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_7157542
_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_absolute_configuration unk
_chemical_formula_moiety         'C20 H14 Cl4 N2 O4'
_chemical_formula_sum            'C20 H14 Cl4 N2 O4'
_chemical_formula_weight         488.13
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_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                90
_cell_angle_beta                 109.7710(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.82480(10)
_cell_length_b                   16.44070(10)
_cell_length_c                   12.04070(10)
_cell_measurement_reflns_used    19869
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.2600
_cell_measurement_theta_min      3.8950
_cell_volume                     2016.53(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -20.00   6.00   0.50    0.40    --   38.95 -54.00-138.00   52
  2  \w     29.00  64.00   0.50    0.40    --   38.95  54.00   6.00   70
  3  \w     67.00 102.00   0.50    0.40    --   38.95  54.00   6.00   70
  4  \w     80.00 141.00   0.50    0.90    --  100.00  54.00   6.00  122
  5  \w     70.00 118.00   0.50    0.90    --  100.00 -54.00-138.00   96
  6  \w     42.00  68.00   0.50    0.90    --  100.00 -54.00-138.00   52
  7  \w     -7.00  21.00   0.50    0.40    --  -38.95  32.00 120.00   56
  8  \w    -46.00 -20.00   0.50    0.40    --  -38.95  32.00 120.00   52
  9  \w    -72.00 -46.00   0.50    0.40    --  -38.95 -21.00-120.00   52
 10  \w    -46.00 -21.00   0.50    0.40    --  -38.95 -54.00-138.00   50
 11  \w    -80.00 -54.00   0.50    0.40    --  -38.95 -54.00-138.00   52
 12  \w    -56.00  25.00   0.50    0.40    --  -38.95  43.00-180.00  162
 13  \w   -107.00 -79.00   0.50    0.40    --  -38.95 -21.00-120.00   56
 14  \w    -34.00  -8.00   0.50    0.40    --  -38.95  54.00   6.00   52
 15  \w     23.00  49.00   0.50    0.40    --   38.95  21.00  90.00   52
 16  \w     76.00 106.00   0.50    0.40    --   38.95  21.00 -30.00   60
 17  \w     32.00 100.00   0.50    0.40    --   38.95  65.00  30.00  136
 18  \w     24.00  72.00   0.50    0.40    --   38.95  21.00 -30.00   96
 19  \w     22.00  49.00   0.50    0.40    --   38.95 -54.00-138.00   54
 20  \w     76.00 102.00   0.50    0.40    --   38.95  21.00  90.00   52
 21  \w    -17.00  53.00   0.50    0.40    --   38.95 -43.00  90.00  140
 22  \w     35.00  61.00   0.50    0.40    --   38.95  32.00   0.00   52
 23  \w     31.00  80.00   0.50    0.90    --  100.00-111.00 -90.00   98
 24  \w    130.00 156.00   0.50    0.90    --  100.00   7.00 -30.00   52
 25  \w     78.00 124.00   0.50    0.90    --  100.00 -69.00   0.00   92
 26  \w     84.00 155.00   0.50    0.90    --  100.00 133.00-120.00  142
 27  \w     94.00 119.00   0.50    0.90    --  100.00 -22.00  90.00   50
 28  \w     61.00  93.00   0.50    0.90    --  100.00   7.00 -30.00   64
 29  \w     63.00  89.00   0.50    0.90    --  100.00 -22.00  90.00   52
 30  \w     83.00 114.00   0.50    0.90    --  100.00 -30.00-180.00   62
 31  \w     46.00 116.00   0.50    0.90    --  100.00 -45.00  90.00  140
 32  \w     32.00  63.00   0.50    0.90    --  100.00 -30.00-180.00   62
 33  \w     83.00 110.00   0.50    0.90    --  100.00 -45.00   0.00   54
 34  \w    108.00 156.00   0.50    0.90    --  100.00  93.00  60.00   96
 35  \w     78.00 125.00   0.50    0.90    --  100.00  61.00 150.00   94
 36  \w     31.00  75.00   0.50    0.90    --  100.00 -30.00  30.00   88
