# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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_mo_d8v22523_0m
_database_code_depnum_ccdc_archive 'CCDC 2282722'
loop_
_audit_author_name
_audit_author_address
Huiying
;Changzhou University
China
;
_audit_update_record             
;
2023-07-19 deposited with the CCDC.	2023-12-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H22 F3 N3 O'
_chemical_formula_weight         413.43

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'
F F 0.0171 0.0103 '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'

_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                   7.0619(3)
_cell_length_b                   38.6059(14)
_cell_length_c                   8.5233(3)
_cell_angle_alpha                90
_cell_angle_beta                 114.4250(10)
_cell_angle_gamma                90
_cell_volume                     2115.75(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7313
_cell_measurement_theta_min      5.354
_cell_measurement_theta_max      52.949

_exptl_crystal_description       prismatic
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.099
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5073
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21233
_diffrn_reflns_av_unetI/netI     0.0485
_diffrn_reflns_av_R_equivalents  0.0701
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -47
_diffrn_reflns_limit_k_max       47
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.677
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4144
_reflns_number_gt                2951
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0633P)²+0.5901P] 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
_refine_ls_extinction_coef       0.024(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4144
_refine_ls_number_parameters     302
_refine_ls_number_restraints     48
_refine_ls_R_factor_all          0.0770
_refine_ls_R_factor_gt           0.0529
_refine_ls_wR_factor_ref         0.1549
_refine_ls_wR_factor_gt          0.1336
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.031
_refine_ls_shift/su_mean         0.002

