#------------------------------------------------------------------------------
#$Date: 2022-04-28 01:15:14 +0300 (Thu, 28 Apr 2022) $
#$Revision: 274723 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/68/1566881.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1566881
loop_
_publ_author_name
'Han, Jianlei'
'Shi, Yonghong'
'Jin, Xue'
'Yang, Xuefeng'
'Duan, Pengfei'
_publ_section_title
;
 Regulating the Excited State Chirality to Fabricate
 High-Performance-Solid-State Circularly Polarized Luminescence Materials
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC01846B
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C51 H32 O4, C H4 O'
_chemical_formula_sum            'C52 H36 O5'
_chemical_formula_weight         740.81
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-07-15
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-08-20 deposited with the CCDC.	2022-04-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2123(2)
_cell_length_b                   17.9092(4)
_cell_length_c                   27.4926(5)
_cell_measurement_reflns_used    10059
_cell_measurement_temperature    169.99(16)
_cell_measurement_theta_max      75.0210
_cell_measurement_theta_min      3.1750
_cell_volume                     3551.12(14)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(16)
_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 0.966
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -22.00  20.00   0.50    1.50    --  -47.45  19.00 -30.00   84
  2  ω    -59.00 -32.00   0.50    4.00    --  -99.00  63.00 -14.00   54
  3  ω    -53.00 -26.00   0.50    4.00    --  -99.00  61.00  60.00   54
  4  ω    -56.00 -28.00   0.50    4.00    --  -99.00  58.00 153.00   56
  5  ω   -116.00 -89.00   0.50    4.00    --  -99.00 -15.00 120.00   54
  6  ω   -125.00 -87.00   0.50    4.00    --  -99.00 -30.00  60.00   76
  7  ω   -100.00 -74.00   0.50    1.50    --  -47.45-125.00   0.00   52
  8  ω   -115.00 -76.00   0.50    4.00    --  -99.00-125.00   0.00   78
  9  ω   -116.00 -82.00   0.50    1.50    --  -47.45-125.00-180.00   68
 10  ω    -13.00  29.00   0.50    1.50    --   47.45 -19.00-120.00   84
 11  ω     31.00  57.00   0.50    4.00    --  103.25 -63.00-151.00   52
 12  ω     35.00  75.00   0.50    4.00    --  103.25 -61.00-120.00   80
 13  ω     42.00  68.00   0.50    4.00    --  103.25 -58.00  12.00   52
 14  ω     35.00  69.00   0.50    4.00    --  103.25-120.00 138.00   68
 15  ω     33.00  60.00   0.50    4.00    --  103.25 -61.00 150.00   54
 16  ω     32.00 119.00   0.50    1.50    --   47.45  58.00 153.00  174
 17  ω    -97.00 -26.00   0.50    4.00    --  -99.00  77.00-120.00  142
 18  ω   -167.00-134.00   0.50    4.00    --  -99.00 -15.00 120.00   66
 19  ω   -168.00-127.00   0.50    4.00    --  -99.00 -30.00  60.00   82
 20  ω   -164.00-135.00   0.50    4.00    --  -99.00-125.00   0.00   58
 21  ω     60.00 131.00   0.50    4.00    --  103.25 155.00  19.00  142
 22  ω     87.00 168.00   0.50    4.00    --  103.25  63.00 -14.00  162
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2118920000
_diffrn_orient_matrix_UB_12      0.0072599000
_diffrn_orient_matrix_UB_13      0.0051136000
_diffrn_orient_matrix_UB_21      -0.0003232000
_diffrn_orient_matrix_UB_22      -0.0628373000
_diffrn_orient_matrix_UB_23      0.0382470000
_diffrn_orient_matrix_UB_31      0.0265771000
_diffrn_orient_matrix_UB_32      -0.0583064000
_diffrn_orient_matrix_UB_33      -0.0406403000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            21470
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.426
_diffrn_reflns_theta_min         2.945
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.700
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67068
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_description       needle
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 2416 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     516
_refine_ls_number_reflns         6941
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0440
_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)+(0.0871P)²+0.1286P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1189
_refine_ls_wR_factor_ref         0.1236
_reflns_Friedel_coverage         0.725
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.917
_reflns_number_gt                6239
_reflns_number_total             6941
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc01846b5.cif
_cod_data_source_block           tx5985
_cod_database_code               1566881
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHO
_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.
