# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_frojjh26
_database_code_depnum_ccdc_archive 'CCDC 2174699'
loop_
_audit_author_name
_audit_author_address
'William W. Brennessel'
;University of Rochester
United States of America
;
_audit_update_record             
;
2022-05-24 deposited with the CCDC.	2022-11-04 downloaded from the CCDC.
;
_audit_creation_date             2022-05-07
_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         'C21 H20 O4'
_chemical_formula_sum            'C21 H20 O4'
_chemical_formula_weight         336.37
_chemical_melting_point          ?
_chemical_oxdiff_formula         ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/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                   11.33020(10)
_cell_length_b                   9.30400(10)
_cell_length_c                   15.25110(10)
_cell_angle_alpha                90
_cell_angle_beta                 92.0390(10)
_cell_angle_gamma                90
_cell_volume                     1606.69(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    19155
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      80.0110
_cell_measurement_theta_min      4.7700
_shelx_estimated_absorpt_T_max   0.957
_shelx_estimated_absorpt_T_min   0.909
_exptl_absorpt_coefficient_mu    0.776
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94365
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.120a (Rigaku Oxford Diffraction, 2021)
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    1.391
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.126
_exptl_crystal_size_mid          0.118
_exptl_crystal_size_min          0.057
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            28132
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        74.504
_diffrn_reflns_theta_max         80.320
_diffrn_reflns_theta_min         4.782
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     25.00 120.00   0.50    0.13    --   47.32  77.00   0.00  190
  2  ω     25.00 120.00   0.50    0.13    --   47.32  77.00 -60.00  190
  3  ω     33.00 120.00   0.50    0.13    --   47.32  57.00 -90.00  174
  4  ω     35.00 121.00   0.50    0.13    --   47.32  35.00-127.00  172
  5  ω     25.00 120.00   0.50    0.13    --   47.32  77.00  30.00  190
  6  ω     25.00 120.00   0.50    0.13    --   47.32  77.00 120.00  190
  7  ω    -26.00  46.00   0.50    0.13    --   47.32 -35.00  75.00  144
  8  ω    101.00 178.00   0.50    0.52    --  113.25  45.00  90.00  154
  9  ω     95.00 178.00   0.50    0.52    --  113.25 125.00  90.00  166
 10  ω     95.00 178.00   0.50    0.52    --  113.25 125.00  60.00  166
 11  ω    101.00 176.00   0.50    0.52    --  113.25  30.00  30.00  150
 12  ω    100.00 178.00   0.50    0.52    --  113.25  15.00   0.00  156
 13  ω    100.00 178.00   0.50    0.52    --  113.25  15.00 -60.00  156
 14  ω    101.00 178.00   0.50    0.52    --  113.25  35.00-127.00  154
 15  ω    100.00 178.00   0.50    0.52    --  113.25  15.00-180.00  156
 16  ω     42.00  79.00   0.50    0.52    --  113.25 -61.00 -90.00   74
 17  ω     42.00  79.00   0.50    0.52    --  113.25 -61.00-180.00   74
 18  ω     42.00  79.00   0.50    0.52    --  113.25 -61.00-120.00   74
 19  ω     42.00  79.00   0.50    0.52    --  113.25 -61.00 -60.00   74
 20  ω     42.00  79.00   0.50    0.52    --  113.25 -61.00  30.00   74
 21  ω     42.00  79.00   0.50    0.52    --  113.25 -61.00  90.00   74
 22  ω     42.00  79.00   0.50    0.52    --  113.25 -61.00 150.00   74
 23  ω     42.00  79.00   0.50    0.52    --  113.25 -61.00  60.00   74
 24  ω     42.00  79.00   0.50    0.52    --  113.25 -61.00-150.00   74
 25  ω     42.00  79.00   0.50    0.52    --  113.25 -61.00 -30.00   74
 26  ω     42.00  79.00   0.50    0.52    --  113.25 -61.00   0.00   74
 27  ω     42.00  79.00   0.50    0.52    --  113.25 -61.00 120.00   74
 28  ω     42.00 106.00   0.50    0.52    --  113.25 -94.00 120.00  128
 29  ω     34.00  95.00   0.50    0.13    --   47.32-125.00 150.00  122
 30  ω     42.00 106.00   0.50    0.52    --  113.25 -94.00 -90.00  128
 31  ω     42.00 106.00   0.50    0.52    --  113.25 -94.00-120.00  128
 32  ω     42.00 106.00   0.50    0.52    --  113.25 -94.00-150.00  128
 33  ω     42.00 111.00   0.50    0.52    --  113.25-125.00-180.00  138
 34  ω    -16.00  28.00   0.50    0.13    --  -47.32  19.00  30.00   88
 35  ω    -16.00  28.00   0.50    0.13    --  -47.32  19.00 -30.00   88
 36  ω    -32.00  26.00   0.50    0.13    --  -47.32  35.00-127.00  116
 37  ω    -65.00 -19.00   0.50    0.52    --  -91.75  61.00  30.00   92
 38  ω   -121.00 -35.00   0.50    0.13    --  -47.32 -35.00  75.00  172
 39  ω   -165.00 -79.00   0.50    0.52    --  -91.75 -35.00  75.00  172
 40  ω   -119.00 -73.00   0.50    0.13    --  -47.32-125.00 150.00   92
 41  ω   -119.00 -73.00   0.50    0.13    --  -47.32-125.00  30.00   92
 42  ω   -119.00 -25.00   0.50    0.13    --  -47.32 -77.00-180.00  188
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0468983000
_diffrn_orient_matrix_UB_12      0.0673144000
_diffrn_orient_matrix_UB_13      0.0842091000
_diffrn_orient_matrix_UB_21      0.1186001000
_diffrn_orient_matrix_UB_22      -0.0322936000
_diffrn_orient_matrix_UB_23      0.0485416000
_diffrn_orient_matrix_UB_31      0.0473668000
_diffrn_orient_matrix_UB_32      0.1477777000
_diffrn_orient_matrix_UB_33      -0.0277883000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3218
_reflns_number_total             3482
_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 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.120a (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, 2015b)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015a)'
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3482
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0358
_refine_ls_restrained_S_all      1.061
_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)+(0.0455P)²+0.5536P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0917
_refine_ls_wR_factor_ref         0.0935
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C6(H6A,H6B), C7(H7A,H7B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C13(H13), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.91542(7) 0.12804(10) 0.72236(5) 0.02689(19) Uani 1 1 d . . . . .
O2 O 0.33316(7) 0.27741(11) 0.51363(6) 0.0313(2) Uani 1 1 d . . . . .
O3 O 0.40469(7) 0.11253(10) 0.41417(5) 0.0283(2) Uani 1 1 d . . . . .
O4 O 0.87541(7) 0.08843(8) 0.51595(5) 0.02115(17) Uani 1 1 d . . . . .
C1 C 1.03283(10) 0.18481(14) 0.73321(8) 0.0272(3) Uani 1 1 d . . . . .
H1A H 1.077760 0.126743 0.777370 0.033 Uiso 1 1 calc R U . . .
H1B H 1.028705 0.284569 0.755472 0.033 Uiso 1 1 calc R U . . .
C2 C 1.09756(10) 0.18396(13) 0.64754(7) 0.0244(2) Uani 1 1 d . . . . .
H2A H 1.109341 0.083586 0.628155 0.029 Uiso 1 1 calc R U . . .
H2B H 1.176189 0.229019 0.656688 0.029 Uiso 1 1 calc R U . . .
C3 C 1.02639(9) 0.26649(12) 0.57674(7) 0.0211(2) Uani 1 1 d . . . . .
H3A H 1.026738 0.370289 0.591030 0.025 Uiso 1 1 calc R U . . .
H3B H 1.063225 0.253895 0.519348 0.025 Uiso 1 1 calc R U . . .
C4 C 0.90109(9) 0.21218(11) 0.57113(7) 0.0192(2) Uani 1 1 d . . . . .
C5 C 0.84217(9) 0.20387(12) 0.65904(7) 0.0218(2) Uani 1 1 d . . . . .
H5 H 0.768736 0.145473 0.649526 0.026 Uiso 1 1 calc R U . . .
C6 C 0.80339(10) 0.35220(13) 0.69003(7) 0.0242(2) Uani 1 1 d . . . . .
H6A H 0.873826 0.407925 0.709875 0.029 Uiso 1 1 calc R U . . .
H6B H 0.751882 0.340970 0.740676 0.029 Uiso 1 1 calc R U . . .
C7 C 0.73622(10) 0.43567(12) 0.61669(7) 0.0235(2) Uani 1 1 d . . . . .
H7A H 0.691614 0.514792 0.643565 0.028 Uiso 1 1 calc R U . . .
H7B H 0.794372 0.479446 0.577775 0.028 Uiso 1 1 calc R U . . .
C8 C 0.65109(9) 0.34479(12) 0.56150(7) 0.0201(2) Uani 1 1 d . . . . .
C9 C 0.52844(10) 0.36281(13) 0.56899(7) 0.0228(2) Uani 1 1 d . . . . .
H9 H 0.497709 0.430569 0.608809 0.027 Uiso 1 1 calc R U . . .
C10 C 0.45479(10) 0.27943(13) 0.51699(7) 0.0228(2) Uani 1 1 d . . . . .
C11 C 0.30053(10) 0.18280(14) 0.44277(9) 0.0307(3) Uani 1 1 d . . . . .
H11A H 0.243030 0.110648 0.462541 0.037 Uiso 1 1 calc R U . . .
H11B H 0.263255 0.238152 0.393746 0.037 Uiso 1 1 calc R U . . .
C12 C 0.49716(9) 0.18063(12) 0.45811(7) 0.0216(2) Uani 1 1 d . . . . .
C13 C 0.61595(9) 0.15949(12) 0.44943(7) 0.0207(2) Uani 1 1 d . . . . .
H13 H 0.644896 0.091186 0.409184 0.025 Uiso 1 1 calc R U . . .
C14 C 0.69301(9) 0.24297(12) 0.50252(7) 0.0187(2) Uani 1 1 d . . . . .
C15 C 0.82360(9) 0.22684(11) 0.49133(7) 0.0184(2) Uani 1 1 d . . . . .
C16 C 0.86681(9) 0.28407(12) 0.40590(7) 0.0191(2) Uani 1 1 d . . . . .
C17 C 0.95903(10) 0.21630(13) 0.36350(7) 0.0230(2) Uani 1 1 d . . . . .
H17 H 0.998575 0.136855 0.390417 0.028 Uiso 1 1 calc R U . . .
C18 C 0.99292(10) 0.26511(14) 0.28193(7) 0.0275(3) Uani 1 1 d . . . . .
H18 H 1.055599 0.218534 0.253469 0.033 Uiso 1 1 calc R U . . .
C19 C 0.93630(10) 0.38087(14) 0.24173(7) 0.0268(3) Uani 1 1 d . . . . .
H19 H 0.959738 0.413356 0.185915 0.032 Uiso 1 1 calc R U . . .
C20 C 0.84492(10) 0.44910(13) 0.28372(7) 0.0245(2) Uani 1 1 d . . . . .
H20 H 0.805723 0.528559 0.256540 0.029 Uiso 1 1 calc R U . . .
C21 C 0.81069(9) 0.40128(12) 0.36553(7) 0.0210(2) Uani 1 1 d . . . . .
H21 H 0.748594 0.448902 0.394074 0.025 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 C1 1.4354(13) . ?
O1 C5 1.4360(13) . ?
O2 C10 1.3773(13) . ?
O2 C11 1.4321(16) . ?
O3 C11 1.4306(15) . ?
O3 C12 1.3778(13) . ?
O4 C4 1.4495(13) . ?
O4 C15 1.4589(13) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.5209(16) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.5310(15) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.5065(14) . ?
C4 C5 1.5209(14) . ?
C4 C15 1.4813(14) . ?
C5 H5 1.0000 . ?
C5 C6 1.5283(16) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.5404(15) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.5153(15) . ?
C8 C9 1.4084(15) . ?
C8 C14 1.4010(15) . ?
C9 H9 0.9500 . ?
C9 C10 1.3711(16) . ?
C10 C12 1.3829(16) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.3713(15) . ?
C13 H13 0.9500 . ?
C13 C14 1.4038(15) . ?
C14 C15 1.5029(14) . ?
C15 C16 1.5054(14) . ?
C16 C17 1.3985(15) . ?
C16 C21 1.3946(15) . ?
C17 H17 0.9500 . ?
C17 C18 1.3911(16) . ?
C18 H18 0.9500 . ?
C18 C19 1.3855(18) . ?
C19 H19 0.9500 . ?
C19 C20 1.3900(17) . ?
C20 H20 0.9500 . ?
C20 C21 1.3928(15) . ?
C21 H21 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C5 114.07(8) . . ?
C10 O2 C11 105.52(9) . . ?
C12 O3 C11 105.24(9) . . ?
C4 O4 C15 61.24(6) . . ?
O1 C1 H1A 109.2 . . ?
O1 C1 H1B 109.2 . . ?
O1 C1 C2 111.85(9) . . ?
H1A C1 H1B 107.9 . . ?
C2 C1 H1A 109.2 . . ?
C2 C1 H1B 109.2 . . ?
C1 C2 H2A 109.6 . . ?
C1 C2 H2B 109.6 . . ?
C1 C2 C3 110.20(9) . . ?
H2A C2 H2B 108.1 . . ?
C3 C2 H2A 109.6 . . ?
C3 C2 H2B 109.6 . . ?
C2 C3 H3A 109.6 . . ?
C2 C3 H3B 109.6 . . ?
H3A C3 H3B 108.2 . . ?
C4 C3 C2 110.09(9) . . ?
C4 C3 H3A 109.6 . . ?
C4 C3 H3B 109.6 . . ?
O4 C4 C3 117.95(9) . . ?
O4 C4 C5 112.72(9) . . ?
O4 C4 C15 59.69(6) . . ?
C3 C4 C5 114.16(9) . . ?
C15 C4 C3 123.06(9) . . ?
C15 C4 C5 117.58(9) . . ?
O1 C5 C4 110.89(9) . . ?
O1 C5 H5 106.8 . . ?
O1 C5 C6 113.66(9) . . ?
C4 C5 H5 106.8 . . ?
C4 C5 C6 111.52(9) . . ?
C6 C5 H5 106.8 . . ?
C5 C6 H6A 109.3 . . ?
C5 C6 H6B 109.3 . . ?
C5 C6 C7 111.76(9) . . ?
H6A C6 H6B 107.9 . . ?
C7 C6 H6A 109.3 . . ?
C7 C6 H6B 109.3 . . ?
C6 C7 H7A 108.7 . . ?
C6 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C8 C7 C6 114.23(9) . . ?
C8 C7 H7A 108.7 . . ?
C8 C7 H7B 108.7 . . ?
C9 C8 C7 119.93(10) . . ?
C14 C8 C7 120.68(9) . . ?
C14 C8 C9 119.38(10) . . ?
C8 C9 H9 121.1 . . ?
C10 C9 C8 117.88(10) . . ?
C10 C9 H9 121.1 . . ?
O2 C10 C12 109.68(10) . . ?
C9 C10 O2 128.08(11) . . ?
C9 C10 C12 122.24(10) . . ?
O2 C11 H11A 110.0 . . ?
O2 C11 H11B 110.0 . . ?
O3 C11 O2 108.50(9) . . ?
O3 C11 H11A 110.0 . . ?
O3 C11 H11B 110.0 . . ?
H11A C11 H11B 108.4 . . ?
O3 C12 C10 110.23(10) . . ?
C13 C12 O3 128.25(11) . . ?
C13 C12 C10 121.51(10) . . ?
C12 C13 H13 121.4 . . ?
C12 C13 C14 117.22(10) . . ?
C14 C13 H13 121.4 . . ?
C8 C14 C13 121.76(10) . . ?
C8 C14 C15 119.87(9) . . ?
C13 C14 C15 118.29(9) . . ?
O4 C15 C4 59.07(6) . . ?
O4 C15 C14 116.60(8) . . ?
O4 C15 C16 113.24(8) . . ?
C4 C15 C14 118.23(9) . . ?
C4 C15 C16 122.83(9) . . ?
C14 C15 C16 114.50(9) . . ?
C17 C16 C15 120.81(10) . . ?
C21 C16 C15 120.10(9) . . ?
C21 C16 C17 119.00(10) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 C16 120.06(11) . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 119.6 . . ?
C19 C18 C17 120.75(11) . . ?
C19 C18 H18 119.6 . . ?
C18 C19 H19 120.3 . . ?
C18 C19 C20 119.46(10) . . ?
C20 C19 H19 120.3 . . ?
C19 C20 H20 119.9 . . ?
C19 C20 C21 120.17(11) . . ?
C21 C20 H20 119.9 . . ?
C16 C21 H21 119.7 . . ?
C20 C21 C16 120.54(10) . . ?
C20 C21 H21 119.7 . . ?

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 C1 C2 C3 55.92(13) . . . . ?
O1 C5 C6 C7 174.01(9) . . . . ?
O2 C10 C12 O3 0.58(13) . . . . ?
O2 C10 C12 C13 -178.93(10) . . . . ?
O3 C12 C13 C14 -179.78(10) . . . . ?
O4 C4 C5 O1 87.45(10) . . . . ?
O4 C4 C5 C6 -144.79(9) . . . . ?
O4 C4 C15 C14 105.70(10) . . . . ?
O4 C4 C15 C16 -99.26(11) . . . . ?
O4 C15 C16 C17 -7.97(14) . . . . ?
O4 C15 C16 C21 168.49(9) . . . . ?
C1 O1 C5 C4 54.41(12) . . . . ?
C1 O1 C5 C6 -72.17(12) . . . . ?
C1 C2 C3 C4 -51.37(12) . . . . ?
C2 C3 C4 O4 -85.84(11) . . . . ?
C2 C3 C4 C5 49.97(12) . . . . ?
C2 C3 C4 C15 -156.20(10) . . . . ?
C3 C4 C5 O1 -50.68(12) . . . . ?
C3 C4 C5 C6 77.08(11) . . . . ?
C3 C4 C15 O4 105.50(11) . . . . ?
C3 C4 C15 C14 -148.79(10) . . . . ?
C3 C4 C15 C16 6.24(16) . . . . ?
C4 O4 C15 C14 -108.47(10) . . . . ?
C4 O4 C15 C16 115.50(10) . . . . ?
C4 C5 C6 C7 47.76(12) . . . . ?
C4 C15 C16 C17 59.16(14) . . . . ?
C4 C15 C16 C21 -124.38(11) . . . . ?
C5 O1 C1 C2 -58.55(13) . . . . ?
C5 C4 C15 O4 -101.50(10) . . . . ?
C5 C4 C15 C14 4.21(14) . . . . ?
C5 C4 C15 C16 159.24(10) . . . . ?
C5 C6 C7 C8 40.56(12) . . . . ?
C6 C7 C8 C9 109.19(11) . . . . ?
C6 C7 C8 C14 -71.09(13) . . . . ?
C7 C8 C9 C10 179.23(10) . . . . ?
C7 C8 C14 C13 -178.73(10) . . . . ?
C7 C8 C14 C15 -2.13(15) . . . . ?
C8 C9 C10 O2 179.34(10) . . . . ?
C8 C9 C10 C12 -0.40(16) . . . . ?
C8 C14 C15 O4 116.94(11) . . . . ?
C8 C14 C15 C4 49.49(14) . . . . ?
C8 C14 C15 C16 -107.57(11) . . . . ?
C9 C8 C14 C13 0.98(16) . . . . ?
C9 C8 C14 C15 177.59(9) . . . . ?
C9 C10 C12 O3 -179.63(10) . . . . ?
C9 C10 C12 C13 0.85(17) . . . . ?
C10 O2 C11 O3 9.06(12) . . . . ?
C10 C12 C13 C14 -0.35(16) . . . . ?
C11 O2 C10 C9 174.28(11) . . . . ?
C11 O2 C10 C12 -5.95(12) . . . . ?
C11 O3 C12 C10 5.05(12) . . . . ?
C11 O3 C12 C13 -175.47(11) . . . . ?
C12 O3 C11 O2 -8.69(12) . . . . ?
C12 C13 C14 C8 -0.55(16) . . . . ?
C12 C13 C14 C15 -177.21(9) . . . . ?
C13 C14 C15 O4 -66.34(12) . . . . ?
C13 C14 C15 C4 -133.79(10) . . . . ?
C13 C14 C15 C16 69.15(13) . . . . ?
C14 C8 C9 C10 -0.49(15) . . . . ?
C14 C15 C16 C17 -144.96(10) . . . . ?
C14 C15 C16 C21 31.51(14) . . . . ?
C15 O4 C4 C3 -113.91(10) . . . . ?
C15 O4 C4 C5 109.68(10) . . . . ?
C15 C4 C5 O1 153.97(9) . . . . ?
C15 C4 C5 C6 -78.28(12) . . . . ?
C15 C16 C17 C18 175.95(10) . . . . ?
C15 C16 C21 C20 -175.74(10) . . . . ?
C16 C17 C18 C19 0.05(17) . . . . ?
C17 C16 C21 C20 0.79(16) . . . . ?
C17 C18 C19 C20 0.24(18) . . . . ?
C18 C19 C20 C21 -0.01(17) . . . . ?
C19 C20 C21 C16 -0.51(16) . . . . ?
C21 C16 C17 C18 -0.56(16) . . . . ?

