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

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

data_mb-js-v-77
_database_code_depnum_ccdc_archive 'CCDC 1053999'
_audit_update_record             
;
2015-03-13 deposited with the CCDC.
2018-12-12 downloaded from the CCDC.
;
_audit_creation_date             2015-03-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C25 H21 Br N2 O8'
_chemical_formula_sum            'C25 H21 Br N2 O8'
_chemical_formula_weight         557.35
_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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/a 1'
_space_group_name_Hall           '-P 2yab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z'

_cell_length_a                   8.5538(5)
_cell_length_b                   28.5184(14)
_cell_length_c                   9.9217(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.085(5)
_cell_angle_gamma                90.00
_cell_volume                     2347.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_exptl_absorpt_coefficient_mu    1.806
_exptl_absorpt_correction_T_max  0.6609
_exptl_absorpt_correction_T_min  0.4654
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     ?
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0546
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12825
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.21
_diffrn_reflns_theta_min         4.20
_diffrn_ambient_temperature      298.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.852
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3748
_reflns_number_total             5425
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.483
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         5425
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0463
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0276P)²+1.0549P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0808
_refine_ls_wR_factor_ref         0.0930
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_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 Ternary CH refined with riding coordinates:
 C8(H8), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C32(H32A,H32B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C13(H13), C28(H28), C25(H25), C12(H12), C26(H26), C29(H29), C27(H27)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C2(H2A,H2B,H2C), C4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Br34 Br 0.18739(4) 0.431594(10) -0.03770(4) 0.04926(12) Uani 1 d . . .
O15 O 0.4196(2) 0.61745(6) -0.20286(18) 0.0308(4) Uani 1 d . . .
O2 O 0.52406(19) 0.67320(6) -0.03610(17) 0.0312(4) Uani 1 d . . .
O23 O -0.0444(2) 0.64164(7) -0.1745(2) 0.0434(5) Uani 1 d . . .
O18 O 0.4484(2) 0.68829(6) -0.35266(18) 0.0366(4) Uani 1 d . . .
O20 O 0.3379(3) 0.73847(7) -0.2286(2) 0.0515(6) Uani 1 d . . .
N4 N 0.6507(2) 0.65825(7) 0.2017(2) 0.0278(5) Uani 1 d . . .
O33 O 0.4701(3) 0.57981(10) 0.4777(2) 0.0708(8) Uani 1 d . . .
O31 O 0.2461(2) 0.57897(8) 0.3038(2) 0.0496(6) Uani 1 d . . .
O22 O 0.0915(2) 0.65563(9) -0.3343(2) 0.0572(6) Uani 1 d . . .
C10 C 0.2251(3) 0.53031(9) -0.0229(3) 0.0274(6) Uani 1 d . . .
H10 H 0.1691 0.5281 0.0462 0.033 Uiso 1 calc . . R
C7 C 0.4021(3) 0.63004(8) 0.1250(2) 0.0254(5) Uani 1 d . . .
C13 C 0.3908(3) 0.53592(10) -0.2303(3) 0.0346(6) Uani 1 d . . .
H13 H 0.4458 0.5381 -0.3002 0.041 Uiso 1 calc . . R
C9 C 0.2769(3) 0.57374(9) -0.0580(2) 0.0240(5) Uani 1 d . . .
N5 N 0.6163(3) 0.63568(8) 0.3130(2) 0.0324(5) Uani 1 d . . .
C28 C 1.0014(3) 0.71859(9) 0.1223(3) 0.0353(6) Uani 1 d . . .
H28 H 1.0271 0.7358 0.0511 0.042 Uiso 1 calc . . R
C8 C 0.2521(3) 0.61863(9) 0.0150(2) 0.0252(5) Uani 1 d . . .
H8 H 0.1579 0.6164 0.0545 0.030 Uiso 1 calc . . R
C21 C 0.0874(3) 0.65148(9) -0.2159(3) 0.0306(6) Uani 1 d . . .
C17 C 0.3847(3) 0.70016(10) -0.2499(3) 0.0289(6) Uani 1 d . . .
