#------------------------------------------------------------------------------
#$Date: 2017-12-11 11:21:15 +0200 (Mon, 11 Dec 2017) $
#$Revision: 204152 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/84/1548416.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_1548416
loop_
_publ_author_name
'Chaosheng Luo'
'Zhen Wang'
'Yong Huang'
_publ_section_title
;
 Asymmetric intramolecular alpha-cyclopropanation of aldehydes using a
 donor/acceptor carbene mimetic
;
_journal_name_full               'Nature Communications'
_journal_page_first              10041
_journal_paper_doi               10.1038/ncomms10041
_journal_volume                  6
_journal_year                    2015
_chemical_formula_sum            'C19 H30 O5'
_chemical_formula_weight         338.43
_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
_cell_angle_alpha                90
_cell_angle_beta                 123.469(9)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   32.5104(5)
_cell_length_b                   7.54200(10)
_cell_length_c                   18.7992(13)
_cell_measurement_reflns_used    22788
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      68.30
_cell_measurement_theta_min      6.50
_cell_volume                     3845.1(5)
_computing_cell_refinement       'CrystalClear-SM Auto 2.0 r4'
_computing_data_collection       'CrystalClear-SM 2.0 r4 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Auto 2.0 r4'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      113(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Rigaku Saturn944+ CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0529
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            24237
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.363
_diffrn_reflns_theta_min         7.085
_exptl_absorpt_coefficient_mu    0.676
_exptl_absorpt_correction_T_max  0.873
_exptl_absorpt_correction_T_min  0.739
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.169
_exptl_crystal_description       block
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.798
_refine_diff_density_min         -0.769
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_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     311
_refine_ls_number_reflns         3441
_refine_ls_number_restraints     23
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.1209
_refine_ls_R_factor_gt           0.1048
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0777P)²+21.5726P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2350
_refine_ls_wR_factor_ref         0.2509
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2873
_reflns_number_total             3441
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ncomms10041-s2.cif
_cod_data_source_block           1
_cod_original_cell_volume        3845.1(4)
_cod_database_code               1548416
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.877
_shelx_estimated_absorpt_t_max   0.877
_shelxl_version_number           2013-2
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'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_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 0.18213(13) 0.0751(4) 1.04264(18) 0.0605(10) Uani 1 1 d D . . . .
O8 O 0.12260(12) 0.1119(4) 0.8544(2) 0.0614(9) Uani 1 1 d D . . . .
C4 C 0.09929(14) 0.5738(5) 0.9693(2) 0.0366(8) Uani 1 1 d D . . . .
H4 H 0.1227 0.6750 0.9976 0.044 Uiso 1 1 calc R U . A 1
C6 C 0.11584(13) 0.2624(4) 0.9571(2) 0.0355(8) Uani 1 1 d D . . . .
C7 C 0.23158(12) 0.0068(5) 1.1086(2) 0.0340(8) Uani 1 1 d . . . . .
