#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/01/2230138.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2230138
loop_
_publ_author_name
'Kato, Yuichi'
'Nagasawa, Atsushi'
'Sasagawa, Kosuke'
'Okamoto, Akiko'
'Yonezawa, Noriyuki'
_publ_section_title
;
 (5-Benzoyl-3,6-dimethoxynaphthalen-2-yl)(phenyl)methanone
;
_journal_coeditor_code           RZ2585
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1250
_journal_paper_doi               10.1107/S160053681101508X
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C26 H20 O4'
_chemical_formula_moiety         'C26 H20 O4'
_chemical_formula_sum            'C26 H20 O4'
_chemical_formula_weight         396.42
_chemical_melting_point_gt       429.4
_chemical_melting_point_lt       431.8
_chemical_name_systematic
;
(5-Benzoyl-3,6-dimethoxynaphthalen-2-yl)(phenyl)methanone
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                96.2220(10)
_cell_angle_beta                 99.6880(10)
_cell_angle_gamma                102.7270(10)
_cell_formula_units_Z            4
_cell_length_a                   8.42828(15)
_cell_length_b                   12.5953(2)
_cell_length_c                   20.0578(4)
_cell_measurement_reflns_used    27981
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      68.22
_cell_measurement_theta_min      3.64
_cell_volume                     2023.77(6)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku, 2010)'
_computing_molecular_graphics    'ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'IL MILIONE (Burla et al., 2007)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_sigmaI/netI    0.0250
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            32431
_diffrn_reflns_theta_full        68.22
_diffrn_reflns_theta_max         68.22
_diffrn_reflns_theta_min         3.64
_exptl_absorpt_coefficient_mu    0.705
_exptl_absorpt_correction_T_max  0.9328
_exptl_absorpt_correction_T_min  0.6771
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
(NUMABS; Higashi, 1999)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.208
_refine_ls_extinction_coef       0.0067(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     546
_refine_ls_number_reflns         7263
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0393
_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)+(0.0636P)²+0.2292P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1150
_reflns_number_gt                5957
_reflns_number_total             7263
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz2585.cif
_cod_data_source_block           I
_cod_original_cell_volume        2023.76(6)
_cod_database_code               2230138
_cod_database_fobs_code          2230138
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.75620(12) 1.12665(8) 0.24000(5) 0.0463(3) Uani d . 1 1 . .
O O2 0.14926(12) 0.65855(8) 0.03150(5) 0.0455(3) Uani d . 1 1 . .
O O3 0.55140(12) 0.85168(9) 0.25446(5) 0.0494(3) Uani d . 1 1 . .
O O4 0.03981(14) 0.81814(11) -0.11186(6) 0.0629(3) Uani d . 1 1 . .
O O5 0.39029(14) 0.33247(9) 0.27240(6) 0.0541(3) Uani d . 1 1 . .
O O6 0.39614(13) 0.86845(9) 0.44885(5) 0.0511(3) Uani d . 1 1 . .
O O7 0.38552(13) 0.58829(10) 0.22876(6) 0.0564(3) Uani d . 1 1 . .
O O8 0.36093(17) 0.79742(14) 0.60807(6) 0.0856(5) Uani d . 1 1 . .
C C1 0.63721(16) 1.08595(11) 0.18260(7) 0.0382(3) Uani d . 1 1 . .
C C2 0.58200(17) 1.15268(11) 0.13624(8) 0.0423(3) Uani d . 1 1 . .
H H2 0.6302 1.2297 0.1434 0.051 Uiso calc R 1 1 . .
C C3 0.45899(17) 1.10584(11) 0.08112(7) 0.0410(3) Uani d . 1 1 . .
H H3 0.4233 1.1509 0.0496 0.049 Uiso calc R 1 1 . .
C C4 0.38305(16) 0.99224(11) 0.06952(7) 0.0364(3) Uani d . 1 1 . .
C C5 0.25120(16) 0.94529(11) 0.01373(7) 0.0383(3) Uani d . 1 1 . .
H H5 0.2160 0.9910 -0.0175 0.046 Uiso calc R 1 1 . .
C C6 0.17237(16) 0.83613(11) 0.00312(7) 0.0377(3) Uani d . 1 1 . .
C C7 0.23026(16) 0.76713(11) 0.04875(7) 0.0367(3) Uani d . 1 1 . .
