# 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_220613lt_auto
_database_code_depnum_ccdc_archive 'CCDC 2210043'
loop_
_audit_author_name
_audit_author_address
NTHU
;National Tsing Hua University
Taiwan
;
_audit_update_record             
;
2022-09-28 deposited with the CCDC.	2023-03-17 downloaded from the CCDC.
;
_audit_creation_date             2022-06-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H21 N O2'
_chemical_formula_sum            'C25 H21 N O2'
_chemical_formula_weight         367.43
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.03855(12)
_cell_length_b                   10.22281(12)
_cell_length_c                   10.74746(12)
_cell_angle_alpha                90.6728(9)
_cell_angle_beta                 100.9741(10)
_cell_angle_gamma                93.6105(10)
_cell_volume                     972.68(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7847
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.6210
_cell_measurement_theta_min      4.3050
_shelx_estimated_absorpt_T_max   0.907
_shelx_estimated_absorpt_T_min   0.880
_exptl_absorpt_coefficient_mu    0.626
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93014
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.51a (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_primary    colourless
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0129
_diffrn_reflns_av_unetI/netI     0.0142
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.936
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10355
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.868
_diffrn_reflns_theta_min         4.335
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -99.00 -26.00   0.50    0.05    --  -71.94 125.00 -60.00  146
  2  ω    -62.00 -31.00   0.50    0.05    --  -76.01 111.00 -90.00   62
  3  ω   -119.00 -40.00   0.50    0.05    --  -76.01 -15.00  90.00  158
  4  ω   -125.00 -47.00   0.50    0.05    --  -76.01 -15.00-180.00  156
  5  ω     52.00  78.00   0.50    0.05    --   56.31  15.00-150.00   52
  6  ω     45.00 109.00   0.50    0.05    --   76.52  15.00   0.00  128
  7  ω     48.00 133.00   0.50    0.05    --   84.37  15.00  60.00  170
  8  ω     90.00 127.00   0.50    0.05    --   76.52  15.00  90.00   74
  9  ω     51.00 116.00   0.50    0.05    --   84.37  15.00 150.00  130
 10  ω     42.00  67.00   0.50    0.05    --   76.52  15.00  90.00   50
 11  ω     60.00  90.00   0.50    0.05    --   84.37 -95.00 120.00   60
 12  ω     32.00  58.00   0.50    0.05    --   76.52-111.00 150.00   52
 13  ω     37.00  63.00   0.50    0.05    --   76.52-111.00  60.00   52
 14  ω     67.00  92.00   0.50    0.05    --   76.52-111.00  60.00   50
 15  ω     20.00  46.00   0.50    0.05    --   56.31-125.00 -30.00   52
 16  ω     16.00  46.00   0.50    0.05    --   56.31 -95.00 -90.00   60
 17  ω     22.00  63.00   0.50    0.05    --   56.31-125.00-120.00   82
 18  ω     37.00  82.00   0.50    0.05    --   76.52 -95.00-180.00   90
 19  ω     35.00  71.00   0.50    0.05    --   76.52 -95.00-120.00   72
 20  ω     40.00  65.00   0.50    0.05    --   76.52 -95.00-150.00   50
 21  ω     59.00  92.00   0.50    0.05    --   76.52-111.00 -60.00   66
 22  ω     65.00  91.00   0.50    0.05    --   84.37 -95.00-180.00   52
 23  ω     35.00  60.00   0.50    0.05    --   76.52 -95.00  60.00   50
 24  ω     66.00  92.00   0.50    0.05    --   84.37 -95.00  60.00   52
 25  ω     46.00  92.00   0.50    0.05    --   84.37 -95.00   0.00   92
 26  ω     66.00  91.00   0.50    0.05    --   84.37 -95.00 -60.00   50
 27  ω     17.00  55.00   0.50    0.05    --   56.31 -95.00  60.00   76
 28  ω     14.00  51.00   0.50    0.05    --   56.31 -95.00 120.00   74
 29  ω     40.00  73.00   0.50    0.05    --   76.52 -95.00 150.00   66
 30  ω     50.00  90.00   0.50    0.05    --   84.37 -95.00 150.00   80
 31  ω     44.00  91.00   0.50    0.05    --   84.37 -95.00  90.00   94
 32  ω     64.00  89.00   0.50    0.05    --   84.37 -95.00  30.00   50
 33  ω     43.00  68.00   0.50    0.05    --   84.37 -95.00 -90.00   50
 34  ω     66.00  91.00   0.50    0.05    --   84.37 -95.00-120.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1433522000
_diffrn_orient_matrix_UB_12      0.0218627000
_diffrn_orient_matrix_UB_13      0.0533202000
_diffrn_orient_matrix_UB_21      -0.0944840000
_diffrn_orient_matrix_UB_22      -0.0878411000
_diffrn_orient_matrix_UB_23      -0.1074720000
_diffrn_orient_matrix_UB_31      0.0282823000
_diffrn_orient_matrix_UB_32      -0.1209123000
_diffrn_orient_matrix_UB_33      0.0832990000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3541
_reflns_number_total             3748
_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 1.171.42.51a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.51a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.51a (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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.0076(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3748
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0328
_refine_ls_restrained_S_all      1.030
_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)+(0.0392P)²+0.3140P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0831
_refine_ls_wR_factor_ref         0.0841
_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:
 C8(H8), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C24(H24), C25(H25), C26(H26), C27(H27), C28(H28)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_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
C1 C 0.41452(11) 0.65531(9) 0.27271(9) 0.0184(2) Uani 1 1 d . . . . .
C2 C 0.27140(11) 0.59761(10) 0.27326(10) 0.0209(2) Uani 1 1 d . . . . .
H2 H 0.232337 0.597775 0.349300 0.025 Uiso 1 1 calc R U . . .
C3 C 0.18500(12) 0.53971(10) 0.16350(10) 0.0233(2) Uani 1 1 d . . . . .
H3 H 0.087801 0.499388 0.165125 0.028 Uiso 1 1 calc R U . . .
C4 C 0.23992(12) 0.54045(10) 0.05144(10) 0.0230(2) Uani 1 1 d . . . . .
H4 H 0.179940 0.501466 -0.023638 0.028 Uiso 1 1 calc R U . . .
C5 C 0.38208(12) 0.59796(10) 0.04900(10) 0.0216(2) Uani 1 1 d . . . . .
H5 H 0.419047 0.598997 -0.028052 0.026 Uiso 1 1 calc R U . . .
C6 C 0.47178(11) 0.65466(10) 0.15958(10) 0.0192(2) Uani 1 1 d . . . . .
C8 C 0.62644(11) 0.64896(10) 0.47422(9) 0.0191(2) Uani 1 1 d . . . . .
H8 H 0.638083 0.556063 0.449653 0.023 Uiso 1 1 calc R U . . .
C9 C 0.50823(11) 0.72070(10) 0.38837(9) 0.0183(2) Uani 1 1 d . . . . .
H9 H 0.531580 0.817071 0.382287 0.022 Uiso 1 1 calc R U . . .
