#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/53/2225312.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2225312
loop_
_publ_author_name
'Gomes, Ligia R.'
'Lima, Carlos F. R. A. C.'
'Santos, Luís M. N. B. F.'
'Brandão, Paula'
'Low, John Nicolson'
_publ_section_title
;
 1,3-Diphenylpropan-2-one (2,4-dinitrophenyl)hydrazone
;
_journal_coeditor_code           LH2985
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o565
_journal_paper_doi               10.1107/S1600536810002746
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C21 H18 N4 O4'
_chemical_formula_moiety         'C21 H18 N4 O4'
_chemical_formula_sum            'C21 H18 N4 O4'
_chemical_formula_weight         390.39
_chemical_melting_point          381.7
_chemical_name_systematic
;
1,3-Diphenylpropan-2-one (2,4-dinitrophenyl)hydrazone
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 109.475(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.2448(9)
_cell_length_b                   5.1013(2)
_cell_length_c                   22.7459(13)
_cell_measurement_reflns_used    211
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      51.44
_cell_measurement_theta_min      15.49
_cell_volume                     1886.50(17)
_computing_cell_refinement       'APEX2 and SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics
'ORTEPII (Johnson, 1976) and PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_sigmaI/netI    0.0456
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            13123
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         29.12
_diffrn_reflns_theta_min         2.60
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.9980
_exptl_absorpt_correction_T_min  0.9619
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2004)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.240
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4973
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0749
_refine_ls_R_factor_gt           0.0456
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0644P)²+0.0648P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1118
_refine_ls_wR_factor_ref         0.1261
_reflns_number_gt                3417
_reflns_number_total             4973
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            lh2985.cif
_cod_data_source_block           I
_cod_original_cell_volume        1886.49(16)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2225312
_cod_database_fobs_code          2225312
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O121 0.38029(6) 0.5908(2) 0.68188(5) 0.0370(3) Uani d . 1 . .
O O122 0.50403(6) 0.43658(19) 0.71259(5) 0.0290(2) Uani d . 1 . .
O O141 0.29905(7) 1.3039(3) 0.54043(6) 0.0478(3) Uani d . 1 . .
O O142 0.38465(7) 1.4722(2) 0.49984(6) 0.0488(3) Uani d . 1 . .
N N1 0.61933(7) 0.6614(2) 0.68083(5) 0.0238(3) Uani d . 1 . .
H H1 0.6085 0.5463 0.7078 0.029 Uiso d . 1 . .
N N2 0.69791(6) 0.7018(2) 0.67903(5) 0.0223(3) Uani d . 1 . .
N N12 0.45159(7) 0.5957(2) 0.68209(5) 0.0249(3) Uani d . 1 . .
N N14 0.36726(8) 1.3166(3) 0.53486(6) 0.0328(3) Uani d . 1 . .
C C2 0.75430(8) 0.5395(3) 0.70889(6) 0.0210(3) Uani d . 1 . .
C C3 0.74525(8) 0.3003(3) 0.74514(6) 0.0245(3) Uani d . 1 . .
H H3A 0.7560 0.1417 0.7240 0.029 Uiso calc R 1 . .
H H3B 0.6878 0.2904 0.7450 0.029 Uiso calc R 1 . .
C C4 0.83751(8) 0.5887(3) 0.70326(6) 0.0235(3) Uani d . 1 . .
H H4A 0.8796 0.5883 0.7454 0.028 Uiso calc R 1 . .
H H4B 0.8379 0.7640 0.6847 0.028 Uiso calc R 1 . .
C C11 0.55764(8) 0.8161(3) 0.64553(6) 0.0218(3) Uani d . 1 . .
C C12 0.47530(8) 0.7921(3) 0.64507(6) 0.0219(3) Uani d . 1 . .
C C13 0.41292(8) 0.9552(3) 0.60887(6) 0.0250(3) Uani d . 1 . .
H H13 0.3583 0.9382 0.6095 0.030 Uiso calc R 1 . .
C C14 0.43201(8) 1.1413(3) 0.57223(6) 0.0261(3) Uani d . 1 . .
