#------------------------------------------------------------------------------
#$Date: 2017-09-12 06:57:15 +0300 (Tue, 12 Sep 2017) $
#$Revision: 200716 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/65/1546538.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_1546538
loop_
_publ_author_name
'Ivanov, Maxim V.'
'Wadumethrige, Shriya H.'
'Wang, Denan'
'Rathore, Rajendra'
_publ_section_title
;
 Through-Space or Through-Bond? The Important Role of Cofaciality in
 Orbital Reordering and Its Implications for Hole (De)stabilization in
 Polychromophoric Assemblies
;
_journal_issue                   29
_journal_name_full               'The Journal of Physical Chemistry C'
_journal_page_first              15639
_journal_paper_doi               10.1021/acs.jpcc.7b05804
_journal_volume                  121
_journal_year                    2017
_chemical_formula_moiety         'C22 H28 O4'
_chemical_formula_sum            'C22 H28 O4'
_chemical_formula_weight         356.44
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2011-12-22
_audit_creation_method
;
  Olex2 1.1-beta
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 113.233(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   28.9533(18)
_cell_length_b                   12.1295(5)
_cell_length_c                   24.9285(15)
_cell_measurement_reflns_used    13281
_cell_measurement_temperature    100.10(14)
_cell_measurement_theta_max      29.5381
_cell_measurement_theta_min      3.4681
_cell_volume                     8044.7(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.10(14)
_diffrn_detector_area_resol_mean 10.3756
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.902
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   16.00   70.00   1.0000   29.4700
omega____ theta____ kappa____ phi______ frames
    -       11.6800   77.0000 -180.0000 54

#__ type_ start__ end____ width___ exp.time_
  2 omega  -32.00   88.00   1.0000   29.4700
omega____ theta____ kappa____ phi______ frames
    -       11.6800   19.0000 -180.0000 120

#__ type_ start__ end____ width___ exp.time_
  3 omega  -91.00  -65.00   1.0000   29.4700
omega____ theta____ kappa____ phi______ frames
    -      -11.8363 -178.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega  -64.00   38.00   1.0000   29.4700
omega____ theta____ kappa____ phi______ frames
    -       11.6800  -37.0000  150.0000 102

#__ type_ start__ end____ width___ exp.time_
  5 omega  -64.00   43.00   1.0000   29.4700
omega____ theta____ kappa____ phi______ frames
    -       11.6800  -67.0000   63.0000 107

#__ type_ start__ end____ width___ exp.time_
  6 omega  -20.00   14.00   1.0000   29.4700
omega____ theta____ kappa____ phi______ frames
    -      -11.8363  -99.0000  -90.0000 34
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0133815000
_diffrn_orient_matrix_UB_12      0.0103367000
_diffrn_orient_matrix_UB_13      -0.0302139000
_diffrn_orient_matrix_UB_21      -0.0154383000
_diffrn_orient_matrix_UB_22      0.0385231000
_diffrn_orient_matrix_UB_23      0.0066049000
_diffrn_orient_matrix_UB_31      0.0171437000
_diffrn_orient_matrix_UB_32      0.0427642000
_diffrn_orient_matrix_UB_33      0.0013700000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            46783
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         29.60
_diffrn_reflns_theta_min         3.48
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91737
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.177
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             3072
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     485
_refine_ls_number_reflns         10208
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0473
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0778P)²+7.4918P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1480
_refine_ls_wR_factor_ref         0.1621
_reflns_number_gt                7896
_reflns_number_total             10208
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jp7b05804_si_003.cif
_cod_data_source_block           raj22j
_cod_depositor_comments          'Adding full bibliography for 1546538.cif.'
_cod_original_cell_volume        8044.7(8)
_cod_database_code               1546538
_chemical_oxdiff_formula         'C22 H28 O4'
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 'x+1/2, -y+1/2, z-1/2'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.45631(4) 0.66575(8) 0.63497(5) 0.0224(2) Uani 1 1 d .
O2 O 0.45095(4) 0.87748(8) 0.61884(4) 0.0187(2) Uani 1 1 d .
O3 O 0.79510(4) 0.88175(8) 0.62567(4) 0.0197(2) Uani 1 1 d .