_olex2_submission_original_sample_id frojjh26
_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 1.131
_oxdiff_exptl_absorpt_empirical_full_min 0.897
####################################################################### 
# 
# 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_frojjh23
_database_code_depnum_ccdc_archive 'CCDC 2174702'
loop_
_audit_author_name
_audit_author_address
'William W. Brennessel'
;University of Rochester
United States of America
;
_audit_update_record             
;
2022-05-24 deposited with the CCDC.	2022-11-04 downloaded from the CCDC.
;

_vrf_PLAT301_frojjh23            
;
PROBLEM: _G Main Residue Disorder ..............(Resd  1  ) .. 12% 
RESPONSE: Part of ring O1/C1-C5 is modeled as disordered over two
positions (0.934(3):0.066(3)), corresponding to a cocrystallization
of two diastereomers (and their inverses by symmetry).
;

_vrf_PLAT860_frojjh23            
;
PROBLEM: _G Number of Least-Squares Restraints ............. 106 
RESPONSE: Analogous bond lengths between the two positions of
the disordered ring were restrained to be similar. Anisotropic
displacement parameters for proximal atoms were restrained to
be similar.
;

_audit_creation_date             2022-02-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H22 O3'
_chemical_formula_sum            'C22 H22 O3'
_chemical_formula_weight         334.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   11.11210(10)
_cell_length_b                   14.44820(10)
_cell_length_c                   11.06860(10)
_cell_angle_alpha                90
_cell_angle_beta                 100.5810(10)
_cell_angle_gamma                90
_cell_volume                     1746.85(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13280
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      80.0630
_cell_measurement_theta_min      4.0280
_shelx_estimated_absorpt_T_max   0.932
_shelx_estimated_absorpt_T_min   0.860
_exptl_absorpt_coefficient_mu    0.665
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89800
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.120a (Rigaku Oxford Diffraction, 2021)
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    1.271
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.234
_exptl_crystal_size_mid          0.139
_exptl_crystal_size_min          0.108
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            20536
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        74.504
_diffrn_reflns_theta_max         80.156
_diffrn_reflns_theta_min         4.047
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     25.00 120.00   0.50    0.06    --   47.26  77.00   0.00  190
  2  ω     25.00 120.00   0.50    0.06    --   47.26  77.00  30.00  190
  3  ω     25.00 120.00   0.50    0.06    --   47.26  77.00  90.00  190
  4  ω     25.00 120.00   0.50    0.06    --   47.26  77.00 -90.00  190
  5  ω     25.00 120.00   0.50    0.06    --   47.26  77.00-120.00  190
  6  ω     25.00 120.00   0.50    0.06    --   47.26  77.00-180.00  190
  7  ω     32.00 120.00   0.50    0.06    --   47.26  57.00-180.00  176
  8  ω     35.00 120.00   0.50    0.06    --   47.26  38.00 150.00  170
  9  ω    136.00 167.00   0.50    0.23    --  113.25 125.00  60.00   62
 10  ω    114.00 147.00   0.50    0.23    --  113.25 125.00  90.00   66
 11  ω    100.00 136.00   0.50    0.23    --  113.25 125.00   0.00   72
 12  ω    122.00 178.00   0.50    0.23    --  113.25 125.00 -30.00  112
 13  ω    153.00 178.00   0.50    0.23    --  113.25 125.00 -90.00   50
 14  ω     95.00 140.00   0.50    0.23    --  113.25 125.00 -90.00   90
 15  ω    106.00 178.00   0.50    0.23    --  113.25 102.00-153.00  144
 16  ω     98.00 131.00   0.50    0.23    --  113.25 125.00  60.00   66
 17  ω    115.00 169.00   0.50    0.23    --  113.25 125.00 150.00  108
 18  ω    114.00 169.00   0.50    0.23    --  113.25  82.00 124.34  110
 19  ω    100.00 144.00   0.50    0.23    --  113.25  15.00 120.00   88
 20  ω     93.00 119.00   0.50    0.23    --  113.25  77.00 120.00   52
 21  ω    121.00 147.00   0.50    0.23    --  113.25  77.00   0.00   52
 22  ω     91.00 118.00   0.50    0.23    --  113.25  77.00   0.00   54
 23  ω     93.00 135.00   0.50    0.23    --  113.25  77.00 -60.00   84
 24  ω     92.00 150.00   0.50    0.23    --  113.25  77.00-120.00  116
 25  ω     93.00 124.00   0.50    0.23    --  113.25  77.00-150.00   62
 26  ω    -73.00 -47.00   0.50    0.06    --  -47.27 102.00-153.00   52
 27  ω     56.00  87.00   0.50    0.23    --  113.25 -94.00 120.00   62
 28  ω     43.00  68.00   0.50    0.23    --  113.25 -61.00 150.00   50
 29  ω     42.00  73.00   0.50    0.23    --  113.25-125.00-120.00   62
 30  ω     76.00 109.00   0.50    0.23    --  113.25-125.00-120.00   66
 31  ω     53.00  79.00   0.50    0.23    --  113.25 -61.00 -90.00   52
 32  ω     42.00  68.00   0.50    0.23    --  113.25-125.00 -30.00   52
 33  ω     82.00 107.00   0.50    0.23    --  113.25-125.00 -30.00   50
 34  ω     47.00  73.00   0.50    0.23    --  113.25 -77.00  60.00   52
 35  ω     90.00 130.00   0.50    0.23    --  113.25 -77.00  60.00   80
 36  ω     58.00  84.00   0.50    0.23    --  113.25-102.00 103.00   52
 37  ω     62.00  88.00   0.50    0.23    --  113.25 -94.00-120.00   52
 38  ω     46.00  73.00   0.50    0.23    --  113.25 -61.00 120.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0649973000
_diffrn_orient_matrix_UB_12      -0.0926724000
_diffrn_orient_matrix_UB_13      -0.0133603000
_diffrn_orient_matrix_UB_21      0.1226717000
_diffrn_orient_matrix_UB_22      0.0428110000
_diffrn_orient_matrix_UB_23      0.0623318000
_diffrn_orient_matrix_UB_31      -0.0248320000
_diffrn_orient_matrix_UB_32      -0.0309813000
_diffrn_orient_matrix_UB_33      0.1263214000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3460
_reflns_number_total             3744
_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 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.120a (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, 2015b)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015a)'
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3744
_refine_ls_number_restraints     106
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0417
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0483P)²+0.7583P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1039
_refine_ls_wR_factor_ref         0.1057
_refine_special_details          
;
Part of ring O1/C1-C5 is modeled as disordered over two positions
(0.934(3):0.066(3)), corresponding to a cocrystallization of two
diastereomers (and their inverses by symmetry). Analogous bond
lengths between the two positions of the disordered ring were
restrained to be similar. Anisotropic displacement parameters
for proximal atoms were restrained to be similar.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C5-O1 \\sim C5-O1'
 with sigma of 0.01
 O1-C1 \\sim O1'-C1'
 with sigma of 0.01
 C1-C2 \\sim C1'-C2
 with sigma of 0.01
 C1-C22 \\sim C1'-C22'
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 1.4A with sigma of 0.005 and
sigma for terminal atoms of 0.01 within 1.4A
C22 \\sim C22': within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
4. Others
 Sof(H2BC)=Sof(H2BD)=Sof(H5B)=Sof(O1')=Sof(C1')=Sof(H1')=Sof(C22')=Sof(H22D)=
 Sof(H22E)=Sof(H22F)=1-FVAR(1)
 Sof(H2AA)=Sof(H2AB)=Sof(H5A)=Sof(O1)=Sof(C1)=Sof(H1)=Sof(C22)=Sof(H22A)=
 Sof(H22B)=Sof(H22C)=FVAR(1)
5.a Riding coordinates:
 C5(H5A), C5(H5B)
5.b Ternary CH refined with riding coordinates:
 C1(H1), C1'(H1')
5.c Secondary CH2 refined with riding coordinates:
 C2(H2AA,H2AB), C2(H2BC,H2BD), C3(H3A,H3B), C6(H6A,H6B), C7(H7A,H7B), C11(H11A,
 H11B)
5.d Aromatic/amide H refined with riding coordinates:
 C9(H9), C13(H13), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
5.e Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C22'(H22D,H22E,H22F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.00736(9) 0.20339(6) 0.07661(10) 0.0323(2) Uani 1 1 d . U . . .
O3 O -0.02101(9) 0.33471(6) -0.04549(9) 0.0286(2) Uani 1 1 d . U . . .
C2 C 0.32732(12) 0.45656(9) 0.71266(11) 0.0234(3) Uani 1 1 d D . . . .
H2AA H 0.320168 0.395717 0.751861 0.028 Uiso 0.934(3) 1 calc R U P A 1
H2AB H 0.376174 0.497841 0.774323 0.028 Uiso 0.934(3) 1 calc R U P A 1
H2BC H 0.387546 0.465978 0.789464 0.028 Uiso 0.066(3) 1 calc R U P A 2
H2BD H 0.277251 0.401336 0.722447 0.028 Uiso 0.066(3) 1 calc R U P A 2
C3 C 0.39278(11) 0.44458(9) 0.60238(11) 0.0227(3) Uani 1 1 d . . . . .
H3A H 0.442646 0.500257 0.594363 0.027 Uiso 1 1 calc R U . . .
H3B H 0.448561 0.390664 0.616831 0.027 Uiso 1 1 calc R U . . .
C4 C 0.30175(11) 0.43028(8) 0.48528(11) 0.0201(2) Uani 1 1 d . U . . .
C5 C 0.20571(11) 0.50602(8) 0.45975(11) 0.0204(2) Uani 1 1 d D . . . .
H5A H 0.127040 0.477949 0.432929 0.024 Uiso 0.934(3) 1 d R U P A 1
H5B H 0.138480 0.471759 0.413879 0.024 Uiso 0.066(3) 1 d R U P A 2
C6 C 0.22979(12) 0.57451(9) 0.36167(12) 0.0236(3) Uani 1 1 d . . . . .
H6A H 0.295487 0.617808 0.398324 0.028 Uiso 1 1 calc R U . . .
H6B H 0.154798 0.611189 0.332669 0.028 Uiso 1 1 calc R U . . .
C7 C 0.26774(11) 0.52497(8) 0.25184(11) 0.0208(2) Uani 1 1 d . . . . .
H7A H 0.256211 0.568082 0.181130 0.025 Uiso 1 1 calc R U . . .
H7B H 0.356097 0.510179 0.272977 0.025 Uiso 1 1 calc R U . . .
C8 C 0.19817(10) 0.43670(8) 0.21259(11) 0.0177(2) Uani 1 1 d . . . . .
C9 C 0.11944(11) 0.43463(8) 0.09744(11) 0.0187(2) Uani 1 1 d . U . . .
H9 H 0.107820 0.487836 0.046195 0.022 Uiso 1 1 calc R U . . .
C10 C 0.06007(11) 0.35314(8) 0.06174(11) 0.0196(2) Uani 1 1 d . U . . .
C11 C -0.05922(13) 0.24116(9) -0.03403(13) 0.0291(3) Uani 1 1 d . . . . .
H11A H -0.148040 0.239278 -0.032752 0.035 Uiso 1 1 calc R U . . .
H11B H -0.043879 0.204330 -0.105086 0.035 Uiso 1 1 calc R U . . .
C12 C 0.07668(11) 0.27476(8) 0.13478(11) 0.0203(2) Uani 1 1 d . U . . .
C13 C 0.15369(11) 0.27402(8) 0.24681(11) 0.0200(2) Uani 1 1 d . U . . .
H13 H 0.165130 0.219614 0.295770 0.024 Uiso 1 1 calc R U . . .
C14 C 0.21544(10) 0.35717(8) 0.28680(10) 0.0179(2) Uani 1 1 d . . . . .
C15 C 0.30165(10) 0.35947(8) 0.40703(11) 0.0191(2) Uani 1 1 d . U . . .
C16 C 0.39100(11) 0.28130(8) 0.43134(10) 0.0192(2) Uani 1 1 d . U . . .
C17 C 0.38130(12) 0.21285(9) 0.51778(11) 0.0244(3) Uani 1 1 d . U . . .
H17 H 0.317516 0.216107 0.564212 0.029 Uiso 1 1 calc R U . . .
C18 C 0.46423(13) 0.13980(9) 0.53667(12) 0.0278(3) Uani 1 1 d . U . . .
H18 H 0.455765 0.092876 0.594659 0.033 Uiso 1 1 calc R U . . .
C19 C 0.55928(12) 0.13518(9) 0.47115(12) 0.0273(3) Uani 1 1 d . U . . .
H19 H 0.616678 0.085840 0.484980 0.033 Uiso 1 1 calc R U . . .
C20 C 0.56970(12) 0.20327(9) 0.38527(13) 0.0277(3) Uani 1 1 d . U . . .
H20 H 0.634669 0.200587 0.340295 0.033 Uiso 1 1 calc R U . . .
C21 C 0.48585(12) 0.27521(9) 0.36472(12) 0.0239(3) Uani 1 1 d . U . . .
H21 H 0.493035 0.320839 0.304651 0.029 Uiso 1 1 calc R U . . .
O1 O 0.20221(11) 0.55925(7) 0.56845(8) 0.0209(3) Uani 0.934(3) 1 d D U P A 1
C1 C 0.19986(13) 0.49780(10) 0.67074(12) 0.0219(3) Uani 0.934(3) 1 d D U P A 1
H1 H 0.139848 0.446840 0.644522 0.026 Uiso 0.934(3) 1 calc R U P A 1
C22 C 0.1586(3) 0.5542(4) 0.7720(3) 0.0343(7) Uani 0.934(3) 1 d D U P A 1
H22A H 0.212420 0.607921 0.791631 0.051 Uiso 0.934(3) 1 calc R U P A 1
H22B H 0.162645 0.515618 0.845499 0.051 Uiso 0.934(3) 1 calc R U P A 1
H22C H 0.074258 0.575188 0.744061 0.051 Uiso 0.934(3) 1 calc R U P A 1
O1' O 0.1554(13) 0.5299(12) 0.5710(9) 0.0231(19) Uani 0.066(3) 1 d D U P A 2
C1' C 0.2451(15) 0.5430(10) 0.6827(14) 0.023(2) Uani 0.066(3) 1 d D U P A 2
H1' H 0.292990 0.601572 0.682571 0.028 Uiso 0.066(3) 1 calc R U P A 2
C22' C 0.143(5) 0.551(7) 0.756(6) 0.035(2) Uani 0.066(3) 1 d D U P A 2
H22D H 0.089049 0.496391 0.740132 0.052 Uiso 0.066(3) 1 calc R U P A 2
H22E H 0.095166 0.606854 0.732493 0.052 Uiso 0.066(3) 1 calc R U P A 2
H22F H 0.177925 0.553200 0.844337 0.052 Uiso 0.066(3) 1 calc R U P A 2


_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 C11 1.4185(16) . ?
O2 C12 1.3745(15) . ?
O3 C10 1.3779(14) . ?
O3 C11 1.4294(16) . ?
C2 H2AA 0.9900 . ?
C2 H2AB 0.9900 . ?
C2 H2BC 0.9900 . ?
C2 H2BD 0.9900 . ?
C2 C3 1.5412(17) . ?
C2 C1 1.5280(18) . ?
C2 C1' 1.546(9) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.5048(16) . ?
C4 C5 1.5184(16) . ?
C4 C15 1.3404(17) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 C6 1.5284(17) . ?
C5 O1 1.4345(14) . ?
C5 O1' 1.484(9) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.5350(17) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.5131(16) . ?
C8 C9 1.4075(16) . ?
C8 C14 1.4051(16) . ?
C9 H9 0.9500 . ?
C9 C10 1.3718(17) . ?
C10 C12 1.3839(17) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.3712(17) . ?
C13 H13 0.9500 . ?
C13 C14 1.4136(16) . ?
C14 C15 1.4906(16) . ?
C15 C16 1.4952(16) . ?
C16 C17 1.3939(17) . ?
C16 C21 1.3956(17) . ?
C17 H17 0.9500 . ?
C17 C18 1.3915(18) . ?
C18 H18 0.9500 . ?
C18 C19 1.3884(19) . ?
C19 H19 0.9500 . ?
C19 C20 1.3875(19) . ?
C20 H20 0.9500 . ?
C20 C21 1.3865(18) . ?
C21 H21 0.9500 . ?
O1 C1 1.4427(16) . ?
C1 H1 1.0000 . ?
C1 C22 1.522(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
O1' C1' 1.451(10) . ?
C1' H1' 1.0000 . ?
C1' C22' 1.522(10) . ?
C22' H22D 0.9800 . ?
C22' H22E 0.9800 . ?
C22' H22F 0.9800 . ?

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
C12 O2 C11 105.92(10) . . ?
C10 O3 C11 105.32(9) . . ?
H2AA C2 H2AB 108.1 . . ?
H2BC C2 H2BD 108.8 . . ?
C3 C2 H2AA 109.6 . . ?
C3 C2 H2AB 109.6 . . ?
C3 C2 H2BC 110.6 . . ?
C3 C2 H2BD 110.6 . . ?
C3 C2 C1' 105.5(7) . . ?
C1 C2 H2AA 109.6 . . ?
C1 C2 H2AB 109.6 . . ?
C1 C2 C3 110.44(10) . . ?
C1' C2 H2BC 110.6 . . ?
C1' C2 H2BD 110.6 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 108.0 . . ?
C4 C3 C2 110.93(10) . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C3 C4 C5 113.56(10) . . ?
C15 C4 C3 125.59(11) . . ?
C15 C4 C5 120.84(11) . . ?
C4 C5 H5A 108.8 . . ?
C4 C5 H5B 100.3 . . ?
C4 C5 C6 112.96(10) . . ?
C6 C5 H5A 108.8 . . ?
C6 C5 H5B 100.3 . . ?
O1 C5 C4 110.89(10) . . ?
O1 C5 H5A 108.8 . . ?
O1 C5 C6 106.49(10) . . ?
O1' C5 C4 111.9(6) . . ?
O1' C5 H5B 100.6 . . ?
O1' C5 C6 125.5(7) . . ?
C5 C6 H6A 109.3 . . ?
C5 C6 H6B 109.3 . . ?
C5 C6 C7 111.72(10) . . ?
H6A C6 H6B 107.9 . . ?
C7 C6 H6A 109.3 . . ?
C7 C6 H6B 109.3 . . ?
C6 C7 H7A 108.6 . . ?
C6 C7 H7B 108.6 . . ?
H7A C7 H7B 107.5 . . ?
C8 C7 C6 114.85(10) . . ?
C8 C7 H7A 108.6 . . ?
C8 C7 H7B 108.6 . . ?
C9 C8 C7 118.54(10) . . ?
C14 C8 C7 120.91(10) . . ?
C14 C8 C9 120.49(11) . . ?
C8 C9 H9 121.1 . . ?
C10 C9 C8 117.72(11) . . ?
C10 C9 H9 121.1 . . ?
O3 C10 C12 109.94(10) . . ?
C9 C10 O3 128.16(11) . . ?
C9 C10 C12 121.90(11) . . ?
O2 C11 O3 108.91(10) . . ?
O2 C11 H11A 109.9 . . ?
O2 C11 H11B 109.9 . . ?
O3 C11 H11A 109.9 . . ?
O3 C11 H11B 109.9 . . ?
H11A C11 H11B 108.3 . . ?
O2 C12 C10 109.70(10) . . ?
C13 C12 O2 128.37(11) . . ?
C13 C12 C10 121.93(11) . . ?
C12 C13 H13 121.2 . . ?
C12 C13 C14 117.58(11) . . ?
C14 C13 H13 121.2 . . ?
C8 C14 C13 120.37(11) . . ?
C8 C14 C15 120.01(11) . . ?
C13 C14 C15 119.60(10) . . ?
C4 C15 C14 121.20(11) . . ?
C4 C15 C16 122.59(11) . . ?
C14 C15 C16 116.14(10) . . ?
C17 C16 C15 121.80(11) . . ?
C17 C16 C21 118.62(11) . . ?
C21 C16 C15 119.57(11) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.58(12) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.29(12) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 120.3 . . ?
C20 C19 C18 119.41(12) . . ?
C20 C19 H19 120.3 . . ?
C19 C20 H20 119.8 . . ?
C21 C20 C19 120.39(12) . . ?
C21 C20 H20 119.8 . . ?
C16 C21 H21 119.7 . . ?
C20 C21 C16 120.70(12) . . ?
C20 C21 H21 119.7 . . ?
C5 O1 C1 109.60(10) . . ?
C2 C1 H1 109.4 . . ?
O1 C1 C2 109.21(11) . . ?
O1 C1 H1 109.4 . . ?
O1 C1 C22 107.5(2) . . ?
C22 C1 C2 111.87(17) . . ?
C22 C1 H1 109.4 . . ?
C1 C22 H22A 109.5 . . ?
C1 C22 H22B 109.5 . . ?
C1 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C1' O1' C5 115.6(12) . . ?
C2 C1' H1' 113.0 . . ?
O1' C1' C2 111.4(10) . . ?
O1' C1' H1' 113.0 . . ?
O1' C1' C22' 90(3) . . ?
C22' C1' C2 114(4) . . ?
C22' C1' H1' 113.0 . . ?
C1' C22' H22D 109.5 . . ?
C1' C22' H22E 109.5 . . ?
C1' C22' H22F 109.5 . . ?
H22D C22' H22E 109.5 . . ?
H22D C22' H22F 109.5 . . ?
H22E C22' H22F 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 C12 C13 C14 179.93(12) . . . . ?
O3 C10 C12 O2 0.31(14) . . . . ?
O3 C10 C12 C13 179.63(11) . . . . ?
C2 C3 C4 C5 54.74(14) . . . . ?
C2 C3 C4 C15 -125.88(13) . . . . ?
C3 C2 C1 O1 -32.48(15) . . . . ?
C3 C2 C1 C22 -151.3(2) . . . . ?
C3 C2 C1' O1' 60.9(15) . . . . ?
C3 C2 C1' C22' 161(4) . . . . ?
C3 C4 C5 C6 102.96(12) . . . . ?
C3 C4 C5 O1 -16.49(15) . . . . ?
C3 C4 C5 O1' -45.2(8) . . . . ?
C3 C4 C15 C14 -173.28(11) . . . . ?
C3 C4 C15 C16 3.47(19) . . . . ?
C4 C5 C6 C7 43.66(14) . . . . ?
C4 C5 O1 C1 -47.39(14) . . . . ?
C4 C5 O1' C1' 46.5(15) . . . . ?
C4 C15 C16 C17 74.22(16) . . . . ?
C4 C15 C16 C21 -106.87(14) . . . . ?
C5 C4 C15 C14 6.06(18) . . . . ?
C5 C4 C15 C16 -177.20(11) . . . . ?
C5 C6 C7 C8 40.18(14) . . . . ?
C5 O1 C1 C2 74.94(14) . . . . ?
C5 O1 C1 C22 -163.53(16) . . . . ?
C5 O1' C1' C2 -56(2) . . . . ?
C5 O1' C1' C22' -173(4) . . . . ?
C6 C5 O1 C1 -170.65(10) . . . . ?
C6 C5 O1' C1' -96.9(13) . . . . ?
C6 C7 C8 C9 112.95(12) . . . . ?
C6 C7 C8 C14 -69.74(14) . . . . ?
C7 C8 C9 C10 178.00(10) . . . . ?
C7 C8 C14 C13 -177.39(10) . . . . ?
C7 C8 C14 C15 1.06(16) . . . . ?
C8 C9 C10 O3 179.68(11) . . . . ?
C8 C9 C10 C12 -0.53(18) . . . . ?
C8 C14 C15 C4 45.21(16) . . . . ?
C8 C14 C15 C16 -131.74(11) . . . . ?
C9 C8 C14 C13 -0.13(17) . . . . ?
C9 C8 C14 C15 178.32(10) . . . . ?
C9 C10 C12 O2 -179.52(11) . . . . ?
C9 C10 C12 C13 -0.20(19) . . . . ?
C10 O3 C11 O2 -4.35(14) . . . . ?
C10 C12 C13 C14 0.74(18) . . . . ?
C11 O2 C12 C10 -3.00(14) . . . . ?
C11 O2 C12 C13 177.73(13) . . . . ?
C11 O3 C10 C9 -177.69(12) . . . . ?
C11 O3 C10 C12 2.49(14) . . . . ?
C12 O2 C11 O3 4.55(15) . . . . ?
C12 C13 C14 C8 -0.57(17) . . . . ?
C12 C13 C14 C15 -179.04(10) . . . . ?
C13 C14 C15 C4 -136.32(12) . . . . ?
C13 C14 C15 C16 46.73(15) . . . . ?
C14 C8 C9 C10 0.68(17) . . . . ?
C14 C15 C16 C17 -108.88(13) . . . . ?
C14 C15 C16 C21 70.03(15) . . . . ?
C15 C4 C5 C6 -76.45(14) . . . . ?
C15 C4 C5 O1 164.10(12) . . . . ?
C15 C4 C5 O1' 135.4(8) . . . . ?
C15 C16 C17 C18 178.62(12) . . . . ?
C15 C16 C21 C20 -179.82(12) . . . . ?
C16 C17 C18 C19 1.3(2) . . . . ?
C17 C16 C21 C20 -0.88(19) . . . . ?
C17 C18 C19 C20 -1.0(2) . . . . ?
C18 C19 C20 C21 -0.2(2) . . . . ?
C19 C20 C21 C16 1.1(2) . . . . ?
C21 C16 C17 C18 -0.30(19) . . . . ?
O1 C5 C6 C7 165.62(10) . . . . ?
C1 C2 C3 C4 -28.13(15) . . . . ?
O1' C5 C6 C7 -173.3(7) . . . . ?
C1' C2 C3 C4 -60.3(7) . . . . ?

