# 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_dtr-384_auto
_database_code_depnum_ccdc_archive 'CCDC 2341135'
_audit_update_record             
;
2024-03-18 deposited with the CCDC.	2025-03-05 downloaded from the CCDC.
;
_audit_creation_date             2023-06-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H20 Br N O2'
_chemical_formula_sum            'C21 H20 Br N O2'
_chemical_formula_weight         398.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N'
_chemical_oxdiff_usercomment     25-04-2023
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   8.9741(2)
_cell_length_b                   18.6365(4)
_cell_length_c                   11.5094(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.833(3)
_cell_angle_gamma                90
_cell_volume                     1869.07(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    16900
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      31.1300
_cell_measurement_theta_min      3.1970
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.213
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.14246
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.69a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            38251
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         3.201
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -23.00  27.00   0.50    0.86    --   -5.21 -99.00 150.00  100
  2  ω    -78.00   8.00   0.50    0.86    --   -5.21 -38.00  60.00  172
  3  ω    -23.00  38.00   0.50    0.86    --    5.37 -99.00  30.00  122
  4  ω    -67.00  -1.00   0.50    0.86    --    5.37 -38.00  90.00  132
  5  ω    -23.00  27.00   0.50    0.86    --   -5.21 -99.00 -60.00  100
  6  ω    -67.00  19.00   0.50    0.86    --    5.37 -38.00 -90.00  172
  7  ω    -67.00  19.00   0.50    0.86    --    5.37 -38.00-150.00  172
  8  ω    -23.00  38.00   0.50    0.86    --    5.37 -99.00-180.00  122
  9  ω     -8.00  78.00   0.50    0.86    --    5.37  38.00  30.00  172
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0715286000
_diffrn_orient_matrix_UB_12      0.0030225000
_diffrn_orient_matrix_UB_13      -0.0423606000
_diffrn_orient_matrix_UB_21      0.0379848000
_diffrn_orient_matrix_UB_22      -0.0025541000
_diffrn_orient_matrix_UB_23      -0.0472806000
_diffrn_orient_matrix_UB_31      -0.0082289000
_diffrn_orient_matrix_UB_32      -0.0378428000
_diffrn_orient_matrix_UB_33      -0.0001898000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3458
_reflns_number_total             3823
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.69a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.69a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.69a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3823
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0250
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0182P)²+1.5837P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0555
_refine_ls_wR_factor_ref         0.0568
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, H00K of C00J, H00A of C00A, H00H of C00H, H00O of C00M,
  H00L of C00K, H00E of C00D, H00D of C00C, H00Q of C00O, H00P of C00N
 At 1.5 times of:
  All C(H,H,H) groups, H00I of C00I
2.a Secondary CH2 refined with riding coordinates:
 C00B(H00B,H00C), C00F(H00F,H00G), C00L(H00M,H00N)
2.b Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00C(H00D), C00D(H00E), C00H(H00H), C00J(H00K), C00K(H00L),
 C00M(H00O), C00N(H00P), C00O(H00Q)
2.c Idealised Me refined as rotating group:
 C00P(H00R,H00S,H00T)
2.d Idealised tetrahedral OH refined as rotating group:
 C00I(H00I)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Br01 Br 0.64483(2) 0.28700(2) 0.35327(2) 0.01914(6) Uani 1 1 d . . . . .
O002 O 0.58453(14) 0.58293(7) 0.86568(11) 0.0213(3) Uani 1 1 d . . . . .
O003 O 0.80656(14) 0.59429(7) 0.80934(11) 0.0210(3) Uani 1 1 d . . . . .
N004 N 0.69766(16) 0.49875(8) 0.61698(12) 0.0137(3) Uani 1 1 d . . . . .
C005 C 0.70442(19) 0.53637(9) 0.51510(15) 0.0136(3) Uani 1 1 d . . . . .
C006 C 0.68007(19) 0.56920(9) 0.79589(15) 0.0147(3) Uani 1 1 d . . . . .
C007 C 0.83598(19) 0.33451(9) 0.35776(16) 0.0150(3) Uani 1 1 d . . . . .
C008 C 0.77002(19) 0.43255(9) 0.61476(15) 0.0137(3) Uani 1 1 d . . . . .
C009 C 0.82314(19) 0.42759(9) 0.51288(15) 0.0135(3) Uani 1 1 d . . . . .
C00A C 0.8125(2) 0.52154(9) 0.34249(15) 0.0163(3) Uani 1 1 d . . . . .
H00A H 0.868318 0.494437 0.297192 0.020 Uiso 1 1 calc R U . . .
C00B C 0.91268(19) 0.36699(9) 0.47635(15) 0.0146(3) Uani 1 1 d . . . . .
H00B H 1.015184 0.384943 0.472407 0.018 Uiso 1 1 calc R U . . .
H00C H 0.927903 0.329170 0.538471 0.018 Uiso 1 1 calc R U . . .
C00C C 0.7383(2) 0.31369(9) 0.70817(16) 0.0172(4) Uani 1 1 d . . . . .
H00D H 0.683891 0.296195 0.632341 0.021 Uiso 1 1 calc R U . . .
C00D C 0.7630(2) 0.26908(10) 0.80798(17) 0.0204(4) Uani 1 1 d . . . . .
H00E H 0.725550 0.221219 0.800167 0.024 Uiso 1 1 calc R U . . .
C00E C 0.78494(18) 0.49385(9) 0.44882(15) 0.0132(3) Uani 1 1 d . . . . .
C00F C 0.60241(19) 0.51858(9) 0.69713(15) 0.0150(3) Uani 1 1 d . . . . .
H00F H 0.572087 0.474493 0.733623 0.018 Uiso 1 1 calc R U . . .
H00G H 0.507620 0.541552 0.650047 0.018 Uiso 1 1 calc R U . . .
C00G C 0.79314(19) 0.38407(9) 0.71921(15) 0.0145(3) Uani 1 1 d . . . . .
C00H C 0.8734(2) 0.40864(10) 0.83134(16) 0.0176(4) Uani 1 1 d . . . . .
H00H H 0.911290 0.456425 0.839672 0.021 Uiso 1 1 calc R U . . .
C00I C 0.8867(2) 0.33613(10) 0.25923(17) 0.0212(4) Uani 1 1 d . . . . .
H00I H 0.824900 0.314186 0.204397 0.032 Uiso 1 1 calc R U . . .
C00J C 0.8984(2) 0.36414(10) 0.93071(16) 0.0198(4) Uani 1 1 d . . . . .
H00K H 0.953552 0.381249 1.006574 0.024 Uiso 1 1 calc R U . . .
C00K C 0.8422(2) 0.29442(10) 0.91861(16) 0.0202(4) Uani 1 1 d . . . . .
