# Electronic Supplementary Material (ESI) for RSC Advances
# This journal is © The Royal Society of Chemistry 2012
data_global
_journal_name_full 'RSC Advances'
_journal_coden_cambridge 1500
_journal_year ?
_journal_volume ?
_journal_page_first ?
_publ_contact_author_email hsprlab@gmail.com
_publ_contact_author_name 'H. S. P. Rao'
loop_
_publ_author_name
'H. S. P. Rao'
S.Vijjapu
data_4b
_database_code_depnum_ccdc_archive 'CCDC 797133'
#TrackingRef '9992_web_deposit_cif_file_0_H.S.P.Rao_1331128862.RScb.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
10-Hydroxy-10-(2-oxopentyl)phenanthren-9(10H)-one
;
_chemical_name_common
10-Hydroxy-10-(2-oxopentyl)phenanthren-9(10H)-one
_chemical_melting_point ?
_chemical_formula_moiety 'C19 H18 O3'
_chemical_formula_sum 'C19 H18 O3'
_chemical_formula_weight 294.33
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'
_symmetry_cell_setting triclinic
_symmetry_space_group_name_H-M 'P -1'
_space_group_name_Hall '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 8.2005(8)
_cell_length_b 9.5269(16)
_cell_length_c 11.4959(15)
_cell_angle_alpha 65.961(14)
_cell_angle_beta 85.022(9)
_cell_angle_gamma 66.268(12)
_cell_volume 747.66(21)
_cell_formula_units_Z 2
_cell_measurement_temperature 293(2)
_cell_measurement_reflns_used 1650
_cell_measurement_theta_min 2.4990
_cell_measurement_theta_max 29.2120
_exptl_crystal_description block
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.38
_exptl_crystal_size_mid 0.36
_exptl_crystal_size_min 0.36
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.307
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 312
_exptl_absorpt_coefficient_mu 0.088
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.967
_exptl_absorpt_correction_T_max 0.969
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan 5 2010,16:28:46)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details ?
_diffrn_ambient_temperature 293(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Xcalibur, Eos'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean 15.9821
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 4851
_diffrn_reflns_av_R_equivalents 0.0270
_diffrn_reflns_av_sigmaI/netI 0.0628
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_k_max 9
_diffrn_reflns_limit_l_min -13
_diffrn_reflns_limit_l_max 13
_diffrn_reflns_theta_min 2.50
_diffrn_reflns_theta_max 24.99
_reflns_number_total 2628
_reflns_number_gt 1470
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'CrysAlis CCD (Oxford Diffraction, 2009)'
_computing_cell_refinement 'CrysAlis RED (Oxford Diffraction, 2009)'
_computing_data_reduction 'CrysAlis RED (Oxford Diffraction, 2009)'
_computing_structure_solution 'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material 'PLATON (Spek, 2009)'
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 2628
_refine_ls_number_parameters 201
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0785
_refine_ls_R_factor_gt 0.0367
_refine_ls_wR_factor_ref 0.1102
_refine_ls_wR_factor_gt 0.0935
_refine_ls_goodness_of_fit_ref 0.601
_refine_ls_restrained_S_all 0.601
_refine_ls_shift/su_max 0.015
_refine_ls_shift/su_mean 0.002
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.86939(15) 0.21869(16) 0.30394(11) 0.0463(4) Uani 1 1 d . . .
H2 H 0.9034 0.1723 0.3804 0.069 Uiso 1 1 calc R . .
C5 C 0.4749(2) 0.1186(2) 0.31468(15) 0.0362(4) Uani 1 1 d . . .
C14 C 0.5768(2) 0.2143(2) 0.28692(15) 0.0359(4) Uani 1 1 d . . .
C6 C 0.5628(2) -0.0622(2) 0.34085(15) 0.0373(4) Uani 1 1 d . . .
C12 C 0.8546(2) -0.0503(2) 0.36166(16) 0.0369(4) Uani 1 1 d . . .
O1 O 0.99341(15) -0.11520(17) 0.42959(12) 0.0532(4) Uani 1 1 d . . .
C11 C 0.7492(2) -0.1437(2) 0.35999(15) 0.0367(4) Uani 1 1 d . . .
O3 O 1.08502(17) -0.05407(18) 0.14812(13) 0.0597(4) Uani 1 1 d . . .
C13 C 0.7774(2) 0.1364(2) 0.27609(15) 0.0352(4) Uani 1 1 d . . .
C1 C 0.4941(2) 0.3840(2) 0.25983(17) 0.0472(5) Uani 1 1 d . . .
H1 H 0.5627 0.4467 0.2418 0.057 Uiso 1 1 calc R . .
C4 C 0.2905(2) 0.1991(3) 0.31463(17) 0.0485(5) Uani 1 1 d . . .
H4 H 0.2207 0.1375 0.3338 0.058 Uiso 1 1 calc R . .
C15 C 0.8025(2) 0.1630(2) 0.13436(16) 0.0408(5) Uani 1 1 d . . .
H15A H 0.7419 0.1077 0.1114 0.049 Uiso 1 1 calc R . .
H15B H 0.7465 0.2821 0.0803 0.049 Uiso 1 1 calc R . .
C16 C 0.9973(2) 0.0956(3) 0.10825(16) 0.0401(4) Uani 1 1 d . . .
C7 C 0.4669(2) -0.1592(3) 0.35124(17) 0.0504(5) Uani 1 1 d . . .
H7 H 0.3426 -0.1090 0.3404 0.060 Uiso 1 1 calc R . .
C10 C 0.8347(3) -0.3139(2) 0.38669(17) 0.0501(5) Uani 1 1 d . . .
H10 H 0.9588 -0.3664 0.3995 0.060 Uiso 1 1 calc R . .
C2 C 0.3111(3) 0.4612(3) 0.25933(18) 0.0569(6) Uani 1 1 d . . .
H2A H 0.2563 0.5754 0.2406 0.068 Uiso 1 1 calc R . .
C17 C 1.0715(2) 0.2233(3) 0.03545(17) 0.0474(5) Uani 1 1 d . . .
H17A H 1.0597 0.2895 0.0837 0.057 Uiso 1 1 calc R . .
H17B H 0.9975 0.2986 -0.0448 0.057 Uiso 1 1 calc R . .
C8 C 0.5536(3) -0.3273(3) 0.37721(19) 0.0591(6) Uani 1 1 d . . .
H8 H 0.4872 -0.3890 0.3833 0.071 Uiso 1 1 calc R . .
C9 C 0.7374(3) -0.4054(3) 0.39435(19) 0.0605(6) Uani 1 1 d . . .
H9 H 0.7952 -0.5189 0.4110 0.073 Uiso 1 1 calc R . .
C3 C 0.2101(2) 0.3677(3) 0.28677(19) 0.0566(6) Uani 1 1 d . . .
H3 H 0.0867 0.4192 0.2864 0.068 Uiso 1 1 calc R . .
C19 C 1.3344(3) 0.2955(3) -0.04602(19) 0.0669(7) Uani 1 1 d . . .
H19A H 1.2604 0.3860 -0.1212 0.100 Uiso 1 1 calc R . .
H19B H 1.4547 0.2499 -0.0673 0.100 Uiso 1 1 calc R . .
H19C H 1.3332 0.3367 0.0177 0.100 Uiso 1 1 calc R . .
C18 C 1.2632(2) 0.1596(3) 0.00557(19) 0.0539(6) Uani 1 1 d . . .
H18A H 1.2725 0.1131 -0.0569 0.065 Uiso 1 1 calc R . .
H18B H 1.3367 0.0699 0.0827 0.065 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O2 0.0474(7) 0.0537(9) 0.0502(8) -0.0208(7) -0.0019(6) -0.0312(7)
C5 0.0356(9) 0.0489(13) 0.0281(9) -0.0156(9) 0.0023(7) -0.0208(9)
C14 0.0374(9) 0.0437(12) 0.0330(10) -0.0188(9) 0.0036(7) -0.0192(9)
C6 0.0444(10) 0.0429(12) 0.0282(9) -0.0102(8) 0.0027(7) -0.0253(9)
C12 0.0351(9) 0.0430(11) 0.0339(9) -0.0168(9) 0.0022(7) -0.0155(8)
O1 0.0447(7) 0.0595(10) 0.0508(8) -0.0172(7) -0.0127(6) -0.0187(6)
C11 0.0441(10) 0.0388(12) 0.0285(9) -0.0109(8) 0.0000(7) -0.0200(9)
O3 0.0562(8) 0.0457(10) 0.0689(10) -0.0184(8) 0.0101(7) -0.0185(7)
C13 0.0355(9) 0.0406(11) 0.0376(10) -0.0167(9) 0.0004(7) -0.0218(8)
C1 0.0500(11) 0.0458(13) 0.0533(12) -0.0244(10) 0.0051(9) -0.0221(10)
C4 0.0419(11) 0.0643(15) 0.0484(12) -0.0276(11) 0.0110(8) -0.0268(10)
C15 0.0410(10) 0.0471(12) 0.0361(10) -0.0131(9) 0.0018(7) -0.0231(9)
C16 0.0412(10) 0.0455(13) 0.0340(10) -0.0155(9) 0.0004(8) -0.0180(9)
C7 0.0545(11) 0.0619(15) 0.0441(12) -0.0169(11) 0.0030(9) -0.0369(11)
C10 0.0588(12) 0.0422(13) 0.0448(12) -0.0141(10) -0.0024(9) -0.0183(10)
C2 0.0536(12) 0.0505(14) 0.0635(14) -0.0321(11) 0.0017(10) -0.0083(11)
C17 0.0464(10) 0.0520(13) 0.0412(11) -0.0140(10) 0.0059(8) -0.0228(9)
C8 0.0881(16) 0.0530(15) 0.0514(13) -0.0160(11) 0.0032(11) -0.0476(13)
C9 0.0853(15) 0.0447(14) 0.0537(13) -0.0166(11) -0.0036(11) -0.0299(12)
C3 0.0358(10) 0.0732(18) 0.0620(14) -0.0371(12) 0.0094(9) -0.0144(11)
C19 0.0605(13) 0.0877(18) 0.0578(14) -0.0234(13) 0.0158(10) -0.0434(13)
C18 0.0490(11) 0.0619(15) 0.0514(13) -0.0229(11) 0.0136(9) -0.0250(10)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
O2 C13 1.4175(19) . ?
O2 H2 0.8200 . ?
C5 C4 1.393(2) . ?
C5 C14 1.401(2) . ?
C5 C6 1.481(2) . ?
C14 C1 1.383(3) . ?
C14 C13 1.526(2) . ?
C6 C11 1.397(2) . ?
C6 C7 1.402(2) . ?
C12 O1 1.2176(18) . ?
C12 C11 1.474(2) . ?
C12 C13 1.519(2) . ?
C11 C10 1.391(3) . ?
O3 C16 1.208(2) . ?
C13 C15 1.552(2) . ?
C1 C2 1.380(2) . ?
C1 H1 0.9300 . ?
C4 C3 1.372(3) . ?
C4 H4 0.9300 . ?
C15 C16 1.517(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.493(2) . ?
C7 C8 1.375(3) . ?
