# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_I
_database_code_depnum_ccdc_archive 'CCDC 1023711'
_audit_update_record             
;
2014-09-10 deposited with the CCDC.
2014-11-27 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C20 H21 N O3'
_chemical_formula_sum            'C20 H21 N O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         323.38
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   7.4058(6)
_cell_length_b                   12.3833(12)
_cell_length_c                   18.9412(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1737.1(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_cell_measurement_temperature    233.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.870
_exptl_crystal_size_mid          0.480
_exptl_crystal_size_min          0.420
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688

_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           
;
;

_diffrn_ambient_temperature      233.(2)

_diffrn_radiation_source         'sealed MicroFocus tube'
_diffrn_source_type              ?

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'doubly curved silicon crystal'

_diffrn_measurement_device_type  'SMART X2S'
_diffrn_measurement_method       omega-scan

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            19092
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_sigmaI/netI    0.0288
_diffrn_reflns_theta_min         2.71
_diffrn_reflns_theta_max         25.06
_diffrn_reflns_theta_full        25.06
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22

_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.
;

_reflns_number_total             3070
_reflns_number_gt                2793
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0352
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.0978
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_number_reflns         3070
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0476P)²+0.2534P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.158
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.026(2)
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.7(13)

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'

_computing_cell_refinement       'SAINT V7.66A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.66A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C11 0.4794(2) 0.20600(16) 0.65166(11) 0.0566(5) Uani d . 1.0 A 1
H H11 0.4191 0.2371 0.613 0.068 Uiso calc R 1.0 A 1
O O2 1.04135(17) 0.01209(12) 0.53082(7) 0.0633(4) Uani d . 1.0 A 1
O O3 1.05248(17) 0.23379(10) 0.54342(6) 0.0554(3) Uani d . 1.0 A 1
C C9 0.5671(4) 0.2120(2) 0.77433(13) 0.0815(8) Uani d . 1.0 A 1
H H9 0.5663 0.2466 0.8185 0.098 Uiso calc R 1.0 A 1
C C10 0.4791(3) 0.25827(19) 0.71776(14) 0.0758(7) Uani d . 1.0 A 1
H H10 0.4191 0.3246 0.7233 0.091 Uiso calc R 1.0 A 1
C C6 0.5686(2) 0.10893(14) 0.64417(8) 0.0426(4) Uani d . 1.0 A 1
C C12 0.8987(2) 0.05658(14) 0.54584(8) 0.0425(4) Uani d . 1.0 A 1
C C13 0.8892(2) 0.17647(14) 0.55642(8) 0.0436(4) Uani d . 1.0 A 1
H H13 0.7762 0.2123 0.5412 0.052 Uiso calc R 1.0 A 1
C C14 0.9877(2) 0.22805(15) 0.61495(9) 0.0436(4) Uani d . 1.0 A 1
H H14 1.0548 0.1779 0.6461 0.052 Uiso calc R 1.0 A 1
C C15 0.9264(2) 0.32917(14) 0.64913(9) 0.0476(4) Uani d . 1.0 A 1
C C16 0.9638(3) 0.34622(17) 0.72025(11) 0.0588(5) Uani d . 1.0 A 1
H H16 1.031 0.2947 0.7455 0.071 Uiso calc R 1.0 A 1
C C17 0.9027(3) 0.4383(2) 0.75413(13) 0.0738(6) Uani d . 1.0 A 1
H H17 0.9276 0.4488 0.8023 0.089 Uiso calc R 1.0 A 1
C C18 0.8063(3) 0.5138(2) 0.71742(15) 0.0796(7) Uani d . 1.0 A 1
H H18 0.7661 0.5767 0.7403 0.096 Uiso calc R 1.0 A 1
C C7 0.6561(3) 0.06461(17) 0.70229(9) 0.0568(5) Uani d . 1.0 A 1
H H7 0.717 -0.0016 0.6977 0.068 Uiso calc R 1.0 A 1
C C8 0.6544(3) 0.1168(2) 0.76637(11) 0.0766(7) Uani d . 1.0 A 1
H H8 0.7146 0.0859 0.8051 0.092 Uiso calc R 1.0 A 1
C C19 0.7674(3) 0.49811(19) 0.64636(15) 0.0761(6) Uani d . 1.0 A 1
H H19 0.7001 0.55 0.6215 0.091 Uiso calc R 1.0 A 1
C C20 0.8276(3) 0.40654(16) 0.61234(11) 0.0599(5) Uani d . 1.0 A 1
H H20 0.8018 0.3963 0.5642 0.072 Uiso calc R 1.0 A 1
C C1 0.5666(2) 0.05105(14) 0.57380(8) 0.0408(4) Uani d . 1.0 A 1
H H1 0.5274 0.1015 0.5363 0.049 Uiso calc R 1.0 A 1
N N1 0.74162(17) 0.00216(11) 0.55431(6) 0.0388(3) Uani d . 1.0 A 1
C C3 0.7220(3) -0.11445(16) 0.53797(11) 0.0573(5) Uani d . 1.0 A 1
C C2 0.4471(3) -0.04863(16) 0.57318(12) 0.0638(5) Uani d . 1.0 A 1
H H2A 0.4353 -0.0777 0.6211 0.077 Uiso calc R 1.0 A 1
H H2B 0.3264 -0.0301 0.5558 0.077 Uiso calc R 1.0 A 1
C C5 0.7570(4) -0.1369(2) 0.46056(12) 0.0910(8) Uani d . 1.0 A 1
H H5A 0.6882 -0.0867 0.4319 0.136 Uiso calc R 1.0 A 1
H H5B 0.7204 -0.2102 0.4495 0.136 Uiso calc R 1.0 A 1
H H5C 0.8847 -0.1283 0.4507 0.136 Uiso calc R 1.0 A 1
C C4 0.8319(4) -0.18550(18) 0.58552(13) 0.0912(9) Uani d . 1.0 A 1
H H4A 0.9593 -0.1718 0.5777 0.137 Uiso calc R 1.0 A 1
H H4B 0.8055 -0.2606 0.5753 0.137 Uiso calc R 1.0 A 1
H H4C 0.8019 -0.1701 0.6343 0.137 Uiso calc R 1.0 A 1
O O1A 0.5221(4) -0.1203(4) 0.5317(4) 0.0642(17) Uani d P 0.553(11) A 1
O O1B 0.5585(6) -0.1415(2) 0.5744(4) 0.0476(15) Uani d P 0.447(11) A 2


