# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_2h
_database_code_depnum_ccdc_archive 'CCDC 2304259'
_audit_update_record             
;
2024-04-26 deposited with the CCDC.	2025-01-24 downloaded from the CCDC.
;
_audit_creation_date             2023-10-23
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H24 F N'
_chemical_formula_sum            'C27 H24 F N'
_chemical_formula_weight         381.47
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N F'
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'
F F 0.0727 0.0534 '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'

_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.91320(10)
_cell_length_b                   5.92270(10)
_cell_length_c                   19.3324(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.3780(10)
_cell_angle_gamma                90
_cell_volume                     1003.87(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6268
_cell_measurement_temperature    99.98(13)
_cell_measurement_theta_max      73.8920
_cell_measurement_theta_min      4.6370
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.620
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64689
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            10432
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.371
_diffrn_reflns_theta_min         4.651
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(13)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -33.00  22.00   0.50    0.50    --    0.00 -82.00 -60.00  110
  2  ω    -33.00  12.00   0.50    0.50    --    0.00 -19.00 -60.00   90
  3  ω    -32.00  20.00   0.50    0.50    --    0.00 -82.00  60.00  104
  4  ω    -29.00  21.00   0.50    0.50    --    0.00 -82.00-180.00  100
  5  ω    -88.00 -59.00   0.50    0.50    --    0.00 -19.00 -60.00   58
  6  ω     80.00 120.00   0.50    0.86    --   95.80  45.00  30.00   80
  7  ω    110.00 185.00   0.50    0.86    --   95.80  75.00 -68.68  150
  8  ω     75.00 101.00   0.50    0.86    --   95.80  67.00 -52.08   52
  9  ω     73.00  98.00   0.50    0.86    --   95.80  61.00 -90.00   50
 10  ω     48.00  87.00   0.50    0.86    --   95.80 -45.00 -30.00   78
 11  ω    121.00 184.00   0.50    0.86    --   95.80  61.00 -90.00  126
 12  ω     76.00 112.00   0.50    0.86    --   95.80  45.00 -60.00   72
 13  ω      6.00 118.00   0.50    0.86    --   95.80 -61.00 -30.00  224
 14  ω     70.00  96.00   0.50    0.86    --   95.80  75.00 -68.68   52
 15  ω     79.00 185.00   0.50    0.86    --   95.80  30.00-180.00  212
 16  ω    110.00 166.00   0.50    0.86    --   95.80  82.00  90.00  112
 17  ω     73.00 185.00   0.50    0.86    --   95.80  15.00  90.00  224
 18  ω     73.00  99.00   0.50    0.86    --   95.80  61.00 -60.00   52
 19  ω      6.00  47.00   0.50    0.86    --   95.80 -61.00 -90.00   82
 20  ω     76.00 106.00   0.50    0.86    --   95.80 -61.00 -90.00   60
 21  ω     72.00 134.00   0.50    0.86    --   95.80  61.00   0.00  124
 22  ω    139.00 165.00   0.50    0.86    --   95.80  61.00   0.00   52
 23  ω    143.00 177.00   0.50    0.86    --   95.80  45.00  30.00   68
 24  ω    136.00 184.00   0.50    0.86    --   95.80  67.00 -52.08   96
 25  ω     74.00 108.00   0.50    0.86    --   95.80  52.00  -9.46   68
 26  ω     72.00  97.00   0.50    0.86    --   95.80  61.00 -30.00   50
 27  ω     76.00 113.00   0.50    0.86    --   95.80  45.00 -30.00   74
 28  ω     69.00  95.00   0.50    0.86    --   95.80  70.00 -24.46   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0425695000
_diffrn_orient_matrix_UB_12      -0.1152800000
_diffrn_orient_matrix_UB_13      -0.0722937000
_diffrn_orient_matrix_UB_21      0.1570252000
_diffrn_orient_matrix_UB_22      0.0634264000
_diffrn_orient_matrix_UB_23      -0.0169052000
_diffrn_orient_matrix_UB_31      0.0664127000
_diffrn_orient_matrix_UB_32      -0.2244419000
_diffrn_orient_matrix_UB_33      0.0323916000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.764
_reflns_Friedel_fraction_full    0.977
_reflns_Friedel_fraction_max     0.919
_reflns_number_gt                3686
_reflns_number_total             3927
_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 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 1510 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3927
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0404
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0509P)²+0.2447P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1052
_refine_ls_wR_factor_ref         0.1070
_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 Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C17(H17),
 C18(H18), C20(H20), C21(H21), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_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
F1 F -0.05481(19) 1.0597(3) 0.63992(9) 0.0443(4) Uani 1 1 d . . . . .
N1 N 0.4868(2) 0.7706(3) 0.62746(10) 0.0265(4) Uani 1 1 d . . . . .
C1 C 0.1720(3) 0.5961(4) 0.72461(12) 0.0254(5) Uani 1 1 d . . . . .
C2 C 0.1327(3) 0.8042(4) 0.69219(12) 0.0275(5) Uani 1 1 d . . . . .
H2 H 0.209617 0.904877 0.682870 0.033 Uiso 1 1 calc R U . . .
C3 C -0.0190(3) 0.8612(4) 0.67398(13) 0.0303(5) Uani 1 1 d . . . . .
C4 C -0.1358(3) 0.7259(5) 0.68699(14) 0.0348(6) Uani 1 1 d . . . . .
H4 H -0.239351 0.770369 0.673636 0.042 Uiso 1 1 calc R U . . .
C5 C -0.0966(3) 0.5223(5) 0.72030(15) 0.0388(6) Uani 1 1 d . . . . .
H5 H -0.174609 0.425608 0.730706 0.047 Uiso 1 1 calc R U . . .
C6 C 0.0555(3) 0.4564(5) 0.73888(14) 0.0319(6) Uani 1 1 d . . . . .
H6 H 0.079862 0.315261 0.761443 0.038 Uiso 1 1 calc R U . . .
C7 C 0.3379(3) 0.5215(4) 0.73852(12) 0.0259(5) Uani 1 1 d . . . . .
H7 H 0.401943 0.657070 0.754261 0.031 Uiso 1 1 calc R U . . .
