# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_slc-5-33-20210310
_audit_block_doi                 10.5517/ccdc.csd.cc27gs2l
_database_code_depnum_ccdc_archive 'CCDC 2069779'
loop_
_audit_author_name
_audit_author_address
slcs
;Henan Normal University
China
;
_audit_update_record             
;
2021-03-11 deposited with the CCDC.	2021-07-13 downloaded from the CCDC.
;
_audit_creation_date             2021-03-10
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H15 Br N2 O2'
_chemical_formula_sum            'C23 H15 Br N2 O2'
_chemical_formula_weight         431.28
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'N1 Br1 C1 H1 O1'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.46680(10)
_cell_length_b                   12.02910(10)
_cell_length_c                   18.2481(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1858.53(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    16164
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.3120
_cell_measurement_theta_min      4.3800
_shelx_estimated_absorpt_T_max   0.741
_shelx_estimated_absorpt_T_min   0.741
_exptl_absorpt_coefficient_mu    3.192
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78324
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            24553
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.427
_diffrn_reflns_theta_min         4.402
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_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    -57.00  31.00   1.00    1.00    --  -35.62  68.00 -47.00   88
  2  ω   -102.00 -14.00   1.00    1.00    --  -35.62 -68.00 179.00   88
  3  ω    -32.00  62.00   1.00    1.00    --   35.62 -76.00  59.00   94
  4  ω     40.00 133.00   1.00    1.24    --  107.12 -76.00  59.00   93
  5  ω     40.00 134.00   1.00    1.24    --  107.12 -77.00 -55.00   94
  6  ω     41.00 129.00   1.00    1.24    --  107.12 -68.00 179.00   88
  7  ω    -32.00  52.00   1.00    1.00    --   35.62 -57.00  90.00   84
  8  ω      1.00  75.00   1.00    1.00    --   35.62 -99.00 -60.00   74
  9  ω     55.00 108.00   1.00    1.00    --   35.62-178.00  90.00   53
 10  ω     39.00 125.00   1.00    1.24    --  107.12 -45.00  60.00   86
 11  ω     38.00 110.00   1.00    1.24    --  107.12 -95.00 -90.00   72
 12  ω     57.00 150.00   1.00    1.24    --  107.12 178.00 -30.00   93
 13  ω     86.00 177.00   1.00    1.24    --  107.12  30.00 -90.00   91
 14  ω     38.00 110.00   1.00    1.24    --  107.12 -95.00   0.00   72
 15  ω   -103.00 -19.00   1.00    1.00    --  -35.62 -57.00 -90.00   84
 16  ω   -103.00 -19.00   1.00    1.00    --  -35.62 -57.00  90.00   84
 17  ω   -103.00  -9.00   1.00    1.00    --  -35.62 -77.00  30.00   94
 18  ω     57.00 108.00   1.00    1.00    --   35.62 178.00 -60.00   51
 19  ω      6.00 107.00   1.00    1.00    --   35.62  19.00  60.00  101
 20  ω     69.00 178.00   1.00    1.24    --  107.12  15.00  60.00  109
 21  ω     80.00 175.00   1.00    1.24    --  107.12  77.00  60.00   95
 22  ω     69.00 178.00   1.00    1.24    --  107.12  15.00-180.00  109
 23  ω     80.00 175.00   1.00    1.24    --  107.12  77.00 150.00   95
 24  ω     89.00 174.00   1.00    1.24    --  107.12  61.00-150.00   85
 25  ω     80.00 175.00   1.00    1.24    --  107.12  77.00  90.00   95
 26  ω     80.00 175.00   1.00    1.24    --  107.12  77.00 -30.00   95
 27  ω     80.00 175.00   1.00    1.24    --  107.12  77.00-180.00   95
 28  ω     80.00 175.00   1.00    1.24    --  107.12  77.00 -90.00   95
 29  ω     86.00 177.00   1.00    1.24    --  107.12  30.00 -30.00   91
 30  ω    -32.00  52.00   1.00    1.00    --   35.62 -57.00-120.00   84
 31  ω      9.00  86.00   1.00    1.00    --   35.62  77.00 -30.00   77
 32  ω      9.00 103.00   1.00    1.00    --   35.62  77.00-120.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0580518000
_diffrn_orient_matrix_UB_12      -0.0579384000
_diffrn_orient_matrix_UB_13      0.0703373000
_diffrn_orient_matrix_UB_21      -0.1293956000
_diffrn_orient_matrix_UB_22      0.0890430000
_diffrn_orient_matrix_UB_23      0.0089376000
_diffrn_orient_matrix_UB_31      -0.1138594000
_diffrn_orient_matrix_UB_32      -0.0716425000
_diffrn_orient_matrix_UB_33      -0.0458194000
_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         0.736
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                3529
_reflns_number_total             3613
_reflns_odcompleteness_completeness 99.95
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 
;
 Flack x determined using 1470 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.026(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3613
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0271
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0410P)²+0.4514P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0731
_refine_ls_wR_factor_ref         0.0736
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C23(H23), C20(H20), C12(H12), C15(H15), C22(H22), C21(H21),
 C16(H16), C7(H7), C4(H4), C5(H5), C6(H6)
2.b Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C)
;
_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
Br17 Br 0.06213(5) 1.14287(3) 0.32947(2) 0.06207(14) Uani 1 1 d . . . . .
O28 O 0.2630(3) 0.62480(19) 0.29007(11) 0.0470(5) Uani 1 1 d . . . . .
N1 N 0.2056(3) 0.66233(18) 0.40858(12) 0.0333(5) Uani 1 1 d . . . . .
O27 O 0.1427(4) 0.6984(2) 0.52649(13) 0.0600(7) Uani 1 1 d . . . . .
N18 N 0.2759(3) 0.39840(18) 0.31538(12) 0.0330(5) Uani 1 1 d . . . . .
C10 C 0.2580(3) 0.5927(2) 0.35246(14) 0.0324(5) Uani 1 1 d . . . . .
C9 C 0.3189(3) 0.4776(2) 0.37425(14) 0.0313(5) Uani 1 1 d . . . . .
C19 C 0.4994(3) 0.4820(2) 0.37283(14) 0.0312(5) Uani 1 1 d . . . . .
C25 C 0.4036(3) 0.3619(2) 0.28612(13) 0.0320(5) Uani 1 1 d . . . . .
C24 C 0.5477(3) 0.4093(2) 0.31795(14) 0.0318(5) Uani 1 1 d . . . . .
C13 C 0.2407(4) 0.9691(3) 0.39134(17) 0.0421(7) Uani 1 1 d . . . . .
H13 H 0.310376 1.025854 0.403789 0.051 Uiso 1 1 calc R U . . .
C3 C 0.2026(3) 0.5114(3) 0.49931(15) 0.0354(6) Uani 1 1 d . . . . .
C23 C 0.7072(4) 0.3927(3) 0.30359(16) 0.0402(7) Uani 1 1 d . . . . .
