# 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_a-6-b
_database_code_depnum_ccdc_archive 'CCDC 2258767'
loop_
_audit_author_name
_audit_author_address
ffg
;grfrf
China
;
_audit_update_record             
;
2023-04-25 deposited with the CCDC.	2023-09-10 downloaded from the CCDC.
;
_audit_creation_date             2022-06-22
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H27 N3 O'
_chemical_formula_sum            'C28 H27 N3 O'
_chemical_formula_weight         421.52
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.5239(7)
_cell_length_b                   9.0245(8)
_cell_length_c                   16.1748(14)
_cell_angle_alpha                90
_cell_angle_beta                 90.02(2)
_cell_angle_gamma                90
_cell_volume                     1098.26(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7922
_cell_measurement_temperature    99.95(19)
_cell_measurement_theta_max      71.1410
_cell_measurement_theta_min      2.7350
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.611
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79618
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11455
_diffrn_reflns_point_group_measured_fraction_full 0.949
_diffrn_reflns_point_group_measured_fraction_max 0.912
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.183
_diffrn_reflns_theta_min         2.732
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.95(19)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     80.00 130.00   0.50    0.50    --   42.30  77.00 -90.00  100
  2  ω     96.00 124.00   0.50    0.50    --   42.30  77.00-120.00   56
  3  ω    -25.00  19.00   0.50    0.50    --   42.30 -82.00-180.00   88
  4  ω    -46.00  61.00   0.50    0.50    --   42.30 -57.00  60.00  214
  5  ω     83.00 117.00   0.50    0.50    --   42.30  77.00-180.00   68
  6  ω     30.00 142.00   0.50    0.80    --  101.60 -38.00  90.00  224
  7  ω     21.00 129.00   0.50    0.80    --  101.60 -77.00  30.00  216
  8  ω     28.00 108.00   0.50    0.80    --  101.60 -63.00-150.00  160
  9  ω     21.00 105.00   0.50    0.80    --  101.60 -63.00  30.00  168
 10  ω     23.00 191.00   0.50    0.80    --  101.60  25.00  60.00  336
 11  ω    166.00 191.00   0.50    0.80    --  101.60  50.00 -30.00   50
 12  ω     12.00 132.00   0.50    0.50    --   42.30  57.00  30.00  240
 13  ω     12.00 132.00   0.50    0.50    --   42.30  57.00 150.00  240
 14  ω    -33.00  86.00   0.50    0.50    --   42.30 -82.00 -60.00  238
 15  ω     12.00 132.00   0.50    0.50    --   42.30  57.00-180.00  240
 16  ω    -33.00  63.00   0.50    0.50    --   42.30 -82.00-150.00  192
 17  ω     12.00 132.00   0.50    0.50    --   42.30  57.00 -90.00  240
 18  ω    166.00 191.00   0.50    0.50    --  101.60  82.00 150.00   50
 19  ω     61.00  86.00   0.50    0.50    --   42.30 -82.00-120.00   50
 20  ω     42.00 144.00   0.50    0.50    --  101.60 -82.00-150.00  204
 21  ω     94.00 178.00   0.50    0.50    --  101.60 -25.00 -60.00  168
 22  ω     30.00  58.00   0.50    0.50    --  101.60 -50.00 -90.00   56
 23  ω     97.00 132.00   0.50    0.50    --  101.60 -50.00 -90.00   70
 24  ω     21.00  51.00   0.50    0.50    --  101.60 -25.00 -60.00   60
 25  ω     64.00 100.00   0.50    0.50    --  101.60 -82.00 120.00   72
 26  ω     72.00  98.00   0.50    0.50    --  101.60 -82.00  60.00   52
 27  ω     86.00 143.00   0.50    0.50    --  101.60 -82.00-120.00  114
 28  ω     51.00  64.50   0.50    0.50    --  101.60 -82.00-180.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0279346000
_diffrn_orient_matrix_UB_12      0.1687434000
_diffrn_orient_matrix_UB_13      -0.0042470000
_diffrn_orient_matrix_UB_21      0.1928797000
_diffrn_orient_matrix_UB_22      -0.0245698000
_diffrn_orient_matrix_UB_23      -0.0276869000
_diffrn_orient_matrix_UB_31      -0.0625410000
_diffrn_orient_matrix_UB_32      -0.0002540000
_diffrn_orient_matrix_UB_33      -0.0911865000
_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         0.780
_reflns_Friedel_fraction_full    0.907
_reflns_Friedel_fraction_max     0.857
_reflns_number_gt                3787
_reflns_number_total             3946
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 1601 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3946
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0331
_refine_ls_restrained_S_all      1.076
_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)+(0.0505P)²+0.1343P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0871
_refine_ls_wR_factor_ref         0.0880
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12), C14(H14), C15(H15), C17(H17), C22(H22)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C25(H25), C26(H26),
 C27(H27), C29(H29), C30(H30), C31(H31)
;
_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 0.7356(2) 0.22515(19) 0.77236(10) 0.0331(4) Uani 1 1 d . . . . .
N1 N 0.2691(2) 0.5545(2) 0.75936(11) 0.0239(4) Uani 1 1 d . . . . .
N2 N 0.2343(2) 0.2355(2) 0.85555(11) 0.0249(4) Uani 1 1 d . . . . .
N3 N 0.6997(2) 0.33432(19) 0.64297(10) 0.0216(4) Uani 1 1 d . . . . .
C2 C 0.3530(3) 0.3306(2) 0.89222(13) 0.0217(4) Uani 1 1 d . . . . .
C3 C 0.5197(3) 0.3549(2) 0.85380(13) 0.0214(4) Uani 1 1 d . . . . .
C4 C 0.6418(3) 0.4468(2) 0.89206(14) 0.0265(5) Uani 1 1 d . . . . .
H4 H 0.752456 0.460897 0.867670 0.032 Uiso 1 1 calc R U . . .
C5 C 0.6032(3) 0.5191(3) 0.96665(14) 0.0321(5) Uani 1 1 d . . . . .
H5 H 0.688155 0.579744 0.991076 0.039 Uiso 1 1 calc R U . . .
C6 C 0.4431(3) 0.5011(3) 1.00331(14) 0.0322(5) Uani 1 1 d . . . . .
H6 H 0.417230 0.551010 1.052167 0.039 Uiso 1 1 calc R U . . .
C7 C 0.3146(3) 0.4062(2) 0.96710(14) 0.0259(5) Uani 1 1 d . . . . .
C8 C 0.1455(3) 0.3825(3) 1.00208(16) 0.0343(6) Uani 1 1 d . . . . .
H8 H 0.114305 0.430346 1.050882 0.041 Uiso 1 1 calc R U . . .
C9 C 0.0282(3) 0.2901(3) 0.96486(16) 0.0356(6) Uani 1 1 d . . . . .
H9 H -0.083994 0.274662 0.987427 0.043 Uiso 1 1 calc R U . . .
C10 C 0.0791(3) 0.2181(3) 0.89147(15) 0.0313(5) Uani 1 1 d . . . . .
H10 H -0.002089 0.154122 0.866856 0.038 Uiso 1 1 calc R U . . .
C12 C 0.8328(3) 0.2834(2) 0.70195(13) 0.0241(4) Uani 1 1 d . . . . .
H12 H 0.911991 0.364311 0.718512 0.029 Uiso 1 1 calc R U . . .
C14 C 0.5596(3) 0.2847(2) 0.77138(13) 0.0235(4) Uani 1 1 d . . . . .
H14 H 0.476177 0.202669 0.763121 0.028 Uiso 1 1 calc R U . . .
C15 C 0.5515(3) 0.3883(2) 0.69222(13) 0.0202(4) Uani 1 1 d . . . . .
H15 H 0.440240 0.369713 0.662464 0.024 Uiso 1 1 calc R U . . .
C16 C 0.9356(3) 0.1593(3) 0.66005(14) 0.0289(5) Uani 1 1 d . . . . .
H16A H 0.925016 0.067545 0.690945 0.035 Uiso 1 1 calc R U . . .
H16B H 1.060367 0.184572 0.654864 0.035 Uiso 1 1 calc R U . . .
C17 C 0.8474(3) 0.1450(3) 0.57412(15) 0.0305(5) Uani 1 1 d . . . . .
H17 H 0.841105 0.040708 0.557583 0.037 Uiso 1 1 calc R U . . .
C18 C 0.9493(3) 0.2345(3) 0.50963(15) 0.0361(6) Uani 1 1 d . . . . .
H18A H 1.057201 0.181675 0.495129 0.043 Uiso 1 1 calc R U . . .
H18B H 0.983473 0.328902 0.533459 0.043 Uiso 1 1 calc R U . . .
C19 C 0.8405(3) 0.2625(4) 0.43083(16) 0.0451(7) Uani 1 1 d . . . . .
H19A H 0.909617 0.321663 0.392469 0.054 Uiso 1 1 calc R U . . .
H19B H 0.813219 0.168750 0.404356 0.054 Uiso 1 1 calc R U . . .
C20 C 0.6685(3) 0.3431(3) 0.45181(15) 0.0388(6) Uani 1 1 d . . . . .
H20A H 0.695688 0.437783 0.477189 0.047 Uiso 1 1 calc R U . . .
H20B H 0.601708 0.361639 0.401573 0.047 Uiso 1 1 calc R U . . .
C21 C 0.5575(3) 0.2503(3) 0.51073(15) 0.0341(5) Uani 1 1 d . . . . .
H21A H 0.518528 0.161248 0.482468 0.041 Uiso 1 1 calc R U . . .
H21B H 0.452578 0.305928 0.526510 0.041 Uiso 1 1 calc R U . . .
C22 C 0.6602(3) 0.2065(2) 0.58876(14) 0.0268(5) Uani 1 1 d . . . . .
H22 H 0.590614 0.133549 0.619851 0.032 Uiso 1 1 calc R U . . .
C23 C 0.4229(3) 0.6303(2) 0.74656(13) 0.0218(4) Uani 1 1 d . . . . .
C24 C 0.5679(3) 0.5533(2) 0.70975(12) 0.0210(4) Uani 1 1 d . . . . .
C25 C 0.7182(3) 0.6308(2) 0.69063(13) 0.0242(4) Uani 1 1 d . . . . .
H25 H 0.810626 0.582830 0.663425 0.029 Uiso 1 1 calc R U . . .
C26 C 0.7368(3) 0.7827(2) 0.71126(15) 0.0293(5) Uani 1 1 d . . . . .
