# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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. 
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data_mx4333
_database_code_depnum_ccdc_archive 'CCDC 1465234'
_audit_update_record             
;
2016-03-14 deposited with the CCDC.
2016-07-13 downloaded from the CCDC.
;
_audit_creation_date             2015-12-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C31 H29 Br2 N O4'
_chemical_formula_sum            'C31 H29 Br2 N O4'
_chemical_formula_weight         639.37
_chemical_absolute_configuration ad
_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'
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      tetragonal
_space_group_IT_number           78
_space_group_name_H-M_alt        'P 43'
_space_group_name_Hall           'P 4cw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x, z+3/4'
'y, -x, z+1/4'

_cell_length_a                   12.3390(3)
_cell_length_b                   12.3390(7)
_cell_length_c                   18.0683(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2750.92(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7783
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4849
_cell_measurement_theta_min      1.6504
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.984
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6689
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.13
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17959
_diffrn_reflns_point_group_measured_fraction_full 0.925
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         1.650
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
scan:
	Number of images: 330
	           Slice: -110.0000 - 55.0000
	     Image width: 0.5000
	        Exp time: 7.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 44.9862
	          2theta: -20.1552
scan:
	Number of images: 240
	           Slice: -110.0000 - 10.0000
	     Image width: 0.5000
	        Exp time: 7.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 44.9862
	          2theta: -20.1552
;
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_number_total             3268
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0236
_diffrn_orient_matrix_UB_12      0.0722
_diffrn_orient_matrix_UB_13      0.0281
_diffrn_orient_matrix_UB_21      -0.0394
_diffrn_orient_matrix_UB_22      0.0142
_diffrn_orient_matrix_UB_23      -0.0694
_diffrn_orient_matrix_UB_31      -0.0456
_diffrn_orient_matrix_UB_32      -0.0231
_diffrn_orient_matrix_UB_33      0.0211
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.793
_reflns_Friedel_fraction_full    0.846
_reflns_Friedel_fraction_max     0.843
_reflns_number_gt                5363
_reflns_number_total             5824
_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       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution    
;
'SHELXT (Sheldrick, 2014)'
;
_refine_diff_density_max         0.754
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details 
;
 Flack x determined using 1865 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.008(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     348
_refine_ls_number_reflns         5824
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0534
_refine_ls_restrained_S_all      1.056
_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)+(0.0597P)²+3.0122P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1270
_refine_ls_wR_factor_ref         0.1321
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C7(H7A,H7B), C8(H8A,H8B), C25(H25A,H25B), C26(H26A,
 H26B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C23(H23)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C30(H30A,H30B,
 H30C), C31(H31A,H31B,H31C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 -0.09202(6) 0.65136(6) 0.19108(5) 0.0545(2) Uani 1 1 d . . . . .
Br2 Br 0.57110(7) 0.51672(8) 0.35461(6) 0.0699(3) Uani 1 1 d . . . . .
O1 O -0.2054(5) 0.1996(6) 0.6040(4) 0.0701(18) Uani 1 1 d . . . . .
O2 O 0.1187(6) 0.0273(5) 0.6226(4) 0.077(2) Uani 1 1 d . . . . .
O3 O 0.0857(4) 0.4822(4) 0.1907(3) 0.0435(10) Uani 1 1 d . . . . .
O4 O 0.3709(5) 0.6369(4) 0.4127(3) 0.0515(13) Uani 1 1 d . . . . .
N1 N -0.0540(6) 0.0970(7) 0.6248(4) 0.069(2) Uani 1 1 d . . . . .
C1 C -0.1930(9) 0.0227(9) 0.8105(7) 0.084(3) Uani 1 1 d . . . . .
H1A H -0.2640 0.0068 0.7915 0.126 Uiso 1 1 calc GR . . . .
H1B H -0.1996 0.0597 0.8570 0.126 Uiso 1 1 calc GR . . . .
H1C H -0.1538 -0.0437 0.8175 0.126 Uiso 1 1 calc GR . . . .
C2 C -0.1324(9) 0.0945(8) 0.7557(6) 0.072(3) Uani 1 1 d . . . . .
H2A H -0.0653 0.1193 0.7778 0.087 Uiso 1 1 calc R . . . .
H2B H -0.1761 0.1576 0.7441 0.087 Uiso 1 1 calc R . . . .
C3 C -0.1070(8) 0.0309(9) 0.6831(6) 0.072(3) Uani 1 1 d . . . . .
H3A H -0.0602 -0.0299 0.6951 0.086 Uiso 1 1 calc R . . . .
H3B H -0.1741 0.0017 0.6635 0.086 Uiso 1 1 calc R . . . .
C4 C -0.1119(7) 0.1780(7) 0.5910(4) 0.055(2) Uani 1 1 d . . . . .
C5 C -0.0343(6) 0.2320(6) 0.5387(4) 0.0417(15) Uani 1 1 d . . . . .
C6 C -0.0507(5) 0.3137(6) 0.4899(4) 0.0399(15) Uani 1 1 d . . . . .
C7 C -0.1586(5) 0.3703(6) 0.4804(4) 0.0431(15) Uani 1 1 d . . . . .
H7A H -0.2015 0.3631 0.5252 0.052 Uiso 1 1 calc R . . . .
H7B H -0.1986 0.3379 0.4398 0.052 Uiso 1 1 calc R . . . .
C8 C -0.1373(6) 0.4895(6) 0.4644(4) 0.0484(17) Uani 1 1 d . . . . .
H8A H -0.2054 0.5280 0.4586 0.058 Uiso 1 1 calc R . . . .
H8B H -0.0975 0.5221 0.5049 0.058 Uiso 1 1 calc R . . . .
C9 C -0.0722(5) 0.4961(5) 0.3941(4) 0.0363(13) Uani 1 1 d . . . . .
C10 C -0.1025(5) 0.5641(5) 0.3362(4) 0.0420(15) Uani 1 1 d . . . . .
