Manganese-Catalyzed Divergent Markovnikov Addition and [2+2+2] Cycloaddition of 2-Carbonyl Indanone with Terminal Alkyne.
Thorve, Pradip Ramdas; Guru, Murali Mohan; Maji, Biplab; The Journal of organic chemistry 84 (2019) 8185–8193; doi:10.1021/acs.joc.9b01173

data_4034676
_publ_section_title
;
 Manganese-Catalyzed Divergent Markovnikov Addition and [2+2+2]
 Cycloaddition of 2-Carbonyl Indanone with Terminal Alkyne.
;
_journal_issue                   12
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8185
_journal_page_last               8193
_journal_paper_doi               10.1021/acs.joc.9b01173
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C28 H24 O3'
_chemical_formula_sum            'C28 H24 O3'
_chemical_formula_weight         408.47
_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
_audit_creation_date             2018-08-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.727(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4827(2)
_cell_length_b                   11.6842(3)
_cell_length_c                   20.2986(5)
_cell_measurement_reflns_used    7244
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      27.3020
_cell_measurement_theta_min      1.9850
_cell_volume                     2007.61(9)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9580
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.913
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -11.00 103.00   1.00    9.00    --   26.72  57.00   0.00  114
  2  \w    -58.00  70.00   1.00    9.00    --   26.72 -77.00 150.00  128
  3  \w   -119.00 -55.00   1.00    9.00    --  -23.50 178.00-120.00   64
  4  \w    -20.00  32.00   1.00    9.00    --  -23.50 -99.00  30.00   52
  5  \w    -49.00  16.00   1.00    9.00    --   26.72 -57.00-120.00   65
  6  \w    -57.00 114.00   1.00    9.00    --   26.72  19.00-120.00  171
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0356804000
_diffrn_orient_matrix_UB_12      -0.0549144000
_diffrn_orient_matrix_UB_13      -0.0026797000
_diffrn_orient_matrix_UB_21      0.0753704000
_diffrn_orient_matrix_UB_22      -0.0260486000
_diffrn_orient_matrix_UB_23      0.0047717000
_diffrn_orient_matrix_UB_31      -0.0076081000
_diffrn_orient_matrix_UB_32      -0.0006787000
_diffrn_orient_matrix_UB_33      0.0345684000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.913
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            16665
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.696
_diffrn_reflns_theta_min         2.011
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81734
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4287
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0444
_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^)+(0.0326P)^2^+1.8971P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1033
_refine_ls_wR_factor_ref         0.1074
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3770
_reflns_number_total             4287
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01173_si_002.cif
_cod_data_source_block           ptppa-51
_cod_database_code               4034676
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H N O'
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.975
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.63
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00L(H00A,H00C), C00T(H00E,H00F)
2.b Aromatic/amide H refined with riding coordinates:
 C004(H004), C00B(H00B), C00D(H00D), C00G(H00G), C00H(H00H), C00I(H00I),
 C00J(H00J), C00K(H00K), C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P),
 C00Q(H00Q), C00R(H00R), C00S(H00S), C00U(H00U)
2.c Idealised Me refined as rotating group:
 C00V(H00L,H00T,H00V)
2.d Idealised tetrahedral OH refined as rotating group:
 O001(H001)
;
_shelx_res_checksum              22208
_shelx_hkl_checksum              82237
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.294
_oxdiff_exptl_absorpt_empirical_full_min 0.734