# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# 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_zhd_2
_audit_block_doi                 10.5517/ccdc.csd.cc27t6pz
_database_code_depnum_ccdc_archive 'CCDC 2079811'
loop_
_audit_author_name
_audit_author_address
'hua zhang'
;Chinese Academy of Sciences University
China
;
_audit_update_record             
;
2021-04-24 deposited with the CCDC.	2021-08-24 downloaded from the CCDC.
;
_audit_creation_date             2020-06-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H21 N O2'
_chemical_formula_sum            'C23 H21 N O2'
_chemical_formula_weight         343.41
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   9.3482(13)
_cell_length_b                   9.9667(14)
_cell_length_c                   11.3283(15)
_cell_angle_alpha                111.927(13)
_cell_angle_beta                 101.129(12)
_cell_angle_gamma                108.193(13)
_cell_volume                     870.9(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2761
_cell_measurement_temperature    150.00(16)
_cell_measurement_theta_max      28.9390
_cell_measurement_theta_min      2.4280
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83116
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.14
_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  0.0477
_diffrn_reflns_av_unetI/netI     0.0640
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6225
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.070
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(16)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -52.00  37.00   1.00    3.50    --   11.74 -57.00  90.00   89
  2  ω    -13.00  82.00   1.00    3.50    --   11.74  77.00 -30.00   95
  3  ω    -51.00  43.00   1.00    3.50    --   11.74 -77.00-150.00   94
  4  ω    -62.00 -37.00   1.00    3.50    --  -11.59 116.00  46.00   25
  5  ω     28.00  53.00   1.00   10.00    --   11.66 -19.00  60.00   25
  6  ω     61.00  83.00   1.00    2.00    --   11.74  37.00   0.00   22
;
_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      -0.0313026000
_diffrn_orient_matrix_UB_12      -0.0276798000
_diffrn_orient_matrix_UB_13      -0.0710989000
_diffrn_orient_matrix_UB_21      -0.0671706000
_diffrn_orient_matrix_UB_22      -0.0632587000
_diffrn_orient_matrix_UB_23      -0.0056379000
_diffrn_orient_matrix_UB_31      -0.0422540000
_diffrn_orient_matrix_UB_32      0.0489311000
_diffrn_orient_matrix_UB_33      0.0105018000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2291
_reflns_number_total             3034
_reflns_odcompleteness_completeness 98.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         3034
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0787
_refine_ls_R_factor_gt           0.0585
_refine_ls_restrained_S_all      1.054
_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)+(0.0769P)²+0.2386P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1441
_refine_ls_wR_factor_ref         0.1644
_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:
 C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C16(H16), C18(H18), C19(H19), C20(H20),
 C21(H21)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   mixed
_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 -0.8542(3) -1.3042(3) -0.5251(2) 0.0244(5) Uani 1 1 d . . . . .
C2 C -1.0053(3) -1.4243(3) -0.6219(2) 0.0291(6) Uani 1 1 d . . . . .
H2 H -1.093659 -1.397653 -0.638498 0.035 Uiso 1 1 calc R U . . .
C3 C -1.0262(3) -1.5783(3) -0.6920(3) 0.0346(6) Uani 1 1 d . . . . .
H3 H -1.128659 -1.657606 -0.756547 0.042 Uiso 1 1 calc R U . . .
C4 C -0.8970(3) -1.6202(3) -0.6690(3) 0.0341(6) Uani 1 1 d . . . . .
H4 H -0.913607 -1.728111 -0.716756 0.041 Uiso 1 1 calc R U . . .
C5 C -0.7483(3) -1.5077(3) -0.5792(2) 0.0285(6) Uani 1 1 d . . . . .
H5 H -0.661517 -1.537167 -0.565599 0.034 Uiso 1 1 calc R U . . .
C6 C -0.7226(3) -1.3461(3) -0.5056(2) 0.0255(5) Uani 1 1 d . . . . .
C7 C -0.5737(3) -1.2226(3) -0.4124(2) 0.0246(5) Uani 1 1 d . . . . .
C8 C -0.5481(3) -1.0672(3) -0.3407(2) 0.0256(5) Uani 1 1 d . . . . .
C9 C -0.6795(3) -1.0240(3) -0.3576(2) 0.0245(5) Uani 1 1 d . . . . .
C10 C -0.8285(3) -1.1432(3) -0.4490(2) 0.0254(5) Uani 1 1 d . . . . .
C11 C -0.3748(3) -0.9708(3) -0.2433(2) 0.0274(6) Uani 1 1 d . . . . .
C12 C -0.3060(3) -1.0937(3) -0.2978(3) 0.0431(7) Uani 1 1 d . . . . .
H12A H -0.241482 -1.064860 -0.351457 0.052 Uiso 1 1 calc R U . . .
H12B H -0.235146 -1.094433 -0.221014 0.052 Uiso 1 1 calc R U . . .
C13 C -0.3678(3) -0.9315(4) -0.0974(3) 0.0427(7) Uani 1 1 d . . . . .
H13A H -0.255620 -0.869283 -0.035529 0.064 Uiso 1 1 calc R U . . .
H13B H -0.413423 -1.030718 -0.091636 0.064 Uiso 1 1 calc R U . . .
H13C H -0.429741 -0.869189 -0.071681 0.064 Uiso 1 1 calc R U . . .
C14 C -0.2821(3) -0.8201(3) -0.2511(3) 0.0377(7) Uani 1 1 d . . . . .
H14A H -0.317454 -0.737542 -0.207300 0.057 Uiso 1 1 calc R U . . .
H14B H -0.302662 -0.844267 -0.346521 0.057 Uiso 1 1 calc R U . . .
H14C H -0.166727 -0.781743 -0.204420 0.057 Uiso 1 1 calc R U . . .
