#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:17:46 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178893 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/22/4112237.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4112237
loop_
_publ_author_name
'Gary A. Molander'
'David J. St. Jean'
'Julia Haas'
_publ_section_title
;
 Toward a General Route to the Eunicellin Diterpenes: The Asymmetric Total
 Synthesis of Deacetoxyalcyonin Acetate
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1642
_journal_page_last               1643
_journal_paper_doi               10.1021/ja0398464
_journal_volume                  126
_journal_year                    2004
_chemical_formula_sum            'C20 H28 O5'
_chemical_formula_weight         348.42
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.3569(13)
_cell_length_b                   11.7844(15)
_cell_length_c                   14.8684(19)
_cell_measurement_temperature    143(1)
_cell_volume                     1814.7(4)
_computing_data_collection       'CrystalClear (Rigaku, 1999)'
_computing_data_reduction        'CrystalClear (Rigaku, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, 1999)'
_diffrn_ambient_temperature      143(1)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       'phi and omega rotations'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0168
_diffrn_reflns_av_sigmaI/netI    0.0213
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8994
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.62
_exptl_absorpt_coefficient_mu    0.090
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3291
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0343
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0493P)²+0.2879P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0835
_refine_ls_wR_factor_ref         0.0858
_reflns_number_gt                3098
_reflns_number_total             3291
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0398464si20031203_080212_4.cif
_cod_data_source_block           cmpd16
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               4112237
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
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
C1 C 0.31462(16) 0.03218(14) 0.54845(12) 0.0303(4) Uani 1 1 d .
C2 C 0.35771(14) 0.15195(13) 0.52567(11) 0.0244(3) Uani 1 1 d .
H2 H 0.2906 0.1870 0.4885 0.032 Uiso 1 1 calc R
C3 C 0.48654(14) 0.16056(13) 0.47461(11) 0.0248(3) Uani 1 1 d .
H3 H 0.5459 0.1029 0.4979 0.033 Uiso 1 1 calc R
C4 C 0.48235(16) 0.15195(14) 0.37212(11) 0.0298(4) Uani 1 1 d .
H4A H 0.5684 0.1644 0.3484 0.040 Uiso 1 1 calc R
H4B H 0.4558 0.0759 0.3553 0.040 Uiso 1 1 calc R
C5 C 0.39130(15) 0.23623(14) 0.33043(10) 0.0273(3) Uani 1 1 d .
C6 C 0.43978(15) 0.35464(14) 0.30380(10) 0.0279(3) Uani 1 1 d .
H6 H 0.5338 0.3588 0.3103 0.037 Uiso 1 1 calc R
C7 C 0.37610(19) 0.45275(15) 0.35371(12) 0.0377(4) Uani 1 1 d .
H7A H 0.2856 0.4345 0.3623 0.050 Uiso 1 1 calc R
H7B H 0.3802 0.5196 0.3158 0.050 Uiso 1 1 calc R
C8 C 0.43456(18) 0.48278(14) 0.44593(11) 0.0338(4) Uani 1 1 d .
H8A H 0.5269 0.4693 0.4437 0.045 Uiso 1 1 calc R
H8B H 0.4217 0.5631 0.4569 0.045 Uiso 1 1 calc R
C9 C 0.37872(16) 0.41695(12) 0.52411(11) 0.0270(3) Uani 1 1 d .
C10 C 0.46059(14) 0.32275(13) 0.56557(10) 0.0243(3) Uani 1 1 d .
H10 H 0.5176 0.3552 0.6115 0.032 Uiso 1 1 calc R
C11 C 0.37994(14) 0.22791(13) 0.60733(10) 0.0234(3) Uani 1 1 d .
H11 H 0.2971 0.2589 0.6276 0.031 Uiso 1 1 calc R
C12 C 0.44488(14) 0.16479(13) 0.68544(10) 0.0262(3) Uani 1 1 d .
H12 H 0.5251 0.1323 0.6618 0.035 Uiso 1 1 calc R
C13 C 0.35829(17) 0.06475(15) 0.71250(12) 0.0371(4) Uani 1 1 d .
H13A H 0.4060 0.0152 0.7527 0.049 Uiso 1 1 calc R
H13B H 0.2841 0.0935 0.7451 0.049 Uiso 1 1 calc R
C14 C 0.31224(18) -0.00279(15) 0.63340(13) 0.0373(4) Uani 1 1 d .
H14 H 0.2794 -0.0749 0.6446 0.050 Uiso 1 1 calc R
C15 C 0.26852(19) -0.03924(15) 0.47149(13) 0.0403(4) Uani 1 1 d .
