Benzannulation of Isobenzopyryliums with Electron-Rich Alkynes: A Modular Access to β-Functionalized Naphthalenes
Wu, An; Qian, Hui; Zhao, Wanxiang; Sun, Jianwei; Chemical Science  (2020) –; doi:10.1039/D0SC02502J

data_1558509
_publ_section_title
;
 Benzannulation of Isobenzopyryliums with Electron-Rich Alkynes: A Modular
 Access to \b-Functionalized Naphthalenes
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC02502J
_journal_year                    2020
_chemical_formula_moiety         'C15 H15 F O2'
_chemical_formula_sum            'C15 H15 F O2'
_chemical_formula_weight         246.27
_chemical_name_systematic        3-Butyl-7-fluoro-2-hydroxy-1-naphthaldehyde
_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
_audit_creation_date             2016-01-14
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2020-04-09 deposited with the CCDC.	2020-07-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.872(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.37471(14)
_cell_length_b                   19.0645(3)
_cell_length_c                   9.32895(18)
_cell_measurement_reflns_used    2687
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      75.3120
_cell_measurement_theta_min      5.6040
_cell_volume                     1217.19(4)
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3587
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details
;
  1 omega   33.00   76.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000  150.0000 43

  2 omega   87.00  178.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   45.0000  -60.0000 91

  3 omega  118.00  177.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  111.0000   90.0000 59

  4 omega   35.00   77.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000 -180.0000 42

  5 omega   36.00  105.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -94.0000  -90.0000 69

  6 omega   32.00  113.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703 -111.0000 -150.0000 81

  7 omega   24.00   98.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       40.9453 -125.0000  -90.0000 74

  8 omega -108.00    1.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9453  -19.0000 -120.0000 109
;
_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      -0.1640809000
_diffrn_orient_matrix_UB_12      0.0335222000
_diffrn_orient_matrix_UB_13      -0.1382161000
_diffrn_orient_matrix_UB_21      0.0801803000
_diffrn_orient_matrix_UB_22      0.0734493000
_diffrn_orient_matrix_UB_23      0.0593051000
_diffrn_orient_matrix_UB_31      0.1315137000
_diffrn_orient_matrix_UB_32      -0.0028893000
_diffrn_orient_matrix_UB_33      -0.0952124000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0121
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3701
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         66.975
_diffrn_reflns_theta_min         4.639
_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    0.810
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86813
_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            colourless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             520
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: chloromethane and hexane'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2115
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0307
_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^)+(0.0500P)^2^+0.2410P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0798
_refine_ls_wR_factor_ref         0.0814
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1980
_reflns_number_total             2115
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc02502j2.cif
_cod_data_source_block           an3cult
_cod_database_code               1558509
_reflns_odcompleteness_completeness 98.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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 Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C7(H7), C8(H8), C10(H10)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              52885
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-01-13
_olex2_submission_special_instructions 'No special instructions were received'