C15 C -0.6664(3) -0.8597(3) -0.2823(2) 0.0257(5) Uani 1 1 d . . . . .
C16 C -0.5984(3) -0.7299(3) -0.3011(2) 0.0284(6) Uani 1 1 d . . . . .
H16 H -0.543397 -0.728338 -0.363220 0.034 Uiso 1 1 calc R U . . .
C17 C -0.7375(3) -0.8097(3) -0.1809(2) 0.0249(5) Uani 1 1 d . . . . .
C18 C -0.8242(3) -0.8850(3) -0.1182(2) 0.0295(6) Uani 1 1 d . . . . .
H18 H -0.846518 -0.993073 -0.140796 0.035 Uiso 1 1 calc R U . . .
C19 C -0.8768(3) -0.7994(3) -0.0230(3) 0.0359(6) Uani 1 1 d . . . . .
H19 H -0.936190 -0.849678 0.019544 0.043 Uiso 1 1 calc R U . . .
C20 C -0.8439(3) -0.6400(3) 0.0116(3) 0.0358(6) Uani 1 1 d . . . . .
H20 H -0.881633 -0.584257 0.077312 0.043 Uiso 1 1 calc R U . . .
C21 C -0.7587(3) -0.5622(3) -0.0470(2) 0.0309(6) Uani 1 1 d . . . . .
H21 H -0.736939 -0.453991 -0.023157 0.037 Uiso 1 1 calc R U . . .
C22 C -0.7047(3) -0.6483(3) -0.1436(2) 0.0258(5) Uani 1 1 d . . . . .
C23 C -0.5548(3) -0.4426(3) -0.2062(3) 0.0333(6) Uani 1 1 d . . . . .
H23A H -0.643138 -0.414067 -0.231426 0.050 Uiso 1 1 calc R U . . .
H23B H -0.493003 -0.439873 -0.266723 0.050 Uiso 1 1 calc R U . . .
H23C H -0.484277 -0.366172 -0.112094 0.050 Uiso 1 1 calc R U . . .
N1 N -0.6201(2) -0.6026(2) -0.2189(2) 0.0278(5) Uani 1 1 d . . . . .
O1 O -0.9611(2) -1.1120(2) -0.47261(19) 0.0348(5) Uani 1 1 d . . . . .
H1 H -0.933(5) -1.008(5) -0.417(5) 0.116(16) Uiso 1 1 d . . . . .
O2 O -0.43785(19) -1.24965(19) -0.38231(17) 0.0317(4) 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 1.413(3) . ?
C1 C6 1.422(3) . ?
C1 C10 1.422(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.367(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.405(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.361(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.423(3) . ?
C6 C7 1.400(3) . ?
C7 C8 1.368(3) . ?
C7 O2 1.384(3) . ?
C8 C9 1.425(3) . ?
C8 C11 1.521(3) . ?
C9 C10 1.384(3) . ?
C9 C15 1.488(3) . ?
C10 O1 1.371(3) . ?
C11 C12 1.541(3) . ?
C11 C13 1.532(3) . ?
C11 C14 1.527(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 O2 1.445(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.367(3) . ?
C15 C17 1.443(3) . ?
C16 H16 0.9500 . ?
C16 N1 1.367(3) . ?
C17 C18 1.402(3) . ?
C17 C22 1.412(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.382(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.398(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.371(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.403(3) . ?
C22 N1 1.373(3) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C23 N1 1.458(3) . ?
O1 H1 0.90(4) . ?

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 118.4(2) . . ?
C2 C1 C10 122.5(2) . . ?
C6 C1 C10 119.1(2) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 C1 120.9(2) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.4(2) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.7(2) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.1(2) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 119.3(2) . . ?
C7 C6 C1 116.7(2) . . ?
C7 C6 C5 124.0(2) . . ?
C8 C7 C6 124.4(2) . . ?
C8 C7 O2 113.7(2) . . ?
O2 C7 C6 121.9(2) . . ?
C7 C8 C9 119.5(2) . . ?
C7 C8 C11 109.13(19) . . ?
C9 C8 C11 131.1(2) . . ?
C8 C9 C15 124.1(2) . . ?
C10 C9 C8 117.6(2) . . ?
C10 C9 C15 118.3(2) . . ?
C9 C10 C1 122.7(2) . . ?
O1 C10 C1 115.8(2) . . ?
O1 C10 C9 121.5(2) . . ?
C8 C11 C12 99.66(19) . . ?
C8 C11 C13 110.19(19) . . ?
C8 C11 C14 115.09(19) . . ?
C13 C11 C12 111.4(2) . . ?
C14 C11 C12 109.3(2) . . ?
C14 C11 C13 110.7(2) . . ?
C11 C12 H12A 109.9 . . ?
C11 C12 H12B 109.9 . . ?
H12A C12 H12B 108.3 . . ?
O2 C12 C11 108.83(19) . . ?
O2 C12 H12A 109.9 . . ?
O2 C12 H12B 109.9 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C9 128.2(2) . . ?
C16 C15 C17 105.8(2) . . ?
C17 C15 C9 125.8(2) . . ?
C15 C16 H16 124.5 . . ?
C15 C16 N1 111.1(2) . . ?
N1 C16 H16 124.5 . . ?
C18 C17 C15 134.2(2) . . ?
C18 C17 C22 119.0(2) . . ?
C22 C17 C15 106.7(2) . . ?
C17 C18 H18 120.6 . . ?
C19 C18 C17 118.9(2) . . ?
C19 C18 H18 120.6 . . ?
C18 C19 H19 119.5 . . ?
C18 C19 C20 121.1(2) . . ?
C20 C19 H19 119.5 . . ?
C19 C20 H20 119.2 . . ?
C21 C20 C19 121.6(2) . . ?
C21 C20 H20 119.2 . . ?