H10 H -0.1610 0.6110 0.3419 0.050 Uiso 1 1 calc R . . . .
C11 C -0.0465(5) 0.5620(5) 0.2713(4) 0.0398(14) Uani 1 1 d . . . . .
C12 C 0.0369(5) 0.4884(5) 0.2595(4) 0.0370(13) Uani 1 1 d . . . . .
C13 C 0.0671(5) 0.4161(5) 0.3156(3) 0.0319(12) Uani 1 1 d . . . . .
C14 C 0.0155(5) 0.4236(5) 0.3845(4) 0.0310(12) Uani 1 1 d . . . . .
C15 C 0.0394(5) 0.3500(5) 0.4480(3) 0.0318(12) Uani 1 1 d . . . . .
C16 C 0.1793(6) 0.5508(7) 0.1853(5) 0.0552(19) Uani 1 1 d . . . . .
H16A H 0.2120 0.5421 0.1375 0.083 Uiso 1 1 calc GR . . . .
H16B H 0.2305 0.5313 0.2230 0.083 Uiso 1 1 calc GR . . . .
H16C H 0.1579 0.6250 0.1919 0.083 Uiso 1 1 calc GR . . . .
C17 C 0.1449(6) 0.3265(5) 0.2936(4) 0.0374(13) Uani 1 1 d . . . . .
H17A H 0.1282 0.3024 0.2444 0.056 Uiso 1 1 calc GR . . . .
H17B H 0.1379 0.2670 0.3275 0.056 Uiso 1 1 calc GR . . . .
H17C H 0.2178 0.3535 0.2950 0.056 Uiso 1 1 calc GR . . . .
C18 C 0.1450(5) 0.3146(5) 0.4664(3) 0.0310(12) Uani 1 1 d . . . . .
C19 C 0.2467(5) 0.3694(5) 0.4419(4) 0.0332(12) Uani 1 1 d . . . . .
C20 C 0.2581(5) 0.4836(5) 0.4403(4) 0.0364(12) Uani 1 1 d . . . . .
C21 C 0.3558(5) 0.5251(5) 0.4129(4) 0.0404(14) Uani 1 1 d . . . . .
C22 C 0.4398(5) 0.4573(6) 0.3912(4) 0.0439(15) Uani 1 1 d . . . . .
C23 C 0.4309(5) 0.3461(6) 0.3990(4) 0.0442(16) Uani 1 1 d . . . . .
H23 H 0.4890 0.3014 0.3869 0.053 Uiso 1 1 calc R . . . .
C24 C 0.3353(5) 0.3017(5) 0.4248(4) 0.0374(14) Uani 1 1 d . . . . .
C25 C 0.3239(6) 0.1828(5) 0.4399(5) 0.0458(15) Uani 1 1 d . . . . .
H25A H 0.3947 0.1486 0.4408 0.055 Uiso 1 1 calc R . . . .
H25B H 0.2809 0.1487 0.4015 0.055 Uiso 1 1 calc R . . . .
C26 C 0.2678(6) 0.1693(6) 0.5156(4) 0.0494(18) Uani 1 1 d . . . . .
H26A H 0.2604 0.0930 0.5274 0.059 Uiso 1 1 calc R . . . .
H26B H 0.3109 0.2034 0.5540 0.059 Uiso 1 1 calc R . . . .
C27 C 0.1578(6) 0.2218(5) 0.5117(4) 0.0396(14) Uani 1 1 d . . . . .
C28 C 0.0678(6) 0.1828(6) 0.5470(4) 0.0416(15) Uani 1 1 d . . . . .
C29 C 0.0539(7) 0.0923(7) 0.6006(5) 0.060(2) Uani 1 1 d . . . . .
C30 C 0.1752(5) 0.5614(6) 0.4725(5) 0.0447(15) Uani 1 1 d . . . . .
H30A H 0.1337 0.5931 0.4332 0.067 Uiso 1 1 calc GR . . . .
H30B H 0.2119 0.6176 0.4995 0.067 Uiso 1 1 calc GR . . . .
H30C H 0.1278 0.5228 0.5053 0.067 Uiso 1 1 calc GR . . . .
C31 C 0.3287(10) 0.6872(8) 0.3483(6) 0.078(3) Uani 1 1 d . . . . .
H31A H 0.3681 0.6625 0.3057 0.118 Uiso 1 1 calc GR . . . .
H31B H 0.3359 0.7644 0.3526 0.118 Uiso 1 1 calc GR . . . .
H31C H 0.2536 0.6686 0.3429 0.118 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 C11 1.906(7) . ?
Br2 C22 1.897(7) . ?
O1 C4 1.207(11) . ?
O2 C29 1.201(11) . ?
O3 C12 1.383(8) . ?
O3 C16 1.435(9) . ?
O4 C21 1.392(8) . ?
O4 C31 1.418(11) . ?
N1 C3 1.485(11) . ?
N1 C4 1.371(12) . ?
N1 C29 1.402(12) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.525(13) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.560(15) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.502(10) . ?
C5 C6 1.355(10) . ?
C5 C28 1.406(10) . ?
C6 C7 1.514(10) . ?
C6 C15 1.417(9) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.521(11) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.505(10) . ?
C9 C10 1.392(10) . ?
C9 C14 1.415(8) . ?
C10 H10 0.9300 . ?
C10 C11 1.361(10) . ?
C11 C12 1.390(9) . ?
C12 C13 1.401(9) . ?
C13 C14 1.401(9) . ?
C13 C17 1.517(8) . ?
C14 C15 1.493(9) . ?
C15 C18 1.414(8) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.492(8) . ?
C18 C27 1.417(9) . ?
C19 C20 1.416(8) . ?
C19 C24 1.410(8) . ?
C20 C21 1.401(9) . ?
C20 C30 1.519(9) . ?
C21 C22 1.389(10) . ?
