# Supplementary Information (SI) for Chemical Science.
# 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_D21009
_database_code_depnum_ccdc_archive 'CCDC 2253010'
loop_
_audit_author_name
_audit_author_address
'Michael Takase '
;California Institute of Technology
United States of America
;
_audit_update_record             
;
2023-03-30 deposited with the CCDC.	2025-05-01 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 H23 Br N2 O2'
_chemical_formula_weight         415.32

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'
Br Br -0.2901 2.4595 '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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   9.430(3)
_cell_length_b                   9.489(2)
_cell_length_c                   21.189(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.651(18)
_cell_angle_gamma                90
_cell_volume                     1892.2(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9840
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      36.33

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    2.190
_shelx_estimated_absorpt_T_min   0.407
_shelx_estimated_absorpt_T_max   0.560
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5241
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_process_details   'SADABS-2016/2 (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 KAPPA'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            53031
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         1.926
_diffrn_reflns_theta_max         36.430
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             9140
_reflns_number_gt                7953
_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       'APEX3 v2019.1-0 (Bruker Nano, 2019)'
_computing_cell_refinement       'SAINT v8.40A (Bruker-AXS, 2013)'
_computing_data_reduction        'SAINT v8.40A (Bruker-AXS, 2013)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0351P)²+0.7206P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9140
_refine_ls_number_parameters     242
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0267
_refine_ls_wR_factor_ref         0.0710
_refine_ls_wR_factor_gt          0.0680
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.002
_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 0.82297(8) 0.66550(8) 0.54410(3) 0.01398(12) Uani 1 1 d . . . . .
C1 C 0.84418(9) 0.79183(9) 0.51543(4) 0.01280(13) Uani 1 1 d . . . . .
O1 O 0.88193(8) 0.90106(7) 0.54220(3) 0.01708(12) Uani 1 1 d . . . . .
C2 C 0.80703(9) 0.77763(9) 0.44456(4) 0.01249(13) Uani 1 1 d . . . . .
C5 C 0.66791(9) 0.86024(10) 0.42948(4) 0.01606(15) Uani 1 1 d . . . . .
H5A H 0.687346 0.962084 0.435359 0.019 Uiso 1 1 calc R U . . .
H5B H 0.636832 0.845184 0.384474 0.019 Uiso 1 1 calc R U . . .
C6 C 0.54918(10) 0.81919(11) 0.46950(5) 0.01779(15) Uani 1 1 d . . . . .
H6 H 0.561554 0.835701 0.513727 0.021 Uiso 1 1 calc R U . . .
C7 C 0.42820(11) 0.76148(12) 0.44739(5) 0.02201(18) Uani 1 1 d . . . . .
H7A H 0.412297 0.743506 0.403407 0.026 Uiso 1 1 calc R U . . .
H7B H 0.357296 0.738028 0.475521 0.026 Uiso 1 1 calc R U . . .
C8 C 0.92944(9) 0.84374(9) 0.40885(4) 0.01223(13) Uani 1 1 d . . . . .
H8 H 0.931961 0.947098 0.418050 0.015 Uiso 1 1 calc R U . . .
N2 N 1.06508(9) 0.78203(9) 0.43378(4) 0.01673(13) Uani 1 1 d D . . . .
H2N1 H 1.1033(16) 0.8353(16) 0.4651(7) 0.025 Uiso 1 1 d D U . . .
H2N2 H 1.1345(16) 0.7879(17) 0.4060(8) 0.025 Uiso 1 1 d D U . . .
C3 C 0.79078(11) 0.61812(9) 0.43513(4) 0.01647(15) Uani 1 1 d . . . . .
H3A H 0.709923 0.597048 0.404475 0.020 Uiso 1 1 calc R U . . .
H3B H 0.878286 0.577402 0.419162 0.020 Uiso 1 1 calc R U . . .
C4 C 0.76391(10) 0.55764(9) 0.50033(4) 0.01598(15) Uani 1 1 d . . . . .
H4A H 0.661032 0.544240 0.505108 0.019 Uiso 1 1 calc R U . . .
H4B H 0.813248 0.466348 0.507329 0.019 Uiso 1 1 calc R U . . .
C11 C 0.83284(9) 0.64494(9) 0.61043(4) 0.01345(13) Uani 1 1 d . . . . .
C12 C 0.73258(10) 0.56311(10) 0.63875(4) 0.01637(15) Uani 1 1 d . . . . .
H12 H 0.657347 0.521354 0.613289 0.020 Uiso 1 1 calc R U . . .
C13 C 0.74060(10) 0.54127(10) 0.70397(4) 0.01716(15) Uani 1 1 d . . . . .
H13 H 0.671885 0.484419 0.722776 0.021 Uiso 1 1 calc R U . . .
C14 C 0.85002(9) 0.60341(9) 0.74121(4) 0.01463(14) Uani 1 1 d . . . . .
O2 O 0.86951(8) 0.58805(8) 0.80526(3) 0.01877(13) Uani 1 1 d . . . . .
C17 C 0.77994(11) 0.48892(11) 0.83447(5) 0.02139(17) Uani 1 1 d . . . . .
H17A H 0.680523 0.518208 0.827469 0.032 Uiso 1 1 calc R U . . .
H17B H 0.805635 0.485246 0.879993 0.032 Uiso 1 1 calc R U . . .
H17C H 0.792324 0.395428 0.815966 0.032 Uiso 1 1 calc R U . . .
C15 C 0.95137(10) 0.68526(10) 0.71295(4) 0.01615(14) Uani 1 1 d . . . . .
H15 H 1.026240 0.727538 0.738434 0.019 Uiso 1 1 calc R U . . .
C16 C 0.94373(10) 0.70539(10) 0.64804(4) 0.01595(15) Uani 1 1 d . . . . .
H16 H 1.013858 0.760250 0.629134 0.019 Uiso 1 1 calc R U . . .
C21 C 0.90931(9) 0.82469(9) 0.33794(4) 0.01191(13) Uani 1 1 d . . . . .
C22 C 0.95359(10) 0.70227(9) 0.30795(4) 0.01451(14) Uani 1 1 d . . . . .
H22 H 0.997002 0.628590 0.332625 0.017 Uiso 1 1 calc R U . . .
C23 C 0.93511(10) 0.68671(9) 0.24270(4) 0.01485(14) Uani 1 1 d . . . . .
H23 H 0.964576 0.602794 0.222888 0.018 Uiso 1 1 calc R U . . .
C24 C 0.87309(9) 0.79535(9) 0.20696(4) 0.01382(14) Uani 1 1 d . . . . .
Br1 Br 0.85221(2) 0.77388(2) 0.11778(2) 0.01928(3) Uani 1 1 d . . . . .
C25 C 0.82861(10) 0.91871(9) 0.23495(4) 0.01621(15) Uani 1 1 d . . . . .
H25 H 0.786327 0.992478 0.209958 0.019 Uiso 1 1 calc R U . . .
C26 C 0.84727(10) 0.93195(9) 0.30034(4) 0.01483(14) Uani 1 1 d . . . . .
H26 H 0.817123 1.015918 0.319901 0.018 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 C1 1.3643(11) . ?
N1 C11 1.4161(12) . ?
N1 C4 1.4671(12) . ?
C1 O1 1.2236(10) . ?
C1 C2 1.5262(13) . ?
C2 C3 1.5333(12) . ?
C2 C5 1.5441(13) . ?
C2 C8 1.5522(12) . ?
C5 C6 1.4984(13) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.3239(14) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9500 . ?
C7 H7B 0.9500 . ?
C8 N2 1.4736(12) . ?
C8 C21 1.5133(12) . ?
C8 H8 1.0000 . ?
N2 H2N1 0.892(13) . ?
N2 H2N2 0.909(14) . ?
C3 C4 1.5319(13) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C11 C12 1.3890(12) . ?
C11 C16 1.3969(13) . ?
C12 C13 1.3948(13) . ?
C12 H12 0.9500 . ?
C13 C14 1.3896(14) . ?
C13 H13 0.9500 . ?
C14 O2 1.3658(11) . ?
C14 C15 1.3956(13) . ?
O2 C17 1.4311(13) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C15 C16 1.3860(13) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C21 C26 1.3978(12) . ?
C21 C22 1.4005(12) . ?
C22 C23 1.3903(13) . ?
C22 H22 0.9500 . ?
C23 C24 1.3864(13) . ?
C23 H23 0.9500 . ?
C24 C25 1.3891(12) . ?
C24 Br1 1.8983(10) . ?
C25 C26 1.3912(13) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?

