#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/59/2225997.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_2225997
loop_
_publ_author_name
'Kalyanaraman, L.'
'Mohan Kumar, R.'
'Vishweshwar, Peddy'
'Pichai, R.'
'Narasimhan, S.'
_publ_section_title
;
 5-Methoxy-2,2-dimethyl-6-[(2E)-2-methylbut-2-enoyl]-10-phenyl-2H,8H-pyrano[2,3-f]chromen-8-one
 (calophyllolide)
;
_journal_coeditor_code           TK2651
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1115
_journal_paper_doi               10.1107/S1600536810013577
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C26 H24 O5'
_chemical_formula_moiety         'C26 H24 O5'
_chemical_formula_sum            'C26 H24 O5'
_chemical_formula_weight         416.47
_chemical_name_common
;
calophyllolide
;
_chemical_name_systematic
;
5-Methoxy-2,2-dimethyl-6-[(2E)-2-methylbut-2-enoyl]-10-phenyl-
2H,8H-pyrano[2,3-f]chromen-8-one
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                96.238(8)
_cell_angle_beta                 104.041(5)
_cell_angle_gamma                110.301(8)
_cell_formula_units_Z            2
_cell_length_a                   8.943(3)
_cell_length_b                   11.559(4)
_cell_length_c                   12.171(3)
_cell_measurement_reflns_used    4735
_cell_measurement_temperature    298
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      2.5
_cell_volume                     1118.7(6)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction
'CrystalStructure (Molecular Structure Corporation & Rigaku, 2006)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material
'CrystalStructure (Molecular Structure Corporation & Rigaku, 2006)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al.,  2003)'
_computing_structure_solution    'SIR2004 (Burla et al.,  2005)'
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.055
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12333
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         27.41
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             440.00
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.50
_refine_diff_density_max         0.34
_refine_diff_density_min         -0.31
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     304
_refine_ls_number_reflns         4480
_refine_ls_R_factor_gt           0.0777
_refine_ls_shift/su_max          0.0180
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
Chebychev polynomial with 3 parameters (Carruthers & Watkin, 1979):
26851.8000, 36815.3000, 10053.3000
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0922
_reflns_number_gt                2706
_reflns_number_total             4480
