#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/43/2224311.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_2224311
loop_
_publ_author_name
'Selig, Roland'
'Schollmeyer, Dieter'
'Albrecht, Wolfgang'
'Laufer, Stefan'
_publ_section_title
;
 2-(3,4,5-Trimethoxyphenyl)-1H-pyrrolo[2,3-b]pyridine
;
_journal_coeditor_code           IM2158
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3097
_journal_paper_doi               10.1107/S1600536809047540
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C16 H16 N2 O3'
_chemical_formula_moiety         'C16 H16 N2 O3'
_chemical_formula_sum            'C16 H16 N2 O3'
_chemical_formula_weight         284.31
_chemical_name_systematic
;
2-(3,4,5-Trimethoxyphenyl)-1H-pyrrolo[2,3-b]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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.778(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.6283(9)
_cell_length_b                   10.1745(4)
_cell_length_c                   18.604(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      70
_cell_measurement_theta_min      66
_cell_volume                     1396.2(2)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'CORINC (Dräger & Gattow, 1971)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1999)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_sigmaI/netI    0.0222
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            2865
_diffrn_reflns_theta_full        69.98
_diffrn_reflns_theta_max         69.98
_diffrn_reflns_theta_min         4.92
_diffrn_standards_decay_%        2
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.776
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.205
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2657
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0446
_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)+(0.0641P)²+0.5259P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.1205
_refine_ls_wR_factor_ref         0.1249
_reflns_number_gt                2352
_reflns_number_total             2657
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            im2158.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2224311
_cod_database_fobs_code          2224311
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_disorder_assembly
_atom_site_disorder_group
N N1 0.62152(18) 0.53967(13) 0.42466(7) 0.0312(3) Uani d . 1 . .
H H1 0.6399 0.4802 0.4653 0.037 Uiso d R 1 . .
C C2 0.7269(2) 0.55266(16) 0.37403(8) 0.0308(3) Uani d . 1 . .
C C3 0.6670(2) 0.65831(17) 0.32906(9) 0.0360(4) Uani d . 1 . .
H H3 0.7158 0.6888 0.2899 0.043 Uiso calc R 1 . .
C C3A 0.5187(2) 0.71430(17) 0.35131(9) 0.0344(4) Uani d . 1 . .
C C4 0.4017(3) 0.82022(19) 0.32915(10) 0.0451(4) Uani d . 1 . .
H H4 0.4120 0.8762 0.2896 0.054 Uiso calc R 1 . .
C C5 0.2705(3) 0.8406(2) 0.36686(11) 0.0524(5) Uani d . 1 . .
H H5 0.1888 0.9123 0.3536 0.063 Uiso calc R 1 . .
C C6 0.2568(3) 0.7568(2) 0.42413(11) 0.0492(5) Uani d . 1 . .
H H6 0.1629 0.7736 0.4481 0.059 Uiso calc R 1 . .
N N7 0.3663(2) 0.65397(15) 0.44823(8) 0.0381(4) Uani d . 1 . .
C C7A 0.4931(2) 0.63661(16) 0.41105(9) 0.0310(3) Uani d . 1 . .
C C8 0.8710(2) 0.45896(16) 0.37109(8) 0.0307(3) Uani d . 1 . .
C C9 0.9838(2) 0.48432(16) 0.32401(9) 0.0330(4) Uani d . 1 . .
H H9 0.9711 0.5640 0.2966 0.040 Uiso calc R 1 . .
C C10 1.1137(2) 0.39363(17) 0.31741(9) 0.0324(4) Uani d . 1 . .
C C11 1.1358(2) 0.27617(16) 0.35828(9) 0.0313(3) Uani d . 1 . .
C C12 1.0243(2) 0.25251(16) 0.40535(9) 0.0326(4) Uani d . 1 . .
C C13 0.8925(2) 0.34277(16) 0.41142(9) 0.0338(4) Uani d . 1 . .
H H13 0.8164 0.3249 0.4435 0.041 Uiso calc R 1 . .
O O14 1.22631(17) 0.40749(13) 0.27123(7) 0.0439(3) Uani d . 1 . .
C C15 1.1984(3) 0.5172(2) 0.22231(10) 0.0454(5) Uani d . 1 . .
