#------------------------------------------------------------------------------
#$Date: 2020-10-06 10:15:09 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257334 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/76/1557674.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_1557674
loop_
_publ_author_name
'Nelson, Ronald'
'Calvelo, Martín'
'García-Fandiño, Rebeca'
'Lledós, Agustí'
'Ujaque, Gregori'
'Mascareñas, José L.'
'López, Fernando'
_publ_section_title
;
 Skeletal diversity in Pt- and Au-catalyzed annulations of allenedienes:
 dissecting unconventional mechanistic pathways
;
_journal_issue                   16
_journal_name_full               'Chemical Science'
_journal_page_first              4209
_journal_page_last               4220
_journal_paper_doi               10.1039/D0SC00650E
_journal_volume                  11
_journal_year                    2020
_chemical_formula_moiety         'C12 H18 O '
_chemical_formula_sum            'C12 H18 O'
_chemical_formula_weight         178.26
_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
_audit_creation_date             2017-03-26
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-11-06 deposited with the CCDC.	2020-03-27 downloaded from the CCDC.
;
_cell_angle_alpha                92.381(5)
_cell_angle_beta                 98.293(6)
_cell_angle_gamma                100.115(6)
_cell_formula_units_Z            6
_cell_length_a                   6.2162(5)
_cell_length_b                   12.5583(8)
_cell_length_c                   20.7881(12)
_cell_measurement_reflns_used    2495
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      71.3840
_cell_measurement_theta_min      4.2900
_cell_volume                     1577.16(19)
_computing_cell_refinement       'CrysAlisPro 1.171.39.23a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.23a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.23a (Rigaku OD, 2015)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -9.00  24.00   0.50    5.00    --    0.00  19.00  30.00   66
  2  ω     -6.00  64.00   0.50    5.00    --    0.00  57.00  90.00  140
  3  ω     48.00  79.00   0.50    5.00    --    0.00  19.00  30.00   62
  4  ω     41.00  73.00   0.50    5.00    --    0.00  77.00 120.00   64
  5  ω     -7.00  20.00   0.50    5.00    --    0.00  77.00 120.00   54
  6  ω     22.00  54.00   0.50   25.00    --   96.84 -30.00   0.00   64
  7  ω     25.00  59.00   0.50   25.00    --   96.84 -30.00  30.00   68
  8  ω     76.00 112.00   0.50   25.00    --   96.84 -61.00   0.00   72
  9  ω     31.00 116.00   0.50   25.00    --   96.84-125.00-150.00  170
 10  ω     37.00  69.00   0.50   25.00    --   96.84 -61.00   0.00   64
 11  ω     38.00 118.00   0.50   25.00    --   96.84 -77.00 -60.00  160
 12  ω     25.00  56.00   0.50   25.00    --   96.84 -30.00-120.00   62
 13  ω     19.00  56.00   0.50   25.00    --   96.84 -30.00 -60.00   74
 14  ω     19.00  55.00   0.50   25.00    --   96.84 -30.00 -30.00   72
 15  ω     22.00 107.00   0.50   25.00    --   96.84 -94.00 -60.00  170
 16  ω     24.00 106.00   0.50   25.00    --   96.84 -94.00-120.00  164
 17  ω     21.00  95.00   0.50   25.00    --   96.84 -94.00-150.00  148
 18  ω     18.00 148.00   0.50   25.00    --   96.84   0.00-180.00  260
 19  ω     20.00  52.00   0.50   25.00    --   96.84 -30.00  90.00   64
 20  ω   -101.00 -28.00   0.50   25.00    --  -84.25  77.00 120.00  146
 21  ω   -145.00 -71.00   0.50   25.00    --  -84.25 -61.00-150.00  148
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1128312000
_diffrn_orient_matrix_UB_12      -0.0974149000
_diffrn_orient_matrix_UB_13      -0.0478232000
_diffrn_orient_matrix_UB_21      -0.2177761000
_diffrn_orient_matrix_UB_22      -0.0011276000
_diffrn_orient_matrix_UB_23      0.0273905000
_diffrn_orient_matrix_UB_31      -0.0689712000
_diffrn_orient_matrix_UB_32      0.0781671000
_diffrn_orient_matrix_UB_33      -0.0509695000
_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  0.0690
_diffrn_reflns_av_sigmaI/netI    0.1206
_diffrn_reflns_av_unetI/netI     0.0973
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            12485
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.055
_diffrn_reflns_theta_max         67.055
_diffrn_reflns_theta_min         3.584
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.531
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85724
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.23a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.126
_exptl_crystal_description       needle
_exptl_crystal_F_000             588
_exptl_crystal_size_max          0.132
_exptl_crystal_size_mid          0.018
_exptl_crystal_size_min          0.007
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         5534
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.1114
_refine_ls_R_factor_gt           0.0591
_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)+(0.0677P)²+0.0455P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1310
_refine_ls_wR_factor_ref         0.1549
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3322
_reflns_number_total             5534
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc00650e2.cif
_cod_data_source_block           17MCD007
_cod_depositor_comments
;Adding full bibliography for 1557674--1557678.cif.

