# Electronic Supplementary Material (ESI) for RSC Advances.
# 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. 
# 
#######################################################################

data_RNT-36
_database_code_depnum_ccdc_archive 'CCDC 1477443'
_audit_update_record             
;
2016-05-01 deposited with the CCDC.
2016-11-08 downloaded from the CCDC.
;
_audit_creation_date             2016-03-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_formula_moiety         'C18 H17 Br N2 O2'
_chemical_formula_sum            'C18 H17 Br N2 O2'
_chemical_formula_weight         373.25
_chemical_oxdiff_formula         C18H17BrN2O2
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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

_symmetry_Int_Tables_number      2
_cell_length_a                   8.1438(7)
_cell_length_b                   9.3009(7)
_cell_length_c                   13.9430(13)
_cell_angle_alpha                76.176(7)
_cell_angle_beta                 88.325(7)
_cell_angle_gamma                78.354(7)
_cell_volume                     1004.21(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1276
_cell_measurement_temperature    293.1(5)
_cell_measurement_theta_max      26.0750
_cell_measurement_theta_min      3.6690
_exptl_absorpt_coefficient_mu    2.055
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80591
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.2343
_exptl_crystal_description       block
_exptl_crystal_F_000             379.5982
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.03
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0574
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7833
_diffrn_reflns_theta_full        28.7211
_diffrn_reflns_theta_max         28.72
_diffrn_reflns_theta_min         3.08
_diffrn_ambient_temperature      293.1(5)
_diffrn_detector_area_resol_mean 8.0640
_diffrn_measured_fraction_theta_full 0.8994
_diffrn_measured_fraction_theta_max 0.8999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -82.00   -7.00   1.0000    8.4700
omega____ theta____ kappa____ phi______ frames
    -      -20.2184   19.0000   60.0000 75

#__ type_ start__ end____ width___ exp.time_
  2 omega  -10.00   25.00   1.0000    8.4700
omega____ theta____ kappa____ phi______ frames
    -      -20.2184  -99.0000 -120.0000 35

#__ type_ start__ end____ width___ exp.time_
  3 omega  -31.00   50.00   1.0000    8.4700
omega____ theta____ kappa____ phi______ frames
    -      -20.2184   57.0000    0.0000 81

#__ type_ start__ end____ width___ exp.time_
  4 omega   -1.00   91.00   1.0000    8.4700
omega____ theta____ kappa____ phi______ frames
    -       22.5622   57.0000 -120.0000 92

#__ type_ start__ end____ width___ exp.time_
  5 omega  -48.00   46.00   1.0000    8.4700
omega____ theta____ kappa____ phi______ frames
    -       22.5622  -57.0000   90.0000 94