C10 C 0.47345(11) 0.76820(9) 0.60937(9) 0.0179(2) Uani 1 1 d . . . . .
C11 C 0.37965(11) 0.87167(10) 0.58543(10) 0.0199(2) Uani 1 1 d . . . . .
H11 H 0.333635 0.889663 0.500861 0.024 Uiso 1 1 calc R U . . .
C12 C 0.35357(12) 0.94848(10) 0.68553(10) 0.0222(2) Uani 1 1 d . . . . .
H12 H 0.287705 1.017727 0.669237 0.027 Uiso 1 1 calc R U . . .
C13 C 0.42297(12) 0.92488(10) 0.80915(10) 0.0234(2) Uani 1 1 d . . . . .
H13 H 0.404615 0.977445 0.877396 0.028 Uiso 1 1 calc R U . . .
C14 C 0.51957(12) 0.82364(11) 0.83221(10) 0.0231(2) Uani 1 1 d . . . . .
H14 H 0.569160 0.808407 0.916452 0.028 Uiso 1 1 calc R U . . .
C15 C 0.54422(11) 0.74459(10) 0.73321(10) 0.0207(2) Uani 1 1 d . . . . .
H15 H 0.609089 0.674672 0.749834 0.025 Uiso 1 1 calc R U . . .
C16 C 0.76737(11) 0.72838(10) 0.53270(9) 0.0198(2) Uani 1 1 d . . . . .
C18 C 1.02277(12) 0.71555(12) 0.63188(12) 0.0320(3) Uani 1 1 d . . . . .
H18A H 1.010507 0.764220 0.709056 0.038 Uiso 1 1 calc R U . . .
H18B H 1.059310 0.778569 0.573453 0.038 Uiso 1 1 calc R U . . .
C19 C 1.13315(12) 0.61253(13) 0.66591(12) 0.0328(3) Uani 1 1 d . . . . .
H19A H 1.150675 0.569887 0.588355 0.049 Uiso 1 1 calc R U . . .
H19B H 1.092306 0.547059 0.718460 0.049 Uiso 1 1 calc R U . . .
H19C H 1.228747 0.653214 0.713208 0.049 Uiso 1 1 calc R U . . .
C21 C 0.62163(11) 0.70962(10) 0.15760(9) 0.0203(2) Uani 1 1 d . . . . .
C22 C 0.74692(12) 0.75386(10) 0.15241(9) 0.0210(2) Uani 1 1 d . . . . .
C23 C 0.89416(11) 0.80655(10) 0.13880(10) 0.0203(2) Uani 1 1 d . . . . .
C24 C 0.99244(12) 0.87287(10) 0.23956(10) 0.0241(2) Uani 1 1 d . . . . .
H24 H 0.962445 0.883333 0.318951 0.029 Uiso 1 1 calc R U . . .
C25 C 1.13362(12) 0.92332(11) 0.22353(11) 0.0262(2) Uani 1 1 d . . . . .
H25 H 1.199460 0.969355 0.291663 0.031 Uiso 1 1 calc R U . . .
C26 C 1.17887(12) 0.90678(11) 0.10847(11) 0.0263(2) Uani 1 1 d . . . . .
H26 H 1.276374 0.939937 0.098453 0.032 Uiso 1 1 calc R U . . .
C27 C 1.08214(12) 0.84200(11) 0.00809(11) 0.0252(2) Uani 1 1 d . . . . .
H27 H 1.113228 0.831428 -0.070832 0.030 Uiso 1 1 calc R U . . .
C28 C 0.94008(12) 0.79250(10) 0.02234(10) 0.0222(2) Uani 1 1 d . . . . .
H28 H 0.873755 0.748952 -0.047080 0.027 Uiso 1 1 calc R U . . .
N7 N 0.48183(9) 0.67732(8) 0.51056(8) 0.01797(19) Uani 1 1 d . . . . .
O17 O 0.87953(8) 0.64979(7) 0.57099(7) 0.02366(18) Uani 1 1 d . . . . .
O20 O 0.77952(8) 0.84624(7) 0.54428(7) 0.02587(19) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.3886(14) . ?
C1 C6 1.4093(14) . ?
C1 C9 1.4893(14) . ?
C2 H2 0.9500 . ?
C2 C3 1.3879(15) . ?
C3 H3 0.9500 . ?
C3 C4 1.3872(15) . ?
C4 H4 0.9500 . ?
C4 C5 1.3840(15) . ?
C5 H5 0.9500 . ?
C5 C6 1.4013(14) . ?
C6 C21 1.4374(14) . ?
C8 H8 1.0000 . ?
C8 C9 1.5067(14) . ?
C8 C16 1.4932(14) . ?
C8 N7 1.4780(12) . ?
C9 H9 1.0000 . ?
C9 N7 1.4483(12) . ?
C10 C11 1.3928(14) . ?
C10 C15 1.3935(14) . ?
C10 N7 1.4187(13) . ?
C11 H11 0.9500 . ?
C11 C12 1.3891(14) . ?
C12 H12 0.9500 . ?
C12 C13 1.3878(15) . ?
C13 H13 0.9500 . ?
C13 C14 1.3902(15) . ?
C14 H14 0.9500 . ?
C14 C15 1.3883(15) . ?
C15 H15 0.9500 . ?
C16 O17 1.3394(12) . ?
C16 O20 1.2058(13) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.4969(17) . ?
C18 O17 1.4539(13) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C21 C22 1.2043(15) . ?
C22 C23 1.4382(14) . ?
C23 C24 1.4008(15) . ?
C23 C28 1.4002(15) . ?
C24 H24 0.9500 . ?
C24 C25 1.3881(15) . ?
C25 H25 0.9500 . ?
C25 C26 1.3862(16) . ?
C26 H26 0.9500 . ?
C26 C27 1.3849(16) . ?
C27 H27 0.9500 . ?
C27 C28 1.3868(15) . ?
C28 H28 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 C1 C6 119.46(9) . . ?
C2 C1 C9 121.58(9) . . ?
C6 C1 C9 118.95(9) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.47(10) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.31(10) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.01(10) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.34(10) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C21 120.53(9) . . ?
C5 C6 C1 119.39(9) . . ?
C5 C6 C21 120.08(9) . . ?
C9 C8 H8 116.7 . . ?
C16 C8 H8 116.7 . . ?
C16 C8 C9 116.24(8) . . ?
N7 C8 H8 116.7 . . ?
N7 C8 C9 58.05(6) . . ?
N7 C8 C16 119.44(8) . . ?
C1 C9 C8 121.06(8) . . ?
C1 C9 H9 115.5 . . ?
C8 C9 H9 115.5 . . ?
N7 C9 C1 117.88(8) . . ?
N7 C9 C8 59.98(6) . . ?
N7 C9 H9 115.5 . . ?
C11 C10 C15 119.87(9) . . ?
C11 C10 N7 119.92(9) . . ?
C15 C10 N7 119.73(9) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.83(9) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.53(10) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 120.3 . . ?
C12 C13 C14 119.40(10) . . ?
C14 C13 H13 120.3 . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.58(10) . . ?
C15 C14 H14 119.7 . . ?
