# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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 2426056'
loop_
_audit_author_name
_audit_author_address
'Yanren Zhu'
;Yunnan University
China
;
_audit_update_record             
;
2025-02-22 deposited with the CCDC.	2025-06-24 downloaded from the CCDC.
;
_audit_creation_date             2024-12-11
_audit_creation_method           
;
FinalCif V89 by Daniel Kratzert, Freiburg 2024,
https://dkratzert.de/finalcif.html
;
_diffrn_source_power             0.07
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C34 H39 N O2'
_chemical_formula_moiety         'C34 H39 N O2'
_chemical_formula_weight         493.66
_exptl_crystal_colour_primary    colourless
_chemical_melting_point          ?
_chemical_absolute_configuration unk
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C15(H15A,H15B), C16(H16A,H16B), C22(H22A,H22B), C23(H23A,H23B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C9(H9), C10(H10), C26(H26),
 C28(H28)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), C32(H32A,H32B,
 H32C), C33(H33A,H33B,H33C), C34(H34A,H34B,H34C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.1352(4)
_cell_length_b                   16.5171(6)
_cell_length_c                   17.9335(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2705.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.00
_cell_measurement_reflns_used    9215
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      28.28
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6979
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0899 before and 0.0702 after correction.
The Ratio of minimum to maximum transmission is 0.9359.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.988
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      100.00
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'mirror optics'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_diffrn_measurement_ambient_temperature_device_make ?
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_source_current           1.4
_diffrn_detector                 CPAD
_diffrn_detector_type            'Bruker PHOTON'
_diffrn_detector_area_resol_mean 7.41
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            28167
_diffrn_reflns_av_unetI/netI     0.0595
_diffrn_reflns_av_R_equivalents  0.0658
_diffrn_reflns_theta_min         2.271
_diffrn_reflns_theta_max         28.313
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_standards_number         0
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6684
_reflns_number_gt                5510
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.776
_reflns_Friedel_fraction_max     0.989
_reflns_Friedel_fraction_full    0.998
_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       'SAINT V8.40B'
_computing_data_reduction        'SAINT V8.40B'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_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)+(0.0349P)²+0.8713P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         6684
_refine_ls_number_parameters     340
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0497
_refine_ls_wR_factor_ref         0.1045
_refine_ls_wR_factor_gt          0.0943
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_Flack   -0.1(8)
_refine_ls_abs_structure_details 
;
 Flack x determined using 1951 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;

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'
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'

_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_
_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 0.5075(2) 0.78329(11) 0.85763(10) 0.0232(4) Uani 1 1 d . . . . .
O2 O 0.6487(2) 0.49047(10) 0.94811(10) 0.0223(4) Uani 1 1 d . . . . .
N1 N 0.5825(2) 0.61829(12) 0.91724(12) 0.0158(5) Uani 1 1 d . . . . .
H1 H 0.611613 0.668995 0.914610 0.019 Uiso 1 1 calc R U . . .
C1 C 0.2442(3) 0.76316(15) 0.61421(14) 0.0178(5) Uani 1 1 d . . . . .
C2 C 0.1961(3) 0.76740(17) 0.53908(15) 0.0242(6) Uani 1 1 d . . . . .
H2 H 0.228282 0.810602 0.508202 0.029 Uiso 1 1 calc R U . . .
C3 C 0.1039(3) 0.71004(18) 0.51068(16) 0.0272(7) Uani 1 1 d . . . . .
H3 H 0.072432 0.714037 0.460331 0.033 Uiso 1 1 calc R U . . .
C4 C 0.0548(3) 0.64474(18) 0.55521(16) 0.0257(6) Uani 1 1 d . . . . .
H4 H -0.008536 0.604918 0.534696 0.031 Uiso 1 1 calc R U . . .
C5 C 0.0989(3) 0.63923(16) 0.62805(15) 0.0209(6) Uani 1 1 d . . . . .
H5 H 0.065693 0.595428 0.657919 0.025 Uiso 1 1 calc R U . . .
C6 C 0.1941(3) 0.69841(15) 0.65955(14) 0.0178(5) Uani 1 1 d . . . . .
C7 C 0.2421(3) 0.69336(15) 0.73471(14) 0.0179(5) Uani 1 1 d . . . . .
H7 H 0.207477 0.650820 0.765682 0.021 Uiso 1 1 calc R U . . .
C8 C 0.3387(3) 0.74973(14) 0.76317(14) 0.0165(5) Uani 1 1 d . . . . .
C9 C 0.3884(3) 0.81480(15) 0.71742(15) 0.0184(6) Uani 1 1 d . . . . .
H9 H 0.454826 0.853592 0.736999 0.022 Uiso 1 1 calc R U . . .
C10 C 0.3406(3) 0.82145(15) 0.64563(15) 0.0202(6) Uani 1 1 d . . . . .
H10 H 0.372421 0.865836 0.616079 0.024 Uiso 1 1 calc R U . . .
C11 C 0.4009(3) 0.74190(14) 0.83909(14) 0.0167(5) Uani 1 1 d . . . . .
C12 C 0.3444(3) 0.68332(15) 0.89643(14) 0.0160(5) Uani 1 1 d . . . . .
C13 C 0.3414(3) 0.71408(15) 0.97860(14) 0.0200(6) Uani 1 1 d . . . . .
