#------------------------------------------------------------------------------
#$Date: 2024-05-08 04:54:25 +0300 (Wed, 08 May 2024) $
#$Revision: 291770 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/24/2312484.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_2312484
loop_
_publ_author_name
'González-González, Juan Saulo'
'Martínez-Santos, Alfonso'
'Emparán-Legaspi, María José'
'Pineda-Contreras, Armando'
'Martínez-Martínez, Francisco Javier'
'Flores-Alamo, Marcos'
'García-Ortega, Hector'
_publ_section_title
;
 Molecular structure and selective theophylline complexation by
 conformational change of diethyl N,N'-(1,3-phenylene)dicarbamate.
;
_journal_coeditor_code           ZO3045
_journal_issue                   6
_journal_name_full
'Acta crystallographica. Section C, Structural chemistry'
_journal_paper_doi               10.1107/S2053229624003358
_journal_volume                  80
_journal_year                    2024
_chemical_formula_iupac          'C12 H16 N2 O4, C7 H8 N4 O2'
_chemical_formula_moiety         'C12 H16 N2 O4, C7 H8 N4 O2'
_chemical_formula_sum            'C19 H24 N6 O6'
_chemical_formula_weight         432.44
_chemical_name_systematic
;
Diethyl N,N'-(1,3-phenylene)dicarbamate--theophylline (1/1)
;
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                85.742(10)
_cell_angle_beta                 76.887(12)
_cell_angle_gamma                79.803(15)
_cell_formula_units_Z            2
_cell_length_a                   7.5284(14)
_cell_length_b                   11.2362(18)
_cell_length_c                   12.2606(12)
_cell_measurement_reflns_used    1977
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      29.6358
_cell_measurement_theta_min      3.5929
_cell_volume                     993.5(3)
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2013)
;
_computing_data_collection
;
CrysAlis PRO (Agilent, 2013)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2013)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)'
;
_computing_publication_material
;
WinGX and ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2018 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      130(2)
_diffrn_detector_area_resol_mean 10.4685
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.848
_diffrn_measurement_device_type  'Agilent Xcalibur Atlas Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_av_unetI/netI     0.0907
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11140
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.684
_diffrn_reflns_theta_min         3.598
_exptl_absorpt_coefficient_mu    0.11
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2013)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_description       prism
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.29
_refine_diff_density_min         -0.376
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4780
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.1109
_refine_ls_R_factor_gt           0.0619
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0543P)²+0.3739P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1239
_refine_ls_wR_factor_ref         0.1566
_reflns_number_gt                3041
_reflns_number_total             4780
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            zo3045.cif
_cod_data_source_block           1_TEO
_cod_database_code               2312484
_shelx_estimated_absorpt_t_min   0.959
_shelx_estimated_absorpt_t_max   0.992
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.5463(3) 0.2028(2) 0.78512(18) 0.0190(5) Uani d 1 . .
C C1C 0.4338(3) 0.2986(2) 0.35063(19) 0.0215(5) Uani d 1 . .
H H1CA 0.353162 0.244731 0.336241 0.032 Uiso calc 1 . .
H H1CB 0.494817 0.262892 0.410779 0.032 Uiso calc 1 . .
H H1CC 0.52745 0.309502 0.282366 0.032 Uiso calc 1 . .
C C2 0.4500(3) 0.3167(2) 0.81742(18) 0.0177(5) Uani d 1 . .
H H2 0.410633 0.373618 0.762944 0.021 Uiso calc 1 . .
C C2C 0.2423(3) 0.4822(2) 0.30231(18) 0.0201(5) Uani d 1 . .
C C3 0.4111(3) 0.3474(2) 0.92910(18) 0.0189(5) Uani d 1 . .
C C3C 0.0487(4) 0.6642(2) 0.24618(19) 0.0254(6) Uani d 1 . .
H H3CA -0.035569 0.618628 0.223344 0.038 Uiso calc 1 . .
H H3CB 0.143249 0.682163 0.18063 0.038 Uiso calc 1 . .
H H3CC -0.021228 0.740118 0.278817 0.038 Uiso calc 1 . .
C C4 0.4733(3) 0.2640(2) 1.00821(19) 0.0206(5) Uani d 1 . .
H H4 0.450411 0.284584 1.084468 0.025 Uiso calc 1 . .
C C4C 0.1141(3) 0.6329(2) 0.43593(17) 0.0163(5) Uani d 1 . .
C C5 0.5674(3) 0.1523(2) 0.97481(19) 0.0221(6) Uani d 1 . .
H H5 0.607619 0.095673 1.029292 0.026 Uiso calc 1 . .
C C5C 0.1929(3) 0.5649(2) 0.51488(17) 0.0173(5) Uani d 1 . .
