#------------------------------------------------------------------------------
#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/85/1558553.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_1558553
loop_
_publ_author_name
'Luo, Weiwei'
'Sun, Zhicheng'
'Fernando, E. H. Nisala'
'Nesterov, Vladimir'
'Cundari, Thomas R.'
'Wang, Hong'
_publ_section_title
;
 Formal Oxo- and Aza-[3+2] Reactions of α-Enaminones and Quinones: A
 Double Divergent Process and the Roles of Chiral Phosphoric Acid and
 Molecular Sieves
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC02078H
_journal_year                    2020
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C14 H14 O6'
_chemical_formula_sum            'C14 H14 O6'
_chemical_formula_weight         278.25
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-06-04
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.01.05 svn.r3372 for Rigaku Oxford Diffraction, GUI svn.r5289)
;
_audit_update_record
;
2019-06-05 deposited with the CCDC.	2020-07-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.17307(3)
_cell_length_b                   9.46902(5)
_cell_length_c                   36.9162(2)
_cell_measurement_reflns_used    37812
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.4330
_cell_measurement_theta_min      3.6050
_cell_volume                     2507.42(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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 (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     11.00 116.00   0.50    0.50    --   39.20  57.00  60.00  210
  2  ω    102.00 178.00   0.50    0.50    --  116.00 104.00 140.00  152
  3  ω     99.00 178.00   0.50    0.50    --  116.00 111.00 120.00  158
  4  ω     85.00 178.00   0.50    0.50    --  116.00  77.00  30.00  186
  5  ω     99.00 178.00   0.50    0.50    --  116.00 111.00-120.00  158
  6  ω     99.00 178.00   0.50    0.50    --  116.00 111.00-180.00  158
  7  ω     99.00 178.00   0.50    0.50    --  116.00 111.00-150.00  158
  8  ω     85.00 178.00   0.50    0.50    --  116.00  77.00-150.00  186
  9  ω     86.00 178.00   0.50    0.50    --  116.00  45.00 -90.00  184
 10  ω     86.00 178.00   0.50    0.50    --  116.00  61.00  90.00  184
 11  ω     78.00 178.00   0.50    0.50    --  116.00  30.00-120.00  200
 12  ω     86.00 178.00   0.50    0.50    --  116.00  45.00-180.00  184
 13  ω     85.00 178.00   0.50    0.50    --  116.00  77.00-180.00  186
 14  ω     59.00 150.00   0.50    0.50    --  116.00 178.00 -90.00  182
 15  ω     59.00 150.00   0.50    0.50    --  116.00 178.00  60.00  182
 16  ω     35.00 178.00   0.50    0.50    --  116.00  15.00  30.00  286
 17  ω     35.00 111.00   0.50    0.50    --  116.00-104.00  39.00  152
 18  ω     41.00  96.00   0.50    0.50    --  116.00 -77.00  60.00  110
 19  ω     35.00 109.00   0.50    0.50    --  116.00 -94.00 150.00  148
 20  ω     35.00 112.00   0.50    0.50    --  116.00-111.00  90.00  154
 21  ω     35.00 112.00   0.50    0.50    --  116.00-111.00   0.00  154
 22  ω     30.00 100.00   0.50    0.50    --   39.20-125.00 -90.00  140
 23  ω     41.00  96.00   0.50    0.50    --  116.00 -77.00-150.00  110
 24  ω     41.00  96.00   0.50    0.50    --  116.00 -77.00-180.00  110
 25  ω     35.00 112.00   0.50    0.50    --  116.00-111.00-120.00  154
 26  ω     35.00 109.00   0.50    0.50    --  116.00 -94.00-120.00  148
 27  ω     35.00 112.00   0.50    0.50    --  116.00-111.00 -30.00  154
 28  ω     35.00 109.00   0.50    0.50    --  116.00 -94.00-180.00  148
 29  ω     35.00 112.00   0.50    0.50    --  116.00-111.00 -60.00  154
 30  ω     35.00 109.00   0.50    0.50    --  116.00 -94.00  60.00  148
 31  ω     35.00 112.00   0.50    0.50    --  116.00-111.00 150.00  154
 32  ω     13.00  88.00   0.50    0.50    --   39.20-104.00  39.00  150
 33  ω     11.00 116.00   0.50    0.50    --   39.20  57.00-180.00  210
 34  ω      4.00  41.00   0.50    0.50    --   39.20  77.00-120.00   74
