# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_1
_database_code_depnum_ccdc_archive 'CCDC 1060102'
_audit_update_record             
;
2015-04-17 deposited with the CCDC.
2015-06-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        (3S,8R)-3j'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H22 Br N3 O5'
_chemical_formula_sum            'C21 H22 Br N3 O5'
_chemical_formula_weight         476.33

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                   9.8915(4)
_cell_length_b                   9.4814(4)
_cell_length_c                   11.9420(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.048(4)
_cell_angle_gamma                90.00
_cell_volume                     1095.31(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    1357
_cell_measurement_theta_min      3.6810
_cell_measurement_theta_max      25.9810

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             488
_exptl_absorpt_coefficient_mu    1.913
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5976
_exptl_absorpt_correction_T_max  0.8317
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) 
(compiled Dec  3 2012,18:21:49) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(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  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 16.1903
_diffrn_standards_number         4753
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4375
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_sigmaI/netI    0.0487
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.49
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3468
_reflns_number_gt                3305
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_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)+(0.0683P)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       ?
_chemical_absolute_configuration unk
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.002(9)
_refine_ls_number_reflns         3468
_refine_ls_number_parameters     271
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.1077
_refine_ls_wR_factor_gt          0.1030
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_refine_ls_shift/su_max          0.000
_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 0.70856(4) 0.41160(4) 0.02243(3) 0.04483(15) Uani 1 1 d . . .
N1 N 0.9739(3) 0.7520(3) -0.2981(3) 0.0278(7) Uani 1 1 d . . .
N2 N 0.8219(3) 0.4626(4) -0.4513(3) 0.0312(7) Uani 1 1 d . . .
H2A H 0.8291 0.3771 -0.4782 0.037 Uiso 1 1 calc R . .
N3 N 1.0258(3) 0.2716(3) -0.2951(3) 0.0262(7) Uani 1 1 d . . .
C1 C 1.0137(4) 0.8992(5) -0.2984(3) 0.0391(9) Uani 1 1 d . . .
H1A H 1.0553 0.9177 -0.3646 0.059 Uiso 1 1 calc R . .
H1B H 1.0810 0.9206 -0.2278 0.059 Uiso 1 1 calc R . .
H1C H 0.9318 0.9589 -0.3029 0.059 Uiso 1 1 calc R . .
C2 C 0.9779(4) 0.6621(4) -0.3855(3) 0.0269(8) Uani 1 1 d . . .
C3 C 0.9231(4) 0.5156(4) -0.3546(3) 0.0232(7) Uani 1 1 d . . .
C4 C 1.0525(3) 0.4183(4) -0.3353(3) 0.0231(6) Uani 1 1 d . . .
H4A H 1.0793 0.4077 -0.4111 0.028 Uiso 1 1 calc R . .
C5 C 0.7152(4) 0.5491(5) -0.4993(3) 0.0347(9) Uani 1 1 d . . .
C6 C 0.5006(4) 0.5490(5) -0.6454(3) 0.0340(9) Uani 1 1 d . . .
C7 C 0.4347(4) 0.4317(6) -0.7263(4) 0.0529(13) Uani 1 1 d . . .
H7A H 0.4924 0.4124 -0.7820 0.079 Uiso 1 1 calc R . .
H7B H 0.3425 0.4614 -0.7667 0.079 Uiso 1 1 calc R . .
H7C H 0.4269 0.3461 -0.6821 0.079 Uiso 1 1 calc R . .
C8 C 0.4097(5) 0.5772(8) -0.5599(5) 0.0656(17) Uani 1 1 d . . .
H8A H 0.4508 0.6523 -0.5074 0.098 Uiso 1 1 calc R . .
H8B H 0.4020 0.4911 -0.5163 0.098 Uiso 1 1 calc R . .
H8C H 0.3175 0.6064 -0.6009 0.098 Uiso 1 1 calc R . .
C9 C 0.5338(5) 0.6756(6) -0.7101(5) 0.0592(15) Uani 1 1 d . . .
H9A H 0.5759 0.7487 -0.6558 0.089 Uiso 1 1 calc R . .
H9B H 0.4487 0.7122 -0.7585 0.089 Uiso 1 1 calc R . .
H9C H 0.5986 0.6487 -0.7583 0.089 Uiso 1 1 calc R . .
C11 C 0.8871(4) 0.7477(4) -0.1158(3) 0.0300(8) Uani 1 1 d . . .
H11A H 0.9120 0.8426 -0.0960 0.036 Uiso 1 1 calc R . .
C12 C 0.8258(4) 0.6654(5) -0.0453(3) 0.0354(9) Uani 1 1 d . . .
H12A H 0.8097 0.7032 0.0244 0.042 Uiso 1 1 calc R . .
C13 C 0.7878(4) 0.5282(4) -0.0758(3) 0.0286(8) Uani 1 1 d . . .
C14 C 0.8090(3) 0.4695(4) -0.1777(3) 0.0263(7) Uani 1 1 d . . .
H14A H 0.7799 0.3761 -0.1992 0.032 Uiso 1 1 calc R . .
C15 C 0.8731(3) 0.5504(4) -0.2461(3) 0.0230(7) Uani 1 1 d . . .
C16 C 0.9115(4) 0.6898(4) -0.2157(3) 0.0240(7) Uani 1 1 d . . .
C21 C 1.1768(3) 0.4802(4) -0.2531(3) 0.0241(7) Uani 1 1 d . . .
C22 C 1.2870(4) 0.5311(5) -0.2976(4) 0.0441(11) Uani 1 1 d . . .
H22A H 1.2831 0.5254 -0.3776 0.053 Uiso 1 1 calc R . .
C23 C 1.4009(5) 0.5891(6) -0.2275(7) 0.0703(19) Uani 1 1 d . . .
H23A H 1.4752 0.6235 -0.2589 0.084 Uiso 1 1 calc R . .
C24 C 1.4073(5) 0.5974(6) -0.1135(7) 0.0661(19) Uani 1 1 d . . .
H24A H 1.4857 0.6388 -0.0652 0.079 Uiso 1 1 calc R . .
C25 C 1.2995(5) 0.5456(5) -0.0662(5) 0.0516(13) Uani 1 1 d . . .
H25A H 1.3048 0.5505 0.0141 0.062 Uiso 1 1 calc R . .
C26 C 1.1859(4) 0.4876(4) -0.1369(3) 0.0327(9) Uani 1 1 d . . .
H26A H 1.1125 0.4519 -0.1050 0.039 Uiso 1 1 calc R . .
O1 O 1.0244(3) 0.6877(3) -0.4702(2) 0.0390(7) Uani 1 1 d . . .
O2 O 0.7020(3) 0.6677(4) -0.4672(3) 0.0522(10) Uani 1 1 d . . .
O3 O 0.6309(3) 0.4800(3) -0.5842(2) 0.0344(6) Uani 1 1 d . . .
O4 O 0.9076(3) 0.2331(3) -0.3001(3) 0.0380(7) Uani 1 1 d . . .
O5 O 1.1267(3) 0.1984(3) -0.2630(3) 0.0562(10) Uani 1 1 d . . .