 Adding full bibliography for 1557674--1557678.cif.
;
_cod_original_formula_sum        'C12 H18 O '
_cod_database_code               1557674
_cell_oxdiff_length_a            6.2162(5)
_cell_oxdiff_length_b            12.5583(7)
_cell_oxdiff_length_c            20.7881(12)
_cell_oxdiff_angle_alpha         92.381(5)
_cell_oxdiff_angle_beta          98.293(6)
_cell_oxdiff_angle_gamma         100.115(6)
_cell_oxdiff_volume              1577.18(18)
_cell_oxdiff_measurement_reflns_used 2495
_oxdiff_exptl_absorpt_empirical_full_min 0.828
_oxdiff_exptl_absorpt_empirical_full_max 1.279
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_oxdiff_ac3_digest_frames
;
01d08591a90e910b76e79a58123b74ba5302292efc4
;
_diffrn_oxdiff_ac3_digest_hkl
;
01f94e75c0f56d3e793ede73c770d009143d7f
;
_reflns_odcompleteness_completeness 98.10
_reflns_odcompleteness_theta     66.97
_reflns_odcompleteness_iscentric 1
_chemical_oxdiff_formula         'C12 H18 O1'
_shelx_shelxl_version_number     2014/7
_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_min   0.933
_shelx_estimated_absorpt_t_max   0.996
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
C1 C 0.6456(4) 0.7409(2) 0.34347(12) 0.0288(6) Uani 1 1 d . . . . .
H1 H 0.5669 0.7988 0.3574 0.035 Uiso 1 1 calc R U . . .
C2 C 0.8516(4) 0.7407(2) 0.39255(12) 0.0271(6) Uani 1 1 d . . . . .
H2 H 0.9336 0.6893 0.3727 0.032 Uiso 1 1 calc R U . . .
C3 C 1.0242(4) 0.8384(2) 0.41929(12) 0.0286(6) Uani 1 1 d . . . . .
C4 C 1.2092(5) 0.8037(3) 0.46527(14) 0.0395(7) Uani 1 1 d . . . . .
H4A H 1.3249 0.7890 0.4398 0.047 Uiso 1 1 calc R U . . .
H4B H 1.2765 0.8647 0.4977 0.047 Uiso 1 1 calc R U . . .
C5 C 1.1382(5) 0.7050(3) 0.50108(13) 0.0398(8) Uani 1 1 d . . . . .
H5 H 1.2485 0.6802 0.5301 0.048 Uiso 1 1 calc R U . . .
C6 C 0.9342(5) 0.6506(3) 0.49509(13) 0.0386(7) Uani 1 1 d . . . . .
H6 H 0.9015 0.5910 0.5209 0.046 Uiso 1 1 calc R U . . .
C7 C 0.7540(5) 0.6814(2) 0.44829(12) 0.0307(6) Uani 1 1 d . . . . .
H7 H 0.6796 0.7319 0.4719 0.037 Uiso 1 1 calc R U . . .
C8 C 0.5774(5) 0.5888(2) 0.41357(13) 0.0370(7) Uani 1 1 d . . . . .
H8A H 0.4521 0.5732 0.4383 0.044 Uiso 1 1 calc R U . . .
H8B H 0.6398 0.5222 0.4086 0.044 Uiso 1 1 calc R U . . .
C9 C 0.5016(5) 0.6288(2) 0.34665(14) 0.0365(7) Uani 1 1 d . . . . .
H9A H 0.3434 0.6345 0.3419 0.044 Uiso 1 1 calc R U . . .
H9B H 0.5220 0.5779 0.3113 0.044 Uiso 1 1 calc R U . . .
O10 O 0.7024(3) 0.75961(15) 0.28043(9) 0.0301(4) Uani 1 1 d . . . . .
H10 H 0.579(5) 0.758(2) 0.2518(11) 0.045 Uiso 1 1 calc R U . . .
C11 C 1.0338(5) 0.9431(2) 0.40712(13) 0.0328(6) Uani 1 1 d . . . . .
