#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:31:46 +0200 (vie 13 de oct de 2017) $
#$Revision: 201979 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/62/2236208.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_2236208
loop_
_publ_author_name
'Kloubert, Tobias'
'Kretschmer, Robert'
'Görls, Helmar'
'Westerhausen, Matthias'
_publ_section_title
;
 [1-Methoxy-3-(pyridin-2-yl)indolizin-2-yl](pyridin-2-yl)methanone
;
_journal_coeditor_code           GG2090
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2631
_journal_page_last               o2632
_journal_paper_doi               10.1107/S160053681203396X
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C20 H15 N3 O2'
_chemical_formula_moiety         'C20 H15 N3 O2'
_chemical_formula_sum            'C20 H15 N3 O2'
_chemical_formula_weight         329.35
_chemical_name_systematic
;
[1-Methoxy-3-(pyridin-2-yl)indolizin-2-yl](pyridin-2-yl)methanone
;
_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                 107.070(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   25.822(2)
_cell_length_b                   11.4406(9)
_cell_length_c                   11.3602(7)
_cell_measurement_reflns_used    10598
_cell_measurement_temperature    183(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      1.65
_cell_volume                     3208.2(4)
_computing_cell_refinement       'DENZO (Otwinowski, Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction        'DENZO (Otwinowski, Minor, 1997)'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      183(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'phi- + omega-scan'
_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  0.0700
_diffrn_reflns_av_sigmaI/netI    0.0770
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10598
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         1.65
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.276
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         3667
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.1155
_refine_ls_R_factor_gt           0.0541
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0651P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1158
_refine_ls_wR_factor_ref         0.1324
_reflns_number_gt                2207
_reflns_number_total             3667
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gg2090.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2236208
_cod_database_fobs_code          2236208
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
_atom_site_symmetry_multiplicity
O O1 0.04698(6) 0.09288(12) 0.06993(13) 0.0364(4) Uani d . 1 1
O O2 0.12184(6) 0.12783(12) 0.35467(12) 0.0383(4) Uani d . 1 1
N N1 0.15233(6) 0.26387(13) 0.01130(13) 0.0259(4) Uani d . 1 1
N N2 0.22178(7) 0.32179(13) 0.33083(14) 0.0285(4) Uani d . 1 1
N N3 0.08352(7) 0.41960(14) 0.28790(15) 0.0348(4) Uani d . 1 1
C C1 0.18167(9) 0.29453(18) -0.06859(18) 0.0315(5) Uani d . 1 1
H H1 0.2132(10) 0.3465(18) -0.0350(19) 0.042(6) Uiso d . 1 1
C C2 0.16708(9) 0.25249(19) -0.18445(19) 0.0365(5) Uani d . 1 1
H H2 0.1893(9) 0.2805(18) -0.238(2) 0.042(6) Uiso d . 1 1
C C3 0.12207(10) 0.17639(19) -0.22799(19) 0.0381(5) Uani d . 1 1
H H3 0.1124(9) 0.1416(18) -0.313(2) 0.039(6) Uiso d . 1 1
C C4 0.09303(9) 0.14572(17) -0.15113(17) 0.0328(5) Uani d . 1 1
H H4 0.0638(9) 0.0923(18) -0.1749(18) 0.032(6) Uiso d . 1 1
C C5 0.10777(8) 0.18737(16) -0.02876(17) 0.0272(4) Uani d . 1 1
C C6 0.08989(8) 0.16467(15) 0.07313(17) 0.0276(4) Uani d . 1 1
C C7 0.12235(8) 0.22698(15) 0.17367(16) 0.0254(4) Uani d . 1 1
C C8 0.16079(8) 0.28941(15) 0.13492(16) 0.0248(4) Uani d . 1 1
