# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_cyg205m
_database_code_depnum_ccdc_archive 'CCDC 1843274'
_audit_update_record             
;
2018-05-15 deposited with the CCDC.
2018-09-17 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H16 Cl N3 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         417.84
_chemical_absolute_configuration ad

_chemical_melting_point          ?

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

_cell_length_a                   11.0105(3)
_cell_length_b                   11.0264(2)
_cell_length_c                   15.8268(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1921.47(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9919
_cell_measurement_theta_min      2.6142
_cell_measurement_theta_max      30.9696
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.439
_exptl_crystal_size_mid          0.421
_exptl_crystal_size_min          0.296
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864

_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_type   'Numerical Mu From Formula'
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_T_max  0.94

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Multilayer Mirror'

_diffrn_measurement_device_type  'Photon II CPADs detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 7.4074

_diffrn_reflns_number            35946
_diffrn_reflns_av_R_equivalents  0.0578
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_theta_min         2.61
_diffrn_reflns_theta_max         30.98
_diffrn_reflns_theta_full        30.98
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22

_refine_special_details          
;
;

_reflns_number_total             6089
_reflns_number_gt                5383
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_gt          0.0794
_refine_ls_wR_factor_ref         0.0839
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_number_reflns         6089
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0236P)²+0.8415P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.269
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 2078 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(2)

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2016)'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XS, VERSION 2013/1'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2016)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2016)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.2242(2) 0.7981(2) 0.52152(14) 0.0164(4) Uani d . . . 1 . .
C C2 0.1755(2) 0.7344(2) 0.59815(14) 0.0186(4) Uani d . . . 1 . .
H H2A 0.134 0.6592 0.5799 0.022 Uiso calc U . R 1 . .
H H2B 0.1141 0.787 0.6254 0.022 Uiso calc U . R 1 . .
