#------------------------------------------------------------------------------
#$Date: 2019-12-06 12:37:08 +0200 (Fri, 06 Dec 2019) $
#$Revision: 244941 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/64/1556444.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_1556444
loop_
_publ_author_name
'Hardin, A.E.S.'
'Ellington, T.L.'
'Nguyen, S.T.'
'Rheingold, A.L.'
'Tschumper, G.S.'
'Watkins, D.L.'
'Hammer, N.I.'
_publ_section_title
;
 A Raman Spectroscopic and Computational Study of New Aromatic
 Pyrimidine-Based Halogen Bond Acceptors
;
_journal_name_full               Inorganics
_journal_page_first              119
_journal_paper_doi               10.3390/inorganics7100119
_journal_volume                  7
_journal_year                    2019
_chemical_formula_moiety         '2(C8 H3 I N2 O4), 2(C8 H6 N2 S)'
_chemical_formula_sum            'C32 H18 I2 N8 O8 S2'
_chemical_formula_weight         960.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 93.209(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.2195(6)
_cell_length_b                   5.7344(4)
_cell_length_c                   32.1204(16)
_cell_measurement_reflns_used    6939
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.279
_cell_measurement_theta_min      2.539
_cell_volume                     1695.49(18)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'APEX2 v2014.11-0 (Bruker, 2014)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0722
_diffrn_reflns_av_unetI/netI     0.0697
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            14426
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.339
_diffrn_reflns_theta_min         2.267
_diffrn_source                   rotating-anode
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.043
_exptl_absorpt_correction_T_max  0.2627
_exptl_absorpt_correction_T_min  0.1977
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.881
_exptl_crystal_description       plate
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.650
_refine_diff_density_min         -0.990
_refine_diff_density_rms         0.150
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.164
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         4232
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      1.170
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0438
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0173P)²+2.5043P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1022
_refine_ls_wR_factor_ref         0.1040
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3944
_reflns_number_total             4232
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            dwat16_0m_a.cif
_cod_data_source_block           dwat16_0m_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the built-in table derived from the CIF
Core dictionary named 'cif_core.dic' version 2.4.5 last updated on
2014-11-21.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               1556444
_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_max   0.854
_shelx_estimated_absorpt_t_min   0.570
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C14) = Uanis(S1')
Uanis(S1) = Uanis(C14')
3. Rigid body (RIGU) restrains
 C14', C16, C15, S1', C13
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
4. Others
 Sof(H16A)=Sof(H15A)=Sof(C14)=Sof(H14)=Sof(S1)=1-FVAR(1)
 Sof(S1')=Sof(H16)=Sof(H15)=Sof(C14')=Sof(H14')=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C10(H10), C9(H9), C4(H4), C6(H6), C16(H16), C16(H16A), C8(H8),
 C15(H15), C15(H15A), C14'(H14'), C14(H14)
;
loop_
_space_group_symop_operation_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_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 0.83167(2) 0.22913(4) 0.51790(2) 0.01598(9) Uani 1 1 d . . . . .
S1' S 0.6172(3) -0.2085(5) 0.72550(8) 0.0212(6) Uani 0.585(6) 1 d . U P A 1
O2 O 0.4257(3) 1.4818(5) 0.40297(8) 0.0248(6) Uani 1 1 d . . . . .
O4 O 0.8878(3) 0.9484(5) 0.30792(8) 0.0325(7) Uani 1 1 d . . . . .
O1 O 0.4173(3) 1.2806(5) 0.46014(10) 0.0284(7) Uani 1 1 d . . . . .
O3 O 0.7742(4) 1.2817(5) 0.30322(10) 0.0322(7) Uani 1 1 d . . . . .
N3 N 0.8766(3) -0.0573(6) 0.58900(9) 0.0184(6) Uani 1 1 d . . . . .
N4 N 0.9385(3) -0.3942(6) 0.62974(9) 0.0213(6) Uani 1 1 d . . . . .
N2 N 0.8038(3) 1.0946(6) 0.32050(9) 0.0239(7) Uani 1 1 d . . . . .
