#------------------------------------------------------------------------------
#$Date: 2025-08-19 15:18:28 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301805 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/74/2227446.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_2227446
loop_
_publ_author_name
'Olaprath, Waynie'
'Roden, Jennifer'
'Wheeler, Kraig A.'
'McGuire, Mark E.'
_publ_section_title
;
 10,12-Dimethylpteridino[6,7-f][1,10]phenanthroline-11,13(10H,12H)-dione--chloroform
 (1/1)
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2288
_journal_paper_doi               10.1107/S1600536810031570
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C18 H12 N6 O2, C H Cl3'
_chemical_formula_moiety         'C18 H12 N6 O2, C H Cl3'
_chemical_formula_sum            'C19 H13 Cl3 N6 O2'
_chemical_formula_weight         463.70
_chemical_name_systematic
;
10,12-Dimethylpteridino[6,7-f][1,10]phenanthroline-11,13(10H,\
12H)-dione--chloroform (1/1)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 108.0580(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.9043(2)
_cell_length_b                   16.4009(4)
_cell_length_c                   13.4872(4)
_cell_measurement_reflns_used    8311
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      71.869
_cell_measurement_theta_min      4.341
_cell_volume                     1872.63(8)
_computing_cell_refinement       'APEX2 and SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction
;
SAINT (Bruker, 2008) and XPREP (Bruker, 2008)
;
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'X-SEED (Barbour, 2001)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_sigmaI/netI    0.0251
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15543
_diffrn_reflns_theta_full        68.24
_diffrn_reflns_theta_max         68.24
_diffrn_reflns_theta_min         4.38
_exptl_absorpt_coefficient_mu    4.717
_exptl_absorpt_correction_T_max  0.5081
_exptl_absorpt_correction_T_min  0.2243
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.645
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'transparent prism'
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.255
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3370
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0318
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0610P)²+0.6946P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0890
_refine_ls_wR_factor_ref         0.0954
_reflns_number_gt                3115
_reflns_number_total             3370
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            fl2311.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2227446
_cod_database_fobs_code          2227446
loop_
_symmetry_equiv_pos_as_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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 1.11933(6) 0.91490(3) 0.06882(4) 0.03314(15) Uani d . 1 . .
Cl Cl2 1.02227(5) 0.75947(3) 0.13113(3) 0.02516(14) Uani d . 1 . .
Cl Cl3 0.78834(5) 0.87388(3) 0.00893(4) 0.03132(15) Uani d . 1 . .
O O1 0.58359(16) 0.89641(8) 0.76117(10) 0.0252(3) Uani d . 1 . .
O O2 0.50035(16) 1.16797(8) 0.78817(10) 0.0253(3) Uani d . 1 . .
N N1 0.93260(18) 0.83887(9) 0.33300(11) 0.0211(3) Uani d . 1 . .
N N2 0.69578(17) 0.92402(9) 0.59325(11) 0.0185(3) Uani d . 1 . .
N N3 0.53018(17) 1.03163(9) 0.76877(11) 0.0199(3) Uani d . 1 . .
N N4 0.61174(18) 1.12873(9) 0.66532(11) 0.0193(3) Uani d . 1 . .
N N5 0.71061(17) 1.08699(9) 0.53254(11) 0.0185(3) Uani d . 1 . .
N N6 0.94027(18) 0.99643(9) 0.27110(11) 0.0206(3) Uani d . 1 . .
C C1 0.9330(2) 0.76237(11) 0.36516(14) 0.0228(4) Uani d . 1 . .
H H1 0.9744 0.7215 0.3310 0.027 Uiso calc R 1 . .
C C2 0.8759(2) 0.73847(11) 0.44641(15) 0.0232(4) Uani d . 1 . .
H H2 0.8798 0.6829 0.4670 0.028 Uiso calc R 1 . .
C C3 0.8141(2) 0.79660(11) 0.49591(14) 0.0207(4) Uani d . 1 . .
H H3 0.7739 0.7820 0.5510 0.025 Uiso calc R 1 . .
C C4 0.8113(2) 0.87791(10) 0.46354(13) 0.0180(3) Uani d . 1 . .
C C5 0.7528(2) 0.94334(10) 0.51497(13) 0.0181(3) Uani d . 1 . .
