Optically active P5-deltacyclenes: selective oxidation, ligand properties, and a diastereoselective rearrangement reaction.
Keller, I. C.; Bauer, W.; Heinemann, F. W.; Höhn, C; Rohwer, L.; Zenneck, U.; Dalton transactions (Cambridge, England : 2003) 45 (2016) 7267–7277; doi:10.1039/c6dt00548a

data_7038968
_publ_section_title
;
 Optically active P5-deltacyclenes: selective oxidation, ligand
 properties, and a diastereoselective rearrangement reaction.
;
_journal_issue                   17
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              7267
_journal_page_last               7277
_journal_paper_doi               10.1039/c6dt00548a
_journal_volume                  45
_journal_year                    2016
_chemical_formula_moiety         'C20 H37 P5 Se'
_chemical_formula_sum            'C20 H37 P5 Se'
_chemical_formula_weight         511.30
_chemical_properties_physical
'Air-sensitive, Moisture-sensitive, Heat-sensitive'
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2015-08-24
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-08-26 deposited with the CCDC.
2016-04-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 121.5910(10)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   35.8486(5)
_cell_length_b                   10.25200(10)
_cell_length_c                   30.1625(4)
_cell_measurement_reflns_used    7978
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.36
_cell_measurement_theta_min      2.28
_cell_volume                     9442.6(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'SHELXTL 6.12 (Bruker AXS, 2002)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL 6.12 (Bruker AXS, 2002)'
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 83.33
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker Smart APEX II CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0788
_diffrn_reflns_av_unetI/netI     0.0667
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_h_min       -48
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            69504
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        27.000
_diffrn_reflns_theta_max         28.700
_diffrn_reflns_theta_min         2.095
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.934
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.6155
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0830 before and 0.0610 after correction.
The Ratio of minimum to maximum transmission is 0.8252.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_description       plate
_exptl_crystal_F_000             4256
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: n-hexane'
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.558
_refine_diff_density_min         -0.819
_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     530
_refine_ls_number_reflns         12055
_refine_ls_number_restraints     54
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0397
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0349P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0788
_refine_ls_wR_factor_ref         0.0890
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8384
_reflns_number_total             12055
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6dt00548a1.cif
_cod_data_source_block           is1106
_cod_depositor_comments
'Adding full bibliography for 7038967--7038971.cif.'
_cod_database_code               7038968
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.910
_shelx_estimated_absorpt_t_min   0.535
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups, All P(H) groups
2. Uiso/Uaniso restraints and constraints
C51 \\sim C51A \\sim C52 \\sim C52A \\sim C53 \\sim C53A: within 1.7A with
sigma of 0.003 and sigma for terminal atoms of 0.006
Uanis(C51) \\sim Ueq, Uanis(C51A) \\sim Ueq, Uanis(C52) \\sim Ueq, Uanis(C52A)
\\sim Ueq, Uanis(C53) \\sim Ueq, Uanis(C53A) \\sim Ueq: with sigma of 0.005 and
sigma for terminal atoms of 0.01
3. Others
 Sof(C51A)=Sof(H51D)=Sof(H51E)=Sof(H51F)=Sof(C52A)=Sof(H52D)=Sof(H52E)=
 Sof(H52F)=Sof(C53A)=Sof(H53D)=Sof(H53E)=Sof(H53F)=1-FVAR(1)
 Sof(C51)=Sof(H51A)=Sof(H51B)=Sof(H51C)=Sof(C52)=Sof(H52A)=Sof(H52B)=Sof(H52C)=
 Sof(C53)=Sof(H53A)=Sof(H53B)=Sof(H53C)=FVAR(1)
4.a Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C21(H21A,H21B,
 H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C31(H31A,H31B,H31C), C32(H32A,
 H32B,H32C), C33(H33A,H33B,H33C), C41(H41A,H41B,H41C), C42(H42A,H42B,H42C),
 C43(H43A,H43B,H43C), C51(H51A,H51B,H51C), C51A(H51D,H51E,H51F), C52(H52A,H52B,
 H52C), C52A(H52D,H52E,H52F), C53(H53A,H53B,H53C), C53A(H53D,H53E,H53F),
 C61(H61A,H61B,H61C), C62(H62A,H62B,H62C), C63(H63A,H63B,H63C), C71(H71A,H71B,
 H71C), C72(H72A,H72B,H72C), C73(H73A,H73B,H73C), C81(H81A,H81B,H81C), C82(H82A,
 H82B,H82C), C83(H83A,H83B,H83C)
;
_shelx_res_checksum              5736
_olex2_submission_special_instructions 'No special instructions were received'