#------------------------------------------------------------------------------
#$Date: 2025-11-29 20:06:04 +0100 (Sat 29 de Nov de 2025) $
#$Revision: 303682 $
#$URL: svn://www.crystallography.net/cod/cif/7/25/09/7250990.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_7250990
loop_
_publ_author_name
'Marasinghe, Aloka A.'
'Averkiev, Boris B.'
'Aakeröy, Christer B.'
_publ_section_title
;
 Examining intermolecular interactions in crystal structures of
 amide-substituted 2-aminopyrimidine derivatives
;
_journal_issue                   43
_journal_name_full               CrystEngComm
_journal_page_first              7000
_journal_page_last               7011
_journal_paper_doi               10.1039/D5CE00839E
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C7 H9 N3 O'
_chemical_formula_sum            'C7 H9 N3 O'
_chemical_formula_weight         151.17
_chemical_melting_point          400.0(10)
_chemical_name_systematic        N-(pyrimidin-2-yl)propionamide
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-I 2y'
_space_group_name_H-M_alt        'I 1 2/m 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-12-16
_audit_creation_method
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2025-08-25 deposited with the CCDC.	2025-10-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.060(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4300(16)
_cell_length_b                   6.8202(14)
_cell_length_c                   12.068(2)
_cell_measurement_reflns_used    2050
_cell_measurement_temperature    294.20(10)
_cell_measurement_theta_max      71.4440
_cell_measurement_theta_min      5.4510
_cell_volume                     768.5(2)
_computing_cell_refinement       'CrysAlisPro 1.171.43.100a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.43.100a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.100a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.20(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00   6.00   0.50    0.70    --  -48.94 103.00-133.00  160
  2  ω     15.00  70.00   0.50    0.70    --   48.94-103.00 125.00  110
  3  ω    -81.00 -50.00   0.50    3.00    --  -90.00 103.00-133.00   62
  4  ω   -156.00 -84.00   0.50    3.00    --  -90.00-103.00 125.00  144
  5  ω    110.00 168.00   0.50    3.00    --  111.50 103.00-133.00  116
  6  ω     55.00 107.00   0.50    3.00    --  111.50-103.00 125.00  104
  7  ω   -116.00 -79.00   0.50    0.70    --  -48.94-125.00  30.00   74
  8  ω   -117.00 -85.00   0.50    0.70    --  -48.94-125.00-180.00   64
  9  ω   -109.00 -38.00   0.50    0.70    --  -48.94 -77.00 120.00  142
 10  ω   -116.00 -78.00   0.50    0.70    --  -48.94-125.00 -60.00   76
 11  ω    -20.00  16.00   0.50    0.70    --   48.94 -19.00 120.00   72
 12  ω   -160.00 -85.00   0.50    3.00    --  -90.00 -30.00-180.00  150
 13  ω   -161.00-103.00   0.50    3.00    --  -90.00 -45.00 150.00  116
 14  ω     96.00 173.00   0.50    3.00    --  111.50 125.00-180.00  154
 15  ω     57.00 105.00   0.50    3.00    --  111.50 -94.00 150.00   96
 16  ω     43.00 104.00   0.50    3.00    --  111.50 -77.00 -90.00  122
 17  ω    108.00 147.00   0.50    3.00    --  111.50  45.00-180.00   78
 18  ω     97.00 165.00   0.50    3.00    --  111.50 125.00 -90.00  136
 19  ω     56.00  94.00   0.50    3.00    --  111.50 -94.00-150.00   76
 20  ω     68.00 100.00   0.50    3.00    --  111.50 -94.00-180.00   64
 21  ω     64.00  98.00   0.50    3.00    --  111.50 -77.00-150.00   68
 22  ω     49.00  98.00   0.50    3.00    --  111.50 -94.00 -90.00   98
 23  ω     41.00  70.00   0.50    3.00    --  111.50 -61.00-120.00   58
 24  ω    113.00 171.00   0.50    3.00    --  111.50  30.00  30.00  116
 25  ω     43.00  85.00   0.50    3.00    --  111.50 -77.00 -60.00   84
 26  ω     52.00 109.00   0.50    3.00    --  111.50-125.00-150.00  114
 27  ω    105.00 152.00   0.50    3.00    --  111.50  15.00  30.00   94
 28  ω   -129.00-103.00   0.50    3.00    --  -90.00 -93.00  22.00   52
 29  ω   -110.00 -84.00   0.50    0.70    --  -49.69 -57.00   0.00   52
 30  ω    -86.00 -48.00   0.50    0.70    --  -49.69 -19.00-150.00   76
 31  ω   -122.00 -86.00   0.50    0.70    --  -49.69 -19.00   0.00   72
 32  ω    -66.00 -40.00   0.50    0.70    --  -49.69 -57.00   0.00   52
 33  ω    -67.00 -42.00   0.50    0.70    --  -49.69 -19.00   0.00   50
 34  ω     86.00 116.00   0.50    0.70    --   49.69  77.00  90.00   60
 35  ω     31.00  57.00   0.50    0.70    --   49.69  77.00 -30.00   52
 36  ω     31.00  57.00   0.50    0.70    --   49.69  77.00  90.00   52
 37  ω     31.00  57.00   0.50    0.70    --   49.69  77.00 -60.00   52
