#------------------------------------------------------------------------------
#$Date: 2016-08-07 11:14:38 +0300 (Sun, 07 Aug 2016) $
#$Revision: 185191 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/44/7224408.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_7224408
loop_
_publ_author_name
'Puttreddy, Rakesh'
'Beyeh, Ngong Kodiah'
'Rissanen, Kari'
_publ_section_title
;
 Conformational changes in Cmethyl-resorcinarene pyridine N-oxide
 inclusion complexes in the solid state
;
_journal_issue                   26
_journal_name_full               CrystEngComm
_journal_page_first              4971
_journal_paper_doi               10.1039/C6CE00240D
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         '2(C9 H7 N O), 3(C H4 O), 3(O), C32 H32 O8'
_chemical_formula_sum            'C53 H58 N2 O16'
_chemical_formula_weight         979.01
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2016-01-25
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2016-01-28 deposited with the CCDC.
2016-02-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.5611(4)
_cell_length_b                   20.8203(8)
_cell_length_c                   14.9973(4)
_cell_measurement_reflns_used    4649
_cell_measurement_temperature    123.01(10)
_cell_measurement_theta_max      72.2550
_cell_measurement_theta_min      3.9500
_cell_volume                     5171.2(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details
;
  1 omega -112.00  -13.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.1176  -57.0000  -60.0000 99

  2 omega  -72.00   31.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.1176   77.0000 -120.0000 103

  3 omega   43.00   79.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -30.0000  -90.0000 36

  4 omega   27.00  105.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -94.0000   90.0000 78

  5 omega   77.00  171.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154   30.0000  -60.0000 94

  6 omega   31.00   91.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -30.0000  150.0000 60

  7 omega  109.00  139.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  125.0000  -60.0000 30
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0313120000
_diffrn_orient_matrix_UB_12      -0.0012783000
_diffrn_orient_matrix_UB_13      -0.0966243000
_diffrn_orient_matrix_UB_21      -0.0875098000
_diffrn_orient_matrix_UB_22      0.0042134000
_diffrn_orient_matrix_UB_23      0.0345018000
_diffrn_orient_matrix_UB_31      0.0043288000
_diffrn_orient_matrix_UB_32      0.0738830000
_diffrn_orient_matrix_UB_33      -0.0037629000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13761
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        66.750
_diffrn_reflns_theta_max         66.728
_diffrn_reflns_theta_min         3.632
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.775
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83070
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_F_000             2072
_exptl_crystal_size_max          0.2448
_exptl_crystal_size_mid          0.0959
_exptl_crystal_size_min          0.092
_refine_diff_density_max         0.633
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     373
_refine_ls_number_reflns         4622
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0542
_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)+(0.0771P)²+3.1897P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1490
_refine_ls_wR_factor_ref         0.1590
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3758
_reflns_number_total             4622
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ce00240d2.cif
_cod_data_source_block           IsQNO_1
_cod_depositor_comments
'Adding full bibliography for 7224402--7224408.cif.'
_cod_database_code               7224408
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C20 H20 N1 O9'
_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.
;
_reflns_odcompleteness_completeness 97.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 H1S-O1S
 0.85 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O5W) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Fixed Sof: O1W(0.25) H2S(0.5) O2W(0.5) O3W(0.125) O4W(0.125) O5W(0.25)
 O6W(0.25) H2SA(0.5) H2SB(0.5) H2SC(0.5)
5.a Ternary CH refined with riding coordinates:
 C7(H7), C14(H14)
5.b Aromatic/amide H refined with riding coordinates:
 C1A(H1A), C2(H2), C4A(H4A), C5(H5), C5A(H5A), C6A(H6A), C7A(H7A), C8A(H8A),
 C9(H9), C9A(H9A), C12(H12), C15(H15), C18(H18)
5.c Idealised Me refined as rotating group:
 C1S(H1SA,H1SB,H1SC), C2S(H2SA,H2SB,H2SC), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C)
5.d Idealised tetrahedral OH refined as rotating group:
 O2S(H2S), O3(H3), O11(H11), O13(H13), O17(H17)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'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
O1A O 0.48365(11) 0.37043(11) -0.29364(11) 0.0553(6) Uani 1 1 d . . . . .