C9 C 0.16869(17) 0.2370(6) 1.0208(3) 0.0311(11) Uani 0.722(3) 1 d D . P B 1
O3 O 0.19757(12) 0.3584(4) 1.0519(2) 0.0394(9) Uani 0.722(3) 1 d D . P B 1
C11 C 0.09798(17) 0.1089(6) 0.8839(3) 0.0345(12) Uani 0.722(3) 1 d D . P B 1
O5 O 0.06322(13) 0.0146(5) 0.8644(2) 0.0437(9) Uani 0.722(3) 1 d D . P B 1
C22 C 0.10535(19) 0.4465(6) 0.9104(3) 0.0359(12) Uani 0.722(3) 1 d D . P B 1
H22A H 0.1333 0.4831 0.9065 0.043 Uiso 0.722(3) 1 calc R U P B 1
H22B H 0.0749 0.4421 0.8524 0.043 Uiso 0.722(3) 1 calc R U P B 1
C17 C 0.08677(17) 0.4571(7) 1.0215(3) 0.0301(11) Uani 0.722(3) 1 d D . P B 1
C18 C 0.04833(18) 0.5851(8) 0.9535(4) 0.0374(12) Uani 0.722(3) 1 d D . P B 1
C20 C 0.1137(3) 0.4962(13) 1.1110(5) 0.0411(17) Uani 0.722(3) 1 d D . P B 1
H20 H 0.1174 0.6173 1.1274 0.049 Uiso 0.722(3) 1 calc R U P B 1
O15 O 0.13238(16) 0.3844(6) 1.1678(3) 0.0568(12) Uani 0.722(3) 1 d D . P B 1
C24 C 0.0027(3) 0.5163(12) 0.8741(5) 0.0455(19) Uani 0.722(3) 1 d D . P B 1
H24A H -0.0088 0.6031 0.8280 0.068 Uiso 0.722(3) 1 calc R U P B 1
H24B H -0.0231 0.4970 0.8851 0.068 Uiso 0.722(3) 1 calc R U P B 1
H24C H 0.0102 0.4041 0.8573 0.068 Uiso 0.722(3) 1 calc R U P B 1
C9A C 0.1161(5) 0.2407(15) 0.8844(7) 0.035(3) Uani 0.278(3) 1 d D U P B 2
O3A O 0.1186(4) 0.3586(11) 0.8442(6) 0.039(2) Uani 0.278(3) 1 d D . P B 2
C11A C 0.1524(5) 0.1218(14) 1.0338(7) 0.026(3) Uani 0.278(3) 1 d D U P B 2
O5A O 0.1396(3) 0.0352(11) 1.0728(5) 0.035(2) Uani 0.278(3) 1 d D . P B 2
C22A C 0.1449(4) 0.4473(13) 1.0074(7) 0.028(3) Uani 0.278(3) 1 d D . P B 2
H22C H 0.1622 0.4354 1.0700 0.034 Uiso 0.278(3) 1 calc R U P B 2
H22D H 0.1684 0.4861 0.9927 0.034 Uiso 0.278(3) 1 calc R U P B 2
C17A C 0.0575(5) 0.4664(15) 0.9423(9) 0.034(3) Uani 0.278(3) 1 d D . P B 2
C18A C 0.0761(5) 0.5837(16) 1.0226(8) 0.031(3) Uani 0.278(3) 1 d D . P B 2
C20A C 0.0146(7) 0.539(3) 0.8598(11) 0.040(5) Uani 0.278(3) 1 d D . P B 2
H20A H 0.0110 0.6640 0.8520 0.048 Uiso 0.278(3) 1 calc R U P B 2
O15A O -0.0160(4) 0.4422(15) 0.8024(6) 0.053(3) Uani 0.278(3) 1 d D . P B 2
C24A C 0.0940(7) 0.484(3) 1.1050(12) 0.041(5) Uani 0.278(3) 1 d D . P B 2
H24D H 0.0659 0.4567 1.1090 0.061 Uiso 0.278(3) 1 calc R U P B 2
H24E H 0.1177 0.5581 1.1536 0.061 Uiso 0.278(3) 1 calc R U P B 2
H24F H 0.1101 0.3739 1.1056 0.061 Uiso 0.278(3) 1 calc R U P B 2
C10 C 0.11363(16) -0.0054(5) 0.7857(2) 0.0430(9) Uani 1 1 d . . . . .
C12 C 0.26742(17) 0.0466(6) 1.0835(3) 0.0516(11) Uani 1 1 d . . . . .
H12A H 0.2734 0.1747 1.0871 0.062 Uiso 1 1 calc R U . . .
H12B H 0.2536 0.0064 1.0250 0.062 Uiso 1 1 calc R U . . .
H12C H 0.2986 -0.0152 1.1223 0.062 Uiso 1 1 calc R U . . .
C13 C 0.22297(14) -0.1914(5) 1.1064(3) 0.0461(10) Uani 1 1 d . . . . .
H13A H 0.2122 -0.2380 1.0500 0.055 Uiso 1 1 calc R U . . .
