#------------------------------------------------------------------------------
#$Date: 2022-08-06 14:58:03 +0300 (Sat, 06 Aug 2022) $
#$Revision: 277132 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/16/7061655.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7061655
loop_
_publ_author_name
'Zhang, Qi'
'He, Chunlin'
'Pang, Siping'
_publ_section_title
;
 Synthesis of heterocyclic (triazole, furoxan, furazan) fused pyridazine
 di-N-oxides via hypervalent iodine oxidation
;
_journal_issue                   30
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              14324
_journal_page_last               14327
_journal_paper_doi               10.1039/D2NJ02908A
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C4 H N7 O3'
_chemical_formula_sum            'C4 H N7 O3'
_chemical_formula_weight         195.12
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2021-12-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-05-30 deposited with the CCDC.	2022-07-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.035(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3585(14)
_cell_length_b                   5.3944(9)
_cell_length_c                   15.367(2)
_cell_measurement_reflns_used    1363
_cell_measurement_temperature    298
_cell_measurement_theta_max      24.588
_cell_measurement_theta_min      2.474
_cell_volume                     773.9(2)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 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      298
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_av_unetI/netI     0.0454
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5321
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.437
_diffrn_reflns_theta_min         2.473
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.145
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6196
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0683 before and 0.0469 after correction. The Ratio of minimum to maximum transmission is 0.8312. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.675
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.444
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         1582
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.1176
_refine_ls_R_factor_gt           0.0584
_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/[σ²(Fo²)+(0.0638P)²+0.3506P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1328
_refine_ls_wR_factor_ref         0.1638
_reflns_Friedel_coverage         0.000
_reflns_number_gt                884
_reflns_number_total             1582
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2nj02908a2.cif
_cod_data_source_block           20211713zq157_0m
_cod_depositor_comments
'Adding full bibliography for 7061650--7061656.cif.'
_cod_original_cell_volume        773.8(2)
_cod_database_code               7061655
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.983
_olex2_refinement_description
;
1. Restrained distances
 O3-H3
 0.87 with sigma of 0.02
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.6452(2) 0.5936(4) 0.39415(16) 0.0715(7) Uani 1 1 d D . . . .
O1 O 0.0570(3) 0.3403(5) 0.33625(16) 0.0838(8) Uani 1 1 d . . . . .
N5 N 0.4989(3) 0.6089(5) 0.39905(16) 0.0585(7) Uani 1 1 d . . . . .
N7 N 0.0621(3) 0.5533(6) 0.39176(18) 0.0735(8) Uani 1 1 d . . . . .
N2 N 0.6093(4) 0.2048(5) 0.30402(17) 0.0684(8) Uani 1 1 d . . . . .
N8 N 0.2672(3) 0.9921(6) 0.50059(19) 0.0752(8) Uani 1 1 d . . . . .
O2 O -0.0473(3) 0.6333(6) 0.41508(18) 0.0999(9) Uani 1 1 d . . . . .
N6 N 0.1937(3) 0.2819(6) 0.31724(18) 0.0720(8) Uani 1 1 d . . . . .
C2 C 0.2785(3) 0.4480(6) 0.35816(18) 0.0566(8) Uani 1 1 d . . . . .
C4 C 0.1990(3) 0.6159(6) 0.40504(18) 0.0567(8) Uani 1 1 d . . . . .
C1 C 0.4314(3) 0.4391(6) 0.35451(19) 0.0577(8) Uani 1 1 d . . . . .
N1 N 0.7209(4) 0.1314(6) 0.2961(2) 0.0846(10) Uani 1 1 d . . . . .
N4 N 0.4796(4) 0.2527(6) 0.3024(2) 0.0886(10) Uani 1 1 d . . . . .
C3 C 0.2385(3) 0.8234(7) 0.4577(2) 0.0612(8) Uani 1 1 d . . . . .
H3 H 0.684(4) 0.710(6) 0.425(3) 0.114(16) Uiso 1 1 d D . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N5 O3 H3 108(3) . . ?
N6 O1 N7 108.7(2) . . ?
C1 N5 O3 112.4(2) . . ?
O2 N7 O1 118.6(3) . . ?
O2 N7 C4 134.7(4) . . ?
C4 N7 O1 106.7(3) . . ?
N1 N2 N4 168.7(3) . . ?
C2 N6 O1 106.3(3) . . ?
N6 C2 C4 111.0(3) . . ?
N6 C2 C1 121.6(3) . . ?
C4 C2 C1 127.4(3) . . ?
N7 C4 C2 107.3(3) . . ?
N7 C4 C3 120.0(3) . . ?
C2 C4 C3 132.7(3) . . ?
N5 C1 C2 114.2(3) . . ?
N5 C1 N4 131.4(3) . . ?
N4 C1 C2 114.4(3) . . ?
N2 N4 C1 120.0(3) . . ?
N8 C3 C4 178.5(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 N5 1.379(3) . ?
O3 H3 0.855(19) . ?
O1 N7 1.430(4) . ?
O1 N6 1.369(3) . ?
N5 C1 1.283(4) . ?
N7 O2 1.189(3) . ?
N7 C4 1.327(4) . ?
N2 N1 1.131(4) . ?
N2 N4 1.240(4) . ?
N8 C3 1.144(4) . ?
N6 C2 1.326(4) . ?
C2 C4 1.403(4) . ?
C2 C1 1.437(4) . ?
C4 C3 1.415(5) . ?
C1 N4 1.381(4) . ?