O1S O 0.63882(12) 0.35564(17) -0.25816(12) 0.0821(9) Uani 1 1 d D . . . .
H1S H 0.5939(18) 0.369(2) -0.279(3) 0.123 Uiso 1 1 d DR . . . .
O1W O 0.8534(3) 0.2500 -0.0945(4) 0.0598(15) Uani 0.5 2 d S T P A 2
O2S O 0.4507(3) 0.2500 0.3826(3) 0.1008(13) Uani 1 2 d S T P . .
H2S H 0.4112 0.2561 0.4145 0.151 Uiso 0.5 1 calc GR . . . .
O2W O 0.8383(3) 0.2771(3) -0.0121(4) 0.0898(18) Uani 0.5 1 d . . . B -1
O3 O 0.40320(9) 0.36522(8) -0.14229(10) 0.0334(4) Uani 1 1 d . . . . .
H3 H 0.4248 0.3587 -0.1907 0.050 Uiso 1 1 calc GR . . . .
O3W O 0.6327(9) 0.2500 0.4506(15) 0.064(4) Uani 0.25 2 d S T P C 2
O4W O 0.6220(9) 0.2500 0.5082(11) 0.051(3) Uani 0.25 2 d S T P D 3
O5W O 0.5700(7) 0.2711(7) 0.4883(10) 0.088(5) Uani 0.25 1 d . U . E 1
O6W O 0.5989(9) 0.2925(7) 0.4492(9) 0.074(3) Uani 0.25 1 d . . . F -4
O11 O 0.62867(9) 0.50529(8) 0.13578(10) 0.0324(4) Uani 1 1 d . . . . .
H11 H 0.6204 0.5441 0.1339 0.049 Uiso 1 1 calc GR . . . .
O13 O 0.34439(9) 0.50377(8) 0.07381(10) 0.0332(4) Uani 1 1 d . . . . .
H13 H 0.3524 0.5426 0.0718 0.050 Uiso 1 1 calc GR . . . .
O17 O 0.64760(10) 0.36486(8) -0.08499(10) 0.0376(4) Uani 1 1 d . . . . .
H17 H 0.6485 0.3578 -0.1388 0.056 Uiso 1 1 calc GR . . . .
N1A N 0.45121(12) 0.39942(12) -0.36430(13) 0.0406(5) Uani 1 1 d . . . . .
C1 C 0.35876(11) 0.30899(11) -0.01344(14) 0.0284(5) Uani 1 1 d . . . . .
C1A C 0.48544(14) 0.39450(14) -0.44357(15) 0.0401(6) Uani 1 1 d . . . . .
H1A H 0.5338 0.3722 -0.4491 0.048 Uiso 1 1 calc R . . . .
C1S C 0.6959(2) 0.3469(2) -0.3181(2) 0.0866(13) Uani 1 1 d . . . . .
H1SA H 0.6951 0.3031 -0.3379 0.130 Uiso 1 1 calc GR . . . .
H1SB H 0.7475 0.3563 -0.2921 0.130 Uiso 1 1 calc GR . . . .
H1SC H 0.6867 0.3749 -0.3679 0.130 Uiso 1 1 calc GR . . . .
C2 C 0.34491(16) 0.2500 0.02685(19) 0.0288(7) Uani 1 2 d S T P . .
H2 H 0.3250 0.2500 0.0848 0.035 Uiso 1 2 calc RS T P . .
C2A C 0.45044(14) 0.42213(13) -0.51965(15) 0.0375(6) Uani 1 1 d . . . . .
C2S C 0.4265(6) 0.2500 0.2920(5) 0.133(3) Uani 1 2 d S T P . .
H2SA H 0.3797 0.2232 0.2850 0.199 Uiso 0.5 1 calc GR . . G -1
H2SB H 0.4697 0.2337 0.2557 0.199 Uiso 0.5 1 calc GR . . G -1
H2SC H 0.4138 0.2931 0.2739 0.199 Uiso 0.5 1 calc GR . . G -1
C3A C 0.37645(14) 0.45495(13) -0.51084(16) 0.0365(5) Uani 1 1 d . . . . .
C4A C 0.34347(14) 0.46024(14) -0.42420(17) 0.0438(6) Uani 1 1 d . . . . .
