#------------------------------------------------------------------------------
#$Date: 2025-06-02 21:20:34 +0300 (Mon, 02 Jun 2025) $
#$Revision: 299904 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/83/1568310.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_1568310
loop_
_publ_author_name
'Tao, Si-Chen'
'Meng, Fan-Cheng'
'Wang, Tie'
'Zheng, Yan-Long'
_publ_section_title
;
 Ni-catalyzed arylation of alkynes with organoboronic acids and aldehydes
 to access stereodefined allylic alcohols.
;
_journal_issue                   8
_journal_name_full               'Chemical science'
_journal_page_first              2040
_journal_page_last               2045
_journal_paper_doi               10.1039/d2sc05894d
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C28 H32 O2'
_chemical_formula_sum            'C28 H32 O2'
_chemical_formula_weight         400.53
_chemical_name_systematic        1
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-07-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-09-27 deposited with the CCDC.	2023-01-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.304(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.9673(7)
_cell_length_b                   15.1856(5)
_cell_length_c                   18.5806(8)
_cell_measurement_reflns_used    11817
_cell_measurement_temperature    293
_cell_measurement_theta_max      67.8060
_cell_measurement_theta_min      2.4550
_cell_volume                     4933.6(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -42.00  69.00   0.50    1.00    --   42.30 -82.00-150.00  222
  2  ω    -28.00  -2.00   0.50    1.00    --   42.30 -82.00  60.00   52
  3  ω     16.00  70.00   0.50    1.00    --   42.30 -82.00 -90.00  108
  4  ω     24.00  93.00   0.50    1.00    --   42.30  65.00  30.00  138
  5  ω     13.00  72.00   0.50    1.00    --   42.30 -43.00-120.00  118
  6  ω      6.00  70.00   0.50    1.00    --   42.30 -82.00  60.00  128
  7  ω     21.00  64.00   0.50    1.00    --   42.30  65.00 120.00   86
  8  ω     19.00  49.00   0.50    1.00    --   42.30  65.00 -30.00   60
  9  ω     43.00  68.00   0.50    1.00    --   42.30 -77.00-150.00   50
 10  ω     -9.00  65.00   0.50    1.00    --   42.30 -82.00-180.00  148
 11  ω    -46.00   7.00   0.50    1.00    --   42.30 -54.00 120.00  106
 12  ω     10.00  70.00   0.50    1.00    --   42.30 -82.00   0.00  120
 13  ω    -47.00   2.00   0.50    1.00    --   42.30 -82.00   0.00   98
 14  ω    -30.00  -4.00   0.50    1.00    --   42.30 -43.00-120.00   52
 15  ω     44.00  69.00   0.50    1.00    --   42.30 -82.00  90.00   50
 16  ω     42.00  67.00   0.50    1.00    --   42.30 -77.00 -90.00   50
 17  ω     42.00  67.00   0.50    1.00    --   42.30 -77.00 120.00   50
 18  ω      9.00  34.00   0.50    1.00    --   42.30 -77.00-150.00   50
 19  ω     31.00  86.00   0.50    1.00    --   42.30  43.00 120.00  110
 20  ω    -24.00   1.00   0.50    1.00    --   42.30 -77.00  90.00   50
 21  ω    100.00 125.00   0.50    1.00    --   42.30  43.00 120.00   50
 22  ω    -42.00   5.00   0.50    1.00    --   42.30 -82.00 -90.00   94
 23  ω     22.00 120.00   0.50    1.00    --   42.30  65.00-180.00  196
 24  ω     -9.00  16.00   0.50    1.00    --   42.30 -77.00 120.00   50
 25  ω     10.00  70.00   0.50    1.00    --   42.30 -43.00-180.00  120
 26  ω      5.00  34.00   0.50    1.50    --   93.70 -82.00 -90.00   58
 27  ω     59.00  96.00   0.50    1.50    --   93.70 -82.00 -30.00   74
 28  ω     29.00  98.00   0.50    1.50    --   93.70 -82.00-150.00  138
 29  ω     78.00 110.00   0.50    1.50    --   93.70 -33.00 120.00   64
 30  ω     26.00 114.00   0.50    1.50    --   93.70 -82.00  30.00  176
 31  ω      6.00  35.00   0.50    1.50    --   93.70 -33.00 120.00   58
 32  ω      8.00 111.00   0.50    1.50    --   93.70 -59.00 -90.00  206
 33  ω      4.00 180.00   0.50    1.50    --   93.70  -8.00 -90.00  352
 34  ω     12.00  99.00   0.50    1.50    --   93.70 -82.00 120.00  174
 35  ω    117.00 183.00   0.50    1.50    --   93.70  68.00 -90.00  132
 36  ω     73.00  98.00   0.50    1.50    --   93.70  68.00 -90.00   50
 37  ω     70.00  96.00   0.50    1.50    --   93.70 -82.00 -60.00   52
 38  ω      4.00  46.00   0.50    1.50    --   93.70 -42.00  60.00   84
 39  ω    135.00 183.00   0.50    1.50    --   93.70  50.00 -30.00   96
