#------------------------------------------------------------------------------
#$Date: 2016-01-23 05:24:51 +0200 (Sat, 23 Jan 2016) $
#$Revision: 174802 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/85/7118579.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_7118579
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                106.348(10)
_cell_angle_beta                 95.271(9)
_cell_angle_gamma                101.923(10)
_cell_formula_units_Z            2
_cell_length_a                   7.0956(7)
_cell_length_b                   10.6597(13)
_cell_length_c                   13.9430(15)
_cell_measurement_reflns_used    1928
_cell_measurement_temperature    298
_cell_measurement_theta_max      28.7490
_cell_measurement_theta_min      3.0860
_cell_volume                     977.4(2)
_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, 2005)'
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1340
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.847
_diffrn_measurement_details
;
  1 omega  -87.00    6.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.5159  -38.0000 -150.0000 93

  2 omega  -18.00   14.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.5159  -99.0000    0.0000 32

  3 omega  -32.00   51.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.5159   57.0000    0.0000 83

  4 omega  -10.00   86.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6096   77.0000  120.0000 96

  5 omega    6.00   83.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6096   57.0000 -120.0000 77

;
_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  0.0465
_diffrn_reflns_av_sigmaI/netI    0.0668
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7914
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.11
_diffrn_reflns_theta_min         2.97
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61192
_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    1.503
_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         0.991
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.176
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4462
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.176
_refine_ls_R_factor_all          0.1349
_refine_ls_R_factor_gt           0.1076
_refine_ls_shift/su_max          0.170
_refine_ls_shift/su_mean         0.023
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1122P)²+1.2026P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2511
_refine_ls_wR_factor_ref         0.2698
_reflns_number_gt                3499
_reflns_number_total             4462
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c5cc09412g2.cif
_cod_data_source_block           1H2SO4-H2O_2_0
_cod_original_cell_volume        977.41(19)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7118579
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
C1 C 0.7468(7) 0.0300(4) 0.3528(3) 0.0365(10) Uani 1 1 d .
C2 C 0.8637(7) 0.0634(5) 0.2882(3) 0.0477(12) Uani 1 1 d .
H2 H 0.9917 0.1136 0.3123 0.057 Uiso 1 1 calc R
