#------------------------------------------------------------------------------
#$Date: 2025-08-18 17:20:24 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301776 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/51/25/1512585.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_1512585
loop_
_publ_author_name
'Tanis, Paul S.'
'Infantine, Joshua R.'
'Leighton, James L.'
_publ_section_title
;
 Exploiting pseudo c2-symmetry for an efficient synthesis of the f-ring of
 the spongistatins.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5464
_journal_page_last               5467
_journal_paper_doi               10.1021/ol402604s
_journal_volume                  15
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_sum            'C28 H45 N O9 Si'
_chemical_formula_weight         567.74
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.9610(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.6627(7)
_cell_length_b                   13.4490(9)
_cell_length_c                   12.0884(8)
_cell_measurement_reflns_used    9968
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      32.43
_cell_measurement_theta_min      2.27
_cell_volume                     1570.71(19)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0244
_diffrn_reflns_av_sigmaI/netI    0.0310
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            26117
_diffrn_reflns_theta_full        31.00
_diffrn_reflns_theta_max         31.00
_diffrn_reflns_theta_min         1.68
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_T_max  0.9638
_exptl_absorpt_correction_T_min  0.9407
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             612
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.458
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         9939
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0444
_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)+(0.0738P)²+0.1270P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1140
_refine_ls_wR_factor_ref         0.1201
_reflns_number_gt                8837
_reflns_number_total             9939
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol402604s_si_002.cif
_cod_data_source_block           pt4s10
_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 2.4.2 from
2011-04-26.

'_refine_ls_hydrogen_treatment' value 'CONSTR' changed
to 'constr' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               1512585
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
_atom_site_refinement_flags
Si Si 0.38545(5) 1.14024(3) 0.54296(3) 0.02714(9) Uani 1 1 d .
N N 0.57368(13) 0.66988(10) 0.97979(11) 0.0265(3) Uani 1 1 d .
O1 O 0.52391(11) 0.62817(8) 0.88040(8) 0.0260(2) Uani 1 1 d .
O2 O 0.79955(14) 0.90512(11) 0.78323(14) 0.0456(3) Uani 1 1 d .
O3 O 0.81982(12) 1.04645(10) 0.87966(11) 0.0354(3) Uani 1 1 d .
O4 O 0.41054(12) 1.02648(8) 0.59281(8) 0.0259(2) Uani 1 1 d .
O5 O 0.14485(11) 0.94579(9) 0.64264(9) 0.0294(2) Uani 1 1 d .
O6 O 0.47674(10) 0.90363(8) 0.85699(8) 0.02155(19) Uani 1 1 d .
O7 O 0.29573(11) 0.84650(8) 1.02659(8) 0.0236(2) Uani 1 1 d .
O8 O 0.1448(2) 0.83572(17) 0.50314(17) 0.0764(6) Uani 1 1 d .
O9 O 0.56348(12) 0.80576(9) 1.08757(9) 0.0279(2) Uani 1 1 d .
C1 C 0.96090(19) 1.01912(19) 0.90817(19) 0.0460(5) Uani 1 1 d .
H1A H 0.9951 1.0617 0.9684 0.069 Uiso 1 1 calc R
H1B H 1.0194 1.0277 0.8434 0.069 Uiso 1 1 calc R
H1C H 0.9637 0.9495 0.9320 0.069 Uiso 1 1 calc R
C2 C -0.0485(2) 0.94584(19) 0.52293(19) 0.0507(5) Uani 1 1 d .
H2A H -0.0708 0.9335 0.4447 0.076 Uiso 1 1 calc R
H2B H -0.0460 1.0176 0.5366 0.076 Uiso 1 1 calc R
H2C H -0.1193 0.9153 0.5690 0.076 Uiso 1 1 calc R
C3 C 0.1144(3) 1.1916(2) 0.6256(2) 0.0578(6) Uani 1 1 d .
H3A H 0.0183 1.2070 0.6048 0.087 Uiso 1 1 calc R
H3B H 0.1555 1.2484 0.6648 0.087 Uiso 1 1 calc R
H3C H 0.1166 1.1330 0.6739 0.087 Uiso 1 1 calc R
C4 C 0.6250(3) 1.1171(2) 0.4174(3) 0.0687(8) Uani 1 1 d .
H4A H 0.6638 1.1149 0.3430 0.103 Uiso 1 1 calc R
H4B H 0.6408 1.0531 0.4544 0.103 Uiso 1 1 calc R
H4C H 0.6700 1.1702 0.4602 0.103 Uiso 1 1 calc R
C5 C -0.0949(2) 0.99329(17) 1.21043(18) 0.0448(5) Uani 1 1 d .