 40  ω     75.00 100.00   0.50    1.50    --   93.70 -82.00   0.00   50
 41  ω     50.00  96.00   0.50    1.50    --   93.70 -82.00 150.00   92
 42  ω      9.00  93.00   0.50    1.50    --   93.70 -82.00-180.00  168
 43  ω    152.00 183.00   0.50    1.50    --   93.70  68.00-180.00   62
 44  ω    114.00 139.00   0.50    1.50    --   93.70  68.00-180.00   50
 45  ω     49.00 101.00   0.50    1.50    --   93.70 -82.00 -90.00  104
 46  ω     99.00 124.00   0.50    1.50    --   93.70  68.00-150.00   50
 47  ω      8.00 120.00   0.50    1.50    --   93.70 -33.00 -90.00  224
 48  ω     10.00  98.00   0.50    1.50    --   93.70 -82.00-120.00  176
 49  ω     73.00  98.00   0.50    1.50    --   93.70 -82.00  70.41   50
 50  ω     42.00  91.00   0.50    1.50    --   93.70 -82.00  90.00   98
 51  ω     16.00  65.00   0.50    1.50    --   93.70 -82.00  70.41   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0442038000
_diffrn_orient_matrix_UB_12      0.0251858000
_diffrn_orient_matrix_UB_13      -0.0784437000
_diffrn_orient_matrix_UB_21      -0.0738023000
_diffrn_orient_matrix_UB_22      0.0100499000
_diffrn_orient_matrix_UB_23      0.0282074000
_diffrn_orient_matrix_UB_31      0.0190211000
_diffrn_orient_matrix_UB_32      0.0977921000
_diffrn_orient_matrix_UB_33      0.0173211000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1064
_diffrn_reflns_av_unetI/netI     0.0869
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            49159
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        63.687
_diffrn_reflns_theta_max         63.687
_diffrn_reflns_theta_min         3.085
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.510
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.01903
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.89a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.078
_exptl_crystal_description       block
_exptl_crystal_F_000             1728
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.062
_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     549
_refine_ls_number_reflns         8104
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.1251
_refine_ls_R_factor_gt           0.0955
_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)+(0.1891P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2689
_refine_ls_wR_factor_ref         0.3144
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4800
_reflns_number_total             8104
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc05894d2.cif
_cod_data_source_block           2j-danjing4_auto
_cod_depositor_comments
;
Adding full bibliography for 1568308--1568310.cif.

2025-06-02
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C56 H64 O4'
_cod_original_formula_weight         801.07
_cod_original_formula_moiety         '2(C28 H32 O2)'
_cod_original_formula_units_Z            4
_cod_database_code               1568310
_shelx_shelxl_version_number     2018/3
_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   0.980
_shelx_estimated_absorpt_t_min   0.970
_diffrn_oxdiff_digest_frames
;
014f011bcc05c801f8f6b8b718d8b2f1df00028aafc
;
_diffrn_oxdiff_digest_hkl
;
014fc68681347458031dddd37c28cc0746b8ab
;
_reflns_odcompleteness_completeness 99.86
_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 Ternary CH refined with riding coordinates:
 C16(H16), C44(H44)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C13(H13A,H13B), C14(H14A,H14B), C37(H37A,H37B),
 C38(H38A,H38B), C41(H41A,H41B), C42(H42A,H42B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3A), C4(H4), C6(H6), C7(H7), C18(H18), C19(H19), C21(H21), C22(H22),
 C24(H24), C25(H25), C26(H26), C27(H27), C28(H28), C31(H31), C32(H32), C33(H33),
  C34(H34), C46(H46), C47(H47), C49(H49), C50(H50), C52(H52), C53(H53),
 C54(H54), C55(H55), C56(H56)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C11(H11A,H11B,H11C), C15(H15A,H15B,H15C), C29(H29A,H29B,
 H29C), C36(H36A,H36B,H36C), C43(H43A,H43B,H43C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3)
;
_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 22.635
_oxdiff_exptl_absorpt_empirical_full_min 0.404
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'
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 0.53128(13) 0.40777(13) 0.55291(13) 0.0851(6) Uani 1 1 d . . . . .
