#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/32/2213212.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_2213212
loop_
_publ_author_name
'Hoong-Kun Fun'
'Sompong Boonsri'
'Suchada Chantrapromma'
'Nawong Boonnak'
'Chatchanok Karalai'
_publ_section_title
;
 3,6,9-Trimethyl-2,3-dihydrobenzo[de]chromene-7,8-dione
;
_journal_coeditor_code           CI2328
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2127
_journal_page_last               o2129
_journal_paper_doi               10.1107/S1600536807014547
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C15 H14 O3'
_chemical_formula_moiety         'C15 H14 O3'
_chemical_formula_sum            'C15 H14 O3'
_chemical_formula_weight         242.26
_chemical_melting_point          382.0(10)
_chemical_name_common
;
3,6,9-trimethyl-2,3-dihydrobenzo[de]chromene-7,8-dione
;
_chemical_name_systematic
;
3,6,9-trimethyl-2,3-dihydrobenzo[de]chromene-7,8-dione
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.2160(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.16150(10)
_cell_length_b                   18.6558(3)
_cell_length_c                   18.0323(3)
_cell_measurement_reflns_used    7133
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      30.00
_cell_measurement_theta_min      1.14
_cell_volume                     2384.45(6)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL and PLATON (Spek, 2003)'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1998)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type
;
Bruker SMART APEX2 CCD area-detector
;
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0802
_diffrn_reflns_av_sigmaI/netI    0.0831
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            30798
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         1.14
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9912
_exptl_absorpt_correction_T_min  0.9710
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.228
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     661
_refine_ls_number_reflns         7133
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.1133
_refine_ls_R_factor_gt           0.0614
_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)+(0.0867P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1321
_refine_ls_wR_factor_ref         0.1664
_reflns_number_gt                4478
_reflns_number_total             7133
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2328.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value '381-383' was changed to '382.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '381-383' was changed to '382.0(10)'
- the average value was taken and precision was
estimated.

'_symmetry_cell_setting' value 'Monoclinic' changed to
'monoclinic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2213212
_cod_database_fobs_code          2213212
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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
O O1A 0.6580(4) 0.21187(14) 0.70449(15) 0.0282(6) Uani d . 1
O O2A 0.5580(5) 0.05077(16) 0.50539(17) 0.0397(8) Uani d . 1
O O3A 0.5400(5) 0.15793(17) 0.40699(16) 0.0369(7) Uani d . 1
C C1A 0.5790(5) 0.2599(2) 0.5788(2) 0.0206(8) Uani d . 1
C C2A 0.6183(5) 0.1992(2) 0.6299(2) 0.0220(8) Uani d . 1
C C3A 0.6100(6) 0.1286(2) 0.6089(2) 0.0259(9) Uani d . 1
C C4A 0.5695(6) 0.1118(2) 0.5300(2) 0.0290(9) Uani d . 1
C C5A 0.5494(6) 0.1743(2) 0.4720(2) 0.0258(9) Uani d . 1
