Rh(iii)-Catalyzed regioselective C–H [4 + 2] C-annulation of vinyl enaminones with alkynes to form polysubstituted salicylaldehydes
Zhao, Yinsong; Zheng, Qinze; Yu, Chuangui; Liu, Zheng; Wang, Deping; You, Jingsong; Gao, Ge; Organic Chemistry Frontiers 5 (2018) 2875–; doi:10.1039/C8QO00759D

data_1554405
_publ_section_title
;
 Rh(iii)-Catalyzed regioselective C--H [4 + 2] C-annulation of vinyl
 enaminones with alkynes to form polysubstituted salicylaldehydes
;
_journal_issue                   19
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2875
_journal_paper_doi               10.1039/C8QO00759D
_journal_volume                  5
_journal_year                    2018
_chemical_formula_moiety         'C28 H24 O5'
_chemical_formula_sum            'C28 H24 O5'
_chemical_formula_weight         440.47
_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     direct
_audit_creation_date             2018-06-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_audit_update_record
;
2018-06-24 deposited with the CCDC.
2018-09-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.141(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5523(4)
_cell_length_b                   9.8572(3)
_cell_length_c                   23.9209(9)
_cell_measurement_reflns_used    5210
_cell_measurement_temperature    296.83(10)
_cell_measurement_theta_max      72.6460
_cell_measurement_theta_min      4.4280
_cell_volume                     2223.76(14)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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      air
_diffrn_ambient_temperature      296.83(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.979
_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   -104.00  -9.00   1.00    1.00    --  -36.04 -77.00 -60.00   95
  2  \w    -33.00  55.00   1.00    1.00    --   36.04 -38.00 -90.00   88
  3  \w     17.00 105.00   1.00    1.00    --   36.04  38.00 150.00   88
  4  \w      1.00  75.00   1.00    1.00    --   36.04 -99.00 150.00   74
  5  \w      7.00 107.00   1.00    1.00    --   36.04  19.00  90.00  100
  6  \w    100.00 178.00   1.00    1.00    --  108.71 111.00-150.00   78
  7  \w     40.00 126.00   1.00    1.00    --  108.71 -45.00-150.00   86
  8  \w    100.00 178.00   1.00    1.00    --  108.71 111.00-120.00   78
  9  \w     39.00 109.00   1.00    1.00    --  108.71 -94.00  30.00   70
 10  \w     91.00 177.00   1.00    1.00    --  108.71  45.00 -30.00   86
 11  \w     87.00 178.00   1.00    1.00    --  108.71  30.00  30.00   91
 12  \w     40.00 126.00   1.00    1.00    --  108.71 -45.00 -60.00   86
 13  \w   -108.00 -37.00   1.00    1.00    --  -36.04-176.00 -44.00   71
 14  \w   -104.00  -9.00   1.00    1.00    --  -36.04 -77.00   0.00   95
 15  \w     59.00 107.00   1.00    1.00    --   36.04 176.00 -38.00   48
 16  \w     23.00  66.00   1.00    1.00    --   36.04-125.00  30.00   43
 17  \w     17.00 105.00   1.00    1.00    --   36.04  38.00-120.00   88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0878474000
_diffrn_orient_matrix_UB_12      -0.0093989000
_diffrn_orient_matrix_UB_13      0.0485737000
_diffrn_orient_matrix_UB_21      -0.1265427000
_diffrn_orient_matrix_UB_22      -0.0559686000
_diffrn_orient_matrix_UB_23      -0.0415297000
_diffrn_orient_matrix_UB_31      0.0542494000
_diffrn_orient_matrix_UB_32      -0.1457384000
_diffrn_orient_matrix_UB_33      0.0128854000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0683
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            11928
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.120
_diffrn_reflns_theta_min         3.743
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.729
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97383
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.553
_refine_diff_density_rms         0.117
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         4353
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.124
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0673
_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^)+(0.1431P)^2^+0.6952P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2147
_refine_ls_wR_factor_ref         0.2311
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3643
_reflns_number_total             4353
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00759d2.cif
_cod_data_source_block           yjs-zys-2817
_cod_original_cell_volume        2223.76(15)
_cod_database_code               1554405
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C008(H008), C00A(H00A), C00F(H00F), C00I(H00I), C00J(H00J), C00K(H00K),
 C00L(H00L), C00M(H00M), C00N(H00N), C00P(H00P), C00Q(H00Q), C00S(H00S),
 C00T(H00T), C00U(H00U)
2.b Idealised Me refined as rotating group:
 C00V(H00B,H00C,H00D), C00W(H00E,H00G,H00H), C00X(H00O,H00R,H00V)
2.c Idealised tetrahedral OH refined as rotating group:
 O001(H001)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.728
_oxdiff_exptl_absorpt_empirical_full_min 0.678