Metal-free nitro/azido cyclization of 1-acryloyl-2-cyanoindoles to access NO<sub>2</sub>/N<sub>3</sub>-featuring pyrrolo[1,2-<i>a</i>] indolediones.
Liu, Huaqing; Yan, Qinqin; Zeng, Yanzhao; Hou, Xinyi; Wang, Ying; Li, Lijun; Li, Zejiang; Organic & biomolecular chemistry 22 (2024) 6490–6494; doi:10.1039/d4ob01001a

data_7160065
_publ_section_title
;
 Metal-free nitro/azido cyclization of 1-acryloyl-2-cyanoindoles to access
 NO<sub>2</sub>/N<sub>3</sub>-featuring pyrrolo[1,2-<i>a</i>]
 indolediones.
;
_journal_issue                   32
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6490
_journal_page_last               6494
_journal_paper_doi               10.1039/d4ob01001a
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C19 H13 Cl N2 O4'
_chemical_formula_sum            'C19 H13 Cl N2 O4'
_chemical_formula_weight         368.779
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_atom_sites_solution_primary     iterative
_audit_creation_date             2024-06-08
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-06-11 deposited with the CCDC.	2024-07-22 downloaded from the CCDC.
;
_cell_angle_alpha                89.79(3)
_cell_angle_beta                 89.93(3)
_cell_angle_gamma                89.86(3)
_cell_formula_units_Z            8
_cell_length_a                   10.670(9)
_cell_length_b                   10.941(10)
_cell_length_c                   28.681(19)
_cell_measurement_reflns_used    3784
_cell_measurement_temperature    299.00
_cell_measurement_theta_max      21.073
_cell_measurement_theta_min      2.378
_cell_volume                     3348(5)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      299.00
_diffrn_measured_fraction_theta_full 0.9820
_diffrn_measured_fraction_theta_max 0.9820
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0722
_diffrn_reflns_av_unetI/netI     0.0748
_diffrn_reflns_Laue_measured_fraction_full 0.9820
_diffrn_reflns_Laue_measured_fraction_max 0.9820
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            23978
_diffrn_reflns_point_group_measured_fraction_full 0.9820
_diffrn_reflns_point_group_measured_fraction_max 0.9820
_diffrn_reflns_theta_full        21.3239
_diffrn_reflns_theta_max         21.32
_diffrn_reflns_theta_min         1.91
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.257
_exptl_absorpt_correction_T_max  0.7446
_exptl_absorpt_correction_T_min  0.5774
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1144 before and 0.0653 after correction.
The Ratio of minimum to maximum transmission is 0.7754.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_F_000             1522.195
_refine_diff_density_max         0.3929
_refine_diff_density_min         -0.5351
_refine_diff_density_rms         0.0948
_refine_ls_d_res_high            0.9772
_refine_ls_d_res_low             10.6700
_refine_ls_goodness_of_fit_ref   1.1272
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    92
_refine_ls_number_parameters     941
_refine_ls_number_reflns         7374
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.1272
_refine_ls_R_factor_all          0.1044
_refine_ls_R_factor_gt           0.0556
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0447P)^2^+0.6467P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1088
_refine_ls_wR_factor_ref         0.1370
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              11
_reflns_limit_k_min              -11
_reflns_limit_l_max              29
_reflns_limit_l_min              0
_reflns_number_gt                4594
_reflns_number_total             7374
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d4ob01001a2.cif
_cod_data_source_block           mo_052906
_cod_depositor_comments          'Adding full bibliography for 7160065.cif.'
_cod_database_code               7160065
_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:
 C12(H12a,H12b), C31(H31a,H31b), C50(H50a,H50b), C69(H69a,H69b)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C9(H9), C8(H8), C7(H7), C19(H19), C18(H18), C16(H16), C15(H15),
 C26(H26), C27(H27), C28(H28), C29(H29), C38(H38), C37(H37), C35(H35), C34(H34),
  C48(H48), C47(H47), C46(H46), C45(H45), C57(H57), C56(H56), C54(H54),
 C53(H53), C67(H67), C66(H66), C65(H65), C64(H64), C76(H76), C75(H75), C73(H73),
  C72(H72)
2.c Idealised Me refined as rotating group:
 C13(H13a,H13b,H13c), C32(H32a,H32b,H32c), C51(H51a,H51b,H51c), C70(H70a,H70b,
 H70c)
;
_olex2_submission_special_instructions 'No special instructions were received'