H13B H 0.1975 -0.2142 1.1179 0.055 Uiso 1 1 calc R U . . .
H13C H 0.2537 -0.2499 1.1499 0.055 Uiso 1 1 calc R U . . .
C14 C 0.15491(15) 0.0438(6) 0.7749(3) 0.0509(11) Uani 1 1 d . . . . .
H14A H 0.1534 -0.0318 0.7311 0.061 Uiso 1 1 calc R U . . .
H14B H 0.1867 0.0268 0.8291 0.061 Uiso 1 1 calc R U . . .
H14C H 0.1514 0.1683 0.7575 0.061 Uiso 1 1 calc R U . . .
C16 C 0.0418(2) 0.7594(6) 0.9921(4) 0.0660(14) Uani 1 1 d . . . . .
H16A H 0.0733 0.7912 1.0442 0.079 Uiso 1 1 calc R U . B 1
H16B H 0.0170 0.7397 1.0056 0.079 Uiso 1 1 calc R U . B 1
H16C H 0.0309 0.8559 0.9506 0.079 Uiso 1 1 calc R U . B 1
C19 C 0.0815(2) 0.2651(6) 0.9861(4) 0.0715(17) Uani 1 1 d D . . . .
H19A H 0.0911 0.1756 1.0312 0.086 Uiso 1 1 calc R U . B 1
H19B H 0.0472 0.2418 0.9380 0.086 Uiso 1 1 calc R U . B 1
C21 C 0.06412(15) 0.0347(8) 0.7059(3) 0.0622(13) Uani 1 1 d . . . . .
H21A H 0.0574 -0.0502 0.6613 0.075 Uiso 1 1 calc R U . . .
H21B H 0.0643 0.1553 0.6867 0.075 Uiso 1 1 calc R U . . .
H21C H 0.0385 0.0251 0.7180 0.075 Uiso 1 1 calc R U . . .
C23 C 0.1181(3) -0.1961(6) 0.8134(4) 0.0755(17) Uani 1 1 d . . . . .
H23A H 0.1112 -0.2744 0.7664 0.091 Uiso 1 1 calc R U . . .
H23B H 0.0944 -0.2195 0.8290 0.091 Uiso 1 1 calc R U . . .
H23C H 0.1516 -0.2181 0.8627 0.091 Uiso 1 1 calc R U . . .
C25 C 0.24768(14) 0.0856(6) 1.1945(2) 0.0468(10) Uani 1 1 d . . . . .
H25A H 0.2514 0.2142 1.1931 0.070 Uiso 1 1 calc R U . . .
H25B H 0.2793 0.0335 1.2389 0.070 Uiso 1 1 calc R U . . .
H25C H 0.2228 0.0600 1.2071 0.070 Uiso 1 1 calc R U . . .
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
C11A O1 C7 143.5(7) . .
C9 O1 C7 128.3(4) . .
C11A O1 O5A 39.6(6) . .
C7 O1 O5A 110.5(3) . .
C9A O8 C10 155.3(6) . .
C11 O8 C10 122.7(4) . .
C18 C4 C17 60.6(3) . .
C17A C4 C18A 63.1(7) . .
C18 C4 C22 116.6(4) . .
C17 C4 C22 106.5(3) . .
C17A C4 C22A 107.1(6) . .
C18A C4 C22A 114.1(7) . .
C18 C4 H4 119.4 . .
C17 C4 H4 119.4 . .
C22 C4 H4 119.4 . .
C9A C6 C19 141.1(6) . .
C9 C6 C19 118.7(4) . .
C9 C6 C22 111.4(3) . .
C19 C6 C22 102.5(3) . .
C9 C6 C11 107.8(3) . .
C19 C6 C11 109.1(3) . .
C22 C6 C11 106.7(3) . .
C9A C6 C22A 110.6(7) . .
C19 C6 C22A 94.9(5) . .
C9A C6 C11A 113.2(6) . .
C19 C6 C11A 90.8(5) . .
C22A C6 C11A 97.6(6) . .
O1 C7 C12 109.8(3) . .