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 C11 124.10(7) . . ?
C1 N1 C4 113.08(7) . . ?
C11 N1 C4 121.98(7) . . ?
O1 C1 N1 125.77(8) . . ?
O1 C1 C2 124.93(8) . . ?
N1 C1 C2 109.24(7) . . ?
C1 C2 C3 103.31(7) . . ?
C1 C2 C5 107.31(7) . . ?
C3 C2 C5 113.44(7) . . ?
C1 C2 C8 108.23(7) . . ?
C3 C2 C8 114.00(7) . . ?
C5 C2 C8 110.02(7) . . ?
C6 C5 C2 113.98(8) . . ?
C6 C5 H5A 108.8 . . ?
C2 C5 H5A 108.8 . . ?
C6 C5 H5B 108.8 . . ?
C2 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
C7 C6 C5 124.43(9) . . ?
C7 C6 H6 117.8 . . ?
C5 C6 H6 117.8 . . ?
C6 C7 H7A 120.0 . . ?
C6 C7 H7B 120.0 . . ?
H7A C7 H7B 120.0 . . ?
N2 C8 C21 111.07(7) . . ?
N2 C8 C2 108.67(7) . . ?
C21 C8 C2 112.68(7) . . ?
N2 C8 H8 108.1 . . ?
C21 C8 H8 108.1 . . ?
C2 C8 H8 108.1 . . ?
C8 N2 H2N1 110.0(10) . . ?
C8 N2 H2N2 112.8(11) . . ?
H2N1 N2 H2N2 100.0(14) . . ?
C4 C3 C2 105.86(7) . . ?
C4 C3 H3A 110.6 . . ?
C2 C3 H3A 110.6 . . ?
C4 C3 H3B 110.6 . . ?
C2 C3 H3B 110.6 . . ?
H3A C3 H3B 108.7 . . ?
N1 C4 C3 103.35(7) . . ?
N1 C4 H4A 111.1 . . ?
C3 C4 H4A 111.1 . . ?
N1 C4 H4B 111.1 . . ?
C3 C4 H4B 111.1 . . ?
H4A C4 H4B 109.1 . . ?
C12 C11 C16 119.25(8) . . ?
C12 C11 N1 120.15(8) . . ?
C16 C11 N1 120.60(8) . . ?
C11 C12 C13 121.04(8) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C14 C13 C12 119.40(8) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
O2 C14 C13 124.54(8) . . ?
O2 C14 C15 115.67(8) . . ?
C13 C14 C15 119.77(8) . . ?
C14 O2 C17 117.01(8) . . ?
O2 C17 H17A 109.5 . . ?
O2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C15 C14 120.58(8) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C11 119.95(8) . . ?
C15 C16 H16 120.0 . . ?
C11 C16 H16 120.0 . . ?
C26 C21 C22 118.13(8) . . ?
C26 C21 C8 120.03(7) . . ?
C22 C21 C8 121.83(8) . . ?
C23 C22 C21 121.14(8) . . ?
C23 C22 H22 119.4 . . ?
C21 C22 H22 119.4 . . ?
C24 C23 C22 119.08(8) . . ?
C24 C23 H23 120.5 . . ?
C22 C23 H23 120.5 . . ?
C23 C24 C25 121.45(8) . . ?
C23 C24 Br1 118.52(6) . . ?
C25 C24 Br1 120.03(7) . . ?
C24 C25 C26 118.61(8) . . ?
C24 C25 H25 120.7 . . ?
C26 C25 H25 120.7 . . ?
C25 C26 C21 121.58(8) . . ?
C25 C26 H26 119.2 . . ?
C21 C26 H26 119.2 . . ?

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
C11 N1 C1 O1 4.40(14) . . . . ?
C4 N1 C1 O1 174.10(9) . . . . ?
C11 N1 C1 C2 -173.11(8) . . . . ?
C4 N1 C1 C2 -3.42(10) . . . . ?
O1 C1 C2 C3 171.34(9) . . . . ?
N1 C1 C2 C3 -11.12(9) . . . . ?
O1 C1 C2 C5 -68.54(11) . . . . ?
N1 C1 C2 C5 109.00(8) . . . . ?
O1 C1 C2 C8 50.15(11) . . . . ?
N1 C1 C2 C8 -132.31(7) . . . . ?
C1 C2 C5 C6 -53.25(10) . . . . ?
C3 C2 C5 C6 60.20(10) . . . . ?
C8 C2 C5 C6 -170.78(8) . . . . ?
C2 C5 C6 C7 -116.39(11) . . . . ?
C1 C2 C8 N2 51.73(9) . . . . ?
C3 C2 C8 N2 -62.58(9) . . . . ?
C5 C2 C8 N2 168.70(7) . . . . ?
C1 C2 C8 C21 175.27(7) . . . . ?
C3 C2 C8 C21 60.95(10) . . . . ?
C5 C2 C8 C21 -67.77(9) . . . . ?
C1 C2 C3 C4 20.57(9) . . . . ?
C5 C2 C3 C4 -95.27(9) . . . . ?
C8 C2 C3 C4 137.77(8) . . . . ?
C1 N1 C4 C3 16.44(10) . . . . ?
C11 N1 C4 C3 -173.62(8) . . . . ?
C2 C3 C4 N1 -22.45(10) . . . . ?
C1 N1 C11 C12 137.17(9) . . . . ?
C4 N1 C11 C12 -31.65(13) . . . . ?
C1 N1 C11 C16 -43.40(13) . . . . ?
C4 N1 C11 C16 147.79(9) . . . . ?
C16 C11 C12 C13 0.39(14) . . . . ?
N1 C11 C12 C13 179.83(9) . . . . ?
C11 C12 C13 C14 0.55(15) . . . . ?
C12 C13 C14 O2 -179.15(9) . . . . ?
C12 C13 C14 C15 -0.80(14) . . . . ?
C13 C14 O2 C17 7.12(13) . . . . ?
C15 C14 O2 C17 -171.29(8) . . . . ?
O2 C14 C15 C16 178.62(8) . . . . ?
C13 C14 C15 C16 0.13(14) . . . . ?
C14 C15 C16 C11 0.81(14) . . . . ?
C12 C11 C16 C15 -1.06(14) . . . . ?
N1 C11 C16 C15 179.49(9) . . . . ?
N2 C8 C21 C26 -141.92(8) . . . . ?
C2 C8 C21 C26 95.89(9) . . . . ?
N2 C8 C21 C22 36.94(11) . . . . ?
C2 C8 C21 C22 -85.25(10) . . . . ?
C26 C21 C22 C23 -0.73(13) . . . . ?
C8 C21 C22 C23 -179.61(8) . . . . ?
C21 C22 C23 C24 0.71(13) . . . . ?
C22 C23 C24 C25 -0.30(14) . . . . ?
C22 C23 C24 Br1 178.74(7) . . . . ?
C23 C24 C25 C26 -0.06(14) . . . . ?
Br1 C24 C25 C26 -179.09(7) . . . . ?
C24 C25 C26 C21 0.03(14) . . . . ?
C22 C21 C26 C25 0.35(13) . . . . ?
C8 C21 C26 C25 179.25(8) . . . . ?

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
C8 H8 O1 1.00 2.38 3.1416(12) 132.1 3_776 yes
N2 H2N1 O1 0.892(13) 2.511(16) 3.0855(13) 122.6(13) 3_776 yes
C17 H17B O1 0.98 2.62 3.2190(14) 119.7 2_646 yes
C23 H23 O2 0.95 2.49 3.3858(13) 157.1 3_766 yes

_refine_diff_density_max         0.656
_refine_diff_density_min         -0.498
_refine_diff_density_rms         0.064

####################################################################### 
# 
# 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_V20240
_database_code_depnum_ccdc_archive 'CCDC 2253013'
loop_
_audit_author_name
_audit_author_address
'Michael K. Takase'
;California Institute of Technology
United States of America
;
_audit_update_record             
;
2023-03-30 deposited with the CCDC.	2025-05-01 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            'C27 H27 Br N2 O2'
_chemical_formula_weight         491.41

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                   11.8500(11)
_cell_length_b                   49.858(4)
_cell_length_c                   8.0771(10)
_cell_angle_alpha                90
_cell_angle_beta                 90.083(7)
_cell_angle_gamma                90
_cell_volume                     4772.1(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9071
_cell_measurement_theta_min      3.55
_cell_measurement_theta_max      74.40

