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# 
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#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
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data_E233A

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H24 Br N O3'
_chemical_formula_weight         490.38

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.518(4)
_cell_length_b                   10.893(4)
_cell_length_c                   19.602(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2245.8(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    923
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      26.85

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_F_000             1008
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.560
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    1.860
_shelx_estimated_absorpt_T_min   0.422
_shelx_estimated_absorpt_T_max   0.755
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.5737
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2012)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15883
_diffrn_reflns_av_unetI/netI     0.0642
_diffrn_reflns_av_R_equivalents  0.0555
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.078
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5157
_reflns_number_gt                4574
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.765
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.998

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0340P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1791 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.024(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5157
_refine_ls_number_parameters     293
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.0892
_refine_ls_wR_factor_gt          0.0867
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.24570(3) 0.68592(3) 0.74798(2) 0.02989(12) Uani 1 1 d . . . . .
O1 O 0.2710(2) 0.7438(2) 0.58659(10) 0.0230(5) Uani 1 1 d . . . . .
O2 O 0.1904(2) 0.8278(2) 0.49528(11) 0.0313(6) Uani 1 1 d . . . . .
O3 O -0.11652(19) 1.0355(2) 0.60843(10) 0.0230(5) Uani 1 1 d . . . . .
N1 N 0.2233(2) 0.5931(2) 0.74771(13) 0.0197(5) Uani 1 1 d D . . . .
H1N H 0.197(3) 0.586(4) 0.7866(13) 0.030(10) Uiso 1 1 d D . . . .
C1 C 0.3406(3) 0.5503(3) 0.72862(14) 0.0187(6) Uani 1 1 d . . . . .
C2 C 0.4217(3) 0.4682(3) 0.76061(16) 0.0248(7) Uani 1 1 d . . . . .
H2 H 0.4006 0.4329 0.8034 0.030 Uiso 1 1 calc R U . . .
C3 C 0.5344(3) 0.4395(4) 0.72811(16) 0.0285(7) Uani 1 1 d . . . . .
H3 H 0.5914 0.3830 0.7488 0.034 Uiso 1 1 calc R U . . .
C4 C 0.5662(3) 0.4927(3) 0.66474(16) 0.0271(8) Uani 1 1 d . . . . .
H4 H 0.6448 0.4722 0.6438 0.033 Uiso 1 1 calc R U . . .
C5 C 0.4860(3) 0.5734(3) 0.63286(16) 0.0234(7) Uani 1 1 d . . . . .
H5 H 0.5080 0.6088 0.5902 0.028 Uiso 1 1 calc R U . . .
C6 C 0.3708(3) 0.6023(3) 0.66474(15) 0.0189(6) Uani 1 1 d . . . . .
C7 C 0.2655(3) 0.6776(3) 0.64776(14) 0.0199(6) Uani 1 1 d . . . . .
C8 C 0.1764(3) 0.6732(3) 0.69832(14) 0.0183(6) Uani 1 1 d . . . . .
C9 C 0.0431(3) 0.7194(3) 0.70308(14) 0.0167(6) Uani 1 1 d . . . . .
H9 H -0.0132 0.6461 0.6974 0.020 Uiso 1 1 calc R U . . .
C10 C 0.0086(3) 0.8082(3) 0.64462(14) 0.0194(6) Uani 1 1 d . . . . .
H10 H -0.0857 0.8197 0.6466 0.023 Uiso 1 1 calc R U . . .
C11 C 0.0377(3) 0.7483(3) 0.57476(15) 0.0224(7) Uani 1 1 d . . . . .
H11A H 0.0281 0.6582 0.5791 0.027 Uiso 1 1 calc R U . . .
H11B H -0.0258 0.7773 0.5411 0.027 Uiso 1 1 calc R U . . .
C12 C 0.1684(3) 0.7761(3) 0.54830(15) 0.0228(7) Uani 1 1 d . . . . .
C13 C 0.0080(3) 0.7760(3) 0.77132(14) 0.0185(6) Uani 1 1 d . . . . .
C14 C 0.0972(3) 0.8393(3) 0.81021(14) 0.0221(7) Uani 1 1 d . . . . .
H14 H 0.1835 0.8407 0.7958 0.027 Uiso 1 1 calc R U . . .
C15 C 0.0632(3) 0.9001(3) 0.86950(15) 0.0268(7) Uani 1 1 d . . . . .
H15 H 0.1257 0.9422 0.8955 0.032 Uiso 1 1 calc R U . . .