C C6 0.6493(2) 0.98516(11) 0.64097(13) 0.0187(4) Uani d . 1 . .
C C7 0.5877(2) 0.96493(10) 0.72797(13) 0.0193(4) Uani d . 1 . .
C C8 0.5445(2) 1.11330(11) 0.74324(13) 0.0202(4) Uani d . 1 . .
C C9 0.6584(2) 1.06698(10) 0.61137(13) 0.0185(4) Uani d . 1 . .
C C10 0.7584(2) 1.02511(10) 0.48401(13) 0.0179(3) Uani d . 1 . .
C C11 0.8194(2) 1.04465(11) 0.39814(13) 0.0186(3) Uani d . 1 . .
C C12 0.8254(2) 1.12494(11) 0.36400(14) 0.0211(4) Uani d . 1 . .
H H12 0.7857 1.1686 0.3949 0.025 Uiso calc R 1 . .
C C13 0.8895(2) 1.13969(11) 0.28512(14) 0.0221(4) Uani d . 1 . .
H H13 0.8958 1.1936 0.2609 0.027 Uiso calc R 1 . .
C C14 0.9452(2) 1.07352(11) 0.24152(14) 0.0226(4) Uani d . 1 . .
H H14 0.9895 1.0843 0.1872 0.027 Uiso calc R 1 . .
C C15 0.8776(2) 0.98147(10) 0.34867(13) 0.0185(3) Uani d . 1 . .
C C16 0.8732(2) 0.89648(11) 0.38207(13) 0.0181(4) Uani d . 1 . .
C C17 0.4656(2) 1.01675(11) 0.85485(14) 0.0241(4) Uani d . 1 . .
H H17A 0.4159 0.9628 0.8465 0.036 Uiso calc R 1 . .
H H17B 0.3867 1.0586 0.8543 0.036 Uiso calc R 1 . .
H H17C 0.5511 1.0189 0.9213 0.036 Uiso calc R 1 . .
C C18 0.6292(2) 1.21489(11) 0.64044(14) 0.0232(4) Uani d . 1 . .
H H18A 0.7078 1.2195 0.6034 0.035 Uiso calc R 1 . .
H H18B 0.6641 1.2466 0.7051 0.035 Uiso calc R 1 . .
H H18C 0.5275 1.2359 0.5962 0.035 Uiso calc R 1 . .
C C19 0.9722(2) 0.86285(11) 0.10784(14) 0.0226(4) Uani d . 1 . .
H H19 0.9645 0.8881 0.1736 0.027 Uiso calc R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
C1 N1 C16 . . 117.55(15) ?
C6 N2 C5 . . 117.01(15) ?
C7 N3 C8 . . 125.62(15) ?
C7 N3 C17 . . 117.70(15) ?
C8 N3 C17 . . 116.25(14) ?
C9 N4 C8 . . 122.44(15) ?
C9 N4 C18 . . 120.82(14) ?
C8 N4 C18 . . 116.73(14) ?
C9 N5 C10 . . 116.45(15) ?
C14 N6 C15 . . 117.66(15) ?
N1 C1 C2 . . 123.77(16) ?
N1 C1 H1 . . 118.1 ?
C2 C1 H1 . . 118.1 ?
C3 C2 C1 . . 118.95(17) ?
C3 C2 H2 . . 120.5 ?
C1 C2 H2 . . 120.5 ?
C2 C3 C4 . . 118.70(16) ?
C2 C3 H3 . . 120.7 ?
C4 C3 H3 . . 120.7 ?
C3 C4 C16 . . 118.44(16) ?
C3 C4 C5 . . 121.75(15) ?
C16 C4 C5 . . 119.76(16) ?
N2 C5 C10 . . 120.93(16) ?
N2 C5 C4 . . 118.54(15) ?
C10 C5 C4 . . 120.52(15) ?
N2 C6 C9 . . 121.92(16) ?
N2 C6 C7 . . 117.64(16) ?
C9 C6 C7 . . 120.43(16) ?
O1 C7 N3 . . 121.63(16) ?
O1 C7 C6 . . 124.15(16) ?
N3 C7 C6 . . 114.20(15) ?
O2 C8 N4 . . 121.82(16) ?