;
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C10(H10A,H10B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C13(H13), C14(H14), C15(H15), C21(H21), C22(H22),
 C24(H24), C25(H25), C26(H26), C28(H28), C29(H29), C31(H31), C32(H32), C37(H37),
  C38(H38), C40(H40), C41(H41), C43(H43), C44(H44), C45(H45), C47(H47), C48(H48)
2.c Idealised Me refined as rotating group:
 C52(H52A,H52B,H52C)
2.d Idealised tetrahedral OH refined as rotating group:
 O5(H5A)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.056
_oxdiff_exptl_absorpt_empirical_full_min 0.462
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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 0.2310(3) 0.38888(9) 0.44369(6) 0.0350(4) Uani 1 1 d . . . . .
O2 O 0.3284(3) 0.28245(11) 0.40885(7) 0.0482(5) Uani 1 1 d . . . . .
O3 O 0.2109(3) 0.53513(9) 0.51925(6) 0.0328(4) Uani 1 1 d . . . . .
O4 O 0.2644(3) 0.64590(10) 0.55466(7) 0.0429(5) Uani 1 1 d . . . . .
C1 C 0.5676(4) 0.45204(13) 0.49709(9) 0.0318(5) Uani 1 1 d . . . . .
C2 C 0.7157(4) 0.42566(15) 0.45978(10) 0.0403(6) Uani 1 1 d . . . . .
H2A H 0.820113 0.402746 0.476261 0.048 Uiso 1 1 calc R U . . .
H2B H 0.663023 0.389809 0.437231 0.048 Uiso 1 1 calc R U . . .
C3 C 0.7764(4) 0.49673(15) 0.43297(10) 0.0402(6) Uani 1 1 d . . . . .
H3A H 0.876516 0.521701 0.450010 0.048 Uiso 1 1 calc R U . . .
H3B H 0.815574 0.485685 0.399997 0.048 Uiso 1 1 calc R U . . .
C4 C 0.6022(4) 0.54314(14) 0.43340(9) 0.0354(6) Uani 1 1 d . . . . .
C5 C 0.5537(4) 0.60350(14) 0.40478(9) 0.0376(6) Uani 1 1 d . . . . .
H5 H 0.633325 0.620320 0.380535 0.045 Uiso 1 1 calc R U . . .
C6 C 0.3853(5) 0.63868(14) 0.41261(9) 0.0391(6) Uani 1 1 d . . . . .
H6 H 0.349746 0.677692 0.392329 0.047 Uiso 1 1 calc R U . . .
C7 C 0.2680(4) 0.61675(14) 0.45029(9) 0.0354(6) Uani 1 1 d . . . . .
H7 H 0.155924 0.641134 0.455590 0.043 Uiso 1 1 calc R U . . .
C8 C 0.3223(4) 0.55762(14) 0.47975(8) 0.0317(5) Uani 1 1 d . . . . .
C9 C 0.4848(4) 0.51877(13) 0.47067(8) 0.0304(5) Uani 1 1 d . . . . .
C10 C 0.6580(4) 0.47406(14) 0.54663(9) 0.0385(6) Uani 1 1 d . . . . .
H10A H 0.784285 0.491149 0.541843 0.046 Uiso 1 1 calc R U . . .
H10B H 0.587621 0.513441 0.562321 0.046 Uiso 1 1 calc R U . . .
C11 C 0.6545(4) 0.40244(15) 0.57741(10) 0.0410(6) Uani 1 1 d . . . . .
H11A H 0.765024 0.372683 0.572111 0.049 Uiso 1 1 calc R U . . .
H11B H 0.643610 0.413823 0.611786 0.049 Uiso 1 1 calc R U . . .
C12 C 0.4844(4) 0.36313(14) 0.55889(9) 0.0334(5) Uani 1 1 d . . . . .
C13 C 0.3791(4) 0.30802(15) 0.58097(9) 0.0368(6) Uani 1 1 d . . . . .
H13 H 0.412493 0.289766 0.611398 0.044 Uiso 1 1 calc R U . . .
C14 C 0.2237(4) 0.28022(14) 0.55748(9) 0.0367(6) Uani 1 1 d . . . . .
H14 H 0.151037 0.244139 0.572602 0.044 Uiso 1 1 calc R U . . .
C15 C 0.1757(4) 0.30600(14) 0.51136(10) 0.0364(6) Uani 1 1 d . . . . .
H15 H 0.072121 0.287025 0.495467 0.044 Uiso 1 1 calc R U . . .
C16 C 0.2844(4) 0.36032(13) 0.48943(9) 0.0324(5) Uani 1 1 d . . . . .
C17 C 0.4363(4) 0.39067(13) 0.51284(9) 0.0315(5) Uani 1 1 d . . . . .
C18 C 0.2608(4) 0.34333(13) 0.40461(9) 0.0320(5) Uani 1 1 d . . . . .
C19 C 0.2022(4) 0.38001(14) 0.35855(9) 0.0321(5) Uani 1 1 d . . . . .
