# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_150510f
_database_code_depnum_ccdc_archive 'CCDC 1400005'
_audit_update_record             
;
2015-05-15 deposited with the CCDC.
2015-05-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H26 Br N O4'
_chemical_formula_weight         472.37
_chemical_absolute_configuration ad

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   10.7238(9)
_cell_length_b                   7.4576(7)
_cell_length_c                   13.7590(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.5020(10)
_cell_angle_gamma                90.00
_cell_volume                     1098.30(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1425
_cell_measurement_theta_min      2.483
_cell_measurement_theta_max      20.932

_exptl_crystal_description       monoclinic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             488
_exptl_absorpt_coefficient_mu    1.901
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4499
_exptl_absorpt_correction_T_max  0.7767
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5473
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_av_sigmaI/netI    0.1201
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.48
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3598
_reflns_number_gt                2084
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0255P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_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   0.019(16)
_refine_ls_number_reflns         3598
_refine_ls_number_parameters     274
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1096
_refine_ls_R_factor_gt           0.0574
_refine_ls_wR_factor_ref         0.1297
_refine_ls_wR_factor_gt          0.1164
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.20691(7) 0.14432(16) 0.93130(5) 0.0890(4) Uani 1 1 d . . .
N1 N 0.3537(4) 0.4058(7) 0.6614(3) 0.0385(12) Uani 1 1 d . . .
O1 O 0.2234(3) 0.1737(6) 0.6593(3) 0.0453(10) Uani 1 1 d . . .
O2 O 0.4181(3) 0.1360(7) 0.7242(3) 0.0531(11) Uani 1 1 d . . .
O3 O 0.7053(3) 0.6259(7) 0.7643(3) 0.0554(11) Uani 1 1 d . . .
O4 O 0.8290(5) 0.8546(8) 0.8064(5) 0.0849(19) Uani 1 1 d . . .
C1 C 0.3379(6) 0.2241(8) 0.6862(4) 0.0376(15) Uani 1 1 d . . .
C2 C 0.4813(5) 0.4775(8) 0.6694(5) 0.0449(16) Uani 1 1 d . . .
H2 H 0.5355 0.3874 0.7021 0.054 Uiso 1 1 calc R . .
C3 C 0.5253(6) 0.5063(8) 0.5699(5) 0.0518(18) Uani 1 1 d . . .
H3 H 0.6101 0.4995 0.5597 0.062 Uiso 1 1 calc R . .
C4 C 0.4450(7) 0.5413(8) 0.4965(6) 0.0546(19) Uani 1 1 d . . .
H4 H 0.4732 0.5540 0.4343 0.066 Uiso 1 1 calc R . .
C5 C 0.3134(6) 0.5602(7) 0.5109(5) 0.0432(16) Uani 1 1 d . . .
C6 C 0.2666(5) 0.4981(8) 0.5963(4) 0.0332(14) Uani 1 1 d . . .
C7 C 0.1444(5) 0.5260(8) 0.6169(4) 0.0386(15) Uani 1 1 d . . .
H7 H 0.1162 0.4886 0.6762 0.046 Uiso 1 1 calc R . .
C8 C 0.0628(5) 0.6103(9) 0.5489(4) 0.0397(15) Uani 1 1 d . . .
C9 C 0.1067(5) 0.6620(10) 0.4624(4) 0.0494(16) Uani 1 1 d . . .
H9 H 0.0525 0.7150 0.4154 0.059 Uiso 1 1 calc R . .
C10 C 0.2290(6) 0.6371(12) 0.4435(4) 0.0513(16) Uani 1 1 d . . .
H10 H 0.2562 0.6730 0.3836 0.062 Uiso 1 1 calc R . .
C11 C -0.0702(4) 0.6471(11) 0.5723(4) 0.0535(15) Uani 1 1 d . . .
H11A H -0.0799 0.7726 0.5856 0.080 Uiso 1 1 calc R . .
H11B H -0.0900 0.5786 0.6284 0.080 Uiso 1 1 calc R . .
