#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/43/4504379.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_4504379
loop_
_publ_author_name
'Lu, Zhengliang'
'Gamez, Patrick'
'Mutikainen, Ilpo'
'Turpeinen, Urho'
'Reedijk, Jan'
_publ_section_title
;
 Supramolecular Assemblies Generated from Both
 Lone-Pair···π and
 C−H···π Binding Interactions
;
_journal_issue                   9
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1669
_journal_paper_doi               10.1021/cg0704302
_journal_volume                  7
_journal_year                    2007
_chemical_formula_moiety         'C19 H20 N4 O2'
_chemical_formula_sum            'C19 H20 N4 O2'
_chemical_formula_weight         336.39
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 107.72(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.588(3)
_cell_length_b                   13.599(3)
_cell_length_c                   7.735(2)
_cell_measurement_reflns_used    98
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      12.43
_cell_measurement_theta_min      4.32
_cell_volume                     1662.1(7)
_computing_cell_refinement       'DirAx (Duisenberg 1992)'
_computing_data_collection       'COLLECT (Nonius, 2002)'
_computing_data_reduction        'COLLECT/EVAL (Nonius, 2002)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1990)'
_computing_publication_material  'SHELXTL (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       ω-scan
_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  0.0472
_diffrn_reflns_av_sigmaI/netI    0.0445
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11930
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         3.00
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9822
_exptl_absorpt_correction_T_min  0.9822
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.0112(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         1884
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0400
_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)+(0.0310P)²+1.3608P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0773
_refine_ls_wR_factor_ref         0.0907
_reflns_number_gt                1276
_reflns_number_total             1884
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg0704302-file002.cif
_cod_data_source_block           zl001
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1662.1(6)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4504379
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
C1 C 0.32594(12) 0.33467(14) 0.1559(3) 0.0306(4) Uani 1 1 d .
H1A H 0.3222(11) 0.2618(15) 0.157(2) 0.040(5) Uiso 1 1 d .
H1B H 0.3578(12) 0.3565(14) 0.282(3) 0.044(5) Uiso 1 1 d .
H1C H 0.2665(13) 0.3639(15) 0.118(3) 0.048(6) Uiso 1 1 d .
C2 C 0.37063(10) 0.36455(11) 0.0220(2) 0.0217(4) Uani 1 1 d .
H2A H 0.3370(10) 0.3466(11) -0.106(2) 0.020(4) Uiso 1 1 d .
H2B H 0.4279(10) 0.3389(11) 0.052(2) 0.016(4) Uiso 1 1 d .
O3 O 0.37603(6) 0.47138(7) 0.01150(14) 0.0210(3) Uani 1 1 d .
C4 C 0.44018(9) 0.51734(11) 0.13533(19) 0.0161(3) Uani 1 1 d .
N5 N 0.5000 0.46284(13) 0.2500 0.0174(4) Uani 1 2 d S
N6 N 0.43561(7) 0.61507(9) 0.12493(16) 0.0169(3) Uani 1 1 d .
C7 C 0.5000 0.65987(15) 0.2500 0.0154(4) Uani 1 2 d S
N8 N 0.5000 0.76080(12) 0.2500 0.0182(4) Uani 1 2 d S
C9 C 0.43740(9) 0.81685(10) 0.1129(2) 0.0175(3) Uani 1 1 d .
C10 C 0.46272(10) 0.86827(12) -0.0163(2) 0.0238(4) Uani 1 1 d .
H10 H 0.5210(11) 0.8640(12) -0.016(2) 0.030(5) Uiso 1 1 d .
C11 C 0.40462(11) 0.92576(12) -0.1440(2) 0.0277(4) Uani 1 1 d .
H11 H 0.4220(11) 0.9633(13) -0.233(2) 0.035(5) Uiso 1 1 d .
C12 C 0.32127(11) 0.93151(12) -0.1429(2) 0.0256(4) Uani 1 1 d .
H12 H 0.2817(10) 0.9715(12) -0.231(2) 0.025(4) Uiso 1 1 d .
C13 C 0.29603(10) 0.87943(12) -0.0141(2) 0.0251(4) Uani 1 1 d .
H13 H 0.2387(11) 0.8846(12) -0.012(2) 0.029(4) Uiso 1 1 d .
C14 C 0.35397(9) 0.82245(12) 0.1144(2) 0.0217(4) Uani 1 1 d .
H14 H 0.3366(10) 0.7870(13) 0.206(2) 0.030(5) Uiso 1 1 d .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 C1 H1A 108.6(10) . .
C2 C1 H1B 111.4(11) . .
H1A C1 H1B 107.8(15) . .
C2 C1 H1C 109.5(11) . .
H1A C1 H1C 109.5(15) . .
H1B C1 H1C 110.0(16) . .
O3 C2 C1 111.05(13) . .
O3 C2 H2A 102.2(9) . .
C1 C2 H2A 111.7(9) . .
O3 C2 H2B 107.4(9) . .
C1 C2 H2B 113.1(9) . .
H2A C2 H2B 110.8(13) . .
C4 O3 C2 118.06(11) . .
N6 C4 N5 127.63(13) . .
N6 C4 O3 113.66(12) . .
N5 C4 O3 118.71(13) . .
C4 N5 C4 112.62(17) . 2_655
C4 N6 C7 112.91(13) . .
N6 C7 N6 126.30(18) 2_655 .
N6 C7 N8 116.85(9) 2_655 .
N6 C7 N8 116.85(9) . .
C7 N8 C9 121.62(8) . .
C7 N8 C9 121.62(8) . 2_655
C9 N8 C9 116.76(16) . 2_655
C10 C9 C14 119.98(14) . .
C10 C9 N8 119.00(12) . .
C14 C9 N8 120.97(13) . .
C9 C10 C11 119.93(15) . .
C9 C10 H10 119.4(10) . .
C11 C10 H10 120.7(10) . .
C12 C11 C10 120.25(16) . .
C12 C11 H11 119.1(10) . .
C10 C11 H11 120.6(10) . .
C13 C12 C11 119.65(15) . .
C13 C12 H12 120.6(10) . .
C11 C12 H12 119.8(10) . .
C12 C13 C14 120.30(15) . .
C12 C13 H13 119.6(10) . .
C14 C13 H13 120.0(10) . .
C13 C14 C9 119.88(16) . .
C13 C14 H14 120.3(10) . .
C9 C14 H14 119.8(10) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.502(2) .
C1 H1A 0.99(2) .
C1 H1B 1.00(2) .
C1 H1C 1.02(2) .
C2 O3 1.4593(18) .
C2 H2A 1.008(16) .
C2 H2B 0.972(15) .
O3 C4 1.3490(17) .
C4 N6 1.3323(19) .
C4 N5 1.3360(18) .
N5 C4 1.3360(18) 2_655
N6 C7 1.3486(15) .
C7 N6 1.3486(15) 2_655
C7 N8 1.373(3) .
N8 C9 1.4539(17) .
N8 C9 1.4539(17) 2_655
C9 C10 1.386(2) .
C9 C14 1.390(2) .
C10 C11 1.391(2) .
C10 H10 0.968(18) .
C11 C12 1.387(2) .
C11 H11 0.968(19) .
C12 C13 1.387(2) .
C12 H12 0.958(17) .
C13 C14 1.390(2) .
C13 H13 0.959(18) .
C14 H14 0.968(18) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 101440969