C20 C21 H21 121.2 . . ?
C20 C21 C22 117.6(2) . . ?
C22 C21 H21 121.2 . . ?
C21 C22 C17 121.7(2) . . ?
N1 C22 C17 108.04(19) . . ?
N1 C22 C21 130.2(2) . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N1 C23 H23A 109.5 . . ?
N1 C23 H23B 109.5 . . ?
N1 C23 H23C 109.5 . . ?
C16 N1 C22 108.37(19) . . ?
C16 N1 C23 125.8(2) . . ?
C22 N1 C23 125.74(19) . . ?
C10 O1 H1 109(3) . . ?
C7 O2 C12 105.75(18) . . ?

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 -0.1(4) . . . . ?
C1 C6 C7 C8 -0.2(3) . . . . ?
C1 C6 C7 O2 178.31(18) . . . . ?
C2 C1 C6 C5 -2.7(3) . . . . ?
C2 C1 C6 C7 177.8(2) . . . . ?
C2 C1 C10 C9 -177.7(2) . . . . ?
C2 C1 C10 O1 1.7(3) . . . . ?
C2 C3 C4 C5 -1.5(4) . . . . ?
C3 C4 C5 C6 1.0(4) . . . . ?
C4 C5 C6 C1 1.1(3) . . . . ?
C4 C5 C6 C7 -179.4(2) . . . . ?
C5 C6 C7 C8 -179.7(2) . . . . ?
C5 C6 C7 O2 -1.2(3) . . . . ?
C6 C1 C2 C3 2.2(3) . . . . ?
C6 C1 C10 C9 1.0(3) . . . . ?
C6 C1 C10 O1 -179.61(18) . . . . ?
C6 C7 C8 C9 1.2(3) . . . . ?
C6 C7 C8 C11 176.3(2) . . . . ?
C6 C7 O2 C12 172.5(2) . . . . ?
C7 C8 C9 C10 -1.1(3) . . . . ?
C7 C8 C9 C15 178.3(2) . . . . ?
C7 C8 C11 C12 11.5(2) . . . . ?
C7 C8 C11 C13 -105.8(2) . . . . ?
C7 C8 C11 C14 128.2(2) . . . . ?
C8 C7 O2 C12 -8.8(3) . . . . ?
C8 C9 C10 C1 0.0(3) . . . . ?
C8 C9 C10 O1 -179.32(19) . . . . ?
C8 C9 C15 C16 74.0(3) . . . . ?
C8 C9 C15 C17 -111.9(3) . . . . ?
C8 C11 C12 O2 -16.7(2) . . . . ?
C9 C8 C11 C12 -174.3(2) . . . . ?
C9 C8 C11 C13 68.5(3) . . . . ?
C9 C8 C11 C14 -57.5(3) . . . . ?
C9 C15 C16 N1 175.5(2) . . . . ?
C9 C15 C17 C18 4.5(4) . . . . ?
C9 C15 C17 C22 -175.9(2) . . . . ?
C10 C1 C2 C3 -179.1(2) . . . . ?
C10 C1 C6 C5 178.6(2) . . . . ?
C10 C1 C6 C7 -0.9(3) . . . . ?
C10 C9 C15 C16 -106.5(3) . . . . ?
C10 C9 C15 C17 67.5(3) . . . . ?
C11 C8 C9 C10 -174.9(2) . . . . ?
C11 C8 C9 C15 4.5(4) . . . . ?
C11 C12 O2 C7 16.3(3) . . . . ?
C13 C11 C12 O2 99.6(3) . . . . ?
C14 C11 C12 O2 -137.7(2) . . . . ?
C15 C9 C10 C1 -179.43(19) . . . . ?
C15 C9 C10 O1 1.2(3) . . . . ?
C15 C16 N1 C22 -0.1(3) . . . . ?
C15 C16 N1 C23 175.9(2) . . . . ?
C15 C17 C18 C19 -179.6(2) . . . . ?
C15 C17 C22 C21 179.3(2) . . . . ?
C15 C17 C22 N1 0.7(2) . . . . ?
C16 C15 C17 C18 179.6(2) . . . . ?
C16 C15 C17 C22 -0.7(2) . . . . ?
C17 C15 C16 N1 0.5(3) . . . . ?
C17 C18 C19 C20 -0.4(4) . . . . ?
C17 C22 N1 C16 -0.3(3) . . . . ?
C17 C22 N1 C23 -176.4(2) . . . . ?
C18 C17 C22 C21 -1.0(3) . . . . ?
C18 C17 C22 N1 -179.63(19) . . . . ?
C18 C19 C20 C21 0.0(4) . . . . ?
C19 C20 C21 C22 -0.1(4) . . . . ?
C20 C21 C22 C17 0.6(3) . . . . ?
C20 C21 C22 N1 178.9(2) . . . . ?
C21 C22 N1 C16 -178.9(2) . . . . ?
C21 C22 N1 C23 5.1(4) . . . . ?
C22 C17 C18 C19 0.8(3) . . . . ?
O2 C7 C8 C9 -177.37(18) . . . . ?
O2 C7 C8 C11 -2.3(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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.864
_oxdiff_exptl_absorpt_empirical_full_min 0.672
####################################################################### 
# 
# 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_zhd_3_4
_audit_block_doi                 10.5517/ccdc.csd.cc27t6r1
_database_code_depnum_ccdc_archive 'CCDC 2079813'
loop_
_audit_author_name
_audit_author_address
'hua zhang'
;Chinese Academy of Sciences University
China
;
_audit_update_record             
;
2021-04-24 deposited with the CCDC.	2021-08-24 downloaded from the CCDC.