_olex2_submission_original_sample_id frojjh23
_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 1.210
_oxdiff_exptl_absorpt_empirical_full_min 0.813
####################################################################### 
# 
# 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_frojjh27
_database_code_depnum_ccdc_archive 'CCDC 2174700'
loop_
_audit_author_name
_audit_author_address
'William W. Brennessel'
;University of Rochester
United States of America
;
_audit_update_record             
;
2022-05-24 deposited with the CCDC.	2022-11-04 downloaded from the CCDC.
;
_audit_creation_date             2022-05-03
_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         'C21 H22 O3'
_chemical_formula_sum            'C21 H22 O3'
_chemical_formula_weight         322.38
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   14.11320(10)
_cell_length_b                   19.7985(2)
_cell_length_c                   5.92430(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1655.37(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14603
_cell_measurement_temperature    99.97(10)
_cell_measurement_theta_max      79.3750
_cell_measurement_theta_min      3.8320
_shelx_estimated_absorpt_T_max   0.935
_shelx_estimated_absorpt_T_min   0.830
_exptl_absorpt_coefficient_mu    0.680
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87289
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.120a (Rigaku Oxford Diffraction, 2021)
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    1.294
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.284
_exptl_crystal_size_mid          0.227
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            19326
_diffrn_reflns_point_group_measured_fraction_full 0.945
_diffrn_reflns_point_group_measured_fraction_max 0.911
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.166
_diffrn_reflns_theta_min         3.846
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.97(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    101.00 178.00   0.50    0.14    --  113.25  30.00  30.00  154
  2  ω    101.00 178.00   0.50    0.14    --  113.25  45.00  90.00  154
  3  ω    102.00 178.00   0.50    0.14    --  113.25 113.00 -75.00  152
  4  ω    101.00 178.00   0.50    0.14    --  113.25  45.00 -90.00  154
  5  ω    100.00 125.00   0.50    0.14    --  113.25  15.00-180.00   50
  6  ω    -16.00  28.00   0.50    0.05    --  -47.32  19.00 120.00   88
  7  ω    -83.00 -19.00   0.50    0.14    --  -91.75 113.00 -75.00  128
  8  ω    -70.00  25.00   0.50    0.05    --  -47.32  76.00-154.00  190
  9  ω    -46.00 -19.00   0.50    0.14    --  -91.75  47.00  58.00   54
 10  ω   -163.00 -79.00   0.50    0.14    --  -91.75 -47.00 -90.00  168
 11  ω   -119.00 -73.00   0.50    0.05    --  -47.32-125.00-150.00   92
 12  ω   -119.00 -25.00   0.50    0.05    --  -47.32 -77.00-180.00  188
 13  ω   -119.00 -25.00   0.50    0.05    --  -47.32 -77.00-120.00  188
 14  ω   -120.00 -35.00   0.50    0.05    --  -47.32 -38.00 -60.00  170
 15  ω   -120.00 -35.00   0.50    0.05    --  -47.32 -38.00  30.00  170
 16  ω   -119.00 -25.00   0.50    0.05    --  -47.32 -77.00  30.00  188
 17  ω   -119.00 -25.00   0.50    0.05    --  -47.32 -77.00 120.00  188
 18  ω     42.00  79.00   0.50    0.14    --  113.25 -61.00-150.00   74
 19  ω     42.00 106.00   0.50    0.14    --  113.25 -94.00-120.00  128
 20  ω     42.00 114.00   0.50    0.14    --  113.25 -76.00  78.00  144
 21  ω     42.00  79.00   0.50    0.14    --  113.25 -61.00  30.00   74
 22  ω     42.00  79.00   0.50    0.14    --  113.25 -61.00 -90.00   74
 23  ω   -140.00-115.00   0.50    0.14    --  -91.75 -76.00  78.00   50
 24  ω    112.00 138.00   0.50    0.14    --  113.25  45.00 120.00   52
 25  ω    102.00 128.00   0.50    0.14    --  113.25  61.00  30.00   52
 26  ω    147.00 176.00   0.50    0.14    --  113.25  61.00  30.00   58
 27  ω     64.00 105.00   0.50    0.14    --  113.25 -94.00  90.00   82
 28  ω     42.00  67.00   0.50    0.14    --  113.25 -61.00 -60.00   50
 29  ω     49.00  99.00   0.50    0.14    --  113.25 -94.00 -90.00  100
 30  ω     80.00 106.00   0.50    0.14    --  113.25 -94.00-150.00   52
 31  ω     50.00  78.00   0.50    0.14    --  113.25 -61.00 150.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0550468000
_diffrn_orient_matrix_UB_12      0.0509872000
_diffrn_orient_matrix_UB_13      -0.1464899000
_diffrn_orient_matrix_UB_21      -0.0921546000
_diffrn_orient_matrix_UB_22      -0.0396833000
_diffrn_orient_matrix_UB_23      0.0421164000
_diffrn_orient_matrix_UB_31      -0.0198592000
_diffrn_orient_matrix_UB_32      0.0433654000
_diffrn_orient_matrix_UB_33      0.2106530000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.675
_reflns_Friedel_fraction_full    0.878
_reflns_Friedel_fraction_max     0.815
_reflns_number_gt                3221
_reflns_number_total             3305
_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 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.120a (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, 2015b)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015a)'
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 1257 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3305
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0312
_refine_ls_restrained_S_all      1.047
_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)+(0.0432P)²+0.2917P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0777
_refine_ls_wR_factor_ref         0.0783
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C5(H5), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C6(H6A,H6B), C7(H7A,H7B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C13(H13), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.04042(8) 0.42092(7) 0.8277(3) 0.0259(3) Uani 1 1 d . . . . .
O2 O 0.53642(9) 0.40612(6) 0.2142(3) 0.0269(3) Uani 1 1 d . . . . .
O3 O 0.49647(9) 0.29309(6) 0.1695(3) 0.0272(3) Uani 1 1 d . . . . .
C1 C 0.01424(13) 0.43381(10) 0.5982(4) 0.0286(4) Uani 1 1 d . . . . .
H1A H 0.052907 0.471578 0.538961 0.034 Uiso 1 1 calc R U . . .
H1B H -0.053100 0.447702 0.592602 0.034 Uiso 1 1 calc R U . . .
C2 C 0.02827(13) 0.37219(10) 0.4493(4) 0.0271(4) Uani 1 1 d . . . . .
H2A H 0.015173 0.384298 0.290149 0.033 Uiso 1 1 calc R U . . .
H2B H -0.016858 0.336378 0.494425 0.033 Uiso 1 1 calc R U . . .
C3 C 0.13004(12) 0.34559(8) 0.4701(3) 0.0202(3) Uani 1 1 d . . . . .
H3A H 0.136961 0.303153 0.383270 0.024 Uiso 1 1 calc R U . . .
H3B H 0.175153 0.379161 0.408576 0.024 Uiso 1 1 calc R U . . .
C4 C 0.15127(11) 0.33272(8) 0.7199(3) 0.0174(3) Uani 1 1 d . . . . .
H4 H 0.102141 0.300253 0.774915 0.021 Uiso 1 1 calc R U . . .
C5 C 0.13665(12) 0.39870(9) 0.8528(3) 0.0205(4) Uani 1 1 d . . . . .
H5 H 0.145080 0.387090 1.015885 0.025 Uiso 1 1 calc R U . . .
C6 C 0.20546(12) 0.45655(8) 0.8029(3) 0.0230(4) Uani 1 1 d . . . . .
H6A H 0.187047 0.496083 0.895332 0.028 Uiso 1 1 calc R U . . .
H6B H 0.198679 0.469497 0.642309 0.028 Uiso 1 1 calc R U . . .
C7 C 0.31018(12) 0.44041(9) 0.8492(4) 0.0232(4) Uani 1 1 d . . . . .
H7A H 0.345696 0.483312 0.863677 0.028 Uiso 1 1 calc R U . . .
H7B H 0.315125 0.416161 0.994828 0.028 Uiso 1 1 calc R U . . .
C8 C 0.35565(11) 0.39794(8) 0.6664(3) 0.0188(3) Uani 1 1 d . . . . .
C9 C 0.42510(13) 0.42789(8) 0.5285(3) 0.0218(4) Uani 1 1 d . . . . .
H9 H 0.443474 0.473642 0.549018 0.026 Uiso 1 1 calc R U . . .
C10 C 0.46532(11) 0.38874(9) 0.3633(3) 0.0200(4) Uani 1 1 d . . . . .
C11 C 0.54650(13) 0.34851(9) 0.0676(4) 0.0237(4) Uani 1 1 d . . . . .
H11A H 0.519648 0.358633 -0.083022 0.028 Uiso 1 1 calc R U . . .
H11B H 0.614308 0.336958 0.049093 0.028 Uiso 1 1 calc R U . . .
C12 C 0.44095(11) 0.32190(8) 0.3343(3) 0.0195(3) Uani 1 1 d . . . . .
C13 C 0.37274(12) 0.29147(8) 0.4643(3) 0.0184(3) Uani 1 1 d . . . . .
H13 H 0.355822 0.245534 0.441420 0.022 Uiso 1 1 calc R U . . .
C14 C 0.32863(11) 0.33061(8) 0.6326(3) 0.0172(3) Uani 1 1 d . . . . .
C15 C 0.24934(11) 0.30076(8) 0.7757(3) 0.0166(3) Uani 1 1 d . . . . .
H15 H 0.263721 0.314147 0.934763 0.020 Uiso 1 1 calc R U . . .
C16 C 0.24964(11) 0.22367(8) 0.7735(3) 0.0172(3) Uani 1 1 d . . . . .
C17 C 0.19299(12) 0.18493(8) 0.6304(3) 0.0208(4) Uani 1 1 d . . . . .
H17 H 0.151881 0.206662 0.526270 0.025 Uiso 1 1 calc R U . . .
C18 C 0.19617(13) 0.11443(8) 0.6390(4) 0.0233(4) Uani 1 1 d . . . . .
H18 H 0.157853 0.088589 0.539355 0.028 Uiso 1 1 calc R U . . .
C19 C 0.25474(13) 0.08210(8) 0.7914(4) 0.0238(4) Uani 1 1 d . . . . .
H19 H 0.255439 0.034181 0.799624 0.029 Uiso 1 1 calc R U . . .
C20 C 0.31235(13) 0.11983(9) 0.9321(4) 0.0253(4) Uani 1 1 d . . . . .
H20 H 0.353495 0.097845 1.035562 0.030 Uiso 1 1 calc R U . . .
C21 C 0.30998(12) 0.18999(9) 0.9219(3) 0.0219(4) Uani 1 1 d . . . . .
H21 H 0.350294 0.215472 1.017988 0.026 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 C1 1.432(3) . ?
O1 C5 1.4353(19) . ?
O2 C10 1.381(2) . ?
O2 C11 1.441(2) . ?
O3 C11 1.438(2) . ?
O3 C12 1.376(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.518(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.535(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.531(3) . ?
C4 H4 1.0000 . ?
C4 C5 1.539(2) . ?
C4 C15 1.557(2) . ?
C5 H5 1.0000 . ?
C5 C6 1.531(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.537(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.514(2) . ?
C8 C9 1.407(2) . ?
C8 C14 1.401(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.371(3) . ?
C10 C12 1.378(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.372(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.408(2) . ?
C14 C15 1.523(2) . ?
C15 H15 1.0000 . ?
C15 C16 1.526(2) . ?
C16 C17 1.395(2) . ?
C16 C21 1.394(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.397(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.382(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.383(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.391(2) . ?
C21 H21 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C5 113.40(14) . . ?
C10 O2 C11 105.07(13) . . ?
C12 O3 C11 105.16(13) . . ?
O1 C1 H1A 109.2 . . ?
O1 C1 H1B 109.2 . . ?
O1 C1 C2 112.03(15) . . ?
H1A C1 H1B 107.9 . . ?
C2 C1 H1A 109.2 . . ?
C2 C1 H1B 109.2 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 C3 110.55(16) . . ?
H2A C2 H2B 108.1 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
C2 C3 H3A 110.0 . . ?
C2 C3 H3B 110.0 . . ?
H3A C3 H3B 108.4 . . ?
C4 C3 C2 108.54(16) . . ?
C4 C3 H3A 110.0 . . ?
C4 C3 H3B 110.0 . . ?
C3 C4 H4 106.6 . . ?
C3 C4 C5 109.08(14) . . ?
C3 C4 C15 116.51(14) . . ?
C5 C4 H4 106.6 . . ?
C5 C4 C15 110.83(14) . . ?
C15 C4 H4 106.6 . . ?
O1 C5 C4 109.52(14) . . ?
O1 C5 H5 106.4 . . ?
O1 C5 C6 110.55(14) . . ?
C4 C5 H5 106.4 . . ?
C6 C5 C4 116.82(14) . . ?
C6 C5 H5 106.4 . . ?
C5 C6 H6A 108.6 . . ?
C5 C6 H6B 108.6 . . ?
C5 C6 C7 114.85(14) . . ?
H6A C6 H6B 107.5 . . ?
C7 C6 H6A 108.6 . . ?
C7 C6 H6B 108.6 . . ?
C6 C7 H7A 108.9 . . ?
C6 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
C8 C7 C6 113.31(16) . . ?
C8 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
C9 C8 C7 118.46(15) . . ?
C14 C8 C7 121.04(15) . . ?
C14 C8 C9 120.50(16) . . ?
C8 C9 H9 121.2 . . ?
C10 C9 C8 117.68(15) . . ?
C10 C9 H9 121.2 . . ?
C9 C10 O2 128.06(16) . . ?
C9 C10 C12 121.90(16) . . ?
C12 C10 O2 109.95(15) . . ?
O2 C11 H11A 110.2 . . ?
O2 C11 H11B 110.2 . . ?
O3 C11 O2 107.62(14) . . ?
O3 C11 H11A 110.2 . . ?
O3 C11 H11B 110.2 . . ?
H11A C11 H11B 108.5 . . ?
O3 C12 C10 110.14(15) . . ?
C13 C12 O3 128.02(15) . . ?
C13 C12 C10 121.79(16) . . ?
C12 C13 H13 121.1 . . ?
C12 C13 C14 117.78(15) . . ?
C14 C13 H13 121.1 . . ?
C8 C14 C13 120.31(15) . . ?
C8 C14 C15 119.32(15) . . ?
C13 C14 C15 120.36(14) . . ?
C4 C15 H15 105.8 . . ?
C14 C15 C4 112.18(14) . . ?
C14 C15 H15 105.8 . . ?
C14 C15 C16 112.42(13) . . ?
C16 C15 C4 114.02(13) . . ?
C16 C15 H15 105.8 . . ?
C17 C16 C15 123.59(15) . . ?
C21 C16 C15 118.35(15) . . ?
C21 C16 C17 118.06(15) . . ?
C16 C17 H17 119.7 . . ?
C16 C17 C18 120.58(16) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.38(17) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 120.2 . . ?
C18 C19 C20 119.68(16) . . ?
C20 C19 H19 120.2 . . ?
C19 C20 H20 120.0 . . ?
C19 C20 C21 119.94(17) . . ?
C21 C20 H20 120.0 . . ?
C16 C21 H21 119.3 . . ?
C20 C21 C16 121.33(17) . . ?
C20 C21 H21 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
O1 C1 C2 C3 -54.0(2) . . . . ?
O1 C5 C6 C7 173.81(16) . . . . ?
O2 C10 C12 O3 1.3(2) . . . . ?
O2 C10 C12 C13 179.02(16) . . . . ?
O3 C12 C13 C14 176.34(17) . . . . ?
C1 O1 C5 C4 -59.99(19) . . . . ?
C1 O1 C5 C6 70.1(2) . . . . ?
C1 C2 C3 C4 54.62(19) . . . . ?
C2 C3 C4 C5 -57.64(18) . . . . ?
C2 C3 C4 C15 175.98(14) . . . . ?
C3 C4 C5 O1 59.99(18) . . . . ?
C3 C4 C5 C6 -66.62(19) . . . . ?
C3 C4 C15 C14 40.84(19) . . . . ?
C3 C4 C15 C16 -88.40(18) . . . . ?
C4 C5 C6 C7 -60.1(2) . . . . ?
C4 C15 C16 C17 32.7(2) . . . . ?
C4 C15 C16 C21 -147.48(16) . . . . ?
C5 O1 C1 C2 57.4(2) . . . . ?
C5 C4 C15 C14 -84.67(18) . . . . ?
C5 C4 C15 C16 146.10(14) . . . . ?
C5 C6 C7 C8 77.9(2) . . . . ?
C6 C7 C8 C9 111.05(18) . . . . ?
C6 C7 C8 C14 -68.1(2) . . . . ?
C7 C8 C9 C10 -179.78(16) . . . . ?
C7 C8 C14 C13 -178.97(16) . . . . ?
C7 C8 C14 C15 2.6(2) . . . . ?
C8 C9 C10 O2 -177.55(17) . . . . ?
C8 C9 C10 C12 -1.4(3) . . . . ?
C8 C14 C15 C4 68.2(2) . . . . ?
C8 C14 C15 C16 -161.69(15) . . . . ?
C9 C8 C14 C13 1.9(3) . . . . ?
C9 C8 C14 C15 -176.53(16) . . . . ?
C9 C10 C12 O3 -175.45(17) . . . . ?
C9 C10 C12 C13 2.3(3) . . . . ?
C10 O2 C11 O3 -13.54(19) . . . . ?
C10 C12 C13 C14 -0.9(3) . . . . ?
C11 O2 C10 C9 -175.81(18) . . . . ?
C11 O2 C10 C12 7.68(19) . . . . ?
C11 O3 C12 C10 -9.7(2) . . . . ?
C11 O3 C12 C13 172.75(18) . . . . ?
C12 O3 C11 O2 14.31(19) . . . . ?
C12 C13 C14 C8 -1.1(2) . . . . ?
C12 C13 C14 C15 177.30(15) . . . . ?
C13 C14 C15 C4 -110.18(17) . . . . ?
C13 C14 C15 C16 19.9(2) . . . . ?
C14 C8 C9 C10 -0.6(3) . . . . ?
C14 C15 C16 C17 -96.37(19) . . . . ?
C14 C15 C16 C21 83.4(2) . . . . ?
C15 C4 C5 O1 -170.44(14) . . . . ?
C15 C4 C5 C6 62.9(2) . . . . ?
C15 C16 C17 C18 -179.37(16) . . . . ?
C15 C16 C21 C20 178.62(16) . . . . ?
C16 C17 C18 C19 0.8(3) . . . . ?
C17 C16 C21 C20 -1.6(3) . . . . ?
C17 C18 C19 C20 -1.7(3) . . . . ?
C18 C19 C20 C21 1.0(3) . . . . ?
C19 C20 C21 C16 0.7(3) . . . . ?
C21 C16 C17 C18 0.9(3) . . . . ?

