# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_2l
_audit_block_doi                 10.5517/ccdc.csd.cc251kjb
_database_code_depnum_ccdc_archive 'CCDC 1997501'
loop_
_audit_author_name
_audit_author_address
'Ling Zhang'
;The Cambridge Crystallographic Data Centre
China
;
_audit_update_record             
;
2020-04-17 deposited with the CCDC.	2020-07-10 downloaded from the CCDC.
;
_audit_creation_date             2019-07-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H18 O3'
_chemical_formula_sum            'C20 H18 O3'
_chemical_formula_weight         306.34
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.3935(6)
_cell_length_b                   25.0493(16)
_cell_length_c                   8.8978(6)
_cell_angle_alpha                90
_cell_angle_beta                 111.188(8)
_cell_angle_gamma                90
_cell_volume                     1536.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2449
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      72.4760
_cell_measurement_theta_min      5.5940
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.709
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74325
_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    1.324
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0458
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5741
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.358
_diffrn_reflns_theta_min         3.529
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     25.00  71.00   1.00    1.00    --   40.98-125.00  60.00   46
  2  ω     35.00 113.00   1.00    1.00    --  106.95-125.00 -30.00   78
  3  ω     58.00  87.00   1.00    1.00    --   40.98-125.00-120.00   29
  4  ω     23.00  95.00   1.00    1.00    --   40.98-125.00-180.00   72
  5  ω     58.00 103.00   1.00    1.00    --  106.95 -95.00-180.00   45
  6  ω     60.00 157.00   1.00    1.00    --  106.95  15.00 120.00   97
  7  ω    104.00 156.00   1.00    1.00    --  106.95 125.00 150.00   52
  8  ω    105.00 158.00   1.00    1.00    --  106.95 125.00 -90.00   53
  9  ω     37.00 119.00   1.00    1.00    --  106.95-125.00 150.00   82
 10  ω   -116.00 -22.00   1.00    1.00    --  -40.98 -77.00 -30.00   94
;
_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      -0.1704711000
_diffrn_orient_matrix_UB_12      0.0359039000
_diffrn_orient_matrix_UB_13      -0.0032850000
_diffrn_orient_matrix_UB_21      0.1408590000
_diffrn_orient_matrix_UB_22      0.0357104000
_diffrn_orient_matrix_UB_23      0.1316737000
_diffrn_orient_matrix_UB_31      0.0312575000
_diffrn_orient_matrix_UB_32      0.0349249000
_diffrn_orient_matrix_UB_33      -0.1310381000
_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                2488
_reflns_number_total             2996
_reflns_odcompleteness_completeness 99.61
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2996
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0492
_refine_ls_restrained_S_all      1.090
_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)+(0.0519P)²+0.6125P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1220
_refine_ls_wR_factor_ref         0.1307
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C15(H15), C13(H13), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C18(H18), C2(H2), C19(H19), C3(H3), C6(H6), C5(H5), C4(H4)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
O3 O 0.53180(18) 0.80416(5) 0.43983(15) 0.0211(3) Uani 1 1 d . . . . .
O1 O 0.51632(18) 0.65810(5) 0.25351(15) 0.0205(3) Uani 1 1 d . . . . .
O2 O 0.1574(2) 0.71962(6) 0.20111(17) 0.0258(3) Uani 1 1 d . . . . .
C9 C 0.6780(3) 0.73483(7) 0.3443(2) 0.0194(4) Uani 1 1 d . . . . .
C8 C 0.8121(3) 0.69638(7) 0.3320(2) 0.0201(4) Uani 1 1 d . . . . .
H8 H 0.944458 0.701148 0.356870 0.024 Uiso 1 1 calc R . . . .
C10 C 0.5012(3) 0.71040(7) 0.2931(2) 0.0200(4) Uani 1 1 d . . . . .
C11 C 0.3215(3) 0.73851(8) 0.2613(2) 0.0203(4) Uani 1 1 d . . . . .
C7 C 0.7075(3) 0.65066(7) 0.2761(2) 0.0202(4) Uani 1 1 d . . . . .
C15 C 0.6904(3) 0.79276(7) 0.3874(2) 0.0197(4) Uani 1 1 d . . . . .
H15 H 0.815871 0.801830 0.470217 0.024 Uiso 1 1 calc R . . . .
C13 C 0.4215(3) 0.82237(7) 0.1573(2) 0.0199(4) Uani 1 1 d . . . . .
H13 H 0.394832 0.795048 0.073166 0.024 Uiso 1 1 calc R . . . .
C1 C 0.7624(3) 0.59826(8) 0.2358(2) 0.0221(4) Uani 1 1 d . . . . .
C16 C 0.7067(3) 0.88583(8) 0.2835(2) 0.0236(4) Uani 1 1 d . . . . .
H16A H 0.661607 0.896929 0.368395 0.028 Uiso 1 1 calc R . . . .
H16B H 0.847172 0.887952 0.325197 0.028 Uiso 1 1 calc R . . . .
C18 C 0.4098(3) 0.91678(8) 0.0642(2) 0.0273(4) Uani 1 1 d . . . . .
H18 H 0.336591 0.944884 0.004221 0.033 Uiso 1 1 calc R . . . .
C12 C 0.3597(3) 0.79867(8) 0.2964(2) 0.0201(4) Uani 1 1 d . . . . .
C2 C 0.9414(3) 0.59192(8) 0.2180(2) 0.0242(4) Uani 1 1 d . . . . .
H2 H 1.023046 0.621134 0.230071 0.029 Uiso 1 1 calc R . . . .
C14 C 0.6447(3) 0.82816(7) 0.2366(2) 0.0197(4) Uani 1 1 d . . . . .
H14 H 0.708024 0.814076 0.165299 0.024 Uiso 1 1 calc R . . . .
C19 C 0.3190(3) 0.87262(8) 0.0786(2) 0.0251(4) Uani 1 1 d . . . . .
H19 H 0.184053 0.872653 0.037644 0.030 Uiso 1 1 calc R . . . .
C3 C 0.9972(3) 0.54211(9) 0.1824(2) 0.0297(5) Uani 1 1 d . . . . .