;
_audit_creation_date             2021-03-06
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H18 Br N O3'
_chemical_formula_sum            'C23 H18 Br N O3'
_chemical_formula_weight         436.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H13 N13 O13 Br13 '
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      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                   7.5489(4)
_cell_length_b                   9.1816(6)
_cell_length_c                   13.9165(8)
_cell_angle_alpha                89.982(5)
_cell_angle_beta                 85.879(4)
_cell_angle_gamma                71.987(5)
_cell_volume                     914.67(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3178
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.7630
_cell_measurement_theta_min      3.1240
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.272
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84017
_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            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0585
_diffrn_reflns_av_unetI/netI     0.0488
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5619
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        66.601
_diffrn_reflns_theta_max         66.601
_diffrn_reflns_theta_min         3.185
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5368
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     29.00  81.00   1.00    1.00    --   41.80 -99.00  60.00   52
  2  ω     76.00 111.00   1.00    1.00    --  107.51-125.00  90.00   35
  3  ω     64.00 125.00   1.00    1.00    --  107.51 -45.00  60.00   61
  4  ω     81.00 175.00   1.00    1.00    --  107.51  30.00 120.00   94
  5  ω    104.00 176.00   1.00    1.00    --  107.51 125.00 -30.00   72
  6  ω    108.00 133.00   1.00    1.00    --  107.51 -45.00-180.00   25
  7  ω     47.00 156.00   1.00    1.00    --  107.51 -15.00 -90.00  109
  8  ω     41.00 101.00   1.00    1.00    --  107.51 -45.00-180.00   60
  9  ω     39.00 135.00   1.00    1.00    --  107.51 -61.00 -60.00   96
 10  ω     34.00 118.00   1.00    1.00    --  107.51-125.00 -30.00   84
 11  ω     31.00 109.00   1.00    1.00    --  107.51 -94.00 120.00   78
 12  ω      4.00  58.00   1.00    1.00    --   41.80 -99.00 -90.00   54
 13  ω      3.00  46.00   1.00    1.00    --   41.80 -99.00-180.00   43
 14  ω   -113.00 -17.00   1.00    1.00    --  -41.80 -38.00  30.00   96
 15  ω   -116.00 -25.00   1.00    1.00    --  -41.80 -38.00 -60.00   91
;
_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      0.0826500000
_diffrn_orient_matrix_UB_12      -0.1709771000
_diffrn_orient_matrix_UB_13      -0.0288289000
_diffrn_orient_matrix_UB_21      0.1323404000
_diffrn_orient_matrix_UB_22      -0.0234974000
_diffrn_orient_matrix_UB_23      0.0818833000
_diffrn_orient_matrix_UB_31      -0.1482190000
_diffrn_orient_matrix_UB_32      -0.0368864000
_diffrn_orient_matrix_UB_33      0.0692011000
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2928
_reflns_number_total             3214
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.638
_refine_diff_density_min         -1.032
_refine_diff_density_rms         0.098
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3214
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0480
_refine_ls_restrained_S_all      1.075
_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)+(0.0830P)²+0.5401P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1318
_refine_ls_wR_factor_ref         0.1356
_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:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C17(H17), C18(H18), C19(H19), C20(H20)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.02159(5) 0.23824(4) 0.74832(3) 0.04028(18) Uani 1 1 d . . . . .
O1 O 0.7670(4) 0.7830(3) 0.51326(17) 0.0370(6) Uani 1 1 d . . . . .
O2 O 0.5063(4) 0.8518(3) 0.88434(16) 0.0348(6) Uani 1 1 d . . . . .
O3 O 0.5829(3) 0.3699(3) 0.72390(17) 0.0324(5) Uani 1 1 d . . . . .
N1 N 0.6285(4) 0.6606(4) 0.98687(19) 0.0330(7) Uani 1 1 d . . . . .
C1 C 0.7333(5) 0.5087(4) 0.9849(2) 0.0323(7) Uani 1 1 d . . . . .
C2 C 0.7911(6) 0.4165(5) 1.0631(3) 0.0414(9) Uani 1 1 d . . . . .
H2 H 0.755471 0.453520 1.126059 0.050 Uiso 1 1 calc R U . . .
C3 C 0.9033(6) 0.2678(5) 1.0439(3) 0.0457(10) Uani 1 1 d . . . . .
H3 H 0.938523 0.201088 1.094365 0.055 Uiso 1 1 calc R U . . .
C4 C 0.9640(5) 0.2170(5) 0.9495(3) 0.0432(9) Uani 1 1 d . . . . .
H4 H 1.045582 0.118511 0.937772 0.052 Uiso 1 1 calc R U . . .
C5 C 0.9047(5) 0.3112(4) 0.8724(3) 0.0347(8) Uani 1 1 d . . . . .
C6 C 0.7785(4) 0.4584(4) 0.8875(2) 0.0279(7) Uani 1 1 d . . . . .
C7 C 0.6863(5) 0.5875(4) 0.8285(2) 0.0274(7) Uani 1 1 d . . . . .
C8 C 0.6041(5) 0.7055(4) 0.8944(2) 0.0298(7) Uani 1 1 d . . . . .
C9 C 0.4457(5) 0.8955(4) 0.7897(2) 0.0310(7) Uani 1 1 d . . . . .
H9A H 0.366884 1.001434 0.793306 0.037 Uiso 1 1 calc R U . . .
H9B H 0.369327 0.833698 0.771655 0.037 Uiso 1 1 calc R U . . .
C10 C 0.6032(5) 0.8791(4) 0.7087(2) 0.0290(7) Uani 1 1 d . . . . .
C11 C 0.6627(4) 0.7162(4) 0.6665(2) 0.0249(6) Uani 1 1 d . . . . .
C12 C 0.6811(4) 0.5901(4) 0.7239(2) 0.0251(6) Uani 1 1 d . . . . .
C13 C 0.6605(4) 0.4490(4) 0.6777(2) 0.0262(7) Uani 1 1 d . . . . .