#__ type_ start__ end____ width___ exp.time_
  6 omega   49.00  105.00   1.0000    8.4700
omega____ theta____ kappa____ phi______ frames
    -       22.5622 -178.0000  120.0000 56
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0042430000
_diffrn_orient_matrix_UB_12      0.0263030000
_diffrn_orient_matrix_UB_13      -0.0519569000
_diffrn_orient_matrix_UB_21      0.0859655000
_diffrn_orient_matrix_UB_22      -0.0354184000
_diffrn_orient_matrix_UB_23      0.0019495000
_diffrn_orient_matrix_UB_31      -0.0224313000
_diffrn_orient_matrix_UB_32      -0.0669379000
_diffrn_orient_matrix_UB_33      -0.0065090000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              12
_reflns_limit_k_min              -11
_reflns_limit_l_max              18
_reflns_limit_l_min              0
_reflns_number_gt                2729
_reflns_number_total             4519
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2013)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_refine_diff_density_max         0.7468
_refine_diff_density_min         -0.8700
_refine_diff_density_rms         0.1136
_refine_ls_d_res_high            0.7395
_refine_ls_d_res_low             6.6215
_refine_ls_goodness_of_fit_ref   1.0073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    27
_refine_ls_number_parameters     210
_refine_ls_number_reflns         4519
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1026
_refine_ls_R_factor_gt           0.0595
_refine_ls_restrained_S_all      1.0073
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0660P)²+0.5980P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1356
_refine_ls_wR_factor_ref         0.1602
_olex2_refinement_description    
;
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
Br1 Br 0.17104(7) 0.74095(5) 0.42602(4) 0.0940(3) Uani 1.000000 .
O1 O -0.5408(3) 1.4218(2) 0.14489(18) 0.0415(6) Uani 1.000000 .
O2 O 0.0258(3) 1.4645(3) 0.1327(2) 0.0653(8) Uani 1.000000 .
N1 N -0.6599(3) 1.2667(3) 0.0848(2) 0.0496(8) Uani 1.000000 .
N2 N -0.3177(4) 1.0206(4) -0.0073(2) 0.0539(8) Uani 1.000000 .
C13 C -0.1042(4) 1.1548(3) 0.1878(2) 0.0341(7) Uani 1.000000 .
C12 C -0.3377(4) 1.1179(4) 0.0311(2) 0.0381(8) Uani 1.000000 .
C9 C -0.2009(4) 1.2829(3) 0.1077(2) 0.0332(7) Uani 1.000000 .
C14 C 0.0260(4) 1.0508(4) 0.1627(3) 0.0449(9) Uani 1.000000 .
C5 C -0.3237(5) 1.6638(4) 0.2494(3) 0.0429(8) Uani 1.000000 .
C6 C -0.4648(4) 1.6218(4) 0.1982(3) 0.0400(8) Uani 1.000000 .
C2 C -0.2501(4) 1.4280(3) 0.1411(2) 0.0338(7) Uani 1.000000 .
C3 C -0.1190(4) 1.5106(4) 0.1513(3) 0.0424(8) Uani 1.000000 .
C10 C -0.3579(4) 1.2390(3) 0.0779(2) 0.0334(7) Uani 1.000000 .
C15 C 0.1084(5) 0.9292(4) 0.2329(3) 0.0540(10) Uani 1.000000 .
C1 C -0.4075(4) 1.4852(3) 0.1589(2) 0.0349(7) Uani 1.000000 .
C8 C -0.3831(5) 1.8229(4) 0.2648(3) 0.0605(11) Uani 1.000000 .
C11 C -0.5132(4) 1.3025(3) 0.1012(2) 0.0353(8) Uani 1.000000 .
C7 C -0.2789(6) 1.5543(5) 0.3499(3) 0.0626(12) Uani 1.000000 .
C4 C -0.1718(5) 1.6572(4) 0.1827(3) 0.0502(10) Uani 1.000000 .
C18 C -0.1495(4) 1.1330(4) 0.2857(3) 0.0428(8) Uani 1.000000 .
C16 C 0.0598(5) 0.9101(4) 0.3296(3) 0.0490(9) Uani 1.000000 .
C17 C -0.0681(5) 1.0109(4) 0.3570(3) 0.0501(9) Uani 1.000000 .
H23 H -0.1000(5) 0.9976(4) 0.4227(3) 0.0601(11) Uiso 1.000000 R
H21 H -0.2367(4) 1.2020(4) 0.3040(3) 0.0513(10) Uiso 1.000000 R
H9 H 0.0585(4) 1.0633(4) 0.0973(3) 0.0539(10) Uiso 1.000000 R
H15 H 0.1962(5) 0.8603(4) 0.2151(3) 0.0648(12) Uiso 1.000000 R
H8 H -0.1298(4) 1.3001(3) 0.0498(2) 0.0399(8) Uiso 1.000000 R
H11a H -0.5534(4) 1.6041(4) 0.2449(3) 0.0480(10) Uiso 1.000000 R
H11b H -0.5114(4) 1.7063(4) 0.1442(3) 0.0480(10) Uiso 1.000000 R
H17a H -0.410(3) 1.8929(6) 0.2019(4) 0.0907(17) Uiso 1.000000 GR
H17b H -0.481(2) 1.8255(9) 0.3052(17) 0.0907(17) Uiso 1.000000 GR
H17c H -0.2955(14) 1.8504(13) 0.297(2) 0.0907(17) Uiso 1.000000 GR
H19a H -0.3760(11) 1.557(2) 0.3906(8) 0.0939(18) Uiso 1.000000 GR
H19b H -0.241(3) 1.4537(7) 0.3411(3) 0.0939(18) Uiso 1.000000 GR
H19c H -0.191(3) 1.583(2) 0.3811(10) 0.0939(18) Uiso 1.000000 GR
H20a H -0.1970(5) 1.7390(4) 0.1240(3) 0.0602(12) Uiso 1.000000 R
H20b H -0.0781(5) 1.6739(4) 0.2171(3) 0.0602(12) Uiso 1.000000 R
H4a H -0.6441(6) 1.1732(9) 0.083(2) 0.0595(10) Uiso 1.000000 GR
H4b H -0.7259(12) 1.282(3) 0.1323(11) 0.0595(10) Uiso 1.000000 GR


