#------------------------------------------------------------------------------
#$Date: 2020-10-04 06:04:06 +0300 (Sun, 04 Oct 2020) $
#$Revision: 257045 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/78/4517850.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_4517850
loop_
_publ_author_name
'Wang, Shou-Guo'
'Cramer, Nicolai'
_publ_section_title
;
 Asymmetric CpxRh(III)-Catalyzed Acrylic Acid C--H Functionalization with
 Allenes Provides Chiral γ-Lactones
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              8231
_journal_page_last               8236
_journal_paper_doi               10.1021/acscatal.0c02430
_journal_year                    2020
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C20 H18 O2'
_chemical_formula_sum            'C20 H18 O2'
_chemical_formula_weight         290.34
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-12-13
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2019.10.11 svn.r3662 for OlexSys, GUI svn.r5962)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.53867(7)
_cell_length_b                   6.85703(6)
_cell_length_c                   35.6756(3)
_cell_measurement_reflns_used    16014
_cell_measurement_temperature    140.01(13)
_cell_measurement_theta_max      72.4530
_cell_measurement_theta_min      4.9340
_cell_volume                     1599.55(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (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      140.01(13)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2817
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω   -104.00 -65.00   1.00    4.00    --  -40.91-147.00 -87.00   39
  2  ω    -80.00  -5.00   1.00    4.00    --  -40.91 124.00 156.00   75
  3  ω    -84.00 -59.00   1.00    4.00    --  -40.91 147.00 -38.00   25
  4  ω     29.00  95.00   1.00    4.00    --   40.91-124.00  77.00   66
  5  ω     50.00  75.00   1.00    4.00    --   40.91-147.00 -87.00   25
  6  ω     83.00 113.00   1.00   16.00    --  105.15-147.00 -87.00   30
  7  ω    107.00 139.00   1.00   16.00    --  105.15 124.00 156.00   32
  8  ω    123.00 150.00   1.00   16.00    --  105.15 147.00 -38.00   27
  9  ω     55.00 112.00   1.00   16.00    --  105.15-124.00  77.00   57
 10  ω      0.00  30.00   1.00    4.00    --   34.00  83.00 166.04   30
 11  ω   -114.00 -16.00   1.00    4.00    --  -40.91 -38.00 -30.00   98
 12  ω   -114.00 -17.00   1.00    4.00    --  -40.91 -38.00-180.00   97
 13  ω      7.00  32.00   1.00    4.00    --   40.91  83.00 -99.01   25
 14  ω      8.00  39.00   1.00    4.00    --   40.91  77.00   5.23   31
 15  ω     14.00  40.00   1.00    4.00    --   46.00  76.00  76.26   26
 16  ω     12.00  39.00   1.00    4.00    --   46.00  81.00 -42.65   27
 17  ω     15.00  42.00   1.00    4.00    --   46.00  80.00 106.25   27
 18  ω     16.00  41.00   1.00    4.00    --   50.00  82.00-147.05   25
 19  ω     29.00  73.00   1.00    4.00    --   58.00  66.00  43.32   44
 20  ω     30.00  57.00   1.00    4.00    --   58.00  74.00 163.26   27
 21  ω     84.00 131.00   1.00    4.00    --   58.00  66.00  43.32   47
 22  ω     38.00  63.00   1.00    4.00    --   66.00  73.00-165.65   25
 23  ω     75.00 101.00   1.00    4.00    --   66.00  73.00 -85.70   26
 24  ω     34.00  68.00   1.00    4.00    --   66.00  73.00 -85.70   34
 25  ω     37.00  64.00   1.00    4.00    --   66.00  72.00-125.94   27
 26  ω     38.00  64.00   1.00    4.00    --   70.00  74.00  89.00   26
 27  ω     38.00  64.00   1.00    4.00    --   70.00  73.00 -39.40   26
 28  ω    101.00 126.00   1.00    4.00    --   70.00  73.00 -39.40   25
 29  ω     44.00  69.00   1.00    4.00    --   70.00  74.00  20.28   25
 30  ω    103.00 145.00   1.00    4.00    --   70.00  74.00  89.00   42
 31  ω    110.00 137.00   1.00   16.00    --   74.00  70.00 -71.57   27
 32  ω     43.00  81.00   1.00   16.00    --   74.00  71.00 119.04   38
 33  ω     43.00  73.00   1.00   16.00    --   74.00  70.00 -71.57   30
 34  ω     48.00  75.00   1.00   16.00    --   78.00  64.00 154.10   27
 35  ω     46.00  73.00   1.00   16.00    --   78.00  74.00-158.61   27
 36  ω     48.00  75.00   1.00   16.00    --   78.00  74.00 -29.96   27