C14 C 0.7179(4) 0.4177(4) 0.5739(2) 0.0292(7) Uani 1 1 d . . . . .
C15 C 0.7408(4) 0.5355(4) 0.5172(2) 0.0285(7) Uani 1 1 d . . . . .
C16 C 0.7202(4) 0.6881(4) 0.5615(2) 0.0272(7) Uani 1 1 d . . . . .
C17 C 0.7862(5) 0.5100(5) 0.4183(2) 0.0347(8) Uani 1 1 d . . . . .
H17 H 0.798776 0.589264 0.379477 0.042 Uiso 1 1 calc R U . . .
C18 C 0.8122(5) 0.3667(5) 0.3785(3) 0.0400(9) Uani 1 1 d . . . . .
H18 H 0.841454 0.349915 0.312514 0.048 Uiso 1 1 calc R U . . .
C19 C 0.7955(5) 0.2483(5) 0.4353(3) 0.0416(9) Uani 1 1 d . . . . .
H19 H 0.818127 0.151258 0.407841 0.050 Uiso 1 1 calc R U . . .
C20 C 0.7452(5) 0.2727(4) 0.5329(3) 0.0360(8) Uani 1 1 d . . . . .
H20 H 0.729673 0.193480 0.570863 0.043 Uiso 1 1 calc R U . . .
C21 C 0.5545(6) 0.7571(5) 1.0724(2) 0.0405(9) Uani 1 1 d . . . . .
H21A H 0.490977 0.859461 1.053647 0.061 Uiso 1 1 calc R U . . .
H21B H 0.655297 0.758114 1.110513 0.061 Uiso 1 1 calc R U . . .
H21C H 0.468514 0.717313 1.109686 0.061 Uiso 1 1 calc R U . . .
C22 C 0.7674(5) 0.9199(4) 0.7451(3) 0.0363(8) Uani 1 1 d . . . . .
H22A H 0.827933 0.844848 0.790110 0.054 Uiso 1 1 calc R U . . .
H22B H 0.723289 1.019034 0.776504 0.054 Uiso 1 1 calc R U . . .
H22C H 0.854743 0.921637 0.691802 0.054 Uiso 1 1 calc R U . . .
C23 C 0.5038(5) 1.0002(4) 0.6362(3) 0.0350(8) Uani 1 1 d . . . . .
H23A H 0.589578 1.000770 0.581917 0.053 Uiso 1 1 calc R U . . .
H23B H 0.461784 1.099635 0.667195 0.053 Uiso 1 1 calc R U . . .
H23C H 0.398537 0.975158 0.614625 0.053 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
Br1 C5 1.904(4) . ?
O1 C16 1.221(4) . ?
O2 C8 1.331(4) . ?
O2 C9 1.441(4) . ?
O3 C13 1.222(4) . ?
N1 C1 1.373(5) . ?
N1 C8 1.358(4) . ?
N1 C21 1.454(5) . ?
C1 C2 1.390(5) . ?
C1 C6 1.415(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.380(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.391(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.388(5) . ?
C5 C6 1.398(5) . ?
C6 C7 1.461(4) . ?
C7 C8 1.380(5) . ?
C7 C12 1.459(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.551(4) . ?
C10 C11 1.526(5) . ?
C10 C22 1.521(5) . ?
C10 C23 1.552(4) . ?
C11 C12 1.383(4) . ?
C11 C16 1.494(4) . ?
C12 C13 1.501(5) . ?
C13 C14 1.480(4) . ?
C14 C15 1.385(5) . ?
C14 C20 1.398(5) . ?
C15 C16 1.490(5) . ?
C15 C17 1.396(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.379(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.376(6) . ?
C19 H19 0.9300 . ?
C19 C20 1.384(5) . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

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
C8 O2 C9 116.4(3) . . ?
C1 N1 C21 126.4(3) . . ?
C8 N1 C1 108.0(3) . . ?
C8 N1 C21 125.6(3) . . ?
N1 C1 C2 127.5(3) . . ?
N1 C1 C6 108.4(3) . . ?
C2 C1 C6 124.1(4) . . ?
C1 C2 H2 121.3 . . ?
C3 C2 C1 117.5(4) . . ?
C3 C2 H2 121.3 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.4(3) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 121.0(4) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 Br1 116.8(3) . . ?
C4 C5 C6 120.8(4) . . ?
C6 C5 Br1 122.0(3) . . ?
C1 C6 C7 106.9(3) . . ?
C5 C6 C1 115.7(3) . . ?
C5 C6 C7 137.2(3) . . ?
C8 C7 C6 104.1(3) . . ?
C8 C7 C12 128.1(3) . . ?
C12 C7 C6 127.8(3) . . ?
O2 C8 N1 115.2(3) . . ?
O2 C8 C7 132.3(3) . . ?
N1 C8 C7 112.4(3) . . ?
O2 C9 H9A 108.3 . . ?
O2 C9 H9B 108.3 . . ?
O2 C9 C10 115.9(3) . . ?
H9A C9 H9B 107.4 . . ?
C10 C9 H9A 108.3 . . ?
C10 C9 H9B 108.3 . . ?
C9 C10 C23 101.9(3) . . ?
C11 C10 C9 108.8(3) . . ?
C11 C10 C23 112.5(3) . . ?
C22 C10 C9 111.6(3) . . ?
C22 C10 C11 111.7(3) . . ?
C22 C10 C23 109.9(3) . . ?
C12 C11 C10 122.1(3) . . ?
C12 C11 C16 117.8(3) . . ?
C16 C11 C10 119.9(3) . . ?
C7 C12 C13 115.6(3) . . ?
C11 C12 C7 126.3(3) . . ?
C11 C12 C13 117.2(3) . . ?
O3 C13 C12 119.6(3) . . ?