H00L H 0.858230 0.263940 0.986629 0.024 Uiso 1 1 calc R U . . .
C00L C 0.6371(2) 0.63554(12) 0.96033(17) 0.0271(4) Uani 1 1 d . . . . .
H00M H 0.663749 0.681181 0.926204 0.033 Uiso 1 1 calc R U . . .
H00N H 0.729159 0.617542 1.018626 0.033 Uiso 1 1 calc R U . . .
C00M C 0.64408(19) 0.60362(9) 0.47556(16) 0.0165(4) Uani 1 1 d . . . . .
H00O H 0.586617 0.630746 0.519541 0.020 Uiso 1 1 calc R U . . .
C00N C 0.7570(2) 0.58902(9) 0.30484(16) 0.0184(4) Uani 1 1 d . . . . .
H00P H 0.776884 0.608647 0.233884 0.022 Uiso 1 1 calc R U . . .
C00O C 0.6716(2) 0.62903(9) 0.36974(16) 0.0189(4) Uani 1 1 d . . . . .
H00Q H 0.631851 0.674504 0.340278 0.023 Uiso 1 1 calc R U . . .
C00P C 0.5085(2) 0.64696(14) 1.0202(2) 0.0386(6) Uani 1 1 d . . . . .
H00R H 0.418766 0.665600 0.961940 0.058 Uiso 1 1 calc R U . . .
H00S H 0.540205 0.681514 1.085656 0.058 Uiso 1 1 calc R U . . .
H00T H 0.482055 0.601251 1.052356 0.058 Uiso 1 1 calc R U . . .
H00J H 0.979(3) 0.3588(12) 0.260(2) 0.030(6) Uiso 1 1 d . . . . .


_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
Br01 C007 1.9201(17) . ?
O002 C006 1.332(2) . ?
O002 C00L 1.458(2) . ?
O003 C006 1.203(2) . ?
N004 C005 1.380(2) . ?
N004 C008 1.397(2) . ?
N004 C00F 1.448(2) . ?
C005 C00E 1.413(2) . ?
C005 C00M 1.398(2) . ?
C006 C00F 1.513(2) . ?
C007 C00B 1.501(2) . ?
C007 C00I 1.319(3) . ?
C008 C009 1.370(2) . ?
C008 C00G 1.478(2) . ?
C009 C00B 1.503(2) . ?
C009 C00E 1.437(2) . ?
C00A H00A 0.9500 . ?
C00A C00E 1.404(2) . ?
C00A C00N 1.384(2) . ?
C00B H00B 0.9900 . ?
C00B H00C 0.9900 . ?
C00C H00D 0.9500 . ?
C00C C00D 1.392(3) . ?
C00C C00G 1.396(2) . ?
C00D H00E 0.9500 . ?
C00D C00K 1.384(3) . ?
C00F H00F 0.9900 . ?
C00F H00G 0.9900 . ?
C00G C00H 1.396(2) . ?
C00H H00H 0.9500 . ?
C00H C00J 1.387(3) . ?
C00I H00I 0.8400 . ?
C00I H00J 0.93(2) . ?
C00J H00K 0.9500 . ?
C00J C00K 1.388(3) . ?
C00K H00L 0.9500 . ?
C00L H00M 0.9900 . ?
C00L H00N 0.9900 . ?
C00L C00P 1.495(3) . ?
C00M H00O 0.9500 . ?
C00M C00O 1.383(3) . ?
C00N H00P 0.9500 . ?
C00N C00O 1.405(3) . ?
C00O H00Q 0.9500 . ?
C00P H00R 0.9800 . ?
C00P H00S 0.9800 . ?
C00P H00T 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
C006 O002 C00L 116.09(14) . . ?
C005 N004 C008 108.55(13) . . ?
C005 N004 C00F 124.36(14) . . ?
C008 N004 C00F 125.79(14) . . ?
N004 C005 C00E 107.82(14) . . ?
N004 C005 C00M 129.79(16) . . ?
C00M C005 C00E 122.38(16) . . ?
O002 C006 C00F 108.99(14) . . ?
O003 C006 O002 124.83(16) . . ?
O003 C006 C00F 126.16(15) . . ?
C00B C007 Br01 115.01(12) . . ?
C00I C007 Br01 118.48(14) . . ?
C00I C007 C00B 126.51(16) . . ?
N004 C008 C00G 120.02(15) . . ?
C009 C008 N004 109.47(15) . . ?
C009 C008 C00G 130.15(15) . . ?
C008 C009 C00B 127.48(15) . . ?
C008 C009 C00E 106.97(15) . . ?
C00E C009 C00B 125.45(15) . . ?
C00E C00A H00A 120.6 . . ?
C00N C00A H00A 120.6 . . ?
C00N C00A C00E 118.80(16) . . ?
C007 C00B C009 113.44(14) . . ?
C007 C00B H00B 108.9 . . ?
C007 C00B H00C 108.9 . . ?
C009 C00B H00B 108.9 . . ?
C009 C00B H00C 108.9 . . ?
H00B C00B H00C 107.7 . . ?
C00D C00C H00D 119.9 . . ?
C00D C00C C00G 120.18(17) . . ?
C00G C00C H00D 119.9 . . ?
C00C C00D H00E 120.0 . . ?
C00K C00D C00C 120.05(17) . . ?
C00K C00D H00E 120.0 . . ?
C005 C00E C009 107.16(15) . . ?
C00A C00E C005 118.96(15) . . ?
C00A C00E C009 133.87(16) . . ?
N004 C00F C006 113.69(14) . . ?
N004 C00F H00F 108.8 . . ?
N004 C00F H00G 108.8 . . ?
C006 C00F H00F 108.8 . . ?
C006 C00F H00G 108.8 . . ?
H00F C00F H00G 107.7 . . ?
C00C C00G C008 121.49(16) . . ?
C00C C00G C00H 119.01(16) . . ?
C00H C00G C008 119.50(15) . . ?
C00G C00H H00H 119.6 . . ?
C00J C00H C00G 120.81(17) . . ?
C00J C00H H00H 119.6 . . ?
C007 C00I H00I 109.5 . . ?
C007 C00I H00J 119.3(14) . . ?
H00I C00I H00J 131.2 . . ?
C00H C00J H00K 120.2 . . ?
C00H C00J C00K 119.57(17) . . ?
C00K C00J H00K 120.2 . . ?
C00D C00K C00J 120.37(17) . . ?
C00D C00K H00L 119.8 . . ?
C00J C00K H00L 119.8 . . ?
O002 C00L H00M 110.3 . . ?
O002 C00L H00N 110.3 . . ?
O002 C00L C00P 107.03(16) . . ?