H5A H -0.1717 1.0347 1.2260 0.054 Uiso 1 1 calc R
C6 C -0.11651(19) 0.90034(17) 1.16537(18) 0.0432(4) Uani 1 1 d .
H6A H -0.2079 0.8775 1.1500 0.052 Uiso 1 1 calc R
C7 C 0.1967(2) 1.17016(16) 0.52169(19) 0.0457(5) Uani 1 1 d .
H7A H 0.1894 1.2288 0.4724 0.055 Uiso 1 1 calc R
H7B H 0.1524 1.1136 0.4824 0.055 Uiso 1 1 calc R
C8 C 0.4723(3) 1.13700(18) 0.40880(15) 0.0501(5) Uani 1 1 d .
H8A H 0.4286 1.0848 0.3622 0.060 Uiso 1 1 calc R
H8B H 0.4575 1.2016 0.3710 0.060 Uiso 1 1 calc R
C9 C 0.0375(2) 1.02646(16) 1.23302(17) 0.0445(4) Uani 1 1 d .
H9A H 0.0520 1.0906 1.2641 0.053 Uiso 1 1 calc R
C10 C 0.0897(2) 0.90169(16) 0.55106(16) 0.0417(4) Uani 1 1 d .
C11 C 0.14994(18) 0.96559(14) 1.21013(15) 0.0357(4) Uani 1 1 d .
H11A H 0.2411 0.9884 1.2262 0.043 Uiso 1 1 calc R
C12 C 0.4638(2) 1.23386(13) 0.63833(15) 0.0365(4) Uani 1 1 d .
H12A H 0.4240 1.2249 0.7126 0.044 Uiso 1 1 calc R
H12B H 0.5645 1.2209 0.6449 0.044 Uiso 1 1 calc R
C13 C 0.4422(3) 1.34205(15) 0.60239(19) 0.0475(5) Uani 1 1 d .
H13A H 0.4825 1.3866 0.6584 0.071 Uiso 1 1 calc R
H13B H 0.3429 1.3556 0.5942 0.071 Uiso 1 1 calc R
H13C H 0.4874 1.3532 0.5315 0.071 Uiso 1 1 calc R
C14 C 0.71929(18) 0.64927(17) 1.00223(17) 0.0423(4) Uani 1 1 d .
H14A H 0.7452 0.6748 1.0757 0.063 Uiso 1 1 calc R
H14B H 0.7757 0.6818 0.9462 0.063 Uiso 1 1 calc R
H14C H 0.7351 0.5773 1.0000 0.063 Uiso 1 1 calc R
C15 C -0.00360(18) 0.84028(14) 1.14255(16) 0.0358(4) Uani 1 1 d .
H15A H -0.0185 0.7762 1.1115 0.043 Uiso 1 1 calc R
C16 C 0.25133(16) 0.81008(13) 1.13181(13) 0.0296(3) Uani 1 1 d .
H16A H 0.3271 0.8159 1.1876 0.036 Uiso 1 1 calc R
H16B H 0.2239 0.7393 1.1259 0.036 Uiso 1 1 calc R
C17 C 0.47031(18) 0.53028(12) 0.90124(14) 0.0314(3) Uani 1 1 d .
H17A H 0.4417 0.4994 0.8311 0.047 Uiso 1 1 calc R
H17B H 0.3904 0.5352 0.9499 0.047 Uiso 1 1 calc R
H17C H 0.5423 0.4896 0.9370 0.047 Uiso 1 1 calc R
C18 C 0.13506(17) 0.77661(13) 0.79030(15) 0.0312(3) Uani 1 1 d .
H18A H 0.0507 0.8032 0.7552 0.047 Uiso 1 1 calc R
H18B H 0.1137 0.7520 0.8644 0.047 Uiso 1 1 calc R
H18C H 0.1709 0.7219 0.7455 0.047 Uiso 1 1 calc R
C19 C 0.75279(15) 0.98302(12) 0.81241(14) 0.0279(3) Uani 1 1 d .
C20 C 0.13059(16) 0.87226(12) 1.16432(12) 0.0267(3) Uani 1 1 d .
C21 C 0.50839(14) 0.94660(11) 0.75280(11) 0.0216(2) Uani 1 1 d .
H21A H 0.5485 0.8946 0.7037 0.026 Uiso 1 1 calc R
C22 C 0.36944(14) 0.77736(10) 0.96234(11) 0.0201(2) Uani 1 1 d .
H22A H 0.3152 0.7142 0.9569 0.024 Uiso 1 1 calc R
C23 C 0.38204(14) 0.82234(10) 0.84717(11) 0.0206(2) Uani 1 1 d .