O3 C13 C14 121.2(3) . . ?
C14 C13 C12 118.8(3) . . ?
C15 C14 C13 118.9(3) . . ?
C15 C14 C20 120.3(3) . . ?
C20 C14 C13 120.8(3) . . ?
C14 C15 C16 120.3(3) . . ?
C14 C15 C17 119.7(3) . . ?
C17 C15 C16 120.0(3) . . ?
O1 C16 C11 121.0(3) . . ?
O1 C16 C15 119.2(3) . . ?
C15 C16 C11 119.5(3) . . ?
C15 C17 H17 120.2 . . ?
C18 C17 C15 119.6(3) . . ?
C18 C17 H17 120.2 . . ?
C17 C18 H18 119.6 . . ?
C19 C18 C17 120.7(3) . . ?
C19 C18 H18 119.6 . . ?
C18 C19 H19 119.8 . . ?
C18 C19 C20 120.4(4) . . ?
C20 C19 H19 119.8 . . ?
C14 C20 H20 120.4 . . ?
C19 C20 C14 119.3(3) . . ?
C19 C20 H20 120.4 . . ?
N1 C21 H21A 109.5 . . ?
N1 C21 H21B 109.5 . . ?
N1 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C10 C22 H22A 109.5 . . ?
C10 C22 H22B 109.5 . . ?
C10 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C10 C23 H23A 109.5 . . ?
C10 C23 H23B 109.5 . . ?
C10 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C23 H23A O1 0.96 2.21 2.813(5) 120.2 . yes

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 C5 C6 C1 -167.1(2) . . . . ?
Br1 C5 C6 C7 6.1(6) . . . . ?
O2 C9 C10 C11 87.0(3) . . . . ?
O2 C9 C10 C22 -36.7(4) . . . . ?
O2 C9 C10 C23 -153.9(3) . . . . ?
O3 C13 C14 C15 156.7(3) . . . . ?
O3 C13 C14 C20 -22.0(5) . . . . ?
N1 C1 C2 C3 -177.1(3) . . . . ?
N1 C1 C6 C5 172.3(3) . . . . ?
N1 C1 C6 C7 -2.9(4) . . . . ?
C1 N1 C8 O2 -179.2(3) . . . . ?
C1 N1 C8 C7 1.2(4) . . . . ?
C1 C2 C3 C4 3.8(5) . . . . ?
C1 C6 C7 C8 3.5(3) . . . . ?
C1 C6 C7 C12 -175.9(3) . . . . ?
C2 C1 C6 C5 -6.7(5) . . . . ?
C2 C1 C6 C7 178.1(3) . . . . ?
C2 C3 C4 C5 -3.8(6) . . . . ?
C3 C4 C5 Br1 172.3(3) . . . . ?
C3 C4 C5 C6 -1.6(6) . . . . ?
C4 C5 C6 C1 6.5(5) . . . . ?
C4 C5 C6 C7 179.8(4) . . . . ?
C5 C6 C7 C8 -170.1(4) . . . . ?
C5 C6 C7 C12 10.4(6) . . . . ?
C6 C1 C2 C3 1.6(5) . . . . ?
C6 C7 C8 O2 177.6(3) . . . . ?
C6 C7 C8 N1 -3.0(4) . . . . ?
C6 C7 C12 C11 -152.2(3) . . . . ?
C6 C7 C12 C13 39.1(4) . . . . ?
C7 C12 C13 O3 26.9(4) . . . . ?
C7 C12 C13 C14 -159.2(3) . . . . ?
C8 O2 C9 C10 -63.3(4) . . . . ?
C8 N1 C1 C2 -179.9(3) . . . . ?
C8 N1 C1 C6 1.2(4) . . . . ?
C8 C7 C12 C11 28.4(5) . . . . ?
C8 C7 C12 C13 -140.3(3) . . . . ?
C9 O2 C8 N1 -167.9(3) . . . . ?
C9 O2 C8 C7 11.6(5) . . . . ?
C9 C10 C11 C12 -40.7(4) . . . . ?
C9 C10 C11 C16 145.0(3) . . . . ?
C10 C11 C12 C7 -13.5(5) . . . . ?
C10 C11 C12 C13 155.1(3) . . . . ?
C10 C11 C16 O1 19.0(5) . . . . ?
C10 C11 C16 C15 -167.7(3) . . . . ?
C11 C12 C13 O3 -142.9(3) . . . . ?
C11 C12 C13 C14 31.0(4) . . . . ?
C12 C7 C8 O2 -3.0(6) . . . . ?
C12 C7 C8 N1 176.5(3) . . . . ?
C12 C11 C16 O1 -155.5(3) . . . . ?
C12 C11 C16 C15 17.8(4) . . . . ?
C12 C13 C14 C15 -17.1(4) . . . . ?
C12 C13 C14 C20 164.2(3) . . . . ?
C13 C14 C15 C16 4.0(5) . . . . ?
C13 C14 C15 C17 -176.9(3) . . . . ?
C13 C14 C20 C19 178.8(3) . . . . ?
C14 C15 C16 O1 169.5(3) . . . . ?
C14 C15 C16 C11 -3.9(4) . . . . ?
C14 C15 C17 C18 -1.6(5) . . . . ?
C15 C14 C20 C19 0.1(5) . . . . ?
C15 C17 C18 C19 -0.5(5) . . . . ?
C16 C11 C12 C7 160.9(3) . . . . ?
C16 C11 C12 C13 -30.6(4) . . . . ?
C16 C15 C17 C18 177.5(3) . . . . ?
C17 C15 C16 O1 -9.5(5) . . . . ?
C17 C15 C16 C11 177.1(3) . . . . ?
C17 C18 C19 C20 2.5(6) . . . . ?
C18 C19 C20 C14 -2.2(6) . . . . ?