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
O1 O 0.7710(2) 0.66431(4) 0.90551(16) 0.0612(4) Uani 1 1 d . . . . .
N1 N 0.3689(2) 0.69660(4) 0.3031(2) 0.0592(5) Uani 1 1 d . . . . .
N2 N 0.5484(2) 0.67719(5) 0.6287(2) 0.0598(5) Uani 1 1 d . . . . .
H2 H 0.4177 0.6787 0.5638 0.072 Uiso 1 1 calc R U . . .
N3 N 0.6239(3) 0.61775(5) 1.0719(2) 0.0713(5) Uani 1 1 d . . . . .
H3 H 0.7196 0.6316 1.0730 0.086 Uiso 1 1 calc R U . . .
C1 C 0.2775(4) 0.70477(6) 0.1386(3) 0.0698(6) Uani 1 1 d . . . . .
H1 H 0.1343 0.7018 0.0822 0.084 Uiso 1 1 calc R U . . .
C2 C 0.3829(4) 0.71755(6) 0.0440(3) 0.0725(6) Uani 1 1 d . . . . .
H2A H 0.3105 0.7229 -0.0722 0.087 Uiso 1 1 calc R U . . .
C3 C 0.5913(4) 0.72216(5) 0.1223(3) 0.0646(6) Uani 1 1 d . . . . .
H3A H 0.6635 0.7304 0.0602 0.078 Uiso 1 1 calc R U . . .
C4 C 0.6982(3) 0.71435(5) 0.2993(2) 0.0533(5) Uani 1 1 d . . . . .
C5 C 0.9145(3) 0.71842(6) 0.3920(3) 0.0639(6) Uani 1 1 d . . . . .
H5 H 0.9948 0.7271 0.3377 0.077 Uiso 1 1 calc R U . . .
C6 C 1.0047(3) 0.70955(6) 0.5613(3) 0.0652(6) Uani 1 1 d . . . . .
H6 H 1.1475 0.7124 0.6217 0.078 Uiso 1 1 calc R U . . .
C7 C 0.8899(3) 0.69621(5) 0.6479(2) 0.0585(5) Uani 1 1 d . . . . .
H7 H 0.9566 0.6904 0.7639 0.070 Uiso 1 1 calc R U . . .
C8 C 0.6793(3) 0.69177(5) 0.5618(2) 0.0502(5) Uani 1 1 d . . . . .
C9 C 0.5790(3) 0.70138(5) 0.3840(2) 0.0491(4) Uani 1 1 d . . . . .
C10 C 0.5982(3) 0.66071(5) 0.7842(2) 0.0523(5) Uani 1 1 d . . . . .
C11 C 0.4368(3) 0.63875(5) 0.7882(3) 0.0589(5) Uani 1 1 d . . . . .
H11 H 0.3101 0.6389 0.6921 0.071 Uiso 1 1 calc R U . . .
C12 C 0.4544(3) 0.61763(5) 0.9221(2) 0.0549(5) Uani 1 1 d . . . . .
C13 C 0.2825(3) 0.59208(5) 0.8860(2) 0.0564(5) Uani 1 1 d . . . . .
C14 C 0.2994(4) 0.56019(6) 0.8220(4) 0.0839(8) Uani 1 1 d . . . . .
H14 H 0.4226 0.5543 0.8135 0.101 Uiso 1 1 calc R U . . .
C15 C 0.1392(4) 0.53671(6) 0.7703(4) 0.0831(7) Uani 1 1 d . . . . .
H15 H 0.1545 0.5153 0.7270 0.100 Uiso 1 1 calc R U . . .
C16 C -0.0420(3) 0.54476(5) 0.7823(3) 0.0642(6) Uani 1 1 d . . . . .
C17 C -0.0631(4) 0.57685(6) 0.8439(3) 0.0752(6) Uani 1 1 d . . . . .
H17 H -0.1870 0.5828 0.8511 0.090 Uiso 1 1 calc R U . . .
C18 C 0.0990(3) 0.60027(6) 0.8952(3) 0.0690(6) Uani 1 1 d . . . . .
H18 H 0.0832 0.6219 0.9364 0.083 Uiso 1 1 calc R U . . .
C19 C -0.2148(4) 0.51944(7) 0.7276(4) 0.0842(7) Uani 1 1 d D . . . .
C20 C 0.6791(4) 0.59871(6) 1.2360(3) 0.0707(6) Uani 1 1 d . . . . .
C21 C 0.8805(5) 0.61521(8) 1.3599(3) 0.1056(10) Uani 1 1 d . . . . .
H21A H 0.9850 0.6125 1.3162 0.158 Uiso 1 1 calc R U . . .
H21B H 0.9258 0.6042 1.4704 0.158 Uiso 1 1 calc R U . . .
H21C H 0.8581 0.6394 1.3714 0.158 Uiso 1 1 calc R U . . .
C22 C 0.7110(6) 0.56041(7) 1.2151(4) 0.1135(11) Uani 1 1 d . . . . .
H22A H 0.5805 0.5500 1.1428 0.170 Uiso 1 1 calc R U . . .
H22B H 0.7652 0.5494 1.3260 0.170 Uiso 1 1 calc R U . . .
H22C H 0.8076 0.5576 1.1632 0.170 Uiso 1 1 calc R U . . .
C23 C 0.5135(5) 0.60346(8) 1.3044(4) 0.0987(9) Uani 1 1 d . . . . .
H23A H 0.4756 0.6275 1.2977 0.148 Uiso 1 1 calc R U . . .
H23B H 0.5668 0.5959 1.4222 0.148 Uiso 1 1 calc R U . . .
H23C H 0.3932 0.5900 1.2365 0.148 Uiso 1 1 calc R U . . .
F1 F -0.3905(7) 0.53381(15) 0.6116(6) 0.1156(14) Uani 0.75 1 d D U P A 1
F2 F -0.2707(4) 0.51091(7) 0.8559(4) 0.1076(8) Uani 0.75 1 d D U P A 1
F3 F -0.1787(6) 0.49048(8) 0.6640(7) 0.1337(14) Uani 0.75 1 d D U P A 1
F1' F -0.2296(19) 0.5033(3) 0.5801(14) 0.120(3) Uani 0.25 1 d D U P A 2
F2' F -0.403(2) 0.5283(4) 0.657(2) 0.107(2) Uani 0.25 1 d D U P A 2
F3' F -0.1739(17) 0.4929(3) 0.8288(16) 0.142(3) Uani 0.25 1 d D U P A 2


_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
O1 C10 1.238(2) . ?
N1 C1 1.316(3) . ?
N1 C9 1.365(2) . ?
N2 C10 1.378(2) . ?
N2 C8 1.390(2) . ?
N2 H2 0.8600 . ?
N3 C12 1.341(3) . ?
N3 C20 1.483(3) . ?
N3 H3 0.8600 . ?
C1 C2 1.395(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.353(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.412(3) . ?
C3 H3A 0.9300 . ?
C4 C9 1.408(3) . ?
C4 C5 1.409(3) . ?
C5 C6 1.358(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.401(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.370(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.432(2) . ?
C10 C11 1.432(3) . ?
C11 C12 1.366(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.494(3) . ?
C13 C18 1.367(3) . ?
C13 C14 1.372(3) . ?
C14 C15 1.372(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.361(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.378(3) . ?
C16 C19 1.480(3) . ?
C17 C18 1.380(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 F2' 1.256(14) . ?
C19 F3' 1.294(9) . ?
C19 F3 1.313(4) . ?
C19 F1 1.345(5) . ?
C19 F2 1.348(4) . ?
C19 F1' 1.368(11) . ?
C20 C21 1.517(4) . ?
C20 C22 1.518(3) . ?
C20 C23 1.518(4) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

