Blue light-induced diazo cross-coupling: synthesis of allyldiazo compounds through reshuffling of functionalities.
Tian, Jiabao; Ling, Jiahao; Wang, Yanan; Zhou, Lei; Chemical science 16 (2025) 5701–5706; doi:10.1039/d5sc00277j

data_1574039
_publ_section_title
;
 Blue light-induced diazo cross-coupling: synthesis of allyldiazo
 compounds through reshuffling of functionalities.
;
_journal_issue                   13
_journal_name_full               'Chemical science'
_journal_page_first              5701
_journal_page_last               5706
_journal_paper_doi               10.1039/d5sc00277j
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C20 H17 Cl N2 O3'
_chemical_formula_sum            'C20 H17 Cl N2 O3'
_chemical_formula_weight         368.80
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-09-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-07-10 deposited with the CCDC.	2025-02-28 downloaded from the CCDC.
;
_cell_angle_alpha                98.57(2)
_cell_angle_beta                 97.62(2)
_cell_angle_gamma                91.31(3)
_cell_formula_units_Z            2
_cell_length_a                   5.872(3)
_cell_length_b                   7.735(3)
_cell_length_c                   20.137(3)
_cell_measurement_reflns_used    1296
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      75.8680
_cell_measurement_theta_min      4.4838
_cell_volume                     895.6(6)
_computing_cell_refinement       'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_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_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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    -47.00 -13.00   1.00    1.50    --  -40.69 125.00 120.00   34
  2  \w   -112.00 -25.00   1.00    1.50    --  -40.69 -38.00-120.00   87
  3  \w   -113.00 -27.00   1.00    1.50    --  -40.69 -38.00 -30.00   86
  4  \w    -75.00  -7.00   1.00    1.50    --  -40.69 125.00  30.00   68
  5  \w     46.00  92.00   1.00    1.50    --   40.69-125.00 -60.00   46
  6  \w    108.00 156.00   1.00    6.00    --  104.75 125.00 150.00   48
  7  \w     46.00  78.00   1.00    6.00    --  104.75-125.00-120.00   32
  8  \w     32.00 132.00   1.00    6.00    --  104.75 -77.00  60.00  100
  9  \w     95.00 125.00   1.00    6.00    --  104.75 -30.00  30.00   30
 10  \w     44.00  73.00   1.00    6.00    --  104.75 -30.00  30.00   29
 11  \w     84.00 111.00   1.00    6.00    --  104.75-125.00   0.00   27
 12  \w     82.00 113.00   1.00    6.00    --  104.75-125.00-120.00   31
 13  \w     64.00 175.00   1.00    6.00    --  104.75  15.00-120.00  111
 14  \w     37.00  64.00   1.00    6.00    --  104.75-125.00   0.00   27
 15  \w     44.00 113.00   1.00    6.00    --  104.75-125.00  30.00   69
 16  \w    112.00 178.00   1.00    6.00    --  104.75 102.00  59.00   66
 17  \w     85.00 174.00   1.00    6.00    --  104.75  61.00 120.00   89
 18  \w    141.00 168.00   1.00    6.00    --  104.75  77.00-180.00   27
 19  \w     41.00 119.00   1.00    6.00    --  104.75-133.00 -62.78   78
 20  \w      3.00  28.00   1.00    2.00    --   38.00  89.00-113.55   25
 21  \w      4.00  30.00   1.00    2.00    --   38.00  86.00  -9.87   26
 22  \w    -57.00  35.00   1.00    2.00    --  -42.19  19.00 -30.00   92
 23  \w   -110.00 -54.00   1.00    2.00    --  -42.19 -57.00 150.00   56
 24  \w    -44.00 -17.00   1.00    2.00    --  -42.19 -57.00 150.00   27
 25  \w     14.00  39.00   1.00    2.00    --   46.00  78.00  87.49   25
