#------------------------------------------------------------------------------
#$Date: 2015-07-10 23:52:22 +0300 (Fri, 10 Jul 2015) $
#$Revision: 143418 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/04/7220487.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_7220487
loop_
_publ_author_name
'Kuz'mina, Lyudmila G.'
'Vedernikov, Artem I.'
'Howard, Judith A. K.'
'Alfimov, Michael V.'
'Gromov, Sergey P.'
_publ_section_title
;
 Features of styryl dye crystal packings and their influence on [2 + 2]
 photocycloaddition reaction with single crystal retention
;
_journal_issue                   24
_journal_name_full               CrystEngComm
_journal_page_first              4584
_journal_paper_doi               10.1039/C5CE00653H
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'I, C20 H16 N O3 S, 0.5(O)'
_chemical_formula_sum            'C20 H16 I N O3.5 S'
_chemical_formula_weight         485.33
_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_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_primary     iterative
_audit_creation_date             2015-01-21
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.19 svn.r3143 for OlexSys, GUI svn.r4992)
;
_audit_update_record
;
2015-03-25 deposited with the CCDC.
2015-05-18 downloaded from the CCDC.
;
_cell_angle_alpha                93.619(5)
_cell_angle_beta                 104.077(5)
_cell_angle_gamma                105.686(5)
_cell_formula_units_Z            2
_cell_length_a                   7.564(4)
_cell_length_b                   10.338(5)
_cell_length_c                   14.496(7)
_cell_measurement_reflns_used    6820
_cell_measurement_theta_max      27.538
_cell_measurement_theta_min      2.789
_cell_volume                     1048.4(9)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      100.15
_diffrn_measured_fraction_theta_full 0.8850
_diffrn_measured_fraction_theta_max 0.8564
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_av_unetI/netI     0.0859
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8048
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         28.49
_diffrn_reflns_theta_min         2.07
_exptl_absorpt_coefficient_mu    1.647
_exptl_absorpt_correction_T_max  0.9921
_exptl_absorpt_correction_T_min  0.9803
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1340 before and 0.0849 after correction.
The Ratio of minimum to maximum transmission is 0.7732.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellowish
_exptl_crystal_colour_primary    yellowish
_exptl_crystal_density_diffrn    1.5372
_exptl_crystal_description       needle
_exptl_crystal_F_000             479.6267
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.005
_refine_diff_density_max         2.1443
_refine_diff_density_min         -2.5322
_refine_diff_density_rms         0.2422
_refine_ls_d_res_high            0.7450
_refine_ls_d_res_low             9.8577
_refine_ls_goodness_of_fit_ref   1.0319
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    24
_refine_ls_number_parameters     241
_refine_ls_number_reflns         4544
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0319
_refine_ls_R_factor_all          0.0797
_refine_ls_R_factor_gt           0.0696
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0000P)²+13.9291P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1629
_refine_ls_wR_factor_ref         0.1682
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -10
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              19
_reflns_limit_l_min              0
_reflns_number_gt                3915
_reflns_number_total             5306
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c5ce00653h1.cif
_cod_data_source_block           p-1
_cod_depositor_comments
'Adding full bibliography for 7220483--7220487.cif.'
_cod_database_code               7220487
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: S1a(0.7) N1a(0.7) C1a(0.7) C2(0.7) C3(0.7) C4a(0.7) S1b(0.3)
 N1b(0.3) C1b(0.3) C2'(0.3) C3'(0.3) C4b(0.3) O1W(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C14(H14), C16(H16), C17(H17)
3.b Idealised Me refined as rotating group:
 C10(H10a,H10b,H10c), C11(H11a,H11b,H11c), C18(H18a,H18b,H18c), C20(H20a,H20b,
 H20c)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -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_refinement_flags_posn
_atom_site_disorder_group
I1 I 0.19278(8) 0.88574(5) 0.66693(4) 0.02770(16) Uani 1.000000 . .
O1 O -0.6265(9) 0.3665(5) 0.2076(4) 0.0345(13) Uani 1.000000 . .
O2 O -0.6077(10) 0.6132(6) 0.1753(4) 0.0415(15) Uani 1.000000 . .
O3 O 0.2339(11) 0.1434(7) 0.9897(4) 0.0477(16) Uani 1.000000 . .
