#------------------------------------------------------------------------------
#$Date: 2017-11-18 04:23:28 +0200 (Sat, 18 Nov 2017) $
#$Revision: 203315 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/95/7229597.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_7229597
loop_
_publ_author_name
'Markad, Datta'
'Mandal, Sanjay K.'
_publ_section_title
;
 An exploration into the amide--pseudo amide hydrogen bonding synthon
 between a new coformer with two primary amide groups and theophylline
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/C7CE01666B
_journal_year                    2017
_chemical_formula_moiety         'C24 H28 N6 O2, 4(C7 H8 N4 O2)'
_chemical_formula_sum            'C52 H60 N22 O10'
_chemical_formula_weight         1153.22
_chemical_melting_point          507
_chemical_name_common            '[(2bpxg.4THP)n]'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_update_record
;
2017-09-03 deposited with the CCDC.
2017-11-06 downloaded from the CCDC.
;
_cell_angle_alpha                96.84(2)
_cell_angle_beta                 93.49(2)
_cell_angle_gamma                94.57(2)
_cell_formula_units_Z            1
_cell_length_a                   9.536(16)
_cell_length_b                   11.74(2)
_cell_length_c                   12.81(2)
_cell_measurement_reflns_used    1199
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      24.5942
_cell_measurement_theta_min      2.5586
_cell_volume                     1416(4)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker Kappa APEX II'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_radiation_monochromator  Graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_unetI/netI     0.0502
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15263
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.61
_diffrn_source                   'Sealed tube'
_diffrn_source_type              'Fine Focus'
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6037
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             606
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.239
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         4851
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0941
_refine_ls_R_factor_gt           0.0558
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1535
_refine_ls_wR_factor_ref         0.1861
_reflns_number_gt                2814
_reflns_number_total             4851
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7ce01666b2.cif
_cod_data_source_block           I_CCDC1
_cod_original_cell_volume        1416.(4)
_cod_database_code               7229597
loop_
_space_group_symop_operation_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_refinement_flags_adp
_atom_site_refinement_flags_posn
_atom_site_occupancy
