Conformation-Restricted Partially and Fully Fused BODIPY Dimers as Highly Stable Near-Infrared Fluorescent Dyes.
Wang, Jun; Wu, Qinghua; Wang, Shaowu; Yu, Changjiang; Li, Jin; Hao, Erhong; Wei, Yun; Mu, Xiaolong; Jiao, Lijuan; Organic letters 17 (2015) 5360–5363; doi:10.1021/acs.orglett.5b02717

data_1555384
_publ_section_title
;
 Conformation-Restricted Partially and Fully Fused BODIPY Dimers as Highly
 Stable Near-Infrared Fluorescent Dyes.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5360
_journal_page_last               5363
_journal_paper_doi               10.1021/acs.orglett.5b02717
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C30 H32 B2 F4 N4'
_chemical_formula_sum            'C30 H32 B2 F4 N4'
_chemical_formula_weight         546.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yc'
_space_group_name_H-M_alt        'P 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-12-19
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.101(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.718(2)
_cell_length_b                   8.6639(16)
_cell_length_c                   12.342(2)
_cell_measurement_reflns_used    863
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.35
_cell_measurement_theta_min      2.86
_cell_volume                     1334.5(4)
_computing_data_reduction        'SAINT v7.34A (Bruker, 200?)'
_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    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1073
_diffrn_reflns_av_unetI/netI     0.0935
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9278
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.63
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.9882
_exptl_absorpt_correction_T_min  0.9862
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             572
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2352
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.1728
_refine_ls_R_factor_gt           0.0614
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0743P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1313
_refine_ls_wR_factor_ref         0.1804
_reflns_number_gt                979
_reflns_number_total             2352
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b02717_si_002.cif
_cod_data_source_block           130730c
_cod_database_code               1555384
_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. Restrained distances
 C11-C2
 1.5 with sigma of 0.02
 C2-C17
 1.5 with sigma of 0.02
 C17-C16
 1.5 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C17) = Uanis(C16)
4. Others
 Sof(C16)=Sof(H16A)=Sof(H16B)=Sof(H16C)=Sof(C17)=Sof(H17A)=Sof(H17B)=1-FVAR(1)
 Sof(C11)=Sof(H11A)=Sof(H11B)=Sof(C12)=Sof(H12A)=Sof(H12B)=Sof(H12C)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C17(H17A,H17B)
5.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C15(H15)
5.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C12(H12A,H12B,
 H12C), C16(H16A,H16B,H16C)
;