#------------------------------------------------------------------------------
#$Date: 2018-08-23 04:33:40 +0300 (Thu, 23 Aug 2018) $
#$Revision: 210090 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/46/4024644.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_4024644
loop_
_publ_author_name
'Feldman, Ken S.'
'Hester, D. Keith'
'Iyer, Malliga R.'
'Munson, Paul J.'
'Silva López, Carlos'
'Faza, Olalla Nieto'
_publ_section_title
;
 Allenyl Azide Cycloaddition Chemistry. 2,3-Cyclopentennelated Indole
 Synthesis through Indolidene Intermediates
;
_journal_coden_ASTM              JOCEAH
_journal_issue                   14
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4958
_journal_page_last               4974
_journal_paper_doi               10.1021/jo900659w
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C12 H11 N'
_chemical_formula_weight         169.22
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 92.517(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.907(4)
_cell_length_b                   5.6848(16)
_cell_length_c                   12.950(4)
_cell_measurement_reflns_used    2113
_cell_measurement_temperature    108(2)
_cell_measurement_theta_max      28.242
_cell_measurement_theta_min      2.274
_cell_volume                     875.7(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      108(2)
_diffrn_measured_fraction_theta_full 0.949
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0178
_diffrn_reflns_av_sigmaI/netI    0.0245
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5358
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.27
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         2066
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0517
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0693P)²+0.4061P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1320
_refine_ls_wR_factor_ref         0.1390
_reflns_number_gt                1729
_reflns_number_total             2066
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900659w_si_002.cif
_cod_data_source_block           mxr4s
_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.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4024644
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
N1 N 0.32930(10) 0.0574(2) 0.90539(10) 0.0202(3) Uani 1 1 d . . .
C2 C 0.37350(13) 0.2192(3) 0.73047(12) 0.0246(3) Uani 1 1 d . . .
H2 H 0.3246 0.3509 0.7329 0.030 Uiso 1 1 calc R . .
C8 C 0.36354(11) -0.1333(2) 0.96588(11) 0.0183(3) Uani 1 1 d . . .
C1 C 0.38294(11) 0.0598(2) 0.81150(11) 0.0200(3) Uani 1 1 d . . .
C6 C 0.45377(11) -0.1363(2) 0.80915(11) 0.0195(3) Uani 1 1 d . . .
C9 C 0.30725(12) -0.1242(3) 1.05583(11) 0.0218(3) Uani 1 1 d . . .
C5 C 0.51713(12) -0.1751(3) 0.72379(11) 0.0231(3) Uani 1 1 d . . .
H5 H 0.5651 -0.3082 0.7210 0.028 Uiso 1 1 calc R . .
C10 C 0.23639(12) 0.0796(3) 1.04808(12) 0.0257(3) Uani 1 1 d . . .
H10 H 0.1871 0.1310 1.0992 0.031 Uiso 1 1 calc R . .
C7 C 0.44850(11) -0.2728(2) 0.90925(10) 0.0191(3) Uani 1 1 d . . .
H7A H 0.4228 -0.4364 0.8968 0.023 Uiso 1 1 calc R . .
H7B H 0.5223 -0.2752 0.9475 0.023 Uiso 1 1 calc R . .
C4 C 0.50949(13) -0.0157(3) 0.64172(12) 0.0261(4) Uani 1 1 d . . .
H4 H 0.5530 -0.0397 0.5829 0.031 Uiso 1 1 calc R . .
C11 C 0.25118(12) 0.1883(3) 0.95521(12) 0.0251(4) Uani 1 1 d . . .
H11 H 0.2146 0.3268 0.9302 0.030 Uiso 1 1 calc R . .
C3 C 0.43835(13) 0.1786(3) 0.64571(12) 0.0268(4) Uani 1 1 d . . .
H3 H 0.4341 0.2855 0.5893 0.032 Uiso 1 1 calc R . .
C12 C 0.31940(13) -0.2895(3) 1.14543(12) 0.0255(3) Uani 1 1 d . . .
H12A H 0.2941 -0.4467 1.1238 0.038 Uiso 1 1 calc R . .
H12B H 0.2736 -0.2337 1.2015 0.038 Uiso 1 1 calc R . .
H12C H 0.3985 -0.2965 1.1697 0.038 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'
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
C11 N1 C8 110.24(13) . . ?
C11 N1 C1 138.40(13) . . ?