H11C H -0.1255 0.6138 0.5178 0.080 Uiso 1 1 calc R . .
C12 C 0.6070(6) 0.7468(10) 0.7299(5) 0.061(2) Uani 1 1 d . . .
H12A H 0.6200 0.7847 0.6638 0.074 Uiso 1 1 calc R . .
H12B H 0.6064 0.8523 0.7711 0.074 Uiso 1 1 calc R . .
C13 C 0.4857(5) 0.6481(11) 0.7331(4) 0.0511(15) Uani 1 1 d . . .
H13 H 0.4202 0.7286 0.7059 0.061 Uiso 1 1 calc R . .
C14 C 0.4537(6) 0.6037(10) 0.8363(5) 0.067(2) Uani 1 1 d . . .
H14A H 0.3824 0.5235 0.8323 0.080 Uiso 1 1 calc R . .
H14B H 0.5234 0.5374 0.8668 0.080 Uiso 1 1 calc R . .
C15 C 0.4245(10) 0.7538(13) 0.9023(7) 0.116(4) Uani 1 1 d . . .
H15A H 0.4913 0.8412 0.9002 0.139 Uiso 1 1 calc R . .
H15B H 0.3489 0.8113 0.8756 0.139 Uiso 1 1 calc R . .
C16 C 0.4073(7) 0.7129(12) 1.0048(6) 0.090(3) Uani 1 1 d . . .
H16A H 0.3529 0.6113 1.0089 0.135 Uiso 1 1 calc R . .
H16B H 0.3710 0.8146 1.0352 0.135 Uiso 1 1 calc R . .
H16C H 0.4868 0.6861 1.0375 0.135 Uiso 1 1 calc R . .
C17 C 0.1985(6) -0.0153(10) 0.6742(5) 0.062(2) Uani 1 1 d . . .
H17A H 0.2465 -0.0855 0.6315 0.093 Uiso 1 1 calc R . .
H17B H 0.1112 -0.0386 0.6605 0.093 Uiso 1 1 calc R . .
H17C H 0.2215 -0.0467 0.7406 0.093 Uiso 1 1 calc R . .
C18 C 0.8094(5) 0.6965(11) 0.8018(4) 0.0504(19) Uani 1 1 d . . .
C19 C 0.9039(6) 0.5591(10) 0.8313(4) 0.0449(18) Uani 1 1 d . . .
C20 C 0.8821(6) 0.3774(10) 0.8209(5) 0.0510(19) Uani 1 1 d . . .
H20 H 0.8054 0.3388 0.7933 0.061 Uiso 1 1 calc R . .
C21 C 0.9701(6) 0.2525(10) 0.8500(5) 0.0580(19) Uani 1 1 d . . .
H21 H 0.9551 0.1306 0.8411 0.070 Uiso 1 1 calc R . .
C22 C 1.0796(6) 0.3120(13) 0.8924(5) 0.061(2) Uani 1 1 d . . .
C23 C 1.1056(6) 0.4893(15) 0.9069(5) 0.069(2) Uani 1 1 d . . .
H23 H 1.1817 0.5262 0.9364 0.082 Uiso 1 1 calc R . .
C24 C 1.0149(5) 0.6129(14) 0.8761(4) 0.064(2) Uani 1 1 d . . .
H24 H 1.0299 0.7345 0.8862 0.077 Uiso 1 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
Br1 C22 1.904(7) . ?
N1 C1 1.410(7) . ?
N1 C6 1.431(7) . ?
N1 C2 1.467(7) . ?
O1 C1 1.316(7) . ?
O1 C17 1.451(9) . ?
O2 C1 1.179(6) . ?
O3 C18 1.312(7) . ?
O3 C12 1.444(7) . ?
O4 C18 1.199(8) . ?
C2 C3 1.491(8) . ?
C2 C13 1.544(9) . ?
C2 H2 0.9800 . ?
C3 C4 1.313(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.444(9) . ?