C C15 0.51178(9) 1.1705(3) 0.57056(6) 0.0277(3) Uani d . 1 . .
H H15 0.5233 1.3002 0.5446 0.033 Uiso calc R 1 . .
C C16 0.57319(8) 1.0114(3) 0.60642(6) 0.0255(3) Uani d . 1 . .
H H16 0.6274 1.0320 0.6051 0.031 Uiso calc R 1 . .
C C31 0.80301(8) 0.3014(3) 0.81217(6) 0.0231(3) Uani d . 1 . .
C C32 0.86423(9) 0.1136(3) 0.83308(7) 0.0275(3) Uani d . 1 . .
H H32 0.8710 -0.0142 0.8048 0.033 Uiso calc R 1 . .
C C33 0.91584(9) 0.1099(3) 0.89490(7) 0.0331(4) Uani d . 1 . .
H H33 0.9575 -0.0199 0.9087 0.040 Uiso calc R 1 . .
C C34 0.90638(10) 0.2952(3) 0.93612(7) 0.0358(4) Uani d . 1 . .
H H34 0.9411 0.2920 0.9785 0.043 Uiso calc R 1 . .
C C35 0.84621(10) 0.4858(3) 0.91564(7) 0.0351(4) Uani d . 1 . .
H H35 0.8402 0.6149 0.9439 0.042 Uiso calc R 1 . .
C C36 0.79469(9) 0.4891(3) 0.85398(7) 0.0287(3) Uani d . 1 . .
H H36 0.7535 0.6203 0.8403 0.034 Uiso calc R 1 . .
C C41 0.85952(8) 0.3836(3) 0.66334(6) 0.0223(3) Uani d . 1 . .
C C42 0.80419(9) 0.3234(3) 0.60454(6) 0.0338(4) Uani d . 1 . .
H H42 0.7530 0.4126 0.5897 0.041 Uiso calc R 1 . .
C C43 0.82283(10) 0.1359(4) 0.56759(7) 0.0397(4) Uani d . 1 . .
H H43 0.7843 0.0962 0.5277 0.048 Uiso calc R 1 . .
C C44 0.89716(10) 0.0059(3) 0.58834(7) 0.0327(4) Uani d . 1 . .
H H44 0.9097 -0.1244 0.5630 0.039 Uiso calc R 1 . .
C C45 0.95344(9) 0.0661(3) 0.64620(7) 0.0298(3) Uani d . 1 . .
H H45 1.0051 -0.0206 0.6604 0.036 Uiso calc R 1 . .
C C46 0.93414(8) 0.2534(3) 0.68334(6) 0.0256(3) Uani d . 1 . .
H H46 0.9728 0.2928 0.7232 0.031 Uiso calc R 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C11 N1 N2 . . 118.64(11) ?
C11 N1 H1 . . 118.5 ?
N2 N1 H1 . . 122.5 ?
C2 N2 N1 . . 117.64(11) ?
O121 N12 O122 . . 122.07(12) ?
O121 N12 C12 . . 119.13(11) ?
O122 N12 C12 . . 118.80(11) ?
O141 N14 O142 . . 123.39(12) ?
O141 N14 C14 . . 118.74(13) ?
O142 N14 C14 . . 117.87(13) ?
N2 C2 C4 . . 115.01(12) ?
N2 C2 C3 . . 127.69(13) ?
C4 C2 C3 . . 117.19(11) ?
C2 C3 C31 . . 113.14(11) ?
C2 C3 H3A . . 109.0 ?
C31 C3 H3A . . 109.0 ?
C2 C3 H3B . . 109.0 ?
C31 C3 H3B . . 109.0 ?
H3A C3 H3B . . 107.8 ?
C2 C4 C41 . . 111.89(11) ?
C2 C4 H4A . . 109.2 ?
C41 C4 H4A . . 109.2 ?
C2 C4 H4B . . 109.2 ?
C41 C4 H4B . . 109.2 ?
H4A C4 H4B . . 107.9 ?
N1 C11 C16 . . 120.40(12) ?
N1 C11 C12 . . 122.68(12) ?
C16 C11 C12 . . 116.92(12) ?
C13 C12 C11 . . 121.72(13) ?
