# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_12395
_database_code_depnum_ccdc_archive 'CCDC 2124513'
loop_
_audit_author_name
_audit_author_address
dxjbjq
;Qingdao Agricultural University
China
;
_audit_update_record             
;
2021-11-26 deposited with the CCDC.	2022-08-15 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            'C21 H22 N2 O3'
_chemical_formula_weight         350.40

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   8.2810(10)
_cell_length_b                   9.4019(9)
_cell_length_c                   12.3847(13)
_cell_angle_alpha                71.987(9)
_cell_angle_beta                 87.243(9)
_cell_angle_gamma                75.194(9)
_cell_volume                     886.04(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1966
_cell_measurement_theta_min      6.5380
_cell_measurement_theta_max      70.8600

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            WHITE
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_F_000             372
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.713
_shelx_estimated_absorpt_T_min   0.907
_shelx_estimated_absorpt_T_max   0.919
_exptl_absorpt_correction_T_min  0.81847
_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            5368
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.755
_diffrn_reflns_theta_max         67.246
_diffrn_reflns_theta_full        67.246
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3144
_reflns_number_gt                2441
_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       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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)+(0.0477P)²+0.1421P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0189(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3144
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.1260
_refine_ls_wR_factor_gt          0.1135
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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
N1 N 0.5950(2) 0.89737(19) 1.16928(14) 0.0569(5) Uani 1 1 d . . . . .
N2 N 0.28244(17) 0.66891(17) 0.72974(12) 0.0437(4) Uani 1 1 d . . . . .
O1 O -0.19438(18) 0.7392(2) 0.83982(15) 0.0817(5) Uani 1 1 d . . . . .
O2 O 0.7345(2) 0.89404(19) 1.13326(14) 0.0737(5) Uani 1 1 d . . . . .
O3 O 0.5421(2) 0.9475(2) 1.24727(14) 0.0848(6) Uani 1 1 d . . . . .
C1 C 0.4830(2) 0.8364(2) 1.11708(14) 0.0444(4) Uani 1 1 d . . . . .
C2 C 0.5476(2) 0.7571(2) 1.04219(15) 0.0476(5) Uani 1 1 d . . . . .
H2 H 0.659719 0.742460 1.024036 0.057 Uiso 1 1 calc R U . . .
C3 C 0.4412(2) 0.6993(2) 0.99440(15) 0.0471(5) Uani 1 1 d . . . . .
H3 H 0.483465 0.643608 0.944487 0.057 Uiso 1 1 calc R U . . .
C4 C 0.2734(2) 0.7225(2) 1.01901(14) 0.0429(4) Uani 1 1 d . . . . .
C5 C 0.2124(2) 0.8060(2) 1.09389(15) 0.0507(5) Uani 1 1 d . . . . .
H5 H 0.099694 0.823976 1.110564 0.061 Uiso 1 1 calc R U . . .
C6 C 0.3172(3) 0.8628(2) 1.14388(16) 0.0524(5) Uani 1 1 d . . . . .
H6 H 0.276363 0.917612 1.194559 0.063 Uiso 1 1 calc R U . . .
C7 C 0.1572(3) 0.6624(2) 0.96469(15) 0.0502(5) Uani 1 1 d . . . . .
H7A H 0.068903 0.639893 1.016465 0.060 Uiso 1 1 calc R U . . .
H7B H 0.218807 0.566469 0.952261 0.060 Uiso 1 1 calc R U . . .
C8 C 0.0780(2) 0.7777(2) 0.85029(15) 0.0450(4) Uani 1 1 d . . . . .
H8 H 0.019481 0.875463 0.863104 0.054 Uiso 1 1 calc R U . . .
C9 C -0.0496(2) 0.7115(2) 0.81171(16) 0.0486(5) Uani 1 1 d . . . . .
C10 C 0.0152(2) 0.6063(2) 0.74481(14) 0.0405(4) Uani 1 1 d . . . . .
C11 C -0.0863(2) 0.5215(2) 0.72058(17) 0.0541(5) Uani 1 1 d . . . . .
H11 H -0.196135 0.537149 0.743844 0.065 Uiso 1 1 calc R U . . .
