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#$Date: 2024-07-05 20:54:27 +0300 (Fri, 05 Jul 2024) $
#$Revision: 293240 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/99/7159969.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_7159969
loop_
_publ_author_name
'Hemamalini, Vijayakumar'
'Shanthi, Markabandhu'
'Shankar, Bhaskaran'
'Dandela, Rambabu'
'Perumal, Karuppaiah'
'Ramesh, Subburethinam'
_publ_section_title
;
 Visible-light promoted oxidative annulation of 2-naphthols with
 phenylglyoxal monohydrates toward hydroxy-naphthofuranone and its
 derivatives.
;
_journal_issue                   26
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5314
_journal_page_last               5324
_journal_paper_doi               10.1039/d4ob00693c
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C18 H12 O3'
_chemical_formula_sum            'C18 H12 O3'
_chemical_formula_weight         276.28
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-04-22 deposited with the CCDC.	2024-06-06 downloaded from the CCDC.
;
_cell_angle_alpha                96.22(2)
_cell_angle_beta                 97.254(18)
_cell_angle_gamma                106.440(17)
_cell_formula_units_Z            6
_cell_length_a                   10.989(7)
_cell_length_b                   11.463(8)
_cell_length_c                   17.763(13)
_cell_measurement_reflns_used    7293
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.93
_cell_measurement_theta_min      2.27
_cell_volume                     2104(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1000
_diffrn_reflns_av_unetI/netI     0.1194
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            20391
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        24.497
_diffrn_reflns_theta_max         24.497
_diffrn_reflns_theta_min         2.267
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_description       Block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     626
_refine_ls_number_reflns         6952
_refine_ls_number_restraints     417
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.1421
_refine_ls_R_factor_gt           0.0702
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0454P)²+0.8764P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1395
_refine_ls_wR_factor_ref         0.1687
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3888
_reflns_number_total             6952
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob00693c2.cif
_cod_data_source_block           SS-129
_cod_depositor_comments
'Adding full bibliography for 7159969--7159970.cif.'
_cod_database_code               7159969
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.989
_shelx_estimated_absorpt_t_max   0.993
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
O1 O 0.8113(2) 0.6861(2) 0.13826(13) 0.0582(7) Uani 1 1 d . . . . .
O2 O 0.6581(2) 0.5580(2) 0.28830(14) 0.0535(6) Uani 1 1 d . . . . .
O3 O 0.8925(2) 0.5653(2) 0.21748(16) 0.0654(7) Uani 1 1 d . . . . .
H3 H 0.847562 0.500894 0.190787 0.098 Uiso 1 1 calc R U . . .
O7 O 0.7520(3) 0.3776(2) 0.34186(13) 0.0606(7) Uani 1 1 d . . . . .
H7 H 0.723660 0.434080 0.331895 0.091 Uiso 1 1 calc R U . . .
O8 O 0.8551(3) 0.2099(2) 0.41765(15) 0.0673(7) Uani 1 1 d . . . . .
O9 O 0.5648(2) 0.2914(2) 0.39133(13) 0.0592(7) Uani 1 1 d . . . . .
C1 C 0.4704(4) 0.6192(3) 0.1540(2) 0.0504(9) Uani 1 1 d . . . . .
C2 C 0.2584(4) 0.5771(4) 0.1892(3) 0.0723(12) Uani 1 1 d . . . . .
H2 H 0.203458 0.553044 0.224244 0.087 Uiso 1 1 calc R U . . .
C3 C 0.3859(4) 0.5814(3) 0.2062(2) 0.0597(10) Uani 1 1 d . . . . .
H3A H 0.416105 0.559394 0.252169 0.072 Uiso 1 1 calc R U . . .
C4 C 0.6054(3) 0.6328(3) 0.16902(19) 0.0469(9) Uani 1 1 d . . . . .
C5 C 0.6858(3) 0.6063(3) 0.2319(2) 0.0465(9) Uani 1 1 d . . . . .
C6 C 0.8273(3) 0.6529(3) 0.2160(2) 0.0504(9) Uani 1 1 d . . . . .
C7 C 0.9022(3) 0.7667(3) 0.2733(2) 0.0492(9) Uani 1 1 d . . . . .
C8 C 0.9042(3) 0.8836(3) 0.2606(2) 0.0529(10) Uani 1 1 d . . . . .
H8 H 0.864477 0.895049 0.213708 0.064 Uiso 1 1 calc R U . . .
C9 C 0.9648(4) 0.9845(4) 0.3167(2) 0.0606(11) Uani 1 1 d . . . . .
H9 H 0.965613 1.062869 0.307271 0.073 Uiso 1 1 calc R U . . .
C10 C 1.0239(4) 0.9691(4) 0.3865(3) 0.0695(12) Uani 1 1 d . . . . .
H10 H 1.065613 1.037187 0.423702 0.083 Uiso 1 1 calc R U . . .
C11 C 0.6845(4) 0.6750(3) 0.1169(2) 0.0545(10) Uani 1 1 d . . . . .