O2 C8 N3 . . 121.06(16) ?
N4 C8 N3 . . 117.12(15) ?
N5 C9 N4 . . 118.51(16) ?
N5 C9 C6 . . 121.85(16) ?
N4 C9 C6 . . 119.65(16) ?
N5 C10 C5 . . 121.81(16) ?
N5 C10 C11 . . 118.16(15) ?
C5 C10 C11 . . 120.02(15) ?
C12 C11 C15 . . 118.44(16) ?
C12 C11 C10 . . 121.93(16) ?
C15 C11 C10 . . 119.62(15) ?
C13 C12 C11 . . 119.12(16) ?
C13 C12 H12 . . 120.4 ?
C11 C12 H12 . . 120.4 ?
C12 C13 C14 . . 118.39(16) ?
C12 C13 H13 . . 120.8 ?
C14 C13 H13 . . 120.8 ?
N6 C14 C13 . . 124.28(16) ?
N6 C14 H14 . . 117.9 ?
C13 C14 H14 . . 117.9 ?
N6 C15 C11 . . 122.09(16) ?
N6 C15 C16 . . 117.76(15) ?
C11 C15 C16 . . 120.14(15) ?
N1 C16 C4 . . 122.58(16) ?
N1 C16 C15 . . 117.50(15) ?
C4 C16 C15 . . 119.91(15) ?
N3 C17 H17A . . 109.5 ?
N3 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
N3 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
N4 C18 H18A . . 109.5 ?
N4 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
N4 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
Cl2 C19 Cl3 . . 110.94(10) ?
Cl2 C19 Cl1 . . 110.33(10) ?
Cl3 C19 Cl1 . . 108.81(10) ?
Cl2 C19 H19 . . 108.9 ?
Cl3 C19 H19 . . 108.9 ?
Cl1 C19 H19 . . 108.9 ?
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
Cl1 C19 . 1.7747(18) ?
Cl2 C19 . 1.7564(18) ?
Cl3 C19 . 1.7716(19) ?
O1 C7 . 1.214(2) ?
O2 C8 . 1.214(2) ?
N1 C1 . 1.327(2) ?
N1 C16 . 1.352(2) ?
N2 C6 . 1.325(2) ?
N2 C5 . 1.343(2) ?
N3 C7 . 1.392(2) ?
N3 C8 . 1.399(2) ?
N3 C17 . 1.467(2) ?
N4 C9 . 1.384(2) ?
N4 C8 . 1.384(2) ?
N4 C18 . 1.472(2) ?
N5 C9 . 1.327(2) ?
N5 C10 . 1.346(2) ?
N6 C14 . 1.331(2) ?
N6 C15 . 1.352(2) ?
C1 C2 . 1.399(3) ?
C1 H1 . 0.9500 ?
C2 C3 . 1.373(3) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.401(2) ?
C3 H3 . 0.9500 ?
C4 C16 . 1.407(2) ?
C4 C5 . 1.459(2) ?
C5 C10 . 1.410(2) ?
C6 C9 . 1.410(2) ?
C6 C7 . 1.479(2) ?
C10 C11 . 1.459(2) ?
C11 C12 . 1.401(2) ?
C11 C15 . 1.415(2) ?
C12 C13 . 1.376(3) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.396(3) ?
C13 H13 . 0.9500 ?
C14 H14 . 0.9500 ?
C15 C16 . 1.469(2) ?
C17 H17A . 0.9800 ?
C17 H17B . 0.9800 ?
C17 H17C . 0.9800 ?
C18 H18A . 0.9800 ?
C18 H18B . 0.9800 ?
C18 H18C . 0.9800 ?
C19 H19 . 1.0000 ?
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
C19 H19 N1 . 1.00 2.39 3.188(2) 135.8
C19 H19 N6 . 1.00 2.26 3.181(2) 152.4
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
C16 N1 C1 C2 . . . . -0.1(3) ?
N1 C1 C2 C3 . . . . 0.7(3) ?
C1 C2 C3 C4 . . . . -0.4(3) ?
C2 C3 C4 C16 . . . . -0.5(3) ?
C2 C3 C4 C5 . . . . -177.73(17) ?
C6 N2 C5 C10 . . . . -1.6(2) ?
