#------------------------------------------------------------------------------
#$Date: 2021-01-04 02:29:56 +0200 (Mon, 04 Jan 2021) $
#$Revision: 260402 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/99/1559924.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_1559924
loop_
_publ_author_name
'Al-Khdhairawi, Amjad Ayad Qatran'
'Low, Yun-Yee'
'Manshoor, Nurhuda'
'Arya, Aditya'
'Jelecki, Maciej'
'Alshawsh, Mohammed Abdullah'
'Kamran, Sareh'
'Suliman, Rasha Saad'
'Low, Anis'
'Shivanagere Nagojappa, Narendra Babu'
'Weber, Jean-Frédéric F'
_publ_section_title
;
 Asperginols A and B, Diterpene Pyrones, from an Aspergillus sp.
 and the Structure Revision of Previously Reported Analogues.
;
_journal_issue                   12
_journal_name_full               'Journal of natural products'
_journal_page_first              3564
_journal_page_last               3570
_journal_paper_doi               10.1021/acs.jnatprod.0c00618
_journal_volume                  83
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H40 O5'
_chemical_formula_sum            'C27 H40 O5'
_chemical_formula_weight         444.59
_chemical_melting_point          536.5(5)
_chemical_name_common            'Asperginol B'
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-08-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 110.001(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.4336(5)
_cell_length_b                   17.1372(6)
_cell_length_c                   17.1518(12)
_cell_measurement_reflns_used    10190
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.5750
_cell_measurement_theta_min      3.6760
_cell_volume                     3434.2(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'enCIFer (Allen et al., 2004)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -63.00  28.00   1.00    1.00    --  -42.13  57.00 -60.00   91
  2  ω    -76.00 -19.00   1.00    1.00    --  -42.13 -38.00  60.00   57
  3  ω   -125.00  32.00   1.00    1.00    --  -42.13   0.00 -90.00  157
  4  ω     31.00  86.00   1.00    1.00    --   42.13-125.00-180.00   55
  5  ω     30.00 127.00   1.00    2.77    --  106.06 -77.00 -60.00   97
  6  ω     87.00 132.00   1.00    2.77    --  106.06 -30.00 -90.00   45
  7  ω    109.00 171.00   1.00    2.77    --  106.06  30.00 -30.00   62
  8  ω     92.00 175.00   1.00    2.77    --  106.06  77.00   0.00   83
  9  ω     87.00 174.00   1.00    2.77    --  106.06  61.00  60.00   87
 10  ω     82.00 130.00   1.00    2.77    --  106.06  45.00  60.00   48
 11  ω     79.00 178.00   1.00    2.77    --  106.06  30.00 120.00   99
 12  ω     49.00 101.00   1.00    2.77    --  106.06 -95.00 150.00   52
 13  ω     38.00 118.00   1.00    2.77    --  106.06-125.00 120.00   80
 14  ω     33.00 119.00   1.00    2.77    --  106.06-125.00 -60.00   86
 15  ω     40.00  65.00   1.00    2.77    --  106.06 -30.00 -90.00   25
 16  ω     24.00  80.00   1.00    2.77    --  106.06 -95.00-150.00   56
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            26254
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.196
_diffrn_reflns_theta_min         3.765
_exptl_absorpt_coefficient_mu    0.463
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51309
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    0.860
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 4336 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.936
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     593
_refine_ls_number_reflns         13476
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.936
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0527
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1232P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1495
_refine_ls_wR_factor_ref         0.1632
_reflns_Friedel_coverage         0.896
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.942
_reflns_number_gt                10826
_reflns_number_total             13476
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            np0c00618_si_002.cif
_cod_data_source_block           Asperginol_B
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '536-537 K' was changed to
'536.5(5)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1559924
_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.
;
_exptl_absorpt_special_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_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:
 C2(H2), C6(H6), C10(H10), C14(H14), C2A(H2A), C6A(H6A), C10A(H10A), C14A(H14B)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C4(H4A,H4B), C5(H5A,H5B), C8(H8A,H8B), C9(H9A,H9B), C12(H12A,
 H12B), C13(H13A,H13B), C1A(H1AA,H1AB), C4A(H4AA,H4AB), C5A(H5AA,H5AB),
 C8A(H8AA,H8AB), C9A(H9AA,H9AB), C12A(H12C,H12D), C13A(H13C,H13D)
2.c X=CH2 refined with riding coordinates:
 C20(H20A,H20B), C20A(H20C,H20D)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,
 H19C), C6"(H6"A,H6"B,H6"C), C7"(H7"A,H7"B,H7"C), C6'(H6'A,H6'B,H6'C), C7'(H7'A,
 H7'B,H7'C), C16A(H16D,H16E,H16F), C17A(H17D,H17E,H17F), C18A(H18D,H18E,H18F),
 C19A(H19D,H19E,H19F)
2.e Idealised tetrahedral OH refined as rotating group:
 O14(H14A), O3"(H3"), O3'(H3'), O14A(H14C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, 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
C1 C 0.1837(2) 0.47050(16) 0.4959(2) 0.0640(7) Uani 1 1 d . . . . .
H1A H 0.176065 0.526863 0.493308 0.077 Uiso 1 1 calc R . . . .
H1B H 0.186826 0.452786 0.443002 0.077 Uiso 1 1 calc R . . . .
C2 C 0.2989(2) 0.44868(16) 0.56580(19) 0.0600(6) Uani 1 1 d . . . . .
H2 H 0.304774 0.391631 0.567531 0.072 Uiso 1 1 calc R . . . .
C3 C 0.2995(3) 0.4757(2) 0.6500(2) 0.0747(8) Uani 1 1 d . . . . .
C4 C 0.3073(3) 0.5621(2) 0.6633(3) 0.0805(9) Uani 1 1 d . . . . .
H4A H 0.318291 0.573261 0.721004 0.097 Uiso 1 1 calc R . . . .
H4B H 0.235882 0.586128 0.629513 0.097 Uiso 1 1 calc R . . . .
C5 C 0.4056(3) 0.5976(2) 0.6412(3) 0.0804(9) Uani 1 1 d . . . . .
H5A H 0.477649 0.582702 0.682906 0.096 Uiso 1 1 calc R . . . .
H5B H 0.400002 0.654066 0.641816 0.096 Uiso 1 1 calc R . . . .
