Selective electrophilic cyclization of <i>ortho</i>-carbonylarylacetylenols for the synthesis of cyclopenta[<i>a</i>]naphthalenol and 2-phenylnaphthalen-1-ol analogs.
Jantrapirom, Jantra; Yongpanich, Phornphan; Tummatorn, Jumreang; Chainok, Kittipong; Jiajaroen, Suwadee; Thongsornkleeb, Charnsak; Ruchirawat, Somsak; Organic & biomolecular chemistry 21 (2023) 8500–8515; doi:10.1039/d3ob01344h

data_7159565
_publ_section_title
;
 Selective electrophilic cyclization of
 <i>ortho</i>-carbonylarylacetylenols for the synthesis of
 cyclopenta[<i>a</i>]naphthalenol and 2-phenylnaphthalen-1-ol analogs.
;
_journal_issue                   42
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8500
_journal_page_last               8515
_journal_paper_doi               10.1039/d3ob01344h
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C26 H22 O4'
_chemical_formula_sum            'C26 H22 O4'
_chemical_formula_weight         398.43
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-06-09
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-06-09 deposited with the CCDC.	2023-09-06 downloaded from the CCDC.
;
_cell_angle_alpha                80.213(10)
_cell_angle_beta                 76.589(9)
_cell_angle_gamma                67.977(9)
_cell_formula_units_Z            2
_cell_length_a                   8.672(2)
_cell_length_b                   10.126(3)
_cell_length_c                   12.865(4)
_cell_measurement_reflns_used    8330
_cell_measurement_temperature    296
_cell_measurement_theta_max      26.128
_cell_measurement_theta_min      2.601
_cell_volume                     1014.4(5)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296.00
_diffrn_detector                 'Bruker PHOTON 200 area detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_detector_type            'PHOTON II area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'four-circle KAPPA diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST CMOS PHOTON II'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_collimation    '0.5 mm'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0744
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            42799
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.486
_diffrn_reflns_theta_min         2.578
_diffrn_source                   'sealed x-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_target            Mo
_diffrn_source_type              Mo
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6370
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0803 before and 0.0720 after correction.
The Ratio of minimum to maximum transmission is 0.8546.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'light orange'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_description       block
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     356
_refine_ls_number_reflns         4186
_refine_ls_number_restraints     270
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0917
_refine_ls_R_factor_gt           0.0732
_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^)+(0.0544P)^2^+0.7354P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1588
_refine_ls_wR_factor_ref         0.1683
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3384
_reflns_number_total             4186
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01344h2.cif
_cod_data_source_block           4aa'
_cod_depositor_comments
'Adding full bibliography for 7159563--7159565.cif.'
_cod_original_cell_volume        1014.3(5)
_cod_database_code               7159565
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.979
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O4-C13 \\sim O4A-C13A
 with sigma of 0.02
 C11-C12 \\sim C11-C12A
 with sigma of 0.02
 C12-C13 \\sim C12A-C13A
 with sigma of 0.02
 C14-C18 \\sim C14A-C18A
 with sigma of 0.04
 C15-C19 \\sim C15A-C19A
 with sigma of 0.04
 C13-C14 \\sim C13A-C14A
 with sigma of 0.02
 C14-C15 \\sim C14A-C15A
 with sigma of 0.02
 C14-C19 \\sim C14A-C19A
 with sigma of 0.02
 C15-C16 \\sim C15A-C16A
 with sigma of 0.02
 C16-C17 \\sim C16A-C17A
 with sigma of 0.02
 C17-C18 \\sim C17A-C18A
 with sigma of 0.02
 C14-C16 \\sim C14A-C16A
 with sigma of 0.04
 C18-C19 \\sim C18A-C19A
 with sigma of 0.02
 C15-C17 \\sim C15A-C17A
 with sigma of 0.04
 O4-C12 \\sim O4A-C12A
 with sigma of 0.04
 C16-C18 \\sim C16A-C18A
 with sigma of 0.04
 O4-C14 \\sim O4A-C14A
 with sigma of 0.04
 C17-C19 \\sim C17A-C19A
 with sigma of 0.04
 C11-C13 \\sim C11-C13A
 with sigma of 0.04
 C12-C14 \\sim C12A-C14A
 with sigma of 0.04
 C13-C15 \\sim C13A-C15A
 with sigma of 0.04
 C13-C19 \\sim C13A-C19A
 with sigma of 0.04
3. Restrained planarity
 C13A, C14A, C15A, C16A, C17A, C18A, C19A
 with sigma of 0.1
 C13, C14, C19, C18, C17, C16, C15
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
Uanis(O4A) \\sim Ueq, Uanis(C12A) \\sim Ueq, Uanis(C13A) \\sim Ueq, Uanis(C14A)
\\sim Ueq, Uanis(C15A) \\sim Ueq, Uanis(C16A) \\sim Ueq, Uanis(C17A) \\sim Ueq,
Uanis(C18A) \\sim Ueq, Uanis(C19A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(O4) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C14)
\\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C17) \\sim Ueq,
Uanis(C18) \\sim Ueq, Uanis(C19) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
5. Rigid body (RIGU) restrains
 C11, O4A, C12A, C13A, C14A, C15A, C16A, C17A, C18A, C19A
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 O4, C11, C12, C13, C14, C15, C16, C17, C18, C19
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
6. Others
 Sof(H11C)=Sof(H11D)=Sof(O4A)=Sof(H4A)=Sof(C12A)=Sof(H12C)=Sof(H12D)=Sof(C13A)=
 Sof(H13A)=Sof(C14A)=Sof(C15A)=Sof(H15A)=Sof(C16A)=Sof(H16A)=Sof(C17A)=
 Sof(H17A)=Sof(C18A)=Sof(H18A)=Sof(C19A)=Sof(H19A)=1-FVAR(1)
 Sof(O4)=Sof(H4)=Sof(H11A)=Sof(H11B)=Sof(C12)=Sof(H12A)=Sof(H12B)=Sof(C13)=
 Sof(H13)=Sof(C14)=Sof(C15)=Sof(H15)=Sof(C16)=Sof(H16)=Sof(C17)=Sof(H17)=
 Sof(C18)=Sof(H18)=Sof(C19)=Sof(H19)=FVAR(1)
7.a Ternary CH refined with riding coordinates:
 C13(H13), C13A(H13A)
7.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C11(H11C,H11D), C12(H12A,H12B), C12A(H12C,H12D)
7.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19),
 C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), C15A(H15A), C16A(H16A),
 C17A(H17A), C18A(H18A), C19A(H19A)
7.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
7.e Idealised tetrahedral OH refined as rotating group:
 O4(H4), O4A(H4A)
;
_shelx_res_checksum              2802
_shelx_hkl_checksum              74944
_olex2_submission_special_instructions 'No special instructions were received'