A HMPA-H<sub>2</sub>O mediated oxygenative carbocyclization of 2-alkynylphenyl-substituted <i>p</i>-quinone methides to indenones.
Fatma, Shaheen; Ahmad, Feroz; Pankhade, Yogesh A.; Ranga, Pavit K.; Vijaya Anand, Ramasamy; Organic & biomolecular chemistry 22 (2024) 5891–5896; doi:10.1039/d4ob00966e

data_7160017
_publ_section_title
;
 A HMPA-H<sub>2</sub>O mediated oxygenative carbocyclization of
 2-alkynylphenyl-substituted <i>p</i>-quinone methides to indenones.
;
_journal_issue                   29
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5891
_journal_page_last               5896
_journal_paper_doi               10.1039/d4ob00966e
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         '2(C29 H30 O2)'
_chemical_formula_sum            'C58 H60 O4'
_chemical_formula_weight         821.06
_chemical_name_systematic        SF-28-II
_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
_audit_creation_date             2022-03-30
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-11-13 deposited with the CCDC.	2024-07-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.006(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6424(5)
_cell_length_b                   21.0313(8)
_cell_length_c                   19.3533(15)
_cell_measurement_reflns_used    5387
_cell_measurement_temperature    298
_cell_measurement_theta_max      30.6270
_cell_measurement_theta_min      2.7900
_cell_volume                     4738.7(5)
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.889
_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    -69.00 118.20   0.30   10.00    --   29.89  54.00-180.00  624
  2  \w    -69.00 118.20   0.30   10.00    --   29.89  54.00 -60.00  624
;
_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      -0.0497080000
_diffrn_orient_matrix_UB_12      0.0054518000
_diffrn_orient_matrix_UB_13      -0.0208791000
_diffrn_orient_matrix_UB_21      -0.0241852000
_diffrn_orient_matrix_UB_22      -0.0290841000
_diffrn_orient_matrix_UB_23      0.0116598000
_diffrn_orient_matrix_UB_31      -0.0257748000
_diffrn_orient_matrix_UB_32      0.0161566000
_diffrn_orient_matrix_UB_33      0.0275214000
_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  0.0493
_diffrn_reflns_av_unetI/netI     0.0594
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.889
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            44402
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.889
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         32.722
_diffrn_reflns_theta_min         2.610
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68796
_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            'dull dark red'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.151
_exptl_crystal_description       block
_exptl_crystal_F_000             1760
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     573
_refine_ls_number_reflns         15523
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.1724
_refine_ls_R_factor_gt           0.0835
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2014
_refine_ls_wR_factor_ref         0.2625
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6267
_reflns_number_total             15523
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00966e2.cif
_cod_data_source_block           sf-28-ii_rt
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_cell_measurement_temperature' value '298k' was changed to
'298' -- the value should be numeric and without a unit designator.

data item '_diffrn_ambient_temperature' value '298k' was changed to
'298' -- the value should be numeric and without a unit designator.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7160017.cif.
;
_cod_database_code               7160017
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_max   298k
_shelx_estimated_absorpt_t_min   298k
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C005(H005), C00E(H00E), C00I(H00I), C00L(H00L), C00Q(H00Q), C00W(H00W),
 C00Y(H00Y), C010(H010), C011(H011), C012(H012), C014(H014), C015(H015),
 C016(H016), C017(H017), C018(H018), C01A(H01y), C01L(H01s), C01M(H4),
 C01N(H01t), C01O(H01u), C01P(H5), C01Q(H6)
2.b Idealised Me refined as rotating group:
 C013(H01a,H01b,H01c), C019(H01v,H01w,H01x), C01B(H01d,H01e,H01f), C01C(H01g,
 H01h,H01i), C01D(H01j,H01k,H01l), C01E(H01z,H,Ha), C01F(H01,Hb,Hc), C01G(H1,Hd,
 He), C01H(H01m,H01n,H01o), C01I(H2,Hf,Hg), C01J(H01p,H01q,H01r), C01K(H3,Hh,Hi)
2.c Idealised tetrahedral OH refined as rotating group:
 O001(H001), O002(H002)
;
_shelx_res_checksum              56468
_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 1.515
_oxdiff_exptl_absorpt_empirical_full_min 0.765