C8 C 0.3849(3) 0.4331(4) 0.67015(12) 0.0267(5) Uani 1 1 d . . . . .
H8A H 0.490427 0.374157 0.681367 0.032 Uiso 1 1 calc R U . . .
H8B H 0.317154 0.306162 0.651624 0.032 Uiso 1 1 calc R U . . .
C9 C 0.3769(2) 0.6116(4) 0.61393(12) 0.0236(5) Uani 1 1 d . . . . .
C10 C 0.2636(2) 0.6158(4) 0.55310(12) 0.0236(5) Uani 1 1 d . . . . .
C11 C 0.2710(3) 0.7895(4) 0.50502(12) 0.0270(5) Uani 1 1 d . . . . .
H11 H 0.197686 0.796746 0.462827 0.032 Uiso 1 1 calc R U . . .
C12 C 0.3847(3) 0.9510(4) 0.51853(13) 0.0290(5) Uani 1 1 d . . . . .
H12 H 0.391096 1.069063 0.485916 0.035 Uiso 1 1 calc R U . . .
C13 C 0.4884(3) 0.9362(5) 0.58064(13) 0.0299(5) Uani 1 1 d . . . . .
H13 H 0.564749 1.049314 0.590615 0.036 Uiso 1 1 calc R U . . .
C14 C 0.1367(3) 0.4448(5) 0.54001(13) 0.0300(5) Uani 1 1 d . . . . .
H14A H 0.179868 0.293794 0.536784 0.045 Uiso 1 1 calc R U . . .
H14B H 0.068017 0.480700 0.495862 0.045 Uiso 1 1 calc R U . . .
H14C H 0.079718 0.448640 0.578857 0.045 Uiso 1 1 calc R U . . .
C15 C 0.3730(3) 0.3416(5) 0.79655(14) 0.0316(6) Uani 1 1 d . . . . .
H15A H 0.326952 0.389766 0.837101 0.038 Uiso 1 1 calc R U . . .
H15B H 0.323463 0.198322 0.778618 0.038 Uiso 1 1 calc R U . . .
C16 C 0.5409(3) 0.2978(5) 0.82195(13) 0.0299(5) Uani 1 1 d . . . . .
C17 C 0.6110(4) 0.1012(5) 0.8069(2) 0.0552(10) Uani 1 1 d . . . . .
H17 H 0.553234 -0.008662 0.777660 0.066 Uiso 1 1 calc R U . . .
C18 C 0.7637(4) 0.0594(5) 0.8333(2) 0.0536(9) Uani 1 1 d . . . . .
H18 H 0.807206 -0.079444 0.822213 0.064 Uiso 1 1 calc R U . . .
C19 C 0.8544(3) 0.2136(4) 0.87513(13) 0.0267(5) Uani 1 1 d . . . . .
C20 C 0.6317(3) 0.4559(6) 0.86185(18) 0.0536(9) Uani 1 1 d . . . . .
H20 H 0.588254 0.595749 0.872033 0.064 Uiso 1 1 calc R U . . .
C21 C 0.7850(3) 0.4159(6) 0.88750(19) 0.0549(10) Uani 1 1 d . . . . .
H21 H 0.844130 0.529979 0.914223 0.066 Uiso 1 1 calc R U . . .
C22 C 1.0189(3) 0.1715(4) 0.90324(13) 0.0279(5) Uani 1 1 d . . . . .
C23 C 1.1041(3) 0.3228(5) 0.94967(14) 0.0336(6) Uani 1 1 d . . . . .
H23 H 1.056056 0.453752 0.963828 0.040 Uiso 1 1 calc R U . . .
C24 C 1.2576(3) 0.2865(6) 0.97570(15) 0.0423(7) Uani 1 1 d . . . . .
H24 H 1.313713 0.393059 1.006822 0.051 Uiso 1 1 calc R U . . .
C25 C 1.3291(3) 0.0949(6) 0.95636(16) 0.0456(8) Uani 1 1 d . . . . .
H25 H 1.433924 0.068755 0.974473 0.055 Uiso 1 1 calc R U . . .
C26 C 1.2469(3) -0.0572(6) 0.91067(18) 0.0467(7) Uani 1 1 d . . . . .
H26 H 1.295578 -0.188254 0.896994 0.056 Uiso 1 1 calc R U . . .
C27 C 1.0938(3) -0.0205(5) 0.88451(16) 0.0386(6) Uani 1 1 d . . . . .
H27 H 1.038610 -0.127673 0.853275 0.046 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
F1 C3 1.357(3) . ?
N1 C9 1.350(3) . ?
N1 C13 1.336(3) . ?
C1 C2 1.399(3) . ?
C1 C6 1.393(3) . ?
C1 C7 1.520(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.376(3) . ?
C3 C4 1.373(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.382(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.394(4) . ?
C6 H6 0.9500 . ?
C7 H7 1.0000 . ?
C7 C8 1.548(3) . ?
C7 C15 1.538(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.509(3) . ?
C9 C10 1.405(3) . ?
C10 C11 1.396(3) . ?
C10 C14 1.505(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.384(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.380(4) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.511(3) . ?
C16 C17 1.377(4) . ?
C16 C20 1.380(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.387(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.381(4) . ?
C19 C21 1.389(4) . ?
C19 C22 1.490(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.387(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.393(4) . ?
C22 C27 1.399(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.386(4) . ?
C24 H24 0.9500 . ?
C24 C25 1.385(5) . ?
C25 H25 0.9500 . ?
C25 C26 1.377(5) . ?
C26 H26 0.9500 . ?
C26 C27 1.384(4) . ?
C27 H27 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
C13 N1 C9 118.5(2) . . ?
C2 C1 C7 119.5(2) . . ?
C6 C1 C2 118.5(2) . . ?
C6 C1 C7 121.9(2) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 C1 119.1(2) . . ?
C3 C2 H2 120.5 . . ?
F1 C3 C2 118.1(2) . . ?
F1 C3 C4 118.3(2) . . ?
C4 C3 C2 123.5(2) . . ?
C3 C4 H4 121.4 . . ?
C3 C4 C5 117.3(2) . . ?
C5 C4 H4 121.4 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.1(3) . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C5 120.5(3) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C1 C7 H7 107.7 . . ?
C1 C7 C8 110.58(19) . . ?