C12 C 0.8641(5) 0.9889(2) 0.36256(14) 0.0390(7) Uani 1 1 d . . . . .
H12A H 0.9391 1.0400 0.3350 0.059 Uiso 1 1 calc R U . . .
H12B H 0.7779 1.0267 0.3887 0.059 Uiso 1 1 calc R U . . .
H12C H 0.7650 0.9298 0.3350 0.059 Uiso 1 1 calc R U . . .
C13 C 1.2243(6) 1.0309(3) 0.43772(15) 0.0460(8) Uani 1 1 d . . . . .
H13A H 1.3147 1.0564 0.4046 0.069 Uiso 0.45(3) 1 calc R U P . .
H13B H 1.3152 1.0016 0.4727 0.069 Uiso 0.45(3) 1 calc R U P . .
H13C H 1.1664 1.0915 0.4557 0.069 Uiso 0.45(3) 1 calc R U P . .
H13D H 1.2162 1.0432 0.4841 0.069 Uiso 0.55(3) 1 calc R U P . .
H13E H 1.2157 1.0981 0.4160 0.069 Uiso 0.55(3) 1 calc R U P . .
H13F H 1.3645 1.0081 0.4330 0.069 Uiso 0.55(3) 1 calc R U P . .
C21 C 0.2940(5) 0.8679(2) 0.18280(13) 0.0300(6) Uani 1 1 d . . . . .
H21 H 0.1782 0.8627 0.1435 0.036 Uiso 1 1 calc R U . . .
C22 C 0.5020(4) 0.9428(2) 0.17160(12) 0.0258(6) Uani 1 1 d . . . . .
H22 H 0.6195 0.9326 0.2079 0.031 Uiso 1 1 calc R U . . .
C23 C 0.6060(4) 0.9401(2) 0.11011(13) 0.0298(6) Uani 1 1 d . . . . .
C24 C 0.8050(5) 1.0327(2) 0.11348(15) 0.0403(7) Uani 1 1 d . . . . .
H24A H 0.9413 1.0029 0.1257 0.048 Uiso 1 1 calc R U . . .
H24B H 0.8082 1.0588 0.0693 0.048 Uiso 1 1 calc R U . . .
C25 C 0.8120(5) 1.1273(2) 0.15929(14) 0.0376(7) Uani 1 1 d . . . . .
H25 H 0.9418 1.1817 0.1659 0.045 Uiso 1 1 calc R U . . .
C26 C 0.6496(5) 1.1412(2) 0.19164(14) 0.0362(7) Uani 1 1 d . . . . .
H26 H 0.6615 1.2061 0.2181 0.043 Uiso 1 1 calc R U . . .
C27 C 0.4484(5) 1.0556(2) 0.18673(13) 0.0297(6) Uani 1 1 d . . . . .
H27 H 0.3366 1.0709 0.1503 0.036 Uiso 1 1 calc R U . . .
C28 C 0.3379(5) 1.0399(2) 0.24745(13) 0.0347(7) Uani 1 1 d . . . . .
H28A H 0.4498 1.0538 0.2873 0.042 Uiso 1 1 calc R U . . .
H28B H 0.2320 1.0898 0.2497 0.042 Uiso 1 1 calc R U . . .
C29 C 0.2181(6) 0.9226(2) 0.24101(14) 0.0408(7) Uani 1 1 d . . . . .
H29A H 0.0559 0.9189 0.2330 0.049 Uiso 1 1 calc R U . . .
H29B H 0.2569 0.8863 0.2813 0.049 Uiso 1 1 calc R U . . .
O30 O 0.3383(3) 0.76139(14) 0.19597(9) 0.0302(4) Uani 1 1 d . . . . .
H30 H 0.220(5) 0.7218(17) 0.2130(15) 0.045 Uiso 1 1 calc R U . . .
C31 C 0.5521(5) 0.8687(2) 0.05787(13) 0.0363(7) Uani 1 1 d . . . . .
C32 C 0.3677(6) 0.7720(3) 0.04696(15) 0.0458(8) Uani 1 1 d . . . . .
H32A H 0.2465 0.7875 0.0152 0.069 Uiso 1 1 calc R U . . .
H32B H 0.3141 0.7561 0.0882 0.069 Uiso 1 1 calc R U . . .
H32C H 0.4222 0.7092 0.0303 0.069 Uiso 1 1 calc R U . . .
C33 C 0.6842(7) 0.8786(3) 0.00165(16) 0.0555(9) Uani 1 1 d . . . . .
H33A H 0.8400 0.9076 0.0185 0.083 Uiso 0.42(4) 1 calc R U P . .