C12 C -0.0285(3) 0.4159(2) 0.66351(18) 0.0620(6) Uani 1 1 d . . . . .
H12 H -0.098422 0.361612 0.646886 0.074 Uiso 1 1 calc R U . . .
C13 C 0.1352(3) 0.3916(2) 0.63123(17) 0.0615(6) Uani 1 1 d . . . . .
H13 H 0.175994 0.318856 0.593481 0.074 Uiso 1 1 calc R U . . .
C14 C 0.2393(3) 0.4720(2) 0.65338(16) 0.0527(5) Uani 1 1 d . . . . .
H14 H 0.349480 0.452329 0.631053 0.063 Uiso 1 1 calc R U . . .
C15 C 0.1820(2) 0.58394(19) 0.70943(14) 0.0388(4) Uani 1 1 d . . . . .
C16 C 0.4482(3) 0.6595(3) 0.6835(2) 0.0672(6) Uani 1 1 d . . . . .
H16A H 0.509254 0.551581 0.703803 0.081 Uiso 1 1 calc R U . . .
H16B H 0.506887 0.711063 0.719302 0.081 Uiso 1 1 calc R U . . .
C17 C 0.4512(4) 0.7308(4) 0.5539(2) 0.0928(9) Uani 1 1 d . . . . .
H17A H 0.549772 0.770476 0.536220 0.111 Uiso 1 1 calc R U . . .
H17B H 0.462377 0.649374 0.519371 0.111 Uiso 1 1 calc R U . . .
C18 C 0.2986(4) 0.8608(3) 0.4996(2) 0.0844(8) Uani 1 1 d . . . . .
H18A H 0.322945 0.910151 0.421576 0.101 Uiso 1 1 calc R U . . .
H18B H 0.206296 0.815475 0.497627 0.101 Uiso 1 1 calc R U . . .
C19 C 0.2431(3) 0.9832(3) 0.55759(18) 0.0753(7) Uani 1 1 d . . . . .
H19A H 0.187228 1.079318 0.501608 0.090 Uiso 1 1 calc R U . . .
H19B H 0.341278 0.999645 0.586613 0.090 Uiso 1 1 calc R U . . .
C20 C 0.1261(3) 0.9457(2) 0.65501(17) 0.0585(6) Uani 1 1 d . . . . .
H20A H 0.031299 0.923042 0.626861 0.070 Uiso 1 1 calc R U . . .
H20B H 0.084004 1.036806 0.679130 0.070 Uiso 1 1 calc R U . . .
C21 C 0.2042(2) 0.8102(2) 0.75848(15) 0.0451(4) Uani 1 1 d . . . . .
H21 H 0.292139 0.839391 0.790502 0.054 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
N1 O2 1.214(2) . ?
N1 O3 1.217(2) . ?
N1 C1 1.472(2) . ?
N2 C15 1.370(2) . ?
N2 C16 1.454(2) . ?
N2 C21 1.463(2) . ?
O1 C9 1.218(2) . ?
C1 C2 1.371(3) . ?
C1 C6 1.374(3) . ?
C2 C3 1.384(2) . ?
C3 C4 1.385(3) . ?
C4 C5 1.391(3) . ?
C4 C7 1.507(2) . ?
C5 C6 1.383(3) . ?
C7 C8 1.546(3) . ?
C8 C9 1.516(2) . ?
C8 C21 1.521(2) . ?
C9 C10 1.465(2) . ?
C10 C11 1.395(2) . ?
C10 C15 1.412(2) . ?
C11 C12 1.369(3) . ?
C12 C13 1.377(3) . ?
C13 C14 1.369(3) . ?
C14 C15 1.407(2) . ?
C16 C17 1.538(3) . ?
C17 C18 1.526(4) . ?
C18 C19 1.504(3) . ?
C19 C20 1.522(3) . ?
C20 C21 1.527(2) . ?

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
O2 N1 O3 123.70(18) . . ?
O2 N1 C1 118.68(18) . . ?
O3 N1 C1 117.61(18) . . ?
C15 N2 C16 121.29(16) . . ?