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
C1 N1 C9 117.22(18) . . ?
C10 N2 C8 129.27(16) . . ?
C10 N2 H2 115.4 . . ?
C8 N2 H2 115.4 . . ?
C12 N3 C20 132.80(19) . . ?
C12 N3 H3 113.6 . . ?
C20 N3 H3 113.6 . . ?
N1 C1 C2 123.8(2) . . ?
N1 C1 H1 118.1 . . ?
C2 C1 H1 118.1 . . ?
C3 C2 C1 119.53(19) . . ?
C3 C2 H2A 120.2 . . ?
C1 C2 H2A 120.2 . . ?
C2 C3 C4 119.4(2) . . ?
C2 C3 H3A 120.3 . . ?
C4 C3 H3A 120.3 . . ?
C9 C4 C5 119.48(17) . . ?
C9 C4 C3 117.02(18) . . ?
C5 C4 C3 123.50(18) . . ?
C6 C5 C4 119.41(18) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C7 122.20(19) . . ?
C5 C6 H6 118.9 . . ?
C7 C6 H6 118.9 . . ?
C8 C7 C6 120.03(18) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 N2 126.13(17) . . ?
C7 C8 C9 119.14(17) . . ?
N2 C8 C9 114.68(16) . . ?
N1 C9 C4 122.99(16) . . ?
N1 C9 C8 117.28(16) . . ?
C4 C9 C8 119.72(17) . . ?
O1 C10 N2 121.49(17) . . ?
O1 C10 C11 124.46(17) . . ?
N2 C10 C11 114.02(17) . . ?
C12 C11 C10 125.07(18) . . ?
C12 C11 H11 117.5 . . ?
C10 C11 H11 117.5 . . ?
N3 C12 C11 122.04(19) . . ?
N3 C12 C13 121.85(17) . . ?
C11 C12 C13 115.88(17) . . ?
C18 C13 C14 118.1(2) . . ?
C18 C13 C12 122.98(18) . . ?
C14 C13 C12 118.53(18) . . ?
C13 C14 C15 121.7(2) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 H14 119.2 . . ?
C16 C15 C14 120.0(2) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 119.2(2) . . ?
C15 C16 C19 120.2(2) . . ?
C17 C16 C19 120.6(2) . . ?
C16 C17 C18 120.2(2) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C13 C18 C17 120.8(2) . . ?
C13 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
F2' C19 F3' 115.7(9) . . ?
F3 C19 F1 109.0(4) . . ?
F3 C19 F2 107.4(3) . . ?
F1 C19 F2 101.9(3) . . ?
F2' C19 F1' 91.3(10) . . ?
F3' C19 F1' 99.4(8) . . ?
F2' C19 C16 122.7(8) . . ?
F3' C19 C16 112.7(5) . . ?
F3 C19 C16 114.7(3) . . ?
F1 C19 C16 110.4(3) . . ?
F2 C19 C16 112.7(2) . . ?
F1' C19 C16 109.3(6) . . ?
N3 C20 C21 104.69(19) . . ?
N3 C20 C22 111.5(2) . . ?
C21 C20 C22 110.4(2) . . ?
N3 C20 C23 111.0(2) . . ?
C21 C20 C23 109.4(2) . . ?
C22 C20 C23 109.8(2) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

