# 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_20220516-zyk-09113
_database_code_depnum_ccdc_archive 'CCDC 2321372'
loop_
_audit_author_name
_audit_author_address
'Min Zhang'
;Chongqing University
China
;
_audit_update_record             
;
2023-12-22 deposited with the CCDC.	2024-06-10 downloaded from the CCDC.
;
_audit_creation_date             2022-05-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H15 Br O'
_chemical_formula_sum            'C15 H15 Br O'
_chemical_formula_weight         291.18
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H15 Br O'
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'
Br Br -0.2901 2.4595 '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           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                   9.0877(6)
_cell_length_b                   10.7172(12)
_cell_length_c                   14.3707(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1399.6(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1546
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.3120
_cell_measurement_theta_min      2.3620
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.919
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021)
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    1.382
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.28
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0611
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.883
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5784
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.850
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.089
_diffrn_reflns_theta_min         2.371
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0892
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.883
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      2.00  37.00   1.00   24.00    --   18.74  77.00 -60.00   35
  2  ω     21.00  87.00   1.00   24.00    --   18.74  57.00  90.00   66
  3  ω    -81.00  17.00   1.00   24.00    --  -18.93 -19.00-180.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0089053000
_diffrn_orient_matrix_UB_12      -0.0271056000
_diffrn_orient_matrix_UB_13      0.0446784000
_diffrn_orient_matrix_UB_21      -0.0459041000
_diffrn_orient_matrix_UB_22      0.0467915000
_diffrn_orient_matrix_UB_23      0.0194024000
_diffrn_orient_matrix_UB_31      -0.0624462000
_diffrn_orient_matrix_UB_32      -0.0382370000
_diffrn_orient_matrix_UB_33      -0.0079122000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.683
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.806
_reflns_number_gt                1681
_reflns_number_total             3195
_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 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_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         0.623
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 
;
 Flack x determined using 491 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.006(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         3195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1258
_refine_ls_R_factor_gt           0.0565
_refine_ls_restrained_S_all      1.016
_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)+(0.0452P)²+0.9495P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1135
_refine_ls_wR_factor_ref         0.1420
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C11(H11), C13(H13), C12(H12)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
2.d :
 C1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.34412(11) 0.71016(11) 0.50298(7) 0.1038(5) Uani 1 1 d . . . . .
O1 O 0.9599(6) 0.7817(6) 0.0808(3) 0.0778(17) Uani 1 1 d . . . . .
C10 C 0.5054(7) 0.6503(6) 0.2375(5) 0.0484(16) Uani 1 1 d . . . . .
C3 C 0.6577(7) 0.6340(6) 0.1944(4) 0.0464(15) Uani 1 1 d . . . . .
C15 C 0.4939(7) 0.6683(6) 0.3332(5) 0.0539(18) Uani 1 1 d . . . . .
H15 H 0.577537 0.666393 0.370491 0.065 Uiso 1 1 calc R U . . .
C7 C 0.7347(7) 0.7606(6) 0.1692(4) 0.0458(17) Uani 1 1 d . . . . .
C6 C 0.8523(8) 0.7209(8) 0.1000(4) 0.0562(18) Uani 1 1 d . . . . .
C14 C 0.3570(8) 0.6892(7) 0.3725(5) 0.0603(19) Uani 1 1 d . . . . .
C8 C 0.6314(9) 0.8483(7) 0.1157(5) 0.066(2) Uani 1 1 d . . . . .
H8A H 0.594118 0.806180 0.061688 0.098 Uiso 1 1 calc R U . . .
H8B H 0.684621 0.921409 0.096903 0.098 Uiso 1 1 calc R U . . .
H8C H 0.550893 0.872070 0.155168 0.098 Uiso 1 1 calc R U . . .
C2 C 0.7542(9) 0.5627(7) 0.2592(5) 0.0566(19) Uani 1 1 d . . . . .
C5 C 0.8117(8) 0.5962(8) 0.0594(5) 0.071(2) Uani 1 1 d . . . . .
H5A H 0.884011 0.533674 0.076398 0.085 Uiso 1 1 calc R U . . .
H5B H 0.806838 0.601185 -0.007945 0.085 Uiso 1 1 calc R U . . .
C4 C 0.6625(9) 0.5635(7) 0.0994(5) 0.062(2) Uani 1 1 d . . . . .
H4A H 0.653427 0.474121 0.108548 0.075 Uiso 1 1 calc R U . . .
H4B H 0.584105 0.591456 0.058633 0.075 Uiso 1 1 calc R U . . .
C9 C 0.8011(8) 0.8314(7) 0.2524(5) 0.060(2) Uani 1 1 d . . . . .
H9A H 0.724682 0.851339 0.295997 0.091 Uiso 1 1 calc R U . . .
H9B H 0.846415 0.906931 0.230764 0.091 Uiso 1 1 calc R U . . .
H9C H 0.873692 0.780008 0.282176 0.091 Uiso 1 1 calc R U . . .
C11 C 0.3782(8) 0.6536(7) 0.1851(6) 0.066(2) Uani 1 1 d . . . . .
H11 H 0.383090 0.641387 0.121104 0.080 Uiso 1 1 calc R U . . .
C13 C 0.2320(9) 0.6920(8) 0.3204(7) 0.077(2) Uani 1 1 d . . . . .
H13 H 0.140828 0.705322 0.348058 0.093 Uiso 1 1 calc R U . . .
C1 C 0.8323(9) 0.5063(9) 0.3072(6) 0.078(3) Uani 1 1 d . . . . .
H1 H 0.894866 0.461051 0.345694 0.094 Uiso 1 1 calc R U . . .
C12 C 0.2435(9) 0.6748(9) 0.2270(7) 0.079(3) Uani 1 1 d . . . . .
H12 H 0.159064 0.677348 0.190467 0.095 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C14 1.892(7) . ?
O1 C6 1.207(8) . ?
C10 C3 1.526(9) . ?
C10 C15 1.393(9) . ?
C10 C11 1.380(9) . ?
C3 C7 1.568(9) . ?
C3 C2 1.491(10) . ?
C3 C4 1.561(9) . ?
C15 H15 0.9300 . ?
C15 C14 1.384(9) . ?
C7 C6 1.520(9) . ?
C7 C8 1.535(9) . ?
C7 C9 1.539(9) . ?
C6 C5 1.504(11) . ?
C14 C13 1.361(11) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C2 C1 1.159(10) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C4 1.514(10) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C11 H11 0.9300 . ?
C11 C12 1.383(11) . ?
C13 H13 0.9300 . ?
C13 C12 1.359(12) . ?
C1 H1 0.9300 . ?
C12 H12 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
C15 C10 C3 119.0(6) . . ?
C11 C10 C3 122.7(6) . . ?
C11 C10 C15 118.2(6) . . ?
C10 C3 C7 113.5(5) . . ?
C10 C3 C4 115.9(6) . . ?
C2 C3 C10 109.8(5) . . ?
C2 C3 C7 109.0(5) . . ?
C2 C3 C4 106.3(6) . . ?
C4 C3 C7 101.8(5) . . ?
C10 C15 H15 120.3 . . ?
C14 C15 C10 119.5(7) . . ?
C14 C15 H15 120.3 . . ?
C6 C7 C3 102.9(5) . . ?
C6 C7 C8 105.9(6) . . ?
C6 C7 C9 111.7(5) . . ?
C8 C7 C3 111.8(5) . . ?
C8 C7 C9 109.1(6) . . ?
C9 C7 C3 115.0(5) . . ?
O1 C6 C7 124.6(7) . . ?
O1 C6 C5 126.1(7) . . ?
C5 C6 C7 109.3(6) . . ?
C15 C14 Br1 118.6(6) . . ?
C13 C14 Br1 119.4(6) . . ?
C13 C14 C15 122.0(7) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C1 C2 C3 177.8(8) . . ?
C6 C5 H5A 110.5 . . ?
C6 C5 H5B 110.5 . . ?
C6 C5 C4 106.1(6) . . ?
H5A C5 H5B 108.7 . . ?
C4 C5 H5A 110.5 . . ?
C4 C5 H5B 110.5 . . ?
C3 C4 H4A 110.9 . . ?
C3 C4 H4B 110.9 . . ?
C5 C4 C3 104.2(6) . . ?
C5 C4 H4A 110.9 . . ?
C5 C4 H4B 110.9 . . ?
H4A C4 H4B 108.9 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C12 120.6(8) . . ?
C12 C11 H11 119.7 . . ?
C14 C13 H13 120.8 . . ?
C12 C13 C14 118.4(7) . . ?
C12 C13 H13 120.8 . . ?
C2 C1 H1 180.0 . . ?
C11 C12 H12 119.3 . . ?
C13 C12 C11 121.4(8) . . ?
C13 C12 H12 119.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C14 C13 C12 -179.0(7) . . . . ?
O1 C6 C5 C4 -175.5(7) . . . . ?
C10 C3 C7 C6 -161.2(5) . . . . ?
C10 C3 C7 C8 -48.0(7) . . . . ?
C10 C3 C7 C9 77.1(7) . . . . ?
C10 C3 C4 C5 162.7(6) . . . . ?
C10 C15 C14 Br1 178.8(5) . . . . ?
C10 C15 C14 C13 0.4(11) . . . . ?
C10 C11 C12 C13 -0.5(14) . . . . ?
C3 C10 C15 C14 176.9(6) . . . . ?
C3 C10 C11 C12 -176.7(8) . . . . ?
C3 C7 C6 O1 -160.1(7) . . . . ?
C3 C7 C6 C5 20.6(7) . . . . ?
C15 C10 C3 C7 -86.2(7) . . . . ?
C15 C10 C3 C2 36.0(9) . . . . ?
C15 C10 C3 C4 156.4(6) . . . . ?
C15 C10 C11 C12 0.3(11) . . . . ?
C15 C14 C13 C12 -0.6(13) . . . . ?
C7 C3 C4 C5 38.9(7) . . . . ?
C7 C6 C5 C4 3.8(8) . . . . ?
C6 C5 C4 C3 -26.8(8) . . . . ?
C14 C13 C12 C11 0.7(15) . . . . ?
C8 C7 C6 O1 82.4(8) . . . . ?
