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_4035863
_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
_audit_creation_date             2016-09-07
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221)
;
_cell_angle_alpha                90
_cell_angle_beta                 108.474(19)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.008(8)
_cell_length_b                   13.971(15)
_cell_length_c                   7.564(9)
_cell_measurement_reflns_used    1575
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.283
_cell_measurement_theta_min      2.848
_cell_volume                     702.4(14)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'APEX2 v2013.6-2 (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    'ShelXT (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.927
_diffrn_measured_fraction_theta_max 0.765
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Ultra'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_Laue_measured_fraction_full 0.927
_diffrn_reflns_Laue_measured_fraction_max 0.765
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3813
_diffrn_reflns_point_group_measured_fraction_full 0.927
_diffrn_reflns_point_group_measured_fraction_max 0.765
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.535
_diffrn_reflns_theta_min         2.916
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker TXS'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.472
_exptl_absorpt_correction_T_max  0.2590
_exptl_absorpt_correction_T_min  0.2223
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1295 before and 0.0488 after correction.
The Ratio of minimum to maximum transmission is 0.8583.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_description       plate
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.159
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         1239
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.159
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0465
_refine_ls_shift/su_max          0.026
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0259P)^2^+0.5939P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.1035
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1039
_reflns_number_total             1239
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00540_si_009.cif
_cod_data_source_block           dart174
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               4035863
_shelx_estimated_absorpt_t_max   0.963
_shelx_estimated_absorpt_t_min   0.879
_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. Others
 Sof(C4')=Sof(C2')=Sof(C5')=Sof(H4)=Sof(N4')=Sof(C1')=Sof(H4AA)=Sof(H4AB)=
 Sof(H4AC)=Sof(N2')=Sof(C6')=Sof(H2AA)=Sof(N1')=1-FVAR(1)
 Sof(N2)=Sof(C6)=Sof(H6)=Sof(C2)=Sof(N1)=Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=
 Sof(N3)=Sof(C4)=Sof(C5)=Sof(H5)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C5'(H4), C6'(H2AA)
3.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C1'(H4AA,H4AB,H4AC)
;
_shelx_res_checksum              71952
_shelx_hkl_checksum              36358
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'