#------------------------------------------------------------------------------
#$Date: 2025-11-29 20:06:04 +0100 (Sat 29 de Nov de 2025) $
#$Revision: 303682 $
#$URL: svn://www.crystallography.net/cod/cif/7/25/09/7250985.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_7250985
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         'C6 H6 Br N3 O'
_chemical_formula_sum            'C6 H6 Br N3 O'
_chemical_formula_weight         216.05
_chemical_melting_point          506.0(10)
_chemical_name_systematic        N-(5-bromopyrimidin-2-yl)acetamide
_space_group_crystal_system      orthorhombic
_space_group_IT_number           66
_space_group_name_Hall           '-C 2 2c'
_space_group_name_H-M_alt        'C c c m'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-09-18
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.8524(2)
_cell_length_b                   18.7728(2)
_cell_length_c                   6.66220(10)
_cell_measurement_reflns_used    3859
_cell_measurement_temperature    210.00(10)
_cell_measurement_theta_max      79.9120
_cell_measurement_theta_min      4.4030
_cell_volume                     1482.36(4)
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      210.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -116.00 -89.00   0.50    0.20    --  -49.82-125.00 150.00   54
  2  ω   -111.00 -80.00   0.50    0.20    --  -49.82-125.00 -88.00   62
  3  ω   -119.00 -94.00   0.50    0.20    --  -49.82-125.00-180.00   50
  4  ω    -19.00  23.00   0.50    0.20    --  -49.82  19.00 -90.00   84
  5  ω    -55.00 -18.00   0.50    1.00    --  -90.00  49.00 119.00   74
  6  ω   -121.00 -40.00   0.50    0.20    --  -49.82 -49.00 -27.00  162
  7  ω     41.00  93.00   0.50    1.00    --  111.50 -77.00 120.00  104
  8  ω     60.00  90.00   0.50    1.00    --  111.50 -72.00 152.00   60
  9  ω     41.00  66.00   0.50    1.00    --  111.50 -61.00  90.00   50
 10  ω     49.00  98.00   0.50    1.00    --  111.50 -77.00  60.00   98
 11  ω     52.00 103.00   0.50    1.00    --  111.50 -77.00   0.00  102
 12  ω     45.00  70.00   0.50    1.00    --  111.50 -77.00-150.00   50
 13  ω     67.00 100.00   0.50    1.00    --  111.50 -94.00 -60.00   66
 14  ω     71.00  97.00   0.50    1.00    --  111.50-146.00 104.00   52
 15  ω     43.00 111.00   0.50    1.00    --  111.50-125.00 -88.00  136
 16  ω     96.00 122.00   0.50    1.00    --  111.50   0.00   0.00   52
 17  ω    123.00 159.00   0.50    1.00    --  111.50   0.00   0.00   72
 18  ω    115.00 173.00   0.50    1.00    --  111.50  15.00  30.00  116
 19  ω     41.00  71.00   0.50    1.00    --  111.50   0.00   0.00   60
 20  ω    109.00 135.00   0.50    1.00    --  111.50  30.00-120.00   52
 21  ω     93.00 158.00   0.50    1.00    --  111.50  72.00 -77.00  130
 22  ω    124.00 173.00   0.50    1.00    --  111.50 125.00 -30.00   98
 23  ω    151.00 178.00   0.50    1.00    --  111.50 125.00  30.00   54
 24  ω    116.00 142.00   0.50    1.00    --  111.50 125.00  30.00   52
;
_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      -0.0837178000
_diffrn_orient_matrix_UB_12      0.0342554000
_diffrn_orient_matrix_UB_13      -0.1482212000
_diffrn_orient_matrix_UB_21      0.0989256000
_diffrn_orient_matrix_UB_22      0.0354939000
_diffrn_orient_matrix_UB_23      -0.1118324000
_diffrn_orient_matrix_UB_31      0.0098639000
_diffrn_orient_matrix_UB_32      -0.0655819000
_diffrn_orient_matrix_UB_33      -0.1378559000
_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  0.0291
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            4747
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.935
_diffrn_reflns_theta_min         4.412
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    7.106
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67335
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.100a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.936
_exptl_crystal_description       plate
_exptl_crystal_F_000             848
_exptl_crystal_recrystallization_method 'crystallized from acetone and methanol'
_exptl_crystal_size_max          0.154
_exptl_crystal_size_mid          0.078
_exptl_crystal_size_min          0.033
_refine_diff_density_max         0.459
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     71
_refine_ls_number_reflns         890
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.143
_refine_ls_R_factor_all          0.0264
_refine_ls_R_factor_gt           0.0259
_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)+(0.0417P)²+1.5285P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0718
_refine_ls_wR_factor_ref         0.0723
_reflns_Friedel_coverage         0.000
_reflns_number_gt                863
_reflns_number_total             890
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5ce00839e2.cif
_cod_data_source_block           exp_859_auto
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '505-507' was changed to
'506.0(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               7250985
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C6H6Br1N3O
_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
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H10A(0.5) H10B(0.5) H10C(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5)
3.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_shelx_res_file
;
TITL exp_859_auto_a.res in Cccm
    exp_859_auto.res
    created by SHELXL-2018/3 at 16:35:25 on 18-Sep-2024
REM Old TITL exp_859_auto in Ccc2
REM SHELXT solution in Cccm: R1 0.152, Rweak 0.003, Alpha 0.023
REM <I/s> 0.945 for 62 systematic absences, Orientation as input
REM Formula found by SHELXT: C10 N6 O Br
CELL 1.54184 11.8524 18.7728 6.6622 90 90 90
ZERR 8 0.0002 0.0002 0.0001 0 0 0
LATT 7
SYMM -X,-Y,+Z
SYMM -X,+Y,0.5-Z
SYMM +X,-Y,0.5-Z
SFAC C H Br N O
UNIT 48 48 8 24 8
EQIV $1 1-X,1-Y,1-Z

