# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_sar-03a2
_database_code_depnum_ccdc_archive 'CCDC 2235705'
loop_
_audit_author_name
_audit_author_address
'Matthew I. Polson'
;Univeristy of Canterbury
New Zealand
;
_audit_update_record             
;
2023-01-12 deposited with the CCDC.	2023-06-20 downloaded from the CCDC.
;
_audit_creation_date             2023-01-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
loop_
_audit_author_email
matthew.polson@canterbury.ac.nz
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H19 F N2 O2'
_chemical_formula_sum            'C23 H19 F N2 O2'
_chemical_formula_weight         374.40
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C23H19FN2O2
_chemical_oxdiff_usercomment     AS-377
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'
F F 0.0727 0.0534 '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                   12.3101(2)
_cell_length_b                   5.45170(10)
_cell_length_c                   14.3867(2)
_cell_angle_alpha                90
_cell_angle_beta                 106.621(2)
_cell_angle_gamma                90
_cell_volume                     925.16(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    15019
_cell_measurement_temperature    119.9(3)
_cell_measurement_theta_max      77.5110
_cell_measurement_theta_min      3.6790
_shelx_estimated_absorpt_T_max   0.935
_shelx_estimated_absorpt_T_min   0.631
_exptl_absorpt_coefficient_mu    0.764
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.492
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             392
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0234
0 0 1 0.0655
0 1 0 0.3450
0 -1 0 0.3182
-1 0 0 0.0427
1 0 0 0.0803
-1 0 2 0.0532
1 0 -2 0.0465

_exptl_crystal_size_max          0.663
_exptl_crystal_size_mid          0.137
_exptl_crystal_size_min          0.089
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0003 -0.0001 -0.9999 0.0707 -0.0638 -0.0584
-0.0003 0.0001 0.9999 -0.0707 0.0638 0.0584
-0.0011 1.0003 0.0007 -0.1756 0.0082 -0.2213
0.0011 -1.0003 -0.0007 0.1756 -0.0082 0.2213
-1.0000 -0.0005 -0.0009 -0.0342 -0.1240 0.0226
1.0000 0.0005 0.0009 0.0342 0.1240 -0.0226
-1.0005 -0.0004 1.9989 -0.1756 0.0037 0.1395
1.0005 0.0004 -1.9989 0.1756 -0.0037 -0.1395

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0762
_diffrn_reflns_av_unetI/netI     0.0570
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11231
_diffrn_reflns_point_group_measured_fraction_full 0.941
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        67.063
_diffrn_reflns_theta_max         67.063
_diffrn_reflns_theta_min         3.747
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      119.9(3)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -120.00 -34.00   0.50    1.00    --  -47.45 -51.00 104.00  172
  2  ω    -61.00  25.00   0.50    1.00    --  -47.45  51.00-109.00  172
  3  ω    -24.00  61.00   0.50    1.00    --   47.45 -51.00 104.00  170
  4  ω     35.00 122.00   0.50    4.00    --  107.75 -51.00 104.00  174
  5  ω     94.00 178.00   0.50    4.00    --  107.75  51.00-109.00  168
  6  ω     35.00 121.00   0.50    1.00    --   47.45  37.00   0.00  172
  7  ω     34.00  95.00   0.50    1.00    --   47.45-125.00 -30.00  122
  8  ω     34.00 120.00   0.50    1.00    --   47.45  51.00-109.00  172
  9  ω     33.00 120.00   0.50    1.00    --   47.45  57.00  30.00  174
 10  ω     35.00 106.00   0.50    4.00    --  107.75 -94.00  90.00  142
 11  ω     91.00 178.00   0.50    4.00    --  107.75  61.00 -30.00  174
 12  ω     35.00  95.00   0.50    4.00    --  107.75 -94.00-120.00  120
 13  ω     91.00 178.00   0.50    4.00    --  107.75  61.00 150.00  174
 14  ω     95.00 178.00   0.50    4.00    --  107.75  30.00  30.00  166
 15  ω     99.50 178.00   0.50    4.00    --  107.75  77.00  30.00  157
 16  ω     91.00 178.00   0.50    4.00    --  107.75  61.00   0.00  174
 17  ω     35.00 124.00   0.50    4.00    --  107.75 -61.00   0.00  178
 18  ω    102.00 178.00   0.50    4.00    --  107.75  77.00   0.00  152
 19  ω     89.00 178.00   0.50    4.00    --  107.75  67.00   0.35  178
 20  ω     85.00 178.00   0.50    4.00    --  107.75  77.00 -30.00  186
 21  ω     91.00 178.00   0.50    4.00    --  107.75  61.00 -60.00  174
 22  ω     33.00 121.00   0.50    4.00    --  107.75 -30.00-120.00  176
 23  ω     35.00 131.00   0.50    4.00    --  107.75 -77.00 120.00  192
 24  ω     91.00 178.00   0.50    4.00    --  107.75  61.00  30.00  174
 25  ω     95.00 178.00   0.50    4.00    --  107.75  45.00 -30.00  166
 26  ω     33.00 122.00   0.50    4.00    --  107.75 -15.00  30.00  178
 27  ω     35.00 105.00   0.50    4.00    --  107.75-125.00 150.00  140
 28  ω     86.00 178.00   0.50    4.00    --  107.75  74.00 -40.76  184
 29  ω     35.00  95.00   0.50    4.00    --  107.75-125.00 -30.00  120
 30  ω     95.00 178.00   0.50    4.00    --  107.75  45.00 -60.00  166
 31  ω     35.00  95.00   0.50    4.00    --  107.75-125.00  90.00  120
 32  ω   -120.00 -38.00   0.50    1.00    --  -47.45 -77.00 -90.00  164
 33  ω   -120.00 -25.00   0.50    1.00    --  -47.45 -77.00-150.00  190
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu 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      0.0343312000
_diffrn_orient_matrix_UB_12      -0.1754812000
_diffrn_orient_matrix_UB_13      -0.0706798000
_diffrn_orient_matrix_UB_21      0.1239545000
_diffrn_orient_matrix_UB_22      0.0083023000
_diffrn_orient_matrix_UB_23      0.0638732000
_diffrn_orient_matrix_UB_31      -0.0225613000
_diffrn_orient_matrix_UB_32      -0.2213494000
_diffrn_orient_matrix_UB_33      0.0584337000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.700
_reflns_Friedel_fraction_full    0.876
_reflns_Friedel_fraction_max     0.876
_reflns_number_gt                3005
_reflns_number_total             3114
_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 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (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 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.487
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.089
_refine_ls_abs_structure_details 
;
 Flack x determined using 1167 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3114
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0731
_refine_ls_restrained_S_all      1.034
_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)+(0.1644P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1820
_refine_ls_wR_factor_ref         0.1834
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C'(H'A,H'B), C"(H"A,H"B)
2.c Aromatic/amide H refined with riding coordinates:
 C8*(H8*), C2"*(H2"*), C2"(H2"), C7*(H7*), C8(H8), C2'*(H2'*), C7(H7), C3"*
 (H3"*), C3"(H3"), C2'(H2'), C3'(H3'), C4"(H4"), C4'(H4'), C3'*(H3'*)
;
_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 1.02551(16) 0.5940(5) 0.68627(15) 0.0402(6) Uani 1 1 d . . . . .
O1 O 0.4939(2) 0.1365(5) 0.23536(17) 0.0369(6) Uani 1 1 d . . . . .
O2 O 0.5007(2) 0.8016(6) 0.43176(17) 0.0398(7) Uani 1 1 d . . . . .
N1 N 0.6339(2) 0.4199(6) 0.3022(2) 0.0315(7) Uani 1 1 d . . . . .
N3 N 0.4685(2) 0.4579(7) 0.3330(2) 0.0333(7) Uani 1 1 d . . . . .
C1' C 0.7182(2) 0.5120(7) 0.1692(2) 0.0315(8) Uani 1 1 d . . . . .
C4 C 0.5302(3) 0.6518(7) 0.3819(2) 0.0328(7) Uani 1 1 d . . . . .
C9 C 0.9328(2) 0.6071(8) 0.6071(2) 0.0322(8) Uani 1 1 d . . . . .
C1" C 0.2629(3) 0.5088(7) 0.2503(2) 0.0314(8) Uani 1 1 d . . . . .