C C6A 0.5450(5) 0.2486(2) 0.5000(2) 0.0210(8) Uani d . 1
C C7A 0.5062(6) 0.3073(2) 0.4513(2) 0.0268(9) Uani d . 1
C C8A 0.4989(6) 0.3753(2) 0.4825(2) 0.0288(9) Uani d . 1
H H8AA 0.4713 0.4144 0.4509 0.035 Uiso calc R 1
C C9A 0.5309(6) 0.3867(2) 0.5586(2) 0.0287(9) Uani d . 1
H H9AA 0.5256 0.4329 0.5774 0.034 Uiso calc R 1
C C10A 0.5715(5) 0.3286(2) 0.6081(2) 0.0228(8) Uani d . 1
C C11A 0.6075(6) 0.3408(2) 0.6920(2) 0.0250(8) Uani d . 1
H H11A 0.6750 0.3864 0.7013 0.030 Uiso calc R 1
C C12A 0.7348(6) 0.2819(2) 0.7266(2) 0.0296(9) Uani d . 1
H H12A 0.8582 0.2869 0.7109 0.036 Uiso calc R 1
H H12B 0.7500 0.2860 0.7807 0.036 Uiso calc R 1
C C13A 0.6482(7) 0.0684(2) 0.6645(2) 0.0349(10) Uani d . 1
H H13A 0.7416 0.0833 0.7052 0.052 Uiso calc R 1
H H13B 0.6937 0.0274 0.6403 0.052 Uiso calc R 1
H H13C 0.5338 0.0561 0.6835 0.052 Uiso calc R 1
C C14A 0.4724(7) 0.2999(3) 0.3673(2) 0.0344(10) Uani d . 1
H H14A 0.4366 0.3455 0.3450 0.052 Uiso calc R 1
H H14B 0.3731 0.2658 0.3532 0.052 Uiso calc R 1
H H14C 0.5858 0.2836 0.3500 0.052 Uiso calc R 1
C C15A 0.4225(6) 0.3460(2) 0.7260(2) 0.0299(9) Uani d . 1
H H15A 0.4507 0.3567 0.7785 0.045 Uiso calc R 1
H H15B 0.3563 0.3012 0.7193 0.045 Uiso calc R 1
H H15C 0.3452 0.3835 0.7013 0.045 Uiso calc R 1
O O1B 0.0281(6) -0.00811(17) 0.47135(18) 0.0447(9) Uani d . 1
O O2B 0.1842(5) 0.08673(19) 0.71010(17) 0.0439(8) Uani d . 1
O O3B 0.0985(4) 0.21937(17) 0.65883(17) 0.0362(7) Uani d . 1
C C1B 0.0381(6) 0.1206(2) 0.4840(2) 0.0258(9) Uani d . 1
C C2B 0.0554(6) 0.0488(2) 0.5175(2) 0.0309(10) Uani d . 1
C C3B 0.1082(7) 0.0355(2) 0.5917(2) 0.0344(10) Uani d . 1
C C4B 0.1359(6) 0.0942(2) 0.6426(2) 0.0310(9) Uani d . 1
C C5B 0.0954(6) 0.1717(2) 0.6135(2) 0.0270(9) Uani d . 1
C C6B 0.0550(6) 0.1828(2) 0.5303(2) 0.0281(9) Uani d . 1
C C7B 0.0395(6) 0.2515(2) 0.4986(2) 0.0271(9) Uani d . 1
C C8B 0.0118(6) 0.2565(2) 0.4203(3) 0.0327(10) Uani d . 1
H H8BA 0.0028 0.3014 0.3978 0.039 Uiso calc R 1
C C9B -0.0024(6) 0.1962(2) 0.3762(2) 0.0290(9) Uani d . 1
H H9BA -0.0181 0.2016 0.3244 0.035 Uiso calc R 1
C C10B 0.0056(6) 0.1278(2) 0.4060(2) 0.0269(9) Uani d . 1
C C11B -0.0124(7) 0.0629(2) 0.3567(2) 0.0331(10) Uani d . 1
H H11B -0.1054 0.0734 0.3127 0.040 Uiso calc R 1
C C12B -0.0878(8) 0.0028(3) 0.3993(3) 0.0422(12) Uani d . 1
H H12C -0.2159 0.0139 0.4071 0.051 Uiso calc R 1
H H12D -0.0908 -0.0409 0.3702 0.051 Uiso calc R 1
C C13B 0.1301(9) -0.0389(3) 0.6226(3) 0.0489(14) Uani d . 1
H H13D 0.1818 -0.0693 0.5876 0.073 Uiso calc R 1
H H13E 0.0092 -0.0570 0.6306 0.073 Uiso calc R 1
H H13F 0.2136 -0.0382 0.6692 0.073 Uiso calc R 1
C C14B 0.0538(7) 0.3195(2) 0.5433(3) 0.0350(11) Uani d . 1
H H14D 0.1694 0.3195 0.5777 0.052 Uiso calc R 1
H H14E -0.0512 0.3228 0.5708 0.052 Uiso calc R 1
H H14F 0.0525 0.3598 0.5101 0.052 Uiso calc R 1
C C15B 0.1747(7) 0.0454(2) 0.3298(2) 0.0365(11) Uani d . 1
H H15D 0.2093 0.0840 0.2992 0.055 Uiso calc R 1
H H15E 0.1620 0.0020 0.3010 0.055 Uiso calc R 1
H H15F 0.2707 0.0393 0.3723 0.055 Uiso calc R 1
O O1C 0.4970(4) 0.23221(15) 1.19470(15) 0.0305(7) Uani d . 1
O O2C 0.5707(5) 0.40133(17) 1.01213(18) 0.0384(8) Uani d . 1
O O3C 0.6244(4) 0.29885(18) 0.91400(17) 0.0352(7) Uani d . 1
C C1C 0.5238(5) 0.1891(2) 1.0696(2) 0.0200(8) Uani d . 1
C C2C 0.5218(6) 0.2485(2) 1.1238(2) 0.0253(8) Uani d . 1
C C3C 0.5330(6) 0.3195(2) 1.1074(2) 0.0292(9) Uani d . 1
C C4C 0.5597(6) 0.3387(2) 1.0318(2) 0.0289(9) Uani d . 1
C C5C 0.5808(6) 0.2800(2) 0.9737(2) 0.0264(9) Uani d . 1