C10 C15 H15 120.1 . . ?
C14 C15 C10 119.75(10) . . ?
C14 C15 H15 120.1 . . ?
O17 C16 C8 110.22(8) . . ?
O20 C16 C8 125.31(9) . . ?
O20 C16 O17 124.47(9) . . ?
H18A C18 H18B 108.5 . . ?
C19 C18 H18A 110.2 . . ?
C19 C18 H18B 110.2 . . ?
O17 C18 H18A 110.2 . . ?
O17 C18 H18B 110.2 . . ?
O17 C18 C19 107.59(9) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C22 C21 C6 178.02(11) . . ?
C21 C22 C23 176.87(11) . . ?
C24 C23 C22 121.30(9) . . ?
C28 C23 C22 119.53(9) . . ?
C28 C23 C24 119.17(10) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 C23 120.07(10) . . ?
C25 C24 H24 120.0 . . ?
C24 C25 H25 119.9 . . ?
C26 C25 C24 120.24(10) . . ?
C26 C25 H25 119.9 . . ?
C25 C26 H26 120.0 . . ?
C27 C26 C25 120.10(10) . . ?
C27 C26 H26 120.0 . . ?
C26 C27 H27 119.9 . . ?
C26 C27 C28 120.25(10) . . ?
C28 C27 H27 119.9 . . ?
C23 C28 H28 119.9 . . ?
C27 C28 C23 120.16(10) . . ?
C27 C28 H28 119.9 . . ?
C9 N7 C8 61.97(6) . . ?
C10 N7 C8 122.38(8) . . ?
C10 N7 C9 121.41(8) . . ?
C16 O17 C18 115.54(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
C1 C2 C3 C4 -0.90(16) . . . . ?
C1 C9 N7 C8 111.62(10) . . . . ?
C1 C9 N7 C10 -135.69(9) . . . . ?
C2 C1 C6 C5 1.20(14) . . . . ?
C2 C1 C6 C21 -177.80(9) . . . . ?
C2 C1 C9 C8 96.26(12) . . . . ?
C2 C1 C9 N7 26.27(14) . . . . ?
C2 C3 C4 C5 0.64(16) . . . . ?
C3 C4 C5 C6 0.55(15) . . . . ?
C4 C5 C6 C1 -1.47(15) . . . . ?
C4 C5 C6 C21 177.54(9) . . . . ?
C6 C1 C2 C3 -0.03(15) . . . . ?
C6 C1 C9 C8 -85.08(12) . . . . ?
C6 C1 C9 N7 -155.07(9) . . . . ?
C8 C9 N7 C10 112.69(10) . . . . ?
C8 C16 O17 C18 -178.95(9) . . . . ?
C9 C1 C2 C3 178.63(9) . . . . ?
C9 C1 C6 C5 -177.49(9) . . . . ?
C9 C1 C6 C21 3.51(14) . . . . ?
C9 C8 C16 O17 -159.90(8) . . . . ?
C9 C8 C16 O20 20.15(15) . . . . ?
C9 C8 N7 C10 -111.19(10) . . . . ?
C10 C11 C12 C13 1.47(15) . . . . ?
C11 C10 C15 C14 0.64(15) . . . . ?
C11 C10 N7 C8 124.89(10) . . . . ?
C11 C10 N7 C9 50.25(13) . . . . ?
C11 C12 C13 C14 0.20(15) . . . . ?
C12 C13 C14 C15 -1.46(15) . . . . ?
C13 C14 C15 C10 1.04(15) . . . . ?
C15 C10 C11 C12 -1.89(14) . . . . ?
C15 C10 N7 C8 -63.05(12) . . . . ?
C15 C10 N7 C9 -137.69(10) . . . . ?
C16 C8 C9 C1 143.82(9) . . . . ?
C16 C8 C9 N7 -109.78(9) . . . . ?
C16 C8 N7 C9 104.27(10) . . . . ?
C16 C8 N7 C10 -6.92(14) . . . . ?
C19 C18 O17 C16 -179.26(9) . . . . ?
C22 C23 C24 C25 -179.66(10) . . . . ?
C22 C23 C28 C27 -179.55(9) . . . . ?
C23 C24 C25 C26 -0.90(16) . . . . ?
C24 C23 C28 C27 1.02(15) . . . . ?
C24 C25 C26 C27 1.27(16) . . . . ?
C25 C26 C27 C28 -0.48(16) . . . . ?
C26 C27 C28 C23 -0.66(16) . . . . ?
C28 C23 C24 C25 -0.23(15) . . . . ?
N7 C8 C9 C1 -106.40(10) . . . . ?
N7 C8 C16 O17 133.63(9) . . . . ?
N7 C8 C16 O20 -46.32(14) . . . . ?
N7 C10 C11 C12 170.16(9) . . . . ?
N7 C10 C15 C14 -171.42(9) . . . . ?
O20 C16 O17 C18 1.00(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 1.127
_oxdiff_exptl_absorpt_empirical_full_min 0.906
####################################################################### 
# 
# 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_211143lt_auto
_database_code_depnum_ccdc_archive 'CCDC 2210048'
loop_
_audit_author_name
_audit_author_address
NTHU
;National Tsing Hua University
Taiwan
;
_audit_update_record             
;
2022-09-28 deposited with the CCDC.	2023-03-17 downloaded from the CCDC.