C20 C 0.1629(4) 0.33714(14) 0.31635(9) 0.0321(5) Uani 1 1 d . . . . .
C21 C 0.1676(4) 0.25667(15) 0.31464(10) 0.0363(6) Uani 1 1 d . . . . .
H21 H 0.200842 0.230196 0.342407 0.044 Uiso 1 1 calc R U . . .
C22 C 0.1249(4) 0.21893(16) 0.27364(10) 0.0424(6) Uani 1 1 d . . . . .
H22 H 0.128413 0.167019 0.274036 0.051 Uiso 1 1 calc R U . . .
C23 C 0.0745(4) 0.25630(17) 0.22963(10) 0.0414(6) Uani 1 1 d . . . . .
C24 C 0.0370(5) 0.2175(2) 0.18632(11) 0.0518(8) Uani 1 1 d . . . . .
H24 H 0.044831 0.165646 0.185702 0.062 Uiso 1 1 calc R U . . .
C25 C -0.0115(5) 0.2560(2) 0.14459(11) 0.0594(10) Uani 1 1 d . . . . .
H25 H -0.035671 0.229856 0.116059 0.071 Uiso 1 1 calc R U . . .
C26 C -0.0242(5) 0.3324(2) 0.14491(11) 0.0527(8) Uani 1 1 d . . . . .
H26 H -0.059774 0.357159 0.116678 0.063 Uiso 1 1 calc R U . . .
C27 C 0.0151(4) 0.37396(19) 0.18672(10) 0.0431(7) Uani 1 1 d . . . . .
C28 C 0.0109(4) 0.45302(19) 0.18738(10) 0.0469(7) Uani 1 1 d . . . . .
H28 H -0.023577 0.478579 0.159359 0.056 Uiso 1 1 calc R U . . .
C29 C 0.0557(5) 0.49221(18) 0.22762(10) 0.0437(7) Uani 1 1 d . . . . .
H29 H 0.054345 0.544110 0.226628 0.052 Uiso 1 1 calc R U . . .
C30 C 0.1054(4) 0.45481(15) 0.27197(9) 0.0352(6) Uani 1 1 d . . . . .
C31 C 0.1492(4) 0.49468(15) 0.31441(9) 0.0377(6) Uani 1 1 d . . . . .
H31 H 0.148279 0.546602 0.313926 0.045 Uiso 1 1 calc R U . . .
C32 C 0.1936(4) 0.45769(14) 0.35673(9) 0.0358(6) Uani 1 1 d . . . . .
H32 H 0.218290 0.485129 0.384708 0.043 Uiso 1 1 calc R U . . .
C33 C 0.1119(4) 0.37570(15) 0.27289(9) 0.0323(5) Uani 1 1 d . . . . .
C34 C 0.0673(4) 0.33482(16) 0.22981(9) 0.0363(6) Uani 1 1 d . . . . .
C35 C 0.2014(4) 0.58403(13) 0.55723(8) 0.0310(5) Uani 1 1 d . . . . .
C36 C 0.1141(4) 0.54999(14) 0.60104(8) 0.0310(5) Uani 1 1 d . . . . .
C37 C 0.1091(4) 0.47197(14) 0.60441(9) 0.0338(5) Uani 1 1 d . . . . .
H37 H 0.145555 0.443402 0.577831 0.041 Uiso 1 1 calc R U . . .
C38 C 0.0514(4) 0.43669(15) 0.64624(9) 0.0360(6) Uani 1 1 d . . . . .
H38 H 0.047969 0.384812 0.647376 0.043 Uiso 1 1 calc R U . . .
C39 C -0.0022(4) 0.47809(15) 0.68707(9) 0.0344(6) Uani 1 1 d . . . . .
C40 C -0.0539(4) 0.44319(16) 0.73235(10) 0.0395(6) Uani 1 1 d . . . . .
H40 H -0.053763 0.391368 0.734493 0.047 Uiso 1 1 calc R U . . .
C41 C -0.1019(4) 0.48329(18) 0.77125(10) 0.0437(7) Uani 1 1 d . . . . .
H41 H -0.133134 0.458711 0.799900 0.052 Uiso 1 1 calc R U . . .
C42 C -0.1066(4) 0.56266(17) 0.77005(9) 0.0376(6) Uani 1 1 d . . . . .
C43 C -0.1545(4) 0.60599(18) 0.81032(10) 0.0446(7) Uani 1 1 d . . . . .
H43 H -0.183517 0.582323 0.839455 0.054 Uiso 1 1 calc R U . . .
C44 C -0.1602(4) 0.68283(19) 0.80815(10) 0.0449(7) Uani 1 1 d . . . . .
H44 H -0.194839 0.710181 0.835432 0.054 Uiso 1 1 calc R U . . .