H33B H 0.6266 0.9276 -0.0291 0.083 Uiso 0.42(4) 1 calc R U P . .
H33C H 0.6713 0.8069 -0.0207 0.083 Uiso 0.42(4) 1 calc R U P . .
H33D H 0.5852 0.8539 -0.0393 0.083 Uiso 0.58(4) 1 calc R U P . .
H33E H 0.7987 0.8338 0.0082 0.083 Uiso 0.58(4) 1 calc R U P . .
H33F H 0.7540 0.9545 -0.0002 0.083 Uiso 0.58(4) 1 calc R U P . .
C41 C -0.1164(4) 0.5557(2) 0.19599(12) 0.0272(6) Uani 1 1 d . . . . .
H41 H -0.2384 0.5124 0.2156 0.033 Uiso 1 1 calc R U . . .
C42 C 0.0534(4) 0.4860(2) 0.18435(12) 0.0263(6) Uani 1 1 d . . . . .
H42 H 0.1878 0.5379 0.1770 0.032 Uiso 1 1 calc R U . . .
C43 C 0.1379(4) 0.4080(2) 0.23185(12) 0.0275(6) Uani 1 1 d . . . . .
C44 C 0.3082(5) 0.3540(2) 0.20415(13) 0.0331(7) Uani 1 1 d . . . . .
H44A H 0.4569 0.3967 0.2209 0.040 Uiso 1 1 calc R U . . .
H44B H 0.3018 0.2812 0.2211 0.040 Uiso 1 1 calc R U . . .
C45 C 0.2842(5) 0.3413(2) 0.13144(14) 0.0345(7) Uani 1 1 d . . . . .
H45 H 0.3920 0.3107 0.1127 0.041 Uiso 1 1 calc R U . . .
C46 C 0.1214(5) 0.3703(2) 0.09157(14) 0.0374(7) Uani 1 1 d . . . . .
H46 H 0.1095 0.3551 0.0459 0.045 Uiso 1 1 calc R U . . .
C47 C -0.0434(5) 0.4267(2) 0.11771(12) 0.0325(6) Uani 1 1 d . . . . .
H47 H -0.1764 0.3717 0.1226 0.039 Uiso 1 1 calc R U . . .
C48 C -0.1184(6) 0.5182(2) 0.07883(14) 0.0393(7) Uani 1 1 d . . . . .
H48A H 0.0073 0.5618 0.0619 0.047 Uiso 1 1 calc R U . . .
H48B H -0.2354 0.4886 0.0418 0.047 Uiso 1 1 calc R U . . .
C49 C -0.2074(5) 0.5867(2) 0.12762(13) 0.0374(7) Uani 1 1 d . . . . .
H49A H -0.3712 0.5712 0.1204 0.045 Uiso 1 1 calc R U . . .
H49B H -0.1567 0.6649 0.1230 0.045 Uiso 1 1 calc R U . . .
O50 O -0.0091(3) 0.64775(14) 0.23931(8) 0.0292(4) Uani 1 1 d . . . . .
H50 H -0.125(4) 0.6865(18) 0.2543(13) 0.044 Uiso 1 1 calc R U . . .
C51 C 0.0911(5) 0.3882(2) 0.29133(13) 0.0308(6) Uani 1 1 d . . . . .
C52 C -0.0639(5) 0.4396(2) 0.32658(13) 0.0374(7) Uani 1 1 d . . . . .
H52A H -0.0916 0.5056 0.3059 0.056 Uiso 1 1 calc R U . . .
H52B H 0.0029 0.4579 0.3722 0.056 Uiso 1 1 calc R U . . .
H52C H -0.2039 0.3886 0.3245 0.056 Uiso 1 1 calc R U . . .
C53 C 0.1961(6) 0.3087(3) 0.33270(14) 0.0439(8) Uani 1 1 d . . . . .
H53A H 0.3048 0.3487 0.3682 0.066 Uiso 0.56(4) 1 calc R U P . .
H53B H 0.2700 0.2653 0.3057 0.066 Uiso 0.56(4) 1 calc R U P . .
H53C H 0.0814 0.2607 0.3509 0.066 Uiso 0.56(4) 1 calc R U P . .
H53D H 0.1327 0.2345 0.3150 0.066 Uiso 0.44(4) 1 calc R U P . .
H53E H 0.1675 0.3178 0.3776 0.066 Uiso 0.44(4) 1 calc R U P . .
H53F H 0.3561 0.3224 0.3323 0.066 Uiso 0.44(4) 1 calc R U P . .
