From Hydrindane to Decalin: A Mild Transformation through a Dyotropic Ring Expansion.
Santalla, Hugo; Faza, Olalla Nieto; Gómez, Generosa; Fall, Yagamare; Silva López, Carlos; Organic letters 19 (2017) 3648–3651; doi:10.1021/acs.orglett.7b01621

data_1556063
_publ_section_title
;
 From Hydrindane to Decalin: A Mild Transformation through a Dyotropic
 Ring Expansion.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3648
_journal_page_last               3651
_journal_paper_doi               10.1021/acs.orglett.7b01621
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H38 O4 S Si'
_chemical_formula_sum            'C19 H38 O4 S Si'
_chemical_formula_weight         390.64
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-05-29
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 102.088(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.0435(11)
_cell_length_b                   8.0033(7)
_cell_length_c                   23.937(2)
_cell_measurement_reflns_used    9989
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.44
_cell_measurement_theta_min      2.61
_cell_volume                     2256.1(3)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100 CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'Incoatec HeliosTM multilayer optics'
_diffrn_radiation_source         'Incoatec high brillance I\muS microsource'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            42275
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.436
_diffrn_reflns_theta_min         2.611
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5941
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1502 before and 0.0692 after correction.
The Ratio of minimum to maximum transmission is 0.7970.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.150
_exptl_crystal_description       needle
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.366
_exptl_crystal_size_mid          0.082
_exptl_crystal_size_min          0.053
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details
;
 Flack x determined using 3633 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     467
_refine_ls_number_reflns         9222
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0401
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0612P)^2^+0.5470P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0974
_refine_ls_wR_factor_ref         0.1010
_reflns_Friedel_coverage         0.860
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                8448
_reflns_number_total             9222
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b01621_si_002.cif
_cod_data_source_block           32009101_0m_a
_cod_depositor_comments
;

2022-05-28
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        2256.0(3)
_cod_original_formula_moiety     '2(C19 H38 O4 S Si)'
_cod_original_formula_sum        'C38 H76 O8 S2 Si2'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     781.28
_cod_database_code               1556063
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.925
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C4A(H4AA), C5(H5), C2'(H2'), C1'(H1'), C4A'(H4A'), C5'(H5')
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C3'(H3'A,
 H3'B), C4'(H4'A,H4'B), C6'(H6'A,H6'B), C7'(H7'A,H7'B), C8'(H8'A,H8'B)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C21(H21A,H21B,H21C), C51(H51A,H51B,H51C), C52(H52A,H52B,
 H52C), C54(H54A,H54B,H54C), C55(H55A,H55B,H55C), C56(H56A,H56B,H56C), C81(H81A,
 H81B,H81C), C15'(H15D,H15E,H15F), C21'(H21D,H21E,H21F), C51'(H51D,H51E,H51F),
 C52'(H52D,H52E,H52F), C54'(H54D,H54E,H54F), C55'(H55D,H55E,H55F), C56'(H56D,
 H56E,H56F), C81'(H81D,H81E,H81F)
;
_olex2_submission_special_instructions 'No special instructions were received'