#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:38:22 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180309 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/23/7152322.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_7152322
loop_
_publ_author_name
'Huang, Jing-Mei'
'Ye, Zhi-Jun'
'Chen, Dong-Song'
'Zhu, Hong'
_publ_section_title
;
 Iodine mediated/Brønsted acid-catalyzed dimerization of vinylarenes: a
 tandem reaction through Ritter trapping to produce
 N-(4-iodo-1,3-diarylbutyl) acetamides.
;
_journal_issue                   18
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3610
_journal_page_last               3612
_journal_paper_doi               10.1039/c2ob25142f
_journal_volume                  10
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H20 I N O'
_chemical_formula_sum            'C18 H20 I N O'
_chemical_formula_weight         393.25
_chemical_name_systematic
;

?

;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 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                 120.648(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.3319(4)
_cell_length_b                   21.2699(8)
_cell_length_c                   9.3647(4)
_cell_measurement_reflns_used    8170
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      30.47
_cell_measurement_theta_min      2.48
_cell_volume                     1770.50(13)
_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      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0223
_diffrn_reflns_av_sigmaI/netI    0.0331
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12308
_diffrn_reflns_theta_full        30.52
_diffrn_reflns_theta_max         30.52
_diffrn_reflns_theta_min         1.91
_exptl_absorpt_coefficient_mu    1.808
_exptl_absorpt_correction_T_max  0.7138
_exptl_absorpt_correction_T_min  0.6131
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.194
_refine_diff_density_min         -1.047
_refine_diff_density_rms         0.194
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         4293
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.155
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0339
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0501P)²+2.6421P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.1084
_reflns_number_gt                4053
_reflns_number_total             4293
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ob25142f.txt
_cod_data_source_block           ltp64
_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 
;
_cod_original_cell_volume        1770.50(12)
_cod_original_sg_symbol_H-M      Cc
_cod_database_code               7152322
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, 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
C1 C 0.6085(5) 0.78335(19) 0.2899(6) 0.0400(8) Uani 1 1 d .
H1A H 0.5315 0.7897 0.1716 0.048 Uiso 1 1 calc R
H1B H 0.5732 0.7491 0.3332 0.048 Uiso 1 1 calc R
C2 C 0.6226(4) 0.84380(16) 0.3855(5) 0.0325(7) Uani 1 1 d .
H2 H 0.6665 0.8772 0.3476 0.039 Uiso 1 1 calc R
C3 C 0.7222(4) 0.83693(17) 0.5725(5) 0.0334(7) Uani 1 1 d .
C4 C 0.6881(5) 0.7946(2) 0.6605(6) 0.0426(9) Uani 1 1 d .
H4 H 0.6057 0.7665 0.6030 0.051 Uiso 1 1 calc R
C5 C 0.7746(6) 0.7929(2) 0.8345(7) 0.0525(12) Uani 1 1 d .
H5 H 0.7507 0.7635 0.8939 0.063 Uiso 1 1 calc R
C6 C 0.8946(6) 0.8338(3) 0.9207(6) 0.0534(13) Uani 1 1 d .
H6 H 0.9512 0.8335 1.0385 0.064 Uiso 1 1 calc R
C7 C 0.9298(6) 0.8747(3) 0.8321(6) 0.0514(12) Uani 1 1 d .
H7 H 1.0136 0.9021 0.8891 0.062 Uiso 1 1 calc R
C8 C 0.8440(5) 0.8765(2) 0.6600(6) 0.0409(9) Uani 1 1 d .
H8 H 0.8696 0.9055 0.6011 0.049 Uiso 1 1 calc R
C9 C 0.4617(4) 0.86352(17) 0.3355(5) 0.0326(7) Uani 1 1 d .
H9A H 0.4053 0.8729 0.2152 0.039 Uiso 1 1 calc R
H9B H 0.4114 0.8276 0.3544 0.039 Uiso 1 1 calc R
C10 C 0.4522(4) 0.92082(16) 0.4292(4) 0.0289(6) Uani 1 1 d .
