A H-Bond Strategy to Develop Acid-Resistant Photoswitchable Rhodamine Spirolactams for Super-Resolution Single-Molecule Localization Microscopy
Qi, Qingkai; Chi, Weijie; Li, Yuanyuan; Qiao, Qinglong; Chen, Jie; Miao, Lu; Zhang, Yi; Li, Jin; Ji, Wei; Xu, Tao; Liu, Xiaogang; Yoon, Juyoung; Xu, Zhaochao; Chemical Science  (2019) –; doi:10.1039/C9SC01284B

data_1550838
_publ_section_title
;
 A H-Bond Strategy to Develop Acid-Resistant Photoswitchable Rhodamine
 Spirolactams for Super-Resolution Single-Molecule Localization Microscopy
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C9SC01284B
_journal_year                    2019
_chemical_formula_moiety         'C34 H44 N4 O2'
_chemical_formula_sum            'C34 H44 N4 O2'
_chemical_formula_weight         540.73
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-03-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-03-06 deposited with the CCDC.    2019-04-04 downloaded from the CCDC.
;
_cell_angle_alpha                79.257(5)
_cell_angle_beta                 66.321(6)
_cell_angle_gamma                78.199(5)
_cell_formula_units_Z            2
_cell_length_a                   11.0084(7)
_cell_length_b                   12.0389(7)
_cell_length_c                   12.2322(8)
_cell_measurement_reflns_used    2863
_cell_measurement_temperature    130(6)
_cell_measurement_theta_max      29.3070
_cell_measurement_theta_min      3.7810
_cell_volume                     1443.40(17)
_computing_cell_refinement       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_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 (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      130(6)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4070
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.851
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -78.00  11.00   1.00   97.18    --  -11.91 -77.00  90.00   89
  2  \w    -10.00  77.00   1.00   97.18    --   12.07  57.00   0.00   87
  3  \w     45.00  72.00   1.00   97.18    --   12.07  37.00-180.00   27
  4  \w    -61.00  42.00   1.00   97.18    --   12.07 -57.00-150.00  103
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0282730000
_diffrn_orient_matrix_UB_12      0.0285372000
_diffrn_orient_matrix_UB_13      -0.0423805000
_diffrn_orient_matrix_UB_21      -0.0532819000
_diffrn_orient_matrix_UB_22      -0.0331288000
_diffrn_orient_matrix_UB_23      0.0268618000
_diffrn_orient_matrix_UB_31      -0.0376373000
_diffrn_orient_matrix_UB_32      0.0419591000
_diffrn_orient_matrix_UB_33      0.0393236000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0753
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.851
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11619
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.851
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.387
_diffrn_reflns_theta_min         2.867
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.38a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.500
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     376
_refine_ls_number_reflns         6788
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.1224
_refine_ls_R_factor_gt           0.0665
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1041P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1684
_refine_ls_wR_factor_ref         0.1948
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3685
_reflns_number_total             6788
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc01284b4.cif
_cod_data_source_block           p6
_cod_database_code               1550838
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N'
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.990
_reflns_odcompleteness_completeness 99.54
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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
 C21-C20
 1.54 with sigma of 0.01
 H21E_$1-H10
 2.1 with sigma of 0.005
 H21F_$1-H10
 2.1 with sigma of 0.005
 N2-C20 \\sim N2-C20A
 with sigma of 0.02
 C21-C20 \\sim C21A-C20A
 with sigma of 0.02
 C22-C20 \\sim C22-C20A
 with sigma of 0.02
3. Rigid bond restraints
 C25, C24
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
4. Uiso/Uaniso restraints and constraints
Uanis(C21) = Uanis(C21A)
Uanis(C20) = Uanis(C20A)
5. Others
 Sof(C20A)=Sof(H20C)=Sof(H20D)=Sof(C21A)=Sof(H21D)=Sof(H21E)=Sof(H21F)=1-FVAR(1)
 Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(H21C)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C22(H22A,H22B), C24(H24A,H24B), C26(H26A,H26B), C28(H28A,
 H28B), C29(H29A,H29B), C30(H30A,H30B), C20A(H20C,H20D)
6.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C13(H13), C16(H16), C18(H18),
 C19(H19)
6.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C23(H23A,H23B,H23C), C25(H25A,H25B,H25C), C27(H27A,H27B,
 H27C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C), C33(H33A,H33B,H33C),
 C21A(H21D,H21E,H21F)
;
_shelx_res_checksum              28334
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.270
_oxdiff_exptl_absorpt_empirical_full_min 0.600