C6 C 0.4052(2) 0.57122(15) 0.5556(2) 0.0650(7) Uani 1 1 d . . . . .
H6 H 0.328931 0.585886 0.518006 0.078 Uiso 1 1 calc R . . . .
C7 C 0.4065(2) 0.48105(15) 0.5489(2) 0.0603(6) Uani 1 1 d . . . . .
C8 C 0.4068(3) 0.45367(18) 0.4627(2) 0.0724(8) Uani 1 1 d . . . . .
H8A H 0.469557 0.417375 0.470751 0.087 Uiso 1 1 calc R . . . .
H8B H 0.336167 0.425772 0.434832 0.087 Uiso 1 1 calc R . . . .
C9 C 0.4183(2) 0.5190(2) 0.4072(2) 0.0707(7) Uani 1 1 d . . . . .
H9A H 0.348277 0.549358 0.388007 0.085 Uiso 1 1 calc R . . . .
H9B H 0.432719 0.497971 0.359196 0.085 Uiso 1 1 calc R . . . .
C10 C 0.5182(2) 0.57062(16) 0.45745(19) 0.0619(6) Uani 1 1 d . . . . .
H10 H 0.583199 0.536782 0.486318 0.074 Uiso 1 1 calc R . . . .
C11 C 0.4889(2) 0.61893(15) 0.5224(2) 0.0642(7) Uani 1 1 d . . . . .
C12 C 0.6016(2) 0.64092(18) 0.5917(2) 0.0685(7) Uani 1 1 d . . . . .
H12A H 0.636066 0.593602 0.620523 0.082 Uiso 1 1 calc R . . . .
H12B H 0.583355 0.674002 0.631373 0.082 Uiso 1 1 calc R . . . .
C13 C 0.6910(2) 0.68338(17) 0.5629(2) 0.0695(7) Uani 1 1 d . . . . .
H13A H 0.655369 0.728907 0.530862 0.083 Uiso 1 1 calc R . . . .
H13B H 0.752679 0.701513 0.611464 0.083 Uiso 1 1 calc R . . . .
C14 C 0.7421(2) 0.63302(15) 0.5104(2) 0.0640(7) Uani 1 1 d . . . . .
H14 H 0.751937 0.580039 0.533252 0.077 Uiso 1 1 calc R . . . .
C15 C 0.6734(2) 0.62744(19) 0.4186(2) 0.0723(8) Uani 1 1 d . . . . .
C16 C 0.6793(3) 0.7016(3) 0.3703(3) 0.0964(12) Uani 1 1 d . . . . .
H16A H 0.625858 0.697665 0.314728 0.145 Uiso 1 1 calc GR . . . .
H16B H 0.755310 0.707594 0.368723 0.145 Uiso 1 1 calc GR . . . .
H16C H 0.660473 0.746057 0.397204 0.145 Uiso 1 1 calc GR . . . .
C17 C 0.7114(4) 0.5573(3) 0.3801(3) 0.0922(10) Uani 1 1 d . . . . .
H17A H 0.695404 0.510211 0.404447 0.138 Uiso 1 1 calc GR . . . .
H17B H 0.792095 0.560755 0.390141 0.138 Uiso 1 1 calc GR . . . .
H17C H 0.670650 0.556645 0.321386 0.138 Uiso 1 1 calc GR . . . .
C18 C 0.4247(3) 0.69366(19) 0.4832(3) 0.0900(11) Uani 1 1 d . . . . .
H18A H 0.473436 0.725539 0.463326 0.135 Uiso 1 1 calc GR . . . .
H18B H 0.403638 0.722036 0.524001 0.135 Uiso 1 1 calc GR . . . .
H18C H 0.357079 0.680098 0.437675 0.135 Uiso 1 1 calc GR . . . .
C19 C 0.5114(2) 0.44480(19) 0.6157(3) 0.0777(9) Uani 1 1 d . . . . .
H19A H 0.579317 0.457209 0.603550 0.117 Uiso 1 1 calc GR . . . .
H19B H 0.502404 0.389174 0.615914 0.117 Uiso 1 1 calc GR . . . .
H19C H 0.517801 0.465435 0.669109 0.117 Uiso 1 1 calc GR . . . .
C20 C 0.2949(4) 0.4260(3) 0.7077(3) 0.1000(12) Uani 1 1 d . . . . .
H20A H 0.296458 0.444398 0.759137 0.120 Uiso 1 1 calc R . . . .
H20B H 0.290103 0.372705 0.696979 0.120 Uiso 1 1 calc R . . . .
C1" C 1.0104(2) 0.54944(15) 0.0096(2) 0.0671(7) Uani 1 1 d . . . . .
C2" C 0.92894(19) 0.49468(14) 0.01604(18) 0.0559(6) Uani 1 1 d . . . . .
C3" C 0.9495(2) 0.41718(14) 0.0082(2) 0.0599(6) Uani 1 1 d . . . . .
C4" C 1.0504(2) 0.39028(15) -0.0060(2) 0.0676(7) Uani 1 1 d . . . . .
C5" C 1.1240(3) 0.44396(17) -0.0140(3) 0.0760(9) Uani 1 1 d . . . . .
C6" C 1.2356(3) 0.4326(2) -0.0262(4) 0.1054(15) Uani 1 1 d . . . . .
H6"A H 1.238175 0.381379 -0.048133 0.158 Uiso 1 1 calc GR . . . .
H6"B H 1.296591 0.438146 0.025963 0.158 Uiso 1 1 calc GR . . . .
H6"C H 1.244038 0.471015 -0.064487 0.158 Uiso 1 1 calc GR . . . .
C7" C 1.0727(3) 0.30452(19) -0.0096(4) 0.1063(16) Uani 1 1 d . . . . .
H7"A H 1.153351 0.295847 0.004200 0.159 Uiso 1 1 calc GR . . . .
H7"B H 1.032946 0.285506 -0.064644 0.159 Uiso 1 1 calc GR . . . .
H7"C H 1.045989 0.277348 0.029192 0.159 Uiso 1 1 calc GR . . . .
C1' C 0.0046(2) 0.48667(17) 0.5299(3) 0.0755(9) Uani 1 1 d . . . . .