H13A H 0.436458 0.711174 1.004991 0.024 Uiso 1 1 calc R U . . .
H13B H 0.292731 0.767044 0.985888 0.024 Uiso 1 1 calc R U . . .
C14 C 0.2411(3) 0.63949(16) 0.98941(14) 0.0207(6) Uani 1 1 d . . . . .
H14 H 0.171468 0.637545 1.032401 0.025 Uiso 1 1 calc R U . . .
C15 C 0.1830(3) 0.65697(16) 0.90970(14) 0.0188(6) Uani 1 1 d . . . . .
H15A H 0.110252 0.701246 0.906480 0.023 Uiso 1 1 calc R U . . .
H15B H 0.151792 0.608509 0.881376 0.023 Uiso 1 1 calc R U . . .
C16 C 0.3501(3) 0.56996(15) 0.97715(14) 0.0181(6) Uani 1 1 d . . . . .
H16A H 0.299604 0.517623 0.969291 0.022 Uiso 1 1 calc R U . . .
H16B H 0.419742 0.564880 1.019199 0.022 Uiso 1 1 calc R U . . .
C17 C 0.4280(3) 0.60028(14) 0.90418(14) 0.0153(5) Uani 1 1 d . . . . .
C18 C 0.6829(3) 0.56061(15) 0.93320(13) 0.0174(5) Uani 1 1 d . . . . .
C19 C 0.8405(3) 0.58804(16) 0.93191(15) 0.0218(6) Uani 1 1 d . . . . .
H19A H 0.875177 0.595821 0.983124 0.033 Uiso 1 1 calc R U . . .
H19B H 0.847998 0.639238 0.904559 0.033 Uiso 1 1 calc R U . . .
H19C H 0.900649 0.546873 0.907213 0.033 Uiso 1 1 calc R U . . .
C20 C 0.4103(3) 0.54791(14) 0.83367(14) 0.0147(5) Uani 1 1 d . . . . .
C21 C 0.4944(3) 0.56112(14) 0.76908(13) 0.0145(5) Uani 1 1 d . . . . .
C22 C 0.6275(3) 0.61476(16) 0.75413(14) 0.0196(6) Uani 1 1 d . . . . .
H22A H 0.718289 0.589236 0.773042 0.024 Uiso 1 1 calc R U . . .
H22B H 0.615838 0.668563 0.777717 0.024 Uiso 1 1 calc R U . . .
C23 C 0.6304(3) 0.62188(15) 0.66809(14) 0.0204(6) Uani 1 1 d . . . . .
H23A H 0.571624 0.668790 0.651254 0.024 Uiso 1 1 calc R U . . .
H23B H 0.732018 0.628383 0.649819 0.024 Uiso 1 1 calc R U . . .
C24 C 0.5636(3) 0.54188(15) 0.63958(14) 0.0165(5) Uani 1 1 d . . . . .
C25 C 0.4602(3) 0.51995(14) 0.70333(14) 0.0147(5) Uani 1 1 d . . . . .
C26 C 0.3463(3) 0.46423(14) 0.69979(14) 0.0162(5) Uani 1 1 d . . . . .
H26 H 0.324441 0.437764 0.654102 0.019 Uiso 1 1 calc R U . . .
C27 C 0.2644(3) 0.44734(14) 0.76342(14) 0.0149(5) Uani 1 1 d . . . . .
C28 C 0.2986(3) 0.49006(14) 0.82888(14) 0.0159(5) Uani 1 1 d . . . . .
H28 H 0.242680 0.479091 0.872400 0.019 Uiso 1 1 calc R U . . .
C29 C 0.4850(3) 0.55370(16) 0.56512(14) 0.0201(6) Uani 1 1 d . . . . .
H29A H 0.441884 0.502215 0.549138 0.030 Uiso 1 1 calc R U . . .
H29B H 0.555266 0.572247 0.527524 0.030 Uiso 1 1 calc R U . . .
H29C H 0.407469 0.594217 0.570948 0.030 Uiso 1 1 calc R U . . .
C30 C 0.6819(3) 0.47609(16) 0.63244(15) 0.0216(6) Uani 1 1 d . . . . .
H30A H 0.734512 0.470965 0.679833 0.032 Uiso 1 1 calc R U . . .
H30B H 0.750923 0.491109 0.592947 0.032 Uiso 1 1 calc R U . . .
H30C H 0.635739 0.424269 0.619982 0.032 Uiso 1 1 calc R U . . .
C31 C 0.1403(3) 0.38500(15) 0.76527(14) 0.0177(5) Uani 1 1 d . . . . .
C32 C -0.0011(3) 0.42526(18) 0.79095(19) 0.0319(7) Uani 1 1 d . . . . .
H32A H 0.010332 0.444136 0.842428 0.048 Uiso 1 1 calc R U . . .
H32B H -0.081502 0.386081 0.788429 0.048 Uiso 1 1 calc R U . . .
H32C H -0.023003 0.471435 0.758507 0.048 Uiso 1 1 calc R U . . .
C33 C 0.1802(4) 0.31710(17) 0.82017(18) 0.0327(7) Uani 1 1 d . . . . .
H33A H 0.271369 0.291142 0.804165 0.049 Uiso 1 1 calc R U . . .