;
_audit_creation_date             2021-11-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H21 N O2'
_chemical_formula_sum            'C25 H21 N O2'
_chemical_formula_weight         367.43
_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 0.0181 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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.6318(3)
_cell_length_b                   10.8319(4)
_cell_length_c                   11.3759(4)
_cell_angle_alpha                92.501(3)
_cell_angle_beta                 114.674(3)
_cell_angle_gamma                115.008(3)
_cell_volume                     941.83(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6113
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      72.6350
_cell_measurement_theta_min      4.4280
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.646
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89065
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.33a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10151
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.995
_diffrn_reflns_theta_min         4.439
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     41.00  67.00   0.50    0.05    --   69.49  15.00-150.00   52
  2  ω     74.00 116.00   0.50    0.05    --   69.49  15.00-150.00   84
  3  ω     51.00 104.00   0.50    0.05    --   76.49  15.00-180.00  106
  4  ω     60.00 103.00   0.50    0.05    --   56.41  15.00  60.00   86
  5  ω     80.00 116.00   0.50    0.05    --   76.49  15.00 120.00   72
  6  ω     45.00  70.00   0.50    0.05    --   76.49  15.00 120.00   50
  7  ω     54.00  95.00   0.50    0.05    --   80.36-109.00 -13.63   82
  8  ω     32.00  58.00   0.50    0.05    --   56.41-125.00-120.00   52
  9  ω     40.00  97.00   0.50    0.05    --   80.36-113.00-174.40  114
 10  ω     46.00  93.00   0.50    0.05    --   76.49-111.00 -90.00   94
 11  ω     43.00  70.00   0.50    0.05    --   56.41-125.00 -30.00   54
 12  ω     39.00  65.00   0.50    0.05    --   76.49-111.00   0.00   52
 13  ω     35.00  97.00   0.50    0.05    --   80.36-113.00  62.39  124
 14  ω     34.00  92.00   0.50    0.05    --   76.49-111.00 150.00  116
 15  ω     41.00  90.00   0.50    0.05    --   76.49-111.00  90.00   98
 16  ω     46.00  92.00   0.50    0.05    --   76.49-111.00-120.00   92
 17  ω    -92.00 -62.00   0.50    0.05    --  -59.25 -15.00-180.00   60
 18  ω   -120.00 -58.00   0.50    0.05    --  -75.36 -15.00-150.00  124
 19  ω   -102.00 -40.00   0.50    0.05    --  -59.25 -15.00-120.00  124
 20  ω   -114.00 -49.00   0.50    0.05    --  -75.36 -15.00 -90.00  130
 21  ω   -111.00 -51.00   0.50    0.05    --  -75.36 -15.00 -30.00  120
 22  ω    -94.00 -47.00   0.50    0.05    --  -75.36 -15.00 120.00   94
 23  ω    -66.00 -40.00   0.50    0.05    --  -75.36 111.00  90.00   52
 24  ω    -65.00 -39.00   0.50    0.05    --  -75.36 111.00 150.00   52
 25  ω    -64.00 -23.00   0.50    0.05    --  -59.25 125.00  30.00   82
 26  ω    -90.00 -39.00   0.50    0.05    --  -75.36 111.00  60.00  102
 27  ω    -91.00 -31.00   0.50    0.05    --  -75.36 111.00 -30.00  120
 28  ω    -98.00 -34.00   0.50    0.05    --  -80.00 117.00-100.79  128
 29  ω    -55.00 -27.00   0.50    0.05    --  -72.15 125.00-180.00   56
 30  ω    -91.00 -52.00   0.50    0.05    --  -75.36 111.00-120.00   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0211243000
_diffrn_orient_matrix_UB_12      0.0892156000
_diffrn_orient_matrix_UB_13      0.0938765000
_diffrn_orient_matrix_UB_21      0.2002394000
_diffrn_orient_matrix_UB_22      0.0877185000
_diffrn_orient_matrix_UB_23      0.0858307000
_diffrn_orient_matrix_UB_31      0.0023888000
_diffrn_orient_matrix_UB_32      0.1042602000
_diffrn_orient_matrix_UB_33      -0.0879716000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3123
_reflns_number_total             3521
_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 1.171.42.33a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.42.33a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.42.33a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.545
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.0069(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3521
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0363
_refine_ls_restrained_S_all      1.055
_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)+(0.0495P)²+0.2121P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0950
_refine_ls_wR_factor_ref         0.0975
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C26(H26A,H26B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C13(H13), C14(H14),
 C15(H15), C16(H16), C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
2.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C)
;
_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
C1 C 0.50970(15) 0.60214(12) 0.26511(12) 0.0202(3) Uani 1 1 d . . . . .
C3 C 0.46589(15) 0.66133(12) 0.45003(12) 0.0202(3) Uani 1 1 d . . . . .
C4 C 0.62100(16) 0.70327(12) 0.55792(12) 0.0223(3) Uani 1 1 d . . . . .
H4 H 0.620325 0.687138 0.639139 0.027 Uiso 1 1 calc R U . . .
C5 C 0.79142(16) 0.77155(12) 0.56279(12) 0.0232(3) Uani 1 1 d . . . . .
C6 C 0.93752(17) 0.85828(13) 0.68761(13) 0.0286(3) Uani 1 1 d . . . . .
H6 H 0.921362 0.869268 0.763492 0.034 Uiso 1 1 calc R U . . .
C7 C 1.10415(17) 0.92794(14) 0.70254(14) 0.0324(3) Uani 1 1 d . . . . .
H7 H 1.200425 0.988520 0.787183 0.039 Uiso 1 1 calc R U . . .
C8 C 1.13040(17) 0.90909(14) 0.59339(15) 0.0316(3) Uani 1 1 d . . . . .
H8 H 1.244525 0.957305 0.602982 0.038 Uiso 1 1 calc R U . . .
C9 C 0.98971(16) 0.81983(13) 0.47068(14) 0.0274(3) Uani 1 1 d . . . . .
H9 H 1.009417 0.805084 0.397405 0.033 Uiso 1 1 calc R U . . .
C10 C 0.81804(16) 0.75031(12) 0.45173(12) 0.0232(3) Uani 1 1 d . . . . .
C11 C 0.68102(16) 0.64513(13) 0.32354(12) 0.0226(3) Uani 1 1 d . . . . .
H11 H 0.717995 0.602549 0.276496 0.027 Uiso 1 1 calc R U . . .
C12 C 0.37422(16) 0.47916(12) 0.14607(12) 0.0212(3) Uani 1 1 d . . . . .
C13 C 0.41865(17) 0.39444(14) 0.08878(14) 0.0317(3) Uani 1 1 d . . . . .
H13 H 0.537596 0.416868 0.125452 0.038 Uiso 1 1 calc R U . . .
C14 C 0.29137(18) 0.27839(15) -0.02065(15) 0.0345(3) Uani 1 1 d . . . . .
H14 H 0.324049 0.222545 -0.058556 0.041 Uiso 1 1 calc R U . . .
C15 C 0.11692(17) 0.24297(14) -0.07533(13) 0.0289(3) Uani 1 1 d . . . . .
H15 H 0.029902 0.162951 -0.150007 0.035 Uiso 1 1 calc R U . . .
C16 C 0.07101(16) 0.32564(14) -0.01980(13) 0.0272(3) Uani 1 1 d . . . . .
H16 H -0.048250 0.302384 -0.056860 0.033 Uiso 1 1 calc R U . . .
C17 C 0.19824(16) 0.44261(13) 0.08992(12) 0.0235(3) Uani 1 1 d . . . . .
H17 H 0.164734 0.498279 0.127069 0.028 Uiso 1 1 calc R U . . .
C18 C 0.41786(14) 0.78214(12) 0.27254(12) 0.0203(3) Uani 1 1 d . . . . .
C19 C 0.41697(15) 0.80541(13) 0.15210(12) 0.0238(3) Uani 1 1 d . . . . .
H19 H 0.436661 0.747540 0.102771 0.029 Uiso 1 1 calc R U . . .
C20 C 0.38744(16) 0.91270(14) 0.10443(14) 0.0299(3) Uani 1 1 d . . . . .
H20 H 0.387413 0.927368 0.022692 0.036 Uiso 1 1 calc R U . . .
C21 C 0.35794(18) 0.99889(14) 0.17422(14) 0.0340(3) Uani 1 1 d . . . . .
H21 H 0.339211 1.072754 0.141600 0.041 Uiso 1 1 calc R U . . .
C22 C 0.35643(17) 0.97482(14) 0.29242(14) 0.0306(3) Uani 1 1 d . . . . .
H22 H 0.335156 1.032380 0.340555 0.037 Uiso 1 1 calc R U . . .
C23 C 0.38539(16) 0.86824(13) 0.34175(12) 0.0243(3) Uani 1 1 d . . . . .
H23 H 0.383269 0.853345 0.422798 0.029 Uiso 1 1 calc R U . . .