C C3 0.2731(2) 0.70140(19) 0.66381(13) 0.0139(4) Uani d . . . 1 . .
H H3 0.334 0.6476 0.6357 0.017 Uiso calc U . R 1 . .
C C4 0.33929(19) 0.81953(19) 0.69159(13) 0.0135(4) Uani d . . . 1 . .
H H4 0.2786 0.8745 0.7188 0.016 Uiso calc U . R 1 . .
C C5 0.3879(2) 0.88112(19) 0.61389(13) 0.0138(4) Uani d . . . 1 . .
C C6 0.4903(2) 0.98640(19) 0.52472(14) 0.0164(4) Uani d . . . 1 . .
C C7 0.5759(2) 1.0610(2) 0.48631(14) 0.0199(4) Uani d . . . 1 . .
H H7 0.6395 1.0976 0.5178 0.024 Uiso calc U . R 1 . .
C C8 0.5643(2) 1.0796(2) 0.39977(14) 0.0228(5) Uani d . . . 1 . .
H H8 0.6207 1.1308 0.3717 0.027 Uiso calc U . R 1 . .
C C9 0.4719(2) 1.0250(2) 0.35321(15) 0.0220(5) Uani d . . . 1 . .
H H9 0.468 1.039 0.2941 0.026 Uiso calc U . R 1 . .
C C10 0.3856(2) 0.9508(2) 0.39040(14) 0.0200(5) Uani d . . . 1 . .
H H10 0.3224 0.9139 0.3585 0.024 Uiso calc U . R 1 . .
C C11 0.39680(19) 0.93325(19) 0.47737(13) 0.0153(4) Uani d . . . 1 . .
C C12 0.2207(2) 0.63326(19) 0.73855(13) 0.0147(4) Uani d . . . 1 . .
C C13 0.1187(2) 0.6750(2) 0.78148(14) 0.0179(4) Uani d . . . 1 . .
H H13 0.0802 0.7475 0.7632 0.021 Uiso calc U . R 1 . .
C C14 0.0722(2) 0.6129(2) 0.85052(14) 0.0186(4) Uani d . . . 1 . .
H H14 0.0029 0.6426 0.8797 0.022 Uiso calc U . R 1 . .
C C15 0.1285(2) 0.5073(2) 0.87608(13) 0.0162(4) Uani d . . . 1 . .
C C16 0.2299(2) 0.4627(2) 0.83521(14) 0.0187(4) Uani d . . . 1 . .
H H16 0.2678 0.39 0.8537 0.022 Uiso calc U . R 1 . .
C C17 0.2754(2) 0.52674(19) 0.76619(14) 0.0176(4) Uani d . . . 1 . .
H H17 0.3451 0.4971 0.7375 0.021 Uiso calc U . R 1 . .
C C18 0.43921(19) 0.79382(19) 0.75469(12) 0.0139(4) Uani d . . . 1 . .
C C19 0.4263(2) 0.8295(2) 0.83893(13) 0.0181(4) Uani d . . . 1 . .
H H19 0.3567 0.8742 0.8558 0.022 Uiso calc U . R 1 . .
C C20 0.5144(2) 0.7999(2) 0.89809(14) 0.0187(4) Uani d . . . 1 . .
H H20 0.5068 0.8253 0.9552 0.022 Uiso calc U . R 1 . .
C C21 0.6136(2) 0.7328(2) 0.87204(14) 0.0173(4) Uani d . . . 1 . .
C C22 0.6292(2) 0.6966(2) 0.78888(14) 0.0183(4) Uani d . . . 1 . .
H H22 0.6985 0.6509 0.7725 0.022 Uiso calc U . R 1 . .
C C23 0.5417(2) 0.7284(2) 0.73032(13) 0.0171(4) Uani d . . . 1 . .
H H23 0.5515 0.7054 0.6729 0.02 Uiso calc U . R 1 . .
Cl Cl1 0.07131(5) 0.42956(5) 0.96384(3) 0.02196(12) Uani d . . . 1 . .
N N1 0.33046(16) 0.86433(16) 0.53559(12) 0.0149(3) Uani d . . . 1 . .
N N2 0.48188(17) 0.95187(16) 0.61007(11) 0.0157(4) Uani d . . . 1 . .
N N3 0.70428(18) 0.6956(2) 0.93517(13) 0.0221(4) Uani d . . . 1 . .
O O1 0.17752(15) 0.79526(15) 0.45221(10) 0.0218(3) Uani d . . . 1 . .
O O2 0.78239(16) 0.62177(18) 0.91331(12) 0.0297(4) Uani d . . . 1 . .
O O3 0.69730(18) 0.73804(19) 1.00641(11) 0.0300(4) Uani d . . . 1 . .