H33B H 0.101368 0.276862 0.821228 0.049 Uiso 1 1 calc R U . . .
H33C H 0.193216 0.339995 0.870149 0.049 Uiso 1 1 calc R U . . .
C34 C 0.1138(4) 0.3462(2) 0.68873(18) 0.0419(9) Uani 1 1 d . . . . .
H34A H 0.082909 0.387914 0.653198 0.063 Uiso 1 1 calc R U . . .
H34B H 0.037047 0.304984 0.692992 0.063 Uiso 1 1 calc R U . . .
H34C H 0.204427 0.320888 0.671106 0.063 Uiso 1 1 calc R U . . .


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 C11 1.235(3) . ?
O2 C18 1.229(3) . ?
N1 H1 0.8800 . ?
N1 C17 1.462(3) . ?
N1 C18 1.353(3) . ?
C1 C2 1.419(4) . ?
C1 C6 1.419(4) . ?
C1 C10 1.422(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.366(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.415(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.370(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.425(4) . ?
C6 C7 1.420(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.380(4) . ?
C8 C9 1.426(3) . ?
C8 C11 1.481(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.364(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.504(4) . ?
C12 C13 1.559(3) . ?
C12 C15 1.555(4) . ?
C12 C17 1.576(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.548(4) . ?
C14 H14 1.0000 . ?
C14 C15 1.552(4) . ?
C14 C16 1.536(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.571(4) . ?
C17 C20 1.541(3) . ?
C18 C19 1.509(4) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.407(3) . ?
C20 C28 1.401(3) . ?
C21 C22 1.528(4) . ?
C21 C25 1.396(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.548(4) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.543(3) . ?
C24 C25 1.526(3) . ?
C24 C29 1.529(4) . ?
C24 C30 1.538(4) . ?
C25 C26 1.391(3) . ?
C26 H26 0.9500 . ?
C26 C27 1.393(3) . ?
C27 C28 1.405(3) . ?
C27 C31 1.532(4) . ?
C28 H28 0.9500 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 C32 1.524(4) . ?
C31 C33 1.536(4) . ?
C31 C34 1.534(4) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?

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
C17 N1 H1 118.5 . . ?
C18 N1 H1 118.5 . . ?
C18 N1 C17 123.1(2) . . ?
C2 C1 C6 118.8(2) . . ?
C2 C1 C10 122.3(2) . . ?
C6 C1 C10 118.9(2) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.7(3) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 120.9(3) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.7(3) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.8(3) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 119.1(2) . . ?
C1 C6 C7 119.2(2) . . ?
C7 C6 C5 121.6(2) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 C6 120.6(2) . . ?
C8 C7 H7 119.7 . . ?
C7 C8 C9 119.9(2) . . ?
C7 C8 C11 121.8(2) . . ?
C9 C8 C11 118.2(2) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.1(3) . . ?
C10 C9 H9 119.9 . . ?
C1 C10 H10 119.4 . . ?
C9 C10 C1 121.2(2) . . ?
C9 C10 H10 119.4 . . ?
O1 C11 C8 120.1(2) . . ?
O1 C11 C12 116.3(2) . . ?
C8 C11 C12 123.6(2) . . ?
C11 C12 C13 116.3(2) . . ?
C11 C12 C15 127.6(2) . . ?
C11 C12 C17 117.0(2) . . ?
C13 C12 C17 102.1(2) . . ?
C15 C12 C13 85.99(19) . . ?
C15 C12 C17 101.7(2) . . ?
C12 C13 H13A 114.9 . . ?
C12 C13 H13B 114.9 . . ?
H13A C13 H13B 111.9 . . ?
C14 C13 C12 82.49(18) . . ?
C14 C13 H13A 114.9 . . ?
C14 C13 H13B 114.9 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 86.50(19) . . ?
C15 C14 H14 119.9 . . ?
C16 C14 C13 101.1(2) . . ?
C16 C14 H14 119.9 . . ?
C16 C14 C15 103.2(2) . . ?
C12 C15 H15A 114.9 . . ?
C12 C15 H15B 114.9 . . ?
C14 C15 C12 82.47(19) . . ?
C14 C15 H15A 114.9 . . ?
C14 C15 H15B 114.9 . . ?
H15A C15 H15B 111.9 . . ?
C14 C16 H16A 111.8 . . ?
C14 C16 H16B 111.8 . . ?
C14 C16 C17 100.03(19) . . ?
H16A C16 H16B 109.5 . . ?
C17 C16 H16A 111.8 . . ?
C17 C16 H16B 111.8 . . ?
N1 C17 C12 107.8(2) . . ?
N1 C17 C16 111.6(2) . . ?
N1 C17 C20 110.3(2) . . ?
C16 C17 C12 97.57(19) . . ?
C20 C17 C12 111.5(2) . . ?
C20 C17 C16 117.2(2) . . ?
O2 C18 N1 122.5(3) . . ?
O2 C18 C19 121.9(2) . . ?
N1 C18 C19 115.6(2) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C17 122.1(2) . . ?
C28 C20 C17 120.6(2) . . ?
C28 C20 C21 116.9(2) . . ?
C20 C21 C22 132.0(2) . . ?
C25 C21 C20 119.8(2) . . ?
C25 C21 C22 108.2(2) . . ?