_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 C13 1.896(4) . ?
N1 C2 1.355(5) . ?
N1 C16 1.397(5) . ?
N1 C1 1.450(6) . ?
N2 C5 1.364(5) . ?
N2 C3 1.451(4) . ?
N2 H2A 0.8800 . ?
N3 O5 1.210(4) . ?
N3 O4 1.215(4) . ?
N3 C4 1.513(5) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 O1 1.220(5) . ?
C2 C3 1.563(5) . ?
C3 C15 1.517(5) . ?
C3 C4 1.555(5) . ?
C4 C21 1.522(5) . ?
C4 H4A 1.0000 . ?
C5 O2 1.205(6) . ?
C5 O3 1.341(4) . ?
C6 O3 1.493(4) . ?
C6 C9 1.501(7) . ?
C6 C8 1.519(6) . ?
C6 C7 1.526(7) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C11 C12 1.377(6) . ?
C11 C16 1.379(5) . ?
C11 H11A 0.9500 . ?
C12 C13 1.382(6) . ?
C12 H12A 0.9500 . ?
C13 C14 1.394(5) . ?
C14 C15 1.369(5) . ?
C14 H14A 0.9500 . ?
C15 C16 1.401(5) . ?
C21 C26 1.374(5) . ?
C21 C22 1.395(5) . ?
C22 C23 1.371(8) . ?
C22 H22A 0.9500 . ?
C23 C24 1.351(10) . ?
C23 H23A 0.9500 . ?
C24 C25 1.395(9) . ?
C24 H24A 0.9500 . ?
C25 C26 1.372(6) . ?
C25 H25A 0.9500 . ?
C26 H26A 0.9500 . ?