C4 H4 0.9300 . ?
C5 C10 1.381(8) . ?
C5 C6 1.384(8) . ?
C6 C7 1.374(7) . ?
C7 C8 1.391(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.363(7) . ?
C8 C11 1.506(7) . ?
C9 C10 1.365(7) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.497(8) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.518(9) . ?
C13 H13 0.9800 . ?
C14 C15 1.486(11) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.466(11) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.480(9) . ?
C19 C24 1.367(8) . ?
C19 C20 1.381(9) . ?
C20 C21 1.369(9) . ?
C20 H20 0.9300 . ?
C21 C22 1.354(9) . ?
C21 H21 0.9300 . ?
C22 C23 1.364(11) . ?
C23 C24 1.387(12) . ?
C23 H23 0.9300 . ?
C24 H24 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
C1 N1 C6 122.0(5) . . ?
C1 N1 C2 117.2(5) . . ?
C6 N1 C2 116.2(5) . . ?
C1 O1 C17 114.5(5) . . ?
C18 O3 C12 117.7(6) . . ?
O2 C1 O1 127.5(6) . . ?
O2 C1 N1 123.2(6) . . ?
O1 C1 N1 109.3(5) . . ?
N1 C2 C3 109.3(5) . . ?
N1 C2 C13 109.8(4) . . ?
C3 C2 C13 113.7(5) . . ?
N1 C2 H2 108.0 . . ?
C3 C2 H2 108.0 . . ?
C13 C2 H2 108.0 . . ?
C4 C3 C2 120.4(6) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 121.0(7) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C10 C5 C6 116.9(5) . . ?
C10 C5 C4 123.7(6) . . ?
C6 C5 C4 119.5(6) . . ?
C7 C6 C5 121.6(5) . . ?
C7 C6 N1 122.5(5) . . ?
C5 C6 N1 115.8(5) . . ?
C6 C7 C8 119.9(5) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C9 C8 C7 118.6(5) . . ?
C9 C8 C11 121.1(5) . . ?
C7 C8 C11 120.3(5) . . ?
C8 C9 C10 121.0(6) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C9 C10 C5 121.8(5) . . ?
C9 C10 H10 119.1 . . ?
C5 C10 H10 119.1 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O3 C12 C13 107.6(6) . . ?
O3 C12 H12A 110.2 . . ?
C13 C12 H12A 110.2 . . ?
O3 C12 H12B 110.2 . . ?
C13 C12 H12B 110.2 . . ?
H12A C12 H12B 108.5 . . ?
C12 C13 C14 112.4(5) . . ?
C12 C13 C2 112.7(5) . . ?
C14 C13 C2 110.5(6) . . ?
C12 C13 H13 107.0 . . ?
C14 C13 H13 107.0 . . ?
C2 C13 H13 107.0 . . ?
C15 C14 C13 118.4(7) . . ?
C15 C14 H14A 107.7 . . ?
C13 C14 H14A 107.7 . . ?
C15 C14 H14B 107.7 . . ?
C13 C14 H14B 107.7 . . ?
H14A C14 H14B 107.1 . . ?
C16 C15 C14 118.3(8) . . ?
C16 C15 H15A 107.7 . . ?
C14 C15 H15A 107.7 . . ?
C16 C15 H15B 107.7 . . ?
C14 C15 H15B 107.7 . . ?
H15A C15 H15B 107.1 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O1 C17 H17A 109.5 . . ?
O1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O4 C18 O3 123.9(7) . . ?
O4 C18 C19 123.5(6) . . ?
O3 C18 C19 112.5(7) . . ?
C24 C19 C20 118.2(7) . . ?
C24 C19 C18 118.9(7) . . ?
C20 C19 C18 122.8(6) . . ?
C21 C20 C19 121.9(6) . . ?
C21 C20 H20 119.1 . . ?
C19 C20 H20 119.1 . . ?
C22 C21 C20 117.9(7) . . ?
C22 C21 H21 121.1 . . ?
