#------------------------------------------------------------------------------
#$Date: 2015-07-10 23:52:22 +0300 (Fri, 10 Jul 2015) $
#$Revision: 143418 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/04/7220486.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_7220486
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         'I2, C40 H46 N O7 S2'
_chemical_formula_sum            'C40 H46 I2 N O7 S2'
_chemical_formula_weight         982.74
_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                93.69(2)
_cell_angle_beta                 103.61(2)
_cell_angle_gamma                105.59(2)
_cell_formula_units_Z            1
_cell_length_a                   7.808(4)
_cell_length_b                   10.354(6)
_cell_length_c                   13.780(7)
_cell_measurement_reflns_used    979
_cell_measurement_theta_max      54.712
_cell_measurement_theta_min      9.988
_cell_volume                     1033.2(10)
_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      103.15
_diffrn_measured_fraction_theta_full 0.6690
_diffrn_measured_fraction_theta_max 0.6690
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0846
_diffrn_reflns_av_unetI/netI     0.1684
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            2646
_diffrn_reflns_theta_full        59.8358
_diffrn_reflns_theta_max         59.84
_diffrn_reflns_theta_min         9.99
_exptl_absorpt_coefficient_mu    13.304
_exptl_absorpt_correction_T_max  0.9654
_exptl_absorpt_correction_T_min  0.3641
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.5792
_exptl_crystal_F_000             493.6866
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.005
_refine_diff_density_max         1.9329
_refine_diff_density_min         -1.7573
_refine_diff_density_rms         0.3287
_refine_ls_d_res_high            0.8916
_refine_ls_d_res_low             4.4448
_refine_ls_goodness_of_fit_ref   1.1164
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    35
_refine_ls_number_parameters     238
_refine_ls_number_reflns         2045
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.1164
_refine_ls_R_factor_all          0.1565
_refine_ls_R_factor_gt           0.0871
_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)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1902
_refine_ls_wR_factor_ref         0.2280
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              11
_reflns_limit_k_min              -11
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                1266
_reflns_number_total             2045
_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_original_cell_volume        1033.3(10)
_cod_database_code               7220486
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: O1W(0.5)
3.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3)
3.b Secondary CH2 refined with riding coordinates:
 C19(H19a,H19b)
3.c Me refined with riding coordinates:
 C10(H10a,H10b,H10c), C11(H11a,H11b,H11c), C18(H18a,H18b,H18c), C20(H20a,H20b,
 H20c)
3.d Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8), C9(H9), C14(H14), C16(H16), C17(H17)
;
_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
I1 I -0.2323(2) 0.10302(13) -0.17756(10) 0.0524(7) Uani 1.000000 .
S1 S 0.0479(8) 0.5316(5) 0.2422(4) 0.0524(17) Uani 1.000000 .
O1 O -0.6707(18) 0.3760(15) -0.2614(10) 0.056(4) Uani 1.000000 .
O2 O -0.677(2) 0.6217(16) -0.2884(13) 0.098(7) Uani 1.000000 .
O3 O 0.232(2) 0.1426(15) 0.5060(11) 0.067(5) Uani 1.000000 .
N1 N -0.010(2) 0.2833(16) 0.1791(11) 0.045(5) Uani 1.000000 .
C1 C -0.021(3) 0.4011(19) 0.1465(13) 0.036(5) Uiso 1.000000 .
C2 C -0.076(3) 0.419(2) 0.0403(14) 0.053(7) Uani 1.000000 .
H2 H -0.186(3) 0.344(2) 0.0017(14) 0.064(8) Uiso 1.000000 R
C3 C -0.096(3) 0.558(2) 0.0158(14) 0.054(7) Uani 1.000000 .
H3 H -0.057(3) 0.623(2) 0.0794(14) 0.065(8) Uiso 1.000000 R
C4 C -0.273(3) 0.569(2) -0.0497(13) 0.035(6) Uani 1.000000 .
C5 C -0.397(2) 0.4571(19) -0.1188(15) 0.038(6) Uani 1.000000 .
H5 H -0.384(2) 0.3691(19) -0.1146(15) 0.046(7) Uiso 1.000000 R
C6 C -0.544(3) 0.477(2) -0.1949(15) 0.050(6) Uani 1.000000 .
