Visible light-induced direct alkylation of the purine C<sub>8</sub>-H bond with ethers.
Lu, Changtong; Histand, Gary; Lin, Dongen; Organic & biomolecular chemistry 21 (2023) 3167–3171; doi:10.1039/d3ob00147d

data_7159248
_publ_section_title
;
 Visible light-induced direct alkylation of the purine C<sub>8</sub>-H
 bond with ethers.
;
_journal_issue                   15
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3167
_journal_page_last               3171
_journal_paper_doi               10.1039/d3ob00147d
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C16 H14 Cl2 N4 O'
_chemical_formula_sum            'C16 H14 Cl2 N4 O'
_chemical_formula_weight         349.21
_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     direct
_audit_creation_date             2021-12-09
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-10-09 deposited with the CCDC.	2023-03-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.09(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.7826(9)
_cell_length_b                   16.631(3)
_cell_length_c                   19.594(2)
_cell_measurement_reflns_used    2393
_cell_measurement_temperature    179.99(10)
_cell_measurement_theta_max      73.5670
_cell_measurement_theta_min      3.3910
_cell_volume                     1558.5(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      179.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -62.00 -13.00   1.00    1.00    --  -41.11 -57.00 -30.00   49
  2  \w    -78.00 -40.00   1.00    1.00    --  -41.11 -38.00-150.00   38
  3  \w      2.00  74.00   1.00    1.00    --   41.11 -99.00-150.00   72
  4  \w     26.00 110.00   1.00    1.50    --  107.58 -95.00 -60.00   84
  5  \w     35.00 130.00   1.00    1.50    --  107.58 -61.00 120.00   95
  6  \w    129.00 173.00   1.00    1.50    --  107.58  45.00 -90.00   44
  7  \w     82.00 108.00   1.00    1.50    --  107.58  45.00 -90.00   26
  8  \w    102.00 156.00   1.00    1.50    --  107.58 117.00  99.00   54
  9  \w   -116.00 -56.00   1.00    1.00    --  -40.98 -77.00 -30.00   60
 10  \w    118.00 157.00   1.00    1.50    --  107.58  61.00  60.00   39
 11  \w     48.00  79.00   1.00    1.50    --  107.58-125.00  90.00   31
 12  \w     91.00 117.00   1.00    1.50    --  107.58-125.00  90.00   26
 13  \w    112.00 148.00   1.00    1.50    --  107.58  45.00 -60.00   36
 14  \w    144.00 172.00   1.00    1.50    --  107.58 125.00-150.00   28
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1584203000
_diffrn_orient_matrix_UB_12      -0.0516065000
_diffrn_orient_matrix_UB_13      0.0529031000
_diffrn_orient_matrix_UB_21      0.1519467000
_diffrn_orient_matrix_UB_22      -0.0756487000
_diffrn_orient_matrix_UB_23      -0.0266562000
_diffrn_orient_matrix_UB_31      0.2359728000
_diffrn_orient_matrix_UB_32      0.0136851000
_diffrn_orient_matrix_UB_33      0.0516933000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0540
_diffrn_reflns_av_unetI/netI     0.0610
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            5890
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.118
_diffrn_reflns_theta_min         3.486
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.830
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.29326
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_description       needle
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.779
_refine_diff_density_min         -0.864
_refine_diff_density_rms         0.136
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3034
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0796
_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^)+(0.1608P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2037
_refine_ls_wR_factor_ref         0.2175
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2589
_reflns_number_total             3034
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00147d2.cif
_cod_data_source_block           1204
_cod_depositor_comments          'Adding full bibliography for 7159248.cif.'
_cod_database_code               7159248
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.41
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
2. Others
 Sof(H7BC)=Sof(H7BD)=Sof(H9BC)=Sof(H9BD)=Sof(C17)=Sof(H17A)=Sof(H17B)=1-FVAR(1)
 Sof(H7AA)=Sof(H7AB)=Sof(C8)=Sof(H8A)=Sof(H8B)=Sof(H9AA)=Sof(H9AB)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C6(H6)
3.b Secondary CH2 refined with riding coordinates:
 C7(H7AA,H7AB), C7(H7BC,H7BD), C8(H8A,H8B), C9(H9AA,H9AB), C9(H9BC,H9BD),
 C10(H10A,H10B), C17(H17A,H17B)
3.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14), C15(H15), C16(H16)
;
_shelx_res_checksum              43253
_shelx_hkl_checksum              90633
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.629
_oxdiff_exptl_absorpt_empirical_full_min 0.271