#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/10/2221010.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_2221010
loop_
_publ_author_name
'Schinkovitz, Andreas'
'Belaj, Ferdinand'
'Kunert, Olaf'
'Bauer, Rudolf'
_publ_section_title
;
 E-Notopterol
;
_journal_coeditor_code           BT2871
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o545
_journal_paper_doi               10.1107/S1600536809005030
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C21 H22 O5'
_chemical_formula_moiety         'C21 H22 O5'
_chemical_formula_sum            'C21 H22 O5'
_chemical_formula_weight         354.39
_chemical_name_common            E-Notopterol
_chemical_name_systematic
;
4-{[(2E)-5-hydroxy-3,7-dimethyl-
octa-2,6-dien-1-yl]oxy}-7H-furo[3,2-g][1]benzopyran-7-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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                91.802(15)
_cell_angle_beta                 94.240(13)
_cell_angle_gamma                97.473(15)
_cell_formula_units_Z            2
_cell_length_a                   6.4317(10)
_cell_length_b                   8.0912(16)
_cell_length_c                   17.206(3)
_cell_measurement_reflns_used    60
_cell_measurement_temperature    95(2)
_cell_measurement_theta_max      19.80
_cell_measurement_theta_min      15.96
_cell_volume                     884.6(3)
_computing_cell_refinement       'local software'
_computing_data_collection       'local software'
_computing_data_reduction        'local software'
_computing_molecular_graphics    'modified ORTEP (Johnson, 1965)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      95(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Stoe four-circle'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_sigmaI/netI    0.0464
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            4234
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.54
_diffrn_standards_decay_%        0.36
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.214
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3462
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0434
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0482P)²+0.2588P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1125
_reflns_number_gt                2941
_reflns_number_total             3462
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt2871.cif
_cod_data_source_block           I
_cod_database_code               2221010
_cod_database_fobs_code          2221010
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-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_disorder_assembly
_atom_site_disorder_group
O O1 0.08010(16) 1.43591(14) 0.41654(6) 0.0244(3) Uani d . 1 . .
C C2 0.0927(2) 1.43677(19) 0.33658(9) 0.0246(3) Uani d . 1 . .
H H2 -0.0037 1.4827 0.3016 0.028(2) Uiso calc R 1 . .
C C3 0.2568(2) 1.36524(19) 0.31406(9) 0.0226(3) Uani d . 1 . .
H H3 0.2957 1.3524 0.2622 0.028(2) Uiso calc R 1 . .
C C4 0.5403(2) 1.23232(17) 0.40535(8) 0.0177(3) Uani d . 1 . .
C C5 0.7767(2) 1.13743(18) 0.51262(9) 0.0202(3) Uani d . 1 . .
H H5 0.8670 1.1018 0.4760 0.028(2) Uiso calc R 1 . .
C C6 0.8224(2) 1.11882(19) 0.58937(9) 0.0225(3) Uani d . 1 . .
H H6 0.9445 1.0707 0.6059 0.028(2) Uiso calc R 1 . .
C C7 0.6889(2) 1.17088(19) 0.64707(9) 0.0228(3) Uani d . 1 . .
O O7 0.71375(18) 1.15883(16) 0.71723(6) 0.0305(3) Uani d . 1 . .
O O8 0.51411(17) 1.24050(14) 0.62003(6) 0.0231(3) Uani d . 1 . .
C C9 0.2897(2) 1.33880(19) 0.52396(9) 0.0216(3) Uani d . 1 . .
H H9 0.2045 1.3732 0.5626 0.028(2) Uiso calc R 1 . .
C C13 0.3631(2) 1.31129(18) 0.38445(8) 0.0185(3) Uani d . 1 . .
C C14 0.5942(2) 1.21012(17) 0.48527(8) 0.0179(3) Uani d . 1 . .
C C18 0.4657(2) 1.26325(18) 0.54174(8) 0.0189(3) Uani d . 1 . .
C C19 0.2464(2) 1.36067(18) 0.44558(9) 0.0200(3) Uani d . 1 . .
O O4 0.66912(16) 1.17002(14) 0.35580(6) 0.0223(3) Uani d . 1 . .