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C16 1.895(3) . ?
O1 C1 1.375(4) . ?
O1 C11 1.366(4) . ?
O2 C3 1.213(4) . ?
N1 C11 1.343(4) . ?
N2 C12 1.140(4) . ?
C13 C9 1.525(4) . ?
C13 C14 1.381(4) . ?
C13 C18 1.381(5) . ?
C12 C10 1.411(4) . ?
C9 C2 1.506(4) . ?
C9 C10 1.516(4) . ?
C14 C15 1.375(5) . ?
C5 C6 1.531(4) . ?
C5 C8 1.525(5) . ?
C5 C7 1.527(5) . ?
C5 C4 1.526(5) . ?
C6 C1 1.487(4) . ?
C2 C3 1.464(5) . ?
C2 C1 1.326(4) . ?
C3 C4 1.507(5) . ?
C10 C11 1.350(4) . ?
C15 C16 1.374(6) . ?
C18 C17 1.384(5) . ?
C16 C17 1.365(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O1 C1 118.7(2) . . ?
C14 C13 C9 120.1(3) . . ?
C18 C13 C9 121.7(3) . . ?
C18 C13 C14 118.0(3) . . ?
C10 C12 N2 178.4(4) . . ?
C2 C9 C13 112.2(2) . . ?
C10 C9 C13 109.9(3) . . ?
C10 C9 C2 108.9(2) . . ?
C15 C14 C13 121.2(4) . . ?
C8 C5 C6 108.7(3) . . ?
C7 C5 C6 110.7(3) . . ?
C7 C5 C8 108.8(3) . . ?
C4 C5 C6 107.8(3) . . ?
C4 C5 C8 110.7(3) . . ?
C4 C5 C7 110.1(3) . . ?
C1 C6 C5 112.9(3) . . ?
C3 C2 C9 118.4(3) . . ?
C1 C2 C9 122.6(3) . . ?
C1 C2 C3 119.0(3) . . ?
C2 C3 O2 121.1(3) . . ?
C4 C3 O2 121.5(3) . . ?
C4 C3 C2 117.4(3) . . ?
C9 C10 C12 117.7(3) . . ?
C11 C10 C12 119.3(3) . . ?
C11 C10 C9 122.7(3) . . ?
C16 C15 C14 119.5(3) . . ?
C6 C1 O1 110.7(3) . . ?
C2 C1 O1 123.5(3) . . ?
C2 C1 C6 125.8(3) . . ?
N1 C11 O1 109.8(3) . . ?
C10 C11 O1 121.9(3) . . ?
C10 C11 N1 128.2(3) . . ?
C3 C4 C5 114.7(3) . . ?
C17 C18 C13 121.5(3) . . ?
C15 C16 Br1 119.5(3) . . ?
C17 C16 Br1 119.5(3) . . ?
C17 C16 C15 121.0(3) . . ?
C16 C17 C18 118.9(4) . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.040 -0.540 0.500 245.7 17.0 ?

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method ethanol
####################################################################### 
# 
# 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_RNT-65
_database_code_depnum_ccdc_archive 'CCDC 1477627'
_audit_update_record             
;
2016-05-02 deposited with the CCDC.
2016-11-08 downloaded from the CCDC.
;
_audit_creation_date             2016-03-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_formula_moiety         'C21 H25 N O4'
_chemical_formula_sum            'C21 H25 N O4'
_chemical_formula_weight         355.44
_chemical_oxdiff_formula         C21H25NO4
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

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

_symmetry_Int_Tables_number      14
_cell_length_a                   14.2687(10)
_cell_length_b                   8.0116(7)
_cell_length_c                   16.7510(11)
_cell_angle_alpha                90
_cell_angle_beta                 96.487(6)
_cell_angle_gamma                90
_cell_volume                     1902.6(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2370
_cell_measurement_temperature    294.12(18)
_cell_measurement_theta_max      28.1430
_cell_measurement_theta_min      3.9070
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96071
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.2407
_exptl_crystal_description       block
_exptl_crystal_F_000             760.3996
_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.64
_exptl_crystal_size_min          0.53
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8690
_diffrn_reflns_theta_full        28.7895
_diffrn_reflns_theta_max         28.79
_diffrn_reflns_theta_min         3.23
_diffrn_ambient_temperature      294.12(18)
_diffrn_detector_area_resol_mean 8.0640
_diffrn_measured_fraction_theta_full 0.9830
_diffrn_measured_fraction_theta_max 0.9830
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -25.00    0.00   1.0000    4.6300
omega____ theta____ kappa____ phi______ frames
    -      -20.4528  -99.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
  2 omega   33.00   99.00   1.0000    4.6300
omega____ theta____ kappa____ phi______ frames
    -       22.8747 -178.0000  120.0000 66

#__ type_ start__ end____ width___ exp.time_
  3 omega   50.00   97.00   1.0000    4.6300
omega____ theta____ kappa____ phi______ frames
    -       22.8747  178.0000  -90.0000 47

#__ type_ start__ end____ width___ exp.time_
  4 omega   15.00   87.00   1.0000    4.6300
omega____ theta____ kappa____ phi______ frames
    -       22.8747   57.0000 -120.0000 72

