#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/09/4500975.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_4500975
loop_
_publ_author_name
'Orola, Liana'
'Veidis, Mikelis V.'
'Mutikainen, Ilpo'
'Sarcevica, Inese'
_publ_section_title
;
 Neutral and Ionic Supramolecular Complexes of Phenanthridine and Some
 Common Dicarboxylic Acids: Hydrogen Bond and Melting Point Considerations
;
_journal_issue                   9
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              4009
_journal_paper_doi               10.1021/cg200573m
_journal_volume                  11
_journal_year                    2011
_chemical_formula_moiety         'C13 H9 N, 0.5(C4 H4 O4)'
_chemical_formula_sum            'C15 H11 N O2'
_chemical_formula_weight         237.26
_chemical_name_systematic        'phenanthridine fumaric acid 2:1'
_space_group_IT_number           14
_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
_audit_creation_method           CRYSTALS_ver_14.06
_cell_angle_alpha                90
_cell_angle_beta                 97.58(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.900(1)
_cell_length_b                   20.070(4)
_cell_length_c                   14.489(3)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    173
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     1124.2(4)
_diffrn_ambient_temperature      173
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.075
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            13715
_diffrn_reflns_theta_full        26.904
_diffrn_reflns_theta_max         27.453
_diffrn_reflns_theta_min         2.029
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9860
_exptl_absorpt_correction_T_min  0.9842
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.22
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9876
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         1339
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1024
_refine_ls_R_factor_gt           0.0462
_refine_ls_shift/su_max          0.0002679
_refine_ls_shift/su_mean         0.0000323
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.07P)² + 0.55P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1681
_refine_ls_wR_factor_gt          0.1088
_refine_ls_wR_factor_ref         0.1088
_reflns_limit_h_max              4
_reflns_limit_h_min              -5
_reflns_limit_k_max              26
_reflns_limit_k_min              0
_reflns_limit_l_max              18
_reflns_limit_l_min              0
_reflns_number_gt                1339
_reflns_number_total             2534
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   2.17
_oxford_diffrn_Wilson_scale      37.70
_oxford_refine_ls_r_factor_ref   0.0462
_oxford_refine_ls_scale          0.16986(19)
_oxford_reflns_number_all        2533
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_oxford_structure_analysis_title 1
_cod_data_source_file            cg200573m_si_016.cif
_cod_data_source_block           global
_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_sg_symbol_H-M      'P 1 21/c 1 '
_cod_original_formula_sum        'C15 H11 N1 O2'
_cod_database_code               4500975
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
O1 O 0.0900(5) 0.87844(8) 0.49343(13) 0.0415 1.0000 Uani .
C2 C 0.0850(7) 0.92285(13) 0.42749(19) 0.0335 1.0000 Uani .
O3 O 0.1501(6) 0.91102(10) 0.34991(14) 0.0589 1.0000 Uani .
C4 C 0.0043(7) 0.99098(12) 0.45637(18) 0.0324 1.0000 Uani .
N5 N 0.2528(5) 0.75855(10) 0.44083(15) 0.0273 1.0000 Uani .
C6 C 0.1964(6) 0.70256(12) 0.49283(17) 0.0256 1.0000 Uani .
C7 C 0.2654(6) 0.63766(12) 0.46288(17) 0.0239 1.0000 Uani .
C8 C 0.2067(6) 0.58442(12) 0.52164(17) 0.0277 1.0000 Uani .
C9 C 0.0928(7) 0.59518(13) 0.60551(18) 0.0308 1.0000 Uani .
C10 C 0.0231(7) 0.65960(13) 0.63385(18) 0.0324 1.0000 Uani .
C11 C 0.0721(7) 0.71230(13) 0.57829(17) 0.0297 1.0000 Uani .
C12 C 0.3924(6) 0.63001(12) 0.37408(17) 0.0251 1.0000 Uani .
C13 C 0.4598(7) 0.56860(12) 0.33388(18) 0.0288 1.0000 Uani .
C14 C 0.5779(7) 0.56536(14) 0.24928(18) 0.0327 1.0000 Uani .
C15 C 0.6368(7) 0.62317(13) 0.20050(18) 0.0333 1.0000 Uani .
C16 C 0.5754(7) 0.68334(13) 0.23750(17) 0.0305 1.0000 Uani .
C17 C 0.4525(6) 0.68811(12) 0.32406(17) 0.0257 1.0000 Uani .
C18 C 0.3785(6) 0.75103(13) 0.36261(17) 0.0283 1.0000 Uani .