C7 H7 0.9300 . ?
C10 C9 1.374(3) . ?
C10 H10 0.9300 . ?
C2 C3 1.378(3) . ?
C2 H2A 0.9300 . ?
C17 C18 1.505(2) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C8 C9 1.376(3) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C3 H3 0.9300 . ?
C19 C18 1.514(3) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
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
C13 O2 H2 109.5 . . ?
C4 C5 C14 118.08(18) . . ?
C4 C5 C6 121.79(16) . . ?
C14 C5 C6 120.13(14) . . ?
C1 C14 C5 120.09(16) . . ?
C1 C14 C13 119.19(16) . . ?
C5 C14 C13 120.56(16) . . ?
C11 C6 C7 117.37(18) . . ?
C11 C6 C5 119.69(15) . . ?
C7 C6 C5 122.91(16) . . ?
O1 C12 C11 123.08(17) . . ?
O1 C12 C13 120.64(16) . . ?
C11 C12 C13 116.25(14) . . ?
C10 C11 C6 120.72(17) . . ?
C10 C11 C12 119.92(16) . . ?
C6 C11 C12 119.19(16) . . ?
O2 C13 C12 111.18(13) . . ?
O2 C13 C14 112.08(14) . . ?
C12 C13 C14 110.16(13) . . ?
O2 C13 C15 106.21(13) . . ?
C12 C13 C15 109.72(14) . . ?
C14 C13 C15 107.32(13) . . ?
C2 C1 C14 120.74(18) . . ?
C2 C1 H1 119.6 . . ?
C14 C1 H1 119.6 . . ?
C3 C4 C5 121.22(19) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C16 C15 C13 113.24(13) . . ?
C16 C15 H15A 108.9 . . ?
C13 C15 H15A 108.9 . . ?
C16 C15 H15B 108.9 . . ?
C13 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
O3 C16 C17 123.40(17) . . ?
O3 C16 C15 120.22(17) . . ?
C17 C16 C15 116.36(17) . . ?
C8 C7 C6 121.12(18) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C9 C10 C11 120.64(18) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C3 C2 C1 119.5(2) . . ?
C3 C2 H2A 120.3 . . ?
C1 C2 H2A 120.3 . . ?
C16 C17 C18 117.28(18) . . ?
C16 C17 H17A 108.0 . . ?
C18 C17 H17A 108.0 . . ?
C16 C17 H17B 108.0 . . ?
C18 C17 H17B 108.0 . . ?
H17A C17 H17B 107.2 . . ?
C7 C8 C9 120.8(2) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C10 C9 C8 119.3(2) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C4 C3 C2 120.41(18) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C18 C19 112.68(18) . . ?
C17 C18 H18A 109.1 . . ?
C19 C18 H18A 109.1 . . ?
C17 C18 H18B 109.1 . . ?
C19 C18 H18B 109.1 . . ?
H18A C18 H18B 107.8 . . ?
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
C4 C5 C14 C1 -0.3(2) . . . . ?
C6 C5 C14 C1 178.64(16) . . . . ?
C4 C5 C14 C13 -175.61(15) . . . . ?
C6 C5 C14 C13 3.4(2) . . . . ?
C4 C5 C6 C11 -169.86(15) . . . . ?
C14 C5 C6 C11 11.2(2) . . . . ?
C4 C5 C6 C7 8.3(3) . . . . ?
C14 C5 C6 C7 -170.67(15) . . . . ?
C7 C6 C11 C10 0.8(2) . . . . ?
C5 C6 C11 C10 178.99(15) . . . . ?
C7 C6 C11 C12 -174.47(15) . . . . ?
C5 C6 C11 C12 3.8(2) . . . . ?
O1 C12 C11 C10 -29.7(3) . . . . ?
C13 C12 C11 C10 152.30(16) . . . . ?
O1 C12 C11 C6 145.56(17) . . . . ?
C13 C12 C11 C6 -32.4(2) . . . . ?
O1 C12 C13 O2 -9.7(2) . . . . ?
C11 C12 C13 O2 168.36(13) . . . . ?
O1 C12 C13 C14 -134.56(16) . . . . ?
C11 C12 C13 C14 43.49(19) . . . . ?
O1 C12 C13 C15 107.50(18) . . . . ?
C11 C12 C13 C15 -74.45(17) . . . . ?
C1 C14 C13 O2 30.7(2) . . . . ?
C5 C14 C13 O2 -154.00(14) . . . . ?
C1 C14 C13 C12 155.04(16) . . . . ?
C5 C14 C13 C12 -29.6(2) . . . . ?
C1 C14 C13 C15 -85.55(19) . . . . ?
C5 C14 C13 C15 89.77(18) . . . . ?
C5 C14 C1 C2 -0.2(3) . . . . ?
C13 C14 C1 C2 175.13(15) . . . . ?
C14 C5 C4 C3 0.8(3) . . . . ?
C6 C5 C4 C3 -178.18(17) . . . . ?
O2 C13 C15 C16 58.29(19) . . . . ?
C12 C13 C15 C16 -61.97(19) . . . . ?
C14 C13 C15 C16 178.34(15) . . . . ?
C13 C15 C16 O3 71.3(2) . . . . ?
C13 C15 C16 C17 -107.04(18) . . . . ?
C11 C6 C7 C8 -1.0(3) . . . . ?
C5 C6 C7 C8 -179.19(17) . . . . ?
C6 C11 C10 C9 0.2(3) . . . . ?
C12 C11 C10 C9 175.41(16) . . . . ?
C14 C1 C2 C3 0.3(3) . . . . ?
O3 C16 C17 C18 3.2(3) . . . . ?
C15 C16 C17 C18 -178.51(16) . . . . ?
C6 C7 C8 C9 0.3(3) . . . . ?
C11 C10 C9 C8 -1.0(3) . . . . ?
C7 C8 C9 C10 0.7(3) . . . . ?
C5 C4 C3 C2 -0.7(3) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C16 C17 C18 C19 -169.34(16) . . . . ?
_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full 24.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max 0.125
_refine_diff_density_min -0.168
_refine_diff_density_rms 0.030
# Attachment '9995_web_deposit_cif_file_3_H.S.P.Rao_1331128862.RSci.cif'
data_3i
_database_code_depnum_ccdc_archive 'CCDC 805643'
#TrackingRef '9995_web_deposit_cif_file_3_H.S.P.Rao_1331128862.RSci.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
(Z)-10,11,12,13-Tetrahydrocycloocta[d]phenanthro[9,10-b]furan
;
_chemical_name_common
(Z)-10,11,12,13-Tetrahydrocycloocta(d)phenanthro(9,10-b)furan
_chemical_melting_point ?
_chemical_formula_moiety 'C22 H18 O'
_chemical_formula_sum 'C22 H18 O'
_chemical_formula_weight 298.36
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'
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'P 21/c'
_space_group_name_Hall '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a 13.049(3)
_cell_length_b 5.3590(14)
_cell_length_c 21.620(5)
_cell_angle_alpha 90.00
_cell_angle_beta 94.35(2)
_cell_angle_gamma 90.00
_cell_volume 1507.6(6)
_cell_formula_units_Z 4
_cell_measurement_temperature 293(2)
_cell_measurement_reflns_used 750
_cell_measurement_theta_min 2.5385
_cell_measurement_theta_max 29.1926
_exptl_crystal_description plate
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.16
_exptl_crystal_size_mid 0.08
_exptl_crystal_size_min 0.08
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.315
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 632
_exptl_absorpt_coefficient_mu 0.079
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.992
_exptl_absorpt_correction_T_max 0.994
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details ?
_diffrn_ambient_temperature 293(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Xcalibur, Eos'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean 15.9821
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 5373
_diffrn_reflns_av_R_equivalents 0.1469
_diffrn_reflns_av_sigmaI/netI 0.3299
_diffrn_reflns_limit_h_min -15
_diffrn_reflns_limit_h_max 15
_diffrn_reflns_limit_k_min -6
_diffrn_reflns_limit_k_max 6
_diffrn_reflns_limit_l_min -25
_diffrn_reflns_limit_l_max 25
_diffrn_reflns_theta_min 2.54
_diffrn_reflns_theta_max 25.00
_reflns_number_total 2654
_reflns_number_gt 817
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'CrysAlis CCD (Oxford Diffraction, 2009)'
_computing_cell_refinement 'CrysAlis RED (Oxford Diffraction, 2009)'
_computing_data_reduction 'CrysAlis RED (Oxford Diffraction, 2009)'
_computing_structure_solution 'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material 'PLATON (Spek, 2009)'
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0264P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 2654
_refine_ls_number_parameters 208
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.2916
_refine_ls_R_factor_gt 0.0866
_refine_ls_wR_factor_ref 0.1183
_refine_ls_wR_factor_gt 0.0849
_refine_ls_goodness_of_fit_ref 0.865
_refine_ls_restrained_S_all 0.865
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1416(2) 0.8244(6) 0.32664(16) 0.0409(11) Uani 1 1 d . . .
C10 C 0.4730(4) 0.5590(9) 0.4039(2) 0.0404(15) Uani 1 1 d . . .
H10 H 0.4730 0.6804 0.4346 0.048 Uiso 1 1 calc R . .
C12 C 0.3022(3) 0.7059(9) 0.3596(2) 0.0288(14) Uani 1 1 d . . .
C5 C 0.3019(4) 0.3254(10) 0.2693(3) 0.0343(15) Uani 1 1 d . . .
C13 C 0.2218(4) 0.6663(10) 0.3178(2) 0.0321(14) Uani 1 1 d . . .
C22 C 0.0939(3) 1.1566(9) 0.3928(2) 0.0414(15) Uani 1 1 d . . .
H22B H 0.0349 1.0653 0.4057 0.050 Uiso 1 1 calc R . .
H22A H 0.0717 1.2450 0.3550 0.050 Uiso 1 1 calc R . .
C8 C 0.5544(4) 0.2122(10) 0.3584(3) 0.0484(18) Uani 1 1 d . . .
H8 H 0.6091 0.1011 0.3580 0.058 Uiso 1 1 calc R . .
C15 C 0.1736(4) 0.9707(10) 0.3775(2) 0.0349(15) Uani 1 1 d . . .
C7 C 0.4745(4) 0.1931(10) 0.3150(2) 0.0427(16) Uani 1 1 d . . .
H7 H 0.4757 0.0687 0.2851 0.051 Uiso 1 1 calc R . .
C2 C 0.1264(4) 0.2543(11) 0.1873(2) 0.0542(17) Uani 1 1 d . . .
H2 H 0.0683 0.2267 0.1606 0.065 Uiso 1 1 calc R . .
C11 C 0.3896(3) 0.5462(10) 0.3595(2) 0.0297(14) Uani 1 1 d . . .
C21 C 0.1238(3) 1.3489(9) 0.4424(2) 0.0475(16) Uani 1 1 d . . .
H21B H 0.0782 1.4914 0.4365 0.057 Uiso 1 1 calc R . .
H21A H 0.1930 1.4062 0.4368 0.057 Uiso 1 1 calc R . .
C4 C 0.2977(4) 0.1358(11) 0.2234(3) 0.0483(17) Uani 1 1 d . . .
