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_4035858
_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_absolute_configuration ad
_chemical_formula_moiety         'C14 H28 N8 Na2 O8, 2(C7 H8 N4 O), 2(I)'
_chemical_formula_sum            'C28 H44 I2 N16 Na2 O10'
_chemical_formula_weight         1064.57
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   dual
_audit_creation_date             2017-10-09
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   27.7776(14)
_cell_length_b                   44.788(3)
_cell_length_c                   6.8825(4)
_cell_measurement_reflns_used    3374
_cell_measurement_temperature    100
_cell_measurement_theta_max      22.291
_cell_measurement_theta_min      2.337
_cell_volume                     8562.5(9)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX3 v2016.1-0 (Bruker, 2016)'
_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 8.258
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Ultra'
_diffrn_measurement_method       '\w and \f 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  0.0642
_diffrn_reflns_av_unetI/netI     0.0687
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       54
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            16912
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.420
_diffrn_reflns_theta_min         1.725
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker TXS'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.558
_exptl_absorpt_correction_T_max  0.0916
_exptl_absorpt_correction_T_min  0.0667
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/4 (Bruker,2014/4) was used for absorption correction. wR2(int) was 0.0652 before and 0.0579 after correction. The Ratio of minimum to maximum transmission is 0.7282. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            Orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_description       Plank
_exptl_crystal_F_000             4256
_exptl_crystal_size_max          0.053
_exptl_crystal_size_mid          0.021
_exptl_crystal_size_min          0.005
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.085
_refine_ls_abs_structure_details
;
 Flack x determined using 1141 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.028(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         3922
_refine_ls_number_restraints     11
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0370
_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^)+(0.0201P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0556
_refine_ls_wR_factor_ref         0.0611
_reflns_Friedel_coverage         0.825
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                3145
_reflns_number_total             3922
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00540_si_010.cif
_cod_data_source_block           Dart113
_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.

data item '_exptl_crystal_colour_primary' value 'Orange' was changed
to 'orange' 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_original_cell_volume        8562.6(8)
_cod_database_code               4035858
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.922
_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, All O(H) groups, All O(H,H) groups
2. Restrained distances
 O2S-H2S = O1S-H1S
 0.95 with sigma of 0.02
 H2S-H2S_$1
 1.45 with sigma of 0.02
 H1S_$1-H1S
 1.45 with sigma of 0.02
 O3S-H3SA = O3S-H3SB
 0.95 with sigma of 0.02
 H3SB-H3SA
 1.45 with sigma of 0.02
 H4SA-H4SB
 1.45 with sigma of 0.02
 O4S-H4SA = O4S-H4SB
 0.95 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C3B(H3B), C6B(H6B)
3.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C8B(H8BA,H8BB,H8BC), C9B(H9BA,H9BB,H9BC)
;
_shelx_res_checksum              80493
_shelx_hkl_checksum              53373
_olex2_submission_special_instructions 'No special instructions were received'