C8* C 0.9249(3) 0.8002(7) 0.5447(2) 0.0348(8) Uani 1 1 d . . . . .
H8* H 0.982660 0.921422 0.555794 0.042 Uiso 1 1 calc R U . . .
C2"* C 0.1571(3) 0.3940(8) 0.2202(2) 0.0350(8) Uani 1 1 d . . . . .
H2"* H 0.145559 0.243495 0.249338 0.042 Uiso 1 1 calc R U . . .
C2" C 0.2792(3) 0.7251(8) 0.2055(3) 0.0367(8) Uani 1 1 d . . . . .
H2" H 0.350893 0.804300 0.224780 0.044 Uiso 1 1 calc R U . . .
C7* C 0.8296(3) 0.8138(7) 0.4642(2) 0.0323(8) Uani 1 1 d . . . . .
H7* H 0.821775 0.946136 0.419849 0.039 Uiso 1 1 calc R U . . .
C5 C 0.6449(3) 0.6424(7) 0.3594(2) 0.0317(8) Uani 1 1 d . . . . .
H5 H 0.651689 0.786647 0.318458 0.038 Uiso 1 1 calc R U . . .
C8 C 0.8513(3) 0.4272(7) 0.5949(2) 0.0339(8) Uani 1 1 d . . . . .
H8 H 0.859340 0.296967 0.640213 0.041 Uiso 1 1 calc R U . . .
C2 C 0.5293(3) 0.3158(7) 0.2833(2) 0.0316(8) Uani 1 1 d . . . . .
C2'* C 0.6402(3) 0.4787(9) 0.0787(3) 0.0428(9) Uani 1 1 d . . . . .
H2'* H 0.587081 0.348127 0.069065 0.051 Uiso 1 1 calc R U . . .
C7 C 0.7576(3) 0.4419(7) 0.5148(2) 0.0337(8) Uani 1 1 d . . . . .
H7 H 0.700329 0.319692 0.504460 0.040 Uiso 1 1 calc R U . . .
C6 C 0.7460(2) 0.6351(7) 0.4487(2) 0.0304(8) Uani 1 1 d . . . . .
C' C 0.7171(3) 0.3455(7) 0.2522(2) 0.0339(8) Uani 1 1 d . . . . .
H'A H 0.699771 0.176341 0.227302 0.041 Uiso 1 1 calc R U . . .
H'B H 0.793539 0.344241 0.299299 0.041 Uiso 1 1 calc R U . . .
C3"* C 0.0694(3) 0.4961(9) 0.1491(3) 0.0426(9) Uani 1 1 d . . . . .
H3"* H -0.002451 0.417469 0.130009 0.051 Uiso 1 1 calc R U . . .
C3" C 0.1913(3) 0.8266(9) 0.1327(3) 0.0425(9) Uani 1 1 d . . . . .
H3" H 0.203384 0.973667 0.101719 0.051 Uiso 1 1 calc R U . . .
C2' C 0.7954(3) 0.7036(8) 0.1816(3) 0.0427(9) Uani 1 1 d . . . . .
H2' H 0.849547 0.727474 0.242880 0.051 Uiso 1 1 calc R U . . .
C3' C 0.7944(4) 0.8601(10) 0.1056(4) 0.0559(12) Uani 1 1 d . . . . .
H3' H 0.847877 0.990085 0.115040 0.067 Uiso 1 1 calc R U . . .
C4" C 0.0859(3) 0.7142(9) 0.1051(3) 0.0442(10) Uani 1 1 d . . . . .
H4" H 0.025256 0.785962 0.056277 0.053 Uiso 1 1 calc R U . . .
C" C 0.3537(3) 0.3958(8) 0.3336(2) 0.0349(8) Uani 1 1 d . . . . .
H"A H 0.342110 0.451640 0.395514 0.042 Uiso 1 1 calc R U . . .
H"B H 0.345018 0.215235 0.330498 0.042 Uiso 1 1 calc R U . . .
C4' C 0.7172(5) 0.8289(10) 0.0172(4) 0.0606(14) Uani 1 1 d . . . . .
H4' H 0.716057 0.938411 -0.034410 0.073 Uiso 1 1 calc R U . . .
C3'* C 0.6396(4) 0.6346(12) 0.0027(3) 0.0583(13) Uani 1 1 d . . . . .
H3'* H 0.586634 0.610139 -0.059103 0.070 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 C9 1.364(4) . ?
O1 C2 1.204(5) . ?
O2 C4 1.209(5) . ?
N1 C5 1.450(5) . ?
N1 C2 1.361(4) . ?
N1 C' 1.468(4) . ?
N3 C4 1.373(5) . ?
N3 C2 1.407(5) . ?
N3 C" 1.455(4) . ?
C1' C2'* 1.390(5) . ?
C1' C' 1.503(5) . ?
C1' C2' 1.389(5) . ?
C4 C5 1.537(4) . ?
C9 C8* 1.369(5) . ?
C9 C8 1.378(5) . ?
C1" C2"* 1.397(5) . ?
C1" C2" 1.386(6) . ?
C1" C" 1.515(5) . ?
C8* H8* 0.9500 . ?
C8* C7* 1.395(5) . ?
C2"* H2"* 0.9500 . ?
C2"* C3"* 1.375(5) . ?
C2" H2" 0.9500 . ?
C2" C3" 1.388(5) . ?
C7* H7* 0.9500 . ?
C7* C6 1.388(5) . ?
C5 H5 1.0000 . ?
C5 C6 1.512(4) . ?
C8 H8 0.9500 . ?
C8 C7 1.380(5) . ?
C2'* H2'* 0.9500 . ?
C2'* C3'* 1.383(7) . ?
C7 H7 0.9500 . ?
C7 C6 1.399(5) . ?
C' H'A 0.9900 . ?
C' H'B 0.9900 . ?
C3"* H3"* 0.9500 . ?
C3"* C4" 1.389(6) . ?
C3" H3" 0.9500 . ?
C3" C4" 1.386(6) . ?
C2' H2' 0.9500 . ?
C2' C3' 1.384(6) . ?
C3' H3' 0.9500 . ?
C3' C4' 1.362(8) . ?
C4" H4" 0.9500 . ?
C" H"A 0.9900 . ?
C" H"B 0.9900 . ?
C4' H4' 0.9500 . ?
C4' C3'* 1.402(9) . ?
C3'* H3'* 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
C5 N1 C' 122.9(3) . . ?
C2 N1 C5 113.1(3) . . ?
C2 N1 C' 122.7(3) . . ?
C4 N3 C2 112.8(3) . . ?
C4 N3 C" 124.9(3) . . ?
C2 N3 C" 122.3(3) . . ?
C2'* C1' C' 120.3(3) . . ?
C2' C1' C2'* 118.8(4) . . ?
C2' C1' C' 120.9(3) . . ?
O2 C4 N3 127.4(3) . . ?
O2 C4 C5 126.7(3) . . ?
N3 C4 C5 105.9(3) . . ?
F1 C9 C8* 118.3(3) . . ?
F1 C9 C8 118.3(3) . . ?
C8* C9 C8 123.4(3) . . ?
C2"* C1" C" 118.3(3) . . ?
C2" C1" C2"* 118.9(3) . . ?
C2" C1" C" 122.7(3) . . ?
C9 C8* H8* 121.0 . . ?
C9 C8* C7* 118.1(3) . . ?
C7* C8* H8* 121.0 . . ?
C1" C2"* H2"* 119.6 . . ?
C3"* C2"* C1" 120.9(4) . . ?
C3"* C2"* H2"* 119.6 . . ?
C1" C2" H2" 119.8 . . ?
C1" C2" C3" 120.3(3) . . ?
C3" C2" H2" 119.8 . . ?
C8* C7* H7* 119.8 . . ?
C6 C7* C8* 120.4(3) . . ?
C6 C7* H7* 119.8 . . ?
N1 C5 C4 101.8(3) . . ?
N1 C5 H5 109.5 . . ?
N1 C5 C6 112.4(3) . . ?
C4 C5 H5 109.5 . . ?
C6 C5 C4 113.8(3) . . ?
C6 C5 H5 109.5 . . ?
C9 C8 H8 121.0 . . ?
C9 C8 C7 118.0(3) . . ?
C7 C8 H8 121.0 . . ?
O1 C2 N1 128.3(3) . . ?