O4 O 0.79810(4) 0.66769(8) 0.63260(5) 0.0210(2) Uani 1 1 d .
C1 C 0.57914(5) 0.82768(11) 0.62202(5) 0.0144(3) Uani 1 1 d .
C2 C 0.58226(5) 0.71443(11) 0.63069(6) 0.0153(3) Uani 1 1 d .
C3 C 0.54082(5) 0.65907(11) 0.63517(6) 0.0176(3) Uani 1 1 d .
H3 H 0.5427 0.5816 0.6412 0.021 Uiso 1 1 calc R
C4 C 0.49777(5) 0.71388(12) 0.63101(6) 0.0173(3) Uani 1 1 d .
C5 C 0.49477(5) 0.82879(11) 0.62208(6) 0.0153(3) Uani 1 1 d .
C6 C 0.53480(5) 0.88303(11) 0.61742(6) 0.0154(3) Uani 1 1 d .
H6 H 0.5325 0.9604 0.6109 0.018 Uiso 1 1 calc R
C7 C 0.62820(5) 0.64594(11) 0.63647(6) 0.0163(3) Uani 1 1 d .
C8 C 0.61182(6) 0.55553(12) 0.58869(7) 0.0234(3) Uani 1 1 d .
H8A H 0.5987 0.5903 0.5501 0.035 Uiso 1 1 calc R
H8B H 0.5855 0.5098 0.5929 0.035 Uiso 1 1 calc R
H8C H 0.6408 0.5093 0.5929 0.035 Uiso 1 1 calc R
C9 C 0.64975(5) 0.59179(12) 0.69779(7) 0.0219(3) Uani 1 1 d .
H9A H 0.6790 0.5465 0.7018 0.033 Uiso 1 1 calc R
H9B H 0.6239 0.5453 0.7025 0.033 Uiso 1 1 calc R
H9C H 0.6600 0.6494 0.7278 0.033 Uiso 1 1 calc R
C10 C 0.45790(7) 0.55002(15) 0.64345(11) 0.0466(6) Uani 1 1 d .
H10A H 0.4615 0.5132 0.6103 0.070 Uiso 1 1 calc R
H10B H 0.4267 0.5256 0.6464 0.070 Uiso 1 1 calc R
H10C H 0.4866 0.5312 0.6795 0.070 Uiso 1 1 calc R
C11 C 0.44740(5) 0.99447(12) 0.61149(7) 0.0217(3) Uani 1 1 d .
H11A H 0.4512 1.0143 0.5753 0.033 Uiso 1 1 calc R
H11B H 0.4740 1.0298 0.6447 0.033 Uiso 1 1 calc R
H11C H 0.4145 1.0195 0.6094 0.033 Uiso 1 1 calc R
C12 C 0.66993(5) 0.71518(11) 0.63045(6) 0.0151(3) Uani 1 1 d .
C13 C 0.66720(5) 0.82874(11) 0.62301(6) 0.0145(3) Uani 1 1 d .
C14 C 0.70918(5) 0.88530(11) 0.62117(6) 0.0163(3) Uani 1 1 d .
H14 H 0.7074 0.9631 0.6165 0.020 Uiso 1 1 calc R
C15 C 0.75257(5) 0.83172(11) 0.62587(6) 0.0156(3) Uani 1 1 d .
C16 C 0.75458(5) 0.71572(11) 0.63093(6) 0.0164(3) Uani 1 1 d .
C17 C 0.71415(5) 0.66021(11) 0.63392(6) 0.0164(3) Uani 1 1 d .
H17 H 0.7160 0.5824 0.6385 0.020 Uiso 1 1 calc R
C18 C 0.62057(5) 0.89630(11) 0.61502(6) 0.0152(3) Uani 1 1 d .
C19 C 0.59932(5) 0.94372(12) 0.55220(6) 0.0212(3) Uani 1 1 d .
H19A H 0.5888 0.8830 0.5240 0.032 Uiso 1 1 calc R
H19B H 0.6254 0.9872 0.5461 0.032 Uiso 1 1 calc R
H19C H 0.5703 0.9909 0.5468 0.032 Uiso 1 1 calc R
C20 C 0.63523(6) 0.99138(12) 0.65995(7) 0.0247(3) Uani 1 1 d .