C1 C7 C15 113.17(19) . . ?
C8 C7 H7 107.7 . . ?
C15 C7 H7 107.7 . . ?
C15 C7 C8 109.7(2) . . ?
C7 C8 H8A 109.0 . . ?
C7 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C9 C8 C7 113.1(2) . . ?
C9 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
N1 C9 C8 114.2(2) . . ?
N1 C9 C10 122.4(2) . . ?
C10 C9 C8 123.3(2) . . ?
C9 C10 C14 122.2(2) . . ?
C11 C10 C9 117.2(2) . . ?
C11 C10 C14 120.5(2) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.3(2) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 120.9 . . ?
C13 C12 C11 118.2(2) . . ?
C13 C12 H12 120.9 . . ?
N1 C13 C12 123.3(2) . . ?
N1 C13 H13 118.3 . . ?
C12 C13 H13 118.3 . . ?
C10 C14 H14A 109.5 . . ?
C10 C14 H14B 109.5 . . ?
C10 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C7 C15 H15A 108.6 . . ?
C7 C15 H15B 108.6 . . ?
H15A C15 H15B 107.6 . . ?
C16 C15 C7 114.5(2) . . ?
C16 C15 H15A 108.6 . . ?
C16 C15 H15B 108.6 . . ?
C17 C16 C15 122.5(2) . . ?
C17 C16 C20 116.7(2) . . ?
C20 C16 C15 120.8(3) . . ?
C16 C17 H17 119.1 . . ?
C16 C17 C18 121.7(3) . . ?
C18 C17 H17 119.1 . . ?
C17 C18 H18 119.0 . . ?
C19 C18 C17 122.0(3) . . ?
C19 C18 H18 119.0 . . ?
C18 C19 C21 116.1(2) . . ?
C18 C19 C22 122.5(2) . . ?
C21 C19 C22 121.4(2) . . ?
C16 C20 H20 119.2 . . ?
C16 C20 C21 121.7(3) . . ?
C21 C20 H20 119.2 . . ?
C19 C21 H21 119.1 . . ?
C20 C21 C19 121.7(3) . . ?
C20 C21 H21 119.1 . . ?
C23 C22 C19 121.0(2) . . ?
C23 C22 C27 117.3(2) . . ?
C27 C22 C19 121.7(2) . . ?
C22 C23 H23 119.3 . . ?
C24 C23 C22 121.5(3) . . ?
C24 C23 H23 119.3 . . ?
C23 C24 H24 120.0 . . ?
C25 C24 C23 120.1(3) . . ?
C25 C24 H24 120.0 . . ?
C24 C25 H25 120.3 . . ?
C26 C25 C24 119.4(3) . . ?
C26 C25 H25 120.3 . . ?
C25 C26 H26 119.8 . . ?
C25 C26 C27 120.5(3) . . ?
C27 C26 H26 119.8 . . ?
C22 C27 H27 119.4 . . ?
C26 C27 C22 121.2(3) . . ?
C26 C27 H27 119.4 . . ?

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
F1 C3 C4 C5 178.6(2) . . . . ?
N1 C9 C10 C11 1.9(3) . . . . ?
N1 C9 C10 C14 -176.9(2) . . . . ?
C1 C2 C3 F1 -177.3(2) . . . . ?
C1 C2 C3 C4 1.2(4) . . . . ?
C1 C7 C8 C9 63.3(3) . . . . ?
C1 C7 C15 C16 -168.3(2) . . . . ?
C2 C1 C6 C5 0.8(4) . . . . ?
C2 C1 C7 C8 -77.8(3) . . . . ?
C2 C1 C7 C15 158.7(2) . . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
C3 C4 C5 C6 -0.9(4) . . . . ?
C4 C5 C6 C1 0.5(4) . . . . ?
C6 C1 C2 C3 -1.6(3) . . . . ?
C6 C1 C7 C8 97.8(3) . . . . ?
C6 C1 C7 C15 -25.7(3) . . . . ?
C7 C1 C2 C3 174.1(2) . . . . ?
C7 C1 C6 C5 -174.8(2) . . . . ?
C7 C8 C9 N1 71.6(3) . . . . ?
C7 C8 C9 C10 -107.3(2) . . . . ?
C7 C15 C16 C17 -108.9(3) . . . . ?
C7 C15 C16 C20 71.1(4) . . . . ?
C8 C7 C15 C16 67.7(3) . . . . ?
C8 C9 C10 C11 -179.3(2) . . . . ?
C8 C9 C10 C14 2.0(3) . . . . ?
C9 N1 C13 C12 -1.0(3) . . . . ?
C9 C10 C11 C12 -1.1(3) . . . . ?
C10 C11 C12 C13 -0.6(3) . . . . ?
C11 C12 C13 N1 1.7(4) . . . . ?
C13 N1 C9 C8 -179.8(2) . . . . ?
C13 N1 C9 C10 -0.8(3) . . . . ?
C14 C10 C11 C12 177.6(2) . . . . ?
C15 C7 C8 C9 -171.21(19) . . . . ?
C15 C16 C17 C18 -177.0(3) . . . . ?
C15 C16 C20 C21 178.0(3) . . . . ?
C16 C17 C18 C19 -1.0(6) . . . . ?
C16 C20 C21 C19 -0.9(6) . . . . ?
C17 C16 C20 C21 -2.1(5) . . . . ?
C17 C18 C19 C21 -1.9(5) . . . . ?
C17 C18 C19 C22 -179.4(3) . . . . ?
C18 C19 C21 C20 2.8(5) . . . . ?
C18 C19 C22 C23 -175.0(3) . . . . ?
C18 C19 C22 C27 4.7(4) . . . . ?
C19 C22 C23 C24 -179.4(2) . . . . ?
C19 C22 C27 C26 179.7(3) . . . . ?
C20 C16 C17 C18 3.0(5) . . . . ?
C21 C19 C22 C23 7.6(4) . . . . ?
C21 C19 C22 C27 -172.6(3) . . . . ?
C22 C19 C21 C20 -179.6(3) . . . . ?
C22 C23 C24 C25 -0.8(4) . . . . ?
C23 C22 C27 C26 -0.6(4) . . . . ?
