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_7159563
_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 H24 O3'
_chemical_formula_sum            'C26 H24 O3'
_chemical_formula_weight         384.45
_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             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                90
_cell_angle_beta                 108.7630(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.2499(8)
_cell_length_b                   8.8129(3)
_cell_length_c                   20.6678(6)
_cell_measurement_reflns_used    9835
_cell_measurement_temperature    296
_cell_measurement_theta_max      22.887
_cell_measurement_theta_min      2.535
_cell_volume                     4182.2(2)
_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
_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 0.999
_diffrn_measured_fraction_theta_max 0.997
_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  0.1021
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            140566
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.108
_diffrn_reflns_theta_min         2.475
_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    0.079
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.5948
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0921 before and 0.0830 after correction.
The Ratio of minimum to maximum transmission is 0.7981.
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    1.221
_exptl_crystal_description       block
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.0050(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     672
_refine_ls_number_reflns         8279
_refine_ls_number_restraints     540
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0931
_refine_ls_R_factor_gt           0.0577
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0562P)^2^+1.5661P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1306
_refine_ls_wR_factor_ref         0.1503
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5576
_reflns_number_total             8279
_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_database_code               7159563
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.990
_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
 O3A-C13A \\sim O1-C2
 with sigma of 0.02
 C11A-C12A \\sim C11A-C1
 with sigma of 0.02
 C12A-C13A \\sim C1-C2
 with sigma of 0.02
 C13A-C14A \\sim C2-C3
 with sigma of 0.02
 C14A-C15A \\sim C3-C4
 with sigma of 0.02
 C14A-C19A \\sim C3-C8
 with sigma of 0.02
 C15A-C16A \\sim C4-C5
 with sigma of 0.02
 C16A-C17A \\sim C5-C6
 with sigma of 0.02
 C17A-C18A \\sim C6-C7
 with sigma of 0.02
 C18A-C19A \\sim C7-C8
 with sigma of 0.02
 O3A-C12A \\sim O1-C1
 with sigma of 0.04
 O3A-C14A \\sim O1-C3
 with sigma of 0.04
 C11A-C13A \\sim C11A-C2
 with sigma of 0.04
 C12A-C14A \\sim C1-C3
 with sigma of 0.04
 C13A-C15A \\sim C2-C4
 with sigma of 0.04
 C13A-C19A \\sim C2-C8
 with sigma of 0.04
 C14A-C16A \\sim C3-C5
 with sigma of 0.04
 C14A-C18A \\sim C3-C7
 with sigma of 0.04
 C15A-C17A \\sim C4-C6
 with sigma of 0.04
 C15A-C19A \\sim C4-C8
 with sigma of 0.04
 C16A-C18A \\sim C5-C7
 with sigma of 0.04
 C17A-C19A \\sim C6-C8
 with sigma of 0.04
 O3B-C13B \\sim O3C-C13C
 with sigma of 0.02
 C11B-C12B \\sim C11B-C12C
 with sigma of 0.02
 C12B-C13B \\sim C12C-C13C
 with sigma of 0.02
 C13B-C14B \\sim C13C-C14C
 with sigma of 0.02
 C14B-C15B \\sim C14C-C15C
 with sigma of 0.02
 C14B-C19B \\sim C14C-C19C
 with sigma of 0.02
 C15B-C16B \\sim C15C-C16C
 with sigma of 0.02
 C16B-C17B \\sim C16C-C17C
 with sigma of 0.02
 C17B-C18B \\sim C17C-C18C
 with sigma of 0.02
 C18B-C19B \\sim C18C-C19C
 with sigma of 0.02
 O3B-C12B \\sim O3C-C12C
 with sigma of 0.04
 O3B-C14B \\sim O3C-C14C
 with sigma of 0.04
 C11B-C13B \\sim C11B-C13C
 with sigma of 0.04
 C12B-C14B \\sim C12C-C14C
 with sigma of 0.04