C C8 0.35891(15) 0.80916(11) 0.10324(7) 0.0357(3) Uani d . 1 1 . .
H H8 0.3957 0.7617 0.1328 0.043 Uiso calc R 1 1 . .
C C9 0.43812(15) 0.92381(11) 0.11589(7) 0.0340(3) Uani d . 1 1 . .
C C10 0.57067(15) 0.97328(11) 0.17229(7) 0.0350(3) Uani d . 1 1 . .
C C11 0.63953(16) 0.90486(11) 0.22145(7) 0.0354(3) Uani d . 1 1 . .
C C12 0.81623(15) 0.89971(10) 0.22638(7) 0.0342(3) Uani d . 1 1 . .
C C13 0.91210(17) 0.94624(12) 0.18213(7) 0.0419(3) Uani d . 1 1 . .
H H13 0.8666 0.9849 0.1486 0.050 Uiso calc R 1 1 . .
C C14 1.07400(18) 0.93639(14) 0.18677(8) 0.0505(4) Uani d . 1 1 . .
H H14 1.1390 0.9682 0.1563 0.061 Uiso calc R 1 1 . .
C C15 1.14103(18) 0.88071(14) 0.23533(8) 0.0519(4) Uani d . 1 1 . .
H H15 1.2518 0.8736 0.2382 0.062 Uiso calc R 1 1 . .
C C16 1.04694(18) 0.83527(14) 0.27983(9) 0.0526(4) Uani d . 1 1 . .
H H16 1.0936 0.7976 0.3137 0.063 Uiso calc R 1 1 . .
C C17 0.88488(17) 0.84427(12) 0.27543(8) 0.0437(3) Uani d . 1 1 . .
H H17 0.8205 0.8124 0.3061 0.052 Uiso calc R 1 1 . .
C C18 0.02760(17) 0.79442(12) -0.05542(7) 0.0414(3) Uani d . 1 1 . .
C C19 -0.13454(16) 0.73366(10) -0.04292(7) 0.0376(3) Uani d . 1 1 . .
C C20 -0.17214(18) 0.73856(12) 0.02197(8) 0.0448(3) Uani d . 1 1 . .
H H20 -0.0896 0.7760 0.0606 0.054 Uiso calc R 1 1 . .
C C21 -0.3297(2) 0.68907(14) 0.03039(10) 0.0581(4) Uani d . 1 1 . .
H H21 -0.3558 0.6935 0.0747 0.070 Uiso calc R 1 1 . .
C C22 -0.4493(2) 0.63315(14) -0.02576(11) 0.0633(5) Uani d . 1 1 . .
H H22 -0.5573 0.5988 -0.0199 0.076 Uiso calc R 1 1 . .
C C23 -0.4121(2) 0.62724(12) -0.08983(11) 0.0590(5) Uani d . 1 1 . .
H H23 -0.4945 0.5884 -0.1282 0.071 Uiso calc R 1 1 . .
C C24 -0.25615(18) 0.67716(11) -0.09900(8) 0.0464(4) Uani d . 1 1 . .
H H24 -0.2316 0.6730 -0.1436 0.056 Uiso calc R 1 1 . .
C C25 0.8244(2) 1.24308(12) 0.25537(9) 0.0547(4) Uani d . 1 1 . .
H H25A 0.9051 1.2604 0.2987 0.066 Uiso calc R 1 1 . .
H H25B 0.7351 1.2804 0.2592 0.066 Uiso calc R 1 1 . .
H H25C 0.8798 1.2682 0.2187 0.066 Uiso calc R 1 1 . .
C C26 0.1872(2) 0.58516(12) 0.07768(9) 0.0529(4) Uani d . 1 1 . .
H H26A 0.3027 0.5808 0.0801 0.064 Uiso calc R 1 1 . .
H H26B 0.1132 0.5118 0.0614 0.064 Uiso calc R 1 1 . .
H H26C 0.1718 0.6124 0.1232 0.064 Uiso calc R 1 1 . .
C C27 0.36484(18) 0.39304(13) 0.32852(8) 0.0460(3) Uani d . 1 1 . .
C C28 0.3038(2) 0.34626(14) 0.38244(9) 0.0543(4) Uani d . 1 1 . .
H H28 0.2800 0.2688 0.3816 0.065 Uiso calc R 1 1 . .
C C29 0.2792(2) 0.41289(14) 0.43577(9) 0.0550(4) Uani d . 1 1 . .