C22 C23 1.384(10) . ?
C23 H23 0.9300 . ?
C23 C24 1.382(10) . ?
C24 C25 1.499(9) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 C26 1.541(11) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C26 C27 1.505(10) . ?
C27 C28 1.368(10) . ?
C28 C29 1.488(10) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 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
C12 O3 C16 112.2(6) . . ?
C21 O4 C31 112.7(6) . . ?
C4 N1 C3 119.1(8) . . ?
C4 N1 C29 112.7(7) . . ?
C29 N1 C3 128.0(8) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 C3 110.7(8) . . ?
H2A C2 H2B 108.1 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
N1 C3 C2 114.1(8) . . ?
N1 C3 H3A 108.7 . . ?
N1 C3 H3B 108.7 . . ?
C2 C3 H3A 108.7 . . ?
C2 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
O1 C4 N1 125.0(8) . . ?
O1 C4 C5 129.3(8) . . ?
N1 C4 C5 105.7(7) . . ?
C6 C5 C4 130.1(7) . . ?
C6 C5 C28 121.7(6) . . ?
C28 C5 C4 108.2(6) . . ?
C5 C6 C7 123.3(6) . . ?
C5 C6 C15 117.7(6) . . ?
C15 C6 C7 119.0(6) . . ?
C6 C7 H7A 110.0 . . ?
C6 C7 H7B 110.0 . . ?
C6 C7 C8 108.4(6) . . ?
H7A C7 H7B 108.4 . . ?
C8 C7 H7A 110.0 . . ?
C8 C7 H7B 110.0 . . ?
C7 C8 H8A 110.2 . . ?
C7 C8 H8B 110.2 . . ?
H8A C8 H8B 108.5 . . ?
C9 C8 C7 107.8(6) . . ?
C9 C8 H8A 110.2 . . ?
C9 C8 H8B 110.2 . . ?
C10 C9 C8 121.5(6) . . ?
C10 C9 C14 119.7(6) . . ?
C14 C9 C8 118.5(6) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 119.9(6) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 Br1 119.6(5) . . ?
C10 C11 C12 121.4(6) . . ?
C12 C11 Br1 118.7(5) . . ?
O3 C12 C11 119.8(6) . . ?
O3 C12 C13 120.0(6) . . ?
C11 C12 C13 120.1(6) . . ?
C12 C13 C14 118.7(6) . . ?
C12 C13 C17 116.2(6) . . ?
C14 C13 C17 124.6(5) . . ?
C9 C14 C15 116.2(6) . . ?
C13 C14 C9 119.9(6) . . ?
C13 C14 C15 123.6(5) . . ?
C6 C15 C14 116.6(5) . . ?
C18 C15 C6 120.1(6) . . ?
C18 C15 C14 123.4(5) . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C17 H17A 109.5 . . ?
C13 C17 H17B 109.5 . . ?
C13 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 C19 124.4(5) . . ?
C15 C18 C27 119.2(6) . . ?
C27 C18 C19 116.4(5) . . ?
C20 C19 C18 122.7(5) . . ?
C24 C19 C18 116.6(5) . . ?
C24 C19 C20 120.5(6) . . ?
C19 C20 C30 123.6(6) . . ?
C21 C20 C19 117.2(6) . . ?
C21 C20 C30 118.9(6) . . ?
O4 C21 C20 118.6(6) . . ?
C22 C21 O4 119.8(6) . . ?
C22 C21 C20 121.4(6) . . ?
C21 C22 Br2 120.2(5) . . ?
C23 C22 Br2 119.1(5) . . ?
C23 C22 C21 120.6(6) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 C22 119.7(6) . . ?
C24 C23 H23 120.1 . . ?
C19 C24 C25 117.9(6) . . ?
C23 C24 C19 120.1(6) . . ?
C23 C24 C25 122.0(6) . . ?
C24 C25 H25A 110.1 . . ?
C24 C25 H25B 110.1 . . ?
C24 C25 C26 108.0(6) . . ?
H25A C25 H25B 108.4 . . ?
C26 C25 H25A 110.1 . . ?
C26 C25 H25B 110.1 . . ?
C25 C26 H26A 110.0 . . ?
C25 C26 H26B 110.0 . . ?
H26A C26 H26B 108.4 . . ?
C27 C26 C25 108.5(6) . . ?
C27 C26 H26A 110.0 . . ?
C27 C26 H26B 110.0 . . ?
C18 C27 C26 118.3(6) . . ?
C28 C27 C18 117.6(6) . . ?
C28 C27 C26 124.0(6) . . ?
C5 C28 C29 106.9(7) . . ?
C27 C28 C5 121.7(6) . . ?
C27 C28 C29 131.3(7) . . ?
O2 C29 N1 123.9(8) . . ?
O2 C29 C28 129.8(9) . . ?
N1 C29 C28 106.3(7) . . ?
C20 C30 H30A 109.5 . . ?
C20 C30 H30B 109.5 . . ?
C20 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
O4 C31 H31A 109.5 . . ?
O4 C31 H31B 109.5 . . ?
O4 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 C11 C12 O3 0.7(8) . . . . ?
Br1 C11 C12 C13 -175.4(5) . . . . ?
Br2 C22 C23 C24 -179.3(5) . . . . ?
O1 C4 C5 C6 -4.5(14) . . . . ?
O1 C4 C5 C28 175.6(8) . . . . ?
O3 C12 C13 C14 -179.3(6) . . . . ?
O3 C12 C13 C17 -6.3(9) . . . . ?
O4 C21 C22 Br2 -4.6(9) . . . . ?
O4 C21 C22 C23 172.5(7) . . . . ?
N1 C4 C5 C6 177.1(8) . . . . ?
N1 C4 C5 C28 -2.8(8) . . . . ?
C1 C2 C3 N1 176.4(9) . . . . ?
C3 N1 C4 O1 -1.4(13) . . . . ?