C2' C 0.0801(2) 0.43624(15) 0.5083(2) 0.0622(7) Uani 1 1 d . . . . .
C3' C 0.0522(2) 0.35853(15) 0.4959(2) 0.0615(6) Uani 1 1 d . . . . .
C4' C -0.0509(2) 0.32744(15) 0.5049(2) 0.0690(8) Uani 1 1 d . . . . .
C5' C -0.1187(2) 0.37766(17) 0.5265(3) 0.0768(9) Uani 1 1 d . . . . .
C6' C -0.2315(3) 0.3616(2) 0.5368(4) 0.1066(15) Uani 1 1 d . . . . .
H6'A H -0.291663 0.366348 0.484026 0.160 Uiso 1 1 calc GR . . . .
H6'B H -0.243751 0.398441 0.575029 0.160 Uiso 1 1 calc GR . . . .
H6'C H -0.231350 0.309655 0.557780 0.160 Uiso 1 1 calc GR . . . .
C7' C -0.0814(3) 0.24249(19) 0.4875(3) 0.0922(12) Uani 1 1 d . . . . .
H7'A H -0.138641 0.228309 0.510859 0.138 Uiso 1 1 calc GR . . . .
H7'B H -0.014335 0.211062 0.511899 0.138 Uiso 1 1 calc GR . . . .
H7'C H -0.110571 0.234026 0.428623 0.138 Uiso 1 1 calc GR . . . .
C1A C 0.8260(2) 0.52377(17) 0.0340(2) 0.0622(6) Uani 1 1 d . . . . .
H1AA H 0.835906 0.579056 0.046553 0.075 Uiso 1 1 calc R . . . .
H1AB H 0.822728 0.497490 0.083260 0.075 Uiso 1 1 calc R . . . .
C2A C 0.7101(2) 0.51181(15) -0.0368(2) 0.0625(6) Uani 1 1 d . . . . .
H2A H 0.698648 0.455536 -0.046155 0.075 Uiso 1 1 calc R . . . .
C3A C 0.7143(3) 0.5479(2) -0.1162(2) 0.0746(8) Uani 1 1 d . . . . .
C4A C 0.7146(3) 0.6351(2) -0.1183(3) 0.0916(11) Uani 1 1 d . . . . .
H4AA H 0.705971 0.652469 -0.173920 0.110 Uiso 1 1 calc R . . . .
H4AB H 0.787471 0.654135 -0.081021 0.110 Uiso 1 1 calc R . . . .
C5A C 0.6179(3) 0.6693(2) -0.0928(3) 0.0935(12) Uani 1 1 d . . . . .
H5AA H 0.545319 0.659079 -0.136222 0.112 Uiso 1 1 calc R . . . .
H5AB H 0.627556 0.725407 -0.087111 0.112 Uiso 1 1 calc R . . . .
C6A C 0.6148(2) 0.63514(16) -0.0107(2) 0.0682(7) Uani 1 1 d . . . . .
H6A H 0.691439 0.645311 0.029224 0.082 Uiso 1 1 calc R . . . .
C7A C 0.6054(2) 0.54438(15) -0.0150(2) 0.0631(7) Uani 1 1 d . . . . .
C8A C 0.6033(2) 0.50986(17) 0.0679(2) 0.0691(7) Uani 1 1 d . . . . .
H8AA H 0.538323 0.474921 0.056057 0.083 Uiso 1 1 calc R . . . .
H8AB H 0.672024 0.478936 0.092409 0.083 Uiso 1 1 calc R . . . .
C9A C 0.5962(3) 0.5693(2) 0.1311(2) 0.0774(8) Uani 1 1 d . . . . .
H9AA H 0.668535 0.596502 0.154446 0.093 Uiso 1 1 calc R . . . .
H9AB H 0.578663 0.543748 0.175773 0.093 Uiso 1 1 calc R . . . .
C10A C 0.5016(2) 0.62659(17) 0.0864(2) 0.0682(7) Uani 1 1 d . . . . .
H10A H 0.434072 0.596124 0.054678 0.082 Uiso 1 1 calc R . . . .
C11A C 0.5318(2) 0.67968(16) 0.0256(3) 0.0759(9) Uani 1 1 d . . . . .
C12A C 0.4219(3) 0.7085(2) -0.0405(3) 0.0943(13) Uani 1 1 d . . . . .
H12C H 0.385435 0.664452 -0.075019 0.113 Uiso 1 1 calc R . . . .
H12D H 0.442451 0.745662 -0.075674 0.113 Uiso 1 1 calc R . . . .
C13A C 0.3340(3) 0.7471(2) -0.0080(4) 0.1039(15) Uani 1 1 d . . . . .
H13C H 0.272189 0.767687 -0.054962 0.125 Uiso 1 1 calc R . . . .
H13D H 0.370512 0.790927 0.026747 0.125 Uiso 1 1 calc R . . . .
C14A C 0.2818(2) 0.69382(16) 0.0422(3) 0.0763(9) Uani 1 1 d . . . . .
H14B H 0.269882 0.642278 0.015828 0.092 Uiso 1 1 calc R . . . .
C15A C 0.3508(3) 0.6826(2) 0.1327(3) 0.0852(10) Uani 1 1 d . . . . .
C16A C 0.3516(4) 0.7540(4) 0.1858(4) 0.130(2) Uani 1 1 d . . . . .
H16D H 0.385305 0.740570 0.243363 0.195 Uiso 1 1 calc GR . . . .
H16E H 0.274544 0.771678 0.174727 0.195 Uiso 1 1 calc GR . . . .
H16F H 0.395507 0.794841 0.172645 0.195 Uiso 1 1 calc GR . . . .
C17A C 0.3116(4) 0.6106(3) 0.1683(4) 0.1103(14) Uani 1 1 d . . . . .
H17D H 0.307431 0.566666 0.132598 0.165 Uiso 1 1 calc GR . . . .
H17E H 0.237423 0.620165 0.172007 0.165 Uiso 1 1 calc GR . . . .
H17F H 0.365229 0.599667 0.222537 0.165 Uiso 1 1 calc GR . . . .
C18A C 0.6012(3) 0.7509(2) 0.0726(4) 0.1189(19) Uani 1 1 d . . . . .
H18D H 0.550997 0.786057 0.087227 0.178 Uiso 1 1 calc GR . . . .