N1 N 0.4616(3) 1.3157(6) 0.42567(10) 0.0193(6) Uani 1 1 d . . . . .
C12 C 0.7914(4) 0.0176(6) 0.61869(10) 0.0172(7) Uani 1 1 d . . . . .
H12 H 0.7421 0.1621 0.6149 0.021 Uiso 1 1 calc R . . . .
C1 C 0.7830(3) 0.4667(6) 0.47287(10) 0.0163(7) Uani 1 1 d . . . . .
C11 C 0.7726(4) -0.1102(6) 0.65522(10) 0.0153(7) Uani 1 1 d . . . . .
C10 C 0.8528(4) -0.3172(7) 0.65884(11) 0.0200(7) Uani 1 1 d . . . . .
H10 H 0.8456 -0.4079 0.6834 0.024 Uiso 1 1 calc R . . . .
C7 C 0.5688(3) 1.1503(6) 0.40970(10) 0.0159(7) Uani 1 1 d . . . . .
C13 C 0.6715(4) -0.0356(6) 0.68629(10) 0.0175(6) Uani 1 1 d . U . . .
C9 C 0.9450(4) -0.2613(6) 0.59599(13) 0.0212(8) Uani 1 1 d . . . . .
H9 H 1.0038 -0.3163 0.5747 0.025 Uiso 1 1 calc R . . . .
C4 C 0.7775(4) 0.8467(7) 0.38264(10) 0.0162(7) Uani 1 1 d . . . . .
H4 H 0.8484 0.7434 0.3728 0.019 Uiso 1 1 calc R . . . .
C5 C 0.7350(4) 1.0439(6) 0.36015(10) 0.0184(7) Uani 1 1 d . . . . .
C3 C 0.7125(4) 0.8045(6) 0.42034(11) 0.0151(6) Uani 1 1 d . . . . .
C6 C 0.6313(4) 1.2005(6) 0.37261(11) 0.0175(7) Uani 1 1 d . . . . .
H6 H 0.6048 1.3346 0.3566 0.021 Uiso 1 1 calc R . . . .
C16 C 0.4964(4) 0.1798(8) 0.72296(13) 0.0283(8) Uani 1 1 d . U . . .
H16 H 0.4369 0.3056 0.7309 0.034 Uiso 0.585(6) 1 calc R . P A 1
H16A H 0.4306 0.2957 0.7315 0.034 Uiso 0.415(6) 1 calc R . P A 2
C8 C 0.6053(3) 0.9566(6) 0.43379(10) 0.0162(7) Uani 1 1 d . . . . .
H8 H 0.5588 0.9272 0.4589 0.019 Uiso 1 1 calc R . . . .
C2 C 0.7552(3) 0.6126(6) 0.44713(10) 0.0155(7) Uani 1 1 d . . . . .
C15 C 0.5077(4) -0.0259(8) 0.74257(12) 0.0303(8) Uani 1 1 d . U . . .
H15 H 0.4520 -0.0603 0.7658 0.036 Uiso 0.585(6) 1 calc R . P A 1
H15A H 0.4542 -0.0762 0.7654 0.036 Uiso 0.415(6) 1 calc R . P A 2
C14' C 0.593(3) 0.183(3) 0.6861(9) 0.0212(9) Uani 0.585(6) 1 d . U P A 1
H14' H 0.5998 0.3054 0.6664 0.025 Uiso 0.585(6) 1 calc R . P A 1
C14 C 0.634(2) -0.175(4) 0.7192(6) 0.0212(6) Uani 0.415(6) 1 d . . P A 2
H14 H 0.6714 -0.3244 0.7266 0.025 Uiso 0.415(6) 1 calc R . P A 2
S1 S 0.5965(10) 0.2244(9) 0.6849(3) 0.0212(9) Uani 0.415(6) 1 d . . P A 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'
I I -0.4742 1.8119 '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'
S S 0.1246 0.1234 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C15 S1' C13 95.2(2) . .
C12 N3 C9 116.7(3) . .
C9 N4 C10 115.9(3) . .
O4 N2 O3 125.2(3) . .
O4 N2 C5 117.2(3) . .
O3 N2 C5 117.6(3) . .