H4A H 0.2954 0.4825 -0.4159 0.053 Uiso 1 1 calc R . . . .
C5 C 0.40560(17) 0.2500 -0.14294(19) 0.0294(7) Uani 1 2 d S T P . .
H5 H 0.4267 0.2500 -0.2004 0.035 Uiso 1 2 calc RS T P . .
C5A C 0.38087(15) 0.43334(15) -0.35338(16) 0.0470(7) Uani 1 1 d . . . . .
H5A H 0.3587 0.4379 -0.2967 0.056 Uiso 1 1 calc R . . . .
C6 C 0.38983(12) 0.30773(11) -0.10009(14) 0.0291(5) Uani 1 1 d . . . . .
C6A C 0.48676(18) 0.41623(16) -0.60433(17) 0.0517(7) Uani 1 1 d . . . . .
H6A H 0.5362 0.3955 -0.6102 0.062 Uiso 1 1 calc R . . . .
C7 C 0.34242(12) 0.37241(12) 0.03338(14) 0.0303(5) Uani 1 1 d . . . . .
H7 H 0.3155 0.4004 -0.0100 0.036 Uiso 1 1 calc R . . . .
C7A C 0.44928(19) 0.44099(17) -0.67753(18) 0.0601(8) Uani 1 1 d . . . . .
H7A H 0.4730 0.4366 -0.7334 0.072 Uiso 1 1 calc R . . . .
C8 C 0.41930(12) 0.40692(12) 0.06255(13) 0.0284(5) Uani 1 1 d . . . . .
C8A C 0.37518(18) 0.47316(16) -0.66923(19) 0.0566(8) Uani 1 1 d . . . . .
H8A H 0.3503 0.4898 -0.7198 0.068 Uiso 1 1 calc R . . . .
C9 C 0.49343(13) 0.37589(12) 0.07082(13) 0.0289(5) Uani 1 1 d . . . . .
H9 H 0.4957 0.3320 0.0595 0.035 Uiso 1 1 calc R . . . .
C9A C 0.33909(16) 0.48039(14) -0.58807(18) 0.0465(6) Uani 1 1 d . . . . .
H9A H 0.2901 0.5020 -0.5835 0.056 Uiso 1 1 calc R . . . .
C10 C 0.56446(13) 0.40735(12) 0.09529(13) 0.0290(5) Uani 1 1 d . . . . .
C11 C 0.55918(12) 0.47296(11) 0.11334(13) 0.0288(5) Uani 1 1 d . . . . .
C12 C 0.48589(13) 0.50519(12) 0.10820(13) 0.0294(5) Uani 1 1 d . . . . .
H12 H 0.4830 0.5486 0.1224 0.035 Uiso 1 1 calc R . . . .
C13 C 0.41686(12) 0.47227(12) 0.08177(13) 0.0286(5) Uani 1 1 d . . . . .
C14 C 0.64556(13) 0.37291(12) 0.10242(15) 0.0319(5) Uani 1 1 d . . . . .
H14 H 0.6856 0.4005 0.0733 0.038 Uiso 1 1 calc R . . . .
C15 C 0.64624(17) 0.2500 0.0966(2) 0.0301(7) Uani 1 2 d S T P . .
H15 H 0.6460 0.2500 0.1586 0.036 Uiso 1 2 calc RS T P . .
C16 C 0.64640(11) 0.30919(11) 0.05330(14) 0.0292(5) Uani 1 1 d . . . . .
C17 C 0.64616(12) 0.30765(11) -0.03960(15) 0.0306(5) Uani 1 1 d . . . . .
C18 C 0.64567(18) 0.2500 -0.0859(2) 0.0316(7) Uani 1 2 d S T P . .
H18 H 0.6450 0.2500 -0.1479 0.038 Uiso 1 2 calc RS T P . .
C19 C 0.67055(16) 0.36723(13) 0.20051(16) 0.0432(6) Uani 1 1 d . . . . .
H19A H 0.6304 0.3433 0.2326 0.065 Uiso 1 1 calc GR . . . .
H19B H 0.6754 0.4094 0.2259 0.065 Uiso 1 1 calc GR . . . .
