#------------------------------------------------------------------------------
#$Date: 2023-03-04 20:16:40 +0200 (Sat, 04 Mar 2023) $
#$Revision: 281439 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/59/7245964.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_7245964
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         'C7 H9 N3 O2'
_chemical_formula_sum            'C7 H9 N3 O2'
_chemical_formula_weight         167.17
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yac'
_space_group_name_H-M_alt        'P 1 2/n 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                 92.480(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9457(6)
_cell_length_b                   9.3395(6)
_cell_length_c                   8.9601(6)
_cell_measurement_reflns_used    8319
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.30
_cell_measurement_theta_min      3.15
_cell_volume                     747.90(9)
_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      100.15
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.995
_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  0.0465
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            12672
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.315
_diffrn_reflns_theta_min         3.150
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.7253
_exptl_absorpt_correction_T_min  0.6907
_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    1.485
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.251
_exptl_crystal_size_mid          0.237
_exptl_crystal_size_min          0.212
_refine_diff_density_max         0.765
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     113
_refine_ls_number_reflns         1865
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0554
_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/[σ²(Fo²)+(0.0973P)²+0.4563P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1487
_refine_ls_wR_factor_ref         0.1524
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1699
_reflns_number_total             1865
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce01293f2.cif
_cod_data_source_block           32060301_0m
_cod_depositor_comments
'Adding full bibliography for 7245964--7245971.cif.'
_cod_database_code               7245964
_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.
;
_shelx_estimated_absorpt_t_max   0.977
_shelx_estimated_absorpt_t_min   0.972
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C4'(H4'), C5'(H5'), C6'(H6')
2.c Tetrahedral OH refined with riding coordinates:
 O1(H1)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, 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 0.08523(14) 0.30025(13) 0.33151(15) 0.0322(4) Uani 1 1 d . . . . .
H1 H 0.148819 0.260542 0.389511 0.039 Uiso 1 1 calc R U . . .
O2 O 0.18456(11) 0.49969(10) 0.43145(11) 0.0137(3) Uani 1 1 d . . . . .
C2 C 0.09634(15) 0.43804(15) 0.34505(15) 0.0126(3) Uani 1 1 d . . . . .
C3 C -0.01487(16) 0.51144(14) 0.23952(15) 0.0126(3) Uani 1 1 d . . . . .
H3A H -0.116636 0.482551 0.266715 0.015 Uiso 1 1 calc R U . . .
H3B H 0.000206 0.475065 0.137483 0.015 Uiso 1 1 calc R U . . .
C4 C -0.00937(15) 0.67381(15) 0.23468(15) 0.0128(3) Uani 1 1 d . . . . .
H4A H -0.035083 0.714320 0.332404 0.015 Uiso 1 1 calc R U . . .
H4B H 0.092191 0.706733 0.211358 0.015 Uiso 1 1 calc R U . . .
N5 N -0.11802(14) 0.71950(13) 0.11829(13) 0.0137(3) Uani 1 1 d . . . . .
H5 H -0.173(3) 0.650(3) 0.065(3) 0.036(6) Uiso 1 1 d . . . . .
N1' N -0.26113(13) 0.88003(13) -0.01758(13) 0.0119(3) Uani 1 1 d . . . . .
C2' C -0.15296(15) 0.85788(14) 0.09012(15) 0.0112(3) Uani 1 1 d . . . . .
N3' N -0.08129(13) 0.96185(14) 0.16707(13) 0.0127(3) Uani 1 1 d . . . . .
C4' C -0.12244(16) 1.09555(15) 0.13273(15) 0.0146(3) Uani 1 1 d . . . . .
H4' H -0.073155 1.171850 0.184850 0.018 Uiso 1 1 calc R U . . .
C5' C -0.23403(16) 1.12990(15) 0.02434(16) 0.0134(3) Uani 1 1 d . . . . .
H5' H -0.261962 1.226066 0.002718 0.016 Uiso 1 1 calc R U . . .
C6' C -0.30102(15) 1.01504(15) -0.04925(15) 0.0122(3) Uani 1 1 d . . . . .
H6' H -0.377262 1.032416 -0.124170 0.015 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 109.5 . . ?
O1 C2 C3 110.30(12) . . ?
O2 C2 O1 124.79(13) . . ?
O2 C2 C3 124.91(12) . . ?
C2 C3 H3A 108.1 . . ?
C2 C3 H3B 108.1 . . ?
C2 C3 C4 116.80(11) . . ?
H3A C3 H3B 107.3 . . ?
C4 C3 H3A 108.1 . . ?
C4 C3 H3B 108.1 . . ?
C3 C4 H4A 110.3 . . ?
C3 C4 H4B 110.3 . . ?
H4A C4 H4B 108.6 . . ?
N5 C4 C3 106.93(11) . . ?
N5 C4 H4A 110.3 . . ?
N5 C4 H4B 110.3 . . ?
C4 N5 H5 118.8(15) . . ?
C2' N5 C4 123.73(12) . . ?
C2' N5 H5 117.3(16) . . ?
C6' N1' C2' 118.14(12) . . ?
N5 C2' N1' 115.61(12) . . ?
N3' C2' N5 119.74(13) . . ?
N3' C2' N1' 124.65(13) . . ?
C4' N3' C2' 116.04(12) . . ?
N3' C4' H4' 118.1 . . ?
N3' C4' C5' 123.78(13) . . ?
C5' C4' H4' 118.1 . . ?
C4' C5' H5' 122.1 . . ?
C6' C5' C4' 115.76(13) . . ?
C6' C5' H5' 122.1 . . ?
N1' C6' C5' 121.62(13) . . ?
N1' C6' H6' 119.2 . . ?
C5' C6' H6' 119.2 . . ?
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 0.8400 . ?
O1 C2 1.2960(17) . ?
O2 C2 1.2251(17) . ?
C2 C3 1.5075(18) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.5179(19) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 N5 1.4583(17) . ?
N5 H5 0.93(3) . ?
N5 C2' 1.3509(17) . ?
N1' C2' 1.3526(18) . ?
N1' C6' 1.3375(17) . ?
C2' N3' 1.3384(18) . ?
N3' C4' 1.3340(19) . ?
C4' H4' 0.9500 . ?
C4' C5' 1.399(2) . ?
C5' H5' 0.9500 . ?
C5' C6' 1.3822(19) . ?
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' 0.84 1.73 2.5281(16) 156.8 4_666 yes
N5 H5 O2 0.93(3) 2.21(3) 3.1394(16) 175(2) 4_565 yes
C4' H4' O1 0.95 2.24 3.1611(18) 163.5 1_565 yes
C6' H6' N3' 0.95 2.56 3.4988(18) 171.3 4_575 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 -176.24(13) . . . . ?
O2 C2 C3 C4 3.8(2) . . . . ?
C2 C3 C4 N5 175.87(11) . . . . ?
C3 C4 N5 C2' 174.41(12) . . . . ?
C4 N5 C2' N1' -177.14(12) . . . . ?
C4 N5 C2' N3' 3.0(2) . . . . ?
N5 C2' N3' C4' -179.91(12) . . . . ?
N1' C2' N3' C4' 0.22(19) . . . . ?
C2' N1' C6' C5' 0.4(2) . . . . ?
C2' N3' C4' C5' 0.5(2) . . . . ?
N3' C4' C5' C6' -0.7(2) . . . . ?
C4' C5' C6' N1' 0.21(19) . . . . ?
C6' N1' C2' N5 179.48(11) . . . . ?
C6' N1' C2' N3' -0.6(2) . . . . ?