C C6 0.6062(3) 0.1189(2) 0.86387(19) 0.0226(6) Uani d 1 . .
H H6 0.671885 0.040927 0.842405 0.027 Uiso calc 1 . .
C C6C 0.3045(3) 0.4509(2) 0.49485(18) 0.0187(5) Uani d 1 . .
C C8 0.6744(3) 0.0802(2) 0.61652(18) 0.0198(5) Uani d 1 . .
C C8C 0.0308(3) 0.7349(2) 0.58082(19) 0.0209(5) Uani d 1 . .
H H8C -0.025456 0.797994 0.631144 0.025 Uiso calc 1 . .
C C10 0.7646(4) -0.0096(2) 0.44008(19) 0.0242(6) Uani d 1 . .
H H10A 0.709082 -0.082963 0.466538 0.029 Uiso calc 1 . .
H H10B 0.895855 -0.026062 0.445724 0.029 Uiso calc 1 . .
C C11 0.7503(4) 0.0231(2) 0.3206(2) 0.0272(6) Uani d 1 . .
H H11A 0.815312 -0.044205 0.272752 0.041 Uiso calc 1 . .
H H11B 0.806536 0.095447 0.295147 0.041 Uiso calc 1 . .
H H11C 0.619877 0.039493 0.316086 0.041 Uiso calc 1 . .
C C28 0.2235(3) 0.5478(2) 0.91024(18) 0.0193(5) Uani d 1 . .
C C30 0.0354(4) 0.7401(2) 0.92134(19) 0.0249(6) Uani d 1 . .
H H30A -0.058581 0.717608 0.885374 0.03 Uiso calc 1 . .
H H30B 0.129797 0.772846 0.862603 0.03 Uiso calc 1 . .
C C31 -0.0537(4) 0.8331(2) 1.0073(2) 0.0275(6) Uani d 1 . .
H H31A -0.114052 0.90489 0.971246 0.041 Uiso calc 1 . .
H H31B 0.040704 0.855668 1.041478 0.041 Uiso calc 1 . .
H H31C -0.146116 0.79956 1.065306 0.041 Uiso calc 1 . .
N N1C 0.3232(3) 0.41599(18) 0.38423(15) 0.0192(4) Uani d 1 . .
N N3C 0.1380(3) 0.59203(18) 0.32969(14) 0.0190(5) Uani d 1 . .
N N7 0.5761(3) 0.17967(19) 0.67025(15) 0.0200(5) Uani d 1 . .
N N7C 0.1354(3) 0.63331(19) 0.60949(15) 0.0211(5) Uani d 1 . .
H H7C 0.162221 0.613989 0.675449 0.025 Uiso calc 1 . .
N N9C 0.0133(3) 0.73883(19) 0.47468(15) 0.0203(5) Uani d 1 . .
N N27 0.3066(3) 0.45819(18) 0.96964(16) 0.0193(5) Uani d 1 . .
O O2C 0.2650(2) 0.44115(16) 0.20915(12) 0.0250(4) Uani d 1 . .
O O6C 0.3800(2) 0.38575(15) 0.56199(12) 0.0236(4) Uani d 1 . .
O O8 0.7563(2) -0.00796(16) 0.65750(13) 0.0268(4) Uani d 1 . .
O O9 0.6657(2) 0.09231(15) 0.50758(12) 0.0221(4) Uani d 1 . .
O O10 0.2371(3) 0.55224(16) 0.80905(13) 0.0266(4) Uani d 1 . .
O O29 0.1208(2) 0.63513(15) 0.97792(12) 0.0217(4) Uani d 1 . .
H H7 0.526(4) 0.240(3) 0.627(2) 0.026 Uiso d 1 . .
H H27 0.289(4) 0.466(2) 1.047(2) 0.026 Uiso d 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -15 1 0.0329
-1 15 -1 0.0329
1 1 17 0.1859
-1 -1 -17 0.1859
-10 -4 -1 0.0601
10 4 1 0.0601
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
C2 C1 C6 . . 120.5(2) ?
C2 C1 N7 . . 115.91(19) ?
C6 C1 N7 . . 123.6(2) ?
N1C C1C H1CA . . 109.5 ?
N1C C1C H1CB . . 109.5 ?
H1CA C1C H1CB . . 109.5 ?
N1C C1C H1CC . . 109.5 ?
H1CA C1C H1CC . . 109.5 ?
H1CB C1C H1CC . . 109.5 ?
C3 C2 C1 . . 120.2(2) ?
C3 C2 H2 . . 119.9 ?
C1 C2 H2 . . 119.9 ?
O2C C2C N3C . . 122.0(2) ?
O2C C2C N1C . . 120.3(2) ?
N3C C2C N1C . . 117.7(2) ?
C2 C3 C4 . . 119.4(2) ?