H20A H 0.6055 1.0363 0.6542 0.037 Uiso 1 1 calc R
H20B H 0.6609 1.0374 0.6546 0.037 Uiso 1 1 calc R
H20C H 0.6486 0.9608 0.6995 0.037 Uiso 1 1 calc R
C21 C 0.79752(6) 0.99891(12) 0.63119(8) 0.0284(4) Uani 1 1 d .
H21A H 0.7722 1.0322 0.5961 0.043 Uiso 1 1 calc R
H21B H 0.8310 1.0243 0.6359 0.043 Uiso 1 1 calc R
H21C H 0.7909 1.0207 0.6654 0.043 Uiso 1 1 calc R
C22 C 0.79989(6) 0.54995(12) 0.63453(7) 0.0252(3) Uani 1 1 d .
H22A H 0.7716 0.5201 0.6009 0.038 Uiso 1 1 calc R
H22B H 0.7977 0.5243 0.6707 0.038 Uiso 1 1 calc R
H22C H 0.8316 0.5247 0.6332 0.038 Uiso 1 1 calc R
O1A O 0.52236(4) 0.72481(10) 0.46412(4) 0.0270(3) Uani 1 1 d .
O2A O 0.61249(4) 0.72244(10) 0.46796(4) 0.0257(2) Uani 1 1 d .
C1A C 0.54166(5) 0.73134(11) 0.30650(6) 0.0150(3) Uani 1 1 d .
C2A C 0.49306(5) 0.73167(11) 0.30435(6) 0.0150(3) Uani 1 1 d .
C3A C 0.48589(5) 0.72988(12) 0.35742(6) 0.0178(3) Uani 1 1 d .
H3A H 0.4527 0.7308 0.3561 0.021 Uiso 1 1 calc R
C4A C 0.52590(5) 0.72681(12) 0.41093(6) 0.0192(3) Uani 1 1 d .
C5A C 0.57538(5) 0.72567(12) 0.41316(6) 0.0187(3) Uani 1 1 d .
C6A C 0.58272(5) 0.72832(11) 0.36171(6) 0.0172(3) Uani 1 1 d .
H6A H 0.6160 0.7281 0.3633 0.021 Uiso 1 1 calc R
C7A C 0.44606(5) 0.73766(12) 0.24766(6) 0.0165(3) Uani 1 1 d .
C8A C 0.41023(6) 0.64236(15) 0.24624(6) 0.0281(4) Uani 1 1 d .
H8AA H 0.4266 0.5717 0.2462 0.042 Uiso 1 1 calc R
H8AB H 0.3793 0.6482 0.2109 0.042 Uiso 1 1 calc R
H8AC H 0.4020 0.6467 0.2807 0.042 Uiso 1 1 calc R
C9A C 0.41940(6) 0.84836(15) 0.24609(7) 0.0307(4) Uani 1 1 d .
H9AA H 0.4108 0.8539 0.2803 0.046 Uiso 1 1 calc R
H9AB H 0.3886 0.8524 0.2105 0.046 Uiso 1 1 calc R
H9AC H 0.4418 0.9092 0.2465 0.046 Uiso 1 1 calc R
C10A C 0.47365(6) 0.73500(16) 0.46491(7) 0.0301(4) Uani 1 1 d .
H10G H 0.4583 0.8044 0.4462 0.045 Uiso 1 1 calc R
H10H H 0.4765 0.7346 0.5054 0.045 Uiso 1 1 calc R
H10I H 0.4527 0.6730 0.4437 0.045 Uiso 1 1 calc R
C11A C 0.66304(6) 0.73147(18) 0.47295(7) 0.0370(4) Uani 1 1 d .
H11G H 0.6709 0.6693 0.4529 0.056 Uiso 1 1 calc R
H11H H 0.6858 0.7307 0.5143 0.056 Uiso 1 1 calc R
H11I H 0.6672 0.8007 0.4551 0.056 Uiso 1 1 calc R
O1B O 0.64163(4) 0.81059(9) 0.78343(4) 0.0227(2) Uani 1 1 d .
