#------------------------------------------------------------------------------
#$Date: 2025-05-14 13:17:04 +0300 (Wed, 14 May 2025) $
#$Revision: 299663 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/22/1572258.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_1572258
loop_
_publ_author_name
'Sarkar, Koushik'
'Behera, Prativa'
'Roy, Lisa'
'Maji, Biplab'
_publ_section_title
;
 Manganese catalyzed chemo-selective synthesis of acyl cyclopentenes: a
 combined experimental and computational investigation.
;
_journal_issue                   35
_journal_name_full               'Chemical science'
_journal_page_first              14287
_journal_page_last               14294
_journal_paper_doi               10.1039/d4sc02842b
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C23 H26 O'
_chemical_formula_sum            'C23 H26 O'
_chemical_formula_weight         318.43
_chemical_name_systematic
(Z)-3-cyclopropyl-1-(2,3,4,5,6-pentamethylphenyl)-3-phenylprop-2-en-1-one
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-01-20
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-01-20 deposited with the CCDC.	2024-08-05 downloaded from the CCDC.
;
_cell_angle_alpha                103.7839(13)
_cell_angle_beta                 96.8936(18)
_cell_angle_gamma                92.5400(16)
_cell_formula_units_Z            4
_cell_length_a                   9.0547(2)
_cell_length_b                   10.15893(15)
_cell_length_c                   20.6100(3)
_cell_measurement_reflns_used    14418
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.1660
_cell_measurement_theta_min      2.2120
_cell_volume                     1822.69(6)
_computing_cell_refinement       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.58a (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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.996
_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      5.00  41.00   0.50    0.20    --   40.33 -38.00-150.00   72
  2  ω    -24.00   2.00   0.50    0.20    --   40.33 -38.00-150.00   52
  3  ω    -26.00  28.00   0.50    0.20    --   40.33 -25.00  60.00  108
  4  ω    -30.00   0.00   0.50    0.20    --   40.33 -25.00 150.00   60
  5  ω      3.00  29.00   0.50    0.20    --   40.33 -25.00 150.00   52
  6  ω     29.00 105.00   0.50    0.50    --   96.67 -77.00  90.00  152
  7  ω     30.00  56.00   0.50    0.50    --   96.67 -68.00 150.00   52
  8  ω     29.00  67.00   0.50    0.50    --   96.67 -59.00   0.00   76
  9  ω     36.00  62.00   0.50    0.50    --   96.67 -59.00  90.00   52
 10  ω     38.00  67.00   0.50    0.50    --   96.67 -59.00 -30.00   58
 11  ω     43.00  68.00   0.50    0.50    --   96.67 -59.00 -60.00   50
 12  ω     34.00  62.00   0.50    0.50    --   96.67 -59.00 -90.00   56
 13  ω     31.00  56.00   0.50    0.50    --   96.67 -50.00-180.00   50
 14  ω    102.00 127.00   0.50    0.50    --   96.67 -87.00-180.00   50
 15  ω    102.00 127.00   0.50    0.50    --   96.67-145.00-150.00   50
 16  ω     96.00 122.00   0.50    0.50    --   96.67-145.00 -90.00   52
 17  ω     47.00  86.00   0.50    0.50    --   96.67-145.00-150.00   78
 18  ω     45.00  88.00   0.50    0.50    --   96.67-145.00 -90.00   86
 19  ω     36.00 109.00   0.50    0.50    --   96.67-117.00 -90.00  146
 20  ω     65.00  91.00   0.50    0.50    --   96.67-149.00 -46.00   52
 21  ω     27.00  79.00   0.50    0.50    --   96.67 -87.00-180.00  104
 22  ω     53.00 117.00   0.50    0.50    --   96.67 -87.00   0.00  128
 23  ω     60.00  91.00   0.50    0.50    --   96.67 -87.00 -90.00   62
 24  ω     34.00 104.00   0.50    0.50    --   96.67-117.00   0.00  140
 25  ω     61.00 127.00   0.50    0.50    --   96.67-145.00 120.00  132
 26  ω     72.00 106.00   0.50    0.50    --   96.67-124.00 117.00   68
 27  ω     18.00  72.00   0.50    0.20    --   40.33-104.00 150.00  108
 28  ω     33.00  90.00   0.50    0.20    --   40.33-124.00 117.00  114
 29  ω     46.00 106.00   0.50    0.20    --   40.33-149.00 -46.00  120
 30  ω     93.00 157.00   0.50    0.50    --   96.67  50.00 150.00  128
 31  ω     75.00 164.00   0.50    0.50    --   96.67  59.00  90.00  178
 32  ω     81.00 164.00   0.50    0.50    --   96.67  59.00 120.00  166
 33  ω     84.00 149.00   0.50    0.50    --   96.67  42.00  60.00  130
 34  ω     83.00 166.00   0.50    0.50    --   96.67  25.00  30.00  166
 35  ω     78.00 144.00   0.50    0.50    --   96.67  59.00-180.00  132