C13 C12 N12 . . 116.36(12) ?
C11 C12 N12 . . 121.92(11) ?
C14 C13 C12 . . 118.55(13) ?
C14 C13 H13 . . 120.7 ?
C12 C13 H13 . . 120.7 ?
C13 C14 C15 . . 121.84(12) ?
C13 C14 N14 . . 118.98(13) ?
C15 C14 N14 . . 119.16(13) ?
C16 C15 C14 . . 119.63(13) ?
C16 C15 H15 . . 120.2 ?
C14 C15 H15 . . 120.2 ?
C15 C16 C11 . . 121.32(13) ?
C15 C16 H16 . . 119.3 ?
C11 C16 H16 . . 119.3 ?
C32 C31 C36 . . 118.78(13) ?
C32 C31 C3 . . 120.76(12) ?
C36 C31 C3 . . 120.46(12) ?
C31 C32 C33 . . 120.88(14) ?
C31 C32 H32 . . 119.6 ?
C33 C32 H32 . . 119.6 ?
C34 C33 C32 . . 119.82(14) ?
C34 C33 H33 . . 120.1 ?
C32 C33 H33 . . 120.1 ?
C33 C34 C35 . . 119.86(14) ?
C33 C34 H34 . . 120.1 ?
C35 C34 H34 . . 120.1 ?
C34 C35 C36 . . 120.26(14) ?
C34 C35 H35 . . 119.9 ?
C36 C35 H35 . . 119.9 ?
C35 C36 C31 . . 120.39(14) ?
C35 C36 H36 . . 119.8 ?
C31 C36 H36 . . 119.8 ?
C46 C41 C42 . . 118.28(13) ?
C46 C41 C4 . . 121.75(11) ?
C42 C41 C4 . . 119.96(12) ?
C43 C42 C41 . . 120.87(13) ?
C43 C42 H42 . . 119.6 ?
C41 C42 H42 . . 119.6 ?
C44 C43 C42 . . 120.23(13) ?
C44 C43 H43 . . 119.9 ?
C42 C43 H43 . . 119.9 ?
C43 C44 C45 . . 119.72(14) ?
C43 C44 H44 . . 120.1 ?
C45 C44 H44 . . 120.1 ?
C44 C45 C46 . . 119.81(13) ?
C44 C45 H45 . . 120.1 ?
C46 C45 H45 . . 120.1 ?
C41 C46 C45 . . 121.07(12) ?
C41 C46 H46 . . 119.5 ?
C45 C46 H46 . . 119.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O121 N12 . 1.2281(15) ?
O122 N12 . 1.2409(15) ?
O141 N14 . 1.2261(16) ?
O142 N14 . 1.2305(17) ?
N1 C11 . 1.3528(17) ?
N1 N2 . 1.3847(15) ?
N1 H1 . 0.9123 ?
N2 C2 . 1.2854(17) ?
N12 C12 . 1.4525(18) ?
N14 C14 . 1.4615(17) ?
C2 C4 . 1.5036(19) ?
C2 C3 . 1.5093(19) ?
C3 C31 . 1.5180(18) ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C4 C41 . 1.5140(19) ?
C4 H4A . 0.9900 ?
C4 H4B . 0.9900 ?
C11 C16 . 1.420(2) ?
C11 C12 . 1.4218(18) ?
C12 C13 . 1.3917(18) ?
C13 C14 . 1.374(2) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.397(2) ?
C15 C16 . 1.3672(19) ?
C15 H15 . 0.9500 ?
C16 H16 . 0.9500 ?
C31 C32 . 1.387(2) ?
C31 C36 . 1.390(2) ?
C32 C33 . 1.3911(19) ?
C32 H32 . 0.9500 ?
C33 C34 . 1.379(2) ?
C33 H33 . 0.9500 ?
C34 C35 . 1.385(2) ?
C34 H34 . 0.9500 ?
C35 C36 . 1.388(2) ?
C35 H35 . 0.9500 ?
C36 H36 . 0.9500 ?
C41 C46 . 1.3835(18) ?
C41 C42 . 1.3939(18) ?
C42 C43 . 1.380(2) ?