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C11 C6 . 1.379(3) ?
C11 C10 . 1.409(3) ?
C11 H11 . 0.94 ?
O2 C12 . 1.225(2) ?
O3 C13 . 1.4236(19) ?
O3 C14 . 1.439(2) ?
C9 C8 . 1.353(4) ?
C9 C10 . 1.379(4) ?
C9 H9 . 0.94 ?
C10 H10 . 0.94 ?
C6 C7 . 1.390(2) ?
C6 C1 . 1.514(2) ?
C12 N1 . 1.354(2) ?
C12 C13 . 1.500(2) ?
C13 C14 . 1.473(2) ?
C13 H13 . 0.99 ?
C14 C15 . 1.481(3) ?
C14 H14 . 0.99 ?
C15 C16 . 1.391(3) ?
C15 C20 . 1.393(3) ?
C16 C17 . 1.384(3) ?
C16 H16 . 0.94 ?
C17 C18 . 1.367(3) ?
C17 H17 . 0.94 ?
C18 C19 . 1.390(3) ?
C18 H18 . 0.94 ?
C7 C8 . 1.375(3) ?
C7 H7 . 0.94 ?
C8 H8 . 0.94 ?
C19 C20 . 1.378(3) ?
C19 H19 . 0.94 ?
C20 H20 . 0.94 ?
C1 N1 . 1.478(2) ?
C1 C2 . 1.519(3) ?
C1 H1 . 0.99 ?
N1 C3 . 1.484(2) ?
C3 O1A . 1.487(4) ?
C3 C4 . 1.499(3) ?
C3 C5 . 1.515(3) ?
C2 O1A . 1.308(3) ?
C2 H2A . 0.98 ?
C2 H2B . 0.98 ?
C5 H5A . 0.97 ?
C5 H5B . 0.97 ?
C5 H5C . 0.97 ?
C4 H4A . 0.97 ?
C4 H4B . 0.97 ?
C4 H4C . 0.97 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 C11 C10 . . 119.5(2) ?
C6 C11 H11 . . 120.3 ?
C10 C11 H11 . . 120.3 ?
C13 O3 C14 . . 61.93(10) ?
C8 C9 C10 . . 120.1(2) ?
C8 C9 H9 . . 120.0 ?
C10 C9 H9 . . 120.0 ?
C9 C10 C11 . . 119.9(2) ?
C9 C10 H10 . . 120.0 ?
C11 C10 H10 . . 120.0 ?
C11 C6 C7 . . 119.07(16) ?
C11 C6 C1 . . 119.92(16) ?
C7 C6 C1 . . 121.00(15) ?
O2 C12 N1 . . 123.00(16) ?
O2 C12 C13 . . 121.11(15) ?
N1 C12 C13 . . 115.88(14) ?
O3 C13 C14 . . 59.55(10) ?
O3 C13 C12 . . 115.51(14) ?
C14 C13 C12 . . 120.44(14) ?
O3 C13 H13 . . 116.4 ?
C14 C13 H13 . . 116.4 ?
C12 C13 H13 . . 116.4 ?
O3 C14 C13 . . 58.52(10) ?
O3 C14 C15 . . 118.17(14) ?
C13 C14 C15 . . 122.95(15) ?
O3 C14 H14 . . 115.1 ?
C13 C14 H14 . . 115.1 ?
C15 C14 H14 . . 115.1 ?
C16 C15 C20 . . 118.98(19) ?
C16 C15 C14 . . 119.39(17) ?
C20 C15 C14 . . 121.60(17) ?
C17 C16 C15 . . 120.6(2) ?
C17 C16 H16 . . 119.7 ?
C15 C16 H16 . . 119.7 ?
C18 C17 C16 . . 119.9(2) ?
C18 C17 H17 . . 120.1 ?
C16 C17 H17 . . 120.1 ?
C17 C18 C19 . . 120.3(2) ?
C17 C18 H18 . . 119.8 ?
C19 C18 H18 . . 119.8 ?
C8 C7 C6 . . 120.6(2) ?
C8 C7 H7 . . 119.7 ?
C6 C7 H7 . . 119.7 ?
C9 C8 C7 . . 120.8(2) ?
C9 C8 H8 . . 119.6 ?
C7 C8 H8 . . 119.6 ?
C20 C19 C18 . . 120.1(2) ?
C20 C19 H19 . . 120.0 ?
C18 C19 H19 . . 120.0 ?
C19 C20 C15 . . 120.1(2) ?
C19 C20 H20 . . 119.9 ?
C15 C20 H20 . . 119.9 ?
N1 C1 C6 . . 113.92(13) ?
N1 C1 C2 . . 100.15(14) ?
C6 C1 C2 . . 113.41(15) ?
N1 C1 H1 . . 109.7 ?
C6 C1 H1 . . 109.7 ?
C2 C1 H1 . . 109.7 ?
C12 N1 C1 . . 125.42(14) ?
C12 N1 C3 . . 122.92(14) ?
C1 N1 C3 . . 111.41(13) ?
N1 C3 O1A . . 99.3(2) ?
N1 C3 C4 . . 113.13(17) ?
O1A C3 C4 . . 124.0(4) ?
N1 C3 C5 . . 111.35(17) ?
O1A C3 C5 . . 94.8(3) ?
C4 C3 C5 . . 112.41(18) ?
O1A C2 C1 . . 108.0(2) ?
O1A C2 H2A . . 110.1 ?
C1 C2 H2A . . 110.1 ?
O1A C2 H2B . . 110.1 ?
C1 C2 H2B . . 110.1 ?
H2A C2 H2B . . 108.4 ?
C2 O1A C3 . . 110.0(3) ?