C7 C -0.546(3) 0.607(2) -0.2063(18) 0.051(7) Uani 1.000000 .
C8 C -0.430(3) 0.712(2) -0.1358(15) 0.045(6) Uani 1.000000 .
H8 H -0.443(3) 0.801(2) -0.1393(15) 0.054(7) Uiso 1.000000 R
C9 C -0.293(3) 0.691(2) -0.0591(15) 0.054(7) Uani 1.000000 .
H9 H -0.212(3) 0.766(2) -0.0121(15) 0.065(8) Uiso 1.000000 R
C10 C -0.690(3) 0.243(2) -0.2401(15) 0.059(7) Uani 1.000000 .
H10a H -0.786(3) 0.180(2) -0.2944(15) 0.089(11) Uiso 1.000000 R
H10b H -0.573(3) 0.222(2) -0.2345(15) 0.089(11) Uiso 1.000000 R
H10c H -0.724(3) 0.234(2) -0.1763(15) 0.089(11) Uiso 1.000000 R
C11 C -0.631(3) 0.735(2) -0.3385(15) 0.064(8) Uani 1.000000 .
H11a H -0.736(3) 0.732(2) -0.3949(15) 0.096(11) Uiso 1.000000 R
H11b H -0.601(3) 0.818(2) -0.2914(15) 0.096(11) Uiso 1.000000 R
H11c H -0.524(3) 0.734(2) -0.3642(15) 0.096(11) Uiso 1.000000 R
C12 C 0.100(3) 0.4292(19) 0.3330(15) 0.040(6) Uani 1.000000 .
C13 C 0.061(3) 0.295(2) 0.2864(14) 0.043(6) Uani 1.000000 .
C14 C 0.101(3) 0.1932(19) 0.3390(14) 0.041(6) Uani 1.000000 .
H14 H 0.079(3) 0.1042(19) 0.3066(14) 0.049(7) Uiso 1.000000 R
C15 C 0.176(3) 0.228(2) 0.4412(15) 0.064(8) Uani 1.000000 .
C16 C 0.213(3) 0.363(2) 0.4897(17) 0.064(7) Uani 1.000000 .
H16 H 0.268(3) 0.385(2) 0.5602(17) 0.077(9) Uiso 1.000000 R
C17 C 0.170(3) 0.458(2) 0.4346(15) 0.054(7) Uani 1.000000 .
H17 H 0.189(3) 0.547(2) 0.4672(15) 0.064(8) Uiso 1.000000 R
C18 C 0.213(3) 0.010(2) 0.4656(16) 0.058(7) Uani 1.000000 .
H18a H 0.258(3) -0.039(2) 0.5199(16) 0.087(11) Uiso 1.000000 R
H18b H 0.083(3) -0.036(2) 0.4326(16) 0.087(11) Uiso 1.000000 R
H18c H 0.286(3) 0.013(2) 0.4161(16) 0.087(11) Uiso 1.000000 R
C19 C -0.072(3) 0.1513(16) 0.1141(14) 0.047(6) Uani 1.000000 .
H19a H -0.076(3) 0.1673(16) 0.0437(14) 0.056(8) Uiso 1.000000 R
H19b H 0.019(3) 0.1014(16) 0.1352(14) 0.056(8) Uiso 1.000000 R
C20 C -0.255(3) 0.066(2) 0.1179(15) 0.051(6) Uani 1.000000 .
H20a H -0.289(3) -0.020(2) 0.0735(15) 0.077(10) Uiso 1.000000 R
H20b H -0.252(3) 0.048(2) 0.1872(15) 0.077(10) Uiso 1.000000 R
H20c H -0.347(3) 0.114(2) 0.0956(15) 0.077(10) Uiso 1.000000 R
O1W O -0.354(3) 0.241(2) -0.4044(15) 0.031(7) 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 0.01920 0.00962 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 -0.19193 6.94384 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 0.05239 0.03376 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 0.03256 0.01839 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 0.33536 0.55132 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
C12 S1 C1 92.7(10) . .
C10 O1 C6 118.1(15) . .
C11 O2 C7 118.3(15) . .
C18 O3 C15 118.4(16) . .
C13 N1 C1 113.4(16) . .
C19 N1 C1 124.8(14) . .
C19 N1 C13 121.7(16) . .