C C1 0.0260(4) 0.0210(3) 0.1571(2) 0.0812(10) Uani d . . 1
H H12A -0.0506 -0.0382 0.1441 0.122 Uiso calc U R 1
H H12B 0.1088 -0.0072 0.1278 0.122 Uiso calc U R 1
H H12C 0.0016 0.087 0.1247 0.122 Uiso calc U R 1
C C2 -0.0182(3) 0.1455(2) 0.3186(2) 0.0614(7) Uani d . . 1
C C3 -0.0604(4) 0.2764(2) 0.4823(3) 0.0798(10) Uani d . . 1
H H10A -0.0889 0.2548 0.5483 0.12 Uiso calc U R 1
H H10B -0.1421 0.2894 0.4392 0.12 Uiso calc U R 1
H H10C 0.002 0.3457 0.4949 0.12 Uiso calc U R 1
C C4 0.1120(3) 0.1258(2) 0.4842(2) 0.0521(7) Uani d . . 1
C C5 0.1771(3) 0.03450(19) 0.43757(18) 0.0497(6) Uani d . . 1
C C6 0.1530(3) -0.0089(2) 0.32621(19) 0.0530(7) Uani d . . 1
C C7 0.2458(3) 0.0724(2) 0.6062(2) 0.0650(8) Uani d . . 1
H H8 0.2915 0.0672 0.6715 0.078 Uiso calc U R 1
C C8 0.6372(3) 0.0436(2) 0.0341(2) 0.0581(7) Uani d . . 1
H H00U 0.7291 0.0715 0.0576 0.07 Uiso calc U R 1
C C9 0.4220(3) 0.0575(2) -0.06866(19) 0.0564(7) Uani d . . 1
H H00T 0.3684 0.095 -0.1148 0.068 Uiso calc U R 1
C C10 0.5603(3) 0.10335(18) -0.03511(17) 0.0473(6) Uani d . . 1
C C11 0.6273(3) 0.21156(19) -0.07359(18) 0.0548(7) Uani d . . 1
H H00E 0.7059 0.1916 -0.1147 0.066 Uiso calc U R 1
H H00F 0.5586 0.2421 -0.1192 0.066 Uiso calc U R 1
C C12 0.5549(3) 0.3512(2) 0.06398(18) 0.0527(7) Uani d . . 1
H H19A 0.4853 0.2885 0.072 0.063 Uiso calc U R 1
H H19B 0.5126 0.3991 0.0163 0.063 Uiso calc U R 1
C C13 0.5913(3) 0.4232(2) 0.17201(19) 0.0517(7) Uani d . . 1
C C14 0.7698(3) 0.3961(2) -0.02361(19) 0.0569(7) Uani d . . 1
H H00C 0.7887 0.4601 0.0321 0.068 Uiso calc U R 1
H H00D 0.7186 0.4236 -0.082 0.068 Uiso calc U R 1
C C15 0.9092(3) 0.35698(19) -0.05965(18) 0.0514(7) Uani d . . 1
C C16 1.0063(3) 0.3141(2) 0.0091(2) 0.0603(7) Uani d . . 1
H H55 0.9848 0.3057 0.0777 0.072 Uiso calc U R 1
C C17 1.1347(3) 0.2841(2) -0.0262(2) 0.0698(8) Uani d . . 1
H H011 1.2005 0.2562 0.0187 0.084 Uiso calc U R 1
C C18 1.1641(4) 0.2965(2) -0.1305(2) 0.0698(8) Uani d . . 1
H H010 1.2492 0.2769 -0.1564 0.084 Uiso calc U R 1
C C19 1.0624(4) 0.3390(2) -0.1939(2) 0.0741(9) Uani d . . 1
H H013 1.082 0.3475 -0.2629 0.089 Uiso calc U R 1
C C20 0.5123(3) 0.8724(2) 0.7106(2) 0.0676(8) Uani d . . 1
H H00H 0.5572 0.882 0.7806 0.101 Uiso calc U R 1
H H00I 0.4126 0.8551 0.7137 0.101 Uiso calc U R 1
H H00J 0.5291 0.9422 0.6795 0.101 Uiso calc U R 1
C C21 0.6720(3) 0.7136(2) 0.69207(18) 0.0537(7) Uani d . . 1
C C22 0.8223(4) 0.5525(3) 0.6807(2) 0.0749(9) Uani d . . 1
H H01A 0.9048 0.6018 0.7078 0.112 Uiso calc U R 1
H H01B 0.8485 0.4912 0.6313 0.112 Uiso calc U R 1
H H01C 0.7788 0.5208 0.7378 0.112 Uiso calc U R 1
C C23 0.6802(3) 0.5870(2) 0.51657(18) 0.0503(7) Uani d . . 1
C C24 0.5762(3) 0.6568(2) 0.47782(18) 0.0470(6) Uani d . . 1
C C25 0.5247(3) 0.74656(19) 0.53991(17) 0.0471(6) Uani d . . 1
C C26 0.4202(3) 0.7407(2) 0.3851(2) 0.0606(8) Uani d . . 1