C C41 0.6201(2) 1.17328(19) 0.27226(8) 0.0206(3) Uani d . 1 . .
H H411 0.6516 1.2880 0.2540 0.022(3) Uiso calc R 1 . .
H H412 0.4695 1.1328 0.2584 0.022(3) Uiso calc R 1 . .
C C42 0.7567(2) 1.05985(18) 0.23652(8) 0.0197(3) Uani d . 1 . .
H H42 0.8956 1.0633 0.2601 0.030(5) Uiso calc R 1 . .
C C43 0.7031(2) 0.95436(18) 0.17484(8) 0.0198(3) Uani d . 1 . .
C C44 0.8569(2) 0.84090(19) 0.14954(9) 0.0215(3) Uani d . 1 . .
H H441 0.9936 0.8725 0.1801 0.031(3) Uiso calc R 1 . .
H H442 0.8797 0.8576 0.0939 0.031(3) Uiso calc R 1 . .
C C45 0.7817(3) 0.6553(2) 0.16021(9) 0.0247(4) Uani d . 1 . .
H H45 0.6569 0.6179 0.1228 0.026(4) Uiso calc R 1 . .
O O5 0.7265(2) 0.62481(16) 0.23818(7) 0.0342(3) Uani d . 1 . .
H H51 0.6537 0.6973 0.2528 0.068(8) Uiso calc R 1 . .
C C46 0.9538(3) 0.5518(2) 0.14538(9) 0.0246(3) Uani d . 1 . .
H H46 1.0863 0.5869 0.1731 0.022(4) Uiso calc R 1 . .
C C47 0.9430(3) 0.4165(2) 0.09793(9) 0.0251(3) Uani d . 1 . .
C C48 1.1328(3) 0.3278(2) 0.08976(10) 0.0322(4) Uani d . 1 . .
H H481 1.2543 0.3891 0.1207 0.042(3) Uiso calc R 1 . .
H H482 1.1628 0.3221 0.0348 0.042(3) Uiso calc R 1 . .
H H483 1.1048 0.2146 0.1085 0.042(3) Uiso calc R 1 . .
C C49 0.4927(3) 0.9353(2) 0.12808(9) 0.0248(3) Uani d . 1 . .
H H491 0.4120 1.0230 0.1448 0.043(3) Uiso calc R 1 . .
H H492 0.4150 0.8258 0.1365 0.043(3) Uiso calc R 1 . .
H H493 0.5146 0.9448 0.0725 0.043(3) Uiso calc R 1 . .
C C50 0.7499(3) 0.3374(2) 0.04907(10) 0.0335(4) Uani d . 1 . .
H H501 0.6298 0.3945 0.0608 0.058(4) Uiso calc R 1 . .
H H502 0.7204 0.2194 0.0609 0.058(4) Uiso calc R 1 . .
H H503 0.7737 0.3470 -0.0063 0.058(4) 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 0.0016 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C19 O1 C2 . . 105.94(12) ?
C3 C2 O1 . . 112.26(14) ?
C3 C2 H2 . . 123.9 ?
O1 C2 H2 . . 123.9 ?
C2 C3 C13 . . 106.62(14) ?
C2 C3 H3 . . 126.7 ?
C13 C3 H3 . . 126.7 ?
O4 C4 C13 . . 126.59(13) ?
O4 C4 C14 . . 114.47(13) ?
C13 C4 C14 . . 118.94(13) ?
C6 C5 C14 . . 121.15(14) ?
C6 C5 H5 . . 119.4 ?
C14 C5 H5 . . 119.4 ?
C5 C6 C7 . . 121.23(15) ?
C5 C6 H6 . . 119.4 ?
C7 C6 H6 . . 119.4 ?
O7 C7 O8 . . 116.20(14) ?
O7 C7 C6 . . 126.77(15) ?
O8 C7 C6 . . 117.03(13) ?
C7 O8 C18 . . 122.82(12) ?
C18 C9 C19 . . 114.72(14) ?
C18 C9 H9 . . 122.6 ?
C19 C9 H9 . . 122.6 ?
C4 C13 C19 . . 117.12(13) ?
C4 C13 C3 . . 138.18(14) ?