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
C2 N1 C16 111.4(3) . . ?
C2 N1 C1 123.5(3) . . ?
C16 N1 C1 124.6(3) . . ?
C5 N2 C3 118.1(3) . . ?
C5 N2 H2A 120.9 . . ?
C3 N2 H2A 120.9 . . ?
O5 N3 O4 124.4(3) . . ?
O5 N3 C4 116.2(3) . . ?
O4 N3 C4 119.4(3) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 N1 126.2(4) . . ?
O1 C2 C3 125.6(3) . . ?
N1 C2 C3 108.0(3) . . ?
N2 C3 C15 117.5(3) . . ?
N2 C3 C4 108.8(3) . . ?
C15 C3 C4 114.0(3) . . ?
N2 C3 C2 109.6(3) . . ?
C15 C3 C2 101.5(3) . . ?
C4 C3 C2 104.3(3) . . ?
N3 C4 C21 108.7(3) . . ?
N3 C4 C3 113.6(3) . . ?
C21 C4 C3 113.3(3) . . ?
N3 C4 H4A 106.9 . . ?
C21 C4 H4A 106.9 . . ?
C3 C4 H4A 106.9 . . ?
O2 C5 O3 127.3(3) . . ?
O2 C5 N2 123.5(3) . . ?
O3 C5 N2 109.2(4) . . ?
O3 C6 C9 110.0(3) . . ?
O3 C6 C8 108.7(3) . . ?
C9 C6 C8 115.4(5) . . ?
O3 C6 C7 101.7(3) . . ?
C9 C6 C7 111.6(4) . . ?
C8 C6 C7 108.6(4) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C12 C11 C16 118.8(4) . . ?
C12 C11 H11A 120.6 . . ?
C16 C11 H11A 120.6 . . ?
C11 C12 C13 120.2(4) . . ?
C11 C12 H12A 119.9 . . ?
C13 C12 H12A 119.9 . . ?
C12 C13 C14 121.5(4) . . ?
C12 C13 Br1 120.8(3) . . ?
C14 C13 Br1 117.7(3) . . ?
C15 C14 C13 118.0(3) . . ?
C15 C14 H14A 121.0 . . ?
C13 C14 H14A 121.0 . . ?
C14 C15 C16 120.5(3) . . ?
C14 C15 C3 131.4(3) . . ?
C16 C15 C3 107.9(3) . . ?
C11 C16 N1 128.6(3) . . ?
C11 C16 C15 120.8(4) . . ?
N1 C16 C15 110.6(3) . . ?
C26 C21 C22 118.4(4) . . ?
C26 C21 C4 123.0(3) . . ?
C22 C21 C4 118.5(4) . . ?
C23 C22 C21 120.9(5) . . ?
C23 C22 H22A 119.5 . . ?
C21 C22 H22A 119.5 . . ?
C24 C23 C22 119.9(5) . . ?
C24 C23 H23A 120.1 . . ?
C22 C23 H23A 120.1 . . ?
C23 C24 C25 120.6(5) . . ?
C23 C24 H24A 119.7 . . ?
C25 C24 H24A 119.7 . . ?
C26 C25 C24 119.2(5) . . ?
C26 C25 H25A 120.4 . . ?
C24 C25 H25A 120.4 . . ?
C25 C26 C21 121.0(4) . . ?
C25 C26 H26A 119.5 . . ?
C21 C26 H26A 119.5 . . ?
C5 O3 C6 119.6(3) . . ?