C25 C 0.9248(3) 0.66870(10) 0.3350(3) 0.0373(7) Uani 1 d . . .
H25 H 0.8993 0.6519 0.4072 0.045 Uiso 1 calc . . R
C3 C 0.5220(3) 0.65478(9) 0.0894(2) 0.0261(5) Uani 1 d . . .
C14 C 0.3608(3) 0.57577(9) -0.1618(2) 0.0258(5) Uani 1 d . . .
C1 C 0.3852(3) 0.65999(9) -0.1467(2) 0.0251(5) Uani 1 d . . .
C11 C 0.2569(3) 0.49043(9) -0.0907(3) 0.0330(6) Uani 1 d . . .
C16 C 0.2313(3) 0.65811(9) -0.0938(2) 0.0254(5) Uani 1 d . . .
H16 H 0.2194 0.6880 -0.0484 0.030 Uiso 1 calc . . R
C24 C 0.8083(3) 0.67703(9) 0.2138(3) 0.0273(6) Uani 1 d . . .
C6 C 0.4682(3) 0.61879(9) 0.2659(2) 0.0280(6) Uani 1 d . . .
C12 C 0.3388(3) 0.49272(10) -0.1947(3) 0.0362(6) Uani 1 d . . .
H12 H 0.3586 0.4656 -0.2401 0.043 Uiso 1 calc . . R
C26 C 1.0795(3) 0.68549(11) 0.3482(3) 0.0438(7) Uani 1 d . . .
H26 H 1.1580 0.6800 0.4297 0.053 Uiso 1 calc . . R
C19 C 0.4700(4) 0.72590(11) -0.4452(3) 0.0461(8) Uani 1 d . . .
H19A H 0.5042 0.7130 -0.5227 0.069 Uiso 1 calc . . GR
H19B H 0.5503 0.7473 -0.3959 0.069 Uiso 1 calc . . GR
H19C H 0.3698 0.7422 -0.4782 0.069 Uiso 1 calc . . GR
C29 C 0.8461(3) 0.70187(9) 0.1061(3) 0.0325(6) Uani 1 d . . .
H29 H 0.7683 0.7072 0.0241 0.039 Uiso 1 calc . . R
C27 C 1.1182(3) 0.71017(10) 0.2420(3) 0.0402(7) Uani 1 d . . .
H27 H 1.2226 0.7211 0.2510 0.048 Uiso 1 calc . . R
C30 C 0.3984(3) 0.59067(10) 0.3630(3) 0.0372(7) Uani 1 d . . .
C32 C 0.1589(4) 0.55321(14) 0.3900(4) 0.0638(10) Uani 1 d . . .
H32A H 0.0450 0.5606 0.3608 0.077 Uiso 1 calc . . R
H32B H 0.1976 0.5627 0.4862 0.077 Uiso 1 calc . . R
C2 C -0.1919(3) 0.63625(13) -0.2835(4) 0.0600(10) Uani 1 d . . .
H2A H -0.1800 0.6105 -0.3427 0.090 Uiso 1 calc . . GR
H2B H -0.2125 0.6645 -0.3374 0.090 Uiso 1 calc . . GR
H2C H -0.2804 0.6301 -0.2422 0.090 Uiso 1 calc . . GR
C4 C 0.1817(6) 0.50236(16) 0.3781(5) 0.0968(15) Uani 1 d . . .
H4A H 0.1469 0.4932 0.2824 0.145 Uiso 1 calc . . GR
H4B H 0.1193 0.4860 0.4316 0.145 Uiso 1 calc . . GR
H4C H 0.2936 0.4948 0.4127 0.145 Uiso 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
Br34 C11 1.897(3) . ?
O15 C14 1.390(3) . ?
O15 C1 1.396(3) . ?
O2 C3 1.356(3) . ?
O2 C1 1.457(3) . ?
O23 C21 1.320(3) . ?
O23 C2 1.456(4) . ?
O18 C17 1.312(3) . ?