H26 H 0.840884 0.832469 0.697546 0.035 Uiso 1 1 calc R U . . .
C27 C 0.6039(3) 0.8565(3) 0.75095(14) 0.0283(5) Uani 1 1 d . . . . .
H27 H 0.619084 0.954893 0.766500 0.034 Uiso 1 1 calc R U . . .
C28 C 0.4428(3) 0.7824(2) 0.76830(13) 0.0248(5) Uani 1 1 d . . . . .
C29 C 0.2962(3) 0.8541(3) 0.80515(14) 0.0291(5) Uani 1 1 d . . . . .
H29 H 0.303119 0.953458 0.820030 0.035 Uiso 1 1 calc R U . . .
C30 C 0.1446(3) 0.7755(3) 0.81856(14) 0.0316(5) Uani 1 1 d . . . . .
H30 H 0.046691 0.820129 0.843352 0.038 Uiso 1 1 calc R U . . .
C31 C 0.1380(3) 0.6264(3) 0.79447(14) 0.0276(5) Uani 1 1 d . . . . .
H31 H 0.033018 0.574756 0.804118 0.033 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 C12 1.452(3) . ?
O1 C14 1.429(2) . ?
N1 C23 1.360(3) . ?
N1 C31 1.310(3) . ?
N2 C2 1.373(3) . ?
N2 C10 1.313(3) . ?
N3 C12 1.458(3) . ?
N3 C15 1.454(2) . ?
N3 C22 1.479(3) . ?
C2 C3 1.417(3) . ?
C2 C7 1.419(3) . ?
C3 C4 1.384(3) . ?
C3 C14 1.506(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.402(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.352(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.418(3) . ?
C7 C8 1.409(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.355(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.407(4) . ?
C10 H10 0.9300 . ?
C12 H12 0.9800 . ?
C12 C16 1.521(3) . ?
C14 H14 0.9800 . ?
C14 C15 1.586(3) . ?
C15 H15 0.9800 . ?
C15 C24 1.521(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.546(3) . ?
C17 H17 0.9800 . ?
C17 C18 1.526(3) . ?
C17 C22 1.532(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.536(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.522(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.519(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.531(3) . ?
C22 H22 0.9800 . ?
C23 C24 1.424(3) . ?
C23 C28 1.424(3) . ?
C24 C25 1.365(3) . ?
C25 H25 0.9300 . ?
C25 C26 1.417(3) . ?
C26 H26 0.9300 . ?
C26 C27 1.362(3) . ?
C27 H27 0.9300 . ?
C27 C28 1.412(3) . ?
C28 C29 1.411(3) . ?
C29 H29 0.9300 . ?
C29 C30 1.361(3) . ?
C30 H30 0.9300 . ?
C30 C31 1.402(3) . ?
C31 H31 0.9300 . ?

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
C14 O1 C12 108.78(16) . . ?
C31 N1 C23 117.26(19) . . ?
C10 N2 C2 117.5(2) . . ?
C12 N3 C22 106.27(16) . . ?
C15 N3 C12 105.90(16) . . ?
C15 N3 C22 115.59(16) . . ?
N2 C2 C3 118.88(18) . . ?
N2 C2 C7 122.45(18) . . ?
C3 C2 C7 118.67(19) . . ?
C2 C3 C14 119.98(18) . . ?
C4 C3 C2 118.98(19) . . ?
C4 C3 C14 121.01(19) . . ?
C3 C4 H4 119.1 . . ?
C3 C4 C5 121.7(2) . . ?
C5 C4 H4 119.1 . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.4(2) . . ?
C6 C5 H5 119.8 . . ?
C5 C6 H6 120.1 . . ?
C5 C6 C7 119.9(2) . . ?
C7 C6 H6 120.1 . . ?
C6 C7 C2 120.27(19) . . ?
C8 C7 C2 117.0(2) . . ?
C8 C7 C6 122.8(2) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.2(2) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 120.6 . . ?
C8 C9 C10 118.8(2) . . ?
C10 C9 H9 120.6 . . ?
N2 C10 C9 124.1(2) . . ?
N2 C10 H10 118.0 . . ?
C9 C10 H10 118.0 . . ?
O1 C12 N3 106.34(15) . . ?
O1 C12 H12 111.2 . . ?
O1 C12 C16 109.83(18) . . ?
N3 C12 H12 111.2 . . ?
N3 C12 C16 106.87(18) . . ?
C16 C12 H12 111.2 . . ?
O1 C14 C3 109.47(17) . . ?
O1 C14 H14 108.1 . . ?
O1 C14 C15 105.45(16) . . ?
C3 C14 H14 108.1 . . ?
C3 C14 C15 117.31(17) . . ?
C15 C14 H14 108.1 . . ?
N3 C15 C14 102.42(16) . . ?
N3 C15 H15 109.2 . . ?
N3 C15 C24 111.59(16) . . ?
C14 C15 H15 109.2 . . ?
C24 C15 C14 115.05(17) . . ?
C24 C15 H15 109.2 . . ?
C12 C16 H16A 110.9 . . ?
C12 C16 H16B 110.9 . . ?
C12 C16 C17 104.09(18) . . ?
H16A C16 H16B 109.0 . . ?
C17 C16 H16A 110.9 . . ?
C17 C16 H16B 110.9 . . ?
C16 C17 H17 110.2 . . ?
C18 C17 C16 110.8(2) . . ?
C18 C17 H17 110.2 . . ?
C18 C17 C22 112.1(2) . . ?
C22 C17 C16 103.04(17) . . ?
C22 C17 H17 110.2 . . ?
C17 C18 H18A 109.0 . . ?
C17 C18 H18B 109.0 . . ?
C17 C18 C19 112.7(2) . . ?
H18A C18 H18B 107.8 . . ?
C19 C18 H18A 109.0 . . ?
C19 C18 H18B 109.0 . . ?
C18 C19 H19A 109.6 . . ?
C18 C19 H19B 109.6 . . ?
H19A C19 H19B 108.1 . . ?
C20 C19 C18 110.29(19) . . ?
C20 C19 H19A 109.6 . . ?
C20 C19 H19B 109.6 . . ?
C19 C20 H20A 109.6 . . ?
C19 C20 H20B 109.6 . . ?
H20A C20 H20B 108.2 . . ?
C21 C20 C19 110.1(2) . . ?
C21 C20 H20A 109.6 . . ?
C21 C20 H20B 109.6 . . ?
C20 C21 H21A 109.1 . . ?
C20 C21 H21B 109.1 . . ?
C20 C21 C22 112.47(19) . . ?
H21A C21 H21B 107.8 . . ?
C22 C21 H21A 109.1 . . ?
C22 C21 H21B 109.1 . . ?
N3 C22 C17 100.91(16) . . ?
N3 C22 C21 112.88(19) . . ?
N3 C22 H22 109.1 . . ?
C17 C22 H22 109.1 . . ?
C21 C22 C17 115.44(18) . . ?
C21 C22 H22 109.1 . . ?
N1 C23 C24 118.06(19) . . ?
N1 C23 C28 122.45(19) . . ?
C24 C23 C28 119.49(19) . . ?
C23 C24 C15 119.58(18) . . ?
C25 C24 C15 121.77(18) . . ?
C25 C24 C23 118.65(19) . . ?
C24 C25 H25 119.2 . . ?
C24 C25 C26 121.6(2) . . ?
C26 C25 H25 119.2 . . ?
C25 C26 H26 119.6 . . ?
C27 C26 C25 120.8(2) . . ?
C27 C26 H26 119.6 . . ?
C26 C27 H27 120.3 . . ?
C26 C27 C28 119.4(2) . . ?
C28 C27 H27 120.3 . . ?
C27 C28 C23 119.86(19) . . ?
C29 C28 C23 117.6(2) . . ?
C29 C28 C27 122.5(2) . . ?
C28 C29 H29 120.5 . . ?
C30 C29 C28 118.9(2) . . ?
C30 C29 H29 120.5 . . ?
C29 C30 H30 120.5 . . ?
C29 C30 C31 119.0(2) . . ?
C31 C30 H30 120.5 . . ?
N1 C31 C30 124.7(2) . . ?
N1 C31 H31 117.7 . . ?
C30 C31 H31 117.7 . . ?

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 C12 C16 C17 114.37(19) . . . . ?
O1 C14 C15 N3 19.5(2) . . . . ?
O1 C14 C15 C24 -101.80(19) . . . . ?
N1 C23 C24 C15 -4.6(3) . . . . ?
N1 C23 C24 C25 174.96(19) . . . . ?
N1 C23 C28 C27 -177.88(19) . . . . ?
N1 C23 C28 C29 0.6(3) . . . . ?
N2 C2 C3 C4 -177.83(19) . . . . ?
N2 C2 C3 C14 3.9(3) . . . . ?
N2 C2 C7 C6 178.8(2) . . . . ?
N2 C2 C7 C8 -1.5(3) . . . . ?
N3 C12 C16 C17 -0.6(2) . . . . ?
N3 C15 C24 C23 170.81(18) . . . . ?
N3 C15 C24 C25 -8.8(3) . . . . ?
C2 N2 C10 C9 -0.2(3) . . . . ?
C2 C3 C4 C5 -1.6(3) . . . . ?
C2 C3 C14 O1 -136.30(19) . . . . ?
C2 C3 C14 C15 103.7(2) . . . . ?
C2 C7 C8 C9 0.5(3) . . . . ?
C3 C2 C7 C6 -1.5(3) . . . . ?
C3 C2 C7 C8 178.2(2) . . . . ?
C3 C4 C5 C6 -0.3(4) . . . . ?
C3 C14 C15 N3 141.59(17) . . . . ?
C3 C14 C15 C24 20.3(3) . . . . ?
C4 C3 C14 O1 45.5(3) . . . . ?
C4 C3 C14 C15 -74.6(3) . . . . ?
C4 C5 C6 C7 1.4(4) . . . . ?
C5 C6 C7 C2 -0.4(3) . . . . ?
C5 C6 C7 C8 179.9(2) . . . . ?
C6 C7 C8 C9 -179.8(2) . . . . ?
C7 C2 C3 C4 2.5(3) . . . . ?
C7 C2 C3 C14 -175.81(18) . . . . ?
C7 C8 C9 C10 0.5(3) . . . . ?
C8 C9 C10 N2 -0.7(4) . . . . ?
C10 N2 C2 C3 -178.32(19) . . . . ?
C10 N2 C2 C7 1.4(3) . . . . ?
C12 O1 C14 C3 -126.84(18) . . . . ?