L.S. 8
PLAN  6
TEMP -63
HTAB N7 N2_$1
BOND
HTAB
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\exp_859_auto.hkl">
REM </olex2.extras>

WGHT    0.041700    1.528500
FVAR       0.17559
C1    1    0.604103    0.400351    0.500000    10.50000    0.02621    0.01947 =
         0.03659    0.00000    0.00000   -0.00184
BR1   3    0.405089    0.193742    0.500000    10.50000    0.02857    0.02113 =
         0.05985    0.00000    0.00000   -0.00530
N2    4    0.491006    0.405771    0.500000    10.50000    0.02657    0.01818 =
         0.04131    0.00000    0.00000    0.00060
H7    2    0.612467    0.501046    0.500000    10.50000    0.02560
C3    1    0.432680    0.344863    0.500000    10.50000    0.02363    0.02401 =
         0.04152    0.00000    0.00000   -0.00050
AFIX  43
H3    2    0.353402    0.346257    0.500000    10.50000   -1.20000
AFIX   0
C4    1    0.487534    0.279636    0.500000    10.50000    0.02918    0.02045 =
         0.04041    0.00000    0.00000   -0.00427
C5    1    0.603746    0.279571    0.500000    10.50000    0.02637    0.01911 =
         0.04734    0.00000    0.00000    0.00031
AFIX  43
H5    2    0.642046    0.235725    0.500000    10.50000   -1.20000
AFIX   0
N6    4    0.663827    0.339818    0.500000    10.50000    0.02409    0.02048 =
         0.04653    0.00000    0.00000   -0.00130
N7    4    0.657646    0.465772    0.500000    10.50000    0.02650    0.01790 =
         0.05177    0.00000    0.00000    0.00066
C8    1    0.770099    0.485720    0.500000    10.50000    0.02725    0.02380 =
         0.04868    0.00000    0.00000   -0.00366
O9    5    0.790296    0.549304    0.500000    10.50000    0.03360    0.02253 =
         0.08157    0.00000    0.00000   -0.00681
C10   1    0.860757    0.430547    0.500000    10.50000    0.02579    0.02745 =
         0.07815    0.00000    0.00000   -0.00135
PART -1
AFIX 137
H10A  2    0.862692    0.406996    0.629549    10.50000   -1.50000
H10B  2    0.933017    0.453059    0.474534    10.50000   -1.50000
H10C  2    0.845485    0.395726    0.395917    10.50000   -1.50000
AFIX   0
HKLF 4




REM  exp_859_auto_a.res in Cccm
REM wR2 = 0.0723, GooF = S = 1.143, Restrained GooF = 1.143 for all data
REM R1 = 0.0259 for 863 Fo > 4sig(Fo) and 0.0264 for all 890 data
REM 71 parameters refined using 0 restraints