C12 C 0.9610(4) 0.7515(4) 0.3447(2) 0.0677(12) Uani 1 1 d . . . . .
H12 H 0.960042 0.673176 0.354416 0.081 Uiso 1 1 calc R U . . .
C13 C 1.0212(4) 0.8531(5) 0.4013(3) 0.0766(13) Uani 1 1 d . . . . .
H13 H 1.059325 0.842502 0.448783 0.092 Uiso 1 1 calc R U . . .
C14 C 0.6371(5) 0.7041(4) 0.0460(2) 0.0749(13) Uani 1 1 d . . . . .
H14 H 0.691171 0.731358 0.011050 0.090 Uiso 1 1 calc R U . . .
C15 C 0.5085(5) 0.6906(4) 0.0309(3) 0.0849(14) Uani 1 1 d . . . . .
H15 H 0.475344 0.708799 -0.015680 0.102 Uiso 1 1 calc R U . . .
C16 C 0.4225(4) 0.6498(4) 0.0831(2) 0.0633(11) Uani 1 1 d . . . . .
C17 C 0.2895(5) 0.6429(4) 0.0678(3) 0.0852(14) Uani 1 1 d . . . . .
H17 H 0.256552 0.662264 0.021611 0.102 Uiso 1 1 calc R U . . .
C36 C 0.8107(9) 0.5990(6) 0.6128(4) 0.082(2) Uani 0.740(16) 1 d D U P A 1
H36 H 0.833047 0.656595 0.657148 0.098 Uiso 0.740(16) 1 calc R U P A 1
C36A C 0.8379(19) 0.6065(17) 0.6097(10) 0.072(4) Uani 0.260(16) 1 d D U P A 2
H36A H 0.864656 0.664852 0.653801 0.087 Uiso 0.260(16) 1 calc R U P A 2
C37 C 0.8906(8) 0.5287(8) 0.5957(4) 0.087(2) Uani 0.740(16) 1 d D U P A 1
H37 H 0.966882 0.539392 0.628802 0.104 Uiso 0.740(16) 1 calc R U P A 1
C37A C 0.879(2) 0.5017(18) 0.6055(10) 0.072(4) Uani 0.260(16) 1 d D U P A 2
H37A H 0.932672 0.489781 0.646747 0.087 Uiso 0.260(16) 1 calc R U P A 2
C38 C 0.8571(7) 0.4425(8) 0.5295(4) 0.073(2) Uani 0.740(16) 1 d D U P A 1
H38 H 0.911015 0.395497 0.518567 0.088 Uiso 0.740(16) 1 calc R U P A 1
C38A C 0.838(2) 0.4155(17) 0.5394(10) 0.065(4) Uani 0.260(16) 1 d D U P A 2
H38A H 0.865646 0.345624 0.536658 0.078 Uiso 0.260(16) 1 calc R U P A 2
C39 C 0.7432(7) 0.4259(5) 0.4793(3) 0.0480(16) Uani 0.740(16) 1 d D U P A 1
C39A C 0.7573(19) 0.4318(15) 0.4769(9) 0.063(4) Uani 0.260(16) 1 d D U P A 2
C40 C 0.7050(4) 0.3325(3) 0.40672(19) 0.0498(9) Uani 1 1 d D . . . .
C41 C 0.7434(4) 0.2127(3) 0.41267(18) 0.0477(9) Uani 1 1 d . . . . .
C42 C 0.6249(3) 0.1159(3) 0.40754(17) 0.0455(9) Uani 1 1 d . . . . .
C43 C 0.5982(4) -0.0132(3) 0.40959(18) 0.0501(9) Uani 1 1 d . . . . .
C44 C 0.6946(4) -0.0720(4) 0.41725(19) 0.0578(10) Uani 1 1 d . . . . .
H44 H 0.780780 -0.026401 0.423138 0.069 Uiso 1 1 calc R U . . .
C45 C 0.6604(5) -0.1974(4) 0.4160(2) 0.0749(13) Uani 1 1 d . . . . .
H45 H 0.724021 -0.236293 0.420842 0.090 Uiso 1 1 calc R U . . .
C46 C 0.5328(6) -0.2662(4) 0.4075(3) 0.0850(15) Uani 1 1 d . . . . .
H46 H 0.511843 -0.350907 0.406354 0.102 Uiso 1 1 calc R U . . .
C47 C 0.7014(10) 0.5831(8) 0.5649(4) 0.083(2) Uani 0.740(16) 1 d D U P A 1
H47 H 0.647836 0.630164 0.576176 0.100 Uiso 0.740(16) 1 calc R U P A 1
C47A C 0.760(2) 0.6232(17) 0.5498(10) 0.073(3) Uani 0.260(16) 1 d D U P A 2
H47A H 0.732576 0.693074 0.552499 0.087 Uiso 0.260(16) 1 calc R U P A 2
C48 C 0.6663(9) 0.4964(7) 0.4978(4) 0.074(2) Uani 0.740(16) 1 d D U P A 1
H48 H 0.589583 0.486728 0.465333 0.089 Uiso 0.740(16) 1 calc R U P A 1
C48A C 0.720(2) 0.5350(15) 0.4831(9) 0.072(4) Uani 0.260(16) 1 d D U P A 2
H48A H 0.665660 0.547649 0.442127 0.087 Uiso 0.260(16) 1 calc R U P A 2
C49 C 0.4366(5) -0.2120(4) 0.4008(2) 0.0738(13) Uani 1 1 d . . . . .