C20 C21 H21 121.1 . . ?
C21 C22 C23 123.1(7) . . ?
C21 C22 Br1 119.6(7) . . ?
C23 C22 Br1 117.3(6) . . ?
C22 C23 C24 117.8(7) . . ?
C22 C23 H23 121.1 . . ?
C24 C23 H23 121.1 . . ?
C19 C24 C23 121.2(9) . . ?
C19 C24 H24 119.4 . . ?
C23 C24 H24 119.4 . . ?

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
C17 O1 C1 O2 -3.8(9) . . . . ?
C17 O1 C1 N1 175.5(5) . . . . ?
C6 N1 C1 O2 165.3(5) . . . . ?
C2 N1 C1 O2 10.2(8) . . . . ?
C6 N1 C1 O1 -14.1(7) . . . . ?
C2 N1 C1 O1 -169.2(4) . . . . ?
C1 N1 C2 C3 107.9(6) . . . . ?
C6 N1 C2 C3 -48.7(7) . . . . ?
C1 N1 C2 C13 -126.7(5) . . . . ?
C6 N1 C2 C13 76.7(6) . . . . ?
N1 C2 C3 C4 28.3(8) . . . . ?
C13 C2 C3 C4 -94.8(7) . . . . ?
C2 C3 C4 C5 2.6(9) . . . . ?
C3 C4 C5 C10 164.1(7) . . . . ?
C3 C4 C5 C6 -16.2(8) . . . . ?
C10 C5 C6 C7 -5.7(8) . . . . ?
C4 C5 C6 C7 174.6(5) . . . . ?
C10 C5 C6 N1 175.0(6) . . . . ?
C4 C5 C6 N1 -4.7(7) . . . . ?
C1 N1 C6 C7 63.4(8) . . . . ?
C2 N1 C6 C7 -141.2(5) . . . . ?
C1 N1 C6 C5 -117.3(6) . . . . ?
C2 N1 C6 C5 38.1(7) . . . . ?
C5 C6 C7 C8 3.4(9) . . . . ?
N1 C6 C7 C8 -177.4(5) . . . . ?
C6 C7 C8 C9 0.6(9) . . . . ?
C6 C7 C8 C11 -177.9(6) . . . . ?
C7 C8 C9 C10 -2.1(10) . . . . ?
C11 C8 C9 C10 176.4(7) . . . . ?
C8 C9 C10 C5 -0.4(12) . . . . ?
C6 C5 C10 C9 4.2(10) . . . . ?
C4 C5 C10 C9 -176.1(7) . . . . ?
C18 O3 C12 C13 -155.1(5) . . . . ?
O3 C12 C13 C14 66.2(7) . . . . ?
O3 C12 C13 C2 -59.4(7) . . . . ?
N1 C2 C13 C12 -169.8(5) . . . . ?
C3 C2 C13 C12 -47.0(7) . . . . ?
N1 C2 C13 C14 63.6(6) . . . . ?
C3 C2 C13 C14 -173.6(5) . . . . ?
C12 C13 C14 C15 67.0(9) . . . . ?
C2 C13 C14 C15 -166.2(7) . . . . ?
C13 C14 C15 C16 -173.3(7) . . . . ?
C12 O3 C18 O4 -2.3(9) . . . . ?
C12 O3 C18 C19 -178.1(5) . . . . ?
O4 C18 C19 C24 7.5(10) . . . . ?
O3 C18 C19 C24 -176.7(5) . . . . ?
O4 C18 C19 C20 -176.6(7) . . . . ?
O3 C18 C19 C20 -0.8(9) . . . . ?
C24 C19 C20 C21 -3.0(10) . . . . ?
C18 C19 C20 C21 -178.9(6) . . . . ?
C19 C20 C21 C22 1.7(10) . . . . ?
C20 C21 C22 C23 -0.1(10) . . . . ?
C20 C21 C22 Br1 -178.4(5) . . . . ?
C21 C22 C23 C24 -0.2(11) . . . . ?
