#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/28/4022887.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_4022887
loop_
_publ_author_name
'Masayuki Inoue'
'Nayoung Lee'
'Satoshi Kasuya'
'Takaaki Sato'
'Masahiro Hirama'
'Miyako Moriyama'
'Yoshiyasu Fukuyama'
_publ_section_title
;
 Total Synthesis and Bioactivity of an Unnatural Enantiomer
 of Merrilactone A: Development of an Enantioselective
 Desymmetrization Strategy
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3065
_journal_page_last               3075
_journal_paper_doi               10.1021/jo0700474
_journal_volume                  72
_journal_year                    2007
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C26 H26 Cl4 O4 '
_chemical_formula_sum            'C26 H26 Cl4 O4'
_chemical_formula_weight         544.30
_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'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.510(3)
_cell_length_b                   11.488(4)
_cell_length_c                   20.740(6)
_cell_measurement_reflns_used    8715
_cell_measurement_temperature    173.1
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.3
_cell_volume                     2504.1(13)
_computing_cell_refinement       CRYSTALCLEAR
_computing_data_collection       CRYSTALCLEAR
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.6.0'
_computing_structure_refinement  CRYSTALS
_computing_structure_solution    SIR92
_diffrn_ambient_temperature      173.2
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.9920
_diffrn_measured_fraction_theta_max 0.9920
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.028
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            26624
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_exptl_absorpt_coefficient_mu    0.504
_exptl_absorpt_correction_T_max  0.904
_exptl_absorpt_correction_T_min  0.828
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1128.00
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.35
_refine_diff_density_min         -0.45
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  2431 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.02(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     308
_refine_ls_number_reflns         5669
_refine_ls_R_factor_gt           0.0280
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[0.0003Fo² + 1.0000σ(Fo²)]/(4Fo²)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0690
_reflns_number_gt                5281
_reflns_number_total             5669
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            jo0700474si20070201_120108.cif
_cod_data_source_block           '__sato520'
_cod_original_formula_sum        'C26 H26 Cl4 O4 '
_cod_database_code               4022887
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 1/2+X,1/2-Y,-Z
3 -X,1/2+Y,1/2-Z
4 1/2-X,-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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl(1) Cl 0.11871(4) 0.25026(4) 0.12619(2) 0.0405(1) Uani 1.00 1 d .
Cl(2) Cl 0.55113(4) 0.34073(4) 0.25958(2) 0.0376(1) Uani 1.00 1 d .
Cl(3) Cl 0.18924(4) -0.22144(4) 0.38141(2) 0.0437(1) Uani 1.00 1 d .
Cl(4) Cl 0.51791(5) 0.14215(4) 0.36943(2) 0.0418(1) Uani 1.00 1 d .
O(1) O -0.1606(1) 0.2459(1) 0.42012(5) 0.0372(3) Uani 1.00 1 d .
O(2) O 0.2562(1) 0.3272(1) 0.45426(5) 0.0358(3) Uani 1.00 1 d .
O(3) O 0.1767(1) 0.38704(9) 0.25794(5) 0.0276(3) Uani 1.00 1 d .
O(4) O 0.1900(1) 0.09406(9) 0.35796(5) 0.0234(3) Uani 1.00 1 d .
C(1) C 0.0937(2) 0.1190(1) 0.50027(7) 0.0307(4) Uani 1.00 1 d .
C(2) C 0.0338(2) 0.0269(1) 0.47804(8) 0.0323(4) Uani 1.00 1 d .
C(3) C -0.0561(2) 0.0546(1) 0.42407(8) 0.0301(4) Uani 1.00 1 d .
C(4) C -0.0415(1) 0.1878(1) 0.41309(7) 0.0248(4) Uani 1.00 1 d .
C(5) C 0.0163(1) 0.2287(1) 0.34578(7) 0.0222(4) Uani 1.00 1 d .
C(6) C 0.1066(1) 0.3327(1) 0.36467(7) 0.0230(4) Uani 1.00 1 d .
C(7) C 0.1554(1) 0.2974(1) 0.43123(7) 0.0242(4) Uani 1.00 1 d .
C(8) C 0.0337(2) 0.4485(1) 0.37433(8) 0.0325(4) Uani 1.00 1 d .
C(9) C 0.0544(1) 0.2280(1) 0.46538(7) 0.0250(4) Uani 1.00 1 d .