#__ type_ start__ end____ width___ exp.time_
  5 omega  -51.00    1.00   1.0000    4.6300
omega____ theta____ kappa____ phi______ frames
    -       22.8747  -37.0000  -60.0000 52
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0249839000
_diffrn_orient_matrix_UB_12      -0.0404858000
_diffrn_orient_matrix_UB_13      0.0336036000
_diffrn_orient_matrix_UB_21      0.0426109000
_diffrn_orient_matrix_UB_22      0.0367713000
_diffrn_orient_matrix_UB_23      -0.0094532000
_diffrn_orient_matrix_UB_31      -0.0080058000
_diffrn_orient_matrix_UB_32      0.0695818000
_diffrn_orient_matrix_UB_33      0.0244576000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              17
_reflns_limit_h_min              -17
_reflns_limit_k_max              10
_reflns_limit_k_min              0
_reflns_limit_l_max              22
_reflns_limit_l_min              0
_reflns_number_gt                3254
_reflns_number_total             4379
_reflns_odcompleteness_completeness 99.55
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2013)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_refine_diff_density_max         0.5233
_refine_diff_density_min         -0.4454
_refine_diff_density_rms         0.0603
_refine_ls_d_res_high            0.7379
_refine_ls_d_res_low             6.3091
_refine_ls_goodness_of_fit_ref   1.0267
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    38
_refine_ls_number_parameters     239
_refine_ls_number_reflns         4379
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0822
_refine_ls_R_factor_gt           0.0607
_refine_ls_restrained_S_all      1.0267
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0900P)²+0.6380P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1627
_refine_ls_wR_factor_ref         0.1804
_olex2_refinement_description    
;
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
O2 O 0.37803(9) 0.66513(17) 0.70304(7) 0.0379(3) Uani 1.000000 .
O1 O 0.37787(10) 0.8431(2) 0.97061(8) 0.0510(4) Uani 1.000000 .
O4 O 0.08161(10) 0.8229(2) 0.77500(9) 0.0586(5) Uani 1.000000 .
N1 N 0.26141(13) 0.6913(3) 0.60402(9) 0.0514(5) Uani 1.000000 .
H1a H 0.2818(11) 0.5973(11) 0.58811(19) 0.0616(6) Uiso 1.000000 GR
H1b H 0.20104(15) 0.695(2) 0.59357(14) 0.0616(6) Uiso 1.000000 GR
C15 C 0.23265(12) 0.5808(2) 0.86778(10) 0.0332(4) Uani 1.000000 .
C9 C 0.28440(13) 0.7043(2) 0.68342(10) 0.0352(4) Uani 1.000000 .
O3 O 0.09446(11) 0.7923(3) 0.64368(9) 0.0706(6) Uani 1.000000 .
C4 C 0.57135(13) 0.6869(3) 0.86949(11) 0.0383(4) Uani 1.000000 .
C2 C 0.42080(13) 0.8065(2) 0.91429(10) 0.0340(4) Uani 1.000000 .
C10 C 0.22786(12) 0.7482(2) 0.73982(10) 0.0358(4) Uani 1.000000 .
C7 C 0.52445(12) 0.7013(3) 0.78289(10) 0.0367(4) Uani 1.000000 .
H7a H 0.54764(12) 0.8007(3) 0.75854(10) 0.0440(5) Uiso 1.000000 R
H7b H 0.54213(12) 0.6056(3) 0.75241(10) 0.0440(5) Uiso 1.000000 R
C16 C 0.16724(13) 0.5844(3) 0.92326(11) 0.0411(5) Uani 1.000000 .
H16 H 0.14444(13) 0.6864(3) 0.93925(11) 0.0493(6) Uiso 1.000000 R
C8 C 0.42000(12) 0.7099(2) 0.77805(10) 0.0311(4) Uani 1.000000 .
C14 C 0.26396(12) 0.7398(2) 0.82855(10) 0.0318(4) Uani 1.000000 .
H14 H 0.23884(12) 0.8357(2) 0.85558(10) 0.0382(5) Uiso 1.000000 R
C18 C 0.16767(15) 0.2847(3) 0.93336(12) 0.0474(5) Uani 1.000000 .
C3 C 0.52687(13) 0.8175(3) 0.91989(11) 0.0413(5) Uani 1.000000 .
H3a H 0.55268(13) 0.8046(3) 0.97564(11) 0.0495(6) Uiso 1.000000 R
H3b H 0.54419(13) 0.9277(3) 0.90256(11) 0.0495(6) Uiso 1.000000 R
C17 C 0.13567(15) 0.4381(3) 0.95496(12) 0.0496(5) Uani 1.000000 .
H17 H 0.09167(15) 0.4438(3) 0.99182(12) 0.0595(7) Uiso 1.000000 R
C21 C 0.26599(15) 0.4269(3) 0.84765(12) 0.0454(5) Uani 1.000000 .
H21 H 0.31079(15) 0.4210(3) 0.81151(12) 0.0545(6) Uiso 1.000000 R
C11 C 0.13080(14) 0.7893(3) 0.71283(12) 0.0461(5) Uani 1.000000 .
C1 C 0.36996(12) 0.7525(2) 0.83760(10) 0.0309(4) Uani 1.000000 .
C5 C 0.55578(17) 0.5140(3) 0.90267(13) 0.0542(6) Uani 1.000000 .
H5a H 0.48939(18) 0.4945(8) 0.9027(9) 0.0813(9) Uiso 1.000000 GR
H5b H 0.5817(10) 0.4318(3) 0.8697(6) 0.0813(9) Uiso 1.000000 GR
H5c H 0.5864(10) 0.5063(7) 0.9566(4) 0.0813(9) Uiso 1.000000 GR
C20 C 0.23471(17) 0.2814(3) 0.87963(13) 0.0519(5) Uani 1.000000 .
H20 H 0.25894(17) 0.1795(3) 0.86496(13) 0.0623(7) Uiso 1.000000 R
C6 C 0.67697(15) 0.7192(4) 0.87046(15) 0.0600(7) Uani 1.000000 .
H6a H 0.7033(3) 0.6398(14) 0.8363(9) 0.0900(10) Uiso 1.000000 GR
H6b H 0.68671(15) 0.8301(9) 0.8513(10) 0.0900(10) Uiso 1.000000 GR
H6c H 0.7073(2) 0.708(2) 0.9243(2) 0.0900(10) Uiso 1.000000 GR
C19 C 0.1300(2) 0.1256(4) 0.96506(17) 0.0758(8) Uani 1.000000 .
H19a H 0.1812(3) 0.0617(13) 0.9918(11) 0.1137(13) Uiso 1.000000 GR
H19b H 0.0857(11) 0.1516(4) 1.0023(10) 0.1137(13) Uiso 1.000000 GR
H19c H 0.0991(13) 0.0618(13) 0.9212(2) 0.1137(13) Uiso 1.000000 GR
C13 C -0.0656(2) 0.8297(6) 0.8243(2) 0.1082(14) Uani 1.000000 .
H13a H -0.1316(4) 0.852(4) 0.8114(5) 0.162(2) Uiso 1.000000 GR
H13b H -0.0573(19) 0.7171(11) 0.8434(11) 0.162(2) Uiso 1.000000 GR
H13c H -0.0394(15) 0.906(3) 0.8652(7) 0.162(2) Uiso 1.000000 GR
C12 C -0.01895(17) 0.8503(5) 0.75450(18) 0.0884(11) Uani 1.000000 .
H12a H -0.02986(17) 0.9621(5) 0.73326(18) 0.1061(13) Uiso 1.000000 R
H12b H -0.04369(17) 0.7712(5) 0.71358(18) 0.1061(13) Uiso 1.000000 R