 26  \w     14.00  39.00   1.00    2.00    --   46.00  81.00 139.67   25
 27  \w     32.00  66.00   1.00    2.00    --   58.00  60.00 -11.31   34
 28  \w     29.00  58.00   1.00    2.00    --   58.00  66.00-126.98   29
 29  \w     28.00  63.00   1.00    2.00    --   58.00  70.00 164.56   35
 30  \w     28.00  53.00   1.00    2.00    --   58.00  71.00 -86.67   25
 31  \w     33.00  72.00   1.00    2.00    --   62.00  71.00  18.59   39
 32  \w     38.00  64.00   1.00    2.00    --   66.00  64.00 135.04   26
 33  \w     42.00  82.00   1.00    2.00    --   70.00  69.00 -75.21   40
 34  \w     40.00  68.00   1.00    2.00    --   70.00  71.00 -13.26   28
 35  \w     42.00  75.00   1.00    2.00    --   70.00  70.00  68.01   33
 36  \w     50.00  81.00   1.00    8.00    --   78.00  61.00 159.15   31
 37  \w     54.00  80.00   1.00    8.00    --   78.00  47.00-100.84   26
 38  \w    114.00 147.00   1.00    8.00    --   90.00  69.00 150.98   33
 39  \w     64.00  92.00   1.00    8.00    --   90.00  69.00 150.98   28
 40  \w     78.00 122.00   1.00    8.00    --  104.75  61.00 -60.00   44
 41  \w     77.00 139.00   1.00    8.00    --  104.75  62.00  60.76   62
 42  \w     77.00 103.00   1.00    8.00    --  104.75  61.00-150.00   26
 43  \w    132.00 161.00   1.00    8.00    --  104.75  61.00 -30.00   29
 44  \w     78.00 116.00   1.00    8.00    --  104.75  61.00 -30.00   38
 45  \w     78.00 104.00   1.00    8.00    --  104.75  61.00-180.00   26
 46  \w     77.00 151.00   1.00    8.00    --  104.75  61.00  30.00   74
 47  \w    135.00 171.00   1.00    8.00    --  104.75  61.00   0.00   36
 48  \w     77.00 111.00   1.00    8.00    --  104.75  61.00   0.00   34
 49  \w     77.00 123.00   1.00    8.00    --  104.75  61.00  90.00   46
 50  \w    128.00 173.00   1.00    8.00    --  104.75  61.00 -90.00   45
 51  \w     81.00 121.00   1.00    8.00    --  104.75  61.00 -90.00   40
 52  \w     77.00 103.00   1.00    8.00    --  104.75  61.00-120.00   26
 53  \w    133.00 172.00   1.00    8.00    --  104.75  61.00 -60.00   39
 54  \w     57.00  83.00   1.00    8.00    --   82.00  69.00 -72.09   26
 55  \w     52.00  81.00   1.00    8.00    --   82.00  71.00 113.04   29
 56  \w    129.00 154.00   1.00    8.00    --   82.00  71.00 113.04   25
 57  \w     62.00  88.00   1.00    8.00    --   90.00  67.00 -51.12   26
 58  \w     67.00  93.00   1.00    8.00    --   90.00  53.00-149.21   26
 59  \w     58.00  84.00   1.00    8.00    --   82.00  66.00-115.08   26
 60  \w      3.00  28.00   1.00    3.00    --  -42.19  57.00-120.00   25
 61  \w     14.00  39.00   1.00    3.00    --   46.00  80.00-169.67   25
 62  \w     42.00  68.00   1.00    3.00    --   62.00  71.00 -94.20   26
 63  \w     63.00  89.00   1.00   12.00    --   86.00  48.00  64.81   26
 64  \w     66.00  92.00   1.00   12.00    --   94.00  64.00  -7.95   26
 65  \w     89.00 136.00   1.00   12.00    --  104.75 -77.00   0.00   47
 66  \w     77.00 103.00   1.00   12.00    --  104.75  61.00 111.92   26
 67  \w     93.00 119.00   1.00   12.00    --  104.75  45.00-150.00   26
 68  \w     92.00 118.00   1.00   12.00    --  104.75  45.00 -90.00   26
 69  \w     80.00 106.00   1.00   12.00    --  104.75  61.00 120.00   26
 70  \w     86.00 112.00   1.00   12.00    --  104.75  45.00-180.00   26
 71  \w     23.00  49.00   1.00    4.00    --   50.00  70.00 150.79   26
 72  \w     34.00  60.00   1.00    4.00    --   62.00  71.00-119.78   26
 73  \w     45.00  71.00   1.00    4.00    --   70.00  64.00-162.18   26