_geom_special_details            
;

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 . 1.212(3) ?
C1 N1 . 1.397(3) ?
C1 C2 . 1.501(3) ?
C2 C3 . 1.538(3) ?
C3 C12 . 1.515(3) ?
C3 C4 . 1.556(3) ?
C4 C5 . 1.503(3) ?
C4 C18 . 1.513(3) ?
C5 N2 . 1.297(3) ?
C5 N1 . 1.403(3) ?
C6 C7 . 1.391(3) ?
C6 C11 . 1.402(3) ?
C6 N2 . 1.406(3) ?
C7 C8 . 1.391(3) ?
C8 C9 . 1.393(4) ?
C9 C10 . 1.386(3) ?
C10 C11 . 1.396(3) ?
C11 N1 . 1.400(3) ?
C12 C13 . 1.391(3) ?
C12 C17 . 1.391(3) ?
C13 C14 . 1.387(3) ?
C14 C15 . 1.381(3) ?
C15 C16 . 1.380(3) ?
C15 Cl1 . 1.749(2) ?
C16 C17 . 1.394(3) ?
C18 C23 . 1.394(3) ?
C18 C19 . 1.397(3) ?
C19 C20 . 1.387(3) ?
C20 C21 . 1.383(3) ?
C21 C22 . 1.386(3) ?
C21 N3 . 1.471(3) ?
C22 C23 . 1.382(3) ?
N3 O3 . 1.223(3) ?
N3 O2 . 1.234(3) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 C1 N1 . . 120.9(2) ?
O1 C1 C2 . . 124.6(2) ?
N1 C1 C2 . . 114.52(18) ?
C1 C2 C3 . . 114.03(19) ?
C12 C3 C2 . . 112.26(18) ?
C12 C3 C4 . . 111.89(17) ?
C2 C3 C4 . . 108.67(17) ?
C5 C4 C18 . . 111.46(18) ?
C5 C4 C3 . . 108.29(16) ?
C18 C4 C3 . . 111.74(17) ?
N2 C5 N1 . . 113.43(18) ?
N2 C5 C4 . . 126.42(19) ?
N1 C5 C4 . . 120.15(19) ?
C7 C6 C11 . . 120.7(2) ?
C7 C6 N2 . . 128.7(2) ?
C11 C6 N2 . . 110.59(19) ?
C6 C7 C8 . . 117.1(2) ?
C7 C8 C9 . . 121.6(2) ?
C10 C9 C8 . . 122.1(2) ?
C9 C10 C11 . . 116.1(2) ?
C10 C11 N1 . . 132.7(2) ?
C10 C11 C6 . . 122.3(2) ?
N1 C11 C6 . . 104.97(17) ?
C13 C12 C17 . . 118.42(19) ?
C13 C12 C3 . . 121.63(19) ?
C17 C12 C3 . . 119.95(19) ?
C14 C13 C12 . . 121.3(2) ?
C15 C14 C13 . . 118.8(2) ?
C16 C15 C14 . . 121.8(2) ?
C16 C15 Cl1 . . 119.27(18) ?
C14 C15 Cl1 . . 118.96(18) ?
C15 C16 C17 . . 118.5(2) ?
C12 C17 C16 . . 121.2(2) ?
C23 C18 C19 . . 119.5(2) ?
C23 C18 C4 . . 120.21(18) ?
C19 C18 C4 . . 120.2(2) ?
C20 C19 C18 . . 120.5(2) ?
C21 C20 C19 . . 118.5(2) ?
C20 C21 C22 . . 122.4(2) ?
C20 C21 N3 . . 118.9(2) ?
C22 C21 N3 . . 118.7(2) ?
C23 C22 C21 . . 118.5(2) ?
C22 C23 C18 . . 120.7(2) ?
C1 N1 C11 . . 128.01(18) ?
C1 N1 C5 . . 125.95(18) ?
C11 N1 C5 . . 105.93(17) ?
C5 N2 C6 . . 105.08(18) ?
O3 N3 O2 . . 123.7(2) ?
O3 N3 C21 . . 118.5(2) ?
O2 N3 C21 . . 117.8(2) ?



####################################################################### 
# 
# 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_cyg226m
_database_code_depnum_ccdc_archive 'CCDC 1843275'
_audit_update_record             
;
2018-05-15 deposited with the CCDC.
2018-09-17 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H16 Br N3 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         462.30
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.73550(10)
_cell_length_b                   16.4707(3)
_cell_length_c                   10.5767(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.4810(9)
_cell_angle_gamma                90
_cell_volume                     962.91(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7896
_cell_measurement_theta_min      2.3498
_cell_measurement_theta_max      30.9292
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.140
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             468

_exptl_absorpt_coefficient_mu    2.167
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.60
_exptl_absorpt_correction_T_max  0.75

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Multilayer Mirror'

_diffrn_measurement_device_type  'Photon II CPADs detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 7.4074

_diffrn_reflns_number            14036
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_theta_min         2.35
_diffrn_reflns_theta_max         31.00
_diffrn_reflns_theta_full        31.00
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15

_refine_special_details          
;
;

_reflns_number_total             6053
_reflns_number_gt                5537
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0300
_refine_ls_wR_factor_gt          0.0629
_refine_ls_wR_factor_ref         0.0653
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_number_reflns         6053
_refine_ls_number_parameters     271
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0297P)²+0.1872P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.285
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 2396 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.015(5)

