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_4032251
_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         'C35 H46 B N O2'
_chemical_formula_sum            'C35 H46 B N O2'
_chemical_formula_weight         523.54
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2016-11-04
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_cell_angle_alpha                90
_cell_angle_beta                 112.1797(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.6934(11)
_cell_length_b                   18.5229(16)
_cell_length_c                   14.3034(12)
_cell_measurement_reflns_used    9742
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.58
_cell_measurement_theta_min      2.93
_cell_volume                     3114.1(5)
_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      100.62
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0282
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            32281
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_min         2.931
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6917
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0567 before and 0.0513 after correction.
The Ratio of minimum to maximum transmission is 0.9277.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.117
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.492
_refine_diff_density_min         -0.500
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         6763
_refine_ls_number_restraints     41
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0529
_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^)+(0.0560P)^2^+1.9072P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1298
_refine_ls_wR_factor_ref         0.1355
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5946
_reflns_number_total             6763
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b02802_si_001.cif
_cod_data_source_block           rad267_0m
_cod_database_code               4032251
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.972
_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. Restrained distances
 N1-B1 \\sim N1A-B1
 with sigma of 0.005
 N1-C16 \\sim N1A-C2
 with sigma of 0.005
 C16-C1A \\sim C2-C1
 with sigma of 0.005
 N1-C1 \\sim N1A-C1A
 with sigma of 0.005
3. Rigid bond restraints
 C16, C17
 with sigma for 1-2 distances of 0.008 and sigma for 1-3 distances of 0.008
4. Uiso/Uaniso restraints and constraints
C16 \\sim C17: within 1.7A with sigma of 0.01 and sigma for terminal atoms of
0.01
Uanis(O2) \\sim Ueq, Uanis(O1) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.01
Uanis(C17) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C1A) \\sim Ueq: with sigma of
0.005 and sigma for terminal atoms of 0.005
5. Others
 Sof(C1A)=Sof(H1A)=Sof(N1A)=1-FVAR(1)
 Sof(N1)=Sof(C1)=Sof(H1)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C7(H7), C19(H19), C21(H21), C31(H31), C32(H32), C33(H33),
 C34(H34), C35(H35), C1A(H1A)
6.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C13(H13A,H13B,
 H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C23(H23A,H23B,H23C), C24(H24A,
 H24B,H24C), C25(H25A,H25B,H25C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C),
 C29(H29A,H29B,H29C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'