C20 29.9(5) . . . . ?
B1 O1 C11 C12 -20.6(4) . . . . ?
B1 O1 C11 C15 -144.0(4) . . . . ?
B1 O1 C11 C16 99.3(4) . . . . ?
B1 O2 C12 C11 -21.0(4) . . . . ?
B1 O2 C12 C13 -143.2(4) . . . . ?
B1 O2 C12 C14 98.6(4) . . . . ?
B1 C1 C2 C3 139.1(5) . . . . ?
B1 C1 C2 B2 -45.2(5) . . . . ?
B1 C1 C5 C6 -57.6(5) . . . . ?
B1 C1 C5 C10 119.7(4) . . . . ?
B2 O3 C17 C18 -22.3(4) . . . . ?
B2 O3 C17 C21 97.6(4) . . . . ?
B2 O3 C17 C22 -144.3(4) . . . . ?
B2 O4 C18 C17 -24.0(4) . . . . ?
B2 O4 C18 C19 -145.3(4) . . . . ?
B2 O4 C18 C20 95.7(4) . . . . ?
Br2 C30 C31 C32 -179.1(3) . . . . ?
O5 C33 C34 O6 29.1(4) . . . . ?
O5 C33 C34 C35 -84.5(4) . . . . ?
O5 C33 C34 C36 146.4(4) . . . . ?
O8 C39 C40 O7 -23.7(4) . . . . ?
O8 C39 C40 C41 -143.1(4) . . . . ?
O8 C39 C40 C42 89.3(4) . . . . ?
C23 C24 B3 O5 -166.1(4) . . . . ?
C23 C24 B3 O6 11.0(6) . . . . ?
C23 C27 C28 C29 -177.9(4) . . . . ?
C23 C27 C32 C31 177.9(4) . . . . ?
C24 C23 C27 C28 -123.4(4) . . . . ?
C24 C23 C27 C32 58.5(5) . . . . ?
C24 C23 B4 O7 142.4(4) . . . . ?
C24 C23 B4 O8 -46.7(5) . . . . ?
C25 C24 B3 O5 8.1(6) . . . . ?
C25 C24 B3 O6 -174.9(4) . . . . ?
C26 C23 C24 C25 -106.0(5) . . . . ?
C26 C23 C24 B3 67.9(5) . . . . ?
C26 C23 C27 C28 -2.6(5) . . . . ?
C26 C23 C27 C32 179.3(4) . . . . ?
C26 C23 B4 O7 23.9(5) . . . . ?
C26 C23 B4 O8 -165.2(4) . . . . ?
C27 C23 C24 C25 17.5(6) . . . . ?
C27 C23 C24 B3 -168.6(4) . . . . ?
C27 C23 B4 O7 -96.4(4) . . . . ?
C27 C23 B4 O8 74.5(5) . . . . ?
C27 C28 C29 C30 0.5(7) . . . . ?
C28 C27 C32 C31 -0.3(6) . . . . ?
C28 C29 C30 Br2 179.0(3) . . . . ?
C28 C29 C30 C31 -1.1(7) . . . . ?
C29 C30 C31 C32 1.0(6) . . . . ?
C30 C31 C32 C27 -0.3(7) . . . . ?
C32 C27 C28 C29 0.2(6) . . . . ?
C33 O5 B3 O6 7.8(5) . . . . ?
C33 O5 B3 C24 -174.8(4) . . . . ?
C34 O6 B3 O5 12.2(5) . . . . ?
C34 O6 B3 C24 -165.2(4) . . . . ?
C37 C33 C34 O6 -85.3(4) . . . . ?
C37 C33 C34 C35 161.0(4) . . . . ?
C37 C33 C34 C36 31.9(5) . . . . ?
C38 C33 C34 O6 146.6(4) . . . . ?
C38 C33 C34 C35 32.9(5) . . . . ?
C38 C33 C34 C36 -96.2(5) . . . . ?
C39 O8 B4 O7 -5.7(5) . . . . ?
C39 O8 B4 C23 -177.2(3) . . . . ?
C40 O7 B4 O8 -10.7(4) . . . . ?
C40 O7 B4 C23 160.9(3) . . . . ?
C43 C39 C40 O7 90.1(4) . . . . ?
C43 C39 C40 C41 -29.3(5) . . . . ?
C43 C39 C40 C42 -156.8(4) . . . . ?
C44 C39 C40 O7 -141.0(4) . . . . ?
C44 C39 C40 C41 99.6(5) . . . . ?
C44 C39 C40 C42 -28.0(6) . . . . ?
B3 O5 C33 C34 -23.0(4) . . . . ?
B3 O5 C33 C37 96.2(4) . . . . ?
B3 O5 C33 C38 -145.3(4) . . . . ?
B3 O6 C34 C33 -25.5(4) . . . . ?
B3 O6 C34 C35 93.5(4) . . . . ?
B3 O6 C34 C36 -148.4(4) . . . . ?
B4 O7 C40 C39 21.2(4) . . . . ?
B4 O7 C40 C41 144.2(4) . . . . ?
B4 O7 C40 C42 -97.2(4) . . . . ?
B4 O8 C39 C40 18.1(4) . . . . ?
B4 O8 C39 C43 -100.9(4) . . . . ?
B4 O8 C39 C44 140.7(4) . . . . ?
B4 C23 C24 C25 133.6(4) . . . . ?
B4 C23 C24 B3 -52.5(5) . . . . ?
B4 C23 C27 C28 116.5(4) . . . . ?
B4 C23 C27 C32 -61.5(5) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
