#------------------------------------------------------------------------------
#$Date: 2023-12-07 13:49:25 +0200 (Thu, 07 Dec 2023) $
#$Revision: 288135 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/29/2022925.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_2022925
loop_
_publ_author_name
'Bui, Thai Thanh Thu'
'Mac, Dinh Hung'
'Quang Trung, Pham'
'Pham, Chien Thang'
_publ_section_title
;
 Crystal structure of
 4-(naphthalen-2-yl)-2-oxo-6-phenyl-1,2-di-hydro-pyridine-3-carbo-nitrile.
;
_journal_coeditor_code           DJ2070
_journal_issue                   'Pt 11'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              1076
_journal_page_last               1078
_journal_paper_doi               10.1107/S2056989023009180
_journal_volume                  79
_journal_year                    2023
_chemical_formula_iupac          'C22 H14 N2 O'
_chemical_formula_moiety         'C22 H14 N2 O'
_chemical_formula_sum            'C22 H14 N2 O'
_chemical_formula_weight         322.35
_chemical_name_systematic
;
4-(Naphthalen-2-yl)-2-oxo-6-phenyl-1,2-dihydropyridine-3-carbonitrile
;
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.878(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.0845(4)
_cell_length_b                   10.4369(6)
_cell_length_c                   21.6298(11)
_cell_measurement_reflns_used    7569
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.32
_cell_measurement_theta_min      2.71
_cell_volume                     1598.45(15)
_computing_cell_refinement
;
SAINT V8.40A (Bruker, 2019)
;
_computing_data_collection
;
APEX3 (Bruker, 2019)
;
_computing_data_reduction
;
SAINT V8.40A (Bruker, 2019)
;
_computing_molecular_graphics
;
Olex2 1.5 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
Olex2 1.5 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT  (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_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            18613
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.377
_diffrn_reflns_theta_min         2.713
_diffrn_source                   'sealed X-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6550
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.214
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3250
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0479
_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)+(0.0459P)²+0.7178P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1099
_refine_ls_wR_factor_ref         0.1225
_reflns_number_gt                2531
_reflns_number_total             3250
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            dj2070sup1.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 2022925.cif.'
_cod_database_code               2022925
_cod_database_fobs_code          2022925
_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   0.972
_shelx_estimated_absorpt_t_max   0.988
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_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_disorder_assembly
_atom_site_disorder_group
O O2 0.82728(17) 0.39070(12) 0.51570(6) 0.0445(3) Uani d 1 . .
N N1 0.8282(2) 0.59995(14) 0.54490(6) 0.0335(3) Uani d 1 . .
C C6 0.7537(2) 0.70213(16) 0.57481(8) 0.0329(4) Uani d 1 . .
C C2 0.7497(2) 0.47978(16) 0.54354(8) 0.0331(4) Uani d 1 . .
C C48 0.0535(2) 0.45419(16) 0.68796(8) 0.0334(4) Uani d 1 . .
C C60 0.8580(2) 0.82447(16) 0.57434(8) 0.0341(4) Uani d 1 . .
C C4 0.5045(2) 0.56580(17) 0.61101(8) 0.0327(4) Uani d 1 . .
C C3 0.5797(2) 0.46509(16) 0.57786(8) 0.0322(4) Uani d 1 . .
C C41 0.1982(2) 0.46820(17) 0.64419(8) 0.0342(4) Uani d 1 . .
H H41 0.191623 0.420700 0.607804 0.041 Uiso calc 1 . .
C C40 0.3471(2) 0.55046(16) 0.65470(8) 0.0340(4) Uani d 1 . .
C C5 0.5920(2) 0.68616(17) 0.60673(8) 0.0366(4) Uani d 1 . .
H H5 0.538843 0.756446 0.626038 0.044 Uiso calc 1 . .
C C61 0.7640(3) 0.93869(17) 0.56255(8) 0.0409(4) Uani d 1 . .
H H61 0.635429 0.937948 0.552319 0.049 Uiso calc 1 . .
C C49 0.0619(2) 0.52910(18) 0.74242(8) 0.0381(4) Uani d 1 . .
N N31 0.4577(3) 0.23249(18) 0.58144(10) 0.0640(5) Uani d 1 . .
C C42 -0.0972(2) 0.36732(18) 0.67854(9) 0.0411(4) Uani d 1 . .
H H42 -0.101608 0.315499 0.643546 0.049 Uiso calc 1 . .
C C65 1.0507(3) 0.82723(19) 0.58974(9) 0.0443(5) Uani d 1 . .
H H65 1.116142 0.751180 0.597029 0.053 Uiso calc 1 . .
C C47 0.3542(3) 0.62309(19) 0.71018(9) 0.0437(5) Uani d 1 . .
H H47 0.455112 0.678437 0.717990 0.052 Uiso calc 1 . .
C C45 -0.0852(3) 0.51704(19) 0.78517(9) 0.0459(5) Uani d 1 . .
H H45 -0.081273 0.565435 0.821287 0.055 Uiso calc 1 . .
