Expanding a fluorescent RNA alphabet: synthesis, photophysics and utility of isothiazole-derived purine nucleoside surrogates.
Rovira, Alexander R.; Fin, Andrea; Tor, Yitzhak; Chemical science 8 (2017) 2983–2993; doi:10.1039/c6sc05354h

data_1545180
_publ_section_title
;
 Expanding a fluorescent RNA alphabet: synthesis, photophysics and utility
 of isothiazole-derived purine nucleoside surrogates.
;
_journal_issue                   4
_journal_name_full               'Chemical science'
_journal_page_first              2983
_journal_page_last               2993
_journal_paper_doi               10.1039/c6sc05354h
_journal_volume                  8
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C10 H12 N4 O5 S, 1.75(H2 O)'
_chemical_formula_sum            'C10 H15.5 N4 O6.75 S'
_chemical_formula_weight         331.82
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-05-16
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-12-06 deposited with the CCDC.
2017-01-27 downloaded from the CCDC.
;
_cell_angle_alpha                72.0700(10)
_cell_angle_beta                 80.2730(10)
_cell_angle_gamma                86.279(2)
_cell_formula_units_Z            4
_cell_length_a                   8.0883(2)
_cell_length_b                   10.9716(3)
_cell_length_c                   16.0771(4)
_cell_measurement_reflns_used    9799
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      68.272
_cell_measurement_theta_min      2.925
_cell_volume                     1337.78(6)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2014.11-0 (Bruker, 2014)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker X8 APEX II'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            47934
_diffrn_reflns_point_group_measured_fraction_full 0.929
_diffrn_reflns_point_group_measured_fraction_max 0.925
_diffrn_reflns_theta_full        68.000
_diffrn_reflns_theta_max         68.267
_diffrn_reflns_theta_min         2.925
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker Microstar FR-592'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.578
_exptl_absorpt_correction_T_max  0.3200
_exptl_absorpt_correction_T_min  0.2197
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0968 before and 0.0563 after correction.
The Ratio of minimum to maximum transmission is 0.6866.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            Colorless
_exptl_crystal_colour_primary    Colorless
_exptl_crystal_density_diffrn    1.648
_exptl_crystal_description       Blade
_exptl_crystal_F_000             694
_exptl_crystal_size_max          0.234
_exptl_crystal_size_mid          0.116
_exptl_crystal_size_min          0.095
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 3759 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.036(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     817
_refine_ls_number_reflns         9070
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0286
_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^)+(0.0549P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0758
_refine_ls_wR_factor_ref         0.0773
_reflns_Friedel_coverage         0.912
_reflns_Friedel_fraction_full    0.887
_reflns_Friedel_fraction_max     0.883
_reflns_number_gt                8414
_reflns_number_total             9070
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6sc05354h2.cif
_cod_data_source_block           Tor113
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according
to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 1545178--1545180.cif.

 Adding full bibliography for 1545178--1545180.cif.
;
_cod_original_formula_sum        'C10 H15.50 N4 O6.75 S'
_cod_database_code               1545180
_shelx_estimated_absorpt_t_max   0.792
_shelx_estimated_absorpt_t_min   0.584
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O1S(H1SA,H1SB), O2S(H2SA,H2SB), O3S(H3SA,H3SB), O4S(H4SA,H4SB), O5S(H5SA,
 H5SB), O6S(H6SB,H6SA), O7S(H7SA,H7SB)
2.b Ternary CH refined with riding coordinates:
 C2(H2), C3(H3D), C4(H4B), C5(H5), C2A(H2A), C3A(H3AC), C4A(H4AA), C5A(H5A),
 C2B(H2B), C3B(H3BD), C4B(H4BB), C5B(H5B), C2C(H2C), C3C(H3CD), C4C(H4CA),
 C5C(H5C)
2.c Secondary CH2 refined with riding coordinates:
 C1(H1C,H1D), C1A(H1AB,H1AC), C1B(H1BC,H1BD), C1C(H1CC,H1CD)
2.d Aromatic/amide H refined with riding coordinates:
 N1(H1B), N1A(H1AA), N1B(H1BB), N1C(H1CB)
2.e X=CH2 refined with riding coordinates:
 N3(H3B,H3C), N3A(H3AA,H3AB), N3B(H3BB,H3BC), N3C(H3CB,H3CC)
2.f Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3), O4(H4), O1A(H1A), O3A(H3A), O4A(H4A), O1B(H1BA), O3B(H3BA),
 O4B(H4BA), O1C(H1CA), O3C(H3CA), O4C(H4C)
;
_shelx_res_checksum              78964
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'