O1 C2 N3 125.5(3) . . ?
N1 C2 N3 106.2(3) . . ?
C1' C2'* H2'* 119.8 . . ?
C3'* C2'* C1' 120.4(4) . . ?
C3'* C2'* H2'* 119.8 . . ?
C8 C7 H7 119.7 . . ?
C8 C7 C6 120.6(3) . . ?
C6 C7 H7 119.7 . . ?
C7* C6 C5 120.7(3) . . ?
C7* C6 C7 119.5(3) . . ?
C7 C6 C5 119.8(3) . . ?
N1 C' C1' 112.9(3) . . ?
N1 C' H'A 109.0 . . ?
N1 C' H'B 109.0 . . ?
C1' C' H'A 109.0 . . ?
C1' C' H'B 109.0 . . ?
H'A C' H'B 107.8 . . ?
C2"* C3"* H3"* 120.0 . . ?
C2"* C3"* C4" 120.0(3) . . ?
C4" C3"* H3"* 120.0 . . ?
C2" C3" H3" 119.9 . . ?
C4" C3" C2" 120.3(4) . . ?
C4" C3" H3" 119.9 . . ?
C1' C2' H2' 119.6 . . ?
C3' C2' C1' 120.7(4) . . ?
C3' C2' H2' 119.6 . . ?
C2' C3' H3' 119.8 . . ?
C4' C3' C2' 120.4(5) . . ?
C4' C3' H3' 119.8 . . ?
C3"* C4" H4" 120.2 . . ?
C3" C4" C3"* 119.6(3) . . ?
C3" C4" H4" 120.2 . . ?
N3 C" C1" 113.5(3) . . ?
N3 C" H"A 108.9 . . ?
N3 C" H"B 108.9 . . ?
C1" C" H"A 108.9 . . ?
C1" C" H"B 108.9 . . ?
H"A C" H"B 107.7 . . ?
C3' C4' H4' 120.1 . . ?
C3' C4' C3'* 119.8(4) . . ?
C3'* C4' H4' 120.1 . . ?
C2'* C3'* C4' 119.8(4) . . ?
C2'* C3'* H3'* 120.1 . . ?
C4' C3'* H3'* 120.1 . . ?

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 C9 C8* C7* -179.5(3) . . . . ?
F1 C9 C8 C7 179.8(3) . . . . ?
O2 C4 C5 N1 176.9(3) . . . . ?
O2 C4 C5 C6 55.7(5) . . . . ?
N1 C5 C6 C7* 122.7(3) . . . . ?
N1 C5 C6 C7 -55.2(4) . . . . ?
N3 C4 C5 N1 -3.9(3) . . . . ?
N3 C4 C5 C6 -125.0(3) . . . . ?
C1' C2'* C3'* C4' -0.6(6) . . . . ?
C1' C2' C3' C4' 0.2(6) . . . . ?
C4 N3 C2 O1 180.0(3) . . . . ?
C4 N3 C2 N1 0.9(4) . . . . ?
C4 N3 C" C1" 92.9(4) . . . . ?
C4 C5 C6 C7* -122.2(3) . . . . ?
C4 C5 C6 C7 59.9(4) . . . . ?
C9 C8* C7* C6 -0.2(5) . . . . ?
C9 C8 C7 C6 -0.4(5) . . . . ?
C1" C2"* C3"* C4" 1.0(5) . . . . ?
C1" C2" C3" C4" 0.9(6) . . . . ?
C8* C9 C8 C7 0.7(5) . . . . ?
C8* C7* C6 C5 -177.3(3) . . . . ?
C8* C7* C6 C7 0.6(5) . . . . ?
C2"* C1" C2" C3" 0.6(5) . . . . ?
C2"* C1" C" N3 155.4(3) . . . . ?
C2"* C3"* C4" C3" 0.6(5) . . . . ?
C2" C1" C2"* C3"* -1.6(5) . . . . ?
C2" C1" C" N3 -27.1(5) . . . . ?
C2" C3" C4" C3"* -1.5(6) . . . . ?
C5 N1 C2 O1 177.3(3) . . . . ?
C5 N1 C2 N3 -3.7(4) . . . . ?
C5 N1 C' C1' -68.2(4) . . . . ?
C8 C9 C8* C7* -0.4(5) . . . . ?
C8 C7 C6 C7* -0.3(5) . . . . ?
C8 C7 C6 C5 177.6(3) . . . . ?
C2 N1 C5 C4 4.7(4) . . . . ?
C2 N1 C5 C6 126.9(3) . . . . ?
C2 N1 C' C1' 97.9(4) . . . . ?
C2 N3 C4 O2 -178.8(4) . . . . ?
C2 N3 C4 C5 2.0(4) . . . . ?
C2 N3 C" C1" -89.1(4) . . . . ?
C2'* C1' C' N1 -83.3(4) . . . . ?
C2'* C1' C2' C3' 0.5(5) . . . . ?
C' N1 C5 C4 172.0(3) . . . . ?
C' N1 C5 C6 -65.8(4) . . . . ?
C' N1 C2 O1 9.9(5) . . . . ?
C' N1 C2 N3 -171.1(3) . . . . ?
C' C1' C2'* C3'* 178.7(4) . . . . ?
C' C1' C2' C3' -178.5(4) . . . . ?
C2' C1' C2'* C3'* -0.2(5) . . . . ?
C2' C1' C' N1 95.6(3) . . . . ?
C2' C3' C4' C3'* -1.1(7) . . . . ?
C3' C4' C3'* C2'* 1.3(7) . . . . ?
C" N3 C4 O2 -0.7(6) . . . . ?
C" N3 C4 C5 -179.9(3) . . . . ?
C" N3 C2 O1 1.8(5) . . . . ?
C" N3 C2 N1 -177.2(3) . . . . ?
C" C1" C2"* C3"* 176.0(3) . . . . ?
C" C1" C2" C3" -176.9(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 4.262
_oxdiff_exptl_absorpt_empirical_full_min 0.171
####################################################################### 
# 
# 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_sar-07ra
_database_code_depnum_ccdc_archive 'CCDC 2241398'
loop_
_audit_author_name
_audit_author_address
'Polson M.I.J.'
;Univeristy of Canterbury
New Zealand
;
_audit_update_record             
;
2023-02-13 deposited with the CCDC.	2023-06-20 downloaded from the CCDC.