C21 C22 H22A 111.1 . . ?
C21 C22 H22B 111.1 . . ?
C21 C22 C23 103.4(2) . . ?
H22A C22 H22B 109.0 . . ?
C23 C22 H22A 111.1 . . ?
C23 C22 H22B 111.1 . . ?
C22 C23 H23A 110.8 . . ?
C22 C23 H23B 110.8 . . ?
H23A C23 H23B 108.8 . . ?
C24 C23 C22 105.0(2) . . ?
C24 C23 H23A 110.8 . . ?
C24 C23 H23B 110.8 . . ?
C25 C24 C23 101.5(2) . . ?
C25 C24 C29 113.2(2) . . ?
C25 C24 C30 109.2(2) . . ?
C29 C24 C23 111.5(2) . . ?
C29 C24 C30 110.3(2) . . ?
C30 C24 C23 110.8(2) . . ?
C21 C25 C24 112.3(2) . . ?
C26 C25 C21 121.9(2) . . ?
C26 C25 C24 125.9(2) . . ?
C25 C26 H26 120.1 . . ?
C25 C26 C27 119.8(2) . . ?
C27 C26 H26 120.1 . . ?
C26 C27 C28 117.7(2) . . ?
C26 C27 C31 123.4(2) . . ?
C28 C27 C31 118.9(2) . . ?
C20 C28 C27 123.8(2) . . ?
C20 C28 H28 118.1 . . ?
C27 C28 H28 118.1 . . ?
C24 C29 H29A 109.5 . . ?
C24 C29 H29B 109.5 . . ?
C24 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C24 C30 H30A 109.5 . . ?
C24 C30 H30B 109.5 . . ?
C24 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C27 C31 C33 109.2(2) . . ?
C27 C31 C34 112.2(2) . . ?
C32 C31 C27 109.9(2) . . ?
C32 C31 C33 109.0(2) . . ?
C32 C31 C34 108.6(3) . . ?
C34 C31 C33 107.8(2) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C31 C33 H33A 109.5 . . ?
C31 C33 H33B 109.5 . . ?
C31 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C31 C34 H34A 109.5 . . ?
C31 C34 H34B 109.5 . . ?
C31 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 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
O1 C11 C12 C13 39.9(3) . . . . ?
O1 C11 C12 C15 146.2(3) . . . . ?
O1 C11 C12 C17 -81.0(3) . . . . ?
N1 C17 C20 C21 -39.7(3) . . . . ?
N1 C17 C20 C28 146.9(2) . . . . ?
C1 C2 C3 C4 -0.4(4) . . . . ?
C1 C6 C7 C8 -1.3(4) . . . . ?
C2 C1 C6 C5 0.8(4) . . . . ?
C2 C1 C6 C7 179.7(2) . . . . ?
C2 C1 C10 C9 -178.2(3) . . . . ?
C2 C3 C4 C5 0.6(4) . . . . ?
C3 C4 C5 C6 -0.1(4) . . . . ?
C4 C5 C6 C1 -0.6(4) . . . . ?
C4 C5 C6 C7 -179.4(3) . . . . ?
C5 C6 C7 C8 177.5(3) . . . . ?
C6 C1 C2 C3 -0.4(4) . . . . ?
C6 C1 C10 C9 1.8(4) . . . . ?
C6 C7 C8 C9 1.5(4) . . . . ?
C6 C7 C8 C11 -174.4(2) . . . . ?
C7 C8 C9 C10 0.0(4) . . . . ?
C7 C8 C11 O1 165.6(2) . . . . ?
C7 C8 C11 C12 -12.4(4) . . . . ?
C8 C9 C10 C1 -1.6(4) . . . . ?
C8 C11 C12 C13 -142.0(2) . . . . ?
C8 C11 C12 C15 -35.7(4) . . . . ?
C8 C11 C12 C17 97.1(3) . . . . ?
C9 C8 C11 O1 -10.4(4) . . . . ?
C9 C8 C11 C12 171.6(2) . . . . ?
C10 C1 C2 C3 179.6(3) . . . . ?
C10 C1 C6 C5 -179.2(2) . . . . ?
C10 C1 C6 C7 -0.3(4) . . . . ?
C11 C8 C9 C10 176.0(2) . . . . ?
C11 C12 C13 C14 165.1(2) . . . . ?
C11 C12 C15 C14 -155.1(3) . . . . ?
C11 C12 C17 N1 54.6(3) . . . . ?
C11 C12 C17 C16 170.2(2) . . . . ?
C11 C12 C17 C20 -66.5(3) . . . . ?
C12 C13 C14 C15 -34.86(18) . . . . ?
C12 C13 C14 C16 68.0(2) . . . . ?
C12 C17 C20 C21 79.9(3) . . . . ?
C12 C17 C20 C28 -93.5(3) . . . . ?
C13 C12 C15 C14 -34.68(17) . . . . ?
C13 C12 C17 N1 -73.5(2) . . . . ?
C13 C12 C17 C16 42.2(2) . . . . ?
C13 C12 C17 C20 165.4(2) . . . . ?
C13 C14 C15 C12 34.94(18) . . . . ?
C13 C14 C16 C17 -46.9(2) . . . . ?
C14 C16 C17 N1 115.0(2) . . . . ?
