#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/99/2209954.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_2209954
loop_
_publ_author_name
'Ying Chang'
'Gang Xu'
'Qin-Shi Zhao'
'Yang Lu'
'Qi-Tai Zheng'
_publ_section_title
10-Acetonyl-10-hydroxy-1,6-dimethyl-1,2,10,11-tetrahydrophenanthro[1,2-b]furan-11-one
_journal_coeditor_code           NC2018
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3235
_journal_page_last               o3236
_journal_paper_doi               10.1107/S1600536806025438
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C21 H20 O4'
_chemical_formula_moiety         'C21 H20 O4'
_chemical_formula_sum            'C21 H20 O4'
_chemical_formula_weight         336.37
_chemical_name_common            'danshenol A'
_chemical_name_systematic
;
10-Acetonyl-10-hydroxy-1,6-dimethyl-1,2,10,11-
tetrahydrophenanthro[1,2-b]furan-11-one
;
_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                 102.75(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.5180(15)
_cell_length_b                   6.7150(13)
_cell_length_c                   17.161(3)
_cell_measurement_reflns_used    1930
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.21
_cell_measurement_theta_min      2.43
_cell_volume                     845.0(3)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'DENZO (Otwinowski & Minor, 1997)'
_computing_data_reduction        SCALEPACK
_computing_molecular_graphics
'ORTEPII (Johnson, 1976) and PLUTON (Spek, 2003)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_device_type  'MAC DIP 2030K'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotate anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_av_sigmaI/netI    0.0144
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            7044
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.21
_diffrn_reflns_theta_min         2.43
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.216
_refine_ls_extinction_coef       0.081(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         1930
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0649
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1047P)²+0.3521P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1766
_refine_ls_wR_factor_ref         0.1789
_reflns_number_gt                1894
_reflns_number_total             1930
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            nc2018.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2209954
_cod_database_fobs_code          2209954
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 O1 0.8139(3) -0.1269(4) 0.25560(16) 0.0497(7) Uani d . 1
O O2 0.1522(3) 0.0997(5) 0.27739(14) 0.0479(7) Uani d . 1
H H2A 0.0550 0.1287 0.2472 0.072 Uiso calc R 1
O O3 -0.0940(6) 0.2250(12) 0.1253(3) 0.033(2) Uani d D 1
O O4 0.1899(3) -0.1879(5) 0.17424(19) 0.0567(8) Uani d . 1
C C1 0.2721(5) 0.4906(6) 0.3341(2) 0.0479(9) Uani d . 1
H H1A 0.1644 0.4337 0.3057 0.058 Uiso calc R 1
C C2 0.2657(6) 0.6661(8) 0.3733(2) 0.0569(10) Uani d . 1
H H2B 0.1539 0.7289 0.3697 0.068 Uiso calc R 1
C C3 0.4236(6) 0.7535(7) 0.4187(2) 0.0564(10) Uani d . 1
H H3B 0.4146 0.8723 0.4454 0.068 Uiso calc R 1
C C4 0.5921(6) 0.6672(7) 0.4247(2) 0.0517(9) Uani d . 1
C C5 0.6041(5) 0.4828(6) 0.3837(2) 0.0440(8) Uani d . 1
C C6 0.7749(5) 0.3887(8) 0.3876(2) 0.0532(10) Uani d . 1
H H6A 0.8793 0.4447 0.4192 0.064 Uiso calc R 1
C C7 0.7902(5) 0.2187(7) 0.3463(2) 0.0498(9) Uani d . 1
H H7A 0.9037 0.1595 0.3503 0.060 Uiso calc R 1
C C8 0.6319(4) 0.1320(6) 0.29697(18) 0.0389(7) Uani d . 1
C C9 0.4595(4) 0.2136(5) 0.29251(18) 0.0369(7) Uani d . 1
C C10 0.4427(4) 0.3920(6) 0.33581(19) 0.0411(8) Uani d . 1
C C11 0.2953(4) 0.1210(6) 0.23669(18) 0.0381(7) Uani d . 1
C C12 0.3269(4) -0.0894(6) 0.2029(2) 0.0411(7) Uani d . 1
C C13 0.5092(5) -0.1473(6) 0.20540(19) 0.0411(8) Uani d . 1
C C14 0.6469(4) -0.0454(6) 0.2510(2) 0.0413(8) Uani d . 1
C C15 0.7868(5) -0.3021(8) 0.2027(3) 0.0594(11) Uani d . 1
H H15A 0.8367 -0.4200 0.2323 0.071 Uiso calc R 1
H H15B 0.8482 -0.2829 0.1591 0.071 Uiso calc R 1
C C16 0.5818(5) -0.3271(7) 0.1700(2) 0.0492(9) Uani d . 1
H H16A 0.5408 -0.4475 0.1932 0.059 Uiso calc R 1
C C17 0.7590(7) 0.7632(10) 0.4740(3) 0.0744(14) Uani d . 1
H H17A 0.7246 0.8801 0.4993 0.112 Uiso calc R 1
H H17B 0.8398 0.8000 0.4402 0.112 Uiso calc R 1
H H17C 0.8195 0.6714 0.5140 0.112 Uiso calc R 1
C C18 0.2410(5) 0.2579(8) 0.1611(2) 0.0535(10) Uani d . 1
H H18A 0.2319 0.3943 0.1785 0.064 Uiso calc R 1
H H18B 0.3374 0.2530 0.1317 0.064 Uiso calc R 1
C C19 0.0595(8) 0.1996(11) 0.1043(3) 0.054(2) Uani d D 1
C C20 0.0820(13) 0.1231(13) 0.0285(3) 0.065(3) Uani d . 1
H H20A -0.0350 0.0875 -0.0037 0.095 Uiso calc R 1
H H20B 0.1590 0.0076 0.0373 0.095 Uiso calc R 1
H H20C 0.1369 0.2233 0.0016 0.095 Uiso calc R 1
C C21 0.5262(7) -0.3411(14) 0.0797(3) 0.070(2) Uani d . 1
H H21A 0.3964 -0.3570 0.0637 0.108 Uiso calc R 1
H H21B 0.5853 -0.4536 0.0618 0.108 Uiso calc R 1
H H21C 0.5619 -0.2217 0.0565 0.108 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
_geom_angle_publ_flag
C14 O1 C15 106.7(3) yes
C11 O2 H2A 109.5 ?