C15 N2 C21 118.58(14) . . ?
C16 N2 C21 116.02(15) . . ?
C2 C1 C6 122.43(17) . . ?
C2 C1 N1 118.64(18) . . ?
C6 C1 N1 118.93(17) . . ?
C1 C2 C3 118.04(18) . . ?
C2 C3 C4 121.65(17) . . ?
C3 C4 C5 118.39(17) . . ?
C3 C4 C7 121.43(16) . . ?
C5 C4 C7 120.16(17) . . ?
C6 C5 C4 120.86(18) . . ?
C1 C6 C5 118.60(18) . . ?
C4 C7 C8 112.98(14) . . ?
C9 C8 C21 110.10(14) . . ?
C9 C8 C7 107.57(15) . . ?
C21 C8 C7 113.69(16) . . ?
O1 C9 C10 122.82(18) . . ?
O1 C9 C8 121.44(18) . . ?
C10 C9 C8 115.64(15) . . ?
C11 C10 C15 119.56(17) . . ?
C11 C10 C9 119.67(16) . . ?
C15 C10 C9 120.69(15) . . ?
C12 C11 C10 121.80(19) . . ?
C11 C12 C13 118.63(18) . . ?
C14 C13 C12 121.56(19) . . ?
C13 C14 C15 120.98(19) . . ?
N2 C15 C14 122.05(16) . . ?
N2 C15 C10 120.52(15) . . ?
C14 C15 C10 117.44(16) . . ?
N2 C16 C17 115.1(2) . . ?
C18 C17 C16 115.5(2) . . ?
C19 C18 C17 115.6(2) . . ?
C18 C19 C20 114.60(18) . . ?
C19 C20 C21 115.19(19) . . ?
N2 C21 C8 109.74(14) . . ?
N2 C21 C20 112.83(15) . . ?
C8 C21 C20 111.80(16) . . ?

_refine_diff_density_max         0.188
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.037



####################################################################### 
# 
# 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_12349
_database_code_depnum_ccdc_archive 'CCDC 2124547'
loop_
_audit_author_name
_audit_author_address
lhdh
;Qingdao Agricultural University
China
;
_audit_update_record             
;
2021-11-26 deposited with the CCDC.	2022-08-15 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            'C11 H10 Br0.11 N O'
_chemical_formula_weight         181.08

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      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                   13.8236(3)
_cell_length_b                   19.2351(5)
_cell_length_c                   8.2291(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.195(3)
_cell_angle_gamma                90
_cell_volume                     2187.62(10)
_cell_formula_units_Z            9
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_F_000             854
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    1.145
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14147
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.198
_diffrn_reflns_theta_max         71.047
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4181
_reflns_number_gt                3321
_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-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)+(0.2000P)²] 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         4181
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1056
_refine_ls_R_factor_gt           0.0882
_refine_ls_wR_factor_ref         0.3072
_refine_ls_wR_factor_gt          0.2897
_refine_ls_goodness_of_fit_ref   1.289
_refine_ls_restrained_S_all      1.289
_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
Br1 Br -0.24123(5) 0.19962(4) 0.14674(11) 0.0866(4) Uani 1 1 d . . . . .
N1 N -0.0074(2) 0.41710(19) 0.0842(4) 0.0405(8) Uani 1 1 d . . . . .
H1 H -0.047299 0.445539 0.038015 0.049 Uiso 1 1 calc R U . . .
N2 N 0.2684(2) 0.41811(17) 0.3784(4) 0.0338(7) Uani 1 1 d . . . . .
O1 O 0.1256(2) 0.48808(17) 0.0892(4) 0.0507(8) Uani 1 1 d . . . . .
O2 O 0.2632(3) 0.2282(2) 0.1544(5) 0.0609(10) Uani 1 1 d . . . . .
C1 C -0.1216(3) 0.2479(2) 0.1677(5) 0.0444(10) Uani 1 1 d . . . . .
C2 C -0.0431(4) 0.2140(2) 0.2335(6) 0.0467(10) Uani 1 1 d . . . . .
H2 H -0.047840 0.167818 0.265896 0.056 Uiso 1 1 calc R U . . .
