# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_mx10483
_database_code_depnum_ccdc_archive 'CCDC 2179302'
loop_
_audit_author_name
_audit_author_address
'Zi-Hao Fu'
;qust
China
;
_audit_update_record             
;
2022-06-15 deposited with the CCDC.	2024-04-17 downloaded from the CCDC.
;
_audit_creation_date             2022-06-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H16 O2'
_chemical_formula_sum            'C18 H16 O2'
_chemical_formula_weight         264.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNO
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   8.2970(3)
_cell_length_b                   11.4089(5)
_cell_length_c                   29.4395(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2786.73(19)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6964
_cell_measurement_temperature    170.01(10)
_cell_measurement_theta_max      30.9790
_cell_measurement_theta_min      2.7880
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49042
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.45i (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.871
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            16298
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.871
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.086
_diffrn_reflns_theta_min         2.768
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.871
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -101.00  77.00   0.50    8.00    --  -11.60  45.00  30.00  356
  2  ω    -25.00   8.00   0.50    8.00    --  -11.60  45.00   0.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC10 (RCD3): fixed-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0724614000
_diffrn_orient_matrix_UB_12      0.0189014000
_diffrn_orient_matrix_UB_13      0.0105389000
_diffrn_orient_matrix_UB_21      0.0261846000
_diffrn_orient_matrix_UB_22      -0.0242167000
_diffrn_orient_matrix_UB_23      0.0209162000
_diffrn_orient_matrix_UB_31      0.0368760000
_diffrn_orient_matrix_UB_32      0.0541246000
_diffrn_orient_matrix_UB_33      0.0056328000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3255
_reflns_number_total             3902
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3902
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0410
_refine_ls_restrained_S_all      1.056
_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)+(0.0565P)²+0.7767P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1103
_refine_ls_wR_factor_ref         0.1158
_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:
 C2(H2), C3(H3), C5(H5), C6(H6), C9(H9), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C11(H11A,H11B,H11C)
;
_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 0.54110(10) 0.16566(7) 0.58656(3) 0.0311(2) Uani 1 1 d . . . . .
O2 O 0.62534(10) 0.03337(7) 0.67728(3) 0.0332(2) Uani 1 1 d . . . . .
C1 C 0.65032(13) 0.33096(9) 0.54955(3) 0.0232(2) Uani 1 1 d . . . . .
C2 C 0.75812(14) 0.42458(10) 0.55071(4) 0.0272(2) Uani 1 1 d . . . . .
H2 H 0.810200 0.443601 0.577698 0.033 Uiso 1 1 calc R U . . .
C3 C 0.78797(15) 0.48929(10) 0.51191(4) 0.0302(2) Uani 1 1 d . . . . .
H3 H 0.860799 0.551182 0.513115 0.036 Uiso 1 1 calc R U . . .
C4 C 0.71139(14) 0.46368(10) 0.47123(4) 0.0290(2) Uani 1 1 d . . . . .
C5 C 0.60304(16) 0.37096(10) 0.47037(4) 0.0313(3) Uani 1 1 d . . . . .
H5 H 0.550141 0.352819 0.443420 0.038 Uiso 1 1 calc R U . . .
C6 C 0.57238(14) 0.30521(10) 0.50875(4) 0.0281(2) Uani 1 1 d . . . . .
H6 H 0.499418 0.243429 0.507415 0.034 Uiso 1 1 calc R U . . .
C7 C 0.74551(18) 0.53555(11) 0.42964(4) 0.0380(3) Uani 1 1 d . . . . .
H7A H 0.847517 0.512735 0.417043 0.057 Uiso 1 1 calc R U . . .
H7B H 0.748738 0.617063 0.437682 0.057 Uiso 1 1 calc R U . . .
H7C H 0.662097 0.522838 0.407582 0.057 Uiso 1 1 calc R U . . .
C8 C 0.61481(12) 0.25809(9) 0.58996(3) 0.0227(2) Uani 1 1 d . . . . .
C9 C 0.66535(13) 0.29982(9) 0.63535(3) 0.0229(2) Uani 1 1 d . . . . .
H9 H 0.721875 0.369925 0.637810 0.028 Uiso 1 1 calc R U . . .
C10 C 0.63151(12) 0.23899(9) 0.67277(3) 0.0206(2) Uani 1 1 d . . . . .
C11 C 0.67987(14) 0.27897(10) 0.71924(4) 0.0270(2) Uani 1 1 d . . . . .
H11A H 0.751452 0.222435 0.732518 0.041 Uiso 1 1 calc R U . . .