O1 C7 C13 102.8(3) . .
C12 C7 C13 110.5(3) . .
O1 C7 C25 109.4(3) . .
C12 C7 C25 112.4(3) . .
C13 C7 C25 111.4(3) . .
O3 C9 O1 121.9(4) . .
O3 C9 C6 123.0(4) . .
O1 C9 C6 115.0(4) . .
O8 C11 O5 128.5(5) . .
O8 C11 C6 110.9(3) . .
O5 C11 C6 120.5(4) . .
C4 C22 C6 102.8(3) . .
C4 C22 H22A 111.2 . .
C6 C22 H22A 111.2 . .
C4 C22 H22B 111.2 . .
C6 C22 H22B 111.2 . .
H22A C22 H22B 109.1 . .
C20 C17 C4 115.3(5) . .
C20 C17 C18 122.5(6) . .
C4 C17 C18 59.2(3) . .
C20 C17 C19 122.9(6) . .
C4 C17 C19 105.3(4) . .
C18 C17 C19 112.2(4) . .
C24 C18 C4 123.4(5) . .
C24 C18 C17 120.9(6) . .
C4 C18 C17 60.2(3) . .
C24 C18 C16 115.9(5) . .
C4 C18 C16 111.6(4) . .
C17 C18 C16 113.3(5) . .
O15 C20 C17 124.6(8) . .
O15 C20 H20 117.7 . .
C17 C20 H20 117.7 . .
C18 C24 H24A 109.5 . .
C18 C24 H24B 109.5 . .
H24A C24 H24B 109.5 . .
C18 C24 H24C 109.5 . .
H24A C24 H24C 109.5 . .
H24B C24 H24C 109.5 . .
O3A C9A O8 102.3(8) . .
O3A C9A C6 125.2(10) . .
O8 C9A C6 131.3(10) . .
O1 C11A O5A 110.4(10) . .
O1 C11A C6 124.3(9) . .
O5A C11A C6 123.3(10) . .
C11A O5A O1 30.0(6) . .
C4 C22A C6 98.9(6) . .
C4 C22A H22C 112.0 . .
C6 C22A H22C 112.0 . .
C4 C22A H22D 112.0 . .
C6 C22A H22D 112.0 . .
H22C C22A H22D 109.7 . .
C4 C17A C20A 108.9(10) . .
C4 C17A C18A 62.8(7) . .
C20A C17A C18A 115.8(12) . .
C4 C17A C19 104.2(8) . .
C20A C17A C19 137.9(12) . .
C18A C17A C19 102.1(9) . .
C24A C18A C4 125.8(11) . .
C24A C18A C17A 115.8(13) . .
C4 C18A C17A 54.1(6) . .
C24A C18A C16 124.5(11) . .
C4 C18A C16 107.2(7) . .
C17A C18A C16 107.4(9) . .
O15A C20A C17A 122.0(18) . .
O15A C20A H20A 119.0 . .
C17A C20A H20A 119.0 . .
C18A C24A H24D 109.5 . .
C18A C24A H24E 109.5 . .
H24D C24A H24E 109.5 . .
C18A C24A H24F 109.5 . .
H24D C24A H24F 109.5 . .
H24E C24A H24F 109.5 . .
O8 C10 C21 110.0(4) . .
O8 C10 C23 109.8(3) . .
C21 C10 C23 112.4(4) . .
O8 C10 C14 102.2(3) . .
C21 C10 C14 110.9(3) . .
C23 C10 C14 110.9(4) . .
C7 C12 H12A 109.5 . .
C7 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C7 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C7 C13 H13A 109.5 . .
C7 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C7 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C10 C14 H14A 109.5 . .
C10 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C10 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C18 C16 H16A 109.5 . .
C18 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
C18 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
C6 C19 C17 103.9(3) . .
C6 C19 C17A 94.1(5) . .
C6 C19 H19A 111.0 . .
C17 C19 H19A 111.0 . .
C6 C19 H19B 111.0 . .
C17 C19 H19B 111.0 . .
H19A C19 H19B 109.0 . .