H18E H 0.635343 0.777437 0.037581 0.178 Uiso 1 1 calc GR . . . .
H18F H 0.660129 0.733407 0.122044 0.178 Uiso 1 1 calc GR . . . .
C19A C 0.4983(2) 0.5155(2) -0.0858(3) 0.0901(11) Uani 1 1 d . . . . .
H19D H 0.431988 0.542693 -0.083579 0.135 Uiso 1 1 calc GR . . . .
H19E H 0.488858 0.460472 -0.079692 0.135 Uiso 1 1 calc GR . . . .
H19F H 0.507611 0.525260 -0.138292 0.135 Uiso 1 1 calc GR . . . .
C20A C 0.7173(4) 0.5058(4) -0.1777(3) 0.1070(13) Uani 1 1 d . . . . .
H20C H 0.719876 0.529596 -0.225781 0.128 Uiso 1 1 calc R . . . .
H20D H 0.717016 0.451691 -0.173980 0.128 Uiso 1 1 calc R . . . .
O10 O 0.55156(17) 0.62095(13) 0.40303(15) 0.0746(6) Uani 1 1 d . . . . .
O14 O 0.85456(16) 0.66385(11) 0.52050(18) 0.0761(6) Uani 1 1 d . . . . .
H14A H 0.899434 0.627660 0.524991 0.114 Uiso 1 1 calc GR . . . .
O1" O 1.00538(19) 0.62022(12) 0.0158(2) 0.0971(9) Uani 1 1 d . . . . .
O3" O 0.87209(17) 0.36794(11) 0.01756(18) 0.0757(6) Uani 1 1 d . . . . .
H3" H 0.903117 0.326405 0.036039 0.114 Uiso 1 1 calc GR . . . .
O5" O 1.10452(17) 0.52203(11) -0.00667(18) 0.0769(6) Uani 1 1 d . . . . .
O1' O 0.0151(2) 0.55725(12) 0.5397(2) 0.1042(10) Uani 1 1 d . . . . .
O3' O 0.12285(18) 0.31451(12) 0.47259(17) 0.0758(6) Uani 1 1 d . . . . .
H3' H 0.101791 0.268917 0.469497 0.114 Uiso 1 1 calc GR . . . .
O5' O -0.09264(18) 0.45474(12) 0.5387(2) 0.0853(7) Uani 1 1 d . . . . .
O10A O 0.47127(18) 0.67274(16) 0.14544(19) 0.0902(8) Uani 1 1 d . . . . .
O14A O 0.17065(18) 0.72488(12) 0.0349(2) 0.0954(9) Uani 1 1 d . . . . .
H14C H 0.123270 0.689587 0.022879 0.143 Uiso 1 1 calc GR . . . .
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
H1A C1 H1B 107.7 . . ?
C2 C1 H1A 108.8 . . ?
C2 C1 H1B 108.8 . . ?
C2' C1 H1A 108.8 . . ?
C2' C1 H1B 108.8 . . ?
C2' C1 C2 113.8(2) . . ?
C1 C2 H2 107.5 . . ?
C3 C2 C1 111.2(2) . . ?
C3 C2 H2 107.5 . . ?
C3 C2 C7 110.0(2) . . ?
C7 C2 C1 113.0(2) . . ?
C7 C2 H2 107.5 . . ?
C4 C3 C2 115.3(3) . . ?
C20 C3 C2 122.0(4) . . ?
C20 C3 C4 122.6(4) . . ?
C3 C4 H4A 109.3 . . ?
C3 C4 H4B 109.3 . . ?
C3 C4 C5 111.8(3) . . ?
H4A C4 H4B 107.9 . . ?
C5 C4 H4A 109.3 . . ?
C5 C4 H4B 109.3 . . ?
C4 C5 H5A 109.1 . . ?
C4 C5 H5B 109.1 . . ?
C4 C5 C6 112.3(3) . . ?
H5A C5 H5B 107.9 . . ?
C6 C5 H5A 109.1 . . ?
C6 C5 H5B 109.1 . . ?
C5 C6 H6 103.9 . . ?
C5 C6 C7 111.6(3) . . ?
C5 C6 C11 114.0(2) . . ?
C7 C6 H6 103.9 . . ?
C7 C6 C11 117.8(2) . . ?
C11 C6 H6 103.9 . . ?
C6 C7 C2 108.0(2) . . ?
C6 C7 C8 112.0(3) . . ?
C8 C7 C2 110.5(2) . . ?
C19 C7 C2 106.2(2) . . ?
C19 C7 C6 112.0(2) . . ?
C19 C7 C8 108.0(2) . . ?
C7 C8 H8A 108.7 . . ?
C7 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C9 C8 C7 114.1(2) . . ?
C9 C8 H8A 108.7 . . ?
C9 C8 H8B 108.7 . . ?
C8 C9 H9A 110.1 . . ?
C8 C9 H9B 110.1 . . ?
C8 C9 C10 108.0(3) . . ?
H9A C9 H9B 108.4 . . ?
C10 C9 H9A 110.1 . . ?
C10 C9 H9B 110.1 . . ?
C9 C10 H10 108.3 . . ?
C9 C10 C11 112.0(2) . . ?
C11 C10 H10 108.3 . . ?
O10 C10 C9 110.0(2) . . ?
O10 C10 H10 108.3 . . ?
O10 C10 C11 110.0(2) . . ?
C10 C11 C6 109.5(2) . . ?
C10 C11 C12 108.3(2) . . ?
C10 C11 C18 110.5(3) . . ?
C12 C11 C6 112.7(3) . . ?
C18 C11 C6 106.4(2) . . ?
C18 C11 C12 109.4(2) . . ?
C11 C12 H12A 108.4 . . ?
C11 C12 H12B 108.4 . . ?
C11 C12 C13 115.6(3) . . ?
H12A C12 H12B 107.4 . . ?
C13 C12 H12A 108.4 . . ?
C13 C12 H12B 108.4 . . ?
C12 C13 H13A 108.7 . . ?
C12 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
C14 C13 C12 114.3(2) . . ?
C14 C13 H13A 108.7 . . ?
C14 C13 H13B 108.7 . . ?
C13 C14 H14 107.8 . . ?
C15 C14 C13 116.5(2) . . ?