H49 H 0.351250 -0.259706 0.395758 0.089 Uiso 1 1 calc R U . . .
C50 C 0.4675(4) -0.0825(4) 0.40166(19) 0.0587(10) Uani 1 1 d . . . . .
C51 C 0.3703(4) -0.0227(4) 0.3922(2) 0.0687(12) Uani 1 1 d . . . . .
H51 H 0.284930 -0.069818 0.388012 0.082 Uiso 1 1 calc R U . . .
C52 C 0.3960(4) 0.0998(4) 0.3891(2) 0.0654(11) Uani 1 1 d . . . . .
H52 H 0.330735 0.136536 0.382758 0.078 Uiso 1 1 calc R U . . .
C53 C 0.5259(4) 0.1680(4) 0.39594(19) 0.0522(10) Uani 1 1 d . . . . .
C54 C 0.2109(5) 0.6087(4) 0.1196(3) 0.0876(15) Uani 1 1 d . . . . .
H54 H 0.125021 0.606108 0.109016 0.105 Uiso 1 1 calc R U . . .
O4 O 0.6925(2) 0.3582(2) 0.15400(13) 0.0525(6) Uani 1 1 d . . . . .
O5 O 0.8986(2) 0.2805(2) 0.24391(13) 0.0589(7) Uani 1 1 d . . . . .
H5 H 0.865485 0.302638 0.279487 0.088 Uiso 1 1 calc R U . . .
O6 O 0.7500(2) 0.0852(2) 0.20582(13) 0.0538(7) Uani 1 1 d . . . . .
C18 C 0.1826(4) 0.1271(5) 0.1891(2) 0.0738(13) Uani 1 1 d . . . . .
H18 H 0.096717 0.119699 0.191356 0.089 Uiso 1 1 calc R U . . .
C19 C 0.2646(4) 0.2363(4) 0.1749(2) 0.0706(12) Uani 1 1 d . . . . .
H19 H 0.232558 0.301957 0.167761 0.085 Uiso 1 1 calc R U . . .
C20 C 0.3922(4) 0.2497(4) 0.1712(2) 0.0576(10) Uani 1 1 d . . . . .
H20 H 0.445506 0.323719 0.161785 0.069 Uiso 1 1 calc R U . . .
C21 C 0.4415(3) 0.1512(3) 0.18173(18) 0.0458(9) Uani 1 1 d . . . . .
C22 C 0.5748(3) 0.1589(3) 0.18244(17) 0.0413(8) Uani 1 1 d . . . . .
C23 C 0.6851(3) 0.2558(3) 0.17193(17) 0.0430(8) Uani 1 1 d . . . . .
C24 C 0.8026(3) 0.2068(3) 0.18478(18) 0.0454(9) Uani 1 1 d . . . . .
C25 C 0.8614(3) 0.1934(3) 0.11249(18) 0.0467(9) Uani 1 1 d . . . . .
C26 C 0.8189(4) 0.0847(4) 0.0613(2) 0.0680(12) Uani 1 1 d . . . . .
H26 H 0.754994 0.018369 0.071517 0.082 Uiso 1 1 calc R U . . .
C27 C 0.8715(5) 0.0745(5) -0.0056(2) 0.0868(15) Uani 1 1 d . . . . .
H27 H 0.844635 0.000484 -0.039031 0.104 Uiso 1 1 calc R U . . .
C28 C 0.9619(5) 0.1724(5) -0.0220(2) 0.0818(14) Uani 1 1 d . . . . .
H28 H 0.995104 0.165141 -0.067352 0.098 Uiso 1 1 calc R U . . .
C29 C 0.6203(4) 0.0624(3) 0.20050(18) 0.0464(9) Uani 1 1 d . . . . .
C30 C 0.5389(4) -0.0505(3) 0.2126(2) 0.0583(10) Uani 1 1 d . . . . .
H30 H 0.569920 -0.115716 0.222626 0.070 Uiso 1 1 calc R U . . .
C31 C 0.4112(4) -0.0591(4) 0.2090(2) 0.0622(11) Uani 1 1 d . . . . .
H31 H 0.354857 -0.133569 0.215384 0.075 Uiso 1 1 calc R U . . .
C32 C 0.3599(4) 0.0391(4) 0.19598(19) 0.0528(10) Uani 1 1 d . . . . .
C33 C 0.2297(4) 0.0303(4) 0.1997(2) 0.0670(12) Uani 1 1 d . . . . .
H33 H 0.175017 -0.042683 0.209605 0.080 Uiso 1 1 calc R U . . .