C10 C21 H21A 109.5 . .
C10 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
C10 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
C10 C23 H23A 109.5 . .
C10 C23 H23B 109.5 . .
H23A C23 H23B 109.5 . .
C10 C23 H23C 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
C7 C25 H25A 109.5 . .
C7 C25 H25B 109.5 . .
H25A C25 H25B 109.5 . .
C7 C25 H25C 109.5 . .
H25A C25 H25C 109.5 . .
H25B C25 H25C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C11A 0.952(12) .
O1 C9 1.286(5) .
O1 C7 1.479(5) .
O1 O5A 1.786(9) .
O8 C9A 1.199(10) .
O8 C11 1.199(6) .
O8 C10 1.456(5) .
C4 C17A 1.413(13) .
C4 C18 1.515(6) .
C4 C17 1.532(5) .
C4 C18A 1.552(11) .
C4 C22 1.558(6) .
C4 C22A 1.565(10) .
C4 H4 1.0000 .
C6 C9A 1.381(10) .
C6 C9 1.467(6) .
C6 C19 1.489(5) .
C6 C22 1.576(5) .
C6 C11 1.640(6) .
C6 C22A 1.657(10) .
C6 C11A 1.651(11) .
C7 C12 1.508(5) .
C7 C13 1.517(5) .
C7 C25 1.518(5) .
C9 O3 1.207(6) .
C11 O5 1.209(5) .
C22 H22A 0.9900 .
C22 H22B 0.9900 .
C17 C20 1.435(10) .
C17 C18 1.538(7) .
C17 C19 1.563(6) .
C18 C24 1.502(10) .
C18 C16 1.572(7) .
C20 O15 1.226(9) .
C20 H20 0.9500 .
C24 H24A 0.9800 .
C24 H24B 0.9800 .
C24 H24C 0.9800 .
C9A O3A 1.199(13) .
C11A O5A 1.216(12) .
C22A H22C 0.9900 .
C22A H22D 0.9900 .
C17A C20A 1.51(2) .
C17A C18A 1.556(18) .
C17A C19 1.697(12) .
C18A C24A 1.518(17) .
C18A C16 1.620(13) .
C20A O15A 1.226(17) .
C20A H20A 0.9500 .
C24A H24D 0.9800 .
C24A H24E 0.9800 .
C24A H24F 0.9800 .
C10 C21 1.506(6) .
C10 C23 1.509(6) .
C10 C14 1.510(6) .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
C19 H19A 0.9900 .
C19 H19B 0.9900 .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
C23 H23A 0.9800 .
C23 H23B 0.9800 .
C23 H23C 0.9800 .
C25 H25A 0.9800 .
C25 H25B 0.9800 .
C25 H25C 0.9800 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C12 H12A O3 0.98 2.58 3.090(6) 112.7 .
C13 H13B O5A 0.98 2.46 2.963(9) 111.7 .
C21 H21C O5 0.98 2.41 2.999(6) 118.5 .
C23 H23A O15 0.98 2.45 3.336(6) 149.8 6
C23 H23B O5 0.98 2.31 2.918(6) 119.4 .
C25 H25A O3 0.98 2.48 3.043(6) 116.0 .
C25 H25B O15 0.98 2.65 3.616(6) 167.8 4_547
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
C11A O1 C7 C12 -149.6(12) . . . .
C9 O1 C7 C12 -64.8(5) . . . .
O5A O1 C7 C12 -178.2(4) . . . .
C11A O1 C7 C13 92.7(12) . . . .
C9 O1 C7 C13 177.5(4) . . . .
O5A O1 C7 C13 64.2(4) . . . .
C11A O1 C7 C25 -25.7(13) . . . .
C9 O1 C7 C25 59.0(5) . . . .
O5A O1 C7 C25 -54.3(5) . . . .
C11A O1 C9 O3 138.3(9) . . . .
C7 O1 C9 O3 3.0(7) . . . .
O5A O1 C9 O3 123.4(5) . . . .
C11A O1 C9 C6 -40.4(8) . . . .
