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_4034567
_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         'C20 H18 O4 S'
_chemical_formula_sum            'C20 H18 O4 S'
_chemical_formula_weight         354.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-01-11
_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                 104.003(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0617(8)
_cell_length_b                   10.3249(8)
_cell_length_c                   15.3097(11)
_cell_measurement_reflns_used    4157
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      25.236
_cell_measurement_theta_min      2.402
_cell_volume                     1696.6(2)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2014.11-0 (Bruker, 2014)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker X8 APEX II'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_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  0.0352
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11890
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.381
_diffrn_reflns_theta_min         2.737
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_T_max  0.0916
_exptl_absorpt_correction_T_min  0.0635
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0460 before and 0.0393 after correction. The Ratio of minimum to maximum transmission is 0.6932. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            'Light Yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_description       Needle
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.297
_exptl_crystal_size_mid          0.086
_exptl_crystal_size_min          0.074
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3094
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0406
_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^)+(0.0357P)^2^+1.1105P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0894
_refine_ls_wR_factor_ref         0.0952
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2529
_reflns_number_total             3094
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02182_si_002.cif
_cod_data_source_block           PQ_0313
_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               4034567
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.939
_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. Shared sites
{C5B, C5}
{C2B, C2}
3. Uiso/Uaniso restraints and constraints
Uanis(C5) = Uanis(C5B)
Uanis(C5B) = Uanis(C5)
Uanis(C2B) = Uanis(C2)
4. Others
 Fixed Sof: C2(0.5) H2(0.5) C2B(0.5) H2BA(0.5) H2BB(0.5) C5(0.5) H5A(0.5)
 H5B(0.5) C5B(0.5) H5BA(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C2B(H2BA,H2BB), C5(H5A,H5B), C13(H13A,H13B)
5.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5B(H5BA), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C16(H16),
 C17(H17), C18(H18), C19(H19), C20(H20)
5.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_shelx_res_checksum              70500
_shelx_hkl_checksum              86812
_olex2_submission_special_instructions 'No special instructions were received'