 36  ω    100.00 125.00   0.50    0.50    --   96.67 149.00   0.00   50
 37  ω    111.00 165.00   0.50    0.50    --   96.67  96.00  60.00  108
 38  ω    102.00 164.00   0.50    0.50    --   96.67 117.00  30.00  124
 39  ω     90.00 133.00   0.50    0.50    --   96.67 145.00 -60.00   86
 40  ω    105.00 130.00   0.50    0.50    --   96.67 124.00-163.00   50
 41  ω     82.00 108.00   0.50    0.20    --   40.33  77.00 -60.00   52
 42  ω     64.00 106.00   0.50    0.20    --   40.33  25.00  60.00   84
 43  ω     27.00  56.00   0.50    0.20    --   40.33  25.00  60.00   58
 44  ω     14.00  51.00   0.50    0.20    --   40.33  77.00 -60.00   74
 45  ω     -7.00  19.00   0.50    0.20    --  -40.33  64.00  60.00   52
 46  ω    -13.00  34.00   0.50    0.20    --  -40.33  12.00  60.00   94
 47  ω    -53.00 -28.00   0.50    0.20    --  -40.33  64.00  60.00   50
 48  ω    -23.00  31.00   0.50    0.20    --  -40.33  12.00 -60.00  108
 49  ω    -51.00 -14.00   0.50    0.50    --  -82.50  59.00  30.00   74
 50  ω    -42.00 -16.00   0.50    0.50    --  -82.50  42.00 150.00   52
 51  ω    -47.00 -17.00   0.50    0.50    --  -82.50  42.00  90.00   60
 52  ω    -45.00 -19.00   0.50    0.50    --  -82.50  42.00 -90.00   52
 53  ω    -44.00 -16.00   0.50    0.50    --  -82.50  42.00-120.00   56
 54  ω    -44.00 -19.00   0.50    0.50    --  -82.50  50.00-120.00   50
 55  ω    -85.00 -15.00   0.50    0.50    --  -82.50 124.00-163.00  140
 56  ω    -86.00 -11.00   0.50    0.20    --  -40.33 124.00-163.00  150
 57  ω   -104.00 -25.00   0.50    0.20    --  -40.33 149.00   0.00  158
 58  ω   -147.00 -99.00   0.50    0.50    --  -82.50 -68.00   0.00   96
 59  ω    -91.00 -24.00   0.50    0.20    --  -40.33 -50.00 -60.00  134
 60  ω    -49.00 -23.00   0.50    0.20    --  -40.33 -77.00 -30.00   52
 61  ω   -108.00 -67.00   0.50    0.20    --  -40.33 -77.00 -30.00   82
 62  ω   -108.00 -56.00   0.50    0.20    --  -40.33-149.00 -46.00  104
 63  ω   -150.00 -56.00   0.50    0.50    --  -82.50-149.00 -46.00  188
 64  ω   -150.00 -73.00   0.50    0.50    --  -82.50-124.00 117.00  154
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0466322000
_diffrn_orient_matrix_UB_12      0.0353003000
_diffrn_orient_matrix_UB_13      0.0712284000
_diffrn_orient_matrix_UB_21      -0.1633195000
_diffrn_orient_matrix_UB_22      -0.0459620000
_diffrn_orient_matrix_UB_23      -0.0303195000
_diffrn_orient_matrix_UB_31      0.0262944000
_diffrn_orient_matrix_UB_32      -0.1454723000
_diffrn_orient_matrix_UB_33      0.0063301000
_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  0.0594
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            19809
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.310
_diffrn_reflns_theta_min         2.228
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.524
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56864
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.58a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.160
_exptl_crystal_F_000             688
_exptl_crystal_preparation       'hexane in DCM'
_exptl_crystal_recrystallization_method 'hexane in DCM'
_exptl_crystal_size_max          0.002
_exptl_crystal_size_mid          0.001
_exptl_crystal_size_min          0.001
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.0031(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     444
_refine_ls_number_reflns         6602
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0488
_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)+(0.0795P)²+0.4615P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1357
_refine_ls_wR_factor_ref         0.1388
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5997
_reflns_number_total             6602
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc02842b2.cif
_cod_data_source_block           bipksk_int_auto
_cod_depositor_comments
;
Adding full bibliography for 1572257--1572260.cif.

2025-05-14
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C46 H52 O2'
_cod_original_formula_weight         636.87
_cod_original_formula_moiety         '2(C23 H26 O)'
_cod_original_formula_units_Z            2
_cod_original_cell_volume        1822.70(6)
_cod_database_code               1572258
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O'
_chemical_oxdiff_usercomment     100K
_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.