Br1 C22 C23 C24 178.1(5) . . . . ?
C20 C19 C24 C23 2.6(10) . . . . ?
C18 C19 C24 C23 178.7(6) . . . . ?
C22 C23 C24 C19 -1.1(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.691
_refine_diff_density_min         -0.553
_refine_diff_density_rms         0.087
####################################################################### 
# 
# 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_150510g
_database_code_depnum_ccdc_archive 'CCDC 1400167'
_audit_update_record             
;
2015-05-15 deposited with the CCDC.
2015-05-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H24 Br N O4'
_chemical_formula_weight         458.34
_chemical_absolute_configuration ad

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_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                   5.1792(4)
_cell_length_b                   11.1118(9)
_cell_length_c                   36.240(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2085.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1966
_cell_measurement_theta_min      4.489
_cell_measurement_theta_max      20.741

_exptl_crystal_description       monoclinic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             944
_exptl_absorpt_coefficient_mu    2.000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5248
_exptl_absorpt_correction_T_max  0.8250
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10531
_diffrn_reflns_av_R_equivalents  0.0750
_diffrn_reflns_av_sigmaI/netI    0.1054
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_theta_min         2.49
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3655
_reflns_number_gt                2225
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0027P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_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   0.013(11)
_refine_ls_number_reflns         3655
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0941
_refine_ls_R_factor_gt           0.0467
_refine_ls_wR_factor_ref         0.0732
_refine_ls_wR_factor_gt          0.0666
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.002
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.30914(11) 0.57492(4) 0.550833(14) 0.0608(2) Uani 1 1 d . . .
C12 C 0.6601(9) 0.5639(3) 0.34905(11) 0.0311(11) Uani 1 1 d . . .
H12 H 0.8085 0.5624 0.3323 0.037 Uiso 1 1 calc R . .
C6 C 0.6839(11) 0.3583(3) 0.28988(11) 0.0315(12) Uani 1 1 d . . .
C10 C 0.8032(11) 0.4253(4) 0.22965(12) 0.0459(13) Uani 1 1 d . . .
H10 H 0.7761 0.4757 0.2095 0.055 Uiso 1 1 calc R . .
O1 O 0.2727(7) 0.3043(2) 0.36711(8) 0.0457(10) Uani 1 1 d . . .
O2 O 0.4652(8) 0.1692(3) 0.32976(9) 0.0549(12) Uani 1 1 d . . .
O3 O 0.5507(7) 0.5220(2) 0.41187(8) 0.0452(10) Uani 1 1 d . . .
N1 N 0.5213(8) 0.3719(3) 0.32125(10) 0.0330(10) Uani 1 1 d . . .
C18 C 0.3211(12) 0.4745(4) 0.46499(11) 0.0374(13) Uani 1 1 d . . .
O4 O 0.6549(7) 0.3497(2) 0.44052(8) 0.0566(10) Uani 1 1 d . . .
C5 C 0.6483(10) 0.4370(4) 0.26022(11) 0.0342(12) Uani 1 1 d . . .
C19 C 0.1932(10) 0.5838(4) 0.46301(11) 0.0423(13) Uani 1 1 d . . .
H19 H 0.2345 0.6381 0.4444 0.051 Uiso 1 1 calc R . .
C21 C -0.0506(10) 0.5328(4) 0.51621(12) 0.0396(14) Uani 1 1 d . . .
C17 C 0.5269(11) 0.4390(4) 0.43863(12) 0.0404(13) Uani 1 1 d . . .
C9 C 0.9952(13) 0.3418(5) 0.22810(15) 0.0568(17) Uani 1 1 d . . .
H9 H 1.0987 0.3361 0.2072 0.068 Uiso 1 1 calc R . .
C22 C 0.0721(10) 0.4257(4) 0.51846(12) 0.0481(14) Uani 1 1 d . . .
H22 H 0.0306 0.3722 0.5373 0.058 Uiso 1 1 calc R . .
