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_1558508
_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 H16 O2'
_chemical_formula_sum            'C15 H16 O2'
_chemical_formula_weight         228.28
_chemical_name_systematic        3-Butyl-2-hydroxy-1-naphthaldehyde
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-12-03
_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                 99.928(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.3890(5)
_cell_length_b                   12.5456(4)
_cell_length_c                   7.5297(3)
_cell_measurement_reflns_used    1886
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.5170
_cell_measurement_theta_min      4.2470
_cell_volume                     1152.80(8)
_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      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 0.984
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details
;
  1 omega  -90.00  -57.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.3887 -178.0000   90.0000 33

  2 omega  -18.00    9.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       15.8574  -57.0000 -120.0000 27

  3 omega  -42.00   83.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       15.8574   19.0000   60.0000 125
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Mo at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0238325000
_diffrn_orient_matrix_UB_12      0.0462614000
_diffrn_orient_matrix_UB_13      0.0311769000
_diffrn_orient_matrix_UB_21      0.0515934000
_diffrn_orient_matrix_UB_22      0.0145084000
_diffrn_orient_matrix_UB_23      0.0506389000
_diffrn_orient_matrix_UB_31      0.0121657000
_diffrn_orient_matrix_UB_32      0.0290670000
_diffrn_orient_matrix_UB_33      -0.0749190000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4219
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_min         3.191
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49398
_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_colour_primary    colourless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane and hexane'
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2233
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0434
_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^)+(0.0600P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1029
_refine_ls_wR_factor_ref         0.1124
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1680
_reflns_number_total             2233
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc02502j2.cif
_cod_data_source_block           an1molt
_cod_original_cell_volume        1152.81(8)
_cod_database_code               1558508
_reflns_odcompleteness_completeness 99.03
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.04
_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:
 C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C15(H15)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              5934
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-12-03
_olex2_submission_special_instructions 'No special instructions were received'