O18 C19 1.453(3) . ?
O20 C17 1.200(3) . ?
N4 N5 1.370(3) . ?
N4 C3 1.367(3) . ?
N4 C24 1.428(3) . ?
O33 C30 1.195(3) . ?
O31 C30 1.335(3) . ?
O31 C32 1.462(3) . ?
O22 C21 1.190(3) . ?
C10 H10 0.9300 . ?
C10 C9 1.388(3) . ?
C10 C11 1.381(4) . ?
C7 C8 1.504(3) . ?
C7 C3 1.360(3) . ?
C7 C6 1.412(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.380(4) . ?
C13 C12 1.384(4) . ?
C9 C8 1.511(3) . ?
C9 C14 1.392(3) . ?
N5 C6 1.329(3) . ?
C28 H28 0.9300 . ?
C28 C29 1.383(4) . ?
C28 C27 1.374(4) . ?
C8 H8 0.9800 . ?
C8 C16 1.540(3) . ?
C21 C16 1.515(3) . ?
C17 C1 1.536(3) . ?
C25 H25 0.9300 . ?
C25 C24 1.384(4) . ?
C25 C26 1.383(4) . ?
C1 C16 1.533(3) . ?
C11 C12 1.383(4) . ?
C16 H16 0.9800 . ?
C24 C29 1.384(3) . ?
C6 C30 1.485(3) . ?
C12 H12 0.9300 . ?
C26 H26 0.9300 . ?
C26 C27 1.373(4) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C29 H29 0.9300 . ?
C27 H27 0.9300 . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C32 C4 1.472(5) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 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
C14 O15 C1 119.98(18) . . ?
C3 O2 C1 113.66(18) . . ?
C21 O23 C2 116.3(2) . . ?
C17 O18 C19 116.2(2) . . ?
N5 N4 C24 119.5(2) . . ?
C3 N4 N5 109.5(2) . . ?
C3 N4 C24 130.7(2) . . ?
C30 O31 C32 116.8(2) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C11 C10 C9 120.0(2) . . ?
C3 C7 C8 119.2(2) . . ?
C3 C7 C6 103.3(2) . . ?
C6 C7 C8 137.3(2) . . ?
C14 C13 H13 120.1 . . ?
C14 C13 C12 119.8(2) . . ?
C12 C13 H13 120.1 . . ?
C10 C9 C8 123.0(2) . . ?
C10 C9 C14 118.4(2) . . ?
C14 C9 C8 118.5(2) . . ?
C6 N5 N4 105.1(2) . . ?
C29 C28 H28 119.5 . . ?
C27 C28 H28 119.5 . . ?
C27 C28 C29 121.0(3) . . ?
C7 C8 C9 109.7(2) . . ?
C7 C8 H8 111.2 . . ?
C7 C8 C16 106.4(2) . . ?
C9 C8 H8 111.2 . . ?
C9 C8 C16 106.82(19) . . ?
C16 C8 H8 111.2 . . ?
O23 C21 C16 111.5(2) . . ?
O22 C21 O23 124.1(2) . . ?
O22 C21 C16 124.3(2) . . ?
O18 C17 C1 113.0(2) . . ?
O20 C17 O18 126.3(2) . . ?
O20 C17 C1 120.6(2) . . ?
C24 C25 H25 120.2 . . ?
C26 C25 H25 120.2 . . ?
C26 C25 C24 119.5(3) . . ?
O2 C3 N4 122.2(2) . . ?
O2 C3 C7 128.2(2) . . ?
C7 C3 N4 109.5(2) . . ?
O15 C14 C9 122.8(2) . . ?
C13 C14 O15 115.8(2) . . ?
C13 C14 C9 121.4(2) . . ?
O15 C1 O2 108.24(18) . . ?
O15 C1 C17 110.44(19) . . ?
O15 C1 C16 112.87(19) . . ?
O2 C1 C17 100.30(18) . . ?
O2 C1 C16 111.18(19) . . ?
C16 C1 C17 113.0(2) . . ?