S1a S -0.0000(5) 0.5252(4) 0.7480(3) 0.0271(9) Uiso 0.700000 . 1
N1a N -0.0509(18) 0.2769(12) 0.6846(9) 0.020(3) Uiso 0.700000 . 1
C1a C -0.0865(15) 0.3905(11) 0.6572(8) 0.018(2) Uiso 0.700000 . 1
C2 C -0.1859(14) 0.4030(10) 0.5616(6) 0.0188(17) Uiso 0.700000 . 1
C3 C -0.2123(13) 0.5222(9) 0.5378(6) 0.0183(17) Uiso 0.700000 . 1
C4a C -0.3193(17) 0.5446(12) 0.4437(8) 0.017(3) Uiso 0.700000 . 1
S1b S 0.0110(12) 0.5300(9) 0.7288(7) 0.029(2) Uiso 0.300000 . 2
N1b N -0.032(4) 0.283(3) 0.671(2) 0.020(7) Uiso 0.300000 . 2
C1b C -0.062(3) 0.394(2) 0.6332(18) 0.015(5) Uiso 0.300000 . 2
C2' C -0.089(3) 0.414(2) 0.5304(16) 0.023(4) Uiso 0.300000 . 2
C3' C -0.098(3) 0.561(2) 0.5056(16) 0.023(4) Uiso 0.300000 . 2
C4b C -0.287(4) 0.562(3) 0.430(2) 0.023(7) Uiso 0.300000 . 2
C5 C -0.4144(11) 0.4412(7) 0.3681(5) 0.0251(14) Uani 1.000000 . .
C6 C -0.5171(11) 0.4652(7) 0.2816(5) 0.0256(14) Uani 1.000000 . .
C7 C -0.5110(12) 0.6013(8) 0.2646(5) 0.0281(15) Uani 1.000000 . .
C8 C -0.4112(11) 0.7071(8) 0.3379(5) 0.0274(15) Uani 1.000000 . .
H8 H -0.4101(11) 0.7954(8) 0.3282(5) 0.0329(18) Uiso 1.000000 R .
C9 C -0.3127(10) 0.6827(7) 0.4258(5) 0.0247(14) Uani 1.000000 . .
C10 C -0.6816(13) 0.2292(8) 0.2297(6) 0.0372(19) Uani 1.000000 . .
H10a H -0.776(7) 0.1719(16) 0.1753(19) 0.056(3) Uiso 1.000000 GR .
H10b H -0.572(2) 0.197(3) 0.244(5) 0.056(3) Uiso 1.000000 GR .
H10c H -0.733(9) 0.2280(14) 0.284(3) 0.056(3) Uiso 1.000000 GR .
C11 C -0.6031(13) 0.7477(8) 0.1547(6) 0.0352(18) Uani 1.000000 . .
H11a H -0.665(8) 0.7443(11) 0.0881(13) 0.053(3) Uiso 1.000000 GR .
H11b H -0.668(8) 0.786(3) 0.194(4) 0.053(3) Uiso 1.000000 GR .
H11c H -0.4730(13) 0.8031(19) 0.169(4) 0.053(3) Uiso 1.000000 GR .
C12 C 0.0781(13) 0.4261(9) 0.8259(6) 0.0352(18) Uani 1.000000 . .
C13 C 0.0385(11) 0.2916(8) 0.7799(5) 0.0266(15) Uani 1.000000 . .
C14 C 0.0899(12) 0.1908(9) 0.8307(5) 0.0315(17) Uani 1.000000 . .
H14 H 0.0680(12) 0.1036(9) 0.8007(5) 0.038(2) Uiso 1.000000 R .
C15 C 0.1767(16) 0.2288(10) 0.9297(6) 0.045(2) Uani 1.000000 . .
C16 C 0.2086(17) 0.3595(10) 0.9758(6) 0.051(3) Uani 1.000000 . .
H16 H 0.2624(17) 0.3795(10) 1.0419(6) 0.062(3) Uiso 1.000000 R .
C17 C 0.1617(17) 0.4583(10) 0.9250(6) 0.048(2) Uani 1.000000 . .
H17 H 0.1851(17) 0.5453(10) 0.9559(6) 0.058(3) Uiso 1.000000 R .
C18 C 0.2136(14) 0.0095(10) 0.9505(6) 0.042(2) Uani 1.000000 . .
H18a H 0.275(9) 0.0124(10) 0.900(3) 0.063(3) Uiso 1.000000 GR .
H18b H 0.272(9) -0.036(3) 0.9997(14) 0.063(3) Uiso 1.000000 GR .
H18c H 0.0806(14) -0.039(2) 0.926(5) 0.063(3) Uiso 1.000000 GR .
C19 C -0.0959(12) 0.1485(7) 0.6163(5) 0.0271(15) Uani 1.000000 . .
C20 C -0.2896(12) 0.0570(8) 0.6161(6) 0.0326(17) Uani 1.000000 . .
H20a H -0.318(4) -0.027(3) 0.575(4) 0.049(2) Uiso 1.000000 GR .
H20b H -0.289(3) 0.038(5) 0.6802(9) 0.049(2) Uiso 1.000000 GR .
H20c H -0.3851(17) 0.101(3) 0.593(4) 0.049(2) Uiso 1.000000 GR .
O1W O 0.3319(15) 0.7586(10) 0.8942(7) 0.025(2) Uani 0.500000 . .
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_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
I -0.41187 1.83264 20.14720 18.99490 7.51380 2.27350 4.34700 0.38140 27.76600
66.87760 4.07119989395
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
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
C10 O1 C6 117.1(5) . .
