Fluorogenic NIR-Probes Based on 1,2,4,5-Tetrazine Substituted BF2-Azadipyrromethenes
Wu, Dan; O'Shea, Donal; Chem. Commun.  (2017) –; doi:10.1039/C7CC06545K

data_7120654
_publ_section_title
;
 Fluorogenic NIR-Probes Based on 1,2,4,5-Tetrazine Substituted
 BF2-Azadipyrromethenes
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC06545K
_journal_year                    2017
_chemical_formula_moiety         'C41 H27 B F2 N8 O5, C H Cl3'
_chemical_formula_sum            'C42 H28 B Cl3 F2 N8 O5'
_chemical_formula_weight         879.88
_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     direct
_audit_creation_date             2016-07-08
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2017-08-04 deposited with the CCDC.
2017-09-13 downloaded from the CCDC.
;
_cell_angle_alpha                101.0460(14)
_cell_angle_beta                 91.1618(14)
_cell_angle_gamma                105.3224(14)
_cell_formula_units_Z            2
_cell_length_a                   8.3123(4)
_cell_length_b                   14.6491(7)
_cell_length_c                   16.8544(7)
_cell_measurement_reflns_used    9971
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.768
_cell_measurement_theta_min      2.47
_cell_volume                     1937.24(16)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX 3 (Bruker, 2015) '
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'XP (Bruker, 2008-2014)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      99.98
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'DUO Kappa diffractometer'
_diffrn_measurement_device_type  'Bruker APEX DUO KAPPA'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_av_unetI/netI     0.0683
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            22684
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_min         1.472
_diffrn_source                   'sealed X-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.306
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6585
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0617 before and 0.0505 after correction.
The Ratio of minimum to maximum transmission is 0.8832.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            gold
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_description       fragment
_exptl_crystal_F_000             900
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.020
_refine_diff_density_min         -0.813
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     551
_refine_ls_number_reflns         8858
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.1115
_refine_ls_R_factor_gt           0.0590
_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^)+(0.0692P)^2^+1.8347P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1385
_refine_ls_wR_factor_ref         0.1602
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5509
_reflns_number_total             8858
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc06545k3.cif
_cod_data_source_block           tcd538
_cod_original_cell_volume        1937.24(15)
_cod_database_code               7120654
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.925
_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 Ternary CH refined with riding coordinates:
 C1S(H1S)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C14(H14), C15(H15),
 C17(H17), C18(H18), C24(H24), C27(H27), C28(H28), C29(H29), C30(H30), C31(H31),
  C33(H33), C34(H34), C36(H36), C37(H37), C47(H47), C48(H48), C50(H50), C51(H51)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_shelx_res_checksum              22379
_shelx_shelxl_version_number     2014/7
_olex2_exptl_crystal_mounting_method 'Mitegen holder in oil'
_olex2_submission_original_sample_id WD380
_olex2_submission_special_instructions 'No special instructions were received'