#------------------------------------------------------------------------------
#$Date: 2016-02-21 01:03:34 +0100 (dom 21 de feb de 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/37/2233707.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_2233707
loop_
_publ_author_name
'Johnson, Marcelle'
'Lemmerer, Andreas'
_publ_section_title
;
 3-Bromopyridin-2-amine
;
_journal_coeditor_code           ZJ2050
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o385
_journal_paper_doi               10.1107/S1600536811055541
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C5 H5 Br N2'
_chemical_formula_moiety         'C5 H5 Br N2'
_chemical_formula_sum            'C5 H5 Br N2'
_chemical_formula_weight         173.02
_chemical_name_systematic
;
3-Bromopyridin-2-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'
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 109.731(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.2179(6)
_cell_length_b                   4.0007(2)
_cell_length_c                   12.8451(6)
_cell_measurement_reflns_used    2888
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.31
_cell_measurement_theta_min      3.23
_cell_volume                     591.01(5)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker 2004)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg,
1999)
;
_computing_publication_material
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD area-detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0931
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5622
_diffrn_reflns_theta_full        27.98
_diffrn_reflns_theta_max         27.98
_diffrn_reflns_theta_min         1.77
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.836
_exptl_absorpt_correction_T_max  0.5782
_exptl_absorpt_correction_T_min  0.1313
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(XPREP; Bruker, 2004)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.945
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.09
_refine_diff_density_max         1.044
_refine_diff_density_min         -0.769
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     81
_refine_ls_number_reflns         1428
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_gt           0.034
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0479P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0821
_reflns_number_gt                1200
_reflns_number_total             1428
_reflns_threshold_expression     I>2sigma(I)
_iucr_refine_instructions_details
;
TITL 11a_MJ_a in P2(1)/c
CELL  0.71073  12.2179   4.0007  12.8451   90.000  109.731   90.000
ZERR     4.00   0.0006   0.0002   0.0006    0.000    0.003    0.000
LATT   1
SYMM  - X, 1/2 + Y, 1/2 - Z
SFAC  C    H    N    BR
UNIT  20   20   8    4
MERG   2
OMIT    -2.00  56.00
FMAP   2
PLAN    5
SIZE     0.09   0.40   0.50
EQIV $2 -x+2, -y+1, -z+1
HTAB N2 N1_$2
HTAB 3
HTAB
ACTA
BOND
BOND   $H
CONF
L.S.   4
TEMP  -100.00
WGHT    0.047900
FVAR       0.34416
MOLE    1
C2    1    0.818191    0.423548    0.492643    11.00000    0.03088    0.02938 =
         0.02531    0.00306    0.00840    0.00017
C3    1    0.704755    0.366790    0.491158    11.00000    0.02707    0.02556 =
         0.02385    0.00337    0.00386    0.00314
C4    1    0.670224    0.470351    0.577087    11.00000    0.02816    0.03306 =
         0.03195    0.00764    0.01066    0.00698
AFIX  43
H4    2    0.593405    0.428724    0.576319    11.00000   -1.20000
AFIX   0
C5    1    0.749857    0.637414    0.665311    11.00000    0.03589    0.03758 =
         0.02504    0.00363    0.01091    0.00586
AFIX  43
H5    2    0.729019    0.716758    0.725784    11.00000   -1.20000
AFIX   0
C6    1    0.860246    0.683280    0.661503    11.00000    0.03430    0.03666 =
         0.02726    0.00023    0.00791   -0.00101
AFIX  43
