#------------------------------------------------------------------------------
#$Date: 2016-10-08 00:58:55 +0300 (Sat, 08 Oct 2016) $
#$Revision: 187053 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/61/7226125.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_7226125
loop_
_publ_author_name
'Koshti, Vijay S.'
'Thorat, Shridhar H.'
'Gote, Ravindra P.'
'Chikkali, Samir H.'
'Gonnade, Rajesh G.'
_publ_section_title
;
 The impact of modular substitution on crystal packing: the tale of two
 ureas
;
_journal_issue                   37
_journal_name_full               CrystEngComm
_journal_page_first              7078
_journal_paper_doi               10.1039/C6CE01324D
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C13 H11 I N2 S'
_chemical_formula_sum            'C13 H11 I N2 S'
_chemical_formula_weight         354.20
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-06-07 deposited with the CCDC.
2016-08-04 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 99.085(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.7772(11)
_cell_length_b                   5.1405(4)
_cell_length_c                   20.7792(16)
_cell_measurement_reflns_used    4408
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.85
_cell_measurement_theta_min      3.97
_cell_volume                     1347.68(19)
_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-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0432
_diffrn_reflns_av_sigmaI/netI    0.0402
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            7967
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.99
_exptl_absorpt_coefficient_mu    2.510
_exptl_absorpt_correction_T_max  0.5614
_exptl_absorpt_correction_T_min  0.3979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS,(BRUKER,2006)
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.746
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             688
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.693
_refine_diff_density_min         -1.552
_refine_diff_density_rms         0.112
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.186
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         2301
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.186
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0395
_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)+(0.0199P)²+3.6192P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0770
_refine_ls_wR_factor_ref         0.0793
_reflns_number_gt                2065
_reflns_number_total             2301
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ce01324d2.cif
_cod_data_source_block           10april
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN' changed to
'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7226122--7226134.cif.
;
_cod_original_sg_symbol_H-M      'P2(1)/n  '
_cod_database_code               7226125
_solvent_exptl_crystal_recrystallization_method
'Dimethyl Formamide-Ethyl Acetate Mixture'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
I1 I 0.63763(3) 0.65510(7) 0.755136(16) 0.02957(13) Uani 1 1 d .
S1 S 0.44884(10) 0.5921(2) 0.89717(5) 0.0243(3) Uani 1 1 d .
N1 N 0.5427(3) 0.2093(9) 0.84167(17) 0.0221(9) Uani 1 1 d .
N2 N 0.5963(3) 0.2650(8) 0.95142(19) 0.0222(9) Uani 1 1 d .
C1 C 0.5340(4) 0.3425(9) 0.8965(2) 0.0196(10) Uani 1 1 d .
C2 C 0.4738(4) 0.2510(9) 0.7811(2) 0.0183(10) Uani 1 1 d .
C3 C 0.4980(4) 0.4350(9) 0.7363(2) 0.0217(11) Uani 1 1 d .
C4 C 0.4306(4) 0.4708(10) 0.6779(2) 0.0280(12) Uani 1 1 d .
H4 H 0.4449 0.5987 0.6488 0.034 Uiso 1 1 calc R
C5 C 0.3420(4) 0.3143(11) 0.6632(2) 0.0311(12) Uani 1 1 d .
H5 H 0.2974 0.3344 0.6236 0.037 Uiso 1 1 calc R
C6 C 0.3193(4) 0.1289(10) 0.7068(2) 0.0273(11) Uani 1 1 d .
H6 H 0.2586 0.0276 0.6966 0.033 Uiso 1 1 calc R
C7 C 0.3840(4) 0.0913(10) 0.7647(2) 0.0259(12) Uani 1 1 d .
H7 H 0.3691 -0.0384 0.7931 0.031 Uiso 1 1 calc R
C8 C 0.6793(4) 0.0805(9) 0.9589(2) 0.0209(11) Uani 1 1 d .
C9 C 0.7575(4) 0.0847(11) 0.9201(3) 0.0359(14) Uani 1 1 d .
H9 H 0.7546 0.2054 0.8865 0.043 Uiso 1 1 calc R
C10 C 0.8395(5) -0.0900(13) 0.9313(3) 0.0495(17) Uani 1 1 d .
H10 H 0.8917 -0.0878 0.9048 0.059 Uiso 1 1 calc R
C11 C 0.8457(5) -0.2693(13) 0.9813(3) 0.0477(16) Uani 1 1 d .
H11 H 0.9010 -0.3887 0.9880 0.057 Uiso 1 1 calc R
C12 C 0.7691(5) -0.2695(11) 1.0212(3) 0.0363(13) Uani 1 1 d .
H12 H 0.7739 -0.3852 1.0559 0.044 Uiso 1 1 calc R
C13 C 0.6854(4) -0.0978(10) 1.0093(2) 0.0268(12) Uani 1 1 d .
H13 H 0.6327 -0.1016 1.0354 0.032 Uiso 1 1 calc R
H1 H 0.571(4) 0.059(12) 0.842(3) 0.034(16) Uiso 1 1 d .
H2 H 0.581(4) 0.321(10) 0.985(3) 0.024(14) Uiso 1 1 d .