H00M C00L H00N 108.6 . . ?
C00P C00L H00M 110.3 . . ?
C00P C00L H00N 110.3 . . ?
C005 C00M H00O 121.4 . . ?
C00O C00M C005 117.20(16) . . ?
C00O C00M H00O 121.4 . . ?
C00A C00N H00P 119.4 . . ?
C00A C00N C00O 121.14(16) . . ?
C00O C00N H00P 119.4 . . ?
C00M C00O C00N 121.42(16) . . ?
C00M C00O H00Q 119.3 . . ?
C00N C00O H00Q 119.3 . . ?
C00L C00P H00R 109.5 . . ?
C00L C00P H00S 109.5 . . ?
C00L C00P H00T 109.5 . . ?
H00R C00P H00S 109.5 . . ?
H00R C00P H00T 109.5 . . ?
H00S C00P H00T 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
Br01 C007 C00B C009 -65.25(17) . . . . ?
O002 C006 C00F N004 -178.77(14) . . . . ?
O003 C006 C00F N004 2.3(3) . . . . ?
N004 C005 C00E C009 1.71(18) . . . . ?
N004 C005 C00E C00A -177.63(14) . . . . ?
N004 C005 C00M C00O 178.70(16) . . . . ?
N004 C008 C009 C00B 177.62(15) . . . . ?
N004 C008 C009 C00E 0.91(19) . . . . ?
N004 C008 C00G C00C 124.16(18) . . . . ?
N004 C008 C00G C00H -56.7(2) . . . . ?
C005 N004 C008 C009 0.15(18) . . . . ?
C005 N004 C008 C00G 173.94(14) . . . . ?
C005 N004 C00F C006 -89.16(19) . . . . ?
C005 C00M C00O C00N -0.2(3) . . . . ?
C006 O002 C00L C00P 175.43(17) . . . . ?
C008 N004 C005 C00E -1.18(18) . . . . ?
C008 N004 C005 C00M 177.69(17) . . . . ?
C008 N004 C00F C006 105.36(18) . . . . ?
C008 C009 C00B C007 121.96(19) . . . . ?
C008 C009 C00E C005 -1.61(18) . . . . ?
C008 C009 C00E C00A 177.60(18) . . . . ?
C008 C00G C00H C00J -179.26(16) . . . . ?
C009 C008 C00G C00C -63.5(3) . . . . ?
C009 C008 C00G C00H 115.6(2) . . . . ?
C00A C00N C00O C00M 2.2(3) . . . . ?
C00B C009 C00E C005 -178.40(15) . . . . ?
C00B C009 C00E C00A 0.8(3) . . . . ?
C00C C00D C00K C00J -0.5(3) . . . . ?
C00C C00G C00H C00J -0.1(3) . . . . ?
C00D C00C C00G C008 179.41(16) . . . . ?
C00D C00C C00G C00H 0.3(3) . . . . ?
C00E C005 C00M C00O -2.6(2) . . . . ?
C00E C009 C00B C007 -61.9(2) . . . . ?
C00E C00A C00N C00O -1.3(3) . . . . ?
C00F N004 C005 C00E -168.79(15) . . . . ?
C00F N004 C005 C00M 10.1(3) . . . . ?
C00F N004 C008 C009 167.55(15) . . . . ?
C00F N004 C008 C00G -18.7(2) . . . . ?
C00G C008 C009 C00B 4.7(3) . . . . ?
C00G C008 C009 C00E -172.04(16) . . . . ?
C00G C00C C00D C00K 0.0(3) . . . . ?
C00G C00H C00J C00K -0.3(3) . . . . ?
C00H C00J C00K C00D 0.6(3) . . . . ?
C00I C007 C00B C009 114.3(2) . . . . ?
C00L O002 C006 O003 3.6(3) . . . . ?
C00L O002 C006 C00F -175.34(15) . . . . ?
C00M C005 C00E C009 -177.25(15) . . . . ?
C00M C005 C00E C00A 3.4(2) . . . . ?
C00N C00A C00E C005 -1.4(2) . . . . ?
C00N C00A C00E C009 179.50(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.232
_oxdiff_exptl_absorpt_empirical_full_min 0.605
####################################################################### 
# 
# 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_dtr-432_auto
_database_code_depnum_ccdc_archive 'CCDC 2343031'
_audit_update_record             
;
2024-03-24 deposited with the CCDC.	2025-03-05 downloaded from the CCDC.
;
_audit_creation_date             2024-01-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H19 Br F N O2'
_chemical_formula_sum            'C21 H19 Br F N O2'
_chemical_formula_weight         416.28
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O Br F '
_chemical_oxdiff_usercomment     11-07-2023
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   9.0327(5)
_cell_length_b                   19.2302(12)
_cell_length_c                   11.7338(7)
_cell_angle_alpha                90
_cell_angle_beta                 103.989(6)
_cell_angle_gamma                90
_cell_volume                     1977.7(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4417
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.7820
_cell_measurement_theta_min      3.3240
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.101
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82376
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.69a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12933
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.258
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -6.00  69.00   0.50    4.00    --    5.54  38.00 120.00  150
  2  ω     -3.00  24.00   0.50    4.00    --    5.54 -99.00  30.00   54
  3  ω    -11.00  15.00   0.50    4.00    --   -5.23 -99.00   0.00   52
  4  ω    -76.00   2.00   0.50    4.00    --   -5.23 -38.00-150.00  156
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0315814000
_diffrn_orient_matrix_UB_12      -0.0183451000
_diffrn_orient_matrix_UB_13      -0.0526315000
_diffrn_orient_matrix_UB_21      -0.0218974000
_diffrn_orient_matrix_UB_22      0.0319602000
_diffrn_orient_matrix_UB_23      -0.0295626000
_diffrn_orient_matrix_UB_31      0.0712299000
_diffrn_orient_matrix_UB_32      0.0016725000
_diffrn_orient_matrix_UB_33      -0.0153265000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3080
_reflns_number_total             4036
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.69a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.69a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.69a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         4036
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0383
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0325P)²+0.7828P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0817
_refine_ls_wR_factor_ref         0.0872
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00C(H00A,H00B), C00H(H00C,H00G), C00P(H00O,H00P)
2.b Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00E(H00E), C00F(H00F), C00I(H00I), C00J(H00J), C00K(H00K),
 C00M(H00M), C00N(H00N)
2.c Idealised Me refined as rotating group:
 C00Q(H00Q,H00R,H00S)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Br Br 0.65333(3) 0.28858(2) 0.36719(3) 0.06839(13) Uani 1 1 d . . . . .
F002 F 0.8798(3) 0.26673(9) 1.01413(15) 0.0900(6) Uani 1 1 d . . . . .