C C9 0.20472(8) 0.35985(16) 0.21281(16) 0.0265(4) Uani d . 1 1
C C10 0.22672(9) 0.45894(18) 0.17435(19) 0.0323(5) Uani d . 1 1
H H10 0.2123(9) 0.4926(19) 0.095(2) 0.041(6) Uiso d . 1 1
C C11 0.26848(9) 0.51716(19) 0.2576(2) 0.0388(5) Uani d . 1 1
H H11 0.2828(9) 0.5875(19) 0.2335(19) 0.045(6) Uiso d . 1 1
C C12 0.28677(9) 0.47791(19) 0.3779(2) 0.0383(5) Uani d . 1 1
H H12 0.3157(10) 0.513(2) 0.442(2) 0.060(7) Uiso d . 1 1
C C13 0.26168(8) 0.38150(18) 0.40973(18) 0.0328(5) Uani d . 1 1
H H13 0.2725(8) 0.3486(16) 0.4960(19) 0.033(5) Uiso d . 1 1
C C14 0.11818(8) 0.22114(17) 0.30094(17) 0.0270(4) Uani d . 1 1
C C15 0.10492(8) 0.32971(16) 0.36106(16) 0.0271(4) Uani d . 1 1
C C16 0.11300(9) 0.3300(2) 0.48702(19) 0.0372(5) Uani d . 1 1
H H16 0.1298(9) 0.2654(18) 0.5342(18) 0.031(5) Uiso d . 1 1
C C17 0.09646(10) 0.4251(2) 0.5409(2) 0.0424(6) Uani d . 1 1
H H17 0.1002(10) 0.425(2) 0.629(2) 0.053(7) Uiso d . 1 1
C C18 0.07292(9) 0.5171(2) 0.4673(2) 0.0404(6) Uani d . 1 1
H H18 0.0603(9) 0.5834(19) 0.500(2) 0.045(6) Uiso d . 1 1
C C19 0.06806(10) 0.5113(2) 0.3431(2) 0.0423(6) Uani d . 1 1
H H19 0.0544(10) 0.576(2) 0.290(2) 0.056(7) Uiso d . 1 1
C C20 -0.00098(11) 0.1550(2) 0.0648(3) 0.0683(8) Uani d . 1 1
H H20C -0.0300 0.0995 0.0643 0.102 Uiso calc R 1 1
H H20B -0.0117 0.2023 -0.0104 0.102 Uiso calc R 1 1
H H20A 0.0055 0.2061 0.1369 0.102 Uiso calc R 1 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
O O 0.0106 0.0060 '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
C6 O1 C20 113.04(16)
C1 N1 C8 130.92(17)
C1 N1 C5 119.75(16)
C8 N1 C5 109.17(15)
C13 N2 C9 117.51(17)
C15 N3 C19 115.91(17)
C2 C1 N1 119.9(2)
C2 C1 H1 123.6(12)
N1 C1 H1 116.4(12)
C1 C2 C3 121.7(2)
C1 C2 H2 115.6(12)
C3 C2 H2 122.7(12)
C4 C3 C2 119.1(2)
C4 C3 H3 119.4(12)
C2 C3 H3 121.5(12)
C3 C4 C5 120.5(2)
C3 C4 H4 122.0(12)
C5 C4 H4 117.4(12)
C6 C5 N1 106.62(15)
C6 C5 C4 134.18(19)
N1 C5 C4 119.05(18)
O1 C6 C5 123.57(16)
O1 C6 C7 127.84(17)
C5 C6 C7 108.59(17)
C8 C7 C6 108.36(16)
C8 C7 C14 126.37(16)
C6 C7 C14 125.17(17)
N1 C8 C7 107.24(15)
N1 C8 C9 126.40(17)
C7 C8 C9 126.14(16)
N2 C9 C10 121.83(17)
N2 C9 C8 113.07(16)
C10 C9 C8 125.07(17)
C11 C10 C9 119.08(19)
C11 C10 H10 117.7(13)
C9 C10 H10 122.9(13)
C10 C11 C12 119.5(2)
C10 C11 H11 119.9(13)
C12 C11 H11 120.4(13)
C13 C12 C11 117.9(2)
C13 C12 H12 116.9(14)
C11 C12 H12 125.2(14)
N2 C13 C12 124.12(19)
N2 C13 H13 113.5(11)
C12 C13 H13 122.3(11)
O2 C14 C7 120.69(17)
O2 C14 C15 119.34(17)
C7 C14 C15 119.79(16)
N3 C15 C16 123.41(18)
N3 C15 C14 117.44(16)
C16 C15 C14 119.08(18)
C17 C16 C15 119.3(2)
C17 C16 H16 121.3(12)
C15 C16 H16 119.4(12)
C18 C17 C16 118.4(2)
C18 C17 H17 120.9(14)
C16 C17 H17 120.6(14)
C17 C18 C19 118.5(2)
C17 C18 H18 121.3(13)
C19 C18 H18 120.2(13)
N3 C19 C18 124.4(2)
N3 C19 H19 115.0(14)
C18 C19 H19 120.6(14)
O1 C20 H20C 109.5
O1 C20 H20B 109.5
H20C C20 H20B 109.5
O1 C20 H20A 109.5
H20C C20 H20A 109.5
H20B C20 H20A 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C6 1.371(2)
O1 C20 1.414(3)
O2 C14 1.220(2)
N1 C1 1.387(2)
N1 C8 1.387(2)
N1 C5 1.411(2)
N2 C13 1.338(2)
N2 C9 1.354(2)
N3 C15 1.336(2)
N3 C19 1.341(3)
C1 C2 1.347(3)
C1 H1 0.99(2)
C2 C3 1.420(3)
C2 H2 1.00(2)
C3 C4 1.353(3)
C3 H3 1.01(2)
C4 C5 1.412(3)
C4 H4 0.95(2)
C5 C6 1.391(3)
C6 C7 1.398(3)
C7 C8 1.395(3)
C7 C14 1.483(3)
C8 C9 1.459(3)
C9 C10 1.395(3)
C10 C11 1.379(3)
C10 H10 0.95(2)
C11 C12 1.383(3)
C11 H11 0.96(2)
C12 C13 1.380(3)
C12 H12 0.97(2)
C13 H13 1.01(2)
C14 C15 1.505(3)
C15 C16 1.384(3)
C16 C17 1.376(3)
C16 H16 0.94(2)
C17 C18 1.371(3)
C17 H17 0.98(2)
C18 C19 1.382(3)
C18 H18 0.94(2)
C19 H19 0.96(3)
C20 H20C 0.9800
C20 H20B 0.9800
C20 H20A 0.9800
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658059