C3 N1 C4 C5 177.1(8) . . . . ?
C3 N1 C29 O2 4.1(16) . . . . ?
C3 N1 C29 C28 -174.4(9) . . . . ?
C4 N1 C3 C2 -68.1(11) . . . . ?
C4 N1 C29 O2 -179.6(9) . . . . ?
C4 N1 C29 C28 1.9(10) . . . . ?
C4 C5 C6 C7 1.4(12) . . . . ?
C4 C5 C6 C15 178.9(7) . . . . ?
C4 C5 C28 C27 -173.5(6) . . . . ?
C4 C5 C28 C29 3.9(8) . . . . ?
C5 C6 C7 C8 144.3(7) . . . . ?
C5 C6 C15 C14 168.0(6) . . . . ?
C5 C6 C15 C18 -10.7(9) . . . . ?
C5 C28 C29 O2 178.0(9) . . . . ?
C5 C28 C29 N1 -3.6(9) . . . . ?
C6 C5 C28 C27 6.6(11) . . . . ?
C6 C5 C28 C29 -176.0(7) . . . . ?
C6 C7 C8 C9 60.4(7) . . . . ?
C6 C15 C18 C19 -161.7(6) . . . . ?
C6 C15 C18 C27 17.5(9) . . . . ?
C7 C6 C15 C14 -14.4(9) . . . . ?
C7 C6 C15 C18 166.9(6) . . . . ?
C7 C8 C9 C10 129.8(7) . . . . ?
C7 C8 C9 C14 -44.1(8) . . . . ?
C8 C9 C10 C11 -175.0(6) . . . . ?
C8 C9 C14 C13 170.2(6) . . . . ?
C8 C9 C14 C15 -3.3(8) . . . . ?
C9 C10 C11 Br1 177.6(5) . . . . ?
C9 C10 C11 C12 3.9(10) . . . . ?
C9 C14 C15 C6 34.2(8) . . . . ?
C9 C14 C15 C18 -147.1(6) . . . . ?
C10 C9 C14 C13 -3.8(9) . . . . ?
C10 C9 C14 C15 -177.3(6) . . . . ?
C10 C11 C12 O3 174.4(6) . . . . ?
C10 C11 C12 C13 -1.7(10) . . . . ?
C11 C12 C13 C14 -3.3(9) . . . . ?
C11 C12 C13 C17 169.8(6) . . . . ?
C12 C13 C14 C9 5.9(9) . . . . ?
C12 C13 C14 C15 179.0(5) . . . . ?
C13 C14 C15 C6 -139.0(6) . . . . ?
C13 C14 C15 C18 39.7(9) . . . . ?
C14 C9 C10 C11 -1.2(10) . . . . ?
C14 C15 C18 C19 19.7(9) . . . . ?
C14 C15 C18 C27 -161.1(6) . . . . ?
C15 C6 C7 C8 -33.1(8) . . . . ?
C15 C18 C19 C20 40.8(9) . . . . ?
C15 C18 C19 C24 -143.5(6) . . . . ?
C15 C18 C27 C26 165.3(6) . . . . ?
C15 C18 C27 C28 -12.0(9) . . . . ?
C16 O3 C12 C11 92.4(7) . . . . ?
C16 O3 C12 C13 -91.6(7) . . . . ?
C17 C13 C14 C9 -166.5(6) . . . . ?
C17 C13 C14 C15 6.5(9) . . . . ?
C18 C19 C20 C21 -177.1(6) . . . . ?
C18 C19 C20 C30 8.4(10) . . . . ?
C18 C19 C24 C23 177.5(6) . . . . ?
C18 C19 C24 C25 -6.1(8) . . . . ?
C18 C27 C28 C5 0.3(10) . . . . ?
C18 C27 C28 C29 -176.4(7) . . . . ?
C19 C18 C27 C26 -15.4(9) . . . . ?
C19 C18 C27 C28 167.3(6) . . . . ?
C19 C20 C21 O4 -178.1(6) . . . . ?
C19 C20 C21 C22 -2.8(10) . . . . ?
C19 C24 C25 C26 -42.2(8) . . . . ?
C20 C19 C24 C23 -6.7(10) . . . . ?
C20 C19 C24 C25 169.6(6) . . . . ?
C20 C21 C22 Br2 -179.8(5) . . . . ?
C20 C21 C22 C23 -2.7(11) . . . . ?
C21 C22 C23 C24 3.6(11) . . . . ?
C22 C23 C24 C19 1.1(10) . . . . ?
C22 C23 C24 C25 -175.1(7) . . . . ?
C23 C24 C25 C26 134.1(7) . . . . ?
C24 C19 C20 C21 7.4(9) . . . . ?
C24 C19 C20 C30 -167.1(6) . . . . ?
C24 C25 C26 C27 60.6(7) . . . . ?
C25 C26 C27 C18 -32.9(8) . . . . ?
C25 C26 C27 C28 144.2(7) . . . . ?
C26 C27 C28 C5 -176.9(7) . . . . ?
C26 C27 C28 C29 6.4(12) . . . . ?
C27 C18 C19 C20 -138.4(7) . . . . ?
C27 C18 C19 C24 37.2(8) . . . . ?
C27 C28 C29 O2 -4.9(16) . . . . ?
C27 C28 C29 N1 173.4(8) . . . . ?
C28 C5 C6 C7 -178.7(6) . . . . ?
C28 C5 C6 C15 -1.2(10) . . . . ?
C29 N1 C3 C2 107.9(11) . . . . ?
C29 N1 C4 O1 -178.0(8) . . . . ?
C29 N1 C4 C5 0.5(10) . . . . ?
C30 C20 C21 O4 -3.2(10) . . . . ?
C30 C20 C21 C22 172.0(7) . . . . ?
C31 O4 C21 C20 -86.5(9) . . . . ?
C31 O4 C21 C22 98.2(9) . . . . ?