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
C9 N1 C1 C2 0.6(3) . . . . ?
N1 C1 C2 C3 -0.1(4) . . . . ?
C1 C2 C3 C4 -0.8(3) . . . . ?
C2 C3 C4 C9 1.1(3) . . . . ?
C2 C3 C4 C5 -179.8(2) . . . . ?
C9 C4 C5 C6 0.4(3) . . . . ?
C3 C4 C5 C6 -178.6(2) . . . . ?
C4 C5 C6 C7 0.3(3) . . . . ?
C5 C6 C7 C8 -0.1(3) . . . . ?
C6 C7 C8 N2 176.38(19) . . . . ?
C6 C7 C8 C9 -0.9(3) . . . . ?
C10 N2 C8 C7 -8.0(3) . . . . ?
C10 N2 C8 C9 169.36(18) . . . . ?
C1 N1 C9 C4 -0.2(3) . . . . ?
C1 N1 C9 C8 -178.60(18) . . . . ?
C5 C4 C9 N1 -179.80(18) . . . . ?
C3 C4 C9 N1 -0.7(3) . . . . ?
C5 C4 C9 C8 -1.4(3) . . . . ?
C3 C4 C9 C8 177.72(17) . . . . ?
C7 C8 C9 N1 -179.88(18) . . . . ?
N2 C8 C9 N1 2.5(3) . . . . ?
C7 C8 C9 C4 1.6(3) . . . . ?
N2 C8 C9 C4 -175.94(17) . . . . ?
C8 N2 C10 O1 18.4(3) . . . . ?
C8 N2 C10 C11 -159.5(2) . . . . ?
O1 C10 C11 C12 -3.4(3) . . . . ?
N2 C10 C11 C12 174.54(19) . . . . ?
C20 N3 C12 C11 177.8(2) . . . . ?
C20 N3 C12 C13 -8.0(4) . . . . ?
C10 C11 C12 N3 5.8(3) . . . . ?
C10 C11 C12 C13 -168.66(19) . . . . ?
N3 C12 C13 C18 102.3(3) . . . . ?
C11 C12 C13 C18 -83.2(3) . . . . ?
N3 C12 C13 C14 -85.4(3) . . . . ?
C11 C12 C13 C14 89.1(3) . . . . ?
C18 C13 C14 C15 -0.8(4) . . . . ?
C12 C13 C14 C15 -173.6(2) . . . . ?
C13 C14 C15 C16 -0.2(4) . . . . ?
C14 C15 C16 C17 1.1(4) . . . . ?
C14 C15 C16 C19 -179.6(3) . . . . ?
C15 C16 C17 C18 -1.0(4) . . . . ?
C19 C16 C17 C18 179.8(2) . . . . ?
C14 C13 C18 C17 1.0(3) . . . . ?
C12 C13 C18 C17 173.4(2) . . . . ?
C16 C17 C18 C13 -0.1(4) . . . . ?
C15 C16 C19 F2' -144.9(9) . . . . ?
C17 C16 C19 F2' 34.3(10) . . . . ?
C15 C16 C19 F3' 69.2(9) . . . . ?
C17 C16 C19 F3' -111.5(8) . . . . ?
C15 C16 C19 F3 -2.2(5) . . . . ?
C17 C16 C19 F3 177.0(3) . . . . ?
C15 C16 C19 F1 -125.8(4) . . . . ?
C17 C16 C19 F1 53.4(4) . . . . ?
C15 C16 C19 F2 121.0(3) . . . . ?
C17 C16 C19 F2 -59.7(3) . . . . ?
C15 C16 C19 F1' -40.2(6) . . . . ?
C17 C16 C19 F1' 139.0(6) . . . . ?
C12 N3 C20 C21 -171.8(3) . . . . ?
C12 N3 C20 C22 68.8(3) . . . . ?
C12 N3 C20 C23 -53.9(3) . . . . ?

_refine_diff_density_max         0.267
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.030

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_cu_d8v23476_0m
_database_code_depnum_ccdc_archive 'CCDC 2293754'
loop_
_audit_author_name
_audit_author_address
Huiying
;Changzhou University
China
;
_audit_update_record             
;
2023-09-08 deposited with the CCDC.	2023-12-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H22 Br N3 O'
_chemical_formula_weight         424.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
Br Br -0.6763 1.2805 '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      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                   11.3229(3)
_cell_length_b                   6.3163(2)
_cell_length_c                   28.5159(8)
_cell_angle_alpha                90
_cell_angle_beta                 98.615(2)
_cell_angle_gamma                90
_cell_volume                     2016.41(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4552
_cell_measurement_theta_min      6.270
_cell_measurement_theta_max      140.333

