#------------------------------------------------------------------------------
#$Date: 2016-02-17 15:59:55 +0200 (Wed, 17 Feb 2016) $
#$Revision: 176630 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/14/2241420.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_2241420
loop_
_publ_author_name
'Jones, Alan M.'
'Storey, John M. D.'
'Harrison, William T. A.'
_publ_section_title
;
 Investigations into the construction of the pentasubstituted ring
 C of Neosurugatoxin -- a crystallographic study
;
_journal_coeditor_code           GK2648
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              44
_journal_page_last               48
_journal_paper_doi               10.1107/S2056989015023506
_journal_volume                  72
_journal_year                    2016
_chemical_formula_iupac          'C21 H24 O3'
_chemical_formula_moiety         'C21 H24 O3'
_chemical_formula_sum            'C21 H24 O3'
_chemical_formula_weight         324.40
_chemical_name_systematic
(+-)-(3aR,4S,5S,6aS)-4-Benzyloxy-4-methyl-5-phenylhexahydro-1H-cyclopenta[c]furan-5-ol
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 92.3907(16)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.8872(3)
_cell_length_b                   19.3544(6)
_cell_length_c                   6.80460(10)
_cell_measurement_reflns_used    3991
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     1695.75(7)
_computing_cell_refinement
;
SCALEPACK (Otwinowski & Minor, 1997)
;
_computing_data_collection
;
COLLECT (Nonius, 1998)
;
_computing_data_reduction
;
DENZO and SCALEPACK (Otwinowski & Minor, 1997), and SORTAV (Blessing,
1995)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0911
_diffrn_reflns_av_sigmaI/netI    0.0558
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            28187
_diffrn_reflns_theta_full        27.55
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_min         3.16
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.232
_refine_ls_extinction_coef       0.015(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL97 (Sheldrick, 2008)
;
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3899
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0801
_refine_ls_R_factor_gt           0.0526
_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)+(0.0522P)²+0.6264P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1197
_refine_ls_wR_factor_ref         0.1322
_reflns_number_gt                2834
_reflns_number_total             3899
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gk2648sup1.cif
_cod_data_source_block           II
_cod_depositor_comments
;Adding full bibliography for 2241419--2241421.cif.

 Adding full bibliography for 2241419--2241421.cif.
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2241420
_cod_database_fobs_code          2241420
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'
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_symmetry_multiplicity
C C1 0.30147(13) 0.58494(9) 0.3553(2) 0.0281(4) Uani d . 1 1
H H1 0.2965 0.5555 0.2345 0.034 Uiso calc R 1 1
C C2 0.29204(13) 0.66286(9) 0.2994(2) 0.0287(4) Uani d . 1 1
H H2 0.2808 0.6687 0.1541 0.034 Uiso calc R 1 1
C C3 0.39707(14) 0.69274(10) 0.3697(3) 0.0363(4) Uani d . 1 1
H H3A 0.4456 0.6937 0.2608 0.044 Uiso calc R 1 1
H H3B 0.3887 0.7404 0.4198 0.044 Uiso calc R 1 1
