Bent-to-planar Si-rhodamines: a distinct rehybridization lights up NIR-II fluorescence for tracking nitric oxide in the Alzheimer's disease brain.
Xu, Qingshuang; Zhang, Yutao; Zhu, Mingming; Yan, Chenxu; Mao, Wenle; Zhu, Wei-Hong; Guo, Zhiqian; Chemical science 14 (2023) 4091–4101; doi:10.1039/d3sc00193h

data_1568676
_publ_section_title
;
 Bent-to-planar Si-rhodamines: a distinct rehybridization lights up NIR-II
 fluorescence for tracking nitric oxide in the Alzheimer's disease brain.
;
_journal_issue                   15
_journal_name_full               'Chemical science'
_journal_page_first              4091
_journal_page_last               4101
_journal_paper_doi               10.1039/d3sc00193h
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety
'C23 H32 Cl N2 Si, Cl, C0.5 H Cl1.2, C H2 Cl2, C0.5 H Cl0.8'
_chemical_formula_sum            'C25 H36 Cl6 N2 Si'
_chemical_formula_weight         605.35
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2021-12-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-01-04 deposited with the CCDC.	2023-03-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.2241(9)
_cell_length_b                   9.0072(3)
_cell_length_c                   30.4536(11)
_cell_measurement_reflns_used    9876
_cell_measurement_temperature    272(2)
_cell_measurement_theta_max      67.92
_cell_measurement_theta_min      2.90
_cell_volume                     6096.1(4)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      272.0
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0784
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            54262
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.298
_diffrn_reflns_theta_min         2.902
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.646
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.4474
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1535 before and 0.0773 after correction. The Ratio of minimum to maximum transmission is 0.5941. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'dull dark black'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_description       needle
_exptl_crystal_F_000             2528
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         5562
_refine_ls_number_restraints     41
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0912
_refine_ls_R_factor_gt           0.0568
_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^)+(0.0863P)^2^+2.3318P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1454
_refine_ls_wR_factor_ref         0.1648
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3797
_reflns_number_total             5562
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc00193h2.cif
_cod_data_source_block           xqs_p_sirhd_3rd_0ma_a
_cod_depositor_comments
'Adding full bibliography for 1568674--1568676.cif.'
_cod_database_code               1568676
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.895
_shelx_estimated_absorpt_t_min   0.602
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Cl7-C00Y \\sim Cl1-C5
 with sigma of 0.02
 Cl6-C00Y \\sim Cl2-C5
 with sigma of 0.02
 Cl5-C18 \\sim Cl04-C00W
 with sigma of 0.02
 Cl05-C00W \\sim Cl0A-C18
 with sigma of 0.02
 Cl2-Cl1 \\sim Cl7-Cl6
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Cl7 \\sim Cl1 \\sim Cl6 \\sim Cl2: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08
C00Y \\sim C5: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
Cl5 \\sim Cl04 \\sim Cl05 \\sim Cl0A: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
C18 \\sim C00W: within 2A with sigma of 0.04 and sigma for terminal atoms of
0.08
4. Others
 Fixed Sof: Cl04(0.5) Cl05(0.7) Cl6(0.6) Cl7(0.6) C00W(0.5) H0AA(0.5) HC(0.5)
 C00Y(0.6) HF(0.6) H1AA(0.6) Cl1(0.4) Cl2(0.4) C5(0.4) H5A(0.4) H5B(0.4)
 Cl0A(0.3) Cl5(0.5) C18(0.5) H18A(0.5) H18B(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C00M(H00A,H00B), C00P(H00G,H00K), C00Q(H00M,H00N), C00S(H00S,H00T), C00W(H0AA,
 HC), C00Y(HF,H1AA), C5(H5A,H5B), C18(H18A,H18B)
5.b Aromatic/amide H refined with riding coordinates:
 C00F(H00F), C00H(H00H), C00I(H00I), C00J(H00J), C00L(H00L), C00O(H00O)
5.c Idealised Me refined as rotating group:
 C00N(H00C,H00D,H00E), C00R(H00P,H00Q,H00R), C00T(H00U,H00V,H00W), C00U(H00X,
 H00Y,H), C00V(H00Z,HA,HB), C00X(H00,HD,HE)
;
_olex2_submission_special_instructions 'No special instructions were received'