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#$Date: 2024-09-19 04:15:50 +0300 (Thu, 19 Sep 2024) $
#$Revision: 294793 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/93/7249353.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_7249353
loop_
_publ_author_name
'Konovalova, Irina S.'
'Shishkina, Svitlana V.'
'Wyshusek, Maik'
'Patzer, Michael'
'Reiss, Guido J.'
_publ_section_title
;
 Supramolecular architecture of theophylline polymorphs, monohydrate and
 co-crystals with iodine: study from the energetic viewpoint
;
_journal_issue                   41
_journal_name_full               'RSC Advances'
_journal_page_first              29774
_journal_page_last               29788
_journal_paper_doi               10.1039/D4RA04368E
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'C7 H8 N4 O2'
_chemical_formula_sum            'C7 H8 N4 O2'
_chemical_formula_weight         180.17
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yac'
_space_group_name_H-M_alt        'P 1 n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2019/2
_audit_update_record
;
2023-05-22 deposited with the CCDC.	2024-09-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.965(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   3.8744(4)
_cell_length_b                   12.8898(9)
_cell_length_c                   8.1167(6)
_cell_measurement_temperature    290(2)
_cell_volume                     400.40(6)
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.871
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.871
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2386
_diffrn_reflns_point_group_measured_fraction_full 0.820
_diffrn_reflns_point_group_measured_fraction_max 0.680
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.318
_diffrn_reflns_theta_min         2.992
_exptl_absorpt_coefficient_mu    0.114
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_F_000             188
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 360 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -2.0(10)
_refine_ls_extinction_coef       0.015(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     121
_refine_ls_number_reflns         1499
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0491
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0120P)²+0.3000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0908
_refine_ls_wR_factor_ref         0.0983
_reflns_Friedel_coverage         0.550
_reflns_Friedel_fraction_full    0.638
_reflns_Friedel_fraction_max     0.487
_reflns_number_gt                1168
_reflns_number_total             1499
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ra04368e2.cif
_cod_data_source_block           exp_276_2
_cod_original_cell_volume        400.40(5)
_cod_original_sg_symbol_H-M      'P n'
_cod_database_code               7249353
_shelx_shelxl_version_number     2019/2
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.7858(11) -0.4213(3) -0.0816(5) 0.0661(12) Uani 1 1 d . . . . .
N1 N -0.6736(10) -0.0624(3) 0.0068(5) 0.0386(9) Uani 1 1 d . . . . .
C1 C -0.7129(12) -0.3352(4) -0.1222(6) 0.0467(13) Uani 1 1 d . . . . .
O2 O -0.3884(10) -0.2132(3) -0.4688(4) 0.0555(10) Uani 1 1 d . . . . .
N2 N -0.7449(10) -0.2498(3) -0.0228(5) 0.0390(10) Uani 1 1 d . . . . .
C2 C -0.4920(13) -0.2208(4) -0.3336(6) 0.0408(12) Uani 1 1 d . . . . .
C3 C -0.5351(11) -0.1393(3) -0.2205(5) 0.0334(10) Uani 1 1 d . . . . .
N4 N -0.5936(10) -0.3167(3) -0.2735(5) 0.0421(10) Uani 1 1 d . . . . .
C4 C -0.5571(14) 0.0077(4) -0.0928(6) 0.0440(11) Uani 1 1 d . . . . .
H4 H -0.537850 0.078132 -0.068042 0.053 Uiso 1 1 calc R U . . .
N5 N -0.4717(9) -0.0338(3) -0.2311(4) 0.0377(9) Uani 1 1 d . . . . .
H5 H -0.393278 -0.001844 -0.310622 0.045 Uiso 1 1 calc R U . . .
C5 C -0.6577(10) -0.1530(3) -0.0756(5) 0.0336(10) Uani 1 1 d . . . . .
C6 C -0.8532(15) -0.2641(4) 0.1408(6) 0.0561(15) Uani 1 1 d . . . . .
H6A H -0.947777 -0.332563 0.147634 0.084 Uiso 1 1 calc R U . . .
H6B H -1.028067 -0.213615 0.155399 0.084 Uiso 1 1 calc R U . . .