H3 H 1.116720 0.537984 0.171134 0.036 Uiso 1 1 calc R . . . .
C6 C 0.6399(3) 0.55416(8) 0.2145(2) 0.0275(4) Uani 1 1 d . . . . .
H6 H 0.519831 0.558031 0.224878 0.033 Uiso 1 1 calc R . . . .
C5 C 0.6970(3) 0.50470(8) 0.1781(3) 0.0329(5) Uani 1 1 d . . . . .
H5 H 0.614577 0.475524 0.163405 0.040 Uiso 1 1 calc R . . . .
C20 C 0.1940(3) 0.82607(8) 0.3260(2) 0.0263(4) Uani 1 1 d . . . . .
H20A H 0.178092 0.810945 0.419542 0.039 Uiso 1 1 calc GR . . . .
H20B H 0.076872 0.821201 0.234036 0.039 Uiso 1 1 calc GR . . . .
H20C H 0.221496 0.863508 0.343056 0.039 Uiso 1 1 calc GR . . . .
C17 C 0.6253(3) 0.92353(8) 0.1404(2) 0.0284(5) Uani 1 1 d . . . . .
H17A H 0.655599 0.960131 0.176205 0.034 Uiso 1 1 calc R . . . .
H17B H 0.684734 0.915931 0.061722 0.034 Uiso 1 1 calc R . . . .
C4 C 0.8757(3) 0.49837(8) 0.1634(3) 0.0330(5) Uani 1 1 d . . . . .
H4 H 0.914294 0.464921 0.140963 0.040 Uiso 1 1 calc R . . . .


_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
O3 C15 1.439(2) . ?
O3 C12 1.446(2) . ?
O1 C10 1.372(2) . ?
O1 C7 1.366(2) . ?
O2 C11 1.230(2) . ?
C9 C8 1.414(3) . ?
C9 C10 1.364(3) . ?
C9 C15 1.495(3) . ?
C8 C7 1.371(3) . ?
C10 C11 1.439(3) . ?
C11 C12 1.544(3) . ?
C7 C1 1.457(3) . ?
C15 C14 1.541(3) . ?
C13 C12 1.582(2) . ?
C13 C14 1.549(3) . ?
C13 C19 1.505(3) . ?
C1 C2 1.397(3) . ?
C1 C6 1.397(3) . ?
C16 C14 1.527(2) . ?
C16 C17 1.524(3) . ?
C18 C19 1.324(3) . ?
C18 C17 1.499(3) . ?
C12 C20 1.508(3) . ?
C2 C3 1.387(3) . ?
C3 C4 1.388(3) . ?
C6 C5 1.385(3) . ?
C5 C4 1.383(3) . ?

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
C15 O3 C12 104.82(13) . . ?
C7 O1 C10 105.57(14) . . ?
C8 C9 C15 134.51(17) . . ?
C10 C9 C8 106.41(16) . . ?
C10 C9 C15 118.92(16) . . ?
C7 C8 C9 106.14(17) . . ?
O1 C10 C11 124.89(17) . . ?
C9 C10 O1 110.92(16) . . ?
C9 C10 C11 123.49(17) . . ?
O2 C11 C10 126.36(18) . . ?
O2 C11 C12 122.89(17) . . ?
C10 C11 C12 110.45(15) . . ?
O1 C7 C8 110.92(16) . . ?
O1 C7 C1 116.89(16) . . ?
C8 C7 C1 132.17(18) . . ?
O3 C15 C9 107.12(14) . . ?
O3 C15 C14 102.72(14) . . ?
C9 C15 C14 111.16(15) . . ?
C14 C13 C12 103.88(14) . . ?
C19 C13 C12 116.00(15) . . ?
C19 C13 C14 114.08(16) . . ?
C2 C1 C7 119.33(18) . . ?
C6 C1 C7 121.40(19) . . ?
C6 C1 C2 119.27(18) . . ?
C17 C16 C14 111.64(16) . . ?
C19 C18 C17 122.98(18) . . ?
O3 C12 C11 108.03(14) . . ?
O3 C12 C13 104.11(14) . . ?
O3 C12 C20 108.32(15) . . ?
C11 C12 C13 106.92(14) . . ?
C20 C12 C11 112.26(16) . . ?
C20 C12 C13 116.63(16) . . ?
C3 C2 C1 120.05(19) . . ?
C15 C14 C13 101.84(14) . . ?
C16 C14 C15 110.87(15) . . ?
C16 C14 C13 112.21(15) . . ?
C18 C19 C13 123.76(19) . . ?
C2 C3 C4 120.3(2) . . ?
C5 C6 C1 120.1(2) . . ?
C4 C5 C6 120.5(2) . . ?
C18 C17 C16 109.99(16) . . ?
C5 C4 C3 119.8(2) . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.309
_oxdiff_exptl_absorpt_empirical_full_min 0.682
####################################################################### 
# 
# 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_yinduo
_database_code_depnum_ccdc_archive 'CCDC 1984647'
loop_
_audit_author_name
_audit_author_address
'Ling Zhang'
;The Cambridge Crystallographic Data Centre
China
;
_audit_update_record             
;
2020-02-18 deposited with the CCDC.	2020-07-10 downloaded from the CCDC.