H4 H 0.3539 0.0311 0.2203 0.058 Uiso 1 1 calc R . .
C6 C 0.3900(3) 0.3549(10) 0.3138(2) 0.0330(15) Uani 1 1 d . . .
C9 C 0.5552(4) 0.3977(10) 0.4037(2) 0.0452(16) Uani 1 1 d . . .
H9 H 0.6104 0.4122 0.4333 0.054 Uiso 1 1 calc R . .
C14 C 0.2154(4) 0.4811(10) 0.2707(2) 0.0351(15) Uani 1 1 d . . .
C16 C 0.2697(4) 0.9055(9) 0.3993(2) 0.0304(14) Uani 1 1 d . . .
C17 C 0.3299(3) 1.0134(9) 0.4526(3) 0.0395(16) Uani 1 1 d . . .
H17 H 0.3986 1.0496 0.4481 0.047 Uiso 1 1 calc R . .
C1 C 0.1274(4) 0.4428(11) 0.2301(2) 0.0459(17) Uani 1 1 d . . .
H1 H 0.0702 0.5449 0.2324 0.055 Uiso 1 1 calc R . .
C19 C 0.1866(3) 1.0232(9) 0.5223(2) 0.0510(16) Uani 1 1 d . . .
H19B H 0.1861 0.9799 0.5659 0.061 Uiso 1 1 calc R . .
H19A H 0.1577 0.8840 0.4982 0.061 Uiso 1 1 calc R . .
C18 C 0.2937(4) 1.0637(9) 0.5070(3) 0.0450(16) Uani 1 1 d . . .
H18 H 0.3394 1.1295 0.5379 0.054 Uiso 1 1 calc R . .
C3 C 0.2124(4) 0.1053(10) 0.1840(2) 0.0544(18) Uani 1 1 d . . .
H3 H 0.2118 -0.0191 0.1540 0.065 Uiso 1 1 calc R . .
C20 C 0.1198(4) 1.2541(9) 0.5092(2) 0.0489(16) Uani 1 1 d . . .
H20B H 0.1427 1.3858 0.5377 0.059 Uiso 1 1 calc R . .
H20A H 0.0492 1.2143 0.5165 0.059 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.044(2) 0.048(3) 0.029(3) -0.006(2) -0.0049(19) 0.007(2)
C10 0.038(3) 0.034(4) 0.049(4) 0.005(4) 0.003(3) 0.006(3)
C12 0.024(3) 0.033(4) 0.030(4) 0.000(3) 0.005(3) 0.003(3)
C5 0.040(3) 0.032(4) 0.032(4) 0.010(4) 0.007(3) 0.005(3)
C13 0.030(3) 0.041(4) 0.026(4) 0.011(4) 0.004(3) 0.010(3)
C22 0.046(3) 0.039(4) 0.040(4) 0.006(4) 0.007(3) 0.011(3)
C8 0.036(3) 0.049(4) 0.061(5) 0.008(4) 0.007(3) 0.004(3)
C15 0.042(3) 0.038(4) 0.026(4) 0.005(3) 0.009(3) -0.007(3)
C7 0.041(3) 0.046(4) 0.042(4) 0.004(4) 0.012(3) 0.004(3)
C2 0.069(4) 0.064(5) 0.027(4) -0.005(4) -0.010(3) 0.001(4)
C11 0.026(3) 0.035(3) 0.027(4) 0.005(3) -0.002(3) -0.003(3)
C21 0.052(3) 0.034(4) 0.056(5) -0.002(4) 0.003(3) 0.010(3)
C4 0.055(4) 0.049(4) 0.040(4) -0.002(4) -0.005(3) 0.020(3)
C6 0.033(3) 0.037(4) 0.031(4) 0.011(4) 0.011(3) 0.001(3)
C9 0.036(3) 0.057(5) 0.042(4) 0.007(4) 0.000(3) -0.010(3)
C14 0.043(3) 0.039(4) 0.023(4) -0.003(3) 0.001(3) 0.000(3)
C16 0.034(3) 0.039(4) 0.019(4) 0.007(3) 0.004(3) -0.008(3)
C17 0.030(3) 0.038(4) 0.050(5) -0.003(4) 0.000(3) -0.006(3)
C1 0.049(4) 0.053(5) 0.034(4) -0.002(4) -0.003(3) 0.007(4)
C19 0.075(4) 0.045(4) 0.034(4) 0.005(4) 0.007(3) 0.001(3)
C18 0.043(3) 0.047(4) 0.044(5) -0.001(4) -0.006(3) 0.002(3)
C3 0.068(4) 0.064(5) 0.030(4) -0.009(4) -0.004(3) 0.024(4)
C20 0.070(4) 0.045(4) 0.032(4) -0.010(4) 0.011(3) -0.014(3)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C13 1.371(5) . ?
O1 C15 1.389(5) . ?
C10 C9 1.378(5) . ?
C10 C11 1.398(6) . ?
C12 C13 1.348(6) . ?
C12 C11 1.426(6) . ?
C12 C16 1.455(6) . ?
C5 C14 1.406(6) . ?
C5 C4 1.418(6) . ?
C5 C6 1.450(6) . ?
C13 C14 1.420(6) . ?
C22 C15 1.495(5) . ?
C22 C21 1.516(5) . ?
C8 C7 1.352(6) . ?
C8 C9 1.394(6) . ?
C15 C16 1.352(6) . ?
C7 C6 1.402(5) . ?
C2 C1 1.370(6) . ?
C2 C3 1.383(6) . ?
C11 C6 1.424(6) . ?
C21 C20 1.535(6) . ?
C4 C3 1.360(5) . ?
C14 C1 1.406(6) . ?
C16 C17 1.463(6) . ?
C17 C18 1.328(6) . ?
C19 C18 1.476(5) . ?
C19 C20 1.528(5) . ?
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
C13 O1 C15 105.8(4) . . ?
C9 C10 C11 122.2(5) . . ?
C13 C12 C11 119.1(5) . . ?
C13 C12 C16 105.3(4) . . ?
C11 C12 C16 135.4(5) . . ?
C14 C5 C4 116.9(5) . . ?
C14 C5 C6 121.2(5) . . ?
C4 C5 C6 121.9(5) . . ?
C12 C13 O1 111.9(5) . . ?
C12 C13 C14 126.2(5) . . ?
O1 C13 C14 121.9(5) . . ?
C15 C22 C21 117.6(4) . . ?
C7 C8 C9 120.3(5) . . ?
C16 C15 O1 110.2(4) . . ?
C16 C15 C22 137.5(5) . . ?
O1 C15 C22 112.3(5) . . ?
C8 C7 C6 122.1(5) . . ?
C1 C2 C3 119.6(5) . . ?
C10 C11 C6 117.9(5) . . ?
C10 C11 C12 123.4(5) . . ?
C6 C11 C12 118.6(5) . . ?
C22 C21 C20 114.5(4) . . ?
C3 C4 C5 120.7(5) . . ?
C7 C6 C11 118.4(5) . . ?
C7 C6 C5 121.9(5) . . ?
C11 C6 C5 119.6(5) . . ?
C10 C9 C8 119.1(5) . . ?
C5 C14 C1 121.2(5) . . ?
C5 C14 C13 115.3(5) . . ?
C1 C14 C13 123.4(5) . . ?
C15 C16 C12 106.8(5) . . ?
C15 C16 C17 126.9(5) . . ?
C12 C16 C17 126.3(4) . . ?
C18 C17 C16 124.9(4) . . ?
C2 C1 C14 119.7(5) . . ?
C18 C19 C20 112.1(4) . . ?
C17 C18 C19 125.1(5) . . ?
C4 C3 C2 121.8(6) . . ?
C19 C20 C21 112.6(4) . . ?
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full 25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max 0.215
_refine_diff_density_min -0.220
_refine_diff_density_rms 0.054
# Attachment '9993_web_deposit_cif_file_1_H.S.P.Rao_1331128862.RScf.cif'
data_3f
_database_code_depnum_ccdc_archive 'CCDC 805644'
#TrackingRef '9993_web_deposit_cif_file_1_H.S.P.Rao_1331128862.RScf.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
9aSR,12aSR)-11,12-Dihydro-10H-spiro[9a,12a
epoxymethanooxy)cyclopenta[b]phenanthro[9,10-d]furan-14,1'-cyclopentane]
;
_chemical_name_common
;
9aSR,12aSR)-11,12-Dihydro-10H-spiro(9a,12a
epoxymethanooxy)cyclopenta(b)phenanthro(9,10-d)furan-14,1'-cyclopentane)
;
_chemical_melting_point ?
_chemical_formula_moiety 'C24 H22 O3'
_chemical_formula_sum 'C24 H22 O3'
_chemical_formula_weight 358.42
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'
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'P 21/c'
_space_group_name_Hall '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a 11.6236(6)
_cell_length_b 10.7231(7)
_cell_length_c 14.8535(10)
_cell_angle_alpha 90.00
_cell_angle_beta 101.277(5)
_cell_angle_gamma 90.00
_cell_volume 1815.61(19)
_cell_formula_units_Z 4
_cell_measurement_temperature 293(2)
_cell_measurement_reflns_used 3085
_cell_measurement_theta_min 2.7835
_cell_measurement_theta_max 29.2484
_exptl_crystal_description block
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.25
_exptl_crystal_size_mid 0.18
_exptl_crystal_size_min 0.14
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.311
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 760
_exptl_absorpt_coefficient_mu 0.085
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.982
_exptl_absorpt_correction_T_max 0.988
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details ?
_diffrn_ambient_temperature 293(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Xcalibur, Eos'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean 15.9821
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 6628
_diffrn_reflns_av_R_equivalents 0.0307
_diffrn_reflns_av_sigmaI/netI 0.0456
_diffrn_reflns_limit_h_min -13
_diffrn_reflns_limit_h_max 8
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_l_min -16
_diffrn_reflns_limit_l_max 17
_diffrn_reflns_theta_min 2.79
_diffrn_reflns_theta_max 25.00
_reflns_number_total 3195
_reflns_number_gt 1959
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'CrysAlis CCD (Oxford Diffraction, 2009)'
_computing_cell_refinement 'CrysAlis RED (Oxford Diffraction, 2009)'
_computing_data_reduction 'CrysAlis RED (Oxford Diffraction, 2009)'
_computing_structure_solution 'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material 'PLATON (Spek, 2009)'
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 3195
_refine_ls_number_parameters 244
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.1234
_refine_ls_R_factor_gt 0.0733
_refine_ls_wR_factor_ref 0.2153
_refine_ls_wR_factor_gt 0.1934
_refine_ls_goodness_of_fit_ref 1.308
_refine_ls_restrained_S_all 1.308
_refine_ls_shift/su_max 0.040
_refine_ls_shift/su_mean 0.008
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.10488(18) 0.3315(2) 0.08044(16) 0.0451(6) Uani 1 1 d . . .
O3 O 0.38051(17) 0.3235(2) 0.05200(16) 0.0481(7) Uani 1 1 d . . .
O2 O 0.26016(18) 0.4707(2) 0.09060(16) 0.0470(7) Uani 1 1 d . . .
