# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# 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_exp_8949
_database_code_depnum_ccdc_archive 'CCDC 1828278'
loop_
_audit_author_name
_audit_author_address
'Didi Ren' R???'f
_audit_update_record             
;
2018-03-08 deposited with the CCDC.	2020-07-17 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         ?
_chemical_formula_sum            'C19 H17 Cl N2 O'
_chemical_formula_weight         324.79

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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.5569(2)
_cell_length_b                   17.7897(4)
_cell_length_c                   11.2378(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.909(3)
_cell_angle_gamma                90
_cell_volume                     1502.73(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3907
_cell_measurement_theta_min      3.9380
_cell_measurement_theta_max      70.6620

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    2.292
_shelx_estimated_absorpt_T_min   0.820
_shelx_estimated_absorpt_T_max   0.838
_exptl_absorpt_correction_T_min  0.33003
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9001
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.672
_diffrn_reflns_theta_max         67.247
_diffrn_reflns_theta_full        67.247
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2685
_reflns_number_gt                2335
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0989P)²+0.3686P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2685
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.1589
_refine_ls_wR_factor_gt          0.1237
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_restrained_S_all      1.139
_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_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
Cl1 Cl 0.62460(8) 0.66198(3) 0.76727(6) 0.0439(2) Uani 1 1 d . . . . .
N1 N 0.7493(3) 0.43107(10) 1.03074(17) 0.0328(4) Uani 1 1 d . . . . .
N2 N 1.2287(3) 0.16169(12) 1.0181(2) 0.0435(5) Uani 1 1 d . . . . .
H2A H 1.3400 0.1680 1.0113 0.052 Uiso 1 1 calc R U . . .
O1 O 0.6266(2) 0.19748(9) 0.99907(17) 0.0399(4) Uani 1 1 d . . . . .
C1 C 0.6316(3) 0.56472(13) 0.7884(2) 0.0329(5) Uani 1 1 d . . . . .
C2 C 0.6853(3) 0.53751(12) 0.9012(2) 0.0309(5) Uani 1 1 d . . . . .
H2 H 0.7181 0.5705 0.9638 0.037 Uiso 1 1 calc R U . . .
C3 C 0.6900(3) 0.45967(12) 0.92076(19) 0.0279(5) Uani 1 1 d . . . . .
C4 C 0.6385(3) 0.41034(12) 0.8247(2) 0.0289(5) Uani 1 1 d . . . . .
C5 C 0.5895(3) 0.44113(14) 0.7129(2) 0.0360(5) Uani 1 1 d . . . . .
H5 H 0.5600 0.4087 0.6490 0.043 Uiso 1 1 calc R U . . .
C6 C 0.5824(3) 0.51784(14) 0.6916(2) 0.0380(5) Uani 1 1 d . . . . .
H6 H 0.5465 0.5371 0.6160 0.046 Uiso 1 1 calc R U . . .
C7 C 0.8226(3) 0.47633(13) 1.1320(2) 0.0347(5) Uani 1 1 d . . . . .
H7A H 0.7363 0.5127 1.1543 0.042 Uiso 1 1 calc R U . . .
H7B H 0.9288 0.5027 1.1137 0.042 Uiso 1 1 calc R U . . .
C8 C 0.8665(3) 0.41867(14) 1.2318(2) 0.0381(6) Uani 1 1 d . . . . .
H8A H 0.9759 0.4318 1.2802 0.046 Uiso 1 1 calc R U . . .
H8B H 0.7711 0.4154 1.2831 0.046 Uiso 1 1 calc R U . . .
C9 C 0.8870(3) 0.34482(13) 1.1653(2) 0.0353(5) Uani 1 1 d . . . . .
H9A H 1.0069 0.3394 1.1429 0.042 Uiso 1 1 calc R U . . .
H9B H 0.8603 0.3022 1.2143 0.042 Uiso 1 1 calc R U . . .
C10 C 0.7536(3) 0.35077(12) 1.05547(19) 0.0282(5) Uani 1 1 d . . . . .
H10 H 0.6367 0.3357 1.0777 0.034 Uiso 1 1 calc R U . . .
C11 C 0.7933(3) 0.30434(11) 0.9429(2) 0.0276(5) Uani 1 1 d . . . . .
C12 C 0.6456(3) 0.32631(12) 0.8438(2) 0.0323(5) Uani 1 1 d . . . . .
H12A H 0.6674 0.3017 0.7697 0.039 Uiso 1 1 calc R U . . .
H12B H 0.5317 0.3090 0.8658 0.039 Uiso 1 1 calc R U . . .
C13 C 0.9722(3) 0.32504(12) 0.9048(2) 0.0324(5) Uani 1 1 d . . . . .
H13 H 0.9826 0.3706 0.8656 0.039 Uiso 1 1 calc R U . . .
C14 C 1.1156(3) 0.28222(13) 0.9237(2) 0.0340(5) Uani 1 1 d . . . . .
H14 H 1.2240 0.2975 0.8995 0.041 Uiso 1 1 calc R U . . .
C15 C 1.0985(3) 0.21133(13) 0.9829(2) 0.0326(5) Uani 1 1 d . . . . .
C16 C 0.9379(3) 0.18109(12) 1.0095(2) 0.0312(5) Uani 1 1 d . . . . .
C17 C 0.7745(3) 0.22230(12) 0.9833(2) 0.0289(5) Uani 1 1 d . . . . .
C18 C 0.9769(3) 0.10911(14) 1.0620(2) 0.0414(6) Uani 1 1 d . . . . .
H18 H 0.8952 0.0753 1.0880 0.050 Uiso 1 1 calc R U . . .
C19 C 1.1550(4) 0.09943(16) 1.0666(3) 0.0494(7) Uani 1 1 d . . . . .
H19 H 1.2174 0.0576 1.0975 0.059 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
Cl1 C1 1.747(2) . ?
N1 C3 1.369(3) . ?
N1 C10 1.455(3) . ?
N1 C7 1.456(3) . ?
N2 C15 1.350(3) . ?
N2 C19 1.377(3) . ?
O1 C17 1.231(3) . ?
C1 C2 1.379(3) . ?
C1 C6 1.391(4) . ?
C2 C3 1.402(3) . ?
C3 C4 1.414(3) . ?
C4 C5 1.385(3) . ?
C4 C12 1.511(3) . ?
C5 C6 1.386(3) . ?
C7 C8 1.531(3) . ?
C8 C9 1.527(3) . ?
C9 C10 1.515(3) . ?
C10 C11 1.566(3) . ?
C11 C13 1.505(3) . ?
C11 C17 1.540(3) . ?
C11 C12 1.543(3) . ?
C13 C14 1.324(3) . ?
C14 C15 1.438(3) . ?
C15 C16 1.388(3) . ?
C16 C18 1.427(3) . ?
C16 C17 1.440(3) . ?
C18 C19 1.353(4) . ?