N003 N 0.70168(19) 0.50204(10) 0.61501(15) 0.0407(4) Uani 1 1 d . . . . .
O004 O 0.5816(2) 0.58395(12) 0.85441(16) 0.0700(6) Uani 1 1 d . . . . .
O005 O 0.7990(2) 0.59928(11) 0.80101(17) 0.0720(6) Uani 1 1 d . . . . .
C006 C 0.7073(2) 0.53530(12) 0.51187(19) 0.0399(5) Uani 1 1 d . . . . .
C007 C 0.7850(2) 0.49138(12) 0.44918(18) 0.0395(5) Uani 1 1 d . . . . .
C008 C 0.8238(2) 0.42909(12) 0.51660(18) 0.0387(5) Uani 1 1 d . . . . .
C009 C 0.6767(3) 0.57287(13) 0.7868(2) 0.0451(5) Uani 1 1 d . . . . .
C00A C 0.7724(2) 0.43692(12) 0.61708(19) 0.0396(5) Uani 1 1 d . . . . .
C00B C 0.7958(2) 0.39199(12) 0.72171(19) 0.0419(5) Uani 1 1 d . . . . .
C00C C 0.6041(2) 0.52289(13) 0.6911(2) 0.0441(5) Uani 1 1 d . . . . .
H00A H 0.573341 0.481579 0.726884 0.053 Uiso 1 1 calc R U . . .
H00B H 0.512589 0.544148 0.643313 0.053 Uiso 1 1 calc R U . . .
C00D C 0.8093(3) 0.51487(13) 0.3420(2) 0.0478(6) Uani 1 1 d . . . . .
H00D H 0.861785 0.487490 0.299532 0.057 Uiso 1 1 calc R U . . .
C00E C 0.6491(3) 0.59970(13) 0.4687(2) 0.0483(6) Uani 1 1 d . . . . .
H00E H 0.595790 0.627467 0.509991 0.058 Uiso 1 1 calc R U . . .
C00F C 0.8776(3) 0.41657(13) 0.8303(2) 0.0505(6) Uani 1 1 d . . . . .
H00F H 0.913929 0.462018 0.836691 0.061 Uiso 1 1 calc R U . . .
C00G C 0.8440(3) 0.33378(12) 0.3728(2) 0.0463(5) Uani 1 1 d . . . . .
C00H C 0.9143(2) 0.36935(12) 0.4868(2) 0.0449(5) Uani 1 1 d . . . . .
H00C H 1.014517 0.386224 0.483771 0.054 Uiso 1 1 calc R U . . .
H00G H 0.928362 0.335319 0.549504 0.054 Uiso 1 1 calc R U . . .
C00I C 0.9058(3) 0.37470(15) 0.9286(2) 0.0585(7) Uani 1 1 d . . . . .
H00I H 0.960593 0.391338 1.001000 0.070 Uiso 1 1 calc R U . . .
C00J C 0.6736(3) 0.62077(14) 0.3625(2) 0.0555(6) Uani 1 1 d . . . . .
H00J H 0.635854 0.663517 0.331472 0.067 Uiso 1 1 calc R U . . .
C00K C 0.7426(3) 0.32404(13) 0.7145(2) 0.0510(6) Uani 1 1 d . . . . .
H00K H 0.687455 0.306740 0.642752 0.061 Uiso 1 1 calc R U . . .
C00L C 0.8513(3) 0.30826(15) 0.9171(2) 0.0590(7) Uani 1 1 d . . . . .
C00M C 0.7707(3) 0.28164(14) 0.8129(2) 0.0603(7) Uani 1 1 d . . . . .
H00M H 0.735422 0.236051 0.807868 0.072 Uiso 1 1 calc R U . . .
C00N C 0.7540(3) 0.57912(14) 0.3007(2) 0.0563(6) Uani 1 1 d . . . . .
H00N H 0.770538 0.595163 0.230071 0.068 Uiso 1 1 calc R U . . .
C00O C 0.8991(4) 0.33045(18) 0.2803(3) 0.0712(8) Uani 1 1 d . . . . .
C00P C 0.6261(4) 0.6356(2) 0.9478(3) 0.0935(12) Uani 1 1 d . . . . .
H00O H 0.648386 0.679620 0.915271 0.112 Uiso 1 1 calc R U . . .
H00P H 0.716791 0.620216 1.004818 0.112 Uiso 1 1 calc R U . . .
C00Q C 0.4994(5) 0.6437(3) 1.0041(3) 0.1302(19) Uani 1 1 d . . . . .
H00Q H 0.413063 0.662991 0.948817 0.195 Uiso 1 1 calc R U . . .
H00R H 0.529315 0.674316 1.070274 0.195 Uiso 1 1 calc R U . . .
H00S H 0.472595 0.599148 1.030073 0.195 Uiso 1 1 calc R U . . .
H00H H 0.846(3) 0.3070(16) 0.210(3) 0.075(9) Uiso 1 1 d . . . . .
H00L H 0.990(3) 0.3522(15) 0.281(2) 0.067(8) Uiso 1 1 d . . . . .


_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
Br C00G 1.916(2) . ?
F002 C00L 1.364(3) . ?
N003 C006 1.380(3) . ?
N003 C00A 1.403(3) . ?
N003 C00C 1.454(3) . ?
O004 C009 1.320(3) . ?
O004 C00P 1.461(3) . ?
O005 C009 1.190(3) . ?
C006 C007 1.413(3) . ?
C006 C00E 1.392(3) . ?
C007 C008 1.431(3) . ?
C007 C00D 1.402(3) . ?
C008 C00A 1.376(3) . ?
C008 C00H 1.500(3) . ?
C009 C00C 1.503(3) . ?
C00A C00B 1.474(3) . ?
C00B C00F 1.392(3) . ?
C00B C00K 1.388(3) . ?
C00C H00A 0.9700 . ?
C00C H00B 0.9700 . ?
C00D H00D 0.9300 . ?
C00D C00N 1.376(4) . ?
C00E H00E 0.9300 . ?
C00E C00J 1.378(3) . ?
C00F H00F 0.9300 . ?
C00F C00I 1.379(4) . ?
C00G C00H 1.499(3) . ?
C00G C00O 1.301(4) . ?
C00H H00C 0.9700 . ?
C00H H00G 0.9700 . ?
C00I H00I 0.9300 . ?
C00I C00L 1.364(4) . ?
C00J H00J 0.9300 . ?
C00J C00N 1.396(4) . ?
C00K H00K 0.9300 . ?
C00K C00M 1.385(4) . ?
C00L C00M 1.362(4) . ?
C00M H00M 0.9300 . ?
C00N H00N 0.9300 . ?
C00O H00H 0.96(3) . ?
C00O H00L 0.92(3) . ?