C2 C 0.4423(10) 0.4956(3) 0.32994(12) 0.0324(12) Uani 1 1 d . . .
H2 H 0.2968 0.4912 0.3472 0.039 Uiso 1 1 calc R . .
C23 C 0.2570(11) 0.3958(3) 0.49318(12) 0.0501(16) Uani 1 1 d . . .
H23 H 0.3405 0.3219 0.4949 0.060 Uiso 1 1 calc R . .
C20 C 0.0048(12) 0.6128(4) 0.48850(13) 0.0511(16) Uani 1 1 d . . .
H20 H -0.0831 0.6856 0.4869 0.061 Uiso 1 1 calc R . .
C13 C 0.5878(10) 0.6978(3) 0.35481(12) 0.0390(14) Uani 1 1 d . . .
H13A H 0.5459 0.7324 0.3310 0.047 Uiso 1 1 calc R . .
H13B H 0.4333 0.7014 0.3699 0.047 Uiso 1 1 calc R . .
C3 C 0.3483(10) 0.5559(3) 0.29540(12) 0.0382(12) Uani 1 1 d . . .
H3 H 0.2178 0.6133 0.2967 0.046 Uiso 1 1 calc R . .
C11 C 0.7450(11) 0.5033(4) 0.38442(11) 0.0453(15) Uani 1 1 d . . .
H11A H 0.7689 0.4178 0.3802 0.054 Uiso 1 1 calc R . .
H11B H 0.9078 0.5370 0.3927 0.054 Uiso 1 1 calc R . .
C1 C 0.4232(10) 0.2719(4) 0.33814(13) 0.0356(14) Uani 1 1 d . . .
C7 C 0.8775(10) 0.2737(4) 0.28814(13) 0.0410(15) Uani 1 1 d . . .
H7 H 0.9015 0.2213 0.3079 0.049 Uiso 1 1 calc R . .
C8 C 1.0361(11) 0.2649(4) 0.25792(15) 0.0483(15) Uani 1 1 d . . .
H8 H 1.1688 0.2086 0.2573 0.058 Uiso 1 1 calc R . .
C4 C 0.4510(11) 0.5277(4) 0.26285(13) 0.0402(14) Uani 1 1 d . . .
H4 H 0.3946 0.5669 0.2416 0.048 Uiso 1 1 calc R . .
C16 C 0.1661(12) 0.2056(4) 0.38782(12) 0.0643(18) Uani 1 1 d . . .
H16A H 0.0506 0.1605 0.3724 0.096 Uiso 1 1 calc R . .
H16B H 0.0733 0.2363 0.4087 0.096 Uiso 1 1 calc R . .
H16C H 0.3032 0.1542 0.3961 0.096 Uiso 1 1 calc R . .
C14 C 0.7925(11) 0.7742(3) 0.37266(12) 0.0603(17) Uani 1 1 d . . .
H14A H 0.9557 0.7612 0.3601 0.072 Uiso 1 1 calc R . .
H14B H 0.8133 0.7496 0.3982 0.072 Uiso 1 1 calc R . .
C15 C 0.7249(12) 0.9086(3) 0.37134(12) 0.077(2) Uani 1 1 d . . .
H15A H 0.7133 0.9343 0.3461 0.115 Uiso 1 1 calc R . .
H15B H 0.8569 0.9539 0.3837 0.115 Uiso 1 1 calc R . .
H15C H 0.5622 0.9217 0.3834 0.115 Uiso 1 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
Br1 C21 1.894(5) . ?
C12 C11 1.513(5) . ?
C12 C2 1.526(6) . ?
C12 C13 1.548(5) . ?
C12 H12 0.9800 . ?
C6 C7 1.376(6) . ?
C6 C5 1.398(5) . ?
C6 N1 1.423(5) . ?
C10 C9 1.361(7) . ?
C10 C5 1.374(6) . ?
C10 H10 0.9300 . ?
O1 C1 1.356(5) . ?
O1 C16 1.439(4) . ?
O2 C1 1.200(5) . ?
