#------------------------------------------------------------------------------
#$Date: 2019-10-28 18:03:06 +0200 (Mon, 28 Oct 2019) $
#$Revision: 220206 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/50/4515082.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_4515082
loop_
_publ_author_name
'Mandal, Tripti'
'Pathak, Sudipta'
'Dey, Arka'
'Islam, Md Maidul'
'Seth, Saikat Kumar'
'Masum, Abdulla Al'
'Ortega-Castro, Joaquín'
'Ray, Partha Pratim'
'Frontera, Antonio'
'Mukhopadhyay, Subrata'
_publ_section_title
;
 Structures, Photoresponse Properties, and Biological Activity of
 Dicyano-Substituted 4-Aryl-2-pyridone Derivatives.
;
_journal_issue                   4
_journal_name_full               'ACS omega'
_journal_page_first              7200
_journal_page_last               7212
_journal_paper_doi               10.1021/acsomega.9b00289
_journal_volume                  4
_journal_year                    2019
_chemical_formula_sum            'C14 H14 Cl N5 O3'
_chemical_formula_weight         335.75
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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                 98.556(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.8612(4)
_cell_length_b                   8.4861(4)
_cell_length_c                   23.2316(12)
_cell_measurement_reflns_used    1370
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      1.5
_cell_volume                     1532.55(13)
_computing_cell_refinement       'APEX2(Bruker,2007)and SAINT (Bruker,2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT(Bruker,2007)and XPREP(Bruker,2007)'
_computing_molecular_graphics
;    
ORTEP-3 for Windows (Farrugia, 1997), DIAMOND (Brandenburg,
1999) and Mercury (Macrae et al., 2006)
;
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD area-detector'
_diffrn_measurement_method       'ω and φ'
_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  0.0218
_diffrn_reflns_av_sigmaI/netI    0.0213
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8370
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.77
_exptl_absorpt_coefficient_mu    0.272
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.570
_refine_diff_density_min         -0.520
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2522
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0445
_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)+(0.0463P)²+1.4457P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1136
_refine_ls_wR_factor_ref         0.1184
_reflns_number_gt                2190
_reflns_number_total             2522
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ao9b00289_si_003.cif
_cod_data_source_block           tm-11-revised
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4515082
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
Cl1 Cl 0.30132(9) 0.50877(10) 0.22045(3) 0.0577(3) Uani 1 1 d .
C9 C 0.2911(3) 0.1210(3) 0.46519(10) 0.0302(5) Uani 1 1 d D
C7 C 0.5856(3) 0.3109(3) 0.49414(10) 0.0269(5) Uani 1 1 d .
C6 C 0.5375(3) 0.2659(3) 0.43670(10) 0.0258(5) Uani 1 1 d .
C4 C 0.6394(3) 0.3185(3) 0.39109(10) 0.0268(5) Uani 1 1 d .
C8 C 0.4910(3) 0.2605(3) 0.53924(10) 0.0301(5) Uani 1 1 d D
C10 C 0.3923(3) 0.1714(3) 0.42214(10) 0.0284(5) Uani 1 1 d .
C5 C 0.5576(3) 0.3766(3) 0.33871(10) 0.0327(6) Uani 1 1 d .
H5 H 0.4382 0.3837 0.3320 0.039 Uiso 1 1 calc R
C3 C 0.8188(3) 0.3117(3) 0.39889(10) 0.0298(5) Uani 1 1 d .
H3 H 0.8786 0.2743 0.4338 0.036 Uiso 1 1 calc R
C1 C 0.8204(3) 0.4147(3) 0.30428(11) 0.0425(6) Uani 1 1 d .
H1 H 0.8792 0.4465 0.2744 0.051 Uiso 1 1 calc R
C2 C 0.9078(3) 0.3599(3) 0.35535(11) 0.0373(6) Uani 1 1 d .
H2 H 1.0273 0.3550 0.3608 0.045 Uiso 1 1 calc R
N2 N 0.3512(2) 0.1619(2) 0.52231(8) 0.0278(4) Uani 1 1 d .
N1 N 0.6481(3) 0.4223(3) 0.29782(9) 0.0389(5) Uani 1 1 d .
H1A H 0.5938 0.4584 0.2657 0.047 Uiso 1 1 calc R
C11 C 0.7199(3) 0.4212(3) 0.51237(10) 0.0294(5) Uani 1 1 d .
C12 C 0.3331(3) 0.1151(3) 0.36498(11) 0.0368(6) Uani 1 1 d .
N3 N 0.8247(3) 0.5113(3) 0.52851(10) 0.0406(5) Uani 1 1 d .
N4 N 0.2795(3) 0.0676(4) 0.31988(11) 0.0616(7) Uani 1 1 d .