C15 C14 H14 107.8 . . ?
O14 C14 C13 107.5(2) . . ?
O14 C14 H14 107.8 . . ?
O14 C14 C15 109.0(2) . . ?
C14 C15 C16 113.3(3) . . ?
C14 C15 C17 110.6(3) . . ?
C17 C15 C16 109.9(3) . . ?
O10 C15 C14 112.2(2) . . ?
O10 C15 C16 101.8(3) . . ?
O10 C15 C17 108.6(3) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C11 C18 H18A 109.5 . . ?
C11 C18 H18B 109.5 . . ?
C11 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C7 C19 H19A 109.5 . . ?
C7 C19 H19B 109.5 . . ?
C7 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C3 C20 H20A 120.0 . . ?
C3 C20 H20B 120.0 . . ?
H20A C20 H20B 120.0 . . ?
O1" C1" C2" 126.4(3) . . ?
O1" C1" O5" 115.4(2) . . ?
O5" C1" C2" 118.1(2) . . ?
C1" C2" C1A 118.7(2) . . ?
C3" C2" C1" 118.3(2) . . ?
C3" C2" C1A 122.9(2) . . ?
C2" C3" C4" 122.2(2) . . ?
O3" C3" C2" 115.9(2) . . ?
O3" C3" C4" 121.9(2) . . ?
C3" C4" C7" 120.4(3) . . ?
C5" C4" C3" 117.8(2) . . ?
C5" C4" C7" 121.8(3) . . ?
C4" C5" C6" 129.0(3) . . ?
C4" C5" O5" 120.8(2) . . ?
O5" C5" C6" 110.1(3) . . ?
C5" C6" H6"A 109.5 . . ?
C5" C6" H6"B 109.5 . . ?
C5" C6" H6"C 109.5 . . ?
H6"A C6" H6"B 109.5 . . ?
H6"A C6" H6"C 109.5 . . ?
H6"B C6" H6"C 109.5 . . ?
C4" C7" H7"A 109.5 . . ?
C4" C7" H7"B 109.5 . . ?
C4" C7" H7"C 109.5 . . ?
H7"A C7" H7"B 109.5 . . ?
H7"A C7" H7"C 109.5 . . ?
H7"B C7" H7"C 109.5 . . ?
O1' C1' C2' 126.2(3) . . ?
O1' C1' O5' 115.7(3) . . ?
O5' C1' C2' 118.1(2) . . ?
C1' C2' C1 118.6(2) . . ?
C3' C2' C1 122.9(2) . . ?
C3' C2' C1' 118.5(2) . . ?
C2' C3' C4' 121.8(2) . . ?
O3' C3' C2' 116.2(2) . . ?
O3' C3' C4' 121.9(2) . . ?
C3' C4' C7' 120.4(3) . . ?
C5' C4' C3' 117.2(2) . . ?
C5' C4' C7' 122.3(3) . . ?
C4' C5' C6' 128.0(3) . . ?
C4' C5' O5' 121.7(2) . . ?
O5' C5' C6' 110.2(3) . . ?
C5' C6' H6'A 109.5 . . ?
C5' C6' H6'B 109.5 . . ?
C5' C6' H6'C 109.5 . . ?
H6'A C6' H6'B 109.5 . . ?
H6'A C6' H6'C 109.5 . . ?
H6'B C6' H6'C 109.5 . . ?
C4' C7' H7'A 109.5 . . ?
C4' C7' H7'B 109.5 . . ?
C4' C7' H7'C 109.5 . . ?
H7'A C7' H7'B 109.5 . . ?
H7'A C7' H7'C 109.5 . . ?
H7'B C7' H7'C 109.5 . . ?
C2" C1A H1AA 108.5 . . ?
C2" C1A H1AB 108.5 . . ?
C2" C1A C2A 115.2(2) . . ?
H1AA C1A H1AB 107.5 . . ?
C2A C1A H1AA 108.5 . . ?
C2A C1A H1AB 108.5 . . ?
C1A C2A H2A 107.6 . . ?
C1A C2A C7A 112.9(2) . . ?
C3A C2A C1A 110.1(2) . . ?
C3A C2A H2A 107.6 . . ?
C3A C2A C7A 110.8(2) . . ?
C7A C2A H2A 107.6 . . ?
C4A C3A C2A 115.6(3) . . ?
C20A C3A C2A 121.8(4) . . ?
C20A C3A C4A 122.6(4) . . ?
C3A C4A H4AA 109.3 . . ?
C3A C4A H4AB 109.3 . . ?
C3A C4A C5A 111.6(3) . . ?
H4AA C4A H4AB 108.0 . . ?
C5A C4A H4AA 109.3 . . ?
C5A C4A H4AB 109.3 . . ?
C4A C5A H5AA 109.1 . . ?
C4A C5A H5AB 109.1 . . ?
C4A C5A C6A 112.6(3) . . ?
H5AA C5A H5AB 107.8 . . ?
C6A C5A H5AA 109.1 . . ?
C6A C5A H5AB 109.1 . . ?
C5A C6A H6A 104.5 . . ?
C5A C6A C7A 111.2(3) . . ?
C5A C6A C11A 113.8(2) . . ?
C7A C6A H6A 104.5 . . ?
C7A C6A C11A 117.0(2) . . ?
C11A C6A H6A 104.5 . . ?
C6A C7A C2A 108.1(2) . . ?
C8A C7A C2A 111.0(2) . . ?
C8A C7A C6A 111.2(3) . . ?
C19A C7A C2A 105.0(3) . . ?
C19A C7A C6A 112.8(3) . . ?
C19A C7A C8A 108.6(2) . . ?
C7A C8A H8AA 108.5 . . ?
C7A C8A H8AB 108.5 . . ?
H8AA C8A H8AB 107.5 . . ?
C9A C8A C7A 115.1(2) . . ?
C9A C8A H8AA 108.5 . . ?
C9A C8A H8AB 108.5 . . ?
C8A C9A H9AA 110.2 . . ?
C8A C9A H9AB 110.2 . . ?
C8A C9A C10A 107.4(3) . . ?
H9AA C9A H9AB 108.5 . . ?
C10A C9A H9AA 110.2 . . ?
C10A C9A H9AB 110.2 . . ?
C9A C10A H10A 107.7 . . ?
