#------------------------------------------------------------------------------
#$Date: 2017-03-05 21:59:09 +0200 (Sun, 05 Mar 2017) $
#$Revision: 193981 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/55/4025596.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_4025596
loop_
_publ_author_name
'Kana Watanabe'
'Yusuke Iwata'
'Satoshi Adachi'
'Tomoyuki Nishikawa'
'Yuko Yoshida'
'Shunsuke Kameda'
'Mitsuaki Ide'
'Yoko Saikawa'
'Masaya Nakata'
_publ_contact_author_address
;
Department of Applied Chemistry
Faculty of Science and Technology
Keio University
3-14-1 Hiyoshi Kohoku-ku
Yokohama 223-8522
Japan
;
_publ_contact_author_email       ' msynktxa@applc.keio.ac.jp'
_publ_contact_author_fax         ' (81)45 566 1551 '
_publ_contact_author_name        ' Prof. Masaya Nakata'
_publ_contact_author_phone       ' (81)45 566 1577 '
_publ_section_title
;
 Synthetic Studies on Lactonamycins: Synthesis of the Model BCDEF Aglycon
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5573
_journal_page_last               5579
_journal_paper_doi               10.1021/jo100913s
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C19 H14 O4, C6 H14'
_chemical_formula_sum            'C25 H28 O8'
_chemical_formula_weight         456.49
_chemical_melting_point          511.5(5)
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_audit_creation_date             'Fri Jul 31 23:15:40 2009'
_audit_creation_method           'by teXsan'
_cell_angle_alpha                90
_cell_angle_beta                 104.18(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.554(5)
_cell_length_b                   18.044(7)
_cell_length_c                   7.886(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298
_cell_measurement_theta_max      12.3
_cell_measurement_theta_min      10.3
_cell_volume                     2007.9(12)
_computing_cell_refinement       WinAFC
_computing_data_collection       WinAFC
_computing_data_reduction        'teXsan Ver. 1.11'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  'teXsan Ver. 1.11'
_computing_structure_refinement  SHELXL97
_computing_structure_solution    SIR92
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 1.0
_diffrn_measured_fraction_theta_max 27.50
_diffrn_measurement_device_type  'Rigaku AFC7R'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.037
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -2
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5519
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.5
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.952
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North, Phillips & Mathews, 1968)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             912.0
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.17
_refine_diff_density_min         -0.16
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.942
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     354
_refine_ls_number_reflns         4616
_refine_ls_R_factor_gt           0.044
_refine_ls_shift/su_max          -0.0270
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²) + (0.0514P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.144
_reflns_number_gt                1791
_reflns_number_total             4616
_reflns_threshold_expression     >2.0sigma(I)
_cod_data_source_file            jo100913s_si_001.cif
_cod_data_source_block           aglycone4
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '511-512K' was changed to '511.5(5)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 

The following automatic conversions were performed:
data name '_geom_hbond_site_distance_dh' replaced with
'_geom_hbond_distance_DH' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

data
name '_geom_hbond_site_distance_ha' replaced with
'_geom_hbond_distance_HA' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

data
name '_geom_hbond_site_distance_da' replaced with
'_geom_hbond_distance_DA' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

Automatic conversion script
Id: cif_correct_tags 5005 2017-03-03 11:38:54Z antanas 
;
_cod_original_cell_volume        2007.7(12)
_cod_original_formula_sum        'C25 H28 O8 '
_cod_database_code               4025596
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,1/2+y,1/2-z
-x,-y,-z
x,1/2-y,1/2+z
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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O(1) O 0.0955(1) 0.0456(1) 0.4492(2) 0.0597(6) Uani 1.00 d . . .
O(2) O -0.0167(1) 0.0371(2) 0.2018(3) 0.0945(9) Uani 1.00 d . . .
O(3) O 0.3187(1) 0.0284(1) 0.3513(2) 0.0472(5) Uani 1.00 d . . .
O(4) O 0.2243(1) -0.0685(1) 0.4011(2) 0.0624(6) Uani 1.00 d . . .
O(5) O 0.1931(1) 0.0125(1) 0.8016(2) 0.0606(6) Uani 1.00 d . . .
O(6) O 0.3945(1) -0.0325(1) 0.7987(3) 0.0559(5) Uani 1.00 d . . .
O(7) O 0.2846(2) 0.2801(1) 0.5827(3) 0.0673(6) Uani 1.00 d . . .
O(8) O 0.1737(1) 0.1764(1) 0.4252(3) 0.0701(6) Uani 1.00 d . . .
