Solvent-Controlled, Site-Selective N-Alkylation Reactions of Azolo-Fused Ring Heterocycles at N1-, N2-, and N3-Positions, Including Pyrazolo[3,4- d]pyrimidines, Purines, [1,2,3]Triazolo[4,5]pyridines, and Related Deaza-Compounds.
Bookser, Brett C.; Weinhouse, Michael I.; Burns, Aaron C.; Valiere, Andrew N.; Valdez, Lino J.; Stanczak, Pawel; Na, Jim; Rheingold, Arnold L.; Moore, Curtis E.; Dyck, Brian; The Journal of organic chemistry 83 (2018) 6334–6353; doi:10.1021/acs.joc.8b00540

data_4035862
_publ_section_title
;
 Solvent-Controlled, Site-Selective N-Alkylation Reactions of Azolo-Fused
 Ring Heterocycles at N1-, N2-, and N3-Positions, Including Pyrazolo[3,4-
 d]pyrimidines, Purines, [1,2,3]Triazolo[4,5]pyridines, and Related
 Deaza-Compounds.
;
_journal_issue                   12
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6334
_journal_page_last               6353
_journal_paper_doi               10.1021/acs.joc.8b00540
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C6 H5 Cl N4'
_chemical_formula_sum            'C6 H5 Cl N4'
_chemical_formula_weight         168.59
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-08-25
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.259(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.176(3)
_cell_length_b                   12.399(4)
_cell_length_c                   7.156(2)
_cell_measurement_reflns_used    1260
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.42
_cell_measurement_theta_min      5.45
_cell_volume                     722.4(4)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2013.10-0 (Bruker, 2013)'
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_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  0.0528
_diffrn_reflns_av_unetI/netI     0.0511
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            4602
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.621
_diffrn_reflns_theta_min         5.433
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.139
_exptl_absorpt_correction_T_max  0.3200
_exptl_absorpt_correction_T_min  0.1397
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1261 before and 0.0757 after correction.
The Ratio of minimum to maximum transmission is 0.4366.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colorless
_exptl_crystal_colour_primary    colorless
_exptl_crystal_density_diffrn    1.550
_exptl_crystal_description       plate
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.528
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1310
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.126
_refine_ls_R_factor_all          0.0657
_refine_ls_R_factor_gt           0.0545
_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^)+(0.0787P)^2^+1.1127P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1417
_refine_ls_wR_factor_ref         0.1640
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1098
_reflns_number_total             1310
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00540_si_004.cif
_cod_data_source_block           dart168
_cod_database_code               4035862
_shelx_estimated_absorpt_t_max   0.595
_shelx_estimated_absorpt_t_min   0.370
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_shelx_res_checksum              64479
_shelx_hkl_checksum              75736
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'