H23 H 0.739804 0.342705 0.267761 0.048 Uiso 1 1 calc R U . . .
C8 C 0.2593(3) 0.4367(2) 0.44769(15) 0.0339(6) Uani 1 1 d . . . . .
C20 C 0.6064(4) 0.5413(3) 0.41399(17) 0.0406(7) Uani 1 1 d . . . . .
H20 H 0.573694 0.589738 0.450695 0.049 Uiso 1 1 calc R U . . .
C11 C 0.1695(3) 0.7768(2) 0.39042(15) 0.0332(5) Uani 1 1 d . . . . .
C26 C 0.4021(4) 0.2762(3) 0.22601(17) 0.0439(7) Uani 1 1 d . . . . .
H26A H 0.447240 0.208212 0.243830 0.066 Uiso 1 1 calc R U . . .
H26B H 0.462891 0.302817 0.185192 0.066 Uiso 1 1 calc R U . . .
H26C H 0.295296 0.263095 0.210645 0.066 Uiso 1 1 calc R U . . .
C2 C 0.1833(3) 0.6305(2) 0.48181(15) 0.0370(6) Uani 1 1 d . . . . .
C14 C 0.1030(4) 0.9926(2) 0.35564(16) 0.0387(6) Uani 1 1 d . . . . .
C12 C 0.2757(3) 0.8588(3) 0.40892(16) 0.0391(6) Uani 1 1 d . . . . .
H12 H 0.369401 0.840994 0.432786 0.047 Uiso 1 1 calc R U . . .
C15 C -0.0033(3) 0.9113(3) 0.33619(19) 0.0432(7) Uani 1 1 d . . . . .
H15 H -0.095885 0.929181 0.311399 0.052 Uiso 1 1 calc R U . . .
C22 C 0.8161(4) 0.4525(3) 0.34414(19) 0.0493(8) Uani 1 1 d . . . . .
H22 H 0.923443 0.443764 0.335021 0.059 Uiso 1 1 calc R U . . .
C21 C 0.7663(4) 0.5256(3) 0.39828(18) 0.0491(8) Uani 1 1 d . . . . .
H21 H 0.841398 0.565115 0.424816 0.059 Uiso 1 1 calc R U . . .
C16 C 0.0309(3) 0.8019(3) 0.35450(18) 0.0416(7) Uani 1 1 d . . . . .
H16 H -0.039714 0.745596 0.342496 0.050 Uiso 1 1 calc R U . . .
C7 C 0.2690(5) 0.3246(3) 0.46616(18) 0.0491(8) Uani 1 1 d . . . . .
H7 H 0.308474 0.273616 0.432473 0.059 Uiso 1 1 calc R U . . .
C4 C 0.1590(4) 0.4750(3) 0.56883(18) 0.0473(7) Uani 1 1 d . . . . .
H4 H 0.124453 0.526086 0.603584 0.057 Uiso 1 1 calc R U . . .
C5 C 0.1669(5) 0.3641(3) 0.58636(18) 0.0562(9) Uani 1 1 d . . . . .
H5 H 0.136641 0.339662 0.632637 0.067 Uiso 1 1 calc R U . . .
C6 C 0.2202(6) 0.2889(3) 0.5344(2) 0.0616(10) Uani 1 1 d . . . . .
H6 H 0.223128 0.213536 0.545709 0.074 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
Br17 C14 1.902(3) . ?
O28 C10 1.203(3) . ?
N1 C10 1.396(3) . ?
N1 C11 1.449(3) . ?
N1 C2 1.403(4) . ?
O27 C2 1.204(4) . ?
N18 C9 1.481(3) . ?
N18 C25 1.283(4) . ?
C10 C9 1.530(4) . ?
C9 C19 1.530(4) . ?
C9 C8 1.514(4) . ?
C19 C24 1.391(4) . ?
C19 C20 1.376(4) . ?
C25 C24 1.467(4) . ?
C25 C26 1.505(4) . ?
C24 C23 1.390(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.365(4) . ?
C13 C12 1.397(4) . ?
C3 C8 1.387(4) . ?
C3 C2 1.478(4) . ?
C3 C4 1.392(4) . ?
C23 H23 0.9300 . ?
C23 C22 1.384(5) . ?
C8 C7 1.393(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.396(5) . ?
C11 C12 1.377(4) . ?
C11 C16 1.377(4) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C14 C15 1.376(4) . ?
C12 H12 0.9300 . ?
C15 H15 0.9300 . ?
C15 C16 1.388(4) . ?
C22 H22 0.9300 . ?
C22 C21 1.388(5) . ?
C21 H21 0.9300 . ?
C16 H16 0.9300 . ?
C7 H7 0.9300 . ?
C7 C6 1.381(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.374(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.385(5) . ?
C6 H6 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
C10 N1 C11 118.0(2) . . ?
C10 N1 C2 125.3(2) . . ?
C2 N1 C11 116.7(2) . . ?
C25 N18 C9 108.3(2) . . ?
O28 C10 N1 120.8(2) . . ?
O28 C10 C9 121.6(2) . . ?
N1 C10 C9 117.4(2) . . ?
N18 C9 C10 108.1(2) . . ?
N18 C9 C19 104.8(2) . . ?
N18 C9 C8 110.6(2) . . ?
C19 C9 C10 107.5(2) . . ?
C8 C9 C10 114.3(2) . . ?
C8 C9 C19 111.1(2) . . ?
C24 C19 C9 106.5(2) . . ?
C20 C19 C9 131.8(3) . . ?
C20 C19 C24 121.7(3) . . ?
N18 C25 C24 113.8(2) . . ?
N18 C25 C26 122.1(3) . . ?
C24 C25 C26 124.2(2) . . ?
C19 C24 C25 106.6(2) . . ?
C23 C24 C19 120.8(3) . . ?
C23 C24 C25 132.6(3) . . ?
C14 C13 H13 120.4 . . ?
C14 C13 C12 119.1(3) . . ?
C12 C13 H13 120.4 . . ?
C8 C3 C2 121.3(2) . . ?
C8 C3 C4 120.5(3) . . ?
C4 C3 C2 118.2(3) . . ?
C24 C23 H23 120.9 . . ?
C22 C23 C24 118.1(3) . . ?
C22 C23 H23 120.9 . . ?
C3 C8 C9 120.4(3) . . ?
C3 C8 C7 118.9(3) . . ?
C7 C8 C9 120.6(3) . . ?
C19 C20 H20 121.4 . . ?
C19 C20 C21 117.1(3) . . ?
C21 C20 H20 121.4 . . ?
C12 C11 N1 119.1(3) . . ?
C12 C11 C16 121.0(3) . . ?
C16 C11 N1 119.8(3) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N1 C2 C3 117.1(2) . . ?
O27 C2 N1 119.9(3) . . ?
O27 C2 C3 122.9(3) . . ?
C13 C14 Br17 118.1(2) . . ?
C13 C14 C15 122.4(3) . . ?
C15 C14 Br17 119.5(2) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 C13 119.1(3) . . ?