H H29 0.2397 0.3808 0.4724 0.066 Uiso calc R 1 1 . .
C C30 0.31049(17) 0.52816(13) 0.43836(8) 0.0456(3) Uani d . 1 1 . .
C C31 0.28001(18) 0.59751(14) 0.49256(8) 0.0497(4) Uani d U 1 1 . .
H H31 0.2393 0.5657 0.5291 0.060 Uiso calc R 1 1 . .
C C32 0.30714(17) 0.70823(13) 0.49412(7) 0.0456(3) Uani d U 1 1 . .
C C33 0.37117(17) 0.75666(13) 0.44010(7) 0.0434(3) Uani d . 1 1 . .
C C34 0.40361(16) 0.69303(12) 0.38659(7) 0.0411(3) Uani d . 1 1 . .
H H34 0.4465 0.7267 0.3511 0.049 Uiso calc R 1 1 . .
C C35 0.37334(16) 0.57641(12) 0.38400(7) 0.0401(3) Uani d . 1 1 . .
C C36 0.40236(16) 0.50614(12) 0.32941(7) 0.0412(3) Uani d . 1 1 . .
C C37 0.47086(17) 0.55206(11) 0.27136(7) 0.0400(3) Uani d . 1 1 . .
C C38 0.64577(17) 0.55189(11) 0.26701(7) 0.0406(3) Uani d . 1 1 . .
C C39 0.75209(19) 0.52482(14) 0.31930(9) 0.0535(4) Uani d . 1 1 . .
H H39 0.7149 0.5068 0.3598 0.064 Uiso calc R 1 1 . .
C C40 0.9143(2) 0.52407(15) 0.31253(11) 0.0673(5) Uani d U 1 1 . .
H H40 0.9881 0.5068 0.3487 0.081 Uiso calc R 1 1 . .
C C41 0.9670(2) 0.54832(16) 0.25342(12) 0.0731(6) Uani d U 1 1 . .
H H41 1.0764 0.5462 0.2484 0.088 Uiso calc R 1 1 . .
C C42 0.8617(2) 0.57558(17) 0.20157(11) 0.0698(5) Uani d . 1 1 . .
H H42 0.8984 0.5921 0.1608 0.084 Uiso calc R 1 1 . .
C C43 0.70313(19) 0.57898(13) 0.20861(8) 0.0517(4) Uani d . 1 1 . .
H H43 0.6322 0.6001 0.1731 0.062 Uiso calc R 1 1 . .
C C44 0.26992(19) 0.77897(14) 0.55201(8) 0.0515(4) Uani d . 1 1 . .
C C45 0.11741(17) 0.82003(12) 0.54022(7) 0.0426(3) Uani d . 1 1 . .
C C46 0.00223(18) 0.78735(12) 0.47869(8) 0.0456(3) Uani d . 1 1 . .
H H46 0.0234 0.7406 0.4425 0.055 Uiso calc R 1 1 . .
C C47 -0.1424(2) 0.82298(14) 0.47039(9) 0.0545(4) Uani d . 1 1 . .
H H47 -0.2213 0.8000 0.4286 0.065 Uiso calc R 1 1 . .
C C48 -0.1730(2) 0.89198(14) 0.52258(9) 0.0570(4) Uani d . 1 1 . .
H H48 -0.2727 0.9164 0.5166 0.068 Uiso calc R 1 1 . .
C C49 -0.0592(2) 0.92543(13) 0.58321(9) 0.0542(4) Uani d . 1 1 . .
H H49 -0.0804 0.9732 0.6189 0.065 Uiso calc R 1 1 . .
C C50 0.08573(19) 0.88984(12) 0.59252(8) 0.0479(4) Uani d . 1 1 . .
H H50 0.1637 0.9129 0.6345 0.057 Uiso calc R 1 1 . .
C C51 0.3316(2) 0.21502(13) 0.26385(9) 0.0578(4) Uani d . 1 1 . .
H H51A 0.3462 0.1827 0.2193 0.069 Uiso calc R 1 1 . .
H H51B 0.2136 0.1959 0.2661 0.069 Uiso calc R 1 1 . .
H H51C 0.3947 0.1862 0.3003 0.069 Uiso calc R 1 1 . .
C C52 0.46383(19) 0.92637(13) 0.39871(8) 0.0499(4) Uani d . 1 1 . .