C8 C7 C6 C5 -96.9(7) . . . . ?
C2 C3 C7 C6 76.1(6) . . . . ?
C2 C3 C7 C8 -170.7(6) . . . . ?
C2 C3 C7 C9 -45.5(7) . . . . ?
C2 C3 C4 C5 -75.1(7) . . . . ?
C4 C3 C7 C6 -35.9(6) . . . . ?
C4 C3 C7 C8 77.3(7) . . . . ?
C4 C3 C7 C9 -157.6(6) . . . . ?
C9 C7 C6 O1 -36.2(10) . . . . ?
C9 C7 C6 C5 144.5(6) . . . . ?
C11 C10 C3 C7 90.8(8) . . . . ?
C11 C10 C3 C2 -147.0(7) . . . . ?
C11 C10 C3 C4 -26.6(10) . . . . ?
C11 C10 C15 C14 -0.2(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.103
_oxdiff_exptl_absorpt_empirical_full_min 0.913
####################################################################### 
# 
# 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_20221024-zyk10066-1-1
_database_code_depnum_ccdc_archive 'CCDC 2321373'
loop_
_audit_author_name
_audit_author_address
'Min Zhang'
;Chongqing University
China
;
_audit_update_record             
;
2023-12-22 deposited with the CCDC.	2024-06-10 downloaded from the CCDC.
;
_audit_creation_date             2022-10-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H24 O2'
_chemical_formula_sum            'C23 H24 O2'
_chemical_formula_weight         332.42
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C23 H24 O2'
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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.6478(3)
_cell_length_b                   10.5086(5)
_cell_length_c                   26.9042(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1879.50(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2657
_cell_measurement_temperature    293
_cell_measurement_theta_max      26.3720
_cell_measurement_theta_min      3.9280
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91462
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021)
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    1.175
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0591
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.888
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            6986
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.860
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.866
_diffrn_reflns_theta_min         3.418
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0892
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.888
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -40.00  42.00   1.00   18.00    --   18.74 -38.00-150.00   82
  2  ω    -24.00  51.00   1.00   18.00    --   18.74  19.00  90.00   75
  3  ω    -27.00  -2.00   1.00   18.00    --  -18.85 -77.00 120.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0779480000
_diffrn_orient_matrix_UB_12      -0.0416942000
_diffrn_orient_matrix_UB_13      -0.0076626000
_diffrn_orient_matrix_UB_21      -0.0092972000
_diffrn_orient_matrix_UB_22      -0.0340855000
_diffrn_orient_matrix_UB_23      0.0226483000
_diffrn_orient_matrix_UB_31      -0.0721812000
_diffrn_orient_matrix_UB_32      -0.0406674000
_diffrn_orient_matrix_UB_33      -0.0111527000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.684
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.823
_reflns_number_gt                3112
_reflns_number_total             4231
_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 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_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         0.180
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Flack x determined using 902 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.3(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         4231
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0556
_refine_ls_restrained_S_all      1.065
_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)+(0.0456P)²+0.3098P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1219
_refine_ls_wR_factor_ref         0.1392
_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:
 C00F(H00F)
2.b Secondary CH2 refined with riding coordinates:
 C00B(H00B,H00C), C00H(H00H,H00I)
2.c Aromatic/amide H refined with riding coordinates:
 C009(H009), C00A(H00A), C00C(H00D), C00D(H00E), C00G(H00G), C00I(H00J),
 C00L(H00Q), C00M(H00R), C00N(H00S)
2.d Idealised Me refined as rotating group:
 C00J(H00K,H00L,H00M), C00K(H00N,H00O,H00P), C00O(H00T,H00U,H00V)
2.e :
 C00P(H00W)
;
_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
O001 O -0.0836(4) 0.0700(2) 0.33784(10) 0.0621(8) Uani 1 1 d . . . . .
O002 O 0.7260(4) 0.3563(3) 0.12394(10) 0.0634(8) Uani 1 1 d . . . . .
C003 C 0.4162(5) 0.2228(3) 0.24850(12) 0.0408(8) Uani 1 1 d . . . . .
C004 C 0.6347(5) 0.3093(3) 0.16578(13) 0.0444(8) Uani 1 1 d . . . . .
C005 C 0.0367(4) 0.3773(3) 0.38467(11) 0.0355(7) Uani 1 1 d . . . . .
C006 C -0.0248(5) 0.2368(3) 0.39860(12) 0.0402(8) Uani 1 1 d . . . . .
C007 C 0.0970(5) 0.4594(3) 0.42962(13) 0.0397(8) Uani 1 1 d . . . . .
C008 C -0.1316(5) 0.4411(3) 0.35904(13) 0.0430(8) Uani 1 1 d . . . . .
C009 C 0.2928(5) 0.5002(3) 0.43775(14) 0.0498(9) Uani 1 1 d . . . . .
H009 H 0.394189 0.476240 0.415857 0.060 Uiso 1 1 calc R U . . .
C00A C 0.6084(5) 0.1806(3) 0.23900(13) 0.0469(8) Uani 1 1 d . . . . .
H00A H 0.666333 0.122172 0.260660 0.056 Uiso 1 1 calc R U . . .
C00B C 0.2061(5) 0.3561(3) 0.34555(12) 0.0403(8) Uani 1 1 d . . . . .
H00B H 0.225852 0.431878 0.325566 0.048 Uiso 1 1 calc R U . . .
H00C H 0.332037 0.334504 0.361691 0.048 Uiso 1 1 calc R U . . .
C00C C 0.3376(5) 0.3137(3) 0.21638(13) 0.0460(8) Uani 1 1 d . . . . .
H00D H 0.210237 0.346877 0.222503 0.055 Uiso 1 1 calc R U . . .
C00D C 0.7195(5) 0.2220(3) 0.19828(14) 0.0483(9) Uani 1 1 d . . . . .
H00E H 0.848988 0.191513 0.192905 0.058 Uiso 1 1 calc R U . . .
C00E C -0.0027(5) 0.1701(3) 0.34830(12) 0.0425(8) Uani 1 1 d . . . . .
C00F C 0.1316(5) 0.2456(3) 0.31349(13) 0.0415(8) Uani 1 1 d . . . . .
H00F H 0.047741 0.280515 0.286815 0.050 Uiso 1 1 calc R U . . .
C00G C 0.4444(5) 0.3559(3) 0.17561(14) 0.0495(9) Uani 1 1 d . . . . .
H00G H 0.387878 0.416271 0.154542 0.059 Uiso 1 1 calc R U . . .
C00H C 0.2946(6) 0.1621(3) 0.28987(14) 0.0512(9) Uani 1 1 d . . . . .
H00H H 0.386684 0.135516 0.315826 0.061 Uiso 1 1 calc R U . . .
H00I H 0.230873 0.086110 0.276819 0.061 Uiso 1 1 calc R U . . .
C00I C -0.0488(6) 0.4977(4) 0.46322(15) 0.0541(10) Uani 1 1 d . . . . .
H00J H -0.181468 0.472594 0.458305 0.065 Uiso 1 1 calc R U . . .
C00J C 0.9184(5) 0.3081(4) 0.11100(16) 0.0630(11) Uani 1 1 d . . . . .
H00K H 0.956106 0.339609 0.078832 0.094 Uiso 1 1 calc R U . . .
H00L H 0.913755 0.216801 0.110213 0.094 Uiso 1 1 calc R U . . .
H00M H 1.015435 0.335227 0.135200 0.094 Uiso 1 1 calc R U . . .
C00K C 0.1309(7) 0.1749(4) 0.43318(14) 0.0620(11) Uani 1 1 d . . . . .
H00N H 0.262972 0.185084 0.419302 0.093 Uiso 1 1 calc R U . . .
H00O H 0.101384 0.085895 0.436625 0.093 Uiso 1 1 calc R U . . .
H00P H 0.125672 0.214973 0.465215 0.093 Uiso 1 1 calc R U . . .
C00L C -0.0016(7) 0.5728(4) 0.50406(15) 0.0648(11) Uani 1 1 d . . . . .
H00Q H -0.101442 0.596103 0.526495 0.078 Uiso 1 1 calc R U . . .
C00M C 0.3386(6) 0.5769(4) 0.47851(16) 0.0635(12) Uani 1 1 d . . . . .
H00R H 0.470358 0.604004 0.483375 0.076 Uiso 1 1 calc R U . . .
C00N C 0.1934(7) 0.6126(4) 0.51123(16) 0.0648(11) Uani 1 1 d . . . . .
H00S H 0.225684 0.663583 0.538327 0.078 Uiso 1 1 calc R U . . .
C00O C -0.2354(6) 0.2176(4) 0.41967(17) 0.0662(12) Uani 1 1 d . . . . .
H00T H -0.241042 0.250935 0.452862 0.099 Uiso 1 1 calc R U . . .
H00U H -0.266502 0.128363 0.420249 0.099 Uiso 1 1 calc R U . . .
H00V H -0.331369 0.261267 0.399188 0.099 Uiso 1 1 calc R U . . .
C00P C -0.2623(6) 0.4920(5) 0.33809(17) 0.0686(12) Uani 1 1 d . . . . .
H00W H -0.366497 0.532700 0.321378 0.082 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
O001 C00E 1.214(4) . ?
O002 C004 1.371(4) . ?
O002 C00J 1.419(4) . ?
C003 C00A 1.377(5) . ?
C003 C00C 1.391(4) . ?
C003 C00H 1.516(5) . ?
C004 C00D 1.387(5) . ?
C004 C00G 1.381(5) . ?
C005 C006 1.577(4) . ?
C005 C007 1.539(4) . ?
C005 C008 1.476(4) . ?
C005 C00B 1.558(4) . ?
C006 C00E 1.531(4) . ?
C006 C00K 1.536(5) . ?
C006 C00O 1.524(5) . ?
C007 C009 1.388(5) . ?
C007 C00I 1.385(5) . ?
C008 C00P 1.165(5) . ?
C009 H009 0.9300 . ?
C009 C00M 1.395(5) . ?
C00A H00A 0.9300 . ?
C00A C00D 1.391(5) . ?
C00B H00B 0.9700 . ?
C00B H00C 0.9700 . ?
C00B C00F 1.529(4) . ?
C00C H00D 0.9300 . ?