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_F_000             872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    2.899
_shelx_estimated_absorpt_T_min   0.654
_shelx_estimated_absorpt_T_max   0.869
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4997
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16471
_diffrn_reflns_av_unetI/netI     0.0625
_diffrn_reflns_av_R_equivalents  0.1017
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         3.135
_diffrn_reflns_theta_max         66.993
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             3590
_reflns_number_gt                2528
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0773P)²+0.7057P] 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
_refine_ls_extinction_coef       0.0041(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3590
_refine_ls_number_parameters     278
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0884
_refine_ls_R_factor_gt           0.0532
_refine_ls_wR_factor_ref         0.1637
_refine_ls_wR_factor_gt          0.1372
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.005
_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 0.07045(4) 0.54535(9) 0.57158(2) 0.0685(3) Uani 1 1 d . . . . .
O1 O 0.3622(3) 0.5485(6) 0.67391(12) 0.0808(11) Uani 1 1 d . . . . .
N1 N 0.0400(4) 1.0673(7) 0.66130(14) 0.0715(11) Uani 1 1 d . . . . .
N2 N 0.1989(3) 0.7615(7) 0.65922(13) 0.0682(11) Uani 1 1 d . . . . .
H2 H 0.1307 0.7754 0.6416 0.082 Uiso 1 1 calc R U . . .
N3 N 0.3906(4) 0.2455(8) 0.61207(14) 0.0872(14) Uani 1 1 d . . . . .
H3 H 0.3956 0.2647 0.6422 0.105 Uiso 1 1 calc R U . . .
C1 C -0.0393(5) 1.2206(9) 0.6608(2) 0.0847(16) Uani 1 1 d . . . . .
H1 H -0.1072 1.2153 0.6379 0.102 Uiso 1 1 calc R U . . .
C2 C -0.0273(7) 1.3905(11) 0.6925(2) 0.098(2) Uani 1 1 d . . . . .
H2A H -0.0868 1.4928 0.6911 0.118 Uiso 1 1 calc R U . . .
C3 C 0.0717(6) 1.4046(10) 0.7254(2) 0.0930(19) Uani 1 1 d . . . . .
H3A H 0.0820 1.5192 0.7461 0.112 Uiso 1 1 calc R U . . .
C4 C 0.1590(5) 1.2452(9) 0.72809(17) 0.0777(15) Uani 1 1 d . . . . .
C5 C 0.1393(5) 1.0781(8) 0.69407(16) 0.0655(12) Uani 1 1 d . . . . .
C6 C 0.2263(5) 0.9129(8) 0.69508(16) 0.0671(13) Uani 1 1 d . . . . .
C7 C 0.3262(5) 0.9171(10) 0.72866(18) 0.0833(16) Uani 1 1 d . . . . .
H7 H 0.3824 0.8092 0.7296 0.100 Uiso 1 1 calc R U . . .
C8 C 0.3445(6) 1.0834(12) 0.7617(2) 0.095(2) Uani 1 1 d . . . . .
H8 H 0.4130 1.0846 0.7842 0.114 Uiso 1 1 calc R U . . .
C9 C 0.2646(6) 1.2406(12) 0.7613(2) 0.0935(18) Uani 1 1 d . . . . .
H9 H 0.2792 1.3491 0.7835 0.112 Uiso 1 1 calc R U . . .
C10 C 0.2669(4) 0.5945(8) 0.64875(16) 0.0638(12) Uani 1 1 d . . . . .
C11 C 0.2242(4) 0.4774(7) 0.60540(16) 0.0588(11) Uani 1 1 d . . . . .
C12 C 0.2903(4) 0.3235(8) 0.58659(16) 0.0618(11) Uani 1 1 d . . . . .
C13 C 0.2491(4) 0.2453(7) 0.53763(16) 0.0608(11) Uani 1 1 d . . . . .
C14 C 0.2651(4) 0.3679(9) 0.49918(17) 0.0687(12) Uani 1 1 d . . . . .
H14 H 0.3052 0.4964 0.5040 0.082 Uiso 1 1 calc R U . . .
C15 C 0.2230(5) 0.3038(10) 0.45388(18) 0.0834(16) Uani 1 1 d . . . . .
H15 H 0.2342 0.3889 0.4283 0.100 Uiso 1 1 calc R U . . .
C16 C 0.1641(5) 0.1132(12) 0.4462(2) 0.095(2) Uani 1 1 d . . . . .
H16 H 0.1356 0.0693 0.4154 0.114 Uiso 1 1 calc R U . . .
C17 C 0.1476(6) -0.0115(10) 0.4840(3) 0.096(2) Uani 1 1 d . . . . .
H17 H 0.1081 -0.1404 0.4789 0.115 Uiso 1 1 calc R U . . .
C18 C 0.1899(5) 0.0550(8) 0.5300(2) 0.0793(15) Uani 1 1 d . . . . .
H18 H 0.1782 -0.0293 0.5556 0.095 Uiso 1 1 calc R U . . .
C19 C 0.4932(4) 0.1330(9) 0.59755(18) 0.0723(13) Uani 1 1 d D . . . .
C20 C 0.534(3) 0.238(6) 0.5552(7) 0.102(7) Uani 0.5 1 d D U P A 1
H20A H 0.4803 0.2001 0.5270 0.154 Uiso 0.5 1 calc R U P A 1
H20B H 0.6130 0.1913 0.5524 0.154 Uiso 0.5 1 calc R U P A 1
H20C H 0.5334 0.3887 0.5592 0.154 Uiso 0.5 1 calc R U P A 1
C21 C 0.449(4) -0.088(5) 0.5842(19) 0.136(8) Uani 0.5 1 d D U P A 1
H21A H 0.4380 -0.1645 0.6123 0.204 Uiso 0.5 1 calc R U P A 1
H21B H 0.5074 -0.1603 0.5687 0.204 Uiso 0.5 1 calc R U P A 1
H21C H 0.3750 -0.0804 0.5631 0.204 Uiso 0.5 1 calc R U P A 1
C22 C 0.5942(17) 0.170(3) 0.6413(7) 0.111(6) Uani 0.5 1 d D U P A 1
H22A H 0.6121 0.3188 0.6443 0.166 Uiso 0.5 1 calc R U P A 1
H22B H 0.6648 0.0941 0.6366 0.166 Uiso 0.5 1 calc R U P A 1
H22C H 0.5672 0.1209 0.6697 0.166 Uiso 0.5 1 calc R U P A 1
C20' C 0.563(3) 0.287(6) 0.5713(8) 0.100(7) Uani 0.5 1 d D U P A 2
H20D H 0.5127 0.3360 0.5433 0.150 Uiso 0.5 1 calc R U P A 2
H20E H 0.6314 0.2162 0.5625 0.150 Uiso 0.5 1 calc R U P A 2
H20F H 0.5883 0.4047 0.5915 0.150 Uiso 0.5 1 calc R U P A 2
C21' C 0.472(4) -0.076(5) 0.5703(19) 0.132(8) Uani 0.5 1 d D U P A 2
H21D H 0.4036 -0.1461 0.5795 0.198 Uiso 0.5 1 calc R U P A 2
H21E H 0.5409 -0.1646 0.5775 0.198 Uiso 0.5 1 calc R U P A 2
H21F H 0.4573 -0.0472 0.5369 0.198 Uiso 0.5 1 calc R U P A 2
C22' C 0.5648(17) 0.046(3) 0.6439(6) 0.100(5) Uani 0.5 1 d D U P A 2
H22D H 0.5831 0.1594 0.6662 0.150 Uiso 0.5 1 calc R U P A 2
H22E H 0.6377 -0.0169 0.6372 0.150 Uiso 0.5 1 calc R U P A 2
H22F H 0.5181 -0.0592 0.6571 0.150 Uiso 0.5 1 calc R U P A 2


