Transformation of Nonporous Adaptive Pillar[4]arene[1]quinone Crystals into Fluorescent Crystals via Multi-Step Solid-Vapor Postsynthetic Modification for Fluorescence Turn-on Sensing of Ethylenediamine.
Li, Errui; Jie, Kecheng; Fang, Yu; Cai, Peiyu; Huang, Feihe; Journal of the American Chemical Society  (2020) –; doi:10.1021/jacs.0c07482

data_4135211
_publ_section_title
;
 Transformation of Nonporous Adaptive Pillar[4]arene[1]quinone Crystals
 into Fluorescent Crystals via Multi-Step Solid-Vapor Postsynthetic
 Modification for Fluorescence Turn-on Sensing of Ethylenediamine.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c07482
_journal_year                    2020
_chemical_formula_moiety         'C55 H72 N4 O10, C2 H8 N2'
_chemical_formula_sum            'C57 H80 N6 O10'
_chemical_formula_weight         1009.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yc'
_space_group_name_H-M_alt        'P 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2018-12-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.886(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.7932(11)
_cell_length_b                   12.7208(6)
_cell_length_c                   24.3108(13)
_cell_measurement_reflns_used    5483
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      25.77
_cell_measurement_theta_min      2.45
_cell_volume                     5707.3(5)
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      170.01
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_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  0.0684
_diffrn_reflns_av_unetI/netI     0.0594
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            47727
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.450
_diffrn_reflns_theta_min         2.207
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6334
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0905 before and 0.0516 after correction.
The Ratio of minimum to maximum transmission is 0.8497.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_description       NEEDLE
_exptl_crystal_F_000             2176
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.965
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     701
_refine_ls_number_reflns         11677
_refine_ls_number_restraints     41
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.1764
_refine_ls_R_factor_gt           0.0974
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1688P)^2^+3.0996P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2821
_refine_ls_wR_factor_ref         0.3422
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5509
_reflns_number_total             11677
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c07482_si_003.cif
_cod_data_source_block           181119_ler_c2n2_0m_sq
_cod_database_code               4135211
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.994
_shelx_estimated_absorpt_t_min   0.982
_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, All N(H) groups,
  All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C55-C56
 1.53 with sigma of 0.01
 N2-H2B
 0.88 with sigma of 0.02
 C10-C11 \\sim C10-C11A
 with sigma of 0.02
 C11-N4 \\sim C11A-N4A
 with sigma of 0.02
 C10-N4 \\sim C10-N4A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C10 \\sim N4 \\sim C11 \\sim N4A \\sim C11A: within 1.7A with sigma of 0.01 and
sigma for terminal atoms of 0.02
4. Others
 Sof(H10C)=Sof(H10D)=Sof(N4A)=Sof(H4AA)=Sof(H4AB)=Sof(C11A)=Sof(H11C)=
 Sof(H11D)=1-FVAR(1)
 Sof(H10A)=Sof(H10B)=Sof(N4)=Sof(H4A)=Sof(H4B)=Sof(C11)=Sof(H11A)=Sof(H11B)=
 FVAR(1)
 Sof(H51C)=Sof(H51D)=Sof(C52A)=Sof(H52D)=Sof(H52E)=Sof(H52F)=1-FVAR(2)
 Sof(H51A)=Sof(H51B)=Sof(C52)=Sof(H52A)=Sof(H52B)=Sof(H52C)=FVAR(2)
5.a Rotating group:
 N6(H6A,H6B)
5.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C10(H10C,H10D),
 C12(H12A,H12B), C19(H19A,H19B), C21(H21A,H21B), C23(H23A,H23B), C30(H30A,H30B),
  C32(H32A,H32B), C34(H34A,H34B), C40(H40A,H40B), C42(H42A,H42B), C44(H44A,
 H44B), C51(H51A,H51B), C51(H51C,H51D), C53(H53A,H53B), C11(H11A,H11B),
 C11A(H11C,H11D), C55(H55A,H55B), C56(H56A,H56B)
5.c Me refined with riding coordinates:
 C52(H52A,H52B,H52C), C52A(H52D,H52E,H52F)
5.d Aromatic/amide H refined with riding coordinates:
 N1(H1), N3(H3), C14(H14), C17(H17), C25(H25), C28(H28), C36(H36), C39(H39),
 C46(H46), C49(H49)
5.e X=CH2 refined with riding coordinates:
 N4(H4A,H4B), N4A(H4AA,H4AB), N5(H5A,H5B)
5.f Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C22(H22A,H22B,H22C), C31(H31A,H31B,H31C), C33(H33A,H33B,
 H33C), C41(H41A,H41B,H41C), C43(H43A,H43B,H43C), C54(H54A,H54B,H54C)
;
_shelx_res_checksum              50113
_shelx_hkl_checksum              19765
_shelx_fab_checksum              25087
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'