C19 C13 C3 . . 104.68(13) ?
C18 C14 C4 . . 119.34(13) ?
C18 C14 C5 . . 117.56(13) ?
C4 C14 C5 . . 123.09(13) ?
C9 C18 O8 . . 116.11(13) ?
C9 C18 C14 . . 123.71(14) ?
O8 C18 C14 . . 120.18(13) ?
O1 C19 C9 . . 123.36(14) ?
O1 C19 C13 . . 110.49(13) ?
C9 C19 C13 . . 126.15(14) ?
C4 O4 C41 . . 119.53(11) ?
O4 C41 C42 . . 105.47(12) ?
O4 C41 H411 . . 110.6 ?
C42 C41 H411 . . 110.6 ?
O4 C41 H412 . . 110.6 ?
C42 C41 H412 . . 110.6 ?
H411 C41 H412 . . 108.8 ?
C43 C42 C41 . . 126.62(14) ?
C43 C42 H42 . . 116.7 ?
C41 C42 H42 . . 116.7 ?
C42 C43 C49 . . 124.47(14) ?
C42 C43 C44 . . 119.56(14) ?
C49 C43 C44 . . 115.95(13) ?
C43 C44 C45 . . 113.08(13) ?
C43 C44 H441 . . 109.0 ?
C45 C44 H441 . . 109.0 ?
C43 C44 H442 . . 109.0 ?
C45 C44 H442 . . 109.0 ?
H441 C44 H442 . . 107.8 ?
O5 C45 C46 . . 106.58(13) ?
O5 C45 C44 . . 111.88(13) ?
C46 C45 C44 . . 110.45(13) ?
O5 C45 H45 . . 109.3 ?
C46 C45 H45 . . 109.3 ?
C44 C45 H45 . . 109.3 ?
C45 O5 H51 . . 109.5 ?
C47 C46 C45 . . 127.87(15) ?
C47 C46 H46 . . 116.1 ?
C45 C46 H46 . . 116.1 ?
C46 C47 C50 . . 125.44(16) ?
C46 C47 C48 . . 120.82(15) ?
C50 C47 C48 . . 113.73(15) ?
C47 C48 H481 . . 109.5 ?
C47 C48 H482 . . 109.5 ?
H481 C48 H482 . . 109.5 ?
C47 C48 H483 . . 109.5 ?
H481 C48 H483 . . 109.5 ?
H482 C48 H483 . . 109.5 ?
C43 C49 H491 . . 109.5 ?
C43 C49 H492 . . 109.5 ?
H491 C49 H492 . . 109.5 ?
C43 C49 H493 . . 109.5 ?
H491 C49 H493 . . 109.5 ?
H492 C49 H493 . . 109.5 ?
C47 C50 H501 . . 109.5 ?
C47 C50 H502 . . 109.5 ?
H501 C50 H502 . . 109.5 ?
C47 C50 H503 . . 109.5 ?
H501 C50 H503 . . 109.5 ?
H502 C50 H503 . . 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 C19 . 1.3688(18) ?
O1 C2 . 1.3843(19) ?
C2 C3 . 1.343(2) ?
C2 H2 . 0.95 ?
C3 C13 . 1.454(2) ?
C3 H3 . 0.95 ?
C4 O4 . 1.3613(18) ?
C4 C13 . 1.407(2) ?
C4 C14 . 1.416(2) ?
C5 C6 . 1.349(2) ?
C5 C14 . 1.436(2) ?
C5 H5 . 0.95 ?
C6 C7 . 1.447(2) ?
C6 H6 . 0.95 ?
C7 O7 . 1.2145(19) ?
C7 O8 . 1.3788(19) ?
O8 C18 . 1.3834(18) ?
C9 C18 . 1.375(2) ?
C9 C19 . 1.378(2) ?
C9 H9 . 0.95 ?
C13 C19 . 1.413(2) ?
C14 C18 . 1.413(2) ?
O4 C41 . 1.4504(17) ?
C41 C42 . 1.499(2) ?
C41 H411 . 0.99 ?
C41 H412 . 0.99 ?
C42 C43 . 1.336(2) ?
C42 H42 . 0.95 ?