C14 C16 C17 C12 2.5(2) . . . . ?
C14 C16 C17 C20 -116.4(2) . . . . ?
C15 C12 C13 C14 34.78(18) . . . . ?
C15 C12 C17 N1 -161.8(2) . . . . ?
C15 C12 C17 C16 -46.2(2) . . . . ?
C15 C12 C17 C20 77.0(2) . . . . ?
C15 C14 C16 C17 42.1(2) . . . . ?
C16 C14 C15 C12 -65.7(2) . . . . ?
C16 C17 C20 C21 -168.9(2) . . . . ?
C16 C17 C20 C28 17.7(3) . . . . ?
C17 N1 C18 O2 -10.4(4) . . . . ?
C17 N1 C18 C19 169.9(2) . . . . ?
C17 C12 C13 C14 -66.3(2) . . . . ?
C17 C12 C15 C14 66.8(2) . . . . ?
C17 C20 C21 C22 9.9(4) . . . . ?
C17 C20 C21 C25 -170.9(2) . . . . ?
C17 C20 C28 C27 171.8(2) . . . . ?
C18 N1 C17 C12 173.8(2) . . . . ?
C18 N1 C17 C16 67.8(3) . . . . ?
C18 N1 C17 C20 -64.4(3) . . . . ?
C20 C21 C22 C23 -161.7(3) . . . . ?
C20 C21 C25 C24 -179.8(2) . . . . ?
C20 C21 C25 C26 -1.4(4) . . . . ?
C21 C20 C28 C27 -2.0(4) . . . . ?
C21 C22 C23 C24 -30.0(3) . . . . ?
C21 C25 C26 C27 -1.1(4) . . . . ?
C22 C21 C25 C24 -0.4(3) . . . . ?
C22 C21 C25 C26 178.0(2) . . . . ?
C22 C23 C24 C25 29.1(3) . . . . ?
C22 C23 C24 C29 149.9(2) . . . . ?
C22 C23 C24 C30 -86.8(3) . . . . ?
C23 C24 C25 C21 -18.3(3) . . . . ?
C23 C24 C25 C26 163.4(2) . . . . ?
C24 C25 C26 C27 177.1(2) . . . . ?
C25 C21 C22 C23 19.0(3) . . . . ?
C25 C26 C27 C28 1.9(4) . . . . ?
C25 C26 C27 C31 -178.0(2) . . . . ?
C26 C27 C28 C20 -0.4(4) . . . . ?
C26 C27 C31 C32 -123.1(3) . . . . ?
C26 C27 C31 C33 117.4(3) . . . . ?
C26 C27 C31 C34 -2.1(4) . . . . ?
C28 C20 C21 C22 -176.4(2) . . . . ?
C28 C20 C21 C25 2.8(4) . . . . ?
C28 C27 C31 C32 57.0(3) . . . . ?
C28 C27 C31 C33 -62.5(3) . . . . ?
C28 C27 C31 C34 178.0(3) . . . . ?
C29 C24 C25 C21 -137.9(2) . . . . ?
C29 C24 C25 C26 43.8(3) . . . . ?
C30 C24 C25 C21 98.7(3) . . . . ?
C30 C24 C25 C26 -79.6(3) . . . . ?
C31 C27 C28 C20 179.5(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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2426057'
loop_
_audit_author_name
_audit_author_address
'Yanren Zhu'
;Yunnan University
China
;
_audit_update_record             
;
2025-02-22 deposited with the CCDC.	2025-06-24 downloaded from the CCDC.
;
_audit_creation_date             2025-01-13
_audit_creation_method           
;
FinalCif V89 by Daniel Kratzert, Freiburg 2025,
https://dkratzert.de/finalcif.html
;
_shelx_SHELXL_version_number     2018/3
_diffrn_source_power             0.07
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C22 H17 Br N O3'
_chemical_formula_moiety         'C22 H17 Br N O3'
_chemical_formula_weight         423.27
_chemical_melting_point          ?
_exptl_crystal_colour_primary    colourless
_chemical_absolute_configuration unk
_space_group_crystal_system      monoclinic
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.932(15)
 0.068(15)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3.a Riding coordinates:
 O1(H1), N1(H1A)
3.b Ternary CH refined with riding coordinates:
 C7(H7), C12(H12)
3.c Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
3.d Aromatic/amide H refined with riding coordinates:
 C1(H1B), C2(H2), C4(H4), C5(H5), C15(H15), C16(H16), C17(H17), C18(H18)
3.e Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'
_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'

_cell_length_a                   7.4907(3)
_cell_length_b                   15.9278(7)
_cell_length_c                   7.9606(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.271(2)
_cell_angle_gamma                90
_cell_volume                     931.46(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.00
_cell_measurement_reflns_used    8338
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      27.50
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_F_000             430
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    2.229
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6050
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1575 before and 0.0811 after correction.
The Ratio of minimum to maximum transmission is 0.8114.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      100.15
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'mirror optics'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_diffrn_measurement_ambient_temperature_device_make ?
