#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:31:46 +0200 (vie 13 de oct de 2017) $
#$Revision: 201979 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/37/2233704.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_2233704
loop_
_publ_author_name
'van Albada, Gerard A.'
'Ghazzali, Mohamed'
'Al-Farhan, Khalid'
'Reedijk, Jan'
_publ_section_title
;
 2-Chloropyrimidin-4-amine
;
_journal_coeditor_code           ZJ2047
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o302
_journal_paper_doi               10.1107/S1600536811055863
_journal_volume                  68
_journal_year                    2012
_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_name_systematic
;
2-Chloropyrimidin-4-amine
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 100.886(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   3.83162(19)
_cell_length_b                   11.8651(7)
_cell_length_c                   12.7608(7)
_cell_measurement_reflns_used    342
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.3
_cell_volume                     569.70(5)
_computing_cell_refinement       'CrystalClear (Rigaku, 2007)'
_computing_data_collection       'CrystalClear (Rigaku, 2007)'
_computing_data_reduction        'CrystalClear (Rigaku, 2007)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2007)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_sigmaI/netI    0.0224
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9506
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.25
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.551
_exptl_absorpt_correction_T_max  0.8877
_exptl_absorpt_correction_T_min  0.8396
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.272
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         1296
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.136
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0349
_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)+(0.0422P)²+0.0697P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0823
_refine_ls_wR_factor_ref         0.0915
_reflns_number_gt                962
_reflns_number_total             1296
_reflns_threshold_expression     I>2sigma(I)
_iucr_refine_instructions_details
;
TITL 1 in P21/c
CELL  0.71075 3.83162 11.86513 12.76084 90.000 100.886 90.000
ZERR  4 0.00019 0.00066 0.00073 0.000 0.002 0.000
LATT 1
SYMM    -X, .50+Y, .50-Z
SFAC C H N CL
UNIT 16 16 12 4
L.S. 50
BOND $H
ACTA
EQIV $1_-x,1-y,1-z
EQIV $2_x,1/2-y,1/2+z
HTAB N2 N3_$1
HTAB N2 N1_$2
DFIX 0.91 0.02 N2 H2A N2 H2B
FMAP 2
PLAN 10
TEMP 20.0
SIZE 0.400 0.200 0.200! COLORLESS BLOCK
WGHT    0.042200    0.069700
FVAR       0.51672   0.00000
CL1   4    0.058137    0.438673    0.208981    11.00000    0.07180    0.06650 =
         0.03787    0.00597    0.01134    0.00034
N1    3    0.342523    0.256218    0.299872    11.00000    0.05700    0.05015 =
         0.04466   -0.01033    0.01431    0.00053
N2    3    0.211240    0.372618    0.591660    11.00000    0.07753    0.04555 =
         0.03452    0.00068    0.01296    0.00790
H2B   2    0.277205    0.333978    0.650395    11.00000    0.06514
H2A   2    0.102632    0.439470    0.595935    11.00000    0.06122
C2    1    0.203525    0.352941    0.320438    11.00000    0.04309    0.04561 =
         0.03788   -0.00453    0.01012   -0.00552
N3    3    0.153044    0.396725    0.411033    11.00000    0.04963    0.03799 =
         0.03569   -0.00191    0.01123   -0.00096
C4    1    0.261207    0.332271    0.499097    11.00000    0.04391    0.03951 =
         0.03724   -0.00128    0.00919   -0.00342