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_I
_database_code_depnum_ccdc_archive 'CCDC 1030561'
_audit_update_record             
;
2014-10-22 deposited with the CCDC.
2014-11-27 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C25 H29 Br N2 O4'
_chemical_formula_sum            'C25 H29 Br N2 O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         501.41
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   7.8797(17)
_cell_length_b                   12.465(3)
_cell_length_c                   25.404(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2495.2(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2773
_cell_measurement_theta_min      2.9080
_cell_measurement_theta_max      18.4341
_cell_measurement_temperature    300.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.670
_exptl_crystal_size_mid          0.410
_exptl_crystal_size_min          0.300
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1040

_exptl_absorpt_coefficient_mu    1.679
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.44
_exptl_absorpt_correction_T_max  0.63

_exptl_special_details           
;
;

_diffrn_ambient_temperature      300.(2)

_diffrn_source                   'sealed MicroFocus tube'
_diffrn_source_type              ?

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'doubly curved silicon crystal'

_diffrn_measurement_device_type  'SMART X2S'
_diffrn_measurement_method       omega-scan

_diffrn_detector_area_resol_mean 8.3330

_diffrn_reflns_number            17475
_diffrn_reflns_av_R_equivalents  0.0921
_diffrn_reflns_av_sigmaI/netI    0.0848
_diffrn_reflns_theta_min         2.29
_diffrn_reflns_theta_max         23.30
_diffrn_reflns_theta_full        23.30
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28

_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.
;

_reflns_number_total             3589
_reflns_number_gt                2587
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0794
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_gt          0.0948
_refine_ls_wR_factor_ref         0.1078
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_restrained_S_all      0.989
_refine_ls_number_reflns         3589
_refine_ls_number_parameters     304
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0268P)²+0.3456P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.304
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.002(13)