C(10) C 0.2207(1) 0.3547(1) 0.32079(7) 0.0257(4) Uani 1.00 1 d .
C(11) C -0.0880(1) 0.2606(2) 0.29753(8) 0.0305(4) Uani 1.00 1 d .
C(12) C 0.0950(1) 0.1333(1) 0.31417(7) 0.0227(4) Uani 1.00 1 d .
C(13) C 0.2780(2) 0.4033(1) 0.21332(7) 0.0287(4) Uani 1.00 1 d .
C(14) C 0.3374(2) 0.2898(1) 0.19158(7) 0.0261(4) Uani 1.00 1 d .
C(15) C 0.2719(2) 0.2138(1) 0.15048(7) 0.0288(4) Uani 1.00 1 d .
C(16) C 0.3231(2) 0.1110(1) 0.12776(8) 0.0339(4) Uani 1.00 1 d .
C(17) C 0.4450(2) 0.0802(2) 0.14590(9) 0.0384(5) Uani 1.00 1 d .
C(18) C 0.5134(2) 0.1516(2) 0.18676(8) 0.0340(4) Uani 1.00 1 d .
C(19) C 0.4599(1) 0.2544(1) 0.20851(7) 0.0286(4) Uani 1.00 1 d .
C(20) C 0.2756(1) 0.0150(1) 0.32790(7) 0.0259(4) Uani 1.00 1 d .
C(21) C 0.3563(1) -0.0408(1) 0.37923(7) 0.0235(4) Uani 1.00 1 d .
C(22) C 0.3244(2) -0.1476(1) 0.40705(7) 0.0279(4) Uani 1.00 1 d .
C(23) C 0.3984(2) -0.2008(2) 0.45379(8) 0.0361(5) Uani 1.00 1 d .
C(24) C 0.5085(2) -0.1469(2) 0.47393(8) 0.0401(5) Uani 1.00 1 d .
C(25) C 0.5445(2) -0.0412(2) 0.44828(8) 0.0349(4) Uani 1.00 1 d .
C(26) C 0.4683(2) 0.0100(1) 0.40143(7) 0.0272(4) Uani 1.00 1 d .
H(1) H 0.1530 0.1173 0.5335 0.037 Uiso 1.00 1 c R
H(2) H 0.0459 -0.0477 0.4943 0.039 Uiso 1.00 1 c R
H(3) H -0.1429 0.0354 0.4359 0.037 Uiso 1.00 1 c R
H(4) H -0.0333 0.0119 0.3855 0.036 Uiso 1.00 1 c R
H(5) H 0.0100 0.2791 0.4957 0.031 Uiso 1.00 1 c R
H(6) H 0.2730 0.4164 0.3386 0.031 Uiso 1.00 1 c R
H(7) H 0.2720 0.2848 0.3179 0.030 Uiso 1.00 1 c R
H(8) H 0.3429 0.4512 0.2333 0.034 Uiso 1.00 1 c R
H(9) H 0.2461 0.4447 0.1760 0.035 Uiso 1.00 1 c R
H(10) H 0.0403 0.0688 0.3020 0.028 Uiso 1.00 1 c R
H(11) H 0.1349 0.1633 0.2754 0.027 Uiso 1.00 1 c R
H(12) H 0.3293 0.0563 0.2973 0.031 Uiso 1.00 1 c R
H(13) H 0.2285 -0.0442 0.3045 0.031 Uiso 1.00 1 c R
H(14) H 0.2761 0.0629 0.1005 0.041 Uiso 1.00 1 c R
H(15) H 0.4809 0.0116 0.1303 0.046 Uiso 1.00 1 c R
H(16) H 0.5947 0.1305 0.1998 0.041 Uiso 1.00 1 c R
H(17) H 0.3735 -0.2717 0.4716 0.043 Uiso 1.00 1 c R
H(18) H 0.5593 -0.1824 0.5050 0.048 Uiso 1.00 1 c R
H(19) H 0.6182 -0.0045 0.4622 0.042 Uiso 1.00 1 c R
H(20) H -0.0342 0.4370 0.4045 0.039 Uiso 1.00 1 c R
H(21) H -0.0003 0.4741 0.3338 0.039 Uiso 1.00 1 c R
H(22) H 0.0912 0.5064 0.3908 0.039 Uiso 1.00 1 c R
H(23) H -0.0496 0.2855 0.2578 0.037 Uiso 1.00 1 c R
H(24) H -0.1393 0.3225 0.3146 0.037 Uiso 1.00 1 c R
