# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
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# 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 
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data_cu_qsgl359b2_0m
_database_code_depnum_ccdc_archive 'CCDC 1870220'
_audit_update_record             
;
2018-09-27 deposited with the CCDC.
2019-01-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H23 Br N2 O4 S'
_chemical_formula_sum            'C21 H23 Br N2 O4 S'
_chemical_formula_weight         479.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   9.4007(2)
_cell_length_b                   10.8468(2)
_cell_length_c                   21.7267(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2215.42(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9981
_cell_measurement_theta_min      4.07
_cell_measurement_theta_max      70.23

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_F_000             984
_exptl_transmission_factor_min   0.0729
_exptl_transmission_factor_max   0.2751
_exptl_crystal_size_max          0.710
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    3.653
_shelx_estimated_absorpt_T_min   0.181
_shelx_estimated_absorpt_T_max   0.500
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13347
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         4.069
_diffrn_reflns_theta_max         70.227
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.899
_diffrn_reflns_point_group_measured_fraction_full 0.924
_reflns_number_total             3808
_reflns_number_gt                3787
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.616
_reflns_Friedel_fraction_max     0.801
_reflns_Friedel_fraction_full    0.838

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_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)+(0.0476P)²+1.5272P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0033(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1414 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.089(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3808
_refine_ls_number_parameters     266
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0364
_refine_ls_wR_factor_ref         0.0946
_refine_ls_wR_factor_gt          0.0944
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_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 0.66205(7) 1.28832(7) 0.79694(2) 0.0676(3) Uani 1 1 d . . . . .
S1 S 0.68688(10) 1.06052(7) 1.06789(4) 0.0229(2) Uani 1 1 d . . . . .
O1 O 0.7991(3) 0.8556(3) 0.85027(12) 0.0351(7) Uani 1 1 d . . . . .
O2 O 0.9835(3) 0.7407(2) 0.88612(13) 0.0308(6) Uani 1 1 d . . . . .
O3 O 0.8119(3) 1.1123(2) 1.09556(12) 0.0317(6) Uani 1 1 d . . . . .
O4 O 0.5506(3) 1.0798(2) 1.09545(14) 0.0340(7) Uani 1 1 d . . . . .
N1 N 0.7066(3) 0.9132(2) 1.06036(14) 0.0234(6) Uani 1 1 d . . . . .
H2 H 0.6317 0.8647 1.0584 0.028 Uiso 1 1 calc R U . . .
N2 N 0.8098(3) 0.8146(3) 0.94912(13) 0.0256(6) Uani 1 1 d . . . . .
H11 H 0.7316 0.8590 0.9502 0.031 Uiso 1 1 calc R U . . .
C1 C 0.6708(4) 1.2146(3) 0.87611(18) 0.0325(8) Uani 1 1 d . . . . .
C2 C 0.5472(4) 1.1678(4) 0.9013(2) 0.0316(8) Uani 1 1 d . . . . .
H21 H 0.4605 1.1696 0.8788 0.038 Uiso 1 1 calc R U . . .
C3 C 0.5524(4) 1.1182(3) 0.96004(18) 0.0267(8) Uani 1 1 d . . . . .
H22 H 0.4693 1.0844 0.9783 0.032 Uiso 1 1 calc R U . . .
C4 C 0.6807(4) 1.1183(3) 0.99190(15) 0.0207(7) Uani 1 1 d . . . . .
C5 C 0.8516(4) 0.8606(3) 1.05685(17) 0.0235(7) Uani 1 1 d . . . . .
H19 H 0.9191 0.9289 1.0467 0.028 Uiso 1 1 calc R U . . .
C6 C 0.8616(4) 0.7637(3) 1.00603(16) 0.0213(7) Uani 1 1 d . . . . .
H18 H 0.9648 0.7449 1.0000 0.026 Uiso 1 1 calc R U . . .
C7 C 0.8747(4) 0.7981(3) 0.89388(16) 0.0223(7) Uani 1 1 d . . . . .
C8 C 0.8369(4) 0.8493(4) 0.78465(16) 0.0318(8) Uani 1 1 d . . . . .
C9 C 0.7210(6) 0.9287(7) 0.7559(2) 0.0670(18) Uani 1 1 d . . . . .
H1 H 0.6275 0.8984 0.7689 0.100 Uiso 1 1 calc R U . . .
