#------------------------------------------------------------------------------
#$Date: 2017-03-04 10:06:25 +0200 (Sat, 04 Mar 2017) $
#$Revision: 193272 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/22/4032288.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_4032288
loop_
_publ_author_name
'Hasty, Scott J.'
'Bandara, Mithila D.'
'Rath, Nigam P.'
'Demchenko, Alexei V.'
_publ_section_title
;
 S-Benzimidazolyl (SBiz) Imidates as a Platform for Oligosaccharide
 Synthesis via Active-Latent, Armed-Disarmed, Selective, and Orthogonal
 Activations.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1904
_journal_page_last               1911
_journal_paper_doi               10.1021/acs.joc.6b02478
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C9 H11 N2 S, I'
_chemical_formula_sum            'C9 H11 I N2 S'
_chemical_formula_weight         306.16
_chemical_name_systematic
; 
 ? 
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2012
_cell_angle_alpha                67.948(2)
_cell_angle_beta                 88.957(2)
_cell_angle_gamma                70.779(2)
_cell_formula_units_Z            2
_cell_length_a                   6.6795(3)
_cell_length_b                   9.4844(4)
_cell_length_c                   9.9184(4)
_cell_measurement_reflns_used    9878
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      38.53
_cell_measurement_theta_min      3.25
_cell_volume                     545.91(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_unetI/netI     0.0530
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11903
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         39.148
_diffrn_reflns_theta_min         3.718
_exptl_absorpt_coefficient_mu    3.082
_exptl_absorpt_correction_T_max  0.8841
_exptl_absorpt_correction_T_min  0.2698
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'sadabs v2008/1'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.863
_exptl_crystal_description       rod
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.576
_exptl_crystal_size_mid          0.119
_exptl_crystal_size_min          0.041
_refine_diff_density_max         1.087
_refine_diff_density_min         -1.258
_refine_diff_density_rms         0.122
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         6165
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0237
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
; 
 w=1/[σ²(Fo²)+(0.0174P)²] 
 where P=(Fo²+2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0522
_refine_ls_wR_factor_ref         0.0541
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5279
_reflns_number_total             6165
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo6b02478_si_001.cif
_cod_data_source_block           d2413t4
_cod_database_code               4032288
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.270
_shelx_estimated_absorpt_t_max   0.884
_shelxl_version_number           2012-9
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.61128(2) 0.81184(2) 0.76371(2) 0.01816(3) Uani 0.9942(3) 1 d . . P A 1
I1' I 0.504(3) 0.8045(16) 0.7670(15) 0.01816(3) Uani 0.0058(3) 1 d . . P A 2
S1 S 0.91637(5) 0.19785(4) 0.87866(3) 0.01956(6) Uani 1 1 d . . . . .
N1 N 0.88186(16) 0.28631(12) 0.58772(11) 0.01439(16) Uani 1 1 d . . . . .
N2 N 0.74191(15) 0.49444(11) 0.64794(10) 0.01229(15) Uani 1 1 d . . . . .
H2 H 0.697(3) 0.559(2) 0.697(2) 0.028(5) Uiso 1 1 d . . . . .
C1 C 0.84264(17) 0.33381(13) 0.69990(12) 0.01297(17) Uani 1 1 d . . . . .
C2 C 0.80067(17) 0.42152(14) 0.45772(12) 0.01377(17) Uani 1 1 d . . . . .
C3 C 0.7966(2) 0.43875(17) 0.31170(14) 0.0192(2) Uani 1 1 d . . . . .
H3 H 0.8549 0.3482 0.2853 0.023 Uiso 1 1 calc R U . . .
C4 C 0.7033(2) 0.59423(19) 0.20756(14) 0.0224(2) Uani 1 1 d . . . . .
H4 H 0.6972 0.6111 0.1068 0.027 Uiso 1 1 calc R U . . .
C5 C 0.61702(19) 0.72832(17) 0.24645(13) 0.0209(2) Uani 1 1 d . . . . .
H5 H 0.5554 0.8335 0.1713 0.025 Uiso 1 1 calc R U . . .
C6 C 0.61936(19) 0.71135(15) 0.39132(13) 0.01666(19) Uani 1 1 d . . . . .
H6 H 0.5603 0.8017 0.4178 0.020 Uiso 1 1 calc R U . . .
C7 C 0.71327(17) 0.55416(13) 0.49591(12) 0.01247(17) Uani 1 1 d . . . . .