C10 C11 Br34 118.77(19) . . ?
C10 C11 C12 121.3(2) . . ?
C12 C11 Br34 119.9(2) . . ?
C8 C16 H16 108.7 . . ?
C21 C16 C8 113.7(2) . . ?
C21 C16 C1 109.2(2) . . ?
C21 C16 H16 108.7 . . ?
C1 C16 C8 107.67(19) . . ?
C1 C16 H16 108.7 . . ?
C25 C24 N4 118.3(2) . . ?
C25 C24 C29 120.3(2) . . ?
C29 C24 N4 121.4(2) . . ?
C7 C6 C30 129.6(2) . . ?
N5 C6 C7 112.5(2) . . ?
N5 C6 C30 117.8(2) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 C13 119.0(2) . . ?
C11 C12 H12 120.5 . . ?
C25 C26 H26 119.7 . . ?
C27 C26 C25 120.6(3) . . ?
C27 C26 H26 119.7 . . ?
O18 C19 H19A 109.5 . . ?
O18 C19 H19B 109.5 . . ?
O18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C28 C29 C24 119.0(2) . . ?
C28 C29 H29 120.5 . . ?
C24 C29 H29 120.5 . . ?
C28 C27 H27 120.2 . . ?
C26 C27 C28 119.5(3) . . ?
C26 C27 H27 120.2 . . ?
O33 C30 O31 125.0(3) . . ?
O33 C30 C6 124.3(3) . . ?
O31 C30 C6 110.7(2) . . ?
O31 C32 H32A 109.5 . . ?
O31 C32 H32B 109.5 . . ?
O31 C32 C4 110.6(3) . . ?
H32A C32 H32B 108.1 . . ?
C4 C32 H32A 109.5 . . ?
C4 C32 H32B 109.5 . . ?
O23 C2 H2A 109.5 . . ?
O23 C2 H2B 109.5 . . ?
O23 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C32 C4 H4A 109.5 . . ?
C32 C4 H4B 109.5 . . ?
C32 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 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
Br34 C11 C12 C13 -179.0(2) . . . . ?
O15 C1 C16 C8 57.3(2) . . . . ?
O15 C1 C16 C21 -66.6(2) . . . . ?
O2 C1 C16 C8 -64.5(2) . . . . ?
O2 C1 C16 C21 171.6(2) . . . . ?
O23 C21 C16 C8 49.0(3) . . . . ?
O23 C21 C16 C1 169.2(2) . . . . ?
O18 C17 C1 O15 -13.5(3) . . . . ?
O18 C17 C1 O2 100.6(2) . . . . ?
O18 C17 C1 C16 -141.0(2) . . . . ?
O20 C17 C1 O15 170.6(2) . . . . ?
O20 C17 C1 O2 -75.4(3) . . . . ?
O20 C17 C1 C16 43.1(3) . . . . ?
N4 N5 C6 C7 -0.5(3) . . . . ?
N4 N5 C6 C30 177.9(2) . . . . ?
N4 C24 C29 C28 -178.9(2) . . . . ?
O22 C21 C16 C8 -132.6(3) . . . . ?
O22 C21 C16 C1 -12.4(4) . . . . ?
C10 C9 C8 C7 96.9(3) . . . . ?
C10 C9 C8 C16 -148.1(2) . . . . ?
C10 C9 C14 O15 -179.0(2) . . . . ?
C10 C9 C14 C13 0.9(4) . . . . ?
C10 C11 C12 C13 0.6(4) . . . . ?
C7 C8 C16 C21 178.2(2) . . . . ?
C7 C8 C16 C1 57.1(2) . . . . ?
C7 C6 C30 O33 173.3(3) . . . . ?
C7 C6 C30 O31 -6.1(4) . . . . ?
C9 C10 C11 Br34 178.98(18) . . . . ?
C9 C10 C11 C12 -0.6(4) . . . . ?
C9 C8 C16 C21 61.0(3) . . . . ?
C9 C8 C16 C1 -60.1(2) . . . . ?