 38  ω     61.00  89.00   0.50    0.70    --   49.69  77.00 -90.00   56
 39  ω     30.00  84.00   0.50    0.70    --   49.69  77.00-150.00  108
 40  ω     30.00  74.00   0.50    0.70    --   49.69  77.00 150.00   88
 41  ω     37.00  67.00   0.50    0.70    --   49.69  57.00   0.00   60
 42  ω     29.00  55.00   0.50    0.70    --   49.69  77.00 120.00   52
 43  ω     29.00  55.00   0.50    0.70    --   49.69  77.00  30.00   52
 44  ω     49.00  84.00   0.50    0.70    --   49.69  38.00 120.00   70
 45  ω     29.00  59.00   0.50    0.70    --   49.69  77.00 -90.00   60
 46  ω    -61.00 -35.00   0.50    3.00    --  -90.00  57.00-150.00   52
 47  ω   -139.00-113.00   0.50    3.00    --  -90.00 -59.00  88.57   52
 48  ω    -66.00 -41.00   0.50    3.00    --  -90.00  57.00-180.00   50
 49  ω   -125.00 -75.00   0.50    3.00    --  -90.00 -62.00 -71.67  100
 50  ω   -123.00 -98.00   0.50    3.00    --  -90.00 -47.00 -49.83   50
 51  ω   -103.00 -70.00   0.50    3.00    --  -90.00 -77.00  60.00   66
 52  ω   -118.00 -80.00   0.50    3.00    --  -90.00 -53.00 -14.88   76
 53  ω   -139.00-108.00   0.50    3.00    --  -90.00 -71.00  68.56   62
 54  ω    -99.00 -74.00   0.50    3.00    --  -90.00 -71.00  68.56   50
 55  ω   -149.00-123.00   0.50    3.00    --  -90.00 -77.00 -90.00   52
 56  ω   -156.00-127.00   0.50    3.00    --  -90.00 -67.00 175.57   58
 57  ω   -131.00 -70.00   0.50    3.00    --  -90.00 -76.00 -39.17  122
 58  ω   -113.00 -69.00   0.50    3.00    --  -90.00 -77.00 -90.00   88
 59  ω   -107.00 -81.00   0.50    3.00    --  -90.00 -48.00  94.36   52
 60  ω    -94.00 -69.00   0.50    3.00    --  -90.00 -77.00   0.00   50
 61  ω   -100.00 -75.00   0.50    3.00    --  -90.00 -62.00-166.60   50
 62  ω   -115.00 -76.00   0.50    3.00    --  -90.00 -59.00-124.78   78
 63  ω   -155.00-129.00   0.50    3.00    --  -90.00 -62.00-166.60   52
 64  ω    -97.00 -71.00   0.50    3.00    --  -90.00 -77.00 120.00   52
 65  ω   -112.00 -81.00   0.50    3.00    --  -90.00 -52.00 137.13   62
 66  ω   -157.00-131.00   0.50    3.00    --  -90.00 -77.00  60.00   52
 67  ω    -98.00 -73.00   0.50    3.00    --  -90.00 -67.00 175.57   50
 68  ω   -105.00 -79.00   0.50    3.00    --  -90.00 -57.00 120.00   52
 69  ω    -96.00 -71.00   0.50    3.00    --  -90.00 -77.00-120.00   50
 70  ω   -160.00-124.00   0.50    3.00    --  -90.00 -52.00 137.13   72
 71  ω    -95.00 -70.00   0.50    3.00    --  -90.00 -76.00  85.52   50
 72  ω   -102.00 -74.00   0.50    3.00    --  -90.00 -74.00 -15.67   56
 73  ω    -96.00 -71.00   0.50    3.00    --  -90.00 -74.00 148.79   50
 74  ω    -95.00 -70.00   0.50    3.00    --  -90.00 -75.00 -68.91   50
 75  ω   -157.00-144.50   0.50    3.00    --  -90.00 -76.00  85.52   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0049277000
_diffrn_orient_matrix_UB_12      -0.2165696000
_diffrn_orient_matrix_UB_13      -0.0364243000
_diffrn_orient_matrix_UB_21      0.1583553000
_diffrn_orient_matrix_UB_22      0.0113105000
_diffrn_orient_matrix_UB_23      -0.0182484000
_diffrn_orient_matrix_UB_31      0.0466051000
_diffrn_orient_matrix_UB_32      -0.0626051000
_diffrn_orient_matrix_UB_33      0.1223269000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0599
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4507
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.219
_diffrn_reflns_theta_min         5.589
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.759
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.640
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.100a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_description       irregular
_exptl_crystal_F_000             320
_exptl_crystal_recrystallization_method 'crystallized from ethylacetate'
_exptl_crystal_size_max          0.187
_exptl_crystal_size_mid          0.132
_exptl_crystal_size_min          0.078
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     71
_refine_ls_number_reflns         756
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0615
_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)+(0.1328P)²+0.1580P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1712
_refine_ls_wR_factor_ref         0.1980
_reflns_Friedel_coverage         0.000
_reflns_number_gt                563
_reflns_number_total             756
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5ce00839e2.cif
_cod_data_source_block           exp_823a_autor
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '399-401' was changed to
'400.0(10)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7250982--7251002.cif.