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_source_current           1.4
_diffrn_detector                 CPAD
_diffrn_detector_type            'Bruker PHOTON'
_diffrn_detector_area_resol_mean 7.41
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            10558
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_theta_min         2.558
_diffrn_reflns_theta_max         27.511
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_standards_number         0
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.859
_diffrn_reflns_point_group_measured_fraction_full 0.876
_reflns_number_total             3685
_reflns_number_gt                3488
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.661
_reflns_Friedel_fraction_max     0.710
_reflns_Friedel_fraction_full    0.744
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.40B'
_computing_data_reduction        'SAINT V8.40B'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0367P)²+1.2286P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3685
_refine_ls_number_parameters     246
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.0948
_refine_ls_wR_factor_gt          0.0926
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_restrained_S_all      1.110
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.489
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_Flack   0.068(15)
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;

loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.932(15)
2 0.068(15)

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'

_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_
_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 0.94040(6) 0.76655(4) 1.02483(6) 0.02033(14) Uani 1 1 d . . . . .
O1 O 1.0077(5) 0.3790(2) 0.6750(5) 0.0159(7) Uani 1 1 d . . . . .
H1 H 1.068616 0.345896 0.626364 0.024 Uiso 1 1 d R U . . .
O2 O 0.3388(5) 0.5277(3) 0.3006(5) 0.0200(8) Uani 1 1 d . . . . .
O3 O 0.3250(5) 0.3214(2) 0.5930(5) 0.0184(8) Uani 1 1 d . . . . .
N1 N 0.6265(5) 0.3397(3) 0.6098(5) 0.0126(8) Uani 1 1 d . . . . .
H1A H 0.737720 0.321108 0.647178 0.015 Uiso 1 1 d R U . . .
C1 C 0.8931(6) 0.6064(3) 0.6057(6) 0.0139(10) Uani 1 1 d . . . . .
H1B H 0.856083 0.610568 0.484853 0.017 Uiso 1 1 calc R U . . .
C2 C 0.8879(7) 0.6770(3) 0.7061(7) 0.0159(10) Uani 1 1 d . . . . .
H2 H 0.844935 0.729024 0.655133 0.019 Uiso 1 1 calc R U . . .
C3 C 0.9467(7) 0.6708(3) 0.8829(6) 0.0157(10) Uani 1 1 d . . . . .
C4 C 1.0124(7) 0.5960(4) 0.9597(7) 0.0178(10) Uani 1 1 d . . . . .
H4 H 1.055609 0.592911 1.079925 0.021 Uiso 1 1 calc R U . . .
C5 C 1.0137(7) 0.5251(3) 0.8566(6) 0.0159(10) Uani 1 1 d . . . . .
H5 H 1.057470 0.473295 0.907886 0.019 Uiso 1 1 calc R U . . .
C6 C 0.9519(6) 0.5291(3) 0.6794(6) 0.0135(9) Uani 1 1 d . . . . .
C7 C 0.9616(6) 0.4524(3) 0.5698(6) 0.0131(10) Uani 1 1 d . . . . .
H7 H 1.062454 0.461883 0.506125 0.016 Uiso 1 1 calc R U . . .
C8 C 0.7907(7) 0.4318(3) 0.4377(6) 0.0130(9) Uani 1 1 d . . . . .
C9 C 0.7286(7) 0.4861(4) 0.2718(6) 0.0178(11) Uani 1 1 d . . . . .
C10 C 0.6382(7) 0.4022(4) 0.2017(7) 0.0184(11) Uani 1 1 d . . . . .
C11 C 0.8025(7) 0.3573(4) 0.3137(7) 0.0183(11) Uani 1 1 d . . . . .
C12 C 0.4903(7) 0.3889(3) 0.3088(6) 0.0159(10) Uani 1 1 d . . . . .
H12 H 0.457554 0.328037 0.306687 0.019 Uiso 1 1 calc R U . . .
C13 C 0.3189(7) 0.4399(4) 0.2554(7) 0.0199(11) Uani 1 1 d . . . . .
H13A H 0.278368 0.435233 0.129708 0.024 Uiso 1 1 calc R U . . .
H13B H 0.222281 0.415485 0.309282 0.024 Uiso 1 1 calc R U . . .
C14 C 0.3987(7) 0.5406(3) 0.4735(7) 0.0147(10) Uani 1 1 d . . . . .
C15 C 0.3336(7) 0.6113(4) 0.5449(7) 0.0186(11) Uani 1 1 d . . . . .
H15 H 0.252822 0.648883 0.475091 0.022 Uiso 1 1 calc R U . . .
C16 C 0.3885(7) 0.6264(4) 0.7206(7) 0.0194(11) Uani 1 1 d . . . . .
H16 H 0.348204 0.675475 0.769957 0.023 Uiso 1 1 calc R U . . .
C17 C 0.5014(7) 0.5699(3) 0.8225(7) 0.0170(10) Uani 1 1 d . . . . .
H17 H 0.533906 0.578824 0.942641 0.020 Uiso 1 1 calc R U . . .
C18 C 0.5672(7) 0.5001(3) 0.7491(6) 0.0147(10) Uani 1 1 d . . . . .
H18 H 0.645512 0.461985 0.820208 0.018 Uiso 1 1 calc R U . . .
C19 C 0.5208(6) 0.4845(3) 0.5726(6) 0.0130(10) Uani 1 1 d . . . . .
C20 C 0.6030(7) 0.4117(3) 0.4916(6) 0.0129(10) Uani 1 1 d . . . . .
