# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_as-124-a_auto
_database_code_depnum_ccdc_archive 'CCDC 2183577'
loop_
_audit_author_name
_audit_author_address
'TANMAYEE NANDA'
;niser
India
;
_audit_update_record             
;
2022-07-03 deposited with the CCDC.	2023-10-25 downloaded from the CCDC.
;
_audit_creation_date             2022-05-24
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_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_melting_point          ?
_chemical_oxdiff_formula         'C H N O '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.1816(4)
_cell_length_b                   8.6211(3)
_cell_length_c                   17.1645(6)
_cell_angle_alpha                90
_cell_angle_beta                 96.736(3)
_cell_angle_gamma                90
_cell_volume                     1790.15(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10852
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      30.4530
_cell_measurement_theta_min      3.8880
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.984
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78639
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.52a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.814
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            20789
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.814
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.507
_diffrn_reflns_theta_min         3.368
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.814
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     29.00  55.00   0.50   20.00    --    3.51-126.00 101.00   52
  2  ω     17.00  42.00   0.50   20.00    --    3.51-145.00 -66.00   50
  3  ω      0.00  26.00   0.50   20.00    --    3.51  37.00  30.00   52
  4  ω     42.00  69.00   0.50   20.00    --    3.51  37.00  30.00   54
  5  ω    -26.00  20.00   0.50   20.00    --   -4.14  77.00 -90.00   92
  6  ω    -19.00  21.00   0.50   20.00    --   -4.14  77.00-150.00   80
  7  ω     -1.00  25.00   0.50   20.00    --   -4.14 -99.00-150.00   52
  8  ω    -27.00  16.00   0.50   20.00    --   -4.14  77.00   0.00   86
  9  ω    -15.00  17.00   0.50   20.00    --   -4.14  77.00-120.00   64
 10  ω     -8.00  18.00   0.50   20.00    --   -4.14 -99.00 -30.00   52
 11  ω    -42.00  19.00   0.50   20.00    --   -4.14 -77.00 -90.00  122
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0321081000
_diffrn_orient_matrix_UB_12      -0.0045298000
_diffrn_orient_matrix_UB_13      -0.0318265000
_diffrn_orient_matrix_UB_21      0.0480798000
_diffrn_orient_matrix_UB_22      -0.0134136000
_diffrn_orient_matrix_UB_23      0.0266714000
_diffrn_orient_matrix_UB_31      -0.0097814000
_diffrn_orient_matrix_UB_32      -0.0810463000
_diffrn_orient_matrix_UB_33      -0.0026493000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3880
_reflns_number_total             4460
_reflns_odcompleteness_completeness 99.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.42.52a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.52a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.52a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         4460
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0377
_refine_ls_restrained_S_all      1.071
_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)+(0.0421P)²+0.5881P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0938
_refine_ls_wR_factor_ref         0.0969
_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:
 C2(H2), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
 C18(H18), C21(H21), C11(H11), C8(H8), C20(H20), C4(H4), C15(H15), C19(H19),
 C13(H13), C12(H12), C7(H7), C14(H14), C5(H5), C6(H6)
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;
_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
O2 O 0.89390(6) 0.44601(8) 0.34459(4) 0.01662(16) Uani 1 1 d . . . . .
O1 O 0.83862(6) 0.21743(8) 0.38043(5) 0.02012(17) Uani 1 1 d . . . . .
N1 N 0.79933(7) 0.64762(9) 0.44808(5) 0.01312(17) Uani 1 1 d . . . . .
C16 C 0.82362(8) 0.70211(11) 0.37391(5) 0.01309(19) Uani 1 1 d . . . . .
C2 C 0.70322(8) 0.42529(11) 0.37364(5) 0.01273(19) Uani 1 1 d . . . . .
H2 H 0.688610 0.497149 0.327861 0.015 Uiso 1 1 calc R U . . .
C1 C 0.81434(8) 0.35028(12) 0.36719(5) 0.01435(19) Uani 1 1 d . . . . .
C10 C 0.73215(8) 0.43271(11) 0.52366(5) 0.01374(19) Uani 1 1 d . . . . .
C17 C 0.86961(8) 0.60009(11) 0.32302(6) 0.01437(19) Uani 1 1 d . . . . .
