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_1574040
_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      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2023-09-20
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6916(4)
_cell_length_b                   5.8380(3)
_cell_length_c                   40.645(2)
_cell_measurement_reflns_used    9797
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      59.26
_cell_measurement_theta_min      5.09
_cell_volume                     1825.11(16)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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      150.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_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  0.0514
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       52
_diffrn_reflns_limit_l_min       -49
_diffrn_reflns_number            28617
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         59.279
_diffrn_reflns_theta_min         3.785
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.340
_exptl_absorpt_correction_T_max  0.7516
_exptl_absorpt_correction_T_min  0.6430
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1406 before and 0.0753 after correction.
The Ratio of minimum to maximum transmission is 0.8555.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 1450 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.072(7)
_refine_ls_extinction_coef       0.0051(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3750
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0312
_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^)+(0.0495P)^2^+0.1209P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0825
_refine_ls_wR_factor_ref         0.0851
_reflns_Friedel_coverage         0.836
_reflns_Friedel_fraction_full    0.930
_reflns_Friedel_fraction_max     0.860
_reflns_number_gt                3448
_reflns_number_total             3750
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc00277j2.cif
_cod_data_source_block           b23091906a0377_0ma
_cod_depositor_comments
'Adding full bibliography for 1574039--1574041.cif.'
_cod_original_cell_volume        1825.08(16)
_cod_database_code               1574040
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.924
_shelx_estimated_absorpt_t_min   0.814
_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:
 C00J(H00A,H00C), C00P(H00E,H00F)
2.b Aromatic/amide H refined with riding coordinates:
 C007(H007), C008(H008), C00B(H00B), C00D(H00D), C00G(H00G), C00I(H00I),
 C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N)
2.c Idealised Me refined as rotating group:
 C00Q(H00H,H00J,H00O)
;
_shelx_res_checksum              6441
_olex2_submission_special_instructions 'No special instructions were received'