 35  ω      4.00  41.00   0.50    0.50    --   39.20  77.00-180.00   74
 36  ω      4.00  41.00   0.50    0.50    --   39.20  77.00 -90.00   74
 37  ω      4.00  41.00   0.50    0.50    --   39.20  77.00 -30.00   74
 38  ω      4.00  41.00   0.50    0.50    --   39.20  77.00   0.00   74
 39  ω      4.00  41.00   0.50    0.50    --   39.20  77.00  60.00   74
 40  ω      4.00  41.00   0.50    0.50    --   39.20  77.00  30.00   74
 41  ω      4.00  41.00   0.50    0.50    --   39.20  77.00  90.00   74
 42  ω      4.00  41.00   0.50    0.50    --   39.20  77.00 150.00   74
 43  ω    -46.00  16.00   0.50    0.50    --   39.20 -19.00  60.00  124
 44  ω    -46.00  16.00   0.50    0.50    --   39.20 -19.00  30.00  124
 45  ω    -46.00  16.00   0.50    0.50    --   39.20 -19.00  90.00  124
 46  ω    -67.00  37.00   0.50    0.50    --  -39.20  57.00  30.00  208
 47  ω    -45.00 -11.00   0.50    0.50    --  -94.50  30.00 -30.00   68
 48  ω    -45.00 -11.00   0.50    0.50    --  -94.50  30.00   0.00   68
 49  ω    -45.00 -11.00   0.50    0.50    --  -94.50  30.00 -90.00   68
 50  ω    -45.00 -11.00   0.50    0.50    --  -94.50  30.00-180.00   68
 51  ω   -118.00 -78.00   0.50    0.50    --  -39.20-125.00-150.00   80
 52  ω   -118.00 -78.00   0.50    0.50    --  -39.20-125.00-180.00   80
 53  ω   -176.00 -80.00   0.50    0.50    --  -94.50-104.00  39.00  192
 54  ω   -118.00 -78.00   0.50    0.50    --  -39.20-125.00  90.00   80
 55  ω   -171.00 -64.00   0.50    0.50    --  -94.50 -61.00 120.00  214
 56  ω    -45.00 -11.00   0.50    0.50    --  -94.50  30.00 150.00   68
 57  ω    -45.00 -11.00   0.50    0.50    --  -94.50  30.00 120.00   68
 58  ω    -86.00   8.00   0.50    0.50    --  -39.20 104.00 140.00  188
 59  ω      4.00  41.00   0.50    0.50    --   39.20  77.00 -60.00   74
 60  ω    -85.00 -13.00   0.50    0.50    --  -94.50 104.00 140.00  144
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0168024000
_diffrn_orient_matrix_UB_12      -0.0008488000
_diffrn_orient_matrix_UB_13      0.0416136000
_diffrn_orient_matrix_UB_21      0.0584828000
_diffrn_orient_matrix_UB_22      -0.1565022000
_diffrn_orient_matrix_UB_23      0.0006755000
_diffrn_orient_matrix_UB_31      0.2059133000
_diffrn_orient_matrix_UB_32      0.0444454000
_diffrn_orient_matrix_UB_33      0.0032064000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0134
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            52023
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.474
_diffrn_reflns_theta_min         4.792
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.986
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84005
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_description       block
_exptl_crystal_F_000             1168
_exptl_crystal_recrystallization_method 'Vapour deposition'
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.035
_refine_diff_density_max         0.848
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 2120 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_coef       0.00095(17)
_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   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     369
_refine_ls_number_reflns         5118
_refine_ls_number_restraints     39
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0311
_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)+(0.0427P)²+0.8631P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0804
_refine_ls_wR_factor_ref         0.0806
_reflns_Friedel_coverage         0.731
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                5059
_reflns_number_total             5118
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc02078h2.cif
_cod_data_source_block           str0268lt100kcu
_cod_database_code               1558553
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C14H10O6
_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.