C(2) C 0.0659(2) 0.0361(2) 0.2729(4) 0.0664(9) Uani 1.00 d . . .
C(3) C 0.1485(2) 0.0225(3) 0.1947(4) 0.0626(9) Uani 1.00 d . . .
C(3A) C 0.2272(2) 0.0076(2) 0.3546(3) 0.0465(7) Uani 1.00 d . . .
C(5) C 0.2201(2) -0.0763(2) 0.5802(4) 0.0565(8) Uani 1.00 d . . .
C(5A) C 0.2347(2) 0.0003(2) 0.6599(3) 0.0449(6) Uani 1.00 d . . .
C(6) C 0.3401(2) 0.0173(1) 0.7401(3) 0.0406(6) Uani 1.00 d . . .
C(6A) C 0.3692(2) 0.0962(1) 0.7533(3) 0.0376(6) Uani 1.00 d . . .
C(7) C 0.4521(2) 0.1151(2) 0.8674(3) 0.0419(6) Uani 1.00 d . . .
C(7A) C 0.4812(2) 0.1906(2) 0.8905(3) 0.0433(6) Uani 1.00 d . . .
C(8) C 0.5674(2) 0.2111(2) 1.0070(4) 0.0560(7) Uani 1.00 d . . .
C(9) C 0.5920(3) 0.2840(2) 1.0304(5) 0.0694(9) Uani 1.00 d . . .
C(10) C 0.5321(3) 0.3387(3) 0.9410(5) 0.075(1) Uani 1.00 d . . .
C(11) C 0.4494(3) 0.3213(2) 0.8257(5) 0.0629(9) Uani 1.00 d . . .
C(11A) C 0.4219(2) 0.2465(2) 0.7970(3) 0.0462(7) Uani 1.00 d . . .
C(12) C 0.3372(2) 0.2254(2) 0.6740(3) 0.0475(7) Uani 1.00 d . . .
C(12A) C 0.3096(2) 0.1512(2) 0.6500(3) 0.0415(6) Uani 1.00 d . . .
C(13) C 0.2251(2) 0.1307(2) 0.5217(3) 0.0476(7) Uani 1.00 d . . .
C(13A) C 0.1973(2) 0.0497(2) 0.5015(3) 0.0454(7) Uani 1.00 d . . .
C(14) C 0.3537(3) -0.0081(2) 0.2185(5) 0.0629(9) Uani 1.00 d . . .
C(15) C -0.1418(6) 0.2667(6) 0.640(3) 0.262(7) Uani 1.00 d . . .
C(16) C -0.1465(10) 0.2892(9) 0.438(3) 0.32(1) Uani 1.00 d . . .
C(17) C -0.070(2) 0.275(2) 0.62(1) 0.84(7) Uani 1.00 d . . .
C(18) C -0.013(1) 0.276(2) 0.454(9) 0.63(3) Uani 1.00 d . . .
C(19) C 0.0148(7) 0.1712(7) 0.727(2) 0.180(6) Uani 1.00 d . . .
C(20) C 0.0311(9) 0.3369(5) 0.325(1) 0.154(5) Uani 1.00 d . . .
H(3A) H 0.134(2) -0.015(2) 0.109(5) 0.0833(1) Uiso 1.00 d . . .
H(3B) H 0.156(2) 0.071(2) 0.132(5) 0.1030(2) Uiso 1.00 d . . .
H(5A) H 0.270(2) -0.116(2) 0.643(4) 0.0601(1) Uiso 1.00 d . . .
H(5B) H 0.158(2) -0.094(1) 0.586(3) 0.05456(9) Uiso 1.00 d . . .
H(5O) H 0.134(3) -0.002(2) 0.769(4) 0.0936(2) Uiso 1.00 d . . .
H(7) H 0.494(2) 0.077(1) 0.946(3) 0.03680(8) Uiso 1.00 d . . .
H(7O) H 0.235(2) 0.260(2) 0.511(5) 0.0905(2) Uiso 1.00 d . . .
H(8) H 0.606(2) 0.172(2) 1.071(4) 0.0701(1) Uiso 1.00 d . . .
H(9) H 0.645(3) 0.297(2) 1.112(5) 0.1025(2) Uiso 1.00 d . . .
H(10) H 0.549(2) 0.386(2) 0.958(4) 0.0875(2) Uiso 1.00 d . . .
H(11) H 0.409(2) 0.357(2) 0.761(4) 0.0739(1) Uiso 1.00 d . . .