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
C16 N1 C2 O1 178.9(3) . . . . ?
C1 N1 C2 O1 6.1(6) . . . . ?
C16 N1 C2 C3 -5.4(4) . . . . ?
C1 N1 C2 C3 -178.3(3) . . . . ?
C5 N2 C3 C15 63.4(5) . . . . ?
C5 N2 C3 C4 -165.1(3) . . . . ?
C5 N2 C3 C2 -51.7(4) . . . . ?
O1 C2 C3 N2 -52.2(5) . . . . ?
N1 C2 C3 N2 132.1(3) . . . . ?
O1 C2 C3 C15 -177.2(3) . . . . ?
N1 C2 C3 C15 7.2(3) . . . . ?
O1 C2 C3 C4 64.1(4) . . . . ?
N1 C2 C3 C4 -111.5(3) . . . . ?
O5 N3 C4 C21 -42.5(4) . . . . ?
O4 N3 C4 C21 139.8(3) . . . . ?
O5 N3 C4 C3 -169.7(3) . . . . ?
O4 N3 C4 C3 12.6(4) . . . . ?
N2 C3 C4 N3 -67.5(3) . . . . ?
C15 C3 C4 N3 65.8(4) . . . . ?
C2 C3 C4 N3 175.6(3) . . . . ?
N2 C3 C4 C21 167.8(3) . . . . ?
C15 C3 C4 C21 -58.9(4) . . . . ?
C2 C3 C4 C21 50.9(4) . . . . ?
C3 N2 C5 O2 1.4(7) . . . . ?
C3 N2 C5 O3 -177.9(3) . . . . ?
C16 C11 C12 C13 -1.1(6) . . . . ?
C11 C12 C13 C14 -0.4(6) . . . . ?
C11 C12 C13 Br1 178.1(3) . . . . ?
C12 C13 C14 C15 2.1(5) . . . . ?
Br1 C13 C14 C15 -176.5(2) . . . . ?
C13 C14 C15 C16 -2.2(5) . . . . ?
C13 C14 C15 C3 173.6(3) . . . . ?
N2 C3 C15 C14 57.9(5) . . . . ?
C4 C3 C15 C14 -71.2(5) . . . . ?
C2 C3 C15 C14 177.3(3) . . . . ?
N2 C3 C15 C16 -125.9(3) . . . . ?
C4 C3 C15 C16 105.0(3) . . . . ?
C2 C3 C15 C16 -6.5(3) . . . . ?
C12 C11 C16 N1 -178.8(3) . . . . ?
C12 C11 C16 C15 0.9(5) . . . . ?
C2 N1 C16 C11 -179.1(3) . . . . ?
C1 N1 C16 C11 -6.4(6) . . . . ?
C2 N1 C16 C15 1.1(4) . . . . ?
C1 N1 C16 C15 173.9(3) . . . . ?
C14 C15 C16 C11 0.8(5) . . . . ?
C3 C15 C16 C11 -175.9(3) . . . . ?
C14 C15 C16 N1 -179.5(3) . . . . ?
C3 C15 C16 N1 3.8(4) . . . . ?
N3 C4 C21 C26 -53.7(5) . . . . ?
C3 C4 C21 C26 73.5(5) . . . . ?
N3 C4 C21 C22 125.9(4) . . . . ?
C3 C4 C21 C22 -106.9(4) . . . . ?
C26 C21 C22 C23 -1.0(6) . . . . ?
C4 C21 C22 C23 179.3(4) . . . . ?
C21 C22 C23 C24 0.1(8) . . . . ?
C22 C23 C24 C25 0.8(9) . . . . ?
C23 C24 C25 C26 -0.8(8) . . . . ?
C24 C25 C26 C21 -0.2(7) . . . . ?
C22 C21 C26 C25 1.1(6) . . . . ?
C4 C21 C26 C25 -179.3(4) . . . . ?
O2 C5 O3 C6 -3.4(7) . . . . ?
N2 C5 O3 C6 175.9(3) . . . . ?
C9 C6 O3 C5 65.5(5) . . . . ?
C8 C6 O3 C5 -61.7(5) . . . . ?
C7 C6 O3 C5 -176.2(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.054
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane, n-Hexane'
####################################################################### 
# 
# 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_hy1
_database_code_depnum_ccdc_archive 'CCDC 1060112'
_audit_update_record             
;
2015-04-17 deposited with the CCDC.
2015-06-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        (Z)-1j
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H16 Br N2 O3'
_chemical_formula_sum            'C14 H15 Br N2 O3'
_chemical_formula_weight         339.19

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   Pna2(1)

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

_cell_length_a                   7.1573(4)
_cell_length_b                   21.4898(9)
_cell_length_c                   9.4975(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1460.80(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1417
_cell_measurement_theta_min      4.7060
_cell_measurement_theta_max      29.9990