C34 C 0.9533(4) 0.2925(4) 0.0955(2) 0.0586(10) Uani 1 1 d . . . . .
H34 H 0.981017 0.366257 0.129199 0.070 Uiso 1 1 calc R U . . .
C35 C 1.0053(4) 0.2827(4) 0.0275(2) 0.0705(12) Uani 1 1 d . . . . .
H35 H 1.067756 0.349182 0.016053 0.085 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 0.0033 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
_geom_angle_publ_flag
C11 O1 C6 107.7(3) . . ?
C6 O3 H3 109.5 . . ?
C40 O7 H7 109.5 . . ?
C53 O9 C40 107.2(3) . . ?
C3 C1 C16 119.4(4) . . ?
C3 C1 C4 123.7(3) . . ?
C16 C1 C4 116.9(3) . . ?
C3 C2 C54 120.6(4) . . ?
C3 C2 H2 119.7 . . ?
C54 C2 H2 119.7 . . ?
C2 C3 C1 120.2(4) . . ?
C2 C3 H3A 119.9 . . ?
C1 C3 H3A 119.9 . . ?
C11 C4 C1 121.1(3) . . ?
C11 C4 C5 106.5(3) . . ?
C1 C4 C5 132.4(3) . . ?
O2 C5 C4 130.9(3) . . ?
O2 C5 C6 122.9(3) . . ?
C4 C5 C6 106.2(3) . . ?
O3 C6 O1 109.9(3) . . ?
O3 C6 C7 109.7(3) . . ?
O1 C6 C7 109.8(3) . . ?
O3 C6 C5 114.2(3) . . ?
O1 C6 C5 103.4(3) . . ?
C7 C6 C5 109.6(3) . . ?
C8 C7 C12 118.6(3) . . ?
C8 C7 C6 122.4(3) . . ?
C12 C7 C6 118.7(3) . . ?
C7 C8 C9 120.8(4) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C10 C9 C8 120.3(4) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C13 C10 C9 120.1(4) . . ?
C13 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
O1 C11 C4 115.6(3) . . ?
O1 C11 C14 122.2(4) . . ?
C4 C11 C14 122.2(4) . . ?
C13 C12 C7 120.4(4) . . ?
C13 C12 H12 119.8 . . ?
C7 C12 H12 119.8 . . ?
C10 C13 C12 119.8(4) . . ?
C10 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C15 C14 C11 117.1(4) . . ?
C15 C14 H14 121.4 . . ?
C11 C14 H14 121.4 . . ?
C14 C15 C16 123.2(4) . . ?
C14 C15 H15 118.4 . . ?
C16 C15 H15 118.4 . . ?
C1 C16 C15 119.5(4) . . ?
C1 C16 C17 118.4(4) . . ?
C15 C16 C17 122.1(4) . . ?
C54 C17 C16 121.1(5) . . ?
C54 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C47 C36 C37 119.4(6) . . ?
C47 C36 H36 120.3 . . ?
C37 C36 H36 120.3 . . ?
C47A C36A C37A 119.9(12) . . ?
C47A C36A H36A 120.0 . . ?
C37A C36A H36A 120.0 . . ?
C36 C37 C38 120.3(6) . . ?
C36 C37 H37 119.8 . . ?
C38 C37 H37 119.8 . . ?
C38A C37A C36A 119.5(12) . . ?
C38A C37A H37A 120.2 . . ?
C36A C37A H37A 120.2 . . ?
C37 C38 C39 120.4(5) . . ?
C37 C38 H38 119.8 . . ?
C39 C38 H38 119.8 . . ?
C37A C38A C39A 121.1(12) . . ?
C37A C38A H38A 119.5 . . ?
C39A C38A H38A 119.5 . . ?
C48 C39 C38 118.0(5) . . ?
C48 C39 C40 120.8(5) . . ?
C38 C39 C40 121.2(5) . . ?
C48A C39A C38A 117.7(10) . . ?
C48A C39A C40 121.1(12) . . ?
C38A C39A C40 121.0(12) . . ?
O7 C40 O9 109.3(3) . . ?
O7 C40 C39 114.8(4) . . ?
O9 C40 C39 106.3(4) . . ?
O7 C40 C39A 109.8(9) . . ?
O9 C40 C39A 112.0(8) . . ?
O7 C40 C41 105.8(3) . . ?
O9 C40 C41 104.7(3) . . ?
C39 C40 C41 115.5(3) . . ?
C39A C40 C41 115.0(7) . . ?
O8 C41 C42 130.9(3) . . ?
O8 C41 C40 123.1(3) . . ?
C42 C41 C40 105.9(3) . . ?
C53 C42 C43 120.8(4) . . ?
C53 C42 C41 107.1(3) . . ?
C43 C42 C41 132.0(3) . . ?
C44 C43 C50 120.0(4) . . ?
C44 C43 C42 123.3(4) . . ?
C50 C43 C42 116.7(3) . . ?
C45 C44 C43 119.6(4) . . ?
C45 C44 H44 120.2 . . ?
