#------------------------------------------------------------------------------
#$Date: 2016-01-23 05:24:51 +0200 (Sat, 23 Jan 2016) $
#$Revision: 174802 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/85/7118575.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_7118575
loop_
_publ_author_name
'd'Agostino, Simone'
'Spinelli, Floriana'
'Boanini, Elisa'
'Braga, Dario'
'Grepioni, Fabrizia'
_publ_section_title
;
 Single crystal to single crystal [2+2] photoreactions in chloride and
 sulphate salts of 4-amino-cinnamic acid via solid-solution formation: a
 structural and kinetic study.
;
_journal_issue                   9
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              1899
_journal_page_last               1902
_journal_paper_doi               10.1039/c5cc09412g
_journal_volume                  52
_journal_year                    2016
_chemical_formula_sum            'C18 H22 N2 O9 S'
_chemical_formula_weight         442.44
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-11-12 deposited with the CCDC.
2015-12-08 downloaded from the CCDC.
;
_cell_angle_alpha                104.423(12)
_cell_angle_beta                 98.792(11)
_cell_angle_gamma                102.601(12)
_cell_formula_units_Z            2
_cell_length_a                   7.2590(10)
_cell_length_b                   10.5719(15)
_cell_length_c                   13.8895(18)
_cell_measurement_reflns_used    1423
_cell_measurement_temperature    298
_cell_measurement_theta_max      25.0060
_cell_measurement_theta_min      2.9330
_cell_volume                     982.9(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1340
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.842
_diffrn_measurement_details
;
  1 omega  -19.00   18.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.5159  -99.0000   60.0000 37

  2 omega  -19.00   20.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.5159  -99.0000  -60.0000 39

  3 omega    6.00   51.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6096   57.0000  -90.0000 45

  4 omega  -45.00   34.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6096  -57.0000  150.0000 79

  5 omega    2.00   86.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6096   57.0000   60.0000 84

  6 omega  -51.00   36.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6096  -57.0000  -90.0000 87

