#------------------------------------------------------------------------------
#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/67/1556777.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_1556777
loop_
_publ_author_name
'Garai, Mousumi'
'Biradha, Kumar'
_publ_section_title
;
 Exploration and exploitation of homologous series of
 bis(acrylamido)alkanes containing pyridyl and phenyl groups: β-sheet
 versus two-dimensional layers in solid-state photochemical
 [2 + 2] reactions.
;
_journal_issue                   'Pt 5'
_journal_name_full               IUCrJ
_journal_page_first              523
_journal_page_last               533
_journal_paper_doi               10.1107/S2052252515009987
_journal_volume                  2
_journal_year                    2015
_chemical_formula_moiety         'C16 H14 N4 O2'
_chemical_formula_sum            'C16 H14 N4 O2'
_chemical_formula_weight         294.31
_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_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                 101.156(17)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.403(6)
_cell_length_b                   7.160(4)
_cell_length_c                   19.202(11)
_cell_measurement_reflns_used    2475
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.99
_cell_measurement_theta_min      2.00
_cell_volume                     1403.2(14)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker CCD APEX-2'
_diffrn_measurement_method       hemisphere
_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  0.0601
_diffrn_reflns_av_sigmaI/netI    0.0385
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15971
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.00
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'plate like'
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.677
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2475
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.677
_refine_ls_R_factor_all          0.1210
_refine_ls_R_factor_gt           0.0430
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0100P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0749
_refine_ls_wR_factor_ref         0.0801
_reflns_number_gt                1236
_reflns_number_total             2475
_reflns_threshold_expression     >2sigma(I)
_publcif_datablock.id            {1d4b13d6-ca77-4b60-bced-ccbbf816c53a}
_cod_data_source_file            yc5005.cif
_cod_data_source_block           3a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/IUCr/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_cell_volume        1403.1(14)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1556777
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
N11 N 0.14943(19) 0.3152(3) -0.27092(9) 0.0479(6) Uani 1 1 d .
O11 O 0.13155(15) 0.3566(3) 0.06687(8) 0.0625(6) Uani 1 1 d .
C11 C 0.0715(2) 0.3485(3) -0.16133(12) 0.0340(6) Uani 1 1 d .
C12 C 0.1688(2) 0.3313(3) -0.20060(11) 0.0447(7) Uani 1 1 d .
H12 H 0.2550 0.3309 -0.1759 0.054 Uiso 1 1 calc R
C13 C 0.0251(2) 0.3174(3) -0.30499(12) 0.0482(7) Uani 1 1 d .
H13 H 0.0080 0.3038 -0.3541 0.058 Uiso 1 1 calc R
C14 C -0.0786(2) 0.3384(4) -0.27182(12) 0.0503(7) Uani 1 1 d .
H14 H -0.1638 0.3415 -0.2979 0.060 Uiso 1 1 calc R
C15 C -0.0548(2) 0.3551(3) -0.19895(12) 0.0454(7) Uani 1 1 d .
H15 H -0.1241 0.3707 -0.1753 0.054 Uiso 1 1 calc R
C16 C 0.0991(2) 0.3562(3) -0.08336(11) 0.0408(6) Uani 1 1 d .
H16 H 0.0268 0.3700 -0.0619 0.049 Uiso 1 1 calc R
C17 C 0.2131(2) 0.3460(3) -0.04051(11) 0.0429(7) Uani 1 1 d .
H17 H 0.2885 0.3380 -0.0596 0.051 Uiso 1 1 calc R
C18 C 0.2248(2) 0.3470(3) 0.03710(12) 0.0420(7) Uani 1 1 d .
O21 O 0.58052(15) 0.3899(2) 0.15759(8) 0.0585(5) Uani 1 1 d .
N21 N 0.55915(19) 0.2731(3) 0.49254(9) 0.0518(6) Uani 1 1 d .
C21 C 0.6347(2) 0.3454(3) 0.38489(12) 0.0358(6) Uani 1 1 d .
C22 C 0.5404(2) 0.2945(4) 0.42231(12) 0.0530(8) Uani 1 1 d .
H22 H 0.4564 0.2731 0.3965 0.064 Uiso 1 1 calc R
C23 C 0.6812(3) 0.3037(3) 0.52792(12) 0.0531(8) Uani 1 1 d .
H23 H 0.6983 0.2881 0.5769 0.064 Uiso 1 1 calc R
C24 C 0.7814(3) 0.3563(4) 0.49643(13) 0.0587(8) Uani 1 1 d .
H24 H 0.8645 0.3776 0.5234 0.070 Uiso 1 1 calc R
C25 C 0.7582(2) 0.3775(3) 0.42381(12) 0.0483(7) Uani 1 1 d .
H25 H 0.8257 0.4134 0.4012 0.058 Uiso 1 1 calc R
C26 C 0.6090(2) 0.3616(3) 0.30736(11) 0.0411(6) Uani 1 1 d .
H26 H 0.6800 0.3956 0.2872 0.049 Uiso 1 1 calc R
C27 C 0.4972(2) 0.3337(3) 0.26284(11) 0.0427(7) Uani 1 1 d .