;
_audit_creation_date             2023-02-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
loop_
_audit_author_email
matthew.polson@canterbury.ac.nz
_publ_section_exptl              
;
Any special experimental details
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H19 Br N2 O2'
_chemical_formula_sum            'C23 H19 Br N2 O2'
_chemical_formula_weight         435.31
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C23H19N2O2Br
_chemical_oxdiff_usercomment     as-496
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   12.5962(6)
_cell_length_b                   5.2216(2)
_cell_length_c                   15.4025(6)
_cell_angle_alpha                90
_cell_angle_beta                 109.764(5)
_cell_angle_gamma                90
_cell_volume                     953.38(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4200
_cell_measurement_temperature    120.0(2)
_cell_measurement_theta_max      74.1640
_cell_measurement_theta_min      3.0460
_shelx_estimated_absorpt_T_max   0.894
_shelx_estimated_absorpt_T_min   0.656
_exptl_absorpt_coefficient_mu    3.112
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.666
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             444
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0191
0 0 1 0.0175
0 1 0 0.0739
0 -1 0 0.0739
1 0 -1 0.0414
-1 0 1 0.0201
1 0 1 0.0299
-1 0 -1 0.0160

_exptl_crystal_size_max          0.148
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.037
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0007 0.0000 -0.9990 -0.0978 -0.0030 0.0412
0.0007 -0.0000 0.9990 0.0978 0.0030 -0.0412
0.0009 1.0007 -0.0021 0.0934 -0.1879 0.2078
-0.0009 -1.0007 0.0021 -0.0934 0.1879 -0.2078
1.0001 0.0004 -1.0002 -0.0295 0.0925 0.0971
-1.0001 -0.0004 1.0002 0.0295 -0.0925 -0.0971
1.0015 0.0004 0.9977 0.1661 0.0985 0.0148
-1.0015 -0.0004 -0.9977 -0.1661 -0.0985 -0.0148

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0828
_diffrn_reflns_av_unetI/netI     0.0795
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8482
_diffrn_reflns_point_group_measured_fraction_full 0.883
_diffrn_reflns_point_group_measured_fraction_max 0.828
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.307
_diffrn_reflns_theta_min         3.049
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.0(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -77.00  26.00   0.50   30.00    --  -47.20  92.00  58.00  206
  2  ω    -19.00  77.00   0.50   30.00    --   47.20 -92.00 -54.00  192
  3  ω    102.00 178.00   0.50  120.00    --  107.11  92.00  58.00  152
  4  ω    -60.00  26.00   0.50   30.00    --  -47.20  37.00  60.00  172
  5  ω   -120.00 -94.00   0.50   30.00    --  -47.20-125.00  30.00   52
  6  ω   -120.00 -94.00   0.50   30.00    --  -47.20-125.00   0.00   52
  7  ω   -120.00 -94.00   0.50   30.00    --  -47.20-125.00 -30.00   52
  8  ω     34.00 120.00   0.50  120.00    --  107.11 -37.00  30.00  172
  9  ω    110.00 178.00   0.50  120.00    --  107.11  77.00 120.00  136
 10  ω     32.00 120.00   0.50  120.00    --  107.11 -19.00  60.00  176
 11  ω    110.00 178.00   0.50  120.00    --  107.11  77.00   0.00  136
 12  ω    103.00 178.00   0.50  120.00    --  107.11  57.00-150.00  150
 13  ω    103.00 178.00   0.50  120.00    --  107.11  57.00  90.00  150
 14  ω     35.00  80.00   0.50  120.00    --  107.11 -92.00 -54.00   90
 15  ω     35.00 120.00   0.50   30.00    --   47.20  37.00  90.00  170
 16  ω     35.00 120.00   0.50   30.00    --   47.20  37.00 150.00  170
 17  ω     35.00 120.00   0.50   30.00    --   47.20  37.00 -30.00  170
 18  ω     35.00 120.00   0.50   30.00    --   47.20  37.00  30.00  170
 19  ω     34.00  95.00   0.50   30.00    --   47.20-125.00 -90.00  122
 20  ω     35.00 120.00   0.50   30.00    --   47.20  37.00-120.00  170
 21  ω     35.00 130.00   0.50  120.00    --  107.11 -77.00  60.00  190
 22  ω     95.00 141.00   0.50  120.00    --  107.11  37.00-180.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu 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      0.0682879000
_diffrn_orient_matrix_UB_12      0.0934966000
_diffrn_orient_matrix_UB_13      0.0978532000
_diffrn_orient_matrix_UB_21      0.0954828000
_diffrn_orient_matrix_UB_22      -0.1878409000
_diffrn_orient_matrix_UB_23      0.0029651000
_diffrn_orient_matrix_UB_31      0.0557881000
_diffrn_orient_matrix_UB_32      0.2075250000
_diffrn_orient_matrix_UB_33      -0.0412423000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.562
_reflns_Friedel_fraction_full    0.742
_reflns_Friedel_fraction_max     0.671
_reflns_number_gt                2823
_reflns_number_total             3363
_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 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (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 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.849
_refine_diff_density_min         -0.910
_refine_diff_density_rms         0.098
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.00(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3363
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0651
_refine_ls_restrained_S_all      1.012
_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)+(0.1237P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1664
_refine_ls_wR_factor_ref         0.1760
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C"(H"A,H"B), C'(H'A,H'B)
2.c Aromatic/amide H refined with riding coordinates:
 C8*(H8*), C2'*(H2'*), C4"(H4"), C8(H8), C7*(H7*), C2"*(H2"*), C3'*(H3'*), C3"*
 (H3"*), C3"(H3"), C7(H7), C2"(H2"), C2'(H2'), C3'(H3'), C4'(H4')
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 1.05571(7) 0.3863(3) 0.71722(5) 0.0421(3) Uani 1 1 d . . . . .
O1 O 0.4800(5) 0.1218(12) 0.2392(4) 0.0389(14) Uani 1 1 d . . . . .
O2 O 0.5150(6) 0.8011(12) 0.4354(4) 0.0427(16) Uani 1 1 d . . . . .
N3 N 0.4730(6) 0.4403(13) 0.3412(4) 0.0353(19) Uani 1 1 d . . . . .
N1 N 0.6267(5) 0.406(2) 0.3033(4) 0.0343(14) Uani 1 1 d . . . . .
C8* C 0.8389(8) 0.3088(17) 0.5864(6) 0.039(2) Uani 1 1 d . . . . .
H8* H 0.837493 0.164677 0.623689 0.046 Uiso 1 1 calc R U . . .
C2'* C 0.5913(8) 0.7060(19) 0.1384(6) 0.039(2) Uani 1 1 d . . . . .
H2'* H 0.535913 0.705187 0.167671 0.047 Uiso 1 1 calc R U . . .
C2 C 0.5234(7) 0.3046(16) 0.2883(5) 0.0335(19) Uani 1 1 d . . . . .
C" C 0.3612(6) 0.378(3) 0.3431(5) 0.0391(17) Uani 1 1 d . . . . .
H"A H 0.348953 0.470144 0.395077 0.047 Uiso 1 1 calc R U . . .
H"B H 0.357602 0.192167 0.354376 0.047 Uiso 1 1 calc R U . . .
C1' C 0.6808(8) 0.5364(18) 0.1680(6) 0.0371(19) Uani 1 1 d . . . . .
C9 C 0.9311(7) 0.4671(17) 0.6093(5) 0.036(2) Uani 1 1 d . . . . .
C4 C 0.5381(7) 0.6417(18) 0.3876(5) 0.0354(19) Uani 1 1 d . . . . .
C4" C 0.0863(9) 0.570(2) 0.0967(6) 0.047(2) Uani 1 1 d . . . . .
H4" H 0.024758 0.613246 0.042989 0.056 Uiso 1 1 calc R U . . .
C8 C 0.9354(8) 0.6810(18) 0.5568(6) 0.0371(19) Uani 1 1 d . . . . .
H8 H 0.999355 0.790787 0.574207 0.045 Uiso 1 1 calc R U . . .
C' C 0.6961(7) 0.350(2) 0.2470(5) 0.037(2) Uani 1 1 d . . . . .
H'A H 0.678077 0.175511 0.221401 0.044 Uiso 1 1 calc R U . . .
H'B H 0.776302 0.351681 0.287046 0.044 Uiso 1 1 calc R U . . .
C7* C 0.7474(8) 0.363(3) 0.5078(5) 0.043(2) Uani 1 1 d . . . . .
H7* H 0.683266 0.254175 0.491058 0.051 Uiso 1 1 calc R U . . .
C2"* C 0.1700(8) 0.2990(17) 0.2275(6) 0.040(2) Uani 1 1 d . . . . .
H2"* H 0.164751 0.154673 0.263446 0.048 Uiso 1 1 calc R U . . .
C3'* C 0.5808(8) 0.874(3) 0.0682(5) 0.0460(19) Uani 1 1 d . . . . .
H3'* H 0.518279 0.987714 0.048505 0.055 Uiso 1 1 calc R U . . .
C6 C 0.7485(8) 0.5739(17) 0.4533(5) 0.0331(18) Uani 1 1 d . . . . .
C5 C 0.6489(7) 0.6233(17) 0.3667(6) 0.0336(18) Uani 1 1 d . . . . .
H5 H 0.661281 0.782632 0.335359 0.040 Uiso 1 1 calc R U . . .
C3"* C 0.0804(8) 0.361(3) 0.1484(6) 0.046(2) Uani 1 1 d . . . . .
H3"* H 0.014665 0.256639 0.130039 0.056 Uiso 1 1 calc R U . . .
C3" C 0.1822(9) 0.716(2) 0.1236(7) 0.048(2) Uani 1 1 d . . . . .
H3" H 0.187249 0.860105 0.087316 0.058 Uiso 1 1 calc R U . . .
C7 C 0.8432(8) 0.7288(19) 0.4783(6) 0.040(2) Uani 1 1 d . . . . .
H7 H 0.845099 0.871777 0.440724 0.048 Uiso 1 1 calc R U . . .
C2" C 0.2712(8) 0.6596(19) 0.2019(6) 0.042(2) Uani 1 1 d . . . . .
H2" H 0.335897 0.766846 0.220226 0.050 Uiso 1 1 calc R U . . .