H19C H 0.7215 0.3454 0.2045 0.065 Uiso 1 1 calc GR . . . .
C20 C 0.28524(15) 0.36596(13) 0.11368(16) 0.0391(6) Uani 1 1 d . . . . .
H20A H 0.2364 0.3449 0.0953 0.059 Uiso 1 1 calc GR . . . .
H20B H 0.2726 0.4079 0.1364 0.059 Uiso 1 1 calc GR . . . .
H20C H 0.3110 0.3411 0.1594 0.059 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'
N N 0.0311 0.0180 '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
_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
-7 0 -7 0.0590 -6.9999 0.0003 -6.9999 0.8955 0.3710 -0.0039
1 13 0 0.1377 0.9999 13.0003 0.0003 -0.0480 -0.0327 0.9648
7 -1 7 0.0263 6.9999 -1.0003 6.9999 -0.8943 -0.3753 -0.0699
0 -13 0 0.1000 0.0001 -13.0003 -0.0003 0.0166 -0.0548 -0.9605
8 0 -7 0.0558 8.0001 0.0000 -7.0001 0.4259 -0.9416 0.0610
-8 0 7 0.0362 -8.0001 -0.0000 7.0001 -0.4259 0.9416 -0.0610
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
C1S O1S H1S 115(3) . .
C2S O2S H2S 109.5 . .
C6 O3 H3 109.5 . .
C11 O11 H11 109.5 . .
C13 O13 H13 109.5 . .
C17 O17 H17 109.5 . .
O1A N1A C5A 118.71(19) . .
C1A N1A O1A 120.5(2) . .
C1A N1A C5A 120.8(2) . .
C2 C1 C6 116.7(2) . .
C2 C1 C7 122.56(19) . .
C6 C1 C7 120.7(2) . .
N1A C1A H1A 119.2 . .
N1A C1A C2A 121.5(2) . .
C2A C1A H1A 119.2 . .
O1S C1S H1SA 109.5 . .
O1S C1S H1SB 109.5 . .
O1S C1S H1SC 109.5 . .
H1SA C1S H1SB 109.5 . .
H1SA C1S H1SC 109.5 . .
H1SB C1S H1SC 109.5 . .
C1 C2 C1 124.5(3) . 8_565
C1 C2 H2 117.8 . .
C1 C2 H2 117.8 8_565 .
C1A C2A C3A 118.8(2) . .
C1A C2A C6A 121.4(2) . .
C3A C2A C6A 119.8(2) . .
O2S C2S H2SA 109.5 . .
O2S C2S H2SB 109.5 . .
O2S C2S H2SC 109.5 . .
H2SA C2S H2SB 109.5 . .
H2SA C2S H2SC 109.5 . .
H2SB C2S H2SC 109.5 . .
C2A C3A C4A 117.4(2) . .
C2A C3A C9A 119.0(2) . .
C4A C3A C9A 123.6(2) . .
C3A C4A H4A 119.6 . .
C5A C4A C3A 120.9(2) . .
C5A C4A H4A 119.6 . .
C6 C5 H5 120.0 8_565 .
C6 C5 H5 120.0 . .
C6 C5 C6 120.0(3) . 8_565
N1A C5A H5A 119.7 . .
C4A C5A N1A 120.6(2) . .
C4A C5A H5A 119.7 . .
O3 C6 C1 118.2(2) . .
O3 C6 C5 120.78(19) . .
C5 C6 C1 121.1(2) . .
C2A C6A H6A 120.1 . .
C7A C6A C2A 119.9(3) . .
C7A C6A H6A 120.1 . .
C1 C7 H7 106.9 . .
C1 C7 C8 113.14(17) . .
C1 C7 C20 113.30(19) . .
C8 C7 H7 106.9 . .
C8 C7 C20 109.29(18) . .
C20 C7 H7 106.9 . .
C6A C7A H7A 119.8 . .
C6A C7A C8A 120.5(3) . .
C8A C7A H7A 119.8 . .
C9 C8 C7 122.9(2) . .
C13 C8 C7 119.71(19) . .
C13 C8 C9 117.4(2) . .
C7A C8A H8A 119.5 . .
C9A C8A C7A 121.0(3) . .
