#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:42:48 +0200 (vie 13 de oct de 2017) $
#$Revision: 201978 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/03/2220335.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_2220335
loop_
_publ_author_name
'Wan Saffiee, Wan Ainna Mardhiah'
'Idris, Azila'
'Aiyub, Zaharah'
'Abdullah, Zanariah'
'Ng, Seik Weng'
_publ_section_title
;
 N-(Pyrazin-2-yl)-4-toluidine
;
_journal_coeditor_code           SG2277
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2440
_journal_paper_doi               10.1107/S160053680803729X
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C11 H11 N3'
_chemical_formula_moiety         'C11 H11 N3'
_chemical_formula_sum            'C11 H11 N3'
_chemical_formula_weight         185.23
_chemical_name_systematic
;
N-(Pyrazin-2-yl)-4-toluidine
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 105.790(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   21.7179(7)
_cell_length_b                   7.5323(3)
_cell_length_c                   12.0073(5)
_cell_measurement_reflns_used    1368
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.2
_cell_measurement_theta_min      2.9
_cell_volume                     1890.10(13)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       ω
_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  0.0407
_diffrn_reflns_av_sigmaI/netI    0.0519
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6057
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.95
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.258
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         2165
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0822
_refine_ls_R_factor_gt           0.0458
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0652P)²+0.9346P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1125
_refine_ls_wR_factor_ref         0.1346
_reflns_number_gt                1437
_reflns_number_total             2165
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sg2277.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'None' changed to
'none' 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 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'None' changed to
'none' 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_cell_volume        1890.10(10)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2220335
_cod_database_fobs_code          2220335
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
N N1 0.31486(7) 0.7286(2) 0.14663(14) 0.0223(4) Uani d . 1
H H1 0.2746(10) 0.754(3) 0.1433(17) 0.025(5) Uiso d . 1
N N2 0.39338(7) 0.5068(2) 0.20972(13) 0.0215(4) Uani d . 1
N N3 0.30867(7) 0.3328(2) 0.31234(14) 0.0240(4) Uani d . 1
C C1 0.34916(8) 0.8610(2) 0.10751(15) 0.0209(4) Uani d . 1
C C2 0.31332(8) 0.9994(2) 0.04370(15) 0.0225(4) Uani d . 1
H H2 0.2680 0.9977 0.0274 0.027 Uiso calc R 1
C C3 0.34299(9) 1.1385(2) 0.00420(15) 0.0243(4) Uani d . 1
H H3 0.3176 1.2305 -0.0396 0.029 Uiso calc R 1
C C4 0.40936(9) 1.1472(2) 0.02707(15) 0.0231(4) Uani d . 1
C C5 0.44431(8) 1.0095(2) 0.09091(15) 0.0226(4) Uani d . 1
H H5 0.4897 1.0127 0.1081 0.027 Uiso calc R 1
C C6 0.41565(8) 0.8672(2) 0.13069(15) 0.0222(4) Uani d . 1
H H6 0.4412 0.7745 0.1734 0.027 Uiso calc R 1
C C7 0.44137(10) 1.3010(3) -0.01539(18) 0.0302(5) Uani d . 1
H H7A 0.4876 1.2958 0.0203 0.045 Uiso calc R 1