H1 H 0.544606 0.419598 0.514680 0.128 Uiso 1 1 calc GR . . . .
O2 O 0.91978(14) 0.46516(16) 0.62578(17) 0.1090(9) Uani 1 1 d . . . . .
C1 C 0.9243(3) 0.5492(3) 0.5938(4) 0.1455(19) Uani 1 1 d . . . . .
H1A H 0.929827 0.542207 0.543926 0.218 Uiso 1 1 calc GR . . . .
H1B H 0.967669 0.580528 0.622129 0.218 Uiso 1 1 calc GR . . . .
H1C H 0.878491 0.581807 0.593636 0.218 Uiso 1 1 calc GR . . . .
C2 C 0.85548(19) 0.4157(2) 0.5994(2) 0.0838(9) Uani 1 1 d . . . . .
C3 C 0.7980(2) 0.4371(2) 0.5399(2) 0.0846(9) Uani 1 1 d . . . . .
H3A H 0.801176 0.488505 0.513638 0.102 Uiso 1 1 calc R . . . .
C4 C 0.73546(18) 0.3828(2) 0.51879(19) 0.0789(9) Uani 1 1 d . . . . .
H4 H 0.696998 0.398123 0.478020 0.095 Uiso 1 1 calc R . . . .
C5 C 0.72834(17) 0.30591(19) 0.55669(18) 0.0727(8) Uani 1 1 d . . . . .
C6 C 0.78767(19) 0.2852(2) 0.61658(19) 0.0799(9) Uani 1 1 d . . . . .
H6 H 0.784845 0.233695 0.642856 0.096 Uiso 1 1 calc R . . . .
C7 C 0.85026(18) 0.3387(2) 0.6380(2) 0.0820(9) Uani 1 1 d . . . . .
H7 H 0.889192 0.323346 0.678386 0.098 Uiso 1 1 calc R . . . .
C8 C 0.65968(18) 0.2473(2) 0.53259(18) 0.0763(8) Uani 1 1 d . . . . .
C9 C 0.6712(2) 0.1714(3) 0.4837(2) 0.1047(12) Uani 1 1 d . . . . .
H9A H 0.623749 0.138385 0.471182 0.126 Uiso 1 1 calc R . . . .
H9B H 0.679527 0.195955 0.437961 0.126 Uiso 1 1 calc R . . . .
C10 C 0.7324(3) 0.1096(3) 0.5114(3) 0.1377(18) Uani 1 1 d . . . . .
H10A H 0.721123 0.079682 0.553799 0.165 Uiso 1 1 calc R . . . .
H10B H 0.779116 0.142857 0.528959 0.165 Uiso 1 1 calc R . . . .
C11 C 0.7474(3) 0.0412(3) 0.4587(3) 0.1296(16) Uani 1 1 d . . . . .
H11A H 0.765417 0.069052 0.419529 0.194 Uiso 1 1 calc GR . . . .
H11B H 0.700944 0.009782 0.438212 0.194 Uiso 1 1 calc GR . . . .
H11C H 0.785388 0.000737 0.484372 0.194 Uiso 1 1 calc GR . . . .
C12 C 0.59324(17) 0.26568(18) 0.55029(17) 0.0711(8) Uani 1 1 d . . . . .
C13 C 0.52182(17) 0.2100(2) 0.5268(2) 0.0811(9) Uani 1 1 d . . . . .
H13A H 0.517437 0.191219 0.476092 0.097 Uiso 1 1 calc R . . . .
H13B H 0.477704 0.246439 0.527737 0.097 Uiso 1 1 calc R . . . .
C14 C 0.5193(2) 0.1287(2) 0.5744(2) 0.1002(11) Uani 1 1 d . . . . .
H14A H 0.561186 0.089886 0.570739 0.120 Uiso 1 1 calc R . . . .
H14B H 0.526806 0.146713 0.625631 0.120 Uiso 1 1 calc R . . . .
C15 C 0.4455(3) 0.0790(3) 0.5522(4) 0.1437(19) Uani 1 1 d . . . . .
H15A H 0.434410 0.067591 0.499967 0.216 Uiso 1 1 calc GR . . . .