 37  \w     84.00 125.00   0.50    0.90    --  100.00 111.00  60.00   82
 38  \w     61.00 104.00   0.50    0.90    --  100.00 -61.00   0.00   86
 39  \w    107.00 133.00   0.50    0.90    --  100.00  30.00  90.00   52
 40  \w    101.00 157.00   0.50    0.90    --  100.00  93.00-150.00  112
 41  \w     86.00 134.00   0.50    0.90    --  100.00 111.00 -90.00   96
 42  \w     86.00 152.00   0.50    0.90    --  100.00  53.00 -30.00  132
 43  \w     93.00 147.00   0.50    0.90    --  100.00  93.00 -30.00  108
 44  \w     40.00  66.00   0.50    0.90    --  100.00 -54.00-138.00   52
 45  \w    -77.00 -25.00   0.50    0.40    --  -38.95 -32.00  90.00  104
 46  \w     18.00  56.00   0.50    0.40    --   38.95  65.00 120.00   76
 47  \w     82.00 108.00   0.50    0.40    --   38.95  32.00-150.00   52
 48  \w     61.00 101.00   0.50    0.40    --   38.95  65.00 120.00   80
 49  \w     21.00  90.00   0.50    0.40    --   38.95  65.00 150.00  138
 50  \w     15.00  59.00   0.50    0.40    --   38.95 -11.00-150.00   88
 51  \w    -27.00   6.00   0.50    0.40    --   38.95 -11.00-150.00   66
 52  \w     -3.00  48.00   0.50    0.40    --   38.95 -32.00 120.00  102
 53  \w     31.00  57.00   0.50    0.40    --   38.95  65.00  90.00   52
 54  \w     63.00  97.00   0.50    0.40    --   38.95  65.00  90.00   68
 55  \w     86.00 114.00   0.50    0.90    --  100.00  53.00 -60.00   56
 56  \w     76.00 101.00   0.50    0.90    --  100.00  69.00 120.00   50
 57  \w     78.00 110.00   0.50    0.90    --  100.00  61.00 120.00   64
 58  \w    106.00 153.00   0.50    0.90    --  100.00  93.00   0.00   94
 59  \w    114.00 157.00   0.50    0.90    --  100.00  67.00  99.99   86
 60  \w    121.00 154.00   0.50    0.90    --  100.00  69.00  30.00   66
 61  \w    132.00 157.00   0.50    0.90    --  100.00  69.00  60.00   50
 62  \w     93.00 119.00   0.50    0.90    --  100.00  69.00  30.00   52
 63  \w     84.00 110.00   0.50    0.90    --  100.00  45.00 150.00   52
 64  \w    110.00 136.00   0.50    0.90    --  100.00 133.00 120.00   52
 65  \w    118.00 157.00   0.50    0.90    --  100.00 133.00 150.00   78
 66  \w     76.00 102.00   0.50    0.90    --  100.00  67.00  99.99   52
 67  \w    113.00 149.00   0.50    0.90    --  100.00  77.00 120.00   72
 68  \w     80.00 121.00   0.50    0.90    --  100.00  53.00 150.00   82
 69  \w    127.00 153.00   0.50    0.90    --  100.00  53.00 150.00   52
 70  \w     75.00 108.00   0.50    0.90    --  100.00-111.00-120.00   66
 71  \w    132.00 157.00   0.50    0.90    --  100.00  69.00  90.00   50
 72  \w    120.00 146.00   0.50    0.90    --  100.00  61.00 120.00   52
 73  \w     76.00 112.00   0.50    0.90    --  100.00  69.00  60.00   72
 74  \w     36.00  61.00   0.50    0.90    --  100.00-133.00  30.00   50
 75  \w     80.00 120.00   0.50    0.90    --  100.00  53.00-180.00   80
 76  \w     86.00 115.00   0.50    0.90    --  100.00  61.00-150.00   58
 77  \w     80.00 106.00   0.50    0.90    --  100.00  53.00  90.00   52
 78  \w     76.00 105.00   0.50    0.90    --  100.00  69.00  90.00   58
 79  \w     83.00 109.00   0.50    0.90    --  100.00  45.00  90.00   52
 80  \w    132.00 157.00   0.50    0.90    --  100.00  61.00-150.00   50
 81  \w     78.00 107.00   0.50    0.90    --  100.00  61.00  90.00   58
 82  \w     43.00  94.00   0.50    0.90    --  100.00 -93.00  60.00  102
 83  \w     79.00 104.00   0.50    0.90    --  100.00  61.00  60.00   50