C20 C14 C15 C16 -177.2(3) . . . . ?
C20 C14 C15 C17 1.8(5) . . . . ?
C21 N1 C1 C2 -0.4(6) . . . . ?
C21 N1 C1 C6 -179.4(3) . . . . ?
C21 N1 C8 O2 1.3(5) . . . . ?
C21 N1 C8 C7 -178.2(3) . . . . ?
C22 C10 C11 C12 82.9(4) . . . . ?
C22 C10 C11 C16 -91.4(3) . . . . ?
C23 C10 C11 C12 -152.9(3) . . . . ?
C23 C10 C11 C16 32.8(4) . . . . ?

_olex2_date_sample_data_collection 2021-03-06
_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 1.270
_oxdiff_exptl_absorpt_empirical_full_min 0.827
####################################################################### 
# 
# 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_zhd_4
_audit_block_doi                 10.5517/ccdc.csd.cc27t6q0
_database_code_depnum_ccdc_archive 'CCDC 2079812'
loop_
_audit_author_name
_audit_author_address
'hua zhang'
;Chinese Academy of Sciences University
China
;
_audit_update_record             
;
2021-04-24 deposited with the CCDC.	2021-08-24 downloaded from the CCDC.
;
_audit_creation_date             2021-03-29
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H12 O3'
_chemical_formula_sum            'C14 H12 O3'
_chemical_formula_weight         228.24
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   11.3788(6)
_cell_length_b                   16.9785(9)
_cell_length_c                   11.7105(7)
_cell_angle_alpha                90
_cell_angle_beta                 103.517(6)
_cell_angle_gamma                90
_cell_volume                     2199.7(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2558
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      28.9800
_cell_measurement_theta_min      3.0780
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72476
_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            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.14
_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  0.0157
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4318
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.987
_diffrn_reflns_theta_max         24.987
_diffrn_reflns_theta_min         2.197
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(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 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -14.00  24.00   1.00    4.00    --  -11.43 -99.00-150.00   38
  2  ω    -43.00  59.00   1.00    4.00    --  -11.43  77.00 -30.00  102
  3  ω     35.00  73.00   1.00    4.00    --   12.05 178.00 -30.00   38
;
_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      -0.0245365000
_diffrn_orient_matrix_UB_12      0.0102561000
_diffrn_orient_matrix_UB_13      0.0484175000
_diffrn_orient_matrix_UB_21      0.0586376000
_diffrn_orient_matrix_UB_22      0.0099592000
_diffrn_orient_matrix_UB_23      0.0331610000
_diffrn_orient_matrix_UB_31      -0.0084535000
_diffrn_orient_matrix_UB_32      0.0392281000
_diffrn_orient_matrix_UB_33      -0.0209665000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1700
_reflns_number_total             1938
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (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 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.0071(8)
_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   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         1938
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0379
_refine_ls_restrained_S_all      1.014
_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)+(0.0628P)²+0.9194P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1010
_refine_ls_wR_factor_ref         0.1052
_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:
 C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.60158(8) 0.47968(5) 0.38123(8) 0.0213(3) Uani 1 1 d . . . . .
O2 O 0.71871(11) 0.18588(6) 0.27813(10) 0.0419(3) Uani 1 1 d . . . . .
O3 O 0.83029(10) 0.31290(6) 0.20786(10) 0.0372(3) Uani 1 1 d . . . . .
C1 C 0.61074(11) 0.26349(8) 0.38732(11) 0.0209(3) Uani 1 1 d . . . . .
C2 C 0.56268(13) 0.19989(8) 0.43554(13) 0.0287(4) Uani 1 1 d . . . . .
H2 H 0.582270 0.148887 0.417698 0.034 Uiso 1 1 calc R U . . .
C3 C 0.48606(13) 0.21158(9) 0.50974(13) 0.0308(4) Uani 1 1 d . . . . .
H3 H 0.454023 0.168517 0.541104 0.037 Uiso 1 1 calc R U . . .
C4 C 0.45690(13) 0.28709(9) 0.53747(13) 0.0297(4) Uani 1 1 d . . . . .
H4 H 0.406254 0.294701 0.588382 0.036 Uiso 1 1 calc R U . . .
C5 C 0.50300(11) 0.35167(8) 0.48952(11) 0.0238(3) Uani 1 1 d . . . . .
H5 H 0.482688 0.402433 0.507722 0.029 Uiso 1 1 calc R U . . .
C6 C 0.57950(11) 0.34022(8) 0.41434(11) 0.0185(3) Uani 1 1 d . . . . .
C7 C 0.63321(11) 0.40511(7) 0.36280(10) 0.0172(3) Uani 1 1 d . . . . .
C8 C 0.71746(11) 0.39893(7) 0.29896(11) 0.0191(3) Uani 1 1 d . . . . .
C9 C 0.75583(12) 0.32352(8) 0.26619(12) 0.0237(3) Uani 1 1 d . . . . .
C10 C 0.69538(12) 0.25070(8) 0.30897(12) 0.0254(3) Uani 1 1 d . . . . .
C11 C 0.76080(11) 0.48021(8) 0.27471(11) 0.0207(3) Uani 1 1 d . . . . .
C12 C 0.66720(12) 0.53119(8) 0.31632(12) 0.0250(3) Uani 1 1 d . . . . .
H12A H 0.707310 0.573200 0.366843 0.030 Uiso 1 1 calc R U . . .
H12B H 0.611454 0.554569 0.249457 0.030 Uiso 1 1 calc R U . . .
C13 C 0.75750(14) 0.49392(8) 0.14534(12) 0.0304(4) Uani 1 1 d . . . . .
H13A H 0.814009 0.459281 0.121457 0.046 Uiso 1 1 calc R U . . .