H6C H -0.654836 -0.255576 0.226679 0.084 Uiso 1 1 calc R U . . .
C7 C -0.5640(16) -0.4100(4) -0.3799(8) 0.0620(16) Uani 1 1 d . . . . .
H7A H -0.459181 -0.390483 -0.474975 0.093 Uiso 1 1 calc R U . . .
H7B H -0.792435 -0.438117 -0.416751 0.093 Uiso 1 1 calc R U . . .
H7C H -0.421291 -0.461369 -0.316232 0.093 Uiso 1 1 calc R U . . .
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
_geom_angle_publ_flag
C4 N1 C5 103.8(4) . . ?
O1 C1 N2 121.9(5) . . ?
O1 C1 N4 121.4(5) . . ?
N2 C1 N4 116.7(4) . . ?
C5 N2 C1 119.4(4) . . ?
C5 N2 C6 120.9(4) . . ?
C1 N2 C6 119.6(4) . . ?
O2 C2 N4 121.7(4) . . ?
O2 C2 C3 127.3(5) . . ?
N4 C2 C3 111.0(4) . . ?
C5 C3 N5 105.8(4) . . ?
C5 C3 C2 124.1(4) . . ?
N5 C3 C2 130.1(4) . . ?
C1 N4 C2 127.0(4) . . ?
C1 N4 C7 115.9(4) . . ?
C2 N4 C7 117.1(4) . . ?
N5 C4 N1 112.9(4) . . ?
C4 N5 C3 105.8(4) . . ?
C3 C5 N1 111.7(4) . . ?
C3 C5 N2 121.8(4) . . ?
N1 C5 N2 126.6(4) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.204(6) . ?
N1 C4 1.337(6) . ?
N1 C5 1.352(5) . ?
C1 N2 1.381(6) . ?
C1 N4 1.398(6) . ?
O2 C2 1.230(5) . ?
N2 C5 1.379(5) . ?
N2 C6 1.466(6) . ?
C2 N4 1.408(6) . ?
C2 C3 1.421(6) . ?
C3 C5 1.346(6) . ?
C3 N5 1.387(6) . ?
N4 C7 1.495(6) . ?
C4 N5 1.332(5) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 N2 C5 -180.0(5) . . . . ?
N4 C1 N2 C5 -0.4(6) . . . . ?
O1 C1 N2 C6 3.2(7) . . . . ?
N4 C1 N2 C6 -177.2(4) . . . . ?
O2 C2 C3 C5 178.4(5) . . . . ?
N4 C2 C3 C5 -0.1(6) . . . . ?
O2 C2 C3 N5 -0.6(8) . . . . ?
N4 C2 C3 N5 -179.2(4) . . . . ?
O1 C1 N4 C2 -178.3(5) . . . . ?
N2 C1 N4 C2 2.1(6) . . . . ?
O1 C1 N4 C7 0.1(7) . . . . ?
N2 C1 N4 C7 -179.5(4) . . . . ?
O2 C2 N4 C1 179.5(5) . . . . ?
C3 C2 N4 C1 -1.8(6) . . . . ?
O2 C2 N4 C7 1.1(7) . . . . ?
C3 C2 N4 C7 179.8(4) . . . . ?
C5 N1 C4 N5 0.2(5) . . . . ?
N1 C4 N5 C3 -0.4(6) . . . . ?
C5 C3 N5 C4 0.5(5) . . . . ?
C2 C3 N5 C4 179.7(4) . . . . ?
N5 C3 C5 N1 -0.4(5) . . . . ?
C2 C3 C5 N1 -179.7(4) . . . . ?
N5 C3 C5 N2 -179.1(4) . . . . ?
C2 C3 C5 N2 1.6(6) . . . . ?
C4 N1 C5 C3 0.2(5) . . . . ?
C4 N1 C5 N2 178.8(4) . . . . ?
C1 N2 C5 C3 -1.3(6) . . . . ?
C6 N2 C5 C3 175.4(4) . . . . ?
C1 N2 C5 N1 -179.8(4) . . . . ?
C6 N2 C5 N1 -3.1(7) . . . . ?