O2B O 0.73251(4) 0.80993(10) 0.78963(4) 0.0250(2) Uani 1 1 d .
C1B C 0.75821(5) 0.76520(11) 0.94698(6) 0.0148(3) Uani 1 1 d .
C2B C 0.70926(5) 0.76216(11) 0.94335(6) 0.0146(3) Uani 1 1 d .
C3B C 0.66905(5) 0.77577(11) 0.88809(6) 0.0167(3) Uani 1 1 d .
H3B H 0.6354 0.7735 0.8855 0.020 Uiso 1 1 calc R
C4B C 0.67764(5) 0.79228(11) 0.83787(6) 0.0179(3) Uani 1 1 d .
C5B C 0.72758(5) 0.79273(12) 0.84150(6) 0.0182(3) Uani 1 1 d .
C6B C 0.76670(5) 0.77963(11) 0.89514(6) 0.0173(3) Uani 1 1 d .
H6B H 0.8002 0.7803 0.8974 0.021 Uiso 1 1 calc R
C7B C 0.69541(5) 0.74475(11) 0.99595(6) 0.0163(3) Uani 1 1 d .
C8B C 0.66337(6) 0.84340(14) 1.00031(6) 0.0257(3) Uani 1 1 d .
H8BA H 0.6823 0.9119 1.0039 0.039 Uiso 1 1 calc R
H8BB H 0.6553 0.8344 1.0347 0.039 Uiso 1 1 calc R
H8BC H 0.6322 0.8465 0.9651 0.039 Uiso 1 1 calc R
C9B C 0.66393(6) 0.63827(14) 0.98661(6) 0.0264(3) Uani 1 1 d .
H9BA H 0.6541 0.6276 1.0196 0.040 Uiso 1 1 calc R
H9BB H 0.6840 0.5751 0.9838 0.040 Uiso 1 1 calc R
H9BC H 0.6337 0.6445 0.9505 0.040 Uiso 1 1 calc R
C10B C 0.59064(6) 0.80713(17) 0.77705(7) 0.0311(4) Uani 1 1 d .
H10D H 0.5686 0.8241 0.7365 0.047 Uiso 1 1 calc R
H10E H 0.5853 0.8616 0.8031 0.047 Uiso 1 1 calc R
H10F H 0.5828 0.7333 0.7871 0.047 Uiso 1 1 calc R
C11B C 0.78110(6) 0.79439(15) 0.78911(7) 0.0277(3) Uani 1 1 d .
H11D H 0.7795 0.8072 0.7496 0.042 Uiso 1 1 calc R
H11E H 0.7924 0.7188 0.8011 0.042 Uiso 1 1 calc R
H11F H 0.8048 0.8465 0.8162 0.042 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0106 0.0060 '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
C4 O1 C10 116.99(12) . .
C5 O2 C11 116.93(11) . .
C15 O3 C21 116.71(11) . .
C16 O4 C22 116.44(11) . .
C2 C1 C6 118.98(12) . .
C2 C1 C18 123.49(12) . .
C6 C1 C18 117.49(12) . .
C1 C2 C3 118.42(12) . .
C1 C2 C7 123.67(12) . .
C3 C2 C7 117.91(12) . .
C2 C3 H3 118.9 . .
C4 C3 C2 122.24(13) . .
C4 C3 H3 118.9 . .
O1 C4 C3 125.40(13) . .
O1 C4 C5 115.52(12) . .
C3 C4 C5 119.08(12) . .
O2 C5 C4 115.66(11) . .
O2 C5 C6 125.36(12) . .
C6 C5 C4 118.98(12) . .
C1 C6 H6 118.9 . .
C5 C6 C1 122.29(12) . .
C5 C6 H6 118.9 . .
C2 C7 C8 108.77(11) . .
C2 C7 C9 108.68(11) . .
C2 C7 C12 112.67(11) . .
C8 C7 C9 109.88(12) . .
C12 C7 C8 109.14(11) . .
C12 C7 C9 107.67(11) . .
C7 C8 H8A 109.5 . .
C7 C8 H8B 109.5 . .
C7 C8 H8C 109.5 . .
H8A C8 H8B 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C7 C9 H9A 109.5 . .