C7 O1 C9 C6 -175.7(3) . . . .
O5A O1 C9 C6 -55.3(5) . . . .
C9A C6 C9 O3 94.2(7) . . . .
C19 C6 C9 O3 -97.1(5) . . . .
C22 C6 C9 O3 21.6(6) . . . .
C11 C6 C9 O3 138.3(4) . . . .
C22A C6 C9 O3 -14.6(6) . . . .
C11A C6 C9 O3 -150.2(9) . . . .
C9A C6 C9 O1 -87.1(6) . . . .
C19 C6 C9 O1 81.6(5) . . . .
C22 C6 C9 O1 -159.7(4) . . . .
C11 C6 C9 O1 -43.0(5) . . . .
C22A C6 C9 O1 164.1(6) . . . .
C11A C6 C9 O1 28.5(7) . . . .
C9A O8 C11 O5 150.8(9) . . . .
C10 O8 C11 O5 0.2(8) . . . .
C9A O8 C11 C6 -27.0(7) . . . .
C10 O8 C11 C6 -177.5(3) . . . .
C9A C6 C11 O8 28.7(7) . . . .
C9 C6 C11 O8 -55.0(4) . . . .
C19 C6 C11 O8 174.8(4) . . . .
C22 C6 C11 O8 64.8(4) . . . .
C22A C6 C11 O8 17.8(12) . . . .
C11A C6 C11 O8 -93.8(6) . . . .
C9A C6 C11 O5 -149.3(9) . . . .
C9 C6 C11 O5 127.0(5) . . . .
C19 C6 C11 O5 -3.2(6) . . . .
C22 C6 C11 O5 -113.2(5) . . . .
C22A C6 C11 O5 -160.2(10) . . . .
C11A C6 C11 O5 88.3(6) . . . .
C17A C4 C22 C6 -65.2(6) . . . .
C18 C4 C22 C6 -85.9(4) . . . .
C17 C4 C22 C6 -20.9(4) . . . .
C18A C4 C22 C6 -40.8(10) . . . .
C22A C4 C22 C6 50.0(5) . . . .
C9A C6 C22 C4 -180.0(7) . . . .
C9 C6 C22 C4 -88.1(4) . . . .
C19 C6 C22 C4 39.9(4) . . . .
C11 C6 C22 C4 154.5(3) . . . .
C22A C6 C22 C4 -47.9(5) . . . .
C11A C6 C22 C4 -76.5(11) . . . .
C17A C4 C17 C20 -161.5(8) . . . .
C18 C4 C17 C20 -114.2(6) . . . .
C18A C4 C17 C20 -65.7(10) . . . .
C22 C4 C17 C20 134.1(5) . . . .
C22A C4 C17 C20 79.1(6) . . . .
C17A C4 C17 C18 -47.3(6) . . . .
C18A C4 C17 C18 48.5(9) . . . .
C22 C4 C17 C18 -111.7(4) . . . .
C22A C4 C17 C18 -166.7(5) . . . .
C17A C4 C17 C19 59.8(6) . . . .
C18 C4 C17 C19 107.1(4) . . . .
C18A C4 C17 C19 155.6(10) . . . .
C22 C4 C17 C19 -4.6(5) . . . .
C22A C4 C17 C19 -59.7(5) . . . .
C17A C4 C18 C24 -47.7(10) . . . .
C17 C4 C18 C24 -109.4(7) . . . .
C18A C4 C18 C24 -153.7(10) . . . .
C22 C4 C18 C24 -14.7(7) . . . .
C22A C4 C18 C24 -88.0(10) . . . .
C17A C4 C18 C17 61.7(9) . . . .
C18A C4 C18 C17 -44.3(7) . . . .
C22 C4 C18 C17 94.7(4) . . . .
C22A C4 C18 C17 21.4(9) . . . .
C17A C4 C18 C16 166.9(10) . . . .
C17 C4 C18 C16 105.2(5) . . . .
C18A C4 C18 C16 60.9(8) . . . .
