n<sub>N</sub> → π*<sub>Ar</sub> interactions stabilize the <i>E</i>-ac isomers of arylhydrazides and facilitate their S<sub>N</sub>Ar autocyclizations.
Deka, Jugal Kishore Rai; Kalita, Debajit; Sahariah, Biswajit; Sarma, Bani Kanta; Chemical communications (Cambridge, England) 57 (2021) 11236–11239; doi:10.1039/d1cc04533d

data_7129020
_publ_section_title
;
 n<sub>N</sub> \\rightarrow \p*<sub>Ar</sub> interactions stabilize the
 <i>E</i>-ac isomers of arylhydrazides and facilitate their
 S<sub>N</sub>Ar autocyclizations.
;
_journal_issue                   85
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              11236
_journal_page_last               11239
_journal_paper_doi               10.1039/d1cc04533d
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C9 H9 N3 O3'
_chemical_formula_sum            'C9 H9 N3 O3'
_chemical_formula_weight         207.19
_chemical_name_systematic        1,2-dimethyl-6-nitro-1H-indazol-3(2H)-one
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2021-07-01 deposited with the CCDC.	2021-09-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.3475(8)
_cell_length_b                   18.8728(11)
_cell_length_c                   3.9943(2)
_cell_measurement_reflns_used    4449
_cell_measurement_temperature    302(2)
_cell_measurement_theta_max      25.62
_cell_measurement_theta_min      2.72
_cell_volume                     930.80(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      302(2)
_diffrn_measured_fraction_theta_full 0.996
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            9432
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.018
_diffrn_reflns_theta_min         1.971
_diffrn_source                   X-ray
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.862
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_description       Rod
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.117
_exptl_crystal_size_min          0.078
_refine_diff_density_max         0.127
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 618 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(6)
_refine_ls_extinction_coef       0.037(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         1811
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0348
_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^)+(0.0411P)^2^+0.1851P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0860
_refine_ls_wR_factor_ref         0.0937
_reflns_Friedel_coverage         0.733
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                1578
_reflns_number_total             1811
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc04533d2.cif
_cod_data_source_block           JD-metaNO2Ph-F-CY-17C
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7129017--7129022.cif.
;
_cod_database_code               7129020
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_min   0.964
_shelx_estimated_absorpt_t_max   0.991
_shelx_res_checksum              56796