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 5 -11 0.0114
4 -4 -3 0.0645
-4 4 3 0.0645
-1 -7 -3 0.0018
1 7 3 0.0048
0 -5 11 0.0034
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
O10 C1 C2 110.5(2) . . ?
O10 C1 C9 113.1(2) . . ?
C2 C1 C9 104.4(2) . . ?
O10 C1 H1 109.6 . . ?
C2 C1 H1 109.6 . . ?
C9 C1 H1 109.6 . . ?
C3 C2 C1 126.1(2) . . ?
C3 C2 C7 110.7(2) . . ?
C1 C2 C7 101.8(2) . . ?
C3 C2 H2 105.5 . . ?
C1 C2 H2 105.5 . . ?
C7 C2 H2 105.5 . . ?
C11 C3 C2 129.7(2) . . ?
C11 C3 C4 120.3(3) . . ?
C2 C3 C4 110.0(2) . . ?
C5 C4 C3 114.8(3) . . ?
C5 C4 H4A 108.6 . . ?
C3 C4 H4A 108.6 . . ?
C5 C4 H4B 108.6 . . ?
C3 C4 H4B 108.6 . . ?
H4A C4 H4B 107.5 . . ?
C6 C5 C4 124.7(3) . . ?
C6 C5 H5 117.7 . . ?
C4 C5 H5 117.7 . . ?
C5 C6 C7 120.9(3) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C6 C7 C8 116.7(2) . . ?
C6 C7 C2 110.0(2) . . ?
C8 C7 C2 104.3(2) . . ?
C6 C7 H7 108.5 . . ?
C8 C7 H7 108.5 . . ?
C2 C7 H7 108.5 . . ?
C7 C8 C9 105.3(2) . . ?
C7 C8 H8A 110.7 . . ?
C9 C8 H8A 110.7 . . ?
C7 C8 H8B 110.7 . . ?
C9 C8 H8B 110.7 . . ?
H8A C8 H8B 108.8 . . ?
C8 C9 C1 106.5(2) . . ?
C8 C9 H9A 110.4 . . ?
C1 C9 H9A 110.4 . . ?
C8 C9 H9B 110.4 . . ?
C1 C9 H9B 110.4 . . ?
H9A C9 H9B 108.6 . . ?
C1 O10 H10 109.5 . . ?
C3 C11 C12 126.0(3) . . ?
C3 C11 C13 122.4(3) . . ?
C12 C11 C13 111.6(2) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C13 H13D 109.5 . . ?
H13A C13 H13D 141.1 . . ?
H13B C13 H13D 56.3 . . ?
H13C C13 H13D 56.3 . . ?
C11 C13 H13E 109.5 . . ?
H13A C13 H13E 56.3 . . ?
H13B C13 H13E 141.1 . . ?
H13C C13 H13E 56.3 . . ?
H13D C13 H13E 109.5 . . ?
C11 C13 H13F 109.5 . . ?
H13A C13 H13F 56.3 . . ?
H13B C13 H13F 56.3 . . ?
H13C C13 H13F 141.1 . . ?
H13D C13 H13F 109.5 . . ?
H13E C13 H13F 109.5 . . ?
O30 C21 C22 110.8(2) . . ?
O30 C21 C29 112.0(2) . . ?
C22 C21 C29 105.1(2) . . ?
O30 C21 H21 109.6 . . ?
C22 C21 H21 109.6 . . ?
C29 C21 H21 109.6 . . ?
C21 C22 C23 124.9(2) . . ?
C21 C22 C27 102.2(2) . . ?
C23 C22 C27 111.2(2) . . ?
C21 C22 H22 105.7 . . ?
C23 C22 H22 105.7 . . ?
C27 C22 H22 105.7 . . ?
C31 C23 C22 129.4(3) . . ?
C31 C23 C24 119.6(3) . . ?
C22 C23 C24 110.9(2) . . ?
C25 C24 C23 116.6(2) . . ?
C25 C24 H24A 108.2 . . ?
C23 C24 H24A 108.2 . . ?
C25 C24 H24B 108.2 . . ?
C23 C24 H24B 108.2 . . ?
H24A C24 H24B 107.3 . . ?
C26 C25 C24 124.4(3) . . ?
C26 C25 H25 117.8 . . ?
C24 C25 H25 117.8 . . ?
C25 C26 C27 120.3(3) . . ?
C25 C26 H26 119.9 . . ?
C27 C26 H26 119.9 . . ?
C26 C27 C28 117.4(2) . . ?
C26 C27 C22 110.9(2) . . ?
C28 C27 C22 102.9(2) . . ?
C26 C27 H27 108.4 . . ?
C28 C27 H27 108.4 . . ?