H H52A 0.4778 1.0056 0.4119 0.060 Uiso calc R 1 1 . .
H H52B 0.3883 0.9019 0.3542 0.060 Uiso calc R 1 1 . .
H H52C 0.5718 0.9114 0.3956 0.060 Uiso calc R 1 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 O1 C25 . . 118.57(11) ?
C7 O2 C26 . . 117.91(11) ?
C27 O5 C51 . . 118.04(12) ?
C33 O6 C52 . . 118.14(11) ?
O1 C1 C10 . . 115.76(12) ?
O1 C1 C2 . . 123.07(12) ?
C10 C1 C2 . . 121.16(13) ?
C3 C2 C1 . . 119.35(13) ?
C3 C2 H2 . . 120.3 ?
C1 C2 H2 . . 120.3 ?
C2 C3 C4 . . 121.78(13) ?
C2 C3 H3 . . 119.1 ?
C4 C3 H3 . . 119.1 ?
C5 C4 C3 . . 121.30(12) ?
C5 C4 C9 . . 119.27(12) ?
C3 C4 C9 . . 119.41(12) ?
C6 C5 C4 . . 122.06(12) ?
C6 C5 H5 . . 119.0 ?
C4 C5 H5 . . 119.0 ?
C5 C6 C7 . . 118.58(12) ?
C5 C6 C18 . . 118.45(12) ?
C7 C6 C18 . . 122.97(12) ?
O2 C7 C8 . . 124.78(12) ?
O2 C7 C6 . . 113.96(11) ?
C8 C7 C6 . . 121.23(12) ?
C7 C8 C9 . . 120.42(12) ?
C7 C8 H8 . . 119.8 ?
C9 C8 H8 . . 119.8 ?
C4 C9 C10 . . 118.28(12) ?
C4 C9 C8 . . 118.39(12) ?
C10 C9 C8 . . 123.33(12) ?
C1 C10 C9 . . 119.93(12) ?
C1 C10 C11 . . 119.13(12) ?
C9 C10 C11 . . 120.94(12) ?
O3 C11 C12 . . 120.80(12) ?
O3 C11 C10 . . 120.73(12) ?
C12 C11 C10 . . 118.42(11) ?
C17 C12 C13 . . 119.27(12) ?
C17 C12 C11 . . 118.88(12) ?
C13 C12 C11 . . 121.83(12) ?
C14 C13 C12 . . 120.13(14) ?
C14 C13 H13 . . 119.9 ?
C12 C13 H13 . . 119.9 ?
C15 C14 C13 . . 120.28(15) ?
C15 C14 H14 . . 119.9 ?
C13 C14 H14 . . 119.9 ?
C14 C15 C16 . . 119.83(14) ?
C14 C15 H15 . . 120.1 ?
C16 C15 H15 . . 120.1 ?
C15 C16 C17 . . 120.33(14) ?
C15 C16 H16 . . 119.8 ?
C17 C16 H16 . . 119.8 ?
C16 C17 C12 . . 120.16(14) ?
C16 C17 H17 . . 119.9 ?
C12 C17 H17 . . 119.9 ?
O4 C18 C19 . . 120.28(13) ?
O4 C18 C6 . . 119.60(13) ?
C19 C18 C6 . . 119.86(12) ?
C20 C19 C24 . . 119.30(14) ?
C20 C19 C18 . . 122.06(12) ?
C24 C19 C18 . . 118.46(13) ?
C21 C20 C19 . . 120.10(15) ?
C21 C20 H20 . . 120.0 ?
C19 C20 H20 . . 120.0 ?
C22 C21 C20 . . 119.99(17) ?
C22 C21 H21 . . 120.0 ?
C20 C21 H21 . . 120.0 ?
C23 C22 C21 . . 120.04(16) ?
C23 C22 H22 . . 120.0 ?
C21 C22 H22 . . 120.0 ?
C22 C23 C24 . . 120.54(16) ?
C22 C23 H23 . . 119.7 ?
C24 C23 H23 . . 119.7 ?
C23 C24 C19 . . 120.02(16) ?
C23 C24 H24 . . 120.0 ?
C19 C24 H24 . . 120.0 ?
O1 C25 H25A . . 109.5 ?
O1 C25 H25B . . 109.5 ?
H25A C25 H25B . . 109.5 ?
O1 C25 H25C . . 109.5 ?
H25A C25 H25C . . 109.5 ?