_olex2_submission_original_sample_id frojjh27
_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 1.253
_oxdiff_exptl_absorpt_empirical_full_min 0.731
####################################################################### 
# 
# 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_frojjh25
_database_code_depnum_ccdc_archive 'CCDC 2174704'
loop_
_audit_author_name
_audit_author_address
'William W. Brennessel'
;University of Rochester
United States of America
;
_audit_update_record             
;
2022-05-24 deposited with the CCDC.	2022-11-04 downloaded from the CCDC.
;
_audit_creation_date             2022-02-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H22 O3'
_chemical_formula_sum            'C22 H22 O3'
_chemical_formula_weight         334.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/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                   17.2159(2)
_cell_length_b                   10.13720(10)
_cell_length_c                   20.2267(2)
_cell_angle_alpha                90
_cell_angle_beta                 110.5460(10)
_cell_angle_gamma                90
_cell_volume                     3305.44(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    19642
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.5630
_cell_measurement_theta_min      4.6590
_shelx_estimated_absorpt_T_max   0.945
_shelx_estimated_absorpt_T_min   0.891
_exptl_absorpt_coefficient_mu    0.703
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87854
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.120a (Rigaku Oxford Diffraction, 2021)
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    1.344
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.168
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.082
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            35734
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        74.504
_diffrn_reflns_theta_max         80.392
_diffrn_reflns_theta_min         4.179
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -80.00  23.00   0.50    0.39    --  -47.16  99.00  -9.00  206
  2  ω     -1.00  81.00   0.50    0.39    --   47.16 -99.00-115.00  164
  3  ω   -163.00 -86.00   0.50    1.56    --  -91.75 -99.00-115.00  154
  4  ω    -80.00 -19.00   0.50    1.56    --  -91.75  99.00  -9.00  122
  5  ω     42.00 106.00   0.50    1.56    --  113.25 -99.00-115.00  128
  6  ω    107.00 178.00   0.50    1.56    --  113.25  99.00  -9.00  142
  7  ω    -35.00  26.00   0.50    0.39    --  -47.16  38.00 150.00  122
  8  ω    -35.00  26.00   0.50    0.39    --  -47.16  38.00  90.00  122
  9  ω   -119.00 -73.00   0.50    0.39    --  -47.16-125.00  30.00   92
 10  ω   -119.00 -73.00   0.50    0.39    --  -47.16-125.00  90.00   92
 11  ω    -16.00  28.00   0.50    0.39    --  -47.16  19.00 -90.00   88
 12  ω    -65.00 -19.00   0.50    1.56    --  -91.75  61.00-180.00   92
 13  ω     42.00  79.00   0.50    1.56    --  113.25 -61.00 120.00   74
 14  ω     42.00  79.00   0.50    1.56    --  113.25 -61.00   0.00   74
 15  ω     42.00  79.00   0.50    1.56    --  113.25 -61.00  30.00   74
 16  ω     97.00 178.00   0.50    1.56    --  113.25  61.00  30.00  162
 17  ω     42.00  79.00   0.50    1.56    --  113.25 -61.00-120.00   74
 18  ω    100.00 178.00   0.50    1.56    --  113.25  15.00 -90.00  156
 19  ω     42.00 106.00   0.50    1.56    --  113.25 -94.00 -60.00  128
 20  ω     42.00 106.00   0.50    1.56    --  113.25 -94.00 -30.00  128
 21  ω     42.00  79.00   0.50    1.56    --  113.25 -61.00 -90.00   74
 22  ω     42.00 111.00   0.50    1.56    --  113.25-125.00   0.00  138
 23  ω    111.00 178.00   0.50    1.56    --  113.25  30.00 150.00  134
 24  ω    122.00 178.00   0.50    1.56    --  113.25 125.00 -60.00  112
 25  ω     47.00  76.00   0.50    1.56    --  113.25 -61.00 -30.00   58
 26  ω     45.00  70.00   0.50    1.56    --  113.25 -61.00 -60.00   50
 27  ω     74.00 100.00   0.50    1.56    --  113.25 -94.00 120.00   52
 28  ω    117.00 143.00   0.50    1.56    --  113.25  45.00 -30.00   52
 29  ω    153.00 178.00   0.50    1.56    --  113.25  45.00 -30.00   50
 30  ω     42.00  75.00   0.50    1.56    --  113.25 -61.00  90.00   66
 31  ω     48.00  78.00   0.50    1.56    --  113.25 -61.00  60.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0156664000
_diffrn_orient_matrix_UB_12      0.0660534000
_diffrn_orient_matrix_UB_13      -0.0721380000
_diffrn_orient_matrix_UB_21      0.0260363000
_diffrn_orient_matrix_UB_22      -0.1281065000
_diffrn_orient_matrix_UB_23      -0.0275631000
_diffrn_orient_matrix_UB_31      -0.0905947000
_diffrn_orient_matrix_UB_32      -0.0481909000
_diffrn_orient_matrix_UB_33      -0.0255701000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6280
_reflns_number_total             7100
_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 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.120a (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, 2015b)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015a)'
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     453
_refine_ls_number_reflns         7100
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0442
_refine_ls_restrained_S_all      1.059
_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)+(0.0692P)²+0.9432P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1209
_refine_ls_wR_factor_ref         0.1248
_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:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C6(H6A,H6B), C7(H7A,H7B), C11(H11A,
 H11B), C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B), C28(H28A,H28B),
 C29(H29A,H29B), C33(H33A,H33B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C13(H13), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C31(H31),
 C35(H35), C39(H39), C40(H40), C41(H41), C42(H42), C43(H43)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C44(H44A,H44B,H44C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.26462(5) 0.79322(9) 0.58382(5) 0.02473(19) Uani 1 1 d . . . . .
O2 O -0.13130(5) 0.69479(9) 0.66117(5) 0.0271(2) Uani 1 1 d . . . . .
O3 O -0.17349(5) 0.86846(9) 0.58242(5) 0.0264(2) Uani 1 1 d . . . . .
C1 C 0.34295(8) 0.84962(13) 0.62449(7) 0.0275(3) Uani 1 1 d . . . . .
H1A H 0.377940 0.855883 0.594844 0.033 Uiso 1 1 calc R U . . .
H1B H 0.371454 0.790917 0.664853 0.033 Uiso 1 1 calc R U . . .
C2 C 0.33372(8) 0.98657(13) 0.65227(7) 0.0265(3) Uani 1 1 d . . . . .
H2A H 0.334453 0.979799 0.701312 0.032 Uiso 1 1 calc R U . . .
H2B H 0.380586 1.043298 0.652416 0.032 Uiso 1 1 calc R U . . .
C3 C 0.25193(7) 1.04737(12) 0.60507(6) 0.0243(2) Uani 1 1 d . . . . .
H3A H 0.247458 1.139353 0.619796 0.029 Uiso 1 1 calc R U . . .
H3B H 0.249127 1.048207 0.555341 0.029 Uiso 1 1 calc R U . . .
C4 C 0.18218(7) 0.96495(12) 0.61215(6) 0.0213(2) Uani 1 1 d . . . . .
C5 C 0.19657(7) 0.81540(12) 0.60857(6) 0.0214(2) Uani 1 1 d . . . . .
C6 C 0.21407(7) 0.74431(12) 0.68014(6) 0.0234(2) Uani 1 1 d . . . . .
H6A H 0.197128 0.650816 0.670883 0.028 Uiso 1 1 calc R U . . .
H6B H 0.274552 0.745980 0.706652 0.028 Uiso 1 1 calc R U . . .
C7 C 0.16929(7) 0.80491(12) 0.72638(6) 0.0234(2) Uani 1 1 d . . . . .
H7A H 0.176134 0.745898 0.767043 0.028 Uiso 1 1 calc R U . . .
H7B H 0.195501 0.890492 0.745154 0.028 Uiso 1 1 calc R U . . .
C8 C 0.07803(7) 0.82650(12) 0.68688(6) 0.0219(2) Uani 1 1 d . . . . .
C9 C 0.01938(7) 0.74072(12) 0.69754(6) 0.0225(2) Uani 1 1 d . . . . .
H9 H 0.036068 0.670011 0.730327 0.027 Uiso 1 1 calc R U . . .
C10 C -0.06284(8) 0.76247(12) 0.65900(6) 0.0224(2) Uani 1 1 d . . . . .
C11 C -0.19937(8) 0.74489(14) 0.60240(7) 0.0303(3) Uani 1 1 d . . . . .
H11A H -0.213840 0.682025 0.562445 0.036 Uiso 1 1 calc R U . . .
H11B H -0.248735 0.757705 0.616061 0.036 Uiso 1 1 calc R U . . .
C12 C -0.08807(7) 0.86688(12) 0.61224(6) 0.0222(2) Uani 1 1 d . . . . .
C13 C -0.03243(7) 0.95259(12) 0.60076(6) 0.0223(2) Uani 1 1 d . . . . .
H13 H -0.050540 1.024371 0.568824 0.027 Uiso 1 1 calc R U . . .
C14 C 0.05250(7) 0.93029(12) 0.63802(6) 0.0212(2) Uani 1 1 d . . . . .
C15 C 0.11489(7) 1.01532(12) 0.62274(6) 0.0213(2) Uani 1 1 d . . . . .
C16 C 0.09670(7) 1.15994(12) 0.61872(6) 0.0212(2) Uani 1 1 d . . . . .
C17 C 0.10056(7) 1.23755(12) 0.56303(6) 0.0238(2) Uani 1 1 d . . . . .
H17 H 0.117045 1.198548 0.527318 0.029 Uiso 1 1 calc R U . . .
C18 C 0.08071(8) 1.37105(13) 0.55884(6) 0.0258(3) Uani 1 1 d . . . . .
H18 H 0.083662 1.422251 0.520456 0.031 Uiso 1 1 calc R U . . .
C19 C 0.05657(8) 1.42971(12) 0.61071(7) 0.0264(3) Uani 1 1 d . . . . .
H19 H 0.042917 1.520841 0.607980 0.032 Uiso 1 1 calc R U . . .
C20 C 0.05261(8) 1.35363(13) 0.66657(7) 0.0257(3) Uani 1 1 d . . . . .
H20 H 0.036684 1.393298 0.702424 0.031 Uiso 1 1 calc R U . . .
C21 C 0.07173(7) 1.22016(12) 0.67046(6) 0.0235(2) Uani 1 1 d . . . . .
H21 H 0.067876 1.169055 0.708559 0.028 Uiso 1 1 calc R U . . .
C22 C 0.12470(8) 0.75147(12) 0.54963(6) 0.0248(3) Uani 1 1 d . . . . .
H22A H 0.117005 0.796407 0.504871 0.037 Uiso 1 1 calc R U . . .
H22B H 0.073814 0.758852 0.560676 0.037 Uiso 1 1 calc R U . . .
H22C H 0.137200 0.658154 0.545541 0.037 Uiso 1 1 calc R U . . .
O4 O 0.75264(5) 0.42028(9) 0.57384(5) 0.0256(2) Uani 1 1 d . . . . .
O5 O 0.36970(5) 0.52747(9) 0.66524(5) 0.0263(2) Uani 1 1 d . . . . .
O6 O 0.32540(5) 0.34743(9) 0.59103(5) 0.0256(2) Uani 1 1 d . . . . .
C23 C 0.83222(8) 0.36708(13) 0.61355(7) 0.0273(3) Uani 1 1 d . . . . .
H23A H 0.859992 0.425687 0.654138 0.033 Uiso 1 1 calc R U . . .
H23B H 0.866748 0.364502 0.583402 0.033 Uiso 1 1 calc R U . . .
C24 C 0.82620(8) 0.22801(13) 0.64077(7) 0.0274(3) Uani 1 1 d . . . . .
H24A H 0.831852 0.231981 0.691155 0.033 Uiso 1 1 calc R U . . .
H24B H 0.871665 0.172538 0.636745 0.033 Uiso 1 1 calc R U . . .
C25 C 0.74232(7) 0.16729(13) 0.59739(6) 0.0249(3) Uani 1 1 d . . . . .
H25A H 0.735182 0.166937 0.546642 0.030 Uiso 1 1 calc R U . . .
H25B H 0.739205 0.075171 0.612518 0.030 Uiso 1 1 calc R U . . .
C26 C 0.67541(7) 0.24953(12) 0.60935(6) 0.0223(2) Uani 1 1 d . . . . .
C27 C 0.68728(7) 0.39869(12) 0.60205(6) 0.0227(2) Uani 1 1 d . . . . .
C28 C 0.70778(7) 0.47581(12) 0.67228(6) 0.0243(2) Uani 1 1 d . . . . .
H28A H 0.768790 0.478475 0.695924 0.029 Uiso 1 1 calc R U . . .
H28B H 0.688291 0.567835 0.661227 0.029 Uiso 1 1 calc R U . . .
C29 C 0.66948(7) 0.41852(12) 0.72396(6) 0.0238(2) Uani 1 1 d . . . . .
H29A H 0.697939 0.334916 0.743665 0.029 Uiso 1 1 calc R U . . .
H29B H 0.678397 0.480949 0.763588 0.029 Uiso 1 1 calc R U . . .
C30 C 0.57780(7) 0.39273(12) 0.68912(6) 0.0220(2) Uani 1 1 d . . . . .
C31 C 0.51982(8) 0.47995(12) 0.70024(6) 0.0225(2) Uani 1 1 d . . . . .
H31 H 0.537281 0.551920 0.732123 0.027 Uiso 1 1 calc R U . . .
C32 C 0.43735(8) 0.45739(12) 0.66348(6) 0.0227(2) Uani 1 1 d . . . . .
C33 C 0.30089(8) 0.47496(13) 0.60764(7) 0.0269(3) Uani 1 1 d . . . . .
H33A H 0.251357 0.467043 0.621508 0.032 Uiso 1 1 calc R U . . .
H33B H 0.287231 0.533903 0.566090 0.032 Uiso 1 1 calc R U . . .
C34 C 0.41063(7) 0.34906(12) 0.61926(6) 0.0225(2) Uani 1 1 d . . . . .
C35 C 0.46569(7) 0.25944(12) 0.60990(6) 0.0221(2) Uani 1 1 d . . . . .
H35 H 0.446875 0.182803 0.581784 0.027 Uiso 1 1 calc R U . . .
C36 C 0.55111(7) 0.28497(12) 0.64340(6) 0.0216(2) Uani 1 1 d . . . . .
C37 C 0.61184(7) 0.19935(12) 0.62600(6) 0.0220(2) Uani 1 1 d . . . . .
C38 C 0.59518(7) 0.05495(12) 0.62637(6) 0.0220(2) Uani 1 1 d . . . . .
C39 C 0.59210(8) -0.02765(13) 0.57048(6) 0.0263(3) Uani 1 1 d . . . . .
H39 H 0.603149 0.007429 0.531122 0.032 Uiso 1 1 calc R U . . .
C40 C 0.57306(8) -0.16090(13) 0.57152(7) 0.0292(3) Uani 1 1 d . . . . .
H40 H 0.571626 -0.215859 0.533060 0.035 Uiso 1 1 calc R U . . .
C41 C 0.55618(8) -0.21414(13) 0.62811(7) 0.0268(3) Uani 1 1 d . . . . .
H41 H 0.542892 -0.305022 0.628509 0.032 Uiso 1 1 calc R U . . .
C42 C 0.55891(8) -0.13304(13) 0.68429(7) 0.0256(3) Uani 1 1 d . . . . .
H42 H 0.547825 -0.168720 0.723497 0.031 Uiso 1 1 calc R U . . .
C43 C 0.57779(7) 0.00008(13) 0.68330(6) 0.0232(2) Uani 1 1 d . . . . .
H43 H 0.578930 0.054751 0.721776 0.028 Uiso 1 1 calc R U . . .
C44 C 0.61225(8) 0.45670(13) 0.54348(7) 0.0268(3) Uani 1 1 d . . . . .
H44A H 0.623924 0.548370 0.534712 0.040 Uiso 1 1 calc R U . . .
H44B H 0.563662 0.453851 0.558053 0.040 Uiso 1 1 calc R U . . .
H44C H 0.601126 0.405022 0.500182 0.040 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 C1 1.4295(15) . ?
O1 C5 1.4441(14) . ?
O2 C10 1.3776(14) . ?
O2 C11 1.4376(15) . ?
O3 C11 1.4344(16) . ?
O3 C12 1.3799(14) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.5268(18) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.5265(17) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.5104(16) . ?
C4 C5 1.5419(16) . ?
C4 C15 1.3500(17) . ?
C5 C6 1.5489(16) . ?
C5 C22 1.5288(16) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.5339(16) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.5079(16) . ?
C8 C9 1.4053(17) . ?
C8 C14 1.4042(17) . ?
C9 H9 0.9500 . ?
C9 C10 1.3731(17) . ?
C10 C12 1.3839(17) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.3720(17) . ?
C13 H13 0.9500 . ?
C13 C14 1.4085(17) . ?
C14 C15 1.4918(16) . ?
C15 C16 1.4954(16) . ?
C16 C17 1.3944(17) . ?
C16 C21 1.4030(17) . ?
C17 H17 0.9500 . ?
C17 C18 1.3911(18) . ?
C18 H18 0.9500 . ?
C18 C19 1.3904(18) . ?
C19 H19 0.9500 . ?
C19 C20 1.3892(18) . ?
C20 H20 0.9500 . ?
C20 C21 1.3882(18) . ?
C21 H21 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
O4 C23 1.4286(15) . ?
O4 C27 1.4458(14) . ?
O5 C32 1.3753(14) . ?
O5 C33 1.4406(15) . ?
O6 C33 1.4359(15) . ?
O6 C34 1.3752(14) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.5302(18) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.5314(17) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C26 1.5086(16) . ?
C26 C27 1.5398(17) . ?
C26 C37 1.3523(17) . ?
C27 C28 1.5497(17) . ?
C27 C44 1.5309(16) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C28 C29 1.5325(17) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C29 C30 1.5085(16) . ?
C30 C31 1.4094(17) . ?
C30 C36 1.4004(17) . ?
C31 H31 0.9500 . ?
C31 C32 1.3711(17) . ?
C32 C34 1.3888(17) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.3732(17) . ?
C35 H35 0.9500 . ?
C35 C36 1.4104(17) . ?
C36 C37 1.4929(16) . ?
C37 C38 1.4921(17) . ?
C38 C39 1.3928(17) . ?
C38 C43 1.4025(17) . ?
C39 H39 0.9500 . ?
C39 C40 1.3920(18) . ?
C40 H40 0.9500 . ?
C40 C41 1.3854(18) . ?
C41 H41 0.9500 . ?
C41 C42 1.3899(18) . ?
C42 H42 0.9500 . ?
C42 C43 1.3899(18) . ?
C43 H43 0.9500 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C5 117.02(9) . . ?
C10 O2 C11 104.83(9) . . ?
C12 O3 C11 104.80(9) . . ?
O1 C1 H1A 109.2 . . ?
O1 C1 H1B 109.2 . . ?
O1 C1 C2 112.11(10) . . ?
H1A C1 H1B 107.9 . . ?
C2 C1 H1A 109.2 . . ?
C2 C1 H1B 109.2 . . ?
C1 C2 H2A 109.8 . . ?
C1 C2 H2B 109.8 . . ?
H2A C2 H2B 108.3 . . ?
C3 C2 C1 109.23(10) . . ?
C3 C2 H2A 109.8 . . ?
C3 C2 H2B 109.8 . . ?
C2 C3 H3A 110.1 . . ?
C2 C3 H3B 110.1 . . ?
H3A C3 H3B 108.4 . . ?
C4 C3 C2 107.87(10) . . ?
C4 C3 H3A 110.1 . . ?
C4 C3 H3B 110.1 . . ?
C3 C4 C5 113.16(10) . . ?
C15 C4 C3 124.11(11) . . ?
C15 C4 C5 122.70(11) . . ?
O1 C5 C4 109.43(9) . . ?
O1 C5 C6 109.65(9) . . ?
O1 C5 C22 101.34(9) . . ?
C4 C5 C6 113.29(10) . . ?
C22 C5 C4 110.73(10) . . ?
C22 C5 C6 111.74(10) . . ?
C5 C6 H6A 108.7 . . ?
C5 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
C7 C6 C5 114.14(10) . . ?
C7 C6 H6A 108.7 . . ?
C7 C6 H6B 108.7 . . ?
C6 C7 H7A 109.0 . . ?
C6 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 C6 112.84(10) . . ?
C8 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
C9 C8 C7 120.01(11) . . ?
C14 C8 C7 119.48(11) . . ?
C14 C8 C9 120.48(11) . . ?
C8 C9 H9 121.1 . . ?
C10 C9 C8 117.82(11) . . ?
C10 C9 H9 121.1 . . ?
O2 C10 C12 109.63(10) . . ?
C9 C10 O2 128.68(11) . . ?
C9 C10 C12 121.63(11) . . ?
O2 C11 H11A 110.2 . . ?
O2 C11 H11B 110.2 . . ?
O3 C11 O2 107.32(10) . . ?
O3 C11 H11A 110.2 . . ?
O3 C11 H11B 110.2 . . ?
H11A C11 H11B 108.5 . . ?
O3 C12 C10 109.78(10) . . ?
C13 C12 O3 128.23(11) . . ?
C13 C12 C10 121.99(11) . . ?
C12 C13 H13 121.2 . . ?
C12 C13 C14 117.58(11) . . ?
C14 C13 H13 121.2 . . ?
C8 C14 C13 120.44(11) . . ?
C8 C14 C15 120.57(11) . . ?
C13 C14 C15 118.95(10) . . ?
C4 C15 C14 122.32(11) . . ?
C4 C15 C16 122.49(11) . . ?
C14 C15 C16 115.18(10) . . ?
C17 C16 C15 121.91(11) . . ?
C17 C16 C21 118.10(11) . . ?
C21 C16 C15 119.94(11) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 C16 121.18(11) . . ?
C18 C17 H17 119.4 . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.15(12) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 120.4 . . ?
C20 C19 C18 119.28(12) . . ?
C20 C19 H19 120.4 . . ?
C19 C20 H20 119.7 . . ?
C21 C20 C19 120.59(12) . . ?
C21 C20 H20 119.7 . . ?
C16 C21 H21 119.7 . . ?
C20 C21 C16 120.69(12) . . ?
C20 C21 H21 119.7 . . ?
C5 C22 H22A 109.5 . . ?
C5 C22 H22B 109.5 . . ?
C5 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C23 O4 C27 116.53(9) . . ?
C32 O5 C33 104.57(9) . . ?
C34 O6 C33 104.50(9) . . ?
O4 C23 H23A 109.2 . . ?
O4 C23 H23B 109.2 . . ?
O4 C23 C24 112.17(10) . . ?
H23A C23 H23B 107.9 . . ?
C24 C23 H23A 109.2 . . ?
C24 C23 H23B 109.2 . . ?
C23 C24 H24A 109.8 . . ?
C23 C24 H24B 109.8 . . ?
C23 C24 C25 109.48(10) . . ?
H24A C24 H24B 108.2 . . ?
C25 C24 H24A 109.8 . . ?
C25 C24 H24B 109.8 . . ?
C24 C25 H25A 110.1 . . ?
C24 C25 H25B 110.1 . . ?
H25A C25 H25B 108.5 . . ?
C26 C25 C24 107.79(10) . . ?
C26 C25 H25A 110.1 . . ?
C26 C25 H25B 110.1 . . ?
C25 C26 C27 113.13(10) . . ?
C37 C26 C25 124.22(11) . . ?
C37 C26 C27 122.65(11) . . ?
O4 C27 C26 109.53(10) . . ?
O4 C27 C28 109.08(9) . . ?
O4 C27 C44 101.46(9) . . ?
C26 C27 C28 113.74(10) . . ?
C44 C27 C26 110.31(10) . . ?
C44 C27 C28 111.99(10) . . ?
C27 C28 H28A 108.6 . . ?
C27 C28 H28B 108.6 . . ?
H28A C28 H28B 107.5 . . ?
C29 C28 C27 114.83(10) . . ?
C29 C28 H28A 108.6 . . ?
C29 C28 H28B 108.6 . . ?
C28 C29 H29A 109.2 . . ?
C28 C29 H29B 109.2 . . ?
H29A C29 H29B 107.9 . . ?
C30 C29 C28 112.15(10) . . ?
C30 C29 H29A 109.2 . . ?
C30 C29 H29B 109.2 . . ?
C31 C30 C29 120.02(11) . . ?
C36 C30 C29 119.39(11) . . ?
C36 C30 C31 120.53(11) . . ?
C30 C31 H31 121.1 . . ?
C32 C31 C30 117.74(11) . . ?
C32 C31 H31 121.1 . . ?
O5 C32 C34 109.46(10) . . ?
C31 C32 O5 128.67(11) . . ?
C31 C32 C34 121.80(11) . . ?
O5 C33 H33A 110.3 . . ?
O5 C33 H33B 110.3 . . ?
O6 C33 O5 107.23(9) . . ?
O6 C33 H33A 110.3 . . ?
O6 C33 H33B 110.3 . . ?
H33A C33 H33B 108.5 . . ?
O6 C34 C32 109.93(10) . . ?
C35 C34 O6 128.48(11) . . ?
C35 C34 C32 121.56(11) . . ?
C34 C35 H35 121.1 . . ?
C34 C35 C36 117.78(11) . . ?
C36 C35 H35 121.1 . . ?
C30 C36 C35 120.37(11) . . ?
C30 C36 C37 120.96(11) . . ?
C35 C36 C37 118.58(11) . . ?
C26 C37 C36 122.35(11) . . ?
C26 C37 C38 122.95(11) . . ?
C38 C37 C36 114.68(10) . . ?
C39 C38 C37 122.57(11) . . ?
C39 C38 C43 118.02(11) . . ?
C43 C38 C37 119.34(11) . . ?
C38 C39 H39 119.6 . . ?
C40 C39 C38 120.88(12) . . ?
C40 C39 H39 119.6 . . ?
C39 C40 H40 119.7 . . ?
C41 C40 C39 120.62(12) . . ?
C41 C40 H40 119.7 . . ?
C40 C41 H41 120.4 . . ?
C40 C41 C42 119.23(12) . . ?
C42 C41 H41 120.4 . . ?
C41 C42 H42 119.9 . . ?
C43 C42 C41 120.23(11) . . ?
C43 C42 H42 119.9 . . ?
C38 C43 H43 119.5 . . ?
C42 C43 C38 121.02(11) . . ?
C42 C43 H43 119.5 . . ?
C27 C44 H44A 109.5 . . ?
C27 C44 H44B 109.5 . . ?
C27 C44 H44C 109.5 . . ?
H44A C44 H44B 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 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 C1 C2 C3 -23.99(14) . . . . ?
O1 C5 C6 C7 154.98(10) . . . . ?
O2 C10 C12 O3 -0.66(14) . . . . ?
O2 C10 C12 C13 178.74(10) . . . . ?
O3 C12 C13 C14 179.83(11) . . . . ?
C1 O1 C5 C4 58.68(13) . . . . ?
C1 O1 C5 C6 -66.14(13) . . . . ?
C1 O1 C5 C22 175.65(10) . . . . ?
C1 C2 C3 C4 64.96(13) . . . . ?
C2 C3 C4 C5 -45.21(13) . . . . ?
C2 C3 C4 C15 132.85(12) . . . . ?
C3 C4 C5 O1 -12.59(13) . . . . ?
C3 C4 C5 C6 110.09(11) . . . . ?
C3 C4 C5 C22 -123.47(11) . . . . ?
C3 C4 C15 C14 -172.50(11) . . . . ?
C3 C4 C15 C16 8.64(17) . . . . ?
C4 C5 C6 C7 32.42(14) . . . . ?
C4 C15 C16 C17 47.30(16) . . . . ?
C4 C15 C16 C21 -135.28(12) . . . . ?
C5 O1 C1 C2 -38.92(14) . . . . ?
C5 C4 C15 C14 5.38(17) . . . . ?
C5 C4 C15 C16 -173.48(10) . . . . ?
C5 C6 C7 C8 49.49(14) . . . . ?
C6 C7 C8 C9 104.03(13) . . . . ?
C6 C7 C8 C14 -74.08(14) . . . . ?
C7 C8 C9 C10 -178.36(10) . . . . ?
C7 C8 C14 C13 -179.74(10) . . . . ?
C7 C8 C14 C15 2.63(16) . . . . ?
C8 C9 C10 O2 -178.32(11) . . . . ?
C8 C9 C10 C12 -1.47(17) . . . . ?
C8 C14 C15 C4 44.65(16) . . . . ?
C8 C14 C15 C16 -136.40(11) . . . . ?
C9 C8 C14 C13 2.16(17) . . . . ?
C9 C8 C14 C15 -175.47(10) . . . . ?
C9 C10 C12 O3 -178.04(10) . . . . ?
C9 C10 C12 C13 1.35(18) . . . . ?
C10 O2 C11 O3 -18.73(13) . . . . ?
C10 C12 C13 C14 0.56(17) . . . . ?
C11 O2 C10 C9 -170.82(12) . . . . ?
C11 O2 C10 C12 12.03(13) . . . . ?
C11 O3 C12 C10 -11.04(13) . . . . ?
C11 O3 C12 C13 169.61(12) . . . . ?
C12 O3 C11 O2 18.32(13) . . . . ?
C12 C13 C14 C8 -2.27(17) . . . . ?
C12 C13 C14 C15 175.40(10) . . . . ?
C13 C14 C15 C4 -133.01(12) . . . . ?
C13 C14 C15 C16 45.93(15) . . . . ?
C14 C8 C9 C10 -0.27(17) . . . . ?
C14 C15 C16 C17 -131.64(12) . . . . ?
C14 C15 C16 C21 45.78(15) . . . . ?
C15 C4 C5 O1 169.32(10) . . . . ?
C15 C4 C5 C6 -68.00(14) . . . . ?
C15 C4 C5 C22 58.44(14) . . . . ?
C15 C16 C17 C18 177.79(11) . . . . ?
C15 C16 C21 C20 -178.39(11) . . . . ?
C16 C17 C18 C19 0.08(18) . . . . ?
C17 C16 C21 C20 -0.87(17) . . . . ?
C17 C18 C19 C20 0.06(19) . . . . ?
C18 C19 C20 C21 -0.61(19) . . . . ?
C19 C20 C21 C16 1.03(18) . . . . ?
C21 C16 C17 C18 0.32(17) . . . . ?
C22 C5 C6 C7 -93.48(12) . . . . ?
O4 C23 C24 C25 19.72(14) . . . . ?
O4 C27 C28 C29 -153.87(10) . . . . ?
O5 C32 C34 O6 0.58(13) . . . . ?
O5 C32 C34 C35 -177.66(10) . . . . ?
O6 C34 C35 C36 178.36(11) . . . . ?
C23 O4 C27 C26 -58.49(13) . . . . ?
C23 O4 C27 C28 66.59(13) . . . . ?
C23 O4 C27 C44 -175.09(10) . . . . ?
C23 C24 C25 C26 -63.44(13) . . . . ?
C24 C25 C26 C27 47.65(13) . . . . ?
C24 C25 C26 C37 -131.30(12) . . . . ?
C25 C26 C27 O4 9.52(13) . . . . ?
C25 C26 C27 C28 -112.83(11) . . . . ?
C25 C26 C27 C44 120.37(11) . . . . ?
C25 C26 C37 C36 174.65(11) . . . . ?
C25 C26 C37 C38 -7.25(18) . . . . ?
C26 C27 C28 C29 -31.28(14) . . . . ?
C26 C37 C38 C39 -48.86(17) . . . . ?
C26 C37 C38 C43 134.40(12) . . . . ?
C27 O4 C23 C24 42.54(14) . . . . ?
C27 C26 C37 C36 -4.20(17) . . . . ?
C27 C26 C37 C38 173.90(11) . . . . ?
C27 C28 C29 C30 -50.17(14) . . . . ?
C28 C29 C30 C31 -103.04(13) . . . . ?
C28 C29 C30 C36 74.20(14) . . . . ?
C29 C30 C31 C32 175.47(11) . . . . ?
C29 C30 C36 C35 -179.60(10) . . . . ?
C29 C30 C36 C37 -2.99(17) . . . . ?
C30 C31 C32 O5 179.87(11) . . . . ?
C30 C31 C32 C34 3.14(17) . . . . ?
C30 C36 C37 C26 -45.14(17) . . . . ?
C30 C36 C37 C38 136.61(11) . . . . ?
C31 C30 C36 C35 -2.39(17) . . . . ?
C31 C30 C36 C37 174.23(10) . . . . ?
C31 C32 C34 O6 177.87(10) . . . . ?
C31 C32 C34 C35 -0.37(18) . . . . ?
C32 O5 C33 O6 20.34(12) . . . . ?
C32 C34 C35 C36 -3.76(17) . . . . ?
C33 O5 C32 C31 169.98(12) . . . . ?
C33 O5 C32 C34 -12.96(13) . . . . ?
C33 O6 C34 C32 12.11(12) . . . . ?
C33 O6 C34 C35 -169.81(12) . . . . ?
C34 O6 C33 O5 -19.97(12) . . . . ?
C34 C35 C36 C30 5.07(17) . . . . ?
C34 C35 C36 C37 -171.62(10) . . . . ?
C35 C36 C37 C26 131.53(12) . . . . ?
C35 C36 C37 C38 -46.71(14) . . . . ?
C36 C30 C31 C32 -1.73(17) . . . . ?
C36 C37 C38 C39 129.38(12) . . . . ?
C36 C37 C38 C43 -47.37(15) . . . . ?
C37 C26 C27 O4 -171.52(10) . . . . ?
C37 C26 C27 C28 66.14(15) . . . . ?
C37 C26 C27 C44 -60.66(15) . . . . ?
C37 C38 C39 C40 -177.36(12) . . . . ?
C37 C38 C43 C42 177.57(11) . . . . ?
C38 C39 C40 C41 0.4(2) . . . . ?
C39 C38 C43 C42 0.67(18) . . . . ?
C39 C40 C41 C42 -0.4(2) . . . . ?
C40 C41 C42 C43 0.46(19) . . . . ?
C41 C42 C43 C38 -0.62(18) . . . . ?
C43 C38 C39 C40 -0.58(18) . . . . ?
C44 C27 C28 C29 94.64(12) . . . . ?