_reflns_threshold_expression     F²>2σ(F²)
_cod_data_source_file            tk2651.cif
_cod_data_source_block           I
_cod_database_code               2225997
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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
O O1 0.76337(17) 1.04526(10) 0.54924(11) 0.0565(4) Uani . . 1.000
O O2 0.6788(2) 1.17903(13) 0.46095(14) 0.0901(7) Uani . . 1.000
O O3 0.61388(16) 0.61390(10) 0.36909(10) 0.0549(4) Uani . . 1.000
O O4 0.97605(19) 0.78784(14) 0.75890(11) 0.0674(5) Uani . . 1.000
O O5 1.1027(2) 1.10050(18) 0.75198(16) 0.1159(8) Uani . . 1.000
C C1 0.6716(2) 1.07075(17) 0.45404(18) 0.0615(7) Uani . . 1.000
C C2 0.5705(2) 0.96723(17) 0.35769(17) 0.0598(7) Uani . . 1.000
C C3 0.5714(2) 0.85017(16) 0.35387(15) 0.0478(5) Uani . . 1.000
C C4 0.7000(2) 0.71305(14) 0.46131(14) 0.0454(5) Uani . . 1.000
C C5 0.7989(2) 0.69796(16) 0.56201(15) 0.0508(5) Uani . . 1.000
C C6 0.8849(2) 0.80206(17) 0.65664(15) 0.0519(6) Uani . . 1.000
C C7 0.8693(2) 0.91656(15) 0.65085(15) 0.0484(5) Uani . . 1.000
C C8 0.7687(2) 0.92695(14) 0.54971(15) 0.0449(5) Uani . . 1.000
C C9 0.6773(2) 0.82733(14) 0.45266(13) 0.0417(5) Uani . . 1.000
C C10 0.6832(2) 0.51684(16) 0.35424(17) 0.0589(6) Uani . . 1.000
C C11 0.7414(3) 0.48607(17) 0.4694(2) 0.0740(8) Uani . . 1.000
C C12 0.8001(3) 0.57273(18) 0.56640(19) 0.0688(8) Uani . . 1.000
C C13 0.8261(3) 0.5703(2) 0.3035(2) 0.0845(10) Uani . . 1.000
C C14 0.5371(3) 0.40608(18) 0.2700(2) 0.0821(9) Uani . . 1.000
C C15 1.1373(3) 0.7892(2) 0.7603(2) 0.0913(10) Uani . . 1.000
C C16 0.9666(2) 1.02968(17) 0.75119(16) 0.0569(6) Uani . . 1.000
C C17 0.8941(2) 1.05157(16) 0.84342(15) 0.0540(6) Uani . . 1.000
C C18 0.7537(2) 0.9633(2) 0.84800(17) 0.0637(7) Uani . . 1.000
C C19 0.6672(3) 0.9685(3) 0.9381(2) 0.1058(11) Uani . . 1.000
C C20 0.9897(3) 1.1736(2) 0.9313(2) 0.0908(9) Uani . . 1.000
C C21 0.4565(2) 0.74887(17) 0.24960(15) 0.0530(5) Uani . . 1.000
C C22 0.3021(2) 0.6686(2) 0.25190(19) 0.0747(8) Uani . . 1.000
C C23 0.1968(3) 0.5724(2) 0.1561(2) 0.0879(9) Uani . . 1.000
C C24 0.2434(3) 0.5585(2) 0.0590(2) 0.0906(9) Uani . . 1.000
C C25 0.3941(3) 0.6396(2) 0.0550(2) 0.1014(10) Uani . . 1.000
C C26 0.5003(3) 0.7362(2) 0.14927(19) 0.0842(9) Uani . . 1.000
H H2 0.50080 0.98190 0.29290 0.0750 Uiso calc R 1.000
H H11 0.73470 0.40280 0.47280 0.0930 Uiso calc R 1.000
H H12 0.84350 0.55350 0.63820 0.0880 Uiso calc R 1.000
H H18 0.70430 0.88900 0.78860 0.0790 Uiso calc R 1.000
H H22 0.26760 0.67840 0.31910 0.0850 Uiso calc R 1.000
H H23 0.09120 0.51610 0.15790 0.0930 Uiso calc R 1.000
H H24 0.17210 0.49190 -0.00560 0.0950 Uiso calc R 1.000
H H25 0.42410 0.63110 -0.01430 0.1080 Uiso calc R 1.000