H11B H 0.585620 0.286803 0.737907 0.041 Uiso 1 1 calc R U . . .
H11C H 0.733546 0.353303 0.717089 0.041 Uiso 1 1 calc R U . . .
C12 C 0.54665(12) 0.12258(9) 0.67309(3) 0.0214(2) Uani 1 1 d . . . . .
C13 C 0.36723(12) 0.12075(9) 0.67552(3) 0.0202(2) Uani 1 1 d . . . . .
C14 C 0.27334(13) 0.21280(9) 0.65965(4) 0.0249(2) Uani 1 1 d . . . . .
H14 H 0.322082 0.279941 0.648152 0.030 Uiso 1 1 calc R U . . .
C15 C 0.10666(14) 0.20433(11) 0.66101(4) 0.0328(3) Uani 1 1 d . . . . .
H15 H 0.043490 0.265110 0.649769 0.039 Uiso 1 1 calc R U . . .
C16 C 0.03442(14) 0.10566(12) 0.67904(4) 0.0372(3) Uani 1 1 d . . . . .
H16 H -0.077351 0.099748 0.679653 0.045 Uiso 1 1 calc R U . . .
C17 C 0.12774(15) 0.01598(11) 0.69612(5) 0.0359(3) Uani 1 1 d . . . . .
H17 H 0.078668 -0.049238 0.709084 0.043 Uiso 1 1 calc R U . . .
C18 C 0.29372(14) 0.02251(10) 0.69408(4) 0.0273(2) Uani 1 1 d . . . . .
H18 H 0.356236 -0.038848 0.705129 0.033 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.2232(13) . ?
O2 C12 1.2155(13) . ?
C1 C2 1.3936(15) . ?
C1 C6 1.3956(15) . ?
C1 C8 1.4808(14) . ?
C2 H2 0.9300 . ?
C2 C3 1.3824(15) . ?
C3 H3 0.9300 . ?
C3 C4 1.3870(17) . ?
C4 C5 1.3885(18) . ?
C4 C7 1.5005(15) . ?
C5 H5 0.9300 . ?
C5 C6 1.3798(16) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.4793(14) . ?
C9 H9 0.9300 . ?
C9 C10 1.3319(14) . ?
C10 C11 1.4968(14) . ?
C10 C12 1.5032(14) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.4905(14) . ?
C13 C14 1.3885(14) . ?
C13 C18 1.3881(14) . ?
C14 H14 0.9300 . ?
C14 C15 1.3869(16) . ?
C15 H15 0.9300 . ?
C15 C16 1.3814(19) . ?
C16 H16 0.9300 . ?
C16 C17 1.378(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.3805(17) . ?
C18 H18 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
C2 C1 C6 118.67(10) . . ?
C2 C1 C8 122.57(9) . . ?
C6 C1 C8 118.76(10) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.27(10) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.26(11) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C5 118.22(10) . . ?
C3 C4 C7 120.20(11) . . ?
C5 C4 C7 121.58(11) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 C4 121.24(11) . . ?
C6 C5 H5 119.4 . . ?
C1 C6 H6 119.8 . . ?
C5 C6 C1 120.33(11) . . ?
C5 C6 H6 119.8 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O1 C8 C1 121.18(9) . . ?
O1 C8 C9 119.55(9) . . ?
C9 C8 C1 119.24(9) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 C8 121.31(9) . . ?
C10 C9 H9 119.3 . . ?
C9 C10 C11 122.72(9) . . ?
C9 C10 C12 124.36(9) . . ?
C11 C10 C12 112.89(9) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O2 C12 C10 119.27(9) . . ?
O2 C12 C13 121.32(9) . . ?
C13 C12 C10 118.72(8) . . ?
C14 C13 C12 122.25(9) . . ?
C18 C13 C12 117.97(9) . . ?
C18 C13 C14 119.78(10) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.81(11) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.03(11) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.10(11) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.29(11) . . ?
C18 C17 H17 119.9 . . ?
C13 C18 H18 120.0 . . ?
C17 C18 C13 119.94(11) . . ?
C17 C18 H18 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C8 C9 C10 -0.34(16) . . . . ?
O2 C12 C13 C14 -163.15(10) . . . . ?
O2 C12 C13 C18 16.37(15) . . . . ?
C1 C2 C3 C4 0.47(18) . . . . ?
C1 C8 C9 C10 177.86(10) . . . . ?
C2 C1 C6 C5 0.50(17) . . . . ?
C2 C1 C8 O1 -167.91(11) . . . . ?
C2 C1 C8 C9 13.92(16) . . . . ?