C00C C00G 1.380(5) . ?
C00D H00E 0.9300 . ?
C00E C00F 1.518(4) . ?
C00F H00F 0.9800 . ?
C00F C00H 1.532(5) . ?
C00G H00G 0.9300 . ?
C00H H00H 0.9700 . ?
C00H H00I 0.9700 . ?
C00I H00J 0.9300 . ?
C00I C00L 1.389(5) . ?
C00J H00K 0.9600 . ?
C00J H00L 0.9600 . ?
C00J H00M 0.9600 . ?
C00K H00N 0.9600 . ?
C00K H00O 0.9600 . ?
C00K H00P 0.9600 . ?
C00L H00Q 0.9300 . ?
C00L C00N 1.375(6) . ?
C00M H00R 0.9300 . ?
C00M C00N 1.359(6) . ?
C00N H00S 0.9300 . ?
C00O H00T 0.9600 . ?
C00O H00U 0.9600 . ?
C00O H00V 0.9600 . ?
C00P H00W 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
C004 O002 C00J 118.2(3) . . ?
C00A C003 C00C 117.0(3) . . ?
C00A C003 C00H 119.7(3) . . ?
C00C C003 C00H 123.0(3) . . ?
O002 C004 C00D 125.2(3) . . ?
O002 C004 C00G 115.8(3) . . ?
C00G C004 C00D 119.1(3) . . ?
C007 C005 C006 113.9(3) . . ?
C007 C005 C00B 115.0(2) . . ?
C008 C005 C006 109.9(3) . . ?
C008 C005 C007 108.1(3) . . ?
C008 C005 C00B 107.3(3) . . ?
C00B C005 C006 102.4(2) . . ?
C00E C006 C005 101.2(2) . . ?
C00E C006 C00K 106.0(3) . . ?
C00K C006 C005 111.5(3) . . ?
C00O C006 C005 116.8(3) . . ?
C00O C006 C00E 110.9(3) . . ?
C00O C006 C00K 109.7(3) . . ?
C009 C007 C005 122.8(3) . . ?
C00I C007 C005 119.6(3) . . ?
C00I C007 C009 117.6(3) . . ?
C00P C008 C005 178.8(4) . . ?
C007 C009 H009 119.7 . . ?
C007 C009 C00M 120.5(4) . . ?
C00M C009 H009 119.7 . . ?
C003 C00A H00A 118.7 . . ?
C003 C00A C00D 122.6(3) . . ?
C00D C00A H00A 118.7 . . ?
C005 C00B H00B 110.8 . . ?
C005 C00B H00C 110.8 . . ?
H00B C00B H00C 108.9 . . ?
C00F C00B C005 104.8(2) . . ?
C00F C00B H00B 110.8 . . ?
C00F C00B H00C 110.8 . . ?
C003 C00C H00D 119.3 . . ?
C00G C00C C003 121.4(3) . . ?
C00G C00C H00D 119.3 . . ?
C004 C00D C00A 119.2(3) . . ?
C004 C00D H00E 120.4 . . ?
C00A C00D H00E 120.4 . . ?
O001 C00E C006 124.0(3) . . ?
O001 C00E C00F 124.8(3) . . ?
C00F C00E C006 111.3(3) . . ?
C00B C00F H00F 108.2 . . ?
C00B C00F C00H 116.1(3) . . ?
C00E C00F C00B 103.8(3) . . ?
C00E C00F H00F 108.2 . . ?
C00E C00F C00H 111.9(3) . . ?
C00H C00F H00F 108.2 . . ?
C004 C00G H00G 119.7 . . ?
C00C C00G C004 120.6(3) . . ?
C00C C00G H00G 119.7 . . ?
C003 C00H C00F 116.2(3) . . ?
C003 C00H H00H 108.2 . . ?
C003 C00H H00I 108.2 . . ?
C00F C00H H00H 108.2 . . ?
C00F C00H H00I 108.2 . . ?
H00H C00H H00I 107.4 . . ?
C007 C00I H00J 119.2 . . ?
C007 C00I C00L 121.5(4) . . ?
C00L C00I H00J 119.2 . . ?
O002 C00J H00K 109.5 . . ?
O002 C00J H00L 109.5 . . ?
O002 C00J H00M 109.5 . . ?
H00K C00J H00L 109.5 . . ?
H00K C00J H00M 109.5 . . ?
H00L C00J H00M 109.5 . . ?
C006 C00K H00N 109.5 . . ?
C006 C00K H00O 109.5 . . ?
C006 C00K H00P 109.5 . . ?
H00N C00K H00O 109.5 . . ?
H00N C00K H00P 109.5 . . ?
H00O C00K H00P 109.5 . . ?
C00I C00L H00Q 120.1 . . ?
C00N C00L C00I 119.8(4) . . ?
C00N C00L H00Q 120.1 . . ?
C009 C00M H00R 119.6 . . ?
C00N C00M C009 120.9(4) . . ?
C00N C00M H00R 119.6 . . ?
C00L C00N H00S 120.2 . . ?
C00M C00N C00L 119.7(4) . . ?
C00M C00N H00S 120.2 . . ?
C006 C00O H00T 109.5 . . ?
C006 C00O H00U 109.5 . . ?
C006 C00O H00V 109.5 . . ?
H00T C00O H00U 109.5 . . ?
H00T C00O H00V 109.5 . . ?
H00U C00O H00V 109.5 . . ?
C008 C00P H00W 180.0 . . ?

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
O001 C00E C00F C00B -175.9(3) . . . . ?
O001 C00E C00F C00H -49.9(5) . . . . ?
O002 C004 C00D C00A -178.9(3) . . . . ?
O002 C004 C00G C00C 179.1(3) . . . . ?
C003 C00A C00D C004 0.1(5) . . . . ?
C003 C00C C00G C004 -0.6(5) . . . . ?
C005 C006 C00E O001 -159.5(3) . . . . ?
C005 C006 C00E C00F 20.1(3) . . . . ?
C005 C007 C009 C00M 178.6(3) . . . . ?
C005 C007 C00I C00L -179.4(3) . . . . ?
C005 C00B C00F C00E -28.0(3) . . . . ?
C005 C00B C00F C00H -151.2(3) . . . . ?
C006 C005 C007 C009 111.0(4) . . . . ?
C006 C005 C007 C00I -70.6(4) . . . . ?
C006 C005 C00B C00F 40.7(3) . . . . ?
C006 C00E C00F C00B 4.6(4) . . . . ?
C006 C00E C00F C00H 130.5(3) . . . . ?
C007 C005 C006 C00E -161.0(3) . . . . ?
C007 C005 C006 C00K -48.6(4) . . . . ?
C007 C005 C006 C00O 78.6(4) . . . . ?
C007 C005 C00B C00F 164.8(3) . . . . ?
C007 C009 C00M C00N 0.4(6) . . . . ?
C007 C00I C00L C00N 1.2(6) . . . . ?
C008 C005 C006 C00E 77.6(3) . . . . ?
C008 C005 C006 C00K -170.0(3) . . . . ?
C008 C005 C006 C00O -42.8(4) . . . . ?
C008 C005 C007 C009 -126.6(3) . . . . ?
C008 C005 C007 C00I 51.9(4) . . . . ?
C008 C005 C00B C00F -74.9(3) . . . . ?
C009 C007 C00I C00L -0.9(6) . . . . ?
C009 C00M C00N C00L -0.1(7) . . . . ?
C00A C003 C00C C00G 2.6(5) . . . . ?
C00A C003 C00H C00F 153.8(3) . . . . ?
C00B C005 C006 C00E -36.2(3) . . . . ?
C00B C005 C006 C00K 76.2(3) . . . . ?
C00B C005 C006 C00O -156.6(3) . . . . ?
C00B C005 C007 C009 -6.8(4) . . . . ?
C00B C005 C007 C00I 171.7(3) . . . . ?
C00B C00F C00H C003 -70.3(4) . . . . ?
C00C C003 C00A C00D -2.4(5) . . . . ?
C00C C003 C00H C00F -31.5(5) . . . . ?
C00D C004 C00G C00C -1.8(5) . . . . ?
C00E C00F C00H C003 170.8(3) . . . . ?
C00G C004 C00D C00A 2.0(5) . . . . ?
C00H C003 C00A C00D 172.7(3) . . . . ?
C00H C003 C00C C00G -172.2(3) . . . . ?
C00I C007 C009 C00M 0.1(5) . . . . ?
C00I C00L C00N C00M -0.7(7) . . . . ?
C00J O002 C004 C00D 3.3(5) . . . . ?
C00J O002 C004 C00G -177.6(3) . . . . ?
C00K C006 C00E O001 84.1(4) . . . . ?
C00K C006 C00E C00F -96.3(3) . . . . ?
C00O C006 C00E O001 -35.0(5) . . . . ?
C00O C006 C00E C00F 144.6(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.202
_oxdiff_exptl_absorpt_empirical_full_min 0.870
####################################################################### 
# 
# 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_20221027-zyk-py-cy-me
_database_code_depnum_ccdc_archive 'CCDC 2321374'
loop_
_audit_author_name
_audit_author_address
'Min Zhang'
;Chongqing University
China
;
_audit_update_record             
;
2023-12-22 deposited with the CCDC.	2024-06-10 downloaded from the CCDC.
