#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/52/2235214.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_2235214
loop_
_publ_author_name
'Huang, Ping-Hsin'
'Wen, Yuh-Sheng'
'Shen, Jiun-Yi'
_publ_section_title
;
 2-(1H-Pyrrolo[2,3-b]pyridin-2-yl)pyridine
;
_journal_coeditor_code           RK2358
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1943
_journal_paper_doi               10.1107/S1600536812023690
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C12 H9 N3'
_chemical_formula_moiety         'C12 H9 N3'
_chemical_formula_sum            'C12 H9 N3'
_chemical_formula_weight         195.22
_chemical_name_systematic
;
2-(1H-Pyrrolo[2,3-b]pyridin-2-yl)pyridine
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 94.331(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.1416(10)
_cell_length_b                   13.7428(14)
_cell_length_c                   6.7395(7)
_cell_measurement_reflns_used    1871
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      26.25
_cell_measurement_theta_min      2.50
_cell_volume                     936.63(16)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'ω scans'
_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  0.0562
_diffrn_reflns_av_sigmaI/netI    0.0555
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            7069
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.01
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.9957
_exptl_absorpt_correction_T_min  0.9380
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_meas      1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.200
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.187
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2154
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.187
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0638
_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)+(0.0366P)²+0.2976P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1380
_refine_ls_wR_factor_ref         0.1445
_reflns_number_gt                1792
_reflns_number_total             2154
_reflns_threshold_expression     I>2\sa(I)
_cod_data_source_file            rk2358.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2235214
_cod_database_fobs_code          2235214
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
N N1 0.66995(16) 0.94501(12) 0.0034(2) 0.0382(4) Uani d . 1 1
N N2 0.50593(15) 0.92225(11) 0.2357(2) 0.0324(4) Uani d . 1 1
H H2 0.4394 0.9513 0.1684 0.039 Uiso calc R 1 1
N N3 0.27130(16) 0.91454(12) 0.4136(2) 0.0371(4) Uani d . 1 1
C C1 0.7961(2) 0.92562(16) -0.0253(3) 0.0418(5) Uani d . 1 1
H H1 0.8296 0.9475 -0.1454 0.050 Uiso calc R 1 1
C C2 0.8818(2) 0.87517(16) 0.1101(3) 0.0412(5) Uani d . 1 1
H H2A 0.9707 0.8639 0.0808 0.049 Uiso calc R 1 1
C C3 0.8377(2) 0.84179(14) 0.2859(3) 0.0391(5) Uani d . 1 1
H H3 0.8948 0.8070 0.3790 0.047 Uiso calc R 1 1
C C4 0.70684(19) 0.86035(13) 0.3238(3) 0.0333(4) Uani d . 1 1
C C5 0.62979(18) 0.91210(13) 0.1741(3) 0.0316(4) Uani d . 1 1
C C6 0.62305(19) 0.84091(13) 0.4777(3) 0.0351(5) Uani d . 1 1