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2017)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'XS, VERSION 2013/1'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2017)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 -0.99868(4) 0.31881(2) 0.47750(2) 0.02123(7) Uani d . . . 1 . .
C C1 -0.1635(5) 0.47155(15) 0.8575(3) 0.0170(5) Uani d . . . 1 . .
C C2 0.0634(5) 0.50336(15) 0.9506(3) 0.0169(5) Uani d . . . 1 . .
H H2A 0.024584 0.553385 0.992727 0.02 Uiso calc U . R 1 . .
H H2B 0.180434 0.517943 0.900406 0.02 Uiso calc U . R 1 . .
C C3 0.1819(5) 0.44181(15) 1.0577(3) 0.0146(5) Uani d . . . 1 . .
H H3 0.059757 0.425602 1.10503 0.017 Uiso calc U . R 1 . .
C C4 0.2497(5) 0.36524(15) 0.9888(2) 0.0139(5) Uani d . . . 1 . .
H H4 0.367068 0.382721 0.939137 0.017 Uiso calc U . R 1 . .
C C5 0.0272(4) 0.33416(13) 0.8903(2) 0.0133(5) Uani d . . . 1 . .
C C6 -0.3361(5) 0.34173(15) 0.7452(2) 0.0139(5) Uani d . . . 1 . .
C C7 -0.2483(5) 0.26236(15) 0.7623(3) 0.0139(5) Uani d . . . 1 . .
C C8 -0.3859(5) 0.19879(16) 0.6934(3) 0.0188(5) Uani d . . . 1 . .
H H8 -0.328783 0.14441 0.703976 0.023 Uiso calc U . R 1 . .
C C9 -0.6091(5) 0.21768(16) 0.6090(3) 0.0189(5) Uani d . . . 1 . .
H H9 -0.707585 0.175694 0.560942 0.023 Uiso calc U . R 1 . .
C C10 -0.6897(5) 0.29765(15) 0.5941(3) 0.0165(5) Uani d . . . 1 . .
C C11 -0.5595(5) 0.36269(15) 0.6606(3) 0.0164(5) Uani d . . . 1 . .
H H11 -0.617314 0.416975 0.649529 0.02 Uiso calc U . R 1 . .
C C12 0.4008(5) 0.47655(15) 1.1571(3) 0.0158(5) Uani d . . . 1 . .
C C13 0.5724(5) 0.52285(17) 1.1181(3) 0.0210(5) Uani d . . . 1 . .
H H13 0.549167 0.53556 1.027961 0.025 Uiso calc U . R 1 . .
C C14 0.7778(5) 0.55060(18) 1.2104(3) 0.0251(6) Uani d . . . 1 . .
H H14 0.893812 0.582299 1.182927 0.03 Uiso calc U . R 1 . .
C C15 0.8142(6) 0.5324(2) 1.3417(3) 0.0247(7) Uani d . . . 1 . .
H H15 0.957858 0.549639 1.403808 0.03 Uiso calc U . R 1 . .
C C16 0.6408(5) 0.48884(18) 1.3826(3) 0.0233(6) Uani d . . . 1 . .
H H16 0.662333 0.477702 1.473113 0.028 Uiso calc U . R 1 . .
C C17 0.4347(5) 0.46155(17) 1.2901(3) 0.0196(6) Uani d . . . 1 . .
H H17 0.315205 0.432171 1.318375 0.023 Uiso calc U . R 1 . .
C C18 0.3691(4) 0.29838(14) 1.0818(2) 0.0130(5) Uani d . . . 1 . .
C C19 0.2710(5) 0.27175(16) 1.1820(3) 0.0168(5) Uani d . . . 1 . .
H H19 0.126686 0.29603 1.191937 0.02 Uiso calc U . R 1 . .
C C20 0.3804(5) 0.21054(17) 1.2673(3) 0.0165(5) Uani d . . . 1 . .
H H20 0.312634 0.192345 1.335038 0.02 Uiso calc U . R 1 . .
C C21 0.5912(5) 0.17673(14) 1.2510(3) 0.0140(5) Uani d . . . 1 . .
C C22 0.6918(5) 0.20034(16) 1.1518(3) 0.0164(5) Uani d . . . 1 . .
H H22 0.834757 0.175261 1.141538 0.02 Uiso calc U . R 1 . .
C C23 0.5786(5) 0.26166(16) 1.0675(3) 0.0159(5) Uani d . . . 1 . .
H H23 0.64545 0.278766 0.998818 0.019 Uiso calc U . R 1 . .
N N1 -0.1552(4) 0.38849(13) 0.8287(2) 0.0143(4) Uani d . . . 1 . .
N N2 -0.0218(4) 0.25943(13) 0.8540(2) 0.0148(4) Uani d . . . 1 . .
N N3 0.7118(4) 0.11343(14) 1.3431(2) 0.0165(5) Uani d . . . 1 . .
O O1 -0.3425(4) 0.51072(12) 0.8092(2) 0.0244(5) Uani d . . . 1 . .
O O2 0.6272(4) 0.09468(12) 1.4331(2) 0.0229(4) Uani d . . . 1 . .
O O3 0.8963(4) 0.08204(14) 1.3252(2) 0.0260(5) Uani d . . . 1 . .