H27 H 0.4230 0.3021 0.2806 0.051 Uiso 1 1 calc R
C28 C 0.4874(2) 0.3515(4) 0.18536(12) 0.0424(7) Uani 1 1 d .
N31 N 0.34719(17) 0.3318(3) 0.07380(9) 0.0453(6) Uani 1 1 d .
H31 H 0.4123 0.3273 0.0522 0.054 Uiso 1 1 calc R
N32 N 0.36744(17) 0.3237(3) 0.14676(9) 0.0444(6) Uani 1 1 d .
H32 H 0.3029 0.3006 0.1675 0.053 Uiso 1 1 calc 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C13 N11 C12 116.1(2)
C12 C11 C15 116.4(2)
C12 C11 C16 122.7(2)
C15 C11 C16 120.9(2)
C11 C12 N11 125.4(2)
C11 C12 H12 117.3
N11 C12 H12 117.3
N11 C13 C14 123.6(2)
N11 C13 H13 118.2
C14 C13 H13 118.2
C13 C14 C15 118.7(2)
C13 C14 H14 120.6
C15 C14 H14 120.6
C11 C15 C14 119.8(2)
C11 C15 H15 120.1
C14 C15 H15 120.1
C17 C16 C11 127.8(2)
C17 C16 H16 116.1
C11 C16 H16 116.1
C16 C17 C18 121.6(2)
C16 C17 H17 119.2
C18 C17 H17 119.2
O11 C18 N31 121.4(2)
O11 C18 C17 123.9(2)
N31 C18 C17 114.7(2)
C22 N21 C23 115.7(2)
C22 C21 C25 116.6(2)
C22 C21 C26 123.0(2)
C25 C21 C26 120.4(2)
N21 C22 C21 125.5(2)
N21 C22 H22 117.3
C21 C22 H22 117.3
C24 C23 N21 123.7(2)
C24 C23 H23 118.1
N21 C23 H23 118.1
C23 C24 C25 118.9(2)
C23 C24 H24 120.6
C25 C24 H24 120.6
C24 C25 C21 119.6(2)
C24 C25 H25 120.2
C21 C25 H25 120.2
C27 C26 C21 127.6(2)
C27 C26 H26 116.2
C21 C26 H26 116.2
C26 C27 C28 121.3(2)
C26 C27 H27 119.3
C28 C27 H27 119.3
O21 C28 N32 121.6(2)
O21 C28 C27 123.5(2)
N32 C28 C27 114.9(2)
C18 N31 N32 118.88(19)
C18 N31 H31 120.6
N32 N31 H31 120.6
C28 N32 N31 120.01(19)
C28 N32 H32 120.0
N31 N32 H32 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N11 C13 1.332(3)
N11 C12 1.331(3)
O11 C18 1.219(2)
C11 C12 1.380(3)
C11 C15 1.372(3)
C11 C16 1.470(3)
C12 H12 0.9300
C13 C14 1.363(3)
C13 H13 0.9300
C14 C15 1.378(3)
C14 H14 0.9300
C15 H15 0.9300
C16 C17 1.308(3)
C16 H16 0.9300
C17 C18 1.472(3)
C17 H17 0.9300
C18 N31 1.335(3)
O21 C28 1.224(2)
N21 C22 1.333(3)
N21 C23 1.337(3)
C21 C22 1.373(3)
C21 C25 1.375(3)
C21 C26 1.465(3)
C22 H22 0.9300
C23 C24 1.356(3)
C23 H23 0.9300
C24 C25 1.377(3)
C24 H24 0.9300
C25 H25 0.9300
C26 C27 1.319(3)
C26 H26 0.9300
C27 C28 1.477(3)
C27 H27 0.9300
C28 N32 1.337(2)
N31 N32 1.377(2)
N31 H31 0.8600
N32 H32 0.8600
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
C15 C11 C12 N11 -2.1(4)
C16 C11 C12 N11 176.8(2)
C13 N11 C12 C11 0.4(4)
C12 N11 C13 C14 1.3(4)
N11 C13 C14 C15 -1.2(4)
C12 C11 C15 C14 2.1(4)
C16 C11 C15 C14 -176.8(3)
C13 C14 C15 C11 -0.6(4)
C12 C11 C16 C17 -1.0(4)
C15 C11 C16 C17 177.9(3)
C11 C16 C17 C18 -177.0(3)
C16 C17 C18 O11 0.2(4)
C16 C17 C18 N31 178.7(3)
C23 N21 C22 C21 -0.4(4)
C25 C21 C22 N21 -0.4(4)
C26 C21 C22 N21 178.2(2)
C22 N21 C23 C24 1.0(4)
N21 C23 C24 C25 -0.9(4)
C23 C24 C25 C21 0.0(4)
C22 C21 C25 C24 0.5(4)
C26 C21 C25 C24 -178.1(3)
C22 C21 C26 C27 0.7(4)
C25 C21 C26 C27 179.3(3)
C21 C26 C27 C28 -178.6(2)
C26 C27 C28 O21 1.1(4)
C26 C27 C28 N32 -178.5(2)
O11 C18 N31 N32 1.2(4)
C17 C18 N31 N32 -177.4(2)
O21 C28 N32 N31 2.2(4)
C27 C28 N32 N31 -178.3(2)
C18 N31 N32 C28 -164.7(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168305935