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_data_reduction        'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.12078(10) 0.76515(6) 1.00808(3) 0.0990(3) Uani d . 1.0 A 2
O O4 0.5460(4) 0.3396(3) 0.79206(13) 0.0554(9) Uani d . 1.0 A 2
O O3 0.3255(4) 0.2889(3) 0.74026(11) 0.0472(9) Uani d . 1.0 A 2
O O2 0.2724(4) 0.1514(3) 0.83101(13) 0.0501(9) Uani d . 1.0 A 2
N N1 -0.0117(5) 0.1515(3) 0.84674(14) 0.0415(10) Uani d . 1.0 A 2
N N2 0.2705(5) 0.3794(3) 0.81279(13) 0.0400(10) Uani d . 1.0 A 2
C C1 0.1697(6) 0.6462(4) 0.96461(19) 0.0494(13) Uani d . 1.0 A 2
C C2 0.2572(7) 0.5610(4) 0.98508(19) 0.0564(14) Uani d . 1.0 A 2
H H2 0.2919 0.5614 1.0201 0.068 Uiso calc R 1.0 A 2
C C3 0.2929(6) 0.4747(4) 0.95316(19) 0.0502(13) Uani d . 1.0 A 2
H H3 0.3549 0.4175 0.9666 0.06 Uiso calc R 1.0 A 2
C C4 0.2390(5) 0.4714(3) 0.90177(17) 0.0378(11) Uani d . 1.0 A 2
C C5 0.2729(6) 0.3734(4) 0.86990(16) 0.0368(11) Uani d . 1.0 A 2
H H5 0.3573 0.3243 0.8848 0.044 Uiso calc R 1.0 A 2
C C6 0.1336(6) 0.3204(3) 0.83789(16) 0.0385(11) Uani d . 1.0 A 2
H H6 0.0214 0.3544 0.8384 0.046 Uiso calc R 1.0 A 2
C C7 0.1389(7) 0.2004(4) 0.83799(17) 0.0425(12) Uani d . 1.0 A 2
C C8 -0.1726(6) 0.2045(4) 0.86108(18) 0.0421(12) Uani d . 1.0 A 2
H H8 -0.2143 0.2472 0.8314 0.051 Uiso calc R 1.0 A 2
C C9 -0.1596(5) 0.2741(4) 0.90981(17) 0.0418(12) Uani d . 1.0 A 2
C C10 -0.2482(6) 0.3687(4) 0.9125(2) 0.0589(14) Uani d . 1.0 A 2
H H10 -0.3151 0.3893 0.884 0.071 Uiso calc R 1.0 A 2
C C11 -0.2407(7) 0.4341(5) 0.9563(3) 0.0766(18) Uani d . 1.0 A 2
H H11 -0.3026 0.4975 0.9574 0.092 Uiso calc R 1.0 A 2
C C12 -0.1409(8) 0.4046(5) 0.9984(2) 0.0723(16) Uani d . 1.0 A 2
H H12 -0.1342 0.4484 1.0279 0.087 Uiso calc R 1.0 A 2
C C13 0.1139(7) 0.6459(4) 0.9137(2) 0.0596(14) Uani d . 1.0 A 2
H H13 0.0533 0.7038 0.9002 0.072 Uiso calc R 1.0 A 2
C C14 0.1498(7) 0.5573(4) 0.88229(18) 0.0508(14) Uani d . 1.0 A 2