C5    1    0.417666    0.226158    0.488260    11.00000    0.05330    0.04285 =
         0.04717    0.00275    0.00753    0.00474
AFIX  43
H5    2    0.496088    0.180611    0.547326    11.00000   -1.20000
AFIX   0
C6    1    0.449521    0.193099    0.389372    11.00000    0.05501    0.04419 =
         0.06102   -0.00917    0.01316    0.00466
AFIX  43
H6    2    0.550590    0.123011    0.381825    11.00000   -1.20000
HKLF 4
REM   jr242 in P21/c
REM R1 =  0.0349 for    962 Fo > 4sig(Fo)  and  0.0496 for all   1296 data
REM     82 parameters refined using      2 restraints
END
WGHT      0.0415      0.0727
REM Highest difference peak  0.168,  deepest hole -0.272,  1-sigma level  0.047
Q1    1   0.5117  0.2098  0.5177  11.00000  0.05    0.17
Q2    1   0.1435  0.4794  0.4233  11.00000  0.05    0.17
Q3    1   0.3953  0.2847  0.5035  11.00000  0.05    0.16
Q4    1  -0.2878  0.3914  0.1801  11.00000  0.05    0.15
Q5    1   0.4669  0.4344  0.2715  11.00000  0.05    0.15
Q6    1   0.7970  0.1646  0.3544  11.00000  0.05    0.14
Q7    1  -0.1734  0.4322  0.3742  11.00000  0.05    0.14
Q8    1   0.8359  0.2400  0.6400  11.00000  0.05    0.14
Q9    1   0.5896  0.2440  0.6696  11.00000  0.05    0.14
Q10   1  -0.0514  0.3751  0.7349  11.00000  0.05    0.14
;
_cod_data_source_file            zj2047.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2233704
_cod_database_fobs_code          2233704
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_symmetry_multiplicity
Cl Cl1 0.05814(13) 0.43867(4) 0.20898(3) 0.0586(2) Uani d . 1 1
N N1 0.3425(4) 0.25622(13) 0.29987(11) 0.0500(4) Uani d . 1 1
N N2 0.2112(5) 0.37262(14) 0.59166(12) 0.0522(4) Uani d D 1 1
H H2B 0.277(5) 0.3340(17) 0.6504(14) 0.065(6) Uiso d D 1 1
H H2A 0.103(5) 0.4395(14) 0.5959(17) 0.061(6) Uiso d D 1 1
C C2 0.2035(4) 0.35294(14) 0.32044(13) 0.0419(4) Uani d . 1 1
N N3 0.1530(4) 0.39673(11) 0.41103(10) 0.0407(3) Uani d . 1 1
C C4 0.2612(4) 0.33227(13) 0.49910(12) 0.0400(4) Uani d . 1 1
C C5 0.4177(5) 0.22616(15) 0.48826(14) 0.0480(4) Uani d . 1 1
H H5 0.4961 0.1806 0.5473 0.058 Uiso calc R 1 1
C C6 0.4495(5) 0.19310(16) 0.38937(16) 0.0531(5) Uani d . 1 1
H H6 0.5506 0.1230 0.3818 0.064 Uiso calc R 1 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
Cl1 0.0718(4) 0.0665(4) 0.0379(3) 0.0003(2) 0.0113(2) 0.0060(2)
N1 0.0570(9) 0.0502(9) 0.0447(9) 0.0005(7) 0.0143(7) -0.0103(7)
N2 0.0775(11) 0.0455(9) 0.0345(8) 0.0079(8) 0.0130(7) 0.0007(7)
C2 0.0431(9) 0.0456(9) 0.0379(9) -0.0055(7) 0.0101(7) -0.0045(7)
N3 0.0496(8) 0.0380(7) 0.0357(7) -0.0010(6) 0.0112(6) -0.0019(6)
C4 0.0439(9) 0.0395(9) 0.0372(8) -0.0034(7) 0.0092(7) -0.0013(7)
C5 0.0533(10) 0.0429(10) 0.0472(10) 0.0047(8) 0.0075(8) 0.0027(8)
C6 0.0550(11) 0.0442(10) 0.0610(12) 0.0047(8) 0.0132(9) -0.0092(9)
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
C2 N1 C6 112.47(15)
C4 N2 H2B 120.6(14)
C4 N2 H2A 121.3(14)
H2B N2 H2A 118(2)
N1 C2 N3 130.85(16)
N1 C2 Cl1 115.10(12)
N3 C2 Cl1 114.05(13)
C2 N3 C4 115.64(14)
N2 C4 N3 117.56(15)
N2 C4 C5 123.11(16)
N3 C4 C5 119.33(15)
C6 C5 C4 117.77(16)
C6 C5 H5 121.1
C4 C5 H5 121.1
C5 C6 N1 123.94(17)
C5 C6 H6 118.0
N1 C6 H6 118.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C2 1.7518(17)
N1 C2 1.312(2)
N1 C6 1.363(2)
N2 C4 1.322(2)
N2 H2B 0.874(15)
N2 H2A 0.902(16)
C2 N3 1.315(2)
N3 C4 1.358(2)
C4 C5 1.412(2)
C5 C6 1.349(2)
C5 H5 0.9300
C6 H6 0.9300
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 N3 3_566 0.902(16) 2.171(16) 3.069(2) 174.0(19)
N2 H2B N1 4_566 0.874(15) 2.160(16) 3.024(2) 169.5(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 306656
