#------------------------------------------------------------------------------
#$Date: 2020-10-06 12:36:56 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257644 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/97/7059719.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_7059719
loop_
_publ_author_name
'García-Raso, Angel'
'Terrón, Angel'
'Balle, Bartomeu'
'López-Zafra, Adela'
'Frontera, Antonio'
'Barceló-Oliver, Miquel'
'Fiol, Juan J.'
_publ_section_title
;
 Crystal structures of N6-modified-amino acid nucleobase analogs(iii):
 adenine--valeric acid, adenine--hexanoic acid and adenine--gabapentine
;
_journal_issue                   28
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              12236
_journal_page_last               12246
_journal_paper_doi               10.1039/D0NJ02538K
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety         'C11 H15 N5 O2'
_chemical_formula_sum            'C11 H15 N5 O2'
_chemical_formula_weight         249.28
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_creation_date             2019-04-04T14:55:07-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2020-05-16 deposited with the CCDC.	2020-06-22 downloaded from the CCDC.
;
_cell_angle_alpha                102.47(4)
_cell_angle_beta                 91.989(9)
_cell_angle_gamma                98.392(9)
_cell_formula_units_Z            2
_cell_length_a                   7.159(4)
_cell_length_b                   9.126(4)
_cell_length_c                   9.472(4)
_cell_measurement_reflns_used    2152
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.31
_cell_measurement_wavelength     0.71073
_cell_volume                     596.4(5)
_computing_cell_refinement       'SAINT V6.28A integration software'
_computing_data_collection       'Bruker APEX2 software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_diffrn_ambient_temperature      300(2)
_diffrn_detector                 'APEX-II CCD'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'φ or ω oscillation scans'
_diffrn_orient_matrix_UB_11      -0.116647
_diffrn_orient_matrix_UB_12      0.033745
_diffrn_orient_matrix_UB_13      0.01344
_diffrn_orient_matrix_UB_21      0.079339
_diffrn_orient_matrix_UB_22      0.065543
_diffrn_orient_matrix_UB_23      0.037271
_diffrn_orient_matrix_UB_31      0.011467
_diffrn_orient_matrix_UB_32      0.045902
_diffrn_orient_matrix_UB_33      -0.056732
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.034
_diffrn_reflns_av_unetI/netI     0.0511
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2418
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_reduction_process
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.207
_diffrn_source                   'sealed x-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.1
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.897
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        SADABS - Bruker/Siemens area detector absorption and other corrections -
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2418
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0551
_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)+(0.0687P)²+0.1609P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1403
_refine_ls_wR_factor_ref         0.1481
_reflns_Friedel_coverage         0
_reflns_number_gt                1858
_reflns_number_total             2418
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0nj02538k1.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;Adding full bibliography for 7059716--7059719.cif.

 Adding full bibliography for 7059716--7059719.cif.
;
_cod_original_cell_volume        596.3(5)
_cod_database_code               7059719
_shelx_estimated_absorpt_t_min   0.979
_shelx_estimated_absorpt_t_max   0.981
_shelx_shelxl_version_number     2017/1
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
N1 N -0.0288(2) 0.7684(2) 1.03015(18) 0.0365(4) Uani 1 1 d . . . . .
C2 C -0.1681(3) 0.8289(2) 1.1010(2) 0.0383(5) Uani 1 1 d . . . . .
H2 H -0.173607 0.821164 1.197114 0.046 Uiso 1 1 calc R U . . .
N3 N -0.2996(2) 0.8985(2) 1.05238(18) 0.0357(4) Uani 1 1 d . . . . .
C4 C -0.2824(3) 0.9026(2) 0.9124(2) 0.0301(4) Uani 1 1 d . . . . .
C5 C -0.1466(3) 0.8461(2) 0.8263(2) 0.0311(5) Uani 1 1 d . . . . .
C6 C -0.0133(3) 0.7769(2) 0.8909(2) 0.0322(5) Uani 1 1 d . . . . .
N6 N 0.1246(2) 0.7178(2) 0.81766(19) 0.0397(5) Uani 1 1 d . . . . .
H6 H 0.133127 0.726881 0.729526 0.06 Uiso 1 1 calc R U . . .
N7 N -0.1759(2) 0.8674(2) 0.68751(18) 0.0370(4) Uani 1 1 d . . . . .