N5 N4 C3 O2 -178.6(2) . . . . ?
N5 N4 C3 C7 0.0(3) . . . . ?
N5 N4 C24 C25 4.7(3) . . . . ?
N5 N4 C24 C29 -177.1(2) . . . . ?
N5 C6 C30 O33 -4.8(4) . . . . ?
N5 C6 C30 O31 175.8(2) . . . . ?
C8 C7 C3 O2 2.9(4) . . . . ?
C8 C7 C3 N4 -175.6(2) . . . . ?
C8 C7 C6 N5 174.5(3) . . . . ?
C8 C7 C6 C30 -3.7(5) . . . . ?
C8 C9 C14 O15 -1.4(3) . . . . ?
C8 C9 C14 C13 178.5(2) . . . . ?
C17 C1 C16 C8 -176.4(2) . . . . ?
C17 C1 C16 C21 59.7(3) . . . . ?
C25 C24 C29 C28 -0.7(4) . . . . ?
C25 C26 C27 C28 0.7(5) . . . . ?
C3 O2 C1 O15 -87.0(2) . . . . ?
C3 O2 C1 C17 157.3(2) . . . . ?
C3 O2 C1 C16 37.5(3) . . . . ?
C3 N4 N5 C6 0.3(3) . . . . ?
C3 N4 C24 C25 -168.8(3) . . . . ?
C3 N4 C24 C29 9.4(4) . . . . ?
C3 C7 C8 C9 86.4(3) . . . . ?
C3 C7 C8 C16 -28.8(3) . . . . ?
C3 C7 C6 N5 0.5(3) . . . . ?
C3 C7 C6 C30 -177.7(3) . . . . ?
C14 O15 C1 O2 99.1(2) . . . . ?
C14 O15 C1 C17 -152.0(2) . . . . ?
C14 O15 C1 C16 -24.4(3) . . . . ?
C14 C13 C12 C11 0.2(4) . . . . ?
C14 C9 C8 C7 -80.6(3) . . . . ?
C14 C9 C8 C16 34.4(3) . . . . ?
C1 O15 C14 C13 175.4(2) . . . . ?
C1 O15 C14 C9 -4.7(3) . . . . ?
C1 O2 C3 N4 171.6(2) . . . . ?
C1 O2 C3 C7 -6.7(4) . . . . ?
C11 C10 C9 C8 -177.7(2) . . . . ?
C11 C10 C9 C14 -0.2(4) . . . . ?
C24 N4 N5 C6 -174.4(2) . . . . ?
C24 N4 C3 O2 -4.6(4) . . . . ?
C24 N4 C3 C7 174.0(2) . . . . ?
C24 C25 C26 C27 -0.2(5) . . . . ?
C6 C7 C8 C9 -86.9(3) . . . . ?
C6 C7 C8 C16 157.9(3) . . . . ?
C6 C7 C3 O2 178.2(2) . . . . ?
C6 C7 C3 N4 -0.3(3) . . . . ?
C12 C13 C14 O15 179.0(2) . . . . ?
C12 C13 C14 C9 -0.9(4) . . . . ?
C26 C25 C24 N4 178.4(2) . . . . ?
C26 C25 C24 C29 0.2(4) . . . . ?
C19 O18 C17 O20 2.8(4) . . . . ?
C19 O18 C17 C1 -172.8(2) . . . . ?
C29 C28 C27 C26 -1.2(4) . . . . ?
C27 C28 C29 C24 1.2(4) . . . . ?
C30 O31 C32 C4 -89.2(4) . . . . ?
C32 O31 C30 O33 3.7(5) . . . . ?
C32 O31 C30 C6 -176.9(3) . . . . ?
C2 O23 C21 O22 -0.6(4) . . . . ?
C2 O23 C21 C16 177.8(2) . . . . ?

_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_prsk-iv-94
_database_code_depnum_ccdc_archive 'CCDC 1054000'
_audit_update_record             
;
2015-03-13 deposited with the CCDC.
2018-12-12 downloaded from the CCDC.
