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_1574041
_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_absolute_configuration ad
_chemical_formula_moiety         'C21 H19 Cl N2 O3'
_chemical_formula_sum            'C21 H19 Cl N2 O3'
_chemical_formula_weight         382.83
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-12-19
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-07-10 deposited with the CCDC.	2025-02-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.308(11)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   20.171(5)
_cell_length_b                   9.765(4)
_cell_length_c                   39.079(11)
_cell_measurement_reflns_used    9698
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      59.150
_cell_measurement_theta_min      3.863
_cell_volume                     7596(4)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_reflns_av_R_equivalents  0.0659
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       50
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_number            106316
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         59.619
_diffrn_reflns_theta_min         1.993
_diffrn_source_current           3.57
_diffrn_source_power             0.24947159999999996
_diffrn_source_voltage           69.88
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.300
_exptl_absorpt_correction_T_max  0.7516
_exptl_absorpt_correction_T_min  0.5904
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1436 before and 0.0830 after correction.
The Ratio of minimum to maximum transmission is 0.7855.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             3200
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.578
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.46(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     982
_refine_ls_number_reflns         16782
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0588
_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^)+(0.1077P)^2^+2.2691P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1624
_refine_ls_wR_factor_ref         0.1768
_reflns_Friedel_coverage         0.999
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                13456
_reflns_number_total             16782
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc00277j2.cif
_cod_data_source_block           b23121001a0316_0m
_cod_depositor_comments
'Adding full bibliography for 1574039--1574041.cif.'
_cod_database_code               1574041
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.974
_shelx_estimated_absorpt_t_min   0.819
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.54(2)
 0.46(2)
2. 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
3.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C20(H20A,H20B), C24(H24A,H24B), C41(H41A,H41B), C44(H44A,H44B),
 C62(H62A,H62B), C66(H66A,H66B), C83(H83A,H83B)
3.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C9(H9), C10(H10), C12(H12), C13(H13), C15(H15), C16(H16), C18(H18),
 C19(H19), C27(H27), C30(H30), C31(H31), C33(H33), C34(H34), C36(H36), C37(H37),
  C39(H39), C40(H40), C47(H47), C51(H51), C52(H52), C54(H54), C55(H55),
 C57(H57), C58(H58), C60(H60), C61(H61), C69(H69), C72(H72), C73(H73), C75(H75),
  C76(H76), C78(H78), C79(H79), C81(H81), C82(H82)
3.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C21(H21A,H21B,H21C), C26(H26A,H26B,H26C), C42(H42A,H42B,
 H42C), C46(H46A,H46B,H46C), C63(H63A,H63B,H63C), C68(H68A,H68B,H68C), C84(H84A,
 H84B,H84C)
;
_shelx_res_checksum              30437
_olex2_submission_special_instructions 'No special instructions were received'