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    2.822
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6022
_exptl_absorpt_correction_T_max  0.7282
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) 
(compiled Dec  3 2012,18:21:49) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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  'multiwire proportional'
_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            3518
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0422
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.42
_diffrn_reflns_theta_max         25.98
_reflns_number_total             2200
_reflns_number_gt                2075
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_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)+(0.0468P)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    constr
_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)
_refine_ls_number_reflns         2200
_refine_ls_number_parameters     181
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0344
_refine_ls_wR_factor_ref         0.0811
_refine_ls_wR_factor_gt          0.0787
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_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 0.73273(4) 0.685253(15) 0.59140(8) 0.02877(13) Uani 1 1 d . . .
C1 C 0.3809(6) 0.69044(17) -0.1089(4) 0.0297(9) Uani 1 1 d . . .
H1A H 0.3341 0.7152 -0.1881 0.045 Uiso 1 1 calc R . .
H1B H 0.2842 0.6611 -0.0786 0.045 Uiso 1 1 calc R . .
H1C H 0.4924 0.6674 -0.1383 0.045 Uiso 1 1 calc R . .
C2 C 0.4250(5) 0.79592(17) 0.0000(4) 0.0218(8) Uani 1 1 d . . .
C3 C 0.5053(5) 0.81965(15) 0.1379(4) 0.0187(8) Uani 1 1 d . . .
C4 C 0.5442(5) 0.76409(16) 0.2231(4) 0.0195(8) Uani 1 1 d . . .
C5 C 0.4981(5) 0.71253(16) 0.1394(4) 0.0195(8) Uani 1 1 d . . .
C6 C 0.5238(5) 0.65277(17) 0.1884(4) 0.0254(8) Uani 1 1 d . . .
H6A H 0.4943 0.6177 0.1317 0.030 Uiso 1 1 calc R . .
C7 C 0.5942(5) 0.64558(17) 0.3235(4) 0.0250(8) Uani 1 1 d . . .
H7A H 0.6135 0.6049 0.3595 0.030 Uiso 1 1 calc R . .
C8 C 0.6369(5) 0.69657(17) 0.4071(4) 0.0214(8) Uani 1 1 d . . .
C9 C 0.6132(5) 0.75696(16) 0.3580(4) 0.0200(7) Uani 1 1 d . . .
H9A H 0.6432 0.7919 0.4149 0.024 Uiso 1 1 calc R . .
C10 C 0.5111(5) 0.92576(15) 0.0809(5) 0.0241(7) Uani 1 1 d . . .
C11 C 0.2915(6) 1.01117(18) 0.0380(5) 0.0310(9) Uani 1 1 d . . .
C12 C 0.1088(7) 1.0262(2) 0.1115(6) 0.0597(15) Uani 1 1 d . . .
H12A H 0.1325 1.0339 0.2116 0.090 Uiso 1 1 calc R . .
H12B H 0.0227 0.9910 0.1016 0.090 Uiso 1 1 calc R . .
H12C H 0.0531 1.0633 0.0689 0.090 Uiso 1 1 calc R . .
C13 C 0.2630(7) 0.9970(3) -0.1155(5) 0.0484(13) Uani 1 1 d . . .
H13A H 0.1673 0.9646 -0.1256 0.073 Uiso 1 1 calc R . .
H13B H 0.3806 0.9822 -0.1565 0.073 Uiso 1 1 calc R . .
H13C H 0.2224 1.0347 -0.1646 0.073 Uiso 1 1 calc R . .
C14 C 0.4336(7) 1.06221(19) 0.0615(6) 0.0548(16) Uani 1 1 d . . .
H14A H 0.4490 1.0693 0.1628 0.082 Uiso 1 1 calc R . .
H14B H 0.3902 1.1006 0.0165 0.082 Uiso 1 1 calc R . .
H14C H 0.5536 1.0498 0.0205 0.082 Uiso 1 1 calc R . .
O1 O 0.3696(4) 0.82762(13) -0.0978(3) 0.0290(6) Uani 1 1 d . . .
O2 O 0.6291(4) 0.94225(12) -0.0007(3) 0.0367(7) Uani 1 1 d . . .
O3 O 0.3509(3) 0.95316(10) 0.1120(3) 0.0261(6) Uani 1 1 d . . .
N1 N 0.4287(4) 0.73176(14) 0.0080(3) 0.0219(7) Uani 1 1 d . . .
N2 N 0.5393(4) 0.87530(14) 0.1740(3) 0.0239(7) Uani 1 1 d . . .


_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 C8 1.896(4) . ?
C1 N1 1.462(5) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 O1 1.218(5) . ?
C2 N1 1.381(5) . ?
C2 C3 1.518(5) . ?
C3 N2 1.268(4) . ?
C3 C4 1.469(5) . ?
C4 C9 1.381(5) . ?
C4 C5 1.403(5) . ?
C5 C6 1.378(5) . ?
C5 N1 1.406(5) . ?
C6 C7 1.386(6) . ?
C6 H6A 0.9500 . ?
C7 C8 1.388(5) . ?
C7 H7A 0.9500 . ?
C8 C9 1.390(5) . ?
C9 H9A 0.9500 . ?
C10 O2 1.200(5) . ?
C10 O3 1.322(4) . ?
C10 N2 1.414(5) . ?
C11 O3 1.493(4) . ?
C11 C13 1.503(7) . ?
C11 C14 1.512(6) . ?
C11 C12 1.518(6) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