H25B C25 H25C . . 109.5 ?
O2 C26 H26A . . 109.5 ?
O2 C26 H26B . . 109.5 ?
H26A C26 H26B . . 109.5 ?
O2 C26 H26C . . 109.5 ?
H26A C26 H26C . . 109.5 ?
H26B C26 H26C . . 109.5 ?
O5 C27 C36 . . 115.63(13) ?
O5 C27 C28 . . 123.42(14) ?
C36 C27 C28 . . 120.96(14) ?
C29 C28 C27 . . 119.40(15) ?
C29 C28 H28 . . 120.3 ?
C27 C28 H28 . . 120.3 ?
C28 C29 C30 . . 122.05(15) ?
C28 C29 H29 . . 119.0 ?
C30 C29 H29 . . 119.0 ?
C29 C30 C31 . . 122.31(14) ?
C29 C30 C35 . . 118.90(14) ?
C31 C30 C35 . . 118.78(14) ?
C32 C31 C30 . . 122.09(14) ?
C32 C31 H31 . . 119.0 ?
C30 C31 H31 . . 119.0 ?
C31 C32 C33 . . 119.19(14) ?
C31 C32 C44 . . 120.49(14) ?
C33 C32 C44 . . 120.32(14) ?
O6 C33 C34 . . 125.97(13) ?
O6 C33 C32 . . 113.10(13) ?
C34 C33 C32 . . 120.93(14) ?
C33 C34 C35 . . 120.31(13) ?
C33 C34 H34 . . 119.8 ?
C35 C34 H34 . . 119.8 ?
C36 C35 C30 . . 118.47(13) ?
C36 C35 C34 . . 122.84(13) ?
C30 C35 C34 . . 118.69(13) ?
C27 C36 C35 . . 120.16(13) ?
C27 C36 C37 . . 118.84(13) ?
C35 C36 C37 . . 120.99(13) ?
O7 C37 C38 . . 120.84(13) ?
O7 C37 C36 . . 120.69(13) ?
C38 C37 C36 . . 118.47(12) ?
C39 C38 C43 . . 119.07(14) ?
C39 C38 C37 . . 121.92(14) ?
C43 C38 C37 . . 119.01(13) ?
C38 C39 C40 . . 119.94(17) ?
C38 C39 H39 . . 120.0 ?
C40 C39 H39 . . 120.0 ?
C41 C40 C39 . . 119.94(18) ?
C41 C40 H40 . . 120.0 ?
C39 C40 H40 . . 120.0 ?
C42 C41 C40 . . 120.14(16) ?
C42 C41 H41 . . 119.9 ?
C40 C41 H41 . . 119.9 ?
C41 C42 C43 . . 120.15(18) ?
C41 C42 H42 . . 119.9 ?
C43 C42 H42 . . 119.9 ?
C42 C43 C38 . . 120.70(17) ?
C42 C43 H43 . . 119.6 ?
C38 C43 H43 . . 119.6 ?
O8 C44 C45 . . 121.31(15) ?
O8 C44 C32 . . 119.79(15) ?
C45 C44 C32 . . 118.83(13) ?
C50 C45 C46 . . 119.36(14) ?
C50 C45 C44 . . 119.28(14) ?
C46 C45 C44 . . 121.32(14) ?
C47 C46 C45 . . 119.98(15) ?
C47 C46 H46 . . 120.0 ?
C45 C46 H46 . . 120.0 ?
C46 C47 C48 . . 120.27(15) ?
C46 C47 H47 . . 119.9 ?
C48 C47 H47 . . 119.9 ?
C49 C48 C47 . . 120.08(15) ?
C49 C48 H48 . . 120.0 ?
C47 C48 H48 . . 120.0 ?
C48 C49 C50 . . 120.36(15) ?
C48 C49 H49 . . 119.8 ?
C50 C49 H49 . . 119.8 ?
C49 C50 C45 . . 119.94(15) ?
C49 C50 H50 . . 120.0 ?
C45 C50 H50 . . 120.0 ?
O5 C51 H51A . . 109.5 ?
O5 C51 H51B . . 109.5 ?
H51A C51 H51B . . 109.5 ?
O5 C51 H51C . . 109.5 ?
H51A C51 H51C . . 109.5 ?
H51B C51 H51C . . 109.5 ?
O6 C52 H52A . . 109.5 ?
O6 C52 H52B . . 109.5 ?