;
_diffrn_oxdiff_ac3_digest_frames
;
01fa6e92c5b04c14b45882ea8dceb65f8e000578c83
;
_diffrn_oxdiff_ac3_digest_hkl
;
013fa937a9e11914ff5eedb4a72c19eba11306
;
_reflns_odcompleteness_completeness 99.96
_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, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C4A) = Uanis(C5A) = Uanis(C4B) = Uanis(C5B)
3. Rigid body (RIGU) restrains
 C6A, C5A, C4A, C3A, C2A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C6A, C5B, C4B, C3A, C2A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Others
 Sof(H3AC)=Sof(H3AD)=Sof(H6AB)=Sof(C4B)=Sof(H4BA)=Sof(H4BB)=Sof(C5B)=Sof(H5BA)=
 Sof(H5BB)=1-FVAR(1)
 Sof(H3AA)=Sof(H3AB)=Sof(C4A)=Sof(H4AA)=Sof(H4AB)=Sof(C5A)=Sof(H5AA)=Sof(H5AB)=
 Sof(H6AA)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C6A(H6AA), C6A(H6AB), C6(H6B)
5.b Secondary CH2 refined with riding coordinates:
 C3A(H3AA,H3AB), C3A(H3AC,H3AD), C4A(H4AA,H4AB), C5A(H5AA,H5AB), C3(H3A,H3B),
 C4(H4A,H4B), C5(H5A,H5B), C4B(H4BA,H4BB), C5B(H5BA,H5BB)
5.c Aromatic/amide H refined with riding coordinates:
 C10A(H10A), C11A(H11A), C10(H10), C11(H11)
5.d Idealised Me refined as rotating group:
 C14A(H14A,H14B,H14C), C14(H14D,H14E,H14F)
5.e Idealised tetrahedral OH refined as rotating group:
 O2A(H2A), O6A(H6A), O2(H2), O6(H6)
;
_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 1.311
_oxdiff_exptl_absorpt_empirical_full_min 0.797
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 0.6214(2) 0.35649(15) 0.28133(4) 0.0225(3) Uani 1 1 d . . . . .
O1A O 0.2518(2) 0.42898(15) 0.42716(4) 0.0262(3) Uani 1 1 d . . . . .
O2A O 0.5025(2) 0.54263(16) 0.45449(4) 0.0272(3) Uani 1 1 d . . . . .
H2A H 0.553709 0.465424 0.455957 0.041 Uiso 1 1 calc GR . . . .
O3A O 0.3582(3) 0.37861(17) 0.50730(4) 0.0346(4) Uani 1 1 d . . . . .
O4A O 0.0589(2) 0.98814(18) 0.36362(4) 0.0304(4) Uani 1 1 d . . . . .
O5A O 0.1809(2) 0.94686(16) 0.41854(4) 0.0276(3) Uani 1 1 d . . . . .
O6A O 0.0516(2) 0.78438(19) 0.31665(4) 0.0308(4) Uani 1 1 d . . . . .
H6A H 0.034118 0.864829 0.324139 0.046 Uiso 1 1 calc GR . . . .
C1A C 0.3120(3) 0.5248(2) 0.45556(5) 0.0253(4) Uani 1 1 d . . . . .
C2A C 0.2466(3) 0.4466(2) 0.48994(5) 0.0270(4) Uani 1 1 d . U . . .
C3A C 0.0429(3) 0.4553(3) 0.49900(6) 0.0305(5) Uani 1 1 d . U . . .
H3AA H 0.029268 0.480430 0.524337 0.037 Uiso 0.807(5) 1 calc R . P A 1
H3AB H -0.013430 0.363223 0.495513 0.037 Uiso 0.807(5) 1 calc R . P A 1
H3AC H -0.027441 0.403647 0.480899 0.037 Uiso 0.193(5) 1 calc R . P A 2
H3AD H 0.021758 0.410226 0.522228 0.037 Uiso 0.193(5) 1 calc R . P A 2
C4A C -0.0620(4) 0.5651(3) 0.47550(8) 0.0307(5) Uani 0.807(5) 1 d . U P A 1
H4AA H -0.090190 0.522740 0.452214 0.037 Uiso 0.807(5) 1 calc R . P A 1
H4AB H -0.179563 0.587427 0.487162 0.037 Uiso 0.807(5) 1 calc R . P A 1
C5A C 0.0391(5) 0.6948(5) 0.46947(12) 0.0307(5) Uani 0.807(5) 1 d . U P A 1
H5AA H 0.070434 0.736914 0.492635 0.037 Uiso 0.807(5) 1 calc R . P A 1
H5AB H -0.039885 0.760682 0.456448 0.037 Uiso 0.807(5) 1 calc R . P A 1
C6A C 0.2200(3) 0.6695(2) 0.44755(5) 0.0269(5) Uani 1 1 d . U . . .
H6AA H 0.309010 0.746196 0.451884 0.032 Uiso 0.807(5) 1 calc R . P A 1
H6AB H 0.319453 0.739947 0.449769 0.032 Uiso 0.193(5) 1 calc R . P A 2
C7A C 0.1831(3) 0.6536(2) 0.40716(5) 0.0218(4) Uani 1 1 d . . . . .
C8A C 0.1326(3) 0.7515(2) 0.38020(5) 0.0229(4) Uani 1 1 d . . . . .
C9A C 0.1021(3) 0.6991(3) 0.34482(5) 0.0254(4) Uani 1 1 d . . . . .
C10A C 0.1226(3) 0.5558(3) 0.33703(6) 0.0292(5) Uani 1 1 d . . . . .