H15A H 0.3408 -0.0610 0.4350 0.061 Uiso 1 1 calc R
H15B H 0.2085 0.0035 0.4358 0.061 Uiso 1 1 calc R
H15C H 0.2267 -0.1060 0.4944 0.061 Uiso 1 1 calc R
C16 C 0.44752(16) 0.29988(14) 0.15040(11) 0.0306(4) Uani 1 1 d .
C17 C 0.40277(19) 0.32612(15) 0.05728(11) 0.0363(4) Uani 1 1 d .
H17A H 0.4462 0.2773 0.0153 0.054 Uiso 1 1 calc R
H17B H 0.4221 0.4038 0.0433 0.054 Uiso 1 1 calc R
H17C H 0.3113 0.3141 0.0533 0.054 Uiso 1 1 calc R
C18 C 0.48282(15) 0.24198(15) 0.76477(10) 0.0291(4) Uani 1 1 d .
H18 H 0.5474 0.2954 0.7418 0.039 Uiso 1 1 calc R
C19 C 0.37158(18) 0.31329(17) 0.80177(13) 0.0428(5) Uani 1 1 d .
H19A H 0.3360 0.3589 0.7544 0.064 Uiso 1 1 calc R
H19B H 0.4030 0.3617 0.8489 0.064 Uiso 1 1 calc R
H19C H 0.3059 0.2641 0.8253 0.064 Uiso 1 1 calc R
C20 C 0.54775(17) 0.17489(17) 0.83997(12) 0.0388(4) Uani 1 1 d .
H20A H 0.5837 0.2265 0.8832 0.058 Uiso 1 1 calc R
H20B H 0.6153 0.1287 0.8152 0.058 Uiso 1 1 calc R
H20C H 0.4851 0.1272 0.8689 0.058 Uiso 1 1 calc R
O1 O 0.53713(10) 0.27187(9) 0.49601(7) 0.0279(3) Uani 1 1 d .
O2 O 0.27807(11) 0.21458(12) 0.31883(9) 0.0454(3) Uani 1 1 d .
O3 O 0.40305(12) 0.37466(9) 0.21014(8) 0.0316(3) Uani 1 1 d .
O4 O 0.51608(15) 0.22154(12) 0.17152(9) 0.0549(4) Uani 1 1 d .
O5 O 0.27379(12) 0.43998(11) 0.55445(9) 0.0427(3) Uani 1 1 d .
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
C14 C1 C15 123.07(16)
C14 C1 C2 120.38(16)
C15 C1 C2 116.45(15)
C1 C2 C11 114.34(13)
C1 C2 C3 115.23(13)
C11 C2 C3 102.89(12)
O1 C3 C4 106.84(12)
O1 C3 C2 105.37(12)
C4 C3 C2 117.59(13)
C5 C4 C3 112.66(13)
O2 C5 C4 121.76(15)
O2 C5 C6 118.10(14)
C4 C5 C6 120.12(13)
O3 C6 C7 103.22(12)
O3 C6 C5 107.88(12)
C7 C6 C5 114.99(14)
C6 C7 C8 115.95(14)
C9 C8 C7 114.59(14)
O5 C9 C8 121.07(15)
O5 C9 C10 120.82(15)
C8 C9 C10 118.09(14)
O1 C10 C11 106.83(12)
O1 C10 C9 108.64(12)
C11 C10 C9 113.11(12)
C2 C11 C10 100.86(12)
C2 C11 C12 112.58(12)
C10 C11 C12 115.00(12)
C13 C12 C11 108.33(13)
C13 C12 C18 113.69(13)
C11 C12 C18 113.90(13)
C14 C13 C12 112.85(15)
C1 C14 C13 125.14(16)
O4 C16 O3 122.40(16)
O4 C16 C17 125.65(16)
O3 C16 C17 111.95(14)
C20 C18 C19 110.70(14)
C20 C18 C12 111.57(14)
C19 C18 C12 114.08(13)
C10 O1 C3 109.71(11)
C16 O3 C6 115.96(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C14 1.329(3)
C1 C15 1.499(2)
C1 C2 1.518(2)
C2 C11 1.526(2)
C2 C3 1.539(2)
C3 O1 1.4479(19)
C3 C4 1.528(2)
C4 C5 1.503(2)
C5 O2 1.212(2)
C5 C6 1.535(2)
C6 O3 1.4628(19)
C6 C7 1.524(2)
C7 C8 1.540(2)
C8 C9 1.512(2)
C9 O5 1.208(2)
C9 C10 1.527(2)
C10 O1 1.4344(19)
C10 C11 1.527(2)
C11 C12 1.534(2)
C12 C13 1.535(2)
C12 C18 1.540(2)
C13 C14 1.498(3)
C16 O4 1.206(2)
C16 O3 1.333(2)
C16 C17 1.492(2)
C18 C20 1.526(2)
C18 C19 1.528(2)