C C62 0.8604(3) 1.05386(18) 0.56591(10) 0.0499(5) Uani d 1 . .
H H62 0.797354 1.130175 0.557074 0.060 Uiso calc 1 . .
C C30 0.5102(2) 0.33702(19) 0.58021(9) 0.0422(5) Uani d 1 . .
C C43 -0.2373(3) 0.3587(2) 0.72060(9) 0.0478(5) Uani d 1 . .
H H43 -0.336678 0.301691 0.713812 0.057 Uiso calc 1 . .
C C46 0.2157(3) 0.61315(19) 0.75229(9) 0.0467(5) Uani d 1 . .
H H46 0.222902 0.662601 0.788055 0.056 Uiso calc 1 . .
C C44 -0.2314(3) 0.4353(2) 0.77365(9) 0.0490(5) Uani d 1 . .
H H44 -0.328752 0.430277 0.801378 0.059 Uiso calc 1 . .
C C63 1.0496(3) 1.0555(2) 0.58234(10) 0.0541(6) Uani d 1 . .
H H63 1.113658 1.133087 0.585465 0.065 Uiso calc 1 . .
C C64 1.1440(3) 0.9430(2) 0.59413(11) 0.0545(5) Uani d 1 . .
H H64 1.271945 0.944829 0.605168 0.065 Uiso calc 1 . .
H H1 0.937(3) 0.610(2) 0.5249(10) 0.053(6) Uiso d 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
C6 N1 C2 . . 124.23(14) ?
C6 N1 H1 . . 119.1(13) ?
C2 N1 H1 . . 116.7(13) ?
N1 C6 C60 . . 118.17(14) ?
N1 C6 C5 . . 119.25(16) ?
C5 C6 C60 . . 122.49(15) ?
O2 C2 N1 . . 120.53(15) ?
O2 C2 C3 . . 123.93(16) ?
N1 C2 C3 . . 115.50(15) ?
C49 C48 C41 . . 119.03(16) ?
C42 C48 C41 . . 121.83(16) ?
C42 C48 C49 . . 119.14(15) ?
C61 C60 C6 . . 120.54(16) ?
C61 C60 C65 . . 119.16(17) ?
C65 C60 C6 . . 120.18(16) ?
C3 C4 C40 . . 123.54(15) ?
C3 C4 C5 . . 117.71(14) ?
C5 C4 C40 . . 118.54(15) ?
C4 C3 C2 . . 121.73(15) ?
C4 C3 C30 . . 123.54(15) ?
C30 C3 C2 . . 114.38(15) ?
C48 C41 H41 . . 119.4 ?
C40 C41 C48 . . 121.29(16) ?
C40 C41 H41 . . 119.4 ?
C41 C40 C4 . . 123.20(15) ?
C41 C40 C47 . . 118.67(15) ?
C47 C40 C4 . . 118.11(15) ?
C6 C5 C4 . . 121.42(16) ?
C6 C5 H5 . . 119.3 ?
C4 C5 H5 . . 119.3 ?
C60 C61 H61 . . 119.9 ?
C62 C61 C60 . . 120.29(18) ?
C62 C61 H61 . . 119.9 ?
C48 C49 C45 . . 118.78(17) ?
C46 C49 C48 . . 118.80(15) ?
C46 C49 C45 . . 122.42(17) ?
C48 C42 H42 . . 119.8 ?
C43 C42 C48 . . 120.48(18) ?
C43 C42 H42 . . 119.8 ?
C60 C65 H65 . . 120.1 ?
C64 C65 C60 . . 119.83(18) ?
C64 C65 H65 . . 120.1 ?
C40 C47 H47 . . 119.4 ?
C46 C47 C40 . . 121.16(17) ?
C46 C47 H47 . . 119.4 ?
C49 C45 H45 . . 119.8 ?
C44 C45 C49 . . 120.49(18) ?
C44 C45 H45 . . 119.8 ?
C61 C62 H62 . . 120.0 ?
C63 C62 C61 . . 119.97(19) ?
C63 C62 H62 . . 120.0 ?
N31 C30 C3 . . 178.4(2) ?
C42 C43 H43 . . 119.8 ?
C42 C43 C44 . . 120.30(18) ?
C44 C43 H43 . . 119.8 ?
C49 C46 H46 . . 119.5 ?
C47 C46 C49 . . 121.03(17) ?
C47 C46 H46 . . 119.5 ?
C45 C44 C43 . . 120.75(17) ?
C45 C44 H44 . . 119.6 ?
C43 C44 H44 . . 119.6 ?
C62 C63 H63 . . 119.9 ?
C64 C63 C62 . . 120.21(19) ?
C64 C63 H63 . . 119.9 ?
C65 C64 H64 . . 119.7 ?
C63 C64 C65 . . 120.52(19) ?
C63 C64 H64 . . 119.7 ?
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
O2 C2 . 1.245(2) ?
N1 C6 . 1.363(2) ?
N1 C2 . 1.372(2) ?
N1 H1 . 0.90(2) ?
C6 C60 . 1.475(2) ?