H H15A 1.0720 0.5186 0.1929 0.068 Uiso calc R 1 . .
H H15B 1.2787 0.5103 0.1889 0.068 Uiso calc R 1 . .
H H15C 1.2253 0.5984 0.2513 0.068 Uiso calc R 1 . .
O O16 1.25139(16) 0.17927(12) 0.34718(7) 0.0376(3) Uani d . 1 . .
C C17 1.4407(2) 0.2090(2) 0.37068(11) 0.0458(4) Uani d . 1 . .
H H17A 1.4722 0.2711 0.3357 0.069 Uiso calc R 1 . .
H H17B 1.5110 0.1281 0.3721 0.069 Uiso calc R 1 . .
H H17C 1.4684 0.2484 0.4204 0.069 Uiso calc R 1 . .
O O18 1.03203(16) 0.13515(12) 0.44277(7) 0.0399(3) Uani d . 1 . .
C C19 1.1896(3) 0.1164(2) 0.50170(11) 0.0518(5) Uani d . 1 . .
H H19A 1.2953 0.1062 0.4813 0.078 Uiso calc R 1 . .
H H19B 1.1753 0.0372 0.5297 0.078 Uiso calc R 1 . .
H H19C 1.2073 0.1928 0.5349 0.078 Uiso calc R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C7A N1 C2 . . 108.43(13) ?
C7A N1 H1 . . 124.1 ?
C2 N1 H1 . . 127.2 ?
C3 C2 N1 . . 109.17(14) ?
C3 C2 C8 . . 128.68(14) ?
N1 C2 C8 . . 122.09(14) ?
C2 C3 C3A . . 107.69(14) ?
C2 C3 H3 . . 126.2 ?
C3A C3 H3 . . 126.2 ?
C4 C3A C7A . . 117.21(16) ?
C4 C3A C3 . . 136.27(16) ?
C7A C3A C3 . . 106.52(14) ?
C5 C4 C3A . . 117.38(16) ?
C5 C4 H4 . . 121.3 ?
C3A C4 H4 . . 121.3 ?
C4 C5 C6 . . 120.36(17) ?
C4 C5 H5 . . 119.8 ?
C6 C5 H5 . . 119.8 ?
N7 C6 C5 . . 124.90(17) ?
N7 C6 H6 . . 117.5 ?
C5 C6 H6 . . 117.6 ?
C7A N7 C6 . . 113.64(15) ?
N7 C7A N1 . . 125.32(14) ?
N7 C7A C3A . . 126.50(15) ?
N1 C7A C3A . . 108.18(14) ?
C13 C8 C9 . . 119.24(15) ?
C13 C8 C2 . . 121.36(14) ?
C9 C8 C2 . . 119.33(14) ?
C10 C9 C8 . . 120.12(15) ?
C10 C9 H9 . . 119.9 ?
C8 C9 H9 . . 119.9 ?
O14 C10 C9 . . 124.47(15) ?
O14 C10 C11 . . 114.85(14) ?
C9 C10 C11 . . 120.66(14) ?
O16 C11 C12 . . 119.38(15) ?
O16 C11 C10 . . 121.53(14) ?
C12 C11 C10 . . 118.76(14) ?
O18 C12 C13 . . 118.16(14) ?
O18 C12 C11 . . 121.02(14) ?
C13 C12 C11 . . 120.64(15) ?
C12 C13 C8 . . 120.57(14) ?
C12 C13 H13 . . 119.7 ?
C8 C13 H13 . . 119.7 ?
C10 O14 C15 . . 117.87(13) ?
O14 C15 H15A . . 109.5 ?
O14 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
O14 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C11 O16 C17 . . 116.03(13) ?
O16 C17 H17A . . 109.5 ?
O16 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
O16 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C12 O18 C19 . . 115.25(14) ?
O18 C19 H19A . . 109.5 ?
O18 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
O18 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
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
N1 C7A . 1.367(2) ?
N1 C2 . 1.3917(19) ?
N1 H1 . 0.9499 ?
C2 C3 . 1.367(2) ?
C2 C8 . 1.467(2) ?
C3 C3A . 1.419(2) ?
C3 H3 . 0.9500 ?
C3A C4 . 1.393(2) ?
C3A C7A . 1.417(2) ?