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
C3 N1 C10 122.42(18) . . ?
C3 N1 C7 124.27(19) . . ?
C10 N1 C7 113.23(17) . . ?
C15 N2 C19 109.3(2) . . ?
C2 C1 C6 122.6(2) . . ?
C2 C1 Cl1 118.34(18) . . ?
C6 C1 Cl1 119.07(18) . . ?
C1 C2 C3 119.4(2) . . ?
N1 C3 C2 120.6(2) . . ?
N1 C3 C4 119.8(2) . . ?
C2 C3 C4 119.5(2) . . ?
C5 C4 C3 118.3(2) . . ?
C5 C4 C12 121.5(2) . . ?
C3 C4 C12 120.2(2) . . ?
C4 C5 C6 123.2(2) . . ?
C5 C6 C1 116.9(2) . . ?
N1 C7 C8 103.80(18) . . ?
C9 C8 C7 104.06(18) . . ?
C10 C9 C8 104.25(18) . . ?
N1 C10 C9 102.94(17) . . ?
N1 C10 C11 111.45(17) . . ?
C9 C10 C11 117.03(18) . . ?
C13 C11 C17 115.41(17) . . ?
C13 C11 C12 109.70(19) . . ?
C17 C11 C12 111.78(17) . . ?
C13 C11 C10 110.70(17) . . ?
C17 C11 C10 103.30(17) . . ?
C12 C11 C10 105.34(16) . . ?
C4 C12 C11 111.46(17) . . ?
C14 C13 C11 123.9(2) . . ?
C13 C14 C15 117.9(2) . . ?
N2 C15 C16 108.1(2) . . ?
N2 C15 C14 127.7(2) . . ?
C16 C15 C14 124.2(2) . . ?
C15 C16 C18 106.8(2) . . ?
C15 C16 C17 120.6(2) . . ?
C18 C16 C17 132.6(2) . . ?
O1 C17 C16 124.0(2) . . ?
O1 C17 C11 119.70(19) . . ?
C16 C17 C11 116.07(18) . . ?
C19 C18 C16 107.0(2) . . ?
C18 C19 N2 108.9(2) . . ?

