Novel aryltriazole acyclic C-azanucleosides as anticancer candidates.
Zhang, Yanhua; Lin, Yun; Hou, Qianqian; Liu, Xi; Pricl, Sabrina; Peng, Ling; Xia, Yi; Organic & biomolecular chemistry 18 (2020) 9689–9699; doi:10.1039/d0ob02164d

data_7157750
_publ_section_title
;
 Novel aryltriazole acyclic C-azanucleosides as anticancer candidates.
;
_journal_issue                   47
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9689
_journal_page_last               9699
_journal_paper_doi               10.1039/d0ob02164d
_journal_volume                  18
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C11 H13 Cl N4 O'
_chemical_formula_sum            'C11 H13 Cl N4 O'
_chemical_formula_weight         252.70
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-03-25
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_audit_update_record
;
2019-03-27 deposited with the CCDC.	2020-11-17 downloaded from the CCDC.
;
_cell_angle_alpha                97.735(11)
_cell_angle_beta                 94.192(11)
_cell_angle_gamma                92.200(11)
_cell_formula_units_Z            1
_cell_length_a                   4.4944(6)
_cell_length_b                   5.4263(7)
_cell_length_c                   12.2978(16)
_cell_measurement_reflns_used    528
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.6840
_cell_measurement_theta_min      3.9180
_cell_volume                     296.04(7)
_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      293(2)
_diffrn_detector_area_resol_mean 16.0892
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.852
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0157
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.852
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2050
_diffrn_reflns_point_group_measured_fraction_full 0.611
_diffrn_reflns_point_group_measured_fraction_max 0.511
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.948
_diffrn_reflns_theta_min         3.794
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.312
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31624
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_description       block
_exptl_crystal_F_000             132
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 213 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         1604
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0426
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0529P)^2^+0.0062P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.1135
_reflns_Friedel_coverage         0.200
_reflns_Friedel_fraction_full    0.224
_reflns_Friedel_fraction_max     0.170
_reflns_number_gt                1203
_reflns_number_total             1604
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob02164d2.cif
_cod_data_source_block           20190325-xiayi-zyh-716
_cod_depositor_comments          'Adding full bibliography for 7157750.cif.'
_cod_database_code               7157750
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C2(H2A,H2B), C1(H1B,H1C)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C10(H10), C11(H11), C7(H7), C8(H8)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_olex2_submission_special_instructions 'No special instructions were received'