_olex2_submission_original_sample_id frojjh25
_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 1.489
_oxdiff_exptl_absorpt_empirical_full_min 0.721
####################################################################### 
# 
# 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_frojjh30
_database_code_depnum_ccdc_archive 'CCDC 2176208'
loop_
_audit_author_name
_audit_author_address
'William W. Brennessel'
;University of Rochester
United States of America
;
_audit_update_record             
;
2022-05-31 deposited with the CCDC.	2022-11-04 downloaded from the CCDC.
;

_vrf_DIFMX02_frojjh30            
;
PROBLEM: _C  The maximum difference density is > 0.1*ZMAX*0.75
            The relevant atom site should be identified.
RESPONSE: The largest residual peak of 0.62 \%A^3^ is located
1.15 \%A from atom H17. Based on other residual peaks, it appears
to be due to a minor component of disorder of the tail end of the
molecule (the five-membered ring and attached p-methoxyphenyl
group). When modeled, the mass ratio refined to approximately
0.90:0.10 and R1 (strong data) decreased by approximately 0.08.
However, the improvement to the structure appeared to be mostly
cosmetic when the large number of additional parameters and
restraints were taken into account. Thus the final model does
not include the minor disorder in the tail section.
;

_vrf_PLAT097_frojjh30            
;
PROBLEM: _C Large Reported Max.  (Positive) Residual Density .. 0.62 eA-3 
RESPONSE: The largest residual peak of 0.62 \%A^3^ is located
1.15 \%A from atom H17. Based on other residual peaks, it appears
to be due to a minor component of disorder of the tail end of the
molecule (the five-membered ring and attached p-methoxyphenyl
group). When modeled, the mass ratio refined to approximately
0.90:0.10 and R1 (strong data) decreased by approximately 0.08.
However, the improvement to the structure appeared to be mostly
cosmetic when the large number of additional parameters and
restraints were taken into account. Thus the final model does
not include the minor disorder in the tail section.
;

_vrf_PLAT301_frojjh30            
;
PROBLEM: _G Main Residue Disorder ..............(Resd  1  ) .. 11% 
RESPONSE: A small portion of the central part of the molecule
(O1, C13-C15) is modeled as disordered over two positions
(0.601(7):0.399(7)).
;

_vrf_PLAT860_frojjh30            
;
PROBLEM: _G Number of Least-Squares Restraints ............. 36 
RESPONSE: For the disordered part of the molecule, analogous
bond lengths were restrained to be similar. Anisotropic
displacement parameters for proximal atoms were restrained
to be similar.
;

_vrf_PLAT870_frojjh30            
;
PROBLEM: _G ALERTS Related to Twinning Effects Suppressed! 
RESPONSE: The intensity data were scaled and reduced according
to non-merohedral twin law
[ 0.570 0 -0.433 / 0 -1 0 / -1.568 0 -0.566 ], a 180 degree
rotation around reciprocal lattice [0.71 0 -0.71]. There were
3585 unique isolated reflections in the first component, 3591
unique isolated reflections in the second component, and 2276
unique overlapping reflections. Without twin modeling, R1
(strong data) refined to 0.116. The mass ratio of components
refined to 0.6621(14):0.3379(14).
;

_vrf_PLAT931_frojjh30            
;
PROBLEM: _G CIFcalcFCF  Twin Law ( 1 0-1)         Est.d BASF .. 0.40 
RESPONSE: The intensity data were scaled and reduced according
to non-merohedral twin law
[ 0.570 0 -0.433 / 0 -1 0 / -1.568 0 -0.566 ], a 180 degree
rotation around reciprocal lattice [0.71 0 -0.71]. There were
3585 unique isolated reflections in the first component, 3591
unique isolated reflections in the second component, and 2276
unique overlapping reflections. Without twin modeling, R1
(strong data) refined to 0.116. The mass ratio of components
refined to 0.6621(14):0.3379(14).
;

_audit_creation_date             2022-05-31
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C31 H29 N O3'
_chemical_formula_sum            'C31 H29 N O3'
_chemical_formula_weight         463.55
_chemical_melting_point          ?
_chemical_oxdiff_formula         ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   15.9276(3)
_cell_length_b                   5.55609(9)
_cell_length_c                   27.3254(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.7546(18)
_cell_angle_gamma                90
_cell_volume                     2389.99(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    16462
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      78.7420
_cell_measurement_theta_min      3.2870
_shelx_estimated_absorpt_T_max   0.952
_shelx_estimated_absorpt_T_min   0.881
_exptl_absorpt_coefficient_mu    0.651
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63440
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.54a (Rigaku Oxford Diffraction, 2022)
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    1.288
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.104
_exptl_crystal_size_min          0.077
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.044
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            47366
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        74.504
_diffrn_reflns_theta_max         80.341
_diffrn_reflns_theta_min         3.273
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -119.00 -28.00   0.50    0.85    --  -47.32 -69.00 -75.00  182
  2  ω    -67.00  25.00   0.50    0.85    --  -47.32  69.00  56.00  184
  3  ω    -24.00  67.00   0.50    0.85    --   47.32 -69.00 -75.00  182
  4  ω    -79.00 -19.00   0.50    3.40    --  -91.75  69.00  56.00  120
  5  ω   -163.00 -72.00   0.50    3.40    --  -91.75 -69.00 -75.00  182
  6  ω     94.00 178.00   0.50    3.40    --  113.25  69.00  56.00  168
  7  ω     42.00  93.00   0.50    3.40    --  113.25 -69.00 -75.00  102
  8  ω   -119.00 -73.00   0.50    0.85    --  -47.32-125.00   0.00   92
  9  ω    -16.00  28.00   0.50    0.85    --  -47.32  19.00-180.00   88
 10  ω    -65.00 -19.00   0.50    3.40    --  -91.75  61.00-120.00   92
 11  ω    -65.00 -19.00   0.50    3.40    --  -91.75  61.00-180.00   92
 12  ω     42.00  79.00   0.50    3.40    --  113.25 -61.00 -30.00   74
 13  ω     42.00  79.00   0.50    3.40    --  113.25 -61.00  90.00   74
 14  ω    101.00 178.00   0.50    3.40    --  113.25  45.00 -30.00  154
 15  ω     42.00  79.00   0.50    3.40    --  113.25 -61.00   0.00   74
 16  ω     42.00  79.00   0.50    3.40    --  113.25 -61.00  60.00   74
 17  ω     42.00 111.00   0.50    3.40    --  113.25-125.00 -90.00  138
 18  ω    101.00 178.00   0.50    3.40    --  113.25  45.00  30.00  154
 19  ω    101.00 178.00   0.50    3.40    --  113.25  30.00-180.00  154
 20  ω    101.00 178.00   0.50    3.40    --  113.25  30.00   0.00  154
 21  ω     42.00 111.00   0.50    3.40    --  113.25-125.00 -60.00  138
 22  ω     42.00  79.00   0.50    3.40    --  113.25 -61.00-150.00   74
 23  ω     42.00  79.00   0.50    3.40    --  113.25 -61.00-180.00   74
 24  ω     42.00  79.00   0.50    3.40    --  113.25 -61.00 120.00   74
 25  ω     42.00 106.00   0.50    3.40    --  113.25 -94.00 -30.00  128
 26  ω     42.00 106.00   0.50    3.40    --  113.25 -94.00  60.00  128
 27  ω     33.00 120.00   0.50    0.85    --   47.32  57.00 150.00  174
 28  ω     33.00 120.00   0.50    0.85    --   47.32  57.00-150.00  174
 29  ω     25.00 120.00   0.50    0.85    --   47.32  77.00 -30.00  190
 30  ω     25.00  78.00   0.50    0.85    --   47.32  77.00-120.00  106
 31  ω     28.00 120.00   0.50    0.85    --   47.32  69.00  56.00  184
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0345688000
_diffrn_orient_matrix_UB_12      0.2149280000
_diffrn_orient_matrix_UB_13      0.0326147000
_diffrn_orient_matrix_UB_21      -0.0703214000
_diffrn_orient_matrix_UB_22      -0.0372696000
_diffrn_orient_matrix_UB_23      0.0322627000
_diffrn_orient_matrix_UB_31      0.0586405000
_diffrn_orient_matrix_UB_32      -0.1712230000
_diffrn_orient_matrix_UB_33      0.0339453000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                8533
_reflns_number_total             9452
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015a)'
_refine_diff_density_max         0.617
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     355
_refine_ls_number_reflns         9452
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0706
_refine_ls_restrained_S_all      1.100
_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)+(0.0704P)²+1.9418P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1831
_refine_ls_wR_factor_ref         0.1865
_refine_special_details          
;
The intensity data were scaled and reduced according
to non-merohedral twin law
[ 0.570 0 -0.433 / 0 -1 0 / -1.568 0 -0.566 ], a 180 degree
rotation around reciprocal lattice [0.71 0 -0.71]. There were
3585 unique isolated reflections in the first component, 3591
unique isolated reflections in the second component, and 2276
unique overlapping reflections. Without twin modeling, R1
(strong data) refined to 0.116. The mass ratio of components
refined to 0.6621(14):0.3379(14).

A small portion of the central part of the molecule (O1, C13-C15)
is modeled as disordered over two positions (0.601(7):0.399(7)).
Analogous bond lengths were restrained to be similar. Anisotropic
displacement parameters for proximal atoms were restrained to be
similar.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.6621(14)
 0.3379(14)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 C16-C15 \\sim C16-C15'
 with sigma of 0.02
 C15-C14 \\sim C15'-C14'
 with sigma of 0.02
 C14-O1 \\sim C14'-O1'
 with sigma of 0.02
 C14-C13 \\sim C14'-C13'
 with sigma of 0.02
 C13-C12 \\sim C13'-C12
 with sigma of 0.02
 O1-C1 \\sim O1'-C1
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 1.2A with sigma of 0.005 and
sigma for terminal atoms of 0.01 within 1.2A
5. Others
 Sof(H1B)=Sof(H12C)=Sof(H12D)=Sof(O1')=Sof(C13')=Sof(H13C)=Sof(H13D)=Sof(C14')=
 Sof(H14')=Sof(C15')=Sof(H15C)=Sof(H15D)=1-FVAR(1)
 Sof(H1A)=Sof(H12A)=Sof(H12B)=Sof(O1)=Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(C14)=
 Sof(H14)=Sof(C15)=Sof(H15A)=Sof(H15B)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C1(H1A), C1(H1B), C14(H14), C14'(H14')
6.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C12(H12A,H12B), C12(H12C,H12D), C13(H13A,H13B),
 C15(H15A,H15B), C13'(H13C,H13D), C15'(H15C,H15D)
6.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C17(H17), C20(H20), C21(H21), C23(H23),
 C24(H24), C26(H26), C27(H27), C28(H28), C29(H29), C30(H30)
6.d Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.39954(13) 0.6565(4) 0.45512(8) 0.0415(5) Uani 1 1 d . . . . .
O3 O 0.00469(12) 0.5401(3) 0.58430(7) 0.0333(4) Uani 1 1 d . . . . .
N1 N 0.33016(15) 0.7261(5) 0.47833(9) 0.0369(5) Uani 1 1 d . . . . .
C1 C 0.41607(19) 0.4802(7) 0.30341(10) 0.0433(8) Uani 1 1 d D . . . .
H1A H 0.378198 0.376770 0.279523 0.052 Uiso 0.601(7) 1 calc R U P A 1
H1B H 0.376675 0.346929 0.290407 0.052 Uiso 0.399(7) 1 calc R U P A 2
C2 C 0.3749(2) 0.7265(6) 0.29674(12) 0.0495(8) Uani 1 1 d . . . . .
H2A H 0.403930 0.836214 0.322456 0.059 Uiso 1 1 calc R U . . .
H2B H 0.314852 0.713017 0.301733 0.059 Uiso 1 1 calc R U . . .
C3 C 0.3783(2) 0.8369(6) 0.24538(12) 0.0452(8) Uani 1 1 d . . . . .
H3A H 0.335468 0.966827 0.239355 0.054 Uiso 1 1 calc R U . . .
H3B H 0.434940 0.910352 0.245348 0.054 Uiso 1 1 calc R U . . .
C4 C 0.36215(17) 0.6570(5) 0.20367(10) 0.0312(6) Uani 1 1 d . . . . .
C5 C 0.28834(17) 0.6637(5) 0.16916(11) 0.0354(6) Uani 1 1 d . . . . .
H5 H 0.247774 0.787147 0.171253 0.042 Uiso 1 1 calc R U . . .
C6 C 0.27295(17) 0.4943(5) 0.13195(11) 0.0358(6) Uani 1 1 d . . . . .
H6 H 0.221640 0.499751 0.109131 0.043 Uiso 1 1 calc R U . . .
C7 C 0.33247(17) 0.3160(5) 0.12790(10) 0.0326(6) Uani 1 1 d . . . . .
H7 H 0.321818 0.197980 0.102557 0.039 Uiso 1 1 calc R U . . .
C8 C 0.40761(16) 0.3109(5) 0.16105(9) 0.0280(5) Uani 1 1 d . . . . .
H8 H 0.449270 0.192586 0.157405 0.034 Uiso 1 1 calc R U . . .
C9 C 0.42290(15) 0.4766(5) 0.19958(9) 0.0268(5) Uani 1 1 d . . . . .
C10 C 0.50281(16) 0.4613(5) 0.23585(10) 0.0308(6) Uani 1 1 d . . . . .
C11 C 0.50089(17) 0.4677(6) 0.28469(10) 0.0389(7) Uani 1 1 d . . . . .
C12 C 0.57788(18) 0.4627(6) 0.32437(10) 0.0388(7) Uani 1 1 d D . . . .
H12A H 0.625962 0.395857 0.309654 0.047 Uiso 0.601(7) 1 calc R U P A 1
H12B H 0.592617 0.630886 0.334102 0.047 Uiso 0.601(7) 1 calc R U P A 1
H12C H 0.585585 0.616847 0.342676 0.047 Uiso 0.399(7) 1 calc R U P A 2
H12D H 0.630291 0.423458 0.310662 0.047 Uiso 0.399(7) 1 calc R U P A 2
C16 C 0.40569(18) 0.4106(6) 0.45690(10) 0.0376(6) Uani 1 1 d D . . . .
C17 C 0.34412(19) 0.3220(5) 0.48023(11) 0.0384(6) Uani 1 1 d . . . . .
H17 H 0.333568 0.157922 0.486934 0.046 Uiso 1 1 calc R U . . .
C18 C 0.29821(18) 0.5256(5) 0.49270(10) 0.0326(6) Uani 1 1 d . . . . .
C19 C 0.22124(17) 0.5331(5) 0.51703(9) 0.0321(6) Uani 1 1 d . . . . .
C20 C 0.16521(17) 0.7226(5) 0.50840(10) 0.0330(6) Uani 1 1 d . . . . .
H20 H 0.177008 0.849862 0.487250 0.040 Uiso 1 1 calc R U . . .
C21 C 0.09253(17) 0.7312(5) 0.52979(10) 0.0319(6) Uani 1 1 d . . . . .
H21 H 0.054614 0.863324 0.523294 0.038 Uiso 1 1 calc R U . . .
C22 C 0.07445(16) 0.5458(5) 0.56105(9) 0.0281(5) Uani 1 1 d . . . . .
C23 C 0.13000(18) 0.3522(5) 0.57049(10) 0.0332(6) Uani 1 1 d . . . . .
H23 H 0.118042 0.225613 0.591767 0.040 Uiso 1 1 calc R U . . .
C24 C 0.20293(18) 0.3457(5) 0.54856(10) 0.0351(6) Uani 1 1 d . . . . .
H24 H 0.240952 0.213743 0.554844 0.042 Uiso 1 1 calc R U . . .
C25 C 0.58377(15) 0.4457(5) 0.21448(9) 0.0273(5) Uani 1 1 d . . . . .
C26 C 0.60546(16) 0.6281(5) 0.18368(9) 0.0284(5) Uani 1 1 d . . . . .
H26 H 0.567410 0.758443 0.175280 0.034 Uiso 1 1 calc R U . . .
C27 C 0.68196(16) 0.6220(5) 0.16508(10) 0.0299(5) Uani 1 1 d . . . . .
H27 H 0.696511 0.749424 0.144771 0.036 Uiso 1 1 calc R U . . .
C28 C 0.73685(16) 0.4300(5) 0.17619(10) 0.0320(6) Uani 1 1 d . . . . .
H28 H 0.789213 0.425637 0.163579 0.038 Uiso 1 1 calc R U . . .
C29 C 0.71541(17) 0.2443(5) 0.20568(10) 0.0330(6) Uani 1 1 d . . . . .
H29 H 0.753020 0.112096 0.213164 0.040 Uiso 1 1 calc R U . . .
C30 C 0.63895(16) 0.2505(5) 0.22442(10) 0.0309(5) Uani 1 1 d . . . . .
H30 H 0.624178 0.120878 0.244137 0.037 Uiso 1 1 calc R U . . .
C31 C -0.05331(18) 0.7363(5) 0.57584(11) 0.0377(6) Uani 1 1 d . . . . .
H31A H -0.077032 0.743324 0.540605 0.057 Uiso 1 1 calc R U . . .
H31B H -0.023419 0.886977 0.585646 0.057 Uiso 1 1 calc R U . . .
H31C H -0.099355 0.713587 0.595440 0.057 Uiso 1 1 calc R U . . .
O1 O 0.41846(19) 0.3536(8) 0.35091(11) 0.0317(9) Uani 0.601(7) 1 d D U P A 1
C13 C 0.5707(4) 0.3221(14) 0.3707(2) 0.0355(14) Uani 0.601(7) 1 d D U P A 1
H13A H 0.620457 0.352434 0.396350 0.043 Uiso 0.601(7) 1 calc R U P A 1
H13B H 0.567162 0.147434 0.363526 0.043 Uiso 0.601(7) 1 calc R U P A 1
C14 C 0.4897(3) 0.4105(11) 0.38779(17) 0.0308(11) Uani 0.601(7) 1 d D U P A 1
H14 H 0.492941 0.588656 0.392966 0.037 Uiso 0.601(7) 1 calc R U P A 1
C15 C 0.4753(8) 0.288(2) 0.4351(4) 0.031(2) Uani 0.601(7) 1 d D U P A 1
H15A H 0.459872 0.117537 0.428230 0.038 Uiso 0.601(7) 1 calc R U P A 1
H15B H 0.528345 0.292216 0.459242 0.038 Uiso 0.601(7) 1 calc R U P A 1
O1' O 0.4246(3) 0.5067(11) 0.35704(17) 0.0286(13) Uani 0.399(7) 1 d D U P A 2
C13' C 0.5515(6) 0.254(2) 0.3574(4) 0.039(2) Uani 0.399(7) 1 d D U P A 2
H13C H 0.545056 0.104636 0.337581 0.046 Uiso 0.399(7) 1 calc R U P A 2
H13D H 0.597814 0.228313 0.385427 0.046 Uiso 0.399(7) 1 calc R U P A 2
C14' C 0.4679(5) 0.3011(18) 0.3784(3) 0.0354(15) Uani 0.399(7) 1 d D U P A 2
H14' H 0.430092 0.157403 0.371701 0.043 Uiso 0.399(7) 1 calc R U P A 2
C15' C 0.4829(13) 0.350(4) 0.4328(7) 0.040(3) Uani 0.399(7) 1 d D U P A 2
H15C H 0.523607 0.485291 0.438968 0.048 Uiso 0.399(7) 1 calc R U P A 2
H15D H 0.510691 0.206686 0.449651 0.048 Uiso 0.399(7) 1 calc R U P A 2