C21 C 0.4829(7) 0.3021(3) 0.6576(6) 0.0139(10) Uani 1 1 d . . . . .
C22 C 0.5243(7) 0.2347(3) 0.7918(7) 0.0187(11) Uani 1 1 d . . . . .
H22A H 0.476119 0.251223 0.892865 0.028 Uiso 1 1 calc R U . . .
H22B H 0.656301 0.226880 0.824053 0.028 Uiso 1 1 calc R U . . .
H22C H 0.467242 0.181914 0.745918 0.028 Uiso 1 1 calc R U . . .


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 C3 1.904(5) . ?
O1 H1 0.8398 . ?
O1 C7 1.441(6) . ?
O2 C13 1.444(7) . ?
O2 C14 1.377(6) . ?
O3 C21 1.233(6) . ?
N1 H1A 0.8797 . ?
N1 C20 1.472(6) . ?
N1 C21 1.348(6) . ?
C1 H1B 0.9500 . ?
C1 C2 1.385(7) . ?
C1 C6 1.398(7) . ?
C2 H2 0.9500 . ?
C2 C3 1.394(7) . ?
C3 C4 1.385(8) . ?
C4 H4 0.9500 . ?
C4 C5 1.396(8) . ?
C5 H5 0.9500 . ?
C5 C6 1.397(7) . ?
C6 C7 1.511(7) . ?
C7 H7 1.0000 . ?
C7 C8 1.526(7) . ?
C8 C9 1.571(7) . ?
C8 C11 1.556(7) . ?
C8 C20 1.581(7) . ?
C9 C10 1.551(8) . ?
C10 C11 1.547(8) . ?
C10 C12 1.539(7) . ?
C12 H12 1.0000 . ?
C12 C13 1.508(7) . ?
C12 C20 1.574(7) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.391(7) . ?
C14 C19 1.405(7) . ?
C15 H15 0.9500 . ?
C15 C16 1.400(8) . ?
C16 H16 0.9500 . ?
C16 C17 1.384(8) . ?
C17 H17 0.9500 . ?
C17 C18 1.391(7) . ?
C18 H18 0.9500 . ?
C18 C19 1.402(7) . ?
C19 C20 1.516(7) . ?
C21 C22 1.504(7) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

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 O1 H1 109.4 . . ?
C14 O2 C13 113.1(4) . . ?
C20 N1 H1A 117.7 . . ?
C21 N1 H1A 120.7 . . ?
C21 N1 C20 121.6(4) . . ?
C2 C1 H1B 119.5 . . ?
C2 C1 C6 121.0(5) . . ?
C6 C1 H1B 119.5 . . ?
C1 C2 H2 120.5 . . ?
C1 C2 C3 119.0(5) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 Br1 120.1(4) . . ?
C4 C3 Br1 118.4(4) . . ?
C4 C3 C2 121.5(5) . . ?
C3 C4 H4 120.7 . . ?
C3 C4 C5 118.6(5) . . ?
C5 C4 H4 120.7 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.2(5) . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C7 121.1(4) . . ?
C5 C6 C1 118.6(5) . . ?
C5 C6 C7 120.2(5) . . ?
O1 C7 C6 110.7(4) . . ?
O1 C7 H7 107.3 . . ?
O1 C7 C8 107.4(4) . . ?
C6 C7 H7 107.3 . . ?
C6 C7 C8 116.4(4) . . ?
C8 C7 H7 107.3 . . ?
C7 C8 C9 122.1(4) . . ?
C7 C8 C11 117.2(4) . . ?
C7 C8 C20 121.8(4) . . ?
C9 C8 C20 101.9(4) . . ?
C11 C8 C9 86.0(4) . . ?
C11 C8 C20 100.5(4) . . ?
C10 C9 C8 82.3(4) . . ?
C11 C10 C9 87.0(4) . . ?
C12 C10 C9 103.2(4) . . ?
C12 C10 C11 101.2(4) . . ?
C10 C11 C8 82.9(4) . . ?
C10 C12 H12 108.9 . . ?
C10 C12 C20 99.6(4) . . ?
C13 C12 C10 115.8(5) . . ?
C13 C12 H12 108.9 . . ?
C13 C12 C20 114.2(4) . . ?
C20 C12 H12 108.9 . . ?
O2 C13 C12 114.2(4) . . ?
O2 C13 H13A 108.7 . . ?
O2 C13 H13B 108.7 . . ?
C12 C13 H13A 108.7 . . ?
C12 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
O2 C14 C15 117.2(5) . . ?
O2 C14 C19 121.0(5) . . ?
C15 C14 C19 121.8(5) . . ?
C14 C15 H15 120.3 . . ?
C14 C15 C16 119.3(5) . . ?
C16 C15 H15 120.3 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 120.0(5) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C18 120.0(5) . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 119.2 . . ?
C17 C18 C19 121.5(5) . . ?
C19 C18 H18 119.2 . . ?
C14 C19 C20 121.4(5) . . ?
C18 C19 C14 117.2(5) . . ?
C18 C19 C20 121.3(4) . . ?
N1 C20 C8 109.3(4) . . ?
N1 C20 C12 112.8(4) . . ?
N1 C20 C19 109.4(4) . . ?
C12 C20 C8 98.1(4) . . ?
C19 C20 C8 114.6(4) . . ?