_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 C11 1.908(5) . ?
O1 C10 1.237(5) . ?
N1 C1 1.319(6) . ?
N1 C5 1.352(6) . ?
N2 C10 1.365(6) . ?
N2 C6 1.400(6) . ?
N2 H2 0.8600 . ?
N3 C12 1.347(5) . ?
N3 C19 1.473(6) . ?
N3 H3 0.8600 . ?
C1 C2 1.398(8) . ?
C1 H1 0.9300 . ?
C2 C3 1.352(9) . ?
C2 H2A 0.9300 . ?
C3 C4 1.404(8) . ?
C3 H3A 0.9300 . ?
C4 C9 1.410(8) . ?
C4 C5 1.428(7) . ?
C5 C6 1.432(7) . ?
C6 C7 1.368(7) . ?
C7 C8 1.406(8) . ?
C7 H7 0.9300 . ?
C8 C9 1.342(9) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.459(6) . ?
C11 C12 1.383(6) . ?
C12 C13 1.488(6) . ?
C13 C14 1.377(6) . ?
C13 C18 1.378(7) . ?
C14 C15 1.370(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.378(9) . ?
C15 H15 0.9300 . ?
C16 C17 1.371(10) . ?
C16 H16 0.9300 . ?
C17 C18 1.391(9) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.508(16) . ?
C19 C21 1.513(17) . ?
C19 C20' 1.516(16) . ?
C19 C21' 1.531(17) . ?
C19 C22' 1.545(14) . ?
C19 C22 1.580(14) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C20' H20D 0.9600 . ?
C20' H20E 0.9600 . ?
C20' H20F 0.9600 . ?
C21' H21D 0.9600 . ?
C21' H21E 0.9600 . ?
C21' H21F 0.9600 . ?
C22' H22D 0.9600 . ?
C22' H22E 0.9600 . ?
C22' H22F 0.9600 . ?