;
_audit_creation_date             2022-10-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H35 N3 O2'
_chemical_formula_sum            'C25 H35 N3 O2'
_chemical_formula_weight         409.56
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C25 H35 N3 O2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.5199(3)
_cell_length_b                   8.9739(5)
_cell_length_c                   19.7834(10)
_cell_angle_alpha                90
_cell_angle_beta                 96.520(5)
_cell_angle_gamma                90
_cell_volume                     1150.02(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6517
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.5390
_cell_measurement_theta_min      3.8360
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.977
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52110
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021)
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    1.183
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.31
_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  0.0352
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.913
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            16343
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.882
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.173
_diffrn_reflns_theta_min         3.421
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0892
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.913
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     36.00  61.00   1.00   15.32    --   18.74 -99.00 -30.00   25
  2  ω    -39.00  49.00   1.00   15.32    --   18.74 -77.00 150.00   88
  3  ω      1.00  87.00   1.00   15.32    --   18.74  57.00-150.00   86
  4  ω     -3.00  84.00   1.00   15.32    --   18.74  57.00 120.00   87
  5  ω      5.00  86.00   1.00   15.32    --   18.74  57.00 -60.00   81
  6  ω    -38.00  49.00   1.00   15.32    --   18.74 -77.00  60.00   87
  7  ω    -11.00  19.00   1.00   15.32    --   18.74  77.00  30.00   30
  8  ω    -36.00  37.00   1.00   15.32    --   18.74 -57.00 -60.00   73
  9  ω    -40.00  23.00   1.00   15.32    --  -18.93  57.00 -90.00   63
 10  ω    -78.00  -7.00   1.00   15.32    --  -18.93 -38.00 -30.00   71
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0704034000
_diffrn_orient_matrix_UB_12      -0.0478892000
_diffrn_orient_matrix_UB_13      0.0141760000
_diffrn_orient_matrix_UB_21      0.0720960000
_diffrn_orient_matrix_UB_22      -0.0098760000
_diffrn_orient_matrix_UB_23      0.0293054000
_diffrn_orient_matrix_UB_31      -0.0427449000
_diffrn_orient_matrix_UB_32      0.0621151000
_diffrn_orient_matrix_UB_33      0.0155886000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.822
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.847
_reflns_number_gt                4023
_reflns_number_total             5469
_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 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_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         0.159
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Flack x determined using 1449 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         5469
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0498
_refine_ls_restrained_S_all      1.141
_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)+(0.0622P)²+0.0916P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1328
_refine_ls_wR_factor_ref         0.1471
_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:
 C008(H008), C00C(H00C), C00F(H00F), C00G(H00G), C00H(H00H), C00J(H00K)
2.b Secondary CH2 refined with riding coordinates:
 C00K(H00L,H00M), C00L(H00N,H00O), C00M(H00P,H00Q), C00N(H00R,H00S), C00P(H00W,
 H00X), C00Q(H00Y,H), C00R(H00Z,HA), C00S(H00,HB), C00T(H1,HC), C00U(H2,HD)
2.c Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00D(H00D), C00E(H00E)
2.d Idealised Me refined as rotating group:
 C00I(H00A,H00I,H00J), C00O(H00T,H00U,H00V)
;
_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
O001 O 0.7534(3) 0.3838(3) 0.56249(11) 0.0485(6) Uani 1 1 d . . . . .
O002 O 0.8461(4) 0.5888(3) 0.79161(12) 0.0537(7) Uani 1 1 d . . . . .
N003 N 0.5955(4) 0.4742(3) 0.68167(13) 0.0390(6) Uani 1 1 d . . . . .
N004 N 0.4303(4) 0.3716(4) 0.50788(14) 0.0468(7) Uani 1 1 d . . . . .
N005 N 0.5716(4) 0.6235(4) 0.84921(14) 0.0534(8) Uani 1 1 d . . . . .
C006 C 0.6430(5) 0.5731(4) 0.79704(16) 0.0416(8) Uani 1 1 d . . . . .
C007 C 0.5463(5) 0.3927(4) 0.56282(16) 0.0384(7) Uani 1 1 d . . . . .
C008 C 0.7859(5) 0.3515(4) 0.49155(16) 0.0425(8) Uani 1 1 d . . . . .
H008 H 0.859816 0.434550 0.473131 0.051 Uiso 1 1 calc R U . . .
C009 C 0.4648(5) 0.4289(3) 0.62818(15) 0.0381(7) Uani 1 1 d . . . . .
C00A C 0.5100(5) 0.5077(4) 0.73859(16) 0.0389(7) Uani 1 1 d . . . . .
C00B C 0.2526(5) 0.4165(4) 0.62989(17) 0.0441(8) Uani 1 1 d . . . . .
H00B H 0.167948 0.387551 0.591107 0.053 Uiso 1 1 calc R U . . .
C00C C 0.5645(5) 0.3425(4) 0.45438(16) 0.0425(8) Uani 1 1 d . . . . .
H00C H 0.539680 0.240456 0.437742 0.051 Uiso 1 1 calc R U . . .
C00D C 0.1687(5) 0.4470(4) 0.68889(17) 0.0481(8) Uani 1 1 d . . . . .
H00D H 0.027629 0.437413 0.691204 0.058 Uiso 1 1 calc R U . . .
C00E C 0.3008(5) 0.4926(4) 0.74494(17) 0.0452(8) Uani 1 1 d . . . . .
H00E H 0.250293 0.512730 0.786106 0.054 Uiso 1 1 calc R U . . .
C00F C 0.5187(5) 0.4496(4) 0.39476(16) 0.0425(7) Uani 1 1 d . . . . .
H00F H 0.543000 0.551018 0.412187 0.051 Uiso 1 1 calc R U . . .
C00G C 0.9362(5) 0.6587(4) 0.85481(17) 0.0459(8) Uani 1 1 d . . . . .
H00G H 1.021643 0.585710 0.881995 0.055 Uiso 1 1 calc R U . . .
C00H C 0.7446(5) 0.6970(4) 0.89118(16) 0.0451(8) Uani 1 1 d . . . . .
H00H H 0.722705 0.804877 0.887715 0.054 Uiso 1 1 calc R U . . .
C00I C 0.9103(6) 0.2112(5) 0.4890(2) 0.0615(11) Uani 1 1 d . . . . .
H00A H 1.039709 0.222719 0.516904 0.092 Uiso 1 1 calc R U . . .
H00I H 0.935233 0.191977 0.442891 0.092 Uiso 1 1 calc R U . . .
H00J H 0.835527 0.129301 0.505531 0.092 Uiso 1 1 calc R U . . .
C00J C 0.7581(5) 0.6546(4) 0.96644(17) 0.0478(8) Uani 1 1 d . . . . .
H00K H 0.793141 0.548594 0.970790 0.057 Uiso 1 1 calc R U . . .
C00K C 0.6611(6) 0.4239(5) 0.33952(19) 0.0523(9) Uani 1 1 d . . . . .
H00L H 0.803550 0.435631 0.359042 0.063 Uiso 1 1 calc R U . . .
H00M H 0.643699 0.322740 0.322589 0.063 Uiso 1 1 calc R U . . .
C00L C 0.6154(6) 0.5327(5) 0.28060(19) 0.0627(11) Uani 1 1 d . . . . .
H00N H 0.647359 0.633149 0.296559 0.075 Uiso 1 1 calc R U . . .
H00O H 0.703206 0.509672 0.245558 0.075 Uiso 1 1 calc R U . . .
C00M C 0.2933(5) 0.4400(5) 0.36343(18) 0.0540(9) Uani 1 1 d . . . . .
H00P H 0.264261 0.339855 0.346567 0.065 Uiso 1 1 calc R U . . .
H00Q H 0.203409 0.460470 0.398173 0.065 Uiso 1 1 calc R U . . .
C00N C 0.9288(7) 0.7441(5) 1.00802(18) 0.0601(10) Uani 1 1 d . . . . .
H00R H 1.060770 0.719407 0.992676 0.072 Uiso 1 1 calc R U . . .
H00S H 0.904405 0.849601 1.000009 0.072 Uiso 1 1 calc R U . . .
C00O C 1.0680(6) 0.7889(5) 0.8390(2) 0.0630(11) Uani 1 1 d . . . . .
H00T H 1.175977 0.755046 0.813553 0.094 Uiso 1 1 calc R U . . .
H00U H 1.127731 0.833863 0.880679 0.094 Uiso 1 1 calc R U . . .
H00V H 0.984420 0.860908 0.812651 0.094 Uiso 1 1 calc R U . . .
C00P C 0.5517(6) 0.6792(6) 0.99464(18) 0.0621(11) Uani 1 1 d . . . . .
H00W H 0.508243 0.781643 0.986422 0.074 Uiso 1 1 calc R U . . .
H00X H 0.448131 0.615029 0.970616 0.074 Uiso 1 1 calc R U . . .
C00Q C 0.2485(6) 0.5503(6) 0.3056(2) 0.0666(12) Uani 1 1 d . . . . .
H00Y H 0.266493 0.650940 0.323094 0.080 Uiso 1 1 calc R U . . .
H H 0.106208 0.539407 0.285768 0.080 Uiso 1 1 calc R U . . .
C00R C 0.7324(9) 0.7383(6) 1.1101(2) 0.0808(15) Uani 1 1 d . . . . .
H00Z H 0.696930 0.843195 1.106226 0.097 Uiso 1 1 calc R U . . .
HA H 0.742254 0.711099 1.157773 0.097 Uiso 1 1 calc R U . . .
C00S C 0.5646(8) 0.6470(6) 1.0704(2) 0.0758(13) Uani 1 1 d . . . . .
H00 H 0.432958 0.669677 1.086431 0.091 Uiso 1 1 calc R U . . .
HB H 0.592640 0.541931 1.078228 0.091 Uiso 1 1 calc R U . . .
C00T C 0.9386(8) 0.7131(6) 1.0839(2) 0.0761(14) Uani 1 1 d . . . . .
H1 H 0.981440 0.610716 1.092720 0.091 Uiso 1 1 calc R U . . .
HC H 1.041085 0.777598 1.108245 0.091 Uiso 1 1 calc R U . . .
C00U C 0.3919(7) 0.5253(6) 0.2506(2) 0.0707(12) Uani 1 1 d . . . . .
H2 H 0.363845 0.428539 0.229667 0.085 Uiso 1 1 calc R U . . .
HD H 0.365730 0.600681 0.215533 0.085 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
O001 C007 1.354(4) . ?
O001 C008 1.472(4) . ?
O002 C006 1.348(4) . ?
O002 C00G 1.461(4) . ?
N003 C009 1.344(4) . ?
N003 C00A 1.346(4) . ?
N004 C007 1.266(4) . ?
N004 C00C 1.471(4) . ?
N005 C006 1.263(4) . ?
N005 C00H 1.478(4) . ?
C006 C00A 1.485(5) . ?
C007 C009 1.488(4) . ?
C008 H008 0.9800 . ?
C008 C00C 1.546(5) . ?
C008 C00I 1.501(5) . ?
C009 C00B 1.392(4) . ?
C00A C00E 1.391(5) . ?