C C6C 0.5520(6) 0.2039(2) 0.9942(2) 0.0235(8) Uani d . 1
C C7C 0.5458(6) 0.1485(2) 0.9417(2) 0.0281(9) Uani d . 1
C C8C 0.5140(6) 0.0791(2) 0.9657(2) 0.0291(9) Uani d . 1
H H8CA 0.5122 0.0415 0.9318 0.035 Uiso calc R 1
C C9C 0.4853(6) 0.0645(2) 1.0381(2) 0.0278(9) Uani d . 1
H H9CA 0.4622 0.0176 1.0516 0.033 Uiso calc R 1
C C10C 0.4904(5) 0.1192(2) 1.0918(2) 0.0232(8) Uani d . 1
C C11C 0.4568(6) 0.1035(2) 1.1708(2) 0.0263(9) Uani d . 1
H H11C 0.3210 0.1059 1.1728 0.032 Uiso calc R 1
C C12C 0.5541(6) 0.1611(2) 1.2211(2) 0.0303(9) Uani d . 1
H H12E 0.5240 0.1547 1.2715 0.036 Uiso calc R 1
H H12F 0.6896 0.1564 1.2231 0.036 Uiso calc R 1
C C13C 0.5224(7) 0.3783(2) 1.1636(3) 0.0379(11) Uani d . 1
H H13G 0.5332 0.3581 1.2130 0.057 Uiso calc R 1
H H13H 0.4037 0.4027 1.1524 0.057 Uiso calc R 1
H H13I 0.6234 0.4117 1.1613 0.057 Uiso calc R 1
C C14C 0.5694(6) 0.1594(3) 0.8602(2) 0.0320(10) Uani d . 1
H H14G 0.5439 0.1153 0.8333 0.048 Uiso calc R 1
H H14H 0.6964 0.1744 0.8571 0.048 Uiso calc R 1
H H14I 0.4830 0.1956 0.8385 0.048 Uiso calc R 1
C C15C 0.5297(7) 0.0300(2) 1.2000(2) 0.0327(10) Uani d . 1
H H15G 0.5087 0.0245 1.2511 0.049 Uiso calc R 1
H H15H 0.6623 0.0265 1.1974 0.049 Uiso calc R 1
H H15I 0.4637 -0.0071 1.1700 0.049 Uiso calc R 1
O O1D 1.0754(5) 0.37834(17) 1.05163(17) 0.0385(8) Uani d . 1
O O2D 0.9971(4) 0.16851(17) 1.18210(17) 0.0344(7) Uani d . 1
O O3D 0.9832(4) 0.08972(17) 1.05741(17) 0.0362(7) Uani d . 1
C C1D 1.0648(5) 0.2665(2) 0.9836(2) 0.0225(8) Uani d . 1
C C2D 1.0529(6) 0.3061(2) 1.0529(2) 0.0289(9) Uani d . 1
C C3D 1.0312(6) 0.2760(2) 1.1192(2) 0.0299(9) Uani d . 1
C C4D 1.0137(6) 0.1999(2) 1.1236(2) 0.0293(9) Uani d . 1
C C5D 1.0099(5) 0.1535(2) 1.0520(2) 0.0267(9) Uani d . 1
C C6D 1.0425(5) 0.1904(2) 0.9816(2) 0.0255(9) Uani d . 1
C C7D 1.0586(5) 0.1517(2) 0.9159(2) 0.0264(9) Uani d . 1
C C8D 1.1000(6) 0.1899(2) 0.8539(2) 0.0283(9) Uani d . 1
H H8DA 1.1119 0.1652 0.8100 0.034 Uiso calc R 1
C C9D 1.1241(5) 0.2637(2) 0.8556(2) 0.0269(9) Uani d . 1
H H9DA 1.1552 0.2872 0.8135 0.032 Uiso calc R 1
C C10D 1.1024(6) 0.3034(2) 0.9195(2) 0.0253(9) Uani d . 1
C C11D 1.1177(6) 0.3842(2) 0.9189(2) 0.0292(9) Uani d . 1
H H11D 1.2514 0.3974 0.9287 0.035 Uiso calc R 1
C C12D 1.0205(7) 0.4143(2) 0.9807(2) 0.0362(11) Uani d . 1
H H12G 1.0501 0.4649 0.9866 0.043 Uiso calc R 1
H H12H 0.8851 0.4099 0.9667 0.043 Uiso calc R 1
C C13D 1.0272(8) 0.3190(3) 1.1908(3) 0.0398(11) Uani d . 1
H H13J 1.0288 0.3693 1.1795 0.060 Uiso calc R 1
H H13K 1.1358 0.3072 1.2263 0.060 Uiso calc R 1
H H13L 0.9147 0.3077 1.2116 0.060 Uiso calc R 1
C C14D 1.0288(6) 0.0721(2) 0.9077(3) 0.0317(10) Uani d . 1
H H14J 1.0474 0.0576 0.8582 0.048 Uiso calc R 1
H H14K 0.9026 0.0604 0.9157 0.048 Uiso calc R 1
H H14L 1.1173 0.0475 0.9440 0.048 Uiso calc R 1
C C15D 1.0303(7) 0.4193(2) 0.8452(2) 0.0329(10) Uani d . 1
H H15J 1.0345 0.4705 0.8506 0.049 Uiso calc R 1
H H15K 0.9015 0.4040 0.8329 0.049 Uiso calc R 1
H H15L 1.1000 0.4053 0.8059 0.049 Uiso calc R 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0000 '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 0.0000 '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_publ_flag
C2A O1A C12A 116.5(3) ?
C10A C1A C6A 120.4(3) ?
C10A C1A C2A 119.2(3) ?
C6A C1A C2A 120.3(3) ?
O1A C2A C3A 115.9(3) ?
O1A C2A C1A 119.0(3) ?
C3A C2A C1A 125.0(4) ?
C2A C3A C4A 118.5(4) ?
C2A C3A C13A 122.5(4) ?
C4A C3A C13A 119.0(4) ?
O2A C4A C3A 123.7(4) ?
O2A C4A C5A 117.3(4) ?
