Thiophene-substituted aza-bodipy as a strategic synthon for the design of near-infrared dyes
Bellier, Quentin; Dalier, Fabrice; Jeanneau, Erwann; Maury, Olivier; Andraud, Chantal; New Journal of Chemistry 36 (2012) 768–; doi:10.1039/c2nj20943h

data_7052861
_publ_section_title
;
 Thiophene-substituted aza-bodipy as a strategic synthon for the design of
 near-infrared dyes
;
_journal_issue                   3
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              768
_journal_paper_doi               10.1039/c2nj20943h
_journal_volume                  36
_journal_year                    2012
_chemical_formula_moiety         'C28 H16 B Br2 F2 N3 S2'
_chemical_formula_sum            'C28 H16 B Br2 F2 N3 S2'
_chemical_formula_weight         667.19
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 106.091(7)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.6060(10)
_cell_length_b                   14.2120(10)
_cell_length_c                   25.060(2)
_cell_measurement_reflns_used    13101
_cell_measurement_temperature    110
_cell_measurement_theta_max      67.3736
_cell_measurement_theta_min      3.6084
_cell_volume                     4998.2(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      110
_diffrn_detector_area_resol_mean 10.4685
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.073
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            54285
_diffrn_reflns_theta_full        66.906
_diffrn_reflns_theta_max         67.483
_diffrn_reflns_theta_min         3.611
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.022
_exptl_absorpt_correction_T_max  0.457
_exptl_absorpt_correction_T_min  0.159
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.773
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2640
_exptl_crystal_size_max          0.355
_exptl_crystal_size_mid          0.171
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.66
_refine_diff_density_min         -0.71
_refine_ls_extinction_coef       48(3)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   1.0071
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     686
_refine_ls_number_reflns         8863
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0402
_refine_ls_shift/su_max          0.0020631
_refine_ls_shift/su_mean         0.0000674
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
0.142E+04 0.241E+04 0.150E+04 626. 139.
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1129
_refine_ls_wR_factor_gt          0.1118
_refine_ls_wR_factor_ref         0.1129
_reflns_limit_h_max              16
_reflns_limit_h_min              -17
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              29
_reflns_limit_l_min              0
_reflns_number_gt                8407
_reflns_number_total             8863
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   1.77
_oxford_diffrn_Wilson_scale      0.26
_oxford_refine_ls_r_factor_ref   0.0418
_oxford_refine_ls_scale          1.004(3)
_oxford_reflns_number_all        8863
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_cod_data_source_file            c2nj20943h.txt
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 21/c '
_cod_database_code               7052861
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S
CONT EXTPARAM
RIDE C ( 19,X'S) H ( 191,X'S)
RIDE C ( 20,X'S) H ( 201,X'S)
RIDE C ( 21,X'S) H ( 211,X'S)
RIDE C ( 24,X'S) H ( 241,X'S)
RIDE C ( 25,X'S) H ( 251,X'S)
RIDE C ( 26,X'S) H ( 261,X'S)
RIDE C ( 27,X'S) H ( 271,X'S)
RIDE C ( 28,X'S) H ( 281,X'S)
RIDE C ( 30,X'S) H ( 301,X'S)
RIDE C ( 32,X'S) H ( 321,X'S)
RIDE C ( 33,X'S) H ( 331,X'S)
RIDE C ( 34,X'S) H ( 341,X'S)
RIDE C ( 35,X'S) H ( 351,X'S)
RIDE C ( 36,X'S) H ( 361,X'S)
RIDE C ( 37,X'S) H ( 371,X'S)
RIDE C ( 38,X'S) H ( 381,X'S)
RIDE C ( 53,X'S) H ( 531,X'S)
RIDE C ( 56,X'S) H ( 561,X'S)
RIDE C ( 57,X'S) H ( 571,X'S)
RIDE C ( 58,X'S) H ( 581,X'S)
RIDE C ( 59,X'S) H ( 591,X'S)
RIDE C ( 60,X'S) H ( 601,X'S)
RIDE C ( 65,X'S) H ( 651,X'S)
RIDE C ( 66,X'S) H ( 661,X'S)
RIDE C ( 68,X'S) H ( 681,X'S)
RIDE C ( 70,X'S) H ( 701,X'S)
RIDE C ( 71,X'S) H ( 711,X'S)
RIDE C ( 72,X'S) H ( 721,X'S)
RIDE C ( 73,X'S) H ( 731,X'S)
RIDE C ( 74,X'S) H ( 741,X'S)
RIDE C ( 75,X'S) H ( 751,X'S)
RIDE C ( 76,X'S) H ( 761,X'S)
END
;
_iucr_refine_instruction_details_restraints
;
NO
REM HREST START (DO NOT REMOVE THIS LINE)
REM HREST END (DO NOT REMOVE THIS LINE)
END
;