C43 C44 H44 120.2 . . ?
C44 C45 C46 120.8(4) . . ?
C44 C45 H45 119.6 . . ?
C46 C45 H45 119.6 . . ?
C49 C46 C45 121.2(4) . . ?
C49 C46 H46 119.4 . . ?
C45 C46 H46 119.4 . . ?
C36 C47 C48 121.0(6) . . ?
C36 C47 H47 119.5 . . ?
C48 C47 H47 119.5 . . ?
C36A C47A C48A 120.0(12) . . ?
C36A C47A H47A 120.0 . . ?
C48A C47A H47A 120.0 . . ?
C39 C48 C47 121.0(5) . . ?
C39 C48 H48 119.5 . . ?
C47 C48 H48 119.5 . . ?
C39A C48A C47A 121.8(12) . . ?
C39A C48A H48A 119.1 . . ?
C47A C48A H48A 119.1 . . ?
C46 C49 C50 119.9(4) . . ?
C46 C49 H49 120.1 . . ?
C50 C49 H49 120.1 . . ?
C43 C50 C49 118.4(4) . . ?
C43 C50 C51 119.7(4) . . ?
C49 C50 C51 121.8(4) . . ?
C52 C51 C50 123.4(4) . . ?
C52 C51 H51 118.3 . . ?
C50 C51 H51 118.3 . . ?
C51 C52 C53 116.6(4) . . ?
C51 C52 H52 121.7 . . ?
C53 C52 H52 121.7 . . ?
O9 C53 C42 114.8(3) . . ?
O9 C53 C52 122.6(4) . . ?
C42 C53 C52 122.6(4) . . ?
C17 C54 C2 120.3(4) . . ?
C17 C54 H54 119.8 . . ?
C2 C54 H54 119.8 . . ?
C24 O5 H5 109.5 . . ?
C29 O6 C24 107.7(2) . . ?
C33 C18 C19 119.3(4) . . ?
C33 C18 H18 120.3 . . ?
C19 C18 H18 120.3 . . ?
C20 C19 C18 121.5(4) . . ?
C20 C19 H19 119.2 . . ?
C18 C19 H19 119.2 . . ?
C19 C20 C21 119.7(4) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C20 C21 C32 119.8(3) . . ?
C20 C21 C22 123.5(3) . . ?
C32 C21 C22 116.7(3) . . ?
C29 C22 C21 120.8(3) . . ?
C29 C22 C23 106.2(3) . . ?
C21 C22 C23 132.9(3) . . ?
O4 C23 C22 130.1(3) . . ?
O4 C23 C24 123.1(3) . . ?
C22 C23 C24 106.8(3) . . ?
O5 C24 O6 109.7(3) . . ?
O5 C24 C25 108.8(3) . . ?
O6 C24 C25 108.9(3) . . ?
O5 C24 C23 112.6(3) . . ?
O6 C24 C23 104.2(3) . . ?
C25 C24 C23 112.6(3) . . ?
C34 C25 C26 119.4(3) . . ?
C34 C25 C24 119.8(3) . . ?
C26 C25 C24 120.7(4) . . ?
C25 C26 C27 120.2(4) . . ?
C25 C26 H26 119.9 . . ?
C27 C26 H26 119.9 . . ?
C28 C27 C26 120.1(4) . . ?
C28 C27 H27 119.9 . . ?
C26 C27 H27 119.9 . . ?
C27 C28 C35 121.1(4) . . ?
C27 C28 H28 119.5 . . ?
C35 C28 H28 119.5 . . ?
O6 C29 C22 115.1(3) . . ?
O6 C29 C30 122.4(3) . . ?
C22 C29 C30 122.6(4) . . ?
C31 C30 C29 116.3(4) . . ?
C31 C30 H30 121.8 . . ?
C29 C30 H30 121.8 . . ?
C30 C31 C32 123.9(4) . . ?
C30 C31 H31 118.1 . . ?
C32 C31 H31 118.1 . . ?
C21 C32 C33 118.3(4) . . ?
C21 C32 C31 119.6(4) . . ?
C33 C32 C31 122.1(4) . . ?
C18 C33 C32 121.3(4) . . ?
C18 C33 H33 119.3 . . ?
C32 C33 H33 119.3 . . ?
C25 C34 C35 120.5(4) . . ?
C25 C34 H34 119.8 . . ?
C35 C34 H34 119.8 . . ?
C28 C35 C34 118.7(4) . . ?
C28 C35 H35 120.6 . . ?
C34 C35 H35 120.6 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.363(4) . ?
O1 C6 1.474(4) . ?
O2 C5 1.227(4) . ?
O3 C6 1.389(4) . ?
O3 H3 0.8200 . ?
O7 C40 1.410(4) . ?
O7 H7 0.8200 . ?
O8 C41 1.229(4) . ?
O9 C53 1.372(4) . ?
O9 C40 1.457(4) . ?
C1 C3 1.409(5) . ?
C1 C16 1.420(5) . ?
C1 C4 1.435(5) . ?
C2 C3 1.381(5) . ?