;
_audit_creation_date             2019-07-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H19 N O3'
_chemical_formula_sum            'C23 H19 N O3'
_chemical_formula_weight         357.39
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   4.9097(6)
_cell_length_b                   20.9012(19)
_cell_length_c                   16.8201(14)
_cell_angle_alpha                90
_cell_angle_beta                 96.123(9)
_cell_angle_gamma                90
_cell_volume                     1716.2(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2330
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      73.0920
_cell_measurement_theta_min      2.6060
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.738
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33640
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.12
_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  0.0440
_diffrn_reflns_av_unetI/netI     0.0590
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6214
_diffrn_reflns_point_group_measured_fraction_full 0.705
_diffrn_reflns_point_group_measured_fraction_max 0.671
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.741
_diffrn_reflns_theta_min         2.642
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -56.00  26.00   1.00    1.00    --  -40.73  38.00 -90.00   82
  2  ω      2.00  46.00   1.00    1.00    --   40.73 -99.00  90.00   44
  3  ω     34.00 135.00   1.00    1.00    --  106.95 -30.00  30.00  101
  4  ω     59.00  97.00   1.00    1.00    --   40.73-125.00-120.00   38
  5  ω     26.00 105.00   1.00    1.00    --  106.95 -95.00-150.00   79
  6  ω    110.00 137.00   1.00    1.00    --  106.95  45.00-180.00   27
  7  ω     95.00 122.00   1.00    1.00    --  106.95 125.00 -90.00   27
  8  ω     98.00 178.00   1.00    1.00    --  106.95 123.00  54.00   80
  9  ω     61.00 125.00   1.00    1.00    --  106.95 -45.00 150.00   64
 10  ω     41.00  97.00   1.00    1.00    --  106.95 -95.00  60.00   56
 11  ω   -111.00 -60.00   1.00    1.00    --  -40.73 -57.00 -60.00   51
;
_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      -0.0064178000
_diffrn_orient_matrix_UB_12      0.0710222000
_diffrn_orient_matrix_UB_13      0.0241484000
_diffrn_orient_matrix_UB_21      -0.0894730000
_diffrn_orient_matrix_UB_22      0.0185592000
_diffrn_orient_matrix_UB_23      -0.0875877000
_diffrn_orient_matrix_UB_31      -0.3026063000
_diffrn_orient_matrix_UB_32      -0.0069786000
_diffrn_orient_matrix_UB_33      0.0149212000
_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         0.373
_reflns_Friedel_fraction_full    0.401
_reflns_Friedel_fraction_max     0.375
_reflns_number_gt                4143
_reflns_number_total             4638
_reflns_odcompleteness_completeness 99.30
_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 (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         0.284
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details 
;
 Flack x determined using 947 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(3)
_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     491
_refine_ls_number_reflns         4638
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0576
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0795P)²+0.7782P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1515
_refine_ls_wR_factor_ref         0.1584
_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 Ternary CH refined with riding coordinates:
 C15B(H15B), C13(H13), C14(H14), C13B(H13B), C14B(H14B), C15(H15)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C8B(H8B), C2(H2), C21(H21), C21B(H21B), C4(H4), C6(H6), C3(H3),
 C18(H18), C6B(H6B), C2B(H2B), C4B(H4B), C19(H19), C20(H20), C20B(H20B),
 C18B(H18B), C3B(H3B), C5(H5), C19B(H19B), C5B(H5B)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C22(H22A,H22B,H22C), C23B(H23D,H23E,H23F), C22B(H22D,
 H22E,H22F)
;
_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 -0.5862(7) -0.35865(17) -0.57741(18) 0.0261(7) Uani 1 1 d . . . . .
O1B O -0.6493(7) -0.74291(17) -0.94394(19) 0.0265(7) Uani 1 1 d . . . . .
O2 O -0.7652(7) -0.37033(18) -0.74903(19) 0.0300(8) Uani 1 1 d . . . . .
O3 O -1.2542(6) -0.26827(17) -0.67700(18) 0.0234(7) Uani 1 1 d . . . . .
O3B O 0.0246(7) -0.65615(17) -0.84181(18) 0.0264(7) Uani 1 1 d . . . . .
O2B O -0.5285(7) -0.60843(19) -0.97775(19) 0.0326(8) Uani 1 1 d . . . . .
N1B N -0.1980(9) -0.5449(2) -0.7335(3) 0.0294(9) Uani 1 1 d . . . . .
N1 N -1.0389(9) -0.1706(2) -0.8034(2) 0.0279(9) Uani 1 1 d . . . . .
C8 C -0.7297(10) -0.2812(2) -0.4993(3) 0.0239(10) Uani 1 1 d . . . . .
H8 H -0.746163 -0.255175 -0.455258 0.029 Uiso 1 1 calc R . . . .
C7B C -0.6424(10) -0.7989(3) -0.9020(3) 0.0251(10) Uani 1 1 d . . . . .
C8B C -0.4439(10) -0.7975(3) -0.8382(3) 0.0259(10) Uani 1 1 d . . . . .
H8B H -0.402010 -0.829510 -0.800453 0.031 Uiso 1 1 calc R . . . .
C7 C -0.5549(10) -0.3316(2) -0.5035(3) 0.0243(10) Uani 1 1 d . . . . .
C10 C -0.7843(10) -0.3240(2) -0.6212(3) 0.0238(10) Uani 1 1 d . . . . .
C16 C -1.1700(10) -0.1279(2) -0.6890(3) 0.0259(10) Uani 1 1 d . . . . .
C9 C -0.8812(10) -0.2766(2) -0.5758(3) 0.0238(10) Uani 1 1 d . . . . .
C1 C -0.3509(10) -0.3609(3) -0.4448(3) 0.0258(10) Uani 1 1 d . . . . .
C2 C -0.1772(10) -0.4087(3) -0.4686(3) 0.0277(11) Uani 1 1 d . . . . .
H2 H -0.193304 -0.422245 -0.521556 0.033 Uiso 1 1 calc R . . . .
C9B C -0.3161(11) -0.7368(2) -0.8418(3) 0.0250(10) Uani 1 1 d . . . . .
C17 C -1.2047(10) -0.1257(2) -0.7729(3) 0.0259(10) Uani 1 1 d . . . . .
C21 C -1.3180(11) -0.0876(3) -0.6447(3) 0.0280(11) Uani 1 1 d . . . . .
H21 H -1.291562 -0.088421 -0.589169 0.034 Uiso 1 1 calc R . . . .
C10B C -0.4483(11) -0.7053(2) -0.9049(3) 0.0264(10) Uani 1 1 d . . . . .
C21B C 0.1915(11) -0.6603(3) -0.6131(3) 0.0285(11) Uani 1 1 d . . . . .
H21B H 0.191802 -0.704649 -0.607942 0.034 Uiso 1 1 calc R . . . .
C4 C 0.0424(10) -0.4165(3) -0.3341(3) 0.0306(11) Uani 1 1 d . . . . .
H4 H 0.172336 -0.435179 -0.296964 0.037 Uiso 1 1 calc R . . . .
C6 C -0.3254(10) -0.3411(3) -0.3655(3) 0.0286(11) Uani 1 1 d . . . . .
