#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:17:46 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178893 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/22/4112236.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_4112236
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            'C16 H24 O2'
_chemical_formula_weight         248.35
_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                   5.6107(8)
_cell_length_b                   9.7250(16)
_cell_length_c                   25.856(4)
_cell_measurement_temperature    143(1)
_cell_volume                     1410.8(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 0.974
_diffrn_measured_fraction_theta_max 0.974
_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  0.0264
_diffrn_reflns_av_sigmaI/netI    0.0389
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            7530
_diffrn_reflns_theta_full        25.32
_diffrn_reflns_theta_max         25.32
_diffrn_reflns_theta_min         2.62
_exptl_absorpt_coefficient_mu    0.075
_exptl_crystal_density_diffrn    1.169
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.122
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2473
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0440
_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)+(0.0410P)²+0.2173P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.0972
_reflns_number_gt                2192
_reflns_number_total             2473
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0398464si20031203_080212_3.cif
_cod_data_source_block           cmpd8
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               4112236
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 0.8303(3) 0.80911(19) 0.61493(7) 0.0320(4) Uani 1 1 d .
C2 C 0.8786(3) 0.66327(19) 0.59781(7) 0.0298(4) Uani 1 1 d .
H2 H 1.0501 0.6446 0.5995 0.040 Uiso 1 1 calc R
C3 C 0.7884(3) 0.6390(2) 0.54228(7) 0.0346(5) Uani 1 1 d .
H3 H 0.8065 0.7225 0.5214 0.046 Uiso 1 1 calc R
C4 C 0.9142(4) 0.5161(2) 0.51609(8) 0.0414(5) Uani 1 1 d .
H4A H 0.8615 0.5096 0.4804 0.055 Uiso 1 1 calc R
H4B H 1.0848 0.5321 0.5159 0.055 Uiso 1 1 calc R
C5 C 0.8629(4) 0.3822(2) 0.54334(7) 0.0389(5) Uani 1 1 d .
C6 C 0.6124(4) 0.3653(2) 0.56395(8) 0.0389(5) Uani 1 1 d .
H6 H 0.5062 0.3526 0.5342 0.052 Uiso 1 1 calc R
C7 C 0.5475(3) 0.5036(2) 0.58957(7) 0.0320(4) Uani 1 1 d .
H7 H 0.3922 0.4969 0.6067 0.043 Uiso 1 1 calc R
C8 C 0.7400(3) 0.55077(19) 0.62842(7) 0.0291(5) Uani 1 1 d .
H8 H 0.8486 0.4734 0.6343 0.039 Uiso 1 1 calc R
C9 C 0.6431(3) 0.5972(2) 0.68107(7) 0.0323(5) Uani 1 1 d .
H9 H 0.5296 0.5272 0.6927 0.043 Uiso 1 1 calc R
C10 C 0.5025(4) 0.7315(2) 0.67330(8) 0.0375(5) Uani 1 1 d .
H10A H 0.3637 0.7138 0.6520 0.050 Uiso 1 1 calc R
H10B H 0.4480 0.7655 0.7065 0.050 Uiso 1 1 calc R
C11 C 0.6567(4) 0.8385(2) 0.64776(7) 0.0363(5) Uani 1 1 d .
H11 H 0.6283 0.9304 0.6555 0.048 Uiso 1 1 calc R
C12 C 0.9899(4) 0.9168(2) 0.59186(8) 0.0439(5) Uani 1 1 d .
H12A H 0.9533 1.0047 0.6068 0.066 Uiso 1 1 calc R
H12B H 0.9652 0.9206 0.5551 0.066 Uiso 1 1 calc R
H12C H 1.1532 0.8940 0.5989 0.066 Uiso 1 1 calc R
C13 C 0.5797(4) 0.2429(2) 0.59939(9) 0.0513(6) Uani 1 1 d .
H13A H 0.6247 0.1604 0.5815 0.077 Uiso 1 1 calc R
H13B H 0.4156 0.2367 0.6097 0.077 Uiso 1 1 calc R
H13C H 0.6780 0.2539 0.6295 0.077 Uiso 1 1 calc R
C14 C 0.8369(4) 0.6098(2) 0.72320(7) 0.0365(5) Uani 1 1 d .
H14 H 0.9458 0.6840 0.7132 0.049 Uiso 1 1 calc R
C15 C 0.9822(5) 0.4782(2) 0.72891(9) 0.0557(6) Uani 1 1 d .
H15A H 1.0856 0.4860 0.7583 0.084 Uiso 1 1 calc R
H15B H 1.0760 0.4640 0.6983 0.084 Uiso 1 1 calc R
H15C H 0.8765 0.4016 0.7337 0.084 Uiso 1 1 calc R
C16 C 0.7278(5) 0.6469(3) 0.77552(8) 0.0580(7) Uani 1 1 d .
H16A H 0.6151 0.5774 0.7854 0.087 Uiso 1 1 calc R
H16B H 0.6483 0.7340 0.7730 0.087 Uiso 1 1 calc R
H16C H 0.8516 0.6525 0.8011 0.087 Uiso 1 1 calc R
O1 O 0.5412(2) 0.60755(13) 0.54995(5) 0.0359(3) Uani 1 1 d .
O2 O 1.0166(3) 0.29397(15) 0.54870(6) 0.0522(4) 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
C11 C1 C12 122.91(19)
C11 C1 C2 121.52(18)
C12 C1 C2 115.57(17)
C1 C2 C3 110.99(15)
C1 C2 C8 114.90(16)
C3 C2 C8 101.64(14)
O1 C3 C2 102.79(15)
O1 C3 C4 109.74(16)
C2 C3 C4 112.17(15)
C5 C4 C3 112.09(16)
O2 C5 C4 121.56(19)
O2 C5 C6 122.6(2)
C4 C5 C6 115.83(17)
C13 C6 C5 114.30(17)
C13 C6 C7 113.40(17)
C5 C6 C7 106.01(17)
O1 C7 C8 105.73(15)
O1 C7 C6 108.20(14)
C8 C7 C6 111.91(15)
C9 C8 C7 114.62(15)
C9 C8 C2 114.87(15)
C7 C8 C2 103.14(14)
C8 C9 C10 108.42(15)
C8 C9 C14 113.57(16)
C10 C9 C14 112.70(16)
C11 C10 C9 110.43(17)
C1 C11 C10 123.73(18)
C15 C14 C16 109.06(18)
C15 C14 C9 112.23(17)
C16 C14 C9 111.18(18)
C3 O1 C7 102.96(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C11 1.323(3)
C1 C12 1.502(3)
C1 C2 1.510(3)
C2 C3 1.541(3)
C2 C8 1.558(3)
C3 O1 1.434(2)
C3 C4 1.544(3)
C4 C5 1.509(3)
C5 O2 1.224(2)
C5 C6 1.512(3)
C6 C13 1.513(3)
C6 C7 1.543(3)
C7 O1 1.440(2)
C7 C8 1.545(3)
C8 C9 1.534(3)
C9 C10 1.539(3)
C9 C14 1.544(3)
C10 C11 1.505(3)
C14 C15 1.525(3)
C14 C16 1.528(3)