C2 C3 N27 . . 123.8(2) ?
C4 C3 N27 . . 116.7(2) ?
N3C C3C H3CA . . 109.5 ?
N3C C3C H3CB . . 109.5 ?
H3CA C3C H3CB . . 109.5 ?
N3C C3C H3CC . . 109.5 ?
H3CA C3C H3CC . . 109.5 ?
H3CB C3C H3CC . . 109.5 ?
C5 C4 C3 . . 119.4(2) ?
C5 C4 H4 . . 120.3 ?
C3 C4 H4 . . 120.3 ?
N9C C4C C5C . . 112.90(19) ?
N9C C4C N3C . . 125.98(19) ?
C5C C4C N3C . . 121.1(2) ?
C4 C5 C6 . . 122.2(2) ?
C4 C5 H5 . . 118.9 ?
C6 C5 H5 . . 118.9 ?
C4C C5C N7C . . 104.4(2) ?
C4C C5C C6C . . 123.7(2) ?
N7C C5C C6C . . 132.0(2) ?
C5 C6 C1 . . 118.2(2) ?
C5 C6 H6 . . 120.9 ?
C1 C6 H6 . . 120.9 ?
O6C C6C C5C . . 126.8(2) ?
O6C C6C N1C . . 121.5(2) ?
C5C C6C N1C . . 111.71(18) ?
O8 C8 O9 . . 124.0(2) ?
O8 C8 N7 . . 126.8(2) ?
O9 C8 N7 . . 109.22(19) ?
N9C C8C N7C . . 113.4(2) ?
N9C C8C H8C . . 123.3 ?
N7C C8C H8C . . 123.3 ?
O9 C10 C11 . . 107.5(2) ?
O9 C10 H10A . . 110.2 ?
C11 C10 H10A . . 110.2 ?
O9 C10 H10B . . 110.2 ?
C11 C10 H10B . . 110.2 ?
H10A C10 H10B . . 108.5 ?
C10 C11 H11A . . 109.5 ?
C10 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C10 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
O10 C28 O29 . . 123.3(2) ?
O10 C28 N27 . . 126.0(2) ?
O29 C28 N27 . . 110.69(18) ?
O29 C30 C31 . . 107.81(18) ?
O29 C30 H30A . . 110.1 ?
C31 C30 H30A . . 110.1 ?
O29 C30 H30B . . 110.1 ?
C31 C30 H30B . . 110.1 ?
H30A C30 H30B . . 108.5 ?
C30 C31 H31A . . 109.5 ?
C30 C31 H31B . . 109.5 ?
H31A C31 H31B . . 109.5 ?
C30 C31 H31C . . 109.5 ?
H31A C31 H31C . . 109.5 ?
H31B C31 H31C . . 109.5 ?
C2C N1C C6C . . 126.1(2) ?
C2C N1C C1C . . 115.60(18) ?
C6C N1C C1C . . 118.33(17) ?
C2C N3C C4C . . 119.69(18) ?
C2C N3C C3C . . 119.50(19) ?
C4C N3C C3C . . 120.8(2) ?
C8 N7 C1 . . 127.66(19) ?
C8 N7 H7 . . 116.0(17) ?
C1 N7 H7 . . 116.3(17) ?
C8C N7C C5C . . 106.38(18) ?
C8C N7C H7C . . 126.8 ?
C5C N7C H7C . . 126.8 ?
C8C N9C C4C . . 102.95(19) ?
C28 N27 C3 . . 126.79(19) ?
C28 N27 H27 . . 118.2(17) ?
C3 N27 H27 . . 114.9(17) ?
C8 O9 C10 . . 114.89(18) ?
C28 O29 C30 . . 115.15(17) ?
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
C1 C2 . 1.391(3) ?
C1 C6 . 1.392(3) ?
C1 N7 . 1.411(3) ?
C1C N1C . 1.462(3) ?
C1C H1CA . 0.98 ?
C1C H1CB . 0.98 ?
C1C H1CC . 0.98 ?
C2 C3 . 1.390(3) ?
C2 H2 . 0.95 ?
C2C O2C . 1.228(3) ?
C2C N3C . 1.360(3) ?
C2C N1C . 1.393(3) ?
C3 C4 . 1.398(3) ?
C3 N27 . 1.408(3) ?
C3C N3C . 1.468(3) ?
C3C H3CA . 0.98 ?
C3C H3CB . 0.98 ?
C3C H3CC . 0.98 ?
C4 C5 . 1.369(3) ?
C4 H4 . 0.95 ?
C4C N9C . 1.349(3) ?
C4C C5C . 1.365(3) ?
C4C N3C . 1.376(3) ?
C5 C6 . 1.390(3) ?
C5 H5 . 0.95 ?
C5C N7C . 1.383(3) ?