H15B H 0.404958 0.113360 0.563778 0.216 Uiso 1 1 calc GR . . . .
H15C H 0.449834 0.024181 0.578561 0.216 Uiso 1 1 calc GR . . . .
C16 C 0.58490(17) 0.34587(18) 0.59619(17) 0.0707(8) Uani 1 1 d . . . . .
H16 H 0.634882 0.374736 0.610929 0.085 Uiso 1 1 calc R . . . .
C17 C 0.55813(17) 0.32368(18) 0.66502(18) 0.0713(8) Uani 1 1 d . . . . .
C18 C 0.48361(18) 0.3352(2) 0.6716(2) 0.0812(9) Uani 1 1 d . . . . .
H18 H 0.446940 0.356942 0.631786 0.097 Uiso 1 1 calc R . . . .
C19 C 0.4634(2) 0.3145(2) 0.7373(2) 0.0907(10) Uani 1 1 d . . . . .
H19 H 0.412798 0.321957 0.740331 0.109 Uiso 1 1 calc R . . . .
C20 C 0.5157(2) 0.2833(2) 0.7982(2) 0.0841(9) Uani 1 1 d . . . . .
C21 C 0.5895(2) 0.2702(2) 0.7898(2) 0.0867(9) Uani 1 1 d . . . . .
H21 H 0.625894 0.246941 0.828997 0.104 Uiso 1 1 calc R . . . .
C22 C 0.61027(18) 0.2906(2) 0.72544(19) 0.0792(8) Uani 1 1 d . . . . .
H22 H 0.660675 0.281986 0.722320 0.095 Uiso 1 1 calc R . . . .
C23 C 0.4943(3) 0.2668(2) 0.8698(3) 0.0969(12) Uani 1 1 d . . . . .
C24 C 0.5473(3) 0.2797(3) 0.9363(3) 0.1164(14) Uani 1 1 d . . . . .
H24 H 0.596343 0.298425 0.935449 0.140 Uiso 1 1 calc R . . . .
C25 C 0.5288(4) 0.2652(4) 1.0038(3) 0.153(2) Uani 1 1 d . . . . .
H25 H 0.565435 0.274324 1.047495 0.184 Uiso 1 1 calc R . . . .
C26 C 0.4590(6) 0.2384(4) 1.0063(5) 0.172(3) Uani 1 1 d . . . . .
H26 H 0.447020 0.229010 1.051747 0.206 Uiso 1 1 calc R . . . .
C27 C 0.4053(5) 0.2248(4) 0.9430(5) 0.157(3) Uani 1 1 d . . . . .
H27 H 0.356715 0.205977 0.945493 0.189 Uiso 1 1 calc R . . . .
C28 C 0.4220(3) 0.2388(3) 0.8732(3) 0.1239(16) Uani 1 1 d . . . . .
H28 H 0.384829 0.229184 0.830049 0.149 Uiso 1 1 calc R . . . .
O3 O 0.46276(12) 0.55884(13) 0.59486(13) 0.0816(6) Uani 1 1 d . . . . .
H3 H 0.488686 0.516288 0.588666 0.122 Uiso 1 1 calc GR . . . .
O4 O 0.74721(19) 0.7953(2) 0.4710(2) 0.1275(10) Uani 1 1 d . . . . .
C29 C 0.7449(4) 0.7601(4) 0.4001(3) 0.160(2) Uani 1 1 d . . . . .
H29A H 0.768679 0.800535 0.372631 0.239 Uiso 1 1 calc GR . . . .
H29B H 0.692622 0.750951 0.374511 0.239 Uiso 1 1 calc GR . . . .
H29C H 0.771702 0.704990 0.405129 0.239 Uiso 1 1 calc GR . . . .
C30 C 0.7217(2) 0.7437(3) 0.5206(3) 0.0977(11) Uani 1 1 d . . . . .
C31 C 0.7209(2) 0.7831(3) 0.5876(3) 0.1050(12) Uani 1 1 d . . . . .
H31 H 0.736332 0.841385 0.595922 0.126 Uiso 1 1 calc R . . . .
C32 C 0.6977(2) 0.7372(3) 0.6411(2) 0.0992(11) Uani 1 1 d . . . . .
H32 H 0.699051 0.764613 0.686113 0.119 Uiso 1 1 calc R . . . .
C33 C 0.6953(2) 0.6589(3) 0.5080(2) 0.0962(11) Uani 1 1 d . . . . .
H33 H 0.693607 0.632148 0.462621 0.115 Uiso 1 1 calc R . . . .
