An Approach to the Synthesis of 1-Propenylnaphthols and 3-Arylnaphtho[2,1-b]furans.
Huang, Jin; Wang, Wei; He, Hai-Yu; Jian, Lei; Fu, Hai-Yan; Zheng, Xue-Li; Chen, Hua; Li, Rui-Xiang; The Journal of organic chemistry 82 (2017) 2523–2534; doi:10.1021/acs.joc.6b02902

data_4032253
_publ_section_title
;
 An Approach to the Synthesis of 1-Propenylnaphthols and
 3-Arylnaphtho[2,1-b]furans.
;
_journal_issue                   5
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2523
_journal_page_last               2534
_journal_paper_doi               10.1021/acs.joc.6b02902
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C19 H16 O'
_chemical_formula_sum            'C19 H16 O'
_chemical_formula_weight         260.34
_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             2014-10-09
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.7995(19)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.75819(13)
_cell_length_b                   8.55021(16)
_cell_length_c                   24.5163(5)
_cell_measurement_reflns_used    4722
_cell_measurement_temperature    293
_cell_measurement_theta_max      72.4830
_cell_measurement_theta_min      5.4770
_cell_volume                     1403.54(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2013)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.9992
_diffrn_measured_fraction_theta_max 0.9992
_diffrn_measurement_details
;
  1 omega   17.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   38.0000  -90.0000 88

  2 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000  -60.0000 84

  3 omega  -31.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -77.0000  120.0000 94

  4 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000   60.0000 74

  5 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000    0.0000 84

  6 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000  -60.0000 67

  7 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000   30.0000 67

  8 omega  -35.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -19.0000   90.0000 101

  9 omega   38.00   91.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 53

 10 omega   91.00  176.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   90.0000 85

 11 omega   38.00   91.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 53

 12 omega   38.00  116.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -30.0000 78

 13 omega   39.00  109.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 70

 14 omega  100.00  178.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -90.0000 78

 15 omega   40.00   98.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 58

 16 omega   38.00   91.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 53

 17 omega   90.00  175.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  150.0000 85

 18 omega   39.00  109.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 70

 19 omega   39.00  109.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   90.0000 70

 20 omega   41.00  126.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000   90.0000 85

 21 omega   38.00   91.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 53

 22 omega   37.00  146.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000   90.0000 109

 23 omega   40.00  135.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -30.0000 95

 24 omega   20.00   73.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000 -180.0000 53
;
_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_UB_11      -0.0594362000
_diffrn_orient_matrix_UB_12      -0.0346963000
_diffrn_orient_matrix_UB_13      -0.0617250000
_diffrn_orient_matrix_UB_21      0.2211614000
_diffrn_orient_matrix_UB_22      0.0083604000
_diffrn_orient_matrix_UB_23      -0.0088158000
_diffrn_orient_matrix_UB_31      0.0221570000
_diffrn_orient_matrix_UB_32      -0.1765647000
_diffrn_orient_matrix_UB_33      0.0116904000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            12016
_diffrn_reflns_theta_full        67.0526
_diffrn_reflns_theta_max         67.05
_diffrn_reflns_theta_min         5.49
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.576
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86144
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
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    1.2319
_exptl_crystal_description
;
;
_exptl_crystal_F_000             553.6035
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.1898
_refine_diff_density_min         -0.2742
_refine_diff_density_rms         0.0525
_refine_ls_d_res_high            0.8372
_refine_ls_d_res_low             8.0651
_refine_ls_goodness_of_fit_ref   1.0658
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    30
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2490
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0658
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0514
_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^)+(0.0893P)^2^+0.1864P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1391
_refine_ls_wR_factor_ref         0.1445
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -8
_reflns_limit_k_max              10
_reflns_limit_k_min              0
_reflns_limit_l_max              29
_reflns_limit_l_min              0
_reflns_number_gt                2221
_reflns_number_total             2490
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo6b02902_si_002.cif
_cod_data_source_block           lrx-ww-03
_cod_depositor_comments
;

2020-08-18
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '0.33(C19 H16 O)'
_cod_original_formula_sum        'C6.333 H5.333 O0.333'
_cod_original_formula_units_Z    12
_cod_original_formula_weight     86.78
_cod_database_code               4032253
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
;
_olex2_submission_special_instructions 'No special instructions were received'