C3A C4A C5A 118.9(4) ?
O3A C5A C6A 124.7(4) ?
O3A C5A C4A 116.8(4) ?
C6A C5A C4A 118.5(3) ?
C7A C6A C1A 119.9(4) ?
C7A C6A C5A 121.9(3) ?
C1A C6A C5A 118.2(3) ?
C8A C7A C6A 118.1(4) ?
C8A C7A C14A 118.8(4) ?
C6A C7A C14A 123.1(4) ?
C9A C8A C7A 122.3(4) ?
C9A C8A H8AA 118.8 ?
C7A C8A H8AA 118.8 ?
C8A C9A C10A 120.3(4) ?
C8A C9A H9AA 119.9 ?
C10A C9A H9AA 119.9 ?
C1A C10A C9A 118.9(4) ?
C1A C10A C11A 120.5(3) ?
C9A C10A C11A 120.6(4) ?
C12A C11A C10A 108.1(3) ?
C12A C11A C15A 112.7(4) y
C10A C11A C15A 111.9(3) ?
C12A C11A H11A 108.0 ?
C10A C11A H11A 108.0 ?
C15A C11A H11A 108.0 ?
O1A C12A C11A 111.2(3) ?
O1A C12A H12A 109.4 ?
C11A C12A H12A 109.4 ?
O1A C12A H12B 109.4 ?
C11A C12A H12B 109.4 ?
H12A C12A H12B 108.0 ?
C3A C13A H13A 109.5 ?
C3A C13A H13B 109.5 ?
H13A C13A H13B 109.5 ?
C3A C13A H13C 109.5 ?
H13A C13A H13C 109.5 ?
H13B C13A H13C 109.5 ?
C7A C14A H14A 109.5 ?
C7A C14A H14B 109.5 ?
H14A C14A H14B 109.5 ?
C7A C14A H14C 109.5 ?
H14A C14A H14C 109.5 ?
H14B C14A H14C 109.5 ?
C11A C15A H15A 109.5 ?
C11A C15A H15B 109.5 ?
H15A C15A H15B 109.5 ?
C11A C15A H15C 109.5 ?
H15A C15A H15C 109.5 ?
H15B C15A H15C 109.5 ?
C2B O1B C12B 117.1(4) ?
C10B C1B C6B 119.9(4) ?
C10B C1B C2B 119.6(4) ?
C6B C1B C2B 120.5(4) ?
O1B C2B C3B 117.4(4) ?
O1B C2B C1B 118.0(4) ?
C3B C2B C1B 124.5(4) ?
C2B C3B C4B 119.1(4) ?
C2B C3B C13B 122.4(4) ?
C4B C3B C13B 118.5(4) ?
O2B C4B C3B 123.1(4) ?
O2B C4B C5B 117.1(4) ?
C3B C4B C5B 119.8(4) ?
O3B C5B C6B 123.9(4) ?
O3B C5B C4B 118.3(4) ?
C6B C5B C4B 117.8(4) ?
C7B C6B C1B 120.7(4) ?
C7B C6B C5B 121.8(4) ?
C1B C6B C5B 117.5(4) ?
C8B C7B C6B 117.6(4) ?
C8B C7B C14B 118.4(4) ?
C6B C7B C14B 124.0(4) ?
C9B C8B C7B 121.2(4) ?
C9B C8B H8BA 119.4 ?
C7B C8B H8BA 119.4 ?
C8B C9B C10B 122.3(4) ?
C8B C9B H9BA 118.8 ?
C10B C9B H9BA 118.8 ?
C9B C10B C1B 118.1(4) ?
C9B C10B C11B 121.4(4) ?
C1B C10B C11B 120.5(4) ?
C10B C11B C12B 107.9(4) ?
C10B C11B C15B 110.9(4) ?
C12B C11B C15B 113.6(4) y
C10B C11B H11B 108.1 ?
C12B C11B H11B 108.1 ?
C15B C11B H11B 108.1 ?
O1B C12B C11B 111.2(4) ?
O1B C12B H12C 109.4 ?
C11B C12B H12C 109.4 ?
O1B C12B H12D 109.4 ?
C11B C12B H12D 109.4 ?
H12C C12B H12D 108.0 ?
C3B C13B H13D 109.5 ?
C3B C13B H13E 109.5 ?
H13D C13B H13E 109.5 ?
C3B C13B H13F 109.5 ?
H13D C13B H13F 109.5 ?
H13E C13B H13F 109.5 ?
C7B C14B H14D 109.5 ?
C7B C14B H14E 109.5 ?
H14D C14B H14E 109.5 ?
C7B C14B H14F 109.5 ?
H14D C14B H14F 109.5 ?
H14E C14B H14F 109.5 ?
C11B C15B H15D 109.5 ?
C11B C15B H15E 109.5 ?
H15D C15B H15E 109.5 ?
C11B C15B H15F 109.5 ?
H15D C15B H15F 109.5 ?
H15E C15B H15F 109.5 ?
C2C O1C C12C 116.7(3) ?
C10C C1C C6C 120.5(4) ?
C10C C1C C2C 119.5(3) ?
C6C C1C C2C 120.0(3) ?