;
_shelx_estimated_absorpt_t_max   0.999
_shelx_estimated_absorpt_t_min   0.999
_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:
 C35(H35), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C19(H19a,H19b), C37(H37a,H37b), C36(H36a,H36b), C18(H18a,H18b)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C12(H12), C15(H15), C32(H32), C43(H43), C42(H42), C8(H8), C40(H40),
 C41(H41), C13(H13), C39(H39), C16(H16)
2.d Idealised Me refined as rotating group:
 C22(H22a,H22b,H22c), C44(H44a,H44b,H44c), C24(H24a,H24b,H24c), C46(H46a,H46b,
 H46c), C21(H21a,H21b,H21c), C20(H20a,H20b,H20c), C47(H47a,H47b,H47c), C23(H23a,
 H23b,H23c), C48(H48a,H48b,H48c), C45(H45a,H45b,H45c)
;
_olex2_exptl_crystal_mounting_method Cu
_olex2_submission_original_sample_id KSK_KC_INT
_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 1.812
_oxdiff_exptl_absorpt_empirical_full_min 0.711
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
O10 O 0.01999(11) 0.05343(10) 0.29731(5) 0.0335(3) Uani 1 1 d . . . . .
C14 C -0.34451(15) -0.34624(14) 0.03324(7) 0.0290(3) Uani 1 1 d . . . . .
H14 H -0.435635 -0.367059 0.003509 0.035 Uiso 1 1 calc R U . . .
C5 C -0.40390(14) 0.00758(13) 0.16348(7) 0.0247(3) Uani 1 1 d . . . . .
O34 O 0.49947(12) 0.49686(13) 0.20541(6) 0.0445(3) Uani 1 1 d . . . . .
C12 C -0.09511(15) -0.23959(13) 0.06148(7) 0.0248(3) Uani 1 1 d . . . . .
H12 H -0.015086 -0.189067 0.050446 0.030 Uiso 1 1 calc R U . . .
C1 C -0.13871(14) 0.00406(12) 0.19389(6) 0.0213(3) Uani 1 1 d . . . . .
C4 C -0.37588(15) 0.08432(13) 0.11753(7) 0.0261(3) Uani 1 1 d . . . . .
C2 C -0.10933(14) 0.07856(13) 0.14721(7) 0.0238(3) Uani 1 1 d . . . . .
C15 C -0.32801(15) -0.39046(13) 0.09196(7) 0.0271(3) Uani 1 1 d . . . . .
H15 H -0.407507 -0.442824 0.102253 0.033 Uiso 1 1 calc R U . . .
C33 C 0.46709(14) 0.31380(13) 0.33267(7) 0.0230(3) Uani 1 1 d . . . . .
C6 C -0.28439(14) -0.03331(12) 0.20200(6) 0.0216(3) Uani 1 1 d . . . . .
C11 C -0.07861(14) -0.28130(12) 0.12139(6) 0.0210(3) Uani 1 1 d . . . . .
C31 C 0.53466(15) 0.47391(14) 0.26073(7) 0.0266(3) Uani 1 1 d . . . . .
C32 C 0.44039(15) 0.37330(14) 0.28126(7) 0.0267(3) Uani 1 1 d . . . . .
H32 H 0.346586 0.346457 0.254055 0.032 Uiso 1 1 calc R U . . .
C3 C -0.22924(15) 0.11855(13) 0.10884(7) 0.0254(3) Uani 1 1 d . . . . .
C19 C 0.21653(17) -0.40671(15) 0.08993(8) 0.0348(3) Uani 1 1 d . . . . .
H19A H 0.153678 -0.386637 0.051240 0.042 Uiso 1 1 calc R U . . .
H19B H 0.322645 -0.416886 0.083973 0.042 Uiso 1 1 calc R U . . .
C29 C 0.76723(17) 0.75994(14) 0.38861(7) 0.0302(3) Uani 1 1 d . . . . .
C43 C 0.62928(15) 0.43519(13) 0.44012(7) 0.0244(3) Uani 1 1 d . . . . .
H43 H 0.552945 0.494824 0.450678 0.029 Uiso 1 1 calc R U . . .
C22 C -0.31209(16) -0.11637(14) 0.25171(7) 0.0277(3) Uani 1 1 d . . . . .
H22A H -0.362776 -0.062864 0.287423 0.042 Uiso 1 1 calc R U . . .
H22B H -0.216651 -0.141026 0.271582 0.042 Uiso 1 1 calc R U . . .
H22C H -0.374835 -0.199151 0.228392 0.042 Uiso 1 1 calc R U . . .
C37 C 0.31942(16) 0.21540(15) 0.41408(8) 0.0319(3) Uani 1 1 d . . . . .
H37A H 0.385244 0.275489 0.452542 0.038 Uiso 1 1 calc R U . . .
H37B H 0.214313 0.202932 0.421615 0.038 Uiso 1 1 calc R U . . .
C35 C 0.34905(15) 0.21837(14) 0.34350(7) 0.0279(3) Uani 1 1 d . . . . .
