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_7159564
_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 H21 Cl O2'
_chemical_formula_sum            'C26 H21 Cl O2'
_chemical_formula_weight         400.88
_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   mixed
_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                67.915(2)
_cell_angle_beta                 80.436(2)
_cell_angle_gamma                65.8900(10)
_cell_formula_units_Z            2
_cell_length_a                   8.9346(5)
_cell_length_b                   10.7463(6)
_cell_length_c                   11.7878(6)
_cell_measurement_reflns_used    9388
_cell_measurement_temperature    100
_cell_measurement_theta_max      72.180
_cell_measurement_theta_min      5.425
_cell_volume                     957.15(9)
_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      100
_diffrn_detector                 'PHOTON 100 CMOS DETECTOR'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_detector_type            'PHOTON 100 CMOS'
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device       '\k-Geometry Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_collimation    '0.6 mm'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            28344
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.481
_diffrn_reflns_theta_min         4.798
_diffrn_source                   'X-ray tube'
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_target            Cu
_diffrn_source_type              'Micro focus tube'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    1.922
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.4568
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1210 before and 0.0945 after correction.
The Ratio of minimum to maximum transmission is 0.6062.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_description       block
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3733
_refine_ls_number_restraints     17
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0429
_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^)+(0.0686P)^2^+0.4215P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1200
_refine_ls_wR_factor_ref         0.1204
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3642
_reflns_number_total             3733
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01344h2.cif
_cod_data_source_block           kcjt_py
_cod_depositor_comments
'Adding full bibliography for 7159563--7159565.cif.'
_cod_database_code               7159564
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.963
_shelx_estimated_absorpt_t_min   0.927
_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
2. Restrained distances
 O1-H1B = O1-H1
 0.84 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(O1) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(O1) \\sim Ueq, Uanis(C2) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 C2
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 O1, C2
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Fixed Sof: H1(0.5) H1B(0.5)
6.a Ternary CH refined with riding coordinates:
 C13(H13)
6.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B)
6.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19),
 C21(H21), C22(H22), C24(H24), C25(H25)
6.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C)
;
_shelx_res_checksum              45430
_shelx_hkl_checksum              21244
_olex2_submission_special_instructions 'No special instructions were received'