H(25) H -0.1407 0.1938 0.2894 0.037 Uiso 1.00 1 c R
H(26) H -0.1853 0.2250 0.4469 0.045 Uiso 1.00 1 c R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
Cl Cl 0.148 0.159
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.011 0.006
;
International Tables for Crystallography
(1992, 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
Cl(1) C(15) C(14) 118.8(1)
Cl(1) C(15) C(16) 117.9(1)
Cl(2) C(19) C(14) 119.7(1)
Cl(2) C(19) C(18) 117.5(1)
Cl(3) C(22) C(21) 119.9(1)
Cl(3) C(22) C(23) 117.2(1)
Cl(4) C(26) C(21) 119.6(1)
Cl(4) C(26) C(25) 117.6(1)
O(1) C(4) C(3) 111.0(1)
O(1) C(4) C(9) 111.1(1)
O(1) C(4) C(5) 106.7(1)
O(2) C(7) C(9) 125.5(1)
O(2) C(7) C(6) 125.1(1)
C(13) O(3) C(10) 112.6(1)
O(3) C(10) C(6) 109.4(1)
O(3) C(13) C(14) 112.9(1)
C(20) O(4) C(12) 111.5(1)
O(4) C(12) C(5) 109.5(1)
O(4) C(20) C(21) 108.6(1)
C(1) C(2) C(3) 113.1(1)
C(9) C(1) C(2) 111.7(1)
C(1) C(9) C(4) 105.5(1)
C(1) C(9) C(7) 118.3(1)
C(2) C(3) C(4) 104.8(1)
C(3) C(4) C(9) 104.7(1)
C(3) C(4) C(5) 117.1(1)
C(4) C(5) C(12) 111.9(1)
C(9) C(4) C(5) 106.1(1)
C(4) C(5) C(6) 103.6(1)
C(4) C(5) C(11) 111.7(1)
C(4) C(9) C(7) 106.7(1)
C(5) C(6) C(7) 103.1(1)
C(5) C(6) C(10) 116.8(1)
C(12) C(5) C(6) 109.0(1)
C(11) C(5) C(6) 114.4(1)
C(5) C(6) C(8) 112.7(1)
C(12) C(5) C(11) 106.3(1)
C(10) C(6) C(7) 108.6(1)
C(6) C(7) C(9) 109.2(1)
C(8) C(6) C(7) 106.1(1)
C(10) C(6) C(8) 108.9(1)
C(13) C(14) C(15) 121.0(1)
C(13) C(14) C(19) 123.8(1)
C(19) C(14) C(15) 115.2(1)
C(14) C(15) C(16) 123.3(2)
C(14) C(19) C(18) 122.8(2)
C(15) C(16) C(17) 119.2(2)
C(16) C(17) C(18) 119.9(2)
C(17) C(18) C(19) 119.7(2)
C(20) C(21) C(22) 122.1(1)
C(20) C(21) C(26) 122.1(1)
C(26) C(21) C(22) 115.8(1)
C(21) C(22) C(23) 122.8(2)
C(21) C(26) C(25) 122.7(2)
C(22) C(23) C(24) 119.0(2)
C(23) C(24) C(25) 120.6(2)
C(24) C(25) C(26) 119.0(2)
H(26) O(1) C(4) 105.1788
O(3) C(10) H(6) 109.9207
O(3) C(10) H(7) 109.8298
O(3) C(13) H(8) 108.8316
O(3) C(13) H(9) 108.9591
O(4) C(12) H(10) 109.9214
O(4) C(12) H(11) 109.7418
O(4) C(20) H(12) 109.9331
O(4) C(20) H(13) 110.1028
H(1) C(1) C(2) 124.3041
C(1) C(2) H(2) 123.3479
H(1) C(1) C(9) 123.9835
C(1) C(9) H(5) 108.7378
H(2) C(2) C(3) 123.5245
C(2) C(3) H(3) 110.8777
C(2) C(3) H(4) 110.7037
H(3) C(3) C(4) 110.7211
H(4) C(3) C(4) 110.7063
H(4) C(3) H(3) 108.9715
C(4) C(9) H(5) 108.5244
C(5) C(11) H(24) 109.7841
C(5) C(11) H(23) 109.3326