H10A H 0.102563 0.523785 0.313530 0.035 Uiso 1 1 calc R . . . .
C11A C 0.1723(3) 0.4608(2) 0.36369(6) 0.0280(5) Uani 1 1 d . . . . .
H11A H 0.185160 0.365026 0.358655 0.034 Uiso 1 1 calc R . . . .
C12A C 0.2023(3) 0.5134(2) 0.39824(5) 0.0239(4) Uani 1 1 d . . . . .
C13A C 0.1191(3) 0.9054(2) 0.38636(6) 0.0240(4) Uani 1 1 d . . . . .
C14A C 0.1771(4) 1.0983(2) 0.42532(7) 0.0320(5) Uani 1 1 d . . . . .
H14A H 0.271744 1.143710 0.411094 0.048 Uiso 1 1 calc GR . . . .
H14B H 0.199881 1.115799 0.450554 0.048 Uiso 1 1 calc GR . . . .
H14C H 0.057103 1.135348 0.418796 0.048 Uiso 1 1 calc GR . . . .
O2 O 0.8003(2) 0.18090(17) 0.25387(4) 0.0263(3) Uani 1 1 d . . . . .
H2 H 0.813112 0.219352 0.234123 0.039 Uiso 1 1 calc GR . . . .
O3 O 0.5256(2) 0.21921(17) 0.20636(4) 0.0273(3) Uani 1 1 d . . . . .
O4 O 0.7009(2) 0.02647(15) 0.41762(4) 0.0238(3) Uani 1 1 d . . . . .
O5 O 0.6073(2) -0.05451(14) 0.36370(4) 0.0218(3) Uani 1 1 d . . . . .
O6 O 0.7140(2) 0.29922(14) 0.42820(3) 0.0226(3) Uani 1 1 d . . . . .
H6 H 0.716181 0.215908 0.434248 0.034 Uiso 1 1 calc GR . . . .
C1 C 0.6266(3) 0.2121(2) 0.26762(5) 0.0212(4) Uani 1 1 d . . . . .
C2 C 0.4765(3) 0.2163(2) 0.23769(5) 0.0224(4) Uani 1 1 d . . . . .
C3 C 0.2755(3) 0.2217(3) 0.24937(6) 0.0301(5) Uani 1 1 d . . . . .
H3A H 0.205149 0.152846 0.235536 0.036 Uiso 1 1 calc R . . . .
H3B H 0.225490 0.314410 0.243842 0.036 Uiso 1 1 calc R . . . .
C4 C 0.2488(3) 0.1921(2) 0.28978(5) 0.0265(4) Uani 1 1 d . . . . .
H4A H 0.277605 0.276227 0.303675 0.032 Uiso 1 1 calc R . . . .
H4B H 0.120068 0.166593 0.294451 0.032 Uiso 1 1 calc R . . . .
C5 C 0.3769(3) 0.0717(2) 0.30129(5) 0.0248(4) Uani 1 1 d . . . . .
H5A H 0.358608 -0.008008 0.285183 0.030 Uiso 1 1 calc R . . . .
H5B H 0.344049 0.041885 0.325603 0.030 Uiso 1 1 calc R . . . .
C6 C 0.5841(3) 0.1158(2) 0.30053(5) 0.0194(4) Uani 1 1 d . . . . .
H6B H 0.665231 0.032502 0.300467 0.023 Uiso 1 1 calc R . . . .
C7 C 0.6323(3) 0.2130(2) 0.33181(5) 0.0184(4) Uani 1 1 d . . . . .
C8 C 0.6569(3) 0.1897(2) 0.36929(5) 0.0182(4) Uani 1 1 d . . . . .
C9 C 0.6881(3) 0.3084(2) 0.39161(5) 0.0191(4) Uani 1 1 d . . . . .
C10 C 0.6936(3) 0.4439(2) 0.37689(5) 0.0214(4) Uani 1 1 d . . . . .
H10 H 0.711711 0.521001 0.392087 0.026 Uiso 1 1 calc R . . . .
C11 C 0.6726(3) 0.4656(2) 0.34010(5) 0.0219(4) Uani 1 1 d . . . . .
H11 H 0.677536 0.555910 0.330232 0.026 Uiso 1 1 calc R . . . .
C12 C 0.6440(3) 0.3481(2) 0.31846(5) 0.0203(4) Uani 1 1 d . . . . .
C13 C 0.6580(3) 0.0482(2) 0.38605(5) 0.0187(4) Uani 1 1 d . . . . .
C14 C 0.6115(3) -0.1956(2) 0.37872(6) 0.0228(4) Uani 1 1 d . . . . .