C11 C12 H12 120.5 . . ?
C14 C15 H15 120.8 . . ?
C14 C15 C16 118.3(3) . . ?
C16 C15 H15 120.8 . . ?
C23 C22 H22 119.8 . . ?
C23 C22 C21 120.5(3) . . ?
C21 C22 H22 119.7 . . ?
C20 C21 H21 119.1 . . ?
C22 C21 C20 121.8(3) . . ?
C22 C21 H21 119.1 . . ?
C11 C16 C15 120.1(3) . . ?
C11 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C8 C7 H7 120.0 . . ?
C6 C7 C8 120.1(3) . . ?
C6 C7 H7 120.0 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.3(3) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 120.3 . . ?
C4 C5 C6 119.4(3) . . ?
C6 C5 H5 120.3 . . ?
C7 C6 C5 120.8(3) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br17 C14 C15 C16 178.6(2) . . . . ?
O28 C10 C9 N18 -38.4(4) . . . . ?
O28 C10 C9 C19 74.3(3) . . . . ?
O28 C10 C9 C8 -162.0(3) . . . . ?
N1 C10 C9 N18 145.7(2) . . . . ?
N1 C10 C9 C19 -101.6(3) . . . . ?
N1 C10 C9 C8 22.1(4) . . . . ?
N1 C11 C12 C13 180.0(3) . . . . ?
N1 C11 C16 C15 -179.2(3) . . . . ?
N18 C9 C19 C24 -0.8(3) . . . . ?
N18 C9 C19 C20 179.4(3) . . . . ?
N18 C9 C8 C3 -143.1(3) . . . . ?
N18 C9 C8 C7 40.7(4) . . . . ?
N18 C25 C24 C19 0.4(3) . . . . ?
N18 C25 C24 C23 179.3(3) . . . . ?
C10 N1 C11 C12 -103.0(3) . . . . ?
C10 N1 C11 C16 76.4(3) . . . . ?
C10 N1 C2 O27 177.4(3) . . . . ?
C10 N1 C2 C3 -6.0(4) . . . . ?
C10 C9 C19 C24 -115.6(2) . . . . ?
C10 C9 C19 C20 64.5(4) . . . . ?
C10 C9 C8 C3 -20.9(4) . . . . ?
C10 C9 C8 C7 162.9(3) . . . . ?
C9 N18 C25 C24 -0.9(3) . . . . ?
C9 N18 C25 C26 177.7(3) . . . . ?
C9 C19 C24 C25 0.3(3) . . . . ?
C9 C19 C24 C23 -178.8(3) . . . . ?
C9 C19 C20 C21 179.9(3) . . . . ?
C9 C8 C7 C6 177.4(3) . . . . ?
C19 C9 C8 C3 100.9(3) . . . . ?
C19 C9 C8 C7 -75.3(4) . . . . ?
C19 C24 C23 C22 -1.6(4) . . . . ?
C19 C20 C21 C22 -0.7(5) . . . . ?
C25 N18 C9 C10 115.5(2) . . . . ?
C25 N18 C9 C19 1.0(3) . . . . ?
C25 N18 C9 C8 -118.7(3) . . . . ?
C25 C24 C23 C22 179.6(3) . . . . ?
C24 C19 C20 C21 0.1(4) . . . . ?
C24 C23 C22 C21 1.0(5) . . . . ?
C13 C14 C15 C16 0.7(5) . . . . ?
C3 C8 C7 C6 1.1(5) . . . . ?
C3 C4 C5 C6 0.7(6) . . . . ?
C23 C22 C21 C20 0.1(5) . . . . ?
C8 C9 C19 C24 118.6(2) . . . . ?
C8 C9 C19 C20 -61.2(4) . . . . ?
C8 C3 C2 N1 7.8(4) . . . . ?
C8 C3 C2 O27 -175.8(3) . . . . ?
C8 C3 C4 C5 -2.1(5) . . . . ?
C8 C7 C6 C5 -2.5(6) . . . . ?
C20 C19 C24 C25 -179.9(3) . . . . ?
C20 C19 C24 C23 1.1(4) . . . . ?
C11 N1 C10 O28 -4.8(4) . . . . ?
C11 N1 C10 C9 171.1(2) . . . . ?
C11 N1 C2 O27 -3.1(4) . . . . ?
C11 N1 C2 C3 173.4(2) . . . . ?
C26 C25 C24 C19 -178.2(3) . . . . ?
C26 C25 C24 C23 0.7(5) . . . . ?
C2 N1 C10 O28 174.6(3) . . . . ?
C2 N1 C10 C9 -9.4(4) . . . . ?
C2 N1 C11 C12 77.5(3) . . . . ?
C2 N1 C11 C16 -103.1(3) . . . . ?
C2 C3 C8 C9 6.3(4) . . . . ?
C2 C3 C8 C7 -177.4(3) . . . . ?
C2 C3 C4 C5 176.5(3) . . . . ?
C14 C13 C12 C11 -0.7(5) . . . . ?
C14 C15 C16 C11 -0.8(5) . . . . ?
C12 C13 C14 Br17 -177.9(2) . . . . ?
C12 C13 C14 C15 0.0(5) . . . . ?
C12 C11 C16 C15 0.2(5) . . . . ?
C16 C11 C12 C13 0.6(4) . . . . ?
C4 C3 C8 C9 -175.1(3) . . . . ?
C4 C3 C8 C7 1.2(5) . . . . ?
C4 C3 C2 N1 -170.8(3) . . . . ?
C4 C3 C2 O27 5.6(5) . . . . ?
C4 C5 C6 C7 1.6(7) . . . . ?

_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 1.361
_oxdiff_exptl_absorpt_empirical_full_min 0.821
####################################################################### 
# 
# 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_slc-20210326
_audit_block_doi                 10.5517/ccdc.csd.cc27m1nl
_database_code_depnum_ccdc_archive 'CCDC 2073889'
loop_
_audit_author_name
_audit_author_address
asas
;Henan Normal University
China
;
_audit_update_record             
;
2021-03-29 deposited with the CCDC.	2021-07-13 downloaded from the CCDC.
