#------------------------------------------------------------------------------
#$Date: 2025-08-22 18:52:37 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301865 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/19/7221996.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_7221996
loop_
_publ_author_name
'Trzesowska-Kruszynska, Agata'
_publ_section_title
;
 Solid-state studies of phthalazinylhydrazones and triazolophthalazines:
 the role of the nitro group
;
_journal_issue                   40
_journal_name_full               CrystEngComm
_journal_page_first              7702
_journal_paper_doi               10.1039/C5CE00846H
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C15 H11 N5 O2'
_chemical_formula_sum            'C15 H11 N5 O2'
_chemical_formula_weight         293.29
_chemical_name_systematic
; 
2-(3-nitrobenzylidene)-1-(phthalazin-1(2H)-ylidene)hydrazine 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_audit_update_record
;
2015-04-28 deposited with the CCDC.
2015-09-04 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 94.009(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.1361(9)
_cell_length_b                   3.7858(3)
_cell_length_c                   24.2876(15)
_cell_measurement_reflns_used    397
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      50
_cell_measurement_theta_min      2
_cell_volume                     1296.61(15)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2009)'
_computing_molecular_graphics
;XP in SHELXTL/PC (Sheldrick, 2008)
 ORTEP-3 W v. 1.062 (Farrugia 2012)
;
_computing_publication_material
;SHELXL (Sheldrick, 2008) and
 PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector_area_resol_mean 12.8
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         '30W microsource with MonoCap capillary'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_sigmaI/netI    0.0195
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            11199
_diffrn_reflns_theta_full        67.00
_diffrn_reflns_theta_max         72.26
_diffrn_reflns_theta_min         3.13
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_time  11.17
_diffrn_standards_number         4
_exptl_absorpt_coefficient_mu    0.873
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.024
_exptl_crystal_size_mid          0.017
_exptl_crystal_size_min          0.013
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2555
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0328
_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)+(0.0530P)²+0.4228P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0891
_refine_ls_wR_factor_ref         0.0929
_reflns_number_gt                2334
_reflns_number_total             2555
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ce00846h2.cif
_cod_data_source_block           con75fr2
_cod_depositor_comments
'Adding full bibliography for 7221992--7222004.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7221996
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 1.10661(8) 0.4183(3) 0.41449(4) 0.0167(2) Uani 1 1 d .
N1 N 1.06136(6) 0.2464(3) 0.45468(4) 0.0183(2) Uani 1 1 d .
H1N H 1.0011 0.1800 0.4487 0.026(4) Uiso 1 1 d R
N2 N 1.09913(7) 0.1587(3) 0.50622(4) 0.0193(2) Uani 1 1 d .
C2 C 1.18675(8) 0.2424(3) 0.51844(5) 0.0193(2) Uani 1 1 d .
H2 H 1.2135 0.1859 0.5543 0.023 Uiso 1 1 calc R
C3 C 1.24656(8) 0.4165(3) 0.48092(4) 0.0176(2) Uani 1 1 d .
C4 C 1.20612(8) 0.5045(3) 0.42829(5) 0.0167(2) Uani 1 1 d .
C5 C 1.34182(8) 0.4972(3) 0.49530(5) 0.0201(2) Uani 1 1 d .
H5 H 1.3693 0.4392 0.5310 0.024 Uiso 1 1 calc R
C6 C 1.39565(8) 0.6615(3) 0.45740(5) 0.0212(3) Uani 1 1 d .
H6 H 1.4603 0.7157 0.4671 0.025 Uiso 1 1 calc R
C7 C 1.35559(8) 0.7484(3) 0.40496(5) 0.0205(3) Uani 1 1 d .
H7 H 1.3933 0.8595 0.3791 0.025 Uiso 1 1 calc R
C8 C 1.26142(8) 0.6740(3) 0.39040(5) 0.0184(2) Uani 1 1 d .
H8 H 1.2342 0.7373 0.3549 0.022 Uiso 1 1 calc R
N3 N 1.06751(6) 0.5105(3) 0.36623(4) 0.0187(2) Uani 1 1 d .
N4 N 0.97094(6) 0.4353(3) 0.35987(4) 0.0188(2) Uani 1 1 d .
C9 C 0.93376(8) 0.5514(3) 0.31363(4) 0.0187(2) Uani 1 1 d .
H9 H 0.9740 0.6593 0.2888 0.022 Uiso 1 1 calc R
C10 C 0.83232(8) 0.5252(3) 0.29743(5) 0.0179(2) Uani 1 1 d .