C3 C 0.0442(3) 0.2499(2) 0.2512(5) 0.0420(9) Uani 1 1 d . . . . .
H3 H 0.097858 0.227804 0.297694 0.050 Uiso 1 1 calc R U . . .
C4 C 0.0512(3) 0.3178(2) 0.2003(4) 0.0320(8) Uani 1 1 d . . . . .
C5 C -0.0309(3) 0.3497(2) 0.1321(4) 0.0354(8) Uani 1 1 d . . . . .
C6 C -0.1190(3) 0.3167(2) 0.1148(5) 0.0423(9) Uani 1 1 d . . . . .
H6 H -0.173163 0.338940 0.070535 0.051 Uiso 1 1 calc R U . . .
C7 C 0.0860(3) 0.4319(2) 0.1198(4) 0.0370(9) Uani 1 1 d . . . . .
C8 C 0.1338(3) 0.3688(2) 0.2003(4) 0.0337(8) Uani 1 1 d . . . . .
C9 C 0.1731(3) 0.38433(19) 0.3769(4) 0.0303(8) Uani 1 1 d . . . . .
H9 H 0.182761 0.338974 0.429003 0.036 Uiso 1 1 calc R U . . .
C10 C 0.0972(3) 0.4215(2) 0.4748(5) 0.0400(9) Uani 1 1 d . . . . .
H10A H 0.039014 0.393370 0.473963 0.048 Uiso 1 1 calc R U . . .
H10B H 0.081475 0.465060 0.420979 0.048 Uiso 1 1 calc R U . . .
C11 C 0.1261(3) 0.4371(2) 0.6513(5) 0.0462(10) Uani 1 1 d . . . . .
H11A H 0.168535 0.400551 0.691499 0.055 Uiso 1 1 calc R U . . .
H11B H 0.068477 0.436899 0.716688 0.055 Uiso 1 1 calc R U . . .
C12 C 0.1774(4) 0.5074(3) 0.6718(6) 0.0581(12) Uani 1 1 d . . . . .
H12A H 0.136590 0.543332 0.624174 0.070 Uiso 1 1 calc R U . . .
H12B H 0.184669 0.517331 0.787006 0.070 Uiso 1 1 calc R U . . .
C13 C 0.2750(4) 0.5111(3) 0.5964(6) 0.0538(11) Uani 1 1 d . . . . .
H13A H 0.318583 0.480190 0.655421 0.065 Uiso 1 1 calc R U . . .
H13B H 0.299779 0.558032 0.609298 0.065 Uiso 1 1 calc R U . . .
C14 C 0.2762(3) 0.4919(2) 0.4148(5) 0.0425(9) Uani 1 1 d . . . . .
H14A H 0.223165 0.515810 0.359808 0.051 Uiso 1 1 calc R U . . .
H14B H 0.335883 0.509130 0.369771 0.051 Uiso 1 1 calc R U . . .
C15 C 0.3508(3) 0.3777(2) 0.3807(4) 0.0358(8) Uani 1 1 d . . . . .
C16 C 0.4358(3) 0.3993(3) 0.4618(6) 0.0488(10) Uani 1 1 d . . . . .
H16 H 0.438396 0.443437 0.507838 0.059 Uiso 1 1 calc R U . . .
C17 C 0.5147(3) 0.3570(3) 0.4745(7) 0.0632(14) Uani 1 1 d . . . . .
H17 H 0.570100 0.372978 0.528501 0.076 Uiso 1 1 calc R U . . .
C18 C 0.5142(4) 0.2894(3) 0.4075(8) 0.0653(15) Uani 1 1 d . . . . .
H18 H 0.567065 0.259835 0.420458 0.078 Uiso 1 1 calc R U . . .
C19 C 0.4334(3) 0.2693(3) 0.3233(6) 0.0547(12) Uani 1 1 d . . . . .
H19 H 0.431757 0.225036 0.277580 0.066 Uiso 1 1 calc R U . . .
C20 C 0.3532(3) 0.3122(2) 0.3027(5) 0.0387(9) Uani 1 1 d . . . . .