H10 H 0.5175 0.9124 0.5508 0.035 Uiso 1 1 calc R
C11 C 0.2918(4) 0.92876(16) 0.3919(5) 0.0323(7) Uani 1 1 d .
C12 C 0.1860(5) 0.9644(2) 0.2582(6) 0.0449(10) Uani 1 1 d .
H12 H 0.2138 0.9863 0.1893 0.054 Uiso 1 1 calc R
C13 C 0.0382(6) 0.9676(2) 0.2265(8) 0.0563(13) Uani 1 1 d .
H13 H -0.0343 0.9916 0.1348 0.068 Uiso 1 1 calc R
C14 C -0.0044(5) 0.9366(3) 0.3258(7) 0.0538(12) Uani 1 1 d .
H14 H -0.1046 0.9398 0.3040 0.065 Uiso 1 1 calc R
C15 C 0.1000(6) 0.9014(3) 0.4559(7) 0.0516(11) Uani 1 1 d .
H15 H 0.0716 0.8800 0.5246 0.062 Uiso 1 1 calc R
C16 C 0.2471(5) 0.8964(2) 0.4893(5) 0.0418(9) Uani 1 1 d .
H16 H 0.3175 0.8710 0.5787 0.050 Uiso 1 1 calc R
C17 C 0.5572(5) 1.02681(18) 0.4878(5) 0.0317(7) Uani 1 1 d .
C18 C 0.6095(5) 1.0823(2) 0.4335(5) 0.0403(9) Uani 1 1 d .
H18A H 0.5268 1.1125 0.3771 0.061 Uiso 1 1 calc R
H18B H 0.6423 1.0686 0.3570 0.061 Uiso 1 1 calc R
H18C H 0.6938 1.1024 0.5306 0.061 Uiso 1 1 calc R
I1 I 0.81579(7) 0.754913(14) 0.30699(8) 0.05164(11) Uani 1 1 d .
N1 N 0.5104(4) 0.97683(16) 0.3901(4) 0.0300(6) Uani 1 1 d .
H1 H 0.5145 0.9773 0.2984 0.036 Uiso 1 1 calc R
O1 O 0.5588(5) 1.02866(16) 0.6212(4) 0.0516(9) Uani 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'
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
C2 C1 I1 113.5(3)
C3 C2 C1 113.6(3)
C3 C2 C9 111.7(3)
C1 C2 C9 106.6(3)
C8 C3 C4 118.4(4)
C8 C3 C2 120.1(4)
C4 C3 C2 121.4(4)
C3 C4 C5 120.2(4)
C6 C5 C4 120.7(5)
C7 C6 C5 118.7(4)
C6 C7 C8 120.6(5)
C3 C8 C7 121.4(5)
C10 C9 C2 114.6(3)
N1 C10 C11 113.0(3)
N1 C10 C9 110.4(3)
C11 C10 C9 109.7(3)
C12 C11 C16 119.1(4)
C12 C11 C10 122.1(4)
C16 C11 C10 118.7(4)
C11 C12 C13 119.2(5)
C14 C13 C12 121.4(5)
C15 C14 C13 118.9(5)
C14 C15 C16 121.2(5)
C15 C16 C11 120.2(4)
O1 C17 N1 122.3(4)
O1 C17 C18 119.8(4)
N1 C17 C18 117.9(3)
C17 N1 C10 122.2(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.531(5)
C1 I1 2.151(4)
C2 C3 1.519(5)
C2 C9 1.538(5)
C3 C8 1.383(6)
C3 C4 1.383(6)
C4 C5 1.404(7)
C5 C6 1.387(8)
C6 C7 1.374(8)
C7 C8 1.389(7)
C9 C10 1.534(5)
C10 N1 1.463(5)
C10 C11 1.519(5)
C11 C12 1.393(6)
C11 C16 1.395(6)
C12 C13 1.401(7)
C13 C14 1.382(9)
C14 C15 1.367(8)
C15 C16 1.391(7)
C17 O1 1.241(4)
C17 N1 1.323(5)
C17 C18 1.492(5)