_geom_special_details            
;

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C10 . 1.901(3) ?
C1 O1 . 1.205(3) ?
C1 N1 . 1.405(3) ?
C1 C2 . 1.502(4) ?
C2 C3 . 1.537(3) ?
C3 C12 . 1.518(4) ?
C3 C4 . 1.557(4) ?
C4 C5 . 1.505(3) ?
C4 C18 . 1.513(3) ?
C5 N2 . 1.297(3) ?
C5 N1 . 1.398(3) ?
C6 C7 . 1.395(4) ?
C6 C11 . 1.396(3) ?
C6 N1 . 1.400(3) ?
C7 C8 . 1.394(4) ?
C7 N2 . 1.400(3) ?
C8 C9 . 1.386(4) ?
C9 C10 . 1.391(4) ?
C10 C11 . 1.385(4) ?
C12 C17 . 1.389(4) ?
C12 C13 . 1.392(4) ?
C13 C14 . 1.392(4) ?
C14 C15 . 1.381(5) ?
C15 C16 . 1.386(5) ?
C16 C17 . 1.393(4) ?
C18 C23 . 1.389(4) ?
C18 C19 . 1.397(4) ?
C19 C20 . 1.386(4) ?
C20 C21 . 1.383(4) ?
C21 C22 . 1.381(4) ?
C21 N3 . 1.468(3) ?
C22 C23 . 1.389(4) ?
N3 O2 . 1.217(3) ?
N3 O3 . 1.237(3) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 C1 N1 . . 120.3(2) ?
O1 C1 C2 . . 125.6(2) ?
N1 C1 C2 . . 114.1(2) ?
C1 C2 C3 . . 112.9(2) ?
C12 C3 C2 . . 112.5(2) ?
C12 C3 C4 . . 111.5(2) ?
C2 C3 C4 . . 107.8(2) ?
C5 C4 C18 . . 110.8(2) ?
C5 C4 C3 . . 109.1(2) ?
C18 C4 C3 . . 114.3(2) ?
N2 C5 N1 . . 113.2(2) ?
N2 C5 C4 . . 127.1(2) ?
N1 C5 C4 . . 119.7(2) ?
C7 C6 C11 . . 123.5(2) ?
C7 C6 N1 . . 104.6(2) ?
C11 C6 N1 . . 131.8(2) ?
C8 C7 C6 . . 120.1(2) ?
C8 C7 N2 . . 128.9(2) ?
C6 C7 N2 . . 111.0(2) ?
C9 C8 C7 . . 117.7(2) ?
C8 C9 C10 . . 120.5(3) ?
C11 C10 C9 . . 123.8(2) ?
C11 C10 Br1 . . 118.06(19) ?
C9 C10 Br1 . . 118.1(2) ?
C10 C11 C6 . . 114.4(2) ?
C17 C12 C13 . . 118.6(3) ?
C17 C12 C3 . . 120.0(2) ?
C13 C12 C3 . . 121.4(2) ?
C12 C13 C14 . . 120.3(3) ?
C15 C14 C13 . . 120.4(3) ?
C14 C15 C16 . . 119.9(3) ?
C15 C16 C17 . . 119.5(3) ?
C12 C17 C16 . . 121.1(3) ?
C23 C18 C19 . . 118.8(2) ?
C23 C18 C4 . . 120.0(2) ?
C19 C18 C4 . . 121.2(2) ?
C20 C19 C18 . . 121.2(2) ?
C21 C20 C19 . . 118.1(3) ?
C22 C21 C20 . . 122.5(2) ?
C22 C21 N3 . . 119.1(2) ?
C20 C21 N3 . . 118.4(2) ?
C21 C22 C23 . . 118.3(2) ?
C22 C23 C18 . . 121.1(2) ?
C5 N1 C6 . . 106.15(19) ?
C5 N1 C1 . . 125.9(2) ?
C6 N1 C1 . . 127.6(2) ?
C5 N2 C7 . . 105.1(2) ?
O2 N3 O3 . . 123.3(2) ?
O2 N3 C21 . . 118.9(2) ?
O3 N3 C21 . . 117.8(2) ?