C00P H00O 0.9700 . ?
C00P H00P 0.9700 . ?
C00P C00Q 1.461(5) . ?
C00Q H00Q 0.9600 . ?
C00Q H00R 0.9600 . ?
C00Q H00S 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C006 N003 C00A 108.42(17) . . ?
C006 N003 C00C 124.49(19) . . ?
C00A N003 C00C 125.18(19) . . ?
C009 O004 C00P 117.4(2) . . ?
N003 C006 C007 107.9(2) . . ?
N003 C006 C00E 129.9(2) . . ?
C00E C006 C007 122.2(2) . . ?
C006 C007 C008 107.36(19) . . ?
C00D C007 C006 118.6(2) . . ?
C00D C007 C008 134.0(2) . . ?
C007 C008 C00H 125.9(2) . . ?
C00A C008 C007 107.09(19) . . ?
C00A C008 C00H 126.8(2) . . ?
O004 C009 C00C 108.80(19) . . ?
O005 C009 O004 124.3(2) . . ?
O005 C009 C00C 126.9(2) . . ?
N003 C00A C00B 120.71(18) . . ?
C008 C00A N003 109.22(19) . . ?
C008 C00A C00B 129.7(2) . . ?
C00F C00B C00A 120.1(2) . . ?
C00K C00B C00A 121.5(2) . . ?
C00K C00B C00F 118.4(2) . . ?
N003 C00C C009 114.52(18) . . ?
N003 C00C H00A 108.6 . . ?
N003 C00C H00B 108.6 . . ?
C009 C00C H00A 108.6 . . ?
C009 C00C H00B 108.6 . . ?
H00A C00C H00B 107.6 . . ?
C007 C00D H00D 120.6 . . ?
C00N C00D C007 118.9(2) . . ?
C00N C00D H00D 120.6 . . ?
C006 C00E H00E 121.2 . . ?
C00J C00E C006 117.5(2) . . ?
C00J C00E H00E 121.2 . . ?
C00B C00F H00F 119.4 . . ?
C00I C00F C00B 121.1(2) . . ?
C00I C00F H00F 119.4 . . ?
C00H C00G Br 114.93(16) . . ?
C00O C00G Br 118.1(2) . . ?
C00O C00G C00H 127.0(3) . . ?
C008 C00H H00C 108.6 . . ?
C008 C00H H00G 108.6 . . ?
C00G C00H C008 114.83(19) . . ?
C00G C00H H00C 108.6 . . ?
C00G C00H H00G 108.6 . . ?
H00C C00H H00G 107.5 . . ?
C00F C00I H00I 120.8 . . ?
C00L C00I C00F 118.3(2) . . ?
C00L C00I H00I 120.8 . . ?
C00E C00J H00J 119.4 . . ?
C00E C00J C00N 121.2(2) . . ?
C00N C00J H00J 119.4 . . ?
C00B C00K H00K 119.6 . . ?
C00M C00K C00B 120.8(2) . . ?
C00M C00K H00K 119.6 . . ?
F002 C00L C00I 118.3(3) . . ?
C00M C00L F002 118.8(3) . . ?
C00M C00L C00I 122.9(2) . . ?
C00K C00M H00M 120.8 . . ?
C00L C00M C00K 118.5(3) . . ?
C00L C00M H00M 120.8 . . ?
C00D C00N C00J 121.5(2) . . ?
C00D C00N H00N 119.3 . . ?
C00J C00N H00N 119.3 . . ?
C00G C00O H00H 121.7(19) . . ?
C00G C00O H00L 119.4(18) . . ?
H00H C00O H00L 119(3) . . ?
O004 C00P H00O 110.1 . . ?
O004 C00P H00P 110.1 . . ?
O004 C00P C00Q 108.0(3) . . ?
H00O C00P H00P 108.4 . . ?
C00Q C00P H00O 110.1 . . ?
C00Q C00P H00P 110.1 . . ?
C00P C00Q H00Q 109.5 . . ?
C00P C00Q H00R 109.5 . . ?
C00P C00Q H00S 109.5 . . ?
H00Q C00Q H00R 109.5 . . ?
H00Q C00Q H00S 109.5 . . ?
H00R C00Q H00S 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
Br C00G C00H C008 -64.2(2) . . . . ?
F002 C00L C00M C00K -179.8(2) . . . . ?
N003 C006 C007 C008 1.4(2) . . . . ?
N003 C006 C007 C00D -178.17(18) . . . . ?
N003 C006 C00E C00J 179.0(2) . . . . ?
N003 C00A C00B C00F -57.1(3) . . . . ?
N003 C00A C00B C00K 125.2(2) . . . . ?
O004 C009 C00C N003 -175.6(2) . . . . ?
O005 C009 C00C N003 4.8(4) . . . . ?
C006 N003 C00A C008 0.6(2) . . . . ?
C006 N003 C00A C00B 174.55(18) . . . . ?
C006 N003 C00C C009 -91.6(3) . . . . ?
C006 C007 C008 C00A -1.0(2) . . . . ?
C006 C007 C008 C00H -176.64(19) . . . . ?
C006 C007 C00D C00N -1.2(3) . . . . ?
C006 C00E C00J C00N -0.1(4) . . . . ?
C007 C006 C00E C00J -1.8(3) . . . . ?
C007 C008 C00A N003 0.3(2) . . . . ?
C007 C008 C00A C00B -173.0(2) . . . . ?
C007 C008 C00H C00G -61.4(3) . . . . ?
C007 C00D C00N C00J -0.6(4) . . . . ?
C008 C007 C00D C00N 179.4(2) . . . . ?
C008 C00A C00B C00F 115.5(3) . . . . ?
C008 C00A C00B C00K -62.2(3) . . . . ?
C009 O004 C00P C00Q 175.1(3) . . . . ?
C00A N003 C006 C007 -1.2(2) . . . . ?
C00A N003 C006 C00E 178.1(2) . . . . ?
C00A N003 C00C C009 105.9(2) . . . . ?
C00A C008 C00H C00G 123.8(2) . . . . ?
C00A C00B C00F C00I -177.6(2) . . . . ?
C00A C00B C00K C00M 177.5(2) . . . . ?
C00B C00F C00I C00L -0.1(4) . . . . ?
C00B C00K C00M C00L 0.3(4) . . . . ?
C00C N003 C006 C007 -166.11(18) . . . . ?
C00C N003 C006 C00E 13.2(3) . . . . ?
C00C N003 C00A C008 165.36(18) . . . . ?
C00C N003 C00A C00B -20.7(3) . . . . ?
C00D C007 C008 C00A 178.4(2) . . . . ?
C00D C007 C008 C00H 2.8(4) . . . . ?
