Acid-Induced Liberation of Polysubstituted Cyclopentadiene Ligands from Cyclopentadienyl Cobalt: A [2 + 2 + 1] Cycloaddition Route toward 1,2,4-Trisubstituted Cyclopentadienes.
Qin, Pengjin; Holland, Ryan L.; Bunker, Kevin D.; O'Connor, Joseph M; Baldridge, Kim K.; Rheingold, Arnold L.; The Journal of organic chemistry 84 (2019) 13992–14004; doi:10.1021/acs.joc.9b02182

data_4034566
_publ_section_title
;
 Acid-Induced Liberation of Polysubstituted Cyclopentadiene Ligands from
 Cyclopentadienyl Cobalt: A [2 + 2 + 1] Cycloaddition Route toward
 1,2,4-Trisubstituted Cyclopentadienes.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              13992
_journal_page_last               14004
_journal_paper_doi               10.1021/acs.joc.9b02182
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C30 H32 O4 Ru S'
_chemical_formula_sum            'C30 H32 O4 Ru S'
_chemical_formula_weight         589.68
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-01-12
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5289)
;
_cell_angle_alpha                90
_cell_angle_beta                 106.128(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.5730(11)
_cell_length_b                   15.4582(11)
_cell_length_c                   11.9655(9)
_cell_measurement_reflns_used    9828
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      26.335
_cell_measurement_theta_min      2.208
_cell_volume                     2767.1(3)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2016)'
_computing_data_collection       'APEX3 v2016.1-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 8.258
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Ultra'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0661
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            58579
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.431
_diffrn_reflns_theta_min         1.361
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker TXS'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.675
_exptl_absorpt_correction_T_max  0.2468
_exptl_absorpt_correction_T_min  0.2041
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1509 before and 0.0848 after correction. The Ratio of minimum to maximum transmission is 0.8270. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'Light Yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_description       Rod
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.217
_exptl_crystal_size_mid          0.153
_exptl_crystal_size_min          0.131
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.569
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     432
_refine_ls_number_reflns         5688
_refine_ls_number_restraints     152
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0300
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0327P)^2^+1.9459P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0743
_refine_ls_wR_factor_ref         0.0814
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4872
_reflns_number_total             5688
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02182_si_002.cif
_cod_data_source_block           OCon_PQ389
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_exptl_crystal_colour_modifier' value 'Light' was changed
to 'light' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_exptl_crystal_colour_primary' value 'Yellow' was changed
to 'yellow' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               4034566
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.917
_shelx_estimated_absorpt_t_min   0.867
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C14B-C13 = C14-C13
 1.5 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C14B) = Uanis(C14)
4. Rigid body (RIGU) restrains
 C16, C15, C19, C18, C17, C27, C26, C30, C29, C28, C16B, C15B, C19B, C18B,
 C17B, C27B, C26B, C30B, C29B, C28B
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
5. Others
 Sof(C15B)=Sof(C16B)=Sof(C17B)=Sof(C18B)=Sof(C19B)=Sof(C26B)=Sof(H26D)=
 Sof(H26E)=Sof(H26F)=Sof(C27B)=Sof(H27D)=Sof(H27E)=Sof(H27F)=Sof(C28B)=
 Sof(H28D)=Sof(H28E)=Sof(H28F)=Sof(C29B)=Sof(H29D)=Sof(H29E)=Sof(H29F)=
 Sof(C30B)=Sof(H30D)=Sof(H30E)=Sof(H30F)=1-FVAR(1)
 Sof(C15)=Sof(C16)=Sof(C17)=Sof(C18)=Sof(C19)=Sof(C26)=Sof(H26A)=Sof(H26B)=
 Sof(H26C)=Sof(C27)=Sof(H27A)=Sof(H27B)=Sof(H27C)=Sof(C28)=Sof(H28A)=Sof(H28B)=
 Sof(H28C)=Sof(C29)=Sof(H29A)=Sof(H29B)=Sof(H29C)=Sof(C30)=Sof(H30A)=Sof(H30B)=
 Sof(H30C)=FVAR(1)
 Sof(H13C)=Sof(H13D)=Sof(C14B)=Sof(H14D)=Sof(H14E)=Sof(H14F)=1-FVAR(2)
 Sof(H13A)=Sof(H13B)=Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(H14C)=FVAR(2)
6.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C13(H13C,H13D)
6.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C21(H21),
 C22(H22), C23(H23), C24(H24), C25(H25)
6.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C14B(H14D,H14E,H14F), C26(H26A,H26B,H26C), C26B(H26D,
 H26E,H26F), C27(H27A,H27B,H27C), C27B(H27D,H27E,H27F), C28(H28A,H28B,H28C),
 C28B(H28D,H28E,H28F), C29(H29A,H29B,H29C), C29B(H29D,H29E,H29F), C30(H30A,H30B,
 H30C), C30B(H30D,H30E,H30F)
;
_shelx_res_checksum              97480
_shelx_hkl_checksum              16016
_olex2_submission_special_instructions 'No special instructions were received'