H(14A) H 0.421(2) 0.002(2) 0.240(4) 0.0807(1) Uiso 1.00 d . . .
H(14B) H 0.348(3) -0.065(2) 0.232(5) 0.1082(2) Uiso 1.00 d . . .
H(14C) H 0.321(3) 0.008(2) 0.106(5) 0.1033(2) Uiso 1.00 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;International Tables for Crystallography
(1992, Vol. C)
;
H H 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C)
;
O O 0.011 0.006
;International Tables for Crystallography
(1992, Vol. C)
;
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C(2) O(1) C(13A) 110.1(2) . . . yes
C(3A) O(3) C(14) 113.9(2) . . . yes
C(3A) O(4) C(5) 111.1(2) . . . yes
C(5A) O(5) H(5O) 107(2) . . . no
C(12) O(7) H(7O) 108(2) . . . no
O(1) C(2) O(2) 120.4(3) . . . yes
O(1) C(2) C(3) 110.8(2) . . . yes
O(2) C(2) C(3) 128.7(3) . . . yes
C(2) C(3) C(3A) 102.0(2) . . . yes
C(2) C(3) H(3A) 111(2) . . . no
C(2) C(3) H(3B) 105(2) . . . no
C(3A) C(3) H(3A) 118(2) . . . no
C(3A) C(3) H(3B) 114(2) . . . no
H(3A) C(3) H(3B) 107(3) . . . no
O(3) C(3A) O(4) 110.7(2) . . . yes
O(3) C(3A) C(3) 118.2(2) . . . yes
O(3) C(3A) C(13A) 109.3(2) . . . yes
O(4) C(3A) C(3) 108.8(2) . . . yes
O(4) C(3A) C(13A) 104.5(2) . . . yes
C(3) C(3A) C(13A) 104.2(2) . . . yes
O(4) C(5) C(5A) 106.5(2) . . . yes
O(4) C(5) H(5A) 110(2) . . . no
O(4) C(5) H(5B) 110(1) . . . no
C(5A) C(5) H(5A) 114(1) . . . no
C(5A) C(5) H(5B) 108(2) . . . no
H(5A) C(5) H(5B) 108(2) . . . no
O(5) C(5A) C(5) 115.3(2) . . . yes
O(5) C(5A) C(6) 102.8(2) . . . yes
O(5) C(5A) C(13A) 114.9(2) . . . yes
C(5) C(5A) C(6) 112.2(2) . . . yes
C(5) C(5A) C(13A) 102.0(2) . . . yes
C(6) C(5A) C(13A) 109.9(2) . . . yes
O(6) C(6) C(5A) 120.0(2) . . . yes
O(6) C(6) C(6A) 122.5(2) . . . yes
C(5A) C(6) C(6A) 117.3(2) . . . yes
C(6) C(6A) C(7) 118.7(2) . . . yes
C(6) C(6A) C(12A) 120.2(2) . . . yes
C(7) C(6A) C(12A) 121.1(2) . . . yes
C(6A) C(7) C(7A) 120.8(2) . . . yes
C(6A) C(7) H(7) 122(1) . . . no
C(7A) C(7) H(7) 117(1) . . . no
C(7) C(7A) C(8) 121.6(2) . . . yes
C(7) C(7A) C(11A) 119.4(2) . . . yes
C(8) C(7A) C(11A) 119.0(3) . . . yes
C(7A) C(8) C(9) 120.3(3) . . . yes
C(7A) C(8) H(8) 117(2) . . . no
C(9) C(8) H(8) 123(2) . . . no
C(8) C(9) C(10) 120.3(3) . . . yes
C(8) C(9) H(9) 120(2) . . . no
C(10) C(9) H(9) 119(2) . . . no
C(9) C(10) C(11) 121.3(4) . . . yes
C(9) C(10) H(10) 120(2) . . . no
C(11) C(10) H(10) 119(2) . . . no
C(10) C(11) C(11A) 120.0(3) . . . yes
C(10) C(11) H(11) 123(2) . . . no
C(11A) C(11) H(11) 117(2) . . . no
C(7A) C(11A) C(11) 119.1(2) . . . yes
C(7A) C(11A) C(12) 118.8(2) . . . yes
C(11) C(11A) C(12) 122.0(2) . . . yes
O(7) C(12) C(11A) 116.9(2) . . . yes
O(7) C(12) C(12A) 121.7(2) . . . yes