H6 H -0.439490 -0.309276 -0.349216 0.034 Uiso 1 1 calc R . . . .
C15B C -0.2103(10) -0.6586(3) -0.7288(3) 0.0251(10) Uani 1 1 d . . . . .
H15B H -0.357577 -0.679548 -0.703501 0.030 Uiso 1 1 calc R . . . .
C13 C -1.0963(10) -0.2328(2) -0.6156(3) 0.0242(10) Uani 1 1 d . . . . .
H13 H -1.212491 -0.215300 -0.576940 0.029 Uiso 1 1 calc R . . . .
C23 C -1.2324(10) -0.3005(3) -0.8132(3) 0.0261(10) Uani 1 1 d . . . . .
H23A H -1.343681 -0.336398 -0.801779 0.039 Uiso 1 1 calc GR . . . .
H23B H -1.111021 -0.312761 -0.851670 0.039 Uiso 1 1 calc GR . . . .
H23C H -1.347911 -0.266134 -0.834495 0.039 Uiso 1 1 calc GR . . . .
C17B C 0.0016(11) -0.5641(3) -0.6756(3) 0.0283(11) Uani 1 1 d . . . . .
C3 C 0.0197(11) -0.4360(3) -0.4131(3) 0.0311(11) Uani 1 1 d . . . . .
H3 H 0.136146 -0.467454 -0.429140 0.037 Uiso 1 1 calc R . . . .
C12 C -1.0665(10) -0.2787(2) -0.7372(3) 0.0238(10) Uani 1 1 d . . . . .
C18 C -1.3874(11) -0.0827(3) -0.8133(3) 0.0318(12) Uani 1 1 d . . . . .
H18 H -1.406524 -0.080002 -0.868784 0.038 Uiso 1 1 calc R . . . .
C6B C -0.8310(11) -0.9087(3) -0.8999(3) 0.0320(12) Uani 1 1 d . . . . .
H6B H -0.691249 -0.918916 -0.860185 0.038 Uiso 1 1 calc R . . . .
C11 C -0.8601(10) -0.3309(2) -0.7057(3) 0.0244(10) Uani 1 1 d . . . . .
C2B C -1.0527(10) -0.8329(3) -0.9919(3) 0.0275(11) Uani 1 1 d . . . . .
H2B H -1.065168 -0.791902 -1.013489 0.033 Uiso 1 1 calc R . . . .
C1B C -0.8452(10) -0.8474(2) -0.9320(3) 0.0246(10) Uani 1 1 d . . . . .
C16B C 0.0058(10) -0.6308(3) -0.6685(3) 0.0255(10) Uani 1 1 d . . . . .
C12B C -0.1886(11) -0.6095(3) -0.8610(3) 0.0273(10) Uani 1 1 d . . . . .
C4B C -1.2279(11) -0.9401(3) -0.9860(3) 0.0317(11) Uani 1 1 d . . . . .
H4B H -1.357331 -0.970807 -1.003632 0.038 Uiso 1 1 calc R . . . .
C19 C -1.5394(11) -0.0440(3) -0.7675(3) 0.0328(12) Uani 1 1 d . . . . .
H19 H -1.667042 -0.015981 -0.793241 0.039 Uiso 1 1 calc R . . . .
C20 C -1.5070(11) -0.0458(2) -0.6842(3) 0.0322(12) Uani 1 1 d . . . . .
H20 H -1.611321 -0.019189 -0.655095 0.039 Uiso 1 1 calc R . . . .
C22 C -0.9716(12) -0.1709(3) -0.8849(3) 0.0328(12) Uani 1 1 d . . . . .
H22A H -1.114364 -0.192064 -0.918495 0.049 Uiso 1 1 calc GR . . . .
H22B H -0.801677 -0.193088 -0.887562 0.049 Uiso 1 1 calc GR . . . .
H22C H -0.954114 -0.127627 -0.902914 0.049 Uiso 1 1 calc GR . . . .
C14 C -0.9680(10) -0.1795(2) -0.6616(3) 0.0238(10) Uani 1 1 d . . . . .
H14 H -0.800164 -0.162413 -0.632453 0.029 Uiso 1 1 calc R . . . .
C13B C -0.0917(10) -0.7020(2) -0.7909(3) 0.0249(10) Uani 1 1 d . . . . .
H13B H 0.046878 -0.731533 -0.765805 0.030 Uiso 1 1 calc R . . . .
C23B C -0.0602(12) -0.5508(3) -0.8948(3) 0.0330(12) Uani 1 1 d . . . . .
H23D H 0.071817 -0.532657 -0.854815 0.050 Uiso 1 1 calc GR . . . .
H23E H -0.200174 -0.519742 -0.910163 0.050 Uiso 1 1 calc GR . . . .
H23F H 0.028973 -0.562697 -0.940640 0.050 Uiso 1 1 calc GR . . . .
C20B C 0.3793(11) -0.6233(3) -0.5649(3) 0.0324(12) Uani 1 1 d . . . . .
H20B H 0.507691 -0.642793 -0.528031 0.039 Uiso 1 1 calc R . . . .
C11B C -0.4052(10) -0.6388(3) -0.9235(3) 0.0267(11) Uani 1 1 d . . . . .
C18B C 0.1844(11) -0.5260(3) -0.6266(3) 0.0318(12) Uani 1 1 d . . . . .
H18B H 0.179355 -0.481582 -0.630489 0.038 Uiso 1 1 calc R . . . .
C14B C -0.3131(11) -0.5989(2) -0.7791(3) 0.0261(10) Uani 1 1 d . . . . .
H14B H -0.513567 -0.596909 -0.786732 0.031 Uiso 1 1 calc R . . . .
C15 C -0.9143(10) -0.2128(2) -0.7417(3) 0.0238(10) Uani 1 1 d . . . . .
H15 H -0.718102 -0.218568 -0.745615 0.029 Uiso 1 1 calc R . . . .
C3B C -1.2414(11) -0.8791(3) -1.0197(3) 0.0325(12) Uani 1 1 d . . . . .
H3B H -1.377050 -0.869474 -1.060805 0.039 Uiso 1 1 calc R . . . .