C11 C 0.2454(3) 0.0439(3) 0.0279(2) 0.0417(9) Uani 1 1 d . . .
C14 C 0.0604(3) 0.1198(3) 0.1189(2) 0.0389(8) Uani 1 1 d . . .
C5 C 0.0905(3) -0.0084(3) 0.1154(2) 0.0390(8) Uani 1 1 d . . .
C12 C 0.2149(3) 0.1733(3) 0.0361(2) 0.0374(8) Uani 1 1 d . . .
C13 C 0.1269(3) 0.2043(3) 0.0778(2) 0.0381(8) Uani 1 1 d . . .
C6 C 0.1822(3) -0.0477(3) 0.0680(2) 0.0392(8) Uani 1 1 d . . .
C1 C -0.0300(3) 0.1576(4) 0.1642(2) 0.0474(9) Uani 1 1 d . . .
H1 H -0.0505 0.2414 0.1645 0.057 Uiso 1 1 calc R . .
C7 C 0.2108(3) -0.1741(3) 0.0590(3) 0.0535(10) Uani 1 1 d . . .
H7 H 0.1702 -0.2352 0.0845 0.064 Uiso 1 1 calc R . .
C10 C 0.3336(3) 0.0056(4) -0.0175(3) 0.0516(10) Uani 1 1 d . . .
H10 H 0.3757 0.0652 -0.0431 0.062 Uiso 1 1 calc R . .
C2 C -0.0866(3) 0.0734(4) 0.2068(3) 0.0576(10) Uani 1 1 d . . .
H2 H -0.1460 0.0993 0.2364 0.069 Uiso 1 1 calc R . .
C4 C 0.0283(3) -0.0923(3) 0.1612(2) 0.0505(10) Uani 1 1 d . . .
H4 H 0.0453 -0.1770 0.1606 0.061 Uiso 1 1 calc R . .
C15 C 0.1860(3) 0.3910(3) 0.0324(2) 0.0411(8) Uani 1 1 d . . .
C17 C 0.3679(3) 0.4048(3) 0.1251(2) 0.0420(8) Uani 1 1 d . . .
C16 C 0.2658(3) 0.2899(3) 0.0026(2) 0.0388(8) Uani 1 1 d . . .
C3 C -0.0567(3) -0.0518(4) 0.2068(3) 0.0599(11) Uani 1 1 d . . .
H3 H -0.0947 -0.1089 0.2380 0.072 Uiso 1 1 calc R . .
C9 C 0.3592(3) -0.1174(4) -0.0251(3) 0.0622(11) Uani 1 1 d . . .
H9 H 0.4183 -0.1407 -0.0558 0.075 Uiso 1 1 calc R . .
C22 C 0.2599(3) 0.3104(4) -0.0988(2) 0.0524(10) Uani 1 1 d . . .
H22A H 0.2074 0.2509 -0.1349 0.063 Uiso 1 1 calc R . .
H22B H 0.3370 0.3025 -0.1140 0.063 Uiso 1 1 calc R . .
C24 C 0.1253(3) 0.4584(4) -0.0544(2) 0.0522(10) Uani 1 1 d . . .
H24A H 0.0509 0.4196 -0.0806 0.063 Uiso 1 1 calc R . .
H24B H 0.1124 0.5457 -0.0424 0.063 Uiso 1 1 calc R . .
C8 C 0.2977(3) -0.2088(4) 0.0129(3) 0.0624(12) Uani 1 1 d . . .
H8 H 0.3153 -0.2927 0.0072 0.075 Uiso 1 1 calc R . .
C18 C 0.3685(3) 0.3397(4) 0.2157(3) 0.0622(11) Uani 1 1 d . . .
H18A H 0.3134 0.3787 0.2483 0.075 Uiso 1 1 calc R . .
H18B H 0.3480 0.2524 0.2060 0.075 Uiso 1 1 calc R . .
C23 C 0.2134(3) 0.4428(4) -0.1161(2) 0.0595(11) Uani 1 1 d . . .
H23A H 0.2765 0.5030 -0.1008 0.071 Uiso 1 1 calc R . .
H23B H 0.1762 0.4536 -0.1800 0.071 Uiso 1 1 calc R . .
C21 C 0.4700(3) 0.4970(4) 0.1438(3) 0.0639(12) Uani 1 1 d . . .
H21A H 0.5156 0.4929 0.0958 0.077 Uiso 1 1 calc R . .
H21B H 0.4417 0.5816 0.1474 0.077 Uiso 1 1 calc R . .
C20 C 0.5425(4) 0.4572(6) 0.2343(4) 0.109(2) Uani 1 1 d . . .
H20A H 0.6210 0.4352 0.2268 0.131 Uiso 1 1 calc R . .
H20B H 0.5484 0.5250 0.2782 0.131 Uiso 1 1 calc R . .
C19 C 0.4879(4) 0.3529(6) 0.2666(4) 0.117(2) Uani 1 1 d . . .
H19A H 0.4871 0.3635 0.3314 0.141 Uiso 1 1 calc R . .
H19B H 0.5321 0.2780 0.2596 0.141 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0484(13) 0.0403(14) 0.0523(15) 0.0001(12) 0.0239(11) -0.0009(10)
O3 0.0346(12) 0.0565(16) 0.0534(16) -0.0055(13) 0.0092(10) -0.0055(10)
O2 0.0500(14) 0.0384(13) 0.0500(15) -0.0061(12) 0.0030(11) -0.0029(10)
C11 0.0337(17) 0.049(2) 0.0377(19) -0.0047(17) -0.0044(14) -0.0023(15)
C14 0.0400(18) 0.0422(19) 0.0312(17) 0.0022(16) -0.0010(13) -0.0115(15)
C5 0.0436(18) 0.0356(18) 0.0323(18) 0.0040(16) -0.0057(14) -0.0124(15)
C12 0.0364(17) 0.0359(19) 0.0376(19) 0.0004(16) 0.0016(14) -0.0113(14)
C13 0.0427(18) 0.0339(18) 0.0368(19) -0.0044(16) 0.0056(15) -0.0038(14)
C6 0.0400(17) 0.0357(18) 0.0360(18) 0.0014(16) -0.0073(14) -0.0065(14)
C1 0.0471(19) 0.050(2) 0.044(2) -0.0024(19) 0.0073(15) -0.0056(17)
C7 0.056(2) 0.040(2) 0.057(3) 0.0026(19) -0.0082(18) -0.0046(17)
C10 0.047(2) 0.050(2) 0.058(2) -0.008(2) 0.0086(17) 0.0008(17)
C2 0.052(2) 0.075(3) 0.047(2) -0.001(2) 0.0134(17) -0.021(2)
C4 0.056(2) 0.042(2) 0.048(2) 0.0002(19) -0.0038(17) -0.0203(17)
C15 0.0407(18) 0.0436(19) 0.0405(19) 0.0018(17) 0.0120(14) -0.0085(15)
C17 0.0436(19) 0.0415(19) 0.0393(19) 0.0003(18) 0.0037(14) -0.0079(15)
C16 0.0391(17) 0.0407(19) 0.0361(18) -0.0056(16) 0.0058(14) -0.0038(14)
C3 0.057(2) 0.071(3) 0.052(2) 0.002(2) 0.0114(18) -0.030(2)
C9 0.047(2) 0.076(3) 0.060(3) -0.012(2) 0.0003(17) 0.012(2)
C22 0.056(2) 0.063(3) 0.041(2) -0.009(2) 0.0176(16) -0.0195(19)
C24 0.0433(19) 0.056(2) 0.054(2) 0.0080(19) 0.0024(16) 0.0039(17)
C8 0.065(2) 0.045(2) 0.067(3) -0.008(2) -0.011(2) 0.014(2)
C18 0.071(2) 0.067(3) 0.046(2) 0.013(2) 0.0029(18) -0.018(2)
C23 0.059(2) 0.079(3) 0.038(2) 0.016(2) 0.0033(16) -0.015(2)
C21 0.065(2) 0.060(2) 0.059(3) 0.010(2) -0.0078(19) -0.027(2)
C20 0.088(3) 0.140(5) 0.081(4) 0.043(3) -0.026(3) -0.065(3)
C19 0.087(4) 0.174(6) 0.077(4) 0.062(4) -0.017(3) -0.033(4)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C13 1.390(4) . ?
O1 C15 1.438(4) . ?
O3 C17 1.423(4) . ?
O3 C16 1.436(3) . ?
O2 C15 1.389(4) . ?
O2 C17 1.442(4) . ?
C11 C10 1.395(5) . ?
C11 C6 1.425(5) . ?
C11 C12 1.443(5) . ?
C14 C13 1.406(4) . ?
C14 C1 1.413(5) . ?
C14 C5 1.421(5) . ?
C5 C4 1.410(5) . ?
C5 C6 1.450(5) . ?
C12 C13 1.338(4) . ?
C12 C16 1.508(4) . ?
C6 C7 1.408(5) . ?
C1 C2 1.347(5) . ?
C1 H1 0.9300 . ?
C7 C8 1.377(6) . ?
C7 H7 0.9300 . ?
C10 C9 1.361(5) . ?
C10 H10 0.9300 . ?
C2 C3 1.387(5) . ?
C2 H2 0.9300 . ?
C4 C3 1.374(5) . ?
C4 H4 0.9300 . ?
C15 C24 1.525(4) . ?
C15 C16 1.547(4) . ?
C17 C18 1.514(5) . ?
C17 C21 1.529(4) . ?
C16 C22 1.511(5) . ?
C3 H3 0.9300 . ?
C9 C8 1.396(6) . ?
C9 H9 0.9300 . ?
C22 C23 1.522(5) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C24 C23 1.513(5) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C8 H8 0.9300 . ?
C18 C19 1.451(5) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C21 C20 1.502(5) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C20 C19 1.415(7) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
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
C13 O1 C15 106.2(2) . . ?
C17 O3 C16 108.6(2) . . ?
C15 O2 C17 108.1(2) . . ?
C10 C11 C6 119.1(3) . . ?
C10 C11 C12 122.7(3) . . ?
C6 C11 C12 118.2(3) . . ?
C13 C14 C1 123.0(3) . . ?
C13 C14 C5 116.6(3) . . ?
C1 C14 C5 120.5(3) . . ?
C4 C5 C14 116.5(3) . . ?
C4 C5 C6 122.9(3) . . ?
C14 C5 C6 120.6(3) . . ?
C13 C12 C11 120.0(3) . . ?
C13 C12 C16 109.4(3) . . ?
C11 C12 C16 130.6(3) . . ?
C12 C13 O1 114.7(3) . . ?
C12 C13 C14 125.2(3) . . ?
O1 C13 C14 120.1(3) . . ?
C7 C6 C11 118.3(3) . . ?
C7 C6 C5 122.4(3) . . ?
C11 C6 C5 119.3(3) . . ?
C2 C1 C14 120.6(4) . . ?
C2 C1 H1 119.7 . . ?
C14 C1 H1 119.7 . . ?
C8 C7 C6 121.1(4) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.4 . . ?
C9 C10 C11 121.2(4) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C1 C2 C3 120.2(4) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C3 C4 C5 121.5(4) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
O2 C15 O1 110.6(3) . . ?