C3 C 0.60737(8) 0.31184(12) 0.36806(5) 0.01420(19) Uani 1 1 d . . . . .
C18 C 0.90115(8) 0.64694(13) 0.25169(6) 0.0178(2) Uani 1 1 d . . . . .
H18 H 0.930918 0.574013 0.218374 0.021 Uiso 1 1 calc R U . . .
C22 C 0.78646(9) 0.76807(12) 0.50730(6) 0.0166(2) Uani 1 1 d . . . . .
H22A H 0.762510 0.718471 0.554511 0.020 Uiso 1 1 calc R U . . .
H22B H 0.727688 0.841102 0.486119 0.020 Uiso 1 1 calc R U . . .
C21 C 0.81094(8) 0.85636(12) 0.34945(6) 0.0162(2) Uani 1 1 d . . . . .
H21 H 0.778889 0.929065 0.381701 0.019 Uiso 1 1 calc R U . . .
C9 C 0.71212(8) 0.52862(11) 0.44887(5) 0.01239(19) Uani 1 1 d . . . . .
H9 H 0.639995 0.583745 0.449471 0.015 Uiso 1 1 calc R U . . .
C11 C 0.83692(8) 0.37348(12) 0.54944(6) 0.0167(2) Uani 1 1 d . . . . .
H11 H 0.897937 0.398803 0.522077 0.020 Uiso 1 1 calc R U . . .
C8 C 0.60889(9) 0.17387(12) 0.41101(6) 0.0184(2) Uani 1 1 d . . . . .
H8 H 0.672354 0.147035 0.445974 0.022 Uiso 1 1 calc R U . . .
C20 C 0.84452(9) 0.90541(12) 0.27853(6) 0.0189(2) Uani 1 1 d . . . . .
H20 H 0.836859 1.011445 0.263842 0.023 Uiso 1 1 calc R U . . .
C4 C 0.51293(8) 0.34883(12) 0.31764(6) 0.0175(2) Uani 1 1 d . . . . .
H4 H 0.511329 0.441671 0.287710 0.021 Uiso 1 1 calc R U . . .
C15 C 0.64451(9) 0.39893(12) 0.56631(6) 0.0186(2) Uani 1 1 d . . . . .
H15 H 0.573402 0.440958 0.550110 0.022 Uiso 1 1 calc R U . . .
C19 C 0.88887(9) 0.80150(13) 0.22927(6) 0.0196(2) Uani 1 1 d . . . . .
H19 H 0.910670 0.835418 0.180720 0.024 Uiso 1 1 calc R U . . .
C13 C 0.76364(10) 0.24223(13) 0.65608(6) 0.0226(2) Uani 1 1 d . . . . .
H13 H 0.774083 0.175533 0.700383 0.027 Uiso 1 1 calc R U . . .
C12 C 0.85225(9) 0.27753(12) 0.61503(6) 0.0205(2) Uani 1 1 d . . . . .
H12 H 0.923377 0.236105 0.631780 0.025 Uiso 1 1 calc R U . . .
C7 C 0.51741(9) 0.07577(13) 0.40258(6) 0.0219(2) Uani 1 1 d . . . . .
H7 H 0.519466 -0.018947 0.431001 0.026 Uiso 1 1 calc R U . . .
C14 C 0.66013(10) 0.30415(13) 0.63248(6) 0.0234(2) Uani 1 1 d . . . . .
H14 H 0.599988 0.282083 0.661295 0.028 Uiso 1 1 calc R U . . .
C23 C 0.89217(10) 0.85849(13) 0.53089(6) 0.0237(2) Uani 1 1 d . . . . .
H23A H 0.914860 0.911213 0.484789 0.036 Uiso 1 1 calc R U . . .
H23B H 0.950626 0.787023 0.552315 0.036 Uiso 1 1 calc R U . . .
H23C H 0.879237 0.935556 0.570779 0.036 Uiso 1 1 calc R U . . .
C5 C 0.42071(9) 0.25182(14) 0.31037(7) 0.0229(2) Uani 1 1 d . . . . .
H5 H 0.356454 0.279283 0.276357 0.027 Uiso 1 1 calc R U . . .