C2 C1 C10 121.1(4) ?
C2 C1 H1A 119.4 ?
C10 C1 H1A 119.4 ?
C1 C2 C3 121.3(4) ?
C1 C2 H2B 119.3 ?
C3 C2 H2B 119.3 ?
C4 C3 C2 121.3(4) ?
C4 C3 H3B 119.4 ?
C2 C3 H3B 119.4 ?
C3 C4 C5 118.9(4) ?
C3 C4 C17 120.2(4) ?
C5 C4 C17 120.9(4) ?
C6 C5 C4 121.0(3) ?
C6 C5 C10 118.5(3) ?
C4 C5 C10 120.5(3) ?
C7 C6 C5 121.9(3) ?
C7 C6 H6A 119.1 ?
C5 C6 H6A 119.1 ?
C6 C7 C8 119.8(3) ?
C6 C7 H7A 120.1 ?
C8 C7 H7A 120.1 ?
C9 C8 C7 121.1(3) ?
C9 C8 C14 118.5(3) ?
C7 C8 C14 120.4(3) ?
C8 C9 C10 119.2(3) ?
C8 C9 C11 119.4(3) ?
C10 C9 C11 121.2(3) ?
C9 C10 C1 123.7(3) ?
C9 C10 C5 119.4(3) ?
C1 C10 C5 116.9(4) ?
O2 C11 C9 109.3(2) ?
O2 C11 C12 106.6(3) ?
C9 C11 C12 115.8(3) ?
O2 C11 C18 112.4(3) ?
C9 C11 C18 108.0(3) ?
C12 C11 C18 104.8(3) ?
O4 C12 C13 125.7(4) yes
O4 C12 C11 116.8(3) yes
C13 C12 C11 117.5(3) ?
C14 C13 C12 119.7(3) ?
C14 C13 C16 110.1(3) ?
C12 C13 C16 129.9(3) ?
C13 C14 O1 114.4(3) ?
C13 C14 C8 126.6(3) ?
O1 C14 C8 118.9(3) ?
O1 C15 C16 107.7(3) ?
O1 C15 H15A 110.2 ?
C16 C15 H15A 110.2 ?
O1 C15 H15B 110.2 ?
C16 C15 H15B 110.2 ?
H15A C15 H15B 108.5 ?
C13 C16 C21 114.8(4) ?
C13 C16 C15 100.9(3) ?
C21 C16 C15 114.2(3) ?
C13 C16 H16A 108.9 ?
C21 C16 H16A 108.9 ?
C15 C16 H16A 108.9 ?
C4 C17 H17A 109.5 ?
C4 C17 H17B 109.5 ?
H17A C17 H17B 109.5 ?
C4 C17 H17C 109.5 ?
H17A C17 H17C 109.5 ?
H17B C17 H17C 109.5 ?
C19 C18 C11 114.0(4) ?
C19 C18 H18A 108.8 ?
C11 C18 H18A 108.8 ?
C19 C18 H18B 108.8 ?
C11 C18 H18B 108.8 ?
H18A C18 H18B 107.7 ?
O3 C19 C20 125.9(6) yes
O3 C19 C18 120.7(6) yes
C20 C19 C18 113.4(6) ?
C19 C20 H20A 109.5 ?
C19 C20 H20B 109.5 ?
H20A C20 H20B 109.5 ?
C19 C20 H20C 109.5 ?
H20A C20 H20C 109.5 ?
H20B C20 H20C 109.5 ?
C16 C21 H21A 109.5 ?
C16 C21 H21B 109.5 ?
H21A C21 H21B 109.5 ?
C16 C21 H21C 109.5 ?
H21A C21 H21C 109.5 ?