_exptl_crystal_description       Plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_F_000             2032
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    2.548
_shelx_estimated_absorpt_T_min   0.515
_shelx_estimated_absorpt_T_max   0.883
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4919
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_process_details   'SADABS-2016/2 (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I\mS HB micro-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 7.69
_diffrn_reflns_number            75046
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_av_R_equivalents  0.0709
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -62
_diffrn_reflns_limit_k_max       62
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.546
_diffrn_reflns_theta_max         74.545
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             9652
_reflns_number_gt                8681
_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       'APEX3 v2019.1-0 (Bruker Nano, 2019)'
_computing_cell_refinement       'SAINT v8.40A (Bruker-AXS, 2013)'
_computing_data_reduction        'SAINT v8.40A (Bruker-AXS, 2013)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0469P)²+11.4189P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9652
_refine_ls_number_parameters     583
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0679
_refine_ls_wR_factor_ref         0.1686
_refine_ls_wR_factor_gt          0.1654
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_restrained_S_all      1.149
_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 0.3314(3) 0.13580(6) 0.2404(4) 0.0329(7) Uani 1 1 d . . . . .
C11 C 0.3013(3) 0.10879(7) 0.1978(5) 0.0312(7) Uani 1 1 d . . . . .
C12 C 0.2057(3) 0.10352(7) 0.1048(5) 0.0339(8) Uani 1 1 d . . . . .
H12 H 0.160761 0.117956 0.065407 0.041 Uiso 1 1 calc R U . . .
C13 C 0.1748(3) 0.07714(8) 0.0684(5) 0.0342(8) Uani 1 1 d . . . . .
H13 H 0.108638 0.073583 0.005570 0.041 Uiso 1 1 calc R U . . .
C14 C 0.2413(3) 0.05622(7) 0.1246(5) 0.0328(8) Uani 1 1 d . . . . .
O2 O 0.2215(2) 0.02946(5) 0.0957(4) 0.0424(7) Uani 1 1 d . . . . .
C17 C 0.1255(5) 0.02250(10) 0.0023(8) 0.0641(15) Uani 1 1 d . . . . .
H17A H 0.057624 0.028943 0.058836 0.096 Uiso 1 1 calc R U . . .
H17B H 0.121787 0.002959 -0.009348 0.096 Uiso 1 1 calc R U . . .
H17C H 0.130396 0.030761 -0.107538 0.096 Uiso 1 1 calc R U . . .
C15 C 0.3362(3) 0.06168(8) 0.2186(5) 0.0384(9) Uani 1 1 d . . . . .
H15 H 0.381224 0.047276 0.258121 0.046 Uiso 1 1 calc R U . . .
C16 C 0.3664(3) 0.08772(8) 0.2558(5) 0.0367(8) Uani 1 1 d . . . . .
H16 H 0.431597 0.091167 0.320992 0.044 Uiso 1 1 calc R U . . .
C1 C 0.2622(3) 0.15220(7) 0.3282(5) 0.0331(8) Uani 1 1 d . . . . .
O1 O 0.1619(2) 0.14877(5) 0.3541(4) 0.0397(6) Uani 1 1 d . . . . .
C2 C 0.3329(3) 0.17532(7) 0.3990(5) 0.0340(8) Uani 1 1 d . . . . .
C5 C 0.2701(4) 0.20183(8) 0.3839(6) 0.0463(10) Uani 1 1 d . . . . .
H5A H 0.249920 0.204947 0.267740 0.069 Uiso 1 1 calc R U . . .
H5B H 0.318584 0.216438 0.423053 0.069 Uiso 1 1 calc R U . . .
H5C H 0.201355 0.201172 0.451040 0.069 Uiso 1 1 calc R U . . .
C6 C 0.3497(3) 0.16783(7) 0.5860(5) 0.0309(7) Uani 1 1 d . . . . .
H6 H 0.274405 0.163129 0.633640 0.037 Uiso 1 1 calc R U . . .
C21 C 0.4009(3) 0.19024(7) 0.6899(5) 0.0317(7) Uani 1 1 d . . . . .
C22 C 0.5144(3) 0.19681(8) 0.6879(5) 0.0370(8) Uani 1 1 d . . . . .
H22 H 0.564341 0.187431 0.616414 0.044 Uiso 1 1 calc R U . . .
C23 C 0.5558(4) 0.21700(8) 0.7894(6) 0.0437(9) Uani 1 1 d . . . . .
H23 H 0.633693 0.221492 0.785288 0.052 Uiso 1 1 calc R U . . .
C24 C 0.4857(4) 0.23061(8) 0.8962(5) 0.0477(10) Uani 1 1 d . . . . .
H24 H 0.514832 0.244363 0.965563 0.057 Uiso 1 1 calc R U . . .
C25 C 0.3728(4) 0.22405(9) 0.9013(6) 0.0522(11) Uani 1 1 d . . . . .
H25 H 0.323774 0.233218 0.975110 0.063 Uiso 1 1 calc R U . . .
C26 C 0.3306(4) 0.20408(8) 0.7989(6) 0.0431(9) Uani 1 1 d . . . . .
H26 H 0.252541 0.199756 0.802929 0.052 Uiso 1 1 calc R U . . .
N2 N 0.4233(3) 0.14403(6) 0.5976(4) 0.0303(6) Uani 1 1 d . . . . .
C7 C 0.3812(3) 0.12357(7) 0.6687(4) 0.0306(7) Uani 1 1 d . . . . .
H7 H 0.306434 0.124481 0.710435 0.037 Uiso 1 1 calc R U . . .
C31 C 0.4457(3) 0.09856(7) 0.6876(4) 0.0298(7) Uani 1 1 d . . . . .
C32 C 0.5529(3) 0.09548(7) 0.6229(5) 0.0345(8) Uani 1 1 d . . . . .
H32 H 0.586094 0.109871 0.563240 0.041 Uiso 1 1 calc R U . . .
C33 C 0.6128(3) 0.07186(8) 0.6433(5) 0.0369(8) Uani 1 1 d . . . . .
H33 H 0.686242 0.069922 0.597771 0.044 Uiso 1 1 calc R U . . .
C34 C 0.5633(3) 0.05109(7) 0.7316(5) 0.0333(8) Uani 1 1 d . . . . .
Br1 Br 0.64622(4) 0.01898(2) 0.76842(6) 0.04709(14) Uani 1 1 d . . . . .
C35 C 0.4570(4) 0.05340(7) 0.7954(5) 0.0394(9) Uani 1 1 d . . . . .
H35 H 0.424141 0.038941 0.854891 0.047 Uiso 1 1 calc R U . . .
C36 C 0.3973(4) 0.07712(8) 0.7725(5) 0.0393(9) Uani 1 1 d . . . . .
H36 H 0.322938 0.078724 0.814960 0.047 Uiso 1 1 calc R U . . .
C3 C 0.4401(3) 0.17418(7) 0.2950(5) 0.0361(8) Uani 1 1 d . . . . .
H3A H 0.506860 0.178473 0.363845 0.043 Uiso 1 1 calc R U . . .
H3B H 0.435882 0.187263 0.202960 0.043 Uiso 1 1 calc R U . . .
C4 C 0.4490(3) 0.14546(7) 0.2267(5) 0.0338(8) Uani 1 1 d . . . . .
H4 H 0.499542 0.134470 0.299068 0.041 Uiso 1 1 calc R U . . .
C8 C 0.4896(4) 0.14426(9) 0.0485(5) 0.0438(9) Uani 1 1 d . . . . .
H8A H 0.485467 0.125729 0.008590 0.066 Uiso 1 1 calc R U . . .
H8B H 0.567774 0.150574 0.042752 0.066 Uiso 1 1 calc R U . . .
H8C H 0.441610 0.155717 -0.020666 0.066 Uiso 1 1 calc R U . . .
N201 N 0.9412(3) 0.13598(6) -0.2554(4) 0.0346(7) Uani 1 1 d . . . . .
C211 C 0.9711(3) 0.10912(7) -0.2970(5) 0.0336(8) Uani 1 1 d . . . . .