;
_audit_creation_date             2021-03-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C23 H20 N2 O2'
_chemical_formula_sum            'C23 H20 N2 O2'
_chemical_formula_weight         356.41
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 N1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.5174(4)
_cell_length_b                   10.7513(5)
_cell_length_c                   10.7978(6)
_cell_angle_alpha                90.516(4)
_cell_angle_beta                 103.384(4)
_cell_angle_gamma                98.725(4)
_cell_volume                     949.80(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3357
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.1870
_cell_measurement_theta_min      5.7780
_shelx_estimated_absorpt_T_max   0.939
_shelx_estimated_absorpt_T_min   0.883
_exptl_absorpt_coefficient_mu    0.639
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93469
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0196
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6678
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.488
_diffrn_reflns_theta_min         4.165
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -103.00 -78.00   1.00    1.00    --  -35.62-150.00-134.00   25
  2  ω    -68.00 -43.00   1.00    1.00    --  -35.62 123.00 108.00   25
  3  ω    -83.00 -56.00   1.00    1.00    --  -35.62 150.00 -89.00   27
  4  ω     36.00  88.00   1.00    1.00    --   35.62-123.00  27.00   52
  5  ω     74.00 101.00   1.00    1.00    --   35.62-150.00-134.00   27
  6  ω    114.00 140.00   1.00    1.47    --  107.12 123.00 108.00   26
  7  ω    101.00 126.00   1.00    1.47    --  107.12 150.00 -89.00   25
  8  ω     78.00 135.00   1.00    1.47    --  107.12-150.00-134.00   57
  9  ω     56.00 113.00   1.00    1.47    --  107.12-123.00  27.00   57
 10  ω    -64.00  33.00   1.00    1.00    --  -35.62  19.00  60.00   97
 11  ω    -63.00 -36.00   1.00    1.00    --  -35.62-178.00   0.00   27
 12  ω    -99.00 -19.00   1.00    1.00    --  -35.62 -57.00-120.00   80
 13  ω    -34.00  -6.00   1.00    1.00    --   35.62 -38.00 120.00   28
 14  ω     -5.00  54.00   1.00    1.00    --   35.62 -38.00 120.00   59
 15  ω     77.00 108.00   1.00    1.00    --   35.62 178.00 -60.00   31
 16  ω     60.00 107.00   1.00    1.00    --   35.62 178.00-180.00   47
 17  ω     90.00 174.00   1.00    1.47    --  107.12  61.00 150.00   84
 18  ω     44.00 101.00   1.00    1.47    --  107.12-111.00 -90.00   57
 19  ω     99.00 124.00   1.00    1.47    --  107.12 -45.00   0.00   25
 20  ω     57.00  83.00   1.00    1.47    --  107.12 -95.00-180.00   26
 21  ω     73.00 109.00   1.00    1.47    --  107.12 -95.00  30.00   36
 22  ω     95.00 120.00   1.00    1.47    --  107.12  45.00 -90.00   25
 23  ω    151.00 176.00   1.00    1.47    --  107.12  45.00 -90.00   25
 24  ω    124.00 177.00   1.00    1.47    --  107.12 111.00  60.00   53
 25  ω     73.00 124.00   1.00    1.47    --  107.12 -30.00  90.00   51
 26  ω     88.00 118.00   1.00    1.47    --  107.12 -61.00   0.00   30
 27  ω     40.00  70.00   1.00    1.47    --  107.12 -61.00   0.00   30
 28  ω     64.00  90.00   1.00    1.47    --  107.12 -45.00-150.00   26
 29  ω     93.00 124.00   1.00    1.47    --  107.12 -45.00-150.00   31
 30  ω     94.00 175.00   1.00    1.47    --  107.12  45.00  90.00   81
 31  ω    101.00 170.00   1.00    1.47    --  107.12 111.00 -30.00   69
 32  ω     42.00  82.00   1.00    1.47    --  107.12 -45.00   0.00   40
 33  ω    103.00 142.00   1.00    1.47    --  107.12 111.00 -90.00   39
 34  ω     95.00 172.00   1.00    1.47    --  107.12  61.00  30.00   77
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0653914000
_diffrn_orient_matrix_UB_12      -0.0541582000
_diffrn_orient_matrix_UB_13      -0.1071825000
_diffrn_orient_matrix_UB_21      -0.0757688000
_diffrn_orient_matrix_UB_22      -0.1338735000
_diffrn_orient_matrix_UB_23      0.0256909000
_diffrn_orient_matrix_UB_31      -0.1594866000
_diffrn_orient_matrix_UB_32      0.0143130000
_diffrn_orient_matrix_UB_33      -0.0969815000
_diffrn_oxdiff_digest_frames     
;
01ce9bc04c9b19a2704d46364866ea1d8c000279978
;
_diffrn_oxdiff_digest_hkl        
;
01276f7eea2229018960702f9e1cd0dffbe6c8
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\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                3095
_reflns_number_total             3614
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.723
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3614
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0561
_refine_ls_restrained_S_all      1.042
_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)+(0.0783P)²+0.4151P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1589
_refine_ls_wR_factor_ref         0.1664
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 N10(H10), N19(H19), C16(H16), C15(H15), C7(H7), C13(H13), C14(H14), C4(H4),
 C6(H6), C23(H23), C5(H5), C27(H27), C26(H26), C24(H24), C25(H25)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O20 O 0.55178(17) 0.92105(13) 0.37089(12) 0.0462(4) Uani 1 1 d . . . . .
N10 N 0.5757(2) 0.85853(16) 0.57003(15) 0.0453(4) Uani 1 1 d . . . . .
H10 H 0.5396 0.9260 0.5858 0.054 Uiso 1 1 calc R . . . .
N19 N 0.5451(2) 0.79201(18) 0.13541(16) 0.0505(4) Uani 1 1 d . . . . .
H19 H 0.5556 0.8453 0.1978 0.061 Uiso 1 1 calc R . . . .
O18 O 0.6804(2) 0.6586(2) 0.05097(17) 0.0777(6) Uani 1 1 d . . . . .
C1 C 0.5922(2) 0.84374(16) 0.45305(17) 0.0352(4) Uani 1 1 d . . . . .
C2 C 0.6645(2) 0.73185(16) 0.41809(16) 0.0339(4) Uani 1 1 d . . . . .
H2 H 0.5846 0.6853 0.3462 0.041 Uiso 1 1 calc R . . . .
C11 C 0.8176(2) 0.78085(15) 0.37063(17) 0.0347(4) Uani 1 1 d . . . . .
C3 C 0.6988(2) 0.64058(16) 0.52331(18) 0.0379(4) Uani 1 1 d . . . . .
C8 C 0.6698(2) 0.66014(18) 0.64227(18) 0.0423(4) Uani 1 1 d . . . . .
C12 C 0.8218(2) 0.77589(18) 0.24236(18) 0.0416(4) Uani 1 1 d . . . . .
C16 C 0.9601(2) 0.82899(17) 0.4604(2) 0.0431(4) Uani 1 1 d . . . . .
H16 H 0.9585 0.8332 0.5462 0.052 Uiso 1 1 calc R . . . .
C17 C 0.6753(3) 0.7336(2) 0.13444(18) 0.0479(5) Uani 1 1 d . . . . .
C22 C 0.3935(3) 0.7741(2) 0.04398(19) 0.0523(5) Uani 1 1 d . . . . .
C15 C 1.1046(2) 0.87091(19) 0.4242(2) 0.0536(5) Uani 1 1 d . . . . .
H15 H 1.1978 0.9052 0.4852 0.064 Uiso 1 1 calc R . . . .
C7 C 0.7018(3) 0.5707(2) 0.7340(2) 0.0554(5) Uani 1 1 d . . . . .