H6 H 0.7281 0.9244 0.7109 0.100 Uiso 1 1 calc R U . . .
H7 H 0.7327 1.0143 0.7693 0.100 Uiso 1 1 calc R U . . .
C10 C 0.7988(4) 1.2144(4) 0.90649(18) 0.0313(8) Uani 1 1 d . . . . .
H24 H 0.8821 1.2466 0.8876 0.038 Uiso 1 1 calc R U . . .
C11 C 0.8032(4) 1.1656(3) 0.96565(17) 0.0258(7) Uani 1 1 d . . . . .
H23 H 0.8900 1.1648 0.9880 0.031 Uiso 1 1 calc R U . . .
C12 C 0.9783(6) 0.9110(7) 0.7749(2) 0.0648(17) Uani 1 1 d . . . . .
H5 H 0.9821 0.9874 0.7990 0.097 Uiso 1 1 calc R U . . .
H3 H 0.9904 0.9302 0.7312 0.097 Uiso 1 1 calc R U . . .
H4 H 1.0547 0.8557 0.7883 0.097 Uiso 1 1 calc R U . . .
C13 C 0.8308(12) 0.7206(5) 0.7628(3) 0.095(3) Uani 1 1 d . . . . .
H8 H 0.9155 0.6762 0.7770 0.143 Uiso 1 1 calc R U . . .
H10 H 0.8274 0.7196 0.7178 0.143 Uiso 1 1 calc R U . . .
H9 H 0.7454 0.6806 0.7793 0.143 Uiso 1 1 calc R U . . .
C14 C 0.7892(4) 0.6440(3) 1.02426(17) 0.0212(7) Uani 1 1 d . . . . .
C15 C 0.7981(4) 0.6080(3) 1.08635(17) 0.0243(7) Uani 1 1 d . . . . .
C16 C 0.8698(4) 0.6882(3) 1.13015(17) 0.0295(8) Uani 1 1 d . . . . .
H13 H 0.8994 0.6553 1.1686 0.035 Uiso 1 1 calc R U . . .
C17 C 0.8952(4) 0.8064(4) 1.11776(18) 0.0293(8) Uani 1 1 d . . . . .
H12 H 0.9411 0.8567 1.1475 0.035 Uiso 1 1 calc R U . . .
C18 C 0.7364(4) 0.4960(3) 1.10416(19) 0.0310(9) Uani 1 1 d . . . . .
H17 H 0.7419 0.4705 1.1459 0.037 Uiso 1 1 calc R U . . .
C19 C 0.6679(4) 0.4223(3) 1.0619(2) 0.0342(9) Uani 1 1 d . . . . .
H16 H 0.6251 0.3472 1.0747 0.041 Uiso 1 1 calc R U . . .
C20 C 0.6615(4) 0.4575(3) 1.0008(2) 0.0325(8) Uani 1 1 d . . . . .
H15 H 0.6158 0.4058 0.9716 0.039 Uiso 1 1 calc R U . . .
C21 C 0.7217(4) 0.5681(3) 0.98210(18) 0.0261(8) Uani 1 1 d . . . . .
H14 H 0.7165 0.5920 0.9401 0.031 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 C1 1.899(4) . ?
S1 O4 1.430(3) . ?
S1 O3 1.435(3) . ?
S1 N1 1.617(3) . ?
S1 C4 1.767(3) . ?
O1 C7 1.338(4) . ?
O1 C8 1.471(4) . ?
O2 C7 1.209(4) . ?
N1 C5 1.479(5) . ?
N1 H2 0.8800 . ?
N2 C7 1.358(5) . ?
N2 C6 1.439(5) . ?
N2 H11 0.8800 . ?
C1 C10 1.373(6) . ?
C1 C2 1.381(6) . ?
C2 C3 1.386(6) . ?
C2 H21 0.9500 . ?
C3 C4 1.390(5) . ?
C3 H22 0.9500 . ?
C4 C11 1.384(5) . ?
C5 C17 1.505(5) . ?
C5 C6 1.528(5) . ?
C5 H19 1.0000 . ?
C6 C14 1.519(5) . ?
C6 H18 1.0000 . ?
C8 C13 1.475(7) . ?
C8 C12 1.504(7) . ?
C8 C9 1.523(7) . ?
C9 H1 0.9800 . ?
