Organophosphine-Catalyzed Intramolecular Hydroacylation of Activated Alkynes
Mondal, Atanu; Hazra, Raju; Grover, Jagdeep; Raghu, Moluguri; Ramasastry, S. S. V.; ACS Catalysis 8 (2018) 2748–; doi:10.1021/acscatal.8b00397

data_4514400
_publ_section_title
;
 Organophosphine-Catalyzed Intramolecular Hydroacylation of Activated
 Alkynes
;
_journal_issue                   4
_journal_name_full               'ACS Catalysis'
_journal_page_first              2748
_journal_paper_doi               10.1021/acscatal.8b00397
_journal_volume                  8
_journal_year                    2018
_chemical_formula_moiety         'C27 H18 O2'
_chemical_formula_sum            'C27 H18 O2'
_chemical_formula_weight         374.44
_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'
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_primary     direct
_audit_creation_date             2017-12-29
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5375)
;
_cell_angle_alpha                90
_cell_angle_beta                 107.604(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.4516(9)
_cell_length_b                   7.5513(4)
_cell_length_c                   15.1340(8)
_cell_measurement_reflns_used    1674
_cell_measurement_temperature    293
_cell_measurement_theta_max      19.3310
_cell_measurement_theta_min      2.8030
_cell_volume                     1900.99(18)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.9506
_diffrn_measured_fraction_theta_max 0.9506
_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    -69.00 118.00   0.50   15.00    --   29.89  54.00-150.00  374
  2  \w    -69.00 118.00   0.50   15.00    --   29.89  54.00-120.00  374
  3  \w    -69.00 118.50   0.50   15.00    --   29.89  54.00  60.00  375
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0402358000
_diffrn_orient_matrix_UB_12      -0.0226903000
_diffrn_orient_matrix_UB_13      -0.0246396000
_diffrn_orient_matrix_UB_21      0.0058657000
_diffrn_orient_matrix_UB_22      -0.0853373000
_diffrn_orient_matrix_UB_23      0.0205420000
_diffrn_orient_matrix_UB_31      -0.0128182000
_diffrn_orient_matrix_UB_32      0.0320414000
_diffrn_orient_matrix_UB_33      0.0372729000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0828
_diffrn_reflns_av_unetI/netI     0.0963
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            26485
_diffrn_reflns_theta_full        32.8056
_diffrn_reflns_theta_max         32.81
_diffrn_reflns_theta_min         2.72
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82486
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.3082
_exptl_crystal_description       plate
_exptl_crystal_F_000             784.3725
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.5470
_refine_diff_density_min         -0.5330
_refine_diff_density_rms         0.1367
_refine_ls_d_res_high            0.6559
_refine_ls_d_res_low             7.4964
_refine_ls_goodness_of_fit_ref   1.0947
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    35
_refine_ls_number_parameters     262
_refine_ls_number_reflns         6711
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0947
_refine_ls_R_factor_all          0.2215
_refine_ls_R_factor_gt           0.0834
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1897
_refine_ls_wR_factor_ref         0.2728
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              22
_reflns_limit_h_min              -26
_reflns_limit_k_max              11
_reflns_limit_k_min              0
_reflns_limit_l_max              22
_reflns_limit_l_min              0
_reflns_number_gt                2401
_reflns_number_total             6711
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            cs8b00397_si_003.cif
_cod_data_source_block           AM-Naph-keto
_cod_depositor_comments
;
         Adding full bibliography for 4514400.cif.

2020-08-18
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        1900.98(18)
_cod_original_formula_moiety     '0.5(C27 H18 O2)'
_cod_original_formula_sum        'C13.5 H9 O'
_cod_original_formula_units_Z    8
_cod_original_formula_weight     187.22
_cod_database_code               4514400
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9a,H9b)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C24(H24), C21(H21), C20(H20), C15(H15), C25(H25), C23(H23),
 C16(H16), C28(H28), C17(H17), C18(H18), C22(H22), C27(H27), C29(H29), C26(H26),
  C5(H5)
;
_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 1.084
_oxdiff_exptl_absorpt_empirical_full_min 0.934