H H00Z 0.3618 0.7572 0.3291 0.073 Uiso calc U R 1
N N1 0.4281(2) 0.80091(18) 0.48375(15) 0.0569(6) Uani d . . 1
N N2 0.5065(2) 0.65453(17) 0.37771(15) 0.0564(6) Uani d . . 1
H H22 0.5168 0.6075 0.3225 0.068 Uiso calc U R 1
N N3 0.7202(2) 0.62082(17) 0.62655(15) 0.0537(6) Uani d . . 1
N N4 0.5709(2) 0.77640(17) 0.64591(14) 0.0510(6) Uani d . . 1
N N5 0.0139(3) 0.18219(17) 0.42710(18) 0.0605(6) Uani d . . 1
N N6 0.0546(2) 0.05399(17) 0.27310(16) 0.0561(6) Uani d . . 1
N N7 0.2649(3) 0.00089(18) 0.51761(15) 0.0590(6) Uani d . . 1
H H17 0.3198 -0.0538 0.512 0.071 Uiso calc U R 1
N N8 0.1543(3) 0.15165(19) 0.59035(17) 0.0655(7) Uani d . . 1
N N9 0.9363(3) 0.36889(19) -0.16135(17) 0.0678(7) Uani d . . 1
N N10 0.6787(2) 0.30237(15) 0.01588(14) 0.0482(6) Uani d . . 1
N N11 0.6942(3) 0.38924(17) 0.23573(16) 0.0614(6) Uani d . . 1
H H4A 0.714 0.4251 0.2981 0.074 Uiso calc U R 1
H H4B 0.7399 0.3318 0.2139 0.074 Uiso calc U R 1
O O1 0.5210(2) 0.50560(15) 0.19850(14) 0.0710(6) Uani d . . 1
O O2 0.7183(2) 0.73738(16) 0.78545(14) 0.0739(6) Uani d . . 1
O O3 0.7331(2) 0.50623(15) 0.46520(14) 0.0686(6) Uani d . . 1
O O4 -0.1066(2) 0.19028(17) 0.26542(17) 0.0818(7) Uani d . . 1
O O5 0.2096(2) -0.08883(16) 0.27909(14) 0.0708(6) Uani 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 0.0000 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
N6 C1 H12A . . 109.5
N6 C1 H12B . . 109.5
H12A C1 H12B . . 109.5
N6 C1 H12C . . 109.5
H12A C1 H12C . . 109.5
H12B C1 H12C . . 109.5
O4 C2 N6 . . 121.2(3)
O4 C2 N5 . . 122.0(3)
N6 C2 N5 . . 116.8(2)
N5 C3 H10A . . 109.5
N5 C3 H10B . . 109.5
H10A C3 H10B . . 109.5
N5 C3 H10C . . 109.5
H10A C3 H10C . . 109.5
H10B C3 H10C . . 109.5
C5 C4 N8 . . 111.9(3)
C5 C4 N5 . . 121.8(2)
N8 C4 N5 . . 126.3(2)
C4 C5 N7 . . 105.6(2)
C4 C5 C6 . . 123.0(2)
N7 C5 C6 . . 131.5(2)
O5 C6 N6 . . 121.7(2)
O5 C6 C5 . . 126.3(2)
N6 C6 C5 . . 112.0(2)
N8 C7 N7 . . 113.6(3)
N8 C7 H8 . . 123.2
N7 C7 H8 . . 123.2
C10 C8 C9 . 2_655 121.3(3)
C10 C8 H00U . . 119.4
C9 C8 H00U 2_655 . 119.4
C8 C9 C10 2_655 . 121.5(2)
C8 C9 H00T 2_655 . 119.3
C10 C9 H00T . . 119.3
C8 C10 C9 . . 117.2(2)
C8 C10 C11 . . 120.6(3)
C9 C10 C11 . . 122.2(2)
N10 C11 C10 . . 112.0(2)
N10 C11 H00E . . 109.2
C10 C11 H00E . . 109.2
N10 C11 H00F . . 109.2
C10 C11 H00F . . 109.2
H00E C11 H00F . . 107.9
N10 C12 C13 . . 113.7(2)
N10 C12 H19A . . 108.8
C13 C12 H19A . . 108.8
N10 C12 H19B . . 108.8
C13 C12 H19B . . 108.8
H19A C12 H19B . . 107.7
O1 C13 N11 . . 123.4(2)
O1 C13 C12 . . 119.0(2)
N11 C13 C12 . . 117.5(2)
N10 C14 C15 . . 113.1(2)
N10 C14 H00C . . 109.0
C15 C14 H00C . . 109.0
N10 C14 H00D . . 109.0
C15 C14 H00D . . 109.0
H00C C14 H00D . . 107.8
N9 C15 C16 . . 121.9(3)
N9 C15 C14 . . 116.4(2)
C16 C15 C14 . . 121.6(2)
C17 C16 C15 . . 119.5(3)
C17 C16 H55 . . 120.2
C15 C16 H55 . . 120.2