C22 C27 H27 108.4 . . ?
C29 C28 C27 105.7(2) . . ?
C29 C28 H28A 110.6 . . ?
C27 C28 H28A 110.6 . . ?
C29 C28 H28B 110.6 . . ?
C27 C28 H28B 110.6 . . ?
H28A C28 H28B 108.7 . . ?
C28 C29 C21 106.3(2) . . ?
C28 C29 H29A 110.5 . . ?
C21 C29 H29A 110.5 . . ?
C28 C29 H29B 110.5 . . ?
C21 C29 H29B 110.5 . . ?
H29A C29 H29B 108.7 . . ?
C21 O30 H30 109.5 . . ?
C23 C31 C32 127.0(3) . . ?
C23 C31 C33 121.1(3) . . ?
C32 C31 C33 111.9(3) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C31 C33 H33A 109.5 . . ?
C31 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C31 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C31 C33 H33D 109.5 . . ?
H33A C33 H33D 141.1 . . ?
H33B C33 H33D 56.3 . . ?
H33C C33 H33D 56.3 . . ?
C31 C33 H33E 109.5 . . ?
H33A C33 H33E 56.3 . . ?
H33B C33 H33E 141.1 . . ?
H33C C33 H33E 56.3 . . ?
H33D C33 H33E 109.5 . . ?
C31 C33 H33F 109.5 . . ?
H33A C33 H33F 56.3 . . ?
H33B C33 H33F 56.3 . . ?
H33C C33 H33F 141.1 . . ?
H33D C33 H33F 109.5 . . ?
H33E C33 H33F 109.5 . . ?
O50 C41 C42 108.9(2) . . ?
O50 C41 C49 113.2(2) . . ?
C42 C41 C49 104.9(2) . . ?
O50 C41 H41 109.9 . . ?
C42 C41 H41 109.9 . . ?
C49 C41 H41 109.9 . . ?
C41 C42 C43 124.9(2) . . ?
C41 C42 C47 103.1(2) . . ?
C43 C42 C47 110.7(2) . . ?
C41 C42 H42 105.6 . . ?
C43 C42 H42 105.6 . . ?
C47 C42 H42 105.6 . . ?
C51 C43 C44 120.3(2) . . ?
C51 C43 C42 129.5(2) . . ?
C44 C43 C42 110.0(2) . . ?
C45 C44 C43 116.2(2) . . ?
C45 C44 H44A 108.2 . . ?
C43 C44 H44A 108.2 . . ?
C45 C44 H44B 108.2 . . ?
C43 C44 H44B 108.2 . . ?
H44A C44 H44B 107.4 . . ?
C46 C45 C44 123.9(3) . . ?
C46 C45 H45 118.0 . . ?
C44 C45 H45 118.0 . . ?
C45 C46 C47 120.6(3) . . ?
C45 C46 H46 119.7 . . ?
C47 C46 H46 119.7 . . ?
C46 C47 C48 116.8(2) . . ?
C46 C47 C42 111.0(2) . . ?
C48 C47 C42 101.9(2) . . ?
C46 C47 H47 108.9 . . ?
C48 C47 H47 108.9 . . ?
C42 C47 H47 108.9 . . ?
C49 C48 C47 104.7(2) . . ?
C49 C48 H48A 110.8 . . ?
C47 C48 H48A 110.8 . . ?
C49 C48 H48B 110.8 . . ?
C47 C48 H48B 110.8 . . ?
H48A C48 H48B 108.9 . . ?
C48 C49 C41 106.4(2) . . ?
C48 C49 H49A 110.4 . . ?
C41 C49 H49A 110.4 . . ?
C48 C49 H49B 110.4 . . ?
C41 C49 H49B 110.4 . . ?
H49A C49 H49B 108.6 . . ?
C41 O50 H50 109.5 . . ?
C43 C51 C52 126.5(2) . . ?
C43 C51 C53 122.3(3) . . ?
C52 C51 C53 111.3(2) . . ?
C51 C52 H52A 109.5 . . ?
C51 C52 H52B 109.5 . . ?
H52A C52 H52B 109.5 . . ?
C51 C52 H52C 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
C51 C53 H53A 109.5 . . ?
C51 C53 H53B 109.5 . . ?
H53A C53 H53B 109.5 . . ?
C51 C53 H53C 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?
C51 C53 H53D 109.5 . . ?
H53A C53 H53D 141.1 . . ?
H53B C53 H53D 56.3 . . ?
H53C C53 H53D 56.3 . . ?
C51 C53 H53E 109.5 . . ?
H53A C53 H53E 56.3 . . ?