 74  \w     44.00  70.00   1.00    4.00    --   74.00  71.00 -98.02   26
 75  \w     55.00  81.00   1.00   16.00    --   82.00  69.00-152.36   26
 76  \w     64.00  90.00   1.00   16.00    --   90.00  55.00-157.09   26
 77  \w     78.00 104.00   1.00   16.00    --  106.00  68.00 130.52   26
 78  \w     81.00 107.00   1.00   16.00    --  106.00  66.00-140.21   26
 79  \w     84.00 109.00   1.00   16.00    --  111.00-111.00 -60.00   25
 80  \w    125.00 163.00   1.00   16.00    --  111.00  61.00-180.00   38
 81  \w    110.00 146.00   1.00   16.00    --  111.00 111.00  30.00   36
 82  \w     54.00  81.00   1.00   16.00    --  111.00-111.00 -60.00   27
 83  \w     44.00  71.00   1.00   16.00    --  111.00 -77.00   0.00   27
 84  \w     61.00  93.00   1.00   16.00    --  111.00 178.00 -60.00   32
 85  \w    146.00 172.00   1.00   16.00    --  111.00  30.00   0.00   26
 86  \w     87.00 122.00   1.00   16.00    --  111.00  30.00   0.00   35
 87  \w     77.00 109.00   1.00   16.00    --  111.00-111.00 -90.00   32
 88  \w    127.00 178.00   1.00   16.00    --  111.00  61.00-120.00   51
 89  \w     80.00 108.00   1.00   16.00    --  111.00-111.00  60.00   28
 90  \w     92.00 124.00   1.00   16.00    --  111.00  45.00-150.00   32
 91  \w    132.00 177.00   1.00   16.00    --  111.00  45.00-150.00   45
 92  \w    120.00 155.00   1.00   16.00    --  111.00 111.00   0.00   35
 93  \w     84.00 115.00   1.00   16.00    --  111.00  61.00-120.00   31
 94  \w    117.00 145.00   1.00   16.00    --  111.00 111.00  90.00   28
 95  \w    149.00 175.00   1.00   16.00    --  111.00 111.00  90.00   26
 96  \w     71.00 106.00   1.00   16.00    --  111.00-111.00-180.00   35
 97  \w     74.00 109.00   1.00   16.00    --  111.00-111.00  90.00   35
 98  \w    110.00 142.00   1.00   16.00    --  111.00 -77.00   0.00   32
 99  \w     40.00  66.00   1.00   16.00    --  111.00-111.00-120.00   26
100  \w     84.00 109.00   1.00   16.00    --  111.00-111.00-120.00   25
101  \w     71.00 110.00   1.00   16.00    --  111.00 -45.00  60.00   39
102  \w     90.00 129.00   1.00   16.00    --  111.00  61.00   0.00   39
103  \w    144.00 170.00   1.00   16.00    --  111.00  61.00 -90.00   26
104  \w    103.00 159.00   1.00   16.00    --  111.00  77.00  90.00   56
105  \w     52.00 101.00   1.00   16.00    --  111.00-102.00 -43.00   49
106  \w    123.00 168.00   1.00   16.00    --  111.00 111.00 -60.00   45
107  \w     87.00 116.00   1.00   16.00    --  111.00  61.00 150.00   29
108  \w    130.00 168.00   1.00   16.00    --  111.00  61.00 150.00   38
109  \w     83.00 115.00   1.00   16.00    --  111.00  61.00 -90.00   32
110  \w     85.00 111.00   1.00   16.00    --  111.00  61.00 -60.00   26
111  \w    134.00 160.00   1.00   16.00    --  111.00  61.00 -60.00   26
112  \w     87.00 113.00   1.00   16.00    --  111.00  61.00  30.00   26
113  \w     76.00 125.00   1.00   16.00    --  111.00 -45.00 -30.00   49
114  \w     89.00 127.00   1.00   16.00    --  111.00  45.00  90.00   38
115  \w     91.00 117.00   1.00   16.00    --  111.00  45.00 150.00   26
116  \w     86.00 112.00   1.00   16.00    --  111.00  61.00-180.00   26
117  \w    129.00 174.00   1.00   16.00    --  111.00  77.00 120.00   45
118  \w    115.00 142.00   1.00   16.00    --  111.00 178.00 -60.00   27
119  \w    -44.00 129.00   1.00    4.00    --   42.19   0.00   0.00  173
120  \w    -44.00 129.00   1.00    4.00    --   42.19   0.00  30.00  173
121  \w    -44.00 125.00   1.00    4.00    --   42.19   0.00  60.00  169