O3 C17 1.344(4) . ?
O3 C11 1.430(5) . ?
N1 C1 1.367(5) . ?
N1 C2 1.469(4) . ?
C18 C23 1.385(5) . ?
C18 C19 1.386(6) . ?
C18 C17 1.485(6) . ?
O4 C17 1.196(5) . ?
C5 C4 1.438(6) . ?
C19 C20 1.381(6) . ?
C19 H19 0.9300 . ?
C21 C22 1.351(6) . ?
C21 C20 1.372(6) . ?
C9 C8 1.394(6) . ?
C9 H9 0.9300 . ?
C22 C23 1.366(6) . ?
C22 H22 0.9300 . ?
C2 C3 1.501(5) . ?
C2 H2 0.9800 . ?
C23 H23 0.9300 . ?
C20 H20 0.9300 . ?
C13 C14 1.505(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C3 C4 1.331(5) . ?
C3 H3 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C7 C8 1.372(6) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C4 H4 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C14 C15 1.535(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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
C11 C12 C2 112.2(4) . . ?
C11 C12 C13 112.6(3) . . ?
C2 C12 C13 111.1(4) . . ?
C11 C12 H12 106.9 . . ?
C2 C12 H12 106.9 . . ?
C13 C12 H12 106.9 . . ?
C7 C6 C5 119.2(5) . . ?
C7 C6 N1 122.7(4) . . ?
C5 C6 N1 118.0(4) . . ?
C9 C10 C5 121.6(5) . . ?
C9 C10 H10 119.2 . . ?
C5 C10 H10 119.2 . . ?
C1 O1 C16 114.9(3) . . ?
C17 O3 C11 117.8(4) . . ?
C1 N1 C6 119.4(4) . . ?
C1 N1 C2 124.2(4) . . ?
C6 N1 C2 115.9(3) . . ?
C23 C18 C19 118.5(5) . . ?
C23 C18 C17 118.6(4) . . ?
C19 C18 C17 122.9(4) . . ?
C10 C5 C6 118.9(5) . . ?
C10 C5 C4 122.3(5) . . ?
C6 C5 C4 118.8(4) . . ?
C20 C19 C18 120.5(4) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C22 C21 C20 121.1(5) . . ?
C22 C21 Br1 120.7(4) . . ?
C20 C21 Br1 118.2(4) . . ?
O4 C17 O3 124.1(5) . . ?
O4 C17 C18 125.5(4) . . ?
O3 C17 C18 110.4(4) . . ?
C10 C9 C8 119.8(5) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C21 C22 C23 120.2(5) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
N1 C2 C3 109.2(4) . . ?
N1 C2 C12 110.9(4) . . ?
C3 C2 C12 113.3(3) . . ?
N1 C2 H2 107.7 . . ?
C3 C2 H2 107.7 . . ?
C12 C2 H2 107.7 . . ?
C22 C23 C18 120.6(4) . . ?
C22 C23 H23 119.7 . . ?
C18 C23 H23 119.7 . . ?
C21 C20 C19 119.1(4) . . ?
C21 C20 H20 120.5 . . ?
C19 C20 H20 120.5 . . ?
C14 C13 C12 115.5(4) . . ?
C14 C13 H13A 108.4 . . ?
C12 C13 H13A 108.4 . . ?
C14 C13 H13B 108.4 . . ?
C12 C13 H13B 108.4 . . ?
H13A C13 H13B 107.5 . . ?
C4 C3 C2 120.3(4) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
O3 C11 C12 108.7(4) . . ?
O3 C11 H11A 110.0 . . ?
C12 C11 H11A 110.0 . . ?
O3 C11 H11B 110.0 . . ?
C12 C11 H11B 110.0 . . ?
H11A C11 H11B 108.3 . . ?
O2 C1 O1 123.5(4) . . ?
O2 C1 N1 126.3(5) . . ?
O1 C1 N1 110.1(4) . . ?
C8 C7 C6 121.4(5) . . ?