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
C1 N1 C5 117.7(5) . . ?
C10 N2 C6 128.1(4) . . ?
C10 N2 H2 116.0 . . ?
C6 N2 H2 116.0 . . ?
C12 N3 C19 131.4(4) . . ?
C12 N3 H3 114.3 . . ?
C19 N3 H3 114.3 . . ?
N1 C1 C2 123.8(6) . . ?
N1 C1 H1 118.1 . . ?
C2 C1 H1 118.1 . . ?
C3 C2 C1 119.3(6) . . ?
C3 C2 H2A 120.4 . . ?
C1 C2 H2A 120.4 . . ?
C2 C3 C4 119.7(6) . . ?
C2 C3 H3A 120.2 . . ?
C4 C3 H3A 120.2 . . ?
C3 C4 C9 124.8(6) . . ?
C3 C4 C5 117.1(5) . . ?
C9 C4 C5 118.1(6) . . ?
N1 C5 C4 122.4(5) . . ?
N1 C5 C6 118.4(4) . . ?
C4 C5 C6 119.2(5) . . ?
C7 C6 N2 126.4(5) . . ?
C7 C6 C5 119.6(5) . . ?
N2 C6 C5 114.0(4) . . ?
C6 C7 C8 120.5(6) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C9 C8 C7 121.0(6) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C8 C9 C4 121.6(6) . . ?
C8 C9 H9 119.2 . . ?
C4 C9 H9 119.2 . . ?
O1 C10 N2 121.7(4) . . ?
O1 C10 C11 121.5(5) . . ?
N2 C10 C11 116.8(4) . . ?
C12 C11 C10 123.7(4) . . ?
C12 C11 Br1 117.9(3) . . ?
C10 C11 Br1 118.4(3) . . ?
N3 C12 C11 120.6(4) . . ?
N3 C12 C13 120.3(4) . . ?
C11 C12 C13 119.1(4) . . ?
C14 C13 C18 118.9(5) . . ?
C14 C13 C12 120.0(5) . . ?
C18 C13 C12 121.0(5) . . ?
C15 C14 C13 121.1(6) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C16 120.1(6) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C17 C16 C15 119.7(6) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 C18 120.0(6) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C13 C18 C17 120.2(6) . . ?
C13 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
N3 C19 C20 111.2(18) . . ?
N3 C19 C21 105.9(13) . . ?
C20 C19 C21 109(2) . . ?
N3 C19 C20' 108.7(19) . . ?
N3 C19 C21' 119.1(14) . . ?
C20' C19 C21' 111(2) . . ?
N3 C19 C22' 105.5(9) . . ?
C20' C19 C22' 113.9(12) . . ?
C21' C19 C22' 99(3) . . ?
N3 C19 C22 102.4(9) . . ?
C20 C19 C22 107.3(12) . . ?
C21 C19 C22 121(3) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C19 C20' H20D 109.5 . . ?
C19 C20' H20E 109.5 . . ?
H20D C20' H20E 109.5 . . ?
C19 C20' H20F 109.5 . . ?
H20D C20' H20F 109.5 . . ?
H20E C20' H20F 109.5 . . ?
C19 C21' H21D 109.5 . . ?
C19 C21' H21E 109.5 . . ?
H21D C21' H21E 109.5 . . ?
C19 C21' H21F 109.5 . . ?
H21D C21' H21F 109.5 . . ?
H21E C21' H21F 109.5 . . ?
C19 C22' H22D 109.5 . . ?
C19 C22' H22E 109.5 . . ?
H22D C22' H22E 109.5 . . ?
C19 C22' H22F 109.5 . . ?
H22D C22' H22F 109.5 . . ?
H22E C22' H22F 109.5 . . ?