H35 H 0.257858 0.202360 0.309246 0.033 Uiso 1 1 calc R U . . .
C7 C -0.01024(14) -0.02427(13) 0.24119(7) 0.0240(3) Uani 1 1 d . . . . .
C44 C 0.83282(17) 0.38636(15) 0.24650(8) 0.0334(3) Uani 1 1 d . . . . .
H44A H 0.889962 0.406617 0.212112 0.050 Uiso 1 1 calc R U . . .
H44B H 0.735306 0.341247 0.224898 0.050 Uiso 1 1 calc R U . . .
H44C H 0.887277 0.326404 0.270079 0.050 Uiso 1 1 calc R U . . .
C9 C 0.06220(14) -0.24731(13) 0.16968(7) 0.0226(3) Uani 1 1 d . . . . .
C27 C 0.93389(15) 0.60198(15) 0.33331(7) 0.0298(3) Uani 1 1 d . . . . .
C24 C -0.50471(18) 0.13564(17) 0.07911(9) 0.0389(4) Uani 1 1 d . . . . .
H24A H -0.593771 0.073358 0.073269 0.058 Uiso 1 1 calc R U . . .
H24B H -0.479265 0.140503 0.034805 0.058 Uiso 1 1 calc R U . . .
H24C H -0.524537 0.226316 0.104375 0.058 Uiso 1 1 calc R U . . .
C42 C 0.75945(16) 0.44830(14) 0.48482(7) 0.0294(3) Uani 1 1 d . . . . .
H42 H 0.771816 0.516849 0.525852 0.035 Uiso 1 1 calc R U . . .
C46 C 0.48702(18) 0.71162(16) 0.36253(9) 0.0386(4) Uani 1 1 d . . . . .
H46A H 0.472152 0.718808 0.409537 0.058 Uiso 1 1 calc R U . . .
H46B H 0.415591 0.641219 0.332793 0.058 Uiso 1 1 calc R U . . .
H46C H 0.471452 0.799011 0.351442 0.058 Uiso 1 1 calc R U . . .
C30 C 0.64432(15) 0.67427(13) 0.35300(7) 0.0258(3) Uani 1 1 d . . . . .
C26 C 0.81116(15) 0.51684(13) 0.29636(7) 0.0245(3) Uani 1 1 d . . . . .
C8 C 0.08521(14) -0.13684(13) 0.22200(7) 0.0252(3) Uani 1 1 d . . . . .
H8 H 0.176710 -0.130683 0.250812 0.030 Uiso 1 1 calc R U . . .
C38 C 0.60985(14) 0.33491(12) 0.37975(6) 0.0210(3) Uani 1 1 d . . . . .
C36 C 0.38479(16) 0.09814(14) 0.37258(7) 0.0299(3) Uani 1 1 d . . . . .
H36A H 0.320265 0.012866 0.354406 0.036 Uiso 1 1 calc R U . . .
H36B H 0.491170 0.085413 0.385328 0.036 Uiso 1 1 calc R U . . .
C21 C -0.20179(19) 0.20294(16) 0.05933(8) 0.0383(4) Uani 1 1 d . . . . .
H21A H -0.246846 0.153785 0.013882 0.057 Uiso 1 1 calc R U . . .
H21B H -0.094160 0.219759 0.059929 0.057 Uiso 1 1 calc R U . . .
H21C H -0.246608 0.289853 0.072151 0.057 Uiso 1 1 calc R U . . .
C40 C 0.85346(15) 0.26274(14) 0.40993(8) 0.0291(3) Uani 1 1 d . . . . .
H40 H 0.930590 0.204007 0.399402 0.035 Uiso 1 1 calc R U . . .
C41 C 0.87148(16) 0.36204(14) 0.46996(8) 0.0308(3) Uani 1 1 d . . . . .
H41 H 0.960301 0.370921 0.500804 0.037 Uiso 1 1 calc R U . . .
C13 C -0.22750(16) -0.27131(14) 0.01785(7) 0.0280(3) Uani 1 1 d . . . . .
H13 H -0.238254 -0.241690 -0.022732 0.034 Uiso 1 1 calc R U . . .
C39 C 0.72314(15) 0.24863(13) 0.36504(7) 0.0247(3) Uani 1 1 d . . . . .
H39 H 0.711207 0.179816 0.324103 0.030 Uiso 1 1 calc R U . . .
C16 C -0.19558(14) -0.35860(13) 0.13600(7) 0.0232(3) Uani 1 1 d . . . . .
H16 H -0.184679 -0.389589 0.176194 0.028 Uiso 1 1 calc R U . . .
C20 C 0.05012(16) 0.11849(15) 0.14028(8) 0.0340(3) Uani 1 1 d . . . . .
H20A H 0.066967 0.217789 0.152545 0.051 Uiso 1 1 calc R U . . .