H H14 0.1126 0.5561 0.8475 0.061 Uiso calc R 1.0 A 2
C C15 0.3984(6) 0.3316(4) 0.78214(18) 0.0409(12) Uani d . 1.0 A 2
C C16 0.4301(6) 0.2349(4) 0.69912(18) 0.0563(13) Uani d . 1.0 A 2
C C17 0.5262(9) 0.1431(5) 0.7242(2) 0.087(2) Uani d . 1.0 A 2
H H17A 0.449 0.0992 0.7439 0.131 Uiso calc R 1.0 A 2
H H17B 0.6118 0.1712 0.7473 0.131 Uiso calc R 1.0 A 2
H H17C 0.579 0.1007 0.6972 0.131 Uiso calc R 1.0 A 2
C C18 0.5409(8) 0.3157(5) 0.6724(2) 0.088(2) Uani d . 1.0 A 2
H H18A 0.5865 0.2852 0.6407 0.132 Uiso calc R 1.0 A 2
H H18B 0.6321 0.3355 0.6955 0.132 Uiso calc R 1.0 A 2
H H18C 0.4751 0.3781 0.6639 0.132 Uiso calc R 1.0 A 2
C C19 0.2966(9) 0.1945(6) 0.6621(2) 0.106(3) Uani d . 1.0 A 2
H H19A 0.2186 0.1494 0.6809 0.159 Uiso calc R 1.0 A 2
H H19B 0.3493 0.154 0.6344 0.159 Uiso calc R 1.0 A 2
H H19C 0.2364 0.2542 0.6472 0.159 Uiso calc R 1.0 A 2
C C20 -0.0592(6) 0.2443(4) 0.95264(17) 0.0523(13) Uani d . 1.0 A 2
H H20 0.0019 0.1805 0.9517 0.063 Uiso calc R 1.0 A 2
C C21 -0.0510(7) 0.3099(5) 0.99652(19) 0.0630(15) Uani d . 1.0 A 2
H H21 0.016 0.2899 1.025 0.076 Uiso calc R 1.0 A 2
C C22 -0.2850(7) 0.1062(5) 0.8689(2) 0.0612(15) Uani d . 1.0 A 2
H H22A -0.2869 0.0858 0.9057 0.073 Uiso calc R 1.0 A 2
H H22B -0.4002 0.1218 0.8578 0.073 Uiso calc R 1.0 A 2
C C24 -0.0321(7) 0.0326(4) 0.8426(2) 0.0632(16) Uani d . 1.0 A 2
C C25 0.0667(9) -0.0263(4) 0.8828(2) 0.091(2) Uani d . 1.0 A 2
H H25A 0.0326 -0.0033 0.9173 0.136 Uiso calc R 1.0 A 2
H H25B 0.1854 -0.0121 0.878 0.136 Uiso calc R 1.0 A 2
H H25C 0.0463 -0.1019 0.8792 0.136 Uiso calc R 1.0 A 2
C C26 0.0040(9) -0.0069(5) 0.7879(2) 0.099(2) Uani d . 1.0 A 2
H H26A -0.0417 -0.0778 0.7838 0.149 Uiso calc R 1.0 A 2
H H26B 0.1245 -0.0087 0.7823 0.149 Uiso calc R 1.0 A 2
H H26C -0.0476 0.0404 0.7628 0.149 Uiso calc R 1.0 A 2
O O1A -0.1833(18) 0.0191(9) 0.8793(11) 0.055(7) Uani d P 0.35(3) B 1
O O1B -0.2179(9) 0.0246(6) 0.8388(8) 0.072(5) Uani d P 0.65(3) A 2