O1C C2C C3C 116.4(4) ?
O1C C2C C1C 118.1(3) ?
C3C C2C C1C 125.4(4) ?
C2C C3C C4C 117.7(4) ?
C2C C3C C13C 123.6(4) ?
C4C C3C C13C 118.7(4) ?
O2C C4C C3C 122.0(4) ?
O2C C4C C5C 117.7(4) ?
C3C C4C C5C 120.3(4) ?
O3C C5C C6C 123.9(4) ?
O3C C5C C4C 117.5(4) ?
C6C C5C C4C 118.6(3) ?
C7C C6C C1C 120.4(4) ?
C7C C6C C5C 122.0(4) ?
C1C C6C C5C 117.6(4) ?
C8C C7C C6C 117.8(4) ?
C8C C7C C14C 118.2(4) ?
C6C C7C C14C 124.0(4) ?
C9C C8C C7C 122.1(4) ?
C9C C8C H8CA 118.9 ?
C7C C8C H8CA 118.9 ?
C8C C9C C10C 121.1(4) ?
C8C C9C H9CA 119.4 ?
C10C C9C H9CA 119.4 ?
C1C C10C C9C 118.0(4) ?
C1C C10C C11C 120.7(4) ?
C9C C10C C11C 121.2(4) ?
C10C C11C C12C 107.9(3) ?
C10C C11C C15C 114.0(3) ?
C12C C11C C15C 108.9(3) y
C10C C11C H11C 108.6 ?
C12C C11C H11C 108.6 ?
C15C C11C H11C 108.6 ?
O1C C12C C11C 111.7(3) ?
O1C C12C H12E 109.3 ?
C11C C12C H12E 109.3 ?
O1C C12C H12F 109.3 ?
C11C C12C H12F 109.3 ?
H12E C12C H12F 107.9 ?
C3C C13C H13G 109.5 ?
C3C C13C H13H 109.5 ?
H13G C13C H13H 109.5 ?
C3C C13C H13I 109.5 ?
H13G C13C H13I 109.5 ?
H13H C13C H13I 109.5 ?
C7C C14C H14G 109.5 ?
C7C C14C H14H 109.5 ?
H14G C14C H14H 109.5 ?
C7C C14C H14I 109.5 ?
H14G C14C H14I 109.5 ?
H14H C14C H14I 109.5 ?
C11C C15C H15G 109.5 ?
C11C C15C H15H 109.5 ?
H15G C15C H15H 109.5 ?
C11C C15C H15I 109.5 ?
H15G C15C H15I 109.5 ?
H15H C15C H15I 109.5 ?
C2D O1D C12D 117.1(3) ?
C10D C1D C6D 120.0(4) ?
C10D C1D C2D 119.8(4) ?
C6D C1D C2D 120.1(4) ?
C3D C2D O1D 117.1(4) ?
C3D C2D C1D 125.1(4) ?
O1D C2D C1D 117.7(4) ?
C2D C3D C4D 118.9(4) ?
C2D C3D C13D 123.4(4) ?
C4D C3D C13D 117.7(4) ?
O2D C4D C3D 122.8(4) ?
O2D C4D C5D 117.2(4) ?
C3D C4D C5D 120.0(4) ?
O3D C5D C6D 124.6(4) ?
O3D C5D C4D 117.7(4) ?
C6D C5D C4D 117.6(4) ?
C7D C6D C1D 120.6(4) ?
C7D C6D C5D 121.4(4) ?
C1D C6D C5D 117.9(4) ?
C8D C7D C6D 117.7(4) ?
C8D C7D C14D 118.0(4) ?
C6D C7D C14D 124.2(4) ?
C9D C8D C7D 122.0(4) ?
C9D C8D H8DA 119.0 ?
C7D C8D H8DA 119.0 ?
C8D C9D C10D 121.1(4) ?
C8D C9D H9DA 119.4 ?
C10D C9D H9DA 119.4 ?
C9D C10D C1D 118.4(4) ?
C9D C10D C11D 120.5(4) ?
C1D C10D C11D 121.1(4) ?
C12D C11D C10D 109.0(4) ?
C12D C11D C15D 108.0(4) y
C10D C11D C15D 114.2(4) ?
C12D C11D H11D 108.5 ?
C10D C11D H11D 108.5 ?
C15D C11D H11D 108.5 ?
O1D C12D C11D 112.7(4) ?
O1D C12D H12G 109.1 ?
C11D C12D H12G 109.1 ?
O1D C12D H12H 109.1 ?
C11D C12D H12H 109.1 ?
H12G C12D H12H 107.8 ?
C3D C13D H13J 109.5 ?
C3D C13D H13K 109.5 ?
H13J C13D H13K 109.5 ?
C3D C13D H13L 109.5 ?
H13J C13D H13L 109.5 ?
H13K C13D H13L 109.5 ?
C7D C14D H14J 109.5 ?
C7D C14D H14K 109.5 ?
H14J C14D H14K 109.5 ?
C7D C14D H14L 109.5 ?
H14J C14D H14L 109.5 ?
H14K C14D H14L 109.5 ?
C11D C15D H15J 109.5 ?