C00E C006 C007 C008 -177.98(19) . . . . ?
C00E C006 C007 C00D 2.5(3) . . . . ?
C00E C00J C00N C00D 1.3(4) . . . . ?
C00F C00B C00K C00M -0.2(3) . . . . ?
C00F C00I C00L F002 179.7(2) . . . . ?
C00F C00I C00L C00M 0.1(4) . . . . ?
C00H C008 C00A N003 175.86(19) . . . . ?
C00H C008 C00A C00B 2.6(4) . . . . ?
C00I C00L C00M C00K -0.2(4) . . . . ?
C00K C00B C00F C00I 0.1(3) . . . . ?
C00O C00G C00H C008 116.2(3) . . . . ?
C00P O004 C009 O005 4.2(4) . . . . ?
C00P O004 C009 C00C -175.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.221
_oxdiff_exptl_absorpt_empirical_full_min 0.813
####################################################################### 
# 
# 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_dtr-67-lt_auto
_database_code_depnum_ccdc_archive 'CCDC 2348444'
_audit_update_record             
;
2024-04-15 deposited with the CCDC.	2025-03-05 downloaded from the CCDC.
;
_audit_creation_date             2024-04-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H23 N O2'
_chemical_formula_sum            'C25 H23 N O2'
_chemical_formula_weight         369.44
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   11.4169(3)
_cell_length_b                   8.2709(2)
_cell_length_c                   20.4762(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.528(2)
_cell_angle_gamma                90
_cell_volume                     1932.84(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    19097
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      30.4340
_cell_measurement_theta_min      3.2200
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.106a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0623
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            38274
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.186
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -19.00  67.00   0.50    1.80    --   -5.53  38.00 -90.00  172
  2  ω    -78.00   8.00   0.50    1.80    --   -5.53 -38.00 -30.00  172
  3  ω    -67.00 -20.00   0.50    1.80    --    5.69 -38.00  30.00   94
  4  ω    -20.00  67.00   0.50    1.80    --   -5.53  57.00 120.00  174
  5  ω    -81.00   7.00   0.50    1.80    --   -5.53 -19.00 150.00  176
  6  ω    -78.00   9.00   0.50    1.80    --   -5.53 -57.00 120.00  174
  7  ω    -23.00  27.00   0.50    1.80    --   -5.53 -99.00  60.00  100
  8  ω    -23.00  27.00   0.50    1.80    --   -5.53 -99.00 -90.00  100
  9  ω    -23.00  27.00   0.50    1.80    --   -5.53 -99.00-150.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0426680000
_diffrn_orient_matrix_UB_12      0.0383341000
_diffrn_orient_matrix_UB_13      0.0192251000
_diffrn_orient_matrix_UB_21      -0.0451684000
_diffrn_orient_matrix_UB_22      -0.0342722000
_diffrn_orient_matrix_UB_23      -0.0200560000
_diffrn_orient_matrix_UB_31      -0.0013347000
_diffrn_orient_matrix_UB_32      -0.0686146000
_diffrn_orient_matrix_UB_33      0.0207198000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3567
_reflns_number_total             3949
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.106a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.106a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.106a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.569
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.109
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.176
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3949
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1162
_refine_ls_R_factor_gt           0.1112
_refine_ls_restrained_S_all      1.176
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0520P)²+15.9612P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2973
_refine_ls_wR_factor_ref         0.2989
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00H(H00B,H00C), C00K(H00H,H00K), C00R(H00R,H00S)
2.b Aromatic/amide H refined with riding coordinates:
 C004(H004), C00A(H00A), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G),
 C00I(H00I), C00J(H00J), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O),
 C00P(H00P), C00Q(H00Q)
2.c Idealised Me refined as rotating group:
 C00S(H00T,H00U,H00V)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O001 O 0.9020(3) 0.4170(5) 0.38569(18) 0.0288(9) Uani 1 1 d . . . . .
O002 O 0.7586(3) 0.2601(5) 0.42480(18) 0.0305(9) Uani 1 1 d . . . . .
N003 N 0.7596(3) 0.4849(5) 0.27343(19) 0.0211(9) Uani 1 1 d . . . . .
C004 C 0.4381(4) 0.7676(7) 0.3215(2) 0.0242(11) Uani 1 1 d . . . . .
H004 H 0.360121 0.727461 0.320077 0.029 Uiso 1 1 calc R U . . .
C005 C 0.8057(4) 0.3623(6) 0.3813(2) 0.0222(10) Uani 1 1 d . . . . .
C006 C 0.7385(4) 0.8511(6) 0.1094(2) 0.0203(10) Uani 1 1 d . . . . .
C007 C 0.8719(4) 0.5646(6) 0.1907(2) 0.0210(10) Uani 1 1 d . . . . .
C008 C 0.6415(4) 0.7363(7) 0.2941(2) 0.0218(10) Uani 1 1 d . . . . .
C009 C 0.8436(4) 0.4324(6) 0.2310(2) 0.0210(10) Uani 1 1 d . . . . .
C00A C 0.9559(4) 0.5416(7) 0.1425(2) 0.0238(11) Uani 1 1 d . . . . .
H00A H 0.976828 0.627731 0.114377 0.029 Uiso 1 1 calc R U . . .
C00B C 0.8027(4) 0.6983(6) 0.2097(2) 0.0197(10) Uani 1 1 d . . . . .
C00C C 0.7344(4) 0.6479(6) 0.2605(2) 0.0198(10) Uani 1 1 d . . . . .
C00D C 0.5776(5) 0.9687(7) 0.3553(2) 0.0266(11) Uani 1 1 d . . . . .
H00D H 0.595696 1.066798 0.377493 0.032 Uiso 1 1 calc R U . . .
C00E C 0.8966(4) 0.2816(6) 0.2255(3) 0.0239(10) Uani 1 1 d . . . . .
H00E H 0.877718 0.195282 0.254010 0.029 Uiso 1 1 calc R U . . .
C00F C 0.6183(4) 0.8362(6) 0.1052(2) 0.0240(11) Uani 1 1 d . . . . .
H00F H 0.574721 0.835679 0.144083 0.029 Uiso 1 1 calc R U . . .
C00G C 0.6666(4) 0.8828(6) 0.3262(2) 0.0236(10) Uani 1 1 d . . . . .
H00G H 0.744519 0.923060 0.327987 0.028 Uiso 1 1 calc R U . . .
C00H C 0.7156(4) 0.3891(6) 0.3265(2) 0.0229(10) Uani 1 1 d . . . . .
H00B H 0.689687 0.282838 0.309188 0.027 Uiso 1 1 calc R U . . .
H00C H 0.646401 0.443909 0.344401 0.027 Uiso 1 1 calc R U . . .
