#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/19/4021941.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_4021941
loop_
_publ_author_name
'Asano, Moriteru'
'Inoue, Munenori'
'Watanabe, Kazuhiro'
'Abe, Hideki'
'Katoh, Tadashi'
_publ_contact_author
;    Tadashi Katoh
    Tohoku Pharmacetucal University
    4-4-1 Komatsushim, Aoba-ku, Sendai
    981-8558, Japan
;
_publ_contact_author_email       katoh@tohoku-pharm.ac.jp
_publ_section_title
;
 Synthetic Studies toward GKK1032s, Novel Antibiotic Antitumor Agents:
 Enantioselective Synthesis of the Fully Elaborated Tricyclic Core via
 an Intramolecular Diels-Alder Cycloaddition
;
_journal_issue                   18
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6942
_journal_page_last               6951
_journal_paper_doi               10.1021/jo0610208
_journal_volume                  71
_journal_year                    2006
_chemical_formula_moiety         ' C16 H30 O5 '
_chemical_formula_sum            'C16 H30 O5'
_chemical_formula_weight         302.40
_chemical_melting_point          375
_chemical_name_systematic
;
(1S,4S,4aR,5R,6S,7S,8aR)-1-Methoxy-4-methoxymethoxy-1,5,7,8a-tetramethyl-
4a,5,6,7,8,8a-hexahydroisochroman-6-ol
;
_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_type_scat_source           'International Tables (1974)'
_cell_angle_alpha                90(0)
_cell_angle_beta                 90(0)
_cell_angle_gamma                90(0)
_cell_formula_units_Z            4
_cell_length_a                   11.195(3)
_cell_length_b                   15.666(6)
_cell_length_c                   9.728(3)
_cell_volume                     1706.1(9)
_computing_cell_refinement       Crystan-GM
_computing_data_collection       Crystan-GM
_computing_data_reduction        Crystan-GM
_computing_molecular_graphics    Crystan-GM
_computing_publication_material  Crystan-GM
_computing_structure_refinement  Crystan-GM
_computing_structure_solution    Crystan-GM
_diffrn_measurement_device       'Mac Science MXC18'
_diffrn_measurement_method       theta/omega
_diffrn_radiation_type           ' Cu K-alpha '
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.00
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1727
_exptl_absorpt_coefficient_mu    6.638
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.20
_exptl_crystal_density_meas      1.18
_exptl_crystal_description       prism
_exptl_crystal_preparation       'diethyl ether'
_exptl_crystal_size_max          0.400000
_exptl_crystal_size_mid          0.300000
_exptl_crystal_size_min          0.250000
_refine_diff_density_max         -0.21
_refine_diff_density_min         0.14
_refine_ls_extinction_coef       0.0000
_refine_ls_extinction_method     Larson
_refine_ls_goodness_of_fit_obs   0.23986E+01
_refine_ls_hydrogen_treatment
;
;
_refine_ls_number_parameters     355
_refine_ls_number_reflns         1617
_refine_ls_R_factor_obs          0.0396
_refine_ls_shift/esd_max         0.0179
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      ' Count statistics    '
_refine_ls_wR_factor_obs         0.0477
_reflns_number_observed          1621
_reflns_number_total             1651
_reflns_observed_criterion       refl_observed_if_F_>_0.20_sigma(F)
_cod_data_source_file            jo0610208si20060706_123204.cif
_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.

'_exptl_absorpt_correction_type' value ' none ' changed to
'none' 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 

The following automatic conversions were performed:

'_chemical_melting_point' value '375K' was changed to '375' - the
value should be numeric and without a unit
designator.