H6    2    0.915023    0.797616    0.721477    11.00000   -1.20000
AFIX   0
N1    3    0.895569    0.578144    0.579346    11.00000    0.02859    0.04082 =
         0.02658   -0.00221    0.00732   -0.00413
N2    3    0.854668    0.335875    0.407666    11.00000    0.03032    0.05677 =
         0.03093   -0.01203    0.01344   -0.01124
BR1   4    0.595568    0.156190    0.365986    11.00000    0.02548    0.03463 =
         0.03161   -0.00178    0.00396    0.00029
H2A   2    0.922918    0.345089    0.414675    11.00000    0.02974
H2B   2    0.819947    0.209810    0.361624    11.00000    0.04303
HKLF    4
REM  11a_MJ_a in P2(1)/c
REM R1 =  0.0340 for   1200 Fo > 4sig(Fo)  and  0.0408 for all   1428 data
REM     81 parameters refined using      0 restraints
END
WGHT      0.0479      0.0000
REM Highest difference peak  1.044,  deepest hole -0.769,  1-sigma level  0.121
Q1    1   0.5430  0.1567  0.4016  11.00000  0.05    1.04
Q2    1   0.6404  0.1591  0.3253  11.00000  0.05    0.97
Q3    1   0.5853  0.3271  0.3167  11.00000  0.05    0.56
Q4    1   0.5832  0.0073  0.3145  11.00000  0.05    0.52
Q5    1   0.7053  0.3549  0.5436  11.00000  0.05    0.32
;
_cod_data_source_file            zj2050.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2233707
_cod_database_fobs_code          2233707
loop_
_space_group_symop_operation_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
C C2 0.8182(2) 0.4235(7) 0.4926(2) 0.0288(6) Uani d . 1
C C3 0.7048(2) 0.3668(6) 0.4912(2) 0.0267(5) Uani d . 1
C C4 0.6702(2) 0.4704(7) 0.5771(2) 0.0309(6) Uani d . 1
H H4 0.5934 0.4287 0.5763 0.037 Uiso calc R 1
C C5 0.7499(3) 0.6374(7) 0.6653(2) 0.0327(6) Uani d . 1
H H5 0.729 0.7168 0.7258 0.039 Uiso calc R 1
C C6 0.8602(3) 0.6833(7) 0.6615(2) 0.0334(6) Uani d . 1
H H6 0.915 0.7976 0.7215 0.04 Uiso calc R 1
N N1 0.8956(2) 0.5781(6) 0.5793(2) 0.0325(5) Uani d . 1
N N2 0.8547(3) 0.3359(7) 0.4077(2) 0.0386(6) Uani d . 1
Br Br1 0.59557(2) 0.15619(6) 0.36599(2) 0.03201(13) Uani d . 1
H H2S 0.923(3) 0.345(7) 0.415(3) 0.030(9) Uiso d . 1
H H2A 0.820(4) 0.210(8) 0.362(4) 0.043(11) Uiso d . 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
C2 0.0309(14) 0.0294(12) 0.0253(12) 0.0002(11) 0.0084(11) 0.0031(10)
C3 0.0271(14) 0.0256(12) 0.0238(12) 0.0031(9) 0.0039(11) 0.0034(9)
C4 0.0282(14) 0.0331(13) 0.0319(13) 0.0070(11) 0.0107(11) 0.0076(12)
C5 0.0359(16) 0.0376(15) 0.0250(13) 0.0059(11) 0.0109(12) 0.0036(10)
C6 0.0343(16) 0.0367(15) 0.0273(13) -0.0010(12) 0.0079(12) 0.0002(11)
N1 0.0286(13) 0.0408(12) 0.0266(11) -0.0041(10) 0.0073(10) -0.0022(10)
N2 0.0303(15) 0.0568(18) 0.0309(13) -0.0112(12) 0.0134(12) -0.0120(12)
Br1 0.02548(18) 0.03463(19) 0.03161(18) 0.00029(10) 0.00396(12) -0.00178(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 0 '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'
Br Br -0.2901 2.4595 '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
N1 C2 N2 117.1(3)
N1 C2 C3 120.2(2)
N2 C2 C3 122.7(3)
C4 C3 C2 120.8(3)
C4 C3 Br1 119.7(2)
C2 C3 Br1 119.5(2)
C3 C4 C5 118.7(3)
C3 C4 H4 120.6
C5 C4 H4 120.6
C6 C5 C4 117.3(3)
C6 C5 H5 121.3
C4 C5 H5 121.3
N1 C6 C5 124.6(3)
N1 C6 H6 117.7
C5 C6 H6 117.7
C6 N1 C2 118.4(2)
C2 N2 H2S 120(3)
C2 N2 H2A 122(3)
H2S N2 H2A 113(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C2 N1 1.344(4)
C2 N2 1.357(4)
C2 C3 1.398(4)
C3 C4 1.372(4)
C3 Br1 1.904(3)
C4 C5 1.390(4)
C4 H4 0.95
C5 C6 1.378(5)
C5 H5 0.95
C6 N1 1.336(4)
C6 H6 0.95
N2 H2S 0.81(4)
N2 H2A 0.78(4)
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 H2S N1 3_766 0.81(4) 2.21(4) 3.019(4) 173(3)
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
N1 C2 C3 C4 0.7(4)
N2 C2 C3 C4 -177.6(3)
N1 C2 C3 Br1 178.6(2)
N2 C2 C3 Br1 0.3(4)
C2 C3 C4 C5 0.9(4)
Br1 C3 C4 C5 -177.04(19)
C3 C4 C5 C6 -1.1(4)
C4 C5 C6 N1 -0.1(4)
C5 C6 N1 C2 1.7(4)
N2 C2 N1 C6 176.5(3)
C3 C2 N1 C6 -1.9(4)