C22B C -0.2901(12) -0.4796(3) -0.7458(3) 0.0351(12) Uani 1 1 d . . . . .
H22D H -0.308168 -0.460020 -0.694957 0.053 Uiso 1 1 calc GR . . . .
H22E H -0.464290 -0.479252 -0.777680 0.053 Uiso 1 1 calc GR . . . .
H22F H -0.159102 -0.456200 -0.772732 0.053 Uiso 1 1 calc GR . . . .
C5 C -0.1295(11) -0.3690(3) -0.3104(3) 0.0305(11) Uani 1 1 d . . . . .
H5 H -0.113329 -0.355678 -0.257354 0.037 Uiso 1 1 calc R . . . .
C19B C 0.3734(11) -0.5565(3) -0.5722(3) 0.0321(12) Uani 1 1 d . . . . .
H19B H 0.499129 -0.532149 -0.539923 0.039 Uiso 1 1 calc R . . . .
C5B C -1.0216(12) -0.9547(3) -0.9262(3) 0.0362(12) Uani 1 1 d . . . . .
H5B H -1.011212 -0.995462 -0.903761 0.043 Uiso 1 1 calc R . . . .


_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 1.360(6) . ?
O1 C10 1.364(6) . ?
O1B C7B 1.364(6) . ?
O1B C10B 1.373(6) . ?
O2 C11 1.225(6) . ?
O3 C13 1.430(6) . ?
O3 C12 1.456(5) . ?
O3B C12B 1.441(6) . ?
O3B C13B 1.443(6) . ?
O2B C11B 1.218(6) . ?
N1B C17B 1.366(7) . ?
N1B C14B 1.444(7) . ?
N1B C22B 1.446(7) . ?
N1 C17 1.378(7) . ?
N1 C22 1.445(6) . ?
N1 C15 1.446(6) . ?
C8 H8 0.9300 . ?
C8 C7 1.365(7) . ?
C8 C9 1.419(6) . ?
C7B C8B 1.372(7) . ?
C7B C1B 1.472(7) . ?
C8B H8B 0.9300 . ?
C8B C9B 1.420(7) . ?
C7 C1 1.464(7) . ?
C10 C9 1.367(7) . ?
C10 C11 1.438(7) . ?
C16 C17 1.403(7) . ?
C16 C21 1.381(7) . ?
C16 C14 1.505(7) . ?
C9 C13 1.500(7) . ?
C1 C2 1.399(7) . ?
C1 C6 1.390(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.393(7) . ?
C9B C10B 1.354(7) . ?
C9B C13B 1.508(7) . ?
C17 C18 1.394(7) . ?
C21 H21 0.9300 . ?
C21 C20 1.390(7) . ?
C10B C11B 1.446(7) . ?
C21B H21B 0.9300 . ?
C21B C16B 1.379(7) . ?
C21B C20B 1.396(7) . ?
C4 H4 0.9300 . ?
C4 C3 1.382(8) . ?
C4 C5 1.390(8) . ?
C6 H6 0.9300 . ?
C6 C5 1.389(7) . ?
C15B H15B 0.9800 . ?
C15B C16B 1.504(7) . ?
C15B C13B 1.543(7) . ?
C15B C14B 1.562(7) . ?
C13 H13 0.9800 . ?
C13 C14 1.530(6) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C23 C12 1.511(7) . ?
C17B C16B 1.399(7) . ?
C17B C18B 1.401(7) . ?
C3 H3 0.9300 . ?
C12 C11 1.544(7) . ?
C12 C15 1.572(7) . ?
C18 H18 0.9300 . ?
C18 C19 1.388(8) . ?
C6B H6B 0.9300 . ?
C6B C1B 1.389(7) . ?
C6B C5B 1.381(8) . ?
C2B H2B 0.9300 . ?
C2B C1B 1.388(7) . ?
C2B C3B 1.385(8) . ?
C12B C23B 1.518(7) . ?
C12B C11B 1.540(7) . ?
C12B C14B 1.582(7) . ?
C4B H4B 0.9300 . ?
C4B C3B 1.393(8) . ?
C4B C5B 1.384(8) . ?
C19 H19 0.9300 . ?
C19 C20 1.394(7) . ?
C20 H20 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C14 H14 0.9800 . ?
C14 C15 1.563(6) . ?
C13B H13B 0.9800 . ?
C23B H23D 0.9600 . ?
C23B H23E 0.9600 . ?
C23B H23F 0.9600 . ?
C20B H20B 0.9300 . ?
C20B C19B 1.400(8) . ?
C18B H18B 0.9300 . ?
C18B C19B 1.388(8) . ?
C14B H14B 0.9800 . ?
C15 H15 0.9800 . ?
C3B H3B 0.9300 . ?
C22B H22D 0.9600 . ?
C22B H22E 0.9600 . ?
C22B H22F 0.9600 . ?
C5 H5 0.9300 . ?
C19B H19B 0.9300 . ?
C5B H5B 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O1 C10 106.1(4) . . ?
C7B O1B C10B 105.5(4) . . ?
C13 O3 C12 104.2(3) . . ?
C12B O3B C13B 105.0(4) . . ?
C17B N1B C14B 111.1(4) . . ?
C17B N1B C22B 124.6(4) . . ?
C14B N1B C22B 124.3(4) . . ?
C17 N1 C22 124.1(4) . . ?
C17 N1 C15 111.7(4) . . ?
C22 N1 C15 123.9(4) . . ?
C7 C8 H8 126.9 . . ?
C7 C8 C9 106.1(4) . . ?
C9 C8 H8 126.9 . . ?
O1B C7B C8B 111.3(5) . . ?
O1B C7B C1B 115.8(4) . . ?
C8B C7B C1B 132.9(5) . . ?
C7B C8B H8B 127.3 . . ?
C7B C8B C9B 105.4(5) . . ?
C9B C8B H8B 127.3 . . ?
O1 C7 C8 111.0(4) . . ?
O1 C7 C1 116.4(4) . . ?
C8 C7 C1 132.6(5) . . ?
O1 C10 C9 110.7(4) . . ?
O1 C10 C11 125.1(4) . . ?