H H26 0.60490 0.79210 0.14550 0.0910 Uiso calc R 1.000
H H131 0.90770 0.53590 0.32850 0.1110 Uiso calc R 1.000
H H132 0.87580 0.65960 0.32870 0.1110 Uiso calc R 1.000
H H133 0.78370 0.54880 0.22140 0.1110 Uiso calc R 1.000
H H141 0.47650 0.35420 0.31270 0.0950 Uiso calc R 1.000
H H142 0.57630 0.35810 0.22430 0.0940 Uiso calc R 1.000
H H143 0.46610 0.43660 0.22100 0.0950 Uiso calc R 1.000
H H151 1.12660 0.70530 0.73490 0.1170 Uiso calc R 1.000
H H152 1.21370 0.82260 0.83630 0.1170 Uiso calc R 1.000
H H153 1.17770 0.83980 0.70910 0.1170 Uiso calc R 1.000
H H191 0.55050 0.92150 0.90490 0.1330 Uiso calc R 1.000
H H192 0.70940 0.93440 1.00040 0.1340 Uiso calc R 1.000
H H193 0.68690 1.05410 0.96610 0.1340 Uiso calc R 1.000
H H201 0.91510 1.20110 0.95980 0.1020 Uiso calc R 1.000
H H202 1.06610 1.16130 0.99370 0.1020 Uiso calc R 1.000
H H203 1.04970 1.23560 0.89570 0.1020 Uiso calc R 1.000
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
O O 0.011 0.006
;
International Tables for Crystallography
(1992, 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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 O1 C8 . . . 121.76(14) no
C4 O3 C10 . . . 117.74(14) no
C6 O4 C15 . . . 115.00(16) no
O1 C1 O2 . . . 116.84(18) no
O1 C1 C2 . . . 117.20(16) no
O2 C1 C2 . . . 125.90(19) no
C1 C2 C3 . . . 123.13(18) no
C2 C3 C9 . . . 118.60(16) no
C2 C3 C21 . . . 118.10(17) no
C9 C3 C21 . . . 123.24(15) no
O3 C4 C5 . . . 120.05(15) no
O3 C4 C9 . . . 117.64(15) no
C5 C4 C9 . . . 122.22(15) no
C4 C5 C6 . . . 118.71(16) no
C4 C5 C12 . . . 117.92(16) no
C6 C5 C12 . . . 123.27(17) no
O4 C6 C5 . . . 119.82(17) no
O4 C6 C7 . . . 119.10(16) no
C5 C6 C7 . . . 120.92(16) no
C6 C7 C8 . . . 118.42(16) no
C6 C7 C16 . . . 120.80(16) no
C8 C7 C16 . . . 120.72(15) no
O1 C8 C7 . . . 115.05(15) no
O1 C8 C9 . . . 120.94(15) no
C7 C8 C9 . . . 124.01(15) no
C3 C9 C4 . . . 126.22(15) no
C3 C9 C8 . . . 118.14(15) no
C4 C9 C8 . . . 115.64(15) no
O3 C10 C11 . . . 109.14(16) no
O3 C10 C13 . . . 107.16(15) no
O3 C10 C14 . . . 103.60(16) no
C11 C10 C13 . . . 111.86(19) no
C11 C10 C14 . . . 112.31(16) no
C13 C10 C14 . . . 112.28(18) no
C10 C11 C12 . . . 121.01(18) no
C5 C12 C11 . . . 119.6(2) no
O5 C16 C7 . . . 118.35(18) no
O5 C16 C17 . . . 121.52(18) no
C7 C16 C17 . . . 120.12(16) no
C16 C17 C18 . . . 119.84(17) no
C16 C17 C20 . . . 116.41(18) no
C18 C17 C20 . . . 123.71(19) no
C17 C18 C19 . . . 126.6(2) no
C3 C21 C22 . . . 120.04(17) no
C3 C21 C26 . . . 121.08(18) no
C22 C21 C26 . . . 118.86(19) no
C21 C22 C23 . . . 120.1(2) no
C22 C23 C24 . . . 120.4(2) no
C23 C24 C25 . . . 119.8(2) no
C24 C25 C26 . . . 120.7(2) no
C21 C26 C25 . . . 120.1(2) no
C1 C2 H2 . . . 118.00 no
