Chiral phosphoric acid catalyzed asymmetric addition of naphthols to para-quinone methides.
Wong, Yuk Fai; Wang, Zhaobin; Sun, Jianwei; Organic & biomolecular chemistry 14 (2016) 5751–5754; doi:10.1039/c6ob00125d

data_7154991
_publ_section_title
;
 Chiral phosphoric acid catalyzed asymmetric addition of naphthols to
 para-quinone methides.
;
_journal_issue                   24
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5751
_journal_page_last               5754
_journal_paper_doi               10.1039/c6ob00125d
_journal_volume                  14
_journal_year                    2016
_chemical_formula_moiety         'C21 H16 O2 S'
_chemical_formula_sum            'C21 H16 O2 S'
_chemical_formula_weight         332.40
_chemical_name_systematic
(S)-1-((4-Hydroxyphenyl)(thiophen-3-yl)methyl)naphthalen-2-ol
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2016-02-22
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-02-22 deposited with the CCDC.
2016-02-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2816(3)
_cell_length_b                   10.4360(3)
_cell_length_c                   15.0467(5)
_cell_measurement_reflns_used    5423
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.9790
_cell_measurement_theta_min      5.1500
_cell_volume                     1614.49(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3587
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details
;
  1 omega   41.00   91.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000  120.0000 50

  2 omega  -96.00   -2.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8203  125.0000  -30.0000 94

  3 omega -115.00  -12.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8203  -57.0000  150.0000 103

  4 omega -120.00   -7.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8203  -77.0000  -90.0000 113

  5 omega   50.00  177.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   15.0000   60.0000 127

  6 omega   92.00  175.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   45.0000  -60.0000 83

  7 omega  108.00  177.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  111.0000 -120.0000 69

  8 omega   56.00  140.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -61.0000 -180.0000 84

  9 omega   67.00  114.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703 -111.0000  -30.0000 47

 10 omega   36.00  128.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -61.0000  -60.0000 92

 11 omega   34.00  108.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -94.0000 -180.0000 74

 12 omega   27.00  108.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -94.0000   90.0000 81
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1343166000
_diffrn_orient_matrix_UB_12      -0.0195389000
_diffrn_orient_matrix_UB_13      -0.0439836000
_diffrn_orient_matrix_UB_21      -0.0665777000
_diffrn_orient_matrix_UB_22      0.0501160000
_diffrn_orient_matrix_UB_23      0.0846953000
_diffrn_orient_matrix_UB_31      0.0057769000
_diffrn_orient_matrix_UB_32      0.1372813000
_diffrn_orient_matrix_UB_33      -0.0370701000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8852
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         66.966
_diffrn_reflns_theta_min         5.158
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    1.852
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77575
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             696
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane and ethyl acetate'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.629
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details
;
 Flack x determined using 1090 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.056(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         2811
_refine_ls_number_restraints     100
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0570
_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^)+(0.0960P)^2^+1.3070P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1486
_refine_ls_wR_factor_ref         0.1503
_reflns_Friedel_coverage         0.742
_reflns_Friedel_fraction_full    0.985
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                2705
_reflns_number_total             2811
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob00125d2.cif
_cod_data_source_block           yong13a
_cod_depositor_comments          'Adding full bibliography for 7154991.cif.'
_cod_original_cell_volume        1614.50(8)
_cod_database_code               7154991
_chemical_oxdiff_formula         'S1 O2 ph3'
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 C23-C24 = C23A-C24A
 1.38 with sigma of 0.01
 O2-C24 = O2A-C24A
 1.4 with sigma of 0.02
 C25-C23
 2.4 with sigma of 0.02
 O2-C25
 2.43 with sigma of 0.04
 C25A-O2A
 2.43 with sigma of 0.04
 O2-C23
 2.43 with sigma of 0.04
 O2A-C23A
 2.43 with sigma of 0.04
 C26-C21 \\sim C25-C26 \\sim C24-C25 \\sim C23-C24 \\sim C22-C23 \\sim C22-C21
 with sigma of 0.02
 C26A-C21 \\sim C26A-C25A \\sim C25A-C24A \\sim C24A-C23A \\sim C23A-C22A \\sim
C22A-C21
 with sigma of 0.02
 O2-C24 \\sim O2A-C24A
 with sigma of 0.02
 O2-C25 \\sim O2-C23 \\sim O2A-C25A \\sim O2A-C23A
 with sigma of 0.02
3. Restrained planarity
 C21, C22, C23, C24, C25, C26
 with sigma of 0.1
 C21, C22A, C23A, C24A, C25A, C26A
 with sigma of 0.1
4. Rigid bond restraints
 C21, C22, C23, C24, C25, C26
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.002
5. Uiso/Uaniso restraints and constraints
C21 \\sim C22 \\sim C23 \\sim C24 \\sim C25 \\sim C26: within 1.5A with sigma
of 0.015 and sigma for terminal atoms of 0.008
Uanis(C26) = Uanis(C26A)
Uanis(C25) = Uanis(C25A)
Uanis(C22) = Uanis(C22A)
Uanis(C24) = Uanis(C24A)
Uanis(C23) = Uanis(C23A)
Uanis(O2) = Uanis(O2A)
6. Others
 Fixed Sof: O2(0.7) O2A(0.3) C22(0.7) H22(0.7) C22A(0.3) H22A(0.3) C23(0.7)
 H23(0.7) C23A(0.3) H23A(0.3) C24(0.7) C24A(0.3) C25(0.7) H25(0.7) C25A(0.3)
 H25A(0.3) C26(0.7) H26(0.7) C26A(0.3) H26A(0.3)
7.a Ternary CH refined with riding coordinates:
 C10(H10)
7.b Aromatic/amide H refined with riding coordinates:
 C1(H1A), C3(H3), C4(H4), C13(H13), C14(H14), C16(H16), C17(H17), C18(H18),
 C19(H19), C22(H22), C22A(H22A), C23(H23), C23A(H23A), C25(H25), C25A(H25A),
 C26(H26), C26A(H26A)
7.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_shelx_res_checksum              35741
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-02-22
_olex2_submission_special_instructions 'No special instructions were received'