C6 C 0.42328(9) 0.11524(14) 0.35299(7) 0.0236(2) Uani 1 1 d . . . . .
H6 H 0.360708 0.048665 0.348302 0.028 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
O2 C1 1.3635(12) . ?
O2 C17 1.4012(12) . ?
O1 C1 1.1979(13) . ?
N1 C16 1.4203(12) . ?
N1 C22 1.4744(12) . ?
N1 C9 1.4781(12) . ?
C16 C17 1.4018(13) . ?
C16 C21 1.3976(14) . ?
C2 H2 1.0000 . ?
C2 C1 1.5159(13) . ?
C2 C3 1.5175(13) . ?
C2 C9 1.5621(13) . ?
C10 C9 1.5223(13) . ?
C10 C11 1.3975(14) . ?
C10 C15 1.3942(14) . ?
C17 C18 1.3856(13) . ?
C3 C8 1.3984(14) . ?
C3 C4 1.3931(14) . ?
C18 H18 0.9500 . ?
C18 C19 1.3901(16) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.5190(15) . ?
C21 H21 0.9500 . ?
C21 C20 1.3945(14) . ?
C9 H9 1.0000 . ?
C11 H11 0.9500 . ?
C11 C12 1.3919(14) . ?
C8 H8 0.9500 . ?
C8 C7 1.3930(15) . ?
C20 H20 0.9500 . ?
C20 C19 1.3844(15) . ?
C4 H4 0.9500 . ?
C4 C5 1.3943(15) . ?
C15 H15 0.9500 . ?
C15 C14 1.3940(15) . ?
C19 H19 0.9500 . ?
C13 H13 0.9500 . ?
C13 C12 1.3901(16) . ?
C13 C14 1.3853(17) . ?
C12 H12 0.9500 . ?
C7 H7 0.9500 . ?
C7 C6 1.3878(17) . ?
C14 H14 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C5 H5 0.9500 . ?
C5 C6 1.3846(17) . ?
C6 H6 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O2 C17 120.92(8) . . ?
C16 N1 C22 115.80(8) . . ?
C16 N1 C9 117.61(7) . . ?
C22 N1 C9 110.35(7) . . ?
C17 C16 N1 119.44(9) . . ?
C21 C16 N1 123.83(9) . . ?
C21 C16 C17 116.61(9) . . ?
C1 C2 H2 106.6 . . ?
C1 C2 C3 114.05(8) . . ?
C1 C2 C9 109.13(7) . . ?
C3 C2 H2 106.6 . . ?
C3 C2 C9 113.45(7) . . ?
C9 C2 H2 106.6 . . ?
O2 C1 C2 115.67(8) . . ?
O1 C1 O2 117.69(9) . . ?
O1 C1 C2 126.64(9) . . ?
C11 C10 C9 121.03(9) . . ?
C15 C10 C9 119.96(9) . . ?
C15 C10 C11 118.98(9) . . ?
O2 C17 C16 121.17(8) . . ?
C18 C17 O2 115.97(9) . . ?
C18 C17 C16 122.70(9) . . ?
C8 C3 C2 123.53(9) . . ?
C4 C3 C2 117.70(9) . . ?
C4 C3 C8 118.76(9) . . ?
C17 C18 H18 120.3 . . ?
C17 C18 C19 119.47(9) . . ?
C19 C18 H18 120.3 . . ?
N1 C22 H22A 109.0 . . ?
N1 C22 H22B 109.0 . . ?
N1 C22 C23 112.94(8) . . ?
H22A C22 H22B 107.8 . . ?
C23 C22 H22A 109.0 . . ?
C23 C22 H22B 109.0 . . ?
C16 C21 H21 119.4 . . ?
C20 C21 C16 121.15(9) . . ?
C20 C21 H21 119.4 . . ?
N1 C9 C2 111.62(7) . . ?
N1 C9 C10 109.91(7) . . ?
N1 C9 H9 107.7 . . ?
C2 C9 H9 107.7 . . ?
C10 C9 C2 112.09(8) . . ?
C10 C9 H9 107.7 . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.27(10) . . ?
C12 C11 H11 119.9 . . ?
C3 C8 H8 120.0 . . ?
C7 C8 C3 120.04(10) . . ?
C7 C8 H8 120.0 . . ?