 37  ω     60.00  86.00   1.00   16.00    --   86.00  64.00  29.50   26
 38  ω     56.00  99.00   1.00   16.00    --   86.00  68.00 152.73   43
 39  ω     60.00  95.00   1.00   16.00    --   90.00  66.00 -66.56   35
 40  ω     61.00  97.00   1.00   16.00    --   90.00  63.00  61.48   36
 41  ω    115.00 163.00   1.00   16.00    --   90.00  63.00  61.48   48
 42  ω    105.00 159.00   1.00   16.00    --   94.00  61.00-118.33   54
 43  ω     65.00 100.00   1.00   16.00    --   94.00  61.00-118.33   35
 44  ω     76.00 171.00   1.00   16.00    --  105.15  61.00 -90.00   95
 45  ω    135.00 167.00   1.00   16.00    --  105.15 111.00  90.00   32
 46  ω    118.00 176.00   1.00   16.00    --  105.15  61.00 -60.00   58
 47  ω     76.00 102.00   1.00   16.00    --  105.15  61.00 120.00   26
 48  ω     33.00 133.00   1.00   16.00    --  105.15 -61.00 120.00  100
 49  ω     77.00 104.00   1.00   16.00    --  105.15  61.00 -60.00   27
 50  ω    104.00 130.00   1.00   16.00    --  105.15 111.00  90.00   26
 51  ω     77.00 175.00   1.00   16.00    --  105.15  61.00 150.00   98
 52  ω     76.00 161.00   1.00   16.00    --  105.15  61.00-150.00   85
 53  ω    126.00 159.00   1.00   16.00    --  105.15  61.00 -30.00   33
 54  ω     36.00 109.00   1.00   16.00    --  105.15-111.00 120.00   73
 55  ω     77.00 104.00   1.00   16.00    --  105.15  61.00 -30.00   27
 56  ω     37.00 106.00   1.00   16.00    --  105.15-111.00 -60.00   69
 57  ω     77.00 120.00   1.00   16.00    --  105.15  61.00-180.00   43
 58  ω     76.00 160.00   1.00   16.00    --  105.15  61.00   0.00   84
 59  ω    116.00 176.00   1.00   16.00    --  105.15  61.00  90.00   60
 60  ω    137.00 178.00   1.00   16.00    --  105.15 111.00 120.00   41
 61  ω    146.00 174.00   1.00   16.00    --  105.15  61.00  60.00   28
 62  ω     76.00 111.00   1.00   16.00    --  105.15  61.00  90.00   35
 63  ω     76.00 144.00   1.00   16.00    --  105.15  61.00  60.00   68
 64  ω     79.00 166.00   1.00   16.00    --  106.00  70.00  18.03   87
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0484376000
_diffrn_orient_matrix_UB_12      -0.1943469000
_diffrn_orient_matrix_UB_13      -0.0197649000
_diffrn_orient_matrix_UB_21      0.0038302000
_diffrn_orient_matrix_UB_22      -0.1043613000
_diffrn_orient_matrix_UB_23      0.0382380000
_diffrn_orient_matrix_UB_31      -0.2305110000
_diffrn_orient_matrix_UB_32      -0.0426272000
_diffrn_orient_matrix_UB_33      -0.0035094000
_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  0.0303
_diffrn_reflns_av_unetI/netI     0.0132
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            27684
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.849
_diffrn_reflns_theta_min         4.959
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.605
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.756
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
 Numerical absorption correction based on Gaussian integration over
 a multifaceted crystal model.
 Empirical absorption correction using spherical harmonics
 as implemented in SCALE3 ABSPACK scaling algorithm
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_description       needle
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.714
_exptl_crystal_size_mid          0.097
_exptl_crystal_size_min          0.038
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
;
 Flack x determined using 1240 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3154
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0264
_refine_ls_R_factor_gt           0.0256
_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)+(0.0348P)²+0.2163P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0655
_refine_ls_wR_factor_ref         0.0663
_reflns_Friedel_coverage         0.681
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                3079
_reflns_number_total             3154
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs0c02430_si_002.cif
_cod_data_source_block           wsg3-4
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Gaussian' was
changed to 'gaussian' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 4517850.cif.