C4 C5 . 1.377(3) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.389(3) ?
C5 H5 . 0.9500 ?
C6 N7 . 1.343(2) ?
C6 H6 . 0.9500 ?
N7 C7A . 1.336(2) ?
C8 C13 . 1.387(2) ?
C8 C9 . 1.400(2) ?
C9 C10 . 1.382(2) ?
C9 H9 . 0.9500 ?
C10 O14 . 1.3681(19) ?
C10 C11 . 1.403(2) ?
C11 O16 . 1.3729(19) ?
C11 C12 . 1.389(2) ?
C12 O18 . 1.3758(19) ?
C12 C13 . 1.387(2) ?
C13 H13 . 0.9500 ?
O14 C15 . 1.422(2) ?
C15 H15A . 0.9800 ?
C15 H15B . 0.9800 ?
C15 H15C . 0.9800 ?
O16 C17 . 1.430(2) ?
C17 H17A . 0.9800 ?
C17 H17B . 0.9800 ?
C17 H17C . 0.9800 ?
O18 C19 . 1.418(2) ?
C19 H19A . 0.9800 ?
C19 H19B . 0.9800 ?
C19 H19C . 0.9800 ?
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
N1 H1 N7 3_666 0.95 2.12 3.061(2) 171
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
C7A N1 C2 C3 . . . . 0.71(18) ?
C7A N1 C2 C8 . . . . -176.55(14) ?
N1 C2 C3 C3A . . . . -0.21(19) ?
C8 C2 C3 C3A . . . . 176.82(16) ?
C2 C3 C3A C4 . . . . 179.8(2) ?
C2 C3 C3A C7A . . . . -0.35(19) ?
C7A C3A C4 C5 . . . . -0.2(3) ?
C3 C3A C4 C5 . . . . 179.6(2) ?
C3A C4 C5 C6 . . . . -0.6(3) ?
C4 C5 C6 N7 . . . . 1.1(4) ?
C5 C6 N7 C7A . . . . -0.7(3) ?
C6 N7 C7A N1 . . . . 179.77(17) ?
C6 N7 C7A C3A . . . . -0.1(3) ?
C2 N1 C7A N7 . . . . 179.17(15) ?
C2 N1 C7A C3A . . . . -0.92(18) ?
C4 C3A C7A N7 . . . . 0.6(3) ?
C3 C3A C7A N7 . . . . -179.31(16) ?
C4 C3A C7A N1 . . . . -179.33(15) ?
C3 C3A C7A N1 . . . . 0.79(18) ?
C3 C2 C8 C13 . . . . -167.47(17) ?
N1 C2 C8 C13 . . . . 9.2(2) ?
C3 C2 C8 C9 . . . . 9.5(3) ?
N1 C2 C8 C9 . . . . -173.77(14) ?
C13 C8 C9 C10 . . . . 0.7(2) ?
C2 C8 C9 C10 . . . . -176.40(14) ?
C8 C9 C10 O14 . . . . 177.84(15) ?
C8 C9 C10 C11 . . . . -0.8(2) ?
O14 C10 C11 O16 . . . . -5.2(2) ?
C9 C10 C11 O16 . . . . 173.52(14) ?
O14 C10 C11 C12 . . . . -178.56(14) ?
C9 C10 C11 C12 . . . . 0.2(2) ?
O16 C11 C12 O18 . . . . 2.1(2) ?
C10 C11 C12 O18 . . . . 175.55(14) ?
O16 C11 C12 C13 . . . . -172.96(15) ?
C10 C11 C12 C13 . . . . 0.5(2) ?
O18 C12 C13 C8 . . . . -175.80(14) ?
C11 C12 C13 C8 . . . . -0.6(2) ?
C9 C8 C13 C12 . . . . 0.0(2) ?
C2 C8 C13 C12 . . . . 177.04(15) ?
C9 C10 O14 C15 . . . . -5.3(2) ?
C11 C10 O14 C15 . . . . 173.38(15) ?
C12 C11 O16 C17 . . . . -117.52(17) ?
C10 C11 O16 C17 . . . . 69.2(2) ?
C13 C12 O18 C19 . . . . -113.18(18) ?
C11 C12 O18 C19 . . . . 71.7(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 19622623