H14D H 0.547832 -0.259257 0.362696 0.034 Uiso 1 1 calc GR . . . .
H14E H 0.550871 -0.195749 0.401909 0.034 Uiso 1 1 calc GR . . . .
H14F H 0.738562 -0.225509 0.381536 0.034 Uiso 1 1 calc GR . . . .
C4B C -0.0218(18) 0.5910(13) 0.5005(3) 0.0307(5) Uani 0.193(5) 1 d . U P A 2
H4BA H -0.007998 0.624324 0.525191 0.037 Uiso 0.193(5) 1 calc R . P A 2
H4BB H -0.154222 0.589290 0.495161 0.037 Uiso 0.193(5) 1 calc R . P A 2
C5B C 0.079(2) 0.711(2) 0.4727(5) 0.0307(5) Uani 0.193(5) 1 d . U P A 2
H5BA H -0.019794 0.754691 0.458897 0.037 Uiso 0.193(5) 1 calc R . P A 2
H5BB H 0.132706 0.783397 0.487999 0.037 Uiso 0.193(5) 1 calc R . P A 2
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
C12 O1 C1 106.71(14) . . ?
C12A O1A C1A 105.86(15) . . ?
C1A O2A H2A 109.5 . . ?
C13A O5A C14A 116.05(17) . . ?
C9A O6A H6A 109.5 . . ?
O1A C1A C2A 101.76(16) . . ?
O1A C1A C6A 106.73(17) . . ?
O2A C1A O1A 110.54(17) . . ?
O2A C1A C2A 112.61(18) . . ?
O2A C1A C6A 107.99(18) . . ?
C2A C1A C6A 116.85(17) . . ?
O3A C2A C1A 119.3(2) . . ?
O3A C2A C3A 123.7(2) . . ?
C3A C2A C1A 116.96(18) . . ?
C2A C3A H3AA 109.1 . . ?
C2A C3A H3AB 109.1 . . ?
C2A C3A H3AC 109.0 . . ?
C2A C3A H3AD 109.0 . . ?
C2A C3A C4A 112.64(19) . . ?
H3AA C3A H3AB 107.8 . . ?
H3AC C3A H3AD 107.8 . . ?
C4A C3A H3AA 109.1 . . ?
C4A C3A H3AB 109.1 . . ?
C4B C3A C2A 113.0(6) . . ?
C4B C3A H3AC 109.0 . . ?
C4B C3A H3AD 109.0 . . ?
C3A C4A H4AA 108.7 . . ?
C3A C4A H4AB 108.7 . . ?
H4AA C4A H4AB 107.6 . . ?
C5A C4A C3A 114.4(3) . . ?
C5A C4A H4AA 108.7 . . ?
C5A C4A H4AB 108.7 . . ?
C4A C5A H5AA 109.3 . . ?
C4A C5A H5AB 109.3 . . ?
C4A C5A C6A 111.7(3) . . ?
H5AA C5A H5AB 107.9 . . ?
C6A C5A H5AA 109.3 . . ?
C6A C5A H5AB 109.3 . . ?
C1A C6A H6AA 110.3 . . ?
C1A C6A H6AB 106.0 . . ?
C5A C6A C1A 113.2(2) . . ?
C5A C6A H6AA 110.3 . . ?
C7A C6A C1A 99.99(16) . . ?
C7A C6A C5A 112.4(2) . . ?
C7A C6A H6AA 110.3 . . ?
C7A C6A H6AB 106.0 . . ?
C5B C6A C1A 114.7(9) . . ?
C5B C6A H6AB 106.0 . . ?
C5B C6A C7A 122.9(8) . . ?
C8A C7A C6A 132.26(19) . . ?
C12A C7A C6A 108.23(18) . . ?
C12A C7A C8A 119.50(19) . . ?
C7A C8A C9A 117.5(2) . . ?
C7A C8A C13A 123.86(19) . . ?
C9A C8A C13A 118.57(19) . . ?
O6A C9A C8A 122.5(2) . . ?
O6A C9A C10A 116.50(19) . . ?
C10A C9A C8A 121.04(19) . . ?
C9A C10A H10A 119.5 . . ?
C11A C10A C9A 120.95(19) . . ?
C11A C10A H10A 119.5 . . ?
C10A C11A H11A 121.2 . . ?
C10A C11A C12A 117.5(2) . . ?
C12A C11A H11A 121.2 . . ?
O1A C12A C11A 122.94(19) . . ?
C7A C12A O1A 113.57(18) . . ?
C7A C12A C11A 123.5(2) . . ?
O4A C13A O5A 122.7(2) . . ?
O4A C13A C8A 123.2(2) . . ?
