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_4034334
_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 H44.75 B O2 S3'
_chemical_formula_sum            'C35 H44.75 B O2 S3'
_chemical_formula_weight         604.45
_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                 107.952(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   33.057(3)
_cell_length_b                   8.1023(6)
_cell_length_c                   26.4753(18)
_cell_measurement_reflns_used    9965
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.31
_cell_measurement_theta_min      2.36
_cell_volume                     6745.9(9)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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 0.998
_diffrn_measured_fraction_theta_max 0.996
_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  0.0581
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            45375
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.429
_diffrn_reflns_theta_min         2.363
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.249
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_correction_T_min  0.6820
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1266 before and 0.0506 after correction. The Ratio of minimum to maximum transmission is 0.9153. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_description       plate
_exptl_crystal_F_000             2590
_exptl_crystal_size_max          0.428
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.036
_refine_diff_density_max         0.509
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     437
_refine_ls_number_reflns         6919
_refine_ls_number_restraints     382
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0512
_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^)+(0.0733P)^2^+5.6073P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1278
_refine_ls_wR_factor_ref         0.1389
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5168
_reflns_number_total             6919
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00398_si_005.cif
_cod_data_source_block           mw280_pp_a
_cod_original_cell_volume        6746.0(9)
_cod_database_code               4034334
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.901
_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 C32-C8 \\sim C34A-C33B \\sim C34B-C33B \\sim C35B-C34B \\sim
C35A-C34A
 with sigma of 0.02
 C34A-C33A \\sim C34B-C33B
 with sigma of 0.01
 C33B-C32 \\sim C33A-C32
 with sigma of 0.01
 C29B-C28 \\sim C29A-C28 \\sim C30A-C29A \\sim C30B-C29B
 with sigma of 0.01
 C31A-C30A \\sim C31B-C30B
 with sigma of 0.01
3. 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
4. Others
 Sof(H32C)=Sof(H32D)=Sof(C33A)=Sof(H33C)=Sof(H33D)=Sof(C34A)=Sof(H34C)=
 Sof(H34D)=Sof(C35A)=Sof(H35D)=Sof(H35E)=Sof(H35F)=1-FVAR(1)
 Sof(H32A)=Sof(H32B)=Sof(C33B)=Sof(H33A)=Sof(H33B)=Sof(C34B)=Sof(H34A)=
 Sof(H34B)=Sof(C35B)=Sof(H35A)=Sof(H35B)=Sof(H35C)=FVAR(1)
 Sof(C29B)=Sof(H29C)=Sof(H29D)=Sof(C30B)=Sof(H30C)=Sof(H30D)=Sof(C31B)=
 Sof(H31D)=Sof(H31E)=Sof(H31F)=1-FVAR(2)
 Sof(H28A)=Sof(H28B)=Sof(C29A)=Sof(H29A)=Sof(H29B)=Sof(C30A)=Sof(H30A)=
 Sof(H30B)=Sof(C31A)=Sof(H31A)=Sof(H31B)=Sof(H31C)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C28(H28A,H28B), C29A(H29A,H29B), C29B(H29C,H29D), C30A(H30A,H30B), C30B(H30C,
 H30D), C32(H32A,H32B), C32(H32C,H32D), C33A(H33C,H33D), C33B(H33A,H33B),
 C34A(H34C,H34D), C34B(H34A,H34B)
5.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C7(H7), C11(H11), C13(H13), C20(H20), C22(H22)
5.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C24(H24A,H24B,
 H24C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C),
 C31A(H31A,H31B,H31C), C31B(H31D,H31E,H31F), C35A(H35D,H35E,H35F), C35B(H35A,
 H35B,H35C)
;
_olex2_submission_special_instructions 'No special instructions were received'