C11A C10A C9A 113.6(2) . . ?
C11A C10A H10A 107.7 . . ?
O10A C10A C9A 110.1(3) . . ?
O10A C10A H10A 107.7 . . ?
O10A C10A C11A 109.9(2) . . ?
C10A C11A C6A 109.2(2) . . ?
C10A C11A C12A 109.5(2) . . ?
C10A C11A C18A 109.7(4) . . ?
C12A C11A C6A 113.8(3) . . ?
C12A C11A C18A 109.2(3) . . ?
C18A C11A C6A 105.3(2) . . ?
C11A C12A H12C 108.3 . . ?
C11A C12A H12D 108.3 . . ?
C11A C12A C13A 115.8(4) . . ?
H12C C12A H12D 107.4 . . ?
C13A C12A H12C 108.3 . . ?
C13A C12A H12D 108.3 . . ?
C12A C13A H13C 108.3 . . ?
C12A C13A H13D 108.3 . . ?
C12A C13A C14A 115.8(3) . . ?
H13C C13A H13D 107.4 . . ?
C14A C13A H13C 108.3 . . ?
C14A C13A H13D 108.3 . . ?
C13A C14A H14B 107.6 . . ?
C15A C14A C13A 116.8(3) . . ?
C15A C14A H14B 107.6 . . ?
O14A C14A C13A 107.8(2) . . ?
O14A C14A H14B 107.6 . . ?
O14A C14A C15A 109.0(3) . . ?
C14A C15A C16A 113.5(4) . . ?
C14A C15A C17A 111.5(3) . . ?
C16A C15A C17A 110.4(4) . . ?
O10A C15A C14A 111.4(3) . . ?
O10A C15A C16A 102.0(3) . . ?
O10A C15A C17A 107.5(3) . . ?
C15A C16A H16D 109.5 . . ?
C15A C16A H16E 109.5 . . ?
C15A C16A H16F 109.5 . . ?
H16D C16A H16E 109.5 . . ?
H16D C16A H16F 109.5 . . ?
H16E C16A H16F 109.5 . . ?
C15A C17A H17D 109.5 . . ?
C15A C17A H17E 109.5 . . ?
C15A C17A H17F 109.5 . . ?
H17D C17A H17E 109.5 . . ?
H17D C17A H17F 109.5 . . ?
H17E C17A H17F 109.5 . . ?
C11A C18A H18D 109.5 . . ?
C11A C18A H18E 109.5 . . ?
C11A C18A H18F 109.5 . . ?
H18D C18A H18E 109.5 . . ?
H18D C18A H18F 109.5 . . ?
H18E C18A H18F 109.5 . . ?
C7A C19A H19D 109.5 . . ?
C7A C19A H19E 109.5 . . ?
C7A C19A H19F 109.5 . . ?
H19D C19A H19E 109.5 . . ?
H19D C19A H19F 109.5 . . ?
H19E C19A H19F 109.5 . . ?
C3A C20A H20C 120.0 . . ?
C3A C20A H20D 120.0 . . ?
H20C C20A H20D 120.0 . . ?
C10 O10 C15 116.3(2) . . ?
C14 O14 H14A 109.5 . . ?
C3" O3" H3" 109.5 . . ?
C5" O5" C1" 122.7(2) . . ?
C3' O3' H3' 109.5 . . ?
C5' O5' C1' 122.7(2) . . ?
C10A O10A C15A 117.8(3) . . ?
C14A O14A H14C 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 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.567(4) . ?
C1 C2' 1.495(3) . ?
C2 H2 0.9800 . ?
C2 C3 1.514(5) . ?
C2 C7 1.564(3) . ?
C3 C4 1.497(5) . ?
C3 C20 1.323(6) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.526(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.535(5) . ?
C6 H6 0.9800 . ?
C6 C7 1.550(3) . ?
C6 C11 1.575(4) . ?
C7 C8 1.554(5) . ?
C7 C19 1.541(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.508(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.528(4) . ?
C10 H10 0.9800 . ?
C10 C11 1.528(4) . ?
C10 O10 1.432(4) . ?
C11 C12 1.542(4) . ?
C11 C18 1.537(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.545(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.533(4) . ?
C14 H14 0.9800 . ?
C14 C15 1.515(5) . ?
C14 O14 1.449(3) . ?
C15 C16 1.533(5) . ?
C15 C17 1.523(5) . ?
C15 O10 1.450(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9300 . ?
C20 H20B 0.9300 . ?
C1" C2" 1.413(3) . ?
C1" O1" 1.221(3) . ?
C1" O5" 1.375(3) . ?
C2" C3" 1.368(3) . ?
C2" C1A 1.501(3) . ?
C3" C4" 1.434(3) . ?
C3" O3" 1.330(3) . ?
C4" C5" 1.338(4) . ?
C4" C7" 1.501(4) . ?
C5" C6" 1.485(4) . ?
C5" O5" 1.373(3) . ?
C6" H6"A 0.9600 . ?
C6" H6"B 0.9600 . ?
C6" H6"C 0.9600 . ?
C7" H7"A 0.9600 . ?
C7" H7"B 0.9600 . ?
C7" H7"C 0.9600 . ?
C1' C2' 1.416(4) . ?
C1' O1' 1.222(4) . ?
C1' O5' 1.381(3) . ?
C2' C3' 1.374(4) . ?
C3' C4' 1.445(3) . ?
C3' O3' 1.320(3) . ?
C4' C5' 1.343(4) . ?
C4' C7' 1.508(4) . ?
C5' C6' 1.497(4) . ?
C5' O5' 1.359(4) . ?
C6' H6'A 0.9600 . ?
C6' H6'B 0.9600 . ?
C6' H6'C 0.9600 . ?
C7' H7'A 0.9600 . ?
C7' H7'B 0.9600 . ?
C7' H7'C 0.9600 . ?
C1A H1AA 0.9700 . ?
C1A H1AB 0.9700 . ?
C1A C2A 1.548(4) . ?
C2A H2A 0.9800 . ?
C2A C3A 1.513(5) . ?
C2A C7A 1.574(3) . ?
C3A C4A 1.494(5) . ?
C3A C20A 1.289(6) . ?
C4A H4AA 0.9700 . ?
C4A H4AB 0.9700 . ?
