#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/27/4022768.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_4022768
loop_
_publ_author_name
'James D. White'
'Laura Quaranta'
'Guoqiang Wang'
_publ_section_title
;
 Studies on the Synthesis of (-)-Gymnodimine. Subunit
 Synthesis and Coupling
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1717
_journal_page_last               1728
_journal_paper_doi               10.1021/jo062396o
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C15 H20 O5'
_chemical_formula_weight         280.31
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_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
_atom_sites_solution_secondary   difmap
_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                   9.3780(11)
_cell_length_b                   10.9680(12)
_cell_length_c                   13.9660(10)
_cell_measurement_reflns_used    63
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.37
_cell_measurement_theta_min      7.5
_cell_volume                     1436.5(3)
_computing_cell_refinement       'Siemens XSCANS'
_computing_data_collection       'Siemens XSCANS'
_computing_data_reduction        'Siemens XSCANS'
_computing_molecular_graphics    'ORTEP III for Windows'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SHELXS-97
_diffrn_ambient_temperature      290(2)
_diffrn_measured_fraction_theta_full 0.923
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       'ω/2θ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_sigmaI/netI    0.0322
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            2560
_diffrn_reflns_theta_full        67.51
_diffrn_reflns_theta_max         67.51
_diffrn_reflns_theta_min         5.13
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.802
_exptl_absorpt_correction_T_max  0.8411
_exptl_absorpt_correction_T_min  0.5005
_exptl_absorpt_correction_type   Semi-empirical
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.111
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2203
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0340
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0472P)²+0.1784P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0910
_refine_ls_wR_factor_ref         0.0933
_reflns_number_gt                2034
_reflns_number_total             2203
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo062396osi20061127_074724.cif
_cod_data_source_block           gw112302
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4022768
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'
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
O1 O 1.64068(15) 0.33267(17) 0.88966(13) 0.0779(5) Uani 1 1 d .
O2 O 1.48680(16) 0.41073(16) 0.99385(12) 0.0685(4) Uani 1 1 d .
O3 O 1.3966(2) 0.47551(18) 0.70720(13) 0.0844(6) Uani 1 1 d .
O4 O 0.97814(13) 0.35805(12) 0.65241(9) 0.0511(3) Uani 1 1 d .
O5 O 0.8186(2) 0.20501(15) 0.64766(12) 0.0796(6) Uani 1 1 d .
C1 C 1.5200(2) 0.3608(2) 0.90885(16) 0.0557(5) Uani 1 1 d .
C2 C 1.38648(17) 0.34964(16) 0.84832(13) 0.0428(4) Uani 1 1 d .
C3 C 1.3778(2) 0.4691(2) 0.79139(16) 0.0534(5) Uani 1 1 d .
H3 H 1.3566 0.5404 0.8245 0.064 Uiso 1 1 calc R
C4 C 1.3690(2) 0.2414(2) 0.78309(16) 0.0545(5) Uani 1 1 d .
H4A H 1.3845 0.1665 0.8185 0.065 Uiso 1 1 calc R
H4B H 1.4380 0.2452 0.7315 0.065 Uiso 1 1 calc R
C5 C 1.2164(2) 0.2438(3) 0.74212(19) 0.0686(7) Uani 1 1 d .
H5A H 1.2207 0.2790 0.6785 0.082 Uiso 1 1 calc R
H5B H 1.1844 0.1602 0.7351 0.082 Uiso 1 1 calc R
C6 C 1.10375(19) 0.31258(18) 0.79864(13) 0.0447(4) Uani 1 1 d .
C7 C 1.12637(18) 0.36201(17) 0.88432(13) 0.0409(4) Uani 1 1 d .
C8 C 1.0182(2) 0.4274(2) 0.94555(16) 0.0545(5) Uani 1 1 d .
H8A H 0.9240 0.4016 0.9279 0.082 Uiso 1 1 calc R
H8B H 1.0269 0.5138 0.9360 0.082 Uiso 1 1 calc R
H8C H 1.0348 0.4085 1.0117 0.082 Uiso 1 1 calc R
C9 C 1.27302(19) 0.34635(19) 0.92658(13) 0.0446(4) Uani 1 1 d .