H7 H 0.6816 0.5831 0.8139 0.067 Uiso 1 1 calc R . . . .
C13 C 0.9706(3) 0.8132(2) 0.2079(2) 0.0541(5) Uani 1 1 d . . . . .
H13 H 0.9752 0.8051 0.1230 0.065 Uiso 1 1 calc R . . . .
C14 C 1.1098(3) 0.8616(2) 0.2981(3) 0.0588(6) Uani 1 1 d . . . . .
H14 H 1.2071 0.8880 0.2739 0.071 Uiso 1 1 calc R . . . .
C9 C 0.6097(3) 0.7770(2) 0.67726(19) 0.0571(6) Uani 1 1 d . . . . .
H9 H 0.6987 0.8246 0.7424 0.069 Uiso 1 1 calc R . . . .
C4 C 0.7610(3) 0.5331(2) 0.4986(2) 0.0580(6) Uani 1 1 d . . . . .
H4 H 0.7814 0.5196 0.4190 0.070 Uiso 1 1 calc R . . . .
C6 C 0.7625(3) 0.4647(2) 0.7081(2) 0.0611(6) Uani 1 1 d . . . . .
H6 H 0.7829 0.4057 0.7699 0.073 Uiso 1 1 calc R . . . .
C23 C 0.3204(3) 0.6562(3) -0.0100(2) 0.0688(7) Uani 1 1 d . . . . .
H23 H 0.3710 0.5861 0.0121 0.083 Uiso 1 1 calc R . . . .
C5 C 0.7930(4) 0.4463(2) 0.5902(3) 0.0711(7) Uani 1 1 d . . . . .
H5 H 0.8352 0.3752 0.5724 0.085 Uiso 1 1 calc R . . . .
C27 C 0.3179(3) 0.8771(3) 0.0107(3) 0.0684(7) Uani 1 1 d . . . . .
H27 H 0.3665 0.9561 0.0479 0.082 Uiso 1 1 calc R . . . .
C26 C 0.1691(4) 0.8637(4) -0.0782(3) 0.0956(11) Uani 1 1 d . . . . .
H26 H 0.1179 0.9335 -0.1004 0.115 Uiso 1 1 calc R . . . .
C24 C 0.1714(4) 0.6438(4) -0.0972(3) 0.0967(11) Uani 1 1 d . . . . .
H24 H 0.1203 0.5644 -0.1320 0.116 Uiso 1 1 calc R . . . .
C25 C 0.0979(4) 0.7468(5) -0.1332(4) 0.1088(13) Uani 1 1 d . . . . .
H25 H 0.0000 0.7376 -0.1948 0.131 Uiso 1 1 calc R . . . .
C21 C 0.4670(6) 0.7546(4) 0.7321(4) 0.1239(17) Uani 1 1 d . . . . .
H21A H 0.4423 0.8338 0.7577 0.186 Uiso 1 1 calc GR . . . .
H21B H 0.4898 0.7040 0.8050 0.186 Uiso 1 1 calc GR . . . .
H21C H 0.3752 0.7114 0.6697 0.186 Uiso 1 1 calc GR . . . .


_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
O20 C1 1.247(2) . ?
N10 H10 0.8600 . ?
N10 C1 1.314(2) . ?
N10 C9 1.461(3) . ?
N19 H19 0.8600 . ?
N19 C17 1.356(3) . ?
N19 C22 1.418(3) . ?
O18 C17 1.216(2) . ?
C1 C2 1.514(2) . ?
C2 H2 0.9800 . ?
C2 C11 1.532(2) . ?
C2 C3 1.514(2) . ?
C11 C12 1.394(3) . ?
C11 C16 1.392(3) . ?
C3 C8 1.383(3) . ?
C3 C4 1.391(3) . ?
C8 C7 1.397(3) . ?
C8 C9 1.503(3) . ?
C12 C17 1.506(3) . ?
C12 C13 1.405(3) . ?
C16 H16 0.9300 . ?
C16 C15 1.388(3) . ?
C22 C23 1.383(4) . ?
C22 C27 1.374(4) . ?
C15 H15 0.9300 . ?
C15 C14 1.377(4) . ?
C7 H7 0.9300 . ?
C7 C6 1.373(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.376(3) . ?
C14 H14 0.9300 . ?
C9 H9 0.9800 . ?
C9 C21 1.460(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.375(3) . ?
C6 H6 0.9300 . ?
C6 C5 1.375(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.382(4) . ?
C5 H5 0.9300 . ?
C27 H27 0.9300 . ?
C27 C26 1.388(4) . ?
C26 H26 0.9300 . ?
C26 C25 1.375(6) . ?
C24 H24 0.9300 . ?
C24 C25 1.368(6) . ?
C25 H25 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
C1 N10 H10 115.3 . . ?
C1 N10 C9 129.39(16) . . ?
C9 N10 H10 115.3 . . ?
C17 N19 H19 116.7 . . ?
C17 N19 C22 126.57(18) . . ?
C22 N19 H19 116.7 . . ?
O20 C1 N10 121.28(16) . . ?
O20 C1 C2 119.42(15) . . ?
N10 C1 C2 119.28(15) . . ?
C1 C2 H2 107.2 . . ?
C1 C2 C11 108.47(14) . . ?
C11 C2 H2 107.2 . . ?
C3 C2 C1 114.46(14) . . ?
C3 C2 H2 107.2 . . ?
C3 C2 C11 111.90(14) . . ?
C12 C11 C2 123.02(16) . . ?
C16 C11 C2 118.24(16) . . ?
C16 C11 C12 118.71(17) . . ?
C8 C3 C2 122.39(16) . . ?
C8 C3 C4 119.10(18) . . ?
C4 C3 C2 118.51(17) . . ?
C3 C8 C7 119.21(18) . . ?
C3 C8 C9 121.88(17) . . ?
C7 C8 C9 118.89(18) . . ?
C11 C12 C17 124.51(17) . . ?
C11 C12 C13 119.40(19) . . ?
C13 C12 C17 116.09(18) . . ?
C11 C16 H16 119.4 . . ?
C15 C16 C11 121.18(19) . . ?
C15 C16 H16 119.4 . . ?
N19 C17 C12 114.24(17) . . ?
O18 C17 N19 124.3(2) . . ?
O18 C17 C12 121.3(2) . . ?
C23 C22 N19 121.6(2) . . ?
C27 C22 N19 118.4(2) . . ?
C27 C22 C23 120.0(2) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 C16 120.0(2) . . ?
C14 C15 H15 120.0 . . ?
C8 C7 H7 119.5 . . ?
C6 C7 C8 121.0(2) . . ?
C6 C7 H7 119.5 . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.8(2) . . ?
C14 C13 H13 119.6 . . ?
C15 C14 H14 120.1 . . ?
C13 C14 C15 119.8(2) . . ?
C13 C14 H14 120.1 . . ?
N10 C9 C8 112.34(16) . . ?
N10 C9 H9 106.8 . . ?
C8 C9 H9 106.8 . . ?