C45 C -0.1145(4) 0.71939(17) 0.76541(10) 0.0410(6) Uani 1 1 d . . . . .
H45 H -0.118906 0.771243 0.764083 0.049 Uiso 1 1 calc R U . . .
C46 C -0.0615(4) 0.67856(16) 0.72407(9) 0.0338(5) Uani 1 1 d . . . . .
C47 C -0.0086(4) 0.71424(15) 0.67952(9) 0.0354(6) Uani 1 1 d . . . . .
H47 H -0.012629 0.766066 0.677635 0.042 Uiso 1 1 calc R U . . .
C48 C 0.0469(4) 0.67499(14) 0.64018(9) 0.0336(5) Uani 1 1 d . . . . .
H48 H 0.081212 0.700470 0.612117 0.040 Uiso 1 1 calc R U . . .
C49 C 0.0542(4) 0.59482(14) 0.64064(9) 0.0311(5) Uani 1 1 d . . . . .
C50 C -0.0034(4) 0.55746(14) 0.68426(9) 0.0306(5) Uani 1 1 d . . . . .
C51 C -0.0576(4) 0.60010(14) 0.72590(9) 0.0318(5) Uani 1 1 d . . . . .
O5 O -0.1234(5) 0.70791(15) 0.47665(12) 0.0823(9) Uani 1 1 d . . . . .
H5A H -0.152696 0.751705 0.472551 0.123 Uiso 1 1 calc R U . . .
C52 C -0.2218(6) 0.67885(18) 0.51575(13) 0.0560(8) Uani 1 1 d . . . . .
H52A H -0.351948 0.679591 0.508494 0.084 Uiso 1 1 calc R U . . .
H52B H -0.198398 0.708512 0.544186 0.084 Uiso 1 1 calc R U . . .
H52C H -0.182897 0.628379 0.521601 0.084 Uiso 1 1 calc R U . . .
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'
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
C18 O1 C16 116.19(18) . . ?
C35 O3 C8 115.77(19) . . ?
C2 C1 C10 111.5(2) . . ?
C9 C1 C2 101.2(2) . . ?
C9 C1 C10 112.5(2) . . ?
C17 C1 C2 113.4(2) . . ?
C17 C1 C9 117.5(2) . . ?
C17 C1 C10 101.24(19) . . ?
C1 C2 H2A 110.7 . . ?
C1 C2 H2B 110.7 . . ?
H2A C2 H2B 108.8 . . ?
C3 C2 C1 105.1(2) . . ?
C3 C2 H2A 110.7 . . ?
C3 C2 H2B 110.7 . . ?
C2 C3 H3A 111.3 . . ?
C2 C3 H3B 111.3 . . ?
H3A C3 H3B 109.2 . . ?
C4 C3 C2 102.5(2) . . ?
C4 C3 H3A 111.3 . . ?
C4 C3 H3B 111.3 . . ?
C5 C4 C3 129.6(2) . . ?
C5 C4 C9 120.6(3) . . ?
C9 C4 C3 109.8(2) . . ?
C4 C5 H5 120.4 . . ?
C4 C5 C6 119.3(3) . . ?
C6 C5 H5 120.4 . . ?
C5 C6 H6 119.3 . . ?
C5 C6 C7 121.3(2) . . ?
C7 C6 H6 119.3 . . ?
C6 C7 H7 120.8 . . ?
C8 C7 C6 118.5(3) . . ?
C8 C7 H7 120.8 . . ?
C7 C8 O3 120.4(2) . . ?
C9 C8 O3 118.5(2) . . ?
C9 C8 C7 121.1(2) . . ?
C4 C9 C1 111.0(2) . . ?
C8 C9 C1 129.8(2) . . ?
C8 C9 C4 119.1(2) . . ?
C1 C10 H10A 110.7 . . ?
C1 C10 H10B 110.7 . . ?
H10A C10 H10B 108.8 . . ?
C11 C10 C1 105.2(2) . . ?
C11 C10 H10A 110.7 . . ?
C11 C10 H10B 110.7 . . ?
C10 C11 H11A 111.3 . . ?
C10 C11 H11B 111.3 . . ?
H11A C11 H11B 109.2 . . ?
C12 C11 C10 102.6(2) . . ?
C12 C11 H11A 111.3 . . ?
C12 C11 H11B 111.3 . . ?
C13 C12 C11 129.2(2) . . ?
C13 C12 C17 120.7(3) . . ?
C17 C12 C11 110.1(2) . . ?
C12 C13 H13 120.2 . . ?
C12 C13 C14 119.7(2) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 H14 119.8 . . ?
C13 C14 C15 120.4(3) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 120.4 . . ?