H9 H 1.2763 0.2649 0.9553 0.053 Uiso 1 1 calc R
C10 C 1.3329(2) 0.4349(2) 1.00038(16) 0.0629(6) Uani 1 1 d .
H10A H 1.3109 0.5188 0.9838 0.075 Uiso 1 1 calc R
H10B H 1.2967 0.4176 1.0640 0.075 Uiso 1 1 calc R
C11 C 0.9604(2) 0.32100(18) 0.74985(14) 0.0483(5) Uani 1 1 d .
H11 H 0.9005 0.3804 0.7835 0.058 Uiso 1 1 calc R
C12 C 0.8792(2) 0.2007(2) 0.73915(15) 0.0591(5) Uani 1 1 d .
H12A H 0.9436 0.1319 0.7448 0.071 Uiso 1 1 calc R
H12B H 0.8058 0.1936 0.7878 0.071 Uiso 1 1 calc R
C13 C 0.8560(2) 0.31760(19) 0.60329(15) 0.0530(5) Uani 1 1 d .
C14 C 0.8946(4) 0.2936(3) 0.50096(17) 0.0841(8) Uani 1 1 d .
H14A H 0.9774 0.2423 0.4985 0.126 Uiso 1 1 calc R
H14B H 0.9146 0.3695 0.4694 0.126 Uiso 1 1 calc R
H14C H 0.8165 0.2537 0.4694 0.126 Uiso 1 1 calc R
C15 C 0.7354(3) 0.4095(3) 0.6136(2) 0.0872(9) Uani 1 1 d .
H15A H 0.7640 0.4859 0.5861 0.131 Uiso 1 1 calc R
H15B H 0.7139 0.4208 0.6802 0.131 Uiso 1 1 calc R
H15C H 0.6523 0.3798 0.5809 0.131 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 '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
C1 O2 C10 110.85(15)
C13 O4 C11 106.26(14)
C12 O5 C13 109.05(15)
O1 C1 O2 121.3(2)
O1 C1 C2 129.2(2)
O2 C1 C2 109.51(16)
C4 C2 C1 119.41(16)
C4 C2 C9 109.81(16)
C1 C2 C9 100.29(15)
C4 C2 C3 110.73(16)
C1 C2 C3 105.31(16)
C9 C2 C3 110.74(15)
O3 C3 C2 123.6(2)
C2 C4 C5 108.18(16)
C6 C5 C4 117.46(18)
C7 C6 C11 121.53(16)
C7 C6 C5 123.97(17)
C11 C6 C5 114.50(17)
C6 C7 C9 116.83(16)
C6 C7 C8 126.60(17)
C9 C7 C8 116.51(16)
C7 C9 C10 121.91(17)
C7 C9 C2 110.70(14)
C10 C9 C2 102.27(15)
O2 C10 C9 101.80(17)
O4 C11 C6 110.10(14)
O4 C11 C12 102.11(15)
C6 C11 C12 115.73(17)
O5 C12 C11 105.20(16)
O4 C13 O5 105.14(16)
O4 C13 C14 108.90(19)
O5 C13 C14 108.79(19)
O4 C13 C15 110.50(18)
O5 C13 C15 110.5(2)
C14 C13 C15 112.7(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.203(3)
O2 C1 1.344(3)
O2 C10 1.471(3)
O3 C3 1.191(2)
O4 C13 1.407(2)
O4 C11 1.430(3)
O5 C12 1.399(3)
O5 C13 1.425(3)
C1 C2 1.516(3)
C2 C4 1.505(3)
C2 C9 1.526(2)
C2 C3 1.535(3)
C4 C5 1.542(3)
C5 C6 1.519(3)
C6 C7 1.331(3)
C6 C11 1.510(3)
C7 C9 1.506(2)
C7 C8 1.508(3)
C9 C10 1.524(3)
C11 C12 1.531(3)
C13 C14 1.497(3)
C13 C15 1.522(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21194135