C16 C17 C18 . . 119.1(3)
C16 C17 H011 . . 120.4
C18 C17 H011 . . 120.4
C19 C18 C17 . . 118.0(3)
C19 C18 H010 . . 121.0
C17 C18 H010 . . 121.0
N9 C19 C18 . . 124.0(3)
N9 C19 H013 . . 118.0
C18 C19 H013 . . 118.0
N4 C20 H00H . . 109.5
N4 C20 H00I . . 109.5
H00H C20 H00I . . 109.5
N4 C20 H00J . . 109.5
H00H C20 H00J . . 109.5
H00I C20 H00J . . 109.5
O2 C21 N4 . . 122.3(2)
O2 C21 N3 . . 120.9(3)
N4 C21 N3 . . 116.8(2)
N3 C22 H01A . . 109.5
N3 C22 H01B . . 109.5
H01A C22 H01B . . 109.5
N3 C22 H01C . . 109.5
H01A C22 H01C . . 109.5
H01B C22 H01C . . 109.5
O3 C23 N3 . . 121.5(2)
O3 C23 C24 . . 126.8(2)
N3 C23 C24 . . 111.6(2)
C25 C24 N2 . . 105.3(2)
C25 C24 C23 . . 123.2(2)
N2 C24 C23 . . 131.6(2)
N1 C25 C24 . . 111.8(2)
N1 C25 N4 . . 126.1(2)
C24 C25 N4 . . 122.1(2)
N2 C26 N1 . . 112.8(2)
N2 C26 H00Z . . 123.6
N1 C26 H00Z . . 123.6
C26 N1 C25 . . 103.5(2)
C26 N2 C24 . . 106.6(2)
C26 N2 H22 . . 126.7
C24 N2 H22 . . 126.7
C21 N3 C23 . . 126.8(2)
C21 N3 C22 . . 114.8(2)
C23 N3 C22 . . 118.4(2)
C25 N4 C21 . . 119.6(2)
C25 N4 C20 . . 120.7(2)
C21 N4 C20 . . 119.7(2)
C4 N5 C2 . . 119.6(2)
C4 N5 C3 . . 119.9(2)
C2 N5 C3 . . 120.4(2)
C2 N6 C6 . . 126.8(2)
C2 N6 C1 . . 116.1(2)
C6 N6 C1 . . 117.1(2)
C7 N7 C5 . . 106.0(2)
C7 N7 H17 . . 127.0
C5 N7 H17 . . 127.0
C7 N8 C4 . . 103.0(2)
C19 N9 C15 . . 117.5(2)
C12 N10 C11 . . 108.9(2)
C12 N10 C14 . . 109.8(2)
C11 N10 C14 . . 110.0(2)
C13 N11 H4A . . 120.0
C13 N11 H4B . . 120.0
H4A N11 H4B . . 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 N6 . 1.494(4)
C1 H12A . 0.96
C1 H12B . 0.96
C1 H12C . 0.96
C2 O4 . 1.240(4)
C2 N6 . 1.412(4)
C2 N5 . 1.413(4)
C3 N5 . 1.492(3)
C3 H10A . 0.96
C3 H10B . 0.96
C3 H10C . 0.96
C4 C5 . 1.375(4)
C4 N8 . 1.385(4)
C4 N5 . 1.408(4)
C5 N7 . 1.397(4)
C5 C6 . 1.455(4)
C6 O5 . 1.233(3)
C6 N6 . 1.429(4)
C7 N8 . 1.350(4)
C7 N7 . 1.360(4)
C7 H8 . 0.93
C8 C10 . 1.403(4)
C8 C9 2_655 1.404(4)
C8 H00U . 0.93
C9 C8 2_655 1.404(4)
C9 C10 . 1.406(4)
C9 H00T . 0.93
C10 C11 . 1.525(4)
C11 N10 . 1.499(3)
C11 H00E . 0.97
C11 H00F . 0.97
C12 N10 . 1.488(4)
C12 C13 . 1.539(4)
C12 H19A . 0.97
C12 H19B . 0.97
C13 O1 . 1.246(3)
C13 N11 . 1.354(4)
C14 N10 . 1.502(4)
C14 C15 . 1.521(4)
C14 H00C . 0.97
C14 H00D . 0.97
C15 N9 . 1.365(4)
C15 C16 . 1.402(4)
C16 C17 . 1.388(4)
C16 H55 . 0.93
C17 C18 . 1.405(5)
C17 H011 . 0.93
C18 C19 . 1.388(4)
C18 H010 . 0.93
C19 N9 . 1.356(4)
C19 H013 . 0.93
C20 N4 . 1.485(3)
C20 H00H . 0.96
C20 H00I . 0.96
C20 H00J . 0.96
C21 O2 . 1.241(3)
C21 N4 . 1.404(4)
C21 N3 . 1.418(3)
C22 N3 . 1.499(4)
C22 H01A . 0.96
C22 H01B . 0.96
C22 H01C . 0.96
C23 O3 . 1.247(3)
C23 N3 . 1.437(4)
C23 C24 . 1.439(4)
C24 C25 . 1.383(3)
C24 N2 . 1.404(4)
C25 N1 . 1.377(3)
C25 N4 . 1.396(4)
C26 N2 . 1.352(4)
C26 N1 . 1.368(3)
C26 H00Z . 0.93
N2 H22 . 0.86
N7 H17 . 0.86
N11 H4A . 0.86
N11 H4B . 0.86