_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 N1 1.409(3) . ?
O2 C16 1.370(4) . ?
O3 C22 1.362(3) . ?
O3 C31 1.425(3) . ?
N1 C18 1.310(4) . ?
C1 H1A 1.0000 . ?
C1 H1B 1.0000 . ?
C1 C2 1.516(5) . ?
C1 C11 1.517(4) . ?
C1 O1 1.472(4) . ?
C1 O1' 1.458(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.540(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.508(4) . ?
C4 C5 1.391(4) . ?
C4 C9 1.410(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.380(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.387(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.387(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.392(4) . ?
C9 C10 1.492(4) . ?
C10 C11 1.340(4) . ?
C10 C25 1.497(3) . ?
C11 C12 1.508(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 H12C 0.9900 . ?
C12 H12D 0.9900 . ?
C12 C13 1.506(7) . ?
C12 C13' 1.564(11) . ?
C16 C17 1.342(4) . ?
C16 C15 1.498(10) . ?
C16 C15' 1.519(16) . ?
C17 H17 0.9500 . ?
C17 C18 1.417(4) . ?
C18 C19 1.482(4) . ?
C19 C20 1.377(4) . ?
C19 C24 1.410(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.375(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.396(4) . ?
C22 C23 1.392(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.386(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.394(4) . ?
C25 C30 1.397(4) . ?
C26 H26 0.9500 . ?
C26 C27 1.390(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.383(4) . ?
C28 H28 0.9500 . ?
C28 C29 1.384(4) . ?
C29 H29 0.9500 . ?
C29 C30 1.392(4) . ?
C30 H30 0.9500 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
O1 C14 1.434(6) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.519(8) . ?
C14 H14 1.0000 . ?
C14 C15 1.510(10) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
O1' C14' 1.414(10) . ?
C13' H13C 0.9900 . ?
C13' H13D 0.9900 . ?
C13' C14' 1.548(11) . ?
C14' H14' 1.0000 . ?
C14' C15' 1.494(17) . ?
C15' H15C 0.9900 . ?
C15' H15D 0.9900 . ?

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 N1 108.3(2) . . ?
C22 O3 C31 117.5(2) . . ?
C18 N1 O2 105.6(2) . . ?
C2 C1 H1A 103.5 . . ?
C2 C1 H1B 112.9 . . ?
C2 C1 C11 113.0(3) . . ?
C11 C1 H1A 103.5 . . ?
C11 C1 H1B 112.9 . . ?
O1 C1 H1A 103.5 . . ?
O1 C1 C2 119.3(3) . . ?
O1 C1 C11 111.8(3) . . ?
O1' C1 H1B 112.9 . . ?
O1' C1 C2 90.1(3) . . ?
O1' C1 C11 113.1(3) . . ?
C1 C2 H2A 108.9 . . ?
C1 C2 H2B 108.9 . . ?
C1 C2 C3 113.3(2) . . ?
H2A C2 H2B 107.7 . . ?
C3 C2 H2A 108.9 . . ?
C3 C2 H2B 108.9 . . ?
C2 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
C4 C3 C2 113.5(3) . . ?
C4 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
C5 C4 C3 121.6(3) . . ?
C5 C4 C9 119.0(2) . . ?
C9 C4 C3 119.4(3) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 C4 121.2(3) . . ?
C6 C5 H5 119.4 . . ?
C5 C6 H6 120.0 . . ?
C5 C6 C7 119.9(3) . . ?
C7 C6 H6 120.0 . . ?
C6 C7 H7 120.2 . . ?
C8 C7 C6 119.6(3) . . ?
C8 C7 H7 120.2 . . ?
C7 C8 H8 119.5 . . ?
C7 C8 C9 121.0(2) . . ?
C9 C8 H8 119.5 . . ?
C4 C9 C10 121.0(2) . . ?
C8 C9 C4 119.2(2) . . ?
C8 C9 C10 119.9(2) . . ?
C9 C10 C25 116.3(2) . . ?
C11 C10 C9 120.9(2) . . ?
C11 C10 C25 122.8(2) . . ?
C10 C11 C1 119.6(2) . . ?
C10 C11 C12 125.2(2) . . ?
C12 C11 C1 115.3(2) . . ?
C11 C12 H12A 108.0 . . ?
C11 C12 H12B 108.0 . . ?
C11 C12 H12C 111.8 . . ?
C11 C12 H12D 111.8 . . ?
C11 C12 C13' 99.7(4) . . ?
H12A C12 H12B 107.3 . . ?
H12C C12 H12D 109.6 . . ?
C13 C12 C11 117.1(3) . . ?
C13 C12 H12A 108.0 . . ?
C13 C12 H12B 108.0 . . ?
C13' C12 H12C 111.8 . . ?
C13' C12 H12D 111.8 . . ?
O2 C16 C15 119.4(5) . . ?
O2 C16 C15' 105.3(8) . . ?
C17 C16 O2 109.2(3) . . ?
C17 C16 C15 131.3(5) . . ?
C17 C16 C15' 145.4(8) . . ?
C16 C17 H17 127.4 . . ?
C16 C17 C18 105.2(3) . . ?
C18 C17 H17 127.4 . . ?
N1 C18 C17 111.6(3) . . ?
N1 C18 C19 119.8(2) . . ?
C17 C18 C19 128.5(3) . . ?
C20 C19 C18 120.2(2) . . ?
C20 C19 C24 118.7(2) . . ?
C24 C19 C18 121.1(3) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 C19 121.3(3) . . ?
C21 C20 H20 119.4 . . ?
C20 C21 H21 120.0 . . ?
C20 C21 C22 120.0(3) . . ?
C22 C21 H21 120.0 . . ?
O3 C22 C21 124.2(2) . . ?
O3 C22 C23 115.9(2) . . ?
C23 C22 C21 119.9(2) . . ?
C22 C23 H23 120.3 . . ?
C24 C23 C22 119.4(3) . . ?
C24 C23 H23 120.3 . . ?
C19 C24 H24 119.7 . . ?
C23 C24 C19 120.7(3) . . ?
C23 C24 H24 119.7 . . ?
C26 C25 C10 120.1(2) . . ?
C26 C25 C30 118.4(2) . . ?
C30 C25 C10 121.5(2) . . ?
C25 C26 H26 119.5 . . ?
C27 C26 C25 121.0(2) . . ?
C27 C26 H26 119.5 . . ?
C26 C27 H27 120.1 . . ?
C28 C27 C26 119.9(2) . . ?
C28 C27 H27 120.1 . . ?
C27 C28 H28 120.0 . . ?
C27 C28 C29 119.9(2) . . ?
C29 C28 H28 120.0 . . ?
C28 C29 H29 119.9 . . ?
C28 C29 C30 120.2(3) . . ?
C30 C29 H29 119.9 . . ?
C25 C30 H30 119.7 . . ?
C29 C30 C25 120.5(2) . . ?
C29 C30 H30 119.7 . . ?
O3 C31 H31A 109.5 . . ?
O3 C31 H31B 109.5 . . ?
O3 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C14 O1 C1 115.2(4) . . ?
C12 C13 H13A 110.6 . . ?
C12 C13 H13B 110.6 . . ?
C12 C13 C14 105.5(5) . . ?
H13A C13 H13B 108.8 . . ?
C14 C13 H13A 110.6 . . ?
C14 C13 H13B 110.6 . . ?
O1 C14 C13 109.3(4) . . ?
O1 C14 H14 109.6 . . ?
O1 C14 C15 107.2(7) . . ?
C13 C14 H14 109.6 . . ?
C15 C14 C13 111.5(6) . . ?
C15 C14 H14 109.6 . . ?
C16 C15 C14 110.8(7) . . ?
C16 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
C14' O1' C1 107.3(5) . . ?
C12 C13' H13C 108.7 . . ?
C12 C13' H13D 108.7 . . ?
H13C C13' H13D 107.6 . . ?
C14' C13' C12 114.3(7) . . ?
C14' C13' H13C 108.7 . . ?
C14' C13' H13D 108.7 . . ?
O1' C14' C13' 112.1(7) . . ?
O1' C14' H14' 109.1 . . ?
O1' C14' C15' 104.9(10) . . ?
C13' C14' H14' 109.1 . . ?
C15' C14' C13' 112.5(10) . . ?
C15' C14' H14' 109.1 . . ?
C16 C15' H15C 108.0 . . ?
C16 C15' H15D 108.0 . . ?
C14' C15' C16 117.0(14) . . ?
C14' C15' H15C 108.0 . . ?
C14' C15' H15D 108.0 . . ?
H15C C15' H15D 107.3 . . ?

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
O2 N1 C18 C17 0.4(3) . . . . ?
O2 N1 C18 C19 -177.6(2) . . . . ?
O2 C16 C17 C18 0.5(3) . . . . ?
O2 C16 C15 C14 -38.8(10) . . . . ?
O2 C16 C15' C14' -91.8(14) . . . . ?
O3 C22 C23 C24 -179.4(2) . . . . ?
N1 O2 C16 C17 -0.3(3) . . . . ?
N1 O2 C16 C15 -179.4(6) . . . . ?
N1 O2 C16 C15' -178.3(8) . . . . ?
N1 C18 C19 C20 24.8(4) . . . . ?
N1 C18 C19 C24 -156.4(3) . . . . ?
C1 C2 C3 C4 40.2(4) . . . . ?
C1 C11 C12 C13 37.4(5) . . . . ?
C1 C11 C12 C13' 50.8(5) . . . . ?
C1 O1 C14 C13 -65.9(6) . . . . ?
C1 O1 C14 C15 173.2(5) . . . . ?
C1 O1' C14' C13' 51.8(9) . . . . ?
C1 O1' C14' C15' 174.2(9) . . . . ?
C2 C1 C11 C10 -74.5(4) . . . . ?
C2 C1 C11 C12 105.7(3) . . . . ?
C2 C1 O1 C14 -86.9(4) . . . . ?
C2 C1 O1' C14' -176.8(6) . . . . ?
C2 C3 C4 C5 110.7(3) . . . . ?
C2 C3 C4 C9 -68.9(4) . . . . ?
C3 C4 C5 C6 -178.1(3) . . . . ?
C3 C4 C9 C8 179.9(2) . . . . ?
C3 C4 C9 C10 -0.1(4) . . . . ?
C4 C5 C6 C7 -1.3(4) . . . . ?
C4 C9 C10 C11 49.1(4) . . . . ?
C4 C9 C10 C25 -129.3(3) . . . . ?
C5 C4 C9 C8 0.3(4) . . . . ?
C5 C4 C9 C10 -179.7(2) . . . . ?
C5 C6 C7 C8 -0.7(4) . . . . ?
C6 C7 C8 C9 2.5(4) . . . . ?
C7 C8 C9 C4 -2.3(4) . . . . ?
C7 C8 C9 C10 177.7(2) . . . . ?
C8 C9 C10 C11 -130.9(3) . . . . ?
C8 C9 C10 C25 50.7(3) . . . . ?
C9 C4 C5 C6 1.5(4) . . . . ?
C9 C10 C11 C1 2.5(5) . . . . ?
C9 C10 C11 C12 -177.7(3) . . . . ?
C9 C10 C25 C26 59.0(3) . . . . ?
C9 C10 C25 C30 -120.7(3) . . . . ?
C10 C11 C12 C13 -142.4(4) . . . . ?
C10 C11 C12 C13' -129.0(5) . . . . ?
C10 C25 C26 C27 177.3(2) . . . . ?
C10 C25 C30 C29 -177.5(2) . . . . ?
C11 C1 C2 C3 44.8(4) . . . . ?
C11 C1 O1 C14 48.1(5) . . . . ?
C11 C1 O1' C14' -61.5(7) . . . . ?
C11 C10 C25 C26 -119.3(3) . . . . ?
C11 C10 C25 C30 61.0(4) . . . . ?
C11 C12 C13 C14 -50.8(5) . . . . ?
C11 C12 C13' C14' -59.5(8) . . . . ?
C12 C13 C14 O1 63.1(6) . . . . ?
C12 C13 C14 C15 -178.6(7) . . . . ?
C12 C13' C14' O1' 9.5(11) . . . . ?
C12 C13' C14' C15' -108.4(12) . . . . ?
C16 O2 N1 C18 0.0(3) . . . . ?
C16 C17 C18 N1 -0.6(3) . . . . ?
C16 C17 C18 C19 177.1(3) . . . . ?
C17 C16 C15 C14 142.4(5) . . . . ?
C17 C16 C15' C14' 91.6(18) . . . . ?
C17 C18 C19 C20 -152.7(3) . . . . ?
C17 C18 C19 C24 26.1(4) . . . . ?
C18 C19 C20 C21 178.7(2) . . . . ?
C18 C19 C24 C23 -178.9(2) . . . . ?
C19 C20 C21 C22 0.2(4) . . . . ?
C20 C19 C24 C23 -0.1(4) . . . . ?
C20 C21 C22 O3 179.2(2) . . . . ?
C20 C21 C22 C23 -0.1(4) . . . . ?
C21 C22 C23 C24 -0.1(4) . . . . ?
C22 C23 C24 C19 0.1(4) . . . . ?
C24 C19 C20 C21 -0.1(4) . . . . ?
C25 C10 C11 C1 -179.2(3) . . . . ?
C25 C10 C11 C12 0.6(5) . . . . ?
C25 C26 C27 C28 1.5(4) . . . . ?
C26 C25 C30 C29 2.7(4) . . . . ?
C26 C27 C28 C29 0.1(4) . . . . ?
C27 C28 C29 C30 -0.3(4) . . . . ?
C28 C29 C30 C25 -1.2(4) . . . . ?
C30 C25 C26 C27 -2.9(4) . . . . ?
C31 O3 C22 C21 0.2(4) . . . . ?
C31 O3 C22 C23 179.5(2) . . . . ?
O1 C1 C2 C3 179.3(3) . . . . ?
O1 C1 C11 C10 147.5(3) . . . . ?
O1 C1 C11 C12 -32.3(4) . . . . ?
O1 C14 C15 C16 -71.8(9) . . . . ?
C13 C14 C15 C16 168.7(6) . . . . ?
C15 C16 C17 C18 179.4(7) . . . . ?
O1' C1 C2 C3 160.1(3) . . . . ?
O1' C1 C11 C10 -175.1(4) . . . . ?
O1' C1 C11 C12 5.1(5) . . . . ?
O1' C14' C15' C16 55.0(16) . . . . ?
C13' C14' C15' C16 177.1(11) . . . . ?
C15' C16 C17 C18 177.1(14) . . . . ?

_olex2_submission_original_sample_id frojjh30
_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 1.719
_oxdiff_exptl_absorpt_empirical_full_min 0.664
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.6621(14)
2 0.3379(14)