C43 C49 . 1.509(2) ?
C43 C44 . 1.512(2) ?
C44 C45 . 1.537(2) ?
C44 H441 . 0.99 ?
C44 H442 . 0.99 ?
C45 O5 . 1.4336(19) ?
C45 C46 . 1.504(2) ?
C45 H45 . 1.00 ?
O5 H51 . 0.84 ?
C46 C47 . 1.337(2) ?
C46 H46 . 0.95 ?
C47 C50 . 1.504(2) ?
C47 C48 . 1.507(2) ?
C48 H481 . 0.98 ?
C48 H482 . 0.98 ?
C48 H483 . 0.98 ?
C49 H491 . 0.98 ?
C49 H492 . 0.98 ?
C49 H493 . 0.98 ?
C50 H501 . 0.98 ?
C50 H502 . 0.98 ?
C50 H503 . 0.98 ?
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
O5 H51 O8 2_676 0.84 2.57 3.2193(16) 134.5
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
C19 O1 C2 C3 . . . . 0.41(17) ?
O1 C2 C3 C13 . . . . 0.19(18) ?
C14 C5 C6 C7 . . . . 0.2(2) ?
C5 C6 C7 O7 . . . . 179.33(15) ?
C5 C6 C7 O8 . . . . -0.2(2) ?
O7 C7 O8 C18 . . . . 179.60(13) ?
C6 C7 O8 C18 . . . . -0.8(2) ?
O4 C4 C13 C19 . . . . 177.50(13) ?
C14 C4 C13 C19 . . . . -1.4(2) ?
O4 C4 C13 C3 . . . . -4.3(3) ?
C14 C4 C13 C3 . . . . 176.88(16) ?
C2 C3 C13 C4 . . . . -179.08(17) ?
C2 C3 C13 C19 . . . . -0.70(16) ?
O4 C4 C14 C18 . . . . -177.18(12) ?
C13 C4 C14 C18 . . . . 1.8(2) ?
O4 C4 C14 C5 . . . . 3.7(2) ?
C13 C4 C14 C5 . . . . -177.31(13) ?
C6 C5 C14 C18 . . . . 0.8(2) ?
C6 C5 C14 C4 . . . . 179.90(14) ?
C19 C9 C18 O8 . . . . 179.60(12) ?
C19 C9 C18 C14 . . . . -0.4(2) ?
C7 O8 C18 C9 . . . . -178.14(13) ?
C7 O8 C18 C14 . . . . 1.8(2) ?
C4 C14 C18 C9 . . . . -0.9(2) ?
C5 C14 C18 C9 . . . . 178.22(14) ?
C4 C14 C18 O8 . . . . 179.09(12) ?
C5 C14 C18 O8 . . . . -1.7(2) ?
C2 O1 C19 C9 . . . . 178.89(14) ?
C2 O1 C19 C13 . . . . -0.87(16) ?
C18 C9 C19 O1 . . . . -178.88(13) ?
C18 C9 C19 C13 . . . . 0.9(2) ?
C4 C13 C19 O1 . . . . 179.76(12) ?
C3 C13 C19 O1 . . . . 0.98(16) ?
C4 C13 C19 C9 . . . . 0.0(2) ?
C3 C13 C19 C9 . . . . -178.78(14) ?
C13 C4 O4 C41 . . . . -3.8(2) ?
C14 C4 O4 C41 . . . . 175.09(12) ?
C4 O4 C41 C42 . . . . -166.21(12) ?
O4 C41 C42 C43 . . . . 141.31(15) ?
C41 C42 C43 C49 . . . . 2.1(2) ?
C41 C42 C43 C44 . . . . -176.19(14) ?
C42 C43 C44 C45 . . . . 113.54(16) ?
C49 C43 C44 C45 . . . . -64.89(17) ?
C43 C44 C45 O5 . . . . -53.12(17) ?
C43 C44 C45 C46 . . . . -171.68(13) ?
O5 C45 C46 C47 . . . . 109.83(18) ?
C44 C45 C46 C47 . . . . -128.43(17) ?
C45 C46 C47 C50 . . . . -0.7(3) ?
C45 C46 C47 C48 . . . . 179.69(15) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4478370