C21 C 0.2771(3) 0.2897(2) 0.1850(5) 0.0418(10) Uani 1 1 d . . . . .
C22 C 0.2201(3) 0.3451(3) 0.0973(4) 0.0424(10) Uani 1 1 d . . . . .
H22A H 0.196375 0.327261 -0.006266 0.051 Uiso 1 1 calc R U . . .
H22B H 0.261668 0.384613 0.076231 0.051 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 1.901(4) . ?
N1 C7 1.348(5) . ?
N1 C5 1.395(5) . ?
N2 C15 1.378(5) . ?
N2 C14 1.454(5) . ?
N2 C9 1.469(5) . ?
O1 C7 1.239(5) . ?
O2 C21 1.224(6) . ?
C1 C2 1.369(7) . ?
C1 C6 1.394(6) . ?
C2 C3 1.395(6) . ?
C3 C4 1.375(6) . ?
C4 C5 1.399(5) . ?
C4 C8 1.505(5) . ?
C5 C6 1.377(6) . ?
C7 C8 1.527(5) . ?
C8 C22 1.547(5) . ?
C8 C9 1.570(5) . ?
C9 C10 1.516(5) . ?
C10 C11 1.528(6) . ?
C11 C12 1.534(7) . ?
C12 C13 1.498(7) . ?
C13 C14 1.540(6) . ?
C15 C16 1.402(6) . ?
C15 C20 1.416(6) . ?
C16 C17 1.364(7) . ?
C17 C18 1.412(8) . ?
C18 C19 1.358(8) . ?
C19 C20 1.390(6) . ?
C20 C21 1.479(6) . ?
C21 C22 1.501(7) . ?

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
C7 N1 C5 111.3(3) . . ?
C15 N2 C14 119.3(3) . . ?
C15 N2 C9 119.4(3) . . ?
C14 N2 C9 119.7(3) . . ?
C2 C1 C6 123.4(4) . . ?
C2 C1 Br1 118.9(3) . . ?
C6 C1 Br1 117.7(3) . . ?
C1 C2 C3 118.9(4) . . ?
C4 C3 C2 120.3(4) . . ?
C3 C4 C5 118.6(4) . . ?
C3 C4 C8 132.6(3) . . ?
C5 C4 C8 108.8(3) . . ?
C6 C5 N1 127.6(4) . . ?
C6 C5 C4 123.2(4) . . ?
N1 C5 C4 109.2(3) . . ?
C5 C6 C1 115.7(4) . . ?
O1 C7 N1 124.4(4) . . ?
O1 C7 C8 126.4(4) . . ?
N1 C7 C8 109.2(3) . . ?
C4 C8 C7 101.4(3) . . ?
C4 C8 C22 113.7(3) . . ?
C7 C8 C22 109.1(3) . . ?
C4 C8 C9 111.9(3) . . ?
C7 C8 C9 112.9(3) . . ?
C22 C8 C9 107.8(3) . . ?
N2 C9 C10 114.7(3) . . ?
N2 C9 C8 112.7(3) . . ?
C10 C9 C8 110.6(3) . . ?
C9 C10 C11 115.4(3) . . ?
C10 C11 C12 112.9(4) . . ?
C13 C12 C11 114.5(4) . . ?
C12 C13 C14 114.7(4) . . ?
N2 C14 C13 115.6(3) . . ?
N2 C15 C16 121.6(4) . . ?
N2 C15 C20 121.6(3) . . ?
C16 C15 C20 116.9(4) . . ?
C17 C16 C15 121.4(5) . . ?
C16 C17 C18 121.5(5) . . ?
C19 C18 C17 117.3(5) . . ?
C18 C19 C20 122.6(5) . . ?
C19 C20 C15 120.0(4) . . ?
C19 C20 C21 117.5(4) . . ?
C15 C20 C21 122.2(4) . . ?
O2 C21 C20 121.5(4) . . ?
O2 C21 C22 120.6(4) . . ?
C20 C21 C22 117.8(4) . . ?
C21 C22 C8 110.4(3) . . ?

_refine_diff_density_max         2.001
_refine_diff_density_min         -1.041
_refine_diff_density_rms         0.189