C C4 0.40989(14) 0.57980(10) 0.4536(3) 0.0350(4) Uani d . 1 1
H H4A 0.4103 0.5463 0.5636 0.042 Uiso calc R 1 1
H H4B 0.4607 0.5644 0.3576 0.042 Uiso calc R 1 1
C C5 0.19910(13) 0.69099(9) 0.4091(2) 0.0269(4) Uani d . 1 1
H H5A 0.2134 0.7385 0.4569 0.032 Uiso calc R 1 1
H H5B 0.1360 0.6919 0.3212 0.032 Uiso calc R 1 1
C C6 0.18412(12) 0.64195(8) 0.5828(2) 0.0225(4) Uani d . 1 1
C C7 0.20787(13) 0.57048(9) 0.4881(2) 0.0242(4) Uani d . 1 1
C C8 0.11588(14) 0.54513(9) 0.3603(2) 0.0300(4) Uani d . 1 1
H H8A 0.1346 0.5021 0.2948 0.045 Uiso calc R 1 1
H H8B 0.0972 0.5802 0.2611 0.045 Uiso calc R 1 1
H H8C 0.0566 0.5368 0.4428 0.045 Uiso calc R 1 1
C C9 0.07863(12) 0.64665(9) 0.6741(2) 0.0237(4) Uani d . 1 1
C C10 0.05847(13) 0.60608(9) 0.8379(2) 0.0284(4) Uani d . 1 1
H H10 0.1113 0.5767 0.8921 0.034 Uiso calc R 1 1
C C11 -0.03727(14) 0.60800(10) 0.9227(2) 0.0317(4) Uani d . 1 1
H H11 -0.0498 0.5796 1.0332 0.038 Uiso calc R 1 1
C C12 -0.11497(14) 0.65112(10) 0.8471(2) 0.0322(4) Uani d . 1 1
H H12 -0.1810 0.6521 0.9042 0.039 Uiso calc R 1 1
C C13 -0.09541(14) 0.69271(10) 0.6879(3) 0.0321(4) Uani d . 1 1
H H13 -0.1479 0.7231 0.6370 0.039 Uiso calc R 1 1
C C14 0.00014(13) 0.69059(9) 0.6015(2) 0.0280(4) Uani d . 1 1
H H14 0.0123 0.7194 0.4917 0.034 Uiso calc R 1 1
C C15 0.24848(15) 0.45363(9) 0.5913(2) 0.0311(4) Uani d . 1 1
H H15A 0.2899 0.4514 0.4721 0.037 Uiso calc R 1 1
H H15B 0.1807 0.4310 0.5618 0.037 Uiso calc R 1 1
C C16 0.30523(13) 0.41712(9) 0.7601(2) 0.0261(4) Uani d . 1 1
C C17 0.31224(14) 0.34524(9) 0.7586(3) 0.0295(4) Uani d . 1 1
H H17 0.2798 0.3199 0.6534 0.035 Uiso calc R 1 1
C C18 0.36607(14) 0.31032(10) 0.9088(3) 0.0324(4) Uani d . 1 1
H H18 0.3709 0.2614 0.9053 0.039 Uiso calc R 1 1
C C19 0.41288(14) 0.34674(10) 1.0645(3) 0.0329(4) Uani d . 1 1
H H19 0.4494 0.3230 1.1680 0.039 Uiso calc R 1 1
C C20 0.40569(14) 0.41784(10) 1.0669(3) 0.0335(4) Uani d . 1 1
H H20 0.4376 0.4430 1.1731 0.040 Uiso calc R 1 1
C C21 0.35245(14) 0.45329(9) 0.9163(2) 0.0297(4) Uani d . 1 1
H H22 0.3483 0.5023 0.9200 0.036 Uiso calc R 1 1
O O1 0.43553(9) 0.64763(7) 0.52482(18) 0.0359(3) Uani d . 1 1
O O2 0.25800(9) 0.65642(6) 0.74180(16) 0.0258(3) Uani d . 1 1
H H2o 0.3204(16) 0.6532(10) 0.697(3) 0.031 Uiso d . 1 1
O O3 0.23287(9) 0.52361(6) 0.64562(15) 0.0276(3) Uani d . 1 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
C4 C1 C2 103.32(14)
C4 C1 C7 116.71(14)
C2 C1 C7 105.08(13)
C4 C1 H1 110.4
C2 C1 H1 110.4
C7 C1 H1 110.4
C3 C2 C5 114.28(15)
C3 C2 C1 103.32(14)
C5 C2 C1 106.17(13)
C3 C2 H2 110.9
C5 C2 H2 110.9
C1 C2 H2 110.9
O1 C3 C2 105.82(14)
O1 C3 H3A 110.6
C2 C3 H3A 110.6
O1 C3 H3B 110.6
C2 C3 H3B 110.6
H3A C3 H3B 108.7
O1 C4 C1 106.40(14)
O1 C4 H4A 110.4
C1 C4 H4A 110.4
O1 C4 H4B 110.4
C1 C4 H4B 110.4
H4A C4 H4B 108.6
C6 C5 C2 106.29(13)
C6 C5 H5A 110.5
C2 C5 H5A 110.5
C6 C5 H5B 110.5
C2 C5 H5B 110.5
H5A C5 H5B 108.7
O2 C6 C9 104.83(12)
O2 C6 C5 111.00(13)
C9 C6 C5 114.90(13)
O2 C6 C7 110.35(12)
C9 C6 C7 114.54(13)
C5 C6 C7 101.38(12)
O3 C7 C8 111.68(13)
O3 C7 C6 107.13(12)
C8 C7 C6 111.09(14)
O3 C7 C1 113.06(13)
C8 C7 C1 109.21(13)
C6 C7 C1 104.43(13)
C7 C8 H8A 109.5
C7 C8 H8B 109.5
H8A C8 H8B 109.5
C7 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C14 C9 C10 117.94(15)
C14 C9 C6 122.61(15)
C10 C9 C6 119.45(14)
C11 C10 C9 121.08(16)