C4A C5A 1.529(5) . ?
C5A H5AA 0.9700 . ?
C5A H5AB 0.9700 . ?
C5A C6A 1.537(5) . ?
C6A H6A 0.9800 . ?
C6A C7A 1.560(4) . ?
C6A C11A 1.574(4) . ?
C7A C8A 1.549(4) . ?
C7A C19A 1.546(5) . ?
C8A H8AA 0.9700 . ?
C8A H8AB 0.9700 . ?
C8A C9A 1.512(5) . ?
C9A H9AA 0.9700 . ?
C9A H9AB 0.9700 . ?
C9A C10A 1.522(4) . ?
C10A H10A 0.9800 . ?
C10A C11A 1.524(5) . ?
C10A O10A 1.434(4) . ?
C11A C12A 1.528(5) . ?
C11A C18A 1.552(5) . ?
C12A H12C 0.9700 . ?
C12A H12D 0.9700 . ?
C12A C13A 1.537(5) . ?
C13A H13C 0.9700 . ?
C13A H13D 0.9700 . ?
C13A C14A 1.541(5) . ?
C14A H14B 0.9800 . ?
C14A C15A 1.508(6) . ?
C14A O14A 1.446(3) . ?
C15A C16A 1.523(6) . ?
C15A C17A 1.529(6) . ?
C15A O10A 1.448(3) . ?
C16A H16D 0.9600 . ?
C16A H16E 0.9600 . ?
C16A H16F 0.9600 . ?
C17A H17D 0.9600 . ?
C17A H17E 0.9600 . ?
C17A H17F 0.9600 . ?
C18A H18D 0.9600 . ?
C18A H18E 0.9600 . ?
C18A H18F 0.9600 . ?
C19A H19D 0.9600 . ?
C19A H19E 0.9600 . ?
C19A H19F 0.9600 . ?
C20A H20C 0.9300 . ?
C20A H20D 0.9300 . ?
O14 H14A 0.8200 . ?
O3" H3" 0.8200 . ?
O3' H3' 0.8200 . ?
O14A H14C 0.8200 . ?
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
C1 C2 C3 C4 -70.6(3) . . . . ?
C1 C2 C3 C20 110.2(4) . . . . ?
C1 C2 C7 C6 67.7(3) . . . . ?
C1 C2 C7 C8 -55.1(3) . . . . ?
C1 C2 C7 C19 -171.9(3) . . . . ?
C1 C2' C3' C4' -177.4(3) . . . . ?
C1 C2' C3' O3' 0.4(5) . . . . ?
C2 C1 C2' C1' 109.4(3) . . . . ?
C2 C1 C2' C3' -73.6(4) . . . . ?
C2 C3 C4 C5 -50.7(4) . . . . ?
C2 C7 C8 C9 126.6(2) . . . . ?
C3 C2 C7 C6 -57.2(3) . . . . ?
C3 C2 C7 C8 -180.0(3) . . . . ?
C3 C2 C7 C19 63.2(3) . . . . ?
C3 C4 C5 C6 49.4(5) . . . . ?
C4 C5 C6 C7 -55.3(4) . . . . ?
C4 C5 C6 C11 168.2(3) . . . . ?
C5 C6 C7 C2 58.5(3) . . . . ?
C5 C6 C7 C8 -179.7(2) . . . . ?
C5 C6 C7 C19 -58.2(3) . . . . ?
C5 C6 C11 C10 157.8(3) . . . . ?
C5 C6 C11 C12 37.2(3) . . . . ?
C5 C6 C11 C18 -82.7(4) . . . . ?
C6 C7 C8 C9 6.1(3) . . . . ?
C6 C11 C12 C13 176.4(2) . . . . ?
C7 C2 C3 C4 55.3(3) . . . . ?
C7 C2 C3 C20 -123.9(3) . . . . ?
C7 C6 C11 C10 24.2(4) . . . . ?
C7 C6 C11 C12 -96.4(3) . . . . ?
C7 C6 C11 C18 143.7(3) . . . . ?
C7 C8 C9 C10 48.8(3) . . . . ?
C8 C9 C10 C11 -72.2(3) . . . . ?
C8 C9 C10 O10 165.2(2) . . . . ?
C9 C10 C11 C6 33.2(3) . . . . ?
C9 C10 C11 C12 156.5(3) . . . . ?
C9 C10 C11 C18 -83.7(3) . . . . ?
C9 C10 O10 C15 -134.8(3) . . . . ?
C10 C11 C12 C13 55.0(3) . . . . ?
C11 C6 C7 C2 -166.9(3) . . . . ?
C11 C6 C7 C8 -45.1(3) . . . . ?
C11 C6 C7 C19 76.4(4) . . . . ?
C11 C10 O10 C15 101.4(3) . . . . ?
C11 C12 C13 C14 -67.2(3) . . . . ?
C12 C13 C14 C15 83.5(3) . . . . ?
C12 C13 C14 O14 -153.9(3) . . . . ?
C13 C14 C15 C16 74.5(3) . . . . ?
C13 C14 C15 C17 -161.5(3) . . . . ?
C13 C14 C15 O10 -40.1(3) . . . . ?
C14 C15 O10 C10 -41.6(4) . . . . ?
C16 C15 O10 C10 -163.0(3) . . . . ?
C17 C15 O10 C10 81.0(4) . . . . ?
C18 C11 C12 C13 -65.5(3) . . . . ?
C19 C7 C8 C9 -117.7(3) . . . . ?
C20 C3 C4 C5 128.5(4) . . . . ?
C1" C2" C3" C4" 0.2(5) . . . . ?
C1" C2" C3" O3" 177.8(3) . . . . ?
C1" C2" C1A C2A 113.9(3) . . . . ?
C2" C1" O5" C5" -2.3(5) . . . . ?
C2" C3" C4" C5" -2.0(5) . . . . ?
C2" C3" C4" C7" 176.7(4) . . . . ?
C2" C1A C2A C3A -54.9(3) . . . . ?
C2" C1A C2A C7A -179.2(2) . . . . ?
C3" C2" C1A C2A -68.2(4) . . . . ?
C3" C4" C5" C6" 177.9(4) . . . . ?
C3" C4" C5" O5" 1.6(6) . . . . ?