O2 N1 C7 116.8(3) . .
O1 N1 O2 124.9(3) . .
O1 N1 C7 118.2(3) . .
N3 C12 H12 118.9 . .
N3 C12 C11 122.2(3) . .
C11 C12 H12 118.9 . .
C2 C1 I1 177.9(3) . .
C12 C11 C13 122.0(3) . .
C10 C11 C12 115.0(3) . .
C10 C11 C13 122.9(3) . .
N4 C10 C11 123.6(3) . .
N4 C10 H10 118.2 . .
C11 C10 H10 118.2 . .
C6 C7 N1 118.9(3) . .
C6 C7 C8 123.3(3) . .
C8 C7 N1 117.8(3) . .
C11 C13 S1' 123.9(3) . .
C11 C13 S1 121.9(4) . .
C14' C13 S1' 109.9(10) . .
C14' C13 C11 125.9(11) . .
C14 C13 C11 123.2(10) . .
C14 C13 S1 114.9(10) . .
N3 C9 H9 116.8 . .
N4 C9 N3 126.5(3) . .
N4 C9 H9 116.8 . .
C5 C4 H4 121.0 . .
C5 C4 C3 118.0(3) . .
C3 C4 H4 121.0 . .
C4 C5 N2 119.0(3) . .
C4 C5 C6 123.9(3) . .
C6 C5 N2 117.1(3) . .
C4 C3 C8 120.0(3) . .
C4 C3 C2 122.2(3) . .
C8 C3 C2 117.7(3) . .
C7 C6 C5 116.2(3) . .
C7 C6 H6 121.9 . .
C5 C6 H6 121.9 . .
C15 C16 H16 125.0 . .
C15 C16 H16A 121.0 . .
C15 C16 C14' 110.0(8) . .
C15 C16 S1 118.0(4) . .
C14' C16 H16 125.0 . .
S1 C16 H16A 121.0 . .
C7 C8 C3 118.7(3) . .
C7 C8 H8 120.7 . .
C3 C8 H8 120.7 . .
C1 C2 C3 172.5(4) . .
S1' C15 H15 121.4 . .
C16 C15 S1' 117.2(3) . .
C16 C15 H15 121.4 . .
C16 C15 H15A 126.9 . .
C16 C15 C14 106.3(7) . .
C14 C15 H15A 126.9 . .
C13 C14' C16 107.6(14) . .
C13 C14' H14' 126.2 . .
C16 C14' H14' 126.2 . .
C13 C14 C15 105.1(14) . .
C13 C14 H14 127.4 . .
C15 C14 H14 127.4 . .
C16 S1 C13 95.5(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 C1 2.019(3) .
S1' C13 1.700(4) .
S1' C15 1.574(5) .
O2 N1 1.234(4) .
O4 N2 1.225(4) .
O1 N1 1.218(4) .
O3 N2 1.232(4) .
N3 C12 1.340(4) .
N3 C9 1.341(5) .
N4 C10 1.333(5) .
N4 C9 1.329(5) .
N2 C5 1.483(4) .
N1 C7 1.482(4) .
C12 H12 0.9500 .
C12 C11 1.403(5) .
C1 C2 1.194(5) .
C11 C10 1.400(5) .
C11 C13 1.467(4) .
C10 H10 0.9500 .
C7 C6 1.383(5) .
C7 C8 1.384(5) .
C13 C14' 1.45(2) .
C13 C14 1.386(17) .
C13 S1 1.643(8) .
C9 H9 0.9500 .
C4 H4 0.9500 .
C4 C5 1.386(5) .
C4 C3 1.402(4) .
C5 C6 1.386(5) .
C3 C8 1.404(5) .
C3 C2 1.438(5) .
C6 H6 0.9500 .
C16 H16 0.9500 .
C16 H16A 0.9500 .
C16 C15 1.339(6) .
C16 C14' 1.52(3) .
C16 S1 1.593(9) .
C8 H8 0.9500 .
C15 H15 0.9500 .
C15 H15A 0.9500 .
C15 C14 1.66(2) .
C14' H14' 0.9500 .
C14 H14 0.9500 .