H H6 0.6466 0.8073 0.5984 0.042 Uiso calc R 1 1
C C7 0.50115(19) 0.87982(13) 0.4198(3) 0.0323(4) Uani d . 1 1
C C8 0.37880(18) 0.87873(13) 0.5192(3) 0.0327(4) Uani d . 1 1
C C9 0.3725(2) 0.84151(14) 0.7108(3) 0.0411(5) Uani d . 1 1
H H9 0.4501 0.8179 0.7828 0.049 Uiso calc R 1 1
C C10 0.2536(2) 0.83931(15) 0.7945(3) 0.0465(6) Uani d . 1 1
H H10 0.2474 0.8138 0.9244 0.056 Uiso calc R 1 1
C C11 0.1429(2) 0.87497(16) 0.6860(3) 0.0460(5) Uani d . 1 1
H H11 0.0586 0.8738 0.7388 0.055 Uiso calc R 1 1
C C12 0.1579(2) 0.91213(16) 0.5003(3) 0.0440(5) Uani d . 1 1
H H12 0.0817 0.9380 0.4283 0.053 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
N1 0.0389(9) 0.0415(9) 0.0336(9) 0.0069(7) -0.0001(7) 0.0021(7)
N2 0.0326(8) 0.0329(8) 0.0306(8) 0.0031(6) -0.0059(6) 0.0030(7)
N3 0.0347(9) 0.0376(9) 0.0382(9) -0.0009(7) -0.0026(7) 0.0040(7)
C1 0.0422(11) 0.0459(12) 0.0373(11) 0.0069(9) 0.0026(9) 0.0005(9)
C2 0.0352(11) 0.0435(12) 0.0444(12) 0.0067(9) -0.0013(9) -0.0031(10)
C3 0.0366(11) 0.0361(11) 0.0426(12) 0.0037(8) -0.0104(9) 0.0006(9)
C4 0.0379(10) 0.0259(9) 0.0341(10) -0.0004(8) -0.0101(8) -0.0009(8)
C5 0.0336(10) 0.0281(9) 0.0319(10) 0.0027(8) -0.0050(8) -0.0030(8)
C6 0.0390(11) 0.0298(10) 0.0344(10) -0.0013(8) -0.0106(8) 0.0053(8)
C7 0.0382(10) 0.0253(9) 0.0321(10) -0.0037(8) -0.0065(8) 0.0015(8)
C8 0.0357(10) 0.0253(9) 0.0358(10) -0.0038(7) -0.0054(8) -0.0002(8)
C9 0.0453(12) 0.0367(11) 0.0401(11) -0.0023(9) -0.0050(9) 0.0062(9)
C10 0.0566(14) 0.0433(12) 0.0397(12) -0.0035(10) 0.0054(10) 0.0083(10)
C11 0.0410(12) 0.0458(12) 0.0521(13) -0.0032(10) 0.0094(10) 0.0023(10)
C12 0.0393(11) 0.0444(12) 0.0473(12) 0.0000(9) -0.0027(9) 0.0011(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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C5 N1 C1 114.66(18)
C5 N2 C7 109.17(15)
C5 N2 H2 125.4
C7 N2 H2 125.4
C12 N3 C8 116.82(17)
N1 C1 C2 124.1(2)
N1 C1 H1 117.9
C2 C1 H1 117.9
C3 C2 C1 120.04(19)
C3 C2 H2A 120.0
C1 C2 H2A 120.0
C2 C3 C4 118.22(19)
C2 C3 H3 120.9
C4 C3 H3 120.9
C3 C4 C6 137.09(19)
C3 C4 C5 116.24(18)
C6 C4 C5 106.67(17)
N1 C5 N2 125.47(17)
N1 C5 C4 126.71(18)
N2 C5 C4 107.81(17)
C7 C6 C4 107.17(17)
C7 C6 H6 126.4
C4 C6 H6 126.4
N2 C7 C6 109.17(17)
N2 C7 C8 120.62(16)
C6 C7 C8 130.19(18)
N3 C8 C9 122.01(18)
N3 C8 C7 115.95(17)
C9 C8 C7 122.04(18)
C10 C9 C8 119.5(2)
C10 C9 H9 120.2
C8 C9 H9 120.2
C9 C10 C11 118.7(2)
C9 C10 H10 120.7
C11 C10 H10 120.7
C12 C11 C10 118.2(2)
C12 C11 H11 120.9
C10 C11 H11 120.9
N3 C12 C11 124.7(2)
N3 C12 H12 117.6
C11 C12 H12 117.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C5 1.328(2)
N1 C1 1.335(3)
N2 C5 1.360(2)
N2 C7 1.376(2)
N2 H2 0.8800
N3 C12 1.329(3)
N3 C8 1.349(2)
C1 C2 1.396(3)
C1 H1 0.9500
C2 C3 1.377(3)
C2 H2A 0.9500
C3 C4 1.393(3)
C3 H3 0.9500
C4 C6 1.415(3)
C4 C5 1.420(3)
C6 C7 1.376(3)
C6 H6 0.9500
C7 C8 1.454(3)
C8 C9 1.395(3)
C9 C10 1.369(3)
C9 H9 0.9500
C10 C11 1.383(3)
C10 H10 0.9500
C11 C12 1.371(3)
C11 H11 0.9500
C12 H12 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
N2 H2 N1 3_675 0.88 2.100 2.944(2) 162
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 29332620