C6 C5 . 1.367(2) ?
C2 C3 . 1.444(2) ?
C48 C41 . 1.425(2) ?
C48 C49 . 1.413(3) ?
C48 C42 . 1.411(2) ?
C60 C61 . 1.385(2) ?
C60 C65 . 1.395(3) ?
C4 C3 . 1.388(2) ?
C4 C40 . 1.494(2) ?
C4 C5 . 1.405(2) ?
C3 C30 . 1.426(3) ?
C41 H41 . 0.9300 ?
C41 C40 . 1.373(2) ?
C40 C47 . 1.419(3) ?
C5 H5 . 0.9300 ?
C61 H61 . 0.9300 ?
C61 C62 . 1.383(3) ?
C49 C45 . 1.421(2) ?
C49 C46 . 1.410(3) ?
N31 C30 . 1.153(3) ?
C42 H42 . 0.9300 ?
C42 C43 . 1.371(3) ?
C65 H65 . 0.9300 ?
C65 C64 . 1.379(3) ?
C47 H47 . 0.9300 ?
C47 C46 . 1.364(2) ?
C45 H45 . 0.9300 ?
C45 C44 . 1.359(3) ?
C62 H62 . 0.9300 ?
C62 C63 . 1.375(3) ?
C43 H43 . 0.9300 ?
C43 C44 . 1.398(3) ?
C46 H46 . 0.9300 ?
C44 H44 . 0.9300 ?
C63 H63 . 0.9300 ?
C63 C64 . 1.370(3) ?
C64 H64 . 0.9300 ?
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 O2 3_766 0.90(2) 1.91(2) 2.8096(18) 172.8(19) 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O2 C2 C3 C4 . . . . 176.33(17) ?
O2 C2 C3 C30 . . . . 3.0(3) ?
N1 C6 C60 C61 . . . . 135.08(17) ?
N1 C6 C60 C65 . . . . -49.1(2) ?
N1 C6 C5 C4 . . . . 2.1(3) ?
N1 C2 C3 C4 . . . . -1.4(2) ?
N1 C2 C3 C30 . . . . -174.79(15) ?
C6 N1 C2 O2 . . . . -179.26(16) ?
C6 N1 C2 C3 . . . . -1.4(2) ?
C6 C60 C61 C62 . . . . 176.01(17) ?
C6 C60 C65 C64 . . . . -174.71(18) ?
C2 N1 C6 C60 . . . . 177.59(15) ?
C2 N1 C6 C5 . . . . 1.1(3) ?
C48 C41 C40 C4 . . . . 178.35(16) ?
C48 C41 C40 C47 . . . . -0.5(3) ?
C48 C49 C45 C44 . . . . -0.3(3) ?
C48 C49 C46 C47 . . . . 0.3(3) ?
C48 C42 C43 C44 . . . . -0.6(3) ?
C60 C6 C5 C4 . . . . -174.25(16) ?
C60 C61 C62 C63 . . . . -1.4(3) ?
C60 C65 C64 C63 . . . . -1.2(3) ?
C4 C40 C47 C46 . . . . -179.62(18) ?
C3 C4 C40 C41 . . . . -37.2(3) ?
C3 C4 C40 C47 . . . . 141.73(18) ?
C3 C4 C5 C6 . . . . -4.7(3) ?
C41 C48 C49 C45 . . . . 178.47(16) ?
C41 C48 C49 C46 . . . . -1.4(3) ?
C41 C48 C42 C43 . . . . -178.05(17) ?
C41 C40 C47 C46 . . . . -0.7(3) ?
C40 C4 C3 C2 . . . . -170.35(16) ?
C40 C4 C3 C30 . . . . 2.4(3) ?
C40 C4 C5 C6 . . . . 170.28(16) ?
C40 C47 C46 C49 . . . . 0.8(3) ?
C5 C6 C60 C61 . . . . -48.6(2) ?
C5 C6 C60 C65 . . . . 127.28(19) ?
C5 C4 C3 C2 . . . . 4.3(2) ?
C5 C4 C3 C30 . . . . 177.09(17) ?
C5 C4 C40 C41 . . . . 148.18(17) ?
C5 C4 C40 C47 . . . . -32.9(2) ?
C61 C60 C65 C64 . . . . 1.2(3) ?
C61 C62 C63 C64 . . . . 1.4(3) ?
C49 C48 C41 C40 . . . . 1.6(3) ?
C49 C48 C42 C43 . . . . 2.2(3) ?
C49 C45 C44 C43 . . . . 2.0(3) ?
C42 C48 C41 C40 . . . . -178.13(16) ?
C42 C48 C49 C45 . . . . -1.8(3) ?
C42 C48 C49 C46 . . . . 178.30(17) ?
C42 C43 C44 C45 . . . . -1.6(3) ?
C65 C60 C61 C62 . . . . 0.1(3) ?
C45 C49 C46 C47 . . . . -179.63(19) ?
C62 C63 C64 C65 . . . . -0.1(3) ?
C46 C49 C45 C44 . . . . 179.63(19) ?