;
_cod_database_code               7250990
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C7H9N3O1
_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   0.943
_shelx_estimated_absorpt_t_min   0.871
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H10A(0.5) H10B(0.5) H11A(0.5) H11B(0.5) H11C(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5)
3.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 7.587
_oxdiff_exptl_absorpt_empirical_full_min 0.436
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, -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
C1 C 0.6091(3) 0.500000 0.1789(2) 0.0592(8) Uani 1 2 d S T P . .
N2 N 0.6792(3) 0.500000 0.2827(2) 0.0673(8) Uani 1 2 d S T P . .
C3 C 0.8208(4) 0.500000 0.2918(3) 0.0691(9) Uani 1 2 d S T P . .
H3 H 0.872966 0.500000 0.363207 0.083 Uiso 1 2 calc R U P . .
C4 C 0.8944(3) 0.500000 0.2021(3) 0.0683(9) Uani 1 2 d S T P . .
H4 H 0.993953 0.500000 0.210534 0.082 Uiso 1 2 calc R U P . .
H7 H 0.421(4) 0.500000 0.088(3) 0.057(8) Uiso 1 2 d S . P . .
C5 C 0.8125(4) 0.500000 0.0986(3) 0.0720(10) Uani 1 2 d S T P . .
H5 H 0.858660 0.500000 0.035376 0.086 Uiso 1 2 calc R U P . .
N6 N 0.6705(3) 0.500000 0.0848(2) 0.0685(9) Uani 1 2 d S T P . .
N7 N 0.4618(3) 0.500000 0.1592(2) 0.0684(9) Uani 1 2 d S T P . .
C8 C 0.3559(3) 0.500000 0.2276(3) 0.0633(9) Uani 1 2 d S T P . .
O9 O 0.2325(2) 0.500000 0.18399(19) 0.0820(9) Uani 1 2 d S T P . .
C10 C 0.3962(4) 0.500000 0.3528(2) 0.0701(10) Uani 1 2 d S T P . .
H10A H 0.453969 0.614927 0.374750 0.084 Uiso 0.5 1 calc R U P . .
H10B H 0.453969 0.385073 0.374750 0.084 Uiso 0.5 1 calc R U P . .
C11 C 0.2667(4) 0.500000 0.4145(3) 0.0789(11) Uani 1 2 d S T P . .
H11A H 0.203984 0.605740 0.387563 0.118 Uiso 0.5 1 calc R U P A -1
H11B H 0.297424 0.516576 0.493246 0.118 Uiso 0.5 1 calc R U P A -1
H11C H 0.216647 0.377683 0.401885 0.118 Uiso 0.5 1 calc R U P A -1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3 -3 -1 0.0175
0 0 -1 0.0925
0 0 1 0.0787
-2 2 1 0.0535
3 2 -3 0.0655
-1 -1 3 0.0778
-3 -1 0 0.0747
3 1 1 0.0367
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
N2 C1 N6 125.3(3) . . ?
N2 C1 N7 121.2(3) . . ?
N6 C1 N7 113.5(3) . . ?
C3 N2 C1 116.1(3) . . ?
N2 C3 C4 123.5(3) . . ?
C3 C4 C5 116.0(3) . . ?
N6 C5 C4 123.0(3) . . ?
C5 N6 C1 116.1(3) . . ?
C1 N7 C8 133.9(3) . . ?
N7 C8 C10 119.9(3) . . ?
O9 C8 N7 118.2(3) . . ?
O9 C8 C10 121.9(3) . . ?
C8 C10 C11 112.7(3) . . ?
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
C1 N2 1.332(4) . ?
C1 N6 1.345(4) . ?
C1 N7 1.376(4) . ?
N2 C3 1.324(4) . ?
C3 C4 1.366(5) . ?
C4 C5 1.373(5) . ?
C5 N6 1.326(4) . ?
N7 C8 1.381(4) . ?
C8 O9 1.208(4) . ?
C8 C10 1.506(4) . ?
C10 C11 1.517(5) . ?
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
N7 H7 N6 0.90(3) 2.14(4) 3.032(4) 178(3) 5_665 yes
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
2.9933 -3.0055 -0.9990 0.6725 0.4582 0.2055
-0.0021 -0.0010 -1.0002 0.0367 0.0179 -0.1224
0.0021 0.0010 1.0002 -0.0367 -0.0179 0.1224
-1.9948 2.0040 0.9994 -0.4606 -0.3115 -0.0962
3.0039 1.9987 -3.0076 -0.3381 0.5532 -0.3530
-0.9982 -0.9980 3.0035 0.1116 -0.2242 0.3834
-3.0072 -1.0006 0.0054 0.2313 -0.4876 -0.0769
3.0092 1.0016 0.9948 -0.2680 0.4697 0.1992