C2' C 0.7607(8) 0.542(2) 0.1236(6) 0.042(2) Uani 1 1 d . . . . .
H2' H 0.823022 0.427636 0.142479 0.051 Uiso 1 1 calc R U . . .
C1" C 0.2671(8) 0.4477(16) 0.2543(5) 0.037(2) Uani 1 1 d . . . . .
C3' C 0.7499(10) 0.712(2) 0.0525(7) 0.052(3) Uani 1 1 d . . . . .
H3' H 0.804141 0.711526 0.022070 0.062 Uiso 1 1 calc R U . . .
C4' C 0.6621(9) 0.879(3) 0.0257(5) 0.052(2) Uani 1 1 d . . . . .
H4' H 0.656372 0.998937 -0.021980 0.063 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
Br01 C9 1.908(8) . ?
O1 C2 1.226(10) . ?
O2 C4 1.210(10) . ?
N3 C2 1.385(10) . ?
N3 C" 1.455(10) . ?
N3 C4 1.376(12) . ?
N1 C2 1.351(11) . ?
N1 C' 1.454(9) . ?
N1 C5 1.459(12) . ?
C8* H8* 0.9500 . ?
C8* C9 1.372(12) . ?
C8* C7* 1.389(13) . ?
C2'* H2'* 0.9500 . ?
C2'* C1' 1.384(14) . ?
C2'* C3'* 1.365(14) . ?
C" H"A 0.9900 . ?
C" H"B 0.9900 . ?
C" C1" 1.520(12) . ?
C1' C' 1.518(12) . ?
C1' C2' 1.394(12) . ?
C9 C8 1.390(12) . ?
C4 C5 1.538(12) . ?
C4" H4" 0.9500 . ?
C4" C3"* 1.370(17) . ?
C4" C3" 1.370(15) . ?
C8 H8 0.9500 . ?
C8 C7 1.387(13) . ?
C' H'A 0.9900 . ?
C' H'B 0.9900 . ?
C7* H7* 0.9500 . ?
C7* C6 1.387(15) . ?
C2"* H2"* 0.9500 . ?
C2"* C3"* 1.390(13) . ?
C2"* C1" 1.389(13) . ?
C3'* H3'* 0.9500 . ?
C3'* C4' 1.389(13) . ?
C6 C5 1.513(12) . ?
C6 C7 1.384(14) . ?
C5 H5 1.0000 . ?
C3"* H3"* 0.9500 . ?
C3" H3" 0.9500 . ?
C3" C2" 1.373(14) . ?
C7 H7 0.9500 . ?
C2" H2" 0.9500 . ?
C2" C1" 1.380(13) . ?
C2' H2' 0.9500 . ?
C2' C3' 1.379(15) . ?
C3' H3' 0.9500 . ?
C3' C4' 1.359(18) . ?
C4' H4' 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
C2 N3 C" 122.5(8) . . ?
C4 N3 C2 112.6(7) . . ?
C4 N3 C" 124.8(8) . . ?
C2 N1 C' 123.9(8) . . ?
C2 N1 C5 112.1(7) . . ?
C' N1 C5 122.5(7) . . ?
C9 C8* H8* 120.6 . . ?
C9 C8* C7* 118.8(8) . . ?
C7* C8* H8* 120.6 . . ?
C1' C2'* H2'* 119.3 . . ?
C3'* C2'* H2'* 119.3 . . ?
C3'* C2'* C1' 121.5(9) . . ?
O1 C2 N3 124.3(8) . . ?
O1 C2 N1 127.9(8) . . ?
N1 C2 N3 107.8(7) . . ?
N3 C" H"A 108.9 . . ?
N3 C" H"B 108.9 . . ?
N3 C" C1" 113.2(7) . . ?
H"A C" H"B 107.8 . . ?
C1" C" H"A 108.9 . . ?
C1" C" H"B 108.9 . . ?
C2'* C1' C' 122.7(8) . . ?
C2'* C1' C2' 117.9(9) . . ?
C2' C1' C' 119.3(8) . . ?
C8* C9 Br01 117.8(7) . . ?
C8* C9 C8 122.1(8) . . ?
C8 C9 Br01 120.1(7) . . ?
O2 C4 N3 128.2(8) . . ?
O2 C4 C5 126.3(8) . . ?
N3 C4 C5 105.5(7) . . ?
C3"* C4" H4" 120.5 . . ?
C3"* C4" C3" 119.0(9) . . ?
C3" C4" H4" 120.5 . . ?
C9 C8 H8 121.1 . . ?
C7 C8 C9 117.7(9) . . ?
C7 C8 H8 121.1 . . ?
N1 C' C1' 114.3(8) . . ?
N1 C' H'A 108.7 . . ?
N1 C' H'B 108.7 . . ?
C1' C' H'A 108.7 . . ?
C1' C' H'B 108.7 . . ?
H'A C' H'B 107.6 . . ?
C8* C7* H7* 119.5 . . ?
C6 C7* C8* 121.0(9) . . ?
C6 C7* H7* 119.5 . . ?
C3"* C2"* H2"* 119.9 . . ?
C1" C2"* H2"* 119.9 . . ?
C1" C2"* C3"* 120.2(9) . . ?
C2'* C3'* H3'* 120.2 . . ?
C2'* C3'* C4' 119.7(11) . . ?
C4' C3'* H3'* 120.2 . . ?
C7* C6 C5 119.6(8) . . ?
C7 C6 C7* 118.6(8) . . ?
C7 C6 C5 121.7(8) . . ?
N1 C5 C4 101.9(7) . . ?
N1 C5 C6 111.8(7) . . ?
N1 C5 H5 110.4 . . ?
C4 C5 H5 110.4 . . ?
C6 C5 C4 111.5(7) . . ?
C6 C5 H5 110.4 . . ?
C4" C3"* C2"* 120.5(10) . . ?
C4" C3"* H3"* 119.8 . . ?
C2"* C3"* H3"* 119.8 . . ?
C4" C3" H3" 119.4 . . ?
C4" C3" C2" 121.3(10) . . ?
C2" C3" H3" 119.4 . . ?
C8 C7 H7 119.1 . . ?
C6 C7 C8 121.8(8) . . ?
C6 C7 H7 119.1 . . ?
C3" C2" H2" 119.8 . . ?
C3" C2" C1" 120.4(10) . . ?
C1" C2" H2" 119.8 . . ?
C1' C2' H2' 119.7 . . ?
C3' C2' C1' 120.6(10) . . ?
C3' C2' H2' 119.7 . . ?
C2"* C1" C" 118.3(8) . . ?
C2" C1" C" 123.1(9) . . ?
C2" C1" C2"* 118.6(9) . . ?
C2' C3' H3' 119.8 . . ?
C4' C3' C2' 120.3(9) . . ?
C4' C3' H3' 119.8 . . ?
C3'* C4' H4' 120.0 . . ?
C3' C4' C3'* 120.0(11) . . ?
C3' C4' H4' 120.0 . . ?

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 C9 C8 C7 179.1(7) . . . . ?
O2 C4 C5 N1 -177.4(8) . . . . ?
O2 C4 C5 C6 63.2(11) . . . . ?
N3 C" C1" C2"* 149.0(9) . . . . ?
N3 C" C1" C2" -34.8(14) . . . . ?
N3 C4 C5 N1 2.9(8) . . . . ?
N3 C4 C5 C6 -116.6(8) . . . . ?
C8* C9 C8 C7 -1.2(13) . . . . ?
C8* C7* C6 C5 178.3(9) . . . . ?
C8* C7* C6 C7 0.6(15) . . . . ?
C2'* C1' C' N1 -14.5(12) . . . . ?
C2'* C1' C2' C3' 0.0(14) . . . . ?
C2'* C3'* C4' C3' 1.8(17) . . . . ?
C2 N3 C" C1" -71.6(13) . . . . ?
C2 N3 C4 O2 176.3(8) . . . . ?
C2 N3 C4 C5 -4.0(9) . . . . ?
C2 N1 C' C1' 92.4(12) . . . . ?
C2 N1 C5 C4 -1.0(9) . . . . ?
C2 N1 C5 C6 118.3(8) . . . . ?
C" N3 C2 O1 -0.2(12) . . . . ?
C" N3 C2 N1 -178.8(8) . . . . ?
C" N3 C4 O2 -1.4(14) . . . . ?