C12 O1 C14 C15 0.2(2) . . . . ?
C12 N3 C15 C14 -31.7(2) . . . . ?
C12 N3 C15 C24 91.95(19) . . . . ?
C12 N3 C22 C17 -42.3(2) . . . . ?
C12 N3 C22 C21 -166.04(17) . . . . ?
C12 C16 C17 C18 95.3(2) . . . . ?
C12 C16 C17 C22 -24.8(2) . . . . ?
C14 O1 C12 N3 -20.1(2) . . . . ?
C14 O1 C12 C16 -135.41(19) . . . . ?
C14 C3 C4 C5 176.6(2) . . . . ?
C14 C15 C24 C23 -73.1(2) . . . . ?
C14 C15 C24 C25 107.4(2) . . . . ?
C15 N3 C12 O1 33.3(2) . . . . ?
C15 N3 C12 C16 150.53(17) . . . . ?
C15 N3 C22 C17 -159.39(17) . . . . ?
C15 N3 C22 C21 76.8(2) . . . . ?
C15 C24 C25 C26 -176.4(2) . . . . ?
C16 C17 C18 C19 -163.0(2) . . . . ?
C16 C17 C22 N3 40.6(2) . . . . ?
C16 C17 C22 C21 162.6(2) . . . . ?
C17 C18 C19 C20 57.8(3) . . . . ?
C18 C17 C22 N3 -78.6(2) . . . . ?
C18 C17 C22 C21 43.4(3) . . . . ?
C18 C19 C20 C21 -60.2(3) . . . . ?
C19 C20 C21 C22 54.9(3) . . . . ?
C20 C21 C22 N3 68.1(2) . . . . ?
C20 C21 C22 C17 -47.2(3) . . . . ?
C22 N3 C12 O1 -90.17(18) . . . . ?
C22 N3 C12 C16 27.1(2) . . . . ?
C22 N3 C15 C14 85.7(2) . . . . ?
C22 N3 C15 C24 -150.71(18) . . . . ?
C22 C17 C18 C19 -48.4(3) . . . . ?
C23 N1 C31 C30 0.9(3) . . . . ?
C23 C24 C25 C26 4.0(3) . . . . ?
C23 C28 C29 C30 0.4(3) . . . . ?
C24 C23 C28 C27 1.9(3) . . . . ?
C24 C23 C28 C29 -179.58(19) . . . . ?
C24 C25 C26 C27 -0.1(3) . . . . ?
C25 C26 C27 C28 -2.9(3) . . . . ?
C26 C27 C28 C23 2.0(3) . . . . ?
C26 C27 C28 C29 -176.5(2) . . . . ?
C27 C28 C29 C30 178.9(2) . . . . ?
C28 C23 C24 C15 175.58(19) . . . . ?
C28 C23 C24 C25 -4.8(3) . . . . ?
C28 C29 C30 C31 -0.8(3) . . . . ?
C29 C30 C31 N1 0.1(4) . . . . ?
C31 N1 C23 C24 178.95(19) . . . . ?
C31 N1 C23 C28 -1.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.843
_oxdiff_exptl_absorpt_empirical_full_min 0.657
####################################################################### 
# 
# 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_a-3-a
_database_code_depnum_ccdc_archive 'CCDC 2258770'
loop_
_audit_author_name
_audit_author_address
ffg
;grfrf
China
;
_audit_update_record             
;
2023-04-25 deposited with the CCDC.	2023-09-10 downloaded from the CCDC.
;
_audit_creation_date             2022-06-11
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H21 N3 O'
_chemical_formula_sum            'C24 H21 N3 O'
_chemical_formula_weight         367.44
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   21.3764(18)
_cell_length_b                   11.6397(10)
_cell_length_c                   15.2354(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3790.8(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1884
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      66.4880
_cell_measurement_theta_min      4.0970
_shelx_estimated_absorpt_T_max   0.934
_shelx_estimated_absorpt_T_min   0.922
_exptl_absorpt_coefficient_mu    0.632
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.30486
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1115
_diffrn_reflns_av_unetI/netI     0.1137
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18443
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.100
_diffrn_reflns_theta_min         4.136
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -46.00  45.00   0.50    0.50    --   42.30 -77.00-120.00  182
  2  ω     82.00 127.00   0.50    0.50    --   42.30  77.00 -30.00   90
  3  ω     49.00  79.00   0.50    0.50    --   42.30 -77.00-120.00   60
  4  ω    -18.00  83.00   0.50    0.50    --   42.30 -82.00  90.00  202
  5  ω     84.00 132.00   0.50    0.50    --   42.30  77.00-120.00   96
  6  ω     73.00 150.00   0.50    1.00    --  102.30  50.00 -30.00  154
  7  ω     30.00 103.00   0.50    1.00    --  102.30 -82.00  60.00  146
  8  ω     98.00 134.00   0.50    1.00    --  102.30  82.00-150.00   72
  9  ω     13.00 146.00   0.50    1.00    --  102.30 -82.00  90.00  266
 10  ω     14.00 135.00   0.50    1.00    --  102.30 -63.00  90.00  242
 11  ω     80.00 168.00   0.50    1.00    --  102.30  50.00-180.00  176
 12  ω     97.00 192.00   0.50    1.00    --  102.30  38.00 -60.00  190
 13  ω    100.00 110.00   0.50    3.00    --  102.30 -82.00   0.00   20
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0821156000
_diffrn_orient_matrix_UB_12      -0.0405772000
_diffrn_orient_matrix_UB_13      0.0207000000
_diffrn_orient_matrix_UB_21      -0.0572749000
_diffrn_orient_matrix_UB_22      0.0593597000
_diffrn_orient_matrix_UB_23      0.0025494000
_diffrn_orient_matrix_UB_31      -0.0141723000
_diffrn_orient_matrix_UB_32      -0.0053155000
_diffrn_orient_matrix_UB_33      -0.1306436000
_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                2445
_reflns_number_total             3680
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.095
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3680
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1320
_refine_ls_R_factor_gt           0.1003
_refine_ls_restrained_S_all      1.037
_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)+(0.1612P)²+0.2456P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2458
_refine_ls_wR_factor_ref         0.2740
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C11(H11), C20(H20)
2.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C9(H9), C13(H13), C14(H14), C15(H15),
 C17(H17), C18(H18), C19(H19)
;
_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 0.36493(12) 0.5827(2) 0.55920(14) 0.0477(7) Uani 1 1 d . . . . .
N1 N 0.34352(15) 0.2888(3) 0.7025(2) 0.0522(8) Uani 1 1 d . . . . .
N2 N 0.33971(15) 0.7081(3) 0.67114(18) 0.0462(7) Uani 1 1 d . . . . .
N3 N 0.41309(16) 0.4594(3) 0.84432(19) 0.0537(8) Uani 1 1 d . . . . .
C1 C 0.41218(16) 0.4264(3) 0.6365(2) 0.0408(8) Uani 1 1 d . . . . .
C2 C 0.46974(17) 0.4536(3) 0.6045(2) 0.0450(8) Uani 1 1 d . . . . .
H2 H 0.476180 0.526396 0.580969 0.054 Uiso 1 1 calc R U . . .
C3 C 0.52008(18) 0.3748(4) 0.6059(2) 0.0493(9) Uani 1 1 d . . . . .
H3 H 0.558716 0.395284 0.582657 0.059 Uiso 1 1 calc R U . . .
C4 C 0.51163(18) 0.2688(4) 0.6415(2) 0.0488(9) Uani 1 1 d . . . . .
H4 H 0.544619 0.216679 0.642410 0.059 Uiso 1 1 calc R U . . .
C5 C 0.45329(18) 0.2374(3) 0.6769(2) 0.0470(9) Uani 1 1 d . . . . .
C6 C 0.40158(17) 0.3154(3) 0.6725(2) 0.0426(8) Uani 1 1 d . . . . .
C7 C 0.3359(2) 0.1872(4) 0.7387(3) 0.0645(11) Uani 1 1 d . . . . .
H7 H 0.296115 0.167733 0.758568 0.077 Uiso 1 1 calc R U . . .
C8 C 0.3843(3) 0.1058(4) 0.7491(3) 0.0723(13) Uani 1 1 d . . . . .
H8 H 0.376704 0.036710 0.777856 0.087 Uiso 1 1 calc R U . . .
C9 C 0.4420(2) 0.1294(3) 0.7168(3) 0.0601(11) Uani 1 1 d . . . . .
H9 H 0.473826 0.075238 0.720885 0.072 Uiso 1 1 calc R U . . .
C10 C 0.35961(17) 0.5129(3) 0.6360(2) 0.0431(8) Uani 1 1 d . . . . .
H10 H 0.319237 0.472982 0.636061 0.052 Uiso 1 1 calc R U . . .
C11 C 0.36193(16) 0.6014(3) 0.7132(2) 0.0407(8) Uani 1 1 d . . . . .
H11 H 0.405531 0.611863 0.731445 0.049 Uiso 1 1 calc R U . . .
C12 C 0.32383(16) 0.5631(3) 0.7917(2) 0.0416(8) Uani 1 1 d . . . . .
C13 C 0.26282(18) 0.5960(3) 0.8031(2) 0.0470(9) Uani 1 1 d . . . . .
H13 H 0.244976 0.647367 0.763588 0.056 Uiso 1 1 calc R U . . .
C14 C 0.22643(19) 0.5537(4) 0.8733(2) 0.0519(9) Uani 1 1 d . . . . .
H14 H 0.185921 0.580828 0.881546 0.062 Uiso 1 1 calc R U . . .
C15 C 0.2505(2) 0.4730(4) 0.9296(2) 0.0556(10) Uani 1 1 d . . . . .
H15 H 0.225659 0.442703 0.974070 0.067 Uiso 1 1 calc R U . . .
C16 C 0.3124(2) 0.4364(3) 0.9198(2) 0.0507(9) Uani 1 1 d . . . . .
C17 C 0.3409(3) 0.3519(4) 0.9743(2) 0.0653(12) Uani 1 1 d . . . . .
H17 H 0.317900 0.317040 1.018745 0.078 Uiso 1 1 calc R U . . .
C18 C 0.4010(3) 0.3227(4) 0.9616(3) 0.0710(13) Uani 1 1 d . . . . .
H18 H 0.419075 0.264471 0.994798 0.085 Uiso 1 1 calc R U . . .
C19 C 0.4363(2) 0.3811(4) 0.8976(3) 0.0666(12) Uani 1 1 d . . . . .