;
_cod_database_code               4517850
_shelx_shelxl_version_number     2018/3
_audit_contact_author            'Farzaneh Fadaei Tirani'
_chemical_oxdiff_formula         'C20 H18 O2'
_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   0.977
_shelx_estimated_absorpt_t_min   0.672
_reflns_odcompleteness_completeness 99.88
_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,H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(H13A)=Sof(H13B)=Sof(H13C)=1-FVAR(1)
 Sof(H13D)=Sof(H13E)=Sof(H13F)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12), C16(H16),
 C17(H17), C18(H18), C19(H19), C20(H20)
3.b Disordered Me refined as rotating group:
 C13(H13A,H13B,H13C,H13D,H13E,H13F)
3.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_olex2_date_sample_data_collection 2019-12-12
_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
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.352
_oxdiff_exptl_absorpt_empirical_full_min 0.783
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 0.68917(14) 0.35961(16) 0.62058(3) 0.0282(2) Uani 1 1 d . . . . .
O2 O 0.96863(15) 0.50880(18) 0.59885(3) 0.0360(3) Uani 1 1 d . . . . .
C1 C 0.4685(2) 0.3743(2) 0.61551(4) 0.0256(3) Uani 1 1 d . . . . .
C2 C 0.7846(2) 0.4973(2) 0.59989(4) 0.0263(3) Uani 1 1 d . . . . .
C3 C 0.6286(2) 0.6167(2) 0.58020(4) 0.0242(3) Uani 1 1 d . . . . .
C4 C 0.4471(2) 0.5441(2) 0.58929(4) 0.0252(3) Uani 1 1 d . . . . .
H4 H 0.320307 0.593197 0.580352 0.030 Uiso 1 1 calc R U . . .
C5 C 0.3644(2) 0.4119(2) 0.65243(4) 0.0263(3) Uani 1 1 d . . . . .
H5 H 0.223747 0.446467 0.651573 0.032 Uiso 1 1 calc R U . . .
C6 C 0.4503(2) 0.4013(2) 0.68604(4) 0.0266(3) Uani 1 1 d . . . . .
H6 H 0.592689 0.374318 0.687135 0.032 Uiso 1 1 calc R U . . .
C7 C 0.3413(2) 0.4282(2) 0.72178(4) 0.0262(3) Uani 1 1 d . . . . .
C8 C 0.1428(2) 0.5034(2) 0.72388(4) 0.0293(3) Uani 1 1 d . . . . .
H8 H 0.074486 0.541439 0.701537 0.035 Uiso 1 1 calc R U . . .
C9 C 0.0443(3) 0.5231(2) 0.75800(4) 0.0339(3) Uani 1 1 d . . . . .
H9 H -0.090197 0.575341 0.758716 0.041 Uiso 1 1 calc R U . . .
C10 C 0.1390(3) 0.4676(2) 0.79132(4) 0.0358(4) Uani 1 1 d . . . . .
C11 C 0.3368(3) 0.3942(2) 0.78935(4) 0.0369(4) Uani 1 1 d . . . . .
H11 H 0.404668 0.356367 0.811747 0.044 Uiso 1 1 calc R U . . .
C12 C 0.4369(2) 0.3750(2) 0.75523(4) 0.0313(3) Uani 1 1 d . . . . .
H12 H 0.572346 0.325009 0.754640 0.038 Uiso 1 1 calc R U . . .
C13 C 0.0282(4) 0.4867(3) 0.82836(5) 0.0511(5) Uani 1 1 d . . . . .
H13A H -0.018150 0.621543 0.831626 0.061 Uiso 0.42(2) 1 calc R U P . .
H13B H 0.121104 0.451817 0.848848 0.061 Uiso 0.42(2) 1 calc R U P . .
H13C H -0.090203 0.399052 0.828613 0.061 Uiso 0.42(2) 1 calc R U P . .
H13D H 0.026651 0.360065 0.841098 0.061 Uiso 0.58(2) 1 calc R U P . .
H13E H -0.112604 0.529791 0.823876 0.061 Uiso 0.58(2) 1 calc R U P . .
H13F H 0.098703 0.582556 0.844112 0.061 Uiso 0.58(2) 1 calc R U P . .
C14 C 0.3935(2) 0.1831(2) 0.59847(4) 0.0329(3) Uani 1 1 d . . . . .
H14A H 0.458216 0.163663 0.573979 0.049 Uiso 1 1 calc R U . . .
H14B H 0.244646 0.188212 0.595374 0.049 Uiso 1 1 calc R U . . .