C21 C20 H20 119.6 . . ?
C19 C20 C21 120.82(10) . . ?
C19 C20 H20 119.6 . . ?
C3 C4 H4 119.5 . . ?
C3 C4 C5 121.08(10) . . ?
C5 C4 H4 119.5 . . ?
C10 C15 H15 119.6 . . ?
C14 C15 C10 120.70(10) . . ?
C14 C15 H15 119.6 . . ?
C18 C19 H19 120.4 . . ?
C20 C19 C18 119.22(9) . . ?
C20 C19 H19 120.4 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C14 C13 C12 120.11(10) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.10(10) . . ?
C13 C12 H12 119.9 . . ?
C8 C7 H7 119.7 . . ?
C6 C7 C8 120.55(10) . . ?
C6 C7 H7 119.7 . . ?
C15 C14 H14 120.1 . . ?
C13 C14 C15 119.78(10) . . ?
C13 C14 H14 120.1 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C4 C5 H5 120.2 . . ?
C6 C5 C4 119.66(10) . . ?
C6 C5 H5 120.2 . . ?
C7 C6 H6 120.1 . . ?
C5 C6 C7 119.89(10) . . ?
C5 C6 H6 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
O2 C17 C18 C19 -174.36(9) . . . . ?
N1 C16 C17 O2 -1.16(13) . . . . ?
N1 C16 C17 C18 -176.32(9) . . . . ?
N1 C16 C21 C20 174.78(9) . . . . ?
C16 N1 C22 C23 -64.29(11) . . . . ?
C16 N1 C9 C2 28.85(11) . . . . ?
C16 N1 C9 C10 153.87(8) . . . . ?
C16 C17 C18 C19 1.04(15) . . . . ?
C16 C21 C20 C19 1.68(15) . . . . ?
C2 C3 C8 C7 179.99(9) . . . . ?
C2 C3 C4 C5 -178.84(9) . . . . ?
C1 O2 C17 C16 55.78(12) . . . . ?
C1 O2 C17 C18 -128.75(9) . . . . ?
C1 C2 C3 C8 48.32(12) . . . . ?
C1 C2 C3 C4 -132.12(9) . . . . ?
C1 C2 C9 N1 57.32(10) . . . . ?
C1 C2 C9 C10 -66.47(10) . . . . ?
C10 C11 C12 C13 -1.09(15) . . . . ?
C10 C15 C14 C13 -0.24(16) . . . . ?
C17 O2 C1 O1 175.66(9) . . . . ?
C17 O2 C1 C2 -4.89(12) . . . . ?
C17 C16 C21 C20 -1.12(14) . . . . ?
C17 C18 C19 C20 -0.48(15) . . . . ?
C3 C2 C1 O2 157.97(8) . . . . ?
C3 C2 C1 O1 -22.64(14) . . . . ?
C3 C2 C9 N1 -174.32(8) . . . . ?
C3 C2 C9 C10 61.89(10) . . . . ?
C3 C8 C7 C6 -1.41(16) . . . . ?
C3 C4 C5 C6 -0.96(16) . . . . ?
C22 N1 C16 C17 160.74(9) . . . . ?
C22 N1 C16 C21 -15.05(13) . . . . ?
C22 N1 C9 C2 164.73(8) . . . . ?
C22 N1 C9 C10 -70.26(10) . . . . ?
C21 C16 C17 O2 174.93(8) . . . . ?
C21 C16 C17 C18 -0.23(14) . . . . ?
C21 C20 C19 C18 -0.84(15) . . . . ?
C9 N1 C16 C17 -65.73(12) . . . . ?
C9 N1 C16 C21 118.48(10) . . . . ?
C9 N1 C22 C23 158.97(8) . . . . ?
C9 C2 C1 O2 -74.00(10) . . . . ?
C9 C2 C1 O1 105.39(11) . . . . ?
C9 C2 C3 C8 -77.46(12) . . . . ?
C9 C2 C3 C4 102.10(10) . . . . ?
C9 C10 C11 C12 -175.74(9) . . . . ?
C9 C10 C15 C14 176.42(9) . . . . ?
C11 C10 C9 N1 -46.98(12) . . . . ?
C11 C10 C9 C2 77.77(11) . . . . ?