H19 H 0.478520 0.363240 0.892647 0.080 Uiso 1 1 calc R U . . .
C20 C 0.32659(18) 0.6809(3) 0.5793(2) 0.0461(8) Uani 1 1 d . . . . .
H20 H 0.282158 0.663480 0.570745 0.055 Uiso 1 1 calc R U . . .
C21 C 0.3462(2) 0.7851(4) 0.5253(3) 0.0582(10) Uani 1 1 d . . . . .
H21A H 0.381324 0.766821 0.487549 0.070 Uiso 1 1 calc R U . . .
H21B H 0.311771 0.812463 0.489350 0.070 Uiso 1 1 calc R U . . .
C22 C 0.3643(2) 0.8738(4) 0.5935(3) 0.0682(12) Uani 1 1 d . . . . .
H22A H 0.398010 0.922343 0.572500 0.082 Uiso 1 1 calc R U . . .
H22B H 0.328878 0.921686 0.609184 0.082 Uiso 1 1 calc R U . . .
C23 C 0.3853(2) 0.8017(4) 0.6705(3) 0.0678(12) Uani 1 1 d . . . . .
H23A H 0.427387 0.772845 0.661853 0.081 Uiso 1 1 calc R U . . .
H23B H 0.383757 0.845193 0.724792 0.081 Uiso 1 1 calc R U . . .
C24 C 0.35105(17) 0.4856(3) 0.8529(2) 0.0438(8) 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
O1 C10 1.429(4) . ?
O1 C20 1.440(4) . ?
N1 C6 1.358(5) . ?
N1 C7 1.315(5) . ?
N2 C11 1.476(4) . ?
N2 C20 1.461(5) . ?
N2 C23 1.461(5) . ?
N3 C19 1.317(6) . ?
N3 C24 1.367(5) . ?
C1 C2 1.361(5) . ?
C1 C6 1.422(5) . ?
C1 C10 1.509(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.415(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.360(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.407(5) . ?
C5 C6 1.432(5) . ?
C5 C9 1.417(6) . ?
C7 H7 0.9300 . ?
C7 C8 1.413(7) . ?
C8 H8 0.9300 . ?
C8 C9 1.355(7) . ?
C9 H9 0.9300 . ?
C10 H10 0.9800 . ?
C10 C11 1.565(5) . ?
C11 H11 0.9800 . ?
C11 C12 1.514(5) . ?
C12 C13 1.370(5) . ?
C12 C24 1.422(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.412(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.372(6) . ?
C15 H15 0.9300 . ?
C15 C16 1.400(6) . ?
C16 C17 1.424(6) . ?
C16 C24 1.431(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.342(7) . ?
C18 H18 0.9300 . ?
C18 C19 1.408(7) . ?
C19 H19 0.9300 . ?
C20 H20 0.9800 . ?
C20 C21 1.525(5) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.516(7) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.511(6) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?

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
C10 O1 C20 103.4(2) . . ?
C7 N1 C6 117.4(4) . . ?
C20 N2 C11 107.2(3) . . ?
C23 N2 C11 114.5(3) . . ?
C23 N2 C20 106.5(3) . . ?
C19 N3 C24 117.4(4) . . ?
C2 C1 C6 119.6(3) . . ?
C2 C1 C10 121.1(3) . . ?
C6 C1 C10 119.3(3) . . ?
C1 C2 H2 119.0 . . ?
C1 C2 C3 122.1(4) . . ?
C3 C2 H2 119.0 . . ?
C2 C3 H3 120.2 . . ?
C4 C3 C2 119.6(4) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.4(3) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 120.1(3) . . ?
C4 C5 C9 123.1(4) . . ?
C9 C5 C6 116.8(4) . . ?
N1 C6 C1 118.8(3) . . ?
N1 C6 C5 123.0(3) . . ?
C1 C6 C5 118.1(3) . . ?
N1 C7 H7 118.0 . . ?
N1 C7 C8 124.0(4) . . ?
C8 C7 H7 118.0 . . ?
C7 C8 H8 120.3 . . ?
C9 C8 C7 119.3(4) . . ?
C9 C8 H8 120.3 . . ?
C5 C9 H9 120.3 . . ?
C8 C9 C5 119.4(4) . . ?
C8 C9 H9 120.3 . . ?
O1 C10 C1 108.9(3) . . ?
O1 C10 H10 109.9 . . ?
O1 C10 C11 103.8(3) . . ?
C1 C10 H10 109.9 . . ?
C1 C10 C11 114.3(3) . . ?
C11 C10 H10 109.9 . . ?
N2 C11 C10 102.6(3) . . ?
N2 C11 H11 108.9 . . ?
N2 C11 C12 114.7(3) . . ?
C10 C11 H11 108.9 . . ?
C12 C11 C10 112.5(3) . . ?
C12 C11 H11 108.9 . . ?
C13 C12 C11 122.0(3) . . ?
C13 C12 C24 118.9(3) . . ?
C24 C12 C11 119.0(3) . . ?
C12 C13 H13 119.2 . . ?
C12 C13 C14 121.5(4) . . ?
C14 C13 H13 119.2 . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.4(4) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 120.1 . . ?
C14 C15 C16 119.8(3) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 C17 123.6(4) . . ?
C15 C16 C24 120.0(4) . . ?
C17 C16 C24 116.4(4) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 C16 120.0(4) . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 120.3 . . ?
C17 C18 C19 119.4(4) . . ?
C19 C18 H18 120.3 . . ?
N3 C19 C18 124.0(5) . . ?
N3 C19 H19 118.0 . . ?
C18 C19 H19 118.0 . . ?
O1 C20 N2 105.5(3) . . ?
O1 C20 H20 111.0 . . ?
O1 C20 C21 111.1(3) . . ?
N2 C20 H20 111.0 . . ?
N2 C20 C21 107.0(3) . . ?
C21 C20 H20 111.0 . . ?
C20 C21 H21A 111.0 . . ?
C20 C21 H21B 111.0 . . ?
H21A C21 H21B 109.0 . . ?
C22 C21 C20 104.0(3) . . ?
C22 C21 H21A 111.0 . . ?
C22 C21 H21B 111.0 . . ?
C21 C22 H22A 111.1 . . ?
C21 C22 H22B 111.1 . . ?
H22A C22 H22B 109.1 . . ?
C23 C22 C21 103.3(4) . . ?
C23 C22 H22A 111.1 . . ?
C23 C22 H22B 111.1 . . ?
N2 C23 C22 102.8(3) . . ?
N2 C23 H23A 111.2 . . ?
N2 C23 H23B 111.2 . . ?
C22 C23 H23A 111.2 . . ?
C22 C23 H23B 111.2 . . ?
H23A C23 H23B 109.1 . . ?
N3 C24 C12 118.4(3) . . ?
N3 C24 C16 122.6(3) . . ?
C12 C24 C16 119.0(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C10 C11 N2 24.8(3) . . . . ?
O1 C10 C11 C12 148.6(3) . . . . ?
O1 C20 C21 C22 -120.1(3) . . . . ?
N1 C7 C8 C9 -3.3(8) . . . . ?
N2 C11 C12 C13 23.3(5) . . . . ?
N2 C11 C12 C24 -160.2(3) . . . . ?
N2 C20 C21 C22 -5.5(4) . . . . ?
C1 C2 C3 C4 -1.1(5) . . . . ?
C1 C10 C11 N2 143.4(3) . . . . ?
C1 C10 C11 C12 -92.9(4) . . . . ?
C2 C1 C6 N1 -178.7(3) . . . . ?
C2 C1 C6 C5 2.5(5) . . . . ?
C2 C1 C10 O1 34.8(4) . . . . ?
C2 C1 C10 C11 -80.8(4) . . . . ?
C2 C3 C4 C5 -0.1(5) . . . . ?
C3 C4 C5 C6 2.5(5) . . . . ?
C3 C4 C5 C9 -178.3(4) . . . . ?
C4 C5 C6 N1 177.6(3) . . . . ?
C4 C5 C6 C1 -3.6(5) . . . . ?
C4 C5 C9 C8 -179.8(4) . . . . ?
C6 N1 C7 C8 1.0(6) . . . . ?
C6 C1 C2 C3 -0.2(5) . . . . ?
C6 C1 C10 O1 -146.3(3) . . . . ?
C6 C1 C10 C11 98.1(4) . . . . ?
C6 C5 C9 C8 -0.6(6) . . . . ?
C7 N1 C6 C1 -177.3(3) . . . . ?
C7 N1 C6 C5 1.5(5) . . . . ?
C7 C8 C9 C5 2.9(7) . . . . ?
C9 C5 C6 N1 -1.7(5) . . . . ?
C9 C5 C6 C1 177.1(3) . . . . ?
C10 O1 C20 N2 41.0(3) . . . . ?
C10 O1 C20 C21 156.6(3) . . . . ?
C10 C1 C2 C3 178.7(3) . . . . ?
C10 C1 C6 N1 2.5(5) . . . . ?
C10 C1 C6 C5 -176.4(3) . . . . ?
C10 C11 C12 C13 -93.4(4) . . . . ?
C10 C11 C12 C24 83.1(4) . . . . ?
C11 N2 C20 O1 -24.6(4) . . . . ?
C11 N2 C20 C21 -143.0(3) . . . . ?
C11 N2 C23 C22 155.7(4) . . . . ?
C11 C12 C13 C14 175.8(3) . . . . ?
C11 C12 C24 N3 7.7(5) . . . . ?
C11 C12 C24 C16 -171.1(3) . . . . ?
C12 C13 C14 C15 -3.7(5) . . . . ?
C13 C12 C24 N3 -175.7(3) . . . . ?
C13 C12 C24 C16 5.6(5) . . . . ?
C13 C14 C15 C16 3.1(6) . . . . ?
C14 C15 C16 C17 -179.1(4) . . . . ?
C14 C15 C16 C24 1.8(6) . . . . ?
C15 C16 C17 C18 -179.0(4) . . . . ?
C15 C16 C24 N3 175.2(3) . . . . ?
C15 C16 C24 C12 -6.2(5) . . . . ?
C16 C17 C18 C19 3.7(7) . . . . ?
C17 C16 C24 N3 -4.0(5) . . . . ?
C17 C16 C24 C12 174.7(3) . . . . ?
C17 C18 C19 N3 -4.4(7) . . . . ?
C19 N3 C24 C12 -175.1(4) . . . . ?
C19 N3 C24 C16 3.6(5) . . . . ?
C20 O1 C10 C1 -162.5(3) . . . . ?