C11 O2 C7 116.9(6) . .
C18 O3 C15 118.7(7) . .
C19 N1a C13 123.7(9) . .
N1a C1a S1a 113.5(9) . .
C2 C1a S1a 121.8(8) . .
C2 C1a N1a 124.8(10) . .
C3 C2 C1a 121.8(9) . .
C4a C3 C2 126.2(9) . .
C9 C4a C5 117.7(9) . .
C19 N1b C13 116.2(19) . .
N1b C1b S1b 108.0(19) . .
C2' C1b S1b 123.3(17) . .
C2' C1b N1b 126(2) . .
C3' C2' C1b 116.5(19) . .
C3' C2' C1b 115.0(19) 2_566 .
C4b C3' C2' 115(2) . .
C4b C3' C2' 117.1(19) . 2_566
C9 C4b C5 123(2) . .
C5 C6 O1 124.3(6) . .
C7 C6 O1 115.5(6) . .
C7 C6 C5 120.2(7) . .
C6 C7 O2 115.0(7) . .
C8 C7 O2 125.7(7) . .
C8 C7 C6 119.2(6) . .
H8 C8 C7 119.7(4) . .
C9 C8 C7 120.5(7) . .
C9 C8 H8 119.7(4) . .
H10a C10 O1 109.5 . .
H10b C10 O1 109.5 . .
H10b C10 H10a 109.5 . .
H10c C10 O1 109.5 . .
H10c C10 H10a 109.5 . .
H10c C10 H10b 109.5 . .
H11a C11 O2 109.5 . .
H11b C11 O2 109.5 . .
H11b C11 H11a 109.5 . .
H11c C11 O2 109.5 . .
H11c C11 H11a 109.5 . .
H11c C11 H11b 109.5 . .
C17 C12 C13 120.1(8) . .
C14 C13 C12 121.4(7) . .
H14 C14 C13 121.9(4) . .
C15 C14 C13 116.2(8) . .
C15 C14 H14 121.9(5) . .
C14 C15 O3 123.9(8) . .
C16 C15 O3 113.8(8) . .
C16 C15 C14 122.4(8) . .
H16 C16 C15 119.5(5) . .
C17 C16 C15 120.9(9) . .
C17 C16 H16 119.5(5) . .
C16 C17 C12 118.9(8) . .
H17 C17 C12 120.6(5) . .
H17 C17 C16 120.6(5) . .
H18a C18 O3 109.5 . .
H18b C18 O3 109.5 . .
H18b C18 H18a 109.5 . .
H18c C18 O3 109.5 . .
H18c C18 H18a 109.5 . .
H18c C18 H18b 109.5 . .
H20a C20 C19 109.5 . .
H20b C20 C19 109.5 . .
H20b C20 H20a 109.5 . .
H20c C20 C19 109.5 . .
H20c C20 H20a 109.5 . .
H20c C20 H20b 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C6 1.360(9) .
O1 C10 1.447(9) .
O2 C7 1.355(9) .
O2 C11 1.433(9) .
O3 C15 1.359(11) .
O3 C18 1.416(12) .
S1a C1a 1.720(12) .
S1a C12 1.680(9) .
N1a C1a 1.336(16) .
N1a C13 1.360(14) .
N1a C19 1.512(14) .
C1a C2 1.439(14) .
C2 C3 1.353(13) .
C3 C4a 1.474(14) .
C4a C5 1.383(13) .
C4a C9 1.456(14) .
S1b C1b 1.78(3) .
S1b C12 1.879(12) .
N1b C1b 1.35(4) .
N1b C13 1.53(3) .
N1b C19 1.45(3) .
C1b C2' 1.49(3) .
C2' C3' 1.60(3) .
C2' C3' 1.58(3) 2_566
C3' C4b 1.58(4) .
C4b C5 1.44(3) .
C4b C9 1.32(3) .
C5 C6 1.382(9) .
C6 C7 1.434(10) .
C7 C8 1.383(11) .
C8 H8 0.9300 .
C8 C9 1.387(10) .
C10 H10a 0.9600 .
C10 H10b 0.9600 .
C10 H10c 0.9600 .
C11 H11a 0.9600 .
C11 H11b 0.9600 .
C11 H11c 0.9600 .
C12 C13 1.424(11) .
C12 C17 1.399(12) .
C13 C14 1.399(10) .
C14 H14 0.9300 .
C14 C15 1.406(12) .
C15 C16 1.400(14) .
C16 H16 0.9300 .
C16 C17 1.369(14) .
C17 H17 0.9300 .
C18 H18a 0.9600 .
C18 H18b 0.9600 .
C18 H18c 0.9600 .
C19 C20 1.513(11) .
C20 H20a 0.9600 .
C20 H20b 0.9600 .
C20 H20c 0.9600 .