C00B H00B 0.9300 . ?
C00B C00D 1.372(4) . ?
C00C H00C 0.9800 . ?
C00C C00F 1.525(5) . ?
C00D H00D 0.9300 . ?
C00D C00E 1.386(5) . ?
C00E H00E 0.9300 . ?
C00F H00F 0.9800 . ?
C00F C00K 1.530(4) . ?
C00F C00M 1.531(5) . ?
C00G H00G 0.9800 . ?
C00G C00H 1.549(5) . ?
C00G C00O 1.504(5) . ?
C00H H00H 0.9800 . ?
C00H C00J 1.530(5) . ?
C00I H00A 0.9600 . ?
C00I H00I 0.9600 . ?
C00I H00J 0.9600 . ?
C00J H00K 0.9800 . ?
C00J C00N 1.534(5) . ?
C00J C00P 1.530(5) . ?
C00K H00L 0.9700 . ?
C00K H00M 0.9700 . ?
C00K C00L 1.523(5) . ?
C00L H00N 0.9700 . ?
C00L H00O 0.9700 . ?
C00L C00U 1.512(6) . ?
C00M H00P 0.9700 . ?
C00M H00Q 0.9700 . ?
C00M C00Q 1.516(6) . ?
C00N H00R 0.9700 . ?
C00N H00S 0.9700 . ?
C00N C00T 1.521(5) . ?
C00O H00T 0.9600 . ?
C00O H00U 0.9600 . ?
C00O H00V 0.9600 . ?
C00P H00W 0.9700 . ?
C00P H00X 0.9700 . ?
C00P C00S 1.519(5) . ?
C00Q H00Y 0.9700 . ?
C00Q H 0.9700 . ?
C00Q C00U 1.529(6) . ?
C00R H00Z 0.9700 . ?
C00R HA 0.9700 . ?
C00R C00S 1.513(7) . ?
C00R C00T 1.511(7) . ?
C00S H00 0.9700 . ?
C00S HB 0.9700 . ?
C00T H1 0.9700 . ?
C00T HC 0.9700 . ?
C00U H2 0.9700 . ?
C00U HD 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C007 O001 C008 105.6(2) . . ?
C006 O002 C00G 106.3(2) . . ?
C009 N003 C00A 116.1(3) . . ?
C007 N004 C00C 107.4(3) . . ?
C006 N005 C00H 106.9(3) . . ?
O002 C006 C00A 118.1(3) . . ?
N005 C006 O002 118.9(3) . . ?
N005 C006 C00A 122.8(3) . . ?
O001 C007 C009 118.2(3) . . ?
N004 C007 O001 119.1(3) . . ?
N004 C007 C009 122.8(3) . . ?
O001 C008 H008 109.6 . . ?
O001 C008 C00C 103.7(2) . . ?
O001 C008 C00I 109.5(3) . . ?
C00C C008 H008 109.6 . . ?
C00I C008 H008 109.6 . . ?
C00I C008 C00C 114.8(3) . . ?
N003 C009 C007 119.5(3) . . ?
N003 C009 C00B 123.2(3) . . ?
C00B C009 C007 117.2(3) . . ?
N003 C00A C006 118.6(3) . . ?
N003 C00A C00E 123.9(3) . . ?
C00E C00A C006 117.4(3) . . ?
C009 C00B H00B 120.1 . . ?
C00D C00B C009 119.9(3) . . ?
C00D C00B H00B 120.1 . . ?
N004 C00C C008 104.4(3) . . ?
N004 C00C H00C 108.6 . . ?
N004 C00C C00F 111.3(3) . . ?
C008 C00C H00C 108.6 . . ?
C00F C00C C008 115.2(3) . . ?
C00F C00C H00C 108.6 . . ?
C00B C00D H00D 121.1 . . ?
C00B C00D C00E 117.9(3) . . ?
C00E C00D H00D 121.1 . . ?
C00A C00E H00E 120.6 . . ?
C00D C00E C00A 118.9(3) . . ?
C00D C00E H00E 120.6 . . ?
C00C C00F H00F 107.7 . . ?
C00C C00F C00K 112.1(3) . . ?
C00C C00F C00M 111.9(3) . . ?
C00K C00F H00F 107.7 . . ?
C00K C00F C00M 109.6(3) . . ?
C00M C00F H00F 107.7 . . ?
O002 C00G H00G 109.3 . . ?
O002 C00G C00H 103.0(3) . . ?
O002 C00G C00O 109.8(3) . . ?
C00H C00G H00G 109.3 . . ?
C00O C00G H00G 109.3 . . ?
C00O C00G C00H 115.7(3) . . ?
N005 C00H C00G 104.1(3) . . ?
N005 C00H H00H 107.8 . . ?
N005 C00H C00J 113.1(3) . . ?
C00G C00H H00H 107.8 . . ?
C00J C00H C00G 115.9(3) . . ?
C00J C00H H00H 107.8 . . ?
C008 C00I H00A 109.5 . . ?
C008 C00I H00I 109.5 . . ?
C008 C00I H00J 109.5 . . ?
H00A C00I H00I 109.5 . . ?
H00A C00I H00J 109.5 . . ?
H00I C00I H00J 109.5 . . ?
C00H C00J H00K 108.3 . . ?
C00H C00J C00N 110.5(3) . . ?
C00H C00J C00P 111.3(3) . . ?
C00N C00J H00K 108.3 . . ?
C00P C00J H00K 108.3 . . ?
C00P C00J C00N 110.1(3) . . ?
C00F C00K H00L 109.3 . . ?
C00F C00K H00M 109.3 . . ?
H00L C00K H00M 108.0 . . ?
C00L C00K C00F 111.6(3) . . ?
C00L C00K H00L 109.3 . . ?
C00L C00K H00M 109.3 . . ?
C00K C00L H00N 109.3 . . ?
C00K C00L H00O 109.3 . . ?
H00N C00L H00O 108.0 . . ?
C00U C00L C00K 111.6(3) . . ?
C00U C00L H00N 109.3 . . ?
C00U C00L H00O 109.3 . . ?
C00F C00M H00P 109.4 . . ?
C00F C00M H00Q 109.4 . . ?
H00P C00M H00Q 108.0 . . ?
C00Q C00M C00F 111.3(3) . . ?
C00Q C00M H00P 109.4 . . ?
C00Q C00M H00Q 109.4 . . ?
C00J C00N H00R 109.1 . . ?
C00J C00N H00S 109.1 . . ?
H00R C00N H00S 107.9 . . ?
C00T C00N C00J 112.3(3) . . ?
C00T C00N H00R 109.1 . . ?
C00T C00N H00S 109.1 . . ?
C00G C00O H00T 109.5 . . ?
C00G C00O H00U 109.5 . . ?
C00G C00O H00V 109.5 . . ?
H00T C00O H00U 109.5 . . ?
H00T C00O H00V 109.5 . . ?
H00U C00O H00V 109.5 . . ?
C00J C00P H00W 109.1 . . ?
C00J C00P H00X 109.1 . . ?
H00W C00P H00X 107.9 . . ?
C00S C00P C00J 112.3(3) . . ?
C00S C00P H00W 109.1 . . ?
C00S C00P H00X 109.1 . . ?
C00M C00Q H00Y 109.4 . . ?
C00M C00Q H 109.4 . . ?
C00M C00Q C00U 111.1(4) . . ?
H00Y C00Q H 108.0 . . ?
C00U C00Q H00Y 109.4 . . ?
C00U C00Q H 109.4 . . ?
H00Z C00R HA 108.0 . . ?
C00S C00R H00Z 109.4 . . ?
C00S C00R HA 109.4 . . ?
C00T C00R H00Z 109.4 . . ?
C00T C00R HA 109.4 . . ?
C00T C00R C00S 111.1(4) . . ?
C00P C00S H00 109.3 . . ?
C00P C00S HB 109.3 . . ?
C00R C00S C00P 111.4(4) . . ?
C00R C00S H00 109.3 . . ?
C00R C00S HB 109.3 . . ?
H00 C00S HB 108.0 . . ?
C00N C00T H1 109.3 . . ?
C00N C00T HC 109.3 . . ?
C00R C00T C00N 111.8(4) . . ?
C00R C00T H1 109.3 . . ?
C00R C00T HC 109.3 . . ?
H1 C00T HC 107.9 . . ?
C00L C00U C00Q 110.7(3) . . ?
C00L C00U H2 109.5 . . ?
C00L C00U HD 109.5 . . ?
C00Q C00U H2 109.5 . . ?
C00Q C00U HD 109.5 . . ?
H2 C00U HD 108.1 . . ?

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
O001 C007 C009 N003 10.4(4) . . . . ?
O001 C007 C009 C00B -171.0(3) . . . . ?
O001 C008 C00C N004 0.4(3) . . . . ?
O001 C008 C00C C00F 122.8(3) . . . . ?
O002 C006 C00A N003 -3.3(5) . . . . ?
O002 C006 C00A C00E -179.8(3) . . . . ?
O002 C00G C00H N005 8.4(4) . . . . ?
O002 C00G C00H C00J 133.3(3) . . . . ?
N003 C009 C00B C00D -2.0(5) . . . . ?
N003 C00A C00E C00D -3.1(5) . . . . ?
N004 C007 C009 N003 -168.9(3) . . . . ?
N004 C007 C009 C00B 9.7(5) . . . . ?
N004 C00C C00F C00K 178.3(3) . . . . ?
N004 C00C C00F C00M -58.1(3) . . . . ?
N005 C006 C00A N003 171.7(3) . . . . ?
N005 C006 C00A C00E -4.8(5) . . . . ?
N005 C00H C00J C00N -175.3(3) . . . . ?
N005 C00H C00J C00P -52.6(4) . . . . ?
C006 O002 C00G C00H -7.1(3) . . . . ?
C006 O002 C00G C00O -131.0(3) . . . . ?
C006 N005 C00H C00G -6.9(4) . . . . ?
C006 N005 C00H C00J -133.6(3) . . . . ?
C006 C00A C00E C00D 173.2(3) . . . . ?
C007 O001 C008 C00C -0.7(3) . . . . ?
C007 O001 C008 C00I -123.7(3) . . . . ?
C007 N004 C00C C008 0.1(4) . . . . ?
