#------------------------------------------------------------------------------
#$Date: 2025-08-19 15:18:28 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301805 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/37/2223795.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2223795
loop_
_publ_author_name
'Wang, Bin'
'Lu, Ran-Zhe'
'Han, Lu-Na'
'Wei, Wen-Bin'
'Wang, Hai-Bo'
_publ_section_title
;
 5-Chloropyrimidin-2-amine
;
_journal_coeditor_code           HB5158
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2863
_journal_paper_doi               10.1107/S1600536809043645
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C4 H4 Cl N3'
_chemical_formula_moiety         'C4 H4 Cl N3'
_chemical_formula_sum            'C4 H4 Cl N3'
_chemical_formula_weight         129.55
_chemical_melting_point          506
_chemical_name_systematic
;
5-Chloropyrimidin-2-amine
;
_space_group_IT_number           64
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-C 2ac 2'
_symmetry_space_group_name_H-M   'C m c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.6380(15)
_cell_length_b                   8.2240(16)
_cell_length_c                   17.100(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      10
_cell_volume                     1074.1(4)
_computing_cell_refinement       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_av_sigmaI/netI    0.0217
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            1047
_diffrn_reflns_theta_full        25.26
_diffrn_reflns_theta_max         25.26
_diffrn_reflns_theta_min         2.38
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.585
_exptl_absorpt_correction_T_max  0.944
_exptl_absorpt_correction_T_min  0.844
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.218
_refine_ls_extinction_coef       0.025(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   0.920
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     44
_refine_ls_number_reflns         534
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.920
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0334
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.2000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1095
_refine_ls_wR_factor_ref         0.1159
_reflns_number_gt                462
_reflns_number_total             534
_reflns_threshold_expression     I>2Ĭ)
_cod_data_source_file            hb5158.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_Hall     '-C 2bc 2'
_cod_database_code               2223795
_cod_database_fobs_code          2223795
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y+1/2, z+1/2'
'-x, y+1/2, -z+1/2'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1, z+1/2'
'-x+1/2, y+1, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x, y-1/2, -z-1/2'
'x, -y-1/2, z-1/2'
'-x, y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, y, -z-1/2'
'x+1/2, -y, z-1/2'
'-x+1/2, y+1/2, z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl 0.5000 0.22728(9) 0.27440(4) 0.0527(4) Uani d S 1 . .
N N1 0.65713(16) -0.11849(18) 0.41923(8) 0.0360(5) Uani d . 1 . .
C C3 0.5000 -0.1761(3) 0.44284(14) 0.0319(6) Uani d S 1 . .
N N2 0.5000 -0.3014(3) 0.49308(15) 0.0432(7) Uani d S 1 . .
H H2A 0.6021 -0.3434 0.5099 0.052 Uiso d R 1 . .
C C2 0.6542(2) 0.0027(2) 0.36821(10) 0.0364(5) Uani d . 1 . .
H H2C 0.7598 0.0457 0.3507 0.044 Uiso calc R 1 . .
C C1 0.5000 0.0674(3) 0.34019(13) 0.0347(6) Uani d S 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_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Cl 0.0488(6) 0.0514(6) 0.0580(6) 0.000 0.000 0.0225(3)
N1 0.0258(9) 0.0398(9) 0.0424(9) -0.0007(6) 0.0004(5) 0.0045(6)
C3 0.0278(12) 0.0325(13) 0.0354(12) 0.000 0.000 -0.0039(11)
N2 0.0288(11) 0.0450(13) 0.0559(14) 0.000 0.000 0.0179(11)
C2 0.0296(10) 0.0379(10) 0.0418(9) -0.0033(7) 0.0032(7) 0.0013(7)
C1 0.0353(13) 0.0328(13) 0.0359(13) 0.000 0.000 0.0026(10)
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'
Cl Cl 0.1484 0.1585 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 N1 C3 . . 116.44(14) ?
N2 C3 N1 . 12_655 117.41(11) ?
N2 C3 N1 . . 117.41(11) ?
N1 C3 N1 12_655 . 125.2(2) ?
C3 N2 H2A . . 120.0 ?
N1 C2 C1 . . 122.25(15) ?
N1 C2 H2C . . 118.9 ?
C1 C2 H2C . . 118.9 ?
C2 C1 C2 . 12_655 117.4(2) ?
C2 C1 Cl . . 121.28(11) ?
C2 C1 Cl 12_655 . 121.28(11) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl C1 . 1.730(2) ?
N1 C2 . 1.325(2) ?
N1 C3 . 1.3519(18) ?
C3 N2 . 1.341(4) ?
C3 N1 12_655 1.3519(18) ?
N2 H2A . 0.9000 ?
C2 C1 . 1.378(2) ?
C2 H2C . 0.9300 ?
C1 C2 12_655 1.378(2) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N2 H2A N1 13_646 0.90 2.22 3.087(2) 161
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 N1 C3 N2 . . . . 178.5(2) ?
C2 N1 C3 N1 . . . 12_655 -0.8(4) ?
C3 N1 C2 C1 . . . . -0.1(3) ?
N1 C2 C1 C2 . . . 12_655 1.0(4) ?
N1 C2 C1 Cl . . . . 179.28(14) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 79479
