Rh-catalysed direct cyclisation of 1,4-naphthoquinone and 9,10-phenanthraquinone with alkyne: facile access to 1,8-dioxapyrenes and 1,12-dioxaperylenes as orange and red-emitting luminophores
Jing Wang; Dekun Qin; Jingbo Lan; Yangyang Cheng; Shuai Zhang; Qiang Guo; Jie Wu; Di Wu; Jingsong You; Chem.Commun. 51 (2015) 6337–; doi:10.1039/C5cc00312A

data_7116888
_publ_section_title
;
 Rh-catalysed direct cyclisation of 1,4-naphthoquinone and
 9,10-phenanthraquinone with alkyne: facile access to 1,8-dioxapyrenes and
 1,12-dioxaperylenes as orange and red-emitting luminophores
;
_journal_name_full               Chem.Commun.
_journal_page_first              6337
_journal_paper_doi               10.1039/C5cc00312A
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C28 H20 O2'
_chemical_formula_sum            'C28 H20 O2'
_chemical_formula_weight         388.44
_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   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-06-18
_audit_creation_method
;
Olex2 1.2
(compiled 2014.05.21 svn.r2940 for OlexSys, GUI svn.r4846)
;
_audit_update_record
;
2015-01-02 deposited with the CCDC.
2015-03-02 downloaded from the CCDC.
;
_cell_angle_alpha                73.905(2)
_cell_angle_beta                 80.721(2)
_cell_angle_gamma                89.893(2)
_cell_formula_units_Z            4
_cell_length_a                   10.5146(3)
_cell_length_b                   11.1198(3)
_cell_length_c                   18.1537(5)
_cell_measurement_reflns_used    14044
_cell_measurement_temperature    293
_cell_measurement_theta_max      72.5850
_cell_measurement_theta_min      4.1420
_cell_volume                     2010.60(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega   20.00  104.00   1.0000    2.3300
omega____ theta____ kappa____ phi______ frames
    -       36.4171   57.0000   90.0000 84

  2 omega  -31.00   53.00   1.0000    2.3300
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -57.0000 -180.0000 84

  3 omega  -31.00   53.00   1.0000    2.3300
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -57.0000   90.0000 84

  4 omega   23.00   90.00   1.0000    2.3300
omega____ theta____ kappa____ phi______ frames
    -       36.4171 -125.0000 -180.0000 67

  5 omega  -33.00   55.00   1.0000    2.3300
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -38.0000  -60.0000 88

  6 omega    1.00   75.00   1.0000    2.3300
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -99.0000  -30.0000 74

  7 omega    1.00   75.00   1.0000    2.3300
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -99.0000  -60.0000 74

  8 omega   20.00  104.00   1.0000    2.3300
omega____ theta____ kappa____ phi______ frames
    -       36.4171   57.0000   60.0000 84

  9 omega  -31.00   53.00   1.0000    2.3300
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -57.0000   60.0000 84

 10 omega   18.00  106.00   1.0000    2.3300
omega____ theta____ kappa____ phi______ frames
    -       36.4171   38.0000  -60.0000 88

 11 omega   40.00   98.00   1.0000    9.3200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 58

 12 omega   70.00  178.00   1.0000    9.3200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000    0.0000 108

 13 omega   39.00  109.00   1.0000    9.3200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   30.0000 70

 14 omega   38.00   91.00   1.0000    9.3200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 53

 15 omega   70.00  178.00   1.0000    9.3200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000   90.0000 108

 16 omega   39.00  109.00   1.0000    9.3200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 70

 17 omega   40.00   98.00   1.0000    9.3200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   90.0000 58

 18 omega   38.00   91.00   1.0000    9.3200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 53

 19 omega   38.00   91.00   1.0000    9.3200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 53

 20 omega   39.00  109.00   1.0000    9.3200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 70

 21 omega   38.00   91.00   1.0000    9.3200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 53

 22 omega   38.00  117.00   1.0000    9.3200
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -115.0000 -168.0000 79

 23 omega   40.00   98.00   1.0000    9.3200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 58