C7 C9 H9B 109.5 . .
C7 C9 H9C 109.5 . .
H9A C9 H9B 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
O1 C10 H10A 109.5 . .
O1 C10 H10B 109.5 . .
O1 C10 H10C 109.5 . .
H10A C10 H10B 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
O2 C11 H11A 109.5 . .
O2 C11 H11B 109.5 . .
O2 C11 H11C 109.5 . .
H11A C11 H11B 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C13 C12 C7 123.61(12) . .
C13 C12 C17 118.57(12) . .
C17 C12 C7 117.81(12) . .
C12 C13 C14 118.83(12) . .
C12 C13 C18 123.50(12) . .
C14 C13 C18 117.65(12) . .
C13 C14 H14 118.8 . .
C15 C14 C13 122.39(13) . .
C15 C14 H14 118.8 . .
O3 C15 C14 125.42(12) . .
O3 C15 C16 115.78(11) . .
C14 C15 C16 118.80(12) . .
O4 C16 C15 115.48(12) . .
O4 C16 C17 125.44(12) . .
C17 C16 C15 119.08(12) . .
C12 C17 H17 118.9 . .
C16 C17 C12 122.26(13) . .
C16 C17 H17 118.9 . .
C1 C18 C19 107.55(11) . .
C1 C18 C20 109.14(11) . .
C13 C18 C1 112.82(11) . .
C13 C18 C19 108.04(10) . .
C13 C18 C20 109.30(11) . .
C20 C18 C19 109.96(12) . .
C18 C19 H19A 109.5 . .
C18 C19 H19B 109.5 . .
C18 C19 H19C 109.5 . .
H19A C19 H19B 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
C18 C20 H20A 109.5 . .
C18 C20 H20B 109.5 . .
C18 C20 H20C 109.5 . .
H20A C20 H20B 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
O3 C21 H21A 109.5 . .
O3 C21 H21B 109.5 . .
O3 C21 H21C 109.5 . .
H21A C21 H21B 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
O4 C22 H22A 109.5 . .
O4 C22 H22B 109.5 . .
O4 C22 H22C 109.5 . .
H22A C22 H22B 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
C4A O1A C10A 117.69(12) . .
C5A O2A C11A 117.48(11) . .
C2A C1A C6A 119.10(12) . .
C2A C1A C7A 123.50(12) . 2_655
C6A C1A C7A 117.37(12) . 2_655
C1A C2A C3A 118.92(12) . .
C1A C2A C7A 123.75(12) . .
C3A C2A C7A 117.30(12) . .
C2A C3A H3A 119.1 . .
C4A C3A C2A 121.75(13) . .
C4A C3A H3A 119.1 . .
O1A C4A C3A 125.54(13) . .
O1A C4A C5A 115.09(12) . .
C3A C4A C5A 119.37(12) . .
O2A C5A C4A 115.19(12) . .
O2A C5A C6A 125.54(13) . .
C6A C5A C4A 119.27(13) . .
C1A C6A H6A 119.2 . .
C5A C6A C1A 121.58(13) . .
C5A C6A H6A 119.2 . .
C1A C7A C2A 112.45(11) 2_655 .
C1A C7A C8A 109.31(11) 2_655 .
C1A C7A C9A 108.06(12) 2_655 .
C2A C7A C8A 109.31(11) . .
C2A C7A C9A 108.61(11) . .
C9A C7A C8A 109.05(13) . .
C7A C8A H8AA 109.5 . .
C7A C8A H8AB 109.5 . .
C7A C8A H8AC 109.5 . .
H8AA C8A H8AB 109.5 . .
H8AA C8A H8AC 109.5 . .
H8AB C8A H8AC 109.5 . .
C7A C9A H9AA 109.5 . .
C7A C9A H9AB 109.5 . .
C7A C9A H9AC 109.5 . .
H9AA C9A H9AB 109.5 . .
H9AA C9A H9AC 109.5 . .
H9AB C9A H9AC 109.5 . .
O1A C10A H10G 109.5 . .
O1A C10A H10H 109.5 . .
O1A C10A H10I 109.5 . .
H10G C10A H10H 109.5 . .
H10G C10A H10I 109.5 . .