C23 C24 C25 C26 0.6(4) . . . . ?
C24 C25 C26 C27 -0.4(5) . . . . ?
C25 C26 C27 C22 0.4(5) . . . . ?
C27 C22 C23 C24 0.8(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 1.578
_oxdiff_exptl_absorpt_empirical_full_min 0.439
####################################################################### 
# 
# 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_6.9
_database_code_depnum_ccdc_archive 'CCDC 2351360'
_audit_update_record             
;
2024-04-26 deposited with the CCDC.	2025-01-24 downloaded from the CCDC.
;
_audit_creation_date             2023-10-24
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H21 N O2'
_chemical_formula_sum            'C23 H21 N O2'
_chemical_formula_weight         343.41
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'

_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      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'

_cell_length_a                   35.0900(10)
_cell_length_b                   14.7525(4)
_cell_length_c                   6.9356(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3590.32(18)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8067
_cell_measurement_temperature    99.98(18)
_cell_measurement_theta_max      73.9450
_cell_measurement_theta_min      3.9440
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.638
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46354
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0562
_diffrn_reflns_av_unetI/netI     0.0623
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            17944
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.338
_diffrn_reflns_theta_min         2.518
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(18)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -24.00  15.00   0.50    1.00    --    0.00 -82.00-180.00   78
  2  ω    -23.00  27.00   0.50    1.00    --    0.00 -82.00 -90.00  100
  3  ω    -20.00   6.00   0.50    1.00    --    0.00 -82.00  60.00   52
  4  ω    -33.00  -7.00   0.50    1.00    --    0.00 -82.00  90.00   52
  5  ω      6.00 113.00   0.50    1.50    --   95.80 -61.00 150.00  214
  6  ω     65.00 119.00   0.50    1.50    --   95.80 -61.00 -90.00  108
  7  ω     26.00 104.00   0.50    1.50    --   95.80 -77.00 -90.00  156
  8  ω      6.00  62.00   0.50    1.50    --   95.80 -61.00 -90.00  112
  9  ω     98.00 124.00   0.50    1.50    --   95.80  82.00 -60.00   52
 10  ω     22.00 101.00   0.50    1.50    --   95.80 -45.00 -60.00  158
 11  ω     75.00 185.00   0.50    1.50    --   95.80  57.00-104.13  220
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0274189000
_diffrn_orient_matrix_UB_12      0.0727749000
_diffrn_orient_matrix_UB_13      -0.0779618000
_diffrn_orient_matrix_UB_21      0.0327065000
_diffrn_orient_matrix_UB_22      -0.0696973000
_diffrn_orient_matrix_UB_23      0.0000528000
_diffrn_orient_matrix_UB_31      -0.0102760000
_diffrn_orient_matrix_UB_32      -0.0274056000
_diffrn_orient_matrix_UB_33      -0.2080058000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.730
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.952
_reflns_number_gt                6560
_reflns_number_total             7118
_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 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 
;
 Flack x determined using 2525 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(16)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     473
_refine_ls_number_reflns         7118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0444
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0712P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1153
_refine_ls_wR_factor_ref         0.1175
_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 Ternary CH refined with riding coordinates:
 C15(H15), C38(H38)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C17(H17A,H17B), C29(H29A,H29B), C40(H40A,H40B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13), C21(H21),
 C22(H22), C23(H23), C26(H26), C27(H27), C31(H31), C33(H33), C34(H34), C35(H35),
  C36(H36), C44(H44), C45(H45), C46(H46)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C20(H20A,H20B,H20C), C39(H39A,H39B,H39C), C43(H43A,H43B,
 H43C)
;
_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
O1 O 0.34568(6) 0.25424(15) 1.0816(3) 0.0381(5) Uani 1 1 d . . . . .
O2 O 0.37037(5) 0.26275(13) 0.7837(3) 0.0296(4) Uani 1 1 d . . . . .
N1 N 0.29582(6) 0.53996(14) 0.4953(3) 0.0241(4) Uani 1 1 d . . . . .
C1 C 0.31463(7) 0.28965(15) 0.6087(3) 0.0198(5) Uani 1 1 d . . . . .
C2 C 0.30569(7) 0.28288(16) 0.8029(3) 0.0221(5) Uani 1 1 d . . . . .
C3 C 0.26836(7) 0.29227(17) 0.8689(4) 0.0241(5) Uani 1 1 d . . . . .
H3 H 0.262430 0.287414 1.002180 0.029 Uiso 1 1 calc R U . . .
C4 C 0.24032(7) 0.30887(16) 0.7336(3) 0.0217(5) Uani 1 1 d . . . . .
H4 H 0.214629 0.315191 0.774683 0.026 Uiso 1 1 calc R U . . .
C5 C 0.24902(7) 0.31663(14) 0.5360(3) 0.0172(5) Uani 1 1 d . . . . .
C6 C 0.28646(6) 0.30661(15) 0.4730(3) 0.0191(5) Uani 1 1 d . . . . .
H6 H 0.292592 0.311277 0.339923 0.023 Uiso 1 1 calc R U . . .
C7 C 0.34066(8) 0.26527(18) 0.9116(4) 0.0272(6) Uani 1 1 d . . . . .
C8 C 0.35664(7) 0.27587(18) 0.5877(4) 0.0259(5) Uani 1 1 d . . . . .
H8A H 0.362117 0.221972 0.507297 0.031 Uiso 1 1 calc R U . . .
H8B H 0.368761 0.329566 0.527961 0.031 Uiso 1 1 calc R U . . .
C9 C 0.21797(6) 0.33447(15) 0.3946(3) 0.0177(5) Uani 1 1 d . . . . .
C10 C 0.20722(7) 0.26435(16) 0.2696(3) 0.0209(5) Uani 1 1 d . . . . .
H10 H 0.219668 0.207294 0.277684 0.025 Uiso 1 1 calc R U . . .
C11 C 0.17863(7) 0.27718(17) 0.1341(3) 0.0227(5) Uani 1 1 d . . . . .
H11 H 0.171563 0.229212 0.049984 0.027 Uiso 1 1 calc R U . . .
C12 C 0.16046(7) 0.36024(17) 0.1222(3) 0.0225(5) Uani 1 1 d . . . . .