C20 O1 C10 C11 -40.3(3) . . . . ?
C20 N2 C11 C10 -0.2(3) . . . . ?
C20 N2 C11 C12 -122.4(3) . . . . ?
C20 N2 C23 C22 37.4(5) . . . . ?
C20 C21 C22 C23 27.7(5) . . . . ?
C21 C22 C23 N2 -40.2(5) . . . . ?
C23 N2 C11 C10 -118.0(4) . . . . ?
C23 N2 C11 C12 119.7(4) . . . . ?
C23 N2 C20 O1 98.4(4) . . . . ?
C23 N2 C20 C21 -20.0(4) . . . . ?
C24 N3 C19 C18 0.7(7) . . . . ?
C24 C12 C13 C14 -0.8(5) . . . . ?
C24 C16 C17 C18 0.2(6) . . . . ?

_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 2.077
_oxdiff_exptl_absorpt_empirical_full_min 0.333
####################################################################### 
# 
# 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_13-a
_database_code_depnum_ccdc_archive 'CCDC 2258768'
loop_
_audit_author_name
_audit_author_address
ffg
;grfrf
China
;
_audit_update_record             
;
2023-04-25 deposited with the CCDC.	2023-09-10 downloaded from the CCDC.
;
_audit_creation_date             2022-06-27
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H21 Br2 N3 O'
_chemical_formula_sum            'C20 H21 Br2 N3 O'
_chemical_formula_weight         479.22
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.02540(14)
_cell_length_b                   17.1860(4)
_cell_length_c                   9.4103(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.742(2)
_cell_angle_gamma                90
_cell_volume                     960.41(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4017
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      72.9940
_cell_measurement_theta_min      4.7320
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.463
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.23466
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.657
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0706
_diffrn_reflns_av_unetI/netI     0.0603
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4451
_diffrn_reflns_point_group_measured_fraction_full 0.782
_diffrn_reflns_point_group_measured_fraction_max 0.748
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.501
_diffrn_reflns_theta_min         4.768
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -65.00  19.00   1.00    1.00    --  -40.73  38.00  60.00   84
  2  ω    -89.00 -55.00   1.00    1.00    --  -40.73 125.00 -30.00   34
  3  ω   -109.00 -16.00   1.00    1.00    --  -40.73 -38.00  60.00   93
  4  ω     31.00 130.00   1.00    1.00    --  106.95 -30.00 -90.00   99
  5  ω     65.00 128.00   1.00    1.00    --  106.95 -45.00   0.00   63
  6  ω    115.00 174.00   1.00    1.00    --  106.95  30.00  90.00   59
  7  ω     85.00 112.00   1.00    1.00    --  106.95  30.00  90.00   27
  8  ω     42.00 102.00   1.00    1.00    --  106.95 -95.00 150.00   60
  9  ω     34.00 109.00   1.00    1.00    --  106.95 -95.00-150.00   75
 10  ω    -41.00 -16.00   1.00    1.00    --  -40.98 -38.00  60.00   25
 11  ω    -43.00  -4.00   1.00    1.00    --  -40.98 -19.00  60.00   39
 12  ω   -111.00 -85.00   1.00    1.00    --  -40.98 -77.00  60.00   26
 13  ω    -43.00 -17.00   1.00    1.00    --  -40.98 -57.00-180.00   26
 14  ω    -33.00  -8.00   1.00    1.00    --  -40.98 -77.00  60.00   25
 15  ω    -54.00  -9.00   1.00    1.00    --  -40.98 -77.00 150.00   45
 16  ω      1.00  39.00   1.00    1.00    --   40.98 -99.00 -60.00   38
 17  ω    116.00 151.00   1.00    1.00    --  106.95  45.00-180.00   35
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0967021000
_diffrn_orient_matrix_UB_12      0.0084126000
_diffrn_orient_matrix_UB_13      -0.1616060000
_diffrn_orient_matrix_UB_21      0.2396694000
_diffrn_orient_matrix_UB_22      -0.0049676000
_diffrn_orient_matrix_UB_23      -0.0360607000
_diffrn_orient_matrix_UB_31      -0.0226379000
_diffrn_orient_matrix_UB_32      -0.0890991000
_diffrn_orient_matrix_UB_33      -0.0131932000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.486
_reflns_Friedel_fraction_full    0.549
_reflns_Friedel_fraction_max     0.507
_reflns_number_gt                2798
_reflns_number_total             2900
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         1.711
_refine_diff_density_min         -2.417
_refine_diff_density_rms         0.214
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.09(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.186
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2900
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0883
_refine_ls_R_factor_gt           0.0868
_refine_ls_restrained_S_all      1.185
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2504
_refine_ls_wR_factor_ref         0.2544
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C8(H8), C10(H10), C5(H5), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C6(H6A,H6B), C1(H1A,H1B), C4(H4A,H4B), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C20(H20), C12(H12), C18(H18), C17(H17), C13(H13)
;
_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
Br2 Br 0.15548(11) 0.44830(4) 0.08997(6) 0.04255(18) Uani 1 1 d . . . . .
Br1 Br 1.06186(14) 0.18321(4) 0.66888(9) 0.0510(2) Uani 1 1 d . . . . .
O1 O 0.5452(7) 0.5061(3) 0.8705(5) 0.0404(11) Uani 1 1 d . . . . .
N1 N 0.5189(7) 0.6205(3) 0.7329(5) 0.0247(10) Uani 1 1 d . . . . .
N3 N 0.6411(7) 0.5299(3) 0.4153(5) 0.0259(10) Uani 1 1 d . . . . .
C11 C 0.7944(8) 0.4261(4) 0.7624(5) 0.0261(13) Uani 1 1 d . . . . .
N2 N 0.9774(7) 0.4187(4) 0.7015(6) 0.0357(13) Uani 1 1 d . . . . .
C9 C 0.6615(7) 0.5655(3) 0.6687(5) 0.0249(12) Uani 1 1 d . . . . .
H9 H 0.795274 0.592902 0.648254 0.030 Uiso 1 1 calc R U . . .
C8 C 0.6356(8) 0.6898(4) 0.7980(6) 0.0279(13) Uani 1 1 d . . . . .
H8 H 0.786017 0.674735 0.847227 0.033 Uiso 1 1 calc R U . . .
C16 C 0.5345(8) 0.5315(4) 0.5299(6) 0.0261(12) Uani 1 1 d . . . . .
C10 C 0.7313(8) 0.5088(4) 0.7942(6) 0.0270(13) Uani 1 1 d . . . . .
H10 H 0.859196 0.531844 0.858664 0.032 Uiso 1 1 calc R U . . .
C14 C 0.9408(10) 0.2822(4) 0.7082(7) 0.0367(16) Uani 1 1 d . . . . .
C5 C 0.4906(8) 0.7119(4) 0.9120(6) 0.0308(14) Uani 1 1 d . . . . .
H5 H 0.572150 0.746926 0.984966 0.037 Uiso 1 1 calc R U . . .
C3 C 0.2990(10) 0.8160(4) 0.7461(8) 0.0399(17) Uani 1 1 d . . . . .
H3A H 0.383542 0.856647 0.802988 0.048 Uiso 1 1 calc R U . . .
H3B H 0.153714 0.837068 0.703124 0.048 Uiso 1 1 calc R U . . .
C6 C 0.4591(13) 0.6322(4) 0.9749(7) 0.0396(17) Uani 1 1 d . . . . .
H6A H 0.327677 0.631279 1.021837 0.048 Uiso 1 1 calc R U . . .
H6B H 0.590318 0.617412 1.044268 0.048 Uiso 1 1 calc R U . . .
C7 C 0.4279(8) 0.5782(4) 0.8451(6) 0.0316(14) Uani 1 1 d . . . . .
H7 H 0.267139 0.568182 0.812979 0.038 Uiso 1 1 calc R U . . .
C1 C 0.6589(9) 0.7531(4) 0.6913(7) 0.0310(14) Uani 1 1 d . . . . .
H1A H 0.731346 0.732069 0.615132 0.037 Uiso 1 1 calc R U . . .
H1B H 0.754427 0.793963 0.739251 0.037 Uiso 1 1 calc R U . . .
C15 C 1.0502(9) 0.3476(5) 0.6781(9) 0.0441(19) Uani 1 1 d . . . . .
H15 H 1.181679 0.342426 0.639458 0.053 Uiso 1 1 calc R U . . .
C4 C 0.2668(10) 0.7470(4) 0.8421(8) 0.0368(15) Uani 1 1 d . . . . .
H4A H 0.184401 0.763821 0.916747 0.044 Uiso 1 1 calc R U . . .
H4B H 0.177684 0.707520 0.784874 0.044 Uiso 1 1 calc R U . . .
C20 C 0.5279(9) 0.5055(4) 0.2912(6) 0.0317(14) Uani 1 1 d . . . . .
H20 H 0.600697 0.504136 0.211612 0.038 Uiso 1 1 calc R U . . .
C2 C 0.4301(11) 0.7879(4) 0.6248(8) 0.0391(17) Uani 1 1 d . . . . .
H2A H 0.341594 0.748991 0.565538 0.047 Uiso 1 1 calc R U . . .
H2B H 0.453168 0.831476 0.563454 0.047 Uiso 1 1 calc R U . . .
C12 C 0.6738(10) 0.3597(4) 0.7924(7) 0.0372(16) Uani 1 1 d . . . . .
H12 H 0.540760 0.365486 0.829002 0.045 Uiso 1 1 calc R U . . .
C18 C 0.1964(8) 0.4816(4) 0.3930(7) 0.0331(15) Uani 1 1 d . . . . .
H18 H 0.047222 0.465740 0.384952 0.040 Uiso 1 1 calc R U . . .
C17 C 0.3156(9) 0.5053(5) 0.5202(7) 0.0384(16) Uani 1 1 d . . . . .
H17 H 0.249328 0.504017 0.602524 0.046 Uiso 1 1 calc R U . . .
C13 C 0.7475(11) 0.2888(5) 0.7689(7) 0.0414(17) Uani 1 1 d . . . . .
H13 H 0.671635 0.244821 0.792607 0.050 Uiso 1 1 calc R U . . .
C19 C 0.3070(9) 0.4821(4) 0.2741(6) 0.0332(15) 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
Br2 C19 1.908(6) . ?
Br1 C14 1.912(7) . ?
O1 C10 1.431(7) . ?
O1 C7 1.425(8) . ?
N1 C9 1.473(7) . ?
N1 C8 1.464(8) . ?