####################################################################### 
# 
# 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_frojjh24
_database_code_depnum_ccdc_archive 'CCDC 2174703'
loop_
_audit_author_name
_audit_author_address
'William W. Brennessel'
;University of Rochester
United States of America
;
_audit_update_record             
;
2022-05-24 deposited with the CCDC.	2022-11-04 downloaded from the CCDC.
;
_audit_creation_date             2022-02-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H19 Br O2'
_chemical_formula_sum            'C22 H19 Br O2'
_chemical_formula_weight         395.28
_chemical_melting_point          ?
_chemical_oxdiff_formula         ?
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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.14240(10)
_cell_length_b                   9.29770(10)
_cell_length_c                   13.9152(2)
_cell_angle_alpha                93.7290(10)
_cell_angle_beta                 99.1970(10)
_cell_angle_gamma                107.703(2)
_cell_volume                     862.63(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    17905
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.2010
_cell_measurement_theta_min      3.2350
_shelx_estimated_absorpt_T_max   0.781
_shelx_estimated_absorpt_T_min   0.626
_exptl_absorpt_coefficient_mu    3.338
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88565
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.120a (Rigaku Oxford Diffraction, 2021)
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    1.522
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.155
_exptl_crystal_size_mid          0.113
_exptl_crystal_size_min          0.078
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            28144
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        74.504
_diffrn_reflns_theta_max         80.002
_diffrn_reflns_theta_min         3.241
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     25.00 120.00   0.50    0.05    --   47.27  77.00 -60.00  190
  2  ω     25.00 120.00   0.50    0.05    --   47.27  77.00   0.00  190
  3  ω     25.00 120.00   0.50    0.05    --   47.27  77.00  30.00  190
  4  ω     35.00 120.00   0.50    0.05    --   47.27  38.00 150.00  170
  5  ω     42.00 106.00   0.50    0.13    --  113.25 -94.00  43.66  128
  6  ω     42.00 111.00   0.50    0.13    --  113.25-125.00  60.00  138
  7  ω     42.00 111.00   0.50    0.13    --  113.25-125.00  30.00  138
  8  ω     42.00 108.00   0.50    0.13    --  113.25-110.00  59.68  132
  9  ω     42.00 111.00   0.50    0.13    --  113.25-125.00   0.00  138
 10  ω     42.00 106.00   0.50    0.13    --  113.25 -94.00  90.00  128
 11  ω     42.00 111.00   0.50    0.13    --  113.25-125.00 -30.00  138
 12  ω     42.00 106.00   0.50    0.13    --  113.25 -94.00-120.00  128
 13  ω     42.00 107.00   0.50    0.13    --  113.25-103.00-153.00  130
 14  ω     42.00 111.00   0.50    0.13    --  113.25-125.00-180.00  138
 15  ω     15.00  83.00   0.50    0.05    --   47.27-103.00-153.00  136
 16  ω     42.00 106.00   0.50    0.13    --  113.25 -94.00 150.00  128
 17  ω     42.00 106.00   0.50    0.13    --  113.25 -94.00  60.00  128
 18  ω     42.00  79.00   0.50    0.13    --  113.25 -61.00-120.00   74
 19  ω     42.00  79.00   0.50    0.13    --  113.25 -61.00  30.00   74
 20  ω     42.00  79.00   0.50    0.13    --  113.25 -61.00  90.00   74
 21  ω     42.00  79.00   0.50    0.13    --  113.25 -61.00 120.00   74
 22  ω     42.00  79.00   0.50    0.13    --  113.25 -61.00  60.00   74
 23  ω     42.00  79.00   0.50    0.13    --  113.25 -61.00 -90.00   74
 24  ω     42.00  79.00   0.50    0.13    --  113.25 -61.00-150.00   74
 25  ω     42.00  79.00   0.50    0.13    --  113.25 -61.00-180.00   74
 26  ω     42.00  79.00   0.50    0.13    --  113.25 -61.00   0.00   74
 27  ω     42.00  79.00   0.50    0.13    --  113.25 -61.00 150.00   74
 28  ω     95.00 178.00   0.50    0.13    --  113.25 125.00  90.00  166
 29  ω    106.00 178.00   0.50    0.13    --  113.25 103.00 -50.00  144
 30  ω    101.00 178.00   0.50    0.13    --  113.25  45.00   0.00  154
 31  ω    101.00 178.00   0.50    0.13    --  113.25  45.00  30.00  154
 32  ω    101.00 178.00   0.50    0.13    --  113.25  45.00 150.00  154
 33  ω    101.00 178.00   0.50    0.13    --  113.25  30.00 120.00  154
 34  ω    101.00 178.00   0.50    0.13    --  113.25  30.00 -30.00  154
 35  ω    101.00 178.00   0.50    0.13    --  113.25  45.00 -90.00  154
 36  ω    101.00 178.00   0.50    0.13    --  113.25  45.00-120.00  154
 37  ω    101.00 178.00   0.50    0.13    --  113.25  45.00-150.00  154
 38  ω    100.00 178.00   0.50    0.13    --  113.25  15.00  90.00  156
 39  ω   -120.00 -25.00   0.50    0.05    --  -47.27 -77.00 150.00  190
 40  ω   -120.00 -25.00   0.50    0.05    --  -47.27 -77.00  90.00  190
 41  ω   -120.00 -25.00   0.50    0.05    --  -47.27 -77.00  30.00  190
 42  ω   -120.00 -35.00   0.50    0.05    --  -47.27 -38.00  90.00  170
 43  ω   -120.00 -32.00   0.50    0.05    --  -47.27 -57.00 -60.00  176
 44  ω   -120.00 -25.00   0.50    0.05    --  -47.27 -77.00 -90.00  190
 45  ω   -120.00 -25.00   0.50    0.05    --  -47.27 -77.00-150.00  190
 46  ω   -163.00 -86.00   0.50    0.13    --  -91.75 -77.00 -90.00  154
 47  ω   -163.00 -69.00   0.50    0.13    --  -91.75 -77.00-120.00  188
 48  ω   -163.00 -69.00   0.50    0.13    --  -91.75 -77.00-150.00  188
 49  ω   -163.00 -69.00   0.50    0.13    --  -91.75 -77.00-180.00  188
 50  ω   -163.00 -69.00   0.50    0.13    --  -91.75 -77.00 -30.00  188
 51  ω   -163.00 -69.00   0.50    0.13    --  -91.75 -76.00  -8.02  188
 52  ω   -163.00 -69.00   0.50    0.13    --  -91.75 -77.00  30.00  188
 53  ω   -163.00 -74.00   0.50    0.13    --  -91.75 -63.00 -73.12  178
 54  ω   -163.00 -70.00   0.50    0.13    --  -91.75 -75.00  54.82  186
 55  ω   -163.00 -71.00   0.50    0.13    --  -91.75 -72.00  78.08  184
 56  ω   -163.00 -69.00   0.50    0.13    --  -91.75 -77.00 120.00  188
 57  ω   -163.00 -69.00   0.50    0.13    --  -91.75 -77.00 150.00  188
 58  ω   -166.00 -79.00   0.50    0.13    --  -91.75 -30.00-150.00  174
 59  ω   -163.00 -84.00   0.50    0.13    --  -91.75-103.00-153.00  158
 60  ω   -120.00 -73.00   0.50    0.05    --  -47.27-125.00 -90.00   94
 61  ω   -120.00 -73.00   0.50    0.05    --  -47.27-125.00  30.00   94
 62  ω    -16.00  28.00   0.50    0.05    --  -47.27  19.00 -30.00   88
 63  ω    -16.00  28.00   0.50    0.05    --  -47.27  19.00-150.00   88
 64  ω    -59.00  25.00   0.50    0.05    --  -47.27  57.00-120.00  168
 65  ω    -86.00 -13.00   0.50    0.05    --  -47.27 125.00 -90.00  146
 66  ω    -81.00   7.00   0.50    0.05    --  -47.27 103.00 -50.00  176
 67  ω    -81.00 -19.00   0.50    0.13    --  -91.75 103.00 -50.00  124
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.2260438000
_diffrn_orient_matrix_UB_12      -0.0225545000
_diffrn_orient_matrix_UB_13      -0.0231128000
_diffrn_orient_matrix_UB_21      0.0156626000
_diffrn_orient_matrix_UB_22      0.0335041000
_diffrn_orient_matrix_UB_23      -0.1059243000
_diffrn_orient_matrix_UB_31      -0.0426641000
_diffrn_orient_matrix_UB_32      -0.1704954000
_diffrn_orient_matrix_UB_33      -0.0317887000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3503
_reflns_number_total             3680
_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 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.120a (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, 2015b)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015a)'
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.694
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3680
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0325
_refine_ls_restrained_S_all      1.081
_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)+(0.0195P)²+1.5053P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0764
_refine_ls_wR_factor_ref         0.0772
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C6(H6A,H6B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), C18(H18), C19(H19), C21(H21), C22(H22)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.18914(4) 0.99332(3) 0.10522(2) 0.02799(9) Uani 1 1 d . . . . .
O1 O 0.8225(3) 0.26725(18) 0.17694(12) 0.0255(3) Uani 1 1 d . . . . .
O2 O 0.7723(2) 0.53438(18) 0.54061(11) 0.0213(3) Uani 1 1 d . . . . .
C1 C 0.9212(4) 0.3553(3) 0.10905(17) 0.0271(5) Uani 1 1 d . . . . .
H1A H 0.946869 0.286873 0.058851 0.033 Uiso 1 1 calc R U . . .
H1B H 1.051960 0.425874 0.143978 0.033 Uiso 1 1 calc R U . . .
C2 C 0.7961(4) 0.4474(3) 0.05810(17) 0.0270(5) Uani 1 1 d . . . . .
H2A H 0.879980 0.554998 0.062279 0.032 Uiso 1 1 calc R U . . .
H2B H 0.748408 0.406533 -0.012050 0.032 Uiso 1 1 calc R U . . .
C3 C 0.6170(4) 0.4374(3) 0.10782(16) 0.0250(5) Uani 1 1 d . . . . .
H3A H 0.553401 0.513159 0.085116 0.030 Uiso 1 1 calc R U . . .
H3B H 0.516532 0.334982 0.089674 0.030 Uiso 1 1 calc R U . . .
C4 C 0.6845(3) 0.4670(3) 0.21712(16) 0.0212(4) Uani 1 1 d . . . . .
C5 C 0.7933(3) 0.3591(3) 0.25589(16) 0.0218(4) Uani 1 1 d . . . . .
H5 H 0.926422 0.419587 0.296415 0.026 Uiso 1 1 calc R U . . .
C6 C 0.6745(4) 0.2499(3) 0.31783(17) 0.0246(5) Uani 1 1 d . . . . .
H6A H 0.709934 0.154908 0.314193 0.030 Uiso 1 1 calc R U . . .
H6B H 0.529941 0.223618 0.290478 0.030 Uiso 1 1 calc R U . . .
C7 C 0.7145(3) 0.3170(3) 0.42526(16) 0.0214(4) Uani 1 1 d . . . . .
H7A H 0.607291 0.255595 0.456857 0.026 Uiso 1 1 calc R U . . .
H7B H 0.842430 0.306789 0.458436 0.026 Uiso 1 1 calc R U . . .
C8 C 0.7254(3) 0.4791(2) 0.44194(15) 0.0193(4) Uani 1 1 d . . . . .
C9 C 0.7751(3) 0.6831(3) 0.54589(16) 0.0204(4) Uani 1 1 d . . . . .
C10 C 0.8205(3) 0.7805(3) 0.63169(17) 0.0239(5) Uani 1 1 d . . . . .
H10 H 0.853986 0.749359 0.694039 0.029 Uiso 1 1 calc R U . . .
C11 C 0.8142(4) 0.9262(3) 0.62148(17) 0.0259(5) Uani 1 1 d . . . . .
H11 H 0.844481 0.997830 0.678205 0.031 Uiso 1 1 calc R U . . .
C12 C 0.7639(4) 0.9696(3) 0.52917(18) 0.0258(5) Uani 1 1 d . . . . .
H12 H 0.758019 1.069672 0.524686 0.031 Uiso 1 1 calc R U . . .
C13 C 0.7225(3) 0.8708(3) 0.44394(17) 0.0232(5) Uani 1 1 d . . . . .
H13 H 0.690653 0.902675 0.381629 0.028 Uiso 1 1 calc R U . . .
C14 C 0.7287(3) 0.7228(2) 0.45186(16) 0.0197(4) Uani 1 1 d . . . . .
C15 C 0.6984(3) 0.5871(2) 0.38415(16) 0.0190(4) Uani 1 1 d . . . . .
C16 C 0.6476(3) 0.5717(2) 0.27638(16) 0.0197(4) Uani 1 1 d . . . . .
C17 C 0.5391(3) 0.6758(2) 0.23514(15) 0.0197(4) Uani 1 1 d . . . . .
C18 C 0.6215(4) 0.7836(3) 0.17529(17) 0.0239(5) Uani 1 1 d . . . . .
H18 H 0.748667 0.790935 0.159892 0.029 Uiso 1 1 calc R U . . .
C19 C 0.5208(4) 0.8803(3) 0.13785(17) 0.0252(5) Uani 1 1 d . . . . .
H19 H 0.578807 0.954375 0.098058 0.030 Uiso 1 1 calc R U . . .
C20 C 0.3337(4) 0.8664(3) 0.15978(16) 0.0220(4) Uani 1 1 d . . . . .
C21 C 0.2490(3) 0.7620(2) 0.21986(16) 0.0212(4) Uani 1 1 d . . . . .
H21 H 0.121099 0.754297 0.234516 0.025 Uiso 1 1 calc R U . . .
C22 C 0.3540(3) 0.6685(3) 0.25837(16) 0.0217(4) Uani 1 1 d . . . . .
H22 H 0.298689 0.598625 0.301179 0.026 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 C20 1.909(2) . ?
O1 C1 1.422(3) . ?
O1 C5 1.428(3) . ?
O2 C8 1.385(3) . ?
O2 C9 1.374(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.541(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.531(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.501(3) . ?
C4 C5 1.520(3) . ?
C4 C16 1.348(3) . ?
C5 H5 1.0000 . ?
C5 C6 1.522(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.529(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.487(3) . ?
C8 C15 1.365(3) . ?
C9 C10 1.381(3) . ?
C9 C14 1.399(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.385(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.396(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.385(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.402(3) . ?
C14 C15 1.463(3) . ?
C15 C16 1.472(3) . ?
C16 C17 1.501(3) . ?
C17 C18 1.397(3) . ?
C17 C22 1.393(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.390(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.387(3) . ?
C20 C21 1.385(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.390(3) . ?
C22 H22 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C5 112.54(17) . . ?
C9 O2 C8 106.47(16) . . ?
O1 C1 H1A 109.2 . . ?
O1 C1 H1B 109.2 . . ?
O1 C1 C2 111.84(19) . . ?
H1A C1 H1B 107.9 . . ?
C2 C1 H1A 109.2 . . ?
C2 C1 H1B 109.2 . . ?
C1 C2 H2A 109.7 . . ?
C1 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
C3 C2 C1 109.61(19) . . ?
C3 C2 H2A 109.7 . . ?
C3 C2 H2B 109.7 . . ?
C2 C3 H3A 109.7 . . ?
C2 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
C4 C3 C2 109.96(19) . . ?
C4 C3 H3A 109.7 . . ?
C4 C3 H3B 109.7 . . ?
C3 C4 C5 112.16(19) . . ?
C16 C4 C3 125.1(2) . . ?
C16 C4 C5 122.7(2) . . ?
O1 C5 C4 110.72(18) . . ?
O1 C5 H5 109.2 . . ?
O1 C5 C6 106.42(18) . . ?
C4 C5 H5 109.2 . . ?
C4 C5 C6 111.91(19) . . ?
C6 C5 H5 109.2 . . ?
C5 C6 H6A 109.1 . . ?
C5 C6 H6B 109.1 . . ?
C5 C6 C7 112.44(19) . . ?
H6A C6 H6B 107.8 . . ?
C7 C6 H6A 109.1 . . ?
C7 C6 H6B 109.1 . . ?
C6 C7 H7A 108.4 . . ?
C6 C7 H7B 108.4 . . ?
H7A C7 H7B 107.5 . . ?
C8 C7 C6 115.50(18) . . ?
C8 C7 H7A 108.4 . . ?
C8 C7 H7B 108.4 . . ?
O2 C8 C7 112.30(18) . . ?
C15 C8 O2 111.82(19) . . ?
C15 C8 C7 135.9(2) . . ?
O2 C9 C10 124.9(2) . . ?
O2 C9 C14 110.34(19) . . ?
C10 C9 C14 124.8(2) . . ?
C9 C10 H10 122.0 . . ?
C9 C10 C11 116.1(2) . . ?
C11 C10 H10 122.0 . . ?
C10 C11 H11 119.5 . . ?
C10 C11 C12 121.1(2) . . ?
C12 C11 H11 119.5 . . ?
C11 C12 H12 119.1 . . ?
C13 C12 C11 121.9(2) . . ?
C13 C12 H12 119.1 . . ?
C12 C13 H13 120.8 . . ?
C12 C13 C14 118.4(2) . . ?
C14 C13 H13 120.8 . . ?
C9 C14 C13 117.8(2) . . ?
C9 C14 C15 105.78(19) . . ?
C13 C14 C15 136.4(2) . . ?
C8 C15 C14 105.57(19) . . ?
C8 C15 C16 127.8(2) . . ?
C14 C15 C16 126.63(19) . . ?
C4 C16 C15 123.5(2) . . ?
C4 C16 C17 121.0(2) . . ?
C15 C16 C17 115.36(18) . . ?
C18 C17 C16 121.5(2) . . ?
C22 C17 C16 119.9(2) . . ?
C22 C17 C18 118.6(2) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 C17 121.2(2) . . ?
C19 C18 H18 119.4 . . ?
C18 C19 H19 120.7 . . ?
C20 C19 C18 118.6(2) . . ?
C20 C19 H19 120.7 . . ?
C19 C20 Br1 119.23(17) . . ?
C21 C20 Br1 119.22(17) . . ?
C21 C20 C19 121.5(2) . . ?
C20 C21 H21 120.5 . . ?
C20 C21 C22 118.9(2) . . ?
C22 C21 H21 120.5 . . ?
C17 C22 H22 119.5 . . ?
C21 C22 C17 121.0(2) . . ?
C21 C22 H22 119.5 . . ?

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
Br1 C20 C21 C22 179.20(16) . . . . ?
O1 C1 C2 C3 9.2(3) . . . . ?
O1 C5 C6 C7 152.48(18) . . . . ?
O2 C8 C15 C14 -0.6(2) . . . . ?
O2 C8 C15 C16 179.9(2) . . . . ?
O2 C9 C10 C11 -179.7(2) . . . . ?
O2 C9 C14 C13 179.23(19) . . . . ?
O2 C9 C14 C15 -0.9(2) . . . . ?
C1 O1 C5 C4 54.4(2) . . . . ?
C1 O1 C5 C6 176.18(19) . . . . ?
C1 C2 C3 C4 47.3(3) . . . . ?
C2 C3 C4 C5 -56.3(3) . . . . ?
C2 C3 C4 C16 126.4(2) . . . . ?
C3 C4 C5 O1 6.2(3) . . . . ?
C3 C4 C5 C6 -112.3(2) . . . . ?
C3 C4 C16 C15 173.6(2) . . . . ?
C3 C4 C16 C17 -2.9(4) . . . . ?
C4 C5 C6 C7 -86.5(2) . . . . ?
C4 C16 C17 C18 -65.0(3) . . . . ?
C4 C16 C17 C22 116.6(2) . . . . ?
C5 O1 C1 C2 -63.2(2) . . . . ?
C5 C4 C16 C15 -3.4(3) . . . . ?
C5 C4 C16 C17 -179.8(2) . . . . ?
C5 C6 C7 C8 41.9(3) . . . . ?
C6 C7 C8 O2 -176.81(18) . . . . ?
C6 C7 C8 C15 4.1(4) . . . . ?
C7 C8 C15 C14 178.5(2) . . . . ?
C7 C8 C15 C16 -1.0(4) . . . . ?
C8 O2 C9 C10 -178.5(2) . . . . ?
C8 O2 C9 C14 0.6(2) . . . . ?
C8 C15 C16 C4 -23.2(4) . . . . ?
C8 C15 C16 C17 153.4(2) . . . . ?
C9 O2 C8 C7 -179.26(18) . . . . ?
C9 O2 C8 C15 0.1(2) . . . . ?
C9 C10 C11 C12 0.2(3) . . . . ?
C9 C14 C15 C8 1.0(2) . . . . ?
C9 C14 C15 C16 -179.6(2) . . . . ?
C10 C9 C14 C13 -1.7(3) . . . . ?
C10 C9 C14 C15 178.1(2) . . . . ?
C10 C11 C12 C13 -1.4(4) . . . . ?
C11 C12 C13 C14 1.0(4) . . . . ?
C12 C13 C14 C9 0.5(3) . . . . ?
C12 C13 C14 C15 -179.3(2) . . . . ?
C13 C14 C15 C8 -179.3(3) . . . . ?
C13 C14 C15 C16 0.2(4) . . . . ?
C14 C9 C10 C11 1.4(3) . . . . ?
C14 C15 C16 C4 157.4(2) . . . . ?
C14 C15 C16 C17 -25.9(3) . . . . ?
C15 C16 C17 C18 118.3(2) . . . . ?
C15 C16 C17 C22 -60.2(3) . . . . ?
C16 C4 C5 O1 -176.4(2) . . . . ?
C16 C4 C5 C6 65.0(3) . . . . ?
C16 C17 C18 C19 -179.6(2) . . . . ?
C16 C17 C22 C21 -178.9(2) . . . . ?
C17 C18 C19 C20 -1.0(4) . . . . ?
C18 C17 C22 C21 2.6(3) . . . . ?
C18 C19 C20 Br1 -177.80(17) . . . . ?
C18 C19 C20 C21 1.8(3) . . . . ?
C19 C20 C21 C22 -0.4(3) . . . . ?
C20 C21 C22 C17 -1.8(3) . . . . ?
C22 C17 C18 C19 -1.1(3) . . . . ?

_olex2_submission_original_sample_id frojjh24
_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 1.201
_oxdiff_exptl_absorpt_empirical_full_min 0.829
####################################################################### 
# 
# 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_frojjh31
_database_code_depnum_ccdc_archive 'CCDC 2195747'
loop_
_audit_author_name
_audit_author_address
'William W. Brennessel'
;University of Rochester
United States of America
;
_audit_update_record             
;
2022-08-08 deposited with the CCDC.	2022-11-04 downloaded from the CCDC.
;
_audit_creation_date             2022-08-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H27 N O3 S'
_chemical_formula_sum            'C27 H27 N O3 S'
_chemical_formula_weight         445.55
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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           7
_space_group_name_H-M_alt        'P 1 c 1'
_space_group_name_Hall           'P -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'