C11 C10 H10 119.5
C9 C10 H10 119.5
C10 C11 C12 120.28(17)
C10 C11 H11 119.9
C12 C11 H11 119.9
C13 C12 C11 119.30(16)
C13 C12 H12 120.3
C11 C12 H12 120.3
C12 C13 C14 120.61(17)
C12 C13 H13 119.7
C14 C13 H13 119.7
C13 C14 C9 120.75(16)
C13 C14 H14 119.6
C9 C14 H14 119.6
O3 C15 C16 108.51(13)
O3 C15 H15A 110.0
C16 C15 H15A 110.0
O3 C15 H15B 110.0
C16 C15 H15B 110.0
H15A C15 H15B 108.4
C21 C16 C17 118.78(16)
C21 C16 C15 121.85(15)
C17 C16 C15 119.36(15)
C18 C17 C16 120.74(17)
C18 C17 H17 119.6
C16 C17 H17 119.6
C17 C18 C19 120.17(17)
C17 C18 H18 119.9
C19 C18 H18 119.9
C20 C19 C18 119.24(16)
C20 C19 H19 120.4
C18 C19 H19 120.4
C19 C20 C21 120.97(17)
C19 C20 H20 119.5
C21 C20 H20 119.5
C20 C21 C16 120.10(16)
C20 C21 H22 120.0
C16 C21 H22 120.0
C4 O1 C3 103.87(13)
C6 O2 H2o 108.4(12)
C15 O3 C7 116.08(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C4 1.527(2)
C1 C2 1.559(2)
C1 C7 1.562(2)
C1 H1 1.0000
C2 C3 1.530(3)
C2 C5 1.537(2)
C2 H2 1.0000
C3 O1 1.441(2)
C3 H3A 0.9900
C3 H3B 0.9900
C4 O1 1.433(2)
C4 H4A 0.9900
C4 H4B 0.9900
C5 C6 1.534(2)
C5 H5A 0.9900
C5 H5B 0.9900
C6 O2 1.4387(19)
C6 C9 1.521(2)
C6 C7 1.562(2)
C7 O3 1.4305(19)
C7 C8 1.522(2)
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C9 C14 1.396(2)
C9 C10 1.397(2)
C10 C11 1.384(2)
C10 H10 0.9500
C11 C12 1.386(3)
C11 H11 0.9500
C12 C13 1.381(3)
C12 H12 0.9500
C13 C14 1.387(2)
C13 H13 0.9500
C14 H14 0.9500
C15 O3 1.421(2)
C15 C16 1.511(2)
C15 H15A 0.9900
C15 H15B 0.9900
C16 C21 1.391(2)
C16 C17 1.394(2)
C17 C18 1.387(3)
C17 H17 0.9500
C18 C19 1.389(3)
C18 H18 0.9500
C19 C20 1.379(3)
C19 H19 0.9500
C20 C21 1.391(2)
C20 H20 0.9500
C21 H22 0.9500
O2 H2o 0.87(2)
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
O2 H2o O1 . 0.87(2) 1.93(2) 2.7794(17) 162.9(18)
C10 H10 O3 . 0.95 2.56 3.091(2) 116
C5 H5A O2 4_575 0.99 2.58 3.266(2) 126
C19 H19 O1 3_667 0.95 2.58 3.344(2) 138
C12 H12 Cg4 3_567 0.95 2.74 3.6619(19) 165
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
C4 C1 C2 C3 0.84(16)
C7 C1 C2 C3 123.68(14)
C4 C1 C2 C5 -119.73(14)
C7 C1 C2 C5 3.10(17)
C5 C2 C3 O1 89.86(17)
C1 C2 C3 O1 -25.02(17)
C2 C1 C4 O1 23.80(16)
C7 C1 C4 O1 -90.94(17)
C3 C2 C5 C6 -91.02(17)
C1 C2 C5 C6 22.18(17)
C2 C5 C6 O2 79.01(16)
C2 C5 C6 C9 -162.29(13)
C2 C5 C6 C7 -38.20(16)
O2 C6 C7 O3 42.19(17)
C9 C6 C7 O3 -75.80(16)
C5 C6 C7 O3 159.87(12)
O2 C6 C7 C8 164.41(13)
C9 C6 C7 C8 46.42(17)
C5 C6 C7 C8 -77.91(15)
O2 C6 C7 C1 -77.98(15)
C9 C6 C7 C1 164.03(13)
C5 C6 C7 C1 39.70(15)
C4 C1 C7 O3 -29.0(2)
C2 C1 C7 O3 -142.74(13)
C4 C1 C7 C8 -153.99(15)
C2 C1 C7 C8 92.26(16)
C4 C1 C7 C6 87.11(17)
C2 C1 C7 C6 -26.63(16)
O2 C6 C9 C14 124.12(16)
C5 C6 C9 C14 2.0(2)
C7 C6 C9 C14 -114.80(17)
O2 C6 C9 C10 -55.45(18)
C5 C6 C9 C10 -177.55(15)
C7 C6 C9 C10 65.64(19)
C14 C9 C10 C11 1.7(2)
C6 C9 C10 C11 -178.76(15)
C9 C10 C11 C12 -0.7(3)
C10 C11 C12 C13 -0.8(3)
C11 C12 C13 C14 1.3(3)
C12 C13 C14 C9 -0.3(3)
C10 C9 C14 C13 -1.2(2)
C6 C9 C14 C13 179.27(15)
O3 C15 C16 C21 -13.3(2)
O3 C15 C16 C17 167.77(15)
C21 C16 C17 C18 -0.6(2)
C15 C16 C17 C18 178.35(16)
C16 C17 C18 C19 0.7(3)
C17 C18 C19 C20 -0.4(3)
C18 C19 C20 C21 0.0(3)
C19 C20 C21 C16 0.1(3)
C17 C16 C21 C20 0.2(2)
C15 C16 C21 C20 -178.73(16)
C1 C4 O1 C3 -40.50(17)
C2 C3 O1 C4 40.92(17)
C16 C15 O3 C7 162.70(13)
C8 C7 O3 C15 52.94(19)
C6 C7 O3 C15 174.79(14)
C1 C7 O3 C15 -70.71(18)