H12 H 0.141013 0.369609 0.028983 0.027 Uiso 1 1 calc R U . . .
C13 C 0.17065(7) 0.42981(17) 0.2464(3) 0.0222(5) Uani 1 1 d . . . . .
H13 H 0.157906 0.486461 0.237131 0.027 Uiso 1 1 calc R U . . .
C14 C 0.19924(6) 0.41865(15) 0.3850(3) 0.0186(5) Uani 1 1 d . . . . .
C15 C 0.21009(7) 0.49741(15) 0.5167(3) 0.0200(5) Uani 1 1 d . . . . .
H15 H 0.227976 0.473306 0.616501 0.024 Uiso 1 1 calc R U . . .
C16 C 0.17546(8) 0.53644(18) 0.6224(4) 0.0287(6) Uani 1 1 d . . . . .
H16A H 0.156749 0.557930 0.527968 0.043 Uiso 1 1 calc R U . . .
H16B H 0.183562 0.587136 0.703978 0.043 Uiso 1 1 calc R U . . .
H16C H 0.163918 0.489237 0.702829 0.043 Uiso 1 1 calc R U . . .
C17 C 0.23129(7) 0.57202(16) 0.4047(4) 0.0231(5) Uani 1 1 d . . . . .
H17A H 0.216640 0.587125 0.287046 0.028 Uiso 1 1 calc R U . . .
H17B H 0.232613 0.627255 0.485520 0.028 Uiso 1 1 calc R U . . .
C18 C 0.27111(7) 0.54452(15) 0.3478(4) 0.0220(5) Uani 1 1 d . . . . .
C19 C 0.28143(8) 0.52421(17) 0.1571(4) 0.0255(5) Uani 1 1 d . . . . .
C20 C 0.25411(9) 0.5335(2) -0.0086(4) 0.0349(6) Uani 1 1 d . . . . .
H20A H 0.233837 0.488180 0.003911 0.052 Uiso 1 1 calc R U . . .
H20B H 0.267758 0.524021 -0.130171 0.052 Uiso 1 1 calc R U . . .
H20C H 0.242912 0.594356 -0.007456 0.052 Uiso 1 1 calc R U . . .
C21 C 0.31878(8) 0.49616(18) 0.1254(4) 0.0316(6) Uani 1 1 d . . . . .
H21 H 0.326769 0.481149 -0.001548 0.038 Uiso 1 1 calc R U . . .
C22 C 0.34430(8) 0.48989(19) 0.2758(4) 0.0334(6) Uani 1 1 d . . . . .
H22 H 0.369710 0.469887 0.255236 0.040 Uiso 1 1 calc R U . . .
C23 C 0.33162(8) 0.51379(17) 0.4582(4) 0.0285(6) Uani 1 1 d . . . . .
H23 H 0.349224 0.511469 0.562114 0.034 Uiso 1 1 calc R U . . .
O3 O 0.59315(5) 0.92586(12) -0.2518(3) 0.0267(4) Uani 1 1 d . . . . .
O4 O 0.57179(5) 0.91016(13) -0.5547(3) 0.0320(4) Uani 1 1 d . . . . .
N2 N 0.51925(6) 0.63538(14) -0.0031(3) 0.0264(5) Uani 1 1 d . . . . .
C24 C 0.56533(7) 0.90825(16) -0.3838(4) 0.0238(5) Uani 1 1 d . . . . .
C25 C 0.53004(7) 0.88701(15) -0.2794(4) 0.0205(5) Uani 1 1 d . . . . .
C26 C 0.49412(7) 0.86516(17) -0.3503(4) 0.0241(5) Uani 1 1 d . . . . .
H26 H 0.489290 0.863697 -0.484994 0.029 Uiso 1 1 calc R U . . .
C27 C 0.46581(7) 0.84575(16) -0.2195(3) 0.0218(5) Uani 1 1 d . . . . .
H27 H 0.440920 0.832156 -0.265017 0.026 Uiso 1 1 calc R U . . .
C28 C 0.47294(6) 0.84559(15) -0.0193(3) 0.0184(5) Uani 1 1 d . . . . .
C29 C 0.57859(7) 0.91508(19) -0.0564(4) 0.0257(5) Uani 1 1 d . . . . .
H29A H 0.581118 0.972207 0.017369 0.031 Uiso 1 1 calc R U . . .
H29B H 0.592416 0.866380 0.012513 0.031 Uiso 1 1 calc R U . . .
C30 C 0.53733(7) 0.89043(15) -0.0835(3) 0.0192(5) Uani 1 1 d . . . . .
C31 C 0.50905(7) 0.86988(15) 0.0494(3) 0.0197(5) Uani 1 1 d . . . . .
H31 H 0.514072 0.872243 0.183919 0.024 Uiso 1 1 calc R U . . .
C32 C 0.44172(6) 0.82073(15) 0.1171(3) 0.0176(5) Uani 1 1 d . . . . .
C33 C 0.43110(7) 0.88420(16) 0.2575(3) 0.0205(5) Uani 1 1 d . . . . .
H33 H 0.444455 0.940099 0.265510 0.025 Uiso 1 1 calc R U . . .
C34 C 0.40161(7) 0.86722(17) 0.3847(3) 0.0235(5) Uani 1 1 d . . . . .
H34 H 0.394609 0.911318 0.478020 0.028 Uiso 1 1 calc R U . . .
C35 C 0.38231(7) 0.78529(18) 0.3750(4) 0.0246(5) Uani 1 1 d . . . . .
H35 H 0.361849 0.773189 0.460856 0.029 Uiso 1 1 calc R U . . .
C36 C 0.39305(7) 0.72101(16) 0.2390(4) 0.0224(5) Uani 1 1 d . . . . .
H36 H 0.380024 0.664576 0.235692 0.027 Uiso 1 1 calc R U . . .
C37 C 0.42247(7) 0.73679(15) 0.1067(3) 0.0195(5) Uani 1 1 d . . . . .
C38 C 0.43441(7) 0.66177(16) -0.0310(3) 0.0196(5) Uani 1 1 d . . . . .
H38 H 0.452490 0.688999 -0.126229 0.024 Uiso 1 1 calc R U . . .