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
O2 C9 1.376(2) . ?
O2 C8 1.377(2) . ?
O1 C2 1.217(2) . ?
O4 C11 1.347(2) . ?
O4 C12 1.454(3) . ?
N1 C9 1.338(2) . ?
C15 C16 1.390(2) . ?
C15 C14 1.523(3) . ?
C15 C21 1.377(3) . ?
C9 C10 1.356(3) . ?
O3 C11 1.215(3) . ?
C4 C7 1.532(2) . ?
C4 C3 1.527(3) . ?
C4 C5 1.518(3) . ?
C4 C6 1.527(3) . ?
C2 C3 1.508(3) . ?
C2 C1 1.467(2) . ?
C10 C14 1.518(2) . ?
C10 C11 1.445(3) . ?
C7 C8 1.485(2) . ?
C16 C17 1.383(3) . ?
C8 C1 1.335(2) . ?
C14 C1 1.506(2) . ?
C18 C17 1.374(3) . ?
C18 C20 1.386(3) . ?
C18 C19 1.504(3) . ?
C21 C20 1.378(3) . ?
C13 C12 1.418(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O2 C9 117.98(13) . . ?
C12 O4 C11 115.73(18) . . ?
C14 C15 C16 121.51(17) . . ?
C21 C15 C16 117.34(18) . . ?
C21 C15 C14 121.11(15) . . ?
N1 C9 O2 110.01(16) . . ?
C10 C9 O2 122.06(15) . . ?
C10 C9 N1 127.93(18) . . ?
C3 C4 C7 107.90(15) . . ?
C5 C4 C7 110.44(17) . . ?
C5 C4 C3 109.63(16) . . ?
C6 C4 C7 108.80(16) . . ?
C6 C4 C3 110.42(17) . . ?
C6 C4 C5 109.63(18) . . ?
C3 C2 O1 121.79(16) . . ?
C1 C2 O1 120.48(17) . . ?
C1 C2 C3 117.71(15) . . ?
C14 C10 C9 120.50(16) . . ?
C11 C10 C9 117.74(16) . . ?
C11 C10 C14 121.56(16) . . ?
C8 C7 C4 112.56(15) . . ?
C17 C16 C15 120.8(2) . . ?
C7 C8 O2 111.60(14) . . ?
C1 C8 O2 122.30(15) . . ?
C1 C8 C7 126.10(15) . . ?
C10 C14 C15 112.09(15) . . ?
C1 C14 C15 110.69(14) . . ?
C1 C14 C10 108.73(14) . . ?
C20 C18 C17 117.55(19) . . ?
C19 C18 C17 121.5(2) . . ?
C19 C18 C20 120.9(2) . . ?
C2 C3 C4 113.70(15) . . ?
C18 C17 C16 121.65(18) . . ?
C20 C21 C15 121.74(18) . . ?
O3 C11 O4 121.99(18) . . ?
C10 C11 O4 111.60(17) . . ?
C10 C11 O3 126.41(19) . . ?
C8 C1 C2 118.45(15) . . ?
C14 C1 C2 119.97(15) . . ?
C14 C1 C8 121.54(15) . . ?
C21 C20 C18 120.9(2) . . ?
C13 C12 O4 109.3(2) . . ?