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
C5 N1 C1 C2 -1.1(8) . . . . ?
N1 C1 C2 C3 1.5(10) . . . . ?
C1 C2 C3 C4 -2.0(10) . . . . ?
C2 C3 C4 C9 -178.8(6) . . . . ?
C2 C3 C4 C5 2.3(8) . . . . ?
C1 N1 C5 C4 1.4(7) . . . . ?
C1 N1 C5 C6 -180.0(5) . . . . ?
C3 C4 C5 N1 -2.0(8) . . . . ?
C9 C4 C5 N1 179.0(5) . . . . ?
C3 C4 C5 C6 179.4(5) . . . . ?
C9 C4 C5 C6 0.4(7) . . . . ?
C10 N2 C6 C7 -3.4(8) . . . . ?
C10 N2 C6 C5 175.1(5) . . . . ?
N1 C5 C6 C7 -178.3(5) . . . . ?
C4 C5 C6 C7 0.3(7) . . . . ?
N1 C5 C6 N2 3.0(6) . . . . ?
C4 C5 C6 N2 -178.3(4) . . . . ?
N2 C6 C7 C8 177.7(5) . . . . ?
C5 C6 C7 C8 -0.7(8) . . . . ?
C6 C7 C8 C9 0.4(9) . . . . ?
C7 C8 C9 C4 0.4(10) . . . . ?
C3 C4 C9 C8 -179.7(6) . . . . ?
C5 C4 C9 C8 -0.7(9) . . . . ?
C6 N2 C10 O1 5.9(8) . . . . ?
C6 N2 C10 C11 -171.9(5) . . . . ?
O1 C10 C11 C12 -6.7(8) . . . . ?
N2 C10 C11 C12 171.0(4) . . . . ?
O1 C10 C11 Br1 175.2(4) . . . . ?
N2 C10 C11 Br1 -7.1(6) . . . . ?
C19 N3 C12 C11 -160.0(5) . . . . ?
C19 N3 C12 C13 19.9(9) . . . . ?
C10 C11 C12 N3 12.1(8) . . . . ?
Br1 C11 C12 N3 -169.8(4) . . . . ?
C10 C11 C12 C13 -167.8(4) . . . . ?
Br1 C11 C12 C13 10.4(6) . . . . ?
N3 C12 C13 C14 -104.1(6) . . . . ?
C11 C12 C13 C14 75.8(6) . . . . ?
N3 C12 C13 C18 78.9(6) . . . . ?
C11 C12 C13 C18 -101.2(6) . . . . ?
C18 C13 C14 C15 0.2(7) . . . . ?
C12 C13 C14 C15 -176.9(4) . . . . ?
C13 C14 C15 C16 -0.4(8) . . . . ?
C14 C15 C16 C17 0.2(9) . . . . ?
C15 C16 C17 C18 0.2(9) . . . . ?
C14 C13 C18 C17 0.2(8) . . . . ?
C12 C13 C18 C17 177.3(5) . . . . ?
C16 C17 C18 C13 -0.4(9) . . . . ?
C12 N3 C19 C20 44.5(13) . . . . ?
C12 N3 C19 C21 -74(3) . . . . ?
C12 N3 C19 C20' 69.1(11) . . . . ?
C12 N3 C19 C21' -59(3) . . . . ?
C12 N3 C19 C22' -168.4(8) . . . . ?
C12 N3 C19 C22 158.7(9) . . . . ?

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
C7 H7 O1 0.93 2.28 2.866(7) 120.9 .
N3 H3 O1 0.86 2.07 2.655(6) 124.7 .
N2 H2 N1 0.86 2.22 2.646(6) 110.2 .
N2 H2 Br1 0.86 2.48 3.023(4) 121.6 .
C7 H7 O1 0.93 2.28 2.866(7) 120.9 .
N3 H3 O1 0.86 2.07 2.655(6) 124.7 .
N2 H2 N1 0.86 2.22 2.646(6) 110.2 .
N2 H2 Br1 0.86 2.48 3.023(4) 121.6 .
C7 H7 O1 0.93 2.28 2.866(7) 120.9 .
N3 H3 O1 0.86 2.07 2.655(6) 124.7 .
N2 H2 N1 0.86 2.22 2.646(6) 110.2 .
N2 H2 Br1 0.86 2.48 3.023(4) 121.6 .
N2 H2 Br1 0.86 2.48 3.023(4) 121.6 .
N2 H2 N1 0.86 2.22 2.646(6) 110.2 .
N3 H3 O1 0.86 2.07 2.655(6) 124.7 .
C7 H7 O1 0.93 2.28 2.866(7) 120.9 .

_refine_diff_density_max         0.418
_refine_diff_density_min         -0.572
_refine_diff_density_rms         0.078

_shelxl_version_number           2013-4