C11 C10 C15 C14 -1.72(15) . . . . ?
C8 C3 C4 C5 0.74(15) . . . . ?
C8 C7 C6 C5 1.19(17) . . . . ?
C4 C3 C8 C7 0.44(15) . . . . ?
C4 C5 C6 C7 -0.01(17) . . . . ?
C15 C10 C9 N1 134.93(9) . . . . ?
C15 C10 C9 C2 -100.33(10) . . . . ?
C15 C10 C11 C12 2.38(15) . . . . ?
C12 C13 C14 C15 1.56(17) . . . . ?
C14 C13 C12 C11 -0.90(16) . . . . ?

_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 1.336
_oxdiff_exptl_absorpt_empirical_full_min 0.612
####################################################################### 
# 
# 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_pcr_as_140_auto
_database_code_depnum_ccdc_archive 'CCDC 2183578'
loop_
_audit_author_name
_audit_author_address
'TANMAYEE NANDA'
;niser
India
;
_audit_update_record             
;
2022-07-03 deposited with the CCDC.	2023-10-25 downloaded from the CCDC.
;
_audit_creation_date             2022-05-24
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H19 N O2'
_chemical_formula_sum            'C22 H19 N O2'
_chemical_formula_weight         329.38
_chemical_absolute_configuration SS
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.0510(3)
_cell_length_b                   12.5184(6)
_cell_length_c                   16.9921(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1712.56(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5675
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      30.6650
_cell_measurement_theta_min      3.8330
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.984
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.52a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.817
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11357
_diffrn_reflns_point_group_measured_fraction_full 0.936
_diffrn_reflns_point_group_measured_fraction_max 0.718
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.468
_diffrn_reflns_theta_min         3.469
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.817
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      9.00  44.00   0.50   28.55    --    3.51-111.00 103.00   70
  2  ω    -10.00  15.00   0.50   28.55    --    3.51 -77.00 150.00   50
  3  ω    -13.00  18.00   0.50   28.55    --   -4.14 -99.00 -60.00   62
  4  ω    -41.00  -6.00   0.50   28.55    --   -4.14 -77.00 -90.00   70
  5  ω    -26.00  21.00   0.50   28.55    --   -4.14  77.00-180.00   94
  6  ω    -15.00  28.00   0.50   28.55    --   -4.14 -99.00 -90.00   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0449506000
_diffrn_orient_matrix_UB_12      -0.0035327000
_diffrn_orient_matrix_UB_13      -0.0358053000
_diffrn_orient_matrix_UB_21      0.0645383000
_diffrn_orient_matrix_UB_22      -0.0278297000
_diffrn_orient_matrix_UB_23      0.0196758000
_diffrn_orient_matrix_UB_31      -0.0397391000
_diffrn_orient_matrix_UB_32      -0.0492174000
_diffrn_orient_matrix_UB_33      -0.0085549000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.550
_reflns_Friedel_fraction_full    0.855
_reflns_Friedel_fraction_max     0.588
_reflns_number_gt                3322
_reflns_number_total             3736
_reflns_odcompleteness_completeness 99.36
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.42.52a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.52a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.52a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 1086 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3736
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0406
_refine_ls_restrained_S_all      1.035
_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)+(0.0701P)²+0.0421P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1026
_refine_ls_wR_factor_ref         0.1056
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C2(H2A)
2.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C21(H21), C18(H18), C5(H5), C13(H13), C20(H20), C4(H4),
 C11(H11), C8(H8), C6(H6), C12(H12), C7(H7)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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 -0.51761(18) -0.85821(11) -0.35946(8) 0.0269(3) Uani 1 1 d . . . . .
O2 O -0.5210(2) -0.90932(11) -0.20936(9) 0.0291(4) Uani 1 1 d . . . . .
H2 H -0.530194 -0.895489 -0.257531 0.044 Uiso 1 1 calc R U . . .
N1 N -0.3920(2) -0.72057(13) -0.28675(9) 0.0206(3) Uani 1 1 d . . . . .
C10 C -0.1247(2) -0.61942(15) -0.30828(10) 0.0199(4) Uani 1 1 d . . . . .
C17 C -0.4901(2) -0.81785(15) -0.16913(11) 0.0201(4) Uani 1 1 d . . . . .