C2 C3 C4 C5 0.09(17) . . . . ?
C2 C3 C4 C7 179.79(11) . . . . ?
C3 C4 C5 C6 -0.35(17) . . . . ?
C4 C5 C6 C1 0.05(18) . . . . ?
C6 C1 C2 C3 -0.76(17) . . . . ?
C6 C1 C8 O1 12.33(16) . . . . ?
C6 C1 C8 C9 -165.84(10) . . . . ?
C7 C4 C5 C6 179.95(11) . . . . ?
C8 C1 C2 C3 179.48(10) . . . . ?
C8 C1 C6 C5 -179.73(10) . . . . ?
C8 C9 C10 C11 -179.61(10) . . . . ?
C8 C9 C10 C12 2.41(16) . . . . ?
C9 C10 C12 O2 100.49(13) . . . . ?
C9 C10 C12 C13 -88.92(13) . . . . ?
C10 C12 C13 C14 26.46(14) . . . . ?
C10 C12 C13 C18 -154.02(10) . . . . ?
C11 C10 C12 O2 -77.66(12) . . . . ?
C11 C10 C12 C13 92.93(11) . . . . ?
C12 C13 C14 C15 177.28(10) . . . . ?
C12 C13 C18 C17 -178.63(10) . . . . ?
C13 C14 C15 C16 1.46(17) . . . . ?
C14 C13 C18 C17 0.90(16) . . . . ?
C14 C15 C16 C17 0.64(18) . . . . ?
C15 C16 C17 C18 -1.98(19) . . . . ?
C16 C17 C18 C13 1.20(18) . . . . ?
C18 C13 C14 C15 -2.22(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.694
_oxdiff_exptl_absorpt_empirical_full_min 0.601
####################################################################### 
# 
# 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_mx13731
_database_code_depnum_ccdc_archive 'CCDC 2340616'
loop_
_audit_author_name
_audit_author_address
lihaoran
;Qingdao University of Science and Technology
China
;
_audit_update_record             
;
2024-03-15 deposited with the CCDC.	2024-04-17 downloaded from the CCDC.
;
_audit_creation_date             2024-03-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H20 O2'
_chemical_formula_sum            'C20 H20 O2'
_chemical_formula_weight         292.36
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHO
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.7659(4)
_cell_length_b                   14.5214(5)
_cell_length_c                   11.4358(5)
_cell_angle_alpha                90
_cell_angle_beta                 110.658(5)
_cell_angle_gamma                90
_cell_volume                     1672.87(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6604
_cell_measurement_temperature    297.27(10)
_cell_measurement_theta_max      29.0660
_cell_measurement_theta_min      2.0270
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90397
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.45i (Rigaku Oxford Diffraction, 2018)
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    1.161
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0143
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.824
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13131
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.824
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.210
_diffrn_reflns_theta_min         2.364
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297.27(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.824
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -28.00  12.00   0.50    3.00    --    5.00  45.00  60.00   80
  2  ω    -97.00   7.00   0.50    3.00    --   -8.90  45.00 120.00  208
  3  ω     13.00  39.00   0.50    3.00    --   -8.90  45.00 176.32   52
  4  ω    -98.00  12.00   0.50    3.00    --   -8.90  45.00 176.32  220
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC10 (RCD3): fixed-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0281172000
_diffrn_orient_matrix_UB_12      -0.0315759000
_diffrn_orient_matrix_UB_13      -0.0497953000
_diffrn_orient_matrix_UB_21      0.0193736000
_diffrn_orient_matrix_UB_22      0.0289968000
_diffrn_orient_matrix_UB_23      -0.0404433000
_diffrn_orient_matrix_UB_31      0.0615342000
_diffrn_orient_matrix_UB_32      -0.0234407000
_diffrn_orient_matrix_UB_33      0.0166159000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3284
_reflns_number_total             4101
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.035
_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     202
_refine_ls_number_reflns         4101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0537
_refine_ls_restrained_S_all      1.090
_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)+(0.0885P)²+0.2886P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1632
_refine_ls_wR_factor_ref         0.1706
_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:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_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 1.04899(11) 0.68881(8) 0.47863(10) 0.0648(3) Uani 1 1 d . . . . .
O2 O 0.76169(11) 0.62269(9) 0.43108(12) 0.0662(3) Uani 1 1 d . . . . .
C1 C 0.96048(13) 0.59589(9) 0.29897(12) 0.0431(3) Uani 1 1 d . . . . .
C2 C 1.03998(13) 0.52130(10) 0.35480(14) 0.0481(3) Uani 1 1 d . . . . .
