#------------------------------------------------------------------------------
#$Date: 2025-08-19 09:12:48 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301798 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/92/2019207.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_2019207
loop_
_publ_author_name
'Wade, Colin B.'
'Mohanty, Dillip K.'
'Squattrito, Philip J.'
'Amato, Nicholas J.'
'Kirschbaum, Kristin'
_publ_section_title
;
 A series of N-(2-phenylethyl)nitroaniline derivatives as
 precursors for slow and sustained nitric oxide release agents
;
_journal_coeditor_code           CU3041
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1383
_journal_page_last               1389
_journal_paper_doi               10.1107/S0108270113025869
_journal_volume                  69
_journal_year                    2013
_chemical_formula_moiety         'C15 H13 N3 O2'
_chemical_formula_sum            'C15 H13 N3 O2'
_chemical_formula_weight         267.28
_chemical_melting_point          427
_chemical_name_common            2-cyano-4-nitro-N-(2-phenylethyl)aniline
_chemical_name_systematic
;
2-cyano-4-nitro-N-(2-phenylethyl)aniline
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.3840(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4871(5)
_cell_length_b                   16.2700(10)
_cell_length_c                   10.8432(7)
_cell_measurement_reflns_used    23429
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.95
_cell_measurement_theta_min      2.26
_cell_volume                     1317.00(15)
_computing_cell_refinement       'APEX2 (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'APEX2 (Bruker, 2005)'
_computing_molecular_graphics    'CrystalMaker (Palmer, 2013)'
_computing_publication_material  'APEX2 (Bruker, 2005)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device_type  'Bruker APEX DUO CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_av_sigmaI/netI    0.0131
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            23007
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         32.94
_diffrn_reflns_theta_min         2.26
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9908
_exptl_absorpt_correction_T_min  0.9640
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelpiped
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.555
_refine_diff_density_min         -0.200
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         4732
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0378
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0687P)²+0.3103P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1080
_refine_ls_wR_factor_ref         0.1129
_reflns_number_gt                4189
_reflns_number_total             4732
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cu3041.cif
_cod_data_source_block           C15H13N3O2
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               2019207
loop_
_symmetry_equiv_pos_as_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_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_occupancy
_atom_site_symmetry_multiplicity
O O41 0.28684(9) 0.12353(4) 0.29556(6) 0.02323(14) Uani d 1 1
O O42 0.10504(8) 0.03747(4) 0.37421(6) 0.02067(13) Uani d 1 1
N N1 0.65662(8) 0.09507(4) 0.83376(6) 0.01439(12) Uani d 1 1
H H1 0.6214(19) 0.0666(9) 0.8948(14) 0.033(3) Uiso d 1 1
N N2 0.33192(10) -0.05113(4) 0.89432(7) 0.02022(14) Uani d 1 1
N N4 0.23997(8) 0.08139(4) 0.38232(6) 0.01466(13) Uani d 1 1
C C1 0.55906(9) 0.09106(4) 0.72443(6) 0.01199(13) Uani d 1 1
C C2 0.40849(9) 0.03712(4) 0.70702(6) 0.01168(13) Uani d 1 1
C C3 0.30296(9) 0.03411(4) 0.59568(7) 0.01221(13) Uani d 1 1
H H3 0.2029(15) -0.0007(7) 0.5865(11) 0.019(3) Uiso d 1 1
C C4 0.34763(9) 0.08426(4) 0.49902(6) 0.01264(13) Uani d 1 1
C C5 0.49621(10) 0.13679(5) 0.51165(7) 0.01499(14) Uani d 1 1
H H5 0.5272(16) 0.1712(8) 0.4445(11) 0.021(3) Uiso d 1 1