H21B C21 H21C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C14 1.356(4) yes
O1 C15 1.473(5) yes
O2 C11 1.413(3) yes
O2 H2A 0.8200 ?
O3 C19 1.293(8) yes
O4 C12 1.231(4) yes
C1 C2 1.363(6) ?
C1 C10 1.438(5) ?
C1 H1A 0.9300 ?
C2 C3 1.398(7) ?
C2 H2B 0.9300 ?
C3 C4 1.377(6) ?
C3 H3B 0.9300 ?
C4 C5 1.437(6) ?
C4 C17 1.496(6) ?
C5 C6 1.419(6) ?
C5 C10 1.442(5) ?
C6 C7 1.362(6) ?
C6 H6A 0.9300 ?
C7 C8 1.424(4) ?
C7 H7A 0.9300 ?
C8 C9 1.394(4) ?
C8 C14 1.446(5) ?
C9 C10 1.430(5) ?
C9 C11 1.519(4) ?
C11 C12 1.565(5) ?
C11 C18 1.569(5) ?
C12 C13 1.416(4) ?
C13 C14 1.340(5) ?
C13 C16 1.507(6) ?
C15 C16 1.529(5) ?
C15 H15A 0.9700 ?
C15 H15B 0.9700 ?
C16 C21 1.516(5) ?
C16 H16A 0.9800 ?
C17 H17A 0.9600 ?
C17 H17B 0.9600 ?
C17 H17C 0.9600 ?
C18 C19 1.542(6) ?
C18 H18A 0.9700 ?
C18 H18B 0.9700 ?
C19 C20 1.442(9) ?
C20 H20A 0.9600 ?
C20 H20B 0.9600 ?
C20 H20C 0.9600 ?
C21 H21A 0.9600 ?
C21 H21B 0.9600 ?
C21 H21C 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O2 H2A O3 0.82 2.24 2.969(6) 148
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
C10 C1 C2 C3 -2.1(6)
C1 C2 C3 C4 1.0(6)
C2 C3 C4 C5 -0.5(6)
C2 C3 C4 C17 -179.7(4)
C3 C4 C5 C6 179.6(4)
C17 C4 C5 C6 -1.2(6)
C3 C4 C5 C10 1.3(5)
C17 C4 C5 C10 -179.5(4)
C4 C5 C6 C7 -176.9(4)
C10 C5 C6 C7 1.3(6)
C5 C6 C7 C8 0.6(6)
C6 C7 C8 C9 -2.6(6)
C6 C7 C8 C14 178.3(4)
C7 C8 C9 C10 2.5(5)
C14 C8 C9 C10 -178.3(3)
C7 C8 C9 C11 177.6(3)
C14 C8 C9 C11 -3.2(5)
C8 C9 C10 C1 178.7(3)
C11 C9 C10 C1 3.7(5)
C8 C9 C10 C5 -0.6(4)
C11 C9 C10 C5 -175.6(3)
C2 C1 C10 C9 -176.5(3)
C2 C1 C10 C5 2.8(5)
C6 C5 C10 C9 -1.3(5)
C4 C5 C10 C9 177.0(3)
C6 C5 C10 C1 179.3(3)
C4 C5 C10 C1 -2.4(5)
C8 C9 C11 O2 134.0(3)
C10 C9 C11 O2 -51.0(4)
C8 C9 C11 C12 13.6(4)
C10 C9 C11 C12 -171.4(3)
C8 C9 C11 C18 -103.5(4)
C10 C9 C11 C18 71.5(4)
O2 C11 C12 O4 40.8(4)
C9 C11 C12 O4 162.7(3)
C18 C11 C12 O4 -78.5(3)
O2 C11 C12 C13 -141.2(3)
C9 C11 C12 C13 -19.3(4)
C18 C11 C12 C13 99.5(3)
O4 C12 C13 C14 -167.5(4)
C11 C12 C13 C14 14.7(5)
O4 C12 C13 C16 5.3(6)
C11 C12 C13 C16 -172.5(3)
C12 C13 C14 O1 173.1(3)
C16 C13 C14 O1 -1.0(4)
C12 C13 C14 C8 -3.8(6)
C16 C13 C14 C8 -177.9(3)
C15 O1 C14 C13 3.3(4)
C15 O1 C14 C8 -179.6(3)
C9 C8 C14 C13 -2.6(5)
C7 C8 C14 C13 176.7(4)
C9 C8 C14 O1 -179.4(3)
C7 C8 C14 O1 -0.2(5)
C14 O1 C15 C16 -4.2(4)
C14 C13 C16 C21 -124.9(4)
C12 C13 C16 C21 61.8(6)
C14 C13 C16 C15 -1.7(4)
C12 C13 C16 C15 -175.0(4)
O1 C15 C16 C13 3.4(4)
O1 C15 C16 C21 127.1(5)
O2 C11 C18 C19 -51.0(5)
C9 C11 C18 C19 -171.6(4)
C12 C11 C18 C19 64.4(5)
C11 C18 C19 O3 69.5(8)
C11 C18 C19 C20 -112.0(6)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2340706