H2 H 1.090676 0.523023 0.439568 0.058 Uiso 1 1 calc R U . . .
C3 C 1.04404(17) 0.44481(11) 0.28516(18) 0.0606(4) Uani 1 1 d . . . . .
H3 H 1.097324 0.394944 0.322881 0.073 Uiso 1 1 calc R U . . .
C4 C 0.96895(19) 0.44216(12) 0.15923(19) 0.0680(5) Uani 1 1 d . . . . .
H4 H 0.972676 0.390640 0.112277 0.082 Uiso 1 1 calc R U . . .
C5 C 0.88887(19) 0.51493(13) 0.10281(16) 0.0674(5) Uani 1 1 d . . . . .
H5 H 0.838273 0.512579 0.018046 0.081 Uiso 1 1 calc R U . . .
C6 C 0.88365(16) 0.59186(11) 0.17247(14) 0.0553(4) Uani 1 1 d . . . . .
H6 H 0.828667 0.640938 0.134620 0.066 Uiso 1 1 calc R U . . .
C7 C 0.96553(13) 0.67986(10) 0.37534(12) 0.0449(3) Uani 1 1 d . . . . .
C8 C 0.87195(13) 0.75825(9) 0.31664(12) 0.0438(3) Uani 1 1 d . . . . .
C9 C 0.74435(13) 0.75211(9) 0.30281(14) 0.0476(3) Uani 1 1 d . . . . .
H9 H 0.687194 0.798933 0.260502 0.057 Uiso 1 1 calc R U . . .
C10 C 0.68957(14) 0.67405(9) 0.35183(13) 0.0466(3) Uani 1 1 d . . . . .
C11 C 0.54300(13) 0.65974(9) 0.30553(13) 0.0434(3) Uani 1 1 d . . . . .
C12 C 0.46061(15) 0.69108(10) 0.19010(14) 0.0531(4) Uani 1 1 d . . . . .
H12 H 0.495493 0.725670 0.140533 0.064 Uiso 1 1 calc R U . . .
C13 C 0.32672(16) 0.67114(13) 0.14826(17) 0.0656(4) Uani 1 1 d . . . . .
H13 H 0.271993 0.691811 0.070076 0.079 Uiso 1 1 calc R U . . .
C14 C 0.27366(17) 0.62109(13) 0.22101(18) 0.0646(4) Uani 1 1 d . . . . .
H14 H 0.183301 0.607982 0.192237 0.078 Uiso 1 1 calc R U . . .
C15 C 0.35443(17) 0.59034(14) 0.33662(18) 0.0671(5) Uani 1 1 d . . . . .
H15 H 0.318551 0.556844 0.386401 0.081 Uiso 1 1 calc R U . . .
C16 C 0.48851(16) 0.60915(12) 0.37871(15) 0.0577(4) Uani 1 1 d . . . . .
H16 H 0.542898 0.587831 0.456655 0.069 Uiso 1 1 calc R U . . .
C17 C 0.93371(14) 0.84262(10) 0.27839(15) 0.0522(4) Uani 1 1 d . . . . .
C18 C 1.0364(3) 0.81539(19) 0.2210(3) 0.1130(10) Uani 1 1 d . . . . .
H18A H 1.104993 0.779421 0.279955 0.170 Uiso 1 1 calc R U . . .
H18B H 1.074561 0.869867 0.199969 0.170 Uiso 1 1 calc R U . . .
H18C H 0.994397 0.779732 0.146782 0.170 Uiso 1 1 calc R U . . .
C19 C 1.0020(3) 0.90063(19) 0.3936(2) 0.1109(10) Uani 1 1 d . . . . .
H19A H 0.937302 0.922796 0.426913 0.166 Uiso 1 1 calc R U . . .
H19B H 1.045372 0.951970 0.371387 0.166 Uiso 1 1 calc R U . . .
H19C H 1.066624 0.863839 0.455373 0.166 Uiso 1 1 calc R U . . .
C20 C 0.8299(2) 0.90204(16) 0.1844(3) 0.1041(9) Uani 1 1 d . . . . .
H20A H 0.780175 0.865241 0.113604 0.156 Uiso 1 1 calc R U . . .
H20B H 0.872945 0.951308 0.157448 0.156 Uiso 1 1 calc R U . . .
H20C H 0.771034 0.927171 0.222564 0.156 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.2127(16) . ?
O2 C10 1.2181(17) . ?
C1 C2 1.3885(19) . ?
C1 C6 1.3915(19) . ?
C1 C7 1.4896(19) . ?
C2 H2 0.9300 . ?
