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_1550182
_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_absolute_configuration unk
_chemical_formula_moiety
'C37 H33 F3 N2 O3 Ru2 S, 0.5(C4 H8 O), 0.75(C4 O), 0.5(C1.89 O0.5)'
_chemical_formula_sum            'C42.94 H37 F3 N2 O4.5 Ru2 S'
_chemical_formula_weight         944.26
_chemical_name_systematic        '[3-H(OTf)]'
_chemical_properties_physical    Air-sensitive,Moisture-sensitive
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           ' P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_symmetry_Int_Tables_number      18
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_primary     direct
_audit_creation_date             2017-05-05
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2018-06-28 deposited with the CCDC.
2018-11-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.316(4)
_cell_length_b                   29.316(6)
_cell_length_c                   12.6238(19)
_cell_measurement_reflns_used    9679
_cell_measurement_temperature    109(2)
_cell_measurement_theta_max      25.566
_cell_measurement_theta_min      2.336
_cell_volume                     7889(2)
_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  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      108.9
_diffrn_measured_fraction_theta_full 0.9971
_diffrn_measured_fraction_theta_max 0.9971
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0999
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            411552
_diffrn_reflns_theta_full        25.7383
_diffrn_reflns_theta_max         25.74
_diffrn_reflns_theta_min         2.29
_exptl_absorpt_coefficient_mu    0.879
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.5900
_exptl_crystal_description       needle
_exptl_crystal_F_000             3787.9874
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: THF'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.4060
_refine_diff_density_min         -0.4220
_refine_diff_density_rms         0.0725
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.011(15)
_refine_ls_d_res_high            0.8183
_refine_ls_d_res_low             8.8830
_refine_ls_goodness_of_fit_ref   1.0574
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    136
_refine_ls_number_parameters     990
_refine_ls_number_reflns         15037
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0574
_refine_ls_R_factor_all          0.0252
_refine_ls_R_factor_gt           0.0221
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0219P)^2^+7.1743P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0495
_refine_ls_wR_factor_ref         0.0509
_reflns_Friedel_coverage         0.997
_reflns_limit_h_max              26
_reflns_limit_h_min              -25
_reflns_limit_k_max              35
_reflns_limit_k_min              -35
_reflns_limit_l_max              15
_reflns_limit_l_min              -15
_reflns_number_gt                14381
_reflns_number_total             15037
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c8sc03837f2.cif
_cod_data_source_block           mo_XY_595_2_0ma
_cod_original_cell_volume        7888(2)
_cod_database_code               1550182
_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. Others
 Sof(C2A)=Sof(C8A)=Sof(C7A)=Sof(O6A)=Sof(C5A)=1-FVAR(1)
 Sof(O1aa)=Sof(C8ba)=Sof(C9ba)=Sof(C0ca)=Sof(C1ca)=FVAR(1)
 Sof(C83)=Sof(C84)=Sof(O9A)=Sof(C81)=Sof(C82)=1-FVAR(2)
 Sof(O2aa)=Sof(C77)=Sof(C79)=Sof(C80)=FVAR(2)
3.a Free rotating group:
 O1aa(C8ba,C9ba,C0ca,C1ca), O2aa(C77,C79,C80)
3.b Ternary CH refined with riding coordinates:
 C50(H50), C13(H13), C66(H66), C42(H42), C21(H21), C49(H49), C14(H14),
 C65(H65), C6(H6), C30(H30), C5(H5), C58(H58), C41(H41), C57(H57), C22(H22),
 C29(H29), C2(H2), C3(H3), C38(H38), C39(H39)
3.c Secondary CH2 refined with riding coordinates:
 C1aa(H1aa,H1ab), C75(H75a,H75b), C76(H76a,H76b), C0aa(H0aa,H0ab)
3.d Aromatic/amide H refined with riding coordinates:
 C35(H35), C26(H26), C53(H53), C63(H63), C10(H10), C46(H46), C55(H55),
 C45(H45), C27(H27), C54(H54), C69(H69), C8(H8), C52(H52), C33(H33), C71(H71),
 C19(H19), C61(H61), C25(H25), C17(H17), C47(H47), C70(H70), C44(H44), C18(H18),
  C68(H68), C11(H11), C32(H32), C34(H34), C62(H62), C60(H60), C16(H16),
 C24(H24), C9(H9)
3.e Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c), C37(H37a,H37b,H37c), C4(H4a,H4b,H4c), C40(H40a,H40b,H40c)
;
_olex2_submission_special_instructions 'No special instructions were received'