Fluorescent Molecular Rotors of Organoboron Compounds from Schiff Bases: Synthesis, Viscosity, Reversible Thermochromism, Cytotoxicity, and Bioimaging Cells.
Ibarra-Rodrı Guez, Marisol; Muñoz-Flores, Blanca M; Dias, H. V. Rasika; Sánchez, Mario; Gomez-Treviño, Alberto; Santillan, Rosa; Farfán, Norberto; Jiménez-Pérez, Víctor M; The Journal of organic chemistry 82 (2017) 2375–2385; doi:10.1021/acs.joc.6b02802

data_4032252
_publ_section_title
;
 Fluorescent Molecular Rotors of Organoboron Compounds from Schiff Bases:
 Synthesis, Viscosity, Reversible Thermochromism, Cytotoxicity, and
 Bioimaging Cells.
;
_journal_issue                   5
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2375
_journal_page_last               2385
_journal_paper_doi               10.1021/acs.joc.6b02802
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C64 H86 B2 N2 O4, C3 H6 O'
_chemical_formula_sum            'C67 H92 B2 N2 O5'
_chemical_formula_weight         1027.04
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-01-08
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.903(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.851(6)
_cell_length_b                   17.727(6)
_cell_length_c                   18.924(6)
_cell_measurement_reflns_used    9996
_cell_measurement_temperature    101(2)
_cell_measurement_theta_max      25.82
_cell_measurement_theta_min      2.79
_cell_volume                     6278(4)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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      101.2
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            60445
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.998
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         2.788
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6887
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0540 before and 0.0481 after correction.
The Ratio of minimum to maximum transmission is 0.9241.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.087
_exptl_crystal_description       diamond
_exptl_crystal_F_000             2232
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.464
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     787
_refine_ls_number_reflns         12238
_refine_ls_number_restraints     99
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.1061
_refine_ls_R_factor_gt           0.0719
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0827P)^2^+4.9328P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1758
_refine_ls_wR_factor_ref         0.1971
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8440
_reflns_number_total             12238
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b02802_si_001.cif
_cod_data_source_block           rad282_0m
_cod_database_code               4032252
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.984
_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. Rigid bond restraints
 C65, C64
 with sigma for 1-2 distances of 0.008 and sigma for 1-3 distances of 0.008
 C55A, C55, C41, C43, C42, C44, C57, C56, C58A, C58, C56A
 with sigma for 1-2 distances of 0.008 and sigma for 1-3 distances of 0.008
3. Uiso/Uaniso restraints and constraints
C55A \\sim C55 \\sim C41 \\sim C43 \\sim C42 \\sim C44 \\sim C57 \\sim C56
\\sim C58A \\sim C58 \\sim C56A: within 1.7A with sigma of 0.005 and sigma for
terminal atoms of 0.005
4. Others
 Sof(C55A)=Sof(C56A)=Sof(H56A)=Sof(H56B)=Sof(H56C)=Sof(C57A)=Sof(H57A)=
 Sof(H57B)=Sof(H57C)=Sof(C58A)=Sof(H58A)=Sof(H58B)=Sof(H58C)=1-FVAR(1)
 Sof(C55)=Sof(C56)=Sof(H56D)=Sof(H56E)=Sof(H56F)=Sof(C57)=Sof(H57D)=Sof(H57E)=
 Sof(H57F)=Sof(C58)=Sof(H58D)=Sof(H58E)=Sof(H58F)=FVAR(1)
 Fixed Sof: N1A(0.5) N2A(0.5) C66A(0.5) H66A(0.5) C67A(0.5) H67A(0.5) N1(0.5)
 N2(0.5) C66(0.5) H66(0.5) C67(0.5) H67(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C17(H17), C19(H19), C30(H30), C31(H31), C33(H33), C34(H34),
 C37(H37), C39(H39), C51(H51), C53(H53), C66A(H66A), C67A(H67A), C66(H66),
 C67(H67)
5.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C12(H12A,H12B,H12C),
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C), C24(H24A,H24B,H24C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C28(H28A,
 H28B,H28C), C42(H42A,H42B,H42C), C43(H43A,H43B,H43C), C44(H44A,H44B,H44C),
 C46(H46A,H46B,H46C), C47(H47A,H47B,H47C), C48(H48A,H48B,H48C), C60(H60A,H60B,
 H60C), C61(H61A,H61B,H61C), C62(H62A,H62B,H62C), C56A(H56A,H56B,H56C),
 C57A(H57A,H57B,H57C), C58A(H58A,H58B,H58C), C56(H56D,H56E,H56F), C57(H57D,H57E,
 H57F), C58(H58D,H58E,H58F), C64(H64A,H64B,H64C), C65(H65A,H65B,H65C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'