N1 C7 1.463(7) . ?
N3 C16 1.346(7) . ?
N3 C20 1.317(7) . ?
C11 N2 1.332(7) . ?
C11 C10 1.515(8) . ?
C11 C12 1.407(9) . ?
N2 C15 1.330(10) . ?
C9 H9 0.9800 . ?
C9 C16 1.515(7) . ?
C9 C10 1.535(8) . ?
C8 H8 0.9800 . ?
C8 C5 1.542(8) . ?
C8 C1 1.503(8) . ?
C16 C17 1.382(8) . ?
C10 H10 0.9800 . ?
C14 C15 1.357(10) . ?
C14 C13 1.386(10) . ?
C5 H5 0.9800 . ?
C5 C6 1.517(10) . ?
C5 C4 1.521(8) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.523(10) . ?
C3 C2 1.571(10) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.520(9) . ?
C7 H7 0.9800 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.535(8) . ?
C15 H15 0.9300 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C20 H20 0.9300 . ?
C20 C19 1.374(8) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C12 H12 0.9300 . ?
C12 C13 1.327(10) . ?
C18 H18 0.9300 . ?
C18 C17 1.350(9) . ?
C18 C19 1.396(9) . ?
C17 H17 0.9300 . ?
C13 H13 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O1 C10 107.2(5) . . ?
C8 N1 C9 114.9(4) . . ?
C7 N1 C9 107.0(5) . . ?
C7 N1 C8 108.3(5) . . ?
C20 N3 C16 118.1(4) . . ?
N2 C11 C10 115.3(5) . . ?
N2 C11 C12 120.2(6) . . ?
C12 C11 C10 124.5(5) . . ?
C15 N2 C11 118.6(6) . . ?
N1 C9 H9 109.2 . . ?
N1 C9 C16 110.9(4) . . ?
N1 C9 C10 101.2(4) . . ?
C16 C9 H9 109.2 . . ?
C16 C9 C10 116.8(5) . . ?
C10 C9 H9 109.2 . . ?
N1 C8 H8 108.9 . . ?
N1 C8 C5 101.7(4) . . ?
N1 C8 C1 113.7(5) . . ?
C5 C8 H8 108.9 . . ?
C1 C8 H8 108.9 . . ?
C1 C8 C5 114.5(5) . . ?
N3 C16 C9 117.3(4) . . ?
N3 C16 C17 121.3(5) . . ?
C17 C16 C9 121.3(5) . . ?
O1 C10 C11 108.3(5) . . ?
O1 C10 C9 105.7(4) . . ?
O1 C10 H10 107.7 . . ?
C11 C10 C9 119.3(4) . . ?
C11 C10 H10 107.7 . . ?
C9 C10 H10 107.7 . . ?
C15 C14 Br1 118.8(5) . . ?
C15 C14 C13 119.4(7) . . ?
C13 C14 Br1 121.8(6) . . ?
C8 C5 H5 111.3 . . ?
C6 C5 C8 99.9(5) . . ?
C6 C5 H5 111.3 . . ?
C6 C5 C4 111.5(5) . . ?
C4 C5 C8 111.2(5) . . ?
C4 C5 H5 111.3 . . ?
H3A C3 H3B 108.3 . . ?
C4 C3 H3A 109.9 . . ?
C4 C3 H3B 109.9 . . ?
C4 C3 C2 108.8(6) . . ?
C2 C3 H3A 109.9 . . ?
C2 C3 H3B 109.9 . . ?
C5 C6 H6A 110.9 . . ?
C5 C6 H6B 110.9 . . ?
C5 C6 C7 104.2(5) . . ?
H6A C6 H6B 108.9 . . ?
C7 C6 H6A 110.9 . . ?
C7 C6 H6B 110.9 . . ?
O1 C7 N1 108.5(5) . . ?
O1 C7 C6 113.9(5) . . ?
O1 C7 H7 109.6 . . ?
N1 C7 C6 105.4(5) . . ?
N1 C7 H7 109.6 . . ?
C6 C7 H7 109.6 . . ?
C8 C1 H1A 109.2 . . ?
C8 C1 H1B 109.2 . . ?
C8 C1 C2 112.1(5) . . ?
H1A C1 H1B 107.9 . . ?
C2 C1 H1A 109.2 . . ?
C2 C1 H1B 109.2 . . ?
N2 C15 C14 122.8(6) . . ?
N2 C15 H15 118.6 . . ?
C14 C15 H15 118.6 . . ?
C5 C4 C3 111.9(5) . . ?
C5 C4 H4A 109.2 . . ?
C5 C4 H4B 109.2 . . ?
C3 C4 H4A 109.2 . . ?
C3 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
N3 C20 H20 118.6 . . ?
N3 C20 C19 122.9(5) . . ?
C19 C20 H20 118.6 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
C1 C2 C3 110.5(5) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.8(6) . . ?
C13 C12 H12 119.6 . . ?
C17 C18 H18 121.5 . . ?
C17 C18 C19 117.0(5) . . ?
C19 C18 H18 121.5 . . ?
C16 C17 H17 119.5 . . ?
C18 C17 C16 121.0(6) . . ?
C18 C17 H17 119.5 . . ?
C14 C13 H13 120.9 . . ?
C12 C13 C14 118.1(7) . . ?
C12 C13 H13 120.9 . . ?
C20 C19 Br2 120.0(4) . . ?
C20 C19 C18 119.5(5) . . ?
C18 C19 Br2 120.4(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C14 C15 N2 179.7(5) . . . . ?
Br1 C14 C13 C12 -179.7(5) . . . . ?
N1 C9 C16 N3 133.2(5) . . . . ?
N1 C9 C16 C17 -44.8(8) . . . . ?
N1 C9 C10 O1 32.3(5) . . . . ?
N1 C9 C10 C11 154.3(4) . . . . ?
N1 C8 C5 C6 44.4(5) . . . . ?
N1 C8 C5 C4 -73.4(6) . . . . ?
N1 C8 C1 C2 66.4(7) . . . . ?
N3 C16 C17 C18 -4.0(11) . . . . ?
N3 C20 C19 Br2 179.6(5) . . . . ?
N3 C20 C19 C18 -1.8(11) . . . . ?
C11 N2 C15 C14 2.8(10) . . . . ?
C11 C12 C13 C14 -2.9(10) . . . . ?
N2 C11 C10 O1 -174.9(4) . . . . ?
N2 C11 C10 C9 64.3(6) . . . . ?
N2 C11 C12 C13 4.2(9) . . . . ?
C9 N1 C8 C5 -153.7(4) . . . . ?
C9 N1 C8 C1 82.7(6) . . . . ?
C9 N1 C7 O1 11.7(5) . . . . ?
C9 N1 C7 C6 134.1(5) . . . . ?
C9 C16 C17 C18 173.9(6) . . . . ?
C8 N1 C9 C16 -141.4(5) . . . . ?
C8 N1 C9 C10 94.1(5) . . . . ?
C8 N1 C7 O1 -112.7(5) . . . . ?
C8 N1 C7 C6 9.7(6) . . . . ?
C8 C5 C6 C7 -38.8(6) . . . . ?
C8 C5 C4 C3 -54.7(7) . . . . ?
C8 C1 C2 C3 54.1(7) . . . . ?
C16 N3 C20 C19 0.2(10) . . . . ?
C16 C9 C10 O1 -88.2(5) . . . . ?
C16 C9 C10 C11 33.9(6) . . . . ?
C10 O1 C7 N1 9.6(6) . . . . ?
C10 O1 C7 C6 -107.5(6) . . . . ?
C10 C11 N2 C15 176.2(5) . . . . ?
C10 C11 C12 C13 -176.0(6) . . . . ?
C10 C9 C16 N3 -111.6(6) . . . . ?
C10 C9 C16 C17 70.4(7) . . . . ?
C5 C8 C1 C2 -49.9(7) . . . . ?
C5 C6 C7 O1 138.1(5) . . . . ?
C5 C6 C7 N1 19.2(6) . . . . ?
C6 C5 C4 C3 -165.2(6) . . . . ?
C7 O1 C10 C11 -155.2(4) . . . . ?
C7 O1 C10 C9 -26.3(6) . . . . ?
C7 N1 C9 C16 98.3(5) . . . . ?
C7 N1 C9 C10 -26.2(5) . . . . ?
C7 N1 C8 C5 -34.2(5) . . . . ?
C7 N1 C8 C1 -157.7(4) . . . . ?
C1 C8 C5 C6 167.4(5) . . . . ?
C1 C8 C5 C4 49.6(7) . . . . ?
C15 C14 C13 C12 1.5(10) . . . . ?
C4 C5 C6 C7 78.8(6) . . . . ?
C4 C3 C2 C1 -58.6(7) . . . . ?
C20 N3 C16 C9 -175.3(5) . . . . ?
C20 N3 C16 C17 2.7(9) . . . . ?
C2 C3 C4 C5 59.5(7) . . . . ?
C12 C11 N2 C15 -4.1(8) . . . . ?
C12 C11 C10 O1 5.4(7) . . . . ?
C12 C11 C10 C9 -115.4(6) . . . . ?
C17 C18 C19 Br2 179.1(5) . . . . ?
C17 C18 C19 C20 0.5(11) . . . . ?
C13 C14 C15 N2 -1.5(11) . . . . ?
C19 C18 C17 C16 2.3(11) . . . . ?

_olex2_date_sample_data_collection 2022-06-27
_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 2.524
_oxdiff_exptl_absorpt_empirical_full_min 0.327
####################################################################### 
# 
# 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_11a-no
_database_code_depnum_ccdc_archive 'CCDC 2258774'
loop_
_audit_author_name
_audit_author_address
ffg
;grfrf
China
;
_audit_update_record             
;
2023-04-25 deposited with the CCDC.	2023-09-10 downloaded from the CCDC.
