#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/31/4023175.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_4023175
loop_
_publ_author_name
'Jean-Martial L'Helgoual'ch'
'Anne Seggio'
'Floris Chevallier'
'Mitsuhiro Yonehara'
'Erwann Jeanneau'
'Masanobu Uchiyama'
'Florence Mongin'
_publ_contact_author_address
;     Synthèse et Electrosynthèse Organique
 UMR 6510 CNRS, Université de Rennes 1
 Avenue du Général Leclerc
 35042 Rennes Cedex, France.
;
_publ_contact_author_email       florence.mongin@univ-rennes1.fr
_publ_contact_author_name        'MONGIN, Florence'
_publ_section_title
;
 Deprotonative Metalation of Five-Membered Aromatic Heterocycles
 Using Mixed Lithium-Zinc Species
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              177
_journal_page_last               183
_journal_paper_doi               10.1021/jo7020345
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C3 H1 I2 N1 S1'
_chemical_formula_sum            'C3 H I2 N S'
_chemical_formula_weight         336.92
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             07-08-28
_audit_creation_method           CRYSTALS_ver_12.85
_cell_angle_alpha                90
_cell_angle_beta                 117.33(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.363(4)
_cell_length_b                   13.529(6)
_cell_length_c                   7.998(1)
_cell_measurement_reflns_used    1263
_cell_measurement_temperature    295
_cell_measurement_theta_max      27.878
_cell_measurement_theta_min      0.730
_cell_volume                     707.8(5)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1997-2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      295
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.079
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3390
_diffrn_reflns_theta_full        26.996
_diffrn_reflns_theta_max         28.416
_diffrn_reflns_theta_min         3.011
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    9.069
_exptl_absorpt_correction_T_max  0.48
_exptl_absorpt_correction_T_min  0.24
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details   'DIFABS (Walker & Stuart, 1983)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    3.162
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.11
_refine_diff_density_min         -1.52
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.1060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     64
_refine_ls_number_reflns         926
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0796
_refine_ls_R_factor_gt           0.0585
_refine_ls_shift/su_max          0.000248
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 2.31 0.631 1.53 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0835
_refine_ls_wR_factor_gt          0.0673
_refine_ls_wR_factor_ref         0.0637
_reflns_limit_h_max              8
_reflns_limit_h_min              -9
_reflns_limit_k_max              17
_reflns_limit_k_min              0
_reflns_limit_l_max              10
_reflns_limit_l_min              0
_reflns_number_gt                1069
_reflns_number_total             1720
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_r_factor_ref   0.0549
_oxford_refine_ls_scale          0.725(4)
_oxford_reflns_number_all        1715
_oxford_reflns_threshold_expression_ref I>3.0\s(I)
_cod_data_source_file            jo7020345-File003.cif
_cod_data_source_block           jml016
_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/c'
_cod_original_formula_sum        'C3 H1 I2 N S'
_cod_database_code               4023175
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
x,-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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
I1 I 0.99305(11) 0.55037(6) 0.75064(10) 0.0545 1.0000 Uani . . . . . . .
I2 I 0.41314(14) 0.17450(7) 0.63553(14) 0.0719 1.0000 Uani . . . . . . .
S1 S 0.6175(5) 0.3955(2) 0.6934(4) 0.0578 1.0000 Uani . . . . . . .
C2 C 0.8513(16) 0.4141(9) 0.6964(15) 0.0500 1.0000 Uani . . . . . . .
N1 N 0.8043(14) 0.2466(7) 0.6494(14) 0.0554 1.0000 Uani . . . . . . .
C3 C 0.6399(17) 0.2719(8) 0.6595(15) 0.0516 1.0000 Uani . . . . . . .
C1 C 0.923(2) 0.3282(9) 0.6700(18) 0.0590 1.0000 Uani . . . . . . .
H11 H 1.0406 0.3244 0.6543 0.0560 1.0000 Uiso 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
I1 0.0570(5) 0.0554(5) 0.0535(5) -0.0018(3) 0.0273(4) -0.0046(3)
I2 0.0638(6) 0.0746(6) 0.0707(6) 0.0014(4) 0.0251(4) -0.0180(4)
S1 0.0558(16) 0.0587(17) 0.0639(17) -0.0035(13) 0.0317(14) -0.0002(13)
C2 0.050(6) 0.057(6) 0.043(5) 0.001(4) 0.022(5) -0.007(5)
N1 0.052(5) 0.056(6) 0.054(6) 0.008(4) 0.021(4) 0.006(4)
C3 0.055(7) 0.055(6) 0.040(6) -0.003(5) 0.017(5) -0.005(5)
C1 0.070(8) 0.060(7) 0.065(7) 0.011(6) 0.047(7) 0.012(6)
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
I -0.4742 1.8119 20.1472 4.3470 18.9949 0.3814 7.5138 27.7660 2.2735 66.8776
4.0712 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . S1 . C3 . 88.7(6) yes
S1 . C2 . I1 . 122.5(6) yes
S1 . C2 . C1 . 109.6(9) yes
I1 . C2 . C1 . 127.8(9) yes
C3 . N1 . C1 . 110.1(10) yes
S1 . C3 . I2 . 120.3(6) yes
S1 . C3 . N1 . 115.3(9) yes
I2 . C3 . N1 . 124.4(8) yes
N1 . C1 . C2 . 116.3(11) yes
N1 . C1 . H11 . 121.4 no
C2 . C1 . H11 . 122.0 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
I1 . C2 . 2.064(11) yes
I2 . C3 . 2.065(11) yes
S1 . C2 . 1.729(11) yes
S1 . C3 . 1.715(11) yes
C2 . C1 . 1.334(16) yes
N1 . C3 . 1.295(15) yes
N1 . C1 . 1.370(16) yes
C1 . H11 . 0.931 no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658631