C" N3 C4 C5 178.3(8) . . . . ?
C1' C2'* C3'* C4' -0.7(16) . . . . ?
C1' C2' C3' C4' 1.1(15) . . . . ?
C9 C8* C7* C6 -0.4(15) . . . . ?
C9 C8 C7 C6 1.5(13) . . . . ?
C4 N3 C2 O1 -178.0(8) . . . . ?
C4 N3 C2 N1 3.5(9) . . . . ?
C4 N3 C" C1" 105.9(9) . . . . ?
C4" C3" C2" C1" 1.9(15) . . . . ?
C' N1 C2 O1 14.3(15) . . . . ?
C' N1 C2 N3 -167.2(8) . . . . ?
C' N1 C5 C4 165.2(8) . . . . ?
C' N1 C5 C6 -75.6(10) . . . . ?
C' C1' C2' C3' -179.0(9) . . . . ?
C7* C8* C9 Br01 -179.6(7) . . . . ?
C7* C8* C9 C8 0.7(14) . . . . ?
C7* C6 C5 N1 -57.4(11) . . . . ?
C7* C6 C5 C4 55.9(11) . . . . ?
C7* C6 C7 C8 -1.2(13) . . . . ?
C3'* C2'* C1' C' 178.8(9) . . . . ?
C3'* C2'* C1' C2' -0.1(14) . . . . ?
C5 N1 C2 O1 -179.8(8) . . . . ?
C5 N1 C2 N3 -1.3(10) . . . . ?
C5 N1 C' C1' -72.0(10) . . . . ?
C5 C6 C7 C8 -178.8(8) . . . . ?
C3"* C4" C3" C2" -1.2(15) . . . . ?
C3"* C2"* C1" C" 178.0(9) . . . . ?
C3"* C2"* C1" C2" 1.5(13) . . . . ?
C3" C4" C3"* C2"* 0.7(15) . . . . ?
C3" C2" C1" C" -178.3(9) . . . . ?
C3" C2" C1" C2"* -2.0(13) . . . . ?
C7 C6 C5 N1 120.2(9) . . . . ?
C7 C6 C5 C4 -126.5(9) . . . . ?
C2' C1' C' N1 164.4(8) . . . . ?
C2' C3' C4' C3'* -1.9(17) . . . . ?
C1" C2"* C3"* C4" -0.9(15) . . . . ?

_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 2.698
_oxdiff_exptl_absorpt_empirical_full_min 0.404
####################################################################### 
# 
# 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_sar-04a
_database_code_depnum_ccdc_archive 'CCDC 2235706'
loop_
_audit_author_name
_audit_author_address
'Matthew I. Polson'
;Univeristy of Canterbury
New Zealand
;
_audit_update_record             
;
2023-01-12 deposited with the CCDC.	2023-06-20 downloaded from the CCDC.
;
_audit_creation_date             2023-01-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
loop_
_audit_author_email
matthew.polson@canterbury.ac.nz
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H20 N2 O2'
_chemical_formula_sum            'C23 H20 N2 O2'
_chemical_formula_weight         356.41
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C23H20N2O2
_chemical_oxdiff_usercomment     AS-330
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      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                   12.0926(2)
_cell_length_b                   5.4361(2)
_cell_length_c                   13.6728(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.641(2)
_cell_angle_gamma                90
_cell_volume                     894.45(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    11644
_cell_measurement_temperature    120.0(2)
_cell_measurement_theta_max      77.0850
_cell_measurement_theta_min      3.6100
_shelx_estimated_absorpt_T_max   0.945
_shelx_estimated_absorpt_T_min   0.827
_exptl_absorpt_coefficient_mu    0.679
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.648
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             376
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 2 0.0236
1 0 -2 0.0619
2 0 -1 0.0921
-2 0 1 0.0386
-1 0 -2 0.0685
1 0 2 0.0951
0 -1 0 0.1556
0 1 0 0.1355

_exptl_crystal_size_max          0.291
_exptl_crystal_size_mid          0.195
_exptl_crystal_size_min          0.085
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.9998 -0.0001 1.9995 0.2040 0.1098 0.0908
0.9998 0.0001 -1.9995 -0.2040 -0.1098 -0.0908
2.0012 0.0001 -0.9999 -0.0715 -0.2217 -0.1358
-2.0012 -0.0001 0.9999 0.0715 0.2217 0.1358
-1.0019 0.0001 -1.9993 -0.2447 0.1125 0.0297
1.0019 -0.0001 1.9993 0.2447 -0.1125 -0.0297
0.0026 -1.0007 -0.0000 -0.0342 -0.1392 0.2447
-0.0026 1.0007 0.0000 0.0342 0.1392 -0.2447

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0890
_diffrn_reflns_av_unetI/netI     0.0566
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15907
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.465
_diffrn_reflns_theta_min         3.673
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.0(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -120.00 -35.00   0.50    2.50    --  -47.45 -41.00   1.00  170
  2  ω    -60.00  25.00   0.50    2.50    --  -47.45  41.00 154.00  170
  3  ω    -25.00  60.00   0.50    2.50    --   47.45 -41.00   1.00  170
  4  ω     35.00 120.00   0.50    2.50    --   47.45  41.00 154.00  170
  5  ω     35.00 120.00   0.50   10.00    --  107.75 -41.00   1.00  170
  6  ω     96.00 178.00   0.50   10.00    --  107.75  41.00 154.00  164
  7  ω   -120.00 -73.00   0.50    2.50    --  -47.45-125.00 150.00   94
  8  ω   -121.00 -35.00   0.50    2.50    --  -47.45 -37.00 -30.00  172
  9  ω     34.00  95.00   0.50    2.50    --   47.45-125.00 -90.00  122
 10  ω     33.00 120.00   0.50    2.50    --   47.45  57.00-120.00  174
 11  ω     33.00 120.00   0.50    2.50    --   47.45  57.00 -90.00  174
 12  ω     33.00 120.00   0.50    2.50    --   47.45  57.00 -60.00  174
 13  ω     91.00 178.00   0.50   10.00    --  107.75  61.00 -60.00  174
 14  ω     35.00 106.00   0.50   10.00    --  107.75 -94.00  30.00  142
 15  ω     94.00 178.00   0.50   10.00    --  107.75  15.00-120.00  168
 16  ω     85.00 178.00   0.50   10.00    --  107.75  77.00-150.00  186
 17  ω     95.00 170.50   0.50   10.00    --  107.75 125.00  60.00  151
 18  ω     85.00 178.00   0.50   10.00    --  107.75  77.00-180.00  186
 19  ω     91.00 178.00   0.50   10.00    --  107.75  61.00-180.00  174
 20  ω    102.00 178.00   0.50   10.00    --  107.75  77.00-120.00  152
 21  ω     94.00 178.00   0.50   10.00    --  107.75  51.00-131.23  168
 22  ω     35.00 106.00   0.50   10.00    --  107.75 -94.00   0.00  142
 23  ω     91.00 178.00   0.50   10.00    --  107.75  61.00-120.00  174
 24  ω     96.50 178.00   0.50   10.00    --  107.75  77.00 -60.00  163
 25  ω     94.00 178.00   0.50   10.00    --  107.75  15.00  90.00  168
 26  ω    100.50 178.00   0.50   10.00    --  107.75  77.00 -90.00  155
 27  ω     36.00 121.00   0.50   10.00    --  107.75 -45.00-120.00  170
 28  ω     91.00 178.00   0.50   10.00    --  107.75  61.00 -90.00  174
 29  ω     91.00 178.00   0.50   10.00    --  107.75  61.00-150.00  174
 30  ω     95.00 178.00   0.50   10.00    --  107.75  45.00 -60.00  166
 31  ω     36.00 178.00   0.50   10.00    --  107.75   0.00 120.00  284
 32  ω     95.00 178.00   0.50   10.00    --  107.75  45.00 -90.00  166
 33  ω     95.00 178.00   0.50   10.00    --  107.75  30.00 -60.00  166
 34  ω     95.00 178.00   0.50   10.00    --  107.75  36.00-105.71  166
 35  ω     33.00 121.00   0.50   10.00    --  107.75 -30.00-180.00  176
 36  ω     35.00  99.00   0.50   10.00    --  107.75-125.00   0.00  128
 37  ω   -120.00 -25.00   0.50    2.50    --  -47.45 -77.00 120.00  190
 38  ω     25.00 120.00   0.50    2.50    --   47.45  77.00   0.00  190
 39  ω     33.00 120.00   0.50    2.50    --   47.45  57.00-180.00  174
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu 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      0.0203578000
_diffrn_orient_matrix_UB_12      0.0342088000
_diffrn_orient_matrix_UB_13      0.1122041000
_diffrn_orient_matrix_UB_21      -0.1110864000
_diffrn_orient_matrix_UB_22      0.1388417000
_diffrn_orient_matrix_UB_23      -0.0006207000
_diffrn_orient_matrix_UB_31      -0.0602124000
_diffrn_orient_matrix_UB_32      -0.2447077000
_diffrn_orient_matrix_UB_33      0.0153018000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.729
_reflns_Friedel_fraction_full    0.929
_reflns_Friedel_fraction_max     0.905
_reflns_number_gt                3289
_reflns_number_total             3500
_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 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (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 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 
;
 Flack x determined using 1263 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(3)
_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     244
_refine_ls_number_reflns         3500
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0550
_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)+(0.1206P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1485
_refine_ls_wR_factor_ref         0.1526
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C'(H'A,H'B), C"(H"A,H"B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C7*(H7*), C3"(H3"), C2'*(H2'*), C2"(H2"), C2"*(H2"*), C3'(H3'), C8*
 (H8*), C9(H9), C2'(H2'), C7(H7), C4"(H4"), C3"*(H3"*), C4'(H4'), C3'*(H3'*)
;
_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 0.62921(16) 0.8895(4) 0.76726(16) 0.0267(5) Uani 1 1 d . . . . .