C6 N2 C5 C4 . . . . 177.43(15) ?
C3 C4 C5 N2 . . . . -2.1(3) ?
C16 C4 C5 N2 . . . . -179.32(15) ?
C3 C4 C5 C10 . . . . 176.93(16) ?
C16 C4 C5 C10 . . . . -0.3(3) ?
C5 N2 C6 C9 . . . . 0.1(3) ?
C5 N2 C6 C7 . . . . -179.42(15) ?
C8 N3 C7 O1 . . . . 173.01(17) ?
C17 N3 C7 O1 . . . . 0.8(3) ?
C8 N3 C7 C6 . . . . -8.3(2) ?
C17 N3 C7 C6 . . . . 179.50(15) ?
N2 C6 C7 O1 . . . . 3.3(3) ?
C9 C6 C7 O1 . . . . -176.22(17) ?
N2 C6 C7 N3 . . . . -175.31(15) ?
C9 C6 C7 N3 . . . . 5.1(2) ?
C9 N4 C8 O2 . . . . -178.08(16) ?
C18 N4 C8 O2 . . . . 0.8(3) ?
C9 N4 C8 N3 . . . . 2.3(3) ?
C18 N4 C8 N3 . . . . -178.82(15) ?
C7 N3 C8 O2 . . . . -174.77(17) ?
C17 N3 C8 O2 . . . . -2.5(2) ?
C7 N3 C8 N4 . . . . 4.9(3) ?
C17 N3 C8 N4 . . . . 177.20(15) ?
C10 N5 C9 N4 . . . . 178.39(15) ?
C10 N5 C9 C6 . . . . -1.7(2) ?
C8 N4 C9 N5 . . . . 174.92(15) ?
C18 N4 C9 N5 . . . . -4.0(2) ?
C8 N4 C9 C6 . . . . -5.0(3) ?
C18 N4 C9 C6 . . . . 176.14(16) ?
N2 C6 C9 N5 . . . . 1.6(3) ?
C7 C6 C9 N5 . . . . -178.85(16) ?
N2 C6 C9 N4 . . . . -178.51(16) ?
C7 C6 C9 N4 . . . . 1.0(3) ?
C9 N5 C10 C5 . . . . 0.3(2) ?
C9 N5 C10 C11 . . . . -178.90(15) ?
N2 C5 C10 N5 . . . . 1.4(3) ?
C4 C5 C10 N5 . . . . -177.55(16) ?
N2 C5 C10 C11 . . . . -179.40(15) ?
C4 C5 C10 C11 . . . . 1.6(3) ?
N5 C10 C11 C12 . . . . -1.6(3) ?
C5 C10 C11 C12 . . . . 179.22(16) ?
N5 C10 C11 C15 . . . . 177.03(16) ?
C5 C10 C11 C15 . . . . -2.2(2) ?
C15 C11 C12 C13 . . . . -1.0(3) ?
C10 C11 C12 C13 . . . . 177.63(16) ?
C11 C12 C13 C14 . . . . 0.5(3) ?
C15 N6 C14 C13 . . . . -0.2(3) ?
C12 C13 C14 N6 . . . . 0.1(3) ?
C14 N6 C15 C11 . . . . -0.3(3) ?
C14 N6 C15 C16 . . . . -179.49(15) ?
C12 C11 C15 N6 . . . . 1.0(3) ?
C10 C11 C15 N6 . . . . -177.72(16) ?
C12 C11 C15 C16 . . . . -179.93(16) ?
C10 C11 C15 C16 . . . . 1.4(2) ?
C1 N1 C16 C4 . . . . -0.8(3) ?
C1 N1 C16 C15 . . . . 178.08(16) ?
C3 C4 C16 N1 . . . . 1.1(3) ?
C5 C4 C16 N1 . . . . 178.42(15) ?
C3 C4 C16 C15 . . . . -177.78(16) ?
C5 C4 C16 C15 . . . . -0.5(3) ?
N6 C15 C16 N1 . . . . 0.1(2) ?
C11 C15 C16 N1 . . . . -179.05(15) ?
N6 C15 C16 C4 . . . . 179.05(15) ?
C11 C15 C16 C4 . . . . -0.1(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656222
2 PubChem 168309898