C11D C15D H15K 109.5 ?
H15J C15D H15K 109.5 ?
C11D C15D H15L 109.5 ?
H15J C15D H15L 109.5 ?
H15K C15D H15L 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1A C2A 1.354(5) y
O1A C12A 1.450(5) y
O2A C4A 1.221(5) y
O3A C5A 1.204(5) y
C1A C10A 1.391(6) ?
C1A C6A 1.422(5) ?
C1A C2A 1.463(5) ?
C2A C3A 1.369(6) ?
C3A C4A 1.445(6) ?
C3A C13A 1.505(6) ?
C4A C5A 1.559(6) ?
C5A C6A 1.477(6) ?
C6A C7A 1.407(6) ?
C7A C8A 1.391(6) ?
C7A C14A 1.506(6) ?
C8A C9A 1.374(6) ?
C8A H8AA 0.93 ?
C9A C10A 1.407(6) ?
C9A H9AA 0.93 ?
C10A C11A 1.515(5) ?
C11A C12A 1.505(6) ?
C11A C15A 1.540(6) ?
C11A H11A 0.98 ?
C12A H12A 0.97 ?
C12A H12B 0.97 ?
C13A H13A 0.96 ?
C13A H13B 0.96 ?
C13A H13C 0.96 ?
C14A H14A 0.96 ?
C14A H14B 0.96 ?
C14A H14C 0.96 ?
C15A H15A 0.96 ?
C15A H15B 0.96 ?
C15A H15C 0.96 ?
O1B C2B 1.347(5) y
O1B C12B 1.452(6) y
O2B C4B 1.226(5) y
O3B C5B 1.207(5) y
C1B C10B 1.400(6) ?
C1B C6B 1.424(6) ?
C1B C2B 1.467(6) ?
C2B C3B 1.360(6) ?
C3B C4B 1.424(6) ?
C3B C13B 1.495(7) ?
C4B C5B 1.551(6) ?
C5B C6B 1.500(6) ?
C6B C7B 1.403(6) ?
C7B C8B 1.399(6) ?
C7B C14B 1.499(6) ?
C8B C9B 1.373(6) ?
C8B H8BA 0.93 ?
C9B C10B 1.383(6) ?
C9B H9BA 0.93 ?
C10B C11B 1.496(6) ?
C11B C12B 1.502(6) ?
C11B C15B 1.524(6) ?
C11B H11B 0.98 ?
C12B H12C 0.97 ?
C12B H12D 0.97 ?
C13B H13D 0.96 ?
C13B H13E 0.96 ?
C13B H13F 0.96 ?
C14B H14D 0.96 ?
C14B H14E 0.96 ?
C14B H14F 0.96 ?
C15B H15D 0.96 ?
C15B H15E 0.96 ?
C15B H15F 0.96 ?
O1C C2C 1.351(5) y
O1C C12C 1.448(5) y
O2C C4C 1.227(5) y
O3C C5C 1.214(5) y
C1C C10C 1.394(6) ?
C1C C6C 1.430(5) ?
C1C C2C 1.480(6) ?
C2C C3C 1.361(6) ?
C3C C4C 1.449(6) ?
C3C C13C 1.504(6) ?
C4C C5C 1.536(6) ?
C5C C6C 1.490(6) ?
C6C C7C 1.398(6) ?
C7C C8C 1.394(6) ?
C7C C14C 1.517(6) ?
C8C C9C 1.377(6) ?
C8C H8CA 0.93 ?
C9C C10C 1.404(6) ?
C9C H9CA 0.93 ?
C10C C11C 1.507(5) ?
C11C C12C 1.512(6) ?
C11C C15C 1.534(6) ?
C11C H11C 0.98 ?
C12C H12E 0.97 ?
C12C H12F 0.97 ?
C13C H13G 0.96 ?
C13C H13H 0.96 ?
C13C H13I 0.96 ?
C14C H14G 0.96 ?
C14C H14H 0.96 ?
C14C H14I 0.96 ?
C15C H15G 0.96 ?
C15C H15H 0.96 ?
C15C H15I 0.96 ?
O1D C2D 1.359(5) y
O1D C12D 1.448(5) y
O2D C4D 1.227(5) y
O3D C5D 1.211(5) y
C1D C10D 1.404(6) ?
C1D C6D 1.428(6) ?
C1D C2D 1.464(6) ?
C2D C3D 1.349(6) ?
C3D C4D 1.430(6) ?
C3D C13D 1.523(6) ?
C4D C5D 1.551(6) ?
C5D C6D 1.493(6) ?
C6D C7D 1.407(6) ?
C7D C8D 1.393(6) ?
C7D C14D 1.504(6) ?
C8D C9D 1.389(6) ?
C8D H8DA 0.93 ?
C9D C10D 1.396(6) ?
C9D H9DA 0.93 ?
C10D C11D 1.512(6) ?
C11D C12D 1.504(6) ?
C11D C15D 1.532(6) ?
C11D H11D 0.98 ?
C12D H12G 0.97 ?
C12D H12H 0.97 ?
C13D H13J 0.96 ?
C13D H13K 0.96 ?
C13D H13L 0.96 ?
C14D H14J 0.96 ?