'_atom_site_thermal_displace_type' tag value 'Uij' was
replaced with 'Uani' value 30 times.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      ' P 21 21 21 '
_cod_database_code               4021941
loop_
_symmetry_equiv_pos_as_xyz
'    +X,    +Y,    +Z'
' X+1/2, -Y+1/2,     -Z'
' -X+1/2,    -Y,  Z+1/2'
'     -X, Y+1/2, -Z+1/2'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_thermal_displace_type
O(1) -0.55624(10) -0.10440(6) -0.50220(11) 0.052 1.000 Uani
O(2) -0.59916(10) -0.22603(6) -0.63204(12) 0.052 1.000 Uani
O(3) -0.46183(12) 0.10393(7) -0.76539(13) 0.065 1.000 Uani
O(4) -0.75381(11) -0.08591(7) -0.87653(13) 0.062 1.000 Uani
C(5) -0.69420(17) -0.18432(12) -0.70485(21) 0.053 1.000 Uani
C(6) -0.50688(14) -0.16864(8) -0.58609(16) 0.048 1.000 Uani
C(7) -0.45141(14) -0.12174(8) -0.71107(16) 0.043 1.000 Uani
C(8) -0.55236(15) -0.07171(9) -0.78951(16) 0.041 1.000 Uani
C(9) -0.35715(19) -0.05752(12) -0.66240(20) 0.050 1.000 Uani
C(10) -0.49950(17) -0.01879(10) -0.90873(18) 0.049 1.000 Uani
O(11) -0.90729(14) -0.18367(9) -0.91835(19) 0.090 1.000 Uani
C(12) -0.30558(17) -0.00273(12) -0.77748(22) 0.056 1.000 Uani
C(13) -0.4208(2) -0.2257(1) -0.5083(2) 0.062 1.000 Uani
C(14) -0.39198(19) -0.18869(11) -0.80512(22) 0.057 1.000 Uani
C(15) -0.40479(16) 0.04313(10) -0.85368(19) 0.052 1.000 Uani
C(16) -0.65249(16) -0.13314(10) -0.82823(17) 0.048 1.000 Uani
C(17) -0.6090(2) -0.1302(1) -0.3754(2) 0.066 1.000 Uani
C(18) -0.5888(2) 0.0296(1) -0.9971(2) 0.069 1.000 Uani
C(19) -0.8255(2) -0.1267(2) -0.9750(3) 0.090 1.000 Uani
C(20) -0.2116(2) 0.0581(2) -0.7227(3) 0.083 1.000 Uani
C(21) -1.0118(3) -0.1445(3) -0.8703(4) 0.112 1.000 Uani
H(3) -0.4402(17) 0.1509(13) -0.7959(20) 0.071 1.000 Uiso
H(5A) -0.7355(15) -0.1418(11) -0.6424(18) 0.058 1.000 Uani
H(5B) -0.7499(14) -0.2301(10) -0.7279(15) 0.052 1.000 Uani
H(8) -0.5849(14) -0.0343(9) -0.7277(15) 0.037 1.000 Uani
H(9A) -0.3878(15) -0.0238(11) -0.5935(17) 0.047 1.000 Uani
H(9B) -0.2916(15) -0.0863(10) -0.6104(19) 0.057 1.000 Uani
H(10) -0.4587(14) -0.0561(9) -0.9640(16) 0.046 1.000 Uani
H(12) -0.2676(13) -0.0409(10) -0.8444(20) 0.055 1.000 Uani
H(13A) -0.3911(18) -0.2677(12) -0.5635(21) 0.073 1.000 Uiso
H(13B) -0.4628(19) -0.2524(12) -0.4242(21) 0.083 1.000 Uiso