C9 H6 0.9800 . ?
C9 H7 0.9800 . ?
C10 C11 1.390(6) . ?
C10 H24 0.9500 . ?
C11 H23 0.9500 . ?
C12 H5 0.9800 . ?
C12 H3 0.9800 . ?
C12 H4 0.9800 . ?
C13 H8 0.9800 . ?
C13 H10 0.9800 . ?
C13 H9 0.9800 . ?
C14 C21 1.385(5) . ?
C14 C15 1.407(5) . ?
C15 C18 1.401(5) . ?
C15 C16 1.455(6) . ?
C16 C17 1.332(6) . ?
C16 H13 0.9500 . ?
C17 H12 0.9500 . ?
C18 C19 1.377(6) . ?
C18 H17 0.9500 . ?
C19 C20 1.382(6) . ?
C19 H16 0.9500 . ?
C20 C21 1.387(5) . ?
C20 H15 0.9500 . ?
C21 H14 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
O4 S1 O3 120.09(17) . . ?
O4 S1 N1 106.85(16) . . ?
O3 S1 N1 109.60(16) . . ?
O4 S1 C4 108.05(18) . . ?
O3 S1 C4 106.24(17) . . ?
N1 S1 C4 105.05(15) . . ?
C7 O1 C8 122.4(3) . . ?
C5 N1 S1 119.5(2) . . ?
C5 N1 H2 120.3 . . ?
S1 N1 H2 120.3 . . ?
C7 N2 C6 123.8(3) . . ?
C7 N2 H11 118.1 . . ?
C6 N2 H11 118.1 . . ?
C10 C1 C2 123.1(3) . . ?
C10 C1 Br1 118.3(3) . . ?
C2 C1 Br1 118.5(3) . . ?
C1 C2 C3 118.6(4) . . ?
C1 C2 H21 120.7 . . ?
C3 C2 H21 120.7 . . ?
C2 C3 C4 119.2(3) . . ?
C2 C3 H22 120.4 . . ?
C4 C3 H22 120.4 . . ?
C11 C4 C3 121.1(3) . . ?
C11 C4 S1 119.3(3) . . ?
C3 C4 S1 119.6(3) . . ?
N1 C5 C17 110.9(3) . . ?
N1 C5 C6 111.1(3) . . ?
C17 C5 C6 110.5(3) . . ?
N1 C5 H19 108.1 . . ?
C17 C5 H19 108.1 . . ?
C6 C5 H19 108.1 . . ?
N2 C6 C14 113.6(3) . . ?
N2 C6 C5 109.6(3) . . ?
C14 C6 C5 111.9(3) . . ?
N2 C6 H18 107.1 . . ?
C14 C6 H18 107.1 . . ?
C5 C6 H18 107.1 . . ?
O2 C7 O1 126.2(3) . . ?
O2 C7 N2 124.8(3) . . ?
O1 C7 N2 109.0(3) . . ?
O1 C8 C13 110.2(4) . . ?
O1 C8 C12 109.2(4) . . ?
C13 C8 C12 114.2(6) . . ?
O1 C8 C9 101.5(3) . . ?
C13 C8 C9 112.1(5) . . ?
C12 C8 C9 108.9(4) . . ?
C8 C9 H1 109.5 . . ?
C8 C9 H6 109.5 . . ?
H1 C9 H6 109.5 . . ?
C8 C9 H7 109.5 . . ?
H1 C9 H7 109.5 . . ?
H6 C9 H7 109.5 . . ?
C1 C10 C11 118.1(4) . . ?
C1 C10 H24 121.0 . . ?
C11 C10 H24 121.0 . . ?
C4 C11 C10 119.9(3) . . ?
C4 C11 H23 120.1 . . ?
C10 C11 H23 120.1 . . ?
C8 C12 H5 109.5 . . ?
C8 C12 H3 109.5 . . ?
H5 C12 H3 109.5 . . ?
C8 C12 H4 109.5 . . ?
H5 C12 H4 109.5 . . ?
H3 C12 H4 109.5 . . ?
C8 C13 H8 109.5 . . ?
C8 C13 H10 109.5 . . ?
H8 C13 H10 109.5 . . ?
C8 C13 H9 109.5 . . ?
H8 C13 H9 109.5 . . ?
H10 C13 H9 109.5 . . ?
C21 C14 C15 119.8(3) . . ?