C C6 0.59954(10) 0.13990(5) 0.62209(7) 0.01514(14) Uani d 1 1
H H6 0.6992(17) 0.1754(8) 0.6296(12) 0.024(3) Uiso d 1 1
C C7 0.80953(9) 0.14949(5) 0.86030(7) 0.01465(14) Uani d 1 1
H H7A 0.7833(16) 0.2054(7) 0.8259(11) 0.020(3) Uiso d 1 1
H H7B 0.8227(16) 0.1545(8) 0.9503(12) 0.022(3) Uiso d 1 1
C C8 0.98355(10) 0.11550(5) 0.81298(8) 0.01875(15) Uani d 1 1
H H8B 0.9959(18) 0.0584(8) 0.8430(13) 0.029(3) Uiso d 1 1
H H8A 0.9744(18) 0.1137(8) 0.7233(13) 0.030(3) Uiso d 1 1
C C9 1.14367(9) 0.16670(5) 0.85827(7) 0.01476(14) Uani d 1 1
C C10 1.22232(10) 0.15533(5) 0.97834(7) 0.01569(14) Uani d 1 1
H H10 1.1749(18) 0.1134(8) 1.0314(13) 0.027(3) Uiso d 1 1
C C11 1.36857(10) 0.20255(5) 1.02246(7) 0.01573(14) Uani d 1 1
H H11 1.4201(18) 0.1936(8) 1.1055(12) 0.026(3) Uiso d 1 1
C C12 1.43693(10) 0.26274(5) 0.94762(7) 0.01653(14) Uani d 1 1
H H12 1.5371(18) 0.2976(8) 0.9811(13) 0.030(3) Uiso d 1 1
C C13 1.36012(10) 0.27489(5) 0.82797(7) 0.01769(15) Uani d 1 1
H H13 1.4088(18) 0.3160(8) 0.7747(13) 0.028(3) Uiso d 1 1
C C14 1.21486(10) 0.22666(5) 0.78384(7) 0.01678(14) Uani d 1 1
H H14 1.1657(16) 0.2334(8) 0.6966(12) 0.024(3) Uiso d 1 1
C C15 0.36369(9) -0.01308(4) 0.80896(7) 0.01396(13) Uani d 1 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
C1 N1 C7 124.63(6)
C1 N1 H1 118.1(10)
C7 N1 H1 117.0(10)
O42 N4 O41 123.01(7)
O42 N4 C4 118.59(6)
O41 N4 C4 118.40(6)
N1 C1 C6 121.93(6)
N1 C1 C2 121.03(6)
C6 C1 C2 117.04(6)
C3 C2 C1 121.71(6)
C3 C2 C15 119.83(6)
C1 C2 C15 118.43(6)
C4 C3 C2 118.70(6)
C4 C3 H3 120.7(7)
C2 C3 H3 120.6(7)
C3 C4 C5 121.31(7)
C3 C4 N4 119.36(6)
C5 C4 N4 119.32(6)
C6 C5 C4 119.78(7)
C6 C5 H5 119.1(7)
C4 C5 H5 121.1(7)
C5 C6 C1 121.44(7)
C5 C6 H6 119.1(8)
C1 C6 H6 119.5(8)
N1 C7 C8 112.82(6)
N1 C7 H7A 110.5(7)
C8 C7 H7A 110.5(7)
N1 C7 H7B 105.4(7)
C8 C7 H7B 109.9(7)
H7A C7 H7B 107.4(10)
C9 C8 C7 111.37(6)
C9 C8 H8B 111.1(8)
C7 C8 H8B 106.8(8)
C9 C8 H8A 109.7(8)
C7 C8 H8A 110.4(8)
H8B C8 H8A 107.4(11)
C14 C9 C10 118.53(7)
C14 C9 C8 121.69(7)
C10 C9 C8 119.77(7)
C11 C10 C9 120.71(7)
C11 C10 H10 119.6(8)
C9 C10 H10 119.6(8)
C10 C11 C12 120.12(7)
C10 C11 H11 119.1(8)
C12 C11 H11 120.8(8)
C13 C12 C11 119.89(7)
C13 C12 H12 120.6(8)
C11 C12 H12 119.5(8)
C12 C13 C14 119.67(7)
C12 C13 H13 120.3(8)
C14 C13 H13 120.0(8)
C13 C14 C9 121.07(7)
C13 C14 H14 119.1(7)
C9 C14 H14 119.8(7)
N2 C15 C2 177.02(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O41 N4 1.2364(9)
O42 N4 1.2351(9)
N1 C1 1.3456(9)
N1 C7 1.4585(9)
N1 H1 0.866(15)
N2 C15 1.1534(10)
N4 C4 1.4481(9)
C1 C6 1.4163(10)
C1 C2 1.4298(9)
C2 C3 1.3923(10)
C2 C15 1.4346(10)
C3 C4 1.3892(10)
C3 H3 0.938(12)
C4 C5 1.4013(10)
C5 C6 1.3761(10)
C5 H5 0.961(12)
C6 H6 0.942(13)
C7 C8 1.5391(11)
C7 H7A 0.997(12)
C7 H7B 0.976(13)
C8 C9 1.5107(10)
C8 H8B 0.986(14)
C8 H8A 0.970(14)
C9 C14 1.3975(11)
C9 C10 1.3995(11)
C10 C11 1.3921(10)
C10 H10 0.977(13)
C11 C12 1.3938(11)
C11 H11 0.963(13)
C12 C13 1.3925(11)
C12 H12 0.987(14)
C13 C14 1.3957(11)
C13 H13 0.972(14)
C14 H14 0.994(13)
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
N1 H1 N2 3_657 0.866(15) 2.300(15) 3.0287(10) 141.9(12)
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
C7 N1 C1 C6 1.06(11)
C7 N1 C1 C2 -178.63(6)
N1 C1 C2 C3 178.00(7)
C6 C1 C2 C3 -1.70(10)
N1 C1 C2 C15 -0.18(10)
C6 C1 C2 C15 -179.88(6)
C1 C2 C3 C4 0.87(10)
C15 C2 C3 C4 179.03(6)
C2 C3 C4 C5 0.39(11)
C2 C3 C4 N4 179.54(6)
O42 N4 C4 C3 3.91(10)
O41 N4 C4 C3 -176.58(7)
O42 N4 C4 C5 -176.93(7)
O41 N4 C4 C5 2.58(10)
C3 C4 C5 C6 -0.76(11)
N4 C4 C5 C6 -179.91(7)
C4 C5 C6 C1 -0.14(11)
N1 C1 C6 C5 -178.37(7)
C2 C1 C6 C5 1.33(11)
C1 N1 C7 C8 -81.27(9)
N1 C7 C8 C9 -171.53(6)
C7 C8 C9 C14 -98.73(8)
C7 C8 C9 C10 80.25(9)
C14 C9 C10 C11 -0.20(11)
C8 C9 C10 C11 -179.21(7)
C9 C10 C11 C12 0.90(11)
C10 C11 C12 C13 -0.82(11)
C11 C12 C13 C14 0.06(12)
C12 C13 C14 C9 0.65(12)
C10 C9 C14 C13 -0.58(11)
C8 C9 C14 C13 178.41(7)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 4013392