_shelx_SHELXL_version_number     2014/7
_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_mx4330
_database_code_depnum_ccdc_archive 'CCDC 1465240'
_audit_update_record             
;
2016-03-14 deposited with the CCDC.
2016-07-13 downloaded from the CCDC.
;
_audit_creation_date             2015-12-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C31 H29 Br2 N O4'
_chemical_formula_sum            'C31 H29 Br2 N O4'
_chemical_formula_weight         639.37
_chemical_absolute_configuration ad
_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'
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      tetragonal
_space_group_IT_number           76
_space_group_name_H-M_alt        'P 41'
_space_group_name_Hall           'P 4w'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x, z+1/4'
'y, -x, z+3/4'

_cell_length_a                   12.347(3)
_cell_length_b                   12.347(3)
_cell_length_c                   18.073(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2755.1(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8060
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4722
_cell_measurement_theta_min      1.1267
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.980
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6305
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0733
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            31763
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.471
_diffrn_reflns_theta_min         1.649
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 45.0054
	          2theta: -20.1736
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 180.0000
	             XTD: 45.0054
	          2theta: -20.1736
scan:
	Number of images: 280
	           Slice: -110.0000 - 30.0000
	     Image width: 0.5000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 270.0000
	             XTD: 45.0054
	          2theta: -20.1736
;
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_number_total             3268
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0481
_diffrn_orient_matrix_UB_12      0.0387
_diffrn_orient_matrix_UB_13      0.0525
_diffrn_orient_matrix_UB_21      0.0465
_diffrn_orient_matrix_UB_22      0.0660
_diffrn_orient_matrix_UB_23      -0.0061
_diffrn_orient_matrix_UB_31      -0.0312
_diffrn_orient_matrix_UB_32      0.0181
_diffrn_orient_matrix_UB_33      -0.0419
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.938
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                5766
_reflns_number_total             6298
_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       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution    
;
'SHELXT (Sheldrick, 2014)'
;
_refine_diff_density_max         0.794
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.082
_refine_ls_abs_structure_details 
;
 Flack x determined using 2063 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.008(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     348
_refine_ls_number_reflns         6298
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0645
_refine_ls_restrained_S_all      1.100
_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)+(0.0592P)²+4.3962P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1466
_refine_ls_wR_factor_ref         0.1510
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C7(H7A,H7B), C8(H8A,H8B), C25(H25A,H25B), C26(H26A,
 H26B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C23(H23)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C30(H30A,H30B,
 H30C), C31(H31A,H31B,H31C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.51660(10) 0.42865(9) 0.64298(7) 0.0689(4) Uani 1 1 d . . . . .
Br2 Br 0.65154(7) 1.09191(8) 0.80663(5) 0.0527(3) Uani 1 1 d . . . . .
O1 O 0.0267(7) 0.8806(7) 0.3752(5) 0.080(3) Uani 1 1 d . . . . .
O2 O 0.1993(7) 1.2053(6) 0.3938(4) 0.072(2) Uani 1 1 d . . . . .
O3 O 0.6369(5) 0.6290(6) 0.5851(4) 0.0510(16) Uani 1 1 d . . . . .
O4 O 0.4821(5) 0.9137(5) 0.8069(3) 0.0438(13) Uani 1 1 d . . . . .
N1 N 0.0967(8) 1.0542(7) 0.3735(5) 0.067(3) Uani 1 1 d . . . . .
C1 C 0.0227(11) 1.1931(12) 0.1878(8) 0.088(4) Uani 1 1 d . . . . .
H1A H 0.0577 1.1979 0.1405 0.132 Uiso 1 1 calc GR . . . .
H1B H 0.0090 1.2647 0.2063 0.132 Uiso 1 1 calc GR . . . .
H1C H -0.0447 1.1549 0.1826 0.132 Uiso 1 1 calc GR . . . .
C2 C 0.0958(10) 1.1323(11) 0.2418(6) 0.071(3) Uani 1 1 d . . . . .
H2A H 0.1589 1.1760 0.2533 0.085 Uiso 1 1 calc R . . . .
H2B H 0.1204 1.0652 0.2195 0.085 Uiso 1 1 calc R . . . .
C3 C 0.0303(11) 1.1070(11) 0.3152(7) 0.077(3) Uani 1 1 d . . . . .
H3A H 0.0012 1.1742 0.3347 0.093 Uiso 1 1 calc R . . . .
H3B H -0.0303 1.0602 0.3032 0.093 Uiso 1 1 calc R . . . .
C4 C 0.0920(9) 0.9463(9) 0.3968(5) 0.059(3) Uani 1 1 d . . . . .
C5 C 0.1820(7) 0.9315(7) 0.4508(4) 0.0391(18) Uani 1 1 d . . . . .
C6 C 0.2210(6) 0.8411(7) 0.4858(4) 0.0377(17) Uani 1 1 d . . . . .
C7 C 0.1688(8) 0.7316(7) 0.4827(5) 0.050(2) Uani 1 1 d . . . . .
H7A H 0.2021 0.6883 0.4441 0.060 Uiso 1 1 calc R . . . .
H7B H 0.0923 0.7390 0.4715 0.060 Uiso 1 1 calc R . . . .
C8 C 0.1833(7) 0.6758(7) 0.5581(5) 0.0457(19) Uani 1 1 d . . . . .
H8A H 0.1496 0.7187 0.5967 0.055 Uiso 1 1 calc R . . . .
H8B H 0.1492 0.6050 0.5575 0.055 Uiso 1 1 calc R . . . .
C9 C 0.3009(6) 0.6644(7) 0.5729(4) 0.0373(17) Uani 1 1 d . . . . .
C10 C 0.3459(7) 0.5693(7) 0.5988(5) 0.0432(19) Uani 1 1 d . . . . .
H10 H 0.3014 0.5113 0.6112 0.052 Uiso 1 1 calc R . . . .
