Synthesis and Cytotoxic and Antiviral Profiling of Pyrrolo- and Furo-Fused 7-Deazapurine Ribonucleosides.
Tokarenko, Anna; Lišková, Barbora; Smoleń, Sabina; Táborská, Natálie; Tichý, Michal; Gurská, Soňa; Perlíková, Pavla; Frydrych, Ivo; Tloušt'ová, Eva; Znojek, Pawel; Mertlíková-Kaiserová, Helena; Poštová Slavětínská, Lenka; Pohl, Radek; Klepetářová, Blanka; Khalid, Noor-Ul-Ain; Wenren, Yiqian; Laposa, Rebecca R.; Džubák, Petr; Hajdúch, Marián; Hocek, Michal; Journal of medicinal chemistry 61 (2018) 9347–9359; doi:10.1021/acs.jmedchem.8b01258

data_1553278
_publ_section_title
;
 Synthesis and Cytotoxic and Antiviral Profiling of Pyrrolo- and
 Furo-Fused 7-Deazapurine Ribonucleosides.
;
_journal_issue                   20
_journal_name_full               'Journal of medicinal chemistry'
_journal_page_first              9347
_journal_page_last               9359
_journal_paper_doi               10.1021/acs.jmedchem.8b01258
_journal_volume                  61
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C9 H7 Cl1 N6'
_chemical_formula_sum            'C9 H7 Cl N6'
_chemical_formula_weight         234.65
_chemical_name_systematic
7-chloro-8-(1-methyl-1H-pyrrol-3-yl)tetrazolo[1,5-c]pyrimidine
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.436(4)
_cell_length_b                   9.003(6)
_cell_length_c                   21.664(12)
_cell_measurement_reflns_used    1771
_cell_measurement_temperature    180
_cell_measurement_theta_max      23.2609
_cell_measurement_theta_min      2.3374
_cell_volume                     1060.2(12)
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_collection       'Xcalibur, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      180
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction XCALIBUR'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.061
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            31055
_diffrn_reflns_theta_full        25.025
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_min         2.450
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.341
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.82
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       stick
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.89
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.14
_refine_diff_density_min         -0.17
_refine_ls_abs_structure_details 'Flack (1983), 750 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.05(7)
_refine_ls_extinction_coef       199(15)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   1.1252
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         1565
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0296
_refine_ls_shift/su_max          0.0004076
_refine_ls_shift/su_mean         0.0000242
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 0.199 0.120 0.974E-01 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0411
_refine_ls_wR_factor_gt          0.0299
_refine_ls_wR_factor_ref         0.0299
_reflns_limit_h_max              6
_reflns_limit_h_min              -6
_reflns_limit_k_max              10
_reflns_limit_k_min              0
_reflns_limit_l_max              25
_reflns_limit_l_min              0
_reflns_number_gt                1565
_reflns_number_total             1880
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.76
_oxford_diffrn_Wilson_scale      11.15
_oxford_refine_ls_r_factor_ref   0.0296
_oxford_refine_ls_scale          0.3052(6)
_oxford_reflns_number_all        1880
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_iucr_refine_instructions_details_constraints
;
BLOCK SCALE X'S, U'S 
CONT EXTPARAM 
CONT ENANTIO 
RIDE C   (  15,X'S) H   ( 153,X'S) H   ( 152,X'S) H   ( 151,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
END                                                                             
;
_iucr_refine_instructions_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_cod_data_source_file            jm8b01258_si_003.cif
_cod_data_source_block           1
_cod_original_formula_sum        'C9 H7 Cl1 N6'
_cod_database_code               1553278