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C1 . 1.888(5) ?
O4 C15 . 1.194(5) ?
O3 C15 . 1.321(5) ?
O3 C16 . 1.491(5) ?
O2 C7 . 1.230(5) ?
N1 C7 . 1.353(6) ?
N1 C8 . 1.475(5) ?
N1 C24 . 1.494(6) ?
N2 C15 . 1.406(6) ?
N2 C5 . 1.453(5) ?
N2 C6 . 1.453(5) ?
C1 C13 . 1.367(7) ?
C1 C2 . 1.369(7) ?
C2 C3 . 1.376(6) ?
C2 H2 . 0.93 ?
C3 C4 . 1.374(6) ?
C3 H3 . 0.93 ?
C4 C14 . 1.372(6) ?
C4 C5 . 1.490(6) ?
C5 C6 . 1.517(6) ?
C5 H5 . 0.98 ?
C6 C7 . 1.496(6) ?
C6 H6 . 0.98 ?
C8 C9 . 1.515(6) ?
C8 C22 . 1.525(7) ?
C8 H8 . 0.98 ?
C9 C10 . 1.372(7) ?
C9 C20 . 1.396(6) ?
C10 C11 . 1.381(7) ?
C10 H10 . 0.93 ?
C11 C12 . 1.378(7) ?
C11 H11 . 0.93 ?
C12 C21 . 1.377(8) ?
C12 H12 . 0.93 ?
C13 C14 . 1.391(6) ?
C13 H13 . 0.93 ?
C14 H14 . 0.93 ?
C16 C18 . 1.495(7) ?
C16 C19 . 1.499(7) ?
C16 C17 . 1.513(7) ?
C17 H17A . 0.96 ?
C17 H17B . 0.96 ?
C17 H17C . 0.96 ?
C18 H18A . 0.96 ?
C18 H18B . 0.96 ?
C18 H18C . 0.96 ?
C19 H19A . 0.96 ?
C19 H19B . 0.96 ?
C19 H19C . 0.96 ?
C20 C21 . 1.384(6) ?
C20 H20 . 0.93 ?
C21 H21 . 0.93 ?
C22 O1B . 1.378(10) ?
C22 H22A . 0.97 ?
C22 H22B . 0.97 ?
C24 O1B . 1.471(8) ?
C24 C25 . 1.479(7) ?
C24 C26 . 1.501(7) ?
C25 H25A . 0.96 ?
C25 H25B . 0.96 ?
C25 H25C . 0.96 ?
C26 H26A . 0.96 ?
C26 H26B . 0.96 ?
C26 H26C . 0.96 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C15 O3 C16 . . 120.4(3) ?
C7 N1 C8 . . 126.3(4) ?
C7 N1 C24 . . 122.0(4) ?
C8 N1 C24 . . 111.7(4) ?
C15 N2 C5 . . 121.5(4) ?
C15 N2 C6 . . 124.1(4) ?
C5 N2 C6 . . 63.0(3) ?
C13 C1 C2 . . 121.3(4) ?
C13 C1 Br1 . . 119.3(4) ?
C2 C1 Br1 . . 119.3(4) ?
C1 C2 C3 . . 119.1(5) ?
C1 C2 H2 . . 120.5 ?
C3 C2 H2 . . 120.5 ?
C4 C3 C2 . . 121.3(5) ?
C4 C3 H3 . . 119.3 ?
C2 C3 H3 . . 119.3 ?
C14 C4 C3 . . 118.6(4) ?
C14 C4 C5 . . 122.4(4) ?
C3 C4 C5 . . 119.0(4) ?
N2 C5 C4 . . 119.9(4) ?
N2 C5 C6 . . 58.5(3) ?
C4 C5 C6 . . 121.2(4) ?
N2 C5 H5 . . 115.2 ?
C4 C5 H5 . . 115.2 ?
C6 C5 H5 . . 115.2 ?
N2 C6 C7 . . 119.1(4) ?
N2 C6 C5 . . 58.5(3) ?
C7 C6 C5 . . 114.5(4) ?
N2 C6 H6 . . 117.2 ?
C7 C6 H6 . . 117.2 ?
C5 C6 H6 . . 117.2 ?
O2 C7 N1 . . 123.4(4) ?
O2 C7 C6 . . 121.4(5) ?
N1 C7 C6 . . 115.3(5) ?
N1 C8 C9 . . 113.6(4) ?