O5A C13A C8A 114.06(17) . . ?
O5A C14A H14A 109.5 . . ?
O5A C14A H14B 109.5 . . ?
O5A C14A H14C 109.5 . . ?
H14A C14A H14B 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
C1 O2 H2 109.5 . . ?
C13 O5 C14 115.65(15) . . ?
C9 O6 H6 109.5 . . ?
O1 C1 C2 101.90(15) . . ?
O1 C1 C6 105.94(14) . . ?
O2 C1 O1 110.59(16) . . ?
O2 C1 C2 111.90(15) . . ?
O2 C1 C6 109.92(16) . . ?
C2 C1 C6 116.07(17) . . ?
O3 C2 C1 118.82(19) . . ?
O3 C2 C3 123.51(19) . . ?
C3 C2 C1 117.63(16) . . ?
C2 C3 H3A 109.0 . . ?
C2 C3 H3B 109.0 . . ?
C2 C3 C4 113.14(17) . . ?
H3A C3 H3B 107.8 . . ?
C4 C3 H3A 109.0 . . ?
C4 C3 H3B 109.0 . . ?
C3 C4 H4A 109.8 . . ?
C3 C4 H4B 109.8 . . ?
H4A C4 H4B 108.2 . . ?
C5 C4 C3 109.49(17) . . ?
C5 C4 H4A 109.8 . . ?
C5 C4 H4B 109.8 . . ?
C4 C5 H5A 109.2 . . ?
C4 C5 H5B 109.2 . . ?
C4 C5 C6 111.92(17) . . ?
H5A C5 H5B 107.9 . . ?
C6 C5 H5A 109.2 . . ?
C6 C5 H5B 109.2 . . ?
C1 C6 H6B 110.8 . . ?
C5 C6 C1 111.26(16) . . ?
C5 C6 H6B 110.8 . . ?
C7 C6 C1 101.25(15) . . ?
C7 C6 C5 111.69(16) . . ?
C7 C6 H6B 110.8 . . ?
C8 C7 C6 132.84(18) . . ?
C12 C7 C6 107.82(16) . . ?
C12 C7 C8 119.27(17) . . ?
C7 C8 C13 123.56(17) . . ?
C9 C8 C7 117.88(17) . . ?
C9 C8 C13 118.52(16) . . ?
O6 C9 C8 123.21(17) . . ?
O6 C9 C10 116.13(17) . . ?
C10 C9 C8 120.66(16) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 C9 121.15(18) . . ?
C11 C10 H10 119.4 . . ?
C10 C11 H11 121.2 . . ?
C10 C11 C12 117.61(18) . . ?
C12 C11 H11 121.2 . . ?
O1 C12 C11 122.92(17) . . ?
C7 C12 O1 113.69(17) . . ?
C7 C12 C11 123.39(17) . . ?
O4 C13 O5 122.59(18) . . ?
O4 C13 C8 123.62(18) . . ?
O5 C13 C8 113.79(16) . . ?
O5 C14 H14D 109.5 . . ?
O5 C14 H14E 109.5 . . ?
O5 C14 H14F 109.5 . . ?
H14D C14 H14E 109.5 . . ?
H14D C14 H14F 109.5 . . ?
H14E C14 H14F 109.5 . . ?
C3A C4B H4BA 108.0 . . ?
C3A C4B H4BB 108.0 . . ?
C3A C4B C5B 117.3(10) . . ?
H4BA C4B H4BB 107.2 . . ?
C5B C4B H4BA 108.0 . . ?
C5B C4B H4BB 108.0 . . ?
C6A C5B C4B 121.1(14) . . ?
C6A C5B H5BA 107.0 . . ?
C6A C5B H5BB 107.0 . . ?
C4B C5B H5BA 107.0 . . ?
C4B C5B H5BB 107.0 . . ?
H5BA C5B H5BB 106.8 . . ?
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 1.459(2) . ?
O1 C12 1.382(2) . ?
O1A C1A 1.453(3) . ?
O1A C12A 1.380(2) . ?
O2A H2A 0.8200 . ?
O2A C1A 1.377(3) . ?
O3A C2A 1.211(3) . ?
O4A C13A 1.227(3) . ?
O5A C13A 1.327(3) . ?
O5A C14A 1.456(3) . ?
O6A H6A 0.8200 . ?
O6A C9A 1.366(2) . ?
C1A C2A 1.542(3) . ?
C1A C6A 1.550(3) . ?
C2A C3A 1.501(3) . ?
C3A H3AA 0.9700 . ?
C3A H3AB 0.9700 . ?
C3A H3AC 0.9700 . ?
C3A H3AD 0.9700 . ?
