Fluorescence Switching of Intramolecular Lewis Acid-Base Pairs on a Flexible Backbone.
Cao, Yang; Arsenault, Nicole E.; Hean, Duane; Wolf, Michael O.; The Journal of organic chemistry 84 (2019) 5394–5403; doi:10.1021/acs.joc.9b00398

data_4034328
_publ_section_title
;
 Fluorescence Switching of Intramolecular Lewis Acid-Base Pairs on a
 Flexible Backbone.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5394
_journal_page_last               5403
_journal_paper_doi               10.1021/acs.joc.9b00398
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C38 H36 B O P S2'
_chemical_formula_sum            'C38 H36 B O P S2'
_chemical_formula_weight         614.57
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-10-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.913(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   29.6487(11)
_cell_length_b                   13.0893(5)
_cell_length_c                   17.7197(7)
_cell_measurement_reflns_used    6910
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.20
_cell_measurement_theta_min      2.32
_cell_volume                     6826.7(5)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.971
_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  0.0371
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            21755
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_min         2.012
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_correction_T_min  0.6992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1424 before and 0.0474 after correction. The Ratio of minimum to maximum transmission is 0.9384. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_description       plate
_exptl_crystal_F_000             2592
_exptl_crystal_size_max          0.521
_exptl_crystal_size_mid          0.419
_exptl_crystal_size_min          0.071
_platon_squeeze_details
;
TITL mw281_pp_aC 1 2/c 1    R = 0.11
CELL   29.6487   13.0893   17.7197     90.00     96.91     90.00
SPGR C2/c
C101 0.515 0.266 0.700 !       4.60 eA-3
C102 0.989 0.330 0.316 !       4.33 eA-3
C103 1.000 0.406 0.243 !       3.97 eA-3
C104 0.987 0.234 0.223 !       3.23 eA-3
Q105 0.633 0.210 0.158 !       1.21 eA-3
Q106 0.698 0.323 0.312 !       1.07 eA-3
Q107 0.382 0.236 0.242 !       0.72 eA-3
Q108 0.292 0.280 0.237 !       0.57 eA-3
Q109 0.660 0.301 0.293 !       0.57 eA-3
Q110 0.164 0.229 0.060 !       0.55 eA-3
Q111 0.155 0.361 0.121 !       0.53 eA-3
Q112 0.290 0.389 0.144 !       0.53 eA-3
;
_refine_diff_density_max         1.218
_refine_diff_density_min         -0.816
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     390
_refine_ls_number_reflns         6780
_refine_ls_number_restraints     1265
_refine_ls_restrained_S_all      0.973
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0534
_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^)+(0.0687P)^2^+7.9056P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1336
_refine_ls_wR_factor_ref         0.1447
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5145
_reflns_number_total             6780
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00398_si_006.cif
_cod_data_source_block           mw281_pp_a_sq
_cod_database_code               4034328
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.889
_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
 C26A-C21A \\sim C21B-C25B
 with sigma of 0.01
 C17A-C14A \\sim C14B-C17B
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
Uanis(C18A) = Uanis(C22A) = Uanis(C19A) = Uanis(C21A) = Uanis(C20A) =
Uanis(C23B) = Uanis(C18B) = Uanis(C23A) = Uanis(C22B) = Uanis(C21B) =
Uanis(C20B) = Uanis(C19B)
Uanis(C26A) = Uanis(C25B)
Uanis(C16A) = Uanis(C16B)
Uanis(C14A) = Uanis(C13A) = Uanis(C12A) = Uanis(C11A) = Uanis(C10A) = Uanis(C9A)
Uanis(C26B) = Uanis(C24A)
Uanis(C15A) = Uanis(C15B)
Uanis(C9A) = Uanis(C9B)
Uanis(C10A) = Uanis(C10B)
Uanis(C11A) = Uanis(C11B)
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C19B)=Sof(C18B)=Sof(C23B)=Sof(C22B)=Sof(H22B)=Sof(C21B)=Sof(C20B)=
 Sof(H20B)=Sof(C24B)=Sof(H24D)=Sof(H24E)=Sof(H24F)=Sof(C25B)=Sof(H25D)=
 Sof(H25E)=Sof(H25F)=Sof(C26B)=Sof(H26D)=Sof(H26E)=Sof(H26F)=1-FVAR(1)
 Sof(C18A)=Sof(C23A)=Sof(C22A)=Sof(H22A)=Sof(C21A)=Sof(C20A)=Sof(H20A)=
 Sof(C19A)=Sof(C24A)=Sof(H24A)=Sof(H24B)=Sof(H24C)=Sof(C25A)=Sof(H25A)=
 Sof(H25B)=Sof(H25C)=Sof(C26A)=Sof(H26A)=Sof(H26B)=Sof(H26C)=FVAR(1)
 Sof(C9B)=Sof(C10B)=Sof(C11B)=Sof(H11B)=Sof(C12B)=Sof(C13B)=Sof(H13B)=
 Sof(C14B)=Sof(C15B)=Sof(H15D)=Sof(H15E)=Sof(H15F)=Sof(C16B)=Sof(H16D)=
 Sof(H16E)=Sof(H16F)=Sof(C17B)=Sof(H17D)=Sof(H17E)=Sof(H17F)=1-FVAR(2)
 Sof(C14A)=Sof(C13A)=Sof(H13A)=Sof(C12A)=Sof(C11A)=Sof(H11A)=Sof(C10A)=
 Sof(C9A)=Sof(C15A)=Sof(H15A)=Sof(H15B)=Sof(H15C)=Sof(C16A)=Sof(H16A)=Sof(H16B)=
 Sof(H16C)=Sof(C17A)=Sof(H17A)=Sof(H17B)=Sof(H17C)=FVAR(2)
6.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C7(H7), C8(H8), C11B(H11B), C13B(H13B), C13A(H13A),
 C11A(H11A), C22A(H22A), C20A(H20A), C22B(H22B), C20B(H20B), C28(H28), C29(H29),
  C30(H30), C31(H31), C32(H32), C34(H34), C35(H35), C36(H36), C37(H37), C38(H38)
6.b Fitted hexagon refined as free rotating group:
 C14A(C13A,C12A,C11A,C10A,C9A), C18A(C23A,C22A,C21A,C20A,C19A), C19B(C18B,C23B,
 C22B,C21B,C20B)
6.c Idealised Me refined as rotating group:
 C15A(H15A,H15B,H15C), C15B(H15D,H15E,H15F), C16A(H16A,H16B,H16C), C16B(H16D,
 H16E,H16F), C17A(H17A,H17B,H17C), C17B(H17D,H17E,H17F), C24A(H24A,H24B,H24C),
 C24B(H24D,H24E,H24F), C25A(H25A,H25B,H25C), C25B(H25D,H25E,H25F), C26A(H26A,
 H26B,H26C), C26B(H26D,H26E,H26F)
;
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'