H20B H 0.067900 0.083126 0.093544 0.051 Uiso 1 1 calc R U . . .
H20C H 0.118647 0.080388 0.170284 0.051 Uiso 1 1 calc R U . . .
C25 C 0.66766(14) 0.55497(13) 0.30617(7) 0.0225(3) Uani 1 1 d . . . . .
C17 C 0.18124(15) -0.34257(14) 0.16013(7) 0.0278(3) Uani 1 1 d . . . . .
H17 H 0.269866 -0.319413 0.195847 0.033 Uiso 1 1 calc R U . . .
C47 C 0.7445(2) 0.89327(16) 0.43702(9) 0.0473(4) Uani 1 1 d . . . . .
H47A H 0.763231 0.968562 0.416199 0.071 Uiso 1 1 calc R U . . .
H47B H 0.813933 0.905257 0.478672 0.071 Uiso 1 1 calc R U . . .
H47C H 0.641786 0.892091 0.447469 0.071 Uiso 1 1 calc R U . . .
C28 C 0.91212(17) 0.72590(15) 0.37740(7) 0.0322(3) Uani 1 1 d . . . . .
C18 C 0.14702(16) -0.49335(14) 0.12853(8) 0.0323(3) Uani 1 1 d . . . . .
H18A H 0.210089 -0.557191 0.146480 0.039 Uiso 1 1 calc R U . . .
H18B H 0.041122 -0.526942 0.113746 0.039 Uiso 1 1 calc R U . . .
C23 C -0.56161(15) -0.03028(17) 0.17334(9) 0.0368(4) Uani 1 1 d . . . . .
H23A H -0.618121 0.050853 0.180016 0.055 Uiso 1 1 calc R U . . .
H23B H -0.559414 -0.067900 0.213001 0.055 Uiso 1 1 calc R U . . .
H23C H -0.609487 -0.098327 0.133383 0.055 Uiso 1 1 calc R U . . .
C48 C 1.0420(2) 0.82852(19) 0.41102(10) 0.0516(5) Uani 1 1 d . . . . .
H48A H 1.027469 0.913940 0.397713 0.077 Uiso 1 1 calc R U . . .
H48B H 1.135040 0.792927 0.396970 0.077 Uiso 1 1 calc R U . . .
H48C H 1.047308 0.844988 0.460099 0.077 Uiso 1 1 calc R U . . .
C45 C 1.08905(17) 0.5584(2) 0.32362(10) 0.0476(4) Uani 1 1 d . . . . .
H45A H 1.087996 0.459175 0.314936 0.071 Uiso 1 1 calc R U . . .
H45B H 1.158363 0.600007 0.364426 0.071 Uiso 1 1 calc R U . . .
H45C H 1.121277 0.587686 0.285212 0.071 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
C15 C14 H14 120.1 . . ?
C15 C14 C13 119.79(13) . . ?
C13 C14 H14 120.1 . . ?
C4 C5 C6 119.83(12) . . ?
C4 C5 C23 121.11(13) . . ?
C6 C5 C23 119.06(12) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C13 C12 C11 120.40(12) . . ?
C2 C1 C7 118.88(11) . . ?
C6 C1 C2 121.62(12) . . ?
C6 C1 C7 119.21(11) . . ?
C5 C4 C3 120.52(12) . . ?
C5 C4 C24 119.75(13) . . ?
C3 C4 C24 119.69(13) . . ?
C1 C2 C20 120.15(12) . . ?
C3 C2 C1 118.92(12) . . ?
C3 C2 C20 120.90(12) . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.24(12) . . ?
C16 C15 H15 119.9 . . ?
C32 C33 C35 118.55(12) . . ?
C32 C33 C38 124.49(12) . . ?
C35 C33 C38 116.95(11) . . ?
C5 C6 C22 120.69(12) . . ?
C1 C6 C5 119.05(12) . . ?
C1 C6 C22 120.25(12) . . ?
C12 C11 C9 121.55(11) . . ?
C12 C11 C16 119.12(12) . . ?
C16 C11 C9 119.32(11) . . ?
O34 C31 C32 118.33(12) . . ?
O34 C31 C25 118.69(12) . . ?
C32 C31 C25 122.91(12) . . ?
C33 C32 C31 129.71(12) . . ?
C33 C32 H32 115.1 . . ?
C31 C32 H32 115.1 . . ?
C4 C3 C21 119.52(13) . . ?
C2 C3 C4 120.03(12) . . ?
C2 C3 C21 120.42(13) . . ?
H19A C19 H19B 114.8 . . ?
C17 C19 H19A 117.7 . . ?
C17 C19 H19B 117.7 . . ?
C18 C19 H19A 117.7 . . ?
C18 C19 H19B 117.7 . . ?
C18 C19 C17 60.67(10) . . ?
C30 C29 C47 120.18(15) . . ?