C00I C 0.5269(4) 0.6807(7) 0.2928(2) 0.0230(10) Uani 1 1 d . . . . .
H00I H 0.508898 0.581049 0.271770 0.028 Uiso 1 1 calc R U . . .
C00J C 0.4635(4) 0.9144(7) 0.3525(3) 0.0267(11) Uani 1 1 d . . . . .
H00J H 0.402955 0.975923 0.371499 0.032 Uiso 1 1 calc R U . . .
C00K C 0.8002(4) 0.8606(6) 0.1761(2) 0.0232(10) Uani 1 1 d . . . . .
H00H H 0.881434 0.899314 0.170841 0.028 Uiso 1 1 calc R U . . .
H00K H 0.759071 0.939649 0.203681 0.028 Uiso 1 1 calc R U . . .
C00L C 0.8019(5) 0.8528(7) 0.0519(3) 0.0295(12) Uani 1 1 d . . . . .
H00L H 0.884633 0.865289 0.053870 0.035 Uiso 1 1 calc R U . . .
C00M C 0.7433(5) 0.8362(7) -0.0081(3) 0.0332(13) Uani 1 1 d . . . . .
H00M H 0.786552 0.834941 -0.047128 0.040 Uiso 1 1 calc R U . . .
C00N C 0.9783(4) 0.2618(7) 0.1768(3) 0.0287(12) Uani 1 1 d . . . . .
H00N H 1.014305 0.159512 0.170884 0.034 Uiso 1 1 calc R U . . .
C00O C 0.5602(5) 0.8219(7) 0.0455(3) 0.0335(13) Uani 1 1 d . . . . .
H00O H 0.477242 0.812492 0.043445 0.040 Uiso 1 1 calc R U . . .
C00P C 0.6235(5) 0.8215(7) -0.0115(3) 0.0329(13) Uani 1 1 d . . . . .
H00P H 0.584017 0.811103 -0.052737 0.039 Uiso 1 1 calc R U . . .
C00Q C 1.0075(4) 0.3911(7) 0.1368(3) 0.0277(11) Uani 1 1 d . . . . .
H00Q H 1.064639 0.375347 0.104504 0.033 Uiso 1 1 calc R U . . .
C00R C 0.8269(5) 0.2256(8) 0.4846(3) 0.0333(13) Uani 1 1 d . . . . .
H00R H 0.870434 0.322961 0.499386 0.040 Uiso 1 1 calc R U . . .
H00S H 0.883776 0.137637 0.476974 0.040 Uiso 1 1 calc R U . . .
C00S C 0.7413(5) 0.1757(10) 0.5343(3) 0.0480(19) Uani 1 1 d . . . . .
H00T H 0.700504 0.077472 0.519518 0.072 Uiso 1 1 calc R U . . .
H00U H 0.684104 0.262490 0.540241 0.072 Uiso 1 1 calc R U . . .
H00V H 0.782799 0.154220 0.575908 0.072 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
O001 C005 1.190(6) . ?
O002 C005 1.350(6) . ?
O002 C00R 1.462(6) . ?
N003 C009 1.381(6) . ?
N003 C00C 1.402(6) . ?
N003 C00H 1.445(6) . ?
C004 H004 0.9500 . ?
C004 C00I 1.387(7) . ?
C004 C00J 1.397(8) . ?
C005 C00H 1.518(7) . ?
C006 C00F 1.378(7) . ?
C006 C00K 1.522(7) . ?
C006 C00L 1.398(7) . ?
C007 C009 1.413(7) . ?
C007 C00A 1.408(7) . ?
C007 C00B 1.420(7) . ?
C008 C00C 1.473(7) . ?
C008 C00G 1.404(7) . ?
C008 C00I 1.386(7) . ?
C009 C00E 1.392(7) . ?
C00A H00A 0.9500 . ?
C00A C00Q 1.383(8) . ?
C00B C00C 1.381(7) . ?
C00B C00K 1.508(7) . ?
C00D H00D 0.9500 . ?
C00D C00G 1.387(7) . ?
C00D C00J 1.378(7) . ?
C00E H00E 0.9500 . ?
C00E C00N 1.393(7) . ?
C00F H00F 0.9500 . ?
C00F C00O 1.380(8) . ?
C00G H00G 0.9500 . ?
C00H H00B 0.9900 . ?
C00H H00C 0.9900 . ?
C00I H00I 0.9500 . ?
C00J H00J 0.9500 . ?
C00K H00H 0.9900 . ?
C00K H00K 0.9900 . ?
C00L H00L 0.9500 . ?
C00L C00M 1.391(8) . ?
C00M H00M 0.9500 . ?
C00M C00P 1.373(8) . ?
C00N H00N 0.9500 . ?
C00N C00Q 1.394(8) . ?
C00O H00O 0.9500 . ?
C00O C00P 1.390(8) . ?
C00P H00P 0.9500 . ?
C00Q H00Q 0.9500 . ?
C00R H00R 0.9900 . ?
C00R H00S 0.9900 . ?
C00R C00S 1.489(8) . ?
C00S H00T 0.9800 . ?
C00S H00U 0.9800 . ?
C00S H00V 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
C005 O002 C00R 117.5(4) . . ?
C009 N003 C00C 109.0(4) . . ?
C009 N003 C00H 124.1(4) . . ?
C00C N003 C00H 126.5(4) . . ?
C00I C004 H004 120.1 . . ?
C00I C004 C00J 119.9(5) . . ?
C00J C004 H004 120.1 . . ?
O001 C005 O002 124.8(5) . . ?
O001 C005 C00H 127.3(4) . . ?
O002 C005 C00H 107.8(4) . . ?
C00F C006 C00K 119.8(4) . . ?
C00F C006 C00L 119.0(5) . . ?
C00L C006 C00K 121.2(5) . . ?
C009 C007 C00B 107.7(4) . . ?
C00A C007 C009 118.4(5) . . ?
C00A C007 C00B 133.8(5) . . ?
C00G C008 C00C 120.5(4) . . ?
C00I C008 C00C 121.1(5) . . ?
C00I C008 C00G 118.4(5) . . ?
N003 C009 C007 107.3(4) . . ?
N003 C009 C00E 130.0(5) . . ?
C00E C009 C007 122.7(5) . . ?
C007 C00A H00A 120.7 . . ?
C00Q C00A C007 118.7(5) . . ?
C00Q C00A H00A 120.7 . . ?
C007 C00B C00K 124.9(4) . . ?
C00C C00B C007 107.5(4) . . ?
C00C C00B C00K 127.4(4) . . ?
N003 C00C C008 122.4(4) . . ?
C00B C00C N003 108.4(4) . . ?
C00B C00C C008 129.0(5) . . ?