O2 C15 C24 111.3(3) . . ?
O1 C15 C24 112.9(3) . . ?
O2 C15 C16 106.0(2) . . ?
O1 C15 C16 108.6(3) . . ?
C24 C15 C16 107.1(3) . . ?
O3 C17 O2 103.9(2) . . ?
O3 C17 C18 114.4(3) . . ?
O2 C17 C18 113.3(3) . . ?
O3 C17 C21 110.0(3) . . ?
O2 C17 C21 109.7(3) . . ?
C18 C17 C21 105.5(3) . . ?
O3 C16 C12 115.1(3) . . ?
O3 C16 C22 109.2(3) . . ?
C12 C16 C22 120.3(3) . . ?
O3 C16 C15 103.1(2) . . ?
C12 C16 C15 101.0(2) . . ?
C22 C16 C15 105.7(3) . . ?
C4 C3 C2 120.7(4) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C10 C9 C8 120.6(4) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C16 C22 C23 104.5(3) . . ?
C16 C22 H22A 110.9 . . ?
C23 C22 H22A 110.9 . . ?
C16 C22 H22B 110.9 . . ?
C23 C22 H22B 110.9 . . ?
H22A C22 H22B 108.9 . . ?
C23 C24 C15 101.7(3) . . ?
C23 C24 H24A 111.4 . . ?
C15 C24 H24A 111.4 . . ?
C23 C24 H24B 111.4 . . ?
C15 C24 H24B 111.4 . . ?
H24A C24 H24B 109.3 . . ?
C7 C8 C9 119.6(4) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C19 C18 C17 104.9(3) . . ?
C19 C18 H18A 110.8 . . ?
C17 C18 H18A 110.8 . . ?
C19 C18 H18B 110.8 . . ?
C17 C18 H18B 110.8 . . ?
H18A C18 H18B 108.9 . . ?
C24 C23 C22 105.1(3) . . ?
C24 C23 H23A 110.7 . . ?
C22 C23 H23A 110.7 . . ?
C24 C23 H23B 110.7 . . ?
C22 C23 H23B 110.7 . . ?
H23A C23 H23B 108.8 . . ?
C20 C21 C17 105.0(3) . . ?
C20 C21 H21A 110.7 . . ?
C17 C21 H21A 110.7 . . ?
C20 C21 H21B 110.8 . . ?
C17 C21 H21B 110.7 . . ?
H21A C21 H21B 108.8 . . ?
C19 C20 C21 108.5(3) . . ?
C19 C20 H20A 110.0 . . ?
C21 C20 H20A 110.0 . . ?
C19 C20 H20B 110.0 . . ?
C21 C20 H20B 110.0 . . ?
H20A C20 H20B 108.4 . . ?
C20 C19 C18 110.3(4) . . ?
C20 C19 H19A 109.6 . . ?
C18 C19 H19A 109.6 . . ?
C20 C19 H19B 109.6 . . ?
C18 C19 H19B 109.6 . . ?
H19A C19 H19B 108.1 . . ?
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
C13 C14 C5 C4 176.5(3) . . . . ?
C1 C14 C5 C4 -1.9(4) . . . . ?
C13 C14 C5 C6 -2.5(4) . . . . ?
C1 C14 C5 C6 179.2(3) . . . . ?
C10 C11 C12 C13 177.8(3) . . . . ?
C6 C11 C12 C13 -2.1(4) . . . . ?
C10 C11 C12 C16 -1.0(5) . . . . ?
C6 C11 C12 C16 179.1(3) . . . . ?
C11 C12 C13 O1 -179.2(3) . . . . ?
C16 C12 C13 O1 -0.2(4) . . . . ?
C11 C12 C13 C14 2.1(5) . . . . ?
C16 C12 C13 C14 -178.8(3) . . . . ?
C15 O1 C13 C12 1.8(3) . . . . ?
C15 O1 C13 C14 -179.6(3) . . . . ?
C1 C14 C13 C12 178.5(3) . . . . ?
C5 C14 C13 C12 0.2(4) . . . . ?
C1 C14 C13 O1 -0.1(4) . . . . ?
C5 C14 C13 O1 -178.4(3) . . . . ?
C10 C11 C6 C7 -0.8(4) . . . . ?
C12 C11 C6 C7 179.1(3) . . . . ?
C10 C11 C6 C5 179.9(3) . . . . ?
C12 C11 C6 C5 -0.2(4) . . . . ?
C4 C5 C6 C7 4.4(5) . . . . ?
C14 C5 C6 C7 -176.8(3) . . . . ?
C4 C5 C6 C11 -176.4(3) . . . . ?
C14 C5 C6 C11 2.5(4) . . . . ?
C13 C14 C1 C2 -176.3(3) . . . . ?
C5 C14 C1 C2 1.9(5) . . . . ?
C11 C6 C7 C8 0.2(5) . . . . ?
C5 C6 C7 C8 179.5(3) . . . . ?
C6 C11 C10 C9 0.8(5) . . . . ?
C12 C11 C10 C9 -179.1(3) . . . . ?
C14 C1 C2 C3 0.0(5) . . . . ?
C14 C5 C4 C3 0.0(4) . . . . ?
C6 C5 C4 C3 178.9(3) . . . . ?
C17 O2 C15 O1 96.7(3) . . . . ?
C17 O2 C15 C24 -136.9(3) . . . . ?
C17 O2 C15 C16 -20.8(3) . . . . ?
C13 O1 C15 O2 -118.4(3) . . . . ?
C13 O1 C15 C24 116.2(3) . . . . ?
C13 O1 C15 C16 -2.5(3) . . . . ?
C16 O3 C17 O2 -30.8(3) . . . . ?
C16 O3 C17 C18 93.3(3) . . . . ?
C16 O3 C17 C21 -148.2(3) . . . . ?
C15 O2 C17 O3 32.0(3) . . . . ?
C15 O2 C17 C18 -92.7(3) . . . . ?
C15 O2 C17 C21 149.6(3) . . . . ?
C17 O3 C16 C12 -91.0(3) . . . . ?
C17 O3 C16 C22 130.1(3) . . . . ?
C17 O3 C16 C15 18.0(3) . . . . ?
C13 C12 C16 O3 109.0(3) . . . . ?
C11 C12 C16 O3 -72.1(4) . . . . ?
C13 C12 C16 C22 -117.0(3) . . . . ?
C11 C12 C16 C22 62.0(4) . . . . ?
C13 C12 C16 C15 -1.3(3) . . . . ?
C11 C12 C16 C15 177.6(3) . . . . ?
O2 C15 C16 O3 1.8(3) . . . . ?
O1 C15 C16 O3 -117.0(3) . . . . ?
C24 C15 C16 O3 120.7(3) . . . . ?
O2 C15 C16 C12 121.2(3) . . . . ?
O1 C15 C16 C12 2.3(3) . . . . ?
C24 C15 C16 C12 -119.9(3) . . . . ?
O2 C15 C16 C22 -112.8(3) . . . . ?
O1 C15 C16 C22 128.4(3) . . . . ?
C24 C15 C16 C22 6.1(3) . . . . ?
C5 C4 C3 C2 1.9(5) . . . . ?
C1 C2 C3 C4 -2.0(6) . . . . ?
C11 C10 C9 C8 -0.2(5) . . . . ?
O3 C16 C22 C23 -92.1(3) . . . . ?
C12 C16 C22 C23 131.4(3) . . . . ?
C15 C16 C22 C23 18.2(3) . . . . ?
O2 C15 C24 C23 87.5(3) . . . . ?
O1 C15 C24 C23 -147.4(3) . . . . ?
C16 C15 C24 C23 -27.9(3) . . . . ?
C6 C7 C8 C9 0.4(5) . . . . ?
C10 C9 C8 C7 -0.4(5) . . . . ?
O3 C17 C18 C19 97.9(4) . . . . ?
O2 C17 C18 C19 -143.2(4) . . . . ?
C21 C17 C18 C19 -23.1(5) . . . . ?
C15 C24 C23 C22 39.6(4) . . . . ?
C16 C22 C23 C24 -36.7(3) . . . . ?
O3 C17 C21 C20 -109.1(4) . . . . ?
O2 C17 C21 C20 137.2(4) . . . . ?
C18 C17 C21 C20 14.7(5) . . . . ?
C17 C21 C20 C19 -0.7(7) . . . . ?
C21 C20 C19 C18 -14.6(7) . . . . ?
C17 C18 C19 C20 23.7(7) . . . . ?
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full 25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max 0.508
_refine_diff_density_min -0.251
_refine_diff_density_rms 0.053
# Attachment '9994_web_deposit_cif_file_2_H.S.P.Rao_1331128862.RScg.cif'
data_3g
_database_code_depnum_ccdc_archive 'CCDC 811040'
#TrackingRef '9994_web_deposit_cif_file_2_H.S.P.Rao_1331128862.RScg.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
10,11,12,13-Tetrahydrophenanthro[9,10-b]benzofuran-13-ol
;
_chemical_name_common
10,11,12,13-Tetrahydrophenanthro(9,10-b)benzofuran-13-ol
_chemical_melting_point ?
_chemical_formula_moiety 'C20 H16 O2'
_chemical_formula_sum 'C20 H16 O2'
_chemical_formula_weight 288.33
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'
_symmetry_cell_setting trigonal
_symmetry_space_group_name_H-M 'R -3'
_space_group_name_Hall '-R 3'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
_cell_length_a 17.7499(6)
_cell_length_b 17.7499(6)
_cell_length_c 24.5070(8)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 120.00
_cell_volume 6686.7(4)
_cell_formula_units_Z 18
_cell_measurement_temperature 293(2)
_cell_measurement_reflns_used 3048
_cell_measurement_theta_min 2.7709
_cell_measurement_theta_max 29.1492
_exptl_crystal_description block
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.54
_exptl_crystal_size_mid 0.48
_exptl_crystal_size_min 0.42
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.289
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 2736
_exptl_absorpt_coefficient_mu 0.082
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.957
_exptl_absorpt_correction_T_max 0.966
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details ?
_diffrn_ambient_temperature 293(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Xcalibur, Eos'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean 15.9821
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 4838
_diffrn_reflns_av_R_equivalents 0.0149
_diffrn_reflns_av_sigmaI/netI 0.0232
_diffrn_reflns_limit_h_min -17
_diffrn_reflns_limit_h_max 15
_diffrn_reflns_limit_k_min -19
_diffrn_reflns_limit_k_max 19
_diffrn_reflns_limit_l_min -29
_diffrn_reflns_limit_l_max 19
_diffrn_reflns_theta_min 2.78
_diffrn_reflns_theta_max 24.97
_reflns_number_total 2613
_reflns_number_gt 1992
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'CrysAlis CCD (Oxford Diffraction, 2009)'
_computing_cell_refinement 'CrysAlis RED (Oxford Diffraction, 2009)'
_computing_data_reduction 'CrysAlis RED (Oxford Diffraction, 2009)'
_computing_structure_solution 'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material 'PLATON (Spek, 2009)'
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 2613
_refine_ls_number_parameters 200
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0529
_refine_ls_R_factor_gt 0.0385
_refine_ls_wR_factor_ref 0.1257
_refine_ls_wR_factor_gt 0.1177
_refine_ls_goodness_of_fit_ref 0.923
_refine_ls_restrained_S_all 0.923
_refine_ls_shift/su_max 0.023
_refine_ls_shift/su_mean 0.003
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.73026(6) 0.67271(6) 0.11880(4) 0.0374(3) Uani 1 1 d . . .
