#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/73/1507324.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_1507324
loop_
_publ_author_name
'Su, Qibin'
'Beeler, Aaron B.'
'Lobkovsky, Emil'
'Porco, Jr, John A'
'Panek, James S.'
_publ_section_title
;
 Stereochemical diversity through cyclodimerization: synthesis of
 polyketide-like macrodiolides.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              2149
_journal_page_last               2152
_journal_paper_doi               10.1021/ol034608z
_journal_volume                  5
_journal_year                    2003
_chemical_formula_sum            'C18 H28 O6'
_chemical_formula_weight         340.40
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.618(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.3989(9)
_cell_length_b                   10.2639(10)
_cell_length_c                   10.2739(10)
_cell_measurement_temperature    173(2)
_cell_volume                     967.18(16)
_computing_cell_refinement       SAINT+
_computing_data_collection       SMART
_computing_data_reduction        SAINT+
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker 1K CCD'
_diffrn_measurement_method       '0.3 deg. omega & phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_sigmaI/netI    0.0357
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8515
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.66
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9914
_exptl_absorpt_correction_T_min  0.8496
_exptl_absorpt_correction_type   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.169
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.129
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1.5(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_hydrogen_treatment    isotropic
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         4182
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0365
_refine_ls_shift/su_max          0.104
_refine_ls_shift/su_mean         0.015
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0520P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0807
_refine_ls_wR_factor_ref         0.0869
_reflns_number_gt                3415
_reflns_number_total             4182
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol034608zsi20030408_065000.cif
_cod_data_source_block           porco10
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               1507324
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-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
O1 O 0.58744(14) 0.88179(15) 1.15791(15) 0.0519(4) Uani 1 1 d
O2 O 0.74360(12) 0.91917(14) 0.60879(11) 0.0436(3) Uani 1 1 d
O3 O 0.37213(12) 0.98506(13) 0.63685(12) 0.0387(3) Uani 1 1 d
O4 O 0.25861(16) 0.80664(15) 0.68779(14) 0.0538(4) Uani 1 1 d
O5 O 0.09952(12) 1.02716(13) 1.18552(10) 0.0368(3) Uani 1 1 d
O6 O 0.46496(11) 1.07026(11) 1.13406(11) 0.0355(3) Uani 1 1 d
C1 C 0.58088(17) 0.99537(18) 1.12890(15) 0.0326(4) Uani 1 1 d
C2 C 0.69602(17) 1.0710(2) 1.08029(17) 0.0350(4) Uani 1 1 d
H2B H 0.7851(19) 1.0191(18) 1.0924(16) 0.030(4) Uiso 1 1 d
H2A H 0.720(2) 1.143(2) 1.137(2) 0.042(5) Uiso 1 1 d
C3 C 0.64270(16) 1.11212(18) 0.93708(16) 0.0329(4) Uani 1 1 d
H3 H 0.5664(17) 1.1720(17) 0.9208(15) 0.020(4) Uiso 1 1 d
C4 C 0.70173(16) 1.07192(18) 0.83915(16) 0.0325(4) Uani 1 1 d
H4 H 0.784(2) 1.016(2) 0.8574(18) 0.036(5) Uiso 1 1 d