C11 C 0.4567(7) 0.5601(7) 0.6062(5) 0.0420(18) Uani 1 1 d . . . . .
C12 C 0.5251(6) 0.6434(7) 0.5841(4) 0.0388(17) Uani 1 1 d . . . . .
C13 C 0.4836(6) 0.7413(6) 0.5573(5) 0.0365(15) Uani 1 1 d . . . . .
C14 C 0.3695(6) 0.7537(6) 0.5561(4) 0.0322(14) Uani 1 1 d . . . . .
C15 C 0.3146(6) 0.8552(6) 0.5311(4) 0.0305(14) Uani 1 1 d . . . . .
C16 C 0.6873(9) 0.6711(12) 0.6500(7) 0.081(4) Uani 1 1 d . . . . .
H16A H 0.7642 0.6613 0.6466 0.121 Uiso 1 1 calc GR . . . .
H16B H 0.6603 0.6335 0.6927 0.121 Uiso 1 1 calc GR . . . .
H16C H 0.6711 0.7469 0.6544 0.121 Uiso 1 1 calc GR . . . .
C17 C 0.5612(7) 0.8232(7) 0.5259(5) 0.0441(19) Uani 1 1 d . . . . .
H17A H 0.5913 0.8657 0.5653 0.066 Uiso 1 1 calc GR . . . .
H17B H 0.5235 0.8697 0.4921 0.066 Uiso 1 1 calc GR . . . .
H17C H 0.6185 0.7864 0.5002 0.066 Uiso 1 1 calc GR . . . .
C18 C 0.3509(6) 0.9605(6) 0.5497(4) 0.0303(14) Uani 1 1 d . . . . .
C19 C 0.4239(6) 0.9844(6) 0.6131(4) 0.0294(14) Uani 1 1 d . . . . .
C20 C 0.4161(6) 0.9326(6) 0.6817(4) 0.0311(15) Uani 1 1 d . . . . .
C21 C 0.4890(6) 0.9635(6) 0.7382(4) 0.0353(16) Uani 1 1 d . . . . .
C22 C 0.5621(7) 1.0468(7) 0.7268(5) 0.0410(18) Uani 1 1 d . . . . .
C23 C 0.5641(6) 1.1029(7) 0.6616(5) 0.0410(18) Uani 1 1 d . . . . .
H23 H 0.6106 1.1616 0.6558 0.049 Uiso 1 1 calc R . . . .
C24 C 0.4961(6) 1.0716(6) 0.6037(5) 0.0381(17) Uani 1 1 d . . . . .
C25 C 0.4900(8) 1.1377(7) 0.5336(5) 0.047(2) Uani 1 1 d . . . . .
H25A H 0.5227 1.0984 0.4929 0.056 Uiso 1 1 calc R . . . .
H25B H 0.5281 1.2057 0.5398 0.056 Uiso 1 1 calc R . . . .
C26 C 0.3696(8) 1.1585(6) 0.5178(4) 0.0411(18) Uani 1 1 d . . . . .
H26A H 0.3372 1.1980 0.5586 0.049 Uiso 1 1 calc R . . . .
H26B H 0.3619 1.2018 0.4732 0.049 Uiso 1 1 calc R . . . .
C27 C 0.3132(7) 1.0511(6) 0.5079(4) 0.0388(18) Uani 1 1 d . . . . .
C28 C 0.2319(8) 1.0339(7) 0.4592(4) 0.043(2) Uani 1 1 d . . . . .
C29 C 0.1778(9) 1.1115(8) 0.4071(5) 0.054(2) Uani 1 1 d . . . . .
C30 C 0.3272(6) 0.8550(7) 0.7041(4) 0.0382(17) Uani 1 1 d . . . . .
H30A H 0.2689 0.8592 0.6691 0.057 Uiso 1 1 calc GR . . . .
H30B H 0.3010 0.8740 0.7524 0.057 Uiso 1 1 calc GR . . . .
H30C H 0.3553 0.7826 0.7051 0.057 Uiso 1 1 calc GR . . . .
C31 C 0.5511(8) 0.8211(8) 0.8124(6) 0.054(2) Uani 1 1 d . . . . .
H31A H 0.5306 0.7688 0.7757 0.081 Uiso 1 1 calc GR . . . .
H31B H 0.5440 0.7897 0.8607 0.081 Uiso 1 1 calc GR . . . .
H31C H 0.6249 0.8427 0.8045 0.081 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 C11 1.904(8) . ?
Br2 C22 1.900(9) . ?
O1 C4 1.208(13) . ?
O2 C29 1.211(13) . ?
O3 C12 1.391(10) . ?
O3 C16 1.426(13) . ?
O4 C21 1.387(10) . ?
O4 C31 1.429(11) . ?
N1 C3 1.485(13) . ?
N1 C4 1.398(14) . ?
N1 C29 1.368(14) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.527(15) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.585(18) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.491(12) . ?
C5 C6 1.370(12) . ?
C5 C28 1.415(13) . ?
C6 C7 1.499(12) . ?
C6 C15 1.427(10) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.538(14) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.482(12) . ?
C9 C10 1.381(12) . ?
C9 C14 1.423(10) . ?
C10 H10 0.9300 . ?
C10 C11 1.379(13) . ?
C11 C12 1.389(12) . ?
C12 C13 1.400(11) . ?
C13 C14 1.417(10) . ?
C13 C17 1.504(11) . ?
C14 C15 1.495(10) . ?
C15 C18 1.416(10) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.487(10) . ?
C18 C27 1.428(10) . ?
C19 C20 1.398(10) . ?
C19 C24 1.408(11) . ?
C20 C21 1.414(11) . ?
C20 C30 1.512(10) . ?
C21 C22 1.384(11) . ?
C22 C23 1.368(12) . ?
C23 H23 0.9300 . ?
C23 C24 1.396(12) . ?
C24 C25 1.509(12) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 C26 1.536(14) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C26 C27 1.509(12) . ?