H(13C) -0.353(2) -0.196(1) -0.477(2) 0.087 1.000 Uiso
H(14A) -0.4379(17) -0.2347(12) -0.8182(18) 0.061 1.000 Uiso
H(14B) -0.3674(18) -0.1700(13) -0.8984(23) 0.083 1.000 Uiso
H(14C) -0.3171(17) -0.2118(12) -0.7676(19) 0.068 1.000 Uiso
H(15) -0.3695(15) 0.0732(10) -0.9392(17) 0.059 1.000 Uani
H(16) -0.6293(13) -0.1728(9) -0.9014(20) 0.052 1.000 Uani
H(17A) -0.5531(19) -0.1484(13) -0.3069(23) 0.081 1.000 Uiso
H(17B) -0.6626(18) -0.1819(13) -0.3868(21) 0.079 1.000 Uiso
H(17C) -0.662(2) -0.087(2) -0.348(3) 0.110 1.000 Uiso
H(18A) -0.5472(16) 0.0648(11) -1.0490(20) 0.064 1.000 Uiso
H(18B) -0.6349(18) -0.0125(13) -1.0670(23) 0.093 1.000 Uiso
H(18C) -0.6419(19) 0.0608(14) -0.9385(24) 0.087 1.000 Uiso
H(19A) -0.862(3) -0.083(2) -1.029(3) 0.13 1.000 Uiso
H(19B) -0.770(2) -0.164(2) -1.041(3) 0.13 1.000 Uiso
H(20A) -0.1473(19) 0.0273(14) -0.6753(21) 0.083 1.000 Uiso
H(20B) -0.249(2) 0.103(1) -0.653(3) 0.111 1.000 Uiso
H(20C) -0.1837(19) 0.0937(15) -0.7827(23) 0.084 1.000 Uiso
H(21A) -1.058(3) -0.122(2) -0.958(4) 0.19 1.000 Uiso
H(21B) -0.977(3) -0.114(2) -0.793(3) 0.16 1.000 Uiso
H(21C) -1.061(4) -0.202(3) -0.846(4) 0.23 1.000 Uiso
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C(6) O(1) C(17) 117.5(2) yes
C(5) O(2) C(6) 113.6(2) yes
C(16) O(4) C(19) 116.2(2) yes
O(2) C(5) C(16) 113.8(2) yes
O(1) C(6) O(2) 110.1(2) yes
O(1) C(6) C(7) 105.8(2) yes
O(1) C(6) C(13) 112.4(2) yes
O(2) C(6) C(7) 109.9(2) yes
O(2) C(6) C(13) 104.0(2) yes
C(7) C(6) C(13) 114.6(2) yes
C(6) C(7) C(8) 109.2(2) yes
C(6) C(7) C(9) 110.2(2) yes
C(6) C(7) C(14) 108.4(2) yes
C(8) C(7) C(9) 108.5(2) yes
C(8) C(7) C(14) 111.2(2) yes
C(9) C(7) C(14) 109.4(2) yes
C(7) C(8) C(10) 110.9(2) yes
C(7) C(8) C(16) 109.5(2) yes
C(10) C(8) C(16) 115.8(2) yes
C(7) C(9) C(12) 113.8(2) yes
C(8) C(10) C(15) 110.0(2) yes
C(8) C(10) C(18) 116.1(2) yes
C(15) C(10) C(18) 109.6(2) yes
C(19) O(11) C(21) 113.6(3) yes
C(9) C(12) C(15) 110.4(2) yes
C(9) C(12) C(20) 111.0(2) yes
C(15) C(12) C(20) 112.5(2) yes
O(3) C(15) C(10) 108.8(2) yes
O(3) C(15) C(12) 110.4(2) yes
C(10) C(15) C(12) 112.2(2) yes
O(4) C(16) C(5) 106.8(2) yes
O(4) C(16) C(8) 109.7(2) yes
C(5) C(16) C(8) 111.4(2) yes
O(4) C(19) O(11) 113.4(2) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O(1) C(6) 1.409(2) yes
O(1) C(17) 1.425(3) yes
O(2) C(5) 1.436(3) yes
