#------------------------------------------------------------------------------
#$Date: 2023-03-04 20:16:40 +0200 (Sat, 04 Mar 2023) $
#$Revision: 281439 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/59/7245967.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_7245967
loop_
_publ_author_name
'García-Raso, Angel'
'Terrón, Angel'
'Fiol, Juan J.'
'López-Zafra, Adela'
'Picó, Gemma'
'Vázquez-López, Ezequiel M.'
'Barceló-Oliver, Miquel'
'Frontera, Antonio'
_publ_section_title
;
 Synthesis, structural characterization and DFT study of
 N-(pyrimidyl)-ω-amino acids/peptide: β-alanine, γ-aminobutyric acid,
 5-aminovaleric acid, 6-aminohexanoic acid and glycylglycine
;
_journal_issue                   2
_journal_name_full               CrystEngComm
_journal_page_first              233
_journal_page_last               244
_journal_paper_doi               10.1039/D2CE01293F
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C10 H15 N3 O2'
_chemical_formula_sum            'C10 H15 N3 O2'
_chemical_formula_weight         209.25
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2022-11-14
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-11-14 deposited with the CCDC.	2022-11-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.643(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.7614(3)
_cell_length_b                   17.1948(7)
_cell_length_c                   9.2263(4)
_cell_measurement_reflns_used    8076
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.31
_cell_measurement_theta_min      2.55
_cell_volume                     1046.65(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_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    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            15512
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.374
_diffrn_reflns_theta_min         2.369
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7172
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.276
_exptl_crystal_size_mid          0.147
_exptl_crystal_size_min          0.085
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     144
_refine_ls_number_reflns         2609
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0369
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0508P)²+0.3666P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0964
_refine_ls_wR_factor_ref         0.1001
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2304
_reflns_number_total             2609
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce01293f2.cif
_cod_data_source_block           32061802_0m
_cod_depositor_comments
'Adding full bibliography for 7245964--7245971.cif.'
_cod_database_code               7245967
_shelx_shelxl_version_number     2019/1
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C4'(H4'), C5'(H5'), C6'(H6')
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
O1 O 1.15126(11) 0.65339(4) 0.39873(8) 0.01627(18) Uani 1 1 d . . . . .
H1 H 1.211(3) 0.6063(11) 0.374(2) 0.048(5) Uiso 1 1 d . . . . .
O2 O 1.37553(13) 0.70713(4) 0.28389(10) 0.0215(2) Uani 1 1 d . . . . .
C2 C 1.24147(15) 0.71378(6) 0.35271(11) 0.0138(2) Uani 1 1 d . . . . .
C3 C 1.17059(16) 0.79232(6) 0.39384(12) 0.0164(2) Uani 1 1 d . . . . .
H3A H 1.140652 0.824980 0.303310 0.020 Uiso 1 1 calc R U . . .
H3B H 1.283697 0.817293 0.464949 0.020 Uiso 1 1 calc R U . . .
C4 C 0.98517(15) 0.79240(6) 0.46190(11) 0.0136(2) Uani 1 1 d . . . . .
H4A H 1.009268 0.756788 0.548295 0.016 Uiso 1 1 calc R U . . .
H4B H 0.867380 0.772422 0.387939 0.016 Uiso 1 1 calc R U . . .
C5 C 0.93496(14) 0.87326(6) 0.51223(11) 0.0132(2) Uani 1 1 d . . . . .
H5A H 1.054335 0.894449 0.583025 0.016 Uiso 1 1 calc R U . . .
H5B H 0.903522 0.908430 0.425263 0.016 Uiso 1 1 calc R U . . .
C6 C 0.75467(15) 0.87045(6) 0.58638(11) 0.0138(2) Uani 1 1 d . . . . .
H6A H 0.634393 0.851323 0.513743 0.017 Uiso 1 1 calc R U . . .
H6B H 0.784032 0.833015 0.669857 0.017 Uiso 1 1 calc R U . . .
C7 C 0.70593(15) 0.94920(6) 0.64469(11) 0.0141(2) Uani 1 1 d . . . . .
H7A H 0.824073 0.968421 0.719268 0.017 Uiso 1 1 calc R U . . .
H7B H 0.675865 0.987166 0.562119 0.017 Uiso 1 1 calc R U . . .
N8 N 0.53111(13) 0.94162(5) 0.71228(10) 0.01434(19) Uani 1 1 d . . . . .
H8 H 0.490(2) 0.8950(9) 0.7303(17) 0.028(4) Uiso 1 1 d . . . . .
N1' N 0.30335(13) 0.98511(5) 0.84659(9) 0.01343(19) Uani 1 1 d . . . . .
C2' C 0.45537(14) 1.00157(6) 0.77622(11) 0.0119(2) Uani 1 1 d . . . . .
N3' N 0.53452(13) 1.07286(5) 0.76508(10) 0.01450(19) Uani 1 1 d . . . . .
C4' C 0.45585(16) 1.13072(6) 0.83068(12) 0.0161(2) Uani 1 1 d . . . . .