C4" C5" O5" C1" 0.5(6) . . . . ?
C6" C5" O5" C1" -176.5(4) . . . . ?
C7" C4" C5" C6" -0.7(8) . . . . ?
C7" C4" C5" O5" -177.0(4) . . . . ?
C1' C2' C3' C4' -0.4(5) . . . . ?
C1' C2' C3' O3' 177.3(3) . . . . ?
C2' C1 C2 C3 -59.1(3) . . . . ?
C2' C1 C2 C7 176.6(2) . . . . ?
C2' C1' O5' C5' -0.7(6) . . . . ?
C2' C3' C4' C5' -0.4(5) . . . . ?
C2' C3' C4' C7' 177.5(4) . . . . ?
C3' C4' C5' C6' 177.5(4) . . . . ?
C3' C4' C5' O5' 0.7(6) . . . . ?
C4' C5' O5' C1' -0.1(6) . . . . ?
C6' C5' O5' C1' -177.4(4) . . . . ?
C7' C4' C5' C6' -0.4(7) . . . . ?
C7' C4' C5' O5' -177.2(4) . . . . ?
C1A C2" C3" C4" -177.6(3) . . . . ?
C1A C2" C3" O3" -0.1(4) . . . . ?
C1A C2A C3A C4A -71.4(3) . . . . ?
C1A C2A C3A C20A 108.6(4) . . . . ?
C1A C2A C7A C6A 68.2(3) . . . . ?
C1A C2A C7A C8A -54.0(3) . . . . ?
C1A C2A C7A C19A -171.1(3) . . . . ?
C2A C3A C4A C5A -50.7(5) . . . . ?
C2A C7A C8A C9A 127.4(3) . . . . ?
C3A C2A C7A C6A -55.7(3) . . . . ?
C3A C2A C7A C8A -177.9(3) . . . . ?
C3A C2A C7A C19A 64.9(3) . . . . ?
C3A C4A C5A C6A 50.6(5) . . . . ?
C4A C5A C6A C7A -56.0(4) . . . . ?
C4A C5A C6A C11A 169.4(3) . . . . ?
C5A C6A C7A C2A 57.5(3) . . . . ?
C5A C6A C7A C8A 179.5(2) . . . . ?
C5A C6A C7A C19A -58.2(3) . . . . ?
C5A C6A C11A C10A 159.6(3) . . . . ?
C5A C6A C11A C12A 36.9(4) . . . . ?
C5A C6A C11A C18A -82.6(4) . . . . ?
C6A C7A C8A C9A 7.1(3) . . . . ?
C6A C11A C12A C13A 175.7(3) . . . . ?
C7A C2A C3A C4A 54.3(3) . . . . ?
C7A C2A C3A C20A -125.7(4) . . . . ?
C7A C6A C11A C10A 27.8(4) . . . . ?
C7A C6A C11A C12A -94.9(3) . . . . ?
C7A C6A C11A C18A 145.5(4) . . . . ?
C7A C8A C9A C10A 47.6(3) . . . . ?
C8A C9A C10A C11A -70.2(4) . . . . ?
C8A C9A C10A O10A 166.0(2) . . . . ?
C9A C10A C11A C6A 30.7(4) . . . . ?
C9A C10A C11A C12A 155.9(3) . . . . ?
C9A C10A C11A C18A -84.3(3) . . . . ?
C9A C10A O10A C15A -133.5(3) . . . . ?
C10A C11A C12A C13A 53.2(4) . . . . ?
C11A C6A C7A C2A -169.5(3) . . . . ?
C11A C6A C7A C8A -47.5(4) . . . . ?
C11A C6A C7A C19A 74.9(4) . . . . ?
C11A C10A O10A C15A 100.6(3) . . . . ?
C11A C12A C13A C14A -64.0(5) . . . . ?
C12A C13A C14A C15A 82.7(5) . . . . ?
C12A C13A C14A O14A -154.2(4) . . . . ?
C13A C14A C15A C16A 73.0(4) . . . . ?
C13A C14A C15A C17A -161.6(3) . . . . ?
C13A C14A C15A O10A -41.5(4) . . . . ?
C14A C15A O10A C10A -39.7(4) . . . . ?
C16A C15A O10A C10A -161.1(4) . . . . ?
C17A C15A O10A C10A 82.8(4) . . . . ?
C18A C11A C12A C13A -67.0(4) . . . . ?
C19A C7A C8A C9A -117.6(3) . . . . ?
C20A C3A C4A C5A 129.4(4) . . . . ?
O10 C10 C11 C6 155.8(2) . . . . ?
O10 C10 C11 C12 -80.9(3) . . . . ?
O10 C10 C11 C18 38.9(3) . . . . ?
O14 C14 C15 C16 -47.3(3) . . . . ?
O14 C14 C15 C17 76.6(3) . . . . ?
O14 C14 C15 O10 -161.9(2) . . . . ?
O1" C1" C2" C3" -179.3(4) . . . . ?
O1" C1" C2" C1A -1.4(6) . . . . ?
O1" C1" O5" C5" 178.8(4) . . . . ?
O3" C3" C4" C5" -179.4(4) . . . . ?
O3" C3" C4" C7" -0.8(6) . . . . ?
O5" C1" C2" C3" 1.9(5) . . . . ?
O5" C1" C2" C1A 179.8(3) . . . . ?
O1' C1' C2' C1 0.1(6) . . . . ?
O1' C1' C2' C3' -177.0(4) . . . . ?
O1' C1' O5' C5' 177.4(4) . . . . ?
O3' C3' C4' C5' -178.0(4) . . . . ?
O3' C3' C4' C7' -0.1(5) . . . . ?
O5' C1' C2' C1 178.0(3) . . . . ?
O5' C1' C2' C3' 0.9(5) . . . . ?
O10A C10A C11A C6A 154.6(2) . . . . ?
O10A C10A C11A C12A -80.2(4) . . . . ?
O10A C10A C11A C18A 39.6(3) . . . . ?
O14A C14A C15A C16A -49.5(4) . . . . ?
O14A C14A C15A C17A 75.9(3) . . . . ?
O14A C14A C15A O10A -164.0(2) . . . . ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.696 -0.103 0.250 659.8 108.4 Water
2 -0.132 -0.719 0.750 659.8 108.3 Water