H13B H 0.778820 0.547587 0.134058 0.046 Uiso 1 1 calc R U . . .
H13C H 0.677582 0.483520 0.099031 0.046 Uiso 1 1 calc R U . . .
C14 C 0.88818(12) 0.49446(8) 0.35050(13) 0.0292(4) Uani 1 1 d . . . . .
H14A H 0.887344 0.489260 0.431937 0.044 Uiso 1 1 calc R U . . .
H14B H 0.914234 0.546554 0.336185 0.044 Uiso 1 1 calc R U . . .
H14C H 0.942819 0.456486 0.330887 0.044 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.3473(15) . ?
O1 C12 1.4715(16) . ?
O2 C10 1.2071(16) . ?
O3 C9 1.2196(17) . ?
C1 C2 1.3887(19) . ?
C1 C6 1.4059(18) . ?
C1 C10 1.4931(18) . ?
C2 H2 0.9300 . ?
C2 C3 1.382(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.382(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.389(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.3888(18) . ?
C6 C7 1.4573(18) . ?
C7 C8 1.3506(18) . ?
C8 C9 1.4337(18) . ?
C8 C11 1.5145(17) . ?
C9 C10 1.5538(19) . ?
C11 C12 1.5375(19) . ?
C11 C13 1.5245(19) . ?
C11 C14 1.5316(19) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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 C12 106.79(9) . . ?
C2 C1 C6 119.00(12) . . ?
C2 C1 C10 120.58(12) . . ?
C6 C1 C10 120.42(12) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.69(13) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.17(13) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.20(13) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 120.1 . . ?
C6 C5 C4 119.84(13) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C7 117.05(12) . . ?
C5 C6 C1 120.08(12) . . ?
C5 C6 C7 122.85(12) . . ?
O1 C7 C6 119.37(11) . . ?
O1 C7 C8 114.36(11) . . ?
C8 C7 C6 126.23(11) . . ?
C7 C8 C9 121.17(12) . . ?
C7 C8 C11 109.72(11) . . ?
C9 C8 C11 129.09(12) . . ?
O3 C9 C8 125.23(13) . . ?
O3 C9 C10 118.74(12) . . ?
C8 C9 C10 116.03(11) . . ?
O2 C10 C1 122.34(13) . . ?
O2 C10 C9 118.96(13) . . ?
C1 C10 C9 118.70(11) . . ?
C8 C11 C12 99.99(10) . . ?
C8 C11 C13 113.08(11) . . ?
C8 C11 C14 109.92(11) . . ?
C13 C11 C12 111.78(11) . . ?
C13 C11 C14 110.61(11) . . ?
C14 C11 C12 111.06(11) . . ?
O1 C12 C11 107.57(10) . . ?
O1 C12 H12A 110.2 . . ?
O1 C12 H12B 110.2 . . ?
C11 C12 H12A 110.2 . . ?
C11 C12 H12B 110.2 . . ?
H12A C12 H12B 108.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

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 C7 C8 C9 -176.50(10) . . . . ?
O1 C7 C8 C11 4.89(15) . . . . ?
O3 C9 C10 O2 -4.0(2) . . . . ?
O3 C9 C10 C1 175.78(12) . . . . ?
C1 C2 C3 C4 -0.4(2) . . . . ?
C1 C6 C7 O1 176.74(10) . . . . ?
C1 C6 C7 C8 -5.55(19) . . . . ?
C2 C1 C6 C5 0.89(19) . . . . ?
C2 C1 C6 C7 179.31(11) . . . . ?
C2 C1 C10 O2 5.2(2) . . . . ?
C2 C1 C10 C9 -174.56(12) . . . . ?
C2 C3 C4 C5 1.0(2) . . . . ?
C3 C4 C5 C6 -0.6(2) . . . . ?
C4 C5 C6 C1 -0.35(19) . . . . ?
C4 C5 C6 C7 -178.67(12) . . . . ?
C5 C6 C7 O1 -4.88(18) . . . . ?
C5 C6 C7 C8 172.82(12) . . . . ?
C6 C1 C2 C3 -0.5(2) . . . . ?
C6 C1 C10 O2 -175.47(13) . . . . ?
C6 C1 C10 C9 4.78(19) . . . . ?
C6 C7 C8 C9 5.7(2) . . . . ?
C6 C7 C8 C11 -172.92(11) . . . . ?
C7 O1 C12 C11 -10.36(13) . . . . ?
C7 C8 C9 O3 179.23(13) . . . . ?
C7 C8 C9 C10 -0.31(19) . . . . ?
C7 C8 C11 C12 -10.45(13) . . . . ?
C7 C8 C11 C13 -129.44(12) . . . . ?
C7 C8 C11 C14 106.41(12) . . . . ?
C8 C9 C10 O2 175.60(13) . . . . ?
C8 C9 C10 C1 -4.65(18) . . . . ?
C8 C11 C12 O1 12.24(12) . . . . ?
C9 C8 C11 C12 171.09(13) . . . . ?
C9 C8 C11 C13 52.10(18) . . . . ?
C9 C8 C11 C14 -72.05(16) . . . . ?
C10 C1 C2 C3 178.83(13) . . . . ?
C10 C1 C6 C5 -178.46(11) . . . . ?
C10 C1 C6 C7 -0.04(18) . . . . ?
C11 C8 C9 O3 -2.5(2) . . . . ?
C11 C8 C9 C10 178.00(11) . . . . ?
C12 O1 C7 C6 -178.45(10) . . . . ?
C12 O1 C7 C8 3.58(14) . . . . ?
C13 C11 C12 O1 132.18(11) . . . . ?
C14 C11 C12 O1 -103.77(12) . . . . ?

_olex2_date_sample_data_collection 2021-03-29
_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 1.377
_oxdiff_exptl_absorpt_empirical_full_min 0.800