O2 O 0.95223(7) 0.83339(7) 0.01021(4) 0.0455(3) Uani 1 1 d . . .
H2 H 1.0036 0.8654 0.0025 0.068 Uiso 1 1 calc R . .
C13 C 0.70918(9) 0.62040(9) 0.07349(5) 0.0338(4) Uani 1 1 d . . .
C12 C 0.77931(9) 0.64720(9) 0.03969(5) 0.0323(3) Uani 1 1 d . . .
C14 C 0.62586(9) 0.54552(9) 0.06572(5) 0.0347(4) Uani 1 1 d . . .
C1 C 0.55623(10) 0.52031(10) 0.10182(6) 0.0408(4) Uani 1 1 d . . .
H1 H 0.5626 0.5544 0.1322 0.049 Uiso 1 1 calc R . .
C11 C 0.76992(10) 0.60101(9) -0.01037(6) 0.0349(4) Uani 1 1 d . . .
C5 C 0.61702(10) 0.49551(10) 0.01870(6) 0.0385(4) Uani 1 1 d . . .
C6 C 0.68894(10) 0.52470(10) -0.02049(6) 0.0387(4) Uani 1 1 d . . .
C17 C 0.94518(9) 0.77565(9) 0.05318(6) 0.0354(4) Uani 1 1 d . . .
H17 H 0.9668 0.7379 0.0399 0.043 Uiso 1 1 calc R . .
C15 C 0.81768(9) 0.73292(9) 0.11329(6) 0.0357(4) Uani 1 1 d . . .
C16 C 0.85061(9) 0.72046(9) 0.06686(6) 0.0329(4) Uani 1 1 d . . .
C20 C 0.86273(10) 0.79825(10) 0.15649(6) 0.0439(4) Uani 1 1 d . . .
H20A H 0.8678 0.7703 0.1892 0.053 Uiso 1 1 calc R . .
H20B H 0.8300 0.8269 0.1654 0.053 Uiso 1 1 calc R . .
C10 C 0.83700(11) 0.62941(11) -0.04928(6) 0.0423(4) Uani 1 1 d . . .
H10 H 0.8899 0.6796 -0.0427 0.051 Uiso 1 1 calc R . .
C3 C 0.47012(11) 0.39480(12) 0.04738(7) 0.0551(5) Uani 1 1 d . . .
H3 H 0.4178 0.3437 0.0415 0.066 Uiso 1 1 calc R . .
C18 C 0.99580(10) 0.82266(11) 0.10386(7) 0.0470(4) Uani 1 1 d . . .
H18A H 1.0539 0.8672 0.0933 0.056 Uiso 1 1 calc R . .
H18B H 1.0012 0.7816 0.1273 0.056 Uiso 1 1 calc R . .
C9 C 0.82517(12) 0.58402(12) -0.09661(6) 0.0514(5) Uani 1 1 d . . .
H9 H 0.8700 0.6033 -0.1220 0.062 Uiso 1 1 calc R . .
C7 C 0.68010(12) 0.48047(12) -0.06979(7) 0.0526(5) Uani 1 1 d . . .
H7 H 0.6277 0.4303 -0.0775 0.063 Uiso 1 1 calc R . .
C8 C 0.74658(13) 0.50941(14) -0.10673(7) 0.0585(5) Uani 1 1 d . . .
H8 H 0.7389 0.4787 -0.1389 0.070 Uiso 1 1 calc R . .
C2 C 0.47884(10) 0.44576(11) 0.09274(7) 0.0484(4) Uani 1 1 d . . .
H2A H 0.4325 0.4293 0.1166 0.058 Uiso 1 1 calc R . .
C4 C 0.53683(11) 0.41841(11) 0.01155(7) 0.0505(5) Uani 1 1 d . . .
H4 H 0.5293 0.3829 -0.0183 0.061 Uiso 1 1 calc R . .
C19 C 0.95288(11) 0.86470(11) 0.13564(7) 0.0520(5) Uani 1 1 d . . .
H19A H 0.9480 0.9062 0.1123 0.062 Uiso 1 1 calc R . .
H19B H 0.9895 0.8963 0.1664 0.062 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0319(6) 0.0342(6) 0.0391(6) -0.0023(4) 0.0036(4) 0.0114(5)
O2 0.0303(6) 0.0460(7) 0.0579(7) 0.0205(5) 0.0062(5) 0.0174(5)
C13 0.0352(8) 0.0317(8) 0.0327(8) -0.0005(6) -0.0022(6) 0.0154(7)
C12 0.0324(8) 0.0300(8) 0.0342(8) 0.0030(6) -0.0005(6) 0.0153(6)
C14 0.0311(8) 0.0352(8) 0.0357(7) 0.0043(6) -0.0019(6) 0.0150(7)
C1 0.0375(9) 0.0433(9) 0.0376(8) 0.0019(7) -0.0007(7) 0.0173(8)
C11 0.0391(9) 0.0374(8) 0.0328(8) 0.0033(6) -0.0015(6) 0.0226(7)
C5 0.0371(9) 0.0371(9) 0.0399(8) -0.0016(6) -0.0074(6) 0.0174(7)
C6 0.0394(9) 0.0414(9) 0.0368(8) -0.0021(7) -0.0050(7) 0.0214(8)
C17 0.0316(8) 0.0329(8) 0.0442(9) 0.0065(6) 0.0023(6) 0.0179(7)
C15 0.0318(8) 0.0301(8) 0.0413(8) 0.0021(6) 0.0021(6) 0.0124(7)
C16 0.0318(8) 0.0282(8) 0.0384(8) 0.0047(6) 0.0023(6) 0.0147(7)
C20 0.0425(9) 0.0368(9) 0.0474(9) -0.0070(7) -0.0004(7) 0.0162(8)
C10 0.0428(9) 0.0477(10) 0.0396(8) 0.0062(7) 0.0039(7) 0.0251(8)
C3 0.0374(10) 0.0435(10) 0.0626(11) -0.0021(9) -0.0048(8) 0.0038(8)
C18 0.0343(9) 0.0462(10) 0.0545(10) 0.0033(7) -0.0043(7) 0.0157(8)
C9 0.0550(11) 0.0709(13) 0.0370(9) 0.0019(8) 0.0049(8) 0.0379(10)
C7 0.0474(10) 0.0593(11) 0.0487(10) -0.0168(8) -0.0095(8) 0.0249(9)
C8 0.0618(12) 0.0793(14) 0.0407(10) -0.0171(9) -0.0058(9) 0.0400(11)
C2 0.0328(9) 0.0512(11) 0.0511(10) 0.0087(8) 0.0034(7) 0.0134(8)
C4 0.0433(10) 0.0453(10) 0.0514(10) -0.0094(8) -0.0080(8) 0.0135(8)
C19 0.0416(10) 0.0400(10) 0.0614(11) -0.0113(8) -0.0023(8) 0.0106(8)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C13 1.3739(16) . ?
O1 C15 1.3821(17) . ?
O2 C17 1.4306(16) . ?
O2 H2 0.8200 . ?
C13 C12 1.3675(19) . ?
C13 C14 1.423(2) . ?
C12 C11 1.438(2) . ?
C12 C16 1.446(2) . ?
C14 C1 1.399(2) . ?
C14 C5 1.415(2) . ?
C1 C2 1.367(2) . ?
C1 H1 0.9300 . ?
C11 C10 1.407(2) . ?
C11 C6 1.420(2) . ?
C5 C4 1.408(2) . ?
C5 C6 1.469(2) . ?
C6 C7 1.406(2) . ?
C17 C16 1.499(2) . ?
C17 C18 1.515(2) . ?
C17 H17 0.9800 . ?
C15 C16 1.347(2) . ?
C15 C20 1.476(2) . ?
C20 C19 1.525(2) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C10 C9 1.367(2) . ?
C10 H10 0.9300 . ?
C3 C4 1.361(2) . ?
C3 C2 1.392(2) . ?
C3 H3 0.9300 . ?
C18 C19 1.521(2) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C9 C8 1.383(3) . ?
C9 H9 0.9300 . ?
C7 C8 1.367(2) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C2 H2A 0.9300 . ?
C4 H4 0.9300 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
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
C13 O1 C15 105.35(11) . . ?
C17 O2 H2 109.5 . . ?
C12 C13 O1 111.19(12) . . ?
C12 C13 C14 125.74(13) . . ?
O1 C13 C14 122.97(13) . . ?
C13 C12 C11 119.51(13) . . ?
C13 C12 C16 105.61(12) . . ?
C11 C12 C16 134.87(13) . . ?
C1 C14 C5 120.75(14) . . ?
C1 C14 C13 123.61(14) . . ?
C5 C14 C13 115.64(13) . . ?
C2 C1 C14 120.39(15) . . ?
C2 C1 H1 119.8 . . ?
C14 C1 H1 119.8 . . ?
C10 C11 C6 119.68(14) . . ?
C10 C11 C12 122.52(14) . . ?
C6 C11 C12 117.80(13) . . ?
C4 C5 C14 116.90(14) . . ?
C4 C5 C6 122.64(14) . . ?
C14 C5 C6 120.45(13) . . ?
C7 C6 C11 117.37(14) . . ?
C7 C6 C5 122.00(15) . . ?
C11 C6 C5 120.60(13) . . ?
O2 C17 C16 107.51(11) . . ?
O2 C17 C18 113.17(12) . . ?
C16 C17 C18 109.79(12) . . ?
O2 C17 H17 108.8 . . ?
C16 C17 H17 108.8 . . ?
C18 C17 H17 108.8 . . ?
C16 C15 O1 111.54(12) . . ?
C16 C15 C20 128.75(14) . . ?
O1 C15 C20 119.69(12) . . ?
C15 C16 C12 106.27(12) . . ?
C15 C16 C17 121.19(13) . . ?
C12 C16 C17 132.50(13) . . ?
C15 C20 C19 108.31(13) . . ?
C15 C20 H20A 110.0 . . ?
C19 C20 H20A 110.0 . . ?
C15 C20 H20B 110.0 . . ?
C19 C20 H20B 110.0 . . ?
H20A C20 H20B 108.4 . . ?
C9 C10 C11 120.70(16) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.6 . . ?
C4 C3 C2 121.21(16) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C17 C18 C19 112.68(13) . . ?
C17 C18 H18A 109.1 . . ?
C19 C18 H18A 109.1 . . ?
C17 C18 H18B 109.1 . . ?
C19 C18 H18B 109.1 . . ?
H18A C18 H18B 107.8 . . ?
C10 C9 C8 120.03(16) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C8 C7 C6 121.65(16) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C7 C8 C9 120.57(16) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C1 C2 C3 119.36(15) . . ?
C1 C2 H2A 120.3 . . ?
