#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:08:31 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180289 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/03/7150326.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7150326
loop_
_publ_author_name
'Siu, Jason'
'Baxendale, Ian R.'
'Ley, Steven V.'
_publ_section_title
;
 Microwave assisted Leimgruber-Batcho reaction for the preparation of
 indoles, azaindoles and pyrroylquinolines.
;
_journal_issue                   2
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              160
_journal_page_last               167
_journal_paper_doi               10.1039/b313012f
_journal_volume                  2
_journal_year                    2004
_chemical_formula_moiety         'C11 H11 N3 O2'
_chemical_formula_sum            'C11 H11 N3 O2'
_chemical_formula_weight         217.23
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                101.554(6)
_cell_angle_beta                 92.508(6)
_cell_angle_gamma                103.229(3)
_cell_formula_units_Z            2
_cell_length_a                   7.2055(6)
_cell_length_b                   7.8564(7)
_cell_length_c                   9.9993(8)
_cell_measurement_reflns_used    6384
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      25.03
_cell_measurement_theta_min      1.02
_cell_volume                     537.48(8)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_data_reduction
;
HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0728
_diffrn_reflns_av_sigmaI/netI    0.0751
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5051
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         4.18
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.907
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             228
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         1867
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.1164
_refine_ls_R_factor_gt           0.0787
_refine_ls_shift/su_max          0.380
_refine_ls_shift/su_mean         0.014
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1529P)²+0.0735P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2195
_refine_ls_wR_factor_ref         0.2499
_reflns_number_gt                1241
_reflns_number_total             1867
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b313012f.txt
_cod_data_source_block           sl0312
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7150326
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2754(4) 0.7115(3) 0.8951(3) 0.0587(9) Uani 1 1 d . . .
O2 O 0.1962(4) 0.6083(3) 1.0725(2) 0.0509(8) Uani 1 1 d . . .
N1 N 0.5797(5) 0.2837(4) 0.4672(3) 0.0528(9) Uani 1 1 d . . .
N2 N 0.2535(4) 0.5897(4) 0.9580(3) 0.0360(8) Uani 1 1 d . . .
N3 N 0.1262(4) 0.1055(4) 1.2664(3) 0.0400(8) Uani 1 1 d . . .
C1 C 0.4245(5) 0.2768(4) 0.6960(3) 0.0339(8) Uani 1 1 d . . .
C2 C 0.3983(5) 0.1222(5) 0.7510(3) 0.0368(9) Uani 1 1 d . . .
H2 H 0.4319 0.0184 0.7023 0.044 Uiso 1 1 calc R . .
C3 C 0.3249(5) 0.1216(4) 0.8738(3) 0.0349(8) Uani 1 1 d . . .
H3 H 0.3079 0.0151 0.9080 0.042 Uiso 1 1 calc R . .
C4 C 0.2718(4) 0.2716(4) 0.9546(3) 0.0308(8) Uani 1 1 d . . .
C5 C 0.2970(4) 0.4230(4) 0.8926(3) 0.0320(8) Uani 1 1 d . . .
C6 C 0.3732(4) 0.4257(4) 0.7669(3) 0.0341(8) Uani 1 1 d . . .
H6 H 0.3897 0.5302 0.7303 0.041 Uiso 1 1 calc R . .
C7 C 0.5106(5) 0.2818(4) 0.5695(3) 0.0388(9) Uani 1 1 d . . .
C8 C 0.2020(5) 0.2613(4) 1.0854(3) 0.0355(8) Uani 1 1 d . . .
H8 H 0.1630 0.3617 1.1348 0.043 Uiso 1 1 calc R . .
C9 C 0.1879(4) 0.1159(5) 1.1438(3) 0.0353(8) Uani 1 1 d . . .
H9 H 0.2248 0.0150 1.0932 0.042 Uiso 1 1 calc R . .
C10 C 0.0666(6) 0.2540(5) 1.3516(4) 0.0494(10) Uani 1 1 d . . .
H10A H -0.0362 0.2842 1.3006 0.074 Uiso 1 1 calc R . .