C007 N004 C00C C00F -124.8(3) . . . . ?
C007 C009 C00B C00D 179.4(3) . . . . ?
C008 O001 C007 N004 0.9(4) . . . . ?
C008 O001 C007 C009 -178.4(3) . . . . ?
C008 C00C C00F C00K 59.8(4) . . . . ?
C008 C00C C00F C00M -176.7(3) . . . . ?
C009 N003 C00A C006 -173.8(3) . . . . ?
C009 N003 C00A C00E 2.5(5) . . . . ?
C009 C00B C00D C00E 1.3(5) . . . . ?
C00A N003 C009 C007 178.7(3) . . . . ?
C00A N003 C009 C00B 0.1(4) . . . . ?
C00B C00D C00E C00A 1.1(5) . . . . ?
C00C N004 C007 O001 -0.7(4) . . . . ?
C00C N004 C007 C009 178.7(3) . . . . ?
C00C C00F C00K C00L -179.4(3) . . . . ?
C00C C00F C00M C00Q 178.4(3) . . . . ?
C00F C00K C00L C00U -55.9(4) . . . . ?
C00F C00M C00Q C00U 57.2(5) . . . . ?
C00G O002 C006 N005 3.3(4) . . . . ?
C00G O002 C006 C00A 178.5(3) . . . . ?
C00G C00H C00J C00N 64.6(4) . . . . ?
C00G C00H C00J C00P -172.8(3) . . . . ?
C00H N005 C006 O002 2.6(4) . . . . ?
C00H N005 C006 C00A -172.3(3) . . . . ?
C00H C00J C00N C00T 176.2(3) . . . . ?
C00H C00J C00P C00S -176.5(4) . . . . ?
C00I C008 C00C N004 119.8(3) . . . . ?
C00I C008 C00C C00F -117.8(3) . . . . ?
C00J C00N C00T C00R -54.5(5) . . . . ?
C00J C00P C00S C00R 55.7(6) . . . . ?
C00K C00F C00M C00Q -56.7(4) . . . . ?
C00K C00L C00U C00Q 55.0(5) . . . . ?
C00M C00F C00K C00L 55.8(4) . . . . ?
C00M C00Q C00U C00L -55.8(5) . . . . ?
C00N C00J C00P C00S -53.6(5) . . . . ?
C00O C00G C00H N005 128.3(3) . . . . ?
C00O C00G C00H C00J -106.8(4) . . . . ?
C00P C00J C00N C00T 52.9(5) . . . . ?
C00S C00R C00T C00N 55.3(5) . . . . ?
C00T C00R C00S C00P -55.8(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 1.444
_oxdiff_exptl_absorpt_empirical_full_min 0.503
####################################################################### 
# 
# 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_20230531-zyk11032-1
_database_code_depnum_ccdc_archive 'CCDC 2321378'
loop_
_audit_author_name
_audit_author_address
'Min Zhang'
;Chongqing University
China
;
_audit_update_record             
;
2023-12-22 deposited with the CCDC.	2024-06-10 downloaded from the CCDC.
;
_audit_creation_date             2023-05-31
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C29 H28 O4'
_chemical_formula_sum            'C29 H28 O4'
_chemical_formula_weight         440.51
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C29 H28 O4'
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           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                   12.4747(4)
_cell_length_b                   6.58280(10)
_cell_length_c                   15.4889(4)
_cell_angle_alpha                90
_cell_angle_beta                 110.054(3)
_cell_angle_gamma                90
_cell_volume                     1194.81(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10545
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.3850
_cell_measurement_theta_min      3.9390
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.643
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.12259
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021)
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    1.224
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20099
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.538
_diffrn_reflns_theta_min         3.037
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0892
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_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 -37.00   1.00    1.00    --    0.00 -38.00   0.00   35
  2  ω    -29.00  -2.00   1.00    1.00    --    0.00  88.00  74.00   27
  3  ω     -6.00  26.00   1.00    1.00    --    0.00 -38.00   0.00   32
  4  ω    -66.00 -31.00   1.00    1.00    --    0.00 -57.00 -60.00   35
  5  ω     29.00  64.00   1.00    1.00    --    0.00  57.00 -60.00   35
  6  ω      0.00  31.00   1.00    1.00    --    0.00  88.00  74.00   31
  7  ω    -16.00  19.00   1.00    1.00    --    0.00 -57.00 -60.00   35
  8  ω     24.00  60.00   1.00    1.00    --   54.00  77.00  90.00   36
  9  ω    -15.00  75.00   1.00    1.00    --   54.00 -57.00 -60.00   90
 10  ω     23.00 107.00   1.00    1.00    --   54.00-125.00 120.00   84
 11  ω     25.00  55.00   1.00    1.00    --   54.00  77.00-180.00   30
 12  ω     24.00  58.00   1.00    1.00    --   54.00  77.00 -90.00   34
 13  ω     24.00  65.00   1.00    1.00    --   54.00  77.00  60.00   41
 14  ω     64.00 120.00   1.00    1.00    --   54.00  77.00 -30.00   56
 15  ω     24.00  60.00   1.00    1.00    --   54.00  77.00 -60.00   36
 16  ω     27.00  57.00   1.00    1.00    --   54.00  77.00   0.00   30
 17  ω     -6.00  74.00   1.00    1.00    --   54.00 -57.00 120.00   80
 18  ω     73.00 123.00   1.00    1.00    --   54.00  77.00  60.00   50
 19  ω     78.00 118.00   1.00    1.00    --   54.00  77.00   0.00   40
 20  ω     80.00 113.00   1.00    1.00    --   54.00  77.00-180.00   33
 21  ω     78.00 122.00   1.00    1.00    --   54.00  77.00 -90.00   44
 22  ω     74.00 121.00   1.00    1.00    --   54.00  77.00-120.00   47
 23  ω     25.00  65.00   1.00    1.00    --   54.00  77.00-150.00   40
 24  ω     32.00  57.00   1.00    1.00    --   54.00  77.00-120.00   25
 25  ω     25.00  57.00   1.00    1.00    --   54.00  77.00  30.00   32
 26  ω     25.00  59.00   1.00    1.00    --   54.00  77.00 -30.00   34
 27  ω     -6.00  75.00   1.00    1.00    --   54.00 -57.00-150.00   81
 28  ω     87.00 124.00   1.00    1.00    --   54.00  77.00-150.00   37
 29  ω     24.00 101.00   1.00    1.00    --   54.00  77.00 150.00   77
 30  ω     83.00 109.00   1.00    1.00    --   54.00  77.00  90.00   26
 31  ω     26.00  58.00   1.00    1.00    --   54.00  77.00 120.00   32
 32  ω     78.00 105.00   1.00    1.00    --  108.00  77.00 120.00   27
 33  ω     78.00 104.00   1.00    1.00    --  108.00  77.00 -30.00   26
 34  ω     79.00 105.00   1.00    1.00    --  108.00  77.00-150.00   26
 35  ω    127.00 178.00   1.00    1.00    --  108.00  77.00  30.00   51
 36  ω     78.00 104.00   1.00    1.00    --  108.00  77.00  30.00   26
 37  ω     86.00 136.00   1.00    1.00    --  108.00  63.00 -60.00   50
 38  ω    134.00 178.00   1.00    1.00    --  108.00  77.00 -60.00   44
 39  ω    129.00 155.00   1.00    1.00    --  108.00  77.00-120.00   26
 40  ω     81.00 107.00   1.00    1.00    --  108.00  77.00-120.00   26
 41  ω     86.00 133.00   1.00    1.00    --  108.00  63.00   0.00   47
 42  ω    102.00 137.00   1.00    1.00    --  108.00 -77.00 150.00   35
 43  ω    121.00 177.00   1.00    1.00    --  108.00  77.00   2.29   56
 44  ω     39.00  80.00   1.00    1.00    --  108.00 -77.00 150.00   41
 45  ω     87.00 140.00   1.00    1.00    --  108.00  50.00-120.00   53
 46  ω     87.00 148.00   1.00    1.00    --  108.00  63.00-150.00   61
 47  ω    106.00 177.00   1.00    1.00    --  108.00 111.00 150.00   71
 48  ω     81.00 109.00   1.00    1.00    --  108.00-111.00  30.00   28
 49  ω     78.00 110.00   1.00    1.00    --  108.00  77.00-180.00   32
 50  ω     78.00 104.00   1.00    1.00    --  108.00  77.00 -60.00   26
 51  ω     94.00 152.00   1.00    1.00    --  108.00  50.00 -90.00   58
 52  ω    133.00 171.00   1.00    1.00    --  108.00  77.00 -90.00   38
 53  ω     80.00 105.00   1.00    1.00    --  108.00  77.00 -90.00   25
 54  ω     47.00  73.00   1.00    1.00    --  108.00 -63.00 -60.00   26
 55  ω     74.00 135.00   1.00    1.00    --  108.00 -77.00-120.00   61
 56  ω    109.00 146.00   1.00    1.00    --  108.00 -91.00  90.00   37
 57  ω    143.00 169.00   1.00    1.00    --  108.00  63.00-180.00   26
 58  ω     62.00 113.00   1.00    1.00    --  108.00-111.00 150.00   51
 59  ω     87.00 127.00   1.00    1.00    --  108.00  63.00-120.00   40
 60  ω     86.00 112.00   1.00    1.00    --  108.00  63.00 120.00   26
 61  ω     82.00 149.00   1.00    1.00    --  108.00  38.00  60.00   67
 62  ω     62.00  88.00   1.00    1.00    --  108.00 -91.00  90.00   26
