#------------------------------------------------------------------------------
#$Date: 2019-09-20 17:12:36 +0200 (vie 20 de sep de 2019) $
#$Revision: 218620 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/61/1506105.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_1506105
loop_
_publ_author_name
'Feldman, Ken S.'
'Iyer, Malliga R.'
'Hester, II, D. Keith'
_publ_section_title
;
 Allenyl azide cycloaddition chemistry. Synthesis of annelated indoles
 from 2-(allenyl)phenyl azide substrates
;
_journal_coden_ASTM              ORLEF7
_journal_issue                   14
_journal_name_full               'Organic Letters'
_journal_page_first              3113
_journal_page_last               3116
_journal_paper_doi               10.1021/ol061216u
_journal_volume                  8
_journal_year                    2006
_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(5)
_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            ol061216usi20060518_081936.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_values 1715 2011-07-08 13:25:40Z adriana 

 Updated bibliographic information.

 Antanas Vaitkus,
 2019-09-20
;
_cod_original_cell_volume        875.7(4)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1506105
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
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_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0194(6) 0.0170(6) 0.0239(6) -0.0007(5) -0.0033(5) 0.0024(5)
C2 0.0252(7) 0.0205(7) 0.0272(8) 0.0026(6) -0.0100(6) -0.0015(6)
C8 0.0184(6) 0.0156(6) 0.0206(7) -0.0008(5) -0.0030(5) -0.0004(5)
C1 0.0191(6) 0.0195(7) 0.0208(7) -0.0003(5) -0.0059(5) -0.0037(5)
C6 0.0200(6) 0.0181(7) 0.0201(7) -0.0002(5) -0.0031(5) -0.0035(5)
C9 0.0202(7) 0.0216(7) 0.0235(7) -0.0035(5) -0.0011(5) -0.0029(6)
C5 0.0228(7) 0.0228(7) 0.0237(7) -0.0009(6) -0.0005(6) -0.0013(6)
C10 0.0211(7) 0.0235(7) 0.0325(8) -0.0058(6) 0.0003(6) 0.0012(6)
C7 0.0201(7) 0.0161(6) 0.0209(7) -0.0002(5) -0.0007(5) 0.0010(5)
C4 0.0273(7) 0.0305(8) 0.0203(7) -0.0002(6) -0.0015(6) -0.0056(6)
C11 0.0203(7) 0.0211(7) 0.0334(8) -0.0042(6) -0.0022(6) 0.0049(6)
C3 0.0309(8) 0.0259(8) 0.0226(8) 0.0046(6) -0.0094(6) -0.0061(6)
C12 0.0262(8) 0.0259(8) 0.0245(8) -0.0013(6) 0.0025(6) -0.0013(6)
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
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
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
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