END

WGHT      0.0417      1.5285

REM Instructions for potential hydrogen bonds
HTAB N7 N2_$1
HTAB C3 O9_$1

REM Highest difference peak  0.459,  deepest hole -0.473,  1-sigma level  0.077
Q1    1   0.3995  0.1955  0.6535  11.00000  0.05    0.46
Q2    1   0.4590  0.3071  0.5000  10.50000  0.05    0.33
Q3    1   0.7122  0.4689  0.5000  10.50000  0.05    0.26
Q4    1   0.6369  0.3132  0.5000  10.50000  0.05    0.25
Q5    1   0.5365  0.2758  0.5000  10.50000  0.05    0.24
Q6    1   0.8136  0.4606  0.5000  10.50000  0.05    0.21
;
_shelx_res_checksum              85463
_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 1.374
_oxdiff_exptl_absorpt_empirical_full_min 0.711
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x, y, -z+1/2'
'x, -y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, 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, -y, z-1/2'
'-x, y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, y+1/2, -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 0.6041(2) 0.40035(15) 0.500000 0.0274(5) Uani 1 2 d S T P . .
Br1 Br 0.40509(2) 0.19374(2) 0.500000 0.03652(16) Uani 1 2 d S T P . .
N2 N 0.4910(2) 0.40577(12) 0.500000 0.0287(5) Uani 1 2 d S T P . .
H7 H 0.612(3) 0.501(2) 0.500000 0.026(8) Uiso 1 2 d S . P . .
C3 C 0.4327(2) 0.34486(15) 0.500000 0.0297(5) Uani 1 2 d S T P . .
H3 H 0.353402 0.346257 0.500000 0.036 Uiso 1 2 calc R U P . .
C4 C 0.4875(2) 0.27964(14) 0.500000 0.0300(5) Uani 1 2 d S T P . .
C5 C 0.6037(2) 0.27957(15) 0.500000 0.0309(6) Uani 1 2 d S T P . .
H5 H 0.642046 0.235725 0.500000 0.037 Uiso 1 2 calc R U P . .
N6 N 0.66383(19) 0.33982(12) 0.500000 0.0304(5) Uani 1 2 d S T P . .
N7 N 0.6576(2) 0.46577(13) 0.500000 0.0321(5) Uani 1 2 d S T P . .
C8 C 0.7701(2) 0.48572(15) 0.500000 0.0332(6) Uani 1 2 d S T P . .
O9 O 0.7903(2) 0.54930(12) 0.500000 0.0459(6) Uani 1 2 d S T P . .
C10 C 0.8608(3) 0.43055(17) 0.500000 0.0438(8) Uani 1 2 d S T P . .
H10A H 0.862692 0.406996 0.629549 0.066 Uiso 0.5 1 calc R U P A -1
H10B H 0.933017 0.453059 0.474534 0.066 Uiso 0.5 1 calc R U P A -1
H10C H 0.845485 0.395726 0.395917 0.066 Uiso 0.5 1 calc R U P A -1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0262(12) 0.0195(12) 0.0366(13) 0.000 0.000 -0.0018(9)
Br1 0.0286(2) 0.0211(2) 0.0598(3) 0.000 0.000 -0.00530(9)
N2 0.0266(11) 0.0182(9) 0.0413(11) 0.000 0.000 0.0006(8)
C3 0.0236(11) 0.0240(13) 0.0415(13) 0.000 0.000 -0.0005(10)
C4 0.0292(13) 0.0205(11) 0.0404(13) 0.000 0.000 -0.0043(11)
C5 0.0264(13) 0.0191(13) 0.0473(16) 0.000 0.000 0.0003(10)
N6 0.0241(11) 0.0205(11) 0.0465(12) 0.000 0.000 -0.0013(9)
N7 0.0265(12) 0.0179(10) 0.0518(13) 0.000 0.000 0.0007(9)
C8 0.0272(12) 0.0238(13) 0.0487(15) 0.000 0.000 -0.0037(10)
O9 0.0336(12) 0.0225(10) 0.0816(17) 0.000 0.000 -0.0068(8)
C10 0.0258(13) 0.0274(14) 0.078(2) 0.000 0.000 -0.0014(11)
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'
Br Br -0.6763 1.2805 '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_
_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 N7 113.0(2) . . ?
N6 C1 N2 126.3(2) . . ?
N6 C1 N7 120.8(2) . . ?
C3 N2 C1 116.8(2) . . ?
N2 C3 C4 120.9(3) . . ?
C3 C4 Br1 120.8(2) . . ?
C5 C4 Br1 121.2(2) . . ?
C5 C4 C3 118.0(3) . . ?
N6 C5 C4 122.1(3) . . ?
C5 N6 C1 115.9(2) . . ?
C1 N7 C8 133.0(3) . . ?
N7 C8 C10 120.4(3) . . ?
O9 C8 N7 117.0(3) . . ?
O9 C8 C10 122.6(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 1.344(4) . ?
C1 N6 1.339(4) . ?
C1 N7 1.382(4) . ?
Br1 C4 1.885(3) . ?
N2 C3 1.336(4) . ?
C3 C4 1.386(4) . ?
C4 C5 1.377(4) . ?
C5 N6 1.337(4) . ?
N7 C8 1.384(4) . ?
C8 O9 1.217(4) . ?
C8 C10 1.492(4) . ?
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 N2 0.85(4) 2.14(4) 2.987(3) 176(3) 9_666 yes