C21 C14 C6 122.7(3) . . ?
C15 C14 C6 117.4(3) . . ?
C18 C15 C14 118.7(4) . . ?
C18 C15 C16 122.0(3) . . ?
C14 C15 C16 119.3(3) . . ?
C17 C16 C15 121.8(3) . . ?
C17 C16 H13 119.1 . . ?
C15 C16 H13 119.1 . . ?
C16 C17 C5 120.3(3) . . ?
C16 C17 H12 119.8 . . ?
C5 C17 H12 119.8 . . ?
C19 C18 C15 120.9(4) . . ?
C19 C18 H17 119.6 . . ?
C15 C18 H17 119.6 . . ?
C18 C19 C20 120.0(3) . . ?
C18 C19 H16 120.0 . . ?
C20 C19 H16 120.0 . . ?
C19 C20 C21 120.2(4) . . ?
C19 C20 H15 119.9 . . ?
C21 C20 H15 119.9 . . ?
C14 C21 C20 120.4(4) . . ?
C14 C21 H14 119.8 . . ?
C20 C21 H14 119.8 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 S1 N1 C5 -156.0(3) . . . . ?
O3 S1 N1 C5 -24.4(3) . . . . ?
C4 S1 N1 C5 89.4(3) . . . . ?
C10 C1 C2 C3 0.0(6) . . . . ?
Br1 C1 C2 C3 -177.6(3) . . . . ?
C1 C2 C3 C4 0.7(6) . . . . ?
C2 C3 C4 C11 -0.8(5) . . . . ?
C2 C3 C4 S1 177.6(3) . . . . ?
O4 S1 C4 C11 149.2(3) . . . . ?
O3 S1 C4 C11 19.1(3) . . . . ?
N1 S1 C4 C11 -97.0(3) . . . . ?
O4 S1 C4 C3 -29.3(3) . . . . ?
O3 S1 C4 C3 -159.4(3) . . . . ?
N1 S1 C4 C3 84.5(3) . . . . ?
S1 N1 C5 C17 100.9(3) . . . . ?
S1 N1 C5 C6 -135.9(3) . . . . ?
C7 N2 C6 C14 -97.2(4) . . . . ?
C7 N2 C6 C5 136.8(3) . . . . ?
N1 C5 C6 N2 52.4(4) . . . . ?
C17 C5 C6 N2 175.9(3) . . . . ?
N1 C5 C6 C14 -74.5(4) . . . . ?
C17 C5 C6 C14 48.9(4) . . . . ?
C8 O1 C7 O2 3.8(6) . . . . ?
C8 O1 C7 N2 -176.4(3) . . . . ?
C6 N2 C7 O2 -1.0(6) . . . . ?
C6 N2 C7 O1 179.2(3) . . . . ?
C7 O1 C8 C13 61.4(6) . . . . ?
C7 O1 C8 C12 -64.8(5) . . . . ?
C7 O1 C8 C9 -179.7(4) . . . . ?
C2 C1 C10 C11 -0.7(6) . . . . ?
Br1 C1 C10 C11 177.0(3) . . . . ?
C3 C4 C11 C10 0.2(5) . . . . ?
S1 C4 C11 C10 -178.3(3) . . . . ?
C1 C10 C11 C4 0.6(6) . . . . ?
N2 C6 C14 C21 22.6(5) . . . . ?
C5 C6 C14 C21 147.3(3) . . . . ?
N2 C6 C14 C15 -160.4(3) . . . . ?
C5 C6 C14 C15 -35.6(4) . . . . ?
C21 C14 C15 C18 -0.8(5) . . . . ?
C6 C14 C15 C18 -177.9(3) . . . . ?
C21 C14 C15 C16 179.7(3) . . . . ?
C6 C14 C15 C16 2.5(5) . . . . ?
C18 C15 C16 C17 -162.1(4) . . . . ?
C14 C15 C16 C17 17.4(6) . . . . ?
C15 C16 C17 C5 -0.9(6) . . . . ?
N1 C5 C17 C16 91.1(4) . . . . ?
C6 C5 C17 C16 -32.5(5) . . . . ?
C14 C15 C18 C19 -0.1(5) . . . . ?
C16 C15 C18 C19 179.4(3) . . . . ?
C15 C18 C19 C20 1.1(6) . . . . ?