C34 C 0.6711(2) 0.6135(2) 0.5633(2) 0.0911(10) Uani 1 1 d . . . . .
H34 H 0.653882 0.555870 0.554403 0.109 Uiso 1 1 calc R . . . .
C35 C 0.67192(18) 0.6510(2) 0.6313(2) 0.0837(9) Uani 1 1 d . . . . .
C36 C 0.8350(3) 0.4833(3) 0.7913(3) 0.1205(14) Uani 1 1 d . . . . .
H36A H 0.859760 0.432540 0.776671 0.181 Uiso 1 1 calc GR . . . .
H36B H 0.821047 0.471487 0.837180 0.181 Uiso 1 1 calc GR . . . .
H36C H 0.869332 0.532639 0.797366 0.181 Uiso 1 1 calc GR . . . .
C37 C 0.7627(3) 0.5047(3) 0.7313(3) 0.1296(16) Uani 1 1 d . . . . .
H37A H 0.777724 0.523847 0.686875 0.156 Uiso 1 1 calc R . . . .
H37B H 0.732453 0.451535 0.719337 0.156 Uiso 1 1 calc R . . . .
C38 C 0.7159(2) 0.5727(3) 0.7540(2) 0.1055(12) Uani 1 1 d . . . . .
H38A H 0.747816 0.623398 0.771403 0.127 Uiso 1 1 calc R . . . .
H38B H 0.696257 0.550769 0.795025 0.127 Uiso 1 1 calc R . . . .
C39 C 0.6487(2) 0.6020(2) 0.6921(2) 0.0872(9) Uani 1 1 d . . . . .
C40 C 0.57577(19) 0.5885(2) 0.69440(18) 0.0763(8) Uani 1 1 d . . . . .
C41 C 0.5514(2) 0.5393(2) 0.75477(18) 0.0834(9) Uani 1 1 d . . . . .
H41A H 0.584328 0.488331 0.767266 0.100 Uiso 1 1 calc R . . . .
H41B H 0.499837 0.517757 0.735412 0.100 Uiso 1 1 calc R . . . .
C42 C 0.5523(3) 0.5902(2) 0.8263(2) 0.0977(11) Uani 1 1 d . . . . .
H42A H 0.603400 0.612775 0.846133 0.117 Uiso 1 1 calc R . . . .
H42B H 0.517852 0.640070 0.815071 0.117 Uiso 1 1 calc R . . . .
C43 C 0.5289(4) 0.5340(3) 0.8835(3) 0.158(2) Uani 1 1 d . . . . .
H43A H 0.475833 0.518624 0.867031 0.237 Uiso 1 1 calc GR . . . .
H43B H 0.536489 0.565932 0.929165 0.237 Uiso 1 1 calc GR . . . .
H43C H 0.559244 0.481324 0.890887 0.237 Uiso 1 1 calc GR . . . .
C44 C 0.51201(17) 0.62687(19) 0.63443(18) 0.0735(8) Uani 1 1 d . . . . .
H44 H 0.535166 0.658554 0.599124 0.088 Uiso 1 1 calc R . . . .
C45 C 0.46477(17) 0.69077(19) 0.66654(17) 0.0727(8) Uani 1 1 d . . . . .
C46 C 0.49257(18) 0.77552(19) 0.68418(18) 0.0758(8) Uani 1 1 d . . . . .
H46 H 0.538376 0.792365 0.672971 0.091 Uiso 1 1 calc R . . . .
C47 C 0.45397(18) 0.8345(2) 0.71761(19) 0.0803(9) Uani 1 1 d . . . . .
H47 H 0.474795 0.890089 0.729593 0.096 Uiso 1 1 calc R . . . .
C48 C 0.38378(18) 0.8135(2) 0.73438(19) 0.0789(8) Uani 1 1 d . . . . .
C49 C 0.35588(19) 0.7294(2) 0.7151(2) 0.0851(9) Uani 1 1 d . . . . .
H49 H 0.309388 0.712824 0.724965 0.102 Uiso 1 1 calc R . . . .
C50 C 0.39504(19) 0.6701(2) 0.68195(19) 0.0817(9) Uani 1 1 d . . . . .
H50 H 0.374157 0.614543 0.669521 0.098 Uiso 1 1 calc R . . . .
C51 C 0.34330(19) 0.8784(2) 0.7704(2) 0.0835(9) Uani 1 1 d . . . . .
C52 C 0.2653(2) 0.8912(3) 0.7485(2) 0.1022(11) Uani 1 1 d . . . . .