C3A C4A 1.549(4) . ?
C3A C4B 1.367(12) . ?
C4A H4AA 0.9700 . ?
C4A H4AB 0.9700 . ?
C4A C5A 1.443(5) . ?
C5A H5AA 0.9700 . ?
C5A H5AB 0.9700 . ?
C5A C6A 1.548(5) . ?
C6A H6AA 0.9800 . ?
C6A H6AB 0.9800 . ?
C6A C7A 1.522(3) . ?
C6A C5B 1.426(19) . ?
C7A C8A 1.408(3) . ?
C7A C12A 1.375(3) . ?
C8A C9A 1.414(3) . ?
C8A C13A 1.478(3) . ?
C9A C10A 1.395(3) . ?
C10A H10A 0.9300 . ?
C10A C11A 1.380(3) . ?
C11A H11A 0.9300 . ?
C11A C12A 1.386(3) . ?
C14A H14A 0.9600 . ?
C14A H14B 0.9600 . ?
C14A H14C 0.9600 . ?
O2 H2 0.8200 . ?
O2 C1 1.378(2) . ?
O3 C2 1.209(2) . ?
O4 C13 1.223(2) . ?
O5 C13 1.326(2) . ?
O5 C14 1.447(2) . ?
O6 H6 0.8200 . ?
O6 C9 1.366(2) . ?
C1 C2 1.543(3) . ?
C1 C6 1.550(3) . ?
C2 C3 1.505(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.530(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.524(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.544(3) . ?
C6 H6B 0.9800 . ?
C6 C7 1.517(3) . ?
C7 C8 1.412(2) . ?
C7 C12 1.374(3) . ?
C8 C9 1.411(3) . ?
C8 C13 1.476(3) . ?
C9 C10 1.394(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.382(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.385(3) . ?
C14 H14D 0.9600 . ?
C14 H14E 0.9600 . ?
C14 H14F 0.9600 . ?
C4B H4BA 0.9700 . ?
C4B H4BB 0.9700 . ?
C4B C5B 1.69(2) . ?
C5B H5BA 0.9700 . ?
C5B H5BB 0.9700 . ?
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 C2 O3 104.8(2) . . . . ?
O1 C1 C2 C3 -73.2(2) . . . . ?
O1 C1 C6 C5 97.88(18) . . . . ?
O1 C1 C6 C7 -20.92(19) . . . . ?
O1A C1A C2A O3A 99.9(2) . . . . ?
O1A C1A C2A C3A -77.6(2) . . . . ?
O1A C1A C6A C5A 97.3(2) . . . . ?
O1A C1A C6A C7A -22.6(2) . . . . ?
O1A C1A C6A C5B 110.9(8) . . . . ?
O2A C1A C2A O3A -18.5(3) . . . . ?
O2A C1A C2A C3A 163.99(19) . . . . ?
O2A C1A C6A C5A -143.9(2) . . . . ?
O2A C1A C6A C7A 96.30(19) . . . . ?
O2A C1A C6A C5B -130.3(8) . . . . ?
O3A C2A C3A C4A 172.3(2) . . . . ?
O3A C2A C3A C4B 129.4(6) . . . . ?
O6A C9A C10A C11A -179.6(2) . . . . ?
C1A O1A C12A C7A -14.0(2) . . . . ?
C1A O1A C12A C11A 167.0(2) . . . . ?
C1A C2A C3A C4A -10.3(3) . . . . ?
C1A C2A C3A C4B -53.2(6) . . . . ?
C1A C6A C7A C8A -167.0(2) . . . . ?
C1A C6A C7A C12A 14.6(2) . . . . ?
C1A C6A C5B C4B -17.7(15) . . . . ?
C2A C1A C6A C5A -15.7(3) . . . . ?
C2A C1A C6A C7A -135.57(19) . . . . ?
C2A C1A C6A C5B -2.1(8) . . . . ?
C2A C3A C4A C5A -40.9(3) . . . . ?
C2A C3A C4B C5B 31.7(12) . . . . ?
C3A C4A C5A C6A 64.0(4) . . . . ?
C3A C4B C5B C6A 3.0(19) . . . . ?
C4A C5A C6A C1A -33.3(4) . . . . ?
C4A C5A C6A C7A 79.1(3) . . . . ?
C5A C6A C7A C8A 72.6(3) . . . . ?
C5A C6A C7A C12A -105.8(3) . . . . ?
C6A C1A C2A O3A -144.3(2) . . . . ?
C6A C1A C2A C3A 38.1(3) . . . . ?
C6A C7A C8A C9A -177.7(2) . . . . ?
C6A C7A C8A C13A 5.5(4) . . . . ?