H10H C10A H10I 109.5 . .
O2A C11A H11G 109.5 . .
O2A C11A H11H 109.5 . .
O2A C11A H11I 109.5 . .
H11G C11A H11H 109.5 . .
H11G C11A H11I 109.5 . .
H11H C11A H11I 109.5 . .
C4B O1B C10B 117.32(11) . .
C5B O2B C11B 117.30(11) . .
C2B C1B C6B 118.99(12) . .
C2B C1B C7B 124.03(12) . 7_667
C6B C1B C7B 116.98(12) . 7_667
C1B C2B C3B 119.12(12) . .
C1B C2B C7B 123.74(12) . .
C3B C2B C7B 117.14(12) . .
C2B C3B H3B 119.2 . .
C4B C3B C2B 121.57(13) . .
C4B C3B H3B 119.2 . .
O1B C4B C3B 125.71(13) . .
O1B C4B C5B 115.12(12) . .
C3B C4B C5B 119.17(12) . .
O2B C5B C4B 115.12(12) . .
O2B C5B C6B 125.51(13) . .
C6B C5B C4B 119.34(12) . .
C1B C6B H6B 119.1 . .
C5B C6B C1B 121.78(13) . .
C5B C6B H6B 119.1 . .
C1B C7B C2B 112.20(11) 7_667 .
C1B C7B C8B 109.12(11) 7_667 .
C1B C7B C9B 108.90(11) 7_667 .
C2B C7B C8B 108.74(11) . .
C2B C7B C9B 108.95(11) . .
C8B C7B C9B 108.87(12) . .
C7B C8B H8BA 109.5 . .
C7B C8B H8BB 109.5 . .
C7B C8B H8BC 109.5 . .
H8BA C8B H8BB 109.5 . .
H8BA C8B H8BC 109.5 . .
H8BB C8B H8BC 109.5 . .
C7B C9B H9BA 109.5 . .
C7B C9B H9BB 109.5 . .
C7B C9B H9BC 109.5 . .
H9BA C9B H9BB 109.5 . .
H9BA C9B H9BC 109.5 . .
H9BB C9B H9BC 109.5 . .
O1B C10B H10D 109.5 . .
O1B C10B H10E 109.5 . .
O1B C10B H10F 109.5 . .
H10D C10B H10E 109.5 . .
H10D C10B H10F 109.5 . .
H10E C10B H10F 109.5 . .
O2B C11B H11D 109.5 . .
O2B C11B H11E 109.5 . .
O2B C11B H11F 109.5 . .
H11D C11B H11E 109.5 . .
H11D C11B H11F 109.5 . .
H11E C11B H11F 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C4 1.3730(16) .
O1 C10 1.4176(19) .
O2 C5 1.3726(16) .
O2 C11 1.4293(17) .
O3 C15 1.3744(16) .
O3 C21 1.4267(18) .
O4 C16 1.3739(16) .
O4 C22 1.4291(17) .
C1 C2 1.3879(18) .
C1 C6 1.4125(18) .
C1 C18 1.5256(18) .
C2 C3 1.4173(18) .
C2 C7 1.5261(18) .
C3 H3 0.9500 .
C3 C4 1.3800(19) .
C4 C5 1.4087(19) .
C5 C6 1.3771(18) .
C6 H6 0.9500 .
C7 C8 1.549(2) .
C7 C9 1.5509(19) .
C7 C12 1.5268(18) .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C12 C13 1.3879(18) .
C12 C17 1.4155(18) .
C13 C14 1.4121(18) .
C13 C18 1.5240(18) .
C14 H14 0.9500 .
C14 C15 1.3778(18) .
C15 C16 1.4118(19) .
C16 C17 1.3778(19) .
C17 H17 0.9500 .
C18 C19 1.5498(19) .
C18 C20 1.5458(19) .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 0.9800 .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C20 H20C 0.9800 .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
O1A C4A 1.3700(16) .
O1A C10A 1.4234(19) .
O2A C5A 1.3654(16) .
O2A C11A 1.4233(19) .
C1A C2A 1.3866(19) .
C1A C6A 1.4205(18) .
C1A C7A 1.5278(18) 2_655
C2A C3A 1.4180(18) .