C22 C4 C18 C16 -160.0(4) . . . .
C22A C4 C18 C16 126.6(8) . . . .
C20 C17 C18 C24 -144.6(6) . . . .
C4 C17 C18 C24 113.3(6) . . . .
C19 C17 C18 C24 18.2(6) . . . .
C20 C17 C18 C4 102.1(5) . . . .
C19 C17 C18 C4 -95.1(4) . . . .
C20 C17 C18 C16 -0.4(7) . . . .
C4 C17 C18 C16 -102.5(4) . . . .
C19 C17 C18 C16 162.5(4) . . . .
C4 C17 C20 O15 -135.7(6) . . . .
C18 C17 C20 O15 156.2(6) . . . .
C19 C17 C20 O15 -4.9(9) . . . .
C11 O8 C9A O3A -150.3(12) . . . .
C10 O8 C9A O3A -52(2) . . . .
C11 O8 C9A C6 42.2(11) . . . .
C10 O8 C9A C6 140.5(11) . . . .
C9 C6 C9A O3A -94.9(12) . . . .
C19 C6 C9A O3A 101.0(14) . . . .
C22 C6 C9A O3A 14.9(11) . . . .
C11 C6 C9A O3A 158.3(17) . . . .
C22A C6 C9A O3A -26.8(14) . . . .
C11A C6 C9A O3A -135.2(12) . . . .
C9 C6 C9A O8 70.2(14) . . . .
C19 C6 C9A O8 -93.9(14) . . . .
C22 C6 C9A O8 180.0(15) . . . .
C11 C6 C9A O8 -36.7(10) . . . .
C22A C6 C9A O8 138.3(12) . . . .
C11A C6 C9A O8 29.9(16) . . . .
C9 O1 C11A O5A -156.3(13) . . . .
C7 O1 C11A O5A -44.7(17) . . . .
C9 O1 C11A C6 39.2(7) . . . .
C7 O1 C11A C6 150.9(6) . . . .
O5A O1 C11A C6 -164.5(18) . . . .
C9A C6 C11A O1 31.0(14) . . . .
C9 C6 C11A O1 -45.0(9) . . . .
C19 C6 C11A O1 179.6(11) . . . .
C22 C6 C11A O1 -61.4(17) . . . .
C11 C6 C11A O1 70.5(11) . . . .
C22A C6 C11A O1 -85.4(12) . . . .
C9A C6 C11A O5A -131.5(11) . . . .
C9 C6 C11A O5A 152.5(14) . . . .
C19 C6 C11A O5A 17.1(11) . . . .
C22 C6 C11A O5A 136.1(10) . . . .
C11 C6 C11A O5A -92.0(11) . . . .
C22A C6 C11A O5A 112.2(11) . . . .
C6 C11A O5A O1 164.6(18) . . . .
C9 O1 O5A C11A 19.8(11) . . . .
C7 O1 O5A C11A 153.5(12) . . . .
C17A C4 C22A C6 23.6(9) . . . .
C18 C4 C22A C6 49.3(11) . . . .
C17 C4 C22A C6 68.0(5) . . . .
C18A C4 C22A C6 91.2(8) . . . .
C22 C4 C22A C6 -46.0(4) . . . .
C9A C6 C22A C4 95.3(7) . . . .
C9 C6 C22A C4 -174.1(7) . . . .
C19 C6 C22A C4 -54.9(6) . . . .
C22 C6 C22A C4 46.8(4) . . . .
C11 C6 C22A C4 103.3(10) . . . .
C11A C6 C22A C4 -146.3(7) . . . .
C18 C4 C17A C20A 63.8(11) . . . .
C17 C4 C17A C20A 154.1(13) . . . .
C18A C4 C17A C20A 110.0(12) . . . .
C22 C4 C17A C20A -86.7(11) . . . .
C22A C4 C17A C20A -141.2(11) . . . .
C18 C4 C17A C18A -46.2(8) . . . .
C17 C4 C17A C18A 44.1(6) . . . .
C22 C4 C17A C18A 163.3(7) . . . .