H H7B 0.4244 1.4129 0.0056 0.045 Uiso calc R 1
H H7C 0.4328 1.2941 -0.0997 0.045 Uiso calc R 1
C C8 0.33543(8) 0.5719(2) 0.20318(15) 0.0201(4) Uani d . 1
C C9 0.29286(8) 0.4818(2) 0.25360(16) 0.0231(4) Uani d . 1
H H9 0.2514 0.5298 0.2450 0.028 Uiso calc R 1
C C10 0.36764(8) 0.2678(2) 0.32060(16) 0.0231(4) Uani d . 1
H H10 0.3813 0.1616 0.3628 0.028 Uiso calc R 1
C C11 0.40806(9) 0.3538(2) 0.26845(16) 0.0235(4) Uani d . 1
H H11 0.4487 0.3022 0.2742 0.028 Uiso calc R 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
N1 0.0217(8) 0.0194(8) 0.0284(9) 0.0007(6) 0.0110(7) 0.0031(7)
N2 0.0249(8) 0.0191(8) 0.0223(8) 0.0013(6) 0.0095(6) -0.0011(6)
N3 0.0254(8) 0.0213(8) 0.0262(9) -0.0016(6) 0.0087(7) 0.0019(7)
C1 0.0275(9) 0.0177(9) 0.0191(9) -0.0009(7) 0.0089(7) -0.0013(7)
C2 0.0240(9) 0.0224(10) 0.0214(10) 0.0019(8) 0.0067(7) -0.0018(8)
C3 0.0344(10) 0.0191(9) 0.0194(10) 0.0024(8) 0.0072(8) 0.0004(7)
C4 0.0316(10) 0.0193(9) 0.0200(9) -0.0032(8) 0.0096(8) -0.0008(7)
C5 0.0252(9) 0.0222(10) 0.0221(10) -0.0018(8) 0.0093(8) -0.0018(8)
C6 0.0261(9) 0.0207(9) 0.0204(9) 0.0004(7) 0.0071(7) 0.0004(7)
C7 0.0390(11) 0.0250(11) 0.0287(11) -0.0033(9) 0.0128(9) 0.0045(8)
C8 0.0237(9) 0.0196(9) 0.0177(9) -0.0013(7) 0.0065(7) -0.0023(7)
C9 0.0222(9) 0.0211(9) 0.0267(10) 0.0003(7) 0.0079(8) 0.0002(8)
C10 0.0275(9) 0.0187(9) 0.0237(10) 0.0022(7) 0.0077(8) 0.0003(8)
C11 0.0264(9) 0.0211(10) 0.0238(10) 0.0020(8) 0.0080(8) -0.0020(8)
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C8 N1 C1 130.28(15)
C8 N1 H1 113.3(13)
C1 N1 H1 115.9(14)
C8 N2 C11 115.60(15)
C9 N3 C10 116.84(15)
C6 C1 C2 118.44(16)
C6 C1 N1 124.95(16)
C2 C1 N1 116.58(15)
C3 C2 C1 120.81(16)
C3 C2 H2 119.6
C1 C2 H2 119.6
C2 C3 C4 121.50(17)
C2 C3 H3 119.3
C4 C3 H3 119.3
C5 C4 C3 117.08(16)
C5 C4 C7 121.84(16)
C3 C4 C7 121.08(17)
C4 C5 C6 122.59(16)
C4 C5 H5 118.7
C6 C5 H5 118.7
C5 C6 C1 119.58(17)
C5 C6 H6 120.2
C1 C6 H6 120.2
C4 C7 H7A 109.5
C4 C7 H7B 109.5
H7A C7 H7B 109.5
C4 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
N2 C8 N1 121.33(16)
N2 C8 C9 121.10(16)
N1 C8 C9 117.57(15)
N3 C9 C8 122.23(16)
N3 C9 H9 118.9
C8 C9 H9 118.9
N3 C10 C11 120.51(17)
N3 C10 H10 119.7
C11 C10 H10 119.7
N2 C11 C10 123.68(17)
N2 C11 H11 118.2
C10 C11 H11 118.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C8 1.374(2)
N1 C1 1.401(2)
N1 H1 0.89(2)
N2 C8 1.333(2)
N2 C11 1.344(2)
N3 C9 1.320(2)
N3 C10 1.349(2)
C1 C6 1.395(2)
C1 C2 1.398(2)
C2 C3 1.380(3)
C2 H2 0.9500
C3 C4 1.393(3)
C3 H3 0.9500
C4 C5 1.386(3)
C4 C7 1.509(3)
C5 C6 1.388(2)
C5 H5 0.9500
C6 H6 0.9500
C7 H7A 0.9800
C7 H7B 0.9800
C7 H7C 0.9800
C8 C9 1.410(2)
C9 H9 0.9500
C10 C11 1.372(3)
C10 H10 0.9500
C11 H11 0.9500
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
_geom_hbond_publ_flag
N1 H1 N3 4 0.89(2) 2.10(2) 2.963(2) 163(2) yes
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
C8 N1 C1 C6 -7.4(3)
C8 N1 C1 C2 174.81(17)
C6 C1 C2 C3 0.2(3)
N1 C1 C2 C3 178.22(16)
C1 C2 C3 C4 -0.6(3)
C2 C3 C4 C5 0.2(3)
C2 C3 C4 C7 -179.30(17)
C3 C4 C5 C6 0.4(3)
C7 C4 C5 C6 179.96(17)
C4 C5 C6 C1 -0.7(3)
C2 C1 C6 C5 0.4(3)
N1 C1 C6 C5 -177.39(17)
C11 N2 C8 N1 179.29(16)
C11 N2 C8 C9 -1.1(2)
C1 N1 C8 N2 -13.4(3)
C1 N1 C8 C9 166.96(17)
C10 N3 C9 C8 -1.1(3)
N2 C8 C9 N3 2.1(3)
N1 C8 C9 N3 -178.20(16)
C9 N3 C10 C11 -0.8(3)
C8 N2 C11 C10 -0.8(3)
N3 C10 C11 N2 1.8(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 16099723