;
_audit_creation_date             2015-03-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C22 H17 Br N2 O6'
_chemical_formula_sum            'C22 H17 Br N2 O6'
_chemical_formula_weight         485.29
_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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   8.0079(7)
_cell_length_b                   10.6912(11)
_cell_length_c                   12.9965(11)
_cell_angle_alpha                79.773(8)
_cell_angle_beta                 82.666(7)
_cell_angle_gamma                69.817(8)
_cell_volume                     1025.11(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_exptl_absorpt_coefficient_mu    2.048
_exptl_absorpt_correction_T_max  0.6614
_exptl_absorpt_correction_T_min  0.5342
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_unetI/netI     0.0741
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9637
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.14
_diffrn_reflns_theta_min         4.04
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.846
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2760
_reflns_number_total             4659
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4659
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1010
_refine_ls_R_factor_gt           0.0491
_refine_ls_restrained_S_all      0.995
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0339P)²+0.0319P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0872
_refine_ls_wR_factor_ref         0.1046
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_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 Ternary CH refined with riding coordinates:
 C13(H13), C22(H22), C5(H5)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C9(H9), C7(H7), C17(H17), C21(H21), C20(H20), C19(H19), C18(H18)
2.c Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C25(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Br27 Br 0.63652(6) -0.03164(4) 0.32311(4) 0.07604(19) Uani 1 d . . .
O14 O 0.5098(2) 0.71268(18) 0.14292(15) 0.0317(5) Uani 1 d . . .
O29 O 1.1068(2) 0.4066(2) 0.39784(17) 0.0470(6) Uani 1 d . . .
O26 O 0.4219(3) 0.7261(2) 0.42511(18) 0.0480(6) Uani 1 d . . .
O12 O 0.3912(2) 0.54849(19) 0.12363(15) 0.0362(5) Uani 1 d . . .
N2 N 0.9504(3) 0.5727(2) 0.2232(2) 0.0355(6) Uani 1 d . . .
O24 O 0.1940(3) 0.8355(2) 0.32454(18) 0.0535(6) Uani 1 d . . .
O31 O 0.8941(3) 0.3133(3) 0.4204(2) 0.0850(10) Uani 1 d . . .
C13 C 0.3670(3) 0.6567(3) 0.1792(2) 0.0302(6) Uani 1 d . . .
H13 H 0.2534 0.7265 0.1616 0.036 Uiso 1 calc . . R
N1 N 0.8211(3) 0.6582(2) 0.15925(19) 0.0317(6) Uani 1 d . . .
C30 C 1.1953(4) 0.3076(4) 0.4824(3) 0.0579(10) Uani 1 d . . .
H30A H 1.2386 0.2201 0.4606 0.087 Uiso 1 calc . . GR
H30B H 1.1124 0.3074 0.5426 0.087 Uiso 1 calc . . GR
H30C H 1.2937 0.3297 0.5000 0.087 Uiso 1 calc . . GR
C11 C 0.4452(3) 0.4175(3) 0.1745(2) 0.0303(6) Uani 1 d . . .
C10 C 0.4229(4) 0.3218(3) 0.1237(3) 0.0411(8) Uani 1 d . . .
H10 H 0.3705 0.3471 0.0600 0.049 Uiso 1 calc . . R
C9 C 0.4789(4) 0.1886(3) 0.1682(3) 0.0467(8) Uani 1 d . . .
H9 H 0.4639 0.1234 0.1350 0.056 Uiso 1 calc . . R
C3 C 0.8661(3) 0.5009(3) 0.2911(2) 0.0314(7) Uani 1 d . . .
C16 C 0.8656(3) 0.7424(3) 0.0705(2) 0.0323(7) Uani 1 d . . .
C8 C 0.5572(4) 0.1525(3) 0.2621(3) 0.0396(8) Uani 1 d . . .
C7 C 0.5770(3) 0.2482(3) 0.3142(2) 0.0335(7) Uani 1 d . . .