_refine_diff_density_max         0.319
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.103



####################################################################### 
# 
# 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 1922516'
loop_
_audit_author_name
_audit_author_address
'Kang Duan'
;QAU
China
;
_audit_update_record             
;
2019-06-12 deposited with the CCDC.	2020-07-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H21 Br N2 O2'
_chemical_formula_weight         401.30

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'
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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   20.4146(3)
_cell_length_b                   6.41670(10)
_cell_length_c                   14.0402(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1839.19(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7939
_cell_measurement_theta_min      3.8320
_cell_measurement_theta_max      70.8920

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    3.168
_shelx_estimated_absorpt_T_min   0.684
_shelx_estimated_absorpt_T_max   0.722
_exptl_absorpt_correction_T_min  0.34086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11838
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.331
_diffrn_reflns_theta_max         67.211
_diffrn_reflns_theta_full        67.211
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.841
_diffrn_reflns_point_group_measured_fraction_full 0.841
_reflns_number_total             2786
_reflns_number_gt                2694
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.610
_reflns_Friedel_fraction_max     0.667
_reflns_Friedel_fraction_full    0.667

_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       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0460P)²+0.1130P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_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 x determined using 969 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.022(7)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         2786
_refine_ls_number_parameters     229
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0271
_refine_ls_R_factor_gt           0.0261
_refine_ls_wR_factor_ref         0.0705
_refine_ls_wR_factor_gt          0.0699
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.091
_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 0.74524(2) 1.39264(5) 1.19797(5) 0.06847(16) Uani 1 1 d . . . . .
N1 N 0.55861(13) 0.7999(5) 0.8138(2) 0.0580(7) Uani 1 1 d . . . . .
N2 N 0.72827(12) 0.6115(4) 0.9575(2) 0.0465(6) Uani 1 1 d . . . . .
O1 O 0.53911(11) 0.2863(4) 1.04730(18) 0.0599(6) Uani 1 1 d . . . . .
H1 H 0.510720 0.224610 1.077512 0.090 Uiso 1 1 calc R U . . .
O2 O 0.46452(19) 1.0193(5) 0.1401(2) 0.0965(11) Uani 1 1 d . . . . .
H2 H 0.451194 1.073327 0.189352 0.145 Uiso 1 1 calc R U . . .
C1 C 0.51197(15) 0.3768(4) 0.9701(2) 0.0472(7) Uani 1 1 d . . . . .
C2 C 0.45285(16) 0.3117(6) 0.9300(3) 0.0663(9) Uani 1 1 d . . . . .
H2A H 0.430639 0.199246 0.956506 0.080 Uiso 1 1 calc R U . . .
C3 C 0.42696(18) 0.4107(7) 0.8519(4) 0.0813(13) Uani 1 1 d . . . . .
H3 H 0.386849 0.366184 0.828003 0.098 Uiso 1 1 calc R U . . .
C4 C 0.45848(19) 0.5736(8) 0.8081(3) 0.0762(12) Uani 1 1 d . . . . .
H4 H 0.441188 0.637902 0.754330 0.091 Uiso 1 1 calc R U . . .
C5 C 0.51701(15) 0.6372(5) 0.8476(3) 0.0529(8) Uani 1 1 d . . . . .
C6 C 0.54410(12) 0.5418(4) 0.9269(2) 0.0420(6) Uani 1 1 d . . . . .
C7 C 0.60851(12) 0.6487(4) 0.9487(2) 0.0387(6) Uani 1 1 d . . . . .
C8 C 0.60853(14) 0.8053(4) 0.8689(2) 0.0469(7) Uani 1 1 d . . . . .
H8 H 0.642565 0.899734 0.860239 0.056 Uiso 1 1 calc R U . . .
C9 C 0.66740(12) 0.4987(4) 0.9421(2) 0.0384(5) Uani 1 1 d . . . . .
H9 H 0.662946 0.391824 0.991496 0.046 Uiso 1 1 calc R U . . .
C10 C 0.67934(16) 0.3922(4) 0.8472(2) 0.0479(8) Uani 1 1 d . . . . .
H10A H 0.670315 0.485480 0.794407 0.058 Uiso 1 1 calc R U . . .
H10B H 0.652586 0.268074 0.840661 0.058 Uiso 1 1 calc R U . . .
C11 C 0.75217(16) 0.3371(7) 0.8521(3) 0.0552(9) Uani 1 1 d . . . . .
H11A H 0.758750 0.206299 0.885387 0.066 Uiso 1 1 calc R U . . .
H11B H 0.770819 0.326163 0.788785 0.066 Uiso 1 1 calc R U . . .
C12 C 0.78289(15) 0.5172(5) 0.9069(2) 0.0507(7) Uani 1 1 d . . . . .
H12A H 0.815821 0.466979 0.951111 0.061 Uiso 1 1 calc R U . . .
H12B H 0.802997 0.616382 0.863747 0.061 Uiso 1 1 calc R U . . .
C13 C 0.61201(13) 0.7567(5) 1.0464(2) 0.0462(7) Uani 1 1 d . . . . .
H13A H 0.576915 0.858014 1.051449 0.055 Uiso 1 1 calc R U . . .
H13B H 0.606026 0.654006 1.096351 0.055 Uiso 1 1 calc R U . . .
C14 C 0.67672(14) 0.8642(4) 1.0598(2) 0.0409(6) Uani 1 1 d . . . . .
C15 C 0.73315(13) 0.7842(5) 1.0138(2) 0.0401(6) Uani 1 1 d . . . . .
C16 C 0.79279(15) 0.8901(5) 1.0267(3) 0.0489(8) Uani 1 1 d . . . . .
H16 H 0.830305 0.839981 0.996854 0.059 Uiso 1 1 calc R U . . .
C17 C 0.79691(16) 1.0657(5) 1.0822(3) 0.0523(8) Uani 1 1 d . . . . .
H17 H 0.836951 1.132251 1.090762 0.063 Uiso 1 1 calc R U . . .
C18 C 0.74124(16) 1.1425(5) 1.1251(3) 0.0492(8) Uani 1 1 d . . . . .
C19 C 0.68190(15) 1.0435(5) 1.1139(2) 0.0458(7) Uani 1 1 d . . . . .
H19 H 0.644784 1.097986 1.143109 0.055 Uiso 1 1 calc R U . . .
C20 C 0.4404(2) 0.8233(7) 0.1331(4) 0.0904(15) Uani 1 1 d . . . . .
H20A H 0.465026 0.731819 0.173582 0.136 Uiso 1 1 calc R U . . .
H20B H 0.443698 0.776545 0.068284 0.136 Uiso 1 1 calc R U . . .
H20C H 0.395242 0.822539 0.152314 0.136 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C18 1.905(4) . ?
N1 C8 1.281(4) . ?
N1 C5 1.427(4) . ?
N2 C15 1.365(4) . ?
N2 C12 1.454(4) . ?
N2 C9 1.454(4) . ?
O1 C1 1.348(4) . ?
O2 C20 1.355(5) . ?
C1 C6 1.386(4) . ?
C1 C2 1.397(4) . ?
C2 C3 1.373(6) . ?
C3 C4 1.373(6) . ?
C4 C5 1.379(5) . ?
C5 C6 1.385(4) . ?
C6 C7 1.514(3) . ?
C7 C8 1.505(4) . ?
C7 C13 1.539(4) . ?
C7 C9 1.543(3) . ?
C9 C10 1.517(4) . ?
C10 C11 1.530(4) . ?
C11 C12 1.523(5) . ?
C13 C14 1.502(4) . ?
C14 C19 1.383(4) . ?
C14 C15 1.416(4) . ?
C15 C16 1.406(4) . ?
C16 C17 1.373(5) . ?
C17 C18 1.377(5) . ?
C18 C19 1.377(4) . ?