H52 H 0.236427 0.856762 0.710826 0.123 Uiso 1 1 calc R . . . .
C53 C 0.2299(2) 0.9546(3) 0.7820(3) 0.1223(15) Uani 1 1 d . . . . .
H53 H 0.177402 0.963430 0.766248 0.147 Uiso 1 1 calc R . . . .
C54 C 0.2716(3) 1.0044(3) 0.8383(3) 0.1277(16) Uani 1 1 d . . . . .
H54 H 0.247298 1.046607 0.861014 0.153 Uiso 1 1 calc R . . . .
C55 C 0.3477(2) 0.9927(3) 0.8611(3) 0.1209(15) Uani 1 1 d . . . . .
H55 H 0.375664 1.026843 0.899498 0.145 Uiso 1 1 calc R . . . .
C56 C 0.3842(2) 0.9304(3) 0.8277(2) 0.1028(12) Uani 1 1 d . . . . .
H56 H 0.436760 0.922891 0.843739 0.123 Uiso 1 1 calc R . . . .
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
C16 O1 H1 109.5 . . ?
C2 O2 C1 117.9(3) . . ?
O2 C1 H1A 109.5 . . ?
O2 C1 H1B 109.5 . . ?
O2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 C7 115.4(3) . . ?
C3 C2 O2 125.2(3) . . ?
C3 C2 C7 119.4(3) . . ?
C2 C3 H3A 119.9 . . ?
C2 C3 C4 120.3(3) . . ?
C4 C3 H3A 119.9 . . ?
C3 C4 H4 119.2 . . ?
C3 C4 C5 121.7(3) . . ?
C5 C4 H4 119.2 . . ?
C4 C5 C6 117.0(3) . . ?
C4 C5 C8 120.9(3) . . ?
C6 C5 C8 122.1(3) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 C5 121.8(3) . . ?
C7 C6 H6 119.1 . . ?
C2 C7 H7 120.1 . . ?
C6 C7 C2 119.9(3) . . ?
C6 C7 H7 120.1 . . ?
C5 C8 C9 114.5(3) . . ?
C12 C8 C5 121.4(3) . . ?
C12 C8 C9 124.1(3) . . ?
C8 C9 H9A 107.7 . . ?
C8 C9 H9B 107.7 . . ?
H9A C9 H9B 107.1 . . ?
C10 C9 C8 118.6(4) . . ?
C10 C9 H9A 107.7 . . ?
C10 C9 H9B 107.7 . . ?
C9 C10 H10A 108.0 . . ?
C9 C10 H10B 108.0 . . ?
C9 C10 C11 117.0(4) . . ?
H10A C10 H10B 107.3 . . ?
C11 C10 H10A 108.0 . . ?
C11 C10 H10B 108.0 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8 C12 C13 123.9(3) . . ?
C8 C12 C16 121.0(3) . . ?
C16 C12 C13 115.1(2) . . ?
C12 C13 H13A 108.6 . . ?
C12 C13 H13B 108.6 . . ?
C12 C13 C14 114.9(3) . . ?
H13A C13 H13B 107.5 . . ?
C14 C13 H13A 108.6 . . ?
C14 C13 H13B 108.6 . . ?
C13 C14 H14A 109.0 . . ?
C13 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C15 C14 C13 113.0(4) . . ?
C15 C14 H14A 109.0 . . ?
C15 C14 H14B 109.0 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O1 C16 C12 110.4(2) . . ?
O1 C16 H16 108.3 . . ?
O1 C16 C17 108.4(2) . . ?
C12 C16 H16 108.3 . . ?
C17 C16 C12 113.0(2) . . ?
C17 C16 H16 108.3 . . ?
C18 C17 C16 123.5(3) . . ?
C22 C17 C16 118.9(3) . . ?
C22 C17 C18 117.7(3) . . ?
C17 C18 H18 119.9 . . ?
C17 C18 C19 120.2(3) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 118.9 . . ?
C20 C19 C18 122.2(3) . . ?
C20 C19 H19 118.9 . . ?
C19 C20 C21 116.6(3) . . ?
C19 C20 C23 121.6(3) . . ?
C21 C20 C23 121.8(4) . . ?
C20 C21 H21 119.1 . . ?
C22 C21 C20 121.8(3) . . ?
C22 C21 H21 119.1 . . ?
C17 C22 H22 119.3 . . ?
C21 C22 C17 121.5(3) . . ?