 84  \w     82.00 130.00   0.50    0.90    --  100.00 -86.00-180.00   96
 85  \w     76.00 101.00   0.50    0.90    --  100.00  69.00 150.00   50
 86  \w     26.00  51.00   0.50    0.90    --  100.00 -93.00 -30.00   50
 87  \w    108.00 140.00   0.50    0.90    --  100.00 111.00  30.00   64
 88  \w     83.00 109.00   0.50    0.90    --  100.00  77.00  60.00   52
 89  \w     83.00 108.00   0.50    0.90    --  100.00  77.00  90.00   50
 90  \w     83.00 109.00   0.50    0.90    --  100.00  77.00 120.00   52
 91  \w    130.00 156.00   0.50    0.90    --  100.00  53.00 -60.00   52
 92  \w    106.00 131.00   0.50    0.90    --  100.00  22.00 -60.00   50
 93  \w     82.00 108.00   0.50    0.90    --  100.00-111.00-180.00   52
 94  \w     37.00  65.00   0.50    0.90    --  100.00-111.00   0.00   56
 95  \w     86.00 120.00   0.50    0.90    --  100.00  37.00  60.00   68
 96  \w     80.00 110.00   0.50    0.90    --  100.00  53.00 120.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1369845000
_diffrn_orient_matrix_UB_12      -0.0247362000
_diffrn_orient_matrix_UB_13      0.0841085000
_diffrn_orient_matrix_UB_21      0.0640861000
_diffrn_orient_matrix_UB_22      0.0555530000
_diffrn_orient_matrix_UB_23      -0.0680923000
_diffrn_orient_matrix_UB_31      -0.0024101000
_diffrn_orient_matrix_UB_32      0.0712990000
_diffrn_orient_matrix_UB_33      0.0822795000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            25202
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.448
_diffrn_reflns_theta_min         3.901
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.619
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83397
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_description       prism
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 3387 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.009(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     553
_refine_ls_number_reflns         7584
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0241
_refine_ls_R_factor_gt           0.0233
_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^)+(0.0340P)^2^+0.0377P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0580
_refine_ls_wR_factor_ref         0.0585
_reflns_Friedel_coverage         0.895
_reflns_Friedel_fraction_full    0.967
_reflns_Friedel_fraction_max     0.963
_reflns_number_gt                7401
_reflns_number_total             7584
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob00693a2.cif
_cod_data_source_block           15289_htk-02
_cod_depositor_comments
'Adding full bibliography for 7157540--7157542.cif.'
_cod_database_code               7157542
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C20 H14 Cl4 N2 O4'
_reflns_odcompleteness_completeness 99.11
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     70.93
_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 Ternary CH refined with riding coordinates:
 C2(H2A), C2A(H2AB)
2.b Aromatic/amide H refined with riding coordinates:
 C7A(H7A), C16(H16), C15(H15), C15A(H15A), C10A(H10A), C13(H13), C7(H7),
 C10(H10), C9(H9), C13A(H13A), C9A(H9A), C16A(H16A)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C18(H18A,H18B,H18C), C18A(H18D,H18E,H18F), C20A(H20D,
 H20E,H20F)
;
_shelx_res_checksum              50634
_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 2.314
_oxdiff_exptl_absorpt_empirical_full_min 0.853