Brønsted acid-catalyzed aromatic annulation of alkoxyallenes with naphthols: a reaction sequence to larger π-conjugated naphthopyrans with aggregation-induced emission characters
Zhang, Jinlong; Zhu, Lu; Shen, Kang; Yang, Huameng; Hang, Xiao-Chun; Jiang, Gaoxi; Chemical Science  (2019) –; doi:10.1039/C8SC03837F

data_1550512
_publ_section_title
;
 Br\/onsted acid-catalyzed aromatic annulation of alkoxyallenes with
 naphthols: a reaction sequence to larger \p-conjugated naphthopyrans with
 aggregation-induced emission characters
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C8SC03837F
_journal_year                    2019
_chemical_formula_sum            'C41 H28 O2'
_chemical_formula_weight         552.63
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-08-14 deposited with the CCDC.
2018-11-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7427(14)
_cell_length_b                   13.5639(19)
_cell_length_c                   21.658(3)
_cell_measurement_reflns_used    4169
_cell_measurement_temperature    296(2)
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_cell_measurement_theta_min      2.57
_cell_volume                     2862.1(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART APEX II'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 'fine-focus sealed tube'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       '\w scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
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_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13529
_diffrn_reflns_point_group_measured_fraction_full 0.911
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_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            red
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_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
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_exptl_transmission_factor_min   0.5345
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 1419 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   2.7(7)
_refine_ls_extinction_coef       0.0041(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.999
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_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0419
_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^)+(0.0500P)^2^+0.7086P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1020
_refine_ls_wR_factor_ref         0.1106
_reflns_Friedel_coverage         0.776
_reflns_Friedel_fraction_full    0.820
_reflns_Friedel_fraction_max     0.820
_reflns_number_gt                3774
_reflns_number_total             4566
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8sc03837f2.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_cell_volume        2862.0(7)
_cod_database_code               1550512
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.970
_shelx_estimated_absorpt_t_max   0.977
_shelx_res_checksum              99658