C24 C 0.30324(16) 0.59762(12) 0.46336(12) 0.0216(3) Uani 1 1 d . . . . .
C26 C -0.00557(16) 0.46073(13) 0.34531(12) 0.0244(3) Uani 1 1 d . . . . .
H26A H -0.028011 0.531300 0.380844 0.029 Uiso 1 1 calc R U . . .
H26B H -0.002296 0.395374 0.403334 0.029 Uiso 1 1 calc R U . . .
C27 C -0.14648(16) 0.38018(14) 0.20341(13) 0.0290(3) Uani 1 1 d . . . . .
H27A H -0.156183 0.446737 0.148918 0.044 Uiso 1 1 calc R U . . .
H27B H -0.258126 0.324092 0.202216 0.044 Uiso 1 1 calc R U . . .
H27C H -0.117068 0.317147 0.166509 0.044 Uiso 1 1 calc R U . . .
N2 N 0.44954(13) 0.67623(10) 0.32249(9) 0.0194(2) Uani 1 1 d . . . . .
O25 O 0.15989(11) 0.53115(9) 0.34329(8) 0.0231(2) Uani 1 1 d . . . . .
O28 O 0.30258(12) 0.60600(10) 0.56953(9) 0.0283(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C11 1.3376(17) . ?
C1 C12 1.4862(16) . ?
C1 N2 1.4384(15) . ?
C3 C4 1.3384(17) . ?
C3 C24 1.4990(16) . ?
C3 N2 1.4167(14) . ?
C4 H4 0.9500 . ?
C4 C5 1.4623(17) . ?
C5 C6 1.4059(17) . ?
C5 C10 1.4176(18) . ?
C6 H6 0.9500 . ?
C6 C7 1.3825(19) . ?
C7 H7 0.9500 . ?
C7 C8 1.390(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.3838(19) . ?
C9 H9 0.9500 . ?
C9 C10 1.4082(17) . ?
C10 C11 1.4640(17) . ?
C11 H11 0.9500 . ?
C12 C13 1.4009(17) . ?
C12 C17 1.3944(17) . ?
C13 H13 0.9500 . ?
C13 C14 1.3853(19) . ?
C14 H14 0.9500 . ?
C14 C15 1.3853(19) . ?
C15 H15 0.9500 . ?
C15 C16 1.3838(18) . ?
C16 H16 0.9500 . ?
C16 C17 1.3918(17) . ?
C17 H17 0.9500 . ?
C18 C19 1.4010(17) . ?
C18 C23 1.4055(17) . ?
C18 N2 1.3930(15) . ?
C19 H19 0.9500 . ?
C19 C20 1.3898(18) . ?
C20 H20 0.9500 . ?
C20 C21 1.389(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.386(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.3869(17) . ?
C23 H23 0.9500 . ?
C24 O25 1.3378(14) . ?
C24 O28 1.2100(14) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 C27 1.5019(17) . ?
C26 O25 1.4583(14) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 C1 C12 124.52(11) . . ?
C11 C1 N2 118.56(11) . . ?
N2 C1 C12 116.90(10) . . ?
C4 C3 C24 119.54(11) . . ?
C4 C3 N2 122.14(11) . . ?
N2 C3 C24 118.32(10) . . ?
C3 C4 H4 116.9 . . ?
C3 C4 C5 126.27(11) . . ?
C5 C4 H4 116.9 . . ?
C6 C5 C4 117.14(11) . . ?
C6 C5 C10 118.72(12) . . ?
C10 C5 C4 124.07(11) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 C5 121.57(13) . . ?
C7 C6 H6 119.2 . . ?
C6 C7 H7 120.1 . . ?
C6 C7 C8 119.81(12) . . ?
C8 C7 H7 120.1 . . ?
C7 C8 H8 120.1 . . ?
C9 C8 C7 119.76(12) . . ?
C9 C8 H8 120.1 . . ?
C8 C9 H9 119.2 . . ?
C8 C9 C10 121.63(13) . . ?
C10 C9 H9 119.2 . . ?
C5 C10 C11 123.44(11) . . ?
C9 C10 C5 118.43(12) . . ?
C9 C10 C11 117.56(11) . . ?
C1 C11 C10 127.41(11) . . ?
C1 C11 H11 116.3 . . ?
C10 C11 H11 116.3 . . ?
C13 C12 C1 121.12(11) . . ?
C17 C12 C1 120.91(11) . . ?
C17 C12 C13 117.95(11) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.86(12) . . ?
C14 C13 H13 119.6 . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.65(12) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 H15 120.4 . . ?
C16 C15 C14 119.16(12) . . ?
C16 C15 H15 120.4 . . ?
C15 C16 H16 119.7 . . ?
C15 C16 C17 120.51(12) . . ?
C17 C16 H16 119.7 . . ?
C12 C17 H17 119.6 . . ?
C16 C17 C12 120.88(11) . . ?
C16 C17 H17 119.6 . . ?
C19 C18 C23 118.29(11) . . ?
N2 C18 C19 121.00(11) . . ?
N2 C18 C23 120.71(11) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 C18 120.35(12) . . ?
C20 C19 H19 119.8 . . ?
C19 C20 H20 119.4 . . ?
C21 C20 C19 121.15(12) . . ?
C21 C20 H20 119.4 . . ?
C20 C21 H21 120.7 . . ?
C22 C21 C20 118.59(12) . . ?
C22 C21 H21 120.7 . . ?
C21 C22 H22 119.4 . . ?
C21 C22 C23 121.22(13) . . ?
C23 C22 H22 119.4 . . ?
C18 C23 H23 119.8 . . ?
C22 C23 C18 120.39(12) . . ?
C22 C23 H23 119.8 . . ?
O25 C24 C3 111.38(10) . . ?
O28 C24 C3 124.01(11) . . ?
O28 C24 O25 124.61(11) . . ?
H26A C26 H26B 108.5 . . ?
C27 C26 H26A 110.3 . . ?
C27 C26 H26B 110.3 . . ?
O25 C26 H26A 110.3 . . ?
O25 C26 H26B 110.3 . . ?
O25 C26 C27 107.32(9) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C3 N2 C1 116.06(9) . . ?
C18 N2 C1 121.40(9) . . ?
C18 N2 C3 120.76(10) . . ?
C24 O25 C26 115.75(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C12 C13 C14 178.79(12) . . . . ?
C1 C12 C17 C16 -178.62(10) . . . . ?
C3 C4 C5 C6 154.20(12) . . . . ?
C3 C4 C5 C10 -28.78(19) . . . . ?
C3 C24 O25 C26 177.78(9) . . . . ?
C4 C3 C24 O25 -164.79(10) . . . . ?
C4 C3 C24 O28 15.41(18) . . . . ?
C4 C3 N2 C1 60.93(15) . . . . ?
C4 C3 N2 C18 -104.09(13) . . . . ?
C4 C5 C6 C7 -179.73(11) . . . . ?
C4 C5 C10 C9 -178.42(11) . . . . ?
C4 C5 C10 C11 -7.29(18) . . . . ?