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
C8 N1 C5 107.0(3) . . ?
C15 N2 C12 124.4(3) . . ?
C15 N2 C9 123.6(2) . . ?
C12 N2 C9 112.0(2) . . ?
O1 C1 C6 119.1(3) . . ?
O1 C1 C2 123.4(3) . . ?
C6 C1 C2 117.4(3) . . ?
C3 C2 C1 121.1(3) . . ?
C2 C3 C4 122.0(3) . . ?
C3 C4 C5 116.8(4) . . ?
C4 C5 C6 122.6(3) . . ?
C4 C5 N1 126.7(3) . . ?
C6 C5 N1 110.7(3) . . ?
C5 C6 C1 120.0(3) . . ?
C5 C6 C7 108.0(2) . . ?
C1 C6 C7 132.0(3) . . ?
C8 C7 C6 98.8(2) . . ?
C8 C7 C13 111.3(2) . . ?
C6 C7 C13 115.1(2) . . ?
C8 C7 C9 111.8(2) . . ?
C6 C7 C9 112.5(2) . . ?
C13 C7 C9 107.4(2) . . ?
N1 C8 C7 115.6(3) . . ?
N2 C9 C10 102.6(2) . . ?
N2 C9 C7 110.3(2) . . ?
C10 C9 C7 117.3(2) . . ?
C9 C10 C11 102.7(3) . . ?
C12 C11 C10 104.4(3) . . ?
N2 C12 C11 104.3(3) . . ?
C14 C13 C7 111.0(2) . . ?
C19 C14 C15 119.3(3) . . ?
C19 C14 C13 121.2(3) . . ?
C15 C14 C13 119.5(3) . . ?
N2 C15 C16 122.0(3) . . ?
N2 C15 C14 119.9(3) . . ?
C16 C15 C14 118.1(3) . . ?
C17 C16 C15 121.5(3) . . ?
C16 C17 C18 119.4(3) . . ?
C19 C18 C17 120.7(3) . . ?
C19 C18 Br1 119.2(3) . . ?
C17 C18 Br1 120.1(2) . . ?
C18 C19 C14 120.9(3) . . ?

_refine_diff_density_max         0.183
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.066