C2 C54 1.405(6) . ?
C2 H2 0.9300 . ?
C3 H3A 0.9300 . ?
C4 C11 1.382(5) . ?
C4 C5 1.447(5) . ?
C5 C6 1.568(5) . ?
C6 C7 1.520(5) . ?
C7 C8 1.378(5) . ?
C7 C12 1.400(5) . ?
C8 C9 1.386(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.378(5) . ?
C9 H9 0.9300 . ?
C10 C13 1.375(6) . ?
C10 H10 0.9300 . ?
C11 C14 1.412(5) . ?
C12 C13 1.396(5) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.366(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.428(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.430(6) . ?
C17 C54 1.354(6) . ?
C17 H17 0.9300 . ?
C36 C47 1.336(8) . ?
C36 C37 1.388(8) . ?
C36 H36 0.9300 . ?
C36A C47A 1.346(14) . ?
C36A C37A 1.394(14) . ?
C36A H36A 0.9300 . ?
C37 C38 1.389(7) . ?
C37 H37 0.9300 . ?
C37A C38A 1.386(14) . ?
C37A H37A 0.9300 . ?
C38 C39 1.395(7) . ?
C38 H38 0.9300 . ?
C38A C39A 1.397(14) . ?
C38A H38A 0.9300 . ?
C39 C48 1.369(7) . ?
C39 C40 1.515(6) . ?
C39A C48A 1.358(14) . ?
C39A C40 1.523(12) . ?
C40 C41 1.557(5) . ?
C41 C42 1.438(5) . ?
C42 C53 1.386(5) . ?
C42 C43 1.430(5) . ?
C43 C44 1.408(5) . ?
C43 C50 1.411(5) . ?
C44 C45 1.376(5) . ?
C44 H44 0.9300 . ?
C45 C46 1.380(6) . ?
C45 H45 0.9300 . ?
C46 C49 1.368(6) . ?
C46 H46 0.9300 . ?
C47 C48 1.402(7) . ?
C47 H47 0.9300 . ?
C47A C48A 1.406(13) . ?
C47A H47A 0.9300 . ?
C48 H48 0.9300 . ?
C48A H48A 0.9300 . ?
C49 C50 1.424(6) . ?
C49 H49 0.9300 . ?
C50 C51 1.426(6) . ?
C51 C52 1.360(6) . ?
C51 H51 0.9300 . ?
C52 C53 1.402(5) . ?
C52 H52 0.9300 . ?
C54 H54 0.9300 . ?
O4 C23 1.233(4) . ?
O5 C24 1.398(4) . ?
O5 H5 0.8200 . ?
O6 C29 1.364(4) . ?
O6 C24 1.459(4) . ?
C18 C33 1.372(6) . ?
C18 C19 1.389(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.378(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.403(5) . ?
C20 H20 0.9300 . ?
C21 C32 1.412(5) . ?
C21 C22 1.440(5) . ?
C22 C29 1.388(4) . ?
C22 C23 1.442(5) . ?
C23 C24 1.548(5) . ?
C24 C25 1.521(5) . ?
C25 C34 1.379(5) . ?
C25 C26 1.384(5) . ?
C26 C27 1.392(6) . ?
C26 H26 0.9300 . ?
C27 C28 1.359(6) . ?
C27 H27 0.9300 . ?
C28 C35 1.382(6) . ?
C28 H28 0.9300 . ?
C29 C30 1.405(5) . ?
C30 C31 1.371(5) . ?
C30 H30 0.9300 . ?
C31 C32 1.422(5) . ?
C31 H31 0.9300 . ?
C32 C33 1.416(5) . ?
C33 H33 0.9300 . ?
C34 C35 1.407(5) . ?
C34 H34 0.9300 . ?
C35 H35 0.9300 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C54 C2 C3 C1 0.8(6) . . . . ?
C16 C1 C3 C2 -1.5(5) . . . . ?
C4 C1 C3 C2 176.4(3) . . . . ?
C3 C1 C4 C11 -177.3(3) . . . . ?
C16 C1 C4 C11 0.6(5) . . . . ?
C3 C1 C4 C5 5.0(6) . . . . ?
C16 C1 C4 C5 -177.0(4) . . . . ?
C11 C4 C5 O2 -173.4(4) . . . . ?
C1 C4 C5 O2 4.5(6) . . . . ?
C11 C4 C5 C6 6.7(4) . . . . ?
C1 C4 C5 C6 -175.4(3) . . . . ?
C11 O1 C6 O3 128.6(3) . . . . ?
C11 O1 C6 C7 -110.6(3) . . . . ?
C11 O1 C6 C5 6.3(3) . . . . ?
O2 C5 C6 O3 52.7(4) . . . . ?
C4 C5 C6 O3 -127.3(3) . . . . ?
O2 C5 C6 O1 172.1(3) . . . . ?
C4 C5 C6 O1 -7.9(3) . . . . ?
O2 C5 C6 C7 -70.8(4) . . . . ?
C4 C5 C6 C7 109.1(3) . . . . ?