C3 C2 H2A 120.3 . . ?
C3 C4 C5 121.34(16) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C18 C19 C20 112.42(14) . . ?
C18 C19 H19A 109.1 . . ?
C20 C19 H19A 109.1 . . ?
C18 C19 H19B 109.1 . . ?
C20 C19 H19B 109.1 . . ?
H19A C19 H19B 107.9 . . ?
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
C15 O1 C13 C12 -1.54(15) . . . . ?
C15 O1 C13 C14 175.04(13) . . . . ?
O1 C13 C12 C11 -179.34(11) . . . . ?
C14 C13 C12 C11 4.2(2) . . . . ?
O1 C13 C12 C16 1.87(16) . . . . ?
C14 C13 C12 C16 -174.59(13) . . . . ?
C12 C13 C14 C1 179.36(14) . . . . ?
O1 C13 C14 C1 3.3(2) . . . . ?
C12 C13 C14 C5 0.4(2) . . . . ?
O1 C13 C14 C5 -175.70(12) . . . . ?
C5 C14 C1 C2 1.3(2) . . . . ?
C13 C14 C1 C2 -177.66(15) . . . . ?
C13 C12 C11 C10 174.29(14) . . . . ?
C16 C12 C11 C10 -7.4(3) . . . . ?
C13 C12 C11 C6 -4.8(2) . . . . ?
C16 C12 C11 C6 173.55(15) . . . . ?
C1 C14 C5 C4 -2.5(2) . . . . ?
C13 C14 C5 C4 176.54(13) . . . . ?
C1 C14 C5 C6 176.90(14) . . . . ?
C13 C14 C5 C6 -4.1(2) . . . . ?
C10 C11 C6 C7 0.3(2) . . . . ?
C12 C11 C6 C7 179.40(13) . . . . ?
C10 C11 C6 C5 -177.92(14) . . . . ?
C12 C11 C6 C5 1.2(2) . . . . ?
C4 C5 C6 C7 4.6(2) . . . . ?
C14 C5 C6 C7 -174.77(14) . . . . ?
C4 C5 C6 C11 -177.31(15) . . . . ?
C14 C5 C6 C11 3.3(2) . . . . ?
C13 O1 C15 C16 0.55(15) . . . . ?
C13 O1 C15 C20 -178.00(13) . . . . ?
O1 C15 C16 C12 0.56(16) . . . . ?
C20 C15 C16 C12 178.95(14) . . . . ?
O1 C15 C16 C17 -177.43(12) . . . . ?
C20 C15 C16 C17 1.0(2) . . . . ?
C13 C12 C16 C15 -1.46(16) . . . . ?
C11 C12 C16 C15 -179.97(15) . . . . ?
C13 C12 C16 C17 176.21(14) . . . . ?
C11 C12 C16 C17 -2.3(3) . . . . ?
O2 C17 C16 C15 -106.96(15) . . . . ?
C18 C17 C16 C15 16.54(18) . . . . ?
O2 C17 C16 C12 75.66(18) . . . . ?
C18 C17 C16 C12 -160.84(15) . . . . ?
C16 C15 C20 C19 11.2(2) . . . . ?
O1 C15 C20 C19 -170.54(13) . . . . ?
C6 C11 C10 C9 -0.3(2) . . . . ?
C12 C11 C10 C9 -179.43(14) . . . . ?
O2 C17 C18 C19 73.53(17) . . . . ?
C16 C17 C18 C19 -46.59(17) . . . . ?
C11 C10 C9 C8 0.1(3) . . . . ?
C11 C6 C7 C8 0.0(2) . . . . ?
C5 C6 C7 C8 178.18(16) . . . . ?
C6 C7 C8 C9 -0.2(3) . . . . ?
C10 C9 C8 C7 0.2(3) . . . . ?
C14 C1 C2 C3 0.4(2) . . . . ?
C4 C3 C2 C1 -0.9(3) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C14 C5 C4 C3 2.1(2) . . . . ?
C6 C5 C4 C3 -177.29(16) . . . . ?
C17 C18 C19 C20 61.86(19) . . . . ?
C15 C20 C19 C18 -40.69(19) . . . . ?
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full 24.97
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max 0.404
_refine_diff_density_min -0.206
_refine_diff_density_rms 0.037
data_3a
_database_code_depnum_ccdc_archive 'CCDC 813673'
#TrackingRef '9990_web_deposit_cif_file_0_H.S.P.Rao_1331128315.RSca.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
9a,11,11-Trimethyl-9a,12a-dihydrophenanthro[9',10':4,5]
furo[2,3-d][1,3]dioxole
;
_chemical_name_common
;9a,11,11-Trimethyl-9a,12a-dihydrophenanthro(9',10':4,5)
furo(2,3-d)(1,3)dioxole
;
_chemical_melting_point ?
_chemical_formula_moiety 'C20 H18 O3'
_chemical_formula_sum 'C20 H18 O3'
_chemical_formula_weight 306.34
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'
_symmetry_cell_setting orthorhombic
_symmetry_space_group_name_H-M 'P 21 21 21'
_space_group_name_Hall 'P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
_cell_length_a 8.1778(2)
_cell_length_b 8.9545(3)
_cell_length_c 21.7298(6)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 1591.23(8)
_cell_formula_units_Z 4
_cell_measurement_temperature 293(2)
_cell_measurement_reflns_used 5577
_cell_measurement_theta_min 2.6559
_cell_measurement_theta_max 29.2939
_exptl_crystal_description block
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.55
_exptl_crystal_size_mid 0.35
_exptl_crystal_size_min 0.3
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.279
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 648
_exptl_absorpt_coefficient_mu 0.085
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.965
_exptl_absorpt_correction_T_max 0.975
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details ?
_chemical_absolute_configuration .
_diffrn_ambient_temperature 293(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Xcalibur, Eos'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean 15.9821
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 8728
_diffrn_reflns_av_R_equivalents 0.0286
_diffrn_reflns_av_sigmaI/netI 0.0291
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_k_max 10
_diffrn_reflns_limit_l_min -25
_diffrn_reflns_limit_l_max 25
_diffrn_reflns_theta_min 2.66
_diffrn_reflns_theta_max 24.99
_reflns_number_total 2808
_reflns_number_gt 2369
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'CrysAlis CCD (Oxford Diffraction, 2009)'
_computing_cell_refinement 'CrysAlis RED (Oxford Diffraction, 2009)'
_computing_data_reduction 'CrysAlis RED (Oxford Diffraction, 2009)'
_computing_structure_solution 'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material 'PLATON (Spek, 2009)'
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack 0.2(12)
_refine_ls_number_reflns 2808
_refine_ls_number_parameters 211
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0450
_refine_ls_R_factor_gt 0.0341
_refine_ls_wR_factor_ref 0.1092
_refine_ls_wR_factor_gt 0.0997
_refine_ls_goodness_of_fit_ref 0.806
_refine_ls_restrained_S_all 0.806
_refine_ls_shift/su_max 0.020
_refine_ls_shift/su_mean 0.003
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.41364(14) 0.95843(16) 0.21329(6) 0.0424(3) Uani 1 1 d . . .
O1 O 0.65701(15) 0.82277(15) 0.20809(6) 0.0404(3) Uani 1 1 d . . .
C11 C 0.8421(2) 0.7071(2) 0.13424(8) 0.0336(4) Uani 1 1 d . . .
C5 C 0.9310(2) 0.8712(2) 0.04787(8) 0.0368(4) Uani 1 1 d . . .
C6 C 0.9344(2) 0.7282(2) 0.07961(8) 0.0358(4) Uani 1 1 d . . .
O3 O 0.48592(16) 1.10605(16) 0.13317(7) 0.0482(4) Uani 1 1 d . . .
C13 C 0.7452(2) 0.9655(2) 0.12695(8) 0.0336(4) Uani 1 1 d . . .
C14 C 0.8351(2) 0.9903(2) 0.07139(8) 0.0353(4) Uani 1 1 d . . .
C10 C 0.8438(2) 0.5695(2) 0.16501(9) 0.0415(5) Uani 1 1 d . . .
H10 H 0.7812 0.5568 0.2004 0.050 Uiso 1 1 calc R . .
C8 C 1.0284(3) 0.4727(3) 0.09031(11) 0.0545(6) Uani 1 1 d . . .
H8 H 1.0913 0.3939 0.0756 0.065 Uiso 1 1 calc R . .
C16 C 0.5831(2) 0.9691(2) 0.21814(8) 0.0386(4) Uani 1 1 d . . .
C4 C 1.0219(3) 0.8979(3) -0.00615(9) 0.0498(6) Uani 1 1 d . . .
H4 H 1.0866 0.8219 -0.0222 0.060 Uiso 1 1 calc R . .
C12 C 0.7499(2) 0.8319(2) 0.15570(8) 0.0332(4) Uani 1 1 d . . .
C15 C 0.6353(2) 1.0666(2) 0.16287(9) 0.0403(4) Uani 1 1 d . . .
H15 H 0.6942 1.1558 0.1767 0.048 Uiso 1 1 calc R . .
C1 C 0.8312(3) 1.1280(2) 0.04049(10) 0.0471(5) Uani 1 1 d . . .
H1 H 0.7674 1.2056 0.0557 0.056 Uiso 1 1 calc R . .
C7 C 1.0273(2) 0.6052(3) 0.05939(9) 0.0478(5) Uani 1 1 d . . .
H7 H 1.0898 0.6146 0.0238 0.057 Uiso 1 1 calc R . .
C17 C 0.3623(2) 1.0038(2) 0.15294(8) 0.0405(5) Uani 1 1 d . . .
C9 C 0.9362(3) 0.4544(2) 0.14364(11) 0.0526(6) Uani 1 1 d . . .
H9 H 0.9379 0.3638 0.1646 0.063 Uiso 1 1 calc R . .
C3 C 1.0170(3) 1.0329(3) -0.03539(10) 0.0622(7) Uani 1 1 d . . .
H3 H 1.0779 1.0476 -0.0710 0.075 Uiso 1 1 calc R . .
C2 C 0.9216(3) 1.1483(3) -0.01225(10) 0.0606(6) Uani 1 1 d . . .
H2 H 0.9188 1.2398 -0.0325 0.073 Uiso 1 1 calc R . .
C18 C 0.6296(3) 1.0183(3) 0.28163(10) 0.0636(7) Uani 1 1 d . . .
H18A H 0.5810 1.1136 0.2901 0.095 Uiso 1 1 calc R . .
H18B H 0.7465 1.0264 0.2844 0.095 Uiso 1 1 calc R . .
H18C H 0.5913 0.9464 0.3111 0.095 Uiso 1 1 calc R . .
C20 C 0.3495(3) 0.8706(3) 0.11086(10) 0.0592(6) Uani 1 1 d . . .
H20A H 0.3280 0.9039 0.0696 0.089 Uiso 1 1 calc R . .
H20B H 0.2619 0.8073 0.1244 0.089 Uiso 1 1 calc R . .
H20C H 0.4504 0.8159 0.1117 0.089 Uiso 1 1 calc R . .
C19 C 0.2036(2) 1.0891(3) 0.15870(11) 0.0567(6) Uani 1 1 d . . .