C(11A) C(12) C(12A) 121.4(2) . . . yes
C(6A) C(12A) C(12) 118.2(2) . . . yes
C(6A) C(12A) C(13) 121.1(2) . . . yes
C(12) C(12A) C(13) 120.7(2) . . . yes
O(8) C(13) C(12A) 122.9(3) . . . yes
O(8) C(13) C(13A) 118.2(2) . . . yes
C(12A) C(13) C(13A) 118.9(2) . . . yes
O(1) C(13A) C(3A) 102.8(2) . . . yes
O(1) C(13A) C(5A) 109.9(2) . . . yes
O(1) C(13A) C(13) 107.9(2) . . . yes
C(3A) C(13A) C(5A) 102.7(2) . . . yes
C(3A) C(13A) C(13) 116.1(2) . . . yes
C(5A) C(13A) C(13) 116.5(2) . . . yes
O(3) C(14) H(14A) 108(2) . . . no
O(3) C(14) H(14B) 109(2) . . . no
O(3) C(14) H(14C) 111(3) . . . no
H(14A) C(14) H(14B) 106(3) . . . no
H(14A) C(14) H(14C) 111(3) . . . no
H(14B) C(14) H(14C) 111(3) . . . no
C(16) C(15) C(17) 68(4) . . . yes
C(15) C(16) C(17) 40(2) . . . yes
C(15) C(17) C(16) 72(2) . . . yes
C(15) C(17) C(18) 141(6) . . . yes
C(16) C(17) C(18) 72(4) . . . yes
C(17) C(18) C(20) 141(2) . . . yes
C(18) C(20) C(19) 114(2) . . 4_554 yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O(1) C(2) 1.362(3) . . yes
O(1) C(13A) 1.440(3) . . yes
O(2) C(2) 1.196(3) . . yes
O(3) C(3A) 1.389(3) . . yes
O(3) C(14) 1.432(5) . . yes
O(4) C(3A) 1.424(4) . . yes
O(4) C(5) 1.435(4) . . yes
O(5) C(5A) 1.412(3) . . yes
O(5) H(5O) 0.88(4) . . no
O(6) C(6) 1.212(3) . . yes
O(7) C(12) 1.345(3) . . yes
O(7) H(7O) 0.88(3) . . no
O(8) C(13) 1.240(3) . . yes
C(2) C(3) 1.499(5) . . yes
C(3) C(3A) 1.506(4) . . yes
C(3) H(3A) 0.94(3) . . no
C(3) H(3B) 1.02(4) . . no
C(3A) C(13A) 1.534(4) . . yes
C(5) C(5A) 1.512(4) . . yes
C(5) H(5A) 1.05(3) . . no
C(5) H(5B) 0.97(3) . . no
C(5A) C(6) 1.540(3) . . yes
C(5A) C(13A) 1.522(4) . . yes
C(6) C(6A) 1.481(4) . . yes
C(6A) C(7) 1.360(3) . . yes
C(6A) C(12A) 1.434(3) . . yes
C(7) C(7A) 1.424(4) . . yes
C(7) H(7) 1.02(2) . . no
C(7A) C(8) 1.410(4) . . yes
C(7A) C(11A) 1.412(4) . . yes
C(8) C(9) 1.364(5) . . yes
C(8) H(8) 0.97(3) . . no
C(9) C(10) 1.390(6) . . yes
C(9) H(9) 0.90(3) . . no
C(10) C(11) 1.357(5) . . yes
C(10) H(10) 0.89(4) . . no
C(11) C(11A) 1.410(4) . . yes
C(11) H(11) 0.94(3) . . no
C(11A) C(12) 1.422(3) . . yes
C(12) C(12A) 1.396(4) . . yes
C(12A) C(13) 1.437(3) . . yes
C(13) C(13A) 1.515(4) . . yes
C(14) H(14A) 0.97(3) . . no
C(14) H(14B) 1.03(4) . . no
C(14) H(14C) 0.94(4) . . no
C(15) C(16) 1.63(3) . . yes
C(15) C(17) 1.11(4) . . yes
C(16) C(17) 1.59(7) . . yes
C(17) C(18) 1.71(10) . . yes
C(18) C(20) 1.71(5) . . yes
C(19) C(20) 0.77(2) . 4_555 yes
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O(5) H(5O) O(1) . . . 0.88(4) 2.59(3) 2.857(2) 98(2) no
O(7) H(7O) O(8) . . . 0.88(3) 1.80(3) 2.582(3) 146(3) no
O(5) H(5O) O(2) . . 3_556 0.88(3) 1.89(3) 2.713(3) 156(3) no