O2 O 0.52337(16) 0.2366(5) 0.56707(16) 0.0298(5) Uani 1 1 d . . . . .
N1 N 0.73059(18) 0.5850(5) 0.69863(18) 0.0225(5) Uani 1 1 d . . . . .
N3 N 0.54740(18) 0.5782(5) 0.66731(18) 0.0236(5) Uani 1 1 d . . . . .
C2 C 0.6367(2) 0.7058(6) 0.7173(2) 0.0226(6) Uani 1 1 d . . . . .
C6 C 0.7676(2) 0.3996(6) 0.5408(2) 0.0219(6) Uani 1 1 d . . . . .
C4 C 0.5811(2) 0.3808(6) 0.6152(2) 0.0239(6) Uani 1 1 d . . . . .
C8 C 0.9081(3) 0.2588(7) 0.4399(2) 0.0295(7) Uani 1 1 d . . . . .
H8 H 0.963800 0.142883 0.427374 0.035 Uiso 1 1 calc R U . . .
C' C 0.8417(2) 0.6619(6) 0.7357(2) 0.0243(6) Uani 1 1 d . . . . .
H'A H 0.836470 0.811509 0.776292 0.029 Uiso 1 1 calc R U . . .
H'B H 0.883634 0.705268 0.679512 0.029 Uiso 1 1 calc R U . . .
C7* C 0.7453(2) 0.5992(6) 0.4773(2) 0.0252(6) Uani 1 1 d . . . . .
H7* H 0.689780 0.715603 0.489762 0.030 Uiso 1 1 calc R U . . .
C3" C 0.4127(2) 0.3306(7) 0.9258(3) 0.0309(7) Uani 1 1 d . . . . .
H3" H 0.439376 0.186200 0.959487 0.037 Uiso 1 1 calc R U . . .
C2'* C 0.8513(2) 0.2994(6) 0.8533(2) 0.0253(6) Uani 1 1 d . . . . .
H2'* H 0.772878 0.306957 0.853787 0.030 Uiso 1 1 calc R U . . .
C1" C 0.4006(2) 0.5863(6) 0.7804(2) 0.0248(6) Uani 1 1 d . . . . .
C2" C 0.4388(2) 0.3749(6) 0.8304(2) 0.0281(6) Uani 1 1 d . . . . .
H2" H 0.483108 0.260114 0.799259 0.034 Uiso 1 1 calc R U . . .
C1' C 0.9050(2) 0.4667(6) 0.7967(2) 0.0221(6) Uani 1 1 d . . . . .
C" C 0.4323(2) 0.6447(7) 0.6777(2) 0.0273(6) Uani 1 1 d . . . . .
H"A H 0.382648 0.553627 0.628515 0.033 Uiso 1 1 calc R U . . .
H"B H 0.421923 0.822770 0.664692 0.033 Uiso 1 1 calc R U . . .
C5 C 0.7084(2) 0.3759(6) 0.6333(2) 0.0220(6) Uani 1 1 d . . . . .
H5 H 0.732656 0.220992 0.668641 0.026 Uiso 1 1 calc R U . . .
C2"* C 0.3345(2) 0.7504(6) 0.8266(2) 0.0287(7) Uani 1 1 d . . . . .
H2"* H 0.307082 0.893978 0.792861 0.034 Uiso 1 1 calc R U . . .
C3' C 1.0809(2) 0.2770(7) 0.8541(2) 0.0290(7) Uani 1 1 d . . . . .
H3' H 1.159473 0.270211 0.854569 0.035 Uiso 1 1 calc R U . . .
C8* C 0.8045(2) 0.6267(6) 0.3957(2) 0.0273(6) Uani 1 1 d . . . . .
H8* H 0.789487 0.762086 0.352480 0.033 Uiso 1 1 calc R U . . .
C9 C 0.8859(2) 0.4560(6) 0.3773(2) 0.0276(7) Uani 1 1 d . . . . .
H9 H 0.926135 0.475170 0.321518 0.033 Uiso 1 1 calc R U . . .
C2' C 1.0208(2) 0.4538(6) 0.7982(2) 0.0256(6) Uani 1 1 d . . . . .
H2' H 1.058676 0.567408 0.760524 0.031 Uiso 1 1 calc R U . . .
C7 C 0.8486(2) 0.2303(6) 0.5217(2) 0.0261(6) Uani 1 1 d . . . . .
H7 H 0.863627 0.094041 0.564428 0.031 Uiso 1 1 calc R U . . .
C4" C 0.3479(2) 0.4964(7) 0.9718(2) 0.0303(7) Uani 1 1 d . . . . .
H4" H 0.330656 0.467086 1.037050 0.036 Uiso 1 1 calc R U . . .
C3"* C 0.3083(2) 0.7064(7) 0.9217(2) 0.0313(7) Uani 1 1 d . . . . .
H3"* H 0.263208 0.819874 0.952630 0.038 Uiso 1 1 calc R U . . .
C4' C 1.0263(3) 0.1099(7) 0.9094(2) 0.0301(7) Uani 1 1 d . . . . .
H4' H 1.067215 -0.011835 0.947411 0.036 Uiso 1 1 calc R U . . .
C3'* C 0.9114(2) 0.1220(7) 0.9088(2) 0.0292(7) Uani 1 1 d . . . . .
H3'* H 0.873837 0.008207 0.946604 0.035 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 C2 1.218(4) . ?
O2 C4 1.202(4) . ?
N1 C2 1.357(4) . ?
N1 C' 1.450(3) . ?
N1 C5 1.454(4) . ?
N3 C2 1.404(4) . ?
N3 C4 1.372(4) . ?
N3 C" 1.458(3) . ?
C6 C7* 1.400(4) . ?
C6 C5 1.518(3) . ?
C6 C7 1.387(4) . ?
C4 C5 1.535(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.382(5) . ?
C8 C7 1.396(4) . ?
C' H'A 0.9900 . ?
C' H'B 0.9900 . ?
C' C1' 1.510(4) . ?
C7* H7* 0.9500 . ?
C7* C8* 1.392(4) . ?
C3" H3" 0.9500 . ?
C3" C2" 1.393(5) . ?
C3" C4" 1.385(5) . ?
C2'* H2'* 0.9500 . ?
C2'* C1' 1.396(4) . ?
C2'* C3'* 1.388(5) . ?
C1" C2" 1.393(5) . ?
C1" C" 1.524(4) . ?
C1" C2"* 1.390(4) . ?
C2" H2" 0.9500 . ?
C1' C2' 1.400(4) . ?
C" H"A 0.9900 . ?
C" H"B 0.9900 . ?
C5 H5 1.0000 . ?
C2"* H2"* 0.9500 . ?