;
_audit_creation_date             2022-08-12
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H26 Cl3 N3 O4'
_chemical_formula_sum            'C27 H26 Cl3 N3 O4'
_chemical_formula_weight         562.86
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      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                   6.0111(2)
_cell_length_b                   12.8027(4)
_cell_length_c                   34.2524(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2636.01(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4550
_cell_measurement_temperature    169.98(10)
_cell_measurement_theta_max      73.2760
_cell_measurement_theta_min      2.5590
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.475
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39372
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_unetI/netI     0.0540
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            10170
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.720
_diffrn_reflns_theta_min         2.580
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.98(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -65.00  34.00   1.00    1.00    --  -40.73  38.00 -60.00   99
  2  ω      1.00  82.00   1.00    1.00    --   40.73 -99.00  60.00   81
  3  ω     16.00 113.00   1.00    1.00    --   40.73  38.00  90.00   97
  4  ω     88.00 142.00   1.00    1.00    --  107.58  45.00-120.00   54
  5  ω     25.00  93.00   1.00    1.00    --  107.58 -95.00  30.00   68
  6  ω     81.00 172.00   1.00    1.00    --  107.58  30.00   0.00   91
  7  ω    135.00 174.00   1.00    1.00    --  107.58 125.00  90.00   39
  8  ω    150.00 176.00   1.00    1.00    --  107.58  45.00-120.00   26
  9  ω     32.00 141.00   1.00    1.00    --  107.58 -15.00-150.00  109
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1066337000
_diffrn_orient_matrix_UB_12      -0.0351811000
_diffrn_orient_matrix_UB_13      -0.0387490000
_diffrn_orient_matrix_UB_21      -0.0164565000
_diffrn_orient_matrix_UB_22      0.1125402000
_diffrn_orient_matrix_UB_23      -0.0156831000
_diffrn_orient_matrix_UB_31      0.2324509000
_diffrn_orient_matrix_UB_32      0.0241868000
_diffrn_orient_matrix_UB_33      0.0165744000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.699
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.954
_reflns_number_gt                4690
_reflns_number_total             5202
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 1677 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.004(11)
_refine_ls_extinction_coef       0.00106(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         5202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0424
_refine_ls_restrained_S_all      1.027
_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)+(0.0472P)²+0.2033P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1013
_refine_ls_wR_factor_ref         0.1060
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C10(H10), C11(H11), C16(H16), C22(H22)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4A), C5(H5), C6(H6), C18(H18), C19(H19), C20(H20), C24(H24),
 C25(H25), C26(H26)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_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
Cl1 Cl -0.0536(2) 1.22352(8) 0.33270(5) 0.0695(4) Uani 1 1 d . . . . .
Cl2 Cl 0.5592(2) 0.53184(11) 0.55581(3) 0.0602(3) Uani 1 1 d . . . . .
Cl3 Cl 0.7582(2) 0.19080(8) 0.44430(3) 0.0550(3) Uani 1 1 d . . . . .
O1 O -0.0829(5) 0.8109(2) 0.31848(9) 0.0469(7) Uani 1 1 d . . . . .
O2 O 0.2536(4) 0.75299(18) 0.33690(7) 0.0328(5) Uani 1 1 d . . . . .
O3 O 0.2722(4) 0.58539(19) 0.35968(6) 0.0276(5) Uani 1 1 d . . . . .
O4 O 0.7063(4) 0.73337(19) 0.39572(7) 0.0342(6) Uani 1 1 d . . . . .
H4 H 0.673915 0.727673 0.372564 0.051 Uiso 1 1 calc R U . . .
N1 N 0.5142(4) 0.5814(2) 0.35397(8) 0.0244(6) Uani 1 1 d . . . . .
N2 N 0.6510(5) 0.3765(2) 0.41857(8) 0.0302(6) Uani 1 1 d . . . . .
N3 N 0.6152(4) 0.5963(2) 0.48442(8) 0.0291(6) Uani 1 1 d . . . . .
C1 C 0.1849(6) 0.9336(3) 0.34097(10) 0.0306(8) Uani 1 1 d . . . . .
C2 C 0.0457(6) 1.0183(3) 0.33341(11) 0.0364(8) Uani 1 1 d . . . . .
H2 H -0.093952 1.007961 0.322387 0.044 Uiso 1 1 calc R U . . .
C3 C 0.1178(7) 1.1175(3) 0.34247(12) 0.0409(9) Uani 1 1 d . . . . .
C4 C 0.3240(7) 1.1353(3) 0.35925(11) 0.0413(9) Uani 1 1 d . . . . .
H4A H 0.370043 1.202795 0.365252 0.050 Uiso 1 1 calc R U . . .
C5 C 0.4605(7) 1.0504(3) 0.36692(11) 0.0403(9) Uani 1 1 d . . . . .
H5 H 0.598653 1.061108 0.378482 0.048 Uiso 1 1 calc R U . . .
C6 C 0.3942(6) 0.9502(3) 0.35762(10) 0.0333(8) Uani 1 1 d . . . . .
H6 H 0.488361 0.893983 0.362416 0.040 Uiso 1 1 calc R U . . .
C7 C 0.1014(6) 0.8287(3) 0.33121(10) 0.0321(8) Uani 1 1 d . . . . .
C8 C 0.1765(6) 0.6479(3) 0.33080(10) 0.0309(8) Uani 1 1 d . . . . .
H8 H 0.014601 0.646660 0.334128 0.037 Uiso 1 1 calc R U . . .
C9 C 0.2313(7) 0.6096(3) 0.29006(10) 0.0353(8) Uani 1 1 d . . . . .
H9A H 0.191424 0.663364 0.271395 0.042 Uiso 1 1 calc R U . . .
H9B H 0.141552 0.548434 0.284428 0.042 Uiso 1 1 calc R U . . .
C10 C 0.4768(6) 0.5816(3) 0.28454(10) 0.0326(8) Uani 1 1 d . . . . .
H10 H 0.561851 0.646856 0.283725 0.039 Uiso 1 1 calc R U . . .
C11 C 0.5605(6) 0.5174(3) 0.31939(9) 0.0256(7) Uani 1 1 d . . . . .
H11 H 0.722671 0.513364 0.316924 0.031 Uiso 1 1 calc R U . . .
C12 C 0.4740(6) 0.4049(3) 0.31970(10) 0.0315(8) Uani 1 1 d . . . . .
H12A H 0.314812 0.405005 0.324346 0.038 Uiso 1 1 calc R U . . .
H12B H 0.544663 0.366383 0.340688 0.038 Uiso 1 1 calc R U . . .
C13 C 0.5234(8) 0.3514(3) 0.28064(10) 0.0425(10) Uani 1 1 d . . . . .
H13A H 0.683078 0.345145 0.277338 0.051 Uiso 1 1 calc R U . . .
H13B H 0.460859 0.281551 0.280861 0.051 Uiso 1 1 calc R U . . .
C14 C 0.4266(8) 0.4124(3) 0.24639(10) 0.0436(10) Uani 1 1 d . . . . .
H14A H 0.464707 0.377677 0.222118 0.052 Uiso 1 1 calc R U . . .
H14B H 0.265738 0.414212 0.248520 0.052 Uiso 1 1 calc R U . . .
C15 C 0.5173(8) 0.5232(3) 0.24601(10) 0.0422(9) Uani 1 1 d . . . . .
H15A H 0.447651 0.561668 0.224884 0.051 Uiso 1 1 calc R U . . .
H15B H 0.675935 0.520906 0.240906 0.051 Uiso 1 1 calc R U . . .
C16 C 0.6077(5) 0.5504(3) 0.39203(9) 0.0247(7) Uani 1 1 d . . . . .
H16 H 0.764434 0.533695 0.387283 0.030 Uiso 1 1 calc R U . . .
C17 C 0.5093(5) 0.4563(3) 0.41284(9) 0.0253(7) Uani 1 1 d . . . . .
C18 C 0.2924(6) 0.4535(3) 0.42602(10) 0.0333(8) Uani 1 1 d . . . . .
H18 H 0.197852 0.509793 0.421735 0.040 Uiso 1 1 calc R U . . .
C19 C 0.2171(7) 0.3654(3) 0.44577(12) 0.0439(9) Uani 1 1 d . . . . .
H19 H 0.071729 0.362570 0.455014 0.053 Uiso 1 1 calc R U . . .
C20 C 0.3586(8) 0.2829(3) 0.45151(12) 0.0457(10) Uani 1 1 d . . . . .
H20 H 0.312892 0.222450 0.464268 0.055 Uiso 1 1 calc R U . . .
C21 C 0.5720(7) 0.2940(3) 0.43741(11) 0.0387(9) Uani 1 1 d . . . . .
C22 C 0.6065(5) 0.6509(3) 0.41713(9) 0.0252(7) Uani 1 1 d . . . . .
H22 H 0.452204 0.669676 0.423146 0.030 Uiso 1 1 calc R U . . .
C23 C 0.7328(6) 0.6368(3) 0.45480(9) 0.0249(7) Uani 1 1 d . . . . .
C24 C 0.9547(6) 0.6639(3) 0.45840(10) 0.0315(8) Uani 1 1 d . . . . .
H24 H 1.031118 0.693981 0.437639 0.038 Uiso 1 1 calc R U . . .
C25 C 1.0615(6) 0.6449(3) 0.49402(11) 0.0365(8) Uani 1 1 d . . . . .
H25 H 1.211787 0.660273 0.496946 0.044 Uiso 1 1 calc R U . . .
C26 C 0.9430(6) 0.6035(3) 0.52463(11) 0.0366(8) Uani 1 1 d . . . . .
H26 H 1.008878 0.590999 0.548753 0.044 Uiso 1 1 calc R U . . .
C27 C 0.7200(6) 0.5812(3) 0.51784(10) 0.0336(8) 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
Cl1 C3 1.736(4) . ?
Cl2 C27 1.739(4) . ?
Cl3 C21 1.748(4) . ?
O1 C7 1.212(5) . ?
O2 C7 1.346(4) . ?
O2 C8 1.439(4) . ?
O3 N1 1.468(3) . ?
O3 C8 1.396(4) . ?
O4 H4 0.8200 . ?
O4 C22 1.419(4) . ?
N1 C11 1.466(4) . ?
N1 C16 1.474(4) . ?
N2 C17 1.344(4) . ?
N2 C21 1.326(5) . ?
N3 C23 1.341(4) . ?
N3 C27 1.321(4) . ?
C1 C2 1.394(5) . ?
C1 C6 1.398(5) . ?
C1 C7 1.473(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.378(6) . ?
C3 C4 1.385(6) . ?
C4 H4A 0.9300 . ?
C4 C5 1.387(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.381(5) . ?
C6 H6 0.9300 . ?
C8 H8 0.9800 . ?
C8 C9 1.516(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.530(5) . ?
C10 H10 0.9800 . ?
C10 C11 1.534(5) . ?
C10 C15 1.536(5) . ?
C11 H11 0.9800 . ?
C11 C12 1.532(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.532(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.524(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.520(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16 0.9800 . ?
C16 C17 1.520(5) . ?
C16 C22 1.547(4) . ?
C17 C18 1.380(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.390(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.371(6) . ?