C27 C28 1.352(12) . ?
C28 C29 1.500(12) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 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
C12 O3 C16 113.4(8) . . ?
C21 O4 C31 112.4(7) . . ?
C4 N1 C3 127.5(10) . . ?
C29 N1 C3 119.4(10) . . ?
C29 N1 C4 112.9(8) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C1 C2 H2A 109.8 . . ?
C1 C2 H2B 109.8 . . ?
C1 C2 C3 109.3(10) . . ?
H2A C2 H2B 108.3 . . ?
C3 C2 H2A 109.8 . . ?
C3 C2 H2B 109.8 . . ?
N1 C3 C2 113.5(10) . . ?
N1 C3 H3A 108.9 . . ?
N1 C3 H3B 108.9 . . ?
C2 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
O1 C4 N1 124.8(9) . . ?
O1 C4 C5 128.8(10) . . ?
N1 C4 C5 106.4(9) . . ?
C6 C5 C4 131.6(8) . . ?
C6 C5 C28 121.8(7) . . ?
C28 C5 C4 106.6(8) . . ?
C5 C6 C7 124.6(7) . . ?
C5 C6 C15 116.7(7) . . ?
C15 C6 C7 118.6(7) . . ?
C6 C7 H7A 109.9 . . ?
C6 C7 H7B 109.9 . . ?
C6 C7 C8 108.7(7) . . ?
H7A C7 H7B 108.3 . . ?
C8 C7 H7A 109.9 . . ?
C8 C7 H7B 109.9 . . ?
C7 C8 H8A 110.0 . . ?
C7 C8 H8B 110.0 . . ?
H8A C8 H8B 108.4 . . ?
C9 C8 C7 108.4(7) . . ?
C9 C8 H8A 110.0 . . ?
C9 C8 H8B 110.0 . . ?
C10 C9 C8 122.4(8) . . ?
C10 C9 C14 119.4(7) . . ?
C14 C9 C8 118.1(7) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 120.1(8) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 Br1 119.3(6) . . ?
C10 C11 C12 121.0(8) . . ?
C12 C11 Br1 119.6(6) . . ?
O3 C12 C13 118.6(8) . . ?
C11 C12 O3 120.3(7) . . ?
C11 C12 C13 121.0(7) . . ?
C12 C13 C14 117.5(7) . . ?
C12 C13 C17 118.5(7) . . ?
C14 C13 C17 123.7(7) . . ?
C9 C14 C15 116.3(7) . . ?
C13 C14 C9 120.4(7) . . ?
C13 C14 C15 123.1(7) . . ?
C6 C15 C14 116.1(7) . . ?
C18 C15 C6 120.3(7) . . ?
C18 C15 C14 123.7(6) . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C17 H17A 109.5 . . ?
C13 C17 H17B 109.5 . . ?
C13 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 C19 123.9(7) . . ?
C15 C18 C27 119.4(7) . . ?
C27 C18 C19 116.7(7) . . ?
C20 C19 C18 123.4(7) . . ?
C20 C19 C24 120.0(7) . . ?
C24 C19 C18 116.3(7) . . ?
C19 C20 C21 118.3(7) . . ?
C19 C20 C30 125.3(7) . . ?
C21 C20 C30 116.1(7) . . ?
O4 C21 C20 119.2(7) . . ?
C22 C21 O4 120.1(7) . . ?
C22 C21 C20 120.6(7) . . ?
C21 C22 Br2 119.0(6) . . ?
C23 C22 Br2 119.7(6) . . ?
C23 C22 C21 121.1(8) . . ?
C22 C23 H23 120.2 . . ?
C22 C23 C24 119.6(7) . . ?
C24 C23 H23 120.2 . . ?
C19 C24 C25 118.8(8) . . ?
C23 C24 C19 120.2(7) . . ?
C23 C24 C25 120.6(7) . . ?
C24 C25 H25A 110.3 . . ?
C24 C25 H25B 110.3 . . ?
C24 C25 C26 107.2(7) . . ?
H25A C25 H25B 108.5 . . ?
C26 C25 H25A 110.3 . . ?
C26 C25 H25B 110.3 . . ?
C25 C26 H26A 109.9 . . ?
C25 C26 H26B 109.9 . . ?
H26A C26 H26B 108.3 . . ?
C27 C26 C25 108.7(7) . . ?
C27 C26 H26A 109.9 . . ?
C27 C26 H26B 109.9 . . ?
C18 C27 C26 118.5(7) . . ?
C28 C27 C18 117.6(8) . . ?
C28 C27 C26 123.8(8) . . ?
C5 C28 C29 108.0(8) . . ?
C27 C28 C5 122.2(8) . . ?
C27 C28 C29 129.8(9) . . ?
O2 C29 N1 124.5(9) . . ?
O2 C29 C28 129.5(10) . . ?
N1 C29 C28 105.9(9) . . ?
C20 C30 H30A 109.5 . . ?
C20 C30 H30B 109.5 . . ?
C20 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
O4 C31 H31A 109.5 . . ?
O4 C31 H31B 109.5 . . ?
O4 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 C11 C12 O3 3.4(11) . . . . ?
Br1 C11 C12 C13 -179.5(6) . . . . ?
Br2 C22 C23 C24 -178.1(6) . . . . ?
O1 C4 C5 C6 5.8(18) . . . . ?
O1 C4 C5 C28 -177.8(11) . . . . ?
O3 C12 C13 C14 179.3(7) . . . . ?
O3 C12 C13 C17 4.3(11) . . . . ?
O4 C21 C22 Br2 -0.4(10) . . . . ?
O4 C21 C22 C23 -174.6(8) . . . . ?
N1 C4 C5 C6 -173.5(9) . . . . ?
N1 C4 C5 C28 2.9(10) . . . . ?
C1 C2 C3 N1 -176.2(11) . . . . ?
C3 N1 C4 O1 -4.9(19) . . . . ?
