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#$Date: 2022-06-30 01:43:10 +0300 (Thu, 30 Jun 2022) $
#$Revision: 276414 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/51/7245123.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_7245123
loop_
_publ_author_name
'Zaib, Sumera'
'Ibrar, Aliya'
'Ramay, Marriyam'
'Zahra, Shabab'
'Hökelek, Tuncer'
'Simpson, Jim'
'McAdam, Christopher John John'
'Awwad, Nasser S.'
'Ibrahium, Hala A.'
'Frontera, Antonio'
'Khan, Imtiaz'
_publ_section_title
;
 Centroid…centroid and hydrogen bond interactions as robust
 supramolecular units for crystal engineering: X-ray crystallographic,
 computational and urease inhibitory investigations of
 1,2,4-triazolo[3,4-a]phthalazines
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE00351A
_journal_year                    2022
_chemical_formula_moiety         'C10 H7 Cl N4'
_chemical_formula_sum            'C10 H7 Cl N4'
_chemical_formula_weight         218.65
_chemical_name_systematic
;
6-chloro-3-methyl-[1,2,4]triazolo[3,4-a]phthalazine
;
_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   geom
_audit_creation_method           SHELXL-2019/2
_audit_update_record
;
2022-05-08 deposited with the CCDC.	2022-06-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.213(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.80820(10)
_cell_length_b                   7.36850(10)
_cell_length_c                   14.2931(2)
_cell_measurement_reflns_used    8555
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      72.6750
_cell_measurement_theta_min      5.8610
_cell_volume                     927.66(2)
_computing_cell_refinement       'CrysAlisPro (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro (Rigaku OD, 2018)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material
;
SHELXL-2019/2 (Sheldrick, 2015b), enCIFer (Allen et al., 2004), 
PLATON (Spek, 2009),  PublCIF (Westrip 2010), WINGX (Farrugia 2012)
;
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector_area_resol_mean 10.3449
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0141
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16468
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.827
_diffrn_reflns_theta_min         5.891
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    3.379
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.619
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.177
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.088
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1833
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0300
_refine_ls_R_factor_gt           0.0267
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0323P)²+0.5541P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0662
_refine_ls_wR_factor_ref         0.0689
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1679
_reflns_number_total             1833
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce00351a2.cif
_cod_data_source_block           shelx_wingx_JM_rxn34
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7245123
_shelx_shelxl_version_number     2019/2
_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.
;
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
Cl1 Cl 0.25918(4) 0.17880(4) 0.55217(2) 0.01794(11) Uani 1 1 d . . . . .
N2 N 0.61366(13) 0.38976(15) 0.65956(8) 0.0140(2) Uani 1 1 d . . . . .
N1 N 0.47020(13) 0.32005(15) 0.64950(8) 0.0142(2) Uani 1 1 d . . . . .
N4 N 0.84472(13) 0.48371(16) 0.62830(8) 0.0187(3) Uani 1 1 d . . . . .
N3 N 0.81090(14) 0.52179(17) 0.72185(8) 0.0194(3) Uani 1 1 d . . . . .
C3 C 0.72383(15) 0.40491(18) 0.59242(10) 0.0151(3) Uani 1 1 d . . . . .
C4 C 0.68973(16) 0.33791(18) 0.50001(10) 0.0148(3) Uani 1 1 d . . . . .
C9 C 0.54323(15) 0.26340(18) 0.48630(9) 0.0145(3) Uani 1 1 d . . . . .
C2 C 0.67272(16) 0.46476(18) 0.73923(9) 0.0160(3) Uani 1 1 d . . . . .
C8 C 0.50231(16) 0.19749(18) 0.39758(10) 0.0172(3) Uani 1 1 d . . . . .
H8 H 0.406801 0.146946 0.387849 0.021 Uiso 1 1 calc R U . . .
C5 C 0.79209(16) 0.34793(19) 0.42550(10) 0.0183(3) Uani 1 1 d . . . . .
H5 H 0.888432 0.396712 0.434462 0.022 Uiso 1 1 calc R U . . .
C10 C 0.44134(15) 0.26194(18) 0.56626(9) 0.0142(3) Uani 1 1 d . . . . .
C7 C 0.60473(17) 0.2081(2) 0.32476(10) 0.0196(3) Uani 1 1 d . . . . .
H7 H 0.577813 0.163989 0.266043 0.024 Uiso 1 1 calc R U . . .
C1 C 0.59000(17) 0.4737(2) 0.82929(10) 0.0199(3) Uani 1 1 d . . . . .
H1A H 0.584849 0.354581 0.856346 0.030 Uiso 1 1 calc R U . . .
H1B H 0.489072 0.518371 0.818493 0.030 Uiso 1 1 calc R U . . .
H1C H 0.642516 0.553785 0.871332 0.030 Uiso 1 1 calc R U . . .
