#------------------------------------------------------------------------------
#$Date: 2025-07-06 19:54:17 +0200 (Sun 06 de Jul de 2025) $
#$Revision: 301140 $
#$URL: svn://www.crystallography.net/cod/cif/7/16/05/7160580.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_7160580
loop_
_publ_author_name
'Zhu, Chen'
'Zhang, Jing'
'Yang, Jiaxin'
'Li, Xinxin'
'Wang, Xinyu'
'Shi, Hu'
'Jin, Hui'
'Zhang, Lixin'
_publ_section_title
;
 Ketenes as dienophiles in aza-Diels-Alder reactions with
 dicyanohydrazones for accessing pyridazin-3(2H)-ones.
;
_journal_issue                   25
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              6220
_journal_page_last               6224
_journal_paper_doi               10.1039/d5ob00844a
_journal_volume                  23
_journal_year                    2025
_chemical_formula_sum            'C15 H16 N4 O'
_chemical_formula_weight         268.32
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2024-08-27 deposited with the CCDC.	2025-05-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.6652(12)
_cell_length_b                   11.4053(12)
_cell_length_c                   22.148(2)
_cell_measurement_reflns_used    5582
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.68
_cell_measurement_theta_min      2.54
_cell_volume                     2946.7(5)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  CCD
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1179
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            52590
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.101
_diffrn_reflns_theta_max         25.101
_diffrn_reflns_theta_min         2.536
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_transmission_factor_max   0.864
_exptl_transmission_factor_min   0.864
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.158
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2620
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.158
_refine_ls_R_factor_all          0.1454
_refine_ls_R_factor_gt           0.0921
_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)+(0.0840P)²+2.6141P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1930
_refine_ls_wR_factor_ref         0.2229
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1718
_reflns_number_total             2620
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5ob00844a2.cif
_cod_data_source_block           1_a
_cod_depositor_comments          'Adding full bibliography for 7160580.cif.'
_cod_database_code               7160580
_shelx_shelxl_version_number     2014/7
_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_min   0.984
_shelx_estimated_absorpt_t_max   0.984
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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
C1 C 0.0827(3) 0.2896(4) 0.31513(19) 0.0610(11) Uani 1 1 d . . . . .
C2 C 0.0588(4) 0.1670(4) 0.2902(3) 0.0905(17) Uani 1 1 d . . . . .
H2A H 0.0657 0.1104 0.3221 0.136 Uiso 1 1 calc R U . . .
H2B H 0.1132 0.1491 0.2590 0.136 Uiso 1 1 calc R U . . .
H2C H -0.0174 0.1643 0.2739 0.136 Uiso 1 1 calc R U . . .
C3 C -0.0102(4) 0.3207(8) 0.3597(3) 0.168(4) Uani 1 1 d . . . . .
H3A H -0.0040 0.2710 0.3946 0.252 Uiso 1 1 calc R U . . .
H3B H -0.0839 0.3097 0.3413 0.252 Uiso 1 1 calc R U . . .
H3C H -0.0019 0.4011 0.3718 0.252 Uiso 1 1 calc R U . . .
C4 C 0.0800(6) 0.3741(5) 0.2612(3) 0.126(3) Uani 1 1 d . . . . .
H4A H 0.0065 0.3696 0.2418 0.190 Uiso 1 1 calc R U . . .
H4B H 0.1388 0.3527 0.2329 0.190 Uiso 1 1 calc R U . . .
H4C H 0.0930 0.4527 0.2751 0.190 Uiso 1 1 calc R U . . .
C5 C 0.2005(3) 0.2993(3) 0.34467(17) 0.0484(10) Uani 1 1 d . . . . .
C6 C 0.2856(4) 0.2153(4) 0.33784(19) 0.0603(11) Uani 1 1 d . . . . .
H6 H 0.2695 0.1480 0.3158 0.072 Uiso 1 1 calc R U . . .
C7 C 0.3940(3) 0.2285(3) 0.36284(19) 0.0572(11) Uani 1 1 d . . . . .
H7 H 0.4492 0.1705 0.3577 0.069 Uiso 1 1 calc R U . . .
C8 C 0.4189(3) 0.3275(3) 0.39518(16) 0.0450(9) Uani 1 1 d . . . . .
C9 C 0.3362(3) 0.4115(3) 0.40331(18) 0.0530(10) Uani 1 1 d . . . . .
H9 H 0.3526 0.4784 0.4257 0.064 Uiso 1 1 calc R U . . .
C10 C 0.2292(3) 0.3970(4) 0.37851(18) 0.0555(11) Uani 1 1 d . . . . .
H10 H 0.1742 0.4548 0.3847 0.067 Uiso 1 1 calc R U . . .
C11 C 0.5861(3) 0.2726(3) 0.46018(17) 0.0477(9) Uani 1 1 d . . . . .
C12 C 0.6912(3) 0.3110(3) 0.48271(18) 0.0521(10) Uani 1 1 d . . . . .
H12 H 0.7267 0.2676 0.5130 0.062 Uiso 1 1 calc R U . . .
C13 C 0.7441(3) 0.4103(3) 0.46187(16) 0.0443(9) Uani 1 1 d . . . . .
C14 C 0.6839(3) 0.4727(3) 0.41527(17) 0.0456(9) Uani 1 1 d . . . . .
C15 C 0.7363(3) 0.5702(4) 0.38483(19) 0.0571(11) Uani 1 1 d . . . . .
N1 N 0.5330(2) 0.3482(2) 0.41828(13) 0.0445(8) Uani 1 1 d . . . . .
N2 N 0.5825(3) 0.4445(3) 0.39557(14) 0.0484(8) Uani 1 1 d . . . . .