C21 C9 N10 108.8(2) . . ?
C21 C9 C8 115.0(2) . . ?
C21 C9 H9 106.8 . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 121.0(2) . . ?
C5 C4 H4 119.5 . . ?
C7 C6 H6 120.2 . . ?
C7 C6 C5 119.6(2) . . ?
C5 C6 H6 120.2 . . ?
C22 C23 H23 120.4 . . ?
C24 C23 C22 119.2(3) . . ?
C24 C23 H23 120.4 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 120.1(2) . . ?
C6 C5 H5 120.0 . . ?
C22 C27 H27 119.9 . . ?
C22 C27 C26 120.3(3) . . ?
C26 C27 H27 119.9 . . ?
C27 C26 H26 120.2 . . ?
C25 C26 C27 119.6(3) . . ?
C25 C26 H26 120.2 . . ?
C23 C24 H24 119.5 . . ?
C25 C24 C23 120.9(3) . . ?
C25 C24 H24 119.5 . . ?
C26 C25 H25 120.0 . . ?
C24 C25 C26 119.9(3) . . ?
C24 C25 H25 120.0 . . ?
C9 C21 H21A 109.5 . . ?
C9 C21 H21B 109.5 . . ?
C9 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
O20 C1 C2 C11 57.9(2) . . . . ?
O20 C1 C2 C3 -176.40(16) . . . . ?
N10 C1 C2 C11 -121.03(18) . . . . ?
N10 C1 C2 C3 4.7(2) . . . . ?
N19 C22 C23 C24 179.0(2) . . . . ?
N19 C22 C27 C26 -179.8(2) . . . . ?
C1 N10 C9 C8 -0.9(3) . . . . ?
C1 N10 C9 C21 -129.3(3) . . . . ?
C1 C2 C11 C12 -105.22(18) . . . . ?
C1 C2 C11 C16 76.75(19) . . . . ?
C1 C2 C3 C8 -1.5(2) . . . . ?
C1 C2 C3 C4 178.21(18) . . . . ?
C2 C11 C12 C17 5.8(3) . . . . ?
C2 C11 C12 C13 -174.75(16) . . . . ?
C2 C11 C16 C15 177.76(16) . . . . ?
C2 C3 C8 C7 178.89(18) . . . . ?
C2 C3 C8 C9 -3.1(3) . . . . ?
C2 C3 C4 C5 -179.3(2) . . . . ?
C11 C2 C3 C8 122.44(18) . . . . ?
C11 C2 C3 C4 -57.9(2) . . . . ?
C11 C12 C17 N19 51.4(3) . . . . ?
C11 C12 C17 O18 -132.7(2) . . . . ?
C11 C12 C13 C14 -4.0(3) . . . . ?
C11 C16 C15 C14 -2.0(3) . . . . ?
C3 C2 C11 C12 127.57(18) . . . . ?
C3 C2 C11 C16 -50.5(2) . . . . ?
C3 C8 C7 C6 0.5(3) . . . . ?
C3 C8 C9 N10 4.3(3) . . . . ?
C3 C8 C9 C21 129.4(3) . . . . ?
C3 C4 C5 C6 0.4(4) . . . . ?
C8 C3 C4 C5 0.4(4) . . . . ?
C8 C7 C6 C5 0.2(4) . . . . ?
C12 C11 C16 C15 -0.4(3) . . . . ?
C12 C13 C14 C15 1.6(3) . . . . ?
C16 C11 C12 C17 -176.18(17) . . . . ?
C16 C11 C12 C13 3.3(3) . . . . ?
C16 C15 C14 C13 1.4(3) . . . . ?
C17 N19 C22 C23 39.0(3) . . . . ?
C17 N19 C22 C27 -142.0(2) . . . . ?
C17 C12 C13 C14 175.55(19) . . . . ?
C22 N19 C17 O18 2.1(4) . . . . ?
C22 N19 C17 C12 177.89(19) . . . . ?
C22 C23 C24 C25 1.8(5) . . . . ?
C22 C27 C26 C25 -0.2(5) . . . . ?
C7 C8 C9 N10 -177.7(2) . . . . ?
C7 C8 C9 C21 -52.6(3) . . . . ?
C7 C6 C5 C4 -0.7(4) . . . . ?
C13 C12 C17 N19 -128.1(2) . . . . ?
C13 C12 C17 O18 47.9(3) . . . . ?
C9 N10 C1 O20 177.5(2) . . . . ?
C9 N10 C1 C2 -3.7(3) . . . . ?
C9 C8 C7 C6 -177.6(2) . . . . ?
C4 C3 C8 C7 -0.8(3) . . . . ?
C4 C3 C8 C9 177.2(2) . . . . ?
C23 C22 C27 C26 -0.8(4) . . . . ?
C23 C24 C25 C26 -2.8(6) . . . . ?
C27 C22 C23 C24 0.0(4) . . . . ?
C27 C26 C25 C24 2.0(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 1.245
_oxdiff_exptl_absorpt_empirical_full_min 0.679
####################################################################### 
# 
# 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_slc-20210329
_audit_block_doi                 10.5517/ccdc.csd.cc27m1qn
_database_code_depnum_ccdc_archive 'CCDC 2073891'
loop_
_audit_author_name
_audit_author_address
asasas
;Henan Normal University
China
;
_audit_update_record             
;
2021-03-29 deposited with the CCDC.	2021-07-13 downloaded from the CCDC.
