Crystal structures of N6-modified-amino acid nucleobase analogs(iii): adenine–valeric acid, adenine–hexanoic acid and adenine–gabapentine
García-Raso, Angel; Terrón, Angel; Balle, Bartomeu; López-Zafra, Adela; Frontera, Antonio; Barceló-Oliver, Miquel; Fiol, Juan J.; New Journal of Chemistry 44 (2020) 12236–12246; doi:10.1039/D0NJ02538K

data_7059717
_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 H16 N5 O2, Cl'
_chemical_formula_sum            'C11 H16 Cl N5 O2'
_chemical_formula_weight         285.74
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-02-09
_audit_creation_method
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_audit_update_record
;
2020-05-16 deposited with the CCDC.	2020-06-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.104(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.3113(8)
_cell_length_b                   5.2940(4)
_cell_length_c                   20.4958(14)
_cell_measurement_reflns_used    8494
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      68.58
_cell_measurement_theta_min      4.12
_cell_volume                     1334.93(16)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       'Bruker Apex3, 2016'
_computing_data_reduction        'SAINT v8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0633
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            31832
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        66.586
_diffrn_reflns_theta_max         66.586
_diffrn_reflns_theta_min         4.317
_diffrn_source                   'high brilliance microfocus sealed tube'
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.611
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5452
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 19903 reflections, Rint = 0.0568
 (10024 with I > 3sig(I), Rint = 0.0544)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_description       prism
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.363
_exptl_crystal_size_mid          0.207
_exptl_crystal_size_min          0.164
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2330
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.137
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0540
_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/[\s^2^(Fo^2^)+(0.0915P)^2^+0.6279P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1544
_refine_ls_wR_factor_ref         0.1545
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2325
_reflns_number_total             2330
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj02538k1.cif
_cod_data_source_block           1_a_CCDC1
_cod_depositor_comments
;Adding full bibliography for 7059716--7059719.cif.

 Adding full bibliography for 7059716--7059719.cif.
;
_cod_database_code               7059717
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.674
_shelx_estimated_absorpt_t_min   0.451
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C8(H8), N6(H6), N9(H9)
2.c Idealised tetrahedral OH refined as rotating group:
 O16(H16)
;
_shelx_res_checksum              92201
_olex2_date_sample_data_collection 2019-12-19
_olex2_date_sample_submission    2019-12-16
_olex2_exptl_crystal_mounting_method
'cryoloop, covered with Parabar 10312 (previously known as Paratone)'
_olex2_submission_original_sample_id mb191219
_olex2_submission_special_instructions 'No special instructions were received'