H7 H 0.6293 0.2222 0.3779 0.040 Uiso 1 calc . . R
C22 C 0.3594(3) 0.6136(3) 0.2971(2) 0.0296(6) Uani 1 d . . .
H22 H 0.2571 0.5818 0.3166 0.036 Uiso 1 calc . . R
C15 C 0.6619(3) 0.6384(3) 0.1915(2) 0.0288(6) Uani 1 d . . .
C17 C 0.7548(4) 0.8722(3) 0.0461(3) 0.0467(8) Uani 1 d . . .
H17 H 0.6499 0.9053 0.0873 0.056 Uiso 1 calc . . R
C4 C 0.6831(3) 0.5395(3) 0.2741(2) 0.0278(6) Uani 1 d . . .
C6 C 0.5190(3) 0.3818(3) 0.2715(2) 0.0277(6) Uani 1 d . . .
C5 C 0.5287(3) 0.4946(3) 0.3230(2) 0.0282(6) Uani 1 d . . .
H5 H 0.5359 0.4684 0.3989 0.034 Uiso 1 calc . . R
C23 C 0.3329(4) 0.7299(3) 0.3569(2) 0.0326(7) Uani 1 d . . .
C28 C 0.9558(4) 0.3968(3) 0.3751(3) 0.0418(8) Uani 1 d . . .
C21 C 1.0186(4) 0.6915(4) 0.0088(3) 0.0521(9) Uani 1 d . . .
H21 H 1.0925 0.6028 0.0245 0.062 Uiso 1 calc . . R
C20 C 1.0609(5) 0.7754(5) -0.0778(3) 0.0721(12) Uani 1 d . . .
H20 H 1.1639 0.7422 -0.1205 0.086 Uiso 1 calc . . R
C19 C 0.9521(6) 0.9067(5) -0.1011(3) 0.0696(12) Uani 1 d . . .
H19 H 0.9826 0.9627 -0.1581 0.084 Uiso 1 calc . . R
C25 C 0.1464(5) 0.9493(4) 0.3815(3) 0.0717(12) Uani 1 d . . .
H25A H 0.0396 1.0166 0.3562 0.107 Uiso 1 calc . . GR
H25B H 0.2416 0.9865 0.3713 0.107 Uiso 1 calc . . GR
H25C H 0.1265 0.9200 0.4549 0.107 Uiso 1 calc . . GR
C18 C 0.8001(5) 0.9534(4) -0.0399(3) 0.0649(11) Uani 1 d . . .
H18 H 0.7252 1.0416 -0.0562 0.078 Uiso 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
Br27 C8 1.903(3) . ?
O14 C13 1.458(3) . ?
O14 C15 1.365(3) . ?
O29 C30 1.449(4) . ?
O29 C28 1.323(3) . ?
O26 C23 1.193(3) . ?
O12 C13 1.415(3) . ?
O12 C11 1.383(3) . ?
N2 N1 1.377(3) . ?
N2 C3 1.337(3) . ?
O24 C23 1.331(3) . ?
O24 C25 1.450(4) . ?
O31 C28 1.196(4) . ?
C13 H13 0.9800 . ?
C13 C22 1.519(4) . ?
N1 C16 1.420(3) . ?
N1 C15 1.365(3) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C11 C10 1.383(4) . ?
C11 C6 1.395(4) . ?
C10 H10 0.9300 . ?
C10 C9 1.377(4) . ?
C9 H9 0.9300 . ?
C9 C8 1.375(4) . ?
C3 C4 1.414(3) . ?
C3 C28 1.471(4) . ?
C16 C17 1.371(4) . ?
C16 C21 1.373(4) . ?
C8 C7 1.384(4) . ?
C7 H7 0.9300 . ?
C7 C6 1.375(4) . ?
C22 H22 0.9800 . ?
C22 C5 1.531(3) . ?
C22 C23 1.522(4) . ?
C15 C4 1.349(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.380(5) . ?
C4 C5 1.504(4) . ?
C6 C5 1.508(4) . ?
C5 H5 0.9800 . ?
C21 H21 0.9300 . ?