H52A C52 H52B . . 109.5 ?
O6 C52 H52C . . 109.5 ?
H52A C52 H52C . . 109.5 ?
H52B C52 H52C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.3606(16) ?
O1 C25 . 1.4306(17) ?
O2 C7 . 1.3647(16) ?
O2 C26 . 1.4251(17) ?
O3 C11 . 1.2172(16) ?
O4 C18 . 1.2168(17) ?
O5 C27 . 1.3646(18) ?
O5 C51 . 1.4340(18) ?
O6 C33 . 1.3641(18) ?
O6 C52 . 1.4276(18) ?
O7 C37 . 1.2157(17) ?
O8 C44 . 1.2170(18) ?
C1 C10 . 1.3848(19) ?
C1 C2 . 1.408(2) ?
C2 C3 . 1.360(2) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.4090(19) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.4090(19) ?
C4 C9 . 1.4242(18) ?
C5 C6 . 1.3652(19) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.4282(19) ?
C6 C18 . 1.4984(18) ?
C7 C8 . 1.3687(18) ?
C8 C9 . 1.4261(18) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.4252(18) ?
C10 C11 . 1.5045(19) ?
C11 C12 . 1.4921(18) ?
C12 C17 . 1.3875(19) ?
C12 C13 . 1.3892(19) ?
C13 C14 . 1.386(2) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.377(2) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.379(2) ?
C15 H15 . 0.9500 ?
C16 C17 . 1.384(2) ?
C16 H16 . 0.9500 ?
C17 H17 . 0.9500 ?
C18 C19 . 1.4872(19) ?
C19 C20 . 1.389(2) ?
C19 C24 . 1.3927(19) ?
C20 C21 . 1.384(2) ?
C20 H20 . 0.9500 ?
C21 C22 . 1.384(3) ?
C21 H21 . 0.9500 ?
C22 C23 . 1.371(3) ?
C22 H22 . 0.9500 ?
C23 C24 . 1.378(2) ?
C23 H23 . 0.9500 ?
C24 H24 . 0.9500 ?
C25 H25A . 0.9800 ?
C25 H25B . 0.9800 ?
C25 H25C . 0.9800 ?
C26 H26A . 0.9800 ?
C26 H26B . 0.9800 ?
C26 H26C . 0.9800 ?
C27 C36 . 1.387(2) ?
C27 C28 . 1.405(2) ?
C28 C29 . 1.360(2) ?
C28 H28 . 0.9500 ?
C29 C30 . 1.411(2) ?
C29 H29 . 0.9500 ?
C30 C31 . 1.414(2) ?
C30 C35 . 1.426(2) ?
C31 C32 . 1.359(2) ?
C31 H31 . 0.9500 ?
C32 C33 . 1.426(2) ?
C32 C44 . 1.504(2) ?
C33 C34 . 1.370(2) ?
C34 C35 . 1.428(2) ?
C34 H34 . 0.9500 ?
C35 C36 . 1.420(2) ?
C36 C37 . 1.500(2) ?
C37 C38 . 1.4918(19) ?
C38 C39 . 1.384(2) ?
C38 C43 . 1.388(2) ?
C39 C40 . 1.399(2) ?
C39 H39 . 0.9500 ?
C40 C41 . 1.376(3) ?
C40 H40 . 0.9500 ?
C41 C42 . 1.374(3) ?
C41 H41 . 0.9500 ?
C42 C43 . 1.377(2) ?
C42 H42 . 0.9500 ?
C43 H43 . 0.9500 ?
C44 C45 . 1.481(2) ?
C45 C50 . 1.394(2) ?
C45 C46 . 1.395(2) ?
C46 C47 . 1.380(2) ?
C46 H46 . 0.9500 ?
C47 C48 . 1.382(2) ?
C47 H47 . 0.9500 ?
C48 C49 . 1.377(2) ?
C48 H48 . 0.9500 ?
C49 C50 . 1.382(2) ?
C49 H49 . 0.9500 ?
C50 H50 . 0.9500 ?
C51 H51A . 0.9800 ?
C51 H51B . 0.9800 ?
C51 H51C . 0.9800 ?
C52 H52A . 0.9800 ?
C52 H52B . 0.9800 ?