C16 C15 C14 119.2(3) . . ?
C16 C15 H15 120.4 . . ?
C15 C16 O1 119.2(2) . . ?
C17 C16 O1 119.3(2) . . ?
C17 C16 C15 121.4(2) . . ?
C12 C17 C1 111.0(2) . . ?
C16 C17 C1 130.4(2) . . ?
C16 C17 C12 118.6(2) . . ?
O1 C18 C19 111.2(2) . . ?
O2 C18 O1 122.0(2) . . ?
O2 C18 C19 126.8(2) . . ?
C20 C19 C18 120.9(2) . . ?
C32 C19 C18 118.9(2) . . ?
C32 C19 C20 120.1(2) . . ?
C19 C20 C21 124.2(2) . . ?
C19 C20 C33 118.3(2) . . ?
C33 C20 C21 117.5(2) . . ?
C20 C21 H21 119.3 . . ?
C22 C21 C20 121.5(3) . . ?
C22 C21 H21 119.3 . . ?
C21 C22 H22 119.0 . . ?
C21 C22 C23 122.0(3) . . ?
C23 C22 H22 119.0 . . ?
C24 C23 C22 122.3(3) . . ?
C24 C23 C34 119.4(3) . . ?
C34 C23 C22 118.3(2) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 C23 120.3(3) . . ?
C25 C24 H24 119.9 . . ?
C24 C25 H25 119.7 . . ?
C26 C25 C24 120.6(3) . . ?
C26 C25 H25 119.7 . . ?
C25 C26 H26 119.2 . . ?
C25 C26 C27 121.5(3) . . ?
C27 C26 H26 119.2 . . ?
C26 C27 C28 122.6(3) . . ?
C26 C27 C34 118.3(3) . . ?
C28 C27 C34 119.1(3) . . ?
C27 C28 H28 119.2 . . ?
C29 C28 C27 121.7(3) . . ?
C29 C28 H28 119.2 . . ?
C28 C29 H29 119.6 . . ?
C28 C29 C30 120.9(3) . . ?
C30 C29 H29 119.6 . . ?
C31 C30 C29 121.6(2) . . ?
C31 C30 C33 119.1(2) . . ?
C33 C30 C29 119.3(3) . . ?
C30 C31 H31 119.7 . . ?
C32 C31 C30 120.7(2) . . ?
C32 C31 H31 119.7 . . ?
C19 C32 H32 119.3 . . ?
C31 C32 C19 121.4(2) . . ?
C31 C32 H32 119.3 . . ?
C20 C33 C34 120.2(2) . . ?
C30 C33 C20 120.4(2) . . ?
C30 C33 C34 119.3(2) . . ?
C23 C34 C27 119.8(2) . . ?
C23 C34 C33 120.4(2) . . ?
C27 C34 C33 119.7(2) . . ?
O3 C35 C36 112.2(2) . . ?
O4 C35 O3 121.9(2) . . ?
O4 C35 C36 125.8(2) . . ?
C37 C36 C35 118.2(2) . . ?
C37 C36 C49 120.4(2) . . ?
C49 C36 C35 121.1(2) . . ?
C36 C37 H37 119.3 . . ?
C38 C37 C36 121.4(2) . . ?
C38 C37 H37 119.3 . . ?
C37 C38 H38 119.7 . . ?
C37 C38 C39 120.7(2) . . ?
C39 C38 H38 119.7 . . ?
C38 C39 C40 122.3(2) . . ?
C38 C39 C50 119.1(2) . . ?
C50 C39 C40 118.6(2) . . ?
C39 C40 H40 119.1 . . ?
C41 C40 C39 121.7(3) . . ?
C41 C40 H40 119.1 . . ?
C40 C41 H41 119.1 . . ?
C40 C41 C42 121.7(2) . . ?
C42 C41 H41 119.1 . . ?
C41 C42 C51 118.8(2) . . ?
C43 C42 C41 122.9(3) . . ?
C43 C42 C51 118.3(3) . . ?
C42 C43 H43 119.1 . . ?
C44 C43 C42 121.9(3) . . ?
C44 C43 H43 119.1 . . ?
C43 C44 H44 119.9 . . ?
C43 C44 C45 120.1(3) . . ?
C45 C44 H44 119.9 . . ?
C44 C45 H45 119.8 . . ?
C44 C45 C46 120.4(3) . . ?
C46 C45 H45 119.8 . . ?
C45 C46 C47 122.1(3) . . ?
C45 C46 C51 119.8(2) . . ?
C51 C46 C47 118.1(2) . . ?
C46 C47 H47 119.0 . . ?
C48 C47 C46 122.1(2) . . ?
C48 C47 H47 119.0 . . ?