C18 C19 C20 C21 -1.2(6) . . . . ?
C15 C14 C21 C20 0.7(5) . . . . ?
C6 C14 C21 C20 177.7(3) . . . . ?
C19 C20 C21 C14 0.3(6) . . . . ?

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
C13 H8 O2 0.98 2.55 3.047(7) 111.1 .
C12 H4 O2 0.98 2.55 3.042(6) 110.8 .
C10 H24 O4 0.95 2.49 3.253(5) 137.7 2_577
C9 H7 Br1 0.98 3.10 4.040(7) 160.3 .
C9 H6 O3 0.98 2.57 3.525(6) 166.1 4_674
N1 H2 O2 0.88 2.17 2.922(4) 143.3 2_467
C10 H24 O4 0.95 2.49 3.253(5) 137.7 2_577
C9 H7 Br1 0.98 3.10 4.040(7) 160.3 .
C9 H6 O3 0.98 2.57 3.525(6) 166.1 4_674
N1 H2 O2 0.88 2.17 2.922(4) 143.3 2_467
C13 H8 O2 0.98 2.55 3.047(7) 111.1 .
C12 H4 O2 0.98 2.55 3.042(6) 110.8 .
C10 H24 O4 0.95 2.49 3.253(5) 137.7 2_577
C9 H7 Br1 0.98 3.10 4.040(7) 160.3 .
C9 H6 O3 0.98 2.57 3.525(6) 166.1 4_674
N1 H2 O2 0.88 2.17 2.922(4) 143.3 2_467
C13 H8 O2 0.98 2.55 3.047(7) 111.1 .
C12 H4 O2 0.98 2.55 3.042(6) 110.8 .
C10 H24 O4 0.95 2.49 3.253(5) 137.7 2_577
C9 H7 Br1 0.98 3.10 4.040(7) 160.3 .
C9 H6 O3 0.98 2.57 3.525(6) 166.1 4_674
N1 H2 O2 0.88 2.17 2.922(4) 143.3 2_467
C13 H8 O2 0.98 2.55 3.047(7) 111.1 .
C12 H4 O2 0.98 2.55 3.042(6) 110.8 .
C10 H24 O4 0.95 2.49 3.253(5) 137.7 2_577
C9 H7 Br1 0.98 3.10 4.040(7) 160.3 .
C9 H6 O3 0.98 2.57 3.525(6) 166.1 4_674
N1 H2 O2 0.88 2.17 2.922(4) 143.3 2_467
N1 H2 O2 0.88 2.17 2.922(4) 143.3 2_467
C9 H6 O3 0.98 2.57 3.525(6) 166.1 4_674
C9 H7 Br1 0.98 3.10 4.040(7) 160.3 .
C10 H24 O4 0.95 2.49 3.253(5) 137.7 2_577
C12 H4 O2 0.98 2.55 3.042(6) 110.8 .
C13 H8 O2 0.98 2.55 3.047(7) 111.1 .
N1 H2 O2 0.88 2.17 2.922(4) 143.3 2_467
C9 H6 O3 0.98 2.57 3.525(6) 166.1 4_674
C9 H7 Br1 0.98 3.10 4.040(7) 160.3 .
C10 H24 O4 0.95 2.49 3.253(5) 137.7 2_577
C12 H4 O2 0.98 2.55 3.042(6) 110.8 .
C13 H8 O2 0.98 2.55 3.047(7) 111.1 .
N1 H2 O2 0.88 2.17 2.922(4) 143.3 2_467
C9 H6 O3 0.98 2.57 3.525(6) 166.1 4_674
C9 H7 Br1 0.98 3.10 4.040(7) 160.3 .
C10 H24 O4 0.95 2.49 3.253(5) 137.7 2_577
C12 H4 O2 0.98 2.55 3.042(6) 110.8 .
C13 H8 O2 0.98 2.55 3.047(7) 111.1 .
N1 H2 O2 0.88 2.17 2.922(4) 143.3 2_467
C9 H6 O3 0.98 2.57 3.525(6) 166.1 4_674
C9 H7 Br1 0.98 3.10 4.040(7) 160.3 .
C10 H24 O4 0.95 2.49 3.253(5) 137.7 2_577

_refine_diff_density_max         0.904
_refine_diff_density_min         -0.872
_refine_diff_density_rms         0.078