N1 C8 C22 . . 99.9(4) ?
C9 C8 C22 . . 113.1(4) ?
N1 C8 H8 . . 110.0 ?
C9 C8 H8 . . 110.0 ?
C22 C8 H8 . . 110.0 ?
C10 C9 C20 . . 118.6(4) ?
C10 C9 C8 . . 119.9(4) ?
C20 C9 C8 . . 121.5(4) ?
C9 C10 C11 . . 121.7(5) ?
C9 C10 H10 . . 119.2 ?
C11 C10 H10 . . 119.2 ?
C12 C11 C10 . . 119.5(5) ?
C12 C11 H11 . . 120.2 ?
C10 C11 H11 . . 120.2 ?
C21 C12 C11 . . 119.7(5) ?
C21 C12 H12 . . 120.1 ?
C11 C12 H12 . . 120.1 ?
C1 C13 C14 . . 118.6(5) ?
C1 C13 H13 . . 120.7 ?
C14 C13 H13 . . 120.7 ?
C4 C14 C13 . . 121.1(4) ?
C4 C14 H14 . . 119.4 ?
C13 C14 H14 . . 119.4 ?
O4 C15 O3 . . 128.9(4) ?
O4 C15 N2 . . 123.1(5) ?
O3 C15 N2 . . 107.8(4) ?
O3 C16 C18 . . 109.7(4) ?
O3 C16 C19 . . 101.8(4) ?
C18 C16 C19 . . 110.6(5) ?
O3 C16 C17 . . 108.9(4) ?
C18 C16 C17 . . 114.1(5) ?
C19 C16 C17 . . 111.2(5) ?
C16 C17 H17A . . 109.5 ?
C16 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C16 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C16 C18 H18A . . 109.5 ?
C16 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C16 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C16 C19 H19A . . 109.5 ?
C16 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C16 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C21 C20 C9 . . 119.8(5) ?
C21 C20 H20 . . 120.1 ?
C9 C20 H20 . . 120.1 ?
C12 C21 C20 . . 120.7(5) ?
C12 C21 H21 . . 119.7 ?
C20 C21 H21 . . 119.7 ?
O1B C22 C8 . . 107.4(5) ?
O1B C22 H22A . . 110.2 ?
C8 C22 H22A . . 110.2 ?
O1B C22 H22B . . 110.2 ?
C8 C22 H22B . . 110.2 ?
H22A C22 H22B . . 108.5 ?
O1B C24 C25 . . 122.3(9) ?
O1B C24 N1 . . 100.3(5) ?
C25 C24 N1 . . 112.8(5) ?
O1B C24 C26 . . 96.1(8) ?
C25 C24 C26 . . 112.1(5) ?
N1 C24 C26 . . 111.8(5) ?
C24 C25 H25A . . 109.5 ?
C24 C25 H25B . . 109.5 ?
H25A C25 H25B . . 109.5 ?
C24 C25 H25C . . 109.5 ?
H25A C25 H25C . . 109.5 ?
H25B C25 H25C . . 109.5 ?
C24 C26 H26A . . 109.5 ?
C24 C26 H26B . . 109.5 ?
H26A C26 H26B . . 109.5 ?
C24 C26 H26C . . 109.5 ?
H26A C26 H26C . . 109.5 ?
H26B C26 H26C . . 109.5 ?
C22 O1B C24 . . 107.2(8) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C13 C1 C2 C3 . . . . 1.7(8) ?
Br1 C1 C2 C3 . . . . -179.8(4) ?