C30 C29 C28 120.01(13) . . ?
C28 C29 C47 119.75(14) . . ?
C42 C43 H43 119.8 . . ?
C42 C43 C38 120.33(12) . . ?
C38 C43 H43 119.8 . . ?
C6 C22 H22A 109.5 . . ?
C6 C22 H22B 109.5 . . ?
C6 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
H37A C37 H37B 114.8 . . ?
C35 C37 H37A 117.7 . . ?
C35 C37 H37B 117.7 . . ?
C36 C37 H37A 117.7 . . ?
C36 C37 H37B 117.7 . . ?
C36 C37 C35 60.61(9) . . ?
C33 C35 C37 120.99(12) . . ?
C33 C35 H35 114.6 . . ?
C33 C35 C36 122.28(12) . . ?
C37 C35 H35 114.6 . . ?
C36 C35 C37 58.57(9) . . ?
C36 C35 H35 114.6 . . ?
O10 C7 C1 118.52(11) . . ?
O10 C7 C8 118.35(12) . . ?
C8 C7 C1 123.06(11) . . ?
H44A C44 H44B 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C26 C44 H44A 109.5 . . ?
C26 C44 H44B 109.5 . . ?
C26 C44 H44C 109.5 . . ?
C8 C9 C11 123.68(11) . . ?
C8 C9 C17 118.52(12) . . ?
C17 C9 C11 117.78(11) . . ?
C26 C27 C28 120.20(13) . . ?
C26 C27 C45 118.58(14) . . ?
C28 C27 C45 121.21(14) . . ?
C4 C24 H24A 109.5 . . ?
C4 C24 H24B 109.5 . . ?
C4 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C43 C42 H42 119.8 . . ?
C41 C42 C43 120.35(13) . . ?
C41 C42 H42 119.8 . . ?
H46A C46 H46B 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C30 C46 H46A 109.5 . . ?
C30 C46 H46B 109.5 . . ?
C30 C46 H46C 109.5 . . ?
C29 C30 C46 120.82(13) . . ?
C29 C30 C25 119.23(13) . . ?
C25 C30 C46 119.92(13) . . ?
C27 C26 C44 120.82(13) . . ?
C25 C26 C44 120.30(12) . . ?
C25 C26 C27 118.88(13) . . ?
C7 C8 H8 115.2 . . ?
C9 C8 C7 129.65(12) . . ?
C9 C8 H8 115.2 . . ?
C43 C38 C33 121.23(11) . . ?
C39 C38 C33 119.65(11) . . ?
C39 C38 C43 119.04(12) . . ?
C37 C36 C35 60.82(9) . . ?
C37 C36 H36A 117.7 . . ?
C37 C36 H36B 117.7 . . ?
C35 C36 H36A 117.7 . . ?
C35 C36 H36B 117.7 . . ?
H36A C36 H36B 114.8 . . ?
C3 C21 H21A 109.5 . . ?
C3 C21 H21B 109.5 . . ?
C3 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C41 C40 H40 119.8 . . ?
C41 C40 C39 120.30(13) . . ?
C39 C40 H40 119.8 . . ?
C42 C41 C40 119.68(13) . . ?
C42 C41 H41 120.2 . . ?
C40 C41 H41 120.2 . . ?
C14 C13 H13 119.9 . . ?
C12 C13 C14 120.20(13) . . ?
C12 C13 H13 119.9 . . ?
C38 C39 H39 119.8 . . ?
C40 C39 C38 120.30(13) . . ?
C40 C39 H39 119.8 . . ?
C15 C16 C11 120.22(12) . . ?
C15 C16 H16 119.9 . . ?
C11 C16 H16 119.9 . . ?
C2 C20 H20A 109.5 . . ?
C2 C20 H20B 109.5 . . ?
C2 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C30 C25 C31 118.71(12) . . ?
C26 C25 C31 119.52(12) . . ?
C26 C25 C30 121.49(12) . . ?
C19 C17 H17 114.8 . . ?
C19 C17 C18 58.67(10) . . ?
C9 C17 C19 120.38(12) . . ?
C9 C17 H17 114.8 . . ?
C9 C17 C18 122.06(12) . . ?
C18 C17 H17 114.8 . . ?
C29 C47 H47A 109.5 . . ?
C29 C47 H47B 109.5 . . ?
C29 C47 H47C 109.5 . . ?
H47A C47 H47B 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
C29 C28 C27 120.00(13) . . ?
C29 C28 C48 118.55(15) . . ?
C27 C28 C48 121.38(15) . . ?
C19 C18 C17 60.67(10) . . ?
C19 C18 H18A 117.7 . . ?
C19 C18 H18B 117.7 . . ?
C17 C18 H18A 117.7 . . ?
C17 C18 H18B 117.7 . . ?
H18A C18 H18B 114.8 . . ?
C5 C23 H23A 109.5 . . ?