C9 C10 C11 123.8(4) . . ?
C17 C16 C14 109.7(4) . . ?
C21 C16 C17 120.5(5) . . ?
C21 C16 C14 129.7(4) . . ?
C8 C9 C13 136.2(5) . . ?
C10 C9 C8 106.1(4) . . ?
C10 C9 C13 117.6(4) . . ?
C2 C1 C7 120.0(4) . . ?
C6 C1 C7 120.5(5) . . ?
C6 C1 C2 119.5(5) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.1(5) . . ?
C3 C2 H2 120.0 . . ?
C8B C9B C13B 134.9(4) . . ?
C10B C9B C8B 106.9(5) . . ?
C10B C9B C13B 118.1(5) . . ?
N1 C17 C16 109.8(4) . . ?
N1 C17 C18 129.3(4) . . ?
C18 C17 C16 120.9(5) . . ?
C16 C21 H21 120.4 . . ?
C16 C21 C20 119.2(5) . . ?
C20 C21 H21 120.4 . . ?
O1B C10B C11B 124.1(4) . . ?
C9B C10B O1B 110.9(4) . . ?
C9B C10B C11B 124.7(5) . . ?
C16B C21B H21B 120.3 . . ?
C16B C21B C20B 119.5(5) . . ?
C20B C21B H21B 120.3 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.8(5) . . ?
C5 C4 H4 120.1 . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 120.0(5) . . ?
C5 C6 H6 120.0 . . ?
C16B C15B H15B 112.4 . . ?
C16B C15B C13B 113.2(4) . . ?
C16B C15B C14B 102.7(4) . . ?
C13B C15B H15B 112.4 . . ?
C13B C15B C14B 103.1(4) . . ?
C14B C15B H15B 112.4 . . ?
O3 C13 C9 107.9(4) . . ?
O3 C13 H13 111.3 . . ?
O3 C13 C14 103.5(4) . . ?
C9 C13 H13 111.3 . . ?
C9 C13 C14 111.2(4) . . ?
C14 C13 H13 111.3 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C12 C23 H23A 109.5 . . ?
C12 C23 H23B 109.5 . . ?
C12 C23 H23C 109.5 . . ?
N1B C17B C16B 110.8(5) . . ?
N1B C17B C18B 128.2(5) . . ?
C16B C17B C18B 121.0(5) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.2(5) . . ?
C4 C3 H3 119.9 . . ?
O3 C12 C23 108.0(4) . . ?
O3 C12 C11 107.9(4) . . ?
O3 C12 C15 104.0(4) . . ?
C23 C12 C11 110.6(4) . . ?
C23 C12 C15 116.1(4) . . ?
C11 C12 C15 109.7(4) . . ?
C17 C18 H18 121.3 . . ?
C19 C18 C17 117.5(5) . . ?
C19 C18 H18 121.3 . . ?
C1B C6B H6B 119.5 . . ?
C5B C6B H6B 119.5 . . ?
C5B C6B C1B 120.9(5) . . ?
O2 C11 C10 125.5(5) . . ?
O2 C11 C12 123.3(4) . . ?
C10 C11 C12 111.1(4) . . ?
C1B C2B H2B 119.8 . . ?
C3B C2B H2B 119.8 . . ?
C3B C2B C1B 120.3(5) . . ?
C6B C1B C7B 119.9(5) . . ?
C2B C1B C7B 121.0(5) . . ?
C2B C1B C6B 119.1(5) . . ?
C21B C16B C15B 130.6(5) . . ?
C21B C16B C17B 120.4(5) . . ?
C17B C16B C15B 109.0(5) . . ?
O3B C12B C23B 108.1(4) . . ?
O3B C12B C11B 108.5(4) . . ?
O3B C12B C14B 103.8(4) . . ?
C23B C12B C11B 110.5(4) . . ?
C23B C12B C14B 115.3(4) . . ?
C11B C12B C14B 110.4(4) . . ?
C3B C4B H4B 120.1 . . ?
C5B C4B H4B 120.1 . . ?
C5B C4B C3B 119.9(5) . . ?
C18 C19 H19 119.0 . . ?
C18 C19 C20 122.1(5) . . ?
C20 C19 H19 119.0 . . ?
C21 C20 C19 119.7(5) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
N1 C22 H22A 109.5 . . ?
N1 C22 H22B 109.5 . . ?
N1 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C16 C14 C13 112.6(4) . . ?
C16 C14 H14 112.5 . . ?
C16 C14 C15 102.7(4) . . ?
C13 C14 H14 112.5 . . ?
C13 C14 C15 103.2(4) . . ?
C15 C14 H14 112.5 . . ?
O3B C13B C9B 107.1(4) . . ?
O3B C13B C15B 102.3(4) . . ?
O3B C13B H13B 111.9 . . ?
C9B C13B C15B 111.2(4) . . ?
C9B C13B H13B 111.9 . . ?
C15B C13B H13B 111.9 . . ?
C12B C23B H23D 109.5 . . ?
C12B C23B H23E 109.5 . . ?
C12B C23B H23F 109.5 . . ?
H23D C23B H23E 109.5 . . ?
H23D C23B H23F 109.5 . . ?
H23E C23B H23F 109.5 . . ?
C21B C20B H20B 120.2 . . ?
C21B C20B C19B 119.7(5) . . ?
C19B C20B H20B 120.2 . . ?
O2B C11B C10B 126.2(5) . . ?
O2B C11B C12B 123.8(5) . . ?
C10B C11B C12B 109.9(4) . . ?
C17B C18B H18B 121.1 . . ?
C19B C18B C17B 117.8(5) . . ?
C19B C18B H18B 121.1 . . ?
N1B C14B C15B 104.6(4) . . ?
N1B C14B C12B 114.0(4) . . ?
N1B C14B H14B 111.5 . . ?
C15B C14B C12B 103.1(4) . . ?
C15B C14B H14B 111.5 . . ?
C12B C14B H14B 111.5 . . ?
N1 C15 C12 113.6(4) . . ?
N1 C15 C14 104.5(4) . . ?
N1 C15 H15 111.7 . . ?
C12 C15 H15 111.7 . . ?
C14 C15 C12 102.9(4) . . ?