H41 H -0.0418 1.0228 0.4091 0.0381 1.0000 Uiso R
H81 H 0.2476 0.5395 0.5035 0.0312 1.0000 Uiso R
H91 H 0.0582 0.5595 0.6436 0.0355 1.0000 Uiso R
H101 H -0.0603 0.6675 0.6898 0.0390 1.0000 Uiso R
H131 H 0.4346 0.5287 0.3650 0.0339 1.0000 Uiso R
H141 H 0.6064 0.5233 0.2264 0.0385 1.0000 Uiso R
H151 H 0.7132 0.6214 0.1444 0.0376 1.0000 Uiso R
H161 H 0.6038 0.7216 0.2050 0.0361 1.0000 Uiso R
H181 H 0.4276 0.7898 0.3287 0.0344 1.0000 Uiso R
H11 H 0.1329 0.8391 0.4765 0.0611 1.0000 Uiso R
H111 H 0.0168 0.7553 0.5965 0.0345 1.0000 Uiso R
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508
'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . O1 H11 . 114.0 no
O1 . C2 O3 . 124.2(2) yes
O1 . C2 C4 . 114.1(2) yes
O3 . C2 C4 . 121.6(2) yes
C2 . C4 C4 2_576 124.0(3) yes
C2 . C4 H41 . 116.9 no
C4 2_576 C4 H41 . 119.1 no
C6 . N5 C18 . 119.0(2) yes
N5 . C6 C7 . 122.1(2) yes
N5 . C6 C11 . 117.7(2) yes
C7 . C6 C11 . 120.2(2) yes
C6 . C7 C8 . 117.6(2) yes
C6 . C7 C12 . 118.3(2) yes
C8 . C7 C12 . 124.1(2) yes
C7 . C8 C9 . 121.2(2) yes
C7 . C8 H81 . 120.2 no
C9 . C8 H81 . 118.6 no
C8 . C9 C10 . 120.5(2) yes
C8 . C9 H91 . 120.0 no
C10 . C9 H91 . 119.5 no
C9 . C10 C11 . 120.0(2) yes
C9 . C10 H101 . 121.5 no
C11 . C10 H101 . 118.6 no
C6 . C11 C10 . 120.5(2) yes
C6 . C11 H111 . 119.8 no
C10 . C11 H111 . 119.7 no
C7 . C12 C13 . 124.6(2) yes
C7 . C12 C17 . 118.0(2) yes
C13 . C12 C17 . 117.4(2) yes
C12 . C13 C14 . 121.2(2) yes
C12 . C13 H131 . 121.1 no
C14 . C13 H131 . 117.6 no
C13 . C14 C15 . 120.9(3) yes
C13 . C14 H141 . 116.0 no
C15 . C14 H141 . 123.0 no
C14 . C15 C16 . 119.5(2) yes
C14 . C15 H151 . 121.3 no
C16 . C15 H151 . 119.2 no
C15 . C16 C17 . 120.9(2) yes
C15 . C16 H161 . 120.3 no
C17 . C16 H161 . 118.8 no
C12 . C17 C16 . 120.2(2) yes
C12 . C17 C18 . 118.4(2) yes
C16 . C17 C18 . 121.4(2) yes
C17 . C18 N5 . 124.3(2) yes
C17 . C18 H181 . 117.2 no
N5 . C18 H181 . 118.6 no
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
O1 C2 . 1.305(3) yes
O1 H11 . 0.850 no
C2 O3 . 1.208(3) yes
C2 C4 . 1.476(3) yes
C4 C4 2_576 1.320(5) yes
C4 H41 . 0.937 no
N5 C6 . 1.387(3) yes
N5 C18 . 1.302(3) yes
C6 C7 . 1.410(3) yes
C6 C11 . 1.402(3) yes
C7 C8 . 1.404(3) yes
C7 C12 . 1.447(3) yes
C8 C9 . 1.365(3) yes
C8 H81 . 0.959 no
C9 C10 . 1.394(3) yes
C9 H91 . 0.925 no
C10 C11 . 1.358(3) yes
C10 H101 . 0.926 no
C11 H111 . 0.935 no
C12 C13 . 1.403(3) yes
C12 C17 . 1.409(3) yes
C13 C14 . 1.367(4) yes
C13 H131 . 0.931 no
C14 C15 . 1.393(4) yes
C14 H141 . 0.918 no
C15 C16 . 1.355(4) yes
C15 H151 . 0.902 no
C16 C17 . 1.404(3) yes
C16 H161 . 0.916 no
C17 C18 . 1.426(3) yes
C18 H181 . 0.953 no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139144578