C19 C20 C12 112.4(4) . . ?
O3 C21 N1 121.7(5) . . ?
O3 C21 C22 121.4(4) . . ?
N1 C21 C22 116.9(4) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

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
_geom_hbond_publ_flag
O1 H1 O3 0.84 2.03 2.743(5) 142.7 1_655 yes
N1 H1A O1 0.88 2.19 2.870(5) 133.4 . yes

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
Br1 C3 C4 C5 178.7(4) . . . . ?
O1 C7 C8 C9 -163.4(4) . . . . ?
O1 C7 C8 C11 -60.0(5) . . . . ?
O1 C7 C8 C20 64.0(6) . . . . ?
O2 C14 C15 C16 179.0(5) . . . . ?
O2 C14 C19 C18 -176.7(4) . . . . ?
O2 C14 C19 C20 4.9(8) . . . . ?
C1 C2 C3 Br1 -179.7(4) . . . . ?
C1 C2 C3 C4 1.0(7) . . . . ?
C1 C6 C7 O1 -174.1(4) . . . . ?
C1 C6 C7 C8 -51.1(6) . . . . ?
C2 C1 C6 C5 -2.9(7) . . . . ?
C2 C1 C6 C7 -178.6(4) . . . . ?
C2 C3 C4 C5 -2.0(7) . . . . ?
C3 C4 C5 C6 0.5(7) . . . . ?
C4 C5 C6 C1 1.9(7) . . . . ?
C4 C5 C6 C7 177.6(4) . . . . ?
C5 C6 C7 O1 10.3(6) . . . . ?
C5 C6 C7 C8 133.3(5) . . . . ?
C6 C1 C2 C3 1.6(7) . . . . ?
C6 C7 C8 C9 72.0(6) . . . . ?
C6 C7 C8 C11 175.3(4) . . . . ?
C6 C7 C8 C20 -60.6(6) . . . . ?
C7 C8 C9 C10 153.9(5) . . . . ?
C7 C8 C11 C10 -158.5(4) . . . . ?
C7 C8 C20 N1 -57.9(6) . . . . ?
C7 C8 C20 C12 -175.5(5) . . . . ?
C7 C8 C20 C19 65.3(6) . . . . ?
C8 C9 C10 C11 -34.3(3) . . . . ?
C8 C9 C10 C12 66.6(4) . . . . ?
C9 C8 C11 C10 -34.1(3) . . . . ?
C9 C8 C20 N1 161.7(4) . . . . ?
C9 C8 C20 C12 44.0(5) . . . . ?
C9 C8 C20 C19 -75.1(5) . . . . ?
C9 C10 C11 C8 34.6(3) . . . . ?
C9 C10 C12 C13 78.6(5) . . . . ?
C9 C10 C12 C20 -44.4(5) . . . . ?
C10 C12 C13 O2 -74.2(6) . . . . ?
C10 C12 C20 N1 -115.2(4) . . . . ?
C10 C12 C20 C8 -0.3(5) . . . . ?
C10 C12 C20 C19 120.6(4) . . . . ?
C11 C8 C9 C10 34.1(3) . . . . ?
C11 C8 C20 N1 73.6(5) . . . . ?
C11 C8 C20 C12 -44.1(5) . . . . ?
C11 C8 C20 C19 -163.2(4) . . . . ?
C11 C10 C12 C13 168.1(4) . . . . ?
C11 C10 C12 C20 45.2(5) . . . . ?
C12 C10 C11 C8 -68.3(4) . . . . ?
C13 O2 C14 C15 -146.0(5) . . . . ?
C13 O2 C14 C19 34.1(7) . . . . ?
C13 C12 C20 N1 120.7(5) . . . . ?
C13 C12 C20 C8 -124.4(5) . . . . ?
C13 C12 C20 C19 -3.5(6) . . . . ?
C14 O2 C13 C12 -57.2(6) . . . . ?
C14 C15 C16 C17 -2.2(8) . . . . ?
C14 C19 C20 N1 -145.6(5) . . . . ?
C14 C19 C20 C8 91.3(6) . . . . ?
C14 C19 C20 C12 -19.6(7) . . . . ?
C15 C14 C19 C18 3.4(8) . . . . ?
C15 C14 C19 C20 -174.9(4) . . . . ?
C15 C16 C17 C18 3.0(8) . . . . ?
C16 C17 C18 C19 -0.6(8) . . . . ?
C17 C18 C19 C14 -2.6(8) . . . . ?
C17 C18 C19 C20 175.8(5) . . . . ?
C18 C19 C20 N1 36.1(6) . . . . ?
C18 C19 C20 C8 -87.0(6) . . . . ?
C18 C19 C20 C12 162.1(4) . . . . ?
C19 C14 C15 C16 -1.1(8) . . . . ?
C20 N1 C21 O3 6.5(7) . . . . ?
C20 N1 C21 C22 -174.3(4) . . . . ?
C20 C8 C9 C10 -65.8(4) . . . . ?
C20 C8 C11 C10 67.3(4) . . . . ?
C20 C12 C13 O2 40.6(6) . . . . ?
C21 N1 C20 C8 -170.9(4) . . . . ?
C21 N1 C20 C12 -62.9(6) . . . . ?
C21 N1 C20 C19 62.9(6) . . . . ?