C212 C 0.9050(3) 0.08790(8) -0.2431(5) 0.0385(8) Uani 1 1 d . . . . .
H212 H 0.839024 0.091463 -0.180138 0.046 Uiso 1 1 calc R U . . .
C213 C 0.9334(3) 0.06177(8) -0.2792(5) 0.0383(8) Uani 1 1 d . . . . .
H213 H 0.887625 0.047415 -0.240795 0.046 Uiso 1 1 calc R U . . .
C214 C 1.0298(3) 0.05656(8) -0.3726(5) 0.0347(8) Uani 1 1 d . . . . .
O202 O 1.0490(3) 0.02985(6) -0.4048(4) 0.0451(7) Uani 1 1 d . . . . .
C217 C 1.1414(5) 0.02329(10) -0.5088(7) 0.0616(14) Uani 1 1 d . . . . .
H21A H 1.132374 0.032301 -0.615825 0.092 Uiso 1 1 calc R U . . .
H21B H 1.143796 0.003837 -0.525773 0.092 Uiso 1 1 calc R U . . .
H21C H 1.211845 0.029208 -0.456603 0.092 Uiso 1 1 calc R U . . .
C215 C 1.0976(3) 0.07739(8) -0.4267(5) 0.0371(8) Uani 1 1 d . . . . .
H215 H 1.164145 0.073792 -0.488234 0.045 Uiso 1 1 calc R U . . .
C216 C 1.0669(3) 0.10389(8) -0.3895(5) 0.0365(8) Uani 1 1 d . . . . .
H216 H 1.112020 0.118336 -0.428106 0.044 Uiso 1 1 calc R U . . .
C201 C 1.0110(3) 0.15267(7) -0.1683(5) 0.0332(8) Uani 1 1 d . . . . .
O201 O 1.1119(2) 0.14930(5) -0.1448(4) 0.0393(6) Uani 1 1 d . . . . .
C202 C 0.9405(3) 0.17572(7) -0.0978(5) 0.0341(8) Uani 1 1 d . . . . .
C205 C 1.0040(4) 0.20231(8) -0.1132(6) 0.0473(10) Uani 1 1 d . . . . .
H20A H 1.026085 0.205122 -0.228827 0.071 Uiso 1 1 calc R U . . .
H20B H 1.071666 0.201819 -0.043343 0.071 Uiso 1 1 calc R U . . .
H20C H 0.955004 0.217032 -0.077399 0.071 Uiso 1 1 calc R U . . .
C206 C 0.9246(3) 0.16835(7) 0.0894(5) 0.0320(7) Uani 1 1 d . . . . .
H206 H 1.000332 0.163873 0.136747 0.038 Uiso 1 1 calc R U . . .
C221 C 0.8727(3) 0.19068(7) 0.1943(5) 0.0349(8) Uani 1 1 d . . . . .
C222 C 0.7591(3) 0.19690(8) 0.1908(5) 0.0394(9) Uani 1 1 d . . . . .
H222 H 0.710249 0.187406 0.118151 0.047 Uiso 1 1 calc R U . . .
C223 C 0.7156(4) 0.21686(8) 0.2921(6) 0.0457(10) Uani 1 1 d . . . . .
H223 H 0.637318 0.220979 0.288272 0.055 Uiso 1 1 calc R U . . .
C224 C 0.7863(4) 0.23081(8) 0.3990(6) 0.0500(11) Uani 1 1 d . . . . .
H224 H 0.757010 0.244652 0.467486 0.060 Uiso 1 1 calc R U . . .
C225 C 0.8990(4) 0.22440(9) 0.4048(6) 0.0532(12) Uani 1 1 d . . . . .
H225 H 0.947532 0.233658 0.479029 0.064 Uiso 1 1 calc R U . . .
C226 C 0.9424(4) 0.20447(8) 0.3030(6) 0.0462(10) Uani 1 1 d . . . . .
H226 H 1.020566 0.200262 0.307800 0.055 Uiso 1 1 calc R U . . .
N202 N 0.8528(3) 0.14439(6) 0.1018(4) 0.0320(6) Uani 1 1 d . . . . .
C207 C 0.8962(3) 0.12399(7) 0.1713(4) 0.0317(7) Uani 1 1 d . . . . .
H207 H 0.971123 0.124962 0.212728 0.038 Uiso 1 1 calc R U . . .
C231 C 0.8320(3) 0.09887(7) 0.1888(4) 0.0313(7) Uani 1 1 d . . . . .
C232 C 0.8844(4) 0.07672(8) 0.2627(5) 0.0421(9) Uani 1 1 d . . . . .
H232 H 0.960688 0.077937 0.298323 0.051 Uiso 1 1 calc R U . . .
C233 C 0.8246(4) 0.05284(8) 0.2840(6) 0.0463(10) Uani 1 1 d . . . . .
H233 H 0.858898 0.037937 0.337357 0.056 Uiso 1 1 calc R U . . .
C234 C 0.7158(4) 0.05115(8) 0.2269(5) 0.0378(8) Uani 1 1 d . . . . .
Br2 Br 0.63108(5) 0.01932(2) 0.26013(7) 0.06056(17) Uani 1 1 d . . . . .
C235 C 0.6628(4) 0.07255(9) 0.1500(5) 0.0420(9) Uani 1 1 d . . . . .
H235 H 0.587410 0.071018 0.110746 0.050 Uiso 1 1 calc R U . . .
C236 C 0.7225(3) 0.09624(8) 0.1317(5) 0.0392(9) Uani 1 1 d . . . . .
H236 H 0.687395 0.111062 0.078647 0.047 Uiso 1 1 calc R U . . .
C203 C 0.8322(3) 0.17441(8) -0.2017(5) 0.0379(8) Uani 1 1 d . . . . .
H20D H 0.765632 0.178605 -0.132314 0.045 Uiso 1 1 calc R U . . .
H20E H 0.835508 0.187482 -0.293783 0.045 Uiso 1 1 calc R U . . .
C204 C 0.8239(3) 0.14575(8) -0.2693(5) 0.0357(8) Uani 1 1 d . . . . .
H204 H 0.773551 0.134797 -0.196648 0.043 Uiso 1 1 calc R U . . .
C208 C 0.7826(4) 0.14436(9) -0.4468(5) 0.0460(10) Uani 1 1 d . . . . .
H20F H 0.831626 0.155285 -0.517368 0.069 Uiso 1 1 calc R U . . .
H20G H 0.705141 0.151195 -0.452954 0.069 Uiso 1 1 calc R U . . .
H20H H 0.784216 0.125699 -0.484845 0.069 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 C1 1.358(5) . ?
N1 C11 1.434(5) . ?
N1 C4 1.479(5) . ?
C11 C12 1.384(5) . ?
C11 C16 1.384(5) . ?
C12 C13 1.397(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.383(5) . ?
C13 H13 0.9500 . ?
C14 O2 1.375(4) . ?
C14 C15 1.382(5) . ?
O2 C17 1.406(5) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C15 C16 1.380(5) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C1 O1 1.219(5) . ?
C1 C2 1.535(5) . ?
C2 C5 1.522(5) . ?
C2 C3 1.525(6) . ?
C2 C6 1.568(5) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 N2 1.476(4) . ?
C6 C21 1.523(5) . ?
C6 H6 1.0000 . ?
C21 C22 1.385(5) . ?
C21 C26 1.395(6) . ?
C22 C23 1.388(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.378(7) . ?
C23 H23 0.9500 . ?
C24 C25 1.378(7) . ?
C24 H24 0.9500 . ?
C25 C26 1.388(6) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
N2 C7 1.272(5) . ?
C7 C31 1.470(5) . ?
C7 H7 0.9500 . ?
C31 C32 1.383(5) . ?
C31 C36 1.394(5) . ?
C32 C33 1.385(5) . ?
C32 H32 0.9500 . ?
C33 C34 1.388(5) . ?
C33 H33 0.9500 . ?
C34 C35 1.367(6) . ?
C34 Br1 1.901(4) . ?
C35 C36 1.390(6) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C3 C4 1.538(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C8 1.519(6) . ?
C4 H4 1.0000 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
N201 C201 1.368(5) . ?
N201 C211 1.425(5) . ?
N201 C204 1.476(5) . ?
C211 C216 1.384(5) . ?
C211 C212 1.387(5) . ?
C212 C213 1.377(6) . ?
C212 H212 0.9500 . ?
C213 C214 1.395(6) . ?
C213 H213 0.9500 . ?
C214 O202 1.376(5) . ?
C214 C215 1.385(6) . ?
O202 C217 1.419(5) . ?
C217 H21A 0.9800 . ?
C217 H21B 0.9800 . ?
C217 H21C 0.9800 . ?
C215 C216 1.403(5) . ?
C215 H215 0.9500 . ?
C216 H216 0.9500 . ?
C201 O201 1.222(5) . ?
C201 C202 1.531(5) . ?
C202 C205 1.530(5) . ?