N1 C1 S1 112.7(13) . .
C2 C1 S1 122.7(15) . .
C2 C1 N1 124.5(17) . .
H2 C2 C1 111.5(11) . .
C3 C2 C1 118.0(18) . .
C3 C2 C1 113.4(17) 2_565 .
C3 C2 H2 111.5(11) . .
C3 C2 H2 111.5(9) 2_565 .
H3 C3 C2 109.9(10) . .
H3 C3 C2 109.9(9) . 2_565
C4 C3 C2 120.5(18) . .
C4 C3 C2 114.2(16) . 2_565
C4 C3 H3 109.9(10) . .
C5 C4 C3 120.9(17) . .
C9 C4 C3 118.5(17) . .
C9 C4 C5 118.9(17) . .
H5 C5 C4 120.1(11) . .
C6 C5 C4 119.7(18) . .
C6 C5 H5 120.1(12) . .
C5 C6 O1 123.3(19) . .
C7 C6 O1 118.2(18) . .
C7 C6 C5 118.1(18) . .
C6 C7 O2 115.7(19) . .
C8 C7 O2 124(2) . .
C8 C7 C6 120.1(19) . .
H8 C8 C7 119.6(12) . .
C9 C8 C7 121(2) . .
C9 C8 H8 119.6(13) . .
C8 C9 C4 121.5(19) . .
H9 C9 C4 119.2(11) . .
H9 C9 C8 119.2(13) . .
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 . .
C13 C12 S1 109.8(14) . .
C17 C12 S1 131.1(17) . .
C17 C12 C13 119.1(18) . .
C12 C13 N1 111.4(17) . .
C14 C13 N1 125.7(19) . .
C14 C13 C12 122.7(18) . .
H14 C14 C13 122.0(12) . .
C15 C14 C13 116.0(19) . .
C15 C14 H14 122.0(14) . .
C14 C15 O3 125(2) . .
C16 C15 O3 113.2(17) . .
C16 C15 C14 122(2) . .
H16 C16 C15 120.2(12) . .
C17 C16 C15 120(2) . .
C17 C16 H16 120.2(13) . .
C16 C17 C12 121(2) . .
H17 C17 C12 119.7(13) . .
H17 C17 C16 119.7(13) . .
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 . .
H19a C19 N1 108.9(10) . .
H19b C19 N1 108.9(10) . .
H19b C19 H19a 107.7 . .
C20 C19 N1 113.4(19) . .
C20 C19 H19a 108.9(10) . .
C20 C19 H19b 108.9(11) . .
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
S1 C1 1.703(19) .
S1 C12 1.737(19) .
O1 C6 1.34(2) .
O1 C10 1.40(2) .
O2 C7 1.38(2) .
O2 C11 1.41(2) .
O3 C15 1.38(2) .
O3 C18 1.41(2) .
N1 C1 1.34(2) .
N1 C13 1.44(2) .
N1 C19 1.48(2) .
C1 C2 1.46(2) .
C2 H2 1.0000 .
C2 C3 1.53(3) .
C2 C3 1.68(3) 2_565
C3 H3 1.0000 .
C3 C4 1.50(3) .
C4 C5 1.42(2) .
C4 C9 1.33(3) .
C5 H5 0.9500 .
C5 C6 1.43(2) .
C6 C7 1.37(3) .
C7 C8 1.37(3) .
C8 H8 0.9500 .
C8 C9 1.39(3) .
C9 H9 0.9500 .
C10 H10a 0.9800 .
C10 H10b 0.9800 .
C10 H10c 0.9800 .
C11 H11a 0.9800 .
C11 H11b 0.9800 .
C11 H11c 0.9800 .
C12 C13 1.42(3) .
C12 C17 1.36(2) .
C13 C14 1.38(2) .
C14 H14 0.9500 .
C14 C15 1.37(2) .
C15 C16 1.43(3) .
C16 H16 0.9500 .
C16 C17 1.35(3) .
C17 H17 0.9500 .
C18 H18a 0.9800 .
C18 H18b 0.9800 .
C18 H18c 0.9800 .
C19 H19a 0.9900 .
C19 H19b 0.9900 .
C19 C20 1.48(3) .
C20 H20a 0.9800 .
C20 H20b 0.9800 .
C20 H20c 0.9800 .