C6 C 0.74838(17) 0.2845(2) 0.33848(10) 0.0205(3) Uani 1 1 d . . . . .
H6 H 0.815288 0.292776 0.288474 0.025 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
C2 N2 N1 125.92(11) . . ?
C2 N2 C3 106.37(11) . . ?
N1 N2 C3 127.67(11) . . ?
C10 N1 N2 113.57(11) . . ?
C3 N4 N3 106.63(11) . . ?
C2 N3 N4 108.51(11) . . ?
N4 C3 N2 109.69(12) . . ?
N4 C3 C4 132.41(13) . . ?
N2 C3 C4 117.89(12) . . ?
C5 C4 C9 120.31(13) . . ?
C5 C4 C3 123.14(13) . . ?
C9 C4 C3 116.53(12) . . ?
C8 C9 C4 119.35(13) . . ?
C8 C9 C10 123.34(12) . . ?
C4 C9 C10 117.30(12) . . ?
N3 C2 N2 108.80(12) . . ?
N3 C2 C1 127.53(13) . . ?
N2 C2 C1 123.66(13) . . ?
C7 C8 C9 119.64(13) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C6 C5 C4 119.26(13) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
N1 C10 C9 127.02(12) . . ?
N1 C10 Cl1 113.90(10) . . ?
C9 C10 Cl1 119.07(10) . . ?
C8 C7 C6 120.68(13) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C5 C6 C7 120.75(13) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
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
Cl1 C10 1.7285(13) . ?
N2 C2 1.3668(17) . ?
N2 N1 1.3711(16) . ?
N2 C3 1.3719(18) . ?
N1 C10 1.2889(18) . ?
N4 C3 1.3152(18) . ?
N4 N3 1.3995(17) . ?
N3 C2 1.3122(19) . ?
C3 C4 1.4407(19) . ?
C4 C5 1.400(2) . ?
C4 C9 1.4153(19) . ?
C9 C8 1.4037(19) . ?
C9 C10 1.4558(19) . ?
C2 C1 1.483(2) . ?
C8 C7 1.382(2) . ?
C8 H8 0.9300 . ?
C5 C6 1.382(2) . ?
C5 H5 0.9300 . ?
C7 C6 1.398(2) . ?
C7 H7 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C6 H6 0.9300 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C6 H6 N1 0.93 2.55 3.4272(19) 156.7 4_665 yes
C5 H5 N4 0.93 2.67 3.5188(19) 152.3 3_766 yes
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
C2 N2 N1 C10 178.17(12) . . . . ?
C3 N2 N1 C10 0.80(19) . . . . ?
C3 N4 N3 C2 0.26(15) . . . . ?
N3 N4 C3 N2 -0.38(15) . . . . ?
N3 N4 C3 C4 178.94(14) . . . . ?
C2 N2 C3 N4 0.36(15) . . . . ?
N1 N2 C3 N4 178.14(12) . . . . ?
C2 N2 C3 C4 -179.07(11) . . . . ?
N1 N2 C3 C4 -1.29(19) . . . . ?
N4 C3 C4 C5 -0.1(2) . . . . ?
N2 C3 C4 C5 179.15(12) . . . . ?
N4 C3 C4 C9 -178.57(14) . . . . ?
N2 C3 C4 C9 0.70(18) . . . . ?
C5 C4 C9 C8 0.83(19) . . . . ?
C3 C4 C9 C8 179.33(12) . . . . ?
C5 C4 C9 C10 -178.34(12) . . . . ?
C3 C4 C9 C10 0.16(18) . . . . ?
N4 N3 C2 N2 -0.04(15) . . . . ?
N4 N3 C2 C1 178.92(13) . . . . ?
N1 N2 C2 N3 -178.02(12) . . . . ?
C3 N2 C2 N3 -0.19(15) . . . . ?
N1 N2 C2 C1 3.0(2) . . . . ?
C3 N2 C2 C1 -179.19(13) . . . . ?
C4 C9 C8 C7 -0.7(2) . . . . ?
C10 C9 C8 C7 178.38(12) . . . . ?
C9 C4 C5 C6 0.1(2) . . . . ?
C3 C4 C5 C6 -178.31(13) . . . . ?
N2 N1 C10 C9 0.25(19) . . . . ?
N2 N1 C10 Cl1 -178.52(8) . . . . ?
C8 C9 C10 N1 -179.83(13) . . . . ?
C4 C9 C10 N1 -0.7(2) . . . . ?
C8 C9 C10 Cl1 -1.11(18) . . . . ?
C4 C9 C10 Cl1 178.02(10) . . . . ?
C9 C8 C7 C6 -0.3(2) . . . . ?
C4 C5 C6 C7 -1.1(2) . . . . ?
C8 C7 C6 C5 1.2(2) . . . . ?