;
_audit_creation_date             2021-03-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H16 N O3'
_chemical_formula_sum            'C18 H15 N O3'
_chemical_formula_weight         293.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 N1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.4610(5)
_cell_length_b                   10.2760(5)
_cell_length_c                   11.7263(8)
_cell_angle_alpha                70.212(5)
_cell_angle_beta                 73.352(6)
_cell_angle_gamma                70.063(5)
_cell_volume                     780.25(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3349
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.2940
_cell_measurement_theta_min      4.7600
_shelx_estimated_absorpt_T_max   0.934
_shelx_estimated_absorpt_T_min   0.873
_exptl_absorpt_coefficient_mu    0.695
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0179
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6371
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.588
_diffrn_reflns_theta_min         4.084
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -72.00  25.00   1.00    1.00    --  -35.62  95.00 115.00   97
  2  ω     -3.00  72.00   1.00    1.00    --   35.62 -95.00   5.00   75
  3  ω     38.00 110.00   1.00    1.41    --  107.12 -95.00   5.00   72
  4  ω    101.00 177.00   1.00    1.41    --  107.12  95.00 115.00   76
  5  ω   -108.00 -35.00   1.00    1.00    --  -35.62-178.00  90.00   73
  6  ω   -105.00 -17.00   1.00    1.00    --  -35.62 -38.00  30.00   88
  7  ω      9.00 103.00   1.00    1.00    --   35.62  77.00-120.00   94
  8  ω     57.00 108.00   1.00    1.00    --   35.62 178.00   0.00   51
  9  ω     19.00 103.00   1.00    1.00    --   35.62  57.00 -60.00   84
 10  ω     19.00 103.00   1.00    1.00    --   35.62  57.00   0.00   84
 11  ω     39.00 125.00   1.00    1.41    --  107.12 -45.00-150.00   86
 12  ω     38.00 110.00   1.00    1.41    --  107.12 -95.00 120.00   72
 13  ω     57.00 147.00   1.00    1.41    --  107.12 178.00  30.00   90
 14  ω     39.00 102.00   1.00    1.41    --  107.12 -95.00  30.00   63
 15  ω     95.00 157.00   1.00    1.41    --  107.12  61.00  60.00   62
 16  ω    100.00 173.00   1.00    1.41    --  107.12 111.00   0.00   73
 17  ω     65.00 144.00   1.00    1.41    --  107.12 178.00  90.00   79
 18  ω     62.00 107.00   1.00    1.41    --  107.12-111.00-150.00   45
 19  ω     45.00 124.00   1.00    1.41    --  107.12 -30.00   0.00   79
 20  ω     40.00  77.00   1.00    1.41    --  107.12 -45.00  30.00   37
 21  ω     92.00 122.00   1.00    1.41    --  107.12 -45.00  30.00   30
 22  ω     89.00 174.00   1.00    1.41    --  107.12  61.00-180.00   85
 23  ω    110.00 136.00   1.00    1.41    --  107.12  61.00-120.00   26
 24  ω     66.00 113.00   1.00    1.41    --  107.12-111.00  60.00   47
 25  ω     67.00 119.00   1.00    1.41    --  107.12 -45.00  90.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.2151479000
_diffrn_orient_matrix_UB_12      0.0350256000
_diffrn_orient_matrix_UB_13      0.0645360000
_diffrn_orient_matrix_UB_21      0.0601126000
_diffrn_orient_matrix_UB_22      -0.0019203000
_diffrn_orient_matrix_UB_23      0.1158891000
_diffrn_orient_matrix_UB_31      -0.0146968000
_diffrn_orient_matrix_UB_32      0.1617440000
_diffrn_orient_matrix_UB_33      -0.0515378000
_diffrn_oxdiff_digest_frames     
;
01ece809db329e927e2e50b502435495f7017926467
;
_diffrn_oxdiff_digest_hkl        
;
01046198a7d9660251e6c55377418e9f387ff9
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\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                2567
_reflns_number_total             2972
_reflns_odcompleteness_completeness 99.89
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2972
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0552
_refine_ls_restrained_S_all      1.045
_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)+(0.0858P)²+0.2088P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1509
_refine_ls_wR_factor_ref         0.1588
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C15(H15), C4(H4), C6(H6), C5(H5), C14(H14), C12(H12), C13(H13),
 C18(H18)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C19(H19A,H19B,H19C)
2.c Idealised tetrahedral OH refined as rotating group:
 O21(H21)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O21 O 0.4994(2) 1.04824(13) 0.14324(12) 0.0518(4) Uani 1 1 d . . . . .
H21 H 0.5199 1.0837 0.0683 0.078 Uiso 1 1 calc GR . . . .
N9 N 0.4168(2) 0.85847(14) 0.11645(12) 0.0391(3) Uani 1 1 d . . . . .
O17 O 0.0733(2) 0.6731(2) 0.24518(19) 0.0770(5) Uani 1 1 d . . . . .
C1 C 0.4098(2) 0.74122(16) 0.20085(14) 0.0342(3) Uani 1 1 d . . . . .
C2 C 0.3508(2) 0.76037(16) 0.32674(14) 0.0358(4) Uani 1 1 d . . . . .
C10 C 0.4811(2) 0.59925(16) 0.17299(14) 0.0376(4) Uani 1 1 d . . . . .
C3 C 0.3293(3) 0.66502(19) 0.44266(16) 0.0436(4) Uani 1 1 d . . . . .
H3 H 0.3475 0.5681 0.4519 0.052 Uiso 1 1 calc R . . . .
C8 C 0.3519(3) 0.97914(16) 0.17558(15) 0.0418(4) Uani 1 1 d . . . . .
C7 C 0.3208(2) 0.90576(17) 0.31228(15) 0.0402(4) Uani 1 1 d . . . . .
C11 C 0.3696(3) 0.50255(19) 0.20360(17) 0.0473(4) Uani 1 1 d . . . . .
C15 C 0.6750(3) 0.55871(19) 0.11738(17) 0.0475(4) Uani 1 1 d . . . . .
H15 H 0.7504 0.6223 0.0955 0.057 Uiso 1 1 calc R . . . .
C4 C 0.2798(3) 0.7185(2) 0.54470(17) 0.0544(5) Uani 1 1 d . . . . .
H4 H 0.2646 0.6568 0.6237 0.065 Uiso 1 1 calc R . . . .
C6 C 0.2720(3) 0.9587(2) 0.41375(18) 0.0549(5) Uani 1 1 d . . . . .
H6 H 0.2525 1.0557 0.4046 0.066 Uiso 1 1 calc R . . . .
C5 C 0.2528(3) 0.8629(2) 0.52997(18) 0.0605(5) Uani 1 1 d . . . . .
H5 H 0.2211 0.8964 0.5996 0.073 Uiso 1 1 calc R . . . .
C14 C 0.7585(3) 0.4254(2) 0.0938(2) 0.0595(5) Uani 1 1 d . . . . .
H14 H 0.8887 0.4006 0.0560 0.071 Uiso 1 1 calc R . . . .
C12 C 0.4584(4) 0.3683(2) 0.1793(2) 0.0618(6) Uani 1 1 d . . . . .
H12 H 0.3851 0.3035 0.2002 0.074 Uiso 1 1 calc R . . . .
C22 C 0.1646(3) 1.0808(2) 0.1349(2) 0.0646(6) Uani 1 1 d . . . . .
H22A H 0.1203 1.1591 0.1722 0.097 Uiso 1 1 calc GR . . . .
H22B H 0.0672 1.0299 0.1602 0.097 Uiso 1 1 calc GR . . . .
H22C H 0.1884 1.1177 0.0466 0.097 Uiso 1 1 calc GR . . . .
C13 C 0.6503(4) 0.3301(2) 0.1257(2) 0.0646(6) Uani 1 1 d . . . . .
H13 H 0.7068 0.2400 0.1110 0.078 Uiso 1 1 calc R . . . .
C16 C 0.1569(4) 0.5356(3) 0.2550(2) 0.0676(6) Uani 1 1 d . . . . .
O20 O 0.0687(4) 0.4488(3) 0.2984(4) 0.1616(14) Uani 1 1 d . . . . .
C18 C -0.1337(4) 0.7195(5) 0.2957(4) 0.1198(15) Uani 1 1 d . . . . .
H18 H -0.2300 0.7107 0.2653 0.144 Uiso 1 1 calc R . . . .
C19 C -0.1717(5) 0.7768(6) 0.3917(4) 0.145(2) Uani 1 1 d . . . . .
