Modified-amino acid/peptide pyrimidine analogs: synthesis, structural characterization and DFT studies of N-(pyrimidyl)gabapentine and N-(pyrimidyl)baclofen
García-Raso, Angel; Terrón, Angel; Fiol, Juan J.; López-Zafra, Adela; Massanet, Bárbara; Frontera, Antonio; Barceló-Oliver, Miquel; New Journal of Chemistry 45 (2021) 22053–22061; doi:10.1039/D1NJ04639J

data_7061024
_publ_section_title
;
 Modified-amino acid/peptide pyrimidine analogs: synthesis, structural
 characterization and DFT studies of N-(pyrimidyl)gabapentine and
 N-(pyrimidyl)baclofen
;
_journal_issue                   47
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              22053
_journal_page_last               22061
_journal_paper_doi               10.1039/D1NJ04639J
_journal_volume                  45
_journal_year                    2021
_chemical_formula_moiety         'C13 H19 N3 O2'
_chemical_formula_sum            'C13 H19 N3 O2'
_chemical_formula_weight         249.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-11-23
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2021-09-01 deposited with the CCDC.	2021-10-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.168(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.6291(18)
_cell_length_b                   7.1628(8)
_cell_length_c                   10.9025(11)
_cell_measurement_reflns_used    8997
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      68.223
_cell_measurement_theta_min      6.731
_cell_volume                     1297.7(2)
_computing_cell_refinement       'Bruker Apex3, 2016'
_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      293.15
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker 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  0.0576
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            28675
_diffrn_reflns_point_group_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.340
_diffrn_reflns_theta_min         6.178
_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    0.711
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.3312
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1658 before and 0.1036 after correction.
The Ratio of minimum to maximum transmission is 0.4398.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_description       plate
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.491
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.112
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_extinction_coef       0.028(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         4547
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0629
_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^)+(0.1173P)^2^+0.0433P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1496
_refine_ls_wR_factor_ref         0.1505
_reflns_Friedel_coverage         0.918
_reflns_Friedel_fraction_full    0.920
_reflns_Friedel_fraction_max     0.915
_reflns_number_gt                4445
_reflns_number_total             4547
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj04639j2.cif
_cod_data_source_block           1_a_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7061023--7061024.cif.'
_cod_database_code               7061024
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.926
_shelx_estimated_absorpt_t_min   0.740
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.9(3)
 0.1(3)
2. 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
3.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B),
 C17(H17A,H17B), C18(H18A,H18B), C8'(H8'A,H8'B), C10'(H10C,H10D), C14'(H14C,
 H14D), C15'(H15C,H15D), C16'(H16C,H16D), C17'(H17C,H17D), C18'(H18C,H18D)
3.b Aromatic/amide H refined with riding coordinates:
 N7(H7), C4(H4), C5(H5), C6(H6), N7'(H7'), C4'(H4'), C5'(H5'), C6'(H6')
3.c Idealised tetrahedral OH refined as rotating group:
 O13(H13), O13'(H13')
;
_shelx_res_checksum              29802
_olex2_exptl_crystal_mounting_method
'cryoloop, covered with Parabar 10320 (formerly known as Paratone)'
_olex2_submission_special_instructions 'No special instructions were received'