C39 C 0.40106(7) 0.62171(18) -0.1454(4) 0.0264(5) Uani 1 1 d . . . . .
H39A H 0.382352 0.595957 -0.055936 0.040 Uiso 1 1 calc R U . . .
H39B H 0.410517 0.573996 -0.231304 0.040 Uiso 1 1 calc R U . . .
H39C H 0.388997 0.669541 -0.222109 0.040 Uiso 1 1 calc R U . . .
C40 C 0.45616(7) 0.58620(16) 0.0772(4) 0.0224(5) Uani 1 1 d . . . . .
H40A H 0.441091 0.566486 0.190356 0.027 Uiso 1 1 calc R U . . .
H40B H 0.459458 0.533297 -0.009028 0.027 Uiso 1 1 calc R U . . .
C41 C 0.49472(7) 0.61921(16) 0.1433(4) 0.0233(5) Uani 1 1 d . . . . .
C42 C 0.50419(8) 0.63280(19) 0.3361(4) 0.0298(6) Uani 1 1 d . . . . .
C43 C 0.47684(8) 0.6139(2) 0.4972(4) 0.0377(7) Uani 1 1 d . . . . .
H43A H 0.455022 0.655084 0.487435 0.057 Uiso 1 1 calc R U . . .
H43B H 0.489677 0.623080 0.621096 0.057 Uiso 1 1 calc R U . . .
H43C H 0.467932 0.551043 0.488209 0.057 Uiso 1 1 calc R U . . .
C44 C 0.54078(8) 0.6663(2) 0.3754(5) 0.0368(7) Uani 1 1 d . . . . .
H44 H 0.548295 0.677088 0.504975 0.044 Uiso 1 1 calc R U . . .
C45 C 0.56580(8) 0.68356(19) 0.2277(5) 0.0361(6) Uani 1 1 d . . . . .
H45 H 0.590597 0.706520 0.252954 0.043 Uiso 1 1 calc R U . . .
C46 C 0.55385(7) 0.66655(18) 0.0406(4) 0.0306(6) Uani 1 1 d . . . . .
H46 H 0.571223 0.677676 -0.061764 0.037 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
O1 C7 1.203(3) . ?
O2 C7 1.370(3) . ?
O2 C8 1.455(3) . ?
N1 C18 1.342(3) . ?
N1 C23 1.339(3) . ?
C1 C2 1.386(3) . ?
C1 C6 1.388(3) . ?
C1 C8 1.495(3) . ?
C2 C3 1.395(3) . ?
C2 C7 1.464(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.382(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.409(3) . ?
C5 C6 1.393(3) . ?
C5 C9 1.490(3) . ?
C6 H6 0.9500 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.402(3) . ?
C9 C14 1.407(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.388(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.384(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.387(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.399(3) . ?
C14 C15 1.526(3) . ?
C15 H15 1.0000 . ?
C15 C16 1.531(3) . ?
C15 C17 1.539(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.508(3) . ?
C18 C19 1.404(3) . ?
C19 C20 1.503(4) . ?
C19 C21 1.392(4) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21 0.9500 . ?
C21 C22 1.378(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.386(4) . ?
C23 H23 0.9500 . ?
O3 C24 1.363(3) . ?
O3 C29 1.457(3) . ?
O4 C24 1.207(3) . ?
N2 C41 1.352(3) . ?
N2 C46 1.333(3) . ?
C24 C25 1.468(3) . ?
C25 C26 1.391(3) . ?
C25 C30 1.383(3) . ?
C26 H26 0.9500 . ?
C26 C27 1.375(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.411(3) . ?
C28 C31 1.400(3) . ?
C28 C32 1.493(3) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C29 C30 1.505(3) . ?
C30 C31 1.388(3) . ?
C31 H31 0.9500 . ?
C32 C33 1.401(3) . ?
C32 C37 1.412(3) . ?
C33 H33 0.9500 . ?
C33 C34 1.383(3) . ?
C34 H34 0.9500 . ?
C34 C35 1.387(4) . ?
C35 H35 0.9500 . ?
C35 C36 1.389(4) . ?
C36 H36 0.9500 . ?
C36 C37 1.401(3) . ?
C37 C38 1.521(3) . ?
C38 H38 1.0000 . ?
C38 C39 1.532(3) . ?
C38 C40 1.545(3) . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
C40 C41 1.509(3) . ?
C41 C42 1.393(4) . ?
C42 C43 1.499(4) . ?
C42 C44 1.402(4) . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
C44 H44 0.9500 . ?
C44 C45 1.373(4) . ?
C45 H45 0.9500 . ?
C45 C46 1.387(4) . ?
C46 H46 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
C7 O2 C8 110.48(19) . . ?
C23 N1 C18 118.3(2) . . ?
C2 C1 C6 120.7(2) . . ?
C2 C1 C8 107.9(2) . . ?
C6 C1 C8 131.3(2) . . ?
C1 C2 C3 121.6(2) . . ?
C1 C2 C7 108.9(2) . . ?
C3 C2 C7 129.5(2) . . ?
C2 C3 H3 121.2 . . ?
C4 C3 C2 117.6(2) . . ?
C4 C3 H3 121.2 . . ?
C3 C4 H4 119.3 . . ?
C3 C4 C5 121.4(2) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 C9 119.8(2) . . ?
C6 C5 C4 120.1(2) . . ?
C6 C5 C9 120.14(19) . . ?
C1 C6 C5 118.6(2) . . ?
C1 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
O1 C7 O2 121.3(2) . . ?
O1 C7 C2 130.7(3) . . ?
O2 C7 C2 108.0(2) . . ?
O2 C8 C1 104.7(2) . . ?
O2 C8 H8A 110.8 . . ?
O2 C8 H8B 110.8 . . ?
C1 C8 H8A 110.8 . . ?
C1 C8 H8B 110.8 . . ?
H8A C8 H8B 108.9 . . ?
C10 C9 C5 118.3(2) . . ?
C10 C9 C14 119.8(2) . . ?
C14 C9 C5 121.9(2) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.9(2) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 H11 120.2 . . ?
C12 C11 C10 119.6(2) . . ?
C12 C11 H11 120.2 . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 120.0(2) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 119.2 . . ?
C12 C13 C14 121.6(2) . . ?