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 0.0242(2) 0.0312(2) 0.0338(2) -0.00593(15) 0.00624(13) -0.00223(16)
S1 0.0314(7) 0.0253(7) 0.0155(6) 0.0010(5) 0.0011(5) 0.0110(5)
N1 0.029(2) 0.022(3) 0.014(2) -0.0041(16) -0.0016(17) 0.0090(19)
N2 0.027(2) 0.028(2) 0.011(2) -0.0010(17) -0.0019(17) 0.0081(19)
C1 0.022(2) 0.021(3) 0.015(2) 0.0011(19) 0.0017(18) -0.006(2)
C2 0.022(3) 0.020(3) 0.011(2) -0.0028(17) -0.0036(18) 0.008(2)
C3 0.024(3) 0.024(3) 0.016(2) -0.0066(19) -0.0011(19) 0.004(2)
C4 0.033(3) 0.030(3) 0.022(3) 0.007(2) 0.005(2) 0.007(2)
C5 0.030(3) 0.041(3) 0.018(2) -0.003(2) -0.007(2) 0.008(3)
C6 0.023(3) 0.030(3) 0.024(3) 0.002(2) -0.011(2) -0.001(2)
C7 0.027(3) 0.020(3) 0.030(3) 0.002(2) 0.000(2) -0.010(2)
C8 0.021(2) 0.023(3) 0.017(2) -0.0023(18) -0.0040(19) 0.001(2)
C9 0.033(3) 0.048(4) 0.025(3) 0.010(2) 0.002(2) 0.010(3)
C10 0.031(3) 0.074(5) 0.045(4) 0.014(3) 0.013(3) 0.015(3)
C11 0.032(3) 0.055(4) 0.053(4) 0.003(3) -0.001(3) 0.023(3)
C12 0.041(3) 0.027(3) 0.036(3) 0.006(2) -0.008(3) 0.004(3)
C13 0.032(3) 0.027(3) 0.021(2) 0.001(2) 0.000(2) 0.005(2)
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 N1 C2 123.0(4)
C1 N1 H1 123(4)
C2 N1 H1 110(4)
C1 N2 C8 128.7(4)
C1 N2 H2 116(4)
C8 N2 H2 115(4)
N2 C1 N1 116.7(4)
N2 C1 S1 121.1(3)
N1 C1 S1 122.2(3)
C3 C2 C7 119.4(4)
C3 C2 N1 121.2(4)
C7 C2 N1 119.3(4)
C4 C3 C2 120.2(5)
C4 C3 I1 119.0(4)
C2 C3 I1 120.9(3)
C5 C4 C3 119.3(5)
C5 C4 H4 120.3
C3 C4 H4 120.3
C6 C5 C4 120.5(5)
C6 C5 H5 119.8
C4 C5 H5 119.8
C7 C6 C5 121.2(5)
C7 C6 H6 119.4
C5 C6 H6 119.4
C6 C7 C2 119.3(5)
C6 C7 H7 120.4
C2 C7 H7 120.4
C9 C8 C13 119.5(5)
C9 C8 N2 121.7(4)
C13 C8 N2 118.6(4)
C10 C9 C8 119.7(5)
C10 C9 H9 120.2
C8 C9 H9 120.2
C9 C10 C11 121.1(5)
C9 C10 H10 119.5
C11 C10 H10 119.5
C12 C11 C10 119.4(5)
C12 C11 H11 120.3
C10 C11 H11 120.3
C11 C12 C13 119.8(5)
C11 C12 H12 120.1
C13 C12 H12 120.1
C12 C13 C8 120.5(5)
C12 C13 H13 119.7
C8 C13 H13 119.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 C3 2.096(5)
S1 C1 1.684(5)
N1 C1 1.349(6)
N1 C2 1.433(6)
N1 H1 0.85(6)
N2 C1 1.344(6)
N2 C8 1.413(6)
N2 H2 0.80(5)
C2 C3 1.395(7)
C2 C7 1.408(7)
C3 C4 1.385(7)
C4 C5 1.384(7)
C4 H4 0.9300
C5 C6 1.377(7)
C5 H5 0.9300
C6 C7 1.362(7)
C6 H6 0.9300
C7 H7 0.9300
C8 C9 1.379(7)
C8 C13 1.385(6)
C9 C10 1.372(8)
C9 H9 0.9300
C10 C11 1.381(9)
C10 H10 0.9300
C11 C12 1.378(8)
C11 H11 0.9300
C12 C13 1.379(7)
C12 H12 0.9300
C13 H13 0.9300
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
C7 H7 S1 0.93 2.94 3.759(5) 148.1 1_545
N2 H2 S1 0.80(5) 2.59(5) 3.368(4) 168(5) 3_667
N1 H1 I1 0.85(6) 2.96(6) 3.676(4) 143(4) 1_545
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
C8 N2 C1 N1 8.0(7)
C8 N2 C1 S1 -172.6(4)
C2 N1 C1 N2 173.2(4)
C2 N1 C1 S1 -6.2(7)
C1 N1 C2 C3 89.5(6)
C1 N1 C2 C7 -94.8(6)
C7 C2 C3 C4 3.9(7)
N1 C2 C3 C4 179.6(4)
C7 C2 C3 I1 -174.7(3)
N1 C2 C3 I1 0.9(6)
C2 C3 C4 C5 -2.9(7)
I1 C3 C4 C5 175.7(4)
C3 C4 C5 C6 1.6(8)
C4 C5 C6 C7 -1.2(8)
C5 C6 C7 C2 2.2(8)
C3 C2 C7 C6 -3.5(7)
N1 C2 C7 C6 -179.2(4)
C1 N2 C8 C9 48.1(8)
C1 N2 C8 C13 -136.2(5)
C13 C8 C9 C10 1.0(8)
N2 C8 C9 C10 176.7(5)
C8 C9 C10 C11 -0.6(10)
C9 C10 C11 C12 -1.1(10)
C10 C11 C12 C13 2.3(9)
C11 C12 C13 C8 -2.0(8)
C9 C8 C13 C12 0.3(7)
N2 C8 C13 C12 -175.5(5)