C1 C -0.4335(2) -0.77749(16) -0.35180(11) 0.0222(4) Uani 1 1 d . . . . .
C14 C 0.1127(3) -0.50295(17) -0.29989(12) 0.0269(4) Uani 1 1 d . . . . .
H14 H 0.161964 -0.435101 -0.309010 0.032 Uiso 1 1 calc R U . . .
C16 C -0.4271(2) -0.72507(15) -0.20500(11) 0.0185(4) Uani 1 1 d . . . . .
C9 C -0.3029(2) -0.63566(15) -0.33096(10) 0.0195(4) Uani 1 1 d . . . . .
H9 H -0.365731 -0.566782 -0.329762 0.023 Uiso 1 1 calc R U . . .
C15 C -0.0517(3) -0.51986(16) -0.31952(12) 0.0242(4) Uani 1 1 d . . . . .
H15 H -0.115461 -0.462984 -0.340881 0.029 Uiso 1 1 calc R U . . .
C21 C -0.3979(2) -0.63504(16) -0.15910(11) 0.0217(4) Uani 1 1 d . . . . .
H21 H -0.356137 -0.571947 -0.183036 0.026 Uiso 1 1 calc R U . . .
C18 C -0.5181(2) -0.81762(16) -0.08829(12) 0.0230(4) Uani 1 1 d . . . . .
H18 H -0.558416 -0.880850 -0.063980 0.028 Uiso 1 1 calc R U . . .
C5 C -0.7078(3) -0.55927(17) -0.50357(12) 0.0293(5) Uani 1 1 d . . . . .
H5 H -0.819287 -0.541398 -0.490841 0.035 Uiso 1 1 calc R U . . .
C19 C -0.4893(2) -0.72858(17) -0.04217(11) 0.0232(4) Uani 1 1 d . . . . .
C13 C 0.2059(3) -0.58413(19) -0.26709(11) 0.0279(5) Uani 1 1 d . . . . .
H13 H 0.318236 -0.571822 -0.252538 0.033 Uiso 1 1 calc R U . . .
C20 C -0.4291(2) -0.63616(16) -0.07869(12) 0.0238(4) Uani 1 1 d . . . . .
H20 H -0.409363 -0.573752 -0.048284 0.029 Uiso 1 1 calc R U . . .
C2 C -0.3437(3) -0.70157(16) -0.40769(11) 0.0225(4) Uani 1 1 d . . . . .
H2A H -0.242353 -0.734657 -0.431383 0.027 Uiso 1 1 calc R U . . .
C3 C -0.4487(3) -0.64465(15) -0.46810(10) 0.0220(4) Uani 1 1 d . . . . .
C4 C -0.6125(2) -0.61910(16) -0.45155(11) 0.0247(4) Uani 1 1 d . . . . .
H4 H -0.660665 -0.642992 -0.403637 0.030 Uiso 1 1 calc R U . . .
C11 C -0.0290(3) -0.70153(18) -0.27650(13) 0.0292(5) Uani 1 1 d . . . . .
H11 H -0.076409 -0.770300 -0.269193 0.035 Uiso 1 1 calc R U . . .
C8 C -0.3814(3) -0.61159(19) -0.53959(12) 0.0308(5) Uani 1 1 d . . . . .
H8 H -0.270272 -0.629705 -0.552829 0.037 Uiso 1 1 calc R U . . .
C6 C -0.6390(3) -0.52588(19) -0.57411(13) 0.0343(5) Uani 1 1 d . . . . .
H6 H -0.703385 -0.485199 -0.610121 0.041 Uiso 1 1 calc R U . . .
C12 C 0.1348(3) -0.68352(19) -0.25552(13) 0.0319(5) Uani 1 1 d . . . . .
H12 H 0.198624 -0.739627 -0.233100 0.038 Uiso 1 1 calc R U . . .
C22 C -0.5176(3) -0.73118(19) 0.04555(12) 0.0330(5) Uani 1 1 d . . . . .
H22A H -0.564005 -0.800633 0.060528 0.049 Uiso 1 1 calc R U . . .
H22B H -0.595357 -0.674395 0.060293 0.049 Uiso 1 1 calc R U . . .