O(2) C(6) 1.441(2) yes
O(3) C(15) 1.433(3) yes
O(4) C(16) 1.433(3) yes
O(4) C(19) 1.404(3) yes
C(5) C(16) 1.517(3) yes
C(6) C(7) 1.550(3) yes
C(6) C(13) 1.517(3) yes
C(7) C(8) 1.573(3) yes
C(7) C(9) 1.533(3) yes
C(7) C(14) 1.543(3) yes
C(8) C(10) 1.544(3) yes
C(8) C(16) 1.525(3) yes
C(9) C(12) 1.524(3) yes
C(10) C(15) 1.534(3) yes
C(10) C(18) 1.521(3) yes
O(11) C(19) 1.393(4) yes
O(11) C(21) 1.401(4) yes
C(12) C(15) 1.516(3) yes
C(12) C(20) 1.517(4) yes
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_publ_flag
C(17) O(1) C(6) O(2) 64.1(2) yes
C(17) O(1) C(6) C(7) -177.2(2) yes
C(17) O(1) C(6) C(13) -51.4(2) yes
C(5) O(2) C(6) O(1) 57.0(2) yes
C(5) O(2) C(6) C(7) -59.2(2) yes
C(5) O(2) C(6) C(13) 177.7(2) yes
C(6) O(2) C(5) C(16) 56.2(2) yes
C(19) O(4) C(16) C(5) -89.8(2) yes
C(19) O(4) C(16) C(8) 149.4(3) yes
C(16) O(4) C(19) O(11) 81.9(3) yes
O(2) C(5) C(16) O(4) -171.6(2) yes
O(2) C(5) C(16) C(8) -51.9(2) yes
O(1) C(6) C(7) C(8) -60.6(2) yes
O(1) C(6) C(7) C(9) 58.5(2) yes
O(1) C(6) C(7) C(14) 178.2(2) yes
O(2) C(6) C(7) C(8) 58.3(2) yes
O(2) C(6) C(7) C(9) 177.4(2) yes
O(2) C(6) C(7) C(14) -62.9(2) yes
C(13) C(6) C(7) C(8) 175.0(2) yes
C(13) C(6) C(7) C(9) -66.0(2) yes
C(13) C(6) C(7) C(14) 53.7(2) yes
C(6) C(7) C(8) C(10) 175.9(2) yes
C(6) C(7) C(8) C(16) -55.1(2) yes
C(6) C(7) C(9) C(12) -174.9(3) yes
C(9) C(7) C(8) C(10) 55.8(2) yes
C(8) C(7) C(9) C(12) -55.4(2) yes
C(9) C(7) C(8) C(16) -175.2(2) yes
C(14) C(7) C(8) C(10) -64.5(2) yes
C(14) C(7) C(8) C(16) 64.5(2) yes
C(14) C(7) C(9) C(12) 66.1(2) yes
C(7) C(8) C(10) C(15) -57.4(2) yes
C(7) C(8) C(10) C(18) 177.3(3) yes
C(7) C(8) C(16) O(4) 169.4(2) yes
C(7) C(8) C(16) C(5) 51.4(2) yes
C(10) C(8) C(16) O(4) -64.4(2) yes
C(10) C(8) C(16) C(5) 177.7(2) yes
C(16) C(8) C(10) C(15) 177.1(2) yes
C(16) C(8) C(10) C(18) 51.8(2) yes
C(7) C(9) C(12) C(15) 55.6(2) yes
C(7) C(9) C(12) C(20) -179.0(3) yes
C(8) C(10) C(15) O(3) -65.1(2) yes
C(8) C(10) C(15) C(12) 57.3(2) yes
C(18) C(10) C(15) O(3) 63.8(2) yes
C(18) C(10) C(15) C(12) -173.8(3) yes
C(21) O(11) C(19) O(4) 82.6(3) yes
C(9) C(12) C(15) O(3) 66.1(2) yes
C(9) C(12) C(15) C(10) -55.4(2) yes
C(20) C(12) C(15) O(3) -58.5(2) yes
C(20) C(12) C(15) C(10) 180.0(3) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 17242284