C22A C4 C17A C18A 108.8(8) . . . .
C18 C4 C17A C19 -142.6(13) . . . .
C17 C4 C17A C19 -52.3(6) . . . .
C18A C4 C17A C19 -96.4(9) . . . .
C22 C4 C17A C19 66.9(6) . . . .
C22A C4 C17A C19 12.4(9) . . . .
C17A C4 C18A C24A 98.0(16) . . . .
C18 C4 C18A C24A 141.7(19) . . . .
C17 C4 C18A C24A 39.1(13) . . . .
C22 C4 C18A C24A 70.7(19) . . . .
C22A C4 C18A C24A 0.2(17) . . . .
C18 C4 C18A C17A 43.7(7) . . . .
C17 C4 C18A C17A -58.9(8) . . . .
C22 C4 C18A C17A -27.3(11) . . . .
C22A C4 C18A C17A -97.7(8) . . . .
C17A C4 C18A C16 -99.3(10) . . . .
C18 C4 C18A C16 -55.6(7) . . . .
C17 C4 C18A C16 -158.2(13) . . . .
C22 C4 C18A C16 -126.6(7) . . . .
C22A C4 C18A C16 162.9(7) . . . .
C4 C17A C18A C24A -116.9(12) . . . .
C20A C17A C18A C24A 144.2(14) . . . .
C19 C17A C18A C24A -16.9(14) . . . .
C20A C17A C18A C4 -98.9(12) . . . .
C19 C17A C18A C4 100.0(7) . . . .
C4 C17A C18A C16 99.0(7) . . . .
C20A C17A C18A C16 0.0(14) . . . .
C19 C17A C18A C16 -161.1(6) . . . .
C4 C17A C20A O15A 142.7(15) . . . .
C18A C17A C20A O15A -149.1(15) . . . .
C19 C17A C20A O15A 3(3) . . . .
C9A O8 C10 C21 -17.6(18) . . . .
C11 O8 C10 C21 64.5(5) . . . .
C9A O8 C10 C23 -141.9(16) . . . .
C11 O8 C10 C23 -59.8(6) . . . .
C9A O8 C10 C14 100.3(17) . . . .
C11 O8 C10 C14 -177.6(4) . . . .
C24 C18 C16 C18A 151.8(9) . . . .
C4 C18 C16 C18A -60.1(7) . . . .
C17 C18 C16 C18A 5.6(7) . . . .
C24A C18A C16 C18 -141.6(18) . . . .
C4 C18A C16 C18 55.4(6) . . . .
C17A C18A C16 C18 -1.4(5) . . . .
C9A C6 C19 C17 -117.9(9) . . . .
C9 C6 C19 C17 80.1(5) . . . .
C22 C6 C19 C17 -43.2(5) . . . .
C11 C6 C19 C17 -155.9(4) . . . .
C22A C6 C19 C17 14.2(6) . . . .
C11A C6 C19 C17 111.9(5) . . . .
C9A C6 C19 C17A -73.5(10) . . . .
C9 C6 C19 C17A 124.5(6) . . . .
C22 C6 C19 C17A 1.3(6) . . . .
C11 C6 C19 C17A -111.5(6) . . . .
C22A C6 C19 C17A 58.6(7) . . . .
C11A C6 C19 C17A 156.3(7) . . . .
C20 C17 C19 C6 -104.5(6) . . . .
C4 C17 C19 C6 30.2(5) . . . .
C18 C17 C19 C6 92.7(5) . . . .
C20 C17 C19 C17A 173.9(8) . . . .
C4 C17 C19 C17A -51.4(6) . . . .
C18 C17 C19 C17A 11.1(6) . . . .
C4 C17A C19 C6 -48.3(8) . . . .
C20A C17A C19 C6 92.9(15) . . . .
C18A C17A C19 C6 -113.0(8) . . . .
C4 C17A C19 C17 57.5(7) . . . .
C20A C17A C19 C17 -161.4(18) . . . .
C18A C17A C19 C17 -7.3(5) . . . .