C9A C8A H8A 119.5 . .
C8 C9 H9 118.4 . .
C8 C9 C10 123.3(2) . .
C10 C9 H9 118.4 . .
C3A C9A H9A 120.1 . .
C8A C9A C3A 119.8(3) . .
C8A C9A H9A 120.1 . .
C9 C10 C14 122.7(2) . .
C11 C10 C9 117.2(2) . .
C11 C10 C14 120.1(2) . .
O11 C11 C10 118.31(19) . .
O11 C11 C12 120.6(2) . .
C12 C11 C10 121.1(2) . .
C11 C12 H12 120.1 . .
C11 C12 C13 119.7(2) . .
C13 C12 H12 120.1 . .
O13 C13 C8 118.33(19) . .
O13 C13 C12 120.5(2) . .
C12 C13 C8 121.1(2) . .
C10 C14 H14 106.8 . .
C10 C14 C19 109.95(18) . .
C16 C14 C10 112.63(17) . .
C16 C14 H14 106.8 . .
C16 C14 C19 113.3(2) . .
C19 C14 H14 106.8 . .
C16 C15 H15 117.8 . .
C16 C15 H15 117.8 8_565 .
C16 C15 C16 124.4(3) 8_565 .
C15 C16 C14 123.2(2) . .
C15 C16 C17 116.5(2) . .
C17 C16 C14 120.3(2) . .
O17 C17 C16 118.4(2) . .
O17 C17 C18 120.2(2) . .
C18 C17 C16 121.4(2) . .
C17 C18 C17 119.9(3) 8_565 .
C17 C18 H18 120.0 8_565 .
C17 C18 H18 120.0 . .
C14 C19 H19A 109.5 . .
C14 C19 H19B 109.5 . .
C14 C19 H19C 109.5 . .
H19A C19 H19B 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
C7 C20 H20A 109.5 . .
C7 C20 H20B 109.5 . .
C7 C20 H20C 109.5 . .
H20A C20 H20B 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1A N1A 1.333(3) .
O1S H1S 0.852(19) .
O1S C1S 1.317(4) .
O2S H2S 0.8200 .
O2S C2S 1.417(7) .
O3 H3 0.8200 .
O3 C6 1.372(3) .
O5W O5W 0.88(3) 8_565
O11 H11 0.8200 .
O11 C11 1.375(3) .
O13 H13 0.8200 .
O13 C13 1.373(3) .
O17 H17 0.8200 .
O17 C17 1.372(3) .
N1A C1A 1.321(3) .
N1A C5A 1.372(3) .
C1 C2 1.388(3) .
C1 C6 1.398(3) .
C1 C7 1.520(3) .
C1A H1A 0.9300 .
C1A C2A 1.403(3) .
C1S H1SA 0.9600 .
C1S H1SB 0.9600 .
C1S H1SC 0.9600 .
C2 C1 1.388(3) 8_565
C2 H2 0.9300 .
C2A C3A 1.409(3) .
C2A C6A 1.410(3) .
C2S H2SA 0.9600 .
C2S H2SB 0.9600 .
C2S H2SC 0.9600 .
C3A C4A 1.414(3) .
C3A C9A 1.416(3) .
C4A H4A 0.9300 .
C4A C5A 1.351(4) .
C5 H5 0.9300 .
C5 C6 1.388(3) 8_565
C5 C6 1.388(3) .
C5A H5A 0.9300 .
C6A H6A 0.9300 .
C6A C7A 1.363(4) .
C7 H7 0.9800 .
C7 C8 1.526(3) .
C7 C20 1.538(3) .
C7A H7A 0.9300 .
C7A C8A 1.404(4) .
C8 C9 1.393(3) .
C8 C13 1.391(3) .
C8A H8A 0.9300 .
C8A C9A 1.364(4) .
C9 H9 0.9300 .
C9 C10 1.395(3) .
C9A H9A 0.9300 .
C10 C11 1.395(3) .
C10 C14 1.526(3) .
C11 C12 1.389(3) .
C12 H12 0.9300 .
C12 C13 1.391(3) .
C14 H14 0.9800 .
C14 C16 1.518(3) .
C14 C19 1.533(3) .
C15 H15 0.9300 .