C8 N1 C1 111.36(12) . . ?
C1 C2 C3 117.39(14) . . ?
C1 C2 H2 121.3 . . ?
C3 C2 H2 121.3 . . ?
C9 C8 N1 107.93(12) . . ?
C9 C8 C7 143.14(13) . . ?
N1 C8 C7 108.93(12) . . ?
C2 C1 N1 129.73(14) . . ?
C2 C1 C6 122.20(14) . . ?
N1 C1 C6 108.06(12) . . ?
C5 C6 C1 119.66(13) . . ?
C5 C6 C7 130.31(13) . . ?
C1 C6 C7 110.00(12) . . ?
C8 C9 C10 106.21(13) . . ?
C8 C9 C12 127.00(13) . . ?
C10 C9 C12 126.77(13) . . ?
C6 C5 C4 119.02(14) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C11 C10 C9 109.14(14) . . ?
C11 C10 H10 125.4 . . ?
C9 C10 H10 125.4 . . ?
C8 C7 C6 101.61(11) . . ?
C8 C7 H7A 111.4 . . ?
C6 C7 H7A 111.4 . . ?
C8 C7 H7B 111.4 . . ?
C6 C7 H7B 111.4 . . ?
H7A C7 H7B 109.3 . . ?
C3 C4 C5 120.34(14) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C10 C11 N1 106.48(13) . . ?
C10 C11 H11 126.8 . . ?
N1 C11 H11 126.8 . . ?
C2 C3 C4 121.38(14) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
N1 C11 1.3738(19) . ?
N1 C8 1.3882(18) . ?
N1 C1 1.398(2) . ?
C2 C1 1.387(2) . ?
C2 C3 1.389(2) . ?
C2 H2 0.9500 . ?
C8 C9 1.370(2) . ?
C8 C7 1.5020(19) . ?
C1 C6 1.399(2) . ?
C6 C5 1.383(2) . ?
C6 C7 1.5144(19) . ?
C9 C10 1.434(2) . ?
C9 C12 1.495(2) . ?
C5 C4 1.397(2) . ?
C5 H5 0.9500 . ?
C10 C11 1.370(2) . ?
C10 H10 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C4 C3 1.394(2) . ?
C4 H4 0.9500 . ?
C11 H11 0.9500 . ?
C3 H3 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 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
C11 N1 C8 C9 -0.32(16) . . . . ?
C1 N1 C8 C9 -179.70(11) . . . . ?
C11 N1 C8 C7 179.84(11) . . . . ?
C1 N1 C8 C7 0.46(15) . . . . ?
C3 C2 C1 N1 179.48(13) . . . . ?
C3 C2 C1 C6 -0.5(2) . . . . ?
C11 N1 C1 C2 1.6(3) . . . . ?
C8 N1 C1 C2 -179.31(13) . . . . ?
C11 N1 C1 C6 -178.43(16) . . . . ?
C8 N1 C1 C6 0.69(15) . . . . ?
C2 C1 C6 C5 0.0(2) . . . . ?
N1 C1 C6 C5 -179.96(12) . . . . ?
C2 C1 C6 C7 178.44(12) . . . . ?
N1 C1 C6 C7 -1.56(15) . . . . ?
N1 C8 C9 C10 0.27(15) . . . . ?
C7 C8 C9 C10 -179.98(18) . . . . ?
N1 C8 C9 C12 -178.21(13) . . . . ?
C7 C8 C9 C12 1.5(3) . . . . ?
C1 C6 C5 C4 0.4(2) . . . . ?
C7 C6 C5 C4 -177.58(13) . . . . ?
C8 C9 C10 C11 -0.13(16) . . . . ?
C12 C9 C10 C11 178.35(14) . . . . ?
C9 C8 C7 C6 178.96(19) . . . . ?
N1 C8 C7 C6 -1.30(14) . . . . ?
C5 C6 C7 C8 179.91(14) . . . . ?
C1 C6 C7 C8 1.73(14) . . . . ?
C6 C5 C4 C3 -0.4(2) . . . . ?
C9 C10 C11 N1 -0.06(16) . . . . ?
C8 N1 C11 C10 0.23(16) . . . . ?
C1 N1 C11 C10 179.36(16) . . . . ?
C1 C2 C3 C4 0.5(2) . . . . ?
C5 C4 C3 C2 0.0(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21152038