C5 C6 C7 C8 -2.13(19) . . . . ?
C5 C10 C11 C1 33.13(19) . . . . ?
C6 C5 C10 C9 -1.45(17) . . . . ?
C6 C5 C10 C11 169.68(11) . . . . ?
C6 C7 C8 C9 -0.49(19) . . . . ?
C7 C8 C9 C10 2.12(19) . . . . ?
C8 C9 C10 C5 -1.11(18) . . . . ?
C8 C9 C10 C11 -172.77(11) . . . . ?
C9 C10 C11 C1 -155.67(12) . . . . ?
C10 C5 C6 C7 3.09(18) . . . . ?
C11 C1 C12 C13 2.52(19) . . . . ?
C11 C1 C12 C17 -179.02(11) . . . . ?
C11 C1 N2 C3 -67.97(14) . . . . ?
C11 C1 N2 C18 96.94(13) . . . . ?
C12 C1 C11 C10 -169.79(11) . . . . ?
C12 C1 N2 C3 110.22(11) . . . . ?
C12 C1 N2 C18 -84.86(13) . . . . ?
C12 C13 C14 C15 -0.4(2) . . . . ?
C13 C12 C17 C16 -0.12(18) . . . . ?
C13 C14 C15 C16 0.4(2) . . . . ?
C14 C15 C16 C17 -0.25(19) . . . . ?
C15 C16 C17 C12 0.10(19) . . . . ?
C17 C12 C13 C14 0.3(2) . . . . ?
C18 C19 C20 C21 -0.11(19) . . . . ?
C19 C18 C23 C22 -1.11(17) . . . . ?
C19 C18 N2 C1 10.07(17) . . . . ?
C19 C18 N2 C3 174.28(10) . . . . ?
C19 C20 C21 C22 -0.7(2) . . . . ?
C20 C21 C22 C23 0.7(2) . . . . ?
C21 C22 C23 C18 0.27(19) . . . . ?
C23 C18 C19 C20 1.04(17) . . . . ?
C23 C18 N2 C1 -170.12(10) . . . . ?
C23 C18 N2 C3 -5.91(16) . . . . ?
C24 C3 C4 C5 -177.70(10) . . . . ?
C24 C3 N2 C1 -119.67(11) . . . . ?
C24 C3 N2 C18 75.31(14) . . . . ?
C27 C26 O25 C24 -173.88(10) . . . . ?
N2 C1 C11 C10 8.25(18) . . . . ?
N2 C1 C12 C13 -175.55(11) . . . . ?
N2 C1 C12 C17 2.90(16) . . . . ?
N2 C3 C4 C5 1.69(19) . . . . ?
N2 C3 C24 O25 15.80(14) . . . . ?
N2 C3 C24 O28 -164.00(11) . . . . ?
N2 C18 C19 C20 -179.15(11) . . . . ?
N2 C18 C23 C22 179.07(11) . . . . ?
O28 C24 O25 C26 -2.43(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.402
_oxdiff_exptl_absorpt_empirical_full_min 0.685
####################################################################### 
# 
# 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_2205108lt_auto
_database_code_depnum_ccdc_archive 'CCDC 2210060'
loop_
_audit_author_name
_audit_author_address
NTHU
;National Tsing Hua University
Taiwan
;
_audit_update_record             
;
2022-09-28 deposited with the CCDC.	2023-03-17 downloaded from the CCDC.
;
_audit_creation_date             2022-05-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H20 Cl N O2'
_chemical_formula_sum            'C25 H20 Cl N O2'
_chemical_formula_weight         401.87
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O Cl'
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'
Cl Cl 0.3639 0.7018 '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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   11.3472(3)
_cell_length_b                   18.7364(4)
_cell_length_c                   18.9688(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.100(2)
_cell_angle_gamma                90
_cell_volume                     3927.94(14)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8393
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.8480
_cell_measurement_theta_min      4.6220
_shelx_estimated_absorpt_T_max   0.963
_shelx_estimated_absorpt_T_min   0.778
_exptl_absorpt_coefficient_mu    1.890
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81726
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.51a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1680
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            15232
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.192
_diffrn_reflns_theta_min         4.645
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     37.00 105.00   0.50    0.62    --   57.84  15.00-120.00  136
  2  ω     56.00 124.00   0.50    0.62    --   82.82  15.00-120.00  136
  3  ω     77.00 128.00   0.50    0.62    --   82.82  15.00 -30.00  102
  4  ω     55.00 104.00   0.50    0.62    --   74.36  15.00 120.00   98
  5  ω     32.00  57.00   0.50    0.62    --   57.84-125.00  15.00   50
  6  ω     50.00  98.00   0.50    0.62    --   82.82-125.00  90.00   96
  7  ω     59.00 100.00   0.50    0.62    --   74.36-125.00  15.00   82
  8  ω     25.00  63.00   0.50    0.62    --   71.09-125.00  15.00   76
  9  ω     44.00  69.00   0.50    0.62    --   82.82-125.00  15.00   50
 10  ω     39.00  64.00   0.50    0.62    --   74.36 -95.00  30.00   50
 11  ω     17.00  47.00   0.50    0.62    --   57.84 -95.00  30.00   60
 12  ω     33.00  73.00   0.50    0.62    --   71.09 -95.00 -30.00   80
 13  ω     30.00  56.00   0.50    0.62    --   71.09 -95.00 -60.00   52
 14  ω     26.00  60.00   0.50    0.62    --   57.84 -95.00-120.00   68
 15  ω     17.00  44.00   0.50    0.62    --   57.84 -95.00-150.00   54
 16  ω     42.00  76.00   0.50    0.62    --   82.82 -95.00-150.00   68
 17  ω     54.00  99.00   0.50    0.62    --   82.82-125.00-180.00   90
 18  ω   -118.00 -61.00   0.50    0.62    --  -73.84 -15.00 -30.00  114
 19  ω    -97.00 -51.00   0.50    0.62    --  -78.59 115.00  11.53   92
 20  ω    -73.00 -28.00   0.50    0.62    --  -73.84 125.00  93.00   90
 21  ω    -51.00 -20.00   0.50    0.62    --  -61.04 125.00  93.00   62
 22  ω    -97.00 -34.00   0.50    0.62    --  -78.59 114.00  67.15  126
 23  ω    -97.00 -71.00   0.50    0.62    --  -78.59 114.00  -6.99   52
 24  ω    -66.00 -29.00   0.50    0.62    --  -73.90 125.00-180.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1134975000
_diffrn_orient_matrix_UB_12      0.0473211000
_diffrn_orient_matrix_UB_13      -0.0219409000
_diffrn_orient_matrix_UB_21      0.0808067000
_diffrn_orient_matrix_UB_22      0.0669834000
_diffrn_orient_matrix_UB_23      0.0080243000
_diffrn_orient_matrix_UB_31      0.0062048000
_diffrn_orient_matrix_UB_32      -0.0061697000
_diffrn_orient_matrix_UB_33      -0.0799952000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3426
_reflns_number_total             3835
_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 1.171.42.51a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.51a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.51a (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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.451
_refine_diff_density_min         -0.715
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3835
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0447
_refine_ls_restrained_S_all      1.104
_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)+(0.0875P)²+1.4902P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1255
_refine_ls_wR_factor_ref         0.1327
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C7(H7), C8(H8), C10(H10), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
2.c Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C)
;
_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
C2 C 0.52363(14) 0.59993(9) 0.41727(8) 0.0229(3) Uani 1 1 d . . . . .
