#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/23/1512367.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_1512367
loop_
_publ_author_name
'Bharathiraja, Ganesan'
'Sakthivel, Sekarpandi'
'Sengoden, Mani'
'Punniyamurthy, Tharmalingam'
_publ_section_title
;
 A Novel Tandem Sequence to Pyrrole Syntheses by 5-endo-dig Cyclization of
 1,3-Enynes with Amines.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              4996
_journal_page_last               4999
_journal_paper_doi               10.1021/ol402305b
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C24 H19 I N2 O2'
_chemical_formula_sum            'C24 H19 I N2 O2'
_chemical_formula_weight         494.31
_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                67.406(18)
_cell_angle_beta                 73.018(16)
_cell_angle_gamma                82.661(18)
_cell_formula_units_Z            2
_cell_length_a                   10.504(3)
_cell_length_b                   10.554(3)
_cell_length_c                   11.201(3)
_cell_measurement_reflns_used    5427
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      0.801
_cell_measurement_theta_min      0.708
_cell_volume                     1096.3(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    SHELXS-87
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.727
_diffrn_measured_fraction_theta_max 0.801
_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  0.0262
_diffrn_reflns_av_sigmaI/netI    0.0310
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5427
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.03
_exptl_absorpt_coefficient_mu    1.482
_exptl_absorpt_correction_T_max  0.801
_exptl_absorpt_correction_T_min  0.708
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   multi-scan
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'irregular rectangles'
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.497
_refine_diff_density_min         -0.796
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         5427
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0313
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0497P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0790
_refine_ls_wR_factor_ref         0.0883
_reflns_number_gt                3111
_reflns_number_total             5427
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ol402305b_si_002.cif
_cod_data_source_block           tp-1
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_database_code               1512367
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
C22 C 0.0389(5) 0.5759(4) 0.6229(4) 0.0734(13) Uani 1 1 d .
H22 H 0.0111 0.6568 0.5640 0.088 Uiso 1 1 calc R
C21 C -0.0528(4) 0.4736(4) 0.6996(4) 0.0623(10) Uani 1 1 d .
C24 C -0.1955(5) 0.4930(5) 0.6925(5) 0.0981(16) Uani 1 1 d .
H24A H -0.2509 0.5081 0.7709 0.147 Uiso 1 1 calc R
H24B H -0.2238 0.4124 0.6880 0.147 Uiso 1 1 calc R
H24C H -0.2026 0.5709 0.6139 0.147 Uiso 1 1 calc R
C23 C 0.2678(6) 0.6799(5) 0.5455(5) 0.116(2) Uani 1 1 d .
H23A H 0.2748 0.7295 0.5994 0.173 Uiso 1 1 calc R
H23B H 0.2375 0.7411 0.4698 0.173 Uiso 1 1 calc R
H23C H 0.3534 0.6420 0.5146 0.173 Uiso 1 1 calc R
N1 N 0.2280(3) 0.1061(3) 0.8420(2) 0.0430(6) Uani 1 1 d .
N2 N 0.2424(3) -0.0437(3) 1.1823(3) 0.0559(8) Uani 1 1 d .
O1 O 0.1734(3) -0.0197(4) 1.2783(3) 0.0971(11) Uani 1 1 d .
O2 O 0.3254(4) -0.1333(4) 1.1921(3) 0.1152(14) Uani 1 1 d .
I1 I 0.08740(2) 0.29256(3) 1.12940(2) 0.06029(12) Uani 1 1 d .
C16 C 0.1618(3) 0.1694(3) 1.0179(3) 0.0447(8) Uani 1 1 d .
C1 C 0.3274(3) -0.1249(3) 0.9240(3) 0.0440(8) Uani 1 1 d .
C13 C 0.1657(3) 0.2100(3) 0.8853(3) 0.0438(8) Uani 1 1 d .
C14 C 0.2678(3) 0.0008(3) 0.9424(3) 0.0437(8) Uani 1 1 d .
C17 C 0.1209(3) 0.3378(3) 0.7936(3) 0.0468(8) Uani 1 1 d .
C7 C 0.2537(3) 0.1108(3) 0.7065(3) 0.0437(7) Uani 1 1 d .
C15 C 0.2262(3) 0.0412(3) 1.0525(3) 0.0438(8) Uani 1 1 d .
C18 C -0.0099(4) 0.3548(4) 0.7843(3) 0.0571(9) Uani 1 1 d .
H18 H -0.0693 0.2837 0.8368 0.069 Uiso 1 1 calc R
C2 C 0.2557(4) -0.2059(4) 0.8952(3) 0.0504(8) Uani 1 1 d .
H2 H 0.1691 -0.1797 0.8896 0.061 Uiso 1 1 calc R
C12 C 0.1519(4) 0.0849(4) 0.6662(3) 0.0587(10) Uani 1 1 d .