C8 C 0.9901(2) 0.11964(16) 0.60136(17) 0.0245(3) Uani 1 1 d . . . . .
H8A H 1.1017 0.0630 0.6853 0.037 Uiso 1 1 calc R U . . .
H8B H 1.0547 0.1202 0.5118 0.037 Uiso 1 1 calc R U . . .
H8C H 0.8864 0.0638 0.6162 0.037 Uiso 1 1 calc R U . . .
C9 C 0.8327(2) 0.33075(19) 0.97551(15) 0.0252(3) Uani 1 1 d . . . . .
H9A H 0.9008 0.4131 0.9418 0.038 Uiso 1 1 calc R U . . .
H9B H 0.8748 0.2674 1.0809 0.038 Uiso 1 1 calc R U . . .
H9C H 0.6772 0.3840 0.9565 0.038 Uiso 1 1 calc R U . . .
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'
S S 0.1246 0.1234 '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
C1 S1 C9 101.35(6)
C1 N1 C2 108.58(9)
C1 N1 C8 125.30(11)
C2 N1 C8 126.11(10)
C1 N2 C7 108.71(9)
C1 N2 H2 129.1(13)
C7 N2 H2 122.2(13)
N2 C1 N1 109.42(10)
N2 C1 S1 128.86(9)
N1 C1 S1 121.72(9)
N1 C2 C7 106.67(9)
N1 C2 C3 131.76(11)
C7 C2 C3 121.57(11)
C4 C3 C2 116.50(12)
C4 C3 H3 121.8
C2 C3 H3 121.8
C3 C4 C5 121.80(11)
C3 C4 H4 119.1
C5 C4 H4 119.1
C6 C5 C4 121.80(12)
C6 C5 H5 119.1
C4 C5 H5 119.1
C5 C6 C7 116.14(12)
C5 C6 H6 121.9
C7 C6 H6 121.9
N2 C7 C2 106.61(9)
N2 C7 C6 131.21(10)
C2 C7 C6 122.19(11)
N1 C8 H8A 109.5
N1 C8 H8B 109.5
H8A C8 H8B 109.5
N1 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
S1 C9 H9A 109.5
S1 C9 H9B 109.5
H9A C9 H9B 109.5
S1 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.7164(11)
S1 C9 1.8027(15)
N1 C1 1.3407(14)
N1 C2 1.3882(15)
N1 C8 1.4596(16)
N2 C1 1.3370(14)
N2 C7 1.3889(14)
N2 H2 0.896(18)
C2 C7 1.3904(15)
C2 C3 1.3949(16)
C3 C4 1.380(2)
C3 H3 0.9500
C4 C5 1.406(2)
C4 H4 0.9500
C5 C6 1.3843(17)
C5 H5 0.9500
C6 C7 1.3925(16)
C6 H6 0.9500
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 I1 0.896(18) 2.604(19) 3.4600(9) 160.2(17) .
N2 H2 I1' 0.896(18) 2.60(2) 3.468(13) 163.4(17) .
C8 H8A I1' 0.98 2.85 3.632(16) 136.9 1_645
C9 H9B I1' 0.98 3.06 3.532(17) 110.8 2_667
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
C7 N2 C1 N1 0.29(13)
C7 N2 C1 S1 -179.27(8)
C2 N1 C1 N2 -0.80(13)
C8 N1 C1 N2 179.77(11)
C2 N1 C1 S1 178.79(8)
C8 N1 C1 S1 -0.63(16)
C9 S1 C1 N2 -2.50(12)
C9 S1 C1 N1 177.99(10)
C1 N1 C2 C7 0.99(12)
C8 N1 C2 C7 -179.59(11)
C1 N1 C2 C3 -179.08(12)
C8 N1 C2 C3 0.3(2)
N1 C2 C3 C4 -179.31(12)
C7 C2 C3 C4 0.61(17)
C2 C3 C4 C5 0.06(18)
C3 C4 C5 C6 -0.60(19)
C4 C5 C6 C7 0.43(17)
C1 N2 C7 C2 0.33(12)
C1 N2 C7 C6 -179.61(12)
N1 C2 C7 N2 -0.80(11)
C3 C2 C7 N2 179.26(10)
N1 C2 C7 C6 179.15(11)
C3 C2 C7 C6 -0.79(17)
C5 C6 C7 N2 -179.82(11)
C5 C6 C7 C2 0.25(16)