C21 C22 H22 119.3 . . ?
C24 C23 C20 120.4(4) . . ?
C28 C23 C20 122.1(5) . . ?
C28 C23 C24 117.5(4) . . ?
C23 C24 H24 119.2 . . ?
C25 C24 C23 121.6(5) . . ?
C25 C24 H24 119.2 . . ?
C24 C25 H25 119.9 . . ?
C26 C25 C24 120.2(7) . . ?
C26 C25 H25 119.9 . . ?
C25 C26 H26 119.8 . . ?
C25 C26 C27 120.4(7) . . ?
C27 C26 H26 119.8 . . ?
C26 C27 H27 119.5 . . ?
C26 C27 C28 120.9(6) . . ?
C28 C27 H27 119.5 . . ?
C23 C28 C27 119.3(6) . . ?
C23 C28 H28 120.4 . . ?
C27 C28 H28 120.4 . . ?
C44 O3 H3 109.5 . . ?
C30 O4 C29 118.0(4) . . ?
O4 C29 H29A 109.5 . . ?
O4 C29 H29B 109.5 . . ?
O4 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
O4 C30 C31 115.7(4) . . ?
O4 C30 C33 125.3(4) . . ?
C33 C30 C31 119.0(4) . . ?
C30 C31 H31 119.8 . . ?
C32 C31 C30 120.4(4) . . ?
C32 C31 H31 119.8 . . ?
C31 C32 H32 118.7 . . ?
C31 C32 C35 122.6(4) . . ?
C35 C32 H32 118.7 . . ?
C30 C33 H33 120.2 . . ?
C30 C33 C34 119.6(4) . . ?
C34 C33 H33 120.2 . . ?
C33 C34 H34 118.9 . . ?
C35 C34 C33 122.1(4) . . ?
C35 C34 H34 118.9 . . ?
C32 C35 C39 121.0(3) . . ?
C34 C35 C32 116.3(3) . . ?
C34 C35 C39 122.7(3) . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C37 C36 H36A 109.5 . . ?
C37 C36 H36B 109.5 . . ?
C37 C36 H36C 109.5 . . ?
C36 C37 H37A 109.0 . . ?
C36 C37 H37B 109.0 . . ?
H37A C37 H37B 107.8 . . ?
C38 C37 C36 112.8(4) . . ?
C38 C37 H37A 109.0 . . ?
C38 C37 H37B 109.0 . . ?
C37 C38 H38A 108.9 . . ?
C37 C38 H38B 108.9 . . ?
C37 C38 C39 113.5(3) . . ?
H38A C38 H38B 107.7 . . ?
C39 C38 H38A 108.9 . . ?
C39 C38 H38B 108.9 . . ?
C35 C39 C38 113.9(3) . . ?
C40 C39 C35 123.3(3) . . ?
C40 C39 C38 122.8(3) . . ?
C39 C40 C41 124.0(3) . . ?
C39 C40 C44 119.8(3) . . ?
C41 C40 C44 116.1(3) . . ?
C40 C41 H41A 108.1 . . ?
C40 C41 H41B 108.1 . . ?
C40 C41 C42 116.9(3) . . ?
H41A C41 H41B 107.3 . . ?
C42 C41 H41A 108.1 . . ?
C42 C41 H41B 108.1 . . ?
C41 C42 H42A 109.1 . . ?
C41 C42 H42B 109.1 . . ?
H42A C42 H42B 107.9 . . ?
C43 C42 C41 112.3(3) . . ?
C43 C42 H42A 109.1 . . ?
C43 C42 H42B 109.1 . . ?
C42 C43 H43A 109.5 . . ?
C42 C43 H43B 109.5 . . ?
C42 C43 H43C 109.5 . . ?
H43A C43 H43B 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
O3 C44 C40 111.7(2) . . ?
O3 C44 H44 108.3 . . ?
O3 C44 C45 109.2(2) . . ?
C40 C44 H44 108.3 . . ?
C45 C44 C40 110.9(3) . . ?
C45 C44 H44 108.3 . . ?
C46 C45 C44 119.1(3) . . ?
C50 C45 C44 123.9(3) . . ?
C50 C45 C46 117.0(3) . . ?
C45 C46 H46 119.3 . . ?
C47 C46 C45 121.4(3) . . ?
C47 C46 H46 119.3 . . ?
C46 C47 H47 119.1 . . ?
C46 C47 C48 121.9(3) . . ?
C48 C47 H47 119.1 . . ?
C47 C48 C51 120.8(3) . . ?