C6A C7A C12A O1A -1.2(2) . . . . ?
C6A C7A C12A C11A 177.8(2) . . . . ?
C7A C6A C5B C4B 103.9(13) . . . . ?
C7A C8A C9A O6A 179.61(19) . . . . ?
C7A C8A C9A C10A -0.4(3) . . . . ?
C7A C8A C13A O4A -173.2(2) . . . . ?
C7A C8A C13A O5A 7.9(3) . . . . ?
C8A C7A C12A O1A -179.88(18) . . . . ?
C8A C7A C12A C11A -0.8(3) . . . . ?
C8A C9A C10A C11A 0.4(3) . . . . ?
C9A C8A C13A O4A 9.9(3) . . . . ?
C9A C8A C13A O5A -168.92(18) . . . . ?
C9A C10A C11A C12A -0.5(3) . . . . ?
C10A C11A C12A O1A 179.74(19) . . . . ?
C10A C11A C12A C7A 0.8(3) . . . . ?
C12A O1A C1A O2A -94.20(19) . . . . ?
C12A O1A C1A C2A 145.97(16) . . . . ?
C12A O1A C1A C6A 23.0(2) . . . . ?
C12A C7A C8A C9A 0.6(3) . . . . ?
C12A C7A C8A C13A -176.27(19) . . . . ?
C13A C8A C9A O6A -3.4(3) . . . . ?
C13A C8A C9A C10A 176.64(19) . . . . ?
C14A O5A C13A O4A -1.1(3) . . . . ?
C14A O5A C13A C8A 177.69(18) . . . . ?
O2 C1 C2 O3 -13.4(3) . . . . ?
O2 C1 C2 C3 168.67(19) . . . . ?
O2 C1 C6 C5 -142.61(16) . . . . ?
O2 C1 C6 C7 98.59(17) . . . . ?
O3 C2 C3 C4 170.5(2) . . . . ?
O6 C9 C10 C11 178.78(18) . . . . ?
C1 O1 C12 C7 -10.4(2) . . . . ?
C1 O1 C12 C11 170.60(18) . . . . ?
C1 C2 C3 C4 -11.7(3) . . . . ?
C1 C6 C7 C8 -167.8(2) . . . . ?
C1 C6 C7 C12 15.2(2) . . . . ?
C2 C1 C6 C5 -14.4(2) . . . . ?
C2 C1 C6 C7 -133.16(17) . . . . ?
C2 C3 C4 C5 -41.1(3) . . . . ?
C3 C4 C5 C6 69.1(2) . . . . ?
C4 C5 C6 C1 -38.6(2) . . . . ?
C4 C5 C6 C7 73.7(2) . . . . ?
C5 C6 C7 C8 73.7(3) . . . . ?
C5 C6 C7 C12 -103.31(19) . . . . ?
C6 C1 C2 O3 -140.66(19) . . . . ?
C6 C1 C2 C3 41.4(3) . . . . ?
C6 C7 C8 C9 -175.2(2) . . . . ?
C6 C7 C8 C13 7.0(3) . . . . ?
C6 C7 C12 O1 -3.8(2) . . . . ?
C6 C7 C12 C11 175.19(18) . . . . ?
C7 C8 C9 O6 -179.91(17) . . . . ?
C7 C8 C9 C10 0.2(3) . . . . ?
C7 C8 C13 O4 171.04(19) . . . . ?
C7 C8 C13 O5 -9.2(3) . . . . ?
C8 C7 C12 O1 178.68(17) . . . . ?
C8 C7 C12 C11 -2.3(3) . . . . ?
C8 C9 C10 C11 -1.4(3) . . . . ?
C9 C8 C13 O4 -6.8(3) . . . . ?
C9 C8 C13 O5 172.98(18) . . . . ?
C9 C10 C11 C12 0.7(3) . . . . ?
C10 C11 C12 O1 -179.89(19) . . . . ?
C10 C11 C12 C7 1.2(3) . . . . ?
C12 O1 C1 O2 -99.36(17) . . . . ?
C12 O1 C1 C2 141.53(16) . . . . ?
C12 O1 C1 C6 19.7(2) . . . . ?
C12 C7 C8 C9 1.5(3) . . . . ?
C12 C7 C8 C13 -176.28(18) . . . . ?
C13 C8 C9 O6 -2.0(3) . . . . ?
C13 C8 C9 C10 178.15(18) . . . . ?
C14 O5 C13 O4 -1.9(3) . . . . ?
C14 O5 C13 C8 178.34(16) . . . . ?
C5B C6A C7A C8A 64.7(10) . . . . ?
C5B C6A C7A C12A -113.7(10) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168306564