C3 C 0.43161(14) 0.55913(9) 0.38182(8) 0.0243(3) Uani 1 1 d . . . . .
H3 H 0.353044 0.579451 0.374323 0.029 Uiso 1 1 calc R U . . .
C4 C 0.43869(14) 0.48709(9) 0.35352(8) 0.0239(3) Uani 1 1 d . . . . .
C5 C 0.34537(15) 0.46661(9) 0.29424(8) 0.0257(3) Uani 1 1 d . . . . .
H5 H 0.288482 0.500959 0.270460 0.031 Uiso 1 1 calc R U . . .
C6 C 0.33685(15) 0.39667(10) 0.27088(8) 0.0264(4) Uani 1 1 d . . . . .
C7 C 0.41483(15) 0.34414(9) 0.30591(9) 0.0272(4) Uani 1 1 d . . . . .
H7 H 0.405419 0.295832 0.290441 0.033 Uiso 1 1 calc R U . . .
C8 C 0.50659(15) 0.36392(9) 0.36393(9) 0.0261(4) Uani 1 1 d . . . . .
H8 H 0.559796 0.328341 0.388813 0.031 Uiso 1 1 calc R U . . .
C9 C 0.52320(14) 0.43492(9) 0.38698(8) 0.0236(3) Uani 1 1 d . . . . .
C10 C 0.62439(14) 0.44953(9) 0.44798(8) 0.0238(3) Uani 1 1 d . . . . .
H10 H 0.654290 0.410252 0.478480 0.029 Uiso 1 1 calc R U . . .
C11 C 0.67961(14) 0.51226(9) 0.46563(8) 0.0231(3) Uani 1 1 d . . . . .
C12 C 0.70959(14) 0.59631(8) 0.37244(8) 0.0223(3) Uani 1 1 d . . . . .
C13 C 0.82393(15) 0.56739(9) 0.37247(9) 0.0250(3) Uani 1 1 d . . . . .
H13 H 0.858006 0.532282 0.407287 0.030 Uiso 1 1 calc R U . . .
C14 C 0.88742(15) 0.58992(9) 0.32178(9) 0.0285(4) Uani 1 1 d . . . . .
H14 H 0.964880 0.570254 0.322565 0.034 Uiso 1 1 calc R U . . .
C15 C 0.83902(16) 0.64075(9) 0.27010(9) 0.0289(4) Uani 1 1 d . . . . .
H15 H 0.882497 0.655789 0.235423 0.035 Uiso 1 1 calc R U . . .
C16 C 0.72551(16) 0.66938(9) 0.26989(9) 0.0280(4) Uani 1 1 d . . . . .
H16 H 0.691708 0.704314 0.234813 0.034 Uiso 1 1 calc R U . . .
C17 C 0.66127(15) 0.64759(9) 0.32018(8) 0.0249(3) Uani 1 1 d . . . . .
H17 H 0.583969 0.667582 0.319160 0.030 Uiso 1 1 calc R U . . .
C18 C 0.50644(14) 0.67003(9) 0.44983(8) 0.0231(3) Uani 1 1 d . . . . .
C19 C 0.60237(15) 0.70220(9) 0.49950(8) 0.0251(3) Uani 1 1 d . . . . .
H19 H 0.679552 0.679892 0.510401 0.030 Uiso 1 1 calc R U . . .
C20 C 0.58592(16) 0.76613(9) 0.53285(9) 0.0277(4) Uani 1 1 d . . . . .
H20 H 0.651506 0.786505 0.567098 0.033 Uiso 1 1 calc R U . . .
C21 C 0.47475(16) 0.80077(9) 0.51681(9) 0.0277(4) Uani 1 1 d . . . . .
H21 H 0.464028 0.844638 0.539672 0.033 Uiso 1 1 calc R U . . .
C22 C 0.37929(15) 0.77013(9) 0.46667(9) 0.0275(4) Uani 1 1 d . . . . .
H22 H 0.303104 0.793571 0.454897 0.033 Uiso 1 1 calc R U . . .
C23 C 0.39441(15) 0.70584(9) 0.43385(9) 0.0254(3) Uani 1 1 d . . . . .
H23 H 0.328170 0.685562 0.400022 0.031 Uiso 1 1 calc R U . . .
C25 C 0.78114(14) 0.51461(9) 0.53218(9) 0.0249(3) Uani 1 1 d . . . . .
C27 C 0.90459(16) 0.58869(10) 0.62011(9) 0.0303(4) Uani 1 1 d . . . . .
H27A H 0.984771 0.577005 0.610777 0.036 Uiso 1 1 calc R U . . .
H27B H 0.888723 0.556062 0.657956 0.036 Uiso 1 1 calc R U . . .
C28 C 0.90181(16) 0.66494(10) 0.64411(9) 0.0297(4) Uani 1 1 d . . . . .
H28A H 0.919855 0.696541 0.606752 0.045 Uiso 1 1 calc R U . . .
H28B H 0.962451 0.671891 0.689396 0.045 Uiso 1 1 calc R U . . .
H28C H 0.821327 0.676142 0.651842 0.045 Uiso 1 1 calc R U . . .
Cl24 Cl 0.22348(4) 0.37282(2) 0.19626(2) 0.03104(16) Uani 1 1 d . . . . .
N1 N 0.64595(12) 0.57541(7) 0.42441(7) 0.0225(3) Uani 1 1 d . . . . .
O26 O 0.81045(10) 0.58127(6) 0.55384(6) 0.0275(3) Uani 1 1 d . . . . .
O29 O 0.82938(11) 0.46205(7) 0.56246(6) 0.0323(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C2 C3 1.345(2) . ?
C2 C18 1.483(2) . ?
C2 N1 1.439(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.461(2) . ?
C4 C5 1.412(2) . ?
C4 C9 1.415(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.380(2) . ?
C6 C7 1.388(2) . ?
C6 Cl24 1.7414(16) . ?
C7 H7 0.9500 . ?
C7 C8 1.383(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.400(2) . ?
C9 C10 1.460(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.338(2) . ?
C11 C25 1.505(2) . ?
C11 N1 1.422(2) . ?
C12 C13 1.406(2) . ?
C12 C17 1.400(2) . ?
C12 N1 1.403(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.391(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.388(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.395(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.387(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.404(2) . ?
C18 C23 1.408(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.387(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.390(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.393(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.384(2) . ?
C23 H23 0.9500 . ?
C25 O26 1.333(2) . ?
C25 O29 1.207(2) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C27 C28 1.502(2) . ?
C27 O26 1.4601(18) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 C2 C18 123.45(15) . . ?
C3 C2 N1 119.25(15) . . ?
N1 C2 C18 117.30(13) . . ?
C2 C3 H3 116.3 . . ?