C2A C7A 1.5288(18) .
C3A H3A 0.9500 .
C3A C4A 1.380(2) .
C4A C5A 1.411(2) .
C5A C6A 1.3808(19) .
C6A H6A 0.9500 .
C7A C1A 1.5280(18) 2_655
C7A C8A 1.544(2) .
C7A C9A 1.542(2) .
C8A H8AA 0.9800 .
C8A H8AB 0.9800 .
C8A H8AC 0.9800 .
C9A H9AA 0.9800 .
C9A H9AB 0.9800 .
C9A H9AC 0.9800 .
C10A H10G 0.9800 .
C10A H10H 0.9800 .
C10A H10I 0.9800 .
C11A H11G 0.9800 .
C11A H11H 0.9800 .
C11A H11I 0.9800 .
O1B C4B 1.3644(16) .
O1B C10B 1.4217(18) .
O2B C5B 1.3716(16) .
O2B C11B 1.4246(18) .
C1B C2B 1.3848(19) .
C1B C6B 1.4182(18) .
C1B C7B 1.5279(18) 7_667
C2B C3B 1.4195(18) .
C2B C7B 1.5295(18) .
C3B H3B 0.9500 .
C3B C4B 1.3839(19) .
C4B C5B 1.413(2) .
C5B C6B 1.3789(19) .
C6B H6B 0.9500 .
C7B C1B 1.5278(18) 7_667
C7B C8B 1.5439(19) .
C7B C9B 1.545(2) .
C8B H8BA 0.9800 .
C8B H8BB 0.9800 .
C8B H8BC 0.9800 .
C9B H9BA 0.9800 .
C9B H9BB 0.9800 .
C9B H9BC 0.9800 .
C10B H10D 0.9800 .
C10B H10E 0.9800 .
C10B H10F 0.9800 .
C11B H11D 0.9800 .
C11B H11E 0.9800 .
C11B H11F 0.9800 .
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
O1 C4 C5 O2 0.35(17) . .
O1 C4 C5 C6 -179.75(12) . .
O2 C5 C6 C1 179.08(12) . .
O3 C15 C16 O4 -2.57(17) . .
O3 C15 C16 C17 177.28(12) . .
O4 C16 C17 C12 -178.36(12) . .
C1 C2 C3 C4 0.2(2) . .
C1 C2 C7 C8 -122.30(14) . .
C1 C2 C7 C9 118.09(14) . .
C1 C2 C7 C12 -1.16(18) . .
C2 C1 C6 C5 1.0(2) . .
C2 C1 C18 C13 -4.22(18) . .
C2 C1 C18 C19 114.82(14) . .
C2 C1 C18 C20 -125.92(14) . .
C2 C3 C4 O1 -179.95(12) . .
C2 C3 C4 C5 -0.1(2) . .
C2 C7 C12 C13 2.57(18) . .
C2 C7 C12 C17 -178.82(11) . .
C3 C2 C7 C8 58.49(16) . .
C3 C2 C7 C9 -61.12(15) . .
C3 C2 C7 C12 179.64(12) . .
C3 C4 C5 O2 -179.54(12) . .
C3 C4 C5 C6 0.36(19) . .
C4 C5 C6 C1 -0.8(2) . .
C6 C1 C2 C3 -0.63(19) . .
C6 C1 C2 C7 -179.84(12) . .
C6 C1 C18 C13 177.92(11) . .
C6 C1 C18 C19 -63.05(15) . .
C6 C1 C18 C20 56.21(16) . .
C7 C2 C3 C4 179.47(12) . .
C7 C12 C13 C14 176.51(12) . .
C7 C12 C13 C18 -5.2(2) . .
C7 C12 C17 C16 -177.83(12) . .
C8 C7 C12 C13 123.50(14) . .
C8 C7 C12 C17 -57.89(16) . .
C9 C7 C12 C13 -117.26(14) . .
C9 C7 C12 C17 61.35(15) . .
C10 O1 C4 C3 -0.7(2) . .
C10 O1 C4 C5 179.46(16) . .
C11 O2 C5 C4 178.24(12) . .
C11 O2 C5 C6 -1.65(19) . .
C12 C13 C14 C15 0.7(2) . .