C202 C203 1.534(5) . ?
C202 C206 1.568(5) . ?
C205 H20A 0.9800 . ?
C205 H20B 0.9800 . ?
C205 H20C 0.9800 . ?
C206 N202 1.470(5) . ?
C206 C221 1.528(5) . ?
C206 H206 1.0000 . ?
C221 C222 1.382(6) . ?
C221 C226 1.387(6) . ?
C222 C223 1.389(6) . ?
C222 H222 0.9500 . ?
C223 C224 1.390(7) . ?
C223 H223 0.9500 . ?
C224 C225 1.374(7) . ?
C224 H224 0.9500 . ?
C225 C226 1.389(7) . ?
C225 H225 0.9500 . ?
C226 H226 0.9500 . ?
N202 C207 1.270(5) . ?
C207 C231 1.472(5) . ?
C207 H207 0.9500 . ?
C231 C236 1.383(5) . ?
C231 C232 1.400(5) . ?
C232 C233 1.396(6) . ?
C232 H232 0.9500 . ?
C233 C234 1.371(6) . ?
C233 H233 0.9500 . ?
C234 C235 1.385(6) . ?
C234 Br2 1.897(4) . ?
C235 C236 1.385(6) . ?
C235 H235 0.9500 . ?
C236 H236 0.9500 . ?
C203 C204 1.533(5) . ?
C203 H20D 0.9900 . ?
C203 H20E 0.9900 . ?
C204 C208 1.516(6) . ?
C204 H204 1.0000 . ?
C208 H20F 0.9800 . ?
C208 H20G 0.9800 . ?
C208 H20H 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
C1 N1 C11 122.7(3) . . ?
C1 N1 C4 114.4(3) . . ?
C11 N1 C4 121.4(3) . . ?
C12 C11 C16 119.6(3) . . ?
C12 C11 N1 120.7(3) . . ?
C16 C11 N1 119.6(3) . . ?
C11 C12 C13 120.5(3) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C14 C13 C12 119.5(3) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
O2 C14 C15 115.0(3) . . ?
O2 C14 C13 125.3(3) . . ?
C15 C14 C13 119.6(3) . . ?
C14 O2 C17 117.9(3) . . ?
O2 C17 H17A 109.5 . . ?
O2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C15 C14 121.0(3) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C11 119.7(3) . . ?
C15 C16 H16 120.1 . . ?
C11 C16 H16 120.1 . . ?
O1 C1 N1 126.5(3) . . ?
O1 C1 C2 125.0(4) . . ?
N1 C1 C2 108.5(3) . . ?
C5 C2 C3 113.3(3) . . ?
C5 C2 C1 110.8(3) . . ?
C3 C2 C1 102.8(3) . . ?
C5 C2 C6 110.2(3) . . ?
C3 C2 C6 114.7(3) . . ?
C1 C2 C6 104.4(3) . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 C21 108.6(3) . . ?
N2 C6 C2 109.1(3) . . ?
C21 C6 C2 114.0(3) . . ?
N2 C6 H6 108.3 . . ?
C21 C6 H6 108.3 . . ?
C2 C6 H6 108.3 . . ?
C22 C21 C26 118.2(4) . . ?
C22 C21 C6 123.6(3) . . ?
C26 C21 C6 118.2(3) . . ?
C21 C22 C23 120.5(4) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C24 C23 C22 121.0(4) . . ?
C24 C23 H23 119.5 . . ?
C22 C23 H23 119.5 . . ?
C23 C24 C25 119.2(4) . . ?
C23 C24 H24 120.4 . . ?
C25 C24 H24 120.4 . . ?
C24 C25 C26 120.1(4) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C25 C26 C21 121.0(4) . . ?
C25 C26 H26 119.5 . . ?
C21 C26 H26 119.5 . . ?
C7 N2 C6 116.2(3) . . ?
N2 C7 C31 121.5(3) . . ?
N2 C7 H7 119.2 . . ?
C31 C7 H7 119.2 . . ?
C32 C31 C36 118.6(3) . . ?
C32 C31 C7 122.1(3) . . ?
C36 C31 C7 119.2(3) . . ?
C31 C32 C33 121.4(3) . . ?
C31 C32 H32 119.3 . . ?
C33 C32 H32 119.3 . . ?
C32 C33 C34 118.6(4) . . ?
C32 C33 H33 120.7 . . ?
C34 C33 H33 120.7 . . ?
C35 C34 C33 121.4(3) . . ?
C35 C34 Br1 119.2(3) . . ?
C33 C34 Br1 119.3(3) . . ?
C34 C35 C36 119.4(3) . . ?
C34 C35 H35 120.3 . . ?
C36 C35 H35 120.3 . . ?
C35 C36 C31 120.6(4) . . ?
C35 C36 H36 119.7 . . ?
C31 C36 H36 119.7 . . ?
C2 C3 C4 106.8(3) . . ?
C2 C3 H3A 110.4 . . ?
C4 C3 H3A 110.4 . . ?
C2 C3 H3B 110.4 . . ?
C4 C3 H3B 110.4 . . ?
H3A C3 H3B 108.6 . . ?
N1 C4 C8 111.0(3) . . ?
N1 C4 C3 102.2(3) . . ?
C8 C4 C3 113.5(3) . . ?
N1 C4 H4 110.0 . . ?
C8 C4 H4 110.0 . . ?
C3 C4 H4 110.0 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C201 N201 C211 122.8(3) . . ?
C201 N201 C204 114.0(3) . . ?
C211 N201 C204 121.8(3) . . ?
C216 C211 C212 119.3(4) . . ?
C216 C211 N201 120.6(3) . . ?
C212 C211 N201 120.1(3) . . ?
C213 C212 C211 121.2(4) . . ?
C213 C212 H212 119.4 . . ?
C211 C212 H212 119.4 . . ?
C212 C213 C214 119.4(4) . . ?
C212 C213 H213 120.3 . . ?
C214 C213 H213 120.3 . . ?
O202 C214 C215 124.8(4) . . ?
O202 C214 C213 114.8(3) . . ?
C215 C214 C213 120.5(4) . . ?
C214 O202 C217 117.6(3) . . ?
O202 C217 H21A 109.5 . . ?
O202 C217 H21B 109.5 . . ?
H21A C217 H21B 109.5 . . ?
O202 C217 H21C 109.5 . . ?
H21A C217 H21C 109.5 . . ?
H21B C217 H21C 109.5 . . ?
C214 C215 C216 119.2(4) . . ?
C214 C215 H215 120.4 . . ?
C216 C215 H215 120.4 . . ?
C211 C216 C215 120.4(4) . . ?
C211 C216 H216 119.8 . . ?
C215 C216 H216 119.8 . . ?
O201 C201 N201 126.0(3) . . ?
O201 C201 C202 125.5(3) . . ?
N201 C201 C202 108.5(3) . . ?
C205 C202 C201 110.6(3) . . ?
C205 C202 C203 113.8(3) . . ?
C201 C202 C203 102.8(3) . . ?
C205 C202 C206 110.0(3) . . ?
C201 C202 C206 104.4(3) . . ?
C203 C202 C206 114.5(3) . . ?
C202 C205 H20A 109.5 . . ?
C202 C205 H20B 109.5 . . ?
H20A C205 H20B 109.5 . . ?
C202 C205 H20C 109.5 . . ?
H20A C205 H20C 109.5 . . ?
H20B C205 H20C 109.5 . . ?
N202 C206 C221 108.7(3) . . ?
N202 C206 C202 109.0(3) . . ?
C221 C206 C202 114.4(3) . . ?
N202 C206 H206 108.2 . . ?
C221 C206 H206 108.2 . . ?
C202 C206 H206 108.2 . . ?
C222 C221 C226 118.7(4) . . ?
C222 C221 C206 123.0(3) . . ?
C226 C221 C206 118.2(4) . . ?
C221 C222 C223 120.8(4) . . ?
C221 C222 H222 119.6 . . ?
C223 C222 H222 119.6 . . ?
C222 C223 C224 120.1(4) . . ?
C222 C223 H223 120.0 . . ?
C224 C223 H223 120.0 . . ?
C225 C224 C223 119.3(4) . . ?
C225 C224 H224 120.3 . . ?
C223 C224 H224 120.3 . . ?
C224 C225 C226 120.5(4) . . ?
C224 C225 H225 119.7 . . ?
C226 C225 H225 119.7 . . ?
C221 C226 C225 120.6(4) . . ?
C221 C226 H226 119.7 . . ?
C225 C226 H226 119.7 . . ?
C207 N202 C206 116.6(3) . . ?
N202 C207 C231 121.0(3) . . ?
N202 C207 H207 119.5 . . ?
C231 C207 H207 119.5 . . ?
C236 C231 C232 118.9(3) . . ?
C236 C231 C207 122.2(3) . . ?
C232 C231 C207 118.9(3) . . ?
C233 C232 C231 120.0(4) . . ?
C233 C232 H232 120.0 . . ?
C231 C232 H232 120.0 . . ?
C234 C233 C232 119.2(4) . . ?
C234 C233 H233 120.4 . . ?
C232 C233 H233 120.4 . . ?
C233 C234 C235 122.0(4) . . ?