H19A H 0.2195 1.1741 0.1850 0.085 Uiso 1 1 calc R . .
H19B H 0.1213 1.0253 0.1761 0.085 Uiso 1 1 calc R . .
H19C H 0.1690 1.1222 0.1187 0.085 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O2 0.0322(6) 0.0580(9) 0.0369(7) -0.0001(6) -0.0007(5) 0.0062(7)
O1 0.0404(7) 0.0426(7) 0.0384(7) 0.0038(6) 0.0108(6) 0.0098(6)
C11 0.0260(8) 0.0386(10) 0.0363(9) -0.0038(8) -0.0023(8) -0.0002(8)
C5 0.0289(8) 0.0503(11) 0.0313(9) -0.0059(9) -0.0023(7) -0.0098(9)
C6 0.0266(8) 0.0427(11) 0.0381(10) -0.0109(8) -0.0017(7) -0.0050(8)
O3 0.0383(7) 0.0466(9) 0.0596(9) 0.0132(7) -0.0003(6) 0.0082(7)
C13 0.0278(8) 0.0352(10) 0.0377(10) -0.0026(8) -0.0018(8) 0.0001(8)
C14 0.0283(8) 0.0421(11) 0.0354(9) 0.0012(8) -0.0067(7) -0.0088(8)
C10 0.0366(9) 0.0411(11) 0.0467(11) 0.0010(9) 0.0047(9) 0.0012(9)
C8 0.0483(12) 0.0428(13) 0.0724(15) -0.0168(11) 0.0085(11) 0.0080(10)
C16 0.0327(9) 0.0464(11) 0.0368(10) -0.0073(8) -0.0005(8) 0.0090(9)
C4 0.0470(11) 0.0645(15) 0.0378(11) -0.0065(10) 0.0044(9) -0.0135(11)
C12 0.0283(8) 0.0393(10) 0.0319(9) -0.0012(8) 0.0021(8) 0.0003(8)
C15 0.0318(9) 0.0360(10) 0.0529(11) -0.0040(9) -0.0056(9) 0.0039(8)
C1 0.0444(10) 0.0469(12) 0.0500(12) 0.0079(10) -0.0064(9) -0.0077(10)
C7 0.0392(11) 0.0560(13) 0.0480(12) -0.0170(10) 0.0110(9) -0.0016(10)
C17 0.0362(9) 0.0492(12) 0.0361(10) 0.0000(9) -0.0024(8) 0.0062(9)
C9 0.0489(11) 0.0380(11) 0.0708(15) 0.0003(10) -0.0003(10) 0.0049(10)
C3 0.0623(14) 0.0858(18) 0.0386(12) 0.0025(12) 0.0091(11) -0.0268(15)
C2 0.0629(14) 0.0671(16) 0.0519(13) 0.0224(12) -0.0094(12) -0.0227(14)
C18 0.0623(13) 0.0770(17) 0.0515(13) -0.0210(12) -0.0190(11) 0.0234(13)
C20 0.0537(12) 0.0686(16) 0.0554(13) -0.0160(12) -0.0151(10) 0.0072(13)
C19 0.0370(11) 0.0695(16) 0.0637(14) 0.0014(13) -0.0061(10) 0.0143(11)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
O2 C16 1.393(2) . ?
O2 C17 1.436(2) . ?
O1 C12 1.371(2) . ?
O1 C16 1.459(2) . ?
C11 C10 1.402(3) . ?
C11 C6 1.419(3) . ?
C11 C12 1.427(3) . ?
C5 C4 1.410(3) . ?
C5 C14 1.419(3) . ?
C5 C6 1.454(3) . ?
C6 C7 1.408(3) . ?
O3 C17 1.430(2) . ?
O3 C15 1.426(2) . ?
C13 C12 1.350(3) . ?
C13 C14 1.431(3) . ?
C13 C15 1.496(3) . ?
C14 C1 1.404(3) . ?
C10 C9 1.359(3) . ?
C10 H10 0.9300 . ?
C8 C7 1.363(3) . ?
C8 C9 1.392(3) . ?
C8 H8 0.9300 . ?
C16 C18 1.498(3) . ?
C16 C15 1.545(3) . ?
C4 C3 1.367(3) . ?
C4 H4 0.9300 . ?
C15 H15 0.9800 . ?
C1 C2 1.376(3) . ?
C1 H1 0.9300 . ?
C7 H7 0.9300 . ?
C17 C20 1.507(3) . ?
C17 C19 1.511(3) . ?
C9 H9 0.9300 . ?
C3 C2 1.389(4) . ?
C3 H3 0.9300 . ?
C2 H2 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
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
C16 O2 C17 109.92(15) . . ?
C12 O1 C16 107.45(14) . . ?
C10 C11 C6 120.70(17) . . ?
C10 C11 C12 122.55(16) . . ?
C6 C11 C12 116.75(17) . . ?
C4 C5 C14 117.64(19) . . ?
C4 C5 C6 122.26(18) . . ?
C14 C5 C6 120.10(16) . . ?
C7 C6 C11 116.34(18) . . ?
C7 C6 C5 123.43(17) . . ?
C11 C6 C5 120.23(17) . . ?
C17 O3 C15 108.14(14) . . ?
C12 C13 C14 120.88(17) . . ?
C12 C13 C15 108.18(16) . . ?
C14 C13 C15 130.94(18) . . ?
C1 C14 C5 120.00(18) . . ?
C1 C14 C13 121.88(19) . . ?
C5 C14 C13 118.11(17) . . ?
C9 C10 C11 120.58(19) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C7 C8 C9 120.61(19) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
O2 C16 O1 109.84(16) . . ?
O2 C16 C18 110.05(16) . . ?
O1 C16 C18 107.25(16) . . ?
O2 C16 C15 104.76(15) . . ?
O1 C16 C15 106.07(14) . . ?
C18 C16 C15 118.66(19) . . ?
C3 C4 C5 121.4(2) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C13 C12 O1 114.93(16) . . ?
C13 C12 C11 123.92(16) . . ?
O1 C12 C11 121.15(16) . . ?
O3 C15 C13 115.37(16) . . ?
O3 C15 C16 104.78(15) . . ?
C13 C15 C16 103.27(15) . . ?
O3 C15 H15 111.0 . . ?
C13 C15 H15 111.0 . . ?
C16 C15 H15 111.0 . . ?
C2 C1 C14 120.2(2) . . ?
C2 C1 H1 119.9 . . ?
C14 C1 H1 119.9 . . ?
C8 C7 C6 122.04(18) . . ?
C8 C7 H7 119.0 . . ?
C6 C7 H7 119.0 . . ?
O3 C17 O2 104.41(14) . . ?
O3 C17 C20 111.94(16) . . ?
O2 C17 C20 110.52(17) . . ?
O3 C17 C19 107.97(17) . . ?
O2 C17 C19 108.58(16) . . ?
C20 C17 C19 113.01(17) . . ?
C10 C9 C8 119.7(2) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C4 C3 C2 120.4(2) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C1 C2 C3 120.3(2) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 C11 C6 C7 -0.8(3) . . . . ?
C12 C11 C6 C7 178.93(16) . . . . ?
C10 C11 C6 C5 179.63(16) . . . . ?
C12 C11 C6 C5 -0.6(2) . . . . ?
C4 C5 C6 C7 -0.2(3) . . . . ?
C14 C5 C6 C7 -179.57(16) . . . . ?
C4 C5 C6 C11 179.33(16) . . . . ?
C14 C5 C6 C11 -0.1(2) . . . . ?
C4 C5 C14 C1 0.9(2) . . . . ?
C6 C5 C14 C1 -179.64(16) . . . . ?
C4 C5 C14 C13 -178.63(16) . . . . ?
C6 C5 C14 C13 0.8(2) . . . . ?
C12 C13 C14 C1 179.60(17) . . . . ?
C15 C13 C14 C1 0.3(3) . . . . ?
C12 C13 C14 C5 -0.8(2) . . . . ?
C15 C13 C14 C5 179.84(17) . . . . ?
C6 C11 C10 C9 1.1(3) . . . . ?
C12 C11 C10 C9 -178.59(18) . . . . ?
C17 O2 C16 O1 -98.01(17) . . . . ?
C17 O2 C16 C18 144.14(18) . . . . ?
C17 O2 C16 C15 15.53(19) . . . . ?
C12 O1 C16 O2 115.81(16) . . . . ?
C12 O1 C16 C18 -124.61(18) . . . . ?
C12 O1 C16 C15 3.12(18) . . . . ?
C14 C5 C4 C3 -0.7(3) . . . . ?
C6 C5 C4 C3 179.92(18) . . . . ?
C14 C13 C12 O1 -179.37(15) . . . . ?
C15 C13 C12 O1 0.1(2) . . . . ?
C14 C13 C12 C11 0.1(3) . . . . ?
C15 C13 C12 C11 179.60(16) . . . . ?
C16 O1 C12 C13 -2.1(2) . . . . ?
C16 O1 C12 C11 178.35(16) . . . . ?
C10 C11 C12 C13 -179.65(17) . . . . ?
C6 C11 C12 C13 0.6(3) . . . . ?
C10 C11 C12 O1 -0.2(3) . . . . ?
C6 C11 C12 O1 -179.92(15) . . . . ?
C17 O3 C15 C13 94.06(19) . . . . ?
C17 O3 C15 C16 -18.8(2) . . . . ?
C12 C13 C15 O3 -111.87(18) . . . . ?
C14 C13 C15 O3 67.5(2) . . . . ?
C12 C13 C15 C16 1.83(19) . . . . ?
C14 C13 C15 C16 -178.78(17) . . . . ?
O2 C16 C15 O3 2.02(19) . . . . ?
O1 C16 C15 O3 118.19(15) . . . . ?
C18 C16 C15 O3 -121.21(19) . . . . ?
O2 C16 C15 C13 -119.15(16) . . . . ?
O1 C16 C15 C13 -2.97(18) . . . . ?
C18 C16 C15 C13 117.62(18) . . . . ?
C5 C14 C1 C2 -0.7(3) . . . . ?
C13 C14 C1 C2 178.86(17) . . . . ?
C9 C8 C7 C6 0.1(3) . . . . ?
C11 C6 C7 C8 0.2(3) . . . . ?
C5 C6 C7 C8 179.76(18) . . . . ?
C15 O3 C17 O2 28.15(19) . . . . ?
C15 O3 C17 C20 -91.43(19) . . . . ?
C15 O3 C17 C19 143.57(16) . . . . ?
C16 O2 C17 O3 -27.29(19) . . . . ?
C16 O2 C17 C20 93.2(2) . . . . ?
C16 O2 C17 C19 -142.28(17) . . . . ?
C11 C10 C9 C8 -0.8(3) . . . . ?
C7 C8 C9 C10 0.2(3) . . . . ?
C5 C4 C3 C2 0.2(3) . . . . ?
C14 C1 C2 C3 0.2(3) . . . . ?
C4 C3 C2 C1 0.1(3) . . . . ?
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full 24.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max 0.110
_refine_diff_density_min -0.152
_refine_diff_density_rms 0.030