O1 O 0.5251(2) 0.3003(2) 0.59065(7) 0.0455(5) Uani 1 1 d D
O2 O 0.1576(2) 0.0427(2) 0.45404(8) 0.0451(5) Uani 1 1 d D
C13 C 0.2570(3) 0.1036(3) 0.56808(10) 0.0319(5) Uani 1 1 d .
H13A H 0.3388 0.0717 0.6015 0.038 Uiso 1 1 calc R
H13B H 0.1906 0.0115 0.5538 0.038 Uiso 1 1 calc R
C14 C 0.1377(3) 0.2262(3) 0.58683(11) 0.0375(6) Uani 1 1 d .
H14A H 0.2040 0.3131 0.6058 0.045 Uiso 1 1 calc R
H14B H 0.0632 0.2670 0.5531 0.045 Uiso 1 1 calc R
N5 N 0.0328(2) 0.1533(3) 0.62764(9) 0.0361(5) Uani 1 1 d .
H5A H -0.0394 0.0836 0.6086 0.054 Uiso 1 1 calc R
H5B H -0.0269 0.2277 0.6428 0.054 Uiso 1 1 calc R
H5C H 0.1016 0.1047 0.6561 0.054 Uiso 1 1 calc R
O3 O 0.8184(2) 0.3692(3) 0.66741(9) 0.0618(6) Uani 1 1 d .
H3A H 0.8013 0.3933 0.7077 0.093 Uiso 1 1 d R
H3B H 0.7259 0.3514 0.6415 0.093 Uiso 1 1 d R
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'
Cl Cl 0.1484 0.1585 '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
O2 C9 N2 119.5(2)
O2 C9 C10 123.8(2)
N2 C9 C10 116.65(19)
C6 C7 C11 123.4(2)
C6 C7 C8 121.5(2)
C11 C7 C8 114.8(2)
C7 C6 C10 119.2(2)
C7 C6 C4 120.25(19)
C10 C6 C4 120.5(2)
C5 C4 C3 117.3(2)
C5 C4 C6 120.31(19)
C3 C4 C6 122.4(2)
O1 C8 N2 119.2(2)
O1 C8 C7 124.3(2)
N2 C8 C7 116.5(2)
C6 C10 C12 124.2(2)
C6 C10 C9 121.4(2)
C12 C10 C9 114.4(2)
N1 C5 C4 120.4(2)
N1 C5 H5 119.8
C4 C5 H5 119.8
C2 C3 C4 120.5(2)
C2 C3 H3 119.8
C4 C3 H3 119.8
N1 C1 C2 118.9(2)
N1 C1 H1 120.5
C2 C1 H1 120.5
C1 C2 C3 119.8(2)
C1 C2 H2 120.1
C3 C2 H2 120.1
C9 N2 C8 124.34(19)
C9 N2 C13 118.19(19)
C8 N2 C13 117.40(19)
C5 N1 C1 123.1(2)
C5 N1 H1A 118.5
C1 N1 H1A 118.5
N3 C11 C7 177.7(3)
N4 C12 C10 177.1(3)
N2 C13 C14 112.27(19)
N2 C13 H13A 109.1
C14 C13 H13A 109.1
N2 C13 H13B 109.1
C14 C13 H13B 109.1
H13A C13 H13B 107.9
N5 C14 C13 109.0(2)
N5 C14 H14A 109.9
C13 C14 H14A 109.9
N5 C14 H14B 109.9
C13 C14 H14B 109.9
H14A C14 H14B 108.3
C14 N5 H5A 109.5
C14 N5 H5B 109.5
H5A N5 H5B 109.5
C14 N5 H5C 109.5
H5A N5 H5C 109.5
H5B N5 H5C 109.5
H3A O3 H3B 117.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C9 O2 1.237(3)
C9 N2 1.385(3)
C9 C10 1.433(3)
C7 C6 1.385(3)
C7 C11 1.428(3)
C7 C8 1.437(3)
C6 C10 1.395(3)
C6 C4 1.489(3)
C4 C5 1.380(3)
C4 C3 1.396(3)
C8 O1 1.232(3)
C8 N2 1.391(3)
C10 C12 1.423(3)
C5 N1 1.327(3)
C5 H5 0.9300
C3 C2 1.375(3)
C3 H3 0.9300
C1 N1 1.342(3)
C1 C2 1.362(4)
C1 H1 0.9300
C2 H2 0.9300
N2 C13 1.469(3)
N1 H1A 0.8600
C11 N3 1.145(3)
C12 N4 1.143(3)
C13 C14 1.508(3)
C13 H13A 0.9700
C13 H13B 0.9700
C14 N5 1.481(3)
C14 H14A 0.9700
C14 H14B 0.9700
N5 H5A 0.8900
N5 H5B 0.8900
N5 H5C 0.8900
O3 H3A 0.9859
O3 H3B 0.8857