C3 C2 H2 . . . 118.00 no
C10 C11 H11 . . . 119.00 no
C12 C11 H11 . . . 120.00 no
C5 C12 H12 . . . 120.00 no
C11 C12 H12 . . . 120.00 no
C10 C13 H131 . . . 110.00 no
C10 C13 H132 . . . 110.00 no
C10 C13 H133 . . . 109.00 no
H131 C13 H132 . . . 109.00 no
H131 C13 H133 . . . 110.00 no
H132 C13 H133 . . . 109.00 no
C10 C14 H141 . . . 109.00 no
C10 C14 H142 . . . 110.00 no
C10 C14 H143 . . . 109.00 no
H141 C14 H142 . . . 109.00 no
H141 C14 H143 . . . 109.00 no
H142 C14 H143 . . . 110.00 no
O4 C15 H151 . . . 109.00 no
O4 C15 H152 . . . 111.00 no
O4 C15 H153 . . . 109.00 no
H151 C15 H152 . . . 109.00 no
H151 C15 H153 . . . 110.00 no
H152 C15 H153 . . . 109.00 no
C17 C18 H18 . . . 117.00 no
C19 C18 H18 . . . 117.00 no
C18 C19 H191 . . . 110.00 no
C18 C19 H192 . . . 110.00 no
C18 C19 H193 . . . 109.00 no
H191 C19 H192 . . . 110.00 no
H191 C19 H193 . . . 109.00 no
H192 C19 H193 . . . 109.00 no
C17 C20 H201 . . . 110.00 no
C17 C20 H202 . . . 109.00 no
C17 C20 H203 . . . 109.00 no
H201 C20 H202 . . . 110.00 no
H201 C20 H203 . . . 109.00 no
H202 C20 H203 . . . 109.00 no
C21 C22 H22 . . . 120.00 no
C23 C22 H22 . . . 120.00 no
C22 C23 H23 . . . 120.00 no
C24 C23 H23 . . . 119.00 no
C23 C24 H24 . . . 120.00 no
C25 C24 H24 . . . 120.00 no
C24 C25 H25 . . . 119.00 no
C26 C25 H25 . . . 120.00 no
C21 C26 H26 . . . 120.00 no
C25 C26 H26 . . . 120.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . . 1.372(2) no
O1 C8 . . 1.385(2) no
O2 C1 . . 1.223(2) no
O3 C4 . . 1.362(2) no
O3 C10 . . 1.473(2) no
O4 C6 . . 1.373(2) no
O4 C15 . . 1.433(3) no
O5 C16 . . 1.205(3) no
C1 C2 . . 1.433(3) no
C2 C3 . . 1.352(3) no
C3 C9 . . 1.450(2) no
C3 C21 . . 1.499(3) no
C4 C5 . . 1.394(2) no
C4 C9 . . 1.415(2) no
C5 C6 . . 1.412(3) no
C5 C12 . . 1.458(3) no
C6 C7 . . 1.386(3) no
C7 C8 . . 1.382(3) no
C7 C16 . . 1.519(3) no
C8 C9 . . 1.404(2) no
C10 C11 . . 1.498(3) no
C10 C13 . . 1.521(3) no
C10 C14 . . 1.517(3) no
C11 C12 . . 1.323(3) no
C16 C17 . . 1.466(3) no
C17 C18 . . 1.333(3) no
C17 C20 . . 1.502(3) no
C18 C19 . . 1.495(3) no
C21 C22 . . 1.380(3) no
C21 C26 . . 1.378(3) no
C22 C23 . . 1.393(3) no
C23 C24 . . 1.357(4) no
C24 C25 . . 1.365(4) no
C25 C26 . . 1.386(3) no
C2 H2 . . 0.9500 no
C11 H11 . . 0.9500 no
C12 H12 . . 0.9500 no
C13 H131 . . 0.9500 no
C13 H132 . . 0.9500 no
C13 H133 . . 0.9500 no
C14 H141 . . 0.9500 no
C14 H142 . . 0.9500 no
C14 H143 . . 0.9500 no
C15 H151 . . 0.9500 no
C15 H152 . . 0.9500 no
C15 H153 . . 0.9500 no
C18 H18 . . 0.9500 no
C19 H191 . . 0.9500 no
C19 H192 . . 0.9500 no
C19 H193 . . 0.9500 no
C20 H201 . . 0.9500 no
C20 H202 . . 0.9500 no
C20 H203 . . 0.9500 no
C22 H22 . . 0.9500 no
C23 H23 . . 0.9500 no
C24 H24 . . 0.9500 no
