#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/17/4021767.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_4021767
loop_
_publ_author_name
'Manyam Praveen Kumar'
'Rai-Shung Liu'
_publ_section_title
;
 Zn(OTf)₂-Catalyzed Cyclization of Proparyl Alcohols with Anilines,
 Phenols, and Amides for Synthesis of Indoles, Benzofurans,
 and Oxazoles through Different Annulation Mechanisms
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4951
_journal_page_last               4955
_journal_paper_doi               10.1021/jo0606711
_journal_volume                  71
_journal_year                    2006
_chemical_formula_sum            'C16 H15 N'
_chemical_formula_weight         221.29
_chemical_name_systematic
;
?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.603(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.5552(1)
_cell_length_b                   7.6732(1)
_cell_length_c                   12.5769(2)
_cell_measurement_reflns_used    2654
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.16
_cell_measurement_theta_min      3.12
_cell_volume                     625.492(16)
_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      296(2)
_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  0.0414
_diffrn_reflns_av_sigmaI/netI    0.0426
_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       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6370
_diffrn_reflns_theta_max         26.38
_diffrn_reflns_theta_min         1.64
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  0.97427
_exptl_absorpt_correction_T_min  0.88376
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       Columnar
_exptl_crystal_F_000             236
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   6(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     153
_refine_ls_number_reflns         2435
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.990
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0397
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0660P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0908
_refine_ls_wR_factor_ref         0.1136
_reflns_number_gt                1847
_reflns_number_total             2435
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0606711si20060330_012502.cif
_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      'P 21'
_cod_database_code               4021767
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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
N1 N 0.0829(2) 0.4680(3) 0.10198(11) 0.0514(4) Uani 1 1 d
C1 C 0.0945(3) 0.4239 -0.00270(13) 0.0476(4) Uani 1 1 d
C2 C -0.0448(3) 0.4530(4) -0.09565(15) 0.0559(5) Uani 1 1 d
C3 C 0.0028(3) 0.3932(4) -0.19197(16) 0.0593(5) Uani 1 1 d
C4 C 0.1883(3) 0.3038(4) -0.19375(16) 0.0621(6) Uani 1 1 d
C5 C 0.3269(3) 0.2726(4) -0.10235(17) 0.0595(5) Uani 1 1 d
C6 C 0.2826(3) 0.3362(3) -0.00322(15) 0.0484(5) Uani 1 1 d
C7 C 0.3876(3) 0.3311(4) 0.10529(15) 0.0496(5) Uani 1 1 d
C8 C 0.2616(3) 0.4147(4) 0.16705(14) 0.0484(5) Uani 1 1 d
C9 C 0.2820(3) 0.4439(4) 0.28401(14) 0.0526(5) Uani 1 1 d
C10 C 0.4675(3) 0.4951(5) 0.34382(18) 0.0696(6) Uani 1 1 d
C11 C 0.4797(4) 0.5260(5) 0.4528(2) 0.0886(9) Uani 1 1 d
C12 C 0.3108(5) 0.5061(6) 0.50387(18) 0.0933(9) Uani 1 1 d
C13 C 0.1285(4) 0.4559(6) 0.44614(18) 0.0884(9) Uani 1 1 d
C14 C 0.1119(3) 0.4248(5) 0.33668(16) 0.0689(6) Uani 1 1 d
C15 C -0.1465(4) 0.4225(5) -0.29375(17) 0.0828(7) Uani 1 1 d
C16 C 0.5881(3) 0.2430(4) 0.1431(2) 0.0740(7) Uani 1 1 d
H1 H -0.0005 0.5372 0.1229 0.080 Uiso 1 1 d
H2A H -0.1750 0.5135 -0.0968 0.080 Uiso 1 1 d
H4A H 0.2185 0.2654 -0.2638 0.080 Uiso 1 1 d
H5A H 0.4488 0.2094 -0.1014 0.080 Uiso 1 1 d
H10A H 0.5840 0.5030 0.3074 0.080 Uiso 1 1 d
H11A H 0.5905 0.5624 0.4872 0.080 Uiso 1 1 d
H12A H 0.3231 0.5396 0.5768 0.080 Uiso 1 1 d
H13A H 0.0062 0.4147 0.4849 0.080 Uiso 1 1 d
H14A H -0.0155 0.3866 0.2992 0.080 Uiso 1 1 d
H15A H -0.1568 0.3377 -0.3481 0.080 Uiso 1 1 d
H15B H -0.0974 0.5017 -0.3266 0.080 Uiso 1 1 d
H15C H -0.2791 0.4335 -0.2848 0.080 Uiso 1 1 d
H16A H 0.5871 0.1431 0.1153 0.080 Uiso 1 1 d
H16B H 0.6893 0.2878 0.1169 0.080 Uiso 1 1 d
H16C H 0.6208 0.2311 0.2299 0.080 Uiso 1 1 d
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
C1 N1 C8 109.27(14)
C1 N1 H1 126.4
C8 N1 H1 122.6
N1 C1 C2 130.06(17)
N1 C1 C6 107.30(15)
C2 C1 C6 122.64(17)
C3 C2 C1 118.74(18)
C3 C2 H2A 117.5
C1 C2 H2A 123.8
C2 C3 C4 119.35(18)
C2 C3 C15 119.6(2)
C4 C3 C15 121.02(19)
C5 C4 C3 122.61(17)
C5 C4 H4A 120.3
C3 C4 H4A 117.1
C4 C5 C6 118.77(18)
C4 C5 H5A 124.0
C6 C5 H5A 117.2
C1 C6 C5 117.85(17)
C1 C6 C7 107.77(15)
C5 C6 C7 134.37(17)
C8 C7 C6 106.33(15)
C8 C7 C16 127.39(18)
C6 C7 C16 126.19(17)
C7 C8 N1 109.30(15)
C7 C8 C9 131.46(16)
N1 C8 C9 119.13(15)
C14 C9 C10 118.22(18)
C14 C9 C8 120.06(16)
C10 C9 C8 121.70(18)
C11 C10 C9 120.1(2)
C11 C10 H10A 122.4
C9 C10 H10A 117.4
C12 C11 C10 121.0(2)
C12 C11 H11A 119.7
C10 C11 H11A 119.2
C13 C12 C11 119.3(2)
C13 C12 H12A 122.5
C11 C12 H12A 117.9
C12 C13 C14 120.8(2)
C12 C13 H13A 120.7
C14 C13 H13A 117.3
C13 C14 C9 120.48(19)
C13 C14 H14A 118.9
C9 C14 H14A ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.372(2)
N1 C8 1.386(2)
N1 H1 0.8322
C1 C2 1.389(3)
C1 C6 1.405(3)
C2 C3 1.374(3)
C2 H2A 0.9698
C3 C4 1.399(3)
C3 C15 1.508(3)
C4 C5 1.375(3)
C4 H4A 0.9773
C5 C6 1.409(3)
C5 H5A 0.9333
C6 C7 1.434(3)
C7 C8 1.375(3)
C7 C16 1.491(3)
C8 C9 1.474(3)
C9 C14 1.387(3)
C9 C10 1.388(3)
C10 C11 1.382(3)
C10 H10A 0.9487
C11 C12 1.369(4)
C11 H11A 0.8359
C12 C13 1.358(4)
C12 H12A 0.9438
C13 C14 1.385(3)
C13 H13A 1.0472
C14 H14A 0.9425
C15 H15A 0.9389
C15 H15B 0.8270
C15 H15C 0.8968
C16 H16A 0.8416
C16 H16B 0.8556
C16 H16C 1.0852
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9381871