 63  ω     86.00 122.00   1.00    1.00    --  108.00  63.00-180.00   36
 64  ω     37.00 100.00   1.00    1.00    --  108.00-111.00  90.00   63
 65  ω     45.00 111.00   1.00    1.00    --  108.00-111.00 -30.00   66
 66  ω     82.00 133.00   1.00    1.00    --  108.00  38.00 150.00   51
 67  ω    119.00 145.00   1.00    1.00    --  108.00  77.00  60.00   26
 68  ω    141.00 167.00   1.00    1.00    --  108.00  38.00  30.00   26
 69  ω     82.00 110.00   1.00    1.00    --  108.00  38.00  30.00   28
 70  ω     79.00 107.00   1.00    1.00    --  108.00  77.00  60.00   28
 71  ω    153.00 178.00   1.00    1.00    --  108.00  38.00 -60.00   25
 72  ω     82.00 112.00   1.00    1.00    --  108.00  38.00 -60.00   30
 73  ω    107.00 132.00   1.00    1.00    --  108.00  77.00 150.00   25
 74  ω     78.00 104.00   1.00    1.00    --  108.00  77.00  90.00   26
 75  ω     79.00 130.00   1.00    1.00    --  108.00 -50.00   0.00   51
 76  ω     42.00  67.00   1.00    1.00    --  108.00 -50.00   0.00   25
 77  ω     78.00 104.00   1.00    1.00    --  108.00  77.00 150.00   26
 78  ω     92.00 117.00   1.00    1.00    --  108.00  50.00-150.00   25
 79  ω     86.00 123.00   1.00    1.00    --  108.00  63.00  60.00   37
 80  ω     37.00  63.00   1.00    1.00    --  108.00-111.00-120.00   26
 81  ω     72.00 108.00   1.00    1.00    --  108.00-111.00-120.00   36
 82  ω     86.00 151.00   1.00    1.00    --  108.00  63.00  90.00   65
 83  ω    141.00 167.00   1.00    1.00    --  108.00  77.00 120.00   26
 84  ω     89.00 115.00   1.00    1.00    --  108.00  50.00 120.00   26
 85  ω    133.00 159.00   1.00    1.00    --  108.00  50.00 120.00   26
 86  ω     42.00 115.00   1.00    1.00    --  108.00 -25.00-150.00   73
 87  ω    133.00 173.00   1.00    1.00    --  108.00  77.00-150.00   40
 88  ω     88.00 173.00   1.00    1.00    --  108.00  55.00 -27.69   85
 89  ω     78.00 104.00   1.00    1.00    --  108.00  77.00   2.29   26
 90  ω     93.00 130.00   1.00    1.00    --  108.00  50.00  90.00   37
 91  ω     78.00 178.00   1.00    1.00    --  108.00  77.00 133.27  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0113107000
_diffrn_orient_matrix_UB_12      -0.1030473000
_diffrn_orient_matrix_UB_13      -0.0920258000
_diffrn_orient_matrix_UB_21      0.0610224000
_diffrn_orient_matrix_UB_22      0.1816463000
_diffrn_orient_matrix_UB_23      -0.0256106000
_diffrn_orient_matrix_UB_31      0.1158768000
_diffrn_orient_matrix_UB_32      -0.1056567000
_diffrn_orient_matrix_UB_33      0.0456690000
_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         0.826
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                4267
_reflns_number_total             4544
_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 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_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         0.178
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 
;
 Flack x determined using 1820 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         4544
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0364
_refine_ls_restrained_S_all      1.039
_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)+(0.0579P)²+0.0889P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0964
_refine_ls_wR_factor_ref         0.0999
_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:
 C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C21(H21), C12(H12), C26(H26), C28(H28), C15(H15), C14(H14),
 C23(H23), C20(H20), C25(H25)
2.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C18(H18A,H18B,H18C), C29(H29A,H29B,H29C)
2.e :
 C9(H9)
;
_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
O2 O 0.51041(16) 0.3961(3) 0.82426(11) 0.0667(5) Uani 1 1 d . . . . .
O4 O 1.19967(17) 0.0601(4) 0.84882(15) 0.0847(6) Uani 1 1 d . . . . .
O3 O 0.45928(19) 0.0798(3) 0.77303(15) 0.0832(6) Uani 1 1 d . . . . .
C8 C 0.2931(2) 0.6837(3) 0.41152(15) 0.0577(5) Uani 1 1 d . . . . .
C13 C 0.4402(2) 0.4758(4) 0.73940(15) 0.0550(5) Uani 1 1 d . . . . .
C22 C 0.90977(19) -0.0108(3) 0.85880(13) 0.0507(5) Uani 1 1 d . . . . .
C10 C 0.30700(17) 0.6436(3) 0.57229(14) 0.0462(4) Uani 1 1 d . . . . .
C3 C 0.1125(2) 0.6419(4) 0.43791(16) 0.0579(5) Uani 1 1 d . . . . .
H3A H 0.113236 0.505374 0.414527 0.070 Uiso 1 1 calc R U . . .
H3B H 0.075881 0.639184 0.483951 0.070 Uiso 1 1 calc R U . . .
C11 C 0.25770(19) 0.5589(4) 0.63203(15) 0.0528(5) Uani 1 1 d . . . . .
H11 H 0.178679 0.558936 0.615774 0.063 Uiso 1 1 calc R U . . .
C21 C 0.8203(2) -0.1526(4) 0.84127(16) 0.0586(5) Uani 1 1 d . . . . .
H21 H 0.826305 -0.277044 0.814853 0.070 Uiso 1 1 calc R U . . .
C4 C 0.23574(18) 0.7288(3) 0.47864(14) 0.0469(4) Uani 1 1 d . . . . .
C12 C 0.3239(2) 0.4744(4) 0.71538(15) 0.0586(5) Uani 1 1 d . . . . .
H12 H 0.289647 0.417461 0.754394 0.070 Uiso 1 1 calc R U . . .
C16 C 0.5152(2) 0.1910(4) 0.83256(16) 0.0583(6) Uani 1 1 d . . . . .
O1 O 0.0666(3) 1.1505(4) 0.36104(19) 0.1241(11) Uani 1 1 d . . . . .
C26 C 0.9865(2) 0.3220(4) 0.91493(16) 0.0636(6) Uani 1 1 d . . . . .
H26 H 0.978763 0.448800 0.938619 0.076 Uiso 1 1 calc R U . . .
C28 C 0.7966(2) 0.2187(4) 0.91723(14) 0.0573(5) Uani 1 1 d . . . . .
H28 H 0.788061 0.343572 0.942191 0.069 Uiso 1 1 calc R U . . .
C15 C 0.42516(19) 0.6445(4) 0.60038(15) 0.0572(5) Uani 1 1 d . . . . .
H15 H 0.460431 0.701763 0.562144 0.069 Uiso 1 1 calc R U . . .
C27 C 0.89727(19) 0.1805(3) 0.89685(13) 0.0524(5) Uani 1 1 d . . . . .
C14 C 0.4918(2) 0.5629(4) 0.68343(16) 0.0617(6) Uani 1 1 d . . . . .
H14 H 0.570977 0.566970 0.701269 0.074 Uiso 1 1 calc R U . . .
C23 C 1.0118(2) -0.0544(4) 0.84123(15) 0.0576(5) Uani 1 1 d . . . . .
H23 H 1.020172 -0.178633 0.815665 0.069 Uiso 1 1 calc R U . . .
C5 C 0.2129(2) 0.9649(3) 0.47877(15) 0.0520(5) Uani 1 1 d . . . . .
C6 C 0.1799(2) 1.0264(4) 0.56163(17) 0.0650(6) Uani 1 1 d . . . . .
H6A H 0.123575 0.933639 0.567910 0.098 Uiso 1 1 calc R U . . .
H6B H 0.149048 1.161482 0.552676 0.098 Uiso 1 1 calc R U . . .
H6C H 0.246207 1.022492 0.616269 0.098 Uiso 1 1 calc R U . . .
C19 C 0.7121(2) 0.0778(4) 0.90131(14) 0.0563(5) Uani 1 1 d . . . . .
C9 C 0.3366(3) 0.6410(5) 0.3581(2) 0.0817(8) Uani 1 1 d . . . . .
H9 H 0.371229 0.607077 0.315542 0.098 Uiso 1 1 calc R U . . .
C20 C 0.7246(2) -0.1107(4) 0.86240(16) 0.0609(6) Uani 1 1 d . . . . .
H20 H 0.667168 -0.207607 0.850954 0.073 Uiso 1 1 calc R U . . .
C24 C 1.0973(2) 0.0851(4) 0.86173(15) 0.0615(6) Uani 1 1 d . . . . .
C25 C 1.0846(2) 0.2767(5) 0.89835(17) 0.0687(7) Uani 1 1 d . . . . .
H25 H 1.142981 0.372024 0.911154 0.082 Uiso 1 1 calc R U . . .
C2 C 0.0518(2) 0.7876(4) 0.36070(18) 0.0658(6) Uani 1 1 d . . . . .
H2A H 0.063816 0.749205 0.304249 0.079 Uiso 1 1 calc R U . . .
H2B H -0.029558 0.789847 0.349853 0.079 Uiso 1 1 calc R U . . .
C1 C 0.1049(3) 0.9913(4) 0.39420(18) 0.0686(7) Uani 1 1 d . . . . .
C17 C 0.6041(2) 0.1268(5) 0.92239(16) 0.0649(6) Uani 1 1 d . . . . .
H17 H 0.619928 0.241945 0.965015 0.078 Uiso 1 1 calc R U . . .
C7 C 0.3101(3) 1.0992(4) 0.4753(2) 0.0770(8) Uani 1 1 d . . . . .
H7A H 0.375030 1.079584 0.530117 0.115 Uiso 1 1 calc R U . . .
H7B H 0.286732 1.238839 0.471086 0.115 Uiso 1 1 calc R U . . .
H7C H 0.330032 1.064061 0.422603 0.115 Uiso 1 1 calc R U . . .
C18 C 0.5601(3) -0.0490(6) 0.9646(2) 0.0952(11) Uani 1 1 d . . . . .
H18A H 0.494082 -0.006014 0.978226 0.143 Uiso 1 1 calc R U . . .
H18B H 0.618484 -0.091767 1.020166 0.143 Uiso 1 1 calc R U . . .
H18C H 0.539804 -0.160247 0.921928 0.143 Uiso 1 1 calc R U . . .
C29 C 1.2181(3) -0.1312(6) 0.8120(2) 0.0910(10) Uani 1 1 d . . . . .
H29A H 1.159526 -0.153102 0.753496 0.136 Uiso 1 1 calc R U . . .
H29B H 1.215738 -0.238258 0.853433 0.136 Uiso 1 1 calc R U . . .
H29C H 1.291308 -0.130560 0.804446 0.136 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
O2 C13 1.407(3) . ?
O2 C16 1.356(3) . ?