C16 C -0.0619(3) 0.8995(3) 0.89058(16) 0.0288(8) Uani 1 1 d . . . . .
H16 H -0.0856 0.9415 0.9311 0.035 Uiso 1 1 calc R U . . .
C17 C -0.1524(3) 0.8384(3) 0.85330(17) 0.0286(7) Uani 1 1 d . . . . .
H17 H -0.2388 0.8387 0.8676 0.034 Uiso 1 1 calc R U . . .
C18 C -0.1167(3) 0.7762(3) 0.79450(15) 0.0231(7) Uani 1 1 d . . . . .
C19 C 0.0672(3) 0.9360(3) 0.65144(15) 0.0198(6) Uani 1 1 d . . . . .
H19A H 0.0486 0.9686 0.6975 0.024 Uiso 1 1 calc R U . . .
H19B H 0.1607 0.9294 0.6468 0.024 Uiso 1 1 calc R U . . .
C20 C 0.0176(3) 1.0252(3) 0.59859(16) 0.0220(7) Uani 1 1 d . . . . .
H20A H 0.0586 1.1064 0.6043 0.026 Uiso 1 1 calc R U . . .
H20B H 0.0362 0.9947 0.5521 0.026 Uiso 1 1 calc R U . . .
C21 C -0.1758(3) 1.0998(3) 0.55336(16) 0.0256(7) Uani 1 1 d . . . . .
H21A H -0.1512 1.0620 0.5094 0.031 Uiso 1 1 calc R U . . .
H21B H -0.1476 1.1865 0.5531 0.031 Uiso 1 1 calc R U . . .
C22 C -0.3170(3) 1.0937(3) 0.56216(15) 0.0236(7) Uani 1 1 d . . . . .
C23 C -0.3785(4) 0.9815(4) 0.55952(16) 0.0321(8) Uani 1 1 d . . . . .
H23 H -0.3311 0.9080 0.5537 0.039 Uiso 1 1 calc R U . . .
C24 C -0.5102(4) 0.9770(5) 0.56546(18) 0.0481(12) Uani 1 1 d . . . . .
H24 H -0.5532 0.9004 0.5636 0.058 Uiso 1 1 calc R U . . .
C25 C -0.5790(4) 1.0854(6) 0.5742(2) 0.0552(14) Uani 1 1 d . . . . .
H25 H -0.6691 1.0831 0.5775 0.066 Uiso 1 1 calc R U . . .
C26 C -0.5166(4) 1.1940(5) 0.5781(2) 0.0515(12) Uani 1 1 d . . . . .
H26 H -0.5633 1.2675 0.5853 0.062 Uiso 1 1 calc R U . . .
C27 C -0.3871(4) 1.1993(4) 0.57161(18) 0.0353(9) Uani 1 1 d . . . . .
H27 H -0.3452 1.2764 0.5737 0.042 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C18 1.908(3) . ?
O1 C12 1.360(4) . ?
O1 C7 1.400(3) . ?
O2 C12 1.204(4) . ?
O3 C20 1.428(4) . ?
O3 C21 1.430(4) . ?
N1 C1 1.371(4) . ?
N1 C8 1.393(4) . ?
C1 C2 1.386(4) . ?
C1 C6 1.411(4) . ?
C2 C3 1.381(4) . ?
C3 C4 1.411(5) . ?
C4 C5 1.369(5) . ?
C5 C6 1.399(4) . ?
C6 C7 1.418(4) . ?
C7 C8 1.365(4) . ?
C8 C9 1.493(4) . ?
C9 C13 1.519(4) . ?
C9 C10 1.543(4) . ?
C10 C19 1.528(4) . ?
C10 C11 1.547(4) . ?
C11 C12 1.501(4) . ?
C13 C18 1.388(4) . ?
C13 C14 1.392(4) . ?
C14 C15 1.385(4) . ?
C15 C16 1.380(5) . ?
C16 C17 1.372(5) . ?
C17 C18 1.389(4) . ?
C19 C20 1.513(4) . ?
C21 C22 1.497(5) . ?
C22 C27 1.379(5) . ?
C22 C23 1.384(5) . ?
C23 C24 1.390(6) . ?
C24 C25 1.396(7) . ?
C25 C26 1.355(7) . ?
C26 C27 1.369(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
C12 O1 C7 125.0(2) . . ?
C20 O3 C21 111.5(2) . . ?
C1 N1 C8 110.0(2) . . ?
N1 C1 C2 130.5(3) . . ?
N1 C1 C6 107.9(3) . . ?
C2 C1 C6 121.5(3) . . ?
C3 C2 C1 117.8(3) . . ?
C2 C3 C4 121.1(3) . . ?
C5 C4 C3 121.3(3) . . ?
C4 C5 C6 118.3(3) . . ?
C5 C6 C1 120.1(3) . . ?
C5 C6 C7 134.6(3) . . ?
C1 C6 C7 105.4(2) . . ?
C8 C7 O1 131.9(3) . . ?
C8 C7 C6 110.2(3) . . ?
O1 C7 C6 117.8(2) . . ?
C7 C8 N1 106.4(3) . . ?
C7 C8 C9 132.7(3) . . ?
N1 C8 C9 120.0(2) . . ?
C8 C9 C13 114.8(2) . . ?
C8 C9 C10 112.7(2) . . ?
C13 C9 C10 110.0(2) . . ?
C19 C10 C9 114.3(2) . . ?
C19 C10 C11 112.4(3) . . ?
C9 C10 C11 110.3(3) . . ?
C12 C11 C10 113.7(3) . . ?
O2 C12 O1 116.4(3) . . ?
O2 C12 C11 124.7(3) . . ?
O1 C12 C11 118.9(3) . . ?
C18 C13 C14 117.2(3) . . ?
C18 C13 C9 121.2(3) . . ?
C14 C13 C9 121.3(3) . . ?
C15 C14 C13 121.5(3) . . ?
C16 C15 C14 119.7(3) . . ?
C17 C16 C15 120.3(3) . . ?
C16 C17 C18 119.4(3) . . ?
C13 C18 C17 121.9(3) . . ?
C13 C18 Br1 121.0(2) . . ?
C17 C18 Br1 117.1(2) . . ?
C20 C19 C10 112.7(2) . . ?
O3 C20 C19 107.4(2) . . ?
O3 C21 C22 108.9(3) . . ?
C27 C22 C23 119.5(3) . . ?
C27 C22 C21 120.6(4) . . ?
C23 C22 C21 119.9(3) . . ?
C22 C23 C24 119.6(4) . . ?
C23 C24 C25 119.8(4) . . ?
C26 C25 C24 119.6(4) . . ?
C25 C26 C27 120.9(5) . . ?
C26 C27 C22 120.6(4) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N O3 0.81(2) 2.29(2) 3.100(3) 171(4) 3_546

_refine_diff_density_max         0.859
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.071

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 1024217'