H10B H 0.1759 0.3584 1.3762 0.074 Uiso 1 1 calc R . .
H10C H 0.0202 0.2190 1.4352 0.074 Uiso 1 1 calc R . .
C11 C 0.1208(5) -0.0520(5) 1.3221(4) 0.0434(9) Uani 1 1 d . . .
H11A H 0.1634 -0.1416 1.2556 0.065 Uiso 1 1 calc R . .
H11B H -0.0104 -0.1021 1.3412 0.065 Uiso 1 1 calc R . .
H11C H 0.2058 -0.0189 1.4073 0.065 Uiso 1 1 calc R . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 N2 O1 121.1(3) . . ?
O2 N2 C5 120.8(3) . . ?
O1 N2 C5 118.1(3) . . ?
C9 N3 C11 121.2(3) . . ?
C9 N3 C10 121.5(3) . . ?
C11 N3 C10 117.3(3) . . ?
C6 C1 C2 119.5(3) . . ?
C6 C1 C7 120.1(3) . . ?
C2 C1 C7 120.4(3) . . ?
C3 C2 C1 120.0(3) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 123.8(3) . . ?
C2 C3 H3 118.1 . . ?
C4 C3 H3 118.1 . . ?
C5 C4 C3 113.9(3) . . ?
C5 C4 C8 126.1(3) . . ?
C3 C4 C8 120.1(3) . . ?
C6 C5 C4 122.8(3) . . ?
C6 C5 N2 114.3(3) . . ?
C4 C5 N2 122.8(3) . . ?
C1 C6 C5 120.0(3) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
N1 C7 C1 179.2(3) . . ?
C9 C8 C4 124.1(3) . . ?
C9 C8 H8 117.9 . . ?
C4 C8 H8 117.9 . . ?
N3 C9 C8 124.8(3) . . ?
N3 C9 H9 117.6 . . ?
C8 C9 H9 117.6 . . ?
N3 C10 H10A 109.5 . . ?
N3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N3 C11 H11A 109.5 . . ?
N3 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N3 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N2 1.231(4) . ?
O2 N2 1.227(3) . ?
N1 C7 1.158(4) . ?
N2 C5 1.450(4) . ?
N3 C9 1.334(4) . ?
N3 C11 1.449(4) . ?
N3 C10 1.461(5) . ?
C1 C6 1.377(4) . ?
C1 C2 1.410(5) . ?
C1 C7 1.436(5) . ?
C2 C3 1.358(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.429(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.427(4) . ?
C4 C8 1.433(4) . ?
C5 C6 1.396(4) . ?
C6 H6 0.9500 . ?
C8 C9 1.369(5) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.7(5) . . . . ?
C7 C1 C2 C3 177.0(3) . . . . ?
C1 C2 C3 C4 -0.5(5) . . . . ?
C2 C3 C4 C5 1.9(5) . . . . ?
C2 C3 C4 C8 -177.7(3) . . . . ?
C3 C4 C5 C6 -2.2(4) . . . . ?
C8 C4 C5 C6 177.3(3) . . . . ?
C3 C4 C5 N2 -179.4(3) . . . . ?
C8 C4 C5 N2 0.1(5) . . . . ?
O2 N2 C5 C6 -175.8(3) . . . . ?
O1 N2 C5 C6 4.4(4) . . . . ?
O2 N2 C5 C4 1.7(5) . . . . ?
O1 N2 C5 C4 -178.2(3) . . . . ?
C2 C1 C6 C5 0.4(5) . . . . ?
C7 C1 C6 C5 -177.3(3) . . . . ?
C4 C5 C6 C1 1.2(5) . . . . ?
N2 C5 C6 C1 178.6(3) . . . . ?
C6 C1 C7 N1 -169(28) . . . . ?
C2 C1 C7 N1 13(28) . . . . ?
C5 C4 C8 C9 -177.0(3) . . . . ?
C3 C4 C8 C9 2.5(5) . . . . ?
C11 N3 C9 C8 -178.2(3) . . . . ?
C10 N3 C9 C8 -0.1(5) . . . . ?
C4 C8 C9 N3 178.8(3) . . . . ?