H53B C53 H53E 141.1 . . ?
H53C C53 H53E 56.3 . . ?
H53D C53 H53E 109.5 . . ?
C51 C53 H53F 109.5 . . ?
H53A C53 H53F 56.3 . . ?
H53B C53 H53F 56.3 . . ?
H53C C53 H53F 141.1 . . ?
H53D C53 H53F 109.5 . . ?
H53E C53 H53F 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
C1 O10 1.424(3) . ?
C1 C2 1.519(4) . ?
C1 C9 1.539(4) . ?
C1 H1 1.0000 . ?
C2 C3 1.508(4) . ?
C2 C7 1.543(4) . ?
C2 H2 1.0000 . ?
C3 C11 1.342(4) . ?
C3 C4 1.523(4) . ?
C4 C5 1.504(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.317(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.490(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.526(4) . ?
C7 H7 1.0000 . ?
C8 C9 1.537(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
O10 H10 0.90(3) . ?
C11 C12 1.509(4) . ?
C11 C13 1.512(4) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C13 H13D 0.9800 . ?
C13 H13E 0.9800 . ?
C13 H13F 0.9800 . ?
C21 O30 1.442(3) . ?
C21 C22 1.513(4) . ?
C21 C29 1.539(4) . ?
C21 H21 1.0000 . ?
C22 C23 1.515(4) . ?
C22 C27 1.541(3) . ?
C22 H22 1.0000 . ?
C23 C31 1.343(4) . ?
C23 C24 1.533(4) . ?
C24 C25 1.482(4) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.323(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.487(4) . ?
C26 H26 0.9500 . ?
C27 C28 1.525(4) . ?
C27 H27 1.0000 . ?
C28 C29 1.520(4) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
O30 H30 0.94(4) . ?
C31 C32 1.501(4) . ?
C31 C33 1.519(4) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C33 H33D 0.9800 . ?
C33 H33E 0.9800 . ?
C33 H33F 0.9800 . ?
C41 O50 1.436(3) . ?
C41 C42 1.523(4) . ?
C41 C49 1.544(4) . ?
C41 H41 1.0000 . ?
C42 C43 1.523(3) . ?
C42 C47 1.534(4) . ?
C42 H42 1.0000 . ?
C43 C51 1.334(4) . ?
C43 C44 1.520(4) . ?
C44 C45 1.496(4) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C45 C46 1.325(4) . ?
C45 H45 0.9500 . ?
C46 C47 1.493(4) . ?
C46 H46 0.9500 . ?
C47 C48 1.533(4) . ?
C47 H47 1.0000 . ?
C48 C49 1.527(4) . ?
C48 H48A 0.9900 . ?
C48 H48B 0.9900 . ?
C49 H49A 0.9900 . ?
C49 H49B 0.9900 . ?
O50 H50 1.01(3) . ?
C51 C52 1.505(4) . ?
C51 C53 1.517(4) . ?
C52 H52A 0.9800 . ?
C52 H52B 0.9800 . ?
C52 H52C 0.9800 . ?
C53 H53A 0.9800 . ?
C53 H53B 0.9800 . ?
C53 H53C 0.9800 . ?
C53 H53D 0.9800 . ?
C53 H53E 0.9800 . ?
C53 H53F 0.9800 . ?
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
O10 H10 O30 0.90 1.76 2.661(3) 177.5 .
O30 H30 O50 0.94 1.73 2.664(3) 176.1 .
O50 H50 O10 1.01 1.66 2.673(3) 175.1 1_455
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 C1 C2 C3 72.1(3) . . . . ?
C9 C1 C2 C3 -166.0(2) . . . . ?
O10 C1 C2 C7 -161.0(2) . . . . ?
C9 C1 C2 C7 -39.1(2) . . . . ?
C1 C2 C3 C11 0.9(4) . . . . ?
C7 C2 C3 C11 -122.3(3) . . . . ?
C1 C2 C3 C4 -177.8(2) . . . . ?
C7 C2 C3 C4 59.0(3) . . . . ?
C11 C3 C4 C5 150.5(3) . . . . ?
C2 C3 C4 C5 -30.6(3) . . . . ?
C3 C4 C5 C6 -0.4(4) . . . . ?
C4 C5 C6 C7 2.9(5) . . . . ?
C5 C6 C7 C8 143.8(3) . . . . ?
C5 C6 C7 C2 25.3(4) . . . . ?
C3 C2 C7 C6 -56.5(3) . . . . ?
C1 C2 C7 C6 167.2(2) . . . . ?
C3 C2 C7 C8 177.6(2) . . . . ?