C25 H25 . . 0.9500 no
C26 H26 . . 0.9500 no
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
C11 H11 O2 1_545 0.95 2.44 3.381(3) 172 yes
C26 H26 O5 2_776 0.95 2.40 3.225(3) 145 yes
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
C8 O1 C1 O2 . . . . -177.92(18) no
C8 O1 C1 C2 . . . . 4.8(3) no
C1 O1 C8 C7 . . . . 178.65(17) no
C1 O1 C8 C9 . . . . -1.1(3) no
C10 O3 C4 C5 . . . . -28.4(2) no
C10 O3 C4 C9 . . . . 155.07(16) no
C4 O3 C10 C11 . . . . 43.8(2) no
C4 O3 C10 C13 . . . . -77.49(19) no
C4 O3 C10 C14 . . . . 163.64(15) no
C15 O4 C6 C5 . . . . 79.4(2) no
C15 O4 C6 C7 . . . . -105.2(2) no
O1 C1 C2 C3 . . . . -4.8(3) no
O2 C1 C2 C3 . . . . 178.1(2) no
C1 C2 C3 C9 . . . . 1.1(3) no
C1 C2 C3 C21 . . . . 178.37(18) no
C2 C3 C9 C4 . . . . -176.70(19) no
C2 C3 C9 C8 . . . . 2.6(3) no
C21 C3 C9 C4 . . . . 6.2(3) no
C21 C3 C9 C8 . . . . -174.46(17) no
C2 C3 C21 C22 . . . . -95.7(2) no
C2 C3 C21 C26 . . . . 82.5(3) no
C9 C3 C21 C22 . . . . 81.4(3) no
C9 C3 C21 C26 . . . . -100.4(2) no
O3 C4 C5 C6 . . . . -179.18(17) no
O3 C4 C5 C12 . . . . -2.8(3) no
C9 C4 C5 C6 . . . . -2.8(3) no
C9 C4 C5 C12 . . . . 173.62(19) no
O3 C4 C9 C3 . . . . -0.6(3) no
O3 C4 C9 C8 . . . . -179.93(16) no
C5 C4 C9 C3 . . . . -177.06(18) no
C5 C4 C9 C8 . . . . 3.6(3) no
C4 C5 C6 O4 . . . . 176.58(18) no
C4 C5 C6 C7 . . . . 1.2(3) no
C12 C5 C6 O4 . . . . 0.4(3) no
C12 C5 C6 C7 . . . . -175.0(2) no
C4 C5 C12 C11 . . . . 15.4(3) no
C6 C5 C12 C11 . . . . -168.4(2) no
O4 C6 C7 C8 . . . . -176.02(18) no
O4 C6 C7 C16 . . . . 6.7(3) no
C5 C6 C7 C8 . . . . -0.6(3) no
C5 C6 C7 C16 . . . . -177.87(17) no
C6 C7 C8 O1 . . . . -178.13(17) no
C6 C7 C8 C9 . . . . 1.6(3) no
C16 C7 C8 O1 . . . . -0.9(3) no
C16 C7 C8 C9 . . . . 178.89(18) no
C6 C7 C16 O5 . . . . 90.6(2) no
C6 C7 C16 C17 . . . . -90.1(2) no
C8 C7 C16 O5 . . . . -86.6(3) no
C8 C7 C16 C17 . . . . 92.8(2) no
O1 C8 C9 C3 . . . . -2.7(3) no
O1 C8 C9 C4 . . . . 176.71(16) no
C7 C8 C9 C3 . . . . 177.57(18) no
C7 C8 C9 C4 . . . . -3.0(3) no
O3 C10 C11 C12 . . . . -31.7(3) no
C13 C10 C11 C12 . . . . 86.8(3) no
C14 C10 C11 C12 . . . . -145.9(3) no
C10 C11 C12 C5 . . . . 3.7(4) no
O5 C16 C17 C18 . . . . -171.3(2) no
O5 C16 C17 C20 . . . . 6.4(3) no
C7 C16 C17 C18 . . . . 9.4(3) no
C7 C16 C17 C20 . . . . -172.87(17) no
C16 C17 C18 C19 . . . . 177.6(2) no
C20 C17 C18 C19 . . . . 0.1(3) no
C3 C21 C22 C23 . . . . -178.4(2) no
C26 C21 C22 C23 . . . . 3.4(3) no
C3 C21 C26 C25 . . . . 178.2(2) no
C22 C21 C26 C25 . . . . -3.6(3) no
C21 C22 C23 C24 . . . . -1.5(4) no
C22 C23 C24 C25 . . . . -0.3(4) no
C23 C24 C25 C26 . . . . 0.0(4) no
C24 C25 C26 C21 . . . . 2.0(4) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4444746