C14D H14K 0.96 ?
C14D H14L 0.96 ?
C15D H15J 0.96 ?
C15D H15K 0.96 ?
C15D H15L 0.96 ?
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
_geom_hbond_publ_flag
C9C H9CA O2C 2_647 0.93 2.45 3.185(5) 136 y
C8D H8DA O2B 1_655 0.93 2.43 3.352(5) 169 y
C11D H11D O2C 1_655 0.98 2.55 3.449(5) 152 y
C12A H12A O3B 1_655 0.97 2.43 3.248(5) 142 y
C12C H12E O3A 1_556 0.97 2.43 3.368(5) 162 y
C12C H12F O2D 1_555 0.97 2.43 3.349(5) 158 y
C12D H12G O3D 2_757 0.97 2.46 3.343(5) 151 y
C12D H12H O2C 1_555 0.97 2.51 3.358(6) 146 y
C14B H14F O1B 2_556 0.96 2.56 3.273(5) 131 y
C15A H15B O3B 1_555 0.96 2.52 3.410(5) 154 y
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
C12A O1A C2A C3A 158.0(4)
C12A O1A C2A C1A -24.9(5)
C10A C1A C2A O1A -4.0(5)
C6A C1A C2A O1A 177.3(3)
C10A C1A C2A C3A 172.8(4)
C6A C1A C2A C3A -6.0(6)
O1A C2A C3A C4A -179.6(3)
C1A C2A C3A C4A 3.5(6)
O1A C2A C3A C13A -1.8(6)
C1A C2A C3A C13A -178.7(4)
C2A C3A C4A O2A -179.6(4)
C13A C3A C4A O2A 2.5(7)
C2A C3A C4A C5A 3.8(6)
C13A C3A C4A C5A -174.1(4)
O2A C4A C5A O3A -6.2(6)
C3A C4A C5A O3A 170.7(4)
O2A C4A C5A C6A 174.4(4)
C3A C4A C5A C6A -8.7(6)
C10A C1A C6A C7A 0.9(6)
C2A C1A C6A C7A 179.7(4)
C10A C1A C6A C5A -178.3(4)
C2A C1A C6A C5A 0.4(5)
O3A C5A C6A C7A 7.8(6)
C4A C5A C6A C7A -172.8(4)
O3A C5A C6A C1A -173.0(4)
C4A C5A C6A C1A 6.4(5)
C1A C6A C7A C8A -1.2(6)
C5A C6A C7A C8A 178.0(4)
C1A C6A C7A C14A 178.8(4)
C5A C6A C7A C14A -2.0(6)
C6A C7A C8A C9A 1.0(6)
C14A C7A C8A C9A -179.0(4)
C7A C8A C9A C10A -0.5(7)
C6A C1A C10A C9A -0.3(6)
C2A C1A C10A C9A -179.1(4)
C6A C1A C10A C11A 179.9(3)
C2A C1A C10A C11A 1.2(5)
C8A C9A C10A C1A 0.1(6)
C8A C9A C10A C11A 179.8(4)
C1A C10A C11A C12A 27.4(5)
C9A C10A C11A C12A -152.4(4)
C1A C10A C11A C15A -97.3(4)
C9A C10A C11A C15A 83.0(5)
C2A O1A C12A C11A 55.5(5)
C10A C11A C12A O1A -53.7(4)
C15A C11A C12A O1A 70.5(4)
C12B O1B C2B C3B 159.2(4)
C12B O1B C2B C1B -24.6(6)
C10B C1B C2B O1B -3.8(6)
C6B C1B C2B O1B 176.5(4)
C10B C1B C2B C3B 172.1(4)
C6B C1B C2B C3B -7.7(7)
O1B C2B C3B C4B -179.1(4)
C1B C2B C3B C4B 5.0(7)
O1B C2B C3B C13B -1.9(7)
C1B C2B C3B C13B -177.8(5)
C2B C3B C4B O2B -179.7(4)
C13B C3B C4B O2B 3.0(7)
C2B C3B C4B C5B 3.2(6)
C13B C3B C4B C5B -174.1(4)
O2B C4B C5B O3B -5.9(6)
C3B C4B C5B O3B 171.4(4)
O2B C4B C5B C6B 174.0(4)
C3B C4B C5B C6B -8.7(6)
C10B C1B C6B C7B -0.1(6)
C2B C1B C6B C7B 179.7(4)
C10B C1B C6B C5B -178.3(4)
C2B C1B C6B C5B 1.5(6)
O3B C5B C6B C7B 7.8(7)
C4B C5B C6B C7B -172.1(4)
O3B C5B C6B C1B -174.0(4)
C4B C5B C6B C1B 6.1(6)
C1B C6B C7B C8B -1.5(6)
C5B C6B C7B C8B 176.6(4)
C1B C6B C7B C14B 179.4(4)
C5B C6B C7B C14B -2.4(6)
C6B C7B C8B C9B 0.9(6)
C14B C7B C8B C9B 180.0(4)
C7B C8B C9B C10B 1.4(7)
C8B C9B C10B C1B -3.0(6)
C8B C9B C10B C11B 179.3(4)