C5C C6C . 1.407(3) ?
C6 H6 . 0.95 ?
C6C O6C . 1.229(3) ?
C6C N1C . 1.409(3) ?
C8 O8 . 1.210(3) ?
C8 O9 . 1.348(3) ?
C8 N7 . 1.352(3) ?
C8C N9C . 1.334(3) ?
C8C N7C . 1.340(3) ?
C8C H8C . 0.95 ?
C10 O9 . 1.452(3) ?
C10 C11 . 1.507(3) ?
C10 H10A . 0.99 ?
C10 H10B . 0.99 ?
C11 H11A . 0.98 ?
C11 H11B . 0.98 ?
C11 H11C . 0.98 ?
C28 O10 . 1.219(3) ?
C28 O29 . 1.345(3) ?
C28 N27 . 1.346(3) ?
C30 O29 . 1.449(3) ?
C30 C31 . 1.499(4) ?
C30 H30A . 0.99 ?
C30 H30B . 0.99 ?
C31 H31A . 0.98 ?
C31 H31B . 0.98 ?
C31 H31C . 0.98 ?
N7 H7 . 0.91(3) ?
N7C H7C . 0.88 ?
N27 H27 . 0.94(3) ?
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
C6 C1 C2 C3 . . . . -0.6(4) ?
N7 C1 C2 C3 . . . . 178.9(2) ?
C1 C2 C3 C4 . . . . 1.5(4) ?
C1 C2 C3 N27 . . . . -176.7(2) ?
C2 C3 C4 C5 . . . . -1.6(4) ?
N27 C3 C4 C5 . . . . 176.7(2) ?
C3 C4 C5 C6 . . . . 0.9(4) ?
N9C C4C C5C N7C . . . . 0.5(3) ?
N3C C4C C5C N7C . . . . -178.7(2) ?
N9C C4C C5C C6C . . . . -179.9(2) ?
N3C C4C C5C C6C . . . . 0.8(4) ?
C4 C5 C6 C1 . . . . -0.1(4) ?
C2 C1 C6 C5 . . . . -0.1(4) ?
N7 C1 C6 C5 . . . . -179.6(2) ?
C4C C5C C6C O6C . . . . 179.6(2) ?
N7C C5C C6C O6C . . . . -1.0(4) ?
C4C C5C C6C N1C . . . . -0.4(3) ?
N7C C5C C6C N1C . . . . 179.1(2) ?
O2C C2C N1C C6C . . . . -178.2(2) ?
N3C C2C N1C C6C . . . . 1.4(3) ?
O2C C2C N1C C1C . . . . 0.3(3) ?
N3C C2C N1C C1C . . . . 180.0(2) ?
O6C C6C N1C C2C . . . . 179.3(2) ?
C5C C6C N1C C2C . . . . -0.8(3) ?
O6C C6C N1C C1C . . . . 0.8(3) ?
C5C C6C N1C C1C . . . . -179.3(2) ?
O2C C2C N3C C4C . . . . 178.8(2) ?
N1C C2C N3C C4C . . . . -0.8(3) ?
O2C C2C N3C C3C . . . . 0.2(4) ?
N1C C2C N3C C3C . . . . -179.4(2) ?
N9C C4C N3C C2C . . . . -179.3(2) ?
C5C C4C N3C C2C . . . . -0.2(3) ?
N9C C4C N3C C3C . . . . -0.8(4) ?
C5C C4C N3C C3C . . . . 178.3(2) ?
O8 C8 N7 C1 . . . . -0.3(4) ?
O9 C8 N7 C1 . . . . 178.6(2) ?
C2 C1 N7 C8 . . . . 175.6(2) ?
C6 C1 N7 C8 . . . . -4.9(4) ?
N9C C8C N7C C5C . . . . 0.4(3) ?
C4C C5C N7C C8C . . . . -0.5(3) ?
C6C C5C N7C C8C . . . . 180.0(3) ?
N7C C8C N9C C4C . . . . -0.1(3) ?
C5C C4C N9C C8C . . . . -0.2(3) ?
N3C C4C N9C C8C . . . . 178.9(2) ?
O10 C28 N27 C3 . . . . -6.3(4) ?
O29 C28 N27 C3 . . . . 173.9(2) ?
C2 C3 N27 C28 . . . . 2.8(4) ?
C4 C3 N27 C28 . . . . -175.5(2) ?
O8 C8 O9 C10 . . . . -0.4(3) ?
N7 C8 O9 C10 . . . . -179.3(2) ?
C11 C10 O9 C8 . . . . -176.3(2) ?
O10 C28 O29 C30 . . . . -3.8(3) ?
N27 C28 O29 C30 . . . . 175.9(2) ?
C31 C30 O29 C28 . . . . -173.4(2) ?
