Synthesis of Naphthopyrans <i>via</i> Formal (3+3)-Annulation of Propargylic (Aza)-<i>para</i>-Quinone Methides with Naphthols.
Zhang, Xiang-Zhi; Li, Bao Qiong; Qiu, Zong-Wang; Ma, Aijun; Peng, Jin-Bao; Du, Ji-Yuan; Feng, Na; Xu, Xue-Tao; Pan, Han-Peng; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c01791

data_4038877
_publ_section_title
;
 Synthesis of Naphthopyrans <i>via</i> Formal (3+3)-Annulation of
 Propargylic (Aza)-<i>para</i>-Quinone Methides with Naphthols.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01791
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         '3(C31 H21 Cl O2), H2 O'
_chemical_formula_sum            'C93 H65 Cl3 O7'
_chemical_formula_weight         1400.80
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                66.231(2)
_cell_angle_beta                 89.240(2)
_cell_angle_gamma                89.986(2)
_cell_formula_units_Z            1
_cell_length_a                   6.3659(2)
_cell_length_b                   17.1828(6)
_cell_length_c                   20.1654(8)
_cell_measurement_reflns_used    9887
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      72.4842
_cell_measurement_theta_min      2.8647
_cell_volume                     2018.46(13)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'Bruker Instrument Service vV6.2.9'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON II'
_diffrn_radiation_monochromator  'Helixos MX multilayer Optic'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0837
_diffrn_reflns_av_unetI/netI     0.0823
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            36186
_diffrn_reflns_theta_full        72.56
_diffrn_reflns_theta_max         72.56
_diffrn_reflns_theta_min         2.39
_diffrn_source                   'Ius Diamond'
_diffrn_source_type              Microfocus
_exptl_absorpt_coefficient_mu    1.449
_exptl_absorpt_correction_T_max  0.92
_exptl_absorpt_correction_T_min  0.49
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.152
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             730
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.609
_refine_diff_density_min         -0.315
_refine_ls_abs_structure_details
;

Flack x determined using 4022 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.062(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     952
_refine_ls_number_reflns         13489
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0619
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1051P)^2^+0.3965P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1647
_refine_ls_wR_factor_ref         0.1730
_reflns_number_gt                11952
_reflns_number_total             13489
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01791_si_002.cif
_cod_data_source_block           szh_1036
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               4038877
_shelx_res_checksum              78824
_shelx_hkl_checksum              97783
_shelx_fab_checksum              51070