C21 C20 1.393(5) . ?
C20 H20 0.9300 . ?
C20 C19 1.376(5) . ?
C19 H19 0.9300 . ?
C19 C18 1.355(5) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C18 H18 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 O14 C13 110.9(2) . . ?
C28 O29 C30 115.2(2) . . ?
C11 O12 C13 120.0(2) . . ?
C3 N2 N1 104.6(2) . . ?
C23 O24 C25 115.9(2) . . ?
O14 C13 H13 108.1 . . ?
O14 C13 C22 112.1(2) . . ?
O12 C13 O14 108.2(2) . . ?
O12 C13 H13 108.1 . . ?
O12 C13 C22 112.0(2) . . ?
C22 C13 H13 108.1 . . ?
N2 N1 C16 120.7(2) . . ?
C15 N1 N2 109.6(2) . . ?
C15 N1 C16 129.5(2) . . ?
O29 C30 H30A 109.5 . . ?
O29 C30 H30B 109.5 . . ?
O29 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
O12 C11 C6 122.7(2) . . ?
C10 C11 O12 116.2(3) . . ?
C10 C11 C6 121.0(3) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 C11 119.4(3) . . ?
C9 C10 H10 120.3 . . ?
C10 C9 H9 120.2 . . ?
C8 C9 C10 119.7(3) . . ?
C8 C9 H9 120.2 . . ?
N2 C3 C4 112.3(2) . . ?
N2 C3 C28 122.8(2) . . ?
C4 C3 C28 124.8(3) . . ?
C17 C16 N1 120.1(3) . . ?
C17 C16 C21 120.7(3) . . ?
C21 C16 N1 119.2(3) . . ?
C9 C8 Br27 119.7(2) . . ?
C9 C8 C7 121.2(3) . . ?
C7 C8 Br27 119.1(2) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 C8 119.8(3) . . ?
C6 C7 H7 120.1 . . ?
C13 C22 H22 107.9 . . ?
C13 C22 C5 108.0(2) . . ?
C13 C22 C23 112.0(2) . . ?
C5 C22 H22 107.9 . . ?
C23 C22 H22 107.9 . . ?
C23 C22 C5 112.9(2) . . ?
O14 C15 N1 121.7(2) . . ?
C4 C15 O14 128.4(2) . . ?
C4 C15 N1 109.8(2) . . ?
C16 C17 H17 120.2 . . ?
C16 C17 C18 119.6(3) . . ?
C18 C17 H17 120.2 . . ?
C3 C4 C5 135.6(3) . . ?
C15 C4 C3 103.6(2) . . ?
C15 C4 C5 120.7(2) . . ?
C11 C6 C5 116.9(2) . . ?
C7 C6 C11 118.9(2) . . ?
C7 C6 C5 124.2(3) . . ?
C22 C5 H5 111.2 . . ?
C4 C5 C22 106.4(2) . . ?
C4 C5 C6 110.6(2) . . ?
C4 C5 H5 111.2 . . ?
C6 C5 C22 105.9(2) . . ?
C6 C5 H5 111.2 . . ?
O26 C23 O24 124.6(3) . . ?
O26 C23 C22 124.7(3) . . ?
O24 C23 C22 110.7(2) . . ?
O29 C28 C3 114.0(3) . . ?
O31 C28 O29 123.5(3) . . ?
O31 C28 C3 122.5(3) . . ?
C16 C21 H21 120.7 . . ?
C16 C21 C20 118.6(3) . . ?
C20 C21 H21 120.7 . . ?
C21 C20 H20 119.6 . . ?
C19 C20 C21 120.8(4) . . ?
C19 C20 H20 119.6 . . ?
C20 C19 H19 120.4 . . ?
C18 C19 C20 119.2(4) . . ?
C18 C19 H19 120.4 . . ?
O24 C25 H25A 109.5 . . ?
O24 C25 H25B 109.5 . . ?
O24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C17 C18 H18 119.5 . . ?
C19 C18 C17 121.0(4) . . ?
C19 C18 H18 119.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