;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0562
_diffrn_reflns_av_sigmaI/netI    0.1041
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7872
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.21
_diffrn_reflns_theta_min         2.92
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79518
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.491
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.104
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4480
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.1985
_refine_ls_R_factor_gt           0.1049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1968P)²+0.0241P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2810
_refine_ls_wR_factor_ref         0.3746
_reflns_number_gt                1995
_reflns_number_total             4480
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c5cc09412g2.cif
_cod_data_source_block           1H2SO4-H2O_2_70
_cod_original_cell_volume        982.9(2)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7118575
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C7A C -0.4245(11) -0.1406(8) 0.0265(5) 0.050(2) Uiso 0.732(15) 1 d P A 1
H7A H -0.5398 -0.2091 0.0024 0.060 Uiso 0.732(15) 1 calc PR A 1
C8A C -0.3300(11) -0.1143(9) -0.0421(5) 0.054(2) Uiso 0.732(15) 1 d P A 1
H8A H -0.2085 -0.0525 -0.0203 0.065 Uiso 0.732(15) 1 calc PR A 1
C8B C -0.381(4) -0.041(3) -0.034(2) 0.081(9) Uiso 0.268(15) 1 d P . 2
H8B H -0.2444 0.0021 -0.0018 0.097 Uiso 0.268(15) 1 calc PR A 2
C7B C -0.500(4) -0.081(3) 0.047(2) 0.087(9) Uiso 0.268(15) 1 d P . 2
H7B H -0.5893 -0.1714 0.0182 0.105 Uiso 0.268(15) 1 calc PR A 2
C1 C -0.2643(8) 0.0340(6) 0.3475(4) 0.0562(14) Uani 1 1 d . A .
C2 C -0.4425(10) -0.0534(7) 0.3053(5) 0.0766(19) Uani 1 1 d . . .
H2 H -0.5280 -0.0757 0.3458 0.092 Uiso 1 1 calc R . .
C3 C -0.4932(9) -0.1085(7) 0.2000(5) 0.076(2) Uani 1 1 d . A .
H3 H -0.6134 -0.1701 0.1700 0.091 Uiso 1 1 calc R . .
C4 C -0.3699(9) -0.0742(6) 0.1390(4) 0.0639(16) Uani 1 1 d . . .
C5 C -0.1912(10) 0.0104(7) 0.1847(5) 0.080(2) Uani 1 1 d . A .
H5 H -0.1030 0.0311 0.1452 0.096 Uiso 1 1 calc R . .
C6 C -0.1385(9) 0.0664(7) 0.2903(4) 0.0727(19) Uani 1 1 d . . .
H6 H -0.0170 0.1260 0.3209 0.087 Uiso 1 1 calc R A .
C9 C -0.4041(10) -0.1756(7) -0.1489(4) 0.0673(17) Uani 1 1 d . . .
C10 C 0.1728(8) 0.4637(6) 1.2444(4) 0.0575(14) Uani 1 1 d . . .
C11 C 0.0235(9) 0.3618(7) 1.1743(4) 0.0712(18) Uani 1 1 d . . .
H11 H -0.0740 0.3111 1.1963 0.085 Uiso 1 1 calc R . .
C12 C 0.0210(9) 0.3366(7) 1.0727(4) 0.0703(17) Uani 1 1 d . . .
H12 H -0.0790 0.2678 1.0262 0.084 Uiso 1 1 calc R . .
C13 C 0.1621(9) 0.4099(6) 1.0369(4) 0.0604(15) Uani 1 1 d . . .
C14 C 0.3094(9) 0.5162(7) 1.1088(5) 0.0710(18) Uani 1 1 d . . .
H14 H 0.4030 0.5708 1.0870 0.085 Uiso 1 1 calc R . .
C15 C 0.3142(9) 0.5391(7) 1.2117(5) 0.0707(17) Uani 1 1 d . . .
H15 H 0.4147 0.6064 1.2590 0.085 Uiso 1 1 calc R . .
C16 C 0.1649(9) 0.3892(7) 0.9285(4) 0.0658(16) Uani 1 1 d . . .
H16 H 0.2582 0.4527 0.9137 0.079 Uiso 1 1 calc R . .
C17 C 0.0507(9) 0.2912(7) 0.8499(4) 0.0691(17) Uani 1 1 d . . .
H17 H -0.0426 0.2254 0.8625 0.083 Uiso 1 1 calc R . .
C18 C 0.0619(10) 0.2797(7) 0.7434(5) 0.0684(17) Uani 1 1 d . . .