H22C H -0.411686 -0.720214 0.072833 0.049 Uiso 1 1 calc R U . . .
C7 C -0.4781(3) -0.5516(2) -0.59184(13) 0.0368(6) Uani 1 1 d . . . . .
H7 H -0.431476 -0.528413 -0.640268 0.044 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 C1 1.223(2) . ?
O2 H2 0.8400 . ?
O2 C17 1.357(2) . ?
N1 C1 1.357(2) . ?
N1 C16 1.419(2) . ?
N1 C9 1.486(2) . ?
C10 C9 1.499(3) . ?
C10 C15 1.391(3) . ?
C10 C11 1.393(3) . ?
C17 C16 1.406(3) . ?
C17 C18 1.392(3) . ?
C1 C2 1.525(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.381(3) . ?
C14 C13 1.381(3) . ?
C16 C21 1.391(3) . ?
C9 H9 1.0000 . ?
C9 C2 1.578(3) . ?
C15 H15 0.9500 . ?
C21 H21 0.9500 . ?
C21 C20 1.389(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.382(3) . ?
C5 H5 0.9500 . ?
C5 C4 1.389(3) . ?
C5 C6 1.385(3) . ?
C19 C20 1.400(3) . ?
C19 C22 1.508(3) . ?
C13 H13 0.9500 . ?
C13 C12 1.384(3) . ?
C20 H20 0.9500 . ?
C2 H2A 1.0000 . ?
C2 C3 1.508(3) . ?
C3 C4 1.386(3) . ?
C3 C8 1.393(3) . ?
C4 H4 0.9500 . ?
C11 H11 0.9500 . ?
C11 C12 1.384(3) . ?
C8 H8 0.9500 . ?
C8 C7 1.400(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.368(4) . ?
C12 H12 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C7 H7 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
C17 O2 H2 109.5 . . ?
C1 N1 C16 136.70(17) . . ?
C1 N1 C9 94.74(14) . . ?
C16 N1 C9 128.28(15) . . ?
C15 C10 C9 119.37(17) . . ?
C15 C10 C11 118.71(18) . . ?
C11 C10 C9 121.92(18) . . ?
O2 C17 C16 123.01(17) . . ?
O2 C17 C18 117.99(17) . . ?
C18 C17 C16 118.98(18) . . ?
O1 C1 N1 131.05(18) . . ?
O1 C1 C2 135.28(18) . . ?
N1 C1 C2 93.64(15) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C13 C14 C15 120.4(2) . . ?
C17 C16 N1 121.94(17) . . ?
C21 C16 N1 118.91(17) . . ?
C21 C16 C17 119.15(17) . . ?
N1 C9 C10 115.40(15) . . ?
N1 C9 H9 111.2 . . ?
N1 C9 C2 86.73(13) . . ?
C10 C9 H9 111.2 . . ?
C10 C9 C2 118.88(15) . . ?
C2 C9 H9 111.2 . . ?
C10 C15 H15 119.7 . . ?
C14 C15 C10 120.60(19) . . ?
C14 C15 H15 119.7 . . ?
C16 C21 H21 119.6 . . ?
C20 C21 C16 120.87(18) . . ?
C20 C21 H21 119.6 . . ?
C17 C18 H18 118.9 . . ?
C19 C18 C17 122.28(18) . . ?
C19 C18 H18 118.9 . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C6 C5 C4 119.5(2) . . ?
C18 C19 C20 118.25(18) . . ?
C18 C19 C22 121.18(19) . . ?
C20 C19 C22 120.55(19) . . ?
C14 C13 H13 120.2 . . ?
C14 C13 C12 119.63(19) . . ?
C12 C13 H13 120.2 . . ?
C21 C20 C19 120.46(19) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C1 C2 C9 84.84(14) . . ?
C1 C2 H2A 112.3 . . ?
C9 C2 H2A 112.3 . . ?
C3 C2 C1 116.91(17) . . ?
C3 C2 C9 115.61(16) . . ?
C3 C2 H2A 112.3 . . ?
C4 C3 C2 120.27(17) . . ?
C4 C3 C8 118.59(19) . . ?
C8 C3 C2 121.05(19) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 C5 121.38(19) . . ?
C3 C4 H4 119.3 . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.4(2) . . ?