C42 H42 . 0.9500 ?
C43 C44 . 1.379(2) ?
C43 H43 . 0.9500 ?
C44 C45 . 1.3843(19) ?
C44 H44 . 0.9500 ?
C45 C46 . 1.388(2) ?
C45 H45 . 0.9500 ?
C46 H46 . 0.9500 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 O122 . 0.91 1.92 2.5976(15) 129 y
C15 H15 O142 3_686 0.95 2.44 3.314(2) 153 y
C3 H3A N2 1_545 0.99 2.53 3.3811(18) 144 y
C3 H3B O121 2_646 0.99 2.55 3.3138(18) 134 y
C4 H4B Cg41 1_565 0.99 2.79 3.7438(16) 163 y
C45 H45 Cg31 2_746 0.95 2.92 3.7424(18) 145 y
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C11 N1 N2 C2 . . . . -174.48(12) ?
N1 N2 C2 C4 . . . . 177.96(11) ?
N1 N2 C2 C3 . . . . 1.8(2) ?
N2 C2 C3 C31 . . . . -124.82(14) ?
C4 C2 C3 C31 . . . . 59.11(16) ?
N2 C2 C4 C41 . . . . -108.55(13) ?
C3 C2 C4 C41 . . . . 68.02(15) ?
N2 N1 C11 C16 . . . . 1.50(18) ?
N2 N1 C11 C12 . . . . -178.97(11) ?
N1 C11 C12 C13 . . . . 179.34(12) ?
C16 C11 C12 C13 . . . . -1.12(19) ?
N1 C11 C12 N12 . . . . -0.91(19) ?
C16 C11 C12 N12 . . . . 178.63(12) ?
O121 N12 C12 C13 . . . . -3.20(18) ?
O122 N12 C12 C13 . . . . 176.22(12) ?
O121 N12 C12 C11 . . . . 177.04(12) ?
O122 N12 C12 C11 . . . . -3.54(18) ?
C11 C12 C13 C14 . . . . 0.8(2) ?
N12 C12 C13 C14 . . . . -178.94(11) ?
C12 C13 C14 C15 . . . . -0.1(2) ?
C12 C13 C14 N14 . . . . -178.95(12) ?
O141 N14 C14 C13 . . . . 4.8(2) ?
O142 N14 C14 C13 . . . . -176.13(13) ?
O141 N14 C14 C15 . . . . -174.14(13) ?
O142 N14 C14 C15 . . . . 4.95(19) ?
C13 C14 C15 C16 . . . . -0.3(2) ?
N14 C14 C15 C16 . . . . 178.54(12) ?
C14 C15 C16 C11 . . . . 0.0(2) ?
N1 C11 C16 C15 . . . . -179.75(13) ?
C12 C11 C16 C15 . . . . 0.70(19) ?
C2 C3 C31 C32 . . . . -115.42(15) ?
C2 C3 C31 C36 . . . . 65.49(17) ?
C36 C31 C32 C33 . . . . 0.8(2) ?
C3 C31 C32 C33 . . . . -178.27(13) ?
C31 C32 C33 C34 . . . . -0.1(2) ?
C32 C33 C34 C35 . . . . -0.8(2) ?
C33 C34 C35 C36 . . . . 0.9(2) ?
C34 C35 C36 C31 . . . . -0.1(2) ?
C32 C31 C36 C35 . . . . -0.7(2) ?
C3 C31 C36 C35 . . . . 178.37(13) ?
C2 C4 C41 C46 . . . . -129.80(14) ?
C2 C4 C41 C42 . . . . 50.75(18) ?
C46 C41 C42 C43 . . . . 1.0(2) ?
C4 C41 C42 C43 . . . . -179.56(15) ?
C41 C42 C43 C44 . . . . -0.4(3) ?
C42 C43 C44 C45 . . . . -0.6(3) ?
C43 C44 C45 C46 . . . . 1.1(2) ?
C42 C41 C46 C45 . . . . -0.5(2) ?
C4 C41 C46 C45 . . . . -179.95(13) ?
C44 C45 C46 C41 . . . . -0.5(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 277712
2 PubChem 313935