C47 C48 H48 119.2 . . ?
C47 C48 C49 121.6(2) . . ?
C49 C48 H48 119.2 . . ?
C36 C49 C48 124.7(2) . . ?
C36 C49 C50 117.7(2) . . ?
C50 C49 C48 117.6(2) . . ?
C39 C50 C49 120.6(2) . . ?
C39 C50 C51 119.4(2) . . ?
C51 C50 C49 119.9(2) . . ?
C46 C51 C42 119.6(2) . . ?
C46 C51 C50 120.7(2) . . ?
C50 C51 C42 119.7(2) . . ?
C52 O5 H5A 109.5 . . ?
O5 C52 H52A 109.5 . . ?
O5 C52 H52B 109.5 . . ?
O5 C52 H52C 109.5 . . ?
H52A C52 H52B 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
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 C16 1.411(3) . ?
O1 C18 1.366(3) . ?
O2 C18 1.200(3) . ?
O3 C8 1.410(3) . ?
O3 C35 1.364(3) . ?
O4 C35 1.200(3) . ?
C1 C2 1.554(4) . ?
C1 C9 1.520(3) . ?
C1 C10 1.561(3) . ?
C1 C17 1.514(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.535(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.507(4) . ?
C4 C5 1.382(4) . ?
C4 C9 1.399(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.385(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.394(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.390(3) . ?
C8 C9 1.386(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.537(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.503(4) . ?
C12 C13 1.386(4) . ?
C12 C17 1.402(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.386(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.393(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.387(4) . ?
C16 C17 1.382(4) . ?
C18 C19 1.488(3) . ?
C19 C20 1.420(3) . ?
C19 C32 1.394(4) . ?
C20 C21 1.442(4) . ?
C20 C33 1.428(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.350(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.430(4) . ?
C23 C24 1.405(4) . ?
C23 C34 1.407(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.384(5) . ?
C25 H25 0.9300 . ?
C25 C26 1.371(5) . ?
C26 H26 0.9300 . ?
C26 C27 1.398(4) . ?
C27 C28 1.416(5) . ?
C27 C34 1.427(4) . ?
C28 H28 0.9300 . ?
C28 C29 1.349(5) . ?
C29 H29 0.9300 . ?
C29 C30 1.437(4) . ?
C30 C31 1.404(4) . ?
C30 C33 1.418(4) . ?
C31 H31 0.9300 . ?
C31 C32 1.377(4) . ?
C32 H32 0.9300 . ?
C33 C34 1.429(4) . ?
C35 C36 1.489(3) . ?
C36 C37 1.401(3) . ?
C36 C49 1.420(3) . ?
C37 H37 0.9300 . ?
C37 C38 1.376(4) . ?
C38 H38 0.9300 . ?
C38 C39 1.400(4) . ?
C39 C40 1.442(4) . ?
C39 C50 1.423(4) . ?
C40 H40 0.9300 . ?
C40 C41 1.334(4) . ?
C41 H41 0.9300 . ?
C41 C42 1.422(4) . ?
C42 C43 1.395(4) . ?
C42 C51 1.431(4) . ?
C43 H43 0.9300 . ?
C43 C44 1.378(5) . ?
C44 H44 0.9300 . ?
C44 C45 1.385(4) . ?
C45 H45 0.9300 . ?
C45 C46 1.404(4) . ?
C46 C47 1.433(4) . ?
C46 C51 1.406(4) . ?
C47 H47 0.9300 . ?
C47 C48 1.351(4) . ?
C48 H48 0.9300 . ?
C48 C49 1.437(3) . ?
C49 C50 1.435(3) . ?
C50 C51 1.431(4) . ?
O5 H5A 0.8200 . ?
O5 C52 1.389(4) . ?
C52 H52A 0.9600 . ?
C52 H52B 0.9600 . ?
C52 H52C 0.9600 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O5 H5A O4 0.82 2.07 2.872(3) 166.4 4_466 yes
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 C16 C17 C1 -1.5(4) . . . . ?
O1 C16 C17 C12 178.2(2) . . . . ?
O1 C18 C19 C20 -159.3(2) . . . . ?
O1 C18 C19 C32 23.2(4) . . . . ?
O2 C18 C19 C20 21.7(5) . . . . ?
O2 C18 C19 C32 -155.7(3) . . . . ?
O3 C8 C9 C1 0.6(4) . . . . ?
O3 C8 C9 C4 -176.3(2) . . . . ?
O3 C35 C36 C37 20.0(3) . . . . ?
O3 C35 C36 C49 -166.2(2) . . . . ?
O4 C35 C36 C37 -157.1(3) . . . . ?
O4 C35 C36 C49 16.7(4) . . . . ?