C52 H52C . 0.9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C15 H15 O3 1_655 0.95 2.57 3.5191(19) 176
C25 H25C O4 2_675 0.98 2.56 3.348(2) 138
C51 H51C O8 2_666 0.98 2.47 3.371(2) 152
C3 H3 Cg1 2_575 0.95 2.59 3.416(11) 145
C14 H14 Cg2 1_455 0.95 2.86 3.578(9) 133
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C25 O1 C1 C10 . . . . -177.07(12) ?
C25 O1 C1 C2 . . . . 2.29(19) ?
O1 C1 C2 C3 . . . . -178.06(12) ?
C10 C1 C2 C3 . . . . 1.3(2) ?
C1 C2 C3 C4 . . . . 1.0(2) ?
C2 C3 C4 C5 . . . . 177.43(13) ?
C2 C3 C4 C9 . . . . -1.2(2) ?
C3 C4 C5 C6 . . . . -177.64(13) ?
C9 C4 C5 C6 . . . . 0.99(19) ?
C4 C5 C6 C7 . . . . -2.4(2) ?
C4 C5 C6 C18 . . . . 176.84(12) ?
C26 O2 C7 C8 . . . . 7.8(2) ?
C26 O2 C7 C6 . . . . -173.92(13) ?
C5 C6 C7 O2 . . . . -176.53(12) ?
C18 C6 C7 O2 . . . . 4.24(18) ?
C5 C6 C7 C8 . . . . 1.8(2) ?
C18 C6 C7 C8 . . . . -177.42(12) ?
O2 C7 C8 C9 . . . . 178.41(12) ?
C6 C7 C8 C9 . . . . 0.26(19) ?
C5 C4 C9 C10 . . . . -179.44(11) ?
C3 C4 C9 C10 . . . . -0.78(18) ?
C5 C4 C9 C8 . . . . 1.10(18) ?
C3 C4 C9 C8 . . . . 179.75(12) ?
C7 C8 C9 C4 . . . . -1.69(18) ?
C7 C8 C9 C10 . . . . 178.87(12) ?
O1 C1 C10 C9 . . . . 176.13(11) ?
C2 C1 C10 C9 . . . . -3.24(19) ?
O1 C1 C10 C11 . . . . -3.54(17) ?
C2 C1 C10 C11 . . . . 177.08(12) ?
C4 C9 C10 C1 . . . . 2.95(18) ?
C8 C9 C10 C1 . . . . -177.61(12) ?
C4 C9 C10 C11 . . . . -177.38(11) ?
C8 C9 C10 C11 . . . . 2.06(19) ?
C1 C10 C11 O3 . . . . 119.31(15) ?
C9 C10 C11 O3 . . . . -60.36(18) ?
C1 C10 C11 C12 . . . . -63.44(16) ?
C9 C10 C11 C12 . . . . 116.89(13) ?
O3 C11 C12 C17 . . . . -7.9(2) ?
C10 C11 C12 C17 . . . . 174.81(12) ?
O3 C11 C12 C13 . . . . 170.31(13) ?
C10 C11 C12 C13 . . . . -6.93(19) ?
C17 C12 C13 C14 . . . . 0.5(2) ?
C11 C12 C13 C14 . . . . -177.72(13) ?
C12 C13 C14 C15 . . . . -0.2(2) ?
C13 C14 C15 C16 . . . . -0.5(2) ?
C14 C15 C16 C17 . . . . 0.7(2) ?
C15 C16 C17 C12 . . . . -0.4(2) ?
C13 C12 C17 C16 . . . . -0.3(2) ?
C11 C12 C17 C16 . . . . 178.04(13) ?
C5 C6 C18 O4 . . . . 48.67(19) ?
C7 C6 C18 O4 . . . . -132.11(15) ?
C5 C6 C18 C19 . . . . -125.45(14) ?
C7 C6 C18 C19 . . . . 53.78(18) ?
O4 C18 C19 C20 . . . . -156.43(15) ?
C6 C18 C19 C20 . . . . 17.6(2) ?
O4 C18 C19 C24 . . . . 18.6(2) ?
C6 C18 C19 C24 . . . . -167.32(12) ?
C24 C19 C20 C21 . . . . -1.0(2) ?
C18 C19 C20 C21 . . . . 174.04(13) ?
C19 C20 C21 C22 . . . . 1.0(2) ?
C20 C21 C22 C23 . . . . -0.3(2) ?
C21 C22 C23 C24 . . . . -0.3(2) ?
C22 C23 C24 C19 . . . . 0.4(2) ?