C8 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C7 C8 C9 119.0(5) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 H8 120.5 . . ?
C3 C4 C5 120.5(4) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
O1 C16 H16A 109.5 . . ?
O1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C14 C15 112.0(4) . . ?
C13 C14 H14A 109.2 . . ?
C15 C14 H14A 109.2 . . ?
C13 C14 H14B 109.2 . . ?
C15 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
C7 C6 N1 C1 -43.7(6) . . . . ?
C5 C6 N1 C1 138.2(4) . . . . ?
C7 C6 N1 C2 144.5(4) . . . . ?
C5 C6 N1 C2 -33.5(6) . . . . ?
C9 C10 C5 C6 -2.3(7) . . . . ?
C9 C10 C5 C4 177.6(4) . . . . ?
C7 C6 C5 C10 1.9(6) . . . . ?
N1 C6 C5 C10 -179.9(4) . . . . ?
C7 C6 C5 C4 -177.9(4) . . . . ?
N1 C6 C5 C4 0.2(6) . . . . ?
C23 C18 C19 C20 -0.5(7) . . . . ?
C17 C18 C19 C20 -179.3(5) . . . . ?
C11 O3 C17 O4 -1.3(6) . . . . ?
C11 O3 C17 C18 178.7(4) . . . . ?
C23 C18 C17 O4 -4.1(7) . . . . ?
C19 C18 C17 O4 174.7(5) . . . . ?
C23 C18 C17 O3 175.8(4) . . . . ?
C19 C18 C17 O3 -5.3(6) . . . . ?
C5 C10 C9 C8 0.7(7) . . . . ?
C20 C21 C22 C23 0.7(7) . . . . ?
Br1 C21 C22 C23 179.5(4) . . . . ?
C1 N1 C2 C3 -123.5(4) . . . . ?
C6 N1 C2 C3 47.8(5) . . . . ?
C1 N1 C2 C12 110.9(5) . . . . ?
C6 N1 C2 C12 -77.8(5) . . . . ?
C11 C12 C2 N1 -58.6(5) . . . . ?
C13 C12 C2 N1 174.4(3) . . . . ?
C11 C12 C2 C3 178.1(4) . . . . ?
C13 C12 C2 C3 51.1(5) . . . . ?
C21 C22 C23 C18 0.0(7) . . . . ?
C19 C18 C23 C22 -0.1(7) . . . . ?
C17 C18 C23 C22 178.8(4) . . . . ?
C22 C21 C20 C19 -1.3(8) . . . . ?
Br1 C21 C20 C19 179.9(4) . . . . ?
C18 C19 C20 C21 1.2(8) . . . . ?
C11 C12 C13 C14 54.7(6) . . . . ?
C2 C12 C13 C14 -178.6(4) . . . . ?
N1 C2 C3 C4 -32.4(6) . . . . ?
C12 C2 C3 C4 91.8(5) . . . . ?
C17 O3 C11 C12 152.1(4) . . . . ?
C2 C12 C11 O3 -73.3(4) . . . . ?
C13 C12 C11 O3 53.0(5) . . . . ?
C16 O1 C1 O2 0.5(7) . . . . ?
C16 O1 C1 N1 -177.9(4) . . . . ?
C6 N1 C1 O2 2.1(7) . . . . ?
C2 N1 C1 O2 173.1(5) . . . . ?
C6 N1 C1 O1 -179.6(4) . . . . ?
C2 N1 C1 O1 -8.6(6) . . . . ?
C5 C6 C7 C8 -0.1(7) . . . . ?
N1 C6 C7 C8 -178.1(4) . . . . ?
C6 C7 C8 C9 -1.5(7) . . . . ?
C10 C9 C8 C7 1.2(7) . . . . ?
C2 C3 C4 C5 1.6(7) . . . . ?
C10 C5 C4 C3 -163.6(5) . . . . ?
C6 C5 C4 C3 16.3(6) . . . . ?
C12 C13 C14 C15 170.2(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.494
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.059
