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_4034330
_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         'C35 H45 B O S3'
_chemical_formula_sum            'C35 H45 B O S3'
_chemical_formula_weight         588.70
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -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                103.228(5)
_cell_angle_beta                 97.761(5)
_cell_angle_gamma                91.734(5)
_cell_formula_units_Z            2
_cell_length_a                   8.8277(9)
_cell_length_b                   12.8220(13)
_cell_length_c                   15.1587(17)
_cell_measurement_reflns_used    6910
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.20
_cell_measurement_theta_min      2.32
_cell_volume                     1651.6(3)
_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 0.977
_diffrn_measured_fraction_theta_max 0.938
_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  0.0293
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18055
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.460
_diffrn_reflns_theta_min         1.883
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.250
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_correction_T_min  0.5972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1089 before and 0.0464 after correction.
The Ratio of minimum to maximum transmission is 0.8015.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.184
_exptl_crystal_description       plate
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.369
_exptl_crystal_size_mid          0.269
_exptl_crystal_size_min          0.089
_refine_diff_density_max         0.910
_refine_diff_density_min         -0.553
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     460
_refine_ls_number_reflns         6376
_refine_ls_number_restraints     999
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0845
_refine_ls_R_factor_gt           0.0641
_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^)+(0.0618P)^2^+2.6869P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1507
_refine_ls_wR_factor_ref         0.1715
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5003
_reflns_number_total             6376
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00398_si_004.cif
_cod_data_source_block           mw282_pp_a
_cod_database_code               4034330
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.913
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C33B-C32 \\sim C33A-C32 \\sim C33B-C34B \\sim C34A-C33A \\sim C35B-C34B \\sim
C35A-C34A
 with sigma of 0.01
 C17B-C14B \\sim C14A-C17A \\sim C16B-C12B \\sim C16A-C12A \\sim C10A-C15A
\\sim C15B-C10B
 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
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(H32C)=Sof(H32D)=Sof(C33A)=Sof(H33A)=Sof(H33B)=Sof(C34A)=Sof(H34A)=
 Sof(H34B)=Sof(C35A)=Sof(H35A)=Sof(H35B)=Sof(H35C)=1-FVAR(1)
 Sof(H32A)=Sof(H32B)=Sof(C33B)=Sof(H33C)=Sof(H33D)=Sof(C34B)=Sof(H34C)=
 Sof(H34D)=Sof(C35B)=Sof(H35D)=Sof(H35E)=Sof(H35F)=FVAR(1)
 Sof(C9A)=Sof(C10A)=Sof(C11A)=Sof(H11A)=Sof(C12A)=Sof(C13A)=Sof(H13A)=
 Sof(C14A)=Sof(C15A)=Sof(H15A)=Sof(H15B)=Sof(H15C)=Sof(C16A)=Sof(H16A)=
 Sof(H16B)=Sof(H16C)=Sof(C17A)=Sof(H17A)=Sof(H17B)=Sof(H17C)=1-FVAR(2)
 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)=FVAR(2)
6.a Secondary CH2 refined with riding coordinates:
 C28(H28A,H28B), C29(H29A,H29B), C30(H30A,H30B), C32(H32A,H32B), C32(H32C,
 H32D), C33A(H33A,H33B), C33B(H33C,H33D), C34A(H34A,H34B), C34B(H34C,H34D)
6.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C7(H7), C11A(H11A), C13A(H13A), C11B(H11B), C13B(H13B), C20(H20),
 C22(H22)
6.c Fitted hexagon refined as free rotating group:
 C9A(C10A,C11A,C12A,C13A,C14A), C9B(C10B,C11B,C12B,C13B,C14B)
6.d 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), C24(H24A,H24B,H24C),
 C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C31(H31A,H31B,
 H31C), C35A(H35A,H35B,H35C), C35B(H35D,H35E,H35F)
;
_olex2_submission_special_instructions 'No special instructions were received'