C5 C23 H23B 109.5 . . ?
C5 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C28 C48 H48A 109.5 . . ?
C28 C48 H48B 109.5 . . ?
C28 C48 H48C 109.5 . . ?
H48A C48 H48B 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C27 C45 H45A 109.5 . . ?
C27 C45 H45B 109.5 . . ?
C27 C45 H45C 109.5 . . ?
H45A C45 H45B 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 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
O10 C7 1.2271(17) . ?
C14 H14 0.9500 . ?
C14 C15 1.382(2) . ?
C14 C13 1.388(2) . ?
C5 C4 1.400(2) . ?
C5 C6 1.4016(18) . ?
C5 C23 1.5121(18) . ?
O34 C31 1.2255(17) . ?
C12 H12 0.9500 . ?
C12 C11 1.3918(19) . ?
C12 C13 1.3850(19) . ?
C1 C2 1.3999(19) . ?
C1 C6 1.3968(18) . ?
C1 C7 1.5092(18) . ?
C4 C3 1.4007(19) . ?
C4 C24 1.5128(19) . ?
C2 C3 1.3983(19) . ?
C2 C20 1.5148(18) . ?
C15 H15 0.9500 . ?
C15 C16 1.3896(19) . ?
C33 C32 1.3428(19) . ?
C33 C35 1.4835(18) . ?
C33 C38 1.4946(17) . ?
C6 C22 1.5098(18) . ?
C11 C9 1.4927(17) . ?
C11 C16 1.3945(18) . ?
C31 C32 1.4724(19) . ?
C31 C25 1.5098(18) . ?
C32 H32 0.9500 . ?
C3 C21 1.5156(19) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C17 1.517(2) . ?
C19 C18 1.486(2) . ?
C29 C30 1.396(2) . ?
C29 C47 1.517(2) . ?
C29 C28 1.403(2) . ?
C43 H43 0.9500 . ?
C43 C42 1.3866(19) . ?
C43 C38 1.3944(18) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C37 C35 1.517(2) . ?
C37 C36 1.483(2) . ?
C35 H35 1.0000 . ?
C35 C36 1.5143(19) . ?
C7 C8 1.4715(18) . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?
C44 C26 1.508(2) . ?
C9 C8 1.3470(19) . ?
C9 C17 1.4798(18) . ?
C27 C26 1.400(2) . ?
C27 C28 1.403(2) . ?
C27 C45 1.513(2) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C42 H42 0.9500 . ?
C42 C41 1.384(2) . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?
C46 C30 1.5136(19) . ?
C30 C25 1.3997(19) . ?
C26 C25 1.3963(18) . ?
C8 H8 0.9500 . ?
C38 C39 1.3929(18) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C40 H40 0.9500 . ?
C40 C41 1.385(2) . ?
C40 C39 1.3888(19) . ?
C41 H41 0.9500 . ?
C13 H13 0.9500 . ?
C39 H39 0.9500 . ?
C16 H16 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C17 H17 1.0000 . ?
C17 C18 1.5167(19) . ?
C47 H47A 0.9800 . ?
C47 H47B 0.9800 . ?
C47 H47C 0.9800 . ?
C28 C48 1.517(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 0.9800 . ?
C45 H45A 0.9800 . ?
C45 H45B 0.9800 . ?
C45 H45C 0.9800 . ?
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
O10 C7 C8 C9 167.16(14) . . . . ?
C14 C15 C16 C11 0.3(2) . . . . ?
C5 C4 C3 C2 -1.4(2) . . . . ?
C5 C4 C3 C21 -179.37(12) . . . . ?
O34 C31 C32 C33 167.42(15) . . . . ?
O34 C31 C25 C30 92.26(17) . . . . ?
O34 C31 C25 C26 -81.72(17) . . . . ?
C12 C11 C9 C8 92.94(16) . . . . ?
C12 C11 C9 C17 -88.56(15) . . . . ?
C12 C11 C16 C15 -1.58(18) . . . . ?
C1 C2 C3 C4 0.15(19) . . . . ?
C1 C2 C3 C21 178.14(12) . . . . ?
C1 C7 C8 C9 -15.9(2) . . . . ?
C4 C5 C6 C1 0.24(19) . . . . ?
C4 C5 C6 C22 -179.86(12) . . . . ?
C2 C1 C6 C5 -1.47(19) . . . . ?
C2 C1 C6 C22 178.62(11) . . . . ?
C2 C1 C7 O10 94.25(15) . . . . ?
C2 C1 C7 C8 -82.64(16) . . . . ?
C15 C14 C13 C12 -0.7(2) . . . . ?
C33 C35 C36 C37 109.13(15) . . . . ?
C33 C38 C39 C40 -176.80(12) . . . . ?
C6 C5 C4 C3 1.16(19) . . . . ?
C6 C5 C4 C24 -176.27(12) . . . . ?
