Controlled Knoevenagel reactions of methyl groups of 1,3,5,7-tetramethyl BODIPY dyes for unique BODIPY dyes
Zhu, Shilei; Zhang, Jingtuo; Vegesna, Giri; Tiwari, Ashutosh; Luo, Fen-Tair; Zeller, Matthias; Luck, Rudy; Li, Haihua; Green, Sarah; Liu, Haiying; RSC Adv. 2 (2012) 404–; doi:10.1039/C1RA00678A

data_7238448
_publ_section_title
;
 Controlled Knoevenagel reactions of methyl groups of 1,3,5,7-tetramethyl
 BODIPY dyes for unique BODIPY dyes
;
_journal_issue                   2
_journal_name_full               'RSC Adv.'
_journal_page_first              404
_journal_paper_doi               10.1039/C1RA00678A
_journal_volume                  2
_journal_year                    2012
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C22 H21 B1 F2 N2 O3'
_chemical_formula_sum            'C22 H21 B F2 N2 O3'
_chemical_formula_weight         410.22
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2011-04-20T22:32:43-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                81.7570(10)
_cell_angle_beta                 84.9650(10)
_cell_angle_gamma                85.8970(10)
_cell_formula_units_Z            2
_cell_length_a                   6.5685(5)
_cell_length_b                   8.8104(6)
_cell_length_c                   16.4780(10)
_cell_measurement_reflns_used    123
_cell_measurement_temperature    447(2)
_cell_measurement_theta_max      29.6731
_cell_measurement_theta_min      3.802
_cell_measurement_wavelength     0.71073
_cell_volume                     938.42(11)
_computing_cell_refinement       'SAINT V7.66A integration software'
_computing_data_collection       'Bruker APEX2 software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_diffrn_ambient_temperature      447(2)
_diffrn_detector                 'APEX-II CCD'
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       '\f or \w oscillation scans'
_diffrn_orient_matrix_type       'x-axis to radiation source'
_diffrn_orient_matrix_UB_11      0.370364E-1
_diffrn_orient_matrix_UB_12      -0.104673
_diffrn_orient_matrix_UB_13      -0.150403E-1
_diffrn_orient_matrix_UB_21      -0.237882E-1
_diffrn_orient_matrix_UB_22      0.39024E-1
_diffrn_orient_matrix_UB_23      -0.585051E-1
_diffrn_orient_matrix_UB_31      0.146543
_diffrn_orient_matrix_UB_32      0.257298E-1
_diffrn_orient_matrix_UB_33      -0.106908E-1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10755
_diffrn_reflns_theta_full        28
_diffrn_reflns_theta_max         30.25
_diffrn_reflns_theta_min         1.25
_diffrn_source                   'sealed x-ray tube'
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.677
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.059
_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     276
_refine_ls_number_reflns         5282
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.064
_refine_ls_R_factor_gt           0.0477
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0529P)^2^+0.5400P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1132
_refine_ls_wR_factor_ref         0.1258
_reflns_number_gt                4175
_reflns_number_total             5282
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            c1ra00678a.txt
_cod_data_source_block           11rlr004_0m
_cod_database_code               7238448