H14C H 0.429391 0.074678 0.615111 0.049 Uiso 1 1 calc R U . . .
C15 C 0.6786(2) 0.7821(2) 0.55540(4) 0.0237(3) Uani 1 1 d . . . . .
C16 C 0.8442(2) 0.9045(2) 0.56270(4) 0.0278(3) Uani 1 1 d . . . . .
H16 H 0.931943 0.877700 0.583290 0.033 Uiso 1 1 calc R U . . .
C17 C 0.8816(2) 1.0651(2) 0.54009(4) 0.0303(3) Uani 1 1 d . . . . .
H17 H 0.993081 1.149175 0.545619 0.036 Uiso 1 1 calc R U . . .
C18 C 0.7574(2) 1.1037(2) 0.50946(4) 0.0292(3) Uani 1 1 d . . . . .
H18 H 0.783615 1.213691 0.494011 0.035 Uiso 1 1 calc R U . . .
C19 C 0.5947(2) 0.9807(2) 0.50152(4) 0.0278(3) Uani 1 1 d . . . . .
H19 H 0.510442 1.005450 0.480353 0.033 Uiso 1 1 calc R U . . .
C20 C 0.5546(2) 0.8220(2) 0.52437(4) 0.0254(3) Uani 1 1 d . . . . .
H20 H 0.441791 0.739371 0.518927 0.030 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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0191
0 0 1 0.0191
-1 0 0 0.3369
2 1 2 0.3346
1 0 0 0.3773
0 1 1 0.0604
0 -1 -1 0.0272
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
C2 O1 C1 109.96(10) . . ?
O1 C1 C4 102.87(11) . . ?
O1 C1 C5 110.56(11) . . ?
O1 C1 C14 107.96(12) . . ?
C4 C1 C5 111.76(12) . . ?
C4 C1 C14 112.85(12) . . ?
C5 C1 C14 110.52(12) . . ?
O1 C2 C3 109.06(11) . . ?
O2 C2 O1 121.55(13) . . ?
O2 C2 C3 129.38(14) . . ?
C4 C3 C2 106.97(12) . . ?
C4 C3 C15 129.27(13) . . ?
C15 C3 C2 123.76(12) . . ?
C1 C4 H4 124.4 . . ?
C3 C4 C1 111.12(12) . . ?
C3 C4 H4 124.4 . . ?
C1 C5 H5 116.9 . . ?
C6 C5 C1 126.17(13) . . ?
C6 C5 H5 116.9 . . ?
C5 C6 H6 117.6 . . ?
C5 C6 C7 124.83(13) . . ?
C7 C6 H6 117.6 . . ?
C8 C7 C6 122.79(13) . . ?
C12 C7 C6 119.41(13) . . ?
C12 C7 C8 117.79(13) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 C7 120.98(14) . . ?
C9 C8 H8 119.5 . . ?
C8 C9 H9 119.4 . . ?
C8 C9 C10 121.14(15) . . ?
C10 C9 H9 119.4 . . ?
C9 C10 C13 120.59(16) . . ?
C11 C10 C9 118.00(14) . . ?
C11 C10 C13 121.41(16) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 C10 121.15(14) . . ?
C12 C11 H11 119.4 . . ?
C7 C12 H12 119.5 . . ?
C11 C12 C7 120.93(14) . . ?
C11 C12 H12 119.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
C10 C13 H13D 109.5 . . ?
C10 C13 H13E 109.5 . . ?
C10 C13 H13F 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13A C13 H13D 141.1 . . ?
H13A C13 H13E 56.3 . . ?
H13A C13 H13F 56.3 . . ?
H13B C13 H13C 109.5 . . ?
H13B C13 H13D 56.3 . . ?
H13B C13 H13E 141.1 . . ?
H13B C13 H13F 56.3 . . ?
H13C C13 H13D 56.3 . . ?
H13C C13 H13E 56.3 . . ?
H13C C13 H13F 141.1 . . ?
H13D C13 H13E 109.5 . . ?
H13D C13 H13F 109.5 . . ?
H13E C13 H13F 109.5 . . ?
C1 C14 H14A 109.5 . . ?
C1 C14 H14B 109.5 . . ?
C1 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C3 121.52(12) . . ?
C16 C15 C20 118.69(13) . . ?
C20 C15 C3 119.77(12) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.42(13) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C18 120.42(14) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 120.2 . . ?
C19 C18 C17 119.62(13) . . ?
C19 C18 H18 120.2 . . ?
C18 C19 H19 119.9 . . ?