C(5) C(11) H(25) 109.6259
C(5) C(12) H(10) 109.8787
C(5) C(12) H(11) 109.6460
C(6) C(8) H(20) 109.5512
C(6) C(8) H(21) 109.5518
C(6) C(8) H(22) 109.2523
C(6) C(10) H(6) 109.8214
C(6) C(10) H(7) 109.6465
C(7) C(9) H(5) 108.6954
H(21) C(8) H(20) 109.6594
H(22) C(8) H(20) 109.4032
H(22) C(8) H(21) 109.4085
H(7) C(10) H(6) 108.1972
H(24) C(11) H(23) 109.4097
H(25) C(11) H(23) 109.2497
H(25) C(11) H(24) 109.4237
H(11) C(12) H(10) 108.1020
H(8) C(13) C(14) 109.0363
H(9) C(13) C(14) 109.1335
H(9) C(13) H(8) 107.8655
C(15) C(16) H(14) 120.5157
H(14) C(16) C(17) 120.3163
C(16) C(17) H(15) 119.8986
H(15) C(17) C(18) 120.2460
C(17) C(18) H(16) 120.2011
H(16) C(18) C(19) 120.1087
H(12) C(20) C(21) 110.0513
H(13) C(20) C(21) 110.0609
H(13) C(20) H(12) 108.1181
C(22) C(23) H(17) 120.3443
H(17) C(23) C(24) 120.6043
C(23) C(24) H(18) 119.6371
H(18) C(24) C(25) 119.7373
C(24) C(25) H(19) 120.5541
H(19) C(25) C(26) 120.4624
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl(1) C(15) 1.738(2)
Cl(2) C(19) 1.739(2)
Cl(3) C(22) 1.738(2)
Cl(4) C(26) 1.737(2)
O(1) C(4) 1.426(2)
O(2) C(7) 1.212(2)
O(3) C(10) 1.432(2)
O(3) C(13) 1.423(2)
O(4) C(12) 1.423(2)
O(4) C(20) 1.423(2)
C(1) C(2) 1.314(2)
C(1) C(9) 1.503(2)
C(2) C(3) 1.499(2)
C(3) C(4) 1.555(2)
C(4) C(5) 1.593(2)
C(4) C(9) 1.551(2)
C(5) C(6) 1.575(2)
C(5) C(11) 1.529(2)
C(5) C(12) 1.521(2)
C(6) C(7) 1.527(2)
C(6) C(8) 1.548(2)
C(6) C(10) 1.526(2)
C(7) C(9) 1.505(2)
C(8) C(6) 1.548(2)
C(13) C(14) 1.514(2)
C(14) C(15) 1.401(2)
C(14) C(19) 1.395(2)
C(15) C(16) 1.381(2)
C(16) C(17) 1.381(3)
C(17) C(18) 1.382(3)
C(18) C(19) 1.383(2)
C(20) C(21) 1.504(2)
C(21) C(22) 1.396(2)
C(21) C(26) 1.392(2)
C(22) C(23) 1.384(2)
C(23) C(24) 1.377(3)
C(24) C(25) 1.378(3)
C(25) C(26) 1.390(2)
O(1) H(26) 0.6589
C(1) H(1) 0.9294
C(2) H(2) 0.9296
C(3) H(3) 0.9695
C(3) H(4) 0.9693
C(8) H(20) 0.9589
C(8) H(21) 0.9589
C(8) H(22) 0.9619
C(9) H(5) 0.9790
C(10) H(6) 0.9705
C(10) H(7) 0.9700
C(11) H(23) 0.9613
C(11) H(24) 0.9593
C(11) H(25) 0.9612
C(12) H(10) 0.9709
C(12) H(11) 0.9708
C(13) H(8) 0.9700
C(13) H(9) 0.9692
C(16) H(14) 0.9316
C(17) H(15) 0.9312
C(18) H(16) 0.9284
C(20) H(12) 0.9723
C(20) H(13) 0.9715
C(23) H(17) 0.9323
C(24) H(18) 0.9311
C(25) H(19) 0.9285
H(20) C(8) 0.9589
H(21) C(8) 0.9589
H(22) C(8) 0.9619
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 17284157