C12 C11 H11 119.8 . . ?
C3 C8 H8 120.1 . . ?
C3 C8 C7 119.7(2) . . ?
C7 C8 H8 120.1 . . ?
C5 C6 H6 120.1 . . ?
C7 C6 C5 119.9(2) . . ?
C7 C6 H6 120.1 . . ?
C13 C12 C11 120.3(2) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C8 C7 H7 119.6 . . ?
C6 C7 C8 120.9(2) . . ?
C6 C7 H7 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C9 176.1(2) . . . . ?
O1 C1 C2 C3 60.0(3) . . . . ?
O2 C17 C16 N1 0.4(3) . . . . ?
O2 C17 C16 C21 -179.51(18) . . . . ?
O2 C17 C18 C19 179.57(17) . . . . ?
N1 C1 C2 C9 -1.68(14) . . . . ?
N1 C1 C2 C3 -117.83(17) . . . . ?
N1 C16 C21 C20 -179.41(17) . . . . ?
N1 C9 C2 C1 1.53(13) . . . . ?
N1 C9 C2 C3 118.96(17) . . . . ?
C10 C9 C2 C1 118.86(17) . . . . ?
C10 C9 C2 C3 -123.71(19) . . . . ?
C10 C11 C12 C13 -1.0(3) . . . . ?
C17 C16 C21 C20 0.5(3) . . . . ?
C17 C18 C19 C20 -0.3(3) . . . . ?
C17 C18 C19 C22 -178.8(2) . . . . ?
C1 N1 C16 C17 17.7(3) . . . . ?
C1 N1 C16 C21 -162.4(2) . . . . ?
C1 N1 C9 C10 -122.27(17) . . . . ?
C1 N1 C9 C2 -1.72(15) . . . . ?
C1 C2 C3 C4 30.8(3) . . . . ?
C1 C2 C3 C8 -152.68(19) . . . . ?
C14 C13 C12 C11 -0.2(3) . . . . ?
C16 N1 C1 O1 -2.3(4) . . . . ?
C16 N1 C1 C2 175.7(2) . . . . ?
C16 N1 C9 C10 63.1(2) . . . . ?
C16 N1 C9 C2 -176.39(18) . . . . ?
C16 C17 C18 C19 1.3(3) . . . . ?
C16 C21 C20 C19 0.5(3) . . . . ?
C9 N1 C1 O1 -176.2(2) . . . . ?
C9 N1 C1 C2 1.78(15) . . . . ?
C9 N1 C16 C17 -170.04(17) . . . . ?
C9 N1 C16 C21 9.8(3) . . . . ?
C9 C10 C15 C14 -179.34(17) . . . . ?
C9 C10 C11 C12 -179.40(18) . . . . ?
C9 C2 C3 C4 -66.7(2) . . . . ?
C9 C2 C3 C8 109.8(2) . . . . ?
C15 C10 C9 N1 -153.37(17) . . . . ?
C15 C10 C9 C2 105.7(2) . . . . ?
C15 C10 C11 C12 1.0(3) . . . . ?
C15 C14 C13 C12 1.4(3) . . . . ?
C18 C17 C16 N1 178.50(17) . . . . ?
C18 C17 C16 C21 -1.4(3) . . . . ?
C18 C19 C20 C21 -0.6(3) . . . . ?
C5 C6 C7 C8 0.1(4) . . . . ?
C13 C14 C15 C10 -1.5(3) . . . . ?
C2 C3 C4 C5 174.79(19) . . . . ?
C2 C3 C8 C7 -174.96(19) . . . . ?
C3 C8 C7 C6 -0.8(4) . . . . ?
C4 C5 C6 C7 -0.3(3) . . . . ?
C4 C3 C8 C7 1.6(3) . . . . ?
C11 C10 C9 N1 27.0(2) . . . . ?
C11 C10 C9 C2 -73.9(2) . . . . ?
C11 C10 C15 C14 0.3(3) . . . . ?
C8 C3 C4 C5 -1.8(3) . . . . ?
C6 C5 C4 C3 1.1(3) . . . . ?
C22 C19 C20 C21 177.85(19) . . . . ?

_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 2.007
_oxdiff_exptl_absorpt_empirical_full_min 0.530