C8 C -0.3261(3) 0.9344(2) 0.6934(2) 0.0375(5) Uani 1 1 d . . . . .
H8 H -0.379632 0.962138 0.614086 0.045 Uiso 1 1 calc R U . . .
N9 N -0.3957(2) 0.9595(2) 0.82554(18) 0.0357(4) Uani 1 1 d . . . . .
H9 H -0.500(3) 1.0060(13) 0.8521(8) 0.054 Uiso 1 1 calc R U . . .
C10 C 0.2612(3) 0.6392(2) 0.8763(2) 0.0363(5) Uani 1 1 d . . . . .
H10A H 0.196366 0.563376 0.922839 0.044 Uiso 1 1 calc R U . . .
H10B H 0.348624 0.711034 0.947985 0.044 Uiso 1 1 calc R U . . .
C11 C 0.3676(3) 0.5641(3) 0.7532(2) 0.0409(5) Uani 1 1 d . . . . .
H11A H 0.423319 0.641001 0.704055 0.049 Uiso 1 1 calc R U . . .
H11B H 0.277602 0.4914 0.684157 0.049 Uiso 1 1 calc R U . . .
C12 C 0.5229(3) 0.4825(2) 0.7965(2) 0.0365(5) Uani 1 1 d . . . . .
H12A H 0.61919 0.555172 0.859882 0.044 Uiso 1 1 calc R U . . .
H12B H 0.470455 0.40798 0.849479 0.044 Uiso 1 1 calc R U . . .
C13 C 0.6115(4) 0.4041(3) 0.6642(3) 0.0554(7) Uani 1 1 d . . . . .
H13A H 0.517189 0.323144 0.608514 0.066 Uiso 1 1 calc R U . . .
H13B H 0.64405 0.476722 0.60443 0.066 Uiso 1 1 calc R U . . .
C14 C 0.7841(3) 0.3380(3) 0.6929(2) 0.0439(6) Uani 1 1 d . . . . .
H14A H 0.75589 0.271603 0.75927 0.053 Uiso 1 1 calc R U . . .
H14B H 0.883804 0.419634 0.739756 0.053 Uiso 1 1 calc R U . . .
C15 C 0.8540(3) 0.2498(3) 0.5581(2) 0.0380(5) Uani 1 1 d . . . . .
O15 O 0.7512(2) 0.1817(2) 0.45348(17) 0.0534(5) Uani 1 1 d . . . . .
O16 O 1.0369(2) 0.2516(2) 0.56383(18) 0.0587(5) Uani 1 1 d . . . . .
H16 H 1.067945 0.209496 0.484585 0.088 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 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_
_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
C2 N1 C6 118.25(17) . . ?
N3 C2 N1 128.76(19) . . ?
N3 C2 H2 115.6 . . ?
N1 C2 H2 115.6 . . ?
C2 N3 C4 111.55(16) . . ?
N3 C4 N9 127.90(16) . . ?
N3 C4 C5 126.16(17) . . ?
N9 C4 C5 105.92(17) . . ?
C4 C5 N7 109.98(17) . . ?
C4 C5 C6 116.93(18) . . ?
N7 C5 C6 133.07(17) . . ?
N6 C6 N1 119.55(18) . . ?
N6 C6 C5 122.11(18) . . ?
N1 C6 C5 118.33(17) . . ?
C6 N6 C10 124.71(17) . . ?
C6 N6 H6 117.6 . . ?
C10 N6 H6 117.6 . . ?
C8 N7 C5 104.17(16) . . ?
N7 C8 N9 113.50(19) . . ?
N7 C8 H8 123.2 . . ?
N9 C8 H8 123.2 . . ?
C8 N9 C4 106.43(16) . . ?
C8 N9 H9 126.8 . . ?
C4 N9 H9 126.8 . . ?
N6 C10 C11 108.39(16) . . ?
N6 C10 H10A 110 . . ?
C11 C10 H10A 110 . . ?
N6 C10 H10B 110 . . ?
C11 C10 H10B 110 . . ?
H10A C10 H10B 108.4 . . ?
C10 C11 C12 115.34(17) . . ?
C10 C11 H11A 108.4 . . ?
C12 C11 H11A 108.4 . . ?
C10 C11 H11B 108.4 . . ?
C12 C11 H11B 108.4 . . ?
H11A C11 H11B 107.5 . . ?