C14 C13 H13 119.2 . . ?
C9 C14 C15 121.8(2) . . ?
C13 C14 C9 118.1(2) . . ?
C13 C14 C15 120.0(2) . . ?
C14 C15 H15 107.5 . . ?
C14 C15 C16 112.01(19) . . ?
C14 C15 C17 111.31(19) . . ?
C16 C15 H15 107.5 . . ?
C16 C15 C17 110.9(2) . . ?
C17 C15 H15 107.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.0 . . ?
C15 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
C18 C17 C15 112.81(19) . . ?
C18 C17 H17A 109.0 . . ?
C18 C17 H17B 109.0 . . ?
N1 C18 C17 114.4(2) . . ?
N1 C18 C19 122.7(2) . . ?
C19 C18 C17 122.9(2) . . ?
C18 C19 C20 122.4(2) . . ?
C21 C19 C18 117.1(2) . . ?
C21 C19 C20 120.4(2) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21 119.6 . . ?
C22 C21 C19 120.8(3) . . ?
C22 C21 H21 119.6 . . ?
C21 C22 H22 121.1 . . ?
C21 C22 C23 117.7(3) . . ?
C23 C22 H22 121.1 . . ?
N1 C23 C22 123.4(3) . . ?
N1 C23 H23 118.3 . . ?
C22 C23 H23 118.3 . . ?
C24 O3 C29 110.64(18) . . ?
C46 N2 C41 118.0(2) . . ?
O3 C24 C25 108.3(2) . . ?
O4 C24 O3 121.4(2) . . ?
O4 C24 C25 130.4(3) . . ?
C26 C25 C24 129.7(2) . . ?
C30 C25 C24 108.7(2) . . ?
C30 C25 C26 121.5(2) . . ?
C25 C26 H26 121.0 . . ?
C27 C26 C25 118.0(2) . . ?
C27 C26 H26 121.0 . . ?
C26 C27 H27 119.3 . . ?
C26 C27 C28 121.4(2) . . ?
C28 C27 H27 119.3 . . ?
C27 C28 C32 119.6(2) . . ?
C31 C28 C27 119.7(2) . . ?
C31 C28 C32 120.7(2) . . ?
O3 C29 H29A 110.9 . . ?
O3 C29 H29B 110.9 . . ?
O3 C29 C30 104.37(19) . . ?
H29A C29 H29B 108.9 . . ?
C30 C29 H29A 110.9 . . ?
C30 C29 H29B 110.9 . . ?
C25 C30 C29 108.0(2) . . ?
C25 C30 C31 120.8(2) . . ?
C31 C30 C29 131.2(2) . . ?
C28 C31 H31 120.8 . . ?
C30 C31 C28 118.5(2) . . ?
C30 C31 H31 120.8 . . ?
C33 C32 C28 118.1(2) . . ?
C33 C32 C37 119.6(2) . . ?
C37 C32 C28 122.3(2) . . ?
C32 C33 H33 119.3 . . ?
C34 C33 C32 121.4(2) . . ?
C34 C33 H33 119.3 . . ?
C33 C34 H34 120.3 . . ?
C33 C34 C35 119.5(2) . . ?
C35 C34 H34 120.3 . . ?
C34 C35 H35 120.1 . . ?
C34 C35 C36 119.7(2) . . ?
C36 C35 H35 120.1 . . ?
C35 C36 H36 119.0 . . ?
C35 C36 C37 122.1(2) . . ?
C37 C36 H36 119.0 . . ?
C32 C37 C38 122.6(2) . . ?
C36 C37 C32 117.7(2) . . ?
C36 C37 C38 119.6(2) . . ?
C37 C38 H38 107.3 . . ?
C37 C38 C39 113.29(19) . . ?
C37 C38 C40 110.87(19) . . ?
C39 C38 H38 107.3 . . ?
C39 C38 C40 110.50(19) . . ?
C40 C38 H38 107.3 . . ?
C38 C39 H39A 109.5 . . ?
C38 C39 H39B 109.5 . . ?
C38 C39 H39C 109.5 . . ?
H39A C39 H39B 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C38 C40 H40A 109.5 . . ?
C38 C40 H40B 109.5 . . ?
H40A C40 H40B 108.0 . . ?
C41 C40 C38 110.93(19) . . ?
C41 C40 H40A 109.5 . . ?
C41 C40 H40B 109.5 . . ?
N2 C41 C40 113.6(2) . . ?
N2 C41 C42 122.9(2) . . ?
C42 C41 C40 123.5(2) . . ?
C41 C42 C43 122.4(2) . . ?
C41 C42 C44 117.1(3) . . ?
C44 C42 C43 120.5(3) . . ?
C42 C43 H43A 109.5 . . ?
C42 C43 H43B 109.5 . . ?
C42 C43 H43C 109.5 . . ?
H43A C43 H43B 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C42 C44 H44 119.8 . . ?
C45 C44 C42 120.4(3) . . ?
C45 C44 H44 119.8 . . ?
C44 C45 H45 120.9 . . ?
C44 C45 C46 118.1(3) . . ?
C46 C45 H45 120.9 . . ?
N2 C46 C45 123.4(3) . . ?
N2 C46 H46 118.3 . . ?
C45 C46 H46 118.3 . . ?

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
N1 C18 C19 C20 -177.2(2) . . . . ?
N1 C18 C19 C21 1.7(3) . . . . ?
C1 C2 C3 C4 -0.1(4) . . . . ?
C1 C2 C7 O1 -179.4(3) . . . . ?
C1 C2 C7 O2 0.8(3) . . . . ?
C2 C1 C6 C5 0.0(3) . . . . ?
C2 C1 C8 O2 -1.0(3) . . . . ?
C2 C3 C4 C5 -0.4(4) . . . . ?
C3 C2 C7 O1 0.5(5) . . . . ?
C3 C2 C7 O2 -179.3(2) . . . . ?
C3 C4 C5 C6 0.7(4) . . . . ?
C3 C4 C5 C9 179.9(2) . . . . ?
C4 C5 C6 C1 -0.5(3) . . . . ?
C4 C5 C9 C10 -109.0(3) . . . . ?
C4 C5 C9 C14 70.5(3) . . . . ?