C1 C2 C7 C8 41.3(2) . . . . ?
C6 C7 C8 C9 -148.8(2) . . . . ?
C2 C7 C8 C9 -27.2(3) . . . . ?
C7 C8 C9 C1 2.9(3) . . . . ?
O10 C1 C9 C8 143.0(2) . . . . ?
C2 C1 C9 C8 22.9(3) . . . . ?
C2 C3 C11 C12 1.0(5) . . . . ?
C4 C3 C11 C12 179.6(3) . . . . ?
C2 C3 C11 C13 -178.7(3) . . . . ?
C4 C3 C11 C13 -0.1(4) . . . . ?
O30 C21 C22 C23 75.3(3) . . . . ?
C29 C21 C22 C23 -163.5(2) . . . . ?
O30 C21 C22 C27 -157.7(2) . . . . ?
C29 C21 C22 C27 -36.5(2) . . . . ?
C21 C22 C23 C31 -6.7(4) . . . . ?
C27 C22 C23 C31 -129.8(3) . . . . ?
C21 C22 C23 C24 175.7(2) . . . . ?
C27 C22 C23 C24 52.6(3) . . . . ?
C31 C23 C24 C25 160.1(2) . . . . ?
C22 C23 C24 C25 -22.0(3) . . . . ?
C23 C24 C25 C26 -7.2(4) . . . . ?
C24 C25 C26 C27 4.0(4) . . . . ?
C25 C26 C27 C28 145.4(3) . . . . ?
C25 C26 C27 C22 27.5(3) . . . . ?
C21 C22 C27 C26 168.5(2) . . . . ?
C23 C22 C27 C26 -56.1(3) . . . . ?
C21 C22 C27 C28 42.2(3) . . . . ?
C23 C22 C27 C28 177.6(2) . . . . ?
C26 C27 C28 C29 -153.9(2) . . . . ?
C22 C27 C28 C29 -31.8(3) . . . . ?
C27 C28 C29 C21 9.4(3) . . . . ?
O30 C21 C29 C28 137.5(2) . . . . ?
C22 C21 C29 C28 17.2(3) . . . . ?
C22 C23 C31 C32 1.0(4) . . . . ?
C24 C23 C31 C32 178.3(3) . . . . ?
C22 C23 C31 C33 -177.8(3) . . . . ?
C24 C23 C31 C33 -0.4(4) . . . . ?
O50 C41 C42 C43 78.2(3) . . . . ?
C49 C41 C42 C43 -160.3(3) . . . . ?
O50 C41 C42 C47 -154.6(2) . . . . ?
C49 C41 C42 C47 -33.1(3) . . . . ?
C41 C42 C43 C51 -2.8(5) . . . . ?
C47 C42 C43 C51 -126.8(3) . . . . ?
C41 C42 C43 C44 -179.1(2) . . . . ?
C47 C42 C43 C44 56.9(3) . . . . ?
C51 C43 C44 C45 154.9(3) . . . . ?
C42 C43 C44 C45 -28.4(3) . . . . ?
C43 C44 C45 C46 -2.7(4) . . . . ?
C44 C45 C46 C47 4.7(4) . . . . ?
C45 C46 C47 C48 140.6(3) . . . . ?
C45 C46 C47 C42 24.5(4) . . . . ?
C41 C42 C47 C46 168.8(2) . . . . ?
C43 C42 C47 C46 -55.5(3) . . . . ?
C41 C42 C47 C48 43.8(3) . . . . ?
C43 C42 C47 C48 179.5(2) . . . . ?
C46 C47 C48 C49 -158.7(3) . . . . ?
C42 C47 C48 C49 -37.6(3) . . . . ?
C47 C48 C49 C41 17.3(3) . . . . ?
O50 C41 C49 C48 128.4(3) . . . . ?
C42 C41 C49 C48 9.8(3) . . . . ?
C44 C43 C51 C52 176.6(3) . . . . ?
C42 C43 C51 C52 0.6(5) . . . . ?
C44 C43 C51 C53 -2.5(4) . . . . ?
C42 C43 C51 C53 -178.5(3) . . . . ?
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
0.0014 4.9957 -10.9920 0.0389 -0.3070 0.9507
3.9978 -3.9993 -2.9879 0.0814 -0.9479 -0.4360
-3.9978 3.9993 2.9879 -0.0814 0.9479 0.4360
-0.9995 -7.0013 -3.0103 0.9388 0.1431 -0.3249
0.9995 7.0013 3.0103 -0.9388 -0.1431 0.3249
-0.0014 -4.9957 10.9920 -0.0389 0.3070 -0.9507
