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_7129017
_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 H11 N3 O3'
_chemical_formula_sum            'C9 H11 N3 O3'
_chemical_formula_weight         209.21
_chemical_name_systematic        N,N'-dimethyl-4-nitrobenzohydrazide
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2020-11-18
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2021-06-03 deposited with the CCDC.	2021-09-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.021(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.8686(9)
_cell_length_b                   21.053(3)
_cell_length_c                   7.1521(9)
_cell_measurement_reflns_used    1420
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      3.45
_cell_volume                     1030.3(2)
_computing_cell_refinement       'SAINT V8.35A (?, 2016)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.35A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      295.24
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0851
_diffrn_reflns_av_unetI/netI     0.0497
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            13985
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.374
_diffrn_reflns_theta_min         1.935
_diffrn_source                   X-ray
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.9705
_exptl_absorpt_correction_T_min  0.8814
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0977 before and 0.0636 after correction.
The Ratio of minimum to maximum transmission is 0.9082.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_description       Plate
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.222
_exptl_crystal_size_mid          0.154
_exptl_crystal_size_min          0.038
_exptl_transmission_factor_max   0.9705
_exptl_transmission_factor_min   0.8814
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.028(5)
_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   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     143
_refine_ls_number_reflns         2105
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.1246
_refine_ls_R_factor_gt           0.0503
_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^)+(0.0461P)^2^+0.3946P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1092
_refine_ls_wR_factor_ref         0.1519
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1079
_reflns_number_total             2105
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc04533d2.cif
_cod_data_source_block           JD-NO2Ph-NMe_NMe-H
_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_original_cell_volume        1030.2(2)
_cod_database_code               7129017
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.977
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3A), C5(H5), C6(H6), C2(H2)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_shelx_res_checksum              52248
_olex2_submission_special_instructions 'No special instructions were received'