O3 C6 C7 C8 146.1(3) . . . . ?
O1 C6 C7 C8 25.2(5) . . . . ?
C5 C6 C7 C8 -87.8(4) . . . . ?
O3 C6 C7 C12 -40.1(4) . . . . ?
O1 C6 C7 C12 -161.0(3) . . . . ?
C5 C6 C7 C12 86.1(4) . . . . ?
C12 C7 C8 C9 0.9(5) . . . . ?
C6 C7 C8 C9 174.7(3) . . . . ?
C7 C8 C9 C10 -0.2(6) . . . . ?
C8 C9 C10 C13 -1.1(6) . . . . ?
C6 O1 C11 C4 -2.5(4) . . . . ?
C6 O1 C11 C14 177.9(3) . . . . ?
C1 C4 C11 O1 178.9(3) . . . . ?
C5 C4 C11 O1 -2.9(4) . . . . ?
C1 C4 C11 C14 -1.5(6) . . . . ?
C5 C4 C11 C14 176.7(4) . . . . ?
C8 C7 C12 C13 -0.5(6) . . . . ?
C6 C7 C12 C13 -174.5(4) . . . . ?
C9 C10 C13 C12 1.5(6) . . . . ?
C7 C12 C13 C10 -0.7(6) . . . . ?
O1 C11 C14 C15 -179.5(4) . . . . ?
C4 C11 C14 C15 0.9(6) . . . . ?
C11 C14 C15 C16 0.4(7) . . . . ?
C3 C1 C16 C15 178.7(4) . . . . ?
C4 C1 C16 C15 0.6(5) . . . . ?
C3 C1 C16 C17 1.0(6) . . . . ?
C4 C1 C16 C17 -177.1(3) . . . . ?
C14 C15 C16 C1 -1.2(7) . . . . ?
C14 C15 C16 C17 176.4(4) . . . . ?
C1 C16 C17 C54 0.3(7) . . . . ?
C15 C16 C17 C54 -177.3(5) . . . . ?
C47 C36 C37 C38 -0.1(2) . . . . ?
C47A C36A C37A C38A 0.0(2) . . . . ?
C36 C37 C38 C39 0.2(3) . . . . ?
C36A C37A C38A C39A 0.0(3) . . . . ?
C37 C38 C39 C48 -0.4(4) . . . . ?
C37 C38 C39 C40 179.9(5) . . . . ?
C37A C38A C39A C48A 0.0(4) . . . . ?
C37A C38A C39A C40 -175.4(17) . . . . ?
C53 O9 C40 O7 118.6(3) . . . . ?
C53 O9 C40 C39 -117.0(3) . . . . ?
C53 O9 C40 C39A -119.5(8) . . . . ?
C53 O9 C40 C41 5.7(3) . . . . ?
C48 C39 C40 O7 91.5(6) . . . . ?
C38 C39 C40 O7 -88.8(6) . . . . ?
C48 C39 C40 O9 -29.4(6) . . . . ?
C38 C39 C40 O9 150.2(5) . . . . ?
C48 C39 C40 C41 -145.0(6) . . . . ?
C38 C39 C40 C41 34.7(7) . . . . ?
C48A C39A C40 O7 68.5(15) . . . . ?
C38A C39A C40 O7 -116.3(12) . . . . ?
C48A C39A C40 O9 -53.2(15) . . . . ?
C38A C39A C40 O9 122.1(12) . . . . ?
C48A C39A C40 C41 -172.5(12) . . . . ?
C38A C39A C40 C41 2.8(16) . . . . ?
O7 C40 C41 O8 57.0(4) . . . . ?
O9 C40 C41 O8 172.4(3) . . . . ?
C39 C40 C41 O8 -71.1(5) . . . . ?
C39A C40 C41 O8 -64.3(10) . . . . ?
O7 C40 C41 C42 -120.6(3) . . . . ?
O9 C40 C41 C42 -5.2(3) . . . . ?
C39 C40 C41 C42 111.3(4) . . . . ?
C39A C40 C41 C42 118.1(10) . . . . ?
O8 C41 C42 C53 -174.6(4) . . . . ?
C40 C41 C42 C53 2.7(3) . . . . ?
O8 C41 C42 C43 2.9(6) . . . . ?
C40 C41 C42 C43 -179.8(3) . . . . ?
C53 C42 C43 C44 176.7(3) . . . . ?
C41 C42 C43 C44 -0.5(6) . . . . ?
C53 C42 C43 C50 -1.9(5) . . . . ?
C41 C42 C43 C50 -179.1(3) . . . . ?
C50 C43 C44 C45 0.8(5) . . . . ?
C42 C43 C44 C45 -177.7(3) . . . . ?
C43 C44 C45 C46 -0.2(6) . . . . ?
C44 C45 C46 C49 -0.6(7) . . . . ?
C37 C36 C47 C48 0.1(3) . . . . ?
C37A C36A C47A C48A 0.0(3) . . . . ?
C38 C39 C48 C47 0.4(3) . . . . ?