H4' H 0.507650 1.181710 0.824805 0.019 Uiso 1 1 calc R U . . .
C5' C 0.30241(16) 1.12034(6) 0.90699(12) 0.0163(2) Uani 1 1 d . . . . .
H5' H 0.249503 1.162322 0.953738 0.020 Uiso 1 1 calc R U . . .
C6' C 0.23118(15) 1.04521(6) 0.91087(11) 0.0156(2) Uani 1 1 d . . . . .
H6' H 0.125656 1.035832 0.961791 0.019 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 0.0000 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 H1 109.8(11) . . ?
O1 C2 C3 115.36(9) . . ?
O2 C2 O1 122.79(9) . . ?
O2 C2 C3 121.83(9) . . ?
C2 C3 H3A 108.2 . . ?
C2 C3 H3B 108.2 . . ?
C2 C3 C4 116.16(8) . . ?
H3A C3 H3B 107.4 . . ?
C4 C3 H3A 108.2 . . ?
C4 C3 H3B 108.2 . . ?
C3 C4 H4A 109.1 . . ?
C3 C4 H4B 109.1 . . ?
C3 C4 C5 112.63(8) . . ?
H4A C4 H4B 107.8 . . ?
C5 C4 H4A 109.1 . . ?
C5 C4 H4B 109.1 . . ?
C4 C5 H5A 109.4 . . ?
C4 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
C6 C5 C4 111.14(8) . . ?
C6 C5 H5A 109.4 . . ?
C6 C5 H5B 109.4 . . ?
C5 C6 H6A 109.0 . . ?
C5 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C7 C6 C5 112.81(8) . . ?
C7 C6 H6A 109.0 . . ?
C7 C6 H6B 109.0 . . ?
C6 C7 H7A 109.8 . . ?
C6 C7 H7B 109.8 . . ?
H7A C7 H7B 108.3 . . ?
N8 C7 C6 109.31(8) . . ?
N8 C7 H7A 109.8 . . ?
N8 C7 H7B 109.8 . . ?
C7 N8 H8 118.9(10) . . ?
C2' N8 C7 122.81(8) . . ?
C2' N8 H8 116.8(10) . . ?
C6' N1' C2' 116.02(9) . . ?
N8 C2' N1' 116.78(9) . . ?
N8 C2' N3' 117.87(9) . . ?
N3' C2' N1' 125.35(9) . . ?
C4' N3' C2' 116.00(9) . . ?
N3' C4' H4' 118.3 . . ?
N3' C4' C5' 123.44(9) . . ?
C5' C4' H4' 118.3 . . ?
C4' C5' H5' 122.0 . . ?
C6' C5' C4' 115.92(9) . . ?
C6' C5' H5' 122.0 . . ?
N1' C6' C5' 123.26(10) . . ?
N1' C6' H6' 118.4 . . ?
C5' C6' H6' 118.4 . . ?
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
O1 H1 0.956(18) . ?
O1 C2 1.3205(12) . ?
O2 C2 1.2206(13) . ?
C2 C3 1.5090(13) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.5201(14) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.5273(13) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.5236(13) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.5196(13) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 N8 1.4580(13) . ?
N8 H8 0.876(16) . ?
N8 C2' 1.3436(13) . ?
N1' C2' 1.3602(13) . ?
N1' C6' 1.3358(13) . ?
C2' N3' 1.3505(13) . ?
N3' C4' 1.3342(13) . ?
C4' H4' 0.9500 . ?
C4' C5' 1.3870(15) . ?
C5' H5' 0.9500 . ?
C5' C6' 1.3820(15) . ?
C6' H6' 0.9500 . ?
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
O1 H1 N1' 0.956(18) 1.729(19) 2.6790(11) 172.1(17) 4_675 yes
N8 H8 O2 0.876(16) 2.024(16) 2.8964(11) 174.0(14) 4_476 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
O1 C2 C3 C4 -8.75(13) . . . . ?
O2 C2 C3 C4 172.48(10) . . . . ?
C2 C3 C4 C5 175.08(9) . . . . ?
C3 C4 C5 C6 -177.31(8) . . . . ?
C4 C5 C6 C7 177.28(8) . . . . ?
C5 C6 C7 N8 179.42(8) . . . . ?
C6 C7 N8 C2' 178.64(9) . . . . ?
C7 N8 C2' N1' -174.36(9) . . . . ?
C7 N8 C2' N3' 5.99(15) . . . . ?
N8 C2' N3' C4' -179.68(9) . . . . ?
N1' C2' N3' C4' 0.70(15) . . . . ?
C2' N1' C6' C5' 0.52(15) . . . . ?
C2' N3' C4' C5' 0.19(15) . . . . ?
N3' C4' C5' C6' -0.63(16) . . . . ?
C4' C5' C6' N1' 0.25(16) . . . . ?
C6' N1' C2' N8 179.33(9) . . . . ?
C6' N1' C2' N3' -1.04(15) . . . . ?