C14 C15 H15 111.7 . . ?
C2B C3B C4B 120.0(5) . . ?
C2B C3B H3B 120.0 . . ?
C4B C3B H3B 120.0 . . ?
N1B C22B H22D 109.5 . . ?
N1B C22B H22E 109.5 . . ?
N1B C22B H22F 109.5 . . ?
H22D C22B H22E 109.5 . . ?
H22D C22B H22F 109.5 . . ?
H22E C22B H22F 109.5 . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.4(5) . . ?
C6 C5 H5 119.8 . . ?
C20B C19B H19B 119.2 . . ?
C18B C19B C20B 121.5(5) . . ?
C18B C19B H19B 119.2 . . ?
C6B C5B C4B 119.8(6) . . ?
C6B C5B H5B 120.1 . . ?
C4B C5B H5B 120.1 . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.406
_oxdiff_exptl_absorpt_empirical_full_min 0.560
####################################################################### 
# 
# 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_exp_1846
_database_code_depnum_ccdc_archive 'CCDC 1984385'
loop_
_audit_author_name
_audit_author_address
'Ling Zhang'
;The Cambridge Crystallographic Data Centre
China
;
_audit_update_record             
;
2020-02-17 deposited with the CCDC.	2020-07-10 downloaded from the CCDC.
;
_audit_creation_date             2019-06-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H20 O3'
_chemical_formula_sum            'C23 H20 O3'
_chemical_formula_weight         344.39
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   6.8575(3)
_cell_length_b                   17.6675(7)
_cell_length_c                   29.0079(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3514.4(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3921
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.4170
_cell_measurement_theta_min      5.8570
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.681
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92968
_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    1.302
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            8491
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.656
_diffrn_reflns_theta_min         3.047
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -79.00 -41.00   1.00    1.00    --  -41.48  19.00-150.00   38
  2  ω    -16.00  32.00   1.00    1.00    --  -41.48  19.00-150.00   48
  3  ω    -90.00  -6.00   1.00    1.00    --  -41.48 125.00-120.00   84
  4  ω    125.00 177.00   1.00    1.00    --  106.95 100.00 135.00   52
  5  ω     41.00 129.00   1.00    1.00    --  106.95 -54.00 123.00   88
  6  ω     34.00  92.00   1.00    1.00    --  106.95 -77.00  90.00   58
  7  ω     26.00 108.00   1.00    1.00    --  106.95 -95.00 -90.00   82
;
_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      0.1404212000
_diffrn_orient_matrix_UB_12      0.0098673000
_diffrn_orient_matrix_UB_13      -0.0410653000
_diffrn_orient_matrix_UB_21      0.0394116000
_diffrn_orient_matrix_UB_22      0.0823010000
_diffrn_orient_matrix_UB_23      0.0148752000
_diffrn_orient_matrix_UB_31      0.1709447000
_diffrn_orient_matrix_UB_32      -0.0270170000
_diffrn_orient_matrix_UB_33      0.0302080000
_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                2922
_reflns_number_total             3431
_reflns_odcompleteness_completeness 99.94
_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 (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         0.228
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3431
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0456
_refine_ls_restrained_S_all      1.084
_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)+(0.0475P)²+1.8585P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1110
_refine_ls_wR_factor_ref         0.1178
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C3(H3), C14(H14), C11(H11), C19(H19), C12(H12), C23(H23), C20(H20),
 C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C16(H16A,H16B,H16C)
;
_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 0.34252(16) 0.67506(6) 0.53626(4) 0.0207(3) Uani 1 1 d . . . . .
O3 O 0.19832(16) 0.84728(6) 0.61918(4) 0.0211(3) Uani 1 1 d . . . . .
O2 O 0.62209(16) 0.73887(7) 0.60199(4) 0.0256(3) Uani 1 1 d . . . . .
C10 C 0.3246(2) 0.67258(9) 0.68202(5) 0.0189(3) Uani 1 1 d . . . . .
C2 C 0.1100(2) 0.74259(9) 0.57255(6) 0.0188(3) Uani 1 1 d . . . . .
C1 C 0.3045(2) 0.72714(9) 0.56992(6) 0.0197(3) Uani 1 1 d . . . . .
C4 C 0.1643(2) 0.65709(10) 0.51741(6) 0.0207(4) Uani 1 1 d . . . . .
C7 C 0.0415(2) 0.79493(9) 0.61000(6) 0.0202(4) Uani 1 1 d . . . . .
H7 H -0.079371 0.821077 0.601574 0.024 Uiso 1 1 calc R . . . .
C18 C 0.1668(2) 0.59893(10) 0.48190(6) 0.0222(4) Uani 1 1 d . . . . .
C5 C 0.4482(2) 0.75403(9) 0.60227(6) 0.0200(3) Uani 1 1 d . . . . .
C15 C 0.2685(2) 0.60827(9) 0.65777(6) 0.0210(3) Uani 1 1 d . . . . .
H15 H 0.170011 0.611959 0.635844 0.025 Uiso 1 1 calc R . . . .
C3 C 0.0179(2) 0.69686(9) 0.53878(6) 0.0205(3) Uani 1 1 d . . . . .
H3 H -0.114871 0.694320 0.532395 0.025 Uiso 1 1 calc R . . . .
C14 C 0.3563(3) 0.53874(10) 0.66561(6) 0.0228(4) Uani 1 1 d . . . . .
H14 H 0.315326 0.496593 0.649037 0.027 Uiso 1 1 calc R . . . .
C13 C 0.5054(2) 0.53116(10) 0.69803(6) 0.0227(4) Uani 1 1 d . . . . .
C6 C 0.3496(2) 0.80213(9) 0.64014(6) 0.0201(4) Uani 1 1 d . . . . .
C8 C 0.2336(2) 0.74962(9) 0.67456(5) 0.0192(3) Uani 1 1 d . . . . .
H8 H 0.233046 0.775273 0.704512 0.023 Uiso 1 1 calc R . . . .
C11 C 0.4743(2) 0.66444(10) 0.71433(6) 0.0232(4) Uani 1 1 d . . . . .
H11 H 0.515151 0.706478 0.731031 0.028 Uiso 1 1 calc R . . . .