C2"* C3"* 1.389(4) . ?
C3' H3' 0.9500 . ?
C3' C2' 1.389(5) . ?
C3' C4' 1.390(5) . ?
C8* H8* 0.9500 . ?
C8* C9 1.393(5) . ?
C9 H9 0.9500 . ?
C2' H2' 0.9500 . ?
C7 H7 0.9500 . ?
C4" H4" 0.9500 . ?
C4" C3"* 1.391(5) . ?
C3"* H3"* 0.9500 . ?
C4' H4' 0.9500 . ?
C4' C3'* 1.390(4) . ?
C3'* H3'* 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
C2 N1 C' 123.9(3) . . ?
C2 N1 C5 112.8(2) . . ?
C' N1 C5 123.3(2) . . ?
C2 N3 C" 121.7(2) . . ?
C4 N3 C2 112.7(2) . . ?
C4 N3 C" 125.5(2) . . ?
O1 C2 N1 127.8(3) . . ?
O1 C2 N3 125.6(3) . . ?
N1 C2 N3 106.7(3) . . ?
C7* C6 C5 120.3(2) . . ?
C7 C6 C7* 119.6(3) . . ?
C7 C6 C5 120.0(3) . . ?
O2 C4 N3 127.4(2) . . ?
O2 C4 C5 126.6(3) . . ?
N3 C4 C5 105.9(2) . . ?
C9 C8 H8 120.1 . . ?
C9 C8 C7 119.9(3) . . ?
C7 C8 H8 120.1 . . ?
N1 C' H'A 109.0 . . ?
N1 C' H'B 109.0 . . ?
N1 C' C1' 113.1(2) . . ?
H'A C' H'B 107.8 . . ?
C1' C' H'A 109.0 . . ?
C1' C' H'B 109.0 . . ?
C6 C7* H7* 120.1 . . ?
C8* C7* C6 119.8(3) . . ?
C8* C7* H7* 120.1 . . ?
C2" C3" H3" 119.9 . . ?
C4" C3" H3" 119.9 . . ?
C4" C3" C2" 120.2(3) . . ?
C1' C2'* H2'* 119.7 . . ?
C3'* C2'* H2'* 119.7 . . ?
C3'* C2'* C1' 120.6(2) . . ?
C2" C1" C" 121.5(3) . . ?
C2"* C1" C2" 118.9(3) . . ?
C2"* C1" C" 119.5(3) . . ?
C3" C2" H2" 119.7 . . ?
C1" C2" C3" 120.5(3) . . ?
C1" C2" H2" 119.7 . . ?
C2'* C1' C' 121.7(2) . . ?
C2'* C1' C2' 118.6(3) . . ?
C2' C1' C' 119.7(3) . . ?
N3 C" C1" 111.6(2) . . ?
N3 C" H"A 109.3 . . ?
N3 C" H"B 109.3 . . ?
C1" C" H"A 109.3 . . ?
C1" C" H"B 109.3 . . ?
H"A C" H"B 108.0 . . ?
N1 C5 C6 111.8(2) . . ?
N1 C5 C4 101.9(2) . . ?
N1 C5 H5 109.5 . . ?
C6 C5 C4 114.3(2) . . ?
C6 C5 H5 109.5 . . ?
C4 C5 H5 109.5 . . ?
C1" C2"* H2"* 119.7 . . ?
C3"* C2"* C1" 120.6(3) . . ?
C3"* C2"* H2"* 119.7 . . ?
C2' C3' H3' 120.0 . . ?
C2' C3' C4' 120.1(3) . . ?
C4' C3' H3' 120.0 . . ?
C7* C8* H8* 120.0 . . ?
C7* C8* C9 120.1(3) . . ?
C9 C8* H8* 120.0 . . ?
C8 C9 C8* 120.2(3) . . ?
C8 C9 H9 119.9 . . ?
C8* C9 H9 119.9 . . ?
C1' C2' H2' 119.6 . . ?
C3' C2' C1' 120.8(3) . . ?
C3' C2' H2' 119.6 . . ?
C6 C7 C8 120.4(3) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C3" C4" H4" 120.2 . . ?
C3" C4" C3"* 119.6(3) . . ?
C3"* C4" H4" 120.2 . . ?
C2"* C3"* C4" 120.2(3) . . ?
C2"* C3"* H3"* 119.9 . . ?
C4" C3"* H3"* 119.9 . . ?
C3' C4' H4' 120.2 . . ?
C3'* C4' C3' 119.6(3) . . ?
C3'* C4' H4' 120.2 . . ?
C2'* C3'* C4' 120.4(3) . . ?
C2'* C3'* H3'* 119.8 . . ?
C4' C3'* H3'* 119.8 . . ?

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
O2 C4 C5 N1 -177.8(3) . . . . ?
O2 C4 C5 C6 61.4(4) . . . . ?
N1 C' C1' C2'* -31.7(4) . . . . ?
N1 C' C1' C2' 149.3(3) . . . . ?
N3 C4 C5 N1 0.6(3) . . . . ?
N3 C4 C5 C6 -120.3(3) . . . . ?
C2 N1 C' C1' 122.1(3) . . . . ?
C2 N1 C5 C6 121.2(3) . . . . ?
C2 N1 C5 C4 -1.3(3) . . . . ?
C2 N3 C4 O2 178.7(3) . . . . ?
C2 N3 C4 C5 0.4(3) . . . . ?
C2 N3 C" C1" -68.7(4) . . . . ?
C6 C7* C8* C9 0.0(5) . . . . ?
C4 N3 C2 O1 178.7(3) . . . . ?
C4 N3 C2 N1 -1.2(3) . . . . ?
C4 N3 C" C1" 106.6(3) . . . . ?
C' N1 C2 O1 -1.1(5) . . . . ?
C' N1 C2 N3 178.8(2) . . . . ?
C' N1 C5 C6 -56.1(3) . . . . ?
C' N1 C5 C4 -178.6(3) . . . . ?
C' C1' C2' C3' 179.6(3) . . . . ?
C7* C6 C5 N1 -60.1(3) . . . . ?
C7* C6 C5 C4 55.1(4) . . . . ?
C7* C6 C7 C8 0.4(5) . . . . ?
C7* C8* C9 C8 0.0(5) . . . . ?
C3" C4" C3"* C2"* -0.6(5) . . . . ?
C2'* C1' C2' C3' 0.6(4) . . . . ?
C1" C2"* C3"* C4" -0.1(5) . . . . ?
C2" C3" C4" C3"* 0.6(5) . . . . ?
C2" C1" C" N3 -38.2(4) . . . . ?
C2" C1" C2"* C3"* 0.9(4) . . . . ?
C1' C2'* C3'* C4' 0.5(5) . . . . ?
C" N3 C2 O1 -5.4(5) . . . . ?
C" N3 C2 N1 174.7(2) . . . . ?
C" N3 C4 O2 3.0(5) . . . . ?
C" N3 C4 C5 -175.3(3) . . . . ?
C" C1" C2" C3" 177.2(3) . . . . ?
C" C1" C2"* C3"* -177.3(3) . . . . ?
C5 N1 C2 O1 -178.3(3) . . . . ?
C5 N1 C2 N3 1.6(3) . . . . ?
C5 N1 C' C1' -61.0(3) . . . . ?
C5 C6 C7* C8* 176.3(3) . . . . ?
C5 C6 C7 C8 -176.2(3) . . . . ?
C2"* C1" C2" C3" -1.0(4) . . . . ?
C2"* C1" C" N3 139.9(3) . . . . ?
C3' C4' C3'* C2'* 0.1(5) . . . . ?
C9 C8 C7 C6 -0.4(5) . . . . ?
C2' C3' C4' C3'* -0.4(5) . . . . ?
C7 C6 C7* C8* -0.2(4) . . . . ?
C7 C6 C5 N1 116.4(3) . . . . ?
C7 C6 C5 C4 -128.4(3) . . . . ?
C7 C8 C9 C8* 0.2(5) . . . . ?
C4" C3" C2" C1" 0.2(5) . . . . ?
C4' C3' C2' C1' 0.0(5) . . . . ?
C3'* C2'* C1' C' -179.9(3) . . . . ?
C3'* C2'* C1' C2' -0.9(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 6.600
_oxdiff_exptl_absorpt_empirical_full_min 0.384