N1 N -0.2046(7) 0.0941(5) 0.4595(3) 0.0655(13) Uani 1 1 d . . .
H1A H -0.0777 0.1326 0.4771 0.098 Uiso 1 1 calc R A .
H1B H -0.2332 0.0295 0.4896 0.098 Uiso 1 1 calc R . .
H1C H -0.2670 0.1565 0.4792 0.098 Uiso 1 1 calc R . .
N2 N 0.1825(7) 0.4863(5) 1.3536(3) 0.0644(13) Uani 1 1 d . . .
H2B H 0.0639 0.4774 1.3653 0.077 Uiso 1 1 calc R . .
H2C H 0.2559 0.5695 1.3876 0.077 Uiso 1 1 calc R . .
H2D H 0.2336 0.4257 1.3742 0.077 Uiso 1 1 calc R . .
O1 O -0.5548(7) -0.2614(5) -0.1854(4) 0.0922(16) Uani 1 1 d . A .
O2 O -0.2830(7) -0.1371(5) -0.2035(3) 0.0856(15) Uani 1 1 d . A .
H2A H -0.2140 -0.0606 -0.1729 0.128 Uiso 1 1 calc R . .
O1W O 0.1875(7) 0.5982(6) 0.6112(4) 0.0974(16) Uani 1 1 d G . .
H1WA H 0.2551 0.6768 0.5912 0.146 Uiso 1 1 d G . .
H1WB H 0.2153 0.5272 0.5800 0.146 Uiso 1 1 d G . .
O3 O -0.0664(8) 0.2147(6) 0.6729(3) 0.110(2) Uani 1 1 d . . .
O4 O 0.2202(8) 0.3513(6) 0.7346(4) 0.0999(19) Uani 1 1 d . . .
O5 O 0.2265(8) 0.1308(6) 0.4751(4) 0.128(2) Uani 1 1 d . . .
O6 O 0.3557(6) 0.2909(4) 0.3931(3) 0.0702(12) Uani 1 1 d . . .
O7 O 0.3082(9) 0.3643(7) 0.5588(4) 0.1093(19) Uani 1 1 d . . .
O8 O 0.5550(6) 0.2580(5) 0.5328(3) 0.0789(13) Uani 1 1 d . . .
S1 S 0.3609(2) 0.25734(16) 0.48864(10) 0.0601(6) Uani 1 1 d . . .
H4 H 0.244(9) 0.339(6) 0.678(5) 0.063(19) Uiso 1 1 d . . .
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'
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
C8A C7A C4 127.9(7) . .
C7A C8A C9 123.2(7) . .
C7B C8B C7B 92(2) . 2_455
C7B C8B C9 116(2) . .
C7B C8B C9 116.5(19) 2_455 .
C4 C7B C8B 111(2) . .
C4 C7B C8B 125(2) . 2_455
C8B C7B C8B 88(2) . 2_455
C6 C1 C2 121.7(5) . .
C6 C1 N1 118.7(5) . .
C2 C1 N1 119.6(5) . .
C1 C2 C3 118.1(5) . .
C4 C3 C2 121.6(6) . .
C5 C4 C3 118.2(5) . .
C5 C4 C7B 129.8(13) . .
C3 C4 C7B 103.0(13) . .
C5 C4 C7A 121.1(6) . .
C3 C4 C7A 120.3(6) . .
C7B C4 C7A 37.6(12) . .
C4 C5 C6 120.7(6) . .
C1 C6 C5 119.7(6) . .
O1 C9 O2 122.8(6) . .
O1 C9 C8A 124.1(6) . .
O2 C9 C8A 112.9(6) . .
O1 C9 C8B 120.1(11) . .
O2 C9 C8B 111.1(10) . .
C8A C9 C8B 30.3(9) . .
C15 C10 C11 120.1(5) . .
C15 C10 N2 120.0(5) . .
C11 C10 N2 119.8(5) . .
C12 C11 C10 119.5(6) . .
C11 C12 C13 122.0(6) . .
C12 C13 C14 117.9(5) . .
C12 C13 C16 124.4(6) . .
C14 C13 C16 117.6(5) . .
C15 C14 C13 119.8(6) . .
C10 C15 C14 120.6(6) . .
C17 C16 C13 127.6(6) . .
C16 C17 C18 123.9(7) . .
O3 C18 O4 123.2(6) . .
O3 C18 C17 123.5(7) . .
O4 C18 C17 113.2(6) . .
O5 S1 O8 111.3(3) . .
O5 S1 O6 111.2(3) . .
O8 S1 O6 110.5(3) . .
O5 S1 O7 109.2(4) . .
O8 S1 O7 107.4(3) . .
O6 S1 O7 107.0(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C7A C8A 1.306(10) .
C7A C4 1.496(9) .
C8A C9 1.426(9) .
C8B C7B 1.61(4) .
C8B C7B 1.72(5) 2_455
C8B C9 1.81(3) .
C7B C4 1.44(3) .
C7B C8B 1.72(5) 2_455
C1 C6 1.343(8) .
C1 C2 1.359(8) .
C1 N1 1.481(7) .
C2 C3 1.391(9) .
C3 C4 1.375(8) .
C4 C5 1.358(8) .
C5 C6 1.394(8) .
C9 O1 1.202(7) .
C9 O2 1.309(7) .
C10 C15 1.363(8) .
C10 C11 1.389(8) .
C10 N2 1.463(7) .
C11 C12 1.366(8) .
C12 C13 1.378(8) .
C13 C14 1.412(8) .
C13 C16 1.470(8) .
C14 C15 1.383(8) .
C16 C17 1.319(8) .
C17 C18 1.470(9) .
C18 O3 1.185(7) .
C18 O4 1.272(8) .
O5 S1 1.423(5) .
O6 S1 1.455(4) .
O7 S1 1.459(5) .
O8 S1 1.446(5) .