C11 C 0.76794(8) 0.3747(3) 0.33204(4) 0.0180(2) Uani 1 1 d .
H11 H 0.7892 0.2772 0.3668 0.022 Uiso 1 1 calc R
C12 C 0.67277(8) 0.3715(3) 0.31446(4) 0.0183(2) Uani 1 1 d .
C13 C 0.63740(8) 0.5110(3) 0.26429(5) 0.0193(2) Uani 1 1 d .
H13 H 0.5714 0.5065 0.2537 0.023 Uiso 1 1 calc R
C14 C 0.70190(8) 0.6574(3) 0.23014(5) 0.0199(2) Uani 1 1 d .
H14 H 0.6800 0.7544 0.1955 0.024 Uiso 1 1 calc R
C15 C 0.79814(8) 0.6630(3) 0.24623(5) 0.0195(2) Uani 1 1 d .
H15 H 0.8414 0.7615 0.2222 0.023 Uiso 1 1 calc R
N5 N 0.60442(7) 0.2095(3) 0.35012(4) 0.0207(2) Uani 1 1 d .
O1 O 0.63519(6) 0.0494(2) 0.39148(3) 0.0271(2) Uani 1 1 d .
O2 O 0.51972(6) 0.2399(3) 0.33639(4) 0.0342(3) 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 0.0181 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'
O O 0.0492 0.0322 '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
N3 C1 N1 125.23(10)
N3 C1 C4 119.08(10)
N1 C1 C4 115.68(10)
N2 N1 C1 126.63(9)
N2 N1 H1N 112.9
C1 N1 H1N 120.4
C2 N2 N1 117.21(9)
N2 C2 C3 124.10(10)
N2 C2 H2 117.9
C3 C2 H2 117.9
C5 C3 C4 119.90(10)
C5 C3 C2 122.48(10)
C4 C3 C2 117.62(10)
C3 C4 C8 119.72(10)
C3 C4 C1 118.73(10)
C8 C4 C1 121.56(10)
C6 C5 C3 119.76(11)
C6 C5 H5 120.1
C3 C5 H5 120.1
C5 C6 C7 120.41(10)
C5 C6 H6 119.8
C7 C6 H6 119.8
C8 C7 C6 120.47(10)
C8 C7 H7 119.8
C6 C7 H7 119.8
C7 C8 C4 119.74(10)
C7 C8 H8 120.1
C4 C8 H8 120.1
C1 N3 N4 113.22(9)
C9 N4 N3 111.41(9)
N4 C9 C10 123.05(10)
N4 C9 H9 118.5
C10 C9 H9 118.5
C11 C10 C15 118.99(10)
C11 C10 C9 122.08(10)
C15 C10 C9 118.90(10)
C12 C11 C10 118.46(10)
C12 C11 H11 120.8
C10 C11 H11 120.8
C11 C12 C13 123.40(10)
C11 C12 N5 119.02(10)
C13 C12 N5 117.57(10)
C12 C13 C14 117.66(10)
C12 C13 H13 121.2
C14 C13 H13 121.2
C15 C14 C13 120.57(10)
C15 C14 H14 119.7
C13 C14 H14 119.7
C14 C15 C10 120.90(10)
C14 C15 H15 119.6
C10 C15 H15 119.6
O2 N5 O1 123.58(10)
O2 N5 C12 117.93(9)
O1 N5 C12 118.48(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N3 1.3080(14)
C1 N1 1.3685(14)
C1 C4 1.4601(15)
N1 N2 1.3670(13)
N1 H1N 0.8904
N2 C2 1.2927(14)
C2 C3 1.4447(15)
C2 H2 0.9500
C3 C5 1.4009(16)
C3 C4 1.4034(15)
C4 C8 1.4036(15)
C5 C6 1.3825(16)
C5 H5 0.9500
C6 C7 1.3967(16)
C6 H6 0.9500
C7 C8 1.3823(15)
C7 H7 0.9500
C8 H8 0.9500
N3 N4 1.3925(13)
N4 C9 1.2839(15)
C9 C10 1.4636(15)
C9 H9 0.9500
C10 C11 1.4024(15)
C10 C15 1.4030(15)
C11 C12 1.3829(15)
C11 H11 0.9500
C12 C13 1.3886(16)
C12 N5 1.4755(14)
C13 C14 1.3901(16)
C13 H13 0.9500
C14 C15 1.3891(16)
C14 H14 0.9500
C15 H15 0.9500
N5 O2 1.2257(12)
N5 O1 1.2264(13)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 9713767
