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_7061023
_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         'C14 H14 Cl N3 O2'
_chemical_formula_sum            'C14 H14 Cl N3 O2'
_chemical_formula_weight         291.73
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-10-21
_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                 101.152(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9144(5)
_cell_length_b                   8.5835(4)
_cell_length_c                   15.5150(6)
_cell_measurement_reflns_used    9970
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      72.188
_cell_measurement_theta_min      4.566
_cell_volume                     1426.06(11)
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_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  0.0369
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16820
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        66.590
_diffrn_reflns_theta_max         66.590
_diffrn_reflns_theta_min         4.566
_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    2.422
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5134
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1165 before and 0.0630 after correction.
The Ratio of minimum to maximum transmission is 0.6813.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2462
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0494
_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^)+(0.0723P)^2^+0.5573P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1347
_refine_ls_wR_factor_ref         0.1378
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2260
_reflns_number_total             2462
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj04639j2.cif
_cod_data_source_block           1_a
_cod_depositor_comments
'Adding full bibliography for 7061023--7061024.cif.'
_cod_database_code               7061023
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.760
_shelx_estimated_absorpt_t_min   0.389
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 N7(H7), C6(H6), C19(H19), C15(H15), C5(H5), C4(H4), C18(H18), C16(H16)
;
_shelx_res_checksum              67702
_olex2_exptl_crystal_mounting_method cryoloop
_olex2_submission_special_instructions 'No special instructions were received'