#------------------------------------------------------------------------------
#$Date: 2022-08-06 14:58:03 +0300 (Sat, 06 Aug 2022) $
#$Revision: 277132 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/16/7061650.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_7061650
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 Cl2 N4 O4'
_chemical_formula_sum            'C4 Cl2 N4 O4'
_chemical_formula_weight         238.98
_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_primary     dual
_audit_creation_date             2021-11-18
_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                 100.853(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.1210(7)
_cell_length_b                   5.9953(5)
_cell_length_c                   14.5570(12)
_cell_measurement_reflns_used    2908
_cell_measurement_temperature    150
_cell_measurement_theta_max      26.294
_cell_measurement_theta_min      2.849
_cell_volume                     781.78(11)
_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      150.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8446
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.408
_diffrn_reflns_theta_min         2.445
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.824
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6763
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0903 before and 0.0534 after correction. The Ratio of minimum to maximum transmission is 0.9073. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.030
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1604
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0312
_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)+(0.0201P)²+0.5487P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0602
_refine_ls_wR_factor_ref         0.0681
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1301
_reflns_number_total             1604
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2nj02908a2.cif
_cod_data_source_block           mo_20211646_0m
_cod_depositor_comments
'Adding full bibliography for 7061650--7061656.cif.'
_cod_database_code               7061650
_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   0.976
_shelx_estimated_absorpt_t_min   0.900
_olex2_refinement_description
;
1. Restrained distances
 N2-N1
 1.5 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
Cl2 Cl 0.24191(6) 0.68610(10) 0.53813(4) 0.02921(16) Uani 1 1 d . . . . .
Cl1 Cl 0.63786(6) 0.31855(10) 0.91245(4) 0.02981(16) Uani 1 1 d . . . . .
O3 O 0.52899(16) 0.0814(2) 0.60494(10) 0.0257(4) Uani 1 1 d . . . . .
O1 O 0.31419(16) 0.8938(2) 0.72787(11) 0.0260(4) Uani 1 1 d . . . . .
O2 O 0.46491(18) 0.7448(3) 0.87715(11) 0.0295(4) Uani 1 1 d . . . . .
O4 O 0.66395(16) -0.0211(3) 0.74897(11) 0.0282(4) Uani 1 1 d . . . . .
N3 N 0.58341(19) 0.1213(3) 0.70520(13) 0.0211(4) Uani 1 1 d . . . . .
N2 N 0.47272(19) 0.6160(3) 0.81357(12) 0.0202(4) Uani 1 1 d D . . . .
N1 N 0.37066(18) 0.7151(3) 0.71241(12) 0.0193(4) Uani 1 1 d D . . . .
N4 N 0.4388(2) 0.2570(3) 0.56954(13) 0.0248(4) Uani 1 1 d . . . . .
C2 C 0.5241(2) 0.3135(3) 0.72422(14) 0.0172(4) Uani 1 1 d . . . . .
C3 C 0.4371(2) 0.3921(3) 0.64014(14) 0.0177(4) Uani 1 1 d . . . . .
C4 C 0.3571(2) 0.5974(3) 0.63603(14) 0.0186(4) Uani 1 1 d . . . . .
C1 C 0.5398(2) 0.4229(3) 0.81179(15) 0.0198(5) Uani 1 1 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'
Cl Cl 0.1484 0.1585 '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
N4 O3 N3 108.30(14) . . ?
O4 N3 O3 117.44(16) . . ?
O4 N3 C2 136.62(19) . . ?
C2 N3 O3 105.92(15) . . ?
O2 N2 N1 109.67(15) . . ?
O2 N2 C1 131.99(19) . . ?
C1 N2 N1 118.31(16) . . ?
O1 N1 N2 109.11(15) . . ?
O1 N1 C4 130.81(18) . . ?
C4 N1 N2 119.99(16) . . ?
C3 N4 O3 105.89(17) . . ?
N3 C2 C3 107.14(18) . . ?
N3 C2 C1 127.95(19) . . ?
C3 C2 C1 124.90(18) . . ?
N4 C3 C2 112.76(18) . . ?
N4 C3 C4 125.57(19) . . ?
C2 C3 C4 121.67(18) . . ?
N1 C4 Cl2 119.55(16) . . ?
N1 C4 C3 117.78(18) . . ?
C3 C4 Cl2 122.62(16) . . ?
N2 C1 Cl1 118.89(16) . . ?
N2 C1 C2 117.25(18) . . ?
C2 C1 Cl1 123.86(16) . . ?
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
Cl2 C4 1.689(2) . ?
Cl1 C1 1.687(2) . ?
O3 N3 1.470(2) . ?
O3 N4 1.375(2) . ?
O1 N1 1.228(2) . ?
O2 N2 1.218(2) . ?
O4 N3 1.224(2) . ?
N3 C2 1.324(3) . ?
N2 N1 1.695(2) . ?
N2 C1 1.312(3) . ?
N1 C4 1.303(3) . ?
N4 C3 1.311(3) . ?
C2 C3 1.409(3) . ?
C2 C1 1.417(3) . ?
C3 C4 1.426(3) . ?