 C13B-C15B \\sim C13C-C15C
 with sigma of 0.04
 C13B-C19B \\sim C13C-C19C
 with sigma of 0.04
 C14B-C16B \\sim C14C-C16C
 with sigma of 0.04
 C14B-C18B \\sim C14C-C18C
 with sigma of 0.04
 C15B-C17B \\sim C15C-C17C
 with sigma of 0.04
 C15B-C19B \\sim C15C-C19C
 with sigma of 0.04
 C16B-C18B \\sim C16C-C18C
 with sigma of 0.04
 C17B-C19B \\sim C17C-C19C
 with sigma of 0.04
3. Restrained planarity
 C13A, C14A, C15A, C16A, C17A, C18A, C19A
 with sigma of 0.1
 C2, C3, C4, C5, C6, C7, C8
 with sigma of 0.1
 C13B, C14B, C15B, C16B, C17B, C18B, C19B
 with sigma of 0.1
 C13C, C14C, C15C, C16C, C17C, C18C, C19C
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
Uanis(O3A) \\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(O1) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C3) \\sim
Ueq, Uanis(C4) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C7)
\\sim Ueq, Uanis(C8) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms
of 0.02
Uanis(O3B) \\sim Ueq, Uanis(C12B) \\sim Ueq, Uanis(C13B) \\sim Ueq, Uanis(C14B)
\\sim Ueq, Uanis(C15B) \\sim Ueq, Uanis(C16B) \\sim Ueq, Uanis(C17B) \\sim Ueq,
Uanis(C18B) \\sim Ueq, Uanis(C19B) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(O3C) \\sim Ueq, Uanis(C12C) \\sim Ueq, Uanis(C13C) \\sim Ueq, Uanis(C14C)
\\sim Ueq, Uanis(C15C) \\sim Ueq, Uanis(C16C) \\sim Ueq, Uanis(C17C) \\sim Ueq,
Uanis(C18C) \\sim Ueq, Uanis(C19C) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
5. Rigid body (RIGU) restrains
 O3A, C13A, C14A, C15A, C16A, C17A, C18A, C19A, C12A, C11A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C11A, O1, C1, C2, C3, C4, C5, C6, C7, C8
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 O3B, C11B, C12B, C13B, C14B, C15B, C16B, C17B, C18B, C19B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C11B, O3C, C12C, C13C, C14C, C15C, C16C, C17C, C18C, C19C
 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(O1)=Sof(H1)=Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(C2)=Sof(H2)=
 Sof(C3)=Sof(C4)=Sof(H4)=Sof(C5)=Sof(H5)=Sof(C6)=Sof(H6)=Sof(C7)=Sof(H7)=
 Sof(C8)=Sof(H8)=1-FVAR(1)
 Sof(O3A)=Sof(H3A)=Sof(H11A)=Sof(H11B)=Sof(C12A)=Sof(H12A)=Sof(H12B)=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)=FVAR(1)
 Sof(H11G)=Sof(H11H)=Sof(O3C)=Sof(H3C)=Sof(C12C)=Sof(H12E)=Sof(H12F)=Sof(C13C)=
 Sof(H13C)=Sof(C14C)=Sof(C19C)=Sof(H19C)=Sof(C18C)=Sof(H18C)=Sof(C17C)=
 Sof(H17C)=Sof(C16C)=Sof(H16C)=Sof(C15C)=Sof(H15C)=1-FVAR(2)
 Sof(O3B)=Sof(H3B)=Sof(H11E)=Sof(H11F)=Sof(C12B)=Sof(H12C)=Sof(H12D)=Sof(C13B)=
 Sof(H13B)=Sof(C14B)=Sof(C15B)=Sof(H15B)=Sof(C16B)=Sof(H16B)=Sof(C17B)=
 Sof(H17B)=Sof(C18B)=Sof(H18B)=Sof(C19B)=Sof(H19B)=FVAR(2)
7.a Ternary CH refined with riding coordinates:
 C13A(H13A), C13B(H13B), C2(H2), C13C(H13C)
7.b Secondary CH2 refined with riding coordinates:
 C11A(H11A,H11B), C11A(H11C,H11D), C11B(H11E,H11F), C11B(H11G,H11H), C12A(H12A,
 H12B), C12B(H12C,H12D), C1(H1A,H1B), C12C(H12E,H12F)
7.c Aromatic/amide H refined with riding coordinates:
 C2A(H2AA), C2B(H2BA), C4A(H4A), C4B(H4B), C5A(H5A), C5B(H5B), C10A(H10A),
 C10B(H10B), C15A(H15A), C15B(H15B), C16A(H16A), C16B(H16B), C17A(H17A),
 C17B(H17B), C18A(H18A), C18B(H18B), C19A(H19A), C19B(H19B), C22A(H22A),
 C22B(H22B), C23A(H23A), C23B(H23B), C24A(H24A), C24B(H24B), C25A(H25A),
 C25B(H25B), C26A(H26A), C26B(H26B), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8),
 C19C(H19C), C18C(H18C), C17C(H17C), C16C(H16C), C15C(H15C)
7.d Fitted hexagon refined as free rotating group:
 C3(C4,C5,C6,C7,C8), C14C(C19C,C18C,C17C,C16C,C15C)
7.e Idealised Me refined as rotating group:
 C20A(H20A,H20B,H20C), C20B(H20D,H20E,H20F)
7.f Idealised tetrahedral OH refined as rotating group:
 O2A(H2A), O2B(H2B), O3A(H3A), O3B(H3B), O1(H1), O3C(H3C)
;
_shelx_res_checksum              38402
_shelx_hkl_checksum              90242
_olex2_submission_special_instructions 'No special instructions were received'