C19 C -0.0070(3) 0.57385(10) 0.46212(6) 0.0255(4) Uani 1 1 d . . . . .
H19 H -0.124315 0.596773 0.470119 0.031 Uiso 1 1 calc R . . . .
C9 C 0.0220(2) 0.75218(9) 0.65598(6) 0.0209(4) Uani 1 1 d . . . . .
H9A H -0.028719 0.701540 0.651164 0.025 Uiso 1 1 calc R . . . .
H9B H -0.063198 0.779032 0.677074 0.025 Uiso 1 1 calc R . . . .
C17 C 0.4946(3) 0.85332(10) 0.66365(6) 0.0254(4) Uani 1 1 d . . . . .
H17A H 0.560326 0.883546 0.640957 0.038 Uiso 1 1 calc GR . . . .
H17B H 0.588333 0.823221 0.680032 0.038 Uiso 1 1 calc GR . . . .
H17C H 0.427553 0.885785 0.684930 0.038 Uiso 1 1 calc GR . . . .
C12 C 0.5629(2) 0.59531(10) 0.72203(6) 0.0263(4) Uani 1 1 d . . . . .
H12 H 0.662704 0.591753 0.743638 0.032 Uiso 1 1 calc R . . . .
C23 C 0.3419(3) 0.56455(11) 0.46871(6) 0.0279(4) Uani 1 1 d . . . . .
H23 H 0.459051 0.581127 0.481335 0.033 Uiso 1 1 calc R . . . .
C20 C -0.0056(3) 0.51507(11) 0.43068(6) 0.0297(4) Uani 1 1 d . . . . .
H20 H -0.122303 0.498394 0.417899 0.036 Uiso 1 1 calc R . . . .
C21 C 0.1681(3) 0.48070(11) 0.41800(6) 0.0306(4) Uani 1 1 d . . . . .
H21 H 0.168055 0.441009 0.396940 0.037 Uiso 1 1 calc R . . . .
C22 C 0.3419(3) 0.50598(11) 0.43698(6) 0.0329(4) Uani 1 1 d . . . . .
H22 H 0.459037 0.483506 0.428361 0.040 Uiso 1 1 calc R . . . .
C16 C 0.5983(3) 0.45513(11) 0.70655(7) 0.0329(4) Uani 1 1 d . . . . .
H16A H 0.518005 0.426291 0.727209 0.049 Uiso 1 1 calc GR . . . .
H16B H 0.724862 0.462172 0.720015 0.049 Uiso 1 1 calc GR . . . .
H16C H 0.611082 0.428499 0.677866 0.049 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
O1 C1 1.3667(19) . ?
O1 C4 1.3761(19) . ?
O3 C7 1.4431(19) . ?
O3 C6 1.4430(19) . ?
O2 C5 1.222(2) . ?
C10 C15 1.390(2) . ?
C10 C8 1.513(2) . ?
C10 C11 1.398(2) . ?
C2 C1 1.364(2) . ?
C2 C7 1.502(2) . ?
C2 C3 1.418(2) . ?
C1 C5 1.441(2) . ?
C4 C18 1.455(2) . ?
C4 C3 1.373(2) . ?
C7 C9 1.538(2) . ?
C18 C19 1.395(2) . ?
C18 C23 1.399(2) . ?
C5 C6 1.545(2) . ?
C15 C14 1.387(2) . ?
C14 C13 1.395(2) . ?
C13 C12 1.387(2) . ?
C13 C16 1.507(2) . ?
C6 C8 1.578(2) . ?
C6 C17 1.507(2) . ?
C8 C9 1.549(2) . ?
C11 C12 1.383(2) . ?
C19 C20 1.382(3) . ?
C23 C22 1.385(3) . ?
C20 C21 1.387(3) . ?
C21 C22 1.387(3) . ?

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 O1 C4 105.66(13) . . ?
C7 O3 C6 105.01(11) . . ?
C15 C10 C8 123.29(14) . . ?
C15 C10 C11 117.28(15) . . ?
C11 C10 C8 119.42(15) . . ?
C1 C2 C7 118.00(15) . . ?
C1 C2 C3 106.44(15) . . ?
C3 C2 C7 135.33(15) . . ?
O1 C1 C5 123.83(15) . . ?
C2 C1 O1 111.18(14) . . ?
C2 C1 C5 124.49(15) . . ?
O1 C4 C18 115.72(14) . . ?
O1 C4 C3 110.60(14) . . ?
C3 C4 C18 133.59(16) . . ?
O3 C7 C2 107.16(13) . . ?
O3 C7 C9 102.68(12) . . ?
C2 C7 C9 110.61(13) . . ?
C19 C18 C4 120.36(16) . . ?
C19 C18 C23 118.88(16) . . ?
C23 C18 C4 120.68(16) . . ?
O2 C5 C1 126.19(16) . . ?
O2 C5 C6 123.52(15) . . ?
C1 C5 C6 110.20(13) . . ?
C14 C15 C10 121.38(15) . . ?
C4 C3 C2 106.12(14) . . ?
C15 C14 C13 120.92(16) . . ?
C14 C13 C16 120.38(16) . . ?
C12 C13 C14 117.90(15) . . ?
C12 C13 C16 121.72(16) . . ?
O3 C6 C5 108.60(13) . . ?
O3 C6 C8 103.26(12) . . ?
O3 C6 C17 109.47(13) . . ?
C5 C6 C8 110.31(13) . . ?
C17 C6 C5 111.29(14) . . ?
C17 C6 C8 113.52(14) . . ?
C10 C8 C6 114.32(13) . . ?
C10 C8 C9 117.53(14) . . ?
C9 C8 C6 103.58(12) . . ?
C12 C11 C10 121.49(16) . . ?
C20 C19 C18 120.27(17) . . ?
C7 C9 C8 103.56(13) . . ?
C11 C12 C13 121.04(16) . . ?
C22 C23 C18 120.41(17) . . ?
C19 C20 C21 120.67(17) . . ?
C20 C21 C22 119.47(17) . . ?
C23 C22 C21 120.29(18) . . ?


_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 1.182
_oxdiff_exptl_absorpt_empirical_full_min 0.793