C20 H20 0.9300 . ?
C20 C21 1.378(6) . ?
C22 H22 0.9800 . ?
C22 C23 1.508(4) . ?
C23 C24 1.384(5) . ?
C24 H24 0.9300 . ?
C24 C25 1.400(5) . ?
C25 H25 0.9300 . ?
C25 C26 1.374(5) . ?
C26 H26 0.9300 . ?
C26 C27 1.390(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O2 C8 115.7(3) . . ?
C8 O3 N1 109.5(2) . . ?
C22 O4 H4 109.5 . . ?
O3 N1 C16 105.6(2) . . ?
C11 N1 O3 108.4(2) . . ?
C11 N1 C16 119.5(3) . . ?
C21 N2 C17 116.7(3) . . ?
C27 N3 C23 117.4(3) . . ?
C2 C1 C6 119.9(3) . . ?
C2 C1 C7 117.6(3) . . ?
C6 C1 C7 122.5(3) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 C1 119.1(4) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 Cl1 119.4(3) . . ?
C2 C3 C4 121.8(4) . . ?
C4 C3 Cl1 118.9(3) . . ?
C3 C4 H4A 120.7 . . ?
C3 C4 C5 118.6(4) . . ?
C5 C4 H4A 120.7 . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 120.9(4) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 H6 120.2 . . ?
C5 C6 C1 119.7(4) . . ?
C5 C6 H6 120.2 . . ?
O1 C7 O2 122.6(4) . . ?
O1 C7 C1 124.3(3) . . ?
O2 C7 C1 113.1(3) . . ?
O2 C8 H8 108.5 . . ?
O2 C8 C9 111.5(3) . . ?
O3 C8 O2 107.5(3) . . ?
O3 C8 H8 108.5 . . ?
O3 C8 C9 112.2(3) . . ?
C9 C8 H8 108.5 . . ?
C8 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
C8 C9 C10 113.5(3) . . ?
H9A C9 H9B 107.7 . . ?
C10 C9 H9A 108.9 . . ?
C10 C9 H9B 108.9 . . ?
C9 C10 H10 107.9 . . ?
C9 C10 C11 110.2(3) . . ?
C9 C10 C15 111.9(3) . . ?
C11 C10 H10 107.9 . . ?
C11 C10 C15 110.9(3) . . ?
C15 C10 H10 107.9 . . ?
N1 C11 C10 105.5(3) . . ?
N1 C11 H11 106.7 . . ?
N1 C11 C12 117.1(3) . . ?
C10 C11 H11 106.7 . . ?
C12 C11 C10 113.4(3) . . ?
C12 C11 H11 106.7 . . ?
C11 C12 H12A 109.6 . . ?
C11 C12 H12B 109.6 . . ?
C11 C12 C13 110.4(3) . . ?
H12A C12 H12B 108.1 . . ?
C13 C12 H12A 109.6 . . ?
C13 C12 H12B 109.6 . . ?
C12 C13 H13A 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 107.9 . . ?
C14 C13 C12 111.7(3) . . ?
C14 C13 H13A 109.3 . . ?
C14 C13 H13B 109.3 . . ?
C13 C14 H14A 109.6 . . ?
C13 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
C15 C14 C13 110.4(3) . . ?
C15 C14 H14A 109.6 . . ?
C15 C14 H14B 109.6 . . ?
C10 C15 H15A 109.0 . . ?
C10 C15 H15B 109.0 . . ?
C14 C15 C10 112.9(3) . . ?
C14 C15 H15A 109.0 . . ?
C14 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
N1 C16 H16 106.2 . . ?
N1 C16 C17 118.7(3) . . ?
N1 C16 C22 105.5(3) . . ?
C17 C16 H16 106.2 . . ?
C17 C16 C22 113.4(3) . . ?
C22 C16 H16 106.2 . . ?
N2 C17 C16 115.1(3) . . ?
N2 C17 C18 122.1(3) . . ?
C18 C17 C16 122.8(3) . . ?
C17 C18 H18 120.4 . . ?
C17 C18 C19 119.2(4) . . ?
C19 C18 H18 120.4 . . ?
C18 C19 H19 120.2 . . ?
C20 C19 C18 119.5(4) . . ?
C20 C19 H19 120.2 . . ?
C19 C20 H20 121.7 . . ?
C19 C20 C21 116.6(4) . . ?
C21 C20 H20 121.7 . . ?
N2 C21 Cl3 116.0(3) . . ?
N2 C21 C20 125.9(4) . . ?
C20 C21 Cl3 118.1(3) . . ?
O4 C22 C16 109.3(3) . . ?
O4 C22 H22 109.0 . . ?
O4 C22 C23 108.5(3) . . ?
C16 C22 H22 109.0 . . ?
C23 C22 C16 112.0(3) . . ?
C23 C22 H22 109.0 . . ?
N3 C23 C22 115.3(3) . . ?
N3 C23 C24 122.5(3) . . ?
C24 C23 C22 122.1(3) . . ?
C23 C24 H24 120.8 . . ?
C23 C24 C25 118.4(3) . . ?
C25 C24 H24 120.8 . . ?
C24 C25 H25 120.2 . . ?
C26 C25 C24 119.6(3) . . ?
C26 C25 H25 120.2 . . ?
C25 C26 H26 121.6 . . ?
C25 C26 C27 116.8(3) . . ?
C27 C26 H26 121.6 . . ?
N3 C27 Cl2 115.9(3) . . ?
N3 C27 C26 125.1(3) . . ?
C26 C27 Cl2 119.0(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C3 C4 C5 -179.9(3) . . . . ?
O2 C8 C9 C10 75.0(4) . . . . ?
O3 N1 C11 C10 69.2(3) . . . . ?
O3 N1 C11 C12 -58.0(4) . . . . ?
O3 N1 C16 C17 49.5(3) . . . . ?
O3 N1 C16 C22 -78.8(3) . . . . ?
O3 C8 C9 C10 -45.6(4) . . . . ?
O4 C22 C23 N3 153.4(3) . . . . ?
O4 C22 C23 C24 -26.8(4) . . . . ?
N1 O3 C8 O2 -65.9(3) . . . . ?
N1 O3 C8 C9 57.0(3) . . . . ?
N1 C11 C12 C13 176.5(3) . . . . ?
N1 C16 C17 N2 117.9(3) . . . . ?
N1 C16 C17 C18 -64.0(4) . . . . ?
N1 C16 C22 O4 -50.1(3) . . . . ?
N1 C16 C22 C23 -170.4(3) . . . . ?
N2 C17 C18 C19 -0.2(5) . . . . ?
N3 C23 C24 C25 2.1(5) . . . . ?
C1 C2 C3 Cl1 179.4(3) . . . . ?
C1 C2 C3 C4 -0.6(6) . . . . ?
C2 C1 C6 C5 0.8(5) . . . . ?
C2 C1 C7 O1 -3.0(5) . . . . ?
C2 C1 C7 O2 175.4(3) . . . . ?
C2 C3 C4 C5 0.2(6) . . . . ?
C3 C4 C5 C6 0.8(6) . . . . ?
C4 C5 C6 C1 -1.3(6) . . . . ?
C6 C1 C2 C3 0.1(5) . . . . ?
C6 C1 C7 O1 176.4(4) . . . . ?
C6 C1 C7 O2 -5.3(5) . . . . ?
C7 O2 C8 O3 -140.6(3) . . . . ?
C7 O2 C8 C9 96.1(4) . . . . ?
C7 C1 C2 C3 179.5(3) . . . . ?
C7 C1 C6 C5 -178.5(3) . . . . ?
C8 O2 C7 O1 -6.3(5) . . . . ?
C8 O2 C7 C1 175.3(3) . . . . ?
C8 O3 N1 C11 -71.8(3) . . . . ?
C8 O3 N1 C16 159.1(2) . . . . ?
C8 C9 C10 C11 44.9(4) . . . . ?
C8 C9 C10 C15 168.7(3) . . . . ?
C9 C10 C11 N1 -56.0(3) . . . . ?
C9 C10 C11 C12 73.4(4) . . . . ?
C9 C10 C15 C14 -71.3(4) . . . . ?
C10 C11 C12 C13 53.2(4) . . . . ?
C11 N1 C16 C17 -72.8(4) . . . . ?
C11 N1 C16 C22 158.9(3) . . . . ?
C11 C10 C15 C14 52.2(5) . . . . ?
C11 C12 C13 C14 -56.1(4) . . . . ?
C12 C13 C14 C15 57.5(5) . . . . ?
C13 C14 C15 C10 -55.7(5) . . . . ?
C15 C10 C11 N1 179.6(3) . . . . ?
C15 C10 C11 C12 -51.0(4) . . . . ?
C16 N1 C11 C10 -169.9(3) . . . . ?
C16 N1 C11 C12 62.9(4) . . . . ?
C16 C17 C18 C19 -178.2(3) . . . . ?
C16 C22 C23 N3 -86.0(3) . . . . ?
C16 C22 C23 C24 93.9(4) . . . . ?
C17 N2 C21 Cl3 179.6(2) . . . . ?
C17 N2 C21 C20 0.1(5) . . . . ?
C17 C16 C22 O4 178.5(2) . . . . ?
C17 C16 C22 C23 58.2(4) . . . . ?
C17 C18 C19 C20 -0.5(6) . . . . ?
C18 C19 C20 C21 0.9(6) . . . . ?
C19 C20 C21 Cl3 179.7(3) . . . . ?
C19 C20 C21 N2 -0.8(6) . . . . ?
C21 N2 C17 C16 178.5(3) . . . . ?
C21 N2 C17 C18 0.4(5) . . . . ?
C22 C16 C17 N2 -117.6(3) . . . . ?
C22 C16 C17 C18 60.5(4) . . . . ?
C22 C23 C24 C25 -177.8(3) . . . . ?
C23 N3 C27 Cl2 178.3(3) . . . . ?
C23 N3 C27 C26 -0.4(6) . . . . ?
C23 C24 C25 C26 -2.1(5) . . . . ?
C24 C25 C26 C27 0.9(6) . . . . ?
C25 C26 C27 Cl2 -178.3(3) . . . . ?
C25 C26 C27 N3 0.3(6) . . . . ?
C27 N3 C23 C22 179.0(3) . . . . ?
C27 N3 C23 C24 -0.9(5) . . . . ?

_olex2_date_sample_data_collection 2022-08-10
_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 1.737
_oxdiff_exptl_absorpt_empirical_full_min 0.606