N3 N 0.7815(4) 0.6449(4) 0.3607(2) 0.0863(14) Uani 1 1 d . . . . .
N4 N 0.8454(3) 0.4500(3) 0.48199(14) 0.0554(9) Uani 1 1 d . . . . .
H4D H 0.8815 0.4124 0.5098 0.066 Uiso 1 1 calc R U . . .
H4E H 0.8743 0.5131 0.4671 0.066 Uiso 1 1 calc R U . . .
O1 O 0.5349(2) 0.1806(2) 0.47389(13) 0.0630(8) 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'
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
C3 C1 C5 110.4(4) . . ?
C3 C1 C2 108.7(5) . . ?
C5 C1 C2 112.7(4) . . ?
C3 C1 C4 110.3(5) . . ?
C5 C1 C4 107.8(4) . . ?
C2 C1 C4 106.8(4) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C10 C5 C6 116.2(3) . . ?
C10 C5 C1 120.6(3) . . ?
C6 C5 C1 123.2(3) . . ?
C7 C6 C5 122.2(4) . . ?
C7 C6 H6 118.9 . . ?
C5 C6 H6 118.9 . . ?
C8 C7 C6 119.4(4) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C7 C8 C9 119.7(3) . . ?
C7 C8 N1 121.0(3) . . ?
C9 C8 N1 119.1(3) . . ?
C8 C9 C10 120.2(4) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C9 C10 C5 122.2(4) . . ?
C9 C10 H10 118.9 . . ?
C5 C10 H10 118.9 . . ?
O1 C11 C12 126.8(4) . . ?
O1 C11 N1 117.7(3) . . ?
C12 C11 N1 115.5(3) . . ?
C13 C12 C11 122.3(4) . . ?
C13 C12 H12 118.8 . . ?
C11 C12 H12 118.8 . . ?
N4 C13 C12 124.3(3) . . ?
N4 C13 C14 120.1(3) . . ?
C12 C13 C14 115.5(3) . . ?
N2 C14 C15 114.9(3) . . ?
N2 C14 C13 124.2(3) . . ?
C15 C14 C13 120.8(3) . . ?
N3 C15 C14 177.4(5) . . ?
N2 N1 C11 124.0(3) . . ?
N2 N1 C8 113.5(3) . . ?
C11 N1 C8 122.5(3) . . ?
C14 N2 N1 118.0(3) . . ?
C13 N4 H4D 120.0 . . ?
C13 N4 H4E 120.0 . . ?
H4D N4 H4E 120.0 . . ?
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
C1 C3 1.509(7) . ?
C1 C5 1.526(5) . ?
C1 C2 1.529(6) . ?
C1 C4 1.535(7) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C10 1.384(5) . ?
C5 C6 1.389(5) . ?
C6 C7 1.388(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.368(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.371(5) . ?
C8 N1 1.446(5) . ?
C9 C10 1.374(5) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 O1 1.246(4) . ?
C11 C12 1.394(5) . ?
C11 N1 1.410(5) . ?
C12 C13 1.371(5) . ?
C12 H12 0.9300 . ?
C13 N4 1.342(4) . ?
C13 C14 1.437(5) . ?
C14 N2 1.301(4) . ?
C14 C15 1.437(5) . ?
C15 N3 1.136(5) . ?
N1 N2 1.338(4) . ?
N4 H4D 0.8600 . ?
N4 H4E 0.8600 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 C1 C5 C10 -47.3(6) . . . . ?
C2 C1 C5 C10 -169.0(4) . . . . ?
C4 C1 C5 C10 73.4(5) . . . . ?
C3 C1 C5 C6 135.2(5) . . . . ?
C2 C1 C5 C6 13.5(6) . . . . ?
C4 C1 C5 C6 -104.2(5) . . . . ?
C10 C5 C6 C7 -0.7(6) . . . . ?
C1 C5 C6 C7 177.0(4) . . . . ?
C5 C6 C7 C8 -0.3(6) . . . . ?
C6 C7 C8 C9 1.0(6) . . . . ?
C6 C7 C8 N1 -175.6(3) . . . . ?
C7 C8 C9 C10 -0.8(6) . . . . ?
N1 C8 C9 C10 175.9(3) . . . . ?
C8 C9 C10 C5 -0.3(6) . . . . ?
C6 C5 C10 C9 1.0(6) . . . . ?
C1 C5 C10 C9 -176.8(4) . . . . ?
O1 C11 C12 C13 175.7(4) . . . . ?
N1 C11 C12 C13 -5.3(5) . . . . ?
C11 C12 C13 N4 -179.6(3) . . . . ?
C11 C12 C13 C14 0.2(5) . . . . ?
N4 C13 C14 N2 -175.9(3) . . . . ?
C12 C13 C14 N2 4.4(6) . . . . ?
N4 C13 C14 C15 7.1(5) . . . . ?
C12 C13 C14 C15 -172.7(4) . . . . ?
O1 C11 N1 N2 -173.9(3) . . . . ?
C12 C11 N1 N2 7.0(5) . . . . ?
O1 C11 N1 C8 5.4(5) . . . . ?
C12 C11 N1 C8 -173.7(3) . . . . ?
C7 C8 N1 N2 117.8(4) . . . . ?
C9 C8 N1 N2 -58.9(4) . . . . ?
C7 C8 N1 C11 -61.6(5) . . . . ?
C9 C8 N1 C11 121.8(4) . . . . ?
C15 C14 N2 N1 174.3(3) . . . . ?
C13 C14 N2 N1 -3.0(5) . . . . ?
C11 N1 N2 C14 -3.0(5) . . . . ?
C8 N1 N2 C14 177.6(3) . . . . ?