C12 C13 C18 C1 5.63(18) . .
C12 C13 C18 C19 -113.12(14) . .
C12 C13 C18 C20 127.24(14) . .
C13 C12 C17 C16 0.8(2) . .
C13 C14 C15 O3 -178.53(12) . .
C13 C14 C15 C16 2.0(2) . .
C14 C13 C18 C1 -176.04(11) . .
C14 C13 C18 C19 65.20(15) . .
C14 C13 C18 C20 -54.43(15) . .
C14 C15 C16 O4 176.99(12) . .
C14 C15 C16 C17 -3.17(19) . .
C15 C16 C17 C12 1.8(2) . .
C17 C12 C13 C14 -2.09(19) . .
C17 C12 C13 C18 176.22(12) . .
C18 C1 C2 C3 -178.47(12) . .
C18 C1 C2 C7 2.3(2) . .
C18 C1 C6 C5 178.92(12) . .
C18 C13 C14 C15 -177.70(12) . .
C21 O3 C15 C14 11.4(2) . .
C21 O3 C15 C16 -169.07(13) . .
C22 O4 C16 C15 -176.72(12) . .
C22 O4 C16 C17 3.4(2) . .
O1A C4A C5A O2A 0.17(19) . .
O1A C4A C5A C6A -179.54(13) . .
O2A C5A C6A C1A 179.85(13) . .
C1A C2A C3A C4A -0.6(2) . .
C1A C2A C7A C1A 5.87(16) . 2_655
C1A C2A C7A C8A 127.45(14) . .
C1A C2A C7A C9A -113.68(15) . .
C2A C1A C6A C5A 0.0(2) . .
C2A C3A C4A O1A -179.93(13) . .
C2A C3A C4A C5A 0.2(2) . .
C3A C2A C7A C1A -176.18(12) . 2_655
C3A C2A C7A C8A -54.59(16) . .
C3A C2A C7A C9A 64.28(16) . .
C3A C4A C5A O2A -179.91(13) . .
C3A C4A C5A C6A 0.4(2) . .
C4A C5A C6A C1A -0.5(2) . .
C6A C1A C2A C3A 0.51(19) . .
C6A C1A C2A C7A 178.43(12) . .
C7A C1A C2A C3A -177.53(12) 2_655 .
C7A C1A C2A C7A 0.39(18) 2_655 .
C7A C1A C6A C5A 178.18(12) 2_655 .
C7A C2A C3A C4A -178.67(13) . .
C10A O1A C4A C3A -5.0(2) . .
C10A O1A C4A C5A 174.93(13) . .
C11A O2A C5A C4A -174.32(14) . .
C11A O2A C5A C6A 5.4(2) . .
O1B C4B C5B O2B -0.89(18) . .
O1B C4B C5B C6B 177.26(12) . .
O2B C5B C6B C1B 178.22(13) . .
C1B C2B C3B C4B -0.2(2) . .
C1B C2B C7B C1B 1.8(2) . 7_667
C1B C2B C7B C8B 122.60(14) . .
C1B C2B C7B C9B -118.87(14) . .
C2B C1B C6B C5B 1.2(2) . .
C2B C3B C4B O1B -177.17(13) . .
C2B C3B C4B C5B 1.7(2) . .
C3B C2B C7B C1B -178.21(11) . 7_667
C3B C2B C7B C8B -57.41(16) . .
C3B C2B C7B C9B 61.12(15) . .
C3B C4B C5B O2B -179.85(12) . .
C3B C4B C5B C6B -1.7(2) . .
C4B C5B C6B C1B 0.3(2) . .
C6B C1B C2B C3B -1.25(19) . .
C6B C1B C2B C7B 178.74(12) . .
C7B C1B C2B C3B 177.99(12) 7_667 .
C7B C1B C2B C7B -2.0(2) 7_667 .
C7B C1B C6B C5B -178.08(13) 7_667 .
C7B C2B C3B C4B 179.83(12) . .
C10B O1B C4B C3B -3.3(2) . .
C10B O1B C4B C5B 177.85(13) . .
C11B O2B C5B C4B -170.59(13) . .
C11B O2B C5B C6B 11.4(2) . .