H19A H -0.1006 0.8468 0.3697 0.218 Uiso 1 1 calc GR . . . .
H19B H -0.1330 0.7020 0.4628 0.218 Uiso 1 1 calc GR . . . .
H19C H -0.3084 0.8220 0.4105 0.218 Uiso 1 1 calc GR . . . .


_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
O21 H21 0.8200 . ?
O21 C8 1.403(2) . ?
N9 C1 1.280(2) . ?
N9 C8 1.494(2) . ?
O17 C16 1.315(3) . ?
O17 C18 1.459(3) . ?
C1 C2 1.475(2) . ?
C1 C10 1.487(2) . ?
C2 C3 1.383(2) . ?
C2 C7 1.390(2) . ?
C10 C11 1.400(2) . ?
C10 C15 1.387(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.387(3) . ?
C8 C7 1.510(2) . ?
C8 C22 1.523(3) . ?
C7 C6 1.378(2) . ?
C11 C12 1.399(3) . ?
C11 C16 1.490(3) . ?
C15 H15 0.9300 . ?
C15 C14 1.385(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.383(3) . ?
C6 H6 0.9300 . ?
C6 C5 1.387(3) . ?
C5 H5 0.9300 . ?
C14 H14 0.9300 . ?
C14 C13 1.367(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.366(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C13 H13 0.9300 . ?
C16 O20 1.177(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.359(4) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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 O21 H21 109.5 . . ?
C1 N9 C8 108.93(13) . . ?
C16 O17 C18 119.1(2) . . ?
N9 C1 C2 113.10(14) . . ?
N9 C1 C10 122.18(14) . . ?
C2 C1 C10 124.20(13) . . ?
C3 C2 C1 132.63(15) . . ?
C3 C2 C7 121.35(16) . . ?
C7 C2 C1 105.99(13) . . ?
C11 C10 C1 124.81(16) . . ?
C15 C10 C1 116.76(15) . . ?
C15 C10 C11 118.38(16) . . ?
C2 C3 H3 121.1 . . ?
C2 C3 C4 117.89(16) . . ?
C4 C3 H3 121.1 . . ?
O21 C8 N9 109.85(14) . . ?
O21 C8 C7 110.03(14) . . ?
O21 C8 C22 112.20(15) . . ?
N9 C8 C7 103.91(12) . . ?
N9 C8 C22 108.21(16) . . ?
C7 C8 C22 112.29(15) . . ?
C2 C7 C8 107.88(14) . . ?
C6 C7 C2 120.67(16) . . ?
C6 C7 C8 131.45(16) . . ?
C10 C11 C16 124.23(17) . . ?
C12 C11 C10 118.93(19) . . ?
C12 C11 C16 116.75(18) . . ?
C10 C15 H15 119.3 . . ?
C14 C15 C10 121.33(18) . . ?
C14 C15 H15 119.3 . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.60(17) . . ?
C5 C4 H4 119.7 . . ?
C7 C6 H6 121.0 . . ?
C7 C6 C5 118.01(18) . . ?
C5 C6 H6 121.0 . . ?
C4 C5 C6 121.47(18) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C15 C14 H14 119.9 . . ?
C13 C14 C15 120.2(2) . . ?
C13 C14 H14 119.9 . . ?
C11 C12 H12 119.2 . . ?
C13 C12 C11 121.66(19) . . ?
C13 C12 H12 119.2 . . ?
C8 C22 H22A 109.5 . . ?
C8 C22 H22B 109.5 . . ?
C8 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C14 C13 H13 120.3 . . ?
C12 C13 C14 119.46(18) . . ?
C12 C13 H13 120.3 . . ?
O17 C16 C11 113.54(18) . . ?
O20 C16 O17 122.2(3) . . ?
O20 C16 C11 124.2(3) . . ?
O17 C18 H18 123.4 . . ?
C19 C18 O17 113.3(3) . . ?
C19 C18 H18 123.4 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

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
O21 C8 C7 C2 -121.75(15) . . . . ?
O21 C8 C7 C6 58.1(3) . . . . ?
N9 C1 C2 C3 -178.12(17) . . . . ?
N9 C1 C2 C7 -0.08(19) . . . . ?
N9 C1 C10 C11 -123.59(19) . . . . ?
N9 C1 C10 C15 59.3(2) . . . . ?
N9 C8 C7 C2 -4.20(18) . . . . ?
N9 C8 C7 C6 175.67(19) . . . . ?
C1 N9 C8 O21 121.87(15) . . . . ?
C1 N9 C8 C7 4.19(18) . . . . ?
C1 N9 C8 C22 -115.34(16) . . . . ?
C1 C2 C3 C4 176.75(17) . . . . ?
C1 C2 C7 C8 2.78(18) . . . . ?
C1 C2 C7 C6 -177.11(16) . . . . ?
C1 C10 C11 C12 -175.78(16) . . . . ?
C1 C10 C11 C16 7.7(3) . . . . ?
C1 C10 C15 C14 176.42(16) . . . . ?
C2 C1 C10 C11 65.3(2) . . . . ?
C2 C1 C10 C15 -111.84(18) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C2 C7 C6 C5 -0.4(3) . . . . ?
C10 C1 C2 C3 -6.2(3) . . . . ?
C10 C1 C2 C7 171.79(15) . . . . ?
C10 C11 C12 C13 -0.6(3) . . . . ?
C10 C11 C16 O17 13.7(3) . . . . ?
C10 C11 C16 O20 -167.7(3) . . . . ?
C10 C15 C14 C13 -0.3(3) . . . . ?
C3 C2 C7 C8 -178.91(15) . . . . ?
C3 C2 C7 C6 1.2(3) . . . . ?
C3 C4 C5 C6 0.7(3) . . . . ?
C8 N9 C1 C2 -2.70(19) . . . . ?
C8 N9 C1 C10 -174.76(14) . . . . ?
C8 C7 C6 C5 179.78(19) . . . . ?
C7 C2 C3 C4 -1.0(3) . . . . ?
C7 C6 C5 C4 -0.6(3) . . . . ?
C11 C10 C15 C14 -0.9(3) . . . . ?
C11 C12 C13 C14 -0.6(3) . . . . ?
C15 C10 C11 C12 1.3(3) . . . . ?
C15 C10 C11 C16 -175.29(19) . . . . ?
C15 C14 C13 C12 1.0(3) . . . . ?
C12 C11 C16 O17 -163.0(2) . . . . ?
C12 C11 C16 O20 15.7(4) . . . . ?
C22 C8 C7 C2 112.51(17) . . . . ?
C22 C8 C7 C6 -67.6(3) . . . . ?
C16 O17 C18 C19 114.7(4) . . . . ?
C16 C11 C12 C13 176.2(2) . . . . ?
C18 O17 C16 C11 -177.9(2) . . . . ?
C18 O17 C16 O20 3.4(5) . . . . ?

_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 1.615
_oxdiff_exptl_absorpt_empirical_full_min 0.831