 24 omega   40.00  135.00   1.0000    9.3200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   30.0000 95

 25 omega   38.00   91.00   1.0000    9.3200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 53

 26 omega   38.00  116.00   1.0000    9.3200
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -120.0000 78

 27 omega   10.00  104.00   1.0000    2.3300
omega____ theta____ kappa____ phi______ frames
    -       36.4171   77.0000  -90.0000 94

 28 omega   10.00  104.00   1.0000    2.3300
omega____ theta____ kappa____ phi______ frames
    -       36.4171   77.0000 -150.0000 94

 29 omega   20.00  104.00   1.0000    2.3300
omega____ theta____ kappa____ phi______ frames
    -       36.4171   57.0000  -30.0000 84

 30 omega   10.00  104.00   1.0000    2.3300
omega____ theta____ kappa____ phi______ frames
    -       36.4171   77.0000  120.0000 94

 31 omega    7.00  108.00   1.0000    2.3300
omega____ theta____ kappa____ phi______ frames
    -       36.4171   19.0000  120.0000 101

 32 omega   10.00  104.00   1.0000    2.3300
omega____ theta____ kappa____ phi______ frames
    -       36.4171   77.0000  -30.0000 94

 33 omega   10.00  104.00   1.0000    2.3300
omega____ theta____ kappa____ phi______ frames
    -       36.4171   77.0000 -180.0000 94

 34 omega   81.00  176.00   1.0000    9.3200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -150.0000 95

 35 omega   81.00  176.00   1.0000    9.3200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  150.0000 95

 36 omega   81.00  176.00   1.0000    9.3200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 95

 37 omega   91.00  176.00   1.0000    9.3200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   90.0000 85

 38 omega   81.00  176.00   1.0000    9.3200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 95

 39 omega   91.00  176.00   1.0000    9.3200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -90.0000 85

 40 omega   81.00  176.00   1.0000    9.3200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 95

 41 omega   81.00  176.00   1.0000    9.3200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 95

 42 omega   87.00  178.00   1.0000    9.3200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  150.0000 91

 43 omega   81.00  176.00   1.0000    9.3200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   90.0000 95

 44 omega   81.00  176.00   1.0000    9.3200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 95

 45 omega   81.00  176.00   1.0000    9.3200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 95

 46 omega   70.00  178.00   1.0000    9.3200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000 -120.0000 108
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1220289000
_diffrn_orient_matrix_UB_12      -0.0315578000
_diffrn_orient_matrix_UB_13      -0.0493277000
_diffrn_orient_matrix_UB_21      -0.0631687000
_diffrn_orient_matrix_UB_22      0.0436859000
_diffrn_orient_matrix_UB_23      -0.0733024000
_diffrn_orient_matrix_UB_31      0.0566042000
_diffrn_orient_matrix_UB_32      0.1339032000
_diffrn_orient_matrix_UB_33      -0.0148079000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            35551
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.070
_diffrn_reflns_theta_min         4.142
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.624
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.30274
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     545
_refine_ls_number_reflns         7196
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0516
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1050P)^2^+0.1440P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1441
_refine_ls_wR_factor_ref         0.1538
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6091
_reflns_number_total             7196
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc00312a2.cif
_cod_data_source_block           wj01
_cod_original_cell_volume        2010.59(9)
_cod_database_code               7116888
_shelxl_version_number           2014-1
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C6(H6), C8(H8), C10(H10), C11(H11), C14(H14), C16(H16),
 C18(H18), C19(H19), C22(H22), C23(H23), C26(H26), C36(H36), C55(H55), C62(H62),
  C66(H66), C72(H72), C73(H73), C76(H76), C77(H77), C79(H79), C83(H83),
 C85(H85), C103(H103), C106(H106), C110(H110), C112(H112)
2.b Idealised Me refined as rotating group:
 C38(H38A,H38B,H38C), C39(H39A,H39B,H39C), C67(H67A,H67B,H67C), C69(H69A,H69B,
 H69C)
;
_shelx_res_checksum              95604
_shelx_hkl_checksum              88556
_olex2_submission_special_instructions 'No special instructions were received'