C13 C12 C11 110.67(17) . . ?
C13 C12 H12A 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C14 C13 C12 115.89(19) . . ?
C14 C13 H13A 108.3 . . ?
C12 C13 H13A 108.3 . . ?
C14 C13 H13B 108.3 . . ?
C12 C13 H13B 108.3 . . ?
H13A C13 H13B 107.4 . . ?
C13 C14 C15 113.04(18) . . ?
C13 C14 H14A 109 . . ?
C15 C14 H14A 109 . . ?
C13 C14 H14B 109 . . ?
C15 C14 H14B 109 . . ?
H14A C14 H14B 107.8 . . ?
O15 C15 O16 122.59(19) . . ?
O15 C15 C14 123.43(19) . . ?
O16 C15 C14 113.98(19) . . ?
C15 O16 H16 109.5 . . ?
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
N1 C2 1.340(3) . ?
N1 C6 1.345(3) . ?
C2 N3 1.332(2) . ?
C2 H2 0.93 . ?
N3 C4 1.344(3) . ?
C4 N9 1.365(3) . ?
C4 C5 1.377(3) . ?
C5 N7 1.383(3) . ?
C5 C6 1.410(3) . ?
C6 N6 1.337(2) . ?
N6 C10 1.455(2) . ?
N6 H6 0.86 . ?
N7 C8 1.310(2) . ?
C8 N9 1.349(3) . ?
C8 H8 0.93 . ?
N9 H9 0.93(3) . ?
C10 C11 1.510(3) . ?
C10 H10A 0.97 . ?
C10 H10B 0.97 . ?
C11 C12 1.517(3) . ?
C11 H11A 0.97 . ?
C11 H11B 0.97 . ?
C12 C13 1.512(3) . ?
C12 H12A 0.97 . ?
C12 H12B 0.97 . ?
C13 C14 1.493(3) . ?
C13 H13A 0.97 . ?
C13 H13B 0.97 . ?
C14 C15 1.499(3) . ?
C14 H14A 0.97 . ?
C14 H14B 0.97 . ?
C15 O15 1.208(3) . ?
C15 O16 1.307(3) . ?
O16 H16 0.82 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N6 H6 O15 0.86 2.22 3.028(3) 157 2_666 yes
N9 H9 N3 0.93 1.94 2.851(2) 168 2_477 yes
C11 H11B O16 0.97 2.6 3.532(3) 162 1_455 yes
O16 H16 N7 0.82 1.87 2.683(2) 171 2_666 yes
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
C6 N1 C2 N3 0.3(3) . . . . ?
N1 C2 N3 C4 0.9(3) . . . . ?
C2 N3 C4 N9 177.36(19) . . . . ?
C2 N3 C4 C5 -1.1(3) . . . . ?
N3 C4 C5 N7 178.59(19) . . . . ?
N9 C4 C5 N7 -0.2(2) . . . . ?
N3 C4 C5 C6 0.2(3) . . . . ?
N9 C4 C5 C6 -178.51(17) . . . . ?
C2 N1 C6 N6 179.84(18) . . . . ?
C2 N1 C6 C5 -1.3(3) . . . . ?
C4 C5 C6 N6 179.87(18) . . . . ?
N7 C5 C6 N6 2.0(4) . . . . ?
C4 C5 C6 N1 1.0(3) . . . . ?
N7 C5 C6 N1 -176.9(2) . . . . ?
N1 C6 N6 C10 1.6(3) . . . . ?
C5 C6 N6 C10 -177.22(19) . . . . ?
C4 C5 N7 C8 -0.2(2) . . . . ?
C6 C5 N7 C8 177.8(2) . . . . ?
C5 N7 C8 N9 0.5(2) . . . . ?
N7 C8 N9 C4 -0.6(2) . . . . ?
N3 C4 N9 C8 -178.3(2) . . . . ?
C5 C4 N9 C8 0.4(2) . . . . ?
C6 N6 C10 C11 169.22(19) . . . . ?
N6 C10 C11 C12 177.33(18) . . . . ?
C10 C11 C12 C13 176.6(2) . . . . ?
C11 C12 C13 C14 171.7(2) . . . . ?
C12 C13 C14 C15 174.7(2) . . . . ?
C13 C14 C15 O15 -30.9(3) . . . . ?
C13 C14 C15 O16 149.8(2) . . . . ?