####################################################################### 
# 
# 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_RNT-48
_database_code_depnum_ccdc_archive 'CCDC 1477628'
_audit_update_record             
;
2016-05-02 deposited with the CCDC.
2016-11-08 downloaded from the CCDC.
;
_audit_creation_date             2016-03-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_formula_moiety         'C21 H16 Br N O5'
_chemical_formula_sum            'C21 H16 Br N O5'
_chemical_formula_weight         442.27
_chemical_oxdiff_formula         C21H16O5NB
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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

_symmetry_Int_Tables_number      2
_cell_length_a                   8.6633(7)
_cell_length_b                   10.4989(11)
_cell_length_c                   10.9588(10)
_cell_angle_alpha                99.683(8)
_cell_angle_beta                 100.554(7)
_cell_angle_gamma                92.904(7)
_cell_volume                     962.52(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1742
_cell_measurement_temperature    294.3(3)
_cell_measurement_theta_max      26.9160
_cell_measurement_theta_min      3.9530
_exptl_absorpt_coefficient_mu    2.168
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78190
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.5259
_exptl_crystal_description       block
_exptl_crystal_F_000             447.6729
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.12
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7088
_diffrn_reflns_theta_full        28.6406
_diffrn_reflns_theta_max         28.64
_diffrn_reflns_theta_min         3.23
_diffrn_ambient_temperature      294.3(3)
_diffrn_detector_area_resol_mean 8.0640
_diffrn_measured_fraction_theta_full 0.9992
_diffrn_measured_fraction_theta_max 0.9982
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   57.00   93.00   1.0000    9.4700
omega____ theta____ kappa____ phi______ frames
    -       22.4059   57.0000  -90.0000 36

#__ type_ start__ end____ width___ exp.time_
  2 omega   -5.00   26.00   1.0000    9.4700
omega____ theta____ kappa____ phi______ frames
    -       22.4059   77.0000  120.0000 31

#__ type_ start__ end____ width___ exp.time_
  3 omega  -33.00   45.00   1.0000    9.4700
omega____ theta____ kappa____ phi______ frames
    -       22.4059  -57.0000    0.0000 78

#__ type_ start__ end____ width___ exp.time_
  4 omega  -23.00   60.00   1.0000    9.4700
omega____ theta____ kappa____ phi______ frames
    -       22.4059  -99.0000 -120.0000 83

#__ type_ start__ end____ width___ exp.time_
  5 omega  -46.00   43.00   1.0000    9.4700
omega____ theta____ kappa____ phi______ frames
    -       22.4059  -57.0000  120.0000 89