C20 C19 C18 120.19(13) . . ?
C20 C19 H19 119.9 . . ?
C15 C20 H20 119.7 . . ?
C19 C20 C15 120.64(13) . . ?
C19 C20 H20 119.7 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.4579(17) . ?
O1 C2 1.3510(18) . ?
O2 C2 1.2064(18) . ?
C1 C4 1.5003(19) . ?
C1 C5 1.5047(19) . ?
C1 C14 1.526(2) . ?
C2 C3 1.4846(19) . ?
C3 C4 1.327(2) . ?
C3 C15 1.4751(19) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C5 C6 1.3264(19) . ?
C6 H6 0.9500 . ?
C6 C7 1.4723(19) . ?
C7 C8 1.399(2) . ?
C7 C12 1.395(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.384(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.393(2) . ?
C10 C11 1.390(3) . ?
C10 C13 1.513(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.389(2) . ?
C12 H12 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C13 H13D 0.9800 . ?
C13 H13E 0.9800 . ?
C13 H13F 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.395(2) . ?
C15 C20 1.3991(19) . ?
C16 H16 0.9500 . ?
C16 C17 1.386(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.387(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.387(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.385(2) . ?
C20 H20 0.9500 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C4 C3 0.40(16) . . . . ?
O1 C1 C5 C6 -10.8(2) . . . . ?
O1 C2 C3 C4 -1.07(16) . . . . ?
O1 C2 C3 C15 179.32(12) . . . . ?
O2 C2 C3 C4 177.88(16) . . . . ?
O2 C2 C3 C15 -1.7(2) . . . . ?
C1 O1 C2 O2 -177.70(14) . . . . ?
C1 O1 C2 C3 1.35(16) . . . . ?
C1 C5 C6 C7 -176.39(13) . . . . ?
C2 O1 C1 C4 -1.09(15) . . . . ?
C2 O1 C1 C5 -120.55(12) . . . . ?
C2 O1 C1 C14 118.44(13) . . . . ?
C2 C3 C4 C1 0.36(16) . . . . ?
C2 C3 C15 C16 -35.0(2) . . . . ?
C2 C3 C15 C20 146.88(14) . . . . ?
C3 C15 C16 C17 -176.57(13) . . . . ?
C3 C15 C20 C19 177.68(13) . . . . ?
C4 C1 C5 C6 -124.71(16) . . . . ?
C4 C3 C15 C16 145.46(16) . . . . ?
C4 C3 C15 C20 -32.6(2) . . . . ?
C5 C1 C4 C3 119.03(14) . . . . ?
C5 C6 C7 C8 -12.2(2) . . . . ?
C5 C6 C7 C12 166.97(14) . . . . ?
C6 C7 C8 C9 178.80(14) . . . . ?
C6 C7 C12 C11 -178.47(14) . . . . ?
C7 C8 C9 C10 -0.4(2) . . . . ?
C8 C7 C12 C11 0.7(2) . . . . ?
C8 C9 C10 C11 0.8(2) . . . . ?
C8 C9 C10 C13 -178.92(16) . . . . ?
C9 C10 C11 C12 -0.5(2) . . . . ?
C10 C11 C12 C7 -0.3(2) . . . . ?
C12 C7 C8 C9 -0.4(2) . . . . ?
C13 C10 C11 C12 179.29(16) . . . . ?
C14 C1 C4 C3 -115.67(14) . . . . ?
C14 C1 C5 C6 108.71(17) . . . . ?
C15 C3 C4 C1 179.93(13) . . . . ?
C15 C16 C17 C18 -1.4(2) . . . . ?
C16 C15 C20 C19 -0.5(2) . . . . ?
C16 C17 C18 C19 0.1(2) . . . . ?
C17 C18 C19 C20 1.0(2) . . . . ?
C18 C19 C20 C15 -0.8(2) . . . . ?
C20 C15 C16 C17 1.5(2) . . . . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0002 -0.0001 -0.9999 0.0198 -0.0382 0.0035
0.0002 0.0001 0.9999 -0.0198 0.0382 -0.0035
-0.9998 -0.0001 0.0006 -0.0484 -0.0038 0.2305
2.0002 1.0006 1.9980 -0.1371 -0.0204 -0.5107
0.9998 0.0001 -0.0006 0.0484 0.0038 -0.2305
0.0004 1.0003 0.9994 -0.2141 -0.0662 -0.0462
-0.0004 -1.0003 -0.9994 0.2141 0.0662 0.0462