C6 C1 C2 C3 1.27(19) . . . . ?
C6 C1 C2 C20 179.39(12) . . . . ?
C6 C1 C7 O10 -79.75(16) . . . . ?
C6 C1 C7 C8 103.36(15) . . . . ?
C11 C12 C13 C14 -0.6(2) . . . . ?
C11 C9 C8 C7 -4.5(2) . . . . ?
C11 C9 C17 C19 41.07(18) . . . . ?
C11 C9 C17 C18 -28.80(19) . . . . ?
C32 C33 C35 C37 -141.17(14) . . . . ?
C32 C33 C35 C36 148.71(14) . . . . ?
C32 C33 C38 C43 92.28(17) . . . . ?
C32 C33 C38 C39 -91.08(16) . . . . ?
C32 C31 C25 C30 -84.45(16) . . . . ?
C32 C31 C25 C26 101.56(16) . . . . ?
C29 C30 C25 C31 -171.10(12) . . . . ?
C29 C30 C25 C26 2.77(19) . . . . ?
C43 C42 C41 C40 0.4(2) . . . . ?
C43 C38 C39 C40 -0.09(19) . . . . ?
C35 C33 C32 C31 177.83(13) . . . . ?
C35 C33 C38 C43 -88.84(15) . . . . ?
C35 C33 C38 C39 87.79(15) . . . . ?
C7 C1 C2 C3 -172.58(11) . . . . ?
C7 C1 C2 C20 5.53(18) . . . . ?
C7 C1 C6 C5 172.37(11) . . . . ?
C7 C1 C6 C22 -7.54(18) . . . . ?
C44 C26 C25 C31 -7.36(18) . . . . ?
C44 C26 C25 C30 178.82(12) . . . . ?
C9 C11 C16 C15 179.50(12) . . . . ?
C9 C17 C18 C19 108.50(15) . . . . ?
C27 C26 C25 C31 172.36(12) . . . . ?
C27 C26 C25 C30 -1.46(19) . . . . ?
C24 C4 C3 C2 176.08(13) . . . . ?
C24 C4 C3 C21 -1.9(2) . . . . ?
C42 C43 C38 C33 176.48(12) . . . . ?
C42 C43 C38 C39 -0.17(19) . . . . ?
C46 C30 C25 C31 6.57(18) . . . . ?
C46 C30 C25 C26 -179.57(12) . . . . ?
C30 C29 C28 C27 -3.7(2) . . . . ?
C30 C29 C28 C48 173.26(13) . . . . ?
C26 C27 C28 C29 5.0(2) . . . . ?
C26 C27 C28 C48 -171.84(13) . . . . ?
C8 C9 C17 C19 -140.35(14) . . . . ?
C8 C9 C17 C18 149.78(14) . . . . ?
C38 C33 C32 C31 -3.3(2) . . . . ?
C38 C33 C35 C37 39.88(18) . . . . ?
C38 C33 C35 C36 -30.24(18) . . . . ?
C38 C43 C42 C41 0.0(2) . . . . ?
C36 C37 C35 C33 -111.28(14) . . . . ?
C41 C40 C39 C38 0.5(2) . . . . ?
C13 C14 C15 C16 0.9(2) . . . . ?
C13 C12 C11 C9 -179.35(12) . . . . ?
C13 C12 C11 C16 1.76(19) . . . . ?
C39 C40 C41 C42 -0.6(2) . . . . ?
C16 C11 C9 C8 -88.17(16) . . . . ?
C16 C11 C9 C17 90.33(15) . . . . ?
C20 C2 C3 C4 -177.95(12) . . . . ?
C20 C2 C3 C21 0.0(2) . . . . ?
C25 C31 C32 C33 -15.9(2) . . . . ?
C17 C9 C8 C7 177.03(13) . . . . ?
C47 C29 C30 C46 -0.7(2) . . . . ?
C47 C29 C30 C25 176.91(12) . . . . ?
C47 C29 C28 C27 179.22(12) . . . . ?
C47 C29 C28 C48 -3.8(2) . . . . ?
C28 C29 C30 C46 -177.80(13) . . . . ?
C28 C29 C30 C25 -0.16(19) . . . . ?
C28 C27 C26 C44 177.26(12) . . . . ?
C28 C27 C26 C25 -2.45(19) . . . . ?
C18 C19 C17 C9 -111.31(14) . . . . ?
C23 C5 C4 C3 -179.93(13) . . . . ?
C23 C5 C4 C24 2.6(2) . . . . ?
C23 C5 C6 C1 -178.70(12) . . . . ?
C23 C5 C6 C22 1.21(19) . . . . ?
C45 C27 C26 C44 -1.7(2) . . . . ?
C45 C27 C26 C25 178.58(13) . . . . ?
C45 C27 C28 C29 -176.03(13) . . . . ?
C45 C27 C28 C48 7.1(2) . . . . ?