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
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 N1 127.3(4) . . ?
O1 C2 C3 126.4(3) . . ?
N1 C2 C3 106.3(3) . . ?
N2 C3 C4 125.6(3) . . ?
N2 C3 C2 128.5(3) . . ?
C4 C3 C2 105.9(3) . . ?
C9 C4 C5 121.5(3) . . ?
C9 C4 C3 132.0(3) . . ?
C5 C4 C3 106.6(3) . . ?
C6 C5 C4 120.9(3) . . ?
C6 C5 N1 128.4(3) . . ?
C4 C5 N1 110.7(3) . . ?
C5 C6 C7 117.7(4) . . ?
C5 C6 H6A 121.2 . . ?
C7 C6 H6A 121.2 . . ?
C6 C7 C8 121.4(3) . . ?
C6 C7 H7A 119.3 . . ?
C8 C7 H7A 119.3 . . ?
C7 C8 C9 121.2(4) . . ?
C7 C8 Br1 120.5(3) . . ?
C9 C8 Br1 118.3(3) . . ?
C4 C9 C8 117.3(3) . . ?
C4 C9 H9A 121.4 . . ?
C8 C9 H9A 121.4 . . ?
O2 C10 O3 128.5(3) . . ?
O2 C10 N2 122.0(3) . . ?
O3 C10 N2 109.0(3) . . ?
O3 C11 C13 109.0(4) . . ?
O3 C11 C14 110.2(3) . . ?
C13 C11 C14 112.5(4) . . ?
O3 C11 C12 101.9(3) . . ?
C13 C11 C12 111.9(4) . . ?
C14 C11 C12 110.9(4) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C10 O3 C11 120.9(3) . . ?
C2 N1 C5 110.4(3) . . ?
C2 N1 C1 124.1(3) . . ?
C5 N1 C1 125.3(3) . . ?
C3 N2 C10 121.8(3) . . ?

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
O1 C2 C3 N2 -4.4(6) . . . . ?
N1 C2 C3 N2 175.4(4) . . . . ?
O1 C2 C3 C4 177.8(4) . . . . ?
N1 C2 C3 C4 -2.5(4) . . . . ?
N2 C3 C4 C9 3.8(7) . . . . ?
C2 C3 C4 C9 -178.2(4) . . . . ?
N2 C3 C4 C5 -175.7(4) . . . . ?
C2 C3 C4 C5 2.3(4) . . . . ?
C9 C4 C5 C6 -1.3(5) . . . . ?
C3 C4 C5 C6 178.3(3) . . . . ?
C9 C4 C5 N1 179.1(3) . . . . ?
C3 C4 C5 N1 -1.3(4) . . . . ?
C4 C5 C6 C7 0.8(5) . . . . ?
N1 C5 C6 C7 -179.7(3) . . . . ?
C5 C6 C7 C8 0.2(5) . . . . ?
C6 C7 C8 C9 -0.9(5) . . . . ?
C6 C7 C8 Br1 179.9(3) . . . . ?
C5 C4 C9 C8 0.6(5) . . . . ?
C3 C4 C9 C8 -178.8(4) . . . . ?
C7 C8 C9 C4 0.4(5) . . . . ?
Br1 C8 C9 C4 179.6(3) . . . . ?
O2 C10 O3 C11 2.8(6) . . . . ?
N2 C10 O3 C11 175.2(3) . . . . ?
C13 C11 O3 C10 64.0(5) . . . . ?
C14 C11 O3 C10 -59.9(5) . . . . ?
C12 C11 O3 C10 -177.7(4) . . . . ?
O1 C2 N1 C5 -178.5(4) . . . . ?
C3 C2 N1 C5 1.8(4) . . . . ?
O1 C2 N1 C1 6.1(6) . . . . ?
C3 C2 N1 C1 -173.6(3) . . . . ?
C6 C5 N1 C2 -179.9(3) . . . . ?
C4 C5 N1 C2 -0.4(4) . . . . ?
C6 C5 N1 C1 -4.6(6) . . . . ?
C4 C5 N1 C1 175.0(3) . . . . ?
C4 C3 N2 C10 174.9(3) . . . . ?
C2 C3 N2 C10 -2.7(6) . . . . ?
O2 C10 N2 C3 -86.8(5) . . . . ?
O3 C10 N2 C3 100.2(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.98
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.647
_refine_diff_density_min         -0.744
_refine_diff_density_rms         0.084