C40 C39 C48 C47 -179.9(5) . . . . ?
C36 C47 C48 C39 -0.2(3) . . . . ?
C38A C39A C48A C47A 0.0(4) . . . . ?
C40 C39A C48A C47A 175.4(17) . . . . ?
C36A C47A C48A C39A 0.0(3) . . . . ?
C45 C46 C49 C50 0.7(6) . . . . ?
C44 C43 C50 C49 -0.7(5) . . . . ?
C42 C43 C50 C49 177.9(3) . . . . ?
C44 C43 C50 C51 -178.6(3) . . . . ?
C42 C43 C50 C51 0.0(5) . . . . ?
C46 C49 C50 C43 -0.1(6) . . . . ?
C46 C49 C50 C51 177.8(4) . . . . ?
C43 C50 C51 C52 1.1(6) . . . . ?
C49 C50 C51 C52 -176.8(4) . . . . ?
C50 C51 C52 C53 -0.2(6) . . . . ?
C40 O9 C53 C42 -4.5(4) . . . . ?
C40 O9 C53 C52 175.8(3) . . . . ?
C43 C42 C53 O9 -176.8(3) . . . . ?
C41 C42 C53 O9 1.0(4) . . . . ?
C43 C42 C53 C52 2.9(5) . . . . ?
C41 C42 C53 C52 -179.3(3) . . . . ?
C51 C52 C53 O9 177.9(3) . . . . ?
C51 C52 C53 C42 -1.8(5) . . . . ?
C16 C17 C54 C2 -1.1(7) . . . . ?
C3 C2 C54 C17 0.5(7) . . . . ?
C33 C18 C19 C20 0.1(6) . . . . ?
C18 C19 C20 C21 0.2(6) . . . . ?
C19 C20 C21 C32 0.0(5) . . . . ?
C19 C20 C21 C22 -176.9(3) . . . . ?
C20 C21 C22 C29 173.7(3) . . . . ?
C32 C21 C22 C29 -3.4(4) . . . . ?
C20 C21 C22 C23 -1.8(5) . . . . ?
C32 C21 C22 C23 -178.9(3) . . . . ?
C29 C22 C23 O4 178.5(3) . . . . ?
C21 C22 C23 O4 -5.6(6) . . . . ?
C29 C22 C23 C24 0.6(3) . . . . ?
C21 C22 C23 C24 176.5(3) . . . . ?
C29 O6 C24 O5 124.6(3) . . . . ?
C29 O6 C24 C25 -116.4(3) . . . . ?
C29 O6 C24 C23 3.9(3) . . . . ?
O4 C23 C24 O5 60.4(4) . . . . ?
C22 C23 C24 O5 -121.5(3) . . . . ?
O4 C23 C24 O6 179.2(3) . . . . ?
C22 C23 C24 O6 -2.7(3) . . . . ?
O4 C23 C24 C25 -63.0(4) . . . . ?
C22 C23 C24 C25 115.1(3) . . . . ?
O5 C24 C25 C34 -38.5(4) . . . . ?
O6 C24 C25 C34 -158.0(3) . . . . ?
C23 C24 C25 C34 86.9(4) . . . . ?
O5 C24 C25 C26 145.0(3) . . . . ?
O6 C24 C25 C26 25.5(4) . . . . ?
C23 C24 C25 C26 -89.5(4) . . . . ?
C34 C25 C26 C27 2.1(6) . . . . ?
C24 C25 C26 C27 178.5(4) . . . . ?
C25 C26 C27 C28 -2.1(7) . . . . ?
C26 C27 C28 C35 1.3(7) . . . . ?
C24 O6 C29 C22 -4.0(3) . . . . ?
C24 O6 C29 C30 176.2(3) . . . . ?
C21 C22 C29 O6 -174.5(3) . . . . ?
C23 C22 C29 O6 2.1(4) . . . . ?
C21 C22 C29 C30 5.4(5) . . . . ?
C23 C22 C29 C30 -178.1(3) . . . . ?
O6 C29 C30 C31 177.1(3) . . . . ?
C22 C29 C30 C31 -2.7(5) . . . . ?
C29 C30 C31 C32 -1.8(5) . . . . ?
C20 C21 C32 C33 -0.4(5) . . . . ?
C22 C21 C32 C33 176.7(3) . . . . ?
C20 C21 C32 C31 -178.0(3) . . . . ?
C22 C21 C32 C31 -0.9(5) . . . . ?
C30 C31 C32 C21 3.5(5) . . . . ?
C30 C31 C32 C33 -174.0(3) . . . . ?
C19 C18 C33 C32 -0.5(6) . . . . ?
C21 C32 C33 C18 0.7(5) . . . . ?
C31 C32 C33 C18 178.2(4) . . . . ?
C26 C25 C34 C35 -1.3(5) . . . . ?
C24 C25 C34 C35 -177.8(3) . . . . ?
C27 C28 C35 C34 -0.5(7) . . . . ?
C25 C34 C35 C28 0.5(6) . . . . ?