H23A H 0.4214 0.7714 0.7963 0.025 Uiso 1 1 calc R
C24 C 0.51188(15) 0.75506(10) 1.01412(12) 0.0215(2) Uani 1 1 d .
C25 C 0.61560(15) 1.02572(11) 0.77588(13) 0.0260(3) Uani 1 1 d .
H25A H 0.6286 1.0657 0.7081 0.031 Uiso 1 1 calc R
H25B H 0.5814 1.0707 0.8342 0.031 Uiso 1 1 calc R
C26 C 0.24356(14) 0.85857(10) 0.79943(12) 0.0220(2) Uani 1 1 d .
H26A H 0.2074 0.9115 0.8493 0.026 Uiso 1 1 calc R
C27 C 0.27182(15) 0.90549(11) 0.68709(12) 0.0233(3) Uani 1 1 d .
H27A H 0.3077 0.8536 0.6357 0.028 Uiso 1 1 calc R
C28 C 0.37712(14) 0.98924(10) 0.69820(11) 0.0212(2) Uani 1 1 d .
H28A H 0.3391 1.0438 0.7449 0.025 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 0.0033 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'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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
O4 Si C8 103.43(9)
O4 Si C12 110.08(7)
C8 Si C12 112.07(10)
O4 Si C7 112.46(8)
C8 Si C7 109.88(11)
C12 Si C7 108.89(10)
C24 N O1 116.87(12)
C24 N C14 122.12(14)
O1 N C14 113.57(12)
N O1 C17 109.57(11)
C19 O3 C1 115.28(15)
C28 O4 Si 128.34(9)
C10 O5 C27 117.46(14)
C21 O6 C23 112.57(10)
C22 O7 C16 115.07(11)
C9 C5 C6 120.42(18)
C5 C6 C15 119.44(18)
C3 C7 Si 116.46(16)
C4 C8 Si 113.94(17)
C5 C9 C11 119.70(19)
O8 C10 O5 123.40(18)
O8 C10 C2 126.17(19)
O5 C10 C2 110.41(19)
C20 C11 C9 120.83(17)
C13 C12 Si 114.53(13)
C20 C15 C6 121.12(18)
O7 C16 C20 106.77(12)
O2 C19 O3 123.78(15)
O2 C19 C25 125.67(16)
O3 C19 C25 110.50(14)
C11 C20 C15 118.49(15)
C11 C20 C16 120.83(15)
C15 C20 C16 120.55(15)
O6 C21 C25 106.25(11)
O6 C21 C28 110.16(11)
C25 C21 C28 112.15(12)
O7 C22 C23 106.84(10)
O7 C22 C24 111.23(11)
C23 C22 C24 111.46(11)
O6 C23 C22 106.77(10)
O6 C23 C26 110.05(10)
C22 C23 C26 112.86(11)
O9 C24 N 121.13(13)
O9 C24 C22 122.79(13)
N C24 C22 115.87(12)
C19 C25 C21 112.60(13)
C18 C26 C27 111.58(12)
C18 C26 C23 113.19(12)
C27 C26 C23 107.41(11)
O5 C27 C28 108.60(11)
O5 C27 C26 108.92(12)
C28 C27 C26 110.90(11)
O4 C28 C27 110.22(11)
O4 C28 C21 108.75(11)
C27 C28 C21 107.97(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Si O4 1.6606(11)
Si C8 1.8388(19)
Si C12 1.8598(18)
Si C7 1.881(2)
N C24 1.3600(18)
N O1 1.4036(17)
N C14 1.455(2)
O1 C17 1.4385(19)
O2 C19 1.196(2)
O3 C19 1.338(2)
O3 C1 1.448(2)
O4 C28 1.4114(17)
O5 C10 1.357(2)
O5 C27 1.4373(17)
O6 C21 1.4236(16)
O6 C23 1.4293(16)
O7 C22 1.4120(17)
O7 C16 1.4353(18)
O8 C10 1.190(3)
O9 C24 1.2194(18)
C2 C10 1.495(3)
C3 C7 1.525(3)
C4 C8 1.502(4)
C5 C9 1.378(3)
C5 C6 1.378(3)
C6 C15 1.389(3)
C9 C11 1.392(3)
C11 C20 1.383(2)
C12 C13 1.532(3)
C15 C20 1.387(2)
C16 C20 1.493(2)
C18 C26 1.524(2)
C19 C25 1.504(2)
C21 C25 1.508(2)
C21 C28 1.5315(19)
C22 C23 1.5247(18)
C22 C24 1.5321(19)
C23 C26 1.5281(18)
C26 C27 1.526(2)
C27 C28 1.522(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 102106598
