Organocatalytic Asymmetric Sequential 1,6-Addition/Acetalization of 1-Oxotetralin-2-carbaldehyde to ortho-Hydroxyphenyl-Substituted para-Quinone Methides for Synthesis of Spiro-3,4-dihydrocoumarins.
Zhang, Zhi-Pei; Chen, Li; Li, Xin; Cheng, Jin-Pei; The Journal of organic chemistry 83 (2018) 2714–2724; doi:10.1021/acs.joc.7b03177

data_4034971
_publ_section_title
;
 Organocatalytic Asymmetric Sequential 1,6-Addition/Acetalization of
 1-Oxotetralin-2-carbaldehyde to ortho-Hydroxyphenyl-Substituted
 para-Quinone Methides for Synthesis of Spiro-3,4-dihydrocoumarins.
;
_journal_issue                   5
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2714
_journal_page_last               2724
_journal_paper_doi               10.1021/acs.joc.7b03177
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C33 H36 O4'
_chemical_formula_sum            'C33 H36 O4'
_chemical_formula_weight         496.62
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-09-26
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.13710(10)
_cell_length_b                   17.0065(2)
_cell_length_c                   30.3267(3)
_cell_measurement_reflns_used    34944
_cell_measurement_temperature    294.15
_cell_measurement_theta_max      79.1050
_cell_measurement_theta_min      2.9250
_cell_volume                     5743.97(10)
_computing_cell_refinement       'CrysAlisPro 1.171.39.3a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.3a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.3a (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_temperature      294.15
_diffrn_detector                 PILT
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_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   -125.00 -31.00   1.00    5.00    --  -35.00 -72.00 -72.00   94
  2  \w   -119.00 -29.00   1.00    5.00    --  -35.00 -44.00 -36.00   90
  3  \w    -50.00  40.00   1.00    5.00    --  -35.00  72.00 -36.00   90
  4  \w    -50.00  40.00   1.00    5.00    --  -35.00  43.00-144.00   90
  5  \w   -125.00 -20.00   1.00   20.00    -- -110.00  43.00 108.00  105
  6  \w   -200.00-110.00   1.00   20.00    -- -110.00 -72.00-180.00   90
  7  \w   -125.00 -32.00   1.00   20.00    -- -110.00  14.00   0.00   93
  8  \w   -125.00 -32.00   1.00   20.00    -- -110.00  72.00 -72.00   93
  9  \w   -115.00 -20.00   1.00   20.00    -- -110.00  43.00-144.00   95
 10  \w   -113.00 -20.00   1.00   20.00    -- -110.00  72.00   0.00   93
 11  \w   -191.00-101.00   1.00   20.00    -- -110.00 -44.00   0.00   90
 12  \w   -111.00 -20.00   1.00   20.00    -- -110.00  72.00-108.00   91
 13  \w   -187.00 -97.00   1.00   20.00    -- -110.00 -72.00 -36.00   90
 14  \w   -120.00 -30.00   1.00   20.00    -- -110.00  72.00 -36.00   90
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  "'Rigaku Xtalab P200"
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0281142000
_diffrn_orient_matrix_UB_12      -0.0884046000
_diffrn_orient_matrix_UB_13      -0.0039333000
_diffrn_orient_matrix_UB_21      -0.1250650000
_diffrn_orient_matrix_UB_22      -0.0197118000
_diffrn_orient_matrix_UB_23      0.0187191000
_diffrn_orient_matrix_UB_31      -0.0520212000
_diffrn_orient_matrix_UB_32      -0.0004213000
_diffrn_orient_matrix_UB_33      -0.0470605000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0161
_diffrn_reflns_av_unetI/netI     0.0113
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            49348
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.219
_diffrn_reflns_theta_min         2.914
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.586
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78634
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.3a (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    1.149
_exptl_crystal_description       block
_exptl_crystal_F_000             2128
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.130
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details
;
 Flack x determined using 5023 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(3)
_refine_ls_extinction_coef       0.00149(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/8 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     684
_refine_ls_number_reflns         12202
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0332
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0610P)^2^+0.2900P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.0971
_reflns_Friedel_coverage         0.794
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.969
_reflns_number_gt                11763
_reflns_number_total             12202
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b03177_si_002.cif
_cod_data_source_block           p20170922a
_cod_database_code               4034971
_shelx_shelxl_version_number     2014/8
_chemical_oxdiff_formula         C33H36O4
_shelx_estimated_absorpt_t_max   0.872
_shelx_estimated_absorpt_t_min   0.853
_reflns_odcompleteness_completeness 99.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     78.97
_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 Ternary CH refined with riding coordinates:
 C12(H12), C45(H45)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C43(H43A,H43B), C44(H44A,H44B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C8(H8), C14(H14), C15(H15), C16(H16), C17(H17), C21(H21),
 C25(H25), C38(H38), C40(H40), C41(H41), C47(H47), C48(H48), C49(H49), C50(H50),
  C54(H54), C58(H58)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C29(H29A,H29B,
 H29C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C), C33(H33A,H33B,H33C), C52(H52A,
 H52B,H52C), C60(H60A,H60B,H60C), C61(H61A,H61B,H61C), C62(H62A,H62B,H62C),
 C64(H64A,H64B,H64C), C65(H65A,H65B,H65C), C66(H66A,H66B,H66C)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4), O8(H8A)
;
_shelx_res_checksum              30216
_shelx_hkl_checksum              97447
_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 1.263
_oxdiff_exptl_absorpt_empirical_full_min 0.738