C1 C2 C3 C4 -31.7(3) . . . . ?
C1 C10 C11 C12 -30.4(3) . . . . ?
C2 C1 C9 C4 -17.6(3) . . . . ?
C2 C1 C9 C8 165.3(3) . . . . ?
C2 C1 C10 C11 -91.6(3) . . . . ?
C2 C1 C17 C12 101.9(3) . . . . ?
C2 C1 C17 C16 -78.5(3) . . . . ?
C2 C3 C4 C5 -161.3(3) . . . . ?
C2 C3 C4 C9 21.3(3) . . . . ?
C3 C4 C5 C6 -178.7(3) . . . . ?
C3 C4 C9 C1 -2.2(3) . . . . ?
C3 C4 C9 C8 175.3(2) . . . . ?
C4 C5 C6 C7 3.2(4) . . . . ?
C5 C4 C9 C1 -179.8(2) . . . . ?
C5 C4 C9 C8 -2.4(4) . . . . ?
C5 C6 C7 C8 -0.9(4) . . . . ?
C6 C7 C8 O3 177.9(2) . . . . ?
C6 C7 C8 C9 -3.1(4) . . . . ?
C7 C8 C9 C1 -178.4(2) . . . . ?
C7 C8 C9 C4 4.7(4) . . . . ?
C8 O3 C35 O4 9.0(4) . . . . ?
C8 O3 C35 C36 -168.3(2) . . . . ?
C9 C1 C2 C3 30.1(3) . . . . ?
C9 C1 C10 C11 155.6(2) . . . . ?
C9 C1 C17 C12 -140.5(2) . . . . ?
C9 C1 C17 C16 39.2(4) . . . . ?
C9 C4 C5 C6 -1.5(4) . . . . ?
C10 C1 C2 C3 -89.7(3) . . . . ?
C10 C1 C9 C4 101.4(3) . . . . ?
C10 C1 C9 C8 -75.7(3) . . . . ?
C10 C1 C17 C12 -17.6(3) . . . . ?
C10 C1 C17 C16 162.0(3) . . . . ?
C10 C11 C12 C13 -159.3(3) . . . . ?
C10 C11 C12 C17 20.0(3) . . . . ?
C11 C12 C13 C14 178.7(3) . . . . ?
C11 C12 C17 C1 -1.3(3) . . . . ?
C11 C12 C17 C16 179.0(2) . . . . ?
C12 C13 C14 C15 1.6(4) . . . . ?
C13 C12 C17 C1 178.1(2) . . . . ?
C13 C12 C17 C16 -1.6(4) . . . . ?
C13 C14 C15 C16 -0.6(4) . . . . ?
C14 C15 C16 O1 -177.1(2) . . . . ?
C14 C15 C16 C17 -1.6(4) . . . . ?
C15 C16 C17 C1 -177.0(2) . . . . ?
C15 C16 C17 C12 2.7(4) . . . . ?
C16 O1 C18 O2 0.1(4) . . . . ?
C16 O1 C18 C19 -179.0(2) . . . . ?
C17 C1 C2 C3 156.8(2) . . . . ?
C17 C1 C9 C4 -141.6(2) . . . . ?
C17 C1 C9 C8 41.3(4) . . . . ?
C17 C1 C10 C11 29.4(3) . . . . ?
C17 C12 C13 C14 -0.5(4) . . . . ?
C18 O1 C16 C15 -75.0(3) . . . . ?
C18 O1 C16 C17 109.4(3) . . . . ?
C18 C19 C20 C21 2.8(4) . . . . ?
C18 C19 C20 C33 -178.4(2) . . . . ?
C18 C19 C32 C31 176.7(3) . . . . ?
C19 C20 C21 C22 178.5(3) . . . . ?
C19 C20 C33 C30 1.5(4) . . . . ?
C19 C20 C33 C34 -178.7(2) . . . . ?
C20 C19 C32 C31 -0.7(4) . . . . ?
C20 C21 C22 C23 0.6(5) . . . . ?
C20 C33 C34 C23 -0.5(4) . . . . ?
C20 C33 C34 C27 179.5(3) . . . . ?
C21 C20 C33 C30 -179.7(3) . . . . ?
C21 C20 C33 C34 0.1(4) . . . . ?
C21 C22 C23 C24 177.4(3) . . . . ?
C21 C22 C23 C34 -0.9(4) . . . . ?
C22 C23 C24 C25 179.9(3) . . . . ?
C22 C23 C34 C27 -179.1(3) . . . . ?
C22 C23 C34 C33 0.8(4) . . . . ?
C23 C24 C25 C26 -0.2(5) . . . . ?
C24 C23 C34 C27 2.5(4) . . . . ?