C49 C48 C47 116.2(3) . . ?
C49 C48 C51 123.0(3) . . ?
C48 C49 H49 119.1 . . ?
C50 C49 C48 121.8(3) . . ?
C50 C49 H49 119.1 . . ?
C45 C50 H50 119.2 . . ?
C49 C50 C45 121.7(3) . . ?
C49 C50 H50 119.2 . . ?
C52 C51 C48 122.3(3) . . ?
C52 C51 C56 117.8(3) . . ?
C56 C51 C48 119.9(3) . . ?
C51 C52 H52 119.7 . . ?
C53 C52 C51 120.5(4) . . ?
C53 C52 H52 119.7 . . ?
C52 C53 H53 119.9 . . ?
C54 C53 C52 120.2(4) . . ?
C54 C53 H53 119.9 . . ?
C53 C54 H54 119.8 . . ?
C55 C54 C53 120.5(4) . . ?
C55 C54 H54 119.8 . . ?
C54 C55 H55 119.9 . . ?
C54 C55 C56 120.2(4) . . ?
C56 C55 H55 119.9 . . ?
C51 C56 H56 119.6 . . ?
C55 C56 C51 120.8(4) . . ?
C55 C56 H56 119.6 . . ?
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 H1 0.8200 . ?
O1 C16 1.450(4) . ?
O2 C1 1.418(5) . ?
O2 C2 1.371(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.366(5) . ?
C2 C7 1.386(5) . ?
C3 H3A 0.9300 . ?
C3 C4 1.376(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.384(4) . ?
C5 C6 1.388(5) . ?
C5 C8 1.503(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.370(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.511(5) . ?
C8 C12 1.339(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.447(6) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.495(6) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.515(4) . ?
C12 C16 1.514(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.525(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.500(6) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16 0.9800 . ?
C16 C17 1.505(4) . ?
C17 C18 1.383(4) . ?
C17 C22 1.381(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.388(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.378(5) . ?
C20 C21 1.384(5) . ?
C20 C23 1.490(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.368(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.389(6) . ?
C23 C28 1.381(6) . ?
C24 H24 0.9300 . ?
C24 C25 1.387(6) . ?
C25 H25 0.9300 . ?
C25 C26 1.329(10) . ?
C26 H26 0.9300 . ?
C26 C27 1.355(10) . ?
C27 H27 0.9300 . ?
C27 C28 1.412(8) . ?
C28 H28 0.9300 . ?
O3 H3 0.8200 . ?
O3 C44 1.446(4) . ?
O4 C29 1.412(6) . ?
O4 C30 1.367(5) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 C31 1.383(6) . ?
C30 C33 1.373(5) . ?
C31 H31 0.9300 . ?
C31 C32 1.356(5) . ?
C32 H32 0.9300 . ?
C32 C35 1.386(5) . ?
C33 H33 0.9300 . ?
C33 C34 1.389(5) . ?
C34 H34 0.9300 . ?
C34 C35 1.382(5) . ?
C35 C39 1.491(5) . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C36 C37 1.539(6) . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C37 C38 1.455(6) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C38 C39 1.530(5) . ?
C39 C40 1.336(5) . ?
C40 C41 1.495(4) . ?
C40 C44 1.519(5) . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
C41 C42 1.534(5) . ?
C42 H42A 0.9700 . ?
C42 H42B 0.9700 . ?
C42 C43 1.497(6) . ?
C43 H43A 0.9600 . ?
C43 H43B 0.9600 . ?
C43 H43C 0.9600 . ?
C44 H44 0.9800 . ?
C44 C45 1.500(4) . ?
C45 C46 1.392(4) . ?
C45 C50 1.384(4) . ?
C46 H46 0.9300 . ?
C46 C47 1.366(4) . ?
C47 H47 0.9300 . ?
C47 C48 1.404(4) . ?
C48 C49 1.388(4) . ?
C48 C51 1.474(4) . ?
C49 H49 0.9300 . ?
C49 C50 1.374(4) . ?
C50 H50 0.9300 . ?
C51 C52 1.380(5) . ?
C51 C56 1.392(5) . ?
C52 H52 0.9300 . ?
C52 C53 1.380(5) . ?
C53 H53 0.9300 . ?
C53 C54 1.367(6) . ?
C54 H54 0.9300 . ?
C54 C55 1.346(6) . ?
C55 H55 0.9300 . ?
C55 C56 1.378(5) . ?
C56 H56 0.9300 . ?
