Synthetic Approach to Readily Accessible Benzofuran-Fused Borondipyrromethenes as Red-Emitting Laser Dyes.
Belmonte-Vázquez, José L; Avellanal-Zaballa, Edurne; Enríquez-Palacios, Ernesto; Cerdán, Luis; Esnal, Ixone; Bañuelos, Jorge; Villegas-Gómez, Clarisa; López Arbeloa, Iñigo; Peña-Cabrera, Eduardo; The Journal of organic chemistry 84 (2019) 2523–2541; doi:10.1021/acs.joc.8b02933

data_4033735
_publ_section_title
;
 Synthetic Approach to Readily Accessible Benzofuran-Fused
 Borondipyrromethenes as Red-Emitting Laser Dyes.
;
_journal_issue                   5
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2523
_journal_page_last               2541
_journal_paper_doi               10.1021/acs.joc.8b02933
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         '0.25(C2 Cl4), 0.5(C28 H17 B F2 N2 O3)'
_chemical_formula_sum            'C10 H10 B0.25 Cl0.25 F0.25 N2 O3'
_chemical_formula_weight         222.51
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-02-09
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                114.896(4)
_cell_angle_beta                 108.439(4)
_cell_angle_gamma                94.763(3)
_cell_formula_units_Z            4
_cell_length_a                   10.1007(4)
_cell_length_b                   11.0329(5)
_cell_length_c                   12.8754(5)
_cell_measurement_reflns_used    5159
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.8770
_cell_measurement_theta_min      4.0950
_cell_volume                     1195.08(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector_area_resol_mean 5.2012
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details
;
  1 omega -113.00  -86.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3256  -99.0000 -180.0000 27

  2 omega  -31.00   70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.3256  -57.0000   90.0000 101

  3 omega  -37.00   68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.3256  -77.0000 -120.0000 105

  4 omega  -36.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.3256  -77.0000    0.0000 111

  5 omega -155.00 -112.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000 -125.0000   30.0000 43

  6 omega   27.00   63.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -94.0000    0.0000 36

  7 omega   30.00  142.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -77.0000   60.0000 112

  8 omega   31.00   64.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000   30.0000 33

  9 omega   31.00   68.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000  150.0000 37

 10 omega   61.00  103.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -94.0000   30.0000 42

 11 omega   44.00  109.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -94.0000  -60.0000 65

 12 omega   92.00  143.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   30.0000   60.0000 51

 13 omega   79.00  154.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   30.0000 -180.0000 75

 14 omega   36.00   77.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -45.0000  -30.0000 41

 15 omega   87.00  117.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609 -125.0000 -150.0000 30

 16 omega   37.00   77.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -45.0000 -150.0000 40

 17 omega  127.00  152.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   61.0000   60.0000 25

 18 omega   97.00  147.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   45.0000  -60.0000 50

 19 omega   34.00   64.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000   60.0000 30

 20 omega   34.00   66.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000  -90.0000 32

 21 omega   33.00  114.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609 -125.0000  -90.0000 81
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0536751000
_diffrn_orient_matrix_UB_12      -0.1278108000
_diffrn_orient_matrix_UB_13      -0.0034995000
_diffrn_orient_matrix_UB_21      -0.1559589000
_diffrn_orient_matrix_UB_22      -0.0901680000
_diffrn_orient_matrix_UB_23      -0.0757447000
_diffrn_orient_matrix_UB_31      0.0196403000
_diffrn_orient_matrix_UB_32      -0.0287743000
_diffrn_orient_matrix_UB_33      -0.1214300000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8151
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.995
_diffrn_reflns_theta_min         4.108
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.291
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72556
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_description
;
;
_exptl_crystal_F_000             463
_refine_diff_density_max         1.139
_refine_diff_density_min         -2.371
_refine_diff_density_rms         0.182
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.920
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         4489
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.920
_refine_ls_R_factor_all          0.1237
_refine_ls_R_factor_gt           0.1175
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3849
_refine_ls_wR_factor_ref         0.4047
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4004
_reflns_number_total             4489
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02933_si_001.cif
_cod_data_source_block           a20180034_jb141
_cod_original_cell_volume        1195.08(9)
_cod_database_code               4033735
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         C10H10N2O3
_reflns_odcompleteness_completeness 99.51
_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:
 C22(H22), C23(H23), C11(H11), C28(H28), C29(H29), C26(H26), C0CA(H0CA),
 C27(H27), C32(H32), C25(H25), C31(H31), C33(H33), C24(H24), C30(H30)
2.b Idealised Me refined as rotating group:
 C36(H36A,H36B,H36C)
;
_olex2_date_sample_data_collection 2018-02-01
_olex2_submission_special_instructions 'No special instructions were received'