_cell_length_a                   12.17620(10)
_cell_length_b                   11.57040(10)
_cell_length_c                   7.98290(10)
_cell_angle_alpha                90
_cell_angle_beta                 94.5220(10)
_cell_angle_gamma                90
_cell_volume                     1121.158(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    25014
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      78.8700
_cell_measurement_theta_min      3.6380
_shelx_estimated_absorpt_T_max   0.973
_shelx_estimated_absorpt_T_min   0.524
_exptl_absorpt_coefficient_mu    1.516
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62538
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.64a (Rigaku Oxford Diffraction, 2022)
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    1.320
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.489
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.018
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0717
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            34948
_diffrn_reflns_point_group_measured_fraction_full 0.948
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_theta_full        74.504
_diffrn_reflns_theta_max         80.188
_diffrn_reflns_theta_min         3.641
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -14.00  28.00   0.50    0.23    --  -47.28  19.00-180.00   84
  2  ω    -14.00  28.00   0.50    0.23    --  -47.28  19.00-150.00   84
  3  ω    -14.00  28.00   0.50    0.23    --  -47.28  19.00-120.00   84
  4  ω    -14.00  28.00   0.50    0.23    --  -47.28  19.00 -30.00   84
  5  ω    -14.00  28.00   0.50    0.23    --  -47.28  19.00  60.00   84
  6  ω     25.00 119.00   0.50    0.23    --   47.28  77.00  60.00  188
  7  ω     25.00 119.00   0.50    0.23    --   47.28  77.00  30.00  188
  8  ω     32.00 119.00   0.50    0.23    --   47.28  57.00  30.00  174
  9  ω     25.00 119.00   0.50    0.23    --   47.28  77.00-180.00  188
 10  ω     32.00 119.00   0.50    0.23    --   47.28  57.00 -90.00  174
 11  ω     25.00 119.00   0.50    0.23    --   47.28  77.00 -60.00  188
 12  ω     32.00 119.00   0.50    0.23    --   47.28  57.00 150.00  174
 13  ω    101.00 178.00   0.50    0.91    --  113.25  45.00 150.00  154
 14  ω    101.00 178.00   0.50    0.91    --  113.25  30.00 150.00  154
 15  ω    101.00 178.00   0.50    0.91    --  113.25  30.00  90.00  154
 16  ω    100.00 178.00   0.50    0.91    --  113.25  15.00  30.00  156
 17  ω    100.00 178.00   0.50    0.91    --  113.25  15.00 -30.00  156
 18  ω    100.00 178.00   0.50    0.91    --  113.25  15.00-120.00  156
 19  ω     93.00 178.00   0.50    0.91    --  113.25 129.00-138.00  170
 20  ω     95.00 178.00   0.50    0.91    --  113.25 125.00-120.00  166
 21  ω     42.00  76.00   0.50    0.91    --  113.25 -61.00 120.00   68
 22  ω     42.00  76.00   0.50    0.91    --  113.25 -61.00 -30.00   68
 23  ω     42.00  76.00   0.50    0.91    --  113.25 -61.00 -90.00   68
 24  ω     42.00  76.00   0.50    0.91    --  113.25 -61.00-150.00   68
 25  ω     42.00 106.00   0.50    0.91    --  113.25 -94.00-120.00  128
 26  ω     43.00 104.00   0.50    0.23    --   47.28-141.00 -24.00  122
 27  ω     43.00 123.00   0.50    0.91    --  113.25-141.00 -24.00  160
 28  ω     42.00 106.00   0.50    0.91    --  113.25 -94.00 -30.00  128
 29  ω     44.00 111.00   0.50    0.91    --  113.25-125.00  60.00  134
 30  ω     43.00 114.00   0.50    0.91    --  113.25-129.00 147.00  142
 31  ω     42.00 106.00   0.50    0.91    --  113.25 -94.00 150.00  128
 32  ω     37.00  96.00   0.50    0.23    --   47.28-129.00 147.00  118
 33  ω    -47.00 -20.00   0.50    0.91    --  -91.75  45.00-150.00   54
 34  ω    -89.00 -15.00   0.50    0.23    --  -47.28 129.00-138.00  148
 35  ω    -98.00 -21.00   0.50    0.91    --  -91.75 141.00  33.00  154
 36  ω    -47.00 -20.00   0.50    0.91    --  -91.75  45.00-120.00   54
 37  ω   -163.00 -69.00   0.50    0.91    --  -91.75 -77.00 -90.00  188
 38  ω   -119.00 -63.00   0.50    0.23    --  -47.28-141.00 -24.00  112
 39  ω   -118.00 -71.00   0.50    0.23    --  -47.28-129.00 147.00   94
 40  ω   -162.00 -71.00   0.50    0.91    --  -91.75-129.00 147.00  182
 41  ω    -61.00 -30.00   0.50    0.91    --  -91.75 143.00 -57.00   62
 42  ω    -78.00 -36.00   0.50    0.23    --  -47.28 -37.00 -30.00   84
 43  ω    -60.00 -35.00   0.50    0.23    --  -47.28 -37.00  30.00   50
 44  ω     65.00  95.00   0.50    0.23    --   47.28  19.00 120.00   60
 45  ω     25.00  50.00   0.50    0.23    --   47.28  77.00 150.00   50
 46  ω     25.00  53.00   0.50    0.23    --   47.28  77.00-120.00   56
 47  ω     26.00  52.00   0.50    0.23    --   47.28  77.00   0.00   52
 48  ω     35.00  63.00   0.50    0.23    --   47.28  19.00 120.00   56
 49  ω     35.00  62.00   0.50    0.23    --   47.28  57.00  90.00   54
 50  ω     28.00  54.00   0.50    0.23    --   47.28  77.00  90.00   52
 51  ω     33.00  60.00   0.50    0.23    --   47.28  57.00-180.00   54
 52  ω    -98.00 -72.00   0.50    0.91    --  -91.75 -73.00  69.08   52
 53  ω    -95.00 -69.00   0.50    0.91    --  -91.75 -77.00 150.00   52
 54  ω    -96.00 -70.00   0.50    0.91    --  -91.75 -77.00 120.00   52
 55  ω    -95.00 -69.00   0.50    0.91    --  -91.75 -77.00  30.00   52
 56  ω    -97.00 -71.00   0.50    0.91    --  -91.75 -77.00-161.45   52
 57  ω   -101.00 -71.00   0.50    0.91    --  -91.75 -75.00  42.83   60
 58  ω   -101.00 -75.00   0.50    0.91    --  -91.75 -62.00 -88.98   52
 59  ω    -95.00 -69.00   0.50    0.91    --  -91.75 -76.00-116.90   52
 60  ω   -102.00 -76.00   0.50    0.91    --  -91.75 -59.00-124.29   52
 61  ω    -94.00 -69.00   0.50    0.91    --  -91.75 -76.00 138.08   50
 62  ω    -94.00 -69.00   0.50    0.91    --  -91.75 -76.00-132.50   50
 63  ω    -95.00 -69.00   0.50    0.91    --  -91.75 -76.00  16.89   52
 64  ω    -97.00 -71.00   0.50    0.91    --  -91.75 -71.00 -30.41   52
 65  ω    -97.00 -71.00   0.50    0.91    --  -91.75 -77.00 -30.00   52
 66  ω    -99.00 -73.00   0.50    0.91    --  -91.75 -67.00 -56.90   52
 67  ω   -110.00 -69.00   0.50    0.91    --  -91.75 -77.00 -60.00   82
 68  ω   -142.00-116.00   0.50    0.91    --  -91.75 -77.00  90.00   52
 69  ω    -95.00 -69.00   0.50    0.91    --  -91.75 -77.00-150.00   52
 70  ω    -94.00 -69.00   0.50    0.91    --  -91.75 -77.00  90.00   50
 71  ω    -94.00 -69.00   0.50    0.91    --  -91.75 -77.00   0.00   50
 72  ω    -95.00 -69.00   0.50    0.91    --  -91.75 -77.00-180.00   52
 73  ω   -138.00-112.00   0.50    0.91    --  -91.75 -76.00 138.08   52
 74  ω    -95.00 -70.00   0.50    0.91    --  -91.75 -74.00  65.37   50
 75  ω    -95.00 -69.00   0.50    0.91    --  -91.75 -76.00 165.37   52
 76  ω    -94.00 -69.00   0.50    0.91    --  -91.75 -76.00 105.94   50
 77  ω   -101.00 -75.00   0.50    0.91    --  -91.75 -62.00 -31.82   52
 78  ω    -97.00 -71.00   0.50    0.91    --  -91.75 -77.00  60.00   52
 79  ω     45.00  71.00   0.50    0.91    --  113.25-125.00 120.00   52
 80  ω    138.00 168.00   0.50    0.91    --  113.25 143.00 -57.00   60
 81  ω     97.00 131.00   0.50    0.91    --  113.25  61.00-120.00   68
 82  ω    153.00 178.00   0.50    0.91    --  113.25  77.00 150.00   50
 83  ω    109.00 135.00   0.50    0.91    --  113.25 143.00 -57.00   52
 84  ω     98.00 131.00   0.50    0.91    --  113.25  61.00-180.00   66
 85  ω     91.00 121.00   0.50    0.91    --  113.25  77.00 150.00   60
 86  ω    100.00 146.00   0.50    0.91    --  113.25  61.00 -60.00   92
 87  ω    141.00 174.00   0.50    0.91    --  113.25  77.00  90.00   66
 88  ω     42.00  92.00   0.50    0.91    --  113.25 -94.00-150.00  100
 89  ω     92.00 147.00   0.50    0.91    --  113.25  77.00-150.00  110
 90  ω    102.00 137.00   0.50    0.91    --  113.25  45.00  90.00   70
 91  ω     92.00 131.00   0.50    0.91    --  113.25  77.00   0.00   78
 92  ω     91.00 117.00   0.50    0.91    --  113.25  77.00  90.00   52
 93  ω     91.00 122.00   0.50    0.91    --  113.25  77.00-180.00   62
 94  ω     91.00 117.00   0.50    0.91    --  113.25  77.00 120.00   52
 95  ω    135.00 163.00   0.50    0.91    --  113.25  77.00 120.00   56
 96  ω     81.00 107.00   0.50    0.91    --  113.25-125.00  30.00   52
 97  ω     98.00 127.00   0.50    0.91    --  113.25  61.00-150.00   58
 98  ω     48.00  75.00   0.50    0.91    --  113.25-125.00  30.00   54
 99  ω    153.00 178.00   0.50    0.91    --  113.25  61.00   0.00   50
100  ω    134.00 164.00   0.50    0.91    --  113.25  77.00  30.00   60
101  ω     91.00 128.00   0.50    0.91    --  113.25  77.00  30.00   74
102  ω     97.00 135.00   0.50    0.91    --  113.25  61.00   0.00   76
103  ω    141.00 172.00   0.50    0.91    --  113.25  61.00 -30.00   62
104  ω     98.00 141.00   0.50    0.91    --  113.25  77.00-120.00   86
105  ω    103.00 131.00   0.50    0.91    --  113.25  61.00 -30.00   56
106  ω     48.00  75.00   0.50    0.91    --  113.25 -77.00-120.00   54
107  ω    134.00 160.00   0.50    0.91    --  113.25  77.00 -90.00   52
108  ω    131.00 177.00   0.50    0.91    --  113.25  77.00 -60.00   92
109  ω     92.00 118.00   0.50    0.91    --  113.25  77.00 -90.00   52
110  ω     92.00 118.00   0.50    0.91    --  113.25  77.00 -60.00   52
111  ω     99.00 126.00   0.50    0.91    --  113.25  61.00 150.00   54
112  ω    102.00 128.00   0.50    0.91    --  113.25  61.00  60.00   52
113  ω     87.00 114.00   0.50    0.91    --  113.25 -77.00-120.00   54
114  ω     43.00  86.00   0.50    0.91    --  113.25 -94.00  60.00   86
115  ω     76.00 103.00   0.50    0.91    --  113.25-125.00 120.00   54
116  ω    150.00 176.00   0.50    0.91    --  113.25  61.00-180.00   52
117  ω     42.00  67.00   0.50    0.91    --  113.25 -61.00  30.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0102226000
_diffrn_orient_matrix_UB_12      -0.1325632000
_diffrn_orient_matrix_UB_13      0.0109854000
_diffrn_orient_matrix_UB_21      -0.1262828000
_diffrn_orient_matrix_UB_22      -0.0111305000
_diffrn_orient_matrix_UB_23      -0.0255024000
_diffrn_orient_matrix_UB_31      0.0072382000
_diffrn_orient_matrix_UB_32      -0.0060622000
_diffrn_orient_matrix_UB_33      -0.1915817000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.870
_reflns_Friedel_fraction_full    0.895
_reflns_Friedel_fraction_max     0.865
_reflns_number_gt                4400
_reflns_number_total             4549
_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 1.171.42.64a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015a)'
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.464
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 
;
 Flack x determined using 1972 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.002(16)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4549
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0438
_refine_ls_restrained_S_all      1.097
_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)+(0.0806P)²+0.2718P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1208
_refine_ls_wR_factor_ref         0.1219
_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:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C6(H6A,H6B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20), C22(H22), C23(H23), C25(H25), C26(H26)
2.d Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
S1 S 0.28380(6) 0.69961(7) 0.98047(9) 0.0275(2) Uani 1 1 d . . . . .
O1 O 0.61703(19) 0.6078(2) 1.2630(3) 0.0277(5) Uani 1 1 d . . . . .
O2 O 0.2840(2) 0.7931(2) 0.8631(3) 0.0338(6) Uani 1 1 d . . . . .
O3 O 0.2313(2) 0.5933(2) 0.9313(3) 0.0345(6) Uani 1 1 d . . . . .
N1 N 0.4130(2) 0.6656(2) 1.0382(4) 0.0274(6) Uani 1 1 d . . . . .
C1 C 0.5354(3) 0.5269(3) 1.1999(4) 0.0284(7) Uani 1 1 d . . . . .
H1A H 0.533471 0.460968 1.278725 0.034 Uiso 1 1 calc R U . . .
H1B H 0.555358 0.496563 1.090343 0.034 Uiso 1 1 calc R U . . .
C2 C 0.4228(3) 0.5818(3) 1.1780(4) 0.0291(7) Uani 1 1 d . . . . .
H2A H 0.366634 0.520614 1.156847 0.035 Uiso 1 1 calc R U . . .
H2B H 0.407633 0.621741 1.283479 0.035 Uiso 1 1 calc R U . . .
C3 C 0.4959(3) 0.7613(3) 1.0499(4) 0.0247(6) Uani 1 1 d . . . . .
H3A H 0.503606 0.791187 1.166383 0.030 Uiso 1 1 calc R U . . .
H3B H 0.469494 0.825297 0.974930 0.030 Uiso 1 1 calc R U . . .
C4 C 0.6071(3) 0.7210(3) 1.0010(4) 0.0241(6) Uani 1 1 d . . . . .
C5 C 0.6787(3) 0.6550(3) 1.1347(4) 0.0251(6) Uani 1 1 d . . . . .
H5 H 0.714666 0.589607 1.078136 0.030 Uiso 1 1 calc R U . . .
C6 C 0.7690(3) 0.7289(3) 1.2227(5) 0.0317(7) Uani 1 1 d . . . . .
H6A H 0.819587 0.678859 1.293649 0.038 Uiso 1 1 calc R U . . .
H6B H 0.735547 0.785132 1.297142 0.038 Uiso 1 1 calc R U . . .
C7 C 0.8347(3) 0.7943(3) 1.0964(5) 0.0325(8) Uani 1 1 d . . . . .
H7A H 0.795130 0.866267 1.062151 0.039 Uiso 1 1 calc R U . . .
H7B H 0.907445 0.816130 1.151518 0.039 Uiso 1 1 calc R U . . .
C8 C 0.8515(3) 0.7230(3) 0.9419(5) 0.0295(7) Uani 1 1 d . . . . .
C9 C 0.9534(3) 0.6766(4) 0.9144(5) 0.0339(8) Uani 1 1 d . . . . .
H9 H 1.014155 0.691249 0.993652 0.041 Uiso 1 1 calc R U . . .
C10 C 0.9692(3) 0.6092(3) 0.7744(5) 0.0358(8) Uani 1 1 d . . . . .
H10 H 1.038858 0.574921 0.761298 0.043 Uiso 1 1 calc R U . . .
C11 C 0.8818(3) 0.5925(3) 0.6535(5) 0.0317(7) Uani 1 1 d . . . . .
H11 H 0.892189 0.548523 0.555452 0.038 Uiso 1 1 calc R U . . .
C12 C 0.7796(3) 0.6403(3) 0.6766(4) 0.0272(6) Uani 1 1 d . . . . .
H12 H 0.720757 0.630625 0.592327 0.033 Uiso 1 1 calc R U . . .
C13 C 0.7619(3) 0.7025(3) 0.8225(4) 0.0258(7) Uani 1 1 d . . . . .
C14 C 0.6483(3) 0.7418(3) 0.8523(4) 0.0239(6) Uani 1 1 d . . . . .
C15 C 0.5889(3) 0.8034(3) 0.7081(4) 0.0243(6) Uani 1 1 d . . . . .
C16 C 0.4800(3) 0.7780(3) 0.6532(4) 0.0273(7) Uani 1 1 d . . . . .
H16 H 0.442761 0.717140 0.704967 0.033 Uiso 1 1 calc R U . . .
C17 C 0.4253(3) 0.8412(3) 0.5231(4) 0.0298(7) Uani 1 1 d . . . . .
H17 H 0.350518 0.824174 0.488817 0.036 Uiso 1 1 calc R U . . .
C18 C 0.4790(3) 0.9281(3) 0.4439(4) 0.0331(7) Uani 1 1 d . . . . .
H18 H 0.441287 0.971238 0.355935 0.040 Uiso 1 1 calc R U . . .
C19 C 0.5891(3) 0.9522(3) 0.4939(4) 0.0316(7) Uani 1 1 d . . . . .
H19 H 0.626834 1.011133 0.438631 0.038 Uiso 1 1 calc R U . . .
C20 C 0.6436(3) 0.8901(3) 0.6243(4) 0.0271(7) Uani 1 1 d . . . . .
H20 H 0.718698 0.906598 0.656964 0.033 Uiso 1 1 calc R U . . .
C21 C 0.2196(3) 0.7500(3) 1.1581(4) 0.0279(7) Uani 1 1 d . . . . .
C22 C 0.1736(3) 0.6707(3) 1.2638(5) 0.0299(7) Uani 1 1 d . . . . .
H22 H 0.182381 0.590036 1.247356 0.036 Uiso 1 1 calc R U . . .
C23 C 0.1147(3) 0.7114(3) 1.3935(5) 0.0339(8) Uani 1 1 d . . . . .
H23 H 0.083532 0.657740 1.466395 0.041 Uiso 1 1 calc R U . . .
C24 C 0.1005(3) 0.8283(3) 1.4184(5) 0.0334(7) Uani 1 1 d . . . . .
C25 C 0.1513(3) 0.9065(3) 1.3150(5) 0.0328(7) Uani 1 1 d . . . . .
H25 H 0.144804 0.987147 1.334293 0.039 Uiso 1 1 calc R U . . .
C26 C 0.2106(3) 0.8681(3) 1.1856(5) 0.0305(7) Uani 1 1 d . . . . .
H26 H 0.244915 0.921784 1.116268 0.037 Uiso 1 1 calc R U . . .
C27 C 0.0303(4) 0.8704(4) 1.5539(6) 0.0457(10) Uani 1 1 d . . . . .
H27A H 0.064631 0.848029 1.664334 0.069 Uiso 1 1 calc R U . . .
H27B H -0.043196 0.835744 1.537393 0.069 Uiso 1 1 calc R U . . .
H27C H 0.023953 0.954761 1.547944 0.069 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
S1 O2 1.432(3) . ?
S1 O3 1.427(3) . ?
S1 N1 1.651(3) . ?
S1 C21 1.771(4) . ?
O1 C1 1.428(4) . ?
O1 C5 1.426(4) . ?
N1 C2 1.476(4) . ?
N1 C3 1.496(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.509(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.511(4) . ?
C4 C5 1.528(4) . ?
C4 C14 1.347(5) . ?
C5 H5 1.0000 . ?
C5 C6 1.520(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.536(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.511(5) . ?
C8 C9 1.384(5) . ?
C8 C13 1.411(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.388(6) . ?
C10 H10 0.9500 . ?
C10 C11 1.393(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.388(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.400(5) . ?
C13 C14 1.493(5) . ?
C14 C15 1.492(4) . ?
C15 C16 1.395(5) . ?
C15 C20 1.403(5) . ?
C16 H16 0.9500 . ?
C16 C17 1.396(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.380(5) . ?
C18 H18 0.9500 . ?
C18 C19 1.397(5) . ?
C19 H19 0.9500 . ?
C19 C20 1.389(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.394(5) . ?
C21 C26 1.390(5) . ?
C22 H22 0.9500 . ?
C22 C23 1.387(5) . ?
C23 H23 0.9500 . ?
C23 C24 1.380(5) . ?
C24 C25 1.402(6) . ?
C24 C27 1.511(6) . ?
C25 H25 0.9500 . ?
C25 C26 1.379(6) . ?
C26 H26 0.9500 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?

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
O2 S1 N1 108.16(15) . . ?
O2 S1 C21 107.41(16) . . ?
O3 S1 O2 119.70(16) . . ?
O3 S1 N1 105.52(15) . . ?
O3 S1 C21 106.74(16) . . ?
N1 S1 C21 108.99(15) . . ?
C5 O1 C1 112.9(2) . . ?
C2 N1 S1 112.7(2) . . ?
C2 N1 C3 115.1(3) . . ?
C3 N1 S1 117.7(2) . . ?
O1 C1 H1A 109.3 . . ?
O1 C1 H1B 109.3 . . ?
O1 C1 C2 111.4(3) . . ?
H1A C1 H1B 108.0 . . ?
C2 C1 H1A 109.3 . . ?
C2 C1 H1B 109.3 . . ?
N1 C2 C1 112.5(3) . . ?
N1 C2 H2A 109.1 . . ?
N1 C2 H2B 109.1 . . ?
C1 C2 H2A 109.1 . . ?
C1 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
N1 C3 H3A 109.3 . . ?
N1 C3 H3B 109.3 . . ?
N1 C3 C4 111.7(3) . . ?
H3A C3 H3B 107.9 . . ?
C4 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
C3 C4 C5 116.6(3) . . ?
C14 C4 C3 125.2(3) . . ?
C14 C4 C5 118.2(3) . . ?
O1 C5 C4 112.9(3) . . ?
O1 C5 H5 108.0 . . ?
O1 C5 C6 106.6(3) . . ?
C4 C5 H5 108.0 . . ?
C6 C5 C4 113.2(3) . . ?
C6 C5 H5 108.0 . . ?
C5 C6 H6A 109.3 . . ?
C5 C6 H6B 109.3 . . ?
C5 C6 C7 111.6(3) . . ?
H6A C6 H6B 108.0 . . ?
C7 C6 H6A 109.3 . . ?
C7 C6 H6B 109.3 . . ?
C6 C7 H7A 109.2 . . ?
C6 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C8 C7 C6 112.2(3) . . ?
C8 C7 H7A 109.2 . . ?
C8 C7 H7B 109.2 . . ?
C9 C8 C7 121.4(3) . . ?
C9 C8 C13 118.8(4) . . ?
C13 C8 C7 119.7(3) . . ?
C8 C9 H9 119.1 . . ?
C8 C9 C10 121.9(4) . . ?
C10 C9 H9 119.1 . . ?
C9 C10 H10 120.3 . . ?
C9 C10 C11 119.3(3) . . ?
C11 C10 H10 120.3 . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.8(3) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 119.5 . . ?
C11 C12 C13 120.9(3) . . ?
C13 C12 H12 119.5 . . ?
C8 C13 C14 121.2(3) . . ?
C12 C13 C8 119.1(3) . . ?
C12 C13 C14 119.6(3) . . ?
C4 C14 C13 120.1(3) . . ?
C4 C14 C15 125.0(3) . . ?
C15 C14 C13 114.9(3) . . ?
C16 C15 C14 122.2(3) . . ?
C16 C15 C20 118.4(3) . . ?
C20 C15 C14 119.4(3) . . ?
C15 C16 H16 119.7 . . ?
C15 C16 C17 120.7(3) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.4(3) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 120.2 . . ?
C17 C18 C19 119.6(3) . . ?
C19 C18 H18 120.2 . . ?
C18 C19 H19 119.9 . . ?
C20 C19 C18 120.1(3) . . ?
C20 C19 H19 119.9 . . ?
C15 C20 H20 119.7 . . ?
C19 C20 C15 120.7(3) . . ?
C19 C20 H20 119.7 . . ?
C22 C21 S1 119.5(3) . . ?
C26 C21 S1 119.7(3) . . ?
C26 C21 C22 120.7(3) . . ?
C21 C22 H22 120.5 . . ?
C23 C22 C21 119.0(3) . . ?
C23 C22 H22 120.5 . . ?
C22 C23 H23 119.4 . . ?
C24 C23 C22 121.2(4) . . ?
C24 C23 H23 119.4 . . ?
C23 C24 C25 118.8(4) . . ?
C23 C24 C27 120.3(4) . . ?
C25 C24 C27 120.9(4) . . ?
C24 C25 H25 119.5 . . ?
C26 C25 C24 121.0(3) . . ?
C26 C25 H25 119.5 . . ?
C21 C26 H26 120.4 . . ?
C25 C26 C21 119.2(3) . . ?
C25 C26 H26 120.4 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 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
S1 N1 C2 C1 164.6(2) . . . . ?
S1 N1 C3 C4 -146.0(2) . . . . ?
S1 C21 C22 C23 -174.1(3) . . . . ?
S1 C21 C26 C25 173.8(3) . . . . ?
O1 C1 C2 N1 70.2(4) . . . . ?
O1 C5 C6 C7 -174.5(3) . . . . ?
O2 S1 N1 C2 171.5(2) . . . . ?
O2 S1 N1 C3 33.7(3) . . . . ?
O2 S1 C21 C22 157.6(3) . . . . ?
O2 S1 C21 C26 -19.0(3) . . . . ?
O3 S1 N1 C2 -59.3(3) . . . . ?
O3 S1 N1 C3 163.0(2) . . . . ?
O3 S1 C21 C22 28.1(3) . . . . ?
O3 S1 C21 C26 -148.5(3) . . . . ?
N1 S1 C21 C22 -85.4(3) . . . . ?
N1 S1 C21 C26 98.0(3) . . . . ?
N1 C3 C4 C5 -79.9(3) . . . . ?
N1 C3 C4 C14 102.3(4) . . . . ?
C1 O1 C5 C4 60.8(3) . . . . ?
C1 O1 C5 C6 -174.2(3) . . . . ?
C2 N1 C3 C4 77.3(4) . . . . ?
C3 N1 C2 C1 -56.6(4) . . . . ?
C3 C4 C5 O1 20.0(4) . . . . ?
C3 C4 C5 C6 -101.3(3) . . . . ?
C3 C4 C14 C13 176.8(3) . . . . ?
C3 C4 C14 C15 -3.0(5) . . . . ?
C4 C5 C6 C7 -49.8(4) . . . . ?
C4 C14 C15 C16 -46.4(5) . . . . ?
C4 C14 C15 C20 133.5(3) . . . . ?
C5 O1 C1 C2 -99.3(3) . . . . ?
C5 C4 C14 C13 -1.0(4) . . . . ?
C5 C4 C14 C15 179.2(3) . . . . ?
C5 C6 C7 C8 -37.3(4) . . . . ?
C6 C7 C8 C9 -107.3(4) . . . . ?
C6 C7 C8 C13 72.5(4) . . . . ?
C7 C8 C9 C10 178.8(3) . . . . ?
C7 C8 C13 C12 177.4(3) . . . . ?
C7 C8 C13 C14 -5.0(5) . . . . ?
C8 C9 C10 C11 3.4(6) . . . . ?
C8 C13 C14 C4 -47.3(4) . . . . ?
C8 C13 C14 C15 132.6(3) . . . . ?
C9 C8 C13 C12 -2.7(5) . . . . ?
C9 C8 C13 C14 174.8(3) . . . . ?
C9 C10 C11 C12 -1.9(5) . . . . ?
C10 C11 C12 C13 -1.9(5) . . . . ?
C11 C12 C13 C8 4.2(5) . . . . ?
C11 C12 C13 C14 -173.4(3) . . . . ?
C12 C13 C14 C4 130.2(3) . . . . ?
C12 C13 C14 C15 -49.9(4) . . . . ?
C13 C8 C9 C10 -1.0(6) . . . . ?
C13 C14 C15 C16 133.8(3) . . . . ?
C13 C14 C15 C20 -46.4(4) . . . . ?
C14 C4 C5 O1 -162.0(3) . . . . ?
C14 C4 C5 C6 76.7(4) . . . . ?
C14 C15 C16 C17 176.9(3) . . . . ?
C14 C15 C20 C19 -177.4(3) . . . . ?
C15 C16 C17 C18 1.5(5) . . . . ?
C16 C15 C20 C19 2.5(5) . . . . ?
C16 C17 C18 C19 0.5(5) . . . . ?
C17 C18 C19 C20 -1.0(5) . . . . ?
C18 C19 C20 C15 -0.5(5) . . . . ?
C20 C15 C16 C17 -3.0(5) . . . . ?
C21 S1 N1 C2 55.0(3) . . . . ?
C21 S1 N1 C3 -82.7(3) . . . . ?
C21 C22 C23 C24 0.4(5) . . . . ?
C22 C21 C26 C25 -2.8(5) . . . . ?
C22 C23 C24 C25 -3.0(5) . . . . ?
C22 C23 C24 C27 176.3(3) . . . . ?
C23 C24 C25 C26 2.8(5) . . . . ?
C24 C25 C26 C21 0.1(5) . . . . ?
C26 C21 C22 C23 2.5(5) . . . . ?
C27 C24 C25 C26 -176.6(4) . . . . ?

_olex2_submission_original_sample_id frojjh31
_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 1.611
_oxdiff_exptl_absorpt_empirical_full_min 0.519