C00G C00D H00D 119.4 . . ?
C00J C00D H00D 119.4 . . ?
C00J C00D C00G 121.2(5) . . ?
C009 C00E H00E 121.2 . . ?
C009 C00E C00N 117.6(5) . . ?
C00N C00E H00E 121.2 . . ?
C006 C00F H00F 119.4 . . ?
C006 C00F C00O 121.2(5) . . ?
C00O C00F H00F 119.4 . . ?
C008 C00G H00G 120.0 . . ?
C00D C00G C008 120.1(5) . . ?
C00D C00G H00G 120.0 . . ?
N003 C00H C005 113.2(4) . . ?
N003 C00H H00B 108.9 . . ?
N003 C00H H00C 108.9 . . ?
C005 C00H H00B 108.9 . . ?
C005 C00H H00C 108.9 . . ?
H00B C00H H00C 107.8 . . ?
C004 C00I H00I 119.3 . . ?
C008 C00I C004 121.4(5) . . ?
C008 C00I H00I 119.3 . . ?
C004 C00J H00J 120.4 . . ?
C00D C00J C004 119.1(5) . . ?
C00D C00J H00J 120.4 . . ?
C006 C00K H00H 109.3 . . ?
C006 C00K H00K 109.3 . . ?
C00B C00K C006 111.4(4) . . ?
C00B C00K H00H 109.3 . . ?
C00B C00K H00K 109.3 . . ?
H00H C00K H00K 108.0 . . ?
C006 C00L H00L 120.1 . . ?
C00M C00L C006 119.7(5) . . ?
C00M C00L H00L 120.1 . . ?
C00L C00M H00M 119.7 . . ?
C00P C00M C00L 120.6(5) . . ?
C00P C00M H00M 119.7 . . ?
C00E C00N H00N 119.8 . . ?
C00E C00N C00Q 120.4(5) . . ?
C00Q C00N H00N 119.8 . . ?
C00F C00O H00O 120.1 . . ?
C00F C00O C00P 119.7(5) . . ?
C00P C00O H00O 120.1 . . ?
C00M C00P C00O 119.8(5) . . ?
C00M C00P H00P 120.1 . . ?
C00O C00P H00P 120.1 . . ?
C00A C00Q C00N 122.1(5) . . ?
C00A C00Q H00Q 118.9 . . ?
C00N C00Q H00Q 118.9 . . ?
O002 C00R H00R 110.5 . . ?
O002 C00R H00S 110.5 . . ?
O002 C00R C00S 106.4(4) . . ?
H00R C00R H00S 108.6 . . ?
C00S C00R H00R 110.5 . . ?
C00S C00R H00S 110.5 . . ?
C00R C00S H00T 109.5 . . ?
C00R C00S H00U 109.5 . . ?
C00R C00S H00V 109.5 . . ?
H00T C00S H00U 109.5 . . ?
H00T C00S H00V 109.5 . . ?
H00U C00S H00V 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
O001 C005 C00H N003 4.0(8) . . . . ?
O002 C005 C00H N003 -174.6(4) . . . . ?
N003 C009 C00E C00N 178.9(5) . . . . ?
C005 O002 C00R C00S 155.7(5) . . . . ?
C006 C00F C00O C00P 0.4(9) . . . . ?
C006 C00L C00M C00P 1.4(9) . . . . ?
C007 C009 C00E C00N -1.7(7) . . . . ?
C007 C00A C00Q C00N 0.5(8) . . . . ?
C007 C00B C00C N003 -0.1(5) . . . . ?
C007 C00B C00C C008 -174.8(5) . . . . ?
C007 C00B C00K C006 71.0(6) . . . . ?
C009 N003 C00C C008 175.2(4) . . . . ?
C009 N003 C00C C00B 0.1(5) . . . . ?
C009 N003 C00H C005 69.2(6) . . . . ?
C009 C007 C00A C00Q -0.2(7) . . . . ?
C009 C007 C00B C00C 0.1(5) . . . . ?
C009 C007 C00B C00K -175.9(4) . . . . ?
C009 C00E C00N C00Q 1.9(7) . . . . ?
C00A C007 C009 N003 -179.6(4) . . . . ?
C00A C007 C009 C00E 0.9(7) . . . . ?
C00A C007 C00B C00C 179.5(5) . . . . ?
C00A C007 C00B C00K 3.5(8) . . . . ?
C00B C007 C009 N003 -0.1(5) . . . . ?
C00B C007 C009 C00E -179.6(4) . . . . ?
C00B C007 C00A C00Q -179.6(5) . . . . ?
C00C N003 C009 C007 0.0(5) . . . . ?
C00C N003 C009 C00E 179.5(5) . . . . ?
C00C N003 C00H C005 -103.9(5) . . . . ?
C00C C008 C00G C00D 177.2(5) . . . . ?
C00C C008 C00I C004 -176.7(4) . . . . ?
C00C C00B C00K C006 -104.2(6) . . . . ?
C00E C00N C00Q C00A -1.3(8) . . . . ?
C00F C006 C00K C00B 73.7(6) . . . . ?
C00F C006 C00L C00M -1.3(8) . . . . ?
C00F C00O C00P C00M -0.4(9) . . . . ?
C00G C008 C00C N003 126.3(5) . . . . ?
C00G C008 C00C C00B -59.6(7) . . . . ?
C00G C008 C00I C004 0.9(7) . . . . ?
C00G C00D C00J C004 1.9(8) . . . . ?
C00H N003 C009 C007 -174.1(4) . . . . ?
C00H N003 C009 C00E 5.3(8) . . . . ?
C00H N003 C00C C008 -10.8(7) . . . . ?
C00H N003 C00C C00B 174.0(4) . . . . ?
C00I C004 C00J C00D -1.4(7) . . . . ?
C00I C008 C00C N003 -56.1(6) . . . . ?
C00I C008 C00C C00B 117.9(6) . . . . ?
C00I C008 C00G C00D -0.4(7) . . . . ?
C00J C004 C00I C008 0.0(7) . . . . ?
C00J C00D C00G C008 -1.0(8) . . . . ?
C00K C006 C00F C00O -177.9(5) . . . . ?
C00K C006 C00L C00M 177.0(5) . . . . ?
C00K C00B C00C N003 175.8(4) . . . . ?
C00K C00B C00C C008 1.1(8) . . . . ?
C00L C006 C00F C00O 0.4(8) . . . . ?
C00L C006 C00K C00B -104.5(5) . . . . ?
C00L C00M C00P C00O -0.5(9) . . . . ?
C00R O002 C005 O001 5.7(8) . . . . ?
C00R O002 C005 C00H -175.7(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.733
_oxdiff_exptl_absorpt_empirical_full_min 0.660