C233 C234 Br2 120.1(3) . . ?
C235 C234 Br2 117.9(3) . . ?
C234 C235 C236 118.2(4) . . ?
C234 C235 H235 120.9 . . ?
C236 C235 H235 120.9 . . ?
C231 C236 C235 121.7(4) . . ?
C231 C236 H236 119.2 . . ?
C235 C236 H236 119.2 . . ?
C204 C203 C202 106.7(3) . . ?
C204 C203 H20D 110.4 . . ?
C202 C203 H20D 110.4 . . ?
C204 C203 H20E 110.4 . . ?
C202 C203 H20E 110.4 . . ?
H20D C203 H20E 108.6 . . ?
N201 C204 C208 111.1(3) . . ?
N201 C204 C203 102.8(3) . . ?
C208 C204 C203 113.6(3) . . ?
N201 C204 H204 109.7 . . ?
C208 C204 H204 109.7 . . ?
C203 C204 H204 109.7 . . ?
C204 C208 H20F 109.5 . . ?
C204 C208 H20G 109.5 . . ?
H20F C208 H20G 109.5 . . ?
C204 C208 H20H 109.5 . . ?
H20F C208 H20H 109.5 . . ?
H20G C208 H20H 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
C1 N1 C11 C12 59.0(5) . . . . ?
C4 N1 C11 C12 -135.8(4) . . . . ?
C1 N1 C11 C16 -118.5(4) . . . . ?
C4 N1 C11 C16 46.7(5) . . . . ?
C16 C11 C12 C13 -0.3(6) . . . . ?
N1 C11 C12 C13 -177.8(4) . . . . ?
C11 C12 C13 C14 -0.7(6) . . . . ?
C12 C13 C14 O2 -179.0(4) . . . . ?
C12 C13 C14 C15 1.2(6) . . . . ?
C15 C14 O2 C17 179.3(4) . . . . ?
C13 C14 O2 C17 -0.4(6) . . . . ?
O2 C14 C15 C16 179.5(4) . . . . ?
C13 C14 C15 C16 -0.7(6) . . . . ?
C14 C15 C16 C11 -0.3(7) . . . . ?
C12 C11 C16 C15 0.8(6) . . . . ?
N1 C11 C16 C15 178.4(4) . . . . ?
C11 N1 C1 O1 -15.1(6) . . . . ?
C4 N1 C1 O1 178.7(4) . . . . ?
C11 N1 C1 C2 161.8(3) . . . . ?
C4 N1 C1 C2 -4.4(4) . . . . ?
O1 C1 C2 C5 -44.6(5) . . . . ?
N1 C1 C2 C5 138.5(4) . . . . ?
O1 C1 C2 C3 -166.0(4) . . . . ?
N1 C1 C2 C3 17.1(4) . . . . ?
O1 C1 C2 C6 74.0(4) . . . . ?
N1 C1 C2 C6 -102.9(3) . . . . ?
C5 C2 C6 N2 -172.7(3) . . . . ?
C3 C2 C6 N2 -43.4(4) . . . . ?
C1 C2 C6 N2 68.3(3) . . . . ?
C5 C2 C6 C21 -51.1(4) . . . . ?
C3 C2 C6 C21 78.2(4) . . . . ?
C1 C2 C6 C21 -170.1(3) . . . . ?
N2 C6 C21 C22 44.8(5) . . . . ?
C2 C6 C21 C22 -77.0(4) . . . . ?
N2 C6 C21 C26 -132.1(4) . . . . ?
C2 C6 C21 C26 106.0(4) . . . . ?
C26 C21 C22 C23 -1.3(6) . . . . ?
C6 C21 C22 C23 -178.2(4) . . . . ?
C21 C22 C23 C24 1.1(6) . . . . ?
C22 C23 C24 C25 -0.2(7) . . . . ?
C23 C24 C25 C26 -0.5(7) . . . . ?
C24 C25 C26 C21 0.3(7) . . . . ?
C22 C21 C26 C25 0.6(6) . . . . ?
C6 C21 C26 C25 177.7(4) . . . . ?
C21 C6 N2 C7 114.6(3) . . . . ?
C2 C6 N2 C7 -120.6(3) . . . . ?
C6 N2 C7 C31 179.7(3) . . . . ?
N2 C7 C31 C32 -3.1(5) . . . . ?
N2 C7 C31 C36 177.4(4) . . . . ?
C36 C31 C32 C33 -1.1(6) . . . . ?
C7 C31 C32 C33 179.4(4) . . . . ?
C31 C32 C33 C34 -0.4(6) . . . . ?
C32 C33 C34 C35 1.1(6) . . . . ?
C32 C33 C34 Br1 -177.6(3) . . . . ?
C33 C34 C35 C36 -0.4(6) . . . . ?
Br1 C34 C35 C36 178.3(3) . . . . ?
C34 C35 C36 C31 -1.0(6) . . . . ?
C32 C31 C36 C35 1.8(6) . . . . ?
C7 C31 C36 C35 -178.7(4) . . . . ?
C5 C2 C3 C4 -142.7(3) . . . . ?
C1 C2 C3 C4 -23.0(4) . . . . ?
C6 C2 C3 C4 89.6(4) . . . . ?
C1 N1 C4 C8 -131.4(3) . . . . ?
C11 N1 C4 C8 62.2(4) . . . . ?
C1 N1 C4 C3 -10.2(4) . . . . ?
C11 N1 C4 C3 -176.5(3) . . . . ?
C2 C3 C4 N1 20.5(4) . . . . ?
C2 C3 C4 C8 140.1(3) . . . . ?
C201 N201 C211 C216 -58.4(5) . . . . ?
C204 N201 C211 C216 135.8(4) . . . . ?
C201 N201 C211 C212 120.8(4) . . . . ?
C204 N201 C211 C212 -44.9(5) . . . . ?
C216 C211 C212 C213 0.4(6) . . . . ?
N201 C211 C212 C213 -178.8(4) . . . . ?
C211 C212 C213 C214 -0.5(6) . . . . ?
C212 C213 C214 O202 -178.6(4) . . . . ?
C212 C213 C214 C215 0.9(6) . . . . ?
C215 C214 O202 C217 -3.7(6) . . . . ?
C213 C214 O202 C217 175.8(4) . . . . ?
O202 C214 C215 C216 178.1(4) . . . . ?
C213 C214 C215 C216 -1.4(6) . . . . ?
C212 C211 C216 C215 -0.8(6) . . . . ?
N201 C211 C216 C215 178.4(4) . . . . ?
C214 C215 C216 C211 1.3(6) . . . . ?
C211 N201 C201 O201 15.6(6) . . . . ?
C204 N201 C201 O201 -177.6(4) . . . . ?
C211 N201 C201 C202 -161.7(3) . . . . ?
C204 N201 C201 C202 5.1(4) . . . . ?
O201 C201 C202 C205 43.5(5) . . . . ?
N201 C201 C202 C205 -139.1(3) . . . . ?
O201 C201 C202 C203 165.4(4) . . . . ?
N201 C201 C202 C203 -17.3(4) . . . . ?
O201 C201 C202 C206 -74.8(4) . . . . ?
N201 C201 C202 C206 102.6(3) . . . . ?
C205 C202 C206 N202 173.8(3) . . . . ?
C201 C202 C206 N202 -67.5(3) . . . . ?
C203 C202 C206 N202 44.1(4) . . . . ?
C205 C202 C206 C221 51.8(4) . . . . ?
C201 C202 C206 C221 170.5(3) . . . . ?
C203 C202 C206 C221 -77.8(4) . . . . ?
N202 C206 C221 C222 -45.7(5) . . . . ?
C202 C206 C221 C222 76.5(5) . . . . ?
N202 C206 C221 C226 131.4(4) . . . . ?
C202 C206 C221 C226 -106.4(4) . . . . ?
C226 C221 C222 C223 1.0(6) . . . . ?
C206 C221 C222 C223 178.1(4) . . . . ?
C221 C222 C223 C224 -0.2(7) . . . . ?
C222 C223 C224 C225 -0.9(7) . . . . ?
C223 C224 C225 C226 1.1(7) . . . . ?
C222 C221 C226 C225 -0.8(6) . . . . ?
C206 C221 C226 C225 -178.0(4) . . . . ?
C224 C225 C226 C221 -0.2(7) . . . . ?
C221 C206 N202 C207 -114.9(4) . . . . ?
C202 C206 N202 C207 119.7(3) . . . . ?
C206 N202 C207 C231 -179.4(3) . . . . ?
N202 C207 C231 C236 -0.3(6) . . . . ?
N202 C207 C231 C232 178.4(4) . . . . ?
C236 C231 C232 C233 -2.7(6) . . . . ?
C207 C231 C232 C233 178.6(4) . . . . ?
C231 C232 C233 C234 2.1(7) . . . . ?
C232 C233 C234 C235 -0.6(7) . . . . ?
C232 C233 C234 Br2 -178.1(3) . . . . ?
C233 C234 C235 C236 -0.3(7) . . . . ?
Br2 C234 C235 C236 177.3(3) . . . . ?
C232 C231 C236 C235 1.8(6) . . . . ?
C207 C231 C236 C235 -179.5(4) . . . . ?
C234 C235 C236 C231 -0.3(6) . . . . ?
C205 C202 C203 C204 142.4(3) . . . . ?
C201 C202 C203 C204 22.7(4) . . . . ?
C206 C202 C203 C204 -89.9(4) . . . . ?
C201 N201 C204 C208 131.3(4) . . . . ?
C211 N201 C204 C208 -61.8(5) . . . . ?
C201 N201 C204 C203 9.5(4) . . . . ?
C211 N201 C204 C203 176.4(3) . . . . ?
C202 C203 C204 N201 -20.0(4) . . . . ?
C202 C203 C204 C208 -140.1(3) . . . . ?