O4 C24 1.368(3) . ?
O4 C29 1.433(4) . ?
O3 C16 1.196(3) . ?
C8 C4 1.481(3) . ?
C8 C9 1.169(4) . ?
C13 C12 1.369(3) . ?
C13 C14 1.370(4) . ?
C22 C21 1.408(3) . ?
C22 C27 1.421(3) . ?
C22 C23 1.419(3) . ?
C10 C11 1.391(3) . ?
C10 C4 1.525(3) . ?
C10 C15 1.387(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.557(3) . ?
C3 C2 1.517(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.388(3) . ?
C21 H21 0.9300 . ?
C21 C20 1.370(3) . ?
C4 C5 1.580(3) . ?
C12 H12 0.9300 . ?
C16 C17 1.512(3) . ?
O1 C1 1.193(3) . ?
C26 H26 0.9300 . ?
C26 C27 1.404(3) . ?
C26 C25 1.366(4) . ?
C28 H28 0.9300 . ?
C28 C27 1.418(3) . ?
C28 C19 1.361(4) . ?
C15 H15 0.9300 . ?
C15 C14 1.379(3) . ?
C14 H14 0.9300 . ?
C23 H23 0.9300 . ?
C23 C24 1.361(4) . ?
C5 C6 1.531(3) . ?
C5 C1 1.533(3) . ?
C5 C7 1.516(3) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C19 C20 1.411(4) . ?
C19 C17 1.526(3) . ?
C9 H9 0.9300 . ?
C20 H20 0.9300 . ?
C24 C25 1.414(4) . ?
C25 H25 0.9300 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C1 1.507(4) . ?
C17 H17 0.9800 . ?
C17 C18 1.521(4) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 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
C16 O2 C13 116.9(2) . . ?
C24 O4 C29 116.7(2) . . ?
C9 C8 C4 177.5(3) . . ?
C12 C13 O2 120.9(2) . . ?
C12 C13 C14 121.0(2) . . ?
C14 C13 O2 118.0(2) . . ?
C21 C22 C27 118.4(2) . . ?
C21 C22 C23 122.2(2) . . ?
C23 C22 C27 119.5(2) . . ?
C11 C10 C4 122.26(19) . . ?
C15 C10 C11 117.3(2) . . ?
C15 C10 C4 120.47(18) . . ?
H3A C3 H3B 109.0 . . ?
C4 C3 H3A 110.9 . . ?
C4 C3 H3B 110.9 . . ?
C2 C3 H3A 110.9 . . ?
C2 C3 H3B 110.9 . . ?
C2 C3 C4 104.11(19) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 C10 121.4(2) . . ?
C12 C11 H11 119.3 . . ?
C22 C21 H21 119.4 . . ?
C20 C21 C22 121.2(2) . . ?
C20 C21 H21 119.4 . . ?
C8 C4 C10 109.24(17) . . ?
C8 C4 C3 106.85(18) . . ?
C8 C4 C5 109.22(18) . . ?
C10 C4 C3 115.01(17) . . ?
C10 C4 C5 114.03(17) . . ?
C3 C4 C5 102.04(17) . . ?
C13 C12 C11 119.1(2) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
O2 C16 C17 111.1(2) . . ?
O3 C16 O2 122.8(2) . . ?
O3 C16 C17 126.0(2) . . ?
C27 C26 H26 119.4 . . ?
C25 C26 H26 119.4 . . ?
C25 C26 C27 121.2(2) . . ?
C27 C28 H28 119.1 . . ?
C19 C28 H28 119.1 . . ?
C19 C28 C27 121.9(2) . . ?
C10 C15 H15 119.1 . . ?
C14 C15 C10 121.8(2) . . ?
C14 C15 H15 119.1 . . ?
C26 C27 C22 118.6(2) . . ?
C26 C27 C28 122.7(2) . . ?
C28 C27 C22 118.7(2) . . ?
C13 C14 C15 119.3(2) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C22 C23 H23 119.9 . . ?
C24 C23 C22 120.1(2) . . ?
C24 C23 H23 119.9 . . ?
C6 C5 C4 111.20(19) . . ?
C6 C5 C1 106.0(2) . . ?
C1 C5 C4 102.49(18) . . ?
C7 C5 C4 115.3(2) . . ?
C7 C5 C6 108.9(2) . . ?
C7 C5 C1 112.5(2) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C28 C19 C20 119.0(2) . . ?
C28 C19 C17 120.2(2) . . ?
C20 C19 C17 120.8(2) . . ?
C8 C9 H9 180.0 . . ?
C21 C20 C19 120.8(2) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
O4 C24 C25 113.9(2) . . ?
C23 C24 O4 125.5(2) . . ?
C23 C24 C25 120.6(2) . . ?
C26 C25 C24 120.1(2) . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C3 C2 H2A 110.9 . . ?
C3 C2 H2B 110.9 . . ?
H2A C2 H2B 108.9 . . ?
C1 C2 C3 104.43(19) . . ?
C1 C2 H2A 110.9 . . ?
C1 C2 H2B 110.9 . . ?
O1 C1 C5 124.9(3) . . ?
O1 C1 C2 124.7(2) . . ?
C2 C1 C5 110.3(2) . . ?
C16 C17 C19 106.55(18) . . ?
C16 C17 H17 108.6 . . ?
C16 C17 C18 110.4(2) . . ?
C19 C17 H17 108.6 . . ?
C18 C17 C19 114.0(2) . . ?
C18 C17 H17 108.6 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
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 . . ?
O4 C29 H29A 109.5 . . ?
O4 C29 H29B 109.5 . . ?
O4 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 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
O2 C13 C12 C11 178.5(2) . . . . ?
O2 C13 C14 C15 -179.2(2) . . . . ?
O2 C16 C17 C19 -96.5(2) . . . . ?
O2 C16 C17 C18 139.2(2) . . . . ?
O4 C24 C25 C26 -179.8(2) . . . . ?
O3 C16 C17 C19 79.8(3) . . . . ?
O3 C16 C17 C18 -44.5(4) . . . . ?
C8 C4 C5 C6 -166.7(2) . . . . ?
C8 C4 C5 C1 80.4(2) . . . . ?
C8 C4 C5 C7 -42.1(3) . . . . ?
C13 O2 C16 O3 -3.3(4) . . . . ?
C13 O2 C16 C17 173.14(19) . . . . ?
C22 C21 C20 C19 0.9(4) . . . . ?
C22 C23 C24 O4 179.4(2) . . . . ?
C22 C23 C24 C25 -1.7(4) . . . . ?
C10 C11 C12 C13 0.5(4) . . . . ?
C10 C4 C5 C6 -44.2(3) . . . . ?
C10 C4 C5 C1 -157.07(19) . . . . ?
C10 C4 C5 C7 80.4(3) . . . . ?
C10 C15 C14 C13 0.9(4) . . . . ?
C3 C4 C5 C6 80.5(2) . . . . ?
C3 C4 C5 C1 -32.4(2) . . . . ?
C3 C4 C5 C7 -155.0(2) . . . . ?
C3 C2 C1 O1 -165.6(4) . . . . ?
C3 C2 C1 C5 12.6(3) . . . . ?
C11 C10 C4 C8 -143.4(2) . . . . ?
C11 C10 C4 C3 -23.3(3) . . . . ?
C11 C10 C4 C5 94.1(2) . . . . ?
C11 C10 C15 C14 0.8(3) . . . . ?
C21 C22 C27 C26 179.6(2) . . . . ?
C21 C22 C27 C28 1.3(3) . . . . ?
C21 C22 C23 C24 -178.1(2) . . . . ?
C4 C10 C11 C12 177.3(2) . . . . ?
C4 C10 C15 C14 -178.0(2) . . . . ?
C4 C3 C2 C1 -33.4(3) . . . . ?
C4 C5 C1 O1 -169.0(4) . . . . ?
C4 C5 C1 C2 12.9(3) . . . . ?
C12 C13 C14 C15 -2.1(4) . . . . ?
C16 O2 C13 C12 74.4(3) . . . . ?
C16 O2 C13 C14 -108.4(3) . . . . ?
C28 C19 C20 C21 0.4(3) . . . . ?
C28 C19 C17 C16 97.7(3) . . . . ?
C28 C19 C17 C18 -140.3(3) . . . . ?
C15 C10 C11 C12 -1.5(3) . . . . ?
C15 C10 C4 C8 35.3(3) . . . . ?
C15 C10 C4 C3 155.4(2) . . . . ?
C15 C10 C4 C5 -87.2(2) . . . . ?
C27 C22 C21 C20 -1.7(3) . . . . ?
C27 C22 C23 C24 0.8(3) . . . . ?
C27 C26 C25 C24 0.4(4) . . . . ?
C27 C28 C19 C20 -0.8(3) . . . . ?
C27 C28 C19 C17 -178.72(19) . . . . ?
C14 C13 C12 C11 1.4(4) . . . . ?
C23 C22 C21 C20 177.2(2) . . . . ?
C23 C22 C27 C26 0.7(3) . . . . ?
C23 C22 C27 C28 -177.62(19) . . . . ?
C23 C24 C25 C26 1.1(4) . . . . ?
C6 C5 C1 O1 74.3(4) . . . . ?
C6 C5 C1 C2 -103.8(3) . . . . ?
C19 C28 C27 C22 -0.1(3) . . . . ?
C19 C28 C27 C26 -178.4(2) . . . . ?
C20 C19 C17 C16 -80.2(3) . . . . ?
C20 C19 C17 C18 41.8(3) . . . . ?
C25 C26 C27 C22 -1.3(3) . . . . ?
C25 C26 C27 C28 177.0(2) . . . . ?
C2 C3 C4 C8 -73.3(2) . . . . ?
C2 C3 C4 C10 165.26(19) . . . . ?
C2 C3 C4 C5 41.3(2) . . . . ?
C17 C19 C20 C21 178.3(2) . . . . ?
C7 C5 C1 O1 -44.6(4) . . . . ?
C7 C5 C1 C2 137.3(2) . . . . ?
C29 O4 C24 C23 -1.1(4) . . . . ?
C29 O4 C24 C25 179.9(3) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 5.483
_oxdiff_exptl_absorpt_empirical_full_min 0.457