C2 C3 1.376(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.381(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.372(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.385(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.5113(18) . ?
C8 C9 1.3292(19) . ?
C8 C17 1.530(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.477(2) . ?
C10 C11 1.4913(19) . ?
C11 C12 1.382(2) . ?
C11 C16 1.389(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.380(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.372(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.376(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.378(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.524(3) . ?
C17 C19 1.517(3) . ?
C17 C20 1.517(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
C2 C1 C6 119.28(13) . . ?
C2 C1 C7 118.68(12) . . ?
C6 C1 C7 121.96(12) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.25(14) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 119.96(15) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.55(15) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.80(16) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 H6 119.9 . . ?
C5 C6 C1 120.15(15) . . ?
C5 C6 H6 119.9 . . ?
O1 C7 C1 121.33(12) . . ?
O1 C7 C8 120.04(13) . . ?
C1 C7 C8 118.39(11) . . ?
C7 C8 C17 116.19(12) . . ?
C9 C8 C7 120.09(12) . . ?
C9 C8 C17 123.71(13) . . ?
C8 C9 H9 118.6 . . ?
C8 C9 C10 122.73(13) . . ?
C10 C9 H9 118.6 . . ?
O2 C10 C9 121.15(13) . . ?
O2 C10 C11 119.72(13) . . ?
C9 C10 C11 119.11(12) . . ?
C12 C11 C10 122.36(13) . . ?
C12 C11 C16 118.97(13) . . ?
C16 C11 C10 118.59(13) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.14(14) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.56(16) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.84(15) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 120.0 . . ?
C14 C15 C16 120.02(15) . . ?
C16 C15 H15 120.0 . . ?
C11 C16 H16 119.8 . . ?
C15 C16 C11 120.47(15) . . ?
C15 C16 H16 119.8 . . ?
C18 C17 C8 111.72(15) . . ?
C19 C17 C8 108.83(14) . . ?
C19 C17 C18 108.4(2) . . ?
C20 C17 C8 111.87(13) . . ?
C20 C17 C18 107.9(2) . . ?
C20 C17 C19 108.0(2) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C7 C8 C9 -109.63(17) . . . . ?
O1 C7 C8 C17 69.22(18) . . . . ?
O2 C10 C11 C12 -156.48(15) . . . . ?
O2 C10 C11 C16 20.3(2) . . . . ?
C1 C2 C3 C4 0.1(2) . . . . ?
C1 C7 C8 C9 75.90(18) . . . . ?
C1 C7 C8 C17 -105.26(14) . . . . ?
C2 C1 C6 C5 -1.3(2) . . . . ?
C2 C1 C7 O1 9.7(2) . . . . ?
C2 C1 C7 C8 -175.86(12) . . . . ?
C2 C3 C4 C5 -0.7(3) . . . . ?
C3 C4 C5 C6 0.3(3) . . . . ?
C4 C5 C6 C1 0.7(3) . . . . ?
C6 C1 C2 C3 0.9(2) . . . . ?
C6 C1 C7 O1 -167.09(14) . . . . ?
C6 C1 C7 C8 7.3(2) . . . . ?
C7 C1 C2 C3 -175.98(13) . . . . ?
C7 C1 C6 C5 175.46(15) . . . . ?
C7 C8 C9 C10 5.1(2) . . . . ?
C7 C8 C17 C18 40.0(2) . . . . ?
C7 C8 C17 C19 -79.6(2) . . . . ?
C7 C8 C17 C20 161.06(18) . . . . ?
C8 C9 C10 O2 17.1(2) . . . . ?
C8 C9 C10 C11 -164.50(13) . . . . ?
C9 C8 C17 C18 -141.2(2) . . . . ?
C9 C8 C17 C19 99.2(2) . . . . ?
C9 C8 C17 C20 -20.1(2) . . . . ?
C9 C10 C11 C12 25.1(2) . . . . ?
C9 C10 C11 C16 -158.10(14) . . . . ?
C10 C11 C12 C13 175.97(15) . . . . ?
C10 C11 C16 C15 -176.71(15) . . . . ?
C11 C12 C13 C14 0.8(3) . . . . ?
C12 C11 C16 C15 0.2(2) . . . . ?
C12 C13 C14 C15 -0.1(3) . . . . ?
C13 C14 C15 C16 -0.5(3) . . . . ?
C14 C15 C16 C11 0.5(3) . . . . ?
C16 C11 C12 C13 -0.8(2) . . . . ?
C17 C8 C9 C10 -173.69(13) . . . . ?

_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 1.149
_oxdiff_exptl_absorpt_empirical_full_min 0.895