C5 C9 C10 C11 -179.6(2) . . . . ?
C5 C9 C14 C13 179.4(2) . . . . ?
C5 C9 C14 C15 1.1(3) . . . . ?
C6 C1 C2 C3 0.3(4) . . . . ?
C6 C1 C2 C7 -179.8(2) . . . . ?
C6 C1 C8 O2 178.9(2) . . . . ?
C6 C5 C9 C10 70.3(3) . . . . ?
C6 C5 C9 C14 -110.3(3) . . . . ?
C7 O2 C8 C1 1.6(3) . . . . ?
C7 C2 C3 C4 180.0(2) . . . . ?
C8 O2 C7 O1 178.7(3) . . . . ?
C8 O2 C7 C2 -1.5(3) . . . . ?
C8 C1 C2 C3 -179.7(2) . . . . ?
C8 C1 C2 C7 0.2(3) . . . . ?
C8 C1 C6 C5 -180.0(2) . . . . ?
C9 C5 C6 C1 -179.7(2) . . . . ?
C9 C10 C11 C12 0.0(3) . . . . ?
C9 C14 C15 C16 -127.8(2) . . . . ?
C9 C14 C15 C17 107.5(2) . . . . ?
C10 C9 C14 C13 -1.2(3) . . . . ?
C10 C9 C14 C15 -179.5(2) . . . . ?
C10 C11 C12 C13 -0.5(4) . . . . ?
C11 C12 C13 C14 0.2(4) . . . . ?
C12 C13 C14 C9 0.6(3) . . . . ?
C12 C13 C14 C15 178.9(2) . . . . ?
C13 C14 C15 C16 54.0(3) . . . . ?
C13 C14 C15 C17 -70.7(3) . . . . ?
C14 C9 C10 C11 0.9(3) . . . . ?
C14 C15 C17 C18 -71.6(2) . . . . ?
C15 C17 C18 N1 -71.4(3) . . . . ?
C15 C17 C18 C19 107.8(3) . . . . ?
C16 C15 C17 C18 163.0(2) . . . . ?
C17 C18 C19 C20 3.7(4) . . . . ?
C17 C18 C19 C21 -177.5(2) . . . . ?
C18 N1 C23 C22 -1.0(4) . . . . ?
C18 C19 C21 C22 -0.7(4) . . . . ?
C19 C21 C22 C23 -1.0(4) . . . . ?
C20 C19 C21 C22 178.2(2) . . . . ?
C21 C22 C23 N1 1.9(4) . . . . ?
C23 N1 C18 C17 178.3(2) . . . . ?
C23 N1 C18 C19 -0.9(3) . . . . ?
O3 C24 C25 C26 179.6(2) . . . . ?
O3 C24 C25 C30 -1.1(3) . . . . ?
O3 C29 C30 C25 0.6(3) . . . . ?
O3 C29 C30 C31 178.3(2) . . . . ?
O4 C24 C25 C26 -1.6(5) . . . . ?
O4 C24 C25 C30 177.6(3) . . . . ?
N2 C41 C42 C43 -179.5(2) . . . . ?
N2 C41 C42 C44 1.1(4) . . . . ?
C24 O3 C29 C30 -1.4(3) . . . . ?
C24 C25 C26 C27 178.4(2) . . . . ?
C24 C25 C30 C29 0.3(3) . . . . ?
C24 C25 C30 C31 -177.7(2) . . . . ?
C25 C26 C27 C28 -1.6(4) . . . . ?
C25 C30 C31 C28 0.0(3) . . . . ?
C26 C25 C30 C29 179.6(2) . . . . ?
C26 C25 C30 C31 1.6(4) . . . . ?
C26 C27 C28 C31 3.1(4) . . . . ?
C26 C27 C28 C32 -177.7(2) . . . . ?
C27 C28 C31 C30 -2.3(3) . . . . ?
C27 C28 C32 C33 -121.7(2) . . . . ?
C27 C28 C32 C37 57.3(3) . . . . ?
C28 C32 C33 C34 177.8(2) . . . . ?
C28 C32 C37 C36 -178.6(2) . . . . ?
C28 C32 C37 C38 6.0(3) . . . . ?
C29 O3 C24 O4 -177.3(2) . . . . ?
C29 O3 C24 C25 1.6(3) . . . . ?
C29 C30 C31 C28 -177.5(2) . . . . ?
C30 C25 C26 C27 -0.8(4) . . . . ?
C31 C28 C32 C33 57.5(3) . . . . ?
C31 C28 C32 C37 -123.6(2) . . . . ?
C32 C28 C31 C30 178.6(2) . . . . ?
C32 C33 C34 C35 0.7(4) . . . . ?
C32 C37 C38 C39 -131.9(2) . . . . ?
C32 C37 C38 C40 103.2(3) . . . . ?
C33 C32 C37 C36 0.3(3) . . . . ?
C33 C32 C37 C38 -175.1(2) . . . . ?
C33 C34 C35 C36 0.6(4) . . . . ?
C34 C35 C36 C37 -1.5(4) . . . . ?
C35 C36 C37 C32 1.0(3) . . . . ?
C35 C36 C37 C38 176.5(2) . . . . ?
C36 C37 C38 C39 52.8(3) . . . . ?
C36 C37 C38 C40 -72.1(3) . . . . ?
C37 C32 C33 C34 -1.2(3) . . . . ?
C37 C38 C40 C41 -69.5(3) . . . . ?
C38 C40 C41 N2 -68.0(3) . . . . ?
C38 C40 C41 C42 111.3(3) . . . . ?
C39 C38 C40 C41 164.0(2) . . . . ?
C40 C41 C42 C43 1.2(4) . . . . ?
C40 C41 C42 C44 -178.2(2) . . . . ?
C41 N2 C46 C45 -0.3(4) . . . . ?
C41 C42 C44 C45 -0.6(4) . . . . ?
C42 C44 C45 C46 -0.3(4) . . . . ?
C43 C42 C44 C45 180.0(3) . . . . ?
C44 C45 C46 N2 0.8(4) . . . . ?
C46 N2 C41 C40 178.7(2) . . . . ?
C46 N2 C41 C42 -0.7(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 1.853
_oxdiff_exptl_absorpt_empirical_full_min 0.613