_refine_diff_density_max         1.211
_refine_diff_density_min         -0.757
_refine_diff_density_rms         0.084

####################################################################### 
# 
# 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_D19141
_database_code_depnum_ccdc_archive 'CCDC 2253012'
loop_
_audit_author_name
_audit_author_address
'Michael K. Takase'
;California Institute of Technology 
United States of America
;
_audit_update_record             
;
2023-03-30 deposited with the CCDC.	2025-05-01 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            'C26 H26 N2 O2'
_chemical_formula_weight         398.49

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'

_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                   19.640(5)
_cell_length_b                   6.1440(16)
_cell_length_c                   17.135(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.127(6)
_cell_angle_gamma                90
_cell_volume                     2062.3(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9527
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      35.93

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7041
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_process_details   'SADABS-2016/2 (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 KAPPA'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            110686
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.079
_diffrn_reflns_theta_max         35.630
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             9463
_reflns_number_gt                8005
_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       'APEX3 v2019.1-0 (Bruker Nano, 2019)'
_computing_cell_refinement       'SAINT v8.40A (Bruker-AXS, 2013)'
_computing_data_reduction        'SAINT v8.40A (Bruker-AXS, 2013)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0649P)²+0.4930P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9463
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_ref         0.1175
_refine_ls_wR_factor_gt          0.1106
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.83282(3) 0.31324(9) 0.61129(3) 0.01160(9) Uani 1 1 d . . . . .
C1 C 0.86755(3) 0.33512(10) 0.68619(4) 0.01153(10) Uani 1 1 d . . . . .
C2 C 0.91542(4) 0.17841(11) 0.71140(4) 0.01542(12) Uani 1 1 d . . . . .
H2 H 0.923561 0.058776 0.678202 0.019 Uiso 1 1 calc R U . . .
C3 C 0.95174(4) 0.19293(12) 0.78427(4) 0.01547(12) Uani 1 1 d . . . . .
H3 H 0.984123 0.084170 0.800437 0.019 Uiso 1 1 calc R U . . .
C4 C 0.94014(3) 0.36737(11) 0.83285(4) 0.01318(11) Uani 1 1 d . . . . .
O1 O 0.97229(3) 0.39795(9) 0.90590(3) 0.01718(10) Uani 1 1 d . . . . .
C7 C 1.02073(4) 0.23721(13) 0.93258(4) 0.01751(12) Uani 1 1 d . . . . .
H7A H 0.998580 0.094236 0.932129 0.026 Uiso 1 1 calc R U . . .
H7B H 1.038598 0.272277 0.985969 0.026 Uiso 1 1 calc R U . . .
H7C H 1.058352 0.234446 0.897997 0.026 Uiso 1 1 calc R U . . .
C5 C 0.89279(4) 0.52614(12) 0.80795(4) 0.01591(12) Uani 1 1 d . . . . .
H5 H 0.885395 0.646833 0.840945 0.019 Uiso 1 1 calc R U . . .
C6 C 0.85628(3) 0.51103(12) 0.73586(4) 0.01475(11) Uani 1 1 d . . . . .
H6 H 0.823694 0.619581 0.720115 0.018 Uiso 1 1 calc R U . . .
C8 C 0.79595(3) 0.47059(10) 0.57069(4) 0.01105(10) Uani 1 1 d . . . . .
O2 O 0.77931(3) 0.64811(8) 0.59549(3) 0.01565(10) Uani 1 1 d . . . . .
C9 C 0.78341(3) 0.39531(10) 0.48576(4) 0.01089(10) Uani 1 1 d . . . . .
C10 C 0.79201(3) 0.14869(11) 0.49260(4) 0.01382(11) Uani 1 1 d . . . . .
H10A H 0.809534 0.086933 0.444584 0.017 Uiso 1 1 calc R U . . .
H10B H 0.748201 0.077297 0.502176 0.017 Uiso 1 1 calc R U . . .
C11 C 0.84394(3) 0.12129(11) 0.56278(4) 0.01396(11) Uani 1 1 d . . . . .
H11A H 0.835477 -0.014622 0.591570 0.017 Uiso 1 1 calc R U . . .
H11B H 0.891122 0.118652 0.545977 0.017 Uiso 1 1 calc R U . . .
C12 C 0.84119(3) 0.49833(12) 0.44246(4) 0.01579(12) Uani 1 1 d . . . . .
H12A H 0.885365 0.451206 0.466965 0.024 Uiso 1 1 calc R U . . .
H12B H 0.837884 0.657256 0.445225 0.024 Uiso 1 1 calc R U . . .
H12C H 0.837183 0.452229 0.387570 0.024 Uiso 1 1 calc R U . . .
C13 C 0.71335(3) 0.47554(10) 0.45020(4) 0.01148(10) Uani 1 1 d . . . . .
H13 H 0.711283 0.637153 0.456522 0.014 Uiso 1 1 calc R U . . .
C21 C 0.70327(3) 0.42245(11) 0.36374(4) 0.01194(10) Uani 1 1 d . . . . .
C22 C 0.68152(3) 0.21677(11) 0.33761(4) 0.01493(11) Uani 1 1 d . . . . .
H22 H 0.671938 0.107443 0.374468 0.018 Uiso 1 1 calc R U . . .
C23 C 0.67379(4) 0.17110(13) 0.25784(4) 0.01776(12) Uani 1 1 d . . . . .
H23 H 0.659050 0.030743 0.240594 0.021 Uiso 1 1 calc R U . . .
C24 C 0.68757(4) 0.33002(14) 0.20327(4) 0.01824(13) Uani 1 1 d . . . . .
H24 H 0.682162 0.298439 0.148907 0.022 Uiso 1 1 calc R U . . .
C25 C 0.70927(4) 0.53514(13) 0.22865(4) 0.01810(13) Uani 1 1 d . . . . .
H25 H 0.718892 0.644143 0.191695 0.022 Uiso 1 1 calc R U . . .
C26 C 0.71686(4) 0.58035(12) 0.30856(4) 0.01527(11) Uani 1 1 d . . . . .
H26 H 0.731519 0.720935 0.325643 0.018 Uiso 1 1 calc R U . . .
N2 N 0.65883(3) 0.37811(10) 0.49237(3) 0.01306(10) Uani 1 1 d . . . . .
C14 C 0.62265(3) 0.50857(12) 0.52970(4) 0.01443(11) Uani 1 1 d . . . . .
H14 H 0.632899 0.659620 0.528712 0.017 Uiso 1 1 calc R U . . .
C31 C 0.56566(3) 0.43503(12) 0.57426(4) 0.01523(12) Uani 1 1 d . . . . .
C32 C 0.53700(4) 0.58144(14) 0.62473(4) 0.02091(14) Uani 1 1 d . . . . .
H32 H 0.554414 0.725421 0.629640 0.025 Uiso 1 1 calc R U . . .
C33 C 0.48302(4) 0.51795(17) 0.66796(5) 0.02624(17) Uani 1 1 d . . . . .
H33 H 0.463788 0.618127 0.702434 0.031 Uiso 1 1 calc R U . . .
C34 C 0.45745(4) 0.30855(17) 0.66058(5) 0.02695(18) Uani 1 1 d . . . . .
H34 H 0.420620 0.265097 0.690077 0.032 Uiso 1 1 calc R U . . .
C35 C 0.48544(4) 0.16132(16) 0.61012(5) 0.02455(16) Uani 1 1 d . . . . .
H35 H 0.467566 0.017950 0.604996 0.029 Uiso 1 1 calc R U . . .
C36 C 0.53958(4) 0.22411(13) 0.56721(4) 0.01891(13) Uani 1 1 d . . . . .
H36 H 0.558860 0.123242 0.533030 0.023 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 C8 1.3677(9) . ?
N1 C1 1.4158(9) . ?
N1 C11 1.4682(9) . ?
C1 C2 1.3926(9) . ?
C1 C6 1.4031(10) . ?
C2 C3 1.3955(10) . ?
C2 H2 0.9500 . ?
C3 C4 1.3859(10) . ?
C3 H3 0.9500 . ?
C4 O1 1.3737(9) . ?
C4 C5 1.3934(10) . ?
O1 C7 1.4236(9) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C5 C6 1.3859(10) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C8 O2 1.2236(8) . ?
C8 C9 1.5301(9) . ?
C9 C10 1.5282(10) . ?
C9 C12 1.5363(9) . ?
C9 C13 1.5449(9) . ?
C10 C11 1.5291(10) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 N2 1.4624(9) . ?
C13 C21 1.5160(10) . ?
C13 H13 1.0000 . ?
C21 C26 1.3939(10) . ?
C21 C22 1.3973(10) . ?
C22 C23 1.3930(10) . ?
C22 H22 0.9500 . ?
C23 C24 1.3919(11) . ?
C23 H23 0.9500 . ?
C24 C25 1.3901(11) . ?
C24 H24 0.9500 . ?
C25 C26 1.3945(10) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
N2 C14 1.2735(9) . ?
C14 C31 1.4707(10) . ?
C14 H14 0.9500 . ?
C31 C32 1.3943(10) . ?
C31 C36 1.3955(12) . ?
C32 C33 1.3922(12) . ?
C32 H32 0.9500 . ?
C33 C34 1.3836(15) . ?
C33 H33 0.9500 . ?
C34 C35 1.3917(13) . ?
C34 H34 0.9500 . ?
C35 C36 1.3901(11) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N1 C1 126.65(6) . . ?
C8 N1 C11 112.01(5) . . ?
C1 N1 C11 120.53(5) . . ?
C2 C1 C6 118.47(6) . . ?
C2 C1 N1 119.08(6) . . ?
C6 C1 N1 122.44(6) . . ?
C1 C2 C3 121.57(6) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
C4 C3 C2 119.43(6) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
O1 C4 C3 124.65(6) . . ?
O1 C4 C5 115.86(6) . . ?
C3 C4 C5 119.49(6) . . ?
C4 O1 C7 116.77(6) . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C5 C4 121.14(6) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C1 119.89(6) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
O2 C8 N1 126.75(6) . . ?
O2 C8 C9 124.83(6) . . ?
N1 C8 C9 108.26(5) . . ?
C10 C9 C8 102.55(5) . . ?
C10 C9 C12 111.35(5) . . ?
C8 C9 C12 105.12(5) . . ?
C10 C9 C13 115.92(5) . . ?
C8 C9 C13 110.89(5) . . ?
C12 C9 C13 110.24(5) . . ?
C9 C10 C11 103.49(5) . . ?
C9 C10 H10A 111.1 . . ?
C11 C10 H10A 111.1 . . ?
C9 C10 H10B 111.1 . . ?
C11 C10 H10B 111.1 . . ?
H10A C10 H10B 109.0 . . ?
N1 C11 C10 103.82(5) . . ?
N1 C11 H11A 111.0 . . ?
C10 C11 H11A 111.0 . . ?
N1 C11 H11B 111.0 . . ?
C10 C11 H11B 111.0 . . ?
H11A C11 H11B 109.0 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 C21 110.25(5) . . ?
N2 C13 C9 109.73(5) . . ?
C21 C13 C9 111.51(5) . . ?
N2 C13 H13 108.4 . . ?
C21 C13 H13 108.4 . . ?
C9 C13 H13 108.4 . . ?
C26 C21 C22 118.76(6) . . ?
C26 C21 C13 119.69(6) . . ?
C22 C21 C13 121.54(6) . . ?
C23 C22 C21 120.38(6) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C24 C23 C22 120.35(7) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C25 C24 C23 119.72(7) . . ?
C25 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C24 C25 C26 119.77(7) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 H25 120.1 . . ?
C21 C26 C25 121.01(7) . . ?
C21 C26 H26 119.5 . . ?
C25 C26 H26 119.5 . . ?
C14 N2 C13 116.44(6) . . ?
N2 C14 C31 122.70(7) . . ?
N2 C14 H14 118.6 . . ?
C31 C14 H14 118.6 . . ?
C32 C31 C36 119.38(7) . . ?
C32 C31 C14 118.70(7) . . ?
C36 C31 C14 121.92(6) . . ?
C33 C32 C31 120.41(8) . . ?
C33 C32 H32 119.8 . . ?
C31 C32 H32 119.8 . . ?
C34 C33 C32 119.82(8) . . ?
C34 C33 H33 120.1 . . ?
C32 C33 H33 120.1 . . ?
C33 C34 C35 120.28(8) . . ?
C33 C34 H34 119.9 . . ?
C35 C34 H34 119.9 . . ?
C36 C35 C34 119.98(9) . . ?
C36 C35 H35 120.0 . . ?
C34 C35 H35 120.0 . . ?
C35 C36 C31 120.13(7) . . ?
C35 C36 H36 119.9 . . ?
C31 C36 H36 119.9 . . ?