C3 N1 C4 C5 174.5(10) . . . . ?
C3 N1 C29 O2 1.6(16) . . . . ?
C3 N1 C29 C28 -177.0(9) . . . . ?
C4 N1 C3 C2 -107.5(14) . . . . ?
C4 N1 C29 O2 177.6(10) . . . . ?
C4 N1 C29 C28 -0.9(11) . . . . ?
C4 C5 C6 C7 -7.5(15) . . . . ?
C4 C5 C6 C15 175.8(9) . . . . ?
C4 C5 C28 C27 175.9(8) . . . . ?
C4 C5 C28 C29 -3.4(9) . . . . ?
C5 C6 C7 C8 -144.3(8) . . . . ?
C5 C6 C15 C14 -167.8(7) . . . . ?
C5 C6 C15 C18 12.0(10) . . . . ?
C5 C28 C29 O2 -175.7(10) . . . . ?
C5 C28 C29 N1 2.8(10) . . . . ?
C6 C5 C28 C27 -7.2(13) . . . . ?
C6 C5 C28 C29 173.4(8) . . . . ?
C6 C7 C8 C9 -60.4(9) . . . . ?
C6 C15 C18 C19 160.5(7) . . . . ?
C6 C15 C18 C27 -17.0(10) . . . . ?
C7 C6 C15 C14 15.3(10) . . . . ?
C7 C6 C15 C18 -164.9(7) . . . . ?
C7 C8 C9 C10 -134.2(8) . . . . ?
C7 C8 C9 C14 42.6(10) . . . . ?
C8 C9 C10 C11 175.0(8) . . . . ?
C8 C9 C14 C13 -169.4(8) . . . . ?
C8 C9 C14 C15 5.3(10) . . . . ?
C9 C10 C11 Br1 179.3(6) . . . . ?
C9 C10 C11 C12 -3.6(13) . . . . ?
C9 C14 C15 C6 -36.3(9) . . . . ?
C9 C14 C15 C18 144.0(7) . . . . ?
C10 C9 C14 C13 7.5(11) . . . . ?
C10 C9 C14 C15 -177.8(7) . . . . ?
C10 C11 C12 O3 -173.7(8) . . . . ?
C10 C11 C12 C13 3.4(13) . . . . ?
C11 C12 C13 C14 2.2(12) . . . . ?
C11 C12 C13 C17 -172.9(8) . . . . ?
C12 C13 C14 C9 -7.6(11) . . . . ?
C12 C13 C14 C15 178.1(7) . . . . ?
C13 C14 C15 C6 138.2(8) . . . . ?
C13 C14 C15 C18 -41.5(11) . . . . ?
C14 C9 C10 C11 -1.8(12) . . . . ?
C14 C15 C18 C19 -19.8(11) . . . . ?
C14 C15 C18 C27 162.8(7) . . . . ?
C15 C6 C7 C8 32.4(10) . . . . ?
C15 C18 C19 C20 -39.2(10) . . . . ?
C15 C18 C19 C24 147.4(7) . . . . ?
C15 C18 C27 C26 -167.5(7) . . . . ?
C15 C18 C27 C28 9.6(11) . . . . ?
C16 O3 C12 C11 -97.2(11) . . . . ?
C16 O3 C12 C13 85.7(11) . . . . ?
C17 C13 C14 C9 167.2(7) . . . . ?
C17 C13 C14 C15 -7.1(12) . . . . ?
C18 C19 C20 C21 -179.0(7) . . . . ?
C18 C19 C20 C30 -6.7(11) . . . . ?
C18 C19 C24 C23 177.1(7) . . . . ?
C18 C19 C24 C25 3.6(10) . . . . ?
C18 C27 C28 C5 2.3(12) . . . . ?
C18 C27 C28 C29 -178.5(8) . . . . ?
C19 C18 C27 C26 14.9(10) . . . . ?
C19 C18 C27 C28 -168.1(7) . . . . ?
C19 C20 C21 O4 179.6(7) . . . . ?
C19 C20 C21 C22 3.4(11) . . . . ?
C19 C24 C25 C26 43.7(9) . . . . ?
C20 C19 C24 C23 3.4(11) . . . . ?
C20 C19 C24 C25 -170.0(7) . . . . ?
C20 C21 C22 Br2 175.7(6) . . . . ?
C20 C21 C22 C23 1.6(12) . . . . ?
C21 C22 C23 C24 -4.0(13) . . . . ?
C22 C23 C24 C19 1.5(12) . . . . ?
C22 C23 C24 C25 174.9(8) . . . . ?
C23 C24 C25 C26 -129.7(8) . . . . ?
C24 C19 C20 C21 -5.8(10) . . . . ?
C24 C19 C20 C30 166.5(7) . . . . ?
C24 C25 C26 C27 -60.3(8) . . . . ?
C25 C26 C27 C18 33.0(9) . . . . ?
C25 C26 C27 C28 -143.8(8) . . . . ?
C26 C27 C28 C5 179.1(8) . . . . ?
C26 C27 C28 C29 -1.6(14) . . . . ?
C27 C18 C19 C20 138.4(7) . . . . ?
C27 C18 C19 C24 -35.0(9) . . . . ?
C27 C28 C29 O2 5.0(17) . . . . ?
C27 C28 C29 N1 -176.5(9) . . . . ?
C28 C5 C6 C7 176.5(8) . . . . ?
C28 C5 C6 C15 -0.1(12) . . . . ?
C29 N1 C3 C2 67.9(14) . . . . ?
C29 N1 C4 O1 179.5(10) . . . . ?
C29 N1 C4 C5 -1.2(12) . . . . ?
C30 C20 C21 O4 6.6(10) . . . . ?
C30 C20 C21 C22 -169.6(7) . . . . ?
C31 O4 C21 C20 92.0(9) . . . . ?
C31 O4 C21 C22 -91.8(9) . . . . ?

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