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, Xiaochun; Jiang, Gaoxi; Chemical Science  (2019) –; doi:10.1039/C8SC03837F

data_1550180
_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_moiety         'C36 H34 N2 Ru2, C6 H6'
_chemical_formula_sum            'C42 H40 N2 Ru2'
_chemical_formula_weight         774.90
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2017-03-01
_audit_creation_method
;
Olex2 1.2
(compiled 2017.02.23 svn.r3390 for OlexSys, GUI svn.r5320)
;
_audit_update_record
;
2017-03-01 deposited with the CCDC.
2018-11-02 downloaded from the CCDC.
;
_cell_angle_alpha                83.467(3)
_cell_angle_beta                 80.563(2)
_cell_angle_gamma                79.390(3)
_cell_formula_units_Z            4
_cell_length_a                   13.4659(10)
_cell_length_b                   14.5842(12)
_cell_length_c                   17.9402(14)
_cell_measurement_reflns_used    9247
_cell_measurement_temperature    109(2)
_cell_measurement_theta_max      28.26
_cell_measurement_theta_min      2.42
_cell_volume                     3403.4(5)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      108.8
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0670
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            176117
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.357
_diffrn_reflns_theta_min         2.281
_exptl_absorpt_coefficient_mu    0.920
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_description       plate
_exptl_crystal_F_000             1576
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.587
_refine_diff_density_min         -0.829
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     849
_refine_ls_number_reflns         16970
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0255
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0227P)^2^+2.6250P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0538
_refine_ls_wR_factor_ref         0.0578
_reflns_Friedel_coverage         0.000
_reflns_number_gt                14058
_reflns_number_total             16970
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8sc03837f2.cif
_cod_data_source_block           mo_xy_590_3rd_1_0m
_cod_database_code               1550180
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.964
_shelx_estimated_absorpt_t_min   0.859
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C22(H22), C41(H41), C29(H29), C42(H42), C65(H65), C2(H2), C14(H14), C6(H6),
 C13(H13), C30(H30), C21(H21), C58(H58), C3(H3), C39(H39), C66(H66), C5(H5),
 C57(H57), C50(H50), C38(H38), C49(H49)
2.b Aromatic/amide H refined with riding coordinates:
 C55(H55), C32(H32), C27(H27), C68(H68), C19(H19), C26(H26), C25(H25),
 C35(H35), C34(H34), C63(H63), C8(H8), C52(H52), C33(H33), C60(H60), C54(H54),
 C24(H24), C11(H11), C69(H69), C53(H53), C62(H62), C61(H61), C16(H16), C18(H18),
  C47(H47), C71(H71), C70(H70), C17(H17), C44(H44), C10(H10), C9(H9), C79(H79),
 C46(H46), C80(H80), C45(H45), C74(H74), C76(H76), C75(H75), C73(H73), C77(H77),
  C81(H81), C78(H78), C84(H84), C82(H82), C83(H83)
2.c Idealised Me refined as rotating group:
 C37(H37A,H37B,H37C), C1(H1A,H1B,H1C), C40(H40A,H40B,H40C), C4(H4A,H4B,H4C)
;
_olex2_submission_special_instructions 'No special instructions were received'