C20 C19 C24 C23 . . . . 0.3(2) ?
C18 C19 C24 C23 . . . . -174.90(13) ?
C51 O5 C27 C36 . . . . -171.18(13) ?
C51 O5 C27 C28 . . . . 8.4(2) ?
O5 C27 C28 C29 . . . . -178.70(14) ?
C36 C27 C28 C29 . . . . 0.9(2) ?
C27 C28 C29 C30 . . . . 1.1(2) ?
C28 C29 C30 C31 . . . . 177.89(16) ?
C28 C29 C30 C35 . . . . -1.4(2) ?
C29 C30 C31 C32 . . . . -178.62(14) ?
C35 C30 C31 C32 . . . . 0.7(2) ?
C30 C31 C32 C33 . . . . -1.1(2) ?
C30 C31 C32 C44 . . . . 178.77(14) ?
C52 O6 C33 C34 . . . . -0.7(2) ?
C52 O6 C33 C32 . . . . 178.53(12) ?
C31 C32 C33 O6 . . . . -178.54(12) ?
C44 C32 C33 O6 . . . . 1.55(19) ?
C31 C32 C33 C34 . . . . 0.8(2) ?
C44 C32 C33 C34 . . . . -179.15(13) ?
O6 C33 C34 C35 . . . . 179.31(12) ?
C32 C33 C34 C35 . . . . 0.1(2) ?
C29 C30 C35 C36 . . . . -0.2(2) ?
C31 C30 C35 C36 . . . . -179.48(13) ?
C29 C30 C35 C34 . . . . 179.53(13) ?
C31 C30 C35 C34 . . . . 0.2(2) ?
C33 C34 C35 C36 . . . . 179.10(13) ?
C33 C34 C35 C30 . . . . -0.6(2) ?
O5 C27 C36 C35 . . . . 177.17(12) ?
C28 C27 C36 C35 . . . . -2.4(2) ?
O5 C27 C36 C37 . . . . -1.77(19) ?
C28 C27 C36 C37 . . . . 178.60(14) ?
C30 C35 C36 C27 . . . . 2.1(2) ?
C34 C35 C36 C27 . . . . -177.65(13) ?
C30 C35 C36 C37 . . . . -179.02(12) ?
C34 C35 C36 C37 . . . . 1.3(2) ?
C27 C36 C37 O7 . . . . 106.69(17) ?
C35 C36 C37 O7 . . . . -72.25(19) ?
C27 C36 C37 C38 . . . . -73.11(17) ?
C35 C36 C37 C38 . . . . 107.95(15) ?
O7 C37 C38 C39 . . . . 171.32(14) ?
C36 C37 C38 C39 . . . . -8.9(2) ?
O7 C37 C38 C43 . . . . -9.1(2) ?
C36 C37 C38 C43 . . . . 170.69(13) ?
C43 C38 C39 C40 . . . . -0.6(2) ?
C37 C38 C39 C40 . . . . 178.99(14) ?
C38 C39 C40 C41 . . . . -1.2(3) ?
C39 C40 C41 C42 . . . . 1.4(3) ?
C40 C41 C42 C43 . . . . 0.1(3) ?
C41 C42 C43 C38 . . . . -1.9(3) ?
C39 C38 C43 C42 . . . . 2.1(2) ?
C37 C38 C43 C42 . . . . -177.46(15) ?
C31 C32 C44 O8 . . . . 73.7(2) ?
C33 C32 C44 O8 . . . . -106.41(19) ?
C31 C32 C44 C45 . . . . -103.19(17) ?
C33 C32 C44 C45 . . . . 76.72(19) ?
O8 C44 C45 C50 . . . . 6.2(2) ?
C32 C44 C45 C50 . . . . -177.02(14) ?
O8 C44 C45 C46 . . . . -171.66(17) ?
C32 C44 C45 C46 . . . . 5.2(2) ?
C50 C45 C46 C47 . . . . -0.8(2) ?
C44 C45 C46 C47 . . . . 177.00(14) ?
C45 C46 C47 C48 . . . . 0.7(2) ?
C46 C47 C48 C49 . . . . -0.1(3) ?
C47 C48 C49 C50 . . . . -0.4(2) ?
C48 C49 C50 C45 . . . . 0.2(2) ?
C46 C45 C50 C49 . . . . 0.4(2) ?
C44 C45 C50 C49 . . . . -177.50(14) ?