C1 C2 C3 C4 . . . . -1.7(8) ?
C2 C3 C4 C14 . . . . 0.9(7) ?
C2 C3 C4 C5 . . . . -176.6(4) ?
C15 N2 C5 C4 . . . . 134.4(4) ?
C6 N2 C5 C4 . . . . -110.5(4) ?
C15 N2 C5 C6 . . . . -115.2(5) ?
C14 C4 C5 N2 . . . . 23.2(7) ?
C3 C4 C5 N2 . . . . -159.4(4) ?
C14 C4 C5 C6 . . . . -46.0(6) ?
C3 C4 C5 C6 . . . . 131.4(5) ?
C15 N2 C6 C7 . . . . 8.8(6) ?
C5 N2 C6 C7 . . . . -102.4(5) ?
C15 N2 C6 C5 . . . . 111.2(5) ?
C4 C5 C6 N2 . . . . 108.2(4) ?
N2 C5 C6 C7 . . . . 110.3(4) ?
C4 C5 C6 C7 . . . . -141.5(4) ?
C8 N1 C7 O2 . . . . 172.9(4) ?
C24 N1 C7 O2 . . . . -7.1(7) ?
C8 N1 C7 C6 . . . . -6.4(7) ?
C24 N1 C7 C6 . . . . 173.6(4) ?
N2 C6 C7 O2 . . . . 20.3(7) ?
C5 C6 C7 O2 . . . . -45.9(6) ?
N2 C6 C7 N1 . . . . -160.4(4) ?
C5 C6 C7 N1 . . . . 133.4(4) ?
C7 N1 C8 C9 . . . . -55.3(6) ?
C24 N1 C8 C9 . . . . 124.7(4) ?
C7 N1 C8 C22 . . . . -176.1(4) ?
C24 N1 C8 C22 . . . . 3.9(5) ?
N1 C8 C9 C10 . . . . 143.1(4) ?
C22 C8 C9 C10 . . . . -104.0(5) ?
N1 C8 C9 C20 . . . . -37.1(6) ?
C22 C8 C9 C20 . . . . 75.9(6) ?
C20 C9 C10 C11 . . . . -0.3(7) ?
C8 C9 C10 C11 . . . . 179.6(5) ?
C9 C10 C11 C12 . . . . 0.5(8) ?
C10 C11 C12 C21 . . . . -0.6(8) ?
C2 C1 C13 C14 . . . . -0.9(8) ?
Br1 C1 C13 C14 . . . . -179.4(4) ?
C3 C4 C14 C13 . . . . -0.1(7) ?
C5 C4 C14 C13 . . . . 177.3(5) ?
C1 C13 C14 C4 . . . . 0.1(8) ?
C16 O3 C15 O4 . . . . 4.6(7) ?
C16 O3 C15 N2 . . . . 178.0(4) ?
C5 N2 C15 O4 . . . . -45.2(6) ?
C6 N2 C15 O4 . . . . -121.9(5) ?
C5 N2 C15 O3 . . . . 140.9(4) ?
C6 N2 C15 O3 . . . . 64.1(5) ?
C15 O3 C16 C18 . . . . -66.0(6) ?
C15 O3 C16 C19 . . . . 176.9(4) ?
C15 O3 C16 C17 . . . . 59.4(6) ?
C10 C9 C20 C21 . . . . 0.0(7) ?
C8 C9 C20 C21 . . . . -179.9(4) ?
C11 C12 C21 C20 . . . . 0.3(8) ?
C9 C20 C21 C12 . . . . 0.0(7) ?
N1 C8 C22 O1B . . . . -25.5(10) ?
C9 C8 C22 O1B . . . . -146.6(9) ?
C7 N1 C24 O1B . . . . -163.1(9) ?
C8 N1 C24 O1B . . . . 16.9(10) ?
C7 N1 C24 C25 . . . . 65.1(7) ?
C8 N1 C24 C25 . . . . -114.9(5) ?
C7 N1 C24 C26 . . . . -62.3(7) ?
C8 N1 C24 C26 . . . . 117.7(5) ?
C8 C22 O1B C24 . . . . 38.6(13) ?
C25 C24 O1B C22 . . . . 92.0(10) ?
N1 C24 O1B C22 . . . . -33.5(13) ?
C26 C24 O1B C22 . . . . -147.0(10) ?