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
C8 N1 C1 C2 -165.03(6) . . . . ?
C11 N1 C1 C2 3.74(9) . . . . ?
C8 N1 C1 C6 14.04(10) . . . . ?
C11 N1 C1 C6 -177.19(6) . . . . ?
C6 C1 C2 C3 0.16(11) . . . . ?
N1 C1 C2 C3 179.27(6) . . . . ?
C1 C2 C3 C4 -0.12(11) . . . . ?
C2 C3 C4 O1 179.43(7) . . . . ?
C2 C3 C4 C5 -0.44(10) . . . . ?
C3 C4 O1 C7 -0.06(10) . . . . ?
C5 C4 O1 C7 179.81(6) . . . . ?
O1 C4 C5 C6 -178.90(6) . . . . ?
C3 C4 C5 C6 0.98(11) . . . . ?
C4 C5 C6 C1 -0.94(11) . . . . ?
C2 C1 C6 C5 0.37(10) . . . . ?
N1 C1 C6 C5 -178.71(6) . . . . ?
C1 N1 C8 O2 -9.85(11) . . . . ?
C11 N1 C8 O2 -179.43(6) . . . . ?
C1 N1 C8 C9 165.62(6) . . . . ?
C11 N1 C8 C9 -3.95(7) . . . . ?
O2 C8 C9 C10 -162.44(6) . . . . ?
N1 C8 C9 C10 21.98(7) . . . . ?
O2 C8 C9 C12 81.04(8) . . . . ?
N1 C8 C9 C12 -94.54(6) . . . . ?
O2 C8 C9 C13 -38.09(9) . . . . ?
N1 C8 C9 C13 146.33(5) . . . . ?
C8 C9 C10 C11 -30.46(6) . . . . ?
C12 C9 C10 C11 81.50(7) . . . . ?
C13 C9 C10 C11 -151.42(5) . . . . ?
C8 N1 C11 C10 -15.83(7) . . . . ?
C1 N1 C11 C10 173.87(6) . . . . ?
C9 C10 C11 N1 28.62(7) . . . . ?
C10 C9 C13 N2 52.92(7) . . . . ?
C8 C9 C13 N2 -63.45(7) . . . . ?
C12 C9 C13 N2 -179.44(5) . . . . ?
C10 C9 C13 C21 -69.53(7) . . . . ?
C8 C9 C13 C21 174.11(5) . . . . ?
C12 C9 C13 C21 58.11(7) . . . . ?
N2 C13 C21 C26 140.78(6) . . . . ?
C9 C13 C21 C26 -97.07(7) . . . . ?
N2 C13 C21 C22 -40.19(8) . . . . ?
C9 C13 C21 C22 81.96(8) . . . . ?
C26 C21 C22 C23 0.15(10) . . . . ?
C13 C21 C22 C23 -178.88(6) . . . . ?
C21 C22 C23 C24 -0.10(11) . . . . ?
C22 C23 C24 C25 0.13(11) . . . . ?
C23 C24 C25 C26 -0.21(11) . . . . ?
C22 C21 C26 C25 -0.23(10) . . . . ?
C13 C21 C26 C25 178.82(6) . . . . ?
C24 C25 C26 C21 0.26(11) . . . . ?
C21 C13 N2 C14 -121.09(6) . . . . ?
C9 C13 N2 C14 115.72(6) . . . . ?
C13 N2 C14 C31 179.47(6) . . . . ?
N2 C14 C31 C32 168.35(7) . . . . ?
N2 C14 C31 C36 -11.84(10) . . . . ?
C36 C31 C32 C33 0.23(11) . . . . ?
C14 C31 C32 C33 -179.96(7) . . . . ?
C31 C32 C33 C34 -0.27(12) . . . . ?
C32 C33 C34 C35 -0.03(12) . . . . ?
C33 C34 C35 C36 0.36(12) . . . . ?
C34 C35 C36 C31 -0.40(12) . . . . ?
C32 C31 C36 C35 0.11(11) . . . . ?
C14 C31 C36 C35 -179.70(7) . . . . ?

_refine_diff_density_max         0.569
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.053