H12 H 0.0671 0.0666 0.7246 0.070 Uiso 1 1 calc R
C19 C 0.2092(4) 0.4446(4) 0.7153(3) 0.0570(9) Uani 1 1 d .
H19 H 0.2965 0.4342 0.7217 0.068 Uiso 1 1 calc R
C11 C 0.1770(5) 0.0862(5) 0.5368(4) 0.0741(12) Uani 1 1 d .
H11 H 0.1092 0.0673 0.5085 0.089 Uiso 1 1 calc R
C4 C 0.4378(5) -0.3608(5) 0.8793(4) 0.0734(11) Uani 1 1 d .
H4 H 0.4759 -0.4385 0.8620 0.088 Uiso 1 1 calc R
C5 C 0.4565(4) -0.1666(4) 0.9317(4) 0.0637(10) Uani 1 1 d .
H5 H 0.5062 -0.1148 0.9522 0.076 Uiso 1 1 calc R
C8 C 0.3786(4) 0.1403(4) 0.6211(3) 0.0649(11) Uani 1 1 d .
H8 H 0.4468 0.1589 0.6490 0.078 Uiso 1 1 calc R
C3 C 0.3086(4) -0.3226(4) 0.8748(4) 0.0659(11) Uani 1 1 d .
H3 H 0.2576 -0.3764 0.8579 0.079 Uiso 1 1 calc R
C6 C 0.5110(4) -0.2821(5) 0.9099(5) 0.0809(14) Uani 1 1 d .
H6 H 0.5976 -0.3087 0.9155 0.097 Uiso 1 1 calc R
C20 C 0.1698(5) 0.5653(4) 0.6284(3) 0.0662(11) Uani 1 1 d .
C10 C 0.4012(5) 0.1421(5) 0.4924(4) 0.0853(14) Uani 1 1 d .
H10 H 0.4856 0.1617 0.4334 0.102 Uiso 1 1 calc R
C9 C 0.3011(5) 0.1154(5) 0.4514(4) 0.0807(13) Uani 1 1 d .
H9 H 0.3175 0.1170 0.3646 0.097 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'
I I -0.4742 1.8119 '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
C21 C22 C20 123.8(4)
C18 C21 C22 117.3(4)
C18 C21 C24 121.2(4)
C22 C21 C24 121.4(4)
C14 N1 C13 111.3(2)
C14 N1 C7 124.3(3)
C13 N1 C7 124.4(3)
O2 N2 O1 122.1(3)
O2 N2 C15 119.5(3)
O1 N2 C15 118.3(4)
C13 C16 C15 106.7(3)
C13 C16 I1 123.2(3)
C15 C16 I1 129.9(2)
C2 C1 C5 117.9(4)
C2 C1 C14 120.0(3)
C5 C1 C14 122.1(3)
C16 C13 N1 107.4(3)
C16 C13 C17 131.0(3)
N1 C13 C17 121.5(3)
N1 C14 C15 104.6(3)
N1 C14 C1 121.5(3)
C15 C14 C1 133.6(3)
C19 C17 C18 119.0(3)
C19 C17 C13 120.0(3)
C18 C17 C13 120.9(3)
C12 C7 C8 121.2(3)
C12 C7 N1 118.9(3)
C8 C7 N1 119.9(3)
C14 C15 C16 110.0(3)
C14 C15 N2 123.0(3)
C16 C15 N2 126.9(3)
C21 C18 C17 121.4(3)
C3 C2 C1 121.8(4)
C7 C12 C11 119.1(4)
C20 C19 C17 121.2(4)
C9 C11 C12 120.0(4)
C3 C4 C6 119.5(5)
C6 C5 C1 120.9(4)
C7 C8 C10 118.8(4)
C2 C3 C4 119.7(4)
C5 C6 C4 120.2(4)
C19 C20 C22 117.2(4)
C19 C20 C23 119.9(4)
C22 C20 C23 122.9(4)
C9 C10 C8 120.6(4)
C10 C9 C11 120.4(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C22 C21 1.379(6)
C22 C20 1.382(6)
C21 C18 1.367(5)
C21 C24 1.508(6)
C23 C20 1.511(6)
N1 C14 1.367(4)
N1 C13 1.381(4)
N1 C7 1.444(4)
N2 O2 1.197(4)
N2 O1 1.206(4)
N2 C15 1.432(4)
I1 C16 2.068(3)
C16 C13 1.368(4)
C16 C15 1.398(5)
C1 C2 1.385(5)
C1 C5 1.388(5)
C1 C14 1.455(5)
C13 C17 1.467(5)
C14 C15 1.391(4)
C17 C19 1.390(5)
C17 C18 1.392(5)
C7 C12 1.369(4)
C7 C8 1.369(5)
C2 C3 1.358(6)
C12 C11 1.390(5)
C19 C20 1.375(5)
C11 C9 1.362(6)
C4 C3 1.376(6)
C4 C6 1.391(7)
C5 C6 1.357(6)
C8 C10 1.383(5)
C10 C9 1.362(6)