C6B C1B C10B C9B 2.3(6)
C2B C1B C10B C9B -177.5(4)
C6B C1B C10B C11B -180.0(4)
C2B C1B C10B C11B 0.3(6)
C9B C10B C11B C12B -153.9(4)
C1B C10B C11B C12B 28.5(6)
C9B C10B C11B C15B 81.2(5)
C1B C10B C11B C15B -96.5(5)
C2B O1B C12B C11B 55.7(6)
C10B C11B C12B O1B -54.3(5)
C15B C11B C12B O1B 69.0(5)
C12C O1C C2C C3C -157.6(4)
C12C O1C C2C C1C 25.8(5)
C10C C1C C2C O1C 3.4(6)
C6C C1C C2C O1C -179.2(3)
C10C C1C C2C C3C -172.9(4)
C6C C1C C2C C3C 4.5(6)
O1C C2C C3C C4C 180.0(4)
C1C C2C C3C C4C -3.6(7)
O1C C2C C3C C13C 1.0(7)
C1C C2C C3C C13C 177.4(4)
C2C C3C C4C O2C 179.8(4)
C13C C3C C4C O2C -1.2(7)
C2C C3C C4C C5C -2.0(6)
C13C C3C C4C C5C 177.0(4)
O2C C4C C5C O3C 6.6(6)
C3C C4C C5C O3C -171.7(4)
O2C C4C C5C C6C -175.0(4)
C3C C4C C5C C6C 6.7(6)
C10C C1C C6C C7C 0.2(6)
C2C C1C C6C C7C -177.1(4)
C10C C1C C6C C5C 178.1(4)
C2C C1C C6C C5C 0.7(5)
O3C C5C C6C C7C -9.7(6)
C4C C5C C6C C7C 171.9(4)
O3C C5C C6C C1C 172.5(4)
C4C C5C C6C C1C -5.8(5)
C1C C6C C7C C8C -0.9(6)
C5C C6C C7C C8C -178.6(4)
C1C C6C C7C C14C 178.5(4)
C5C C6C C7C C14C 0.8(6)
C6C C7C C8C C9C 1.4(6)
C14C C7C C8C C9C -178.0(4)
C7C C8C C9C C10C -1.3(6)
C6C C1C C10C C9C -0.1(6)
C2C C1C C10C C9C 177.3(4)
C6C C1C C10C C11C -178.8(4)
C2C C1C C10C C11C -1.4(6)
C8C C9C C10C C1C 0.5(6)
C8C C9C C10C C11C 179.3(4)
C1C C10C C11C C12C -26.4(5)
C9C C10C C11C C12C 154.9(4)
C1C C10C C11C C15C -147.6(4)
C9C C10C C11C C15C 33.7(5)
C2C O1C C12C C11C -56.1(5)
C10C C11C C12C O1C 53.4(4)
C15C C11C C12C O1C 177.7(3)
C12D O1D C2D C3D -154.7(4)
C12D O1D C2D C1D 28.8(6)
C10D C1D C2D C3D -175.0(4)
C6D C1D C2D C3D 3.6(7)
C10D C1D C2D O1D 1.3(6)
C6D C1D C2D O1D 179.9(4)
O1D C2D C3D C4D -177.8(4)
C1D C2D C3D C4D -1.5(7)
O1D C2D C3D C13D 1.2(7)
C1D C2D C3D C13D 177.5(4)
C2D C3D C4D O2D 178.6(4)
C13D C3D C4D O2D -0.5(7)
C2D C3D C4D C5D -3.0(6)
C13D C3D C4D C5D 177.9(4)
O2D C4D C5D O3D 3.0(6)
C3D C4D C5D O3D -175.5(4)
O2D C4D C5D C6D -176.1(4)
C3D C4D C5D C6D 5.4(6)
C10D C1D C6D C7D 0.3(6)
C2D C1D C6D C7D -178.3(4)
C10D C1D C6D C5D 177.7(4)
C2D C1D C6D C5D -0.9(6)
O3D C5D C6D C7D -4.9(6)
C4D C5D C6D C7D 174.1(4)
O3D C5D C6D C1D 177.7(4)
C4D C5D C6D C1D -3.3(5)
C1D C6D C7D C8D 1.1(6)
C5D C6D C7D C8D -176.3(4)
C1D C6D C7D C14D -177.1(4)
C5D C6D C7D C14D 5.5(6)
C6D C7D C8D C9D -0.3(6)
C14D C7D C8D C9D 178.0(4)
C7D C8D C9D C10D -1.8(7)
C8D C9D C10D C1D 3.2(6)
C8D C9D C10D C11D -176.3(4)
C6D C1D C10D C9D -2.4(6)
C2D C1D C10D C9D 176.2(4)
C6D C1D C10D C11D 177.1(4)
C2D C1D C10D C11D -4.3(6)
C9D C10D C11D C12D 159.1(4)
C1D C10D C11D C12D -20.4(6)
C9D C10D C11D C15D 38.3(6)
C1D C10D C11D C15D -141.2(4)
C2D O1D C12D C11D -55.5(5)
C10D C11D C12D O1D 48.1(5)
C15D C11D C12D O1D 172.7(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24737446