C24 C23 C34 C33 -177.6(3) . . . . ?
C24 C25 C26 C27 1.5(5) . . . . ?
C25 C26 C27 C28 177.1(3) . . . . ?
C25 C26 C27 C34 -0.7(5) . . . . ?
C26 C27 C28 C29 -177.6(3) . . . . ?
C26 C27 C34 C23 -1.3(4) . . . . ?
C26 C27 C34 C33 178.8(3) . . . . ?
C27 C28 C29 C30 -1.5(5) . . . . ?
C28 C27 C34 C23 -179.2(3) . . . . ?
C28 C27 C34 C33 0.9(4) . . . . ?
C28 C29 C30 C31 -178.9(3) . . . . ?
C28 C29 C30 C33 1.6(4) . . . . ?
C29 C30 C31 C32 178.9(3) . . . . ?
C29 C30 C33 C20 179.3(3) . . . . ?
C29 C30 C33 C34 -0.5(4) . . . . ?
C30 C31 C32 C19 2.0(4) . . . . ?
C30 C33 C34 C23 179.4(3) . . . . ?
C30 C33 C34 C27 -0.7(4) . . . . ?
C31 C30 C33 C20 -0.2(4) . . . . ?
C31 C30 C33 C34 180.0(3) . . . . ?
C32 C19 C20 C21 -179.8(3) . . . . ?
C32 C19 C20 C33 -1.1(4) . . . . ?
C33 C20 C21 C22 -0.2(4) . . . . ?
C33 C30 C31 C32 -1.6(4) . . . . ?
C34 C23 C24 C25 -1.8(5) . . . . ?
C34 C27 C28 C29 0.2(5) . . . . ?
C35 O3 C8 C7 -69.1(3) . . . . ?
C35 O3 C8 C9 111.9(2) . . . . ?
C35 C36 C37 C38 172.1(2) . . . . ?
C35 C36 C49 C48 8.9(4) . . . . ?
C35 C36 C49 C50 -171.1(2) . . . . ?
C36 C37 C38 C39 -0.8(4) . . . . ?
C36 C49 C50 C39 -0.8(4) . . . . ?
C36 C49 C50 C51 177.4(2) . . . . ?
C37 C36 C49 C48 -177.4(3) . . . . ?
C37 C36 C49 C50 2.5(4) . . . . ?
C37 C38 C39 C40 -176.6(3) . . . . ?
C37 C38 C39 C50 2.5(4) . . . . ?
C38 C39 C40 C41 178.9(3) . . . . ?
C38 C39 C50 C49 -1.6(4) . . . . ?
C38 C39 C50 C51 -179.8(2) . . . . ?
C39 C40 C41 C42 0.6(5) . . . . ?
C39 C50 C51 C42 1.1(4) . . . . ?
C39 C50 C51 C46 -179.5(2) . . . . ?
C40 C39 C50 C49 177.4(2) . . . . ?
C40 C39 C50 C51 -0.8(4) . . . . ?
C40 C41 C42 C43 -179.4(3) . . . . ?
C40 C41 C42 C51 -0.3(4) . . . . ?
C41 C42 C43 C44 -179.2(3) . . . . ?
C41 C42 C51 C46 180.0(3) . . . . ?
C41 C42 C51 C50 -0.6(4) . . . . ?
C42 C43 C44 C45 -1.1(5) . . . . ?
C43 C42 C51 C46 -0.9(4) . . . . ?
C43 C42 C51 C50 178.5(3) . . . . ?
C43 C44 C45 C46 -0.2(5) . . . . ?
C44 C45 C46 C47 -178.4(3) . . . . ?
C44 C45 C46 C51 1.0(4) . . . . ?
C45 C46 C47 C48 178.3(3) . . . . ?
C45 C46 C51 C42 -0.4(4) . . . . ?
C45 C46 C51 C50 -179.8(2) . . . . ?
C46 C47 C48 C49 0.7(4) . . . . ?
C47 C46 C51 C42 179.0(2) . . . . ?
C47 C46 C51 C50 -0.4(4) . . . . ?
C47 C48 C49 C36 -178.8(3) . . . . ?
C47 C48 C49 C50 1.2(4) . . . . ?
C48 C49 C50 C39 179.1(2) . . . . ?
C48 C49 C50 C51 -2.7(4) . . . . ?
C49 C36 C37 C38 -1.8(4) . . . . ?
C49 C50 C51 C42 -177.1(2) . . . . ?
C49 C50 C51 C46 2.3(4) . . . . ?
C50 C39 C40 C41 -0.1(4) . . . . ?
C51 C42 C43 C44 1.7(4) . . . . ?
C51 C46 C47 C48 -1.1(4) . . . . ?