122  \w    -44.00 129.00   1.00    4.00    --   42.19   0.00-180.00  173
123  \w    -44.00 129.00   1.00    4.00    --   42.19   0.00-150.00  173
124  \w    -44.00 129.00   1.00    4.00    --   42.19   0.00-120.00  173
125  \w    -44.00 129.00   1.00    4.00    --   42.19   0.00 -90.00  173
126  \w    -44.00 129.00   1.00    4.00    --   42.19   0.00 -60.00  173
127  \w    -44.00 129.00   1.00    4.00    --   42.19   0.00 -30.00  173
128  \w     20.00 122.00   1.00    4.00    --   50.00  70.00 150.79  102
129  \w     32.00  79.00   1.00    4.00    --   62.00  71.00-119.78   47
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0246811000
_diffrn_orient_matrix_UB_12      -0.0166806000
_diffrn_orient_matrix_UB_13      0.0740220000
_diffrn_orient_matrix_UB_21      -0.0839009000
_diffrn_orient_matrix_UB_22      0.1880610000
_diffrn_orient_matrix_UB_23      0.0110012000
_diffrn_orient_matrix_UB_31      -0.2500898000
_diffrn_orient_matrix_UB_32      -0.0707356000
_diffrn_orient_matrix_UB_33      -0.0223878000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            25218
_diffrn_reflns_point_group_measured_fraction_full 0.947
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        65.079
_diffrn_reflns_theta_max         65.079
_diffrn_reflns_theta_min         4.484
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.078
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76205
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.92a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.500
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details
;
 Flack x determined using 2032 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.024(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     471
_refine_ls_number_reflns         5766
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0582
_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^)+(0.1099P)^2^+0.3326P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1722
_refine_ls_wR_factor_ref         0.1779
_reflns_Friedel_coverage         0.899
_reflns_Friedel_fraction_full    0.896
_reflns_Friedel_fraction_max     0.896
_reflns_number_gt                4941
_reflns_number_total             5766
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc00277j2.cif
_cod_data_source_block           a23091303a0377
_cod_depositor_comments
'Adding full bibliography for 1574039--1574041.cif.'
_cod_original_cell_volume        895.6(5)
_cod_database_code               1574039
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C20H17ClN2O3
_chemical_oxdiff_usercomment     Cl1
_shelx_estimated_absorpt_t_max   0.921
_shelx_estimated_absorpt_t_min   0.746
_diffrn_oxdiff_digest_frames
;
011cb8b7c74b36100f8f6ffa1132a0795b029181868
;
_diffrn_oxdiff_digest_hkl
;
015b165af6cc74c507b4c7b6c7028196cc7586
;
_reflns_odcompleteness_completeness 99.72
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00W(H00A,H00B), C00Z(H00C,H00D), C01D(H01I,H01J), C01E(H01C,H01D)
2.b Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00F(H00F), C00H(H00H), C00K(H00K), C00L(H00L), C00M(H00M),
 C00N(H00N), C00O(H00O), C00R(H00R), C00X(H00X), C010(H010), C012(H012),
 C014(H014), C015(H015), C017(H017), C018(H018), C019(H019), C01A(H01A),
 C01B(H01B), C01C(H01H)
2.c Idealised Me refined as rotating group:
 C01F(H01E,H01F,H01G), C01G(H01K,H01L,H01M)
;
_olex2_date_sample_data_collection 2023-09-13
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.481
_oxdiff_exptl_absorpt_empirical_full_min 0.651