C2 C3 C4 127.41(15) . . ?
C4 C3 H3 116.3 . . ?
C5 C4 C3 116.73(15) . . ?
C5 C4 C9 118.63(15) . . ?
C9 C4 C3 124.15(14) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 119.96(15) . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C7 121.94(15) . . ?
C5 C6 Cl24 119.34(13) . . ?
C7 C6 Cl24 118.72(13) . . ?
C6 C7 H7 120.8 . . ?
C8 C7 C6 118.30(16) . . ?
C8 C7 H7 120.8 . . ?
C7 C8 H8 119.1 . . ?
C7 C8 C9 121.80(16) . . ?
C9 C8 H8 119.1 . . ?
C4 C9 C10 123.88(15) . . ?
C8 C9 C4 119.14(15) . . ?
C8 C9 C10 116.87(15) . . ?
C9 C10 H10 116.5 . . ?
C11 C10 C9 127.06(15) . . ?
C11 C10 H10 116.5 . . ?
C10 C11 C25 117.50(15) . . ?
C10 C11 N1 122.76(14) . . ?
N1 C11 C25 119.74(14) . . ?
C17 C12 C13 118.57(15) . . ?
C17 C12 N1 120.50(14) . . ?
N1 C12 C13 120.92(14) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.34(15) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 119.6 . . ?
C15 C14 C13 120.82(16) . . ?
C15 C14 H14 119.6 . . ?
C14 C15 H15 120.5 . . ?
C14 C15 C16 118.91(15) . . ?
C16 C15 H15 120.5 . . ?
C15 C16 H16 119.5 . . ?
C17 C16 C15 120.92(16) . . ?
C17 C16 H16 119.5 . . ?
C12 C17 H17 119.8 . . ?
C16 C17 C12 120.44(15) . . ?
C16 C17 H17 119.8 . . ?
C19 C18 C2 120.31(14) . . ?
C19 C18 C23 117.68(15) . . ?
C23 C18 C2 122.00(14) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 C18 120.86(15) . . ?
C20 C19 H19 119.6 . . ?
C19 C20 H20 119.6 . . ?
C19 C20 C21 120.85(15) . . ?
C21 C20 H20 119.6 . . ?
C20 C21 H21 120.5 . . ?
C20 C21 C22 118.94(16) . . ?
C22 C21 H21 120.5 . . ?
C21 C22 H22 119.7 . . ?
C23 C22 C21 120.60(16) . . ?
C23 C22 H22 119.7 . . ?
C18 C23 H23 119.5 . . ?
C22 C23 C18 121.04(15) . . ?
C22 C23 H23 119.5 . . ?
O26 C25 C11 112.10(14) . . ?
O29 C25 C11 123.63(15) . . ?
O29 C25 O26 124.27(15) . . ?
H27A C27 H27B 108.6 . . ?
C28 C27 H27A 110.3 . . ?
C28 C27 H27B 110.3 . . ?
O26 C27 H27A 110.3 . . ?
O26 C27 H27B 110.3 . . ?
O26 C27 C28 106.86(13) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C11 N1 C2 116.78(13) . . ?
C12 N1 C2 118.93(13) . . ?
C12 N1 C11 120.10(13) . . ?
C25 O26 C27 115.93(13) . . ?

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
C2 C3 C4 C5 -153.82(16) . . . . ?
C2 C3 C4 C9 34.3(2) . . . . ?
C2 C18 C19 C20 -177.00(14) . . . . ?
C2 C18 C23 C22 177.86(14) . . . . ?
C3 C2 C18 C19 165.53(15) . . . . ?
C3 C2 C18 C23 -13.0(2) . . . . ?
C3 C2 N1 C11 -64.37(19) . . . . ?
C3 C2 N1 C12 92.69(18) . . . . ?
C3 C4 C5 C6 -171.28(15) . . . . ?
C3 C4 C9 C8 167.05(15) . . . . ?
C3 C4 C9 C10 -9.0(2) . . . . ?
C4 C5 C6 C7 2.8(2) . . . . ?
C4 C5 C6 Cl24 -178.40(12) . . . . ?
C4 C9 C10 C11 -25.3(3) . . . . ?
C5 C4 C9 C8 -4.7(2) . . . . ?
C5 C4 C9 C10 179.23(14) . . . . ?
C5 C6 C7 C8 -2.9(2) . . . . ?
C6 C7 C8 C9 -0.9(2) . . . . ?
C7 C8 C9 C4 4.7(2) . . . . ?
C7 C8 C9 C10 -178.94(14) . . . . ?
C8 C9 C10 C11 158.58(16) . . . . ?
C9 C4 C5 C6 1.1(2) . . . . ?
C9 C10 C11 C25 178.90(14) . . . . ?
C9 C10 C11 N1 -1.0(3) . . . . ?
C10 C11 C25 O26 -165.61(14) . . . . ?
C10 C11 C25 O29 13.9(2) . . . . ?
C10 C11 N1 C2 60.1(2) . . . . ?
C10 C11 N1 C12 -96.66(19) . . . . ?
C11 C25 O26 C27 177.31(13) . . . . ?
C12 C13 C14 C15 -0.5(2) . . . . ?
C13 C12 C17 C16 -0.3(2) . . . . ?
C13 C12 N1 C2 -172.77(14) . . . . ?
C13 C12 N1 C11 -16.5(2) . . . . ?
C13 C14 C15 C16 0.3(3) . . . . ?
C14 C15 C16 C17 -0.2(3) . . . . ?
C15 C16 C17 C12 0.2(2) . . . . ?
C17 C12 C13 C14 0.4(2) . . . . ?
C17 C12 N1 C2 8.5(2) . . . . ?
C17 C12 N1 C11 164.74(14) . . . . ?
C18 C2 C3 C4 -174.26(14) . . . . ?
C18 C2 N1 C11 115.83(15) . . . . ?
C18 C2 N1 C12 -87.11(17) . . . . ?
C18 C19 C20 C21 -1.4(2) . . . . ?
C19 C18 C23 C22 -0.7(2) . . . . ?
C19 C20 C21 C22 0.2(2) . . . . ?
C20 C21 C22 C23 0.7(2) . . . . ?
C21 C22 C23 C18 -0.4(2) . . . . ?
C23 C18 C19 C20 1.6(2) . . . . ?
C25 C11 N1 C2 -119.77(16) . . . . ?
C25 C11 N1 C12 83.45(18) . . . . ?
C28 C27 O26 C25 -166.47(14) . . . . ?
Cl24 C6 C7 C8 178.31(12) . . . . ?
N1 C2 C3 C4 5.9(2) . . . . ?
N1 C2 C18 C19 -14.7(2) . . . . ?
N1 C2 C18 C23 166.79(14) . . . . ?
N1 C11 C25 O26 14.3(2) . . . . ?
N1 C11 C25 O29 -166.23(15) . . . . ?
N1 C12 C13 C14 -178.35(15) . . . . ?
N1 C12 C17 C16 178.51(15) . . . . ?
O29 C25 O26 C27 -2.2(2) . . . . ?

_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 0.731
