Light-induced one-pot synthesis of pyrimidine derivatives from vinyl azides.
Nguyen, Tuan K.; Titov, Gleb D.; Khoroshilova, Olesya V.; Kinzhalov, Mikhail A.; Rostovskii, Nikolai V.; Organic & biomolecular chemistry 18 (2020) 4971–4982; doi:10.1039/d0ob00693a

data_7157540
_publ_section_title
;
 Light-induced one-pot synthesis of pyrimidine derivatives from vinyl
 azides.
;
_journal_issue                   26
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4971
_journal_page_last               4982
_journal_paper_doi               10.1039/d0ob00693a
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C30 H24 Cl3 N3 O6'
_chemical_formula_sum            'C30 H24 Cl3 N3 O6'
_chemical_formula_weight         628.87
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2020-03-19
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2020-03-31 deposited with the CCDC.	2020-06-15 downloaded from the CCDC.
;
_cell_angle_alpha                100.624(8)
_cell_angle_beta                 113.849(7)
_cell_angle_gamma                110.012(8)
_cell_formula_units_Z            2
_cell_length_a                   10.9534(8)
_cell_length_b                   12.5947(13)
_cell_length_c                   13.2276(10)
_cell_measurement_reflns_used    4284
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.5020
_cell_measurement_theta_min      4.4040
_cell_volume                     1453.4(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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(2)
_diffrn_detector_area_resol_mean 10.3829
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.974
_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    -49.00  36.00   1.00    1.00    --  -40.25  38.00  60.00   85
  2  \w     20.00 114.00   1.00    1.00    --   40.25  38.00 150.00   94
  3  \w    101.00 178.00   1.00    2.00    --  113.00 112.00  90.00   77
  4  \w    124.00 163.00   1.00    2.00    --  113.00 112.00  60.00   39
  5  \w    102.00 171.00   1.00    2.00    --  113.00 112.00 150.00   69
  6  \w    101.00 144.00   1.00    2.00    --  113.00  45.00  30.00   43
  7  \w     88.00 162.00   1.00    2.00    --  113.00  45.00 -90.00   74
  8  \w     89.00 160.00   1.00    2.00    --  113.00  77.00-150.00   71
  9  \w     82.00 169.00   1.00    2.00    --  113.00  77.00 -30.00   87
 10  \w     87.00 112.00   1.00    2.00    --  113.00 -77.00-180.00   25
 11  \w     78.00 115.00   1.00    2.00    --  113.00-112.00-180.00   37
 12  \w     53.00 114.00   1.00    2.00    --  113.00-112.00 -60.00   61
 13  \w     59.00 114.00   1.00    2.00    --  113.00-112.00  30.00   55
 14  \w    115.00 140.00   1.00    2.00    --  113.00 -77.00 120.00   25
 15  \w     57.00 113.00   1.00    2.00    --  113.00-112.00 120.00   56
 16  \w     46.00 137.00   1.00    2.00    --  113.00 -30.00  30.00   91
 17  \w     67.00  99.00   1.00    1.00    --   40.25-129.00 -99.00   32
 18  \w     35.00  86.00   1.00    2.00    --  113.00 -77.00-180.00   51
 19  \w     -5.00  70.00   1.00    1.00    --   40.25 -77.00-180.00   75
 20  \w     42.00  91.00   1.00    2.00    --  113.00-112.00  90.00   49
 21  \w     42.00  97.00   1.00    2.00    --  113.00 -77.00 120.00   55
 22  \w   -114.00 -15.00   1.00    1.00    --  -40.25 -57.00 -90.00   99
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_av_unetI/netI     0.0549
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10997
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.415
_diffrn_reflns_theta_min         3.942
_exptl_absorpt_coefficient_mu    3.272
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.26810
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (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    1.437
_exptl_crystal_description       prism
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.18
_refine_diff_density_max         1.252
_refine_diff_density_min         -0.689
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     382
_refine_ls_number_reflns         5941
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0780
_refine_ls_R_factor_gt           0.0630
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0829P)^2^+2.6003P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1702
_refine_ls_wR_factor_ref         0.1833
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4696
_reflns_number_total             5941
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob00693a2.cif
_cod_data_source_block           9841-11478_htk145
_cod_depositor_comments
'Adding full bibliography for 7157540--7157542.cif.'
_cod_original_cell_volume        1453.4(2)
_cod_database_code               7157540
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.590
_shelx_estimated_absorpt_t_min   0.403
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C25(H25)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C16(H16), C14(H14), C31(H31), C10(H10), C30(H30), C20(H20), C17(H17),
 C27(H27), C13(H13), C28(H28), C11(H11), C19(H19)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C22(H22A,H22B,H22C), C24(H24A,H24B,H24C)
;
_shelx_res_checksum              71083
_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
;