#__ type_ start__ end____ width___ exp.time_
  6 omega  -24.00   58.00   1.0000    9.4700
omega____ theta____ kappa____ phi______ frames
    -       22.4059  -99.0000    0.0000 82
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0497589000
_diffrn_orient_matrix_UB_12      -0.0161803000
_diffrn_orient_matrix_UB_13      0.0407811000
_diffrn_orient_matrix_UB_21      -0.0602638000
_diffrn_orient_matrix_UB_22      -0.0251158000
_diffrn_orient_matrix_UB_23      -0.0530210000
_diffrn_orient_matrix_UB_31      0.0296271000
_diffrn_orient_matrix_UB_32      -0.0619516000
_diffrn_orient_matrix_UB_33      -0.0025898000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              13
_reflns_limit_k_min              -14
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                2923
_reflns_number_total             4309
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2013)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_refine_diff_density_max         0.7323
_refine_diff_density_min         -0.5763
_refine_diff_density_rms         0.0964
_refine_ls_d_res_high            0.7414
_refine_ls_d_res_low             6.2984
_refine_ls_goodness_of_fit_ref   1.0226
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    25
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4309
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0450
_refine_ls_restrained_S_all      1.0226
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0570P)²+0.1780P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1033
_refine_ls_wR_factor_ref         0.1219
_olex2_refinement_description    
;
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
Br1 Br 0.49597(4) 0.24693(4) 0.53785(4) 0.07470(18) Uani 1.000000 .
O3 O 1.0832(2) 0.67673(19) 0.2355(2) 0.0475(5) Uani 1.000000 .
O2 O 0.5262(2) 0.6518(2) 0.1347(2) 0.0536(5) Uani 1.000000 .
O5 O 0.8459(2) 0.25422(18) 0.0556(2) 0.0505(5) Uani 1.000000 .
O4 O 1.1108(3) 0.2828(2) 0.0925(2) 0.0639(6) Uani 1.000000 .
C14 C 0.5835(3) 0.3555(3) 0.2086(3) 0.0396(6) Uani 1.000000 .
C12 C 0.7954(3) 0.5017(2) 0.1552(3) 0.0350(6) Uani 1.000000 .
O1 O 0.6597(2) 0.83940(19) 0.2246(2) 0.0518(5) Uani 1.000000 .
C18 C 0.7813(3) 0.4706(3) 0.3774(3) 0.0459(7) Uani 1.000000 .
C11 C 0.9606(3) 0.4607(3) 0.1498(3) 0.0375(6) Uani 1.000000 .
N1 N 1.2417(3) 0.5238(3) 0.1908(3) 0.0558(7) Uani 1.000000 .
C4 C 0.9428(3) 0.8620(3) 0.2760(3) 0.0442(7) Uani 1.000000 .
C3 C 0.9378(3) 0.7234(3) 0.2304(3) 0.0386(6) Uani 1.000000 .
C13 C 0.7196(3) 0.4408(2) 0.2495(2) 0.0331(6) Uani 1.000000 .
C15 C 0.5147(3) 0.2995(3) 0.2938(3) 0.0458(7) Uani 1.000000 .
C9 C 1.0815(4) 0.9443(3) 0.3255(3) 0.0596(9) Uani 1.000000 .
C10 C 1.0903(3) 0.5479(3) 0.1882(3) 0.0401(6) Uani 1.000000 .
C19 C 0.9836(3) 0.3283(3) 0.0986(3) 0.0463(7) Uani 1.000000 .
C16 C 0.5814(3) 0.3295(3) 0.4199(3) 0.0451(7) Uani 1.000000 .
C8 C 1.0713(5) 1.0739(4) 0.3666(4) 0.0774(11) Uani 1.000000 .
C20 C 0.8583(5) 0.1177(3) 0.0088(4) 0.0600(9) Uani 1.000000 .
C7 C 0.9255(6) 1.1244(4) 0.3622(4) 0.0813(12) Uani 1.000000 .
C2 C 0.8022(3) 0.6477(2) 0.1892(2) 0.0338(6) Uani 1.000000 .
C5 C 0.7991(4) 0.9150(3) 0.2728(3) 0.0493(7) Uani 1.000000 .
C6 C 0.7893(5) 1.0458(3) 0.3171(4) 0.0694(10) Uani 1.000000 .
C17 C 0.7146(4) 0.4165(3) 0.4642(3) 0.0522(8) Uani 1.000000 .
C21 C 0.6960(5) 0.0542(4) -0.0363(5) 0.0909(14) Uani 1.000000 .
C1 C 0.6546(3) 0.7076(3) 0.1797(3) 0.0420(7) Uani 1.000000 .
H18 H 0.7575(4) 0.4377(3) 0.5500(3) 0.0626(9) Uiso 1.000000 R
H17 H 0.8703(3) 0.5287(3) 0.4059(3) 0.0551(8) Uiso 1.000000 R
H21 H 0.5385(3) 0.3360(3) 0.1231(3) 0.0475(7) Uiso 1.000000 R
H20 H 0.4246(3) 0.2424(3) 0.2659(3) 0.0549(8) Uiso 1.000000 R
H1 H 0.6918(5) 1.0792(3) 0.3162(4) 0.0833(12) Uiso 1.000000 R
H2 H 0.9206(6) 1.2125(4) 0.3901(4) 0.0976(14) Uiso 1.000000 R
H3 H 1.1629(5) 1.1286(4) 0.3979(4) 0.0929(14) Uiso 1.000000 R
H4 H 1.1795(4) 0.9110(3) 0.3303(3) 0.0715(10) Uiso 1.000000 R
H15 H 0.7292(3) 0.4744(2) 0.0711(3) 0.0420(7) Uiso 1.000000 R
H14a H 0.6479(15) 0.084(3) -0.1113(18) 0.136(2) Uiso 1.000000 GR
H14b H 0.7001(6) -0.0381(4) -0.055(3) 0.136(2) Uiso 1.000000 GR
H14c H 0.6349(12) 0.076(3) 0.0280(12) 0.136(2) Uiso 1.000000 GR
H1a H 1.2479(3) 0.4554(14) 0.1369(17) 0.0669(8) Uiso 1.000000 GR
H1b H 1.2911(7) 0.5891(10) 0.173(2) 0.0669(8) Uiso 1.000000 GR
H13a H 0.927(4) 0.086(3) 0.086(4) 0.082(12) Uiso 1.000000 .
H13b H 0.923(4) 0.110(3) -0.061(4) 0.075(11) Uiso 1.000000 .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C16 1.906(3) . ?
O3 C3 1.369(3) . ?
O3 C10 1.373(3) . ?
O2 C1 1.208(3) . ?
O5 C19 1.352(3) . ?
O5 C20 1.455(4) . ?
O4 C19 1.232(3) . ?
C14 C13 1.400(3) . ?
C14 C15 1.387(4) . ?
C12 C11 1.523(4) . ?
C12 C13 1.529(3) . ?
C12 C2 1.511(4) . ?
O1 C5 1.376(4) . ?
O1 C1 1.384(3) . ?
C18 C13 1.381(4) . ?
C18 C17 1.383(4) . ?
C11 C10 1.368(4) . ?
C11 C19 1.447(4) . ?
N1 C10 1.345(3) . ?
C4 C3 1.453(4) . ?
C4 C9 1.408(4) . ?
C4 C5 1.387(4) . ?
C3 C2 1.344(4) . ?
C15 C16 1.373(4) . ?
C9 C8 1.373(5) . ?
C16 C17 1.393(4) . ?
C8 C7 1.390(6) . ?
C20 C21 1.485(5) . ?
C7 C6 1.367(5) . ?
C2 C1 1.448(4) . ?
C5 C6 1.390(5) . ?