C15 C16 1.393(3) 8_565
C15 C16 1.393(3) .
C16 C17 1.394(3) .
C17 C18 1.387(3) .
C18 C17 1.387(3) 8_565
C18 H18 0.9300 .
C19 H19A 0.9600 .
C19 H19B 0.9600 .
C19 H19C 0.9600 .
C20 H20A 0.9600 .
C20 H20B 0.9600 .
C20 H20C 0.9600 .
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_4
O1A N1A C1A C2A 177.1(2) . .
O1A N1A C5A C4A -176.1(3) . .
O11 C11 C12 C13 177.31(17) . .
O17 C17 C18 C17 178.46(16) . 8_565
N1A C1A C2A C3A -1.0(4) . .
N1A C1A C2A C6A -179.4(3) . .
C1 C7 C8 C9 -18.6(3) . .
C1 C7 C8 C13 161.13(18) . .
C1A N1A C5A C4A 2.7(4) . .
C1A C2A C3A C4A 2.5(4) . .
C1A C2A C3A C9A -177.2(3) . .
C1A C2A C6A C7A 176.9(3) . .
C2 C1 C6 O3 179.1(2) . .
C2 C1 C6 C5 0.1(3) . .
C2 C1 C7 C8 106.4(2) . .
C2 C1 C7 C20 -18.8(3) . .
C2A C3A C4A C5A -1.6(4) . .
C2A C3A C9A C8A -0.4(4) . .
C2A C6A C7A C8A 0.9(5) . .
C3A C2A C6A C7A -1.5(5) . .
C3A C4A C5A N1A -1.0(4) . .
C4A C3A C9A C8A 179.9(3) . .
C5A N1A C1A C2A -1.7(4) . .
C6 C1 C2 C1 -0.9(4) . 8_565
C6 C1 C7 C8 -72.9(2) . .
C6 C1 C7 C20 162.01(19) . .
C6 C5 C6 O3 -178.39(15) 8_565 .
C6 C5 C6 C1 0.6(4) 8_565 .
C6A C2A C3A C4A -179.0(3) . .
C6A C2A C3A C9A 1.2(4) . .
C6A C7A C8A C9A 0.0(5) . .
C7 C1 C2 C1 179.83(17) . 8_565
C7 C1 C6 O3 -1.6(3) . .
C7 C1 C6 C5 179.4(2) . .
C7 C8 C9 C10 178.35(18) . .
C7 C8 C13 O13 0.1(3) . .
C7 C8 C13 C12 -179.75(18) . .
C7A C8A C9A C3A -0.3(5) . .
C8 C9 C10 C11 1.0(3) . .
C8 C9 C10 C14 -178.85(18) . .
C9 C8 C13 O13 179.84(17) . .
C9 C8 C13 C12 0.0(3) . .
C9 C10 C11 O11 -178.66(17) . .
C9 C10 C11 C12 0.8(3) . .
C9 C10 C14 C16 18.3(3) . .
C9 C10 C14 C19 -109.2(2) . .
C9A C3A C4A C5A 178.1(3) . .
C10 C11 C12 C13 -2.2(3) . .
C10 C14 C16 C15 -107.8(2) . .
C10 C14 C16 C17 71.2(2) . .
C11 C10 C14 C16 -161.58(19) . .
C11 C10 C14 C19 71.0(3) . .
C11 C12 C13 O13 -178.09(17) . .
C11 C12 C13 C8 1.7(3) . .
C13 C8 C9 C10 -1.4(3) . .
C14 C10 C11 O11 1.2(3) . .
C14 C10 C11 C12 -179.32(18) . .
C14 C16 C17 O17 1.9(3) . .
C14 C16 C17 C18 -179.0(2) . .
C15 C16 C17 O17 -179.0(2) . .
C15 C16 C17 C18 0.1(3) . .
C16 C15 C16 C14 179.51(17) 8_565 .
C16 C15 C16 C17 0.5(4) 8_565 .
C16 C17 C18 C17 -0.6(4) . 8_565
C19 C14 C16 C15 17.8(3) . .
C19 C14 C16 C17 -163.2(2) . .
C20 C7 C8 C9 108.6(2) . .
C20 C7 C8 C13 -71.6(2) . .