C5 C 0.65428(17) 1.11265(19) 0.69600(16) 0.0353(4) Uani 1 1 d
H5 H 0.5730(19) 1.1627(19) 0.6873(16) 0.029(4) Uiso 1 1 d
C6 C 0.61544(16) 0.9968(2) 0.60275(16) 0.0366(4) Uani 1 1 d
H6 H 0.5825(17) 1.0300(19) 0.5124(18) 0.033(4) Uiso 1 1 d
C7 C 0.50151(18) 0.9067(2) 0.63800(19) 0.0401(4) Uani 1 1 d
H7B H 0.5337(18) 0.872(2) 0.7266(19) 0.037(5) Uiso 1 1 d
H7A H 0.4790(19) 0.838(2) 0.5704(18) 0.036(5) Uiso 1 1 d
C8 C 0.25976(17) 0.9217(2) 0.67106(14) 0.0357(4) Uani 1 1 d
C9 C 0.14187(17) 1.0150(2) 0.68818(16) 0.0373(4) Uani 1 1 d
H9B H 0.123(2) 1.067(2) 0.608(2) 0.041(5) Uiso 1 1 d
H9A H 0.0591(19) 0.9646(19) 0.6952(17) 0.033(5) Uiso 1 1 d
C10 C 0.19106(16) 1.10045(18) 0.80886(15) 0.0310(3) Uani 1 1 d
H10 H 0.268(2) 1.159(2) 0.8084(17) 0.037(5) Uiso 1 1 d
C11 C 0.13517(16) 1.09423(17) 0.91576(15) 0.0292(3) Uani 1 1 d
H11 H 0.0518(19) 1.0337(18) 0.9120(16) 0.031(4) Uiso 1 1 d
C12 C 0.17751(16) 1.18023(17) 1.03609(16) 0.0294(3) Uani 1 1 d
H12 H 0.2578(18) 1.2296(17) 1.0282(15) 0.026(4) Uiso 1 1 d
C13 C 0.22195(16) 1.10132(17) 1.16460(15) 0.0303(3) Uani 1 1 d
H13 H 0.2522(17) 1.1612(17) 1.2340(16) 0.022(4) Uiso 1 1 d
C14 C 0.34123(17) 1.00224(19) 1.16479(17) 0.0337(4) Uani 1 1 d
H14B H 0.3081(18) 0.9324(18) 1.0932(17) 0.030(4) Uiso 1 1 d
H14A H 0.3748(19) 0.9570(19) 1.2529(18) 0.037(5) Uiso 1 1 d
C15 C 0.7722(2) 1.1968(2) 0.6549(2) 0.0463(5) Uani 1 1 d
H15C H 0.788(3) 1.278(3) 0.706(2) 0.073(8) Uiso 1 1 d
H15B H 0.859(3) 1.149(2) 0.666(2) 0.058(6) Uiso 1 1 d
H15A H 0.748(2) 1.213(2) 0.564(2) 0.052(6) Uiso 1 1 d
C16 C 0.7585(3) 0.8655(4) 0.4868(2) 0.0713(8) Uani 1 1 d
H16C H 0.676(4) 0.800(4) 0.446(3) 0.104(10) Uiso 1 1 d
H16B H 0.848(3) 0.825(2) 0.497(2) 0.058(6) Uiso 1 1 d
H16A H 0.732(4) 0.934(4) 0.423(4) 0.122(14) Uiso 1 1 d
C17 C 0.05199(19) 1.2717(2) 1.0461(2) 0.0388(4) Uani 1 1 d
H17C H -0.038(2) 1.221(2) 1.0483(19) 0.043(5) Uiso 1 1 d
H17B H 0.076(2) 1.316(2) 1.130(2) 0.050(6) Uiso 1 1 d
H17A H 0.0372(19) 1.333(2) 0.9718(19) 0.039(5) Uiso 1 1 d
C18 C 0.0700(2) 1.0401(3) 1.31371(19) 0.0498(5) Uani 1 1 d
H18B H 0.156(3) 1.024(3) 1.384(2) 0.064(7) Uiso 1 1 d
H18C H -0.008(3) 0.973(3) 1.323(2) 0.072(7) Uiso 1 1 d
H18A H 0.034(3) 1.131(3) 1.317(2) 0.065(7) Uiso 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
C16 O2 C6 115.23(15)
C8 O3 C7 115.51(15)
C18 O5 C13 114.72(14)
C1 O6 C14 115.42(14)
O1 C1 O6 122.91(16)
O1 C1 C2 125.58(16)
O6 C1 C2 111.50(16)
C1 C2 C3 111.04(13)
C4 C3 C2 123.53(15)
C3 C4 C5 125.25(15)
C4 C5 C6 112.26(15)
C4 C5 C15 110.39(15)
C6 C5 C15 110.80(15)
O2 C6 C7 106.31(15)
O2 C6 C5 108.87(13)
C7 C6 C5 114.27(14)
O3 C7 C6 107.02(16)
O4 C8 O3 123.11(17)
O4 C8 C9 125.67(16)
O3 C8 C9 111.20(17)
C8 C9 C10 111.45(13)
C11 C10 C9 123.42(15)
C10 C11 C12 125.15(15)
C11 C12 C13 111.94(14)
C11 C12 C17 110.31(13)
C13 C12 C17 109.67(13)
O5 C13 C14 105.16(14)
O5 C13 C12 109.51(12)
C14 C13 C12 114.84(13)
O6 C14 C13 107.79(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.202(2)
O2 C16 1.404(2)
O2 C6 1.434(2)
O3 C8 1.351(2)
O3 C7 1.456(2)
O4 C8 1.193(2)
O5 C18 1.410(2)
O5 C13 1.4345(19)
O6 C1 1.3438(19)
O6 C14 1.4491(19)
C1 C2 1.503(2)
C2 C3 1.507(2)
C3 C4 1.317(2)
C4 C5 1.500(2)
C5 C6 1.521(3)
C5 C15 1.535(3)
C6 C7 1.518(3)
C8 C9 1.504(3)
C9 C10 1.507(2)
C10 C11 1.319(2)
C11 C12 1.500(2)
C12 C13 1.527(2)
C12 C17 1.529(2)
C13 C14 1.513(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30651823