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
C10 O3 C3 118.2(2) . . ?
C20 O5 C19 116.0(2) . . ?
C15 C14 C13 120.9(3) . . ?
C13 C12 C11 112.8(2) . . ?
C2 C12 C11 109.3(2) . . ?
C2 C12 C13 109.5(2) . . ?
C1 O1 C5 122.5(2) . . ?
C17 C18 C13 121.9(3) . . ?
C10 C11 C12 121.5(2) . . ?
C19 C11 C12 120.4(2) . . ?
C19 C11 C10 118.0(2) . . ?
C9 C4 C3 124.9(3) . . ?
C5 C4 C3 116.7(3) . . ?
C5 C4 C9 118.4(3) . . ?
C4 C3 O3 114.0(2) . . ?
C2 C3 O3 123.2(2) . . ?
C2 C3 C4 122.7(2) . . ?
C12 C13 C14 120.7(2) . . ?
C18 C13 C14 118.2(2) . . ?
C18 C13 C12 121.1(2) . . ?
C16 C15 C14 119.1(3) . . ?
C8 C9 C4 119.6(3) . . ?
C11 C10 O3 123.5(2) . . ?
N1 C10 O3 109.2(2) . . ?
N1 C10 C11 127.3(3) . . ?
O4 C19 O5 121.2(3) . . ?
C11 C19 O5 112.3(2) . . ?
C11 C19 O4 126.4(3) . . ?
C15 C16 Br1 119.9(2) . . ?
C17 C16 Br1 118.5(2) . . ?
C17 C16 C15 121.5(3) . . ?
C7 C8 C9 120.7(3) . . ?
C21 C20 O5 107.8(3) . . ?
C6 C7 C8 120.6(4) . . ?
C3 C2 C12 123.1(2) . . ?
C1 C2 C12 117.9(2) . . ?
C1 C2 C3 118.9(2) . . ?
C4 C5 O1 120.9(3) . . ?
C6 C5 O1 117.3(3) . . ?
C6 C5 C4 121.8(3) . . ?
C5 C6 C7 118.8(4) . . ?
C16 C17 C18 118.3(3) . . ?
O1 C1 O2 116.9(2) . . ?
C2 C1 O2 125.2(3) . . ?
C2 C1 O1 117.9(2) . . ?

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method ethanol