C3 C 0.7906(7) 0.0220(5) 0.1848(3) 0.0490(13) Uani 1 1 d .
H3 H 0.8701 0.0442 0.1396 0.059 Uiso 1 1 calc R
C4 C 0.5990(7) -0.0525(5) 0.1496(3) 0.0413(11) Uani 1 1 d .
C5 C 0.4916(7) -0.0923(5) 0.2172(4) 0.0504(13) Uani 1 1 d .
H5 H 0.3673 -0.1488 0.1936 0.060 Uiso 1 1 calc R
C6 C 0.5623(7) -0.0512(5) 0.3188(4) 0.0493(12) Uani 1 1 d .
H6 H 0.4864 -0.0780 0.3638 0.059 Uiso 1 1 calc R
C7 C 0.4961(7) -0.0729(5) 0.0443(3) 0.0481(12) Uani 1 1 d .
H7 H 0.4060 -0.1624 0.0177 0.058 Uiso 1 1 calc R
C8 C 0.3850(7) 0.0424(5) 0.0366(3) 0.0483(12) Uani 1 1 d .
H8 H 0.2459 0.0047 0.0094 0.058 Uiso 1 1 calc R
C9 C 0.4186(7) 0.1571(5) 0.1363(4) 0.0463(12) Uani 1 1 d .
C10 C 0.9490(8) 0.6405(5) 0.8271(4) 0.0562(14) Uani 1 1 d .
H10 H 1.0386 0.6961 0.8030 0.067 Uiso 1 1 calc R
C11 C 0.8087(7) 0.5342(5) 0.7605(3) 0.0395(10) Uani 1 1 d .
C12 C 0.6795(7) 0.4509(5) 0.7955(4) 0.0471(12) Uani 1 1 d .
H12 H 0.5863 0.3788 0.7504 0.057 Uiso 1 1 calc R
C13 C 0.6885(7) 0.4746(5) 0.8989(4) 0.0486(12) Uani 1 1 d .
H13 H 0.6010 0.4173 0.9227 0.058 Uiso 1 1 calc R
C14 C 0.8249(7) 0.5820(5) 0.9677(4) 0.0430(11) Uani 1 1 d .
C15 C 0.9546(8) 0.6629(6) 0.9297(4) 0.0588(15) Uani 1 1 d .
H15 H 1.0487 0.7348 0.9745 0.071 Uiso 1 1 calc R
C16 C 0.8257(7) 0.6029(5) 1.0759(4) 0.0483(12) Uani 1 1 d .
H16 H 0.7398 0.5374 1.0934 0.058 Uiso 1 1 calc R
C17 C 0.9349(8) 0.7047(6) 1.1520(4) 0.0538(13) Uani 1 1 d .
H17 H 1.0186 0.7731 1.1365 0.065 Uiso 1 1 calc R
C18 C 0.9322(8) 0.7162(6) 1.2593(4) 0.0515(13) Uani 1 1 d .
N1 N 0.8157(6) 0.0847(4) 0.4624(3) 0.0424(9) Uani 1 1 d .
H1A H 0.9431 0.1225 0.4738 0.064 Uiso 1 1 calc R
H1B H 0.7933 0.0184 0.4901 0.064 Uiso 1 1 calc R
H1C H 0.7524 0.1464 0.4898 0.064 Uiso 1 1 calc R
N2 N 0.7966(8) 0.5148(5) 0.6518(3) 0.0444(10) Uani 1 1 d .
O1 O 0.5545(6) 0.2529(4) 0.1611(3) 0.0712(12) Uani 1 1 d .
O2 O 0.2896(6) 0.1282(5) 0.1940(3) 0.0563(10) Uani 1 1 d .
O1W O 1.1720(7) 0.6040(6) 0.6144(6) 0.0945(17) Uani 1 1 d G
H1WA H 1.2133 0.6846 0.6140 0.142 Uiso 1 1 d G
H1WB H 1.2461 0.5562 0.5867 0.142 Uiso 1 1 d G
O3 O 1.0546(7) 0.7906(5) 1.3272(3) 0.0860(15) Uani 1 1 d .
O4 O 0.7804(6) 0.6334(5) 1.2736(3) 0.0779(14) Uani 1 1 d .
H4 H 0.7754 0.6512 1.3343 0.117 Uiso 1 1 calc R
O5 O 0.5646(5) 0.2595(4) 0.5259(3) 0.0520(9) Uani 1 1 d .
O6 O 0.2350(5) 0.1325(4) 0.4661(3) 0.0625(11) Uani 1 1 d .
O7 O 0.3782(5) 0.2885(3) 0.3837(2) 0.0496(9) Uani 1 1 d .
O8 O 0.3076(7) 0.3707(4) 0.5482(3) 0.0698(12) Uani 1 1 d .
S1 S 0.37140(16) 0.26096(11) 0.48062(8) 0.0354(3) Uani 1 1 d .
H2B H 0.731(7) 0.578(5) 0.639(4) 0.042(13) Uiso 1 1 d .
H2C H 0.914(9) 0.534(6) 0.645(4) 0.054(18) Uiso 1 1 d .
H2D H 0.754(10) 0.434(7) 0.616(5) 0.07(2) Uiso 1 1 d .
H2A H 0.328(14) 0.181(10) 0.239(8) 0.13(4) 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
C2 C1 C6 121.5(4) . .
C2 C1 N1 119.7(4) . .
C6 C1 N1 118.8(4) . .
C1 C2 C3 119.4(4) . .
C4 C3 C2 119.9(4) . .
C5 C4 C3 118.3(4) . .
C5 C4 C7 118.5(4) . .
C3 C4 C7 122.5(4) . .
C4 C5 C6 121.8(4) . .
C1 C6 C5 118.8(4) . .
C4 C7 C8 119.9(4) . 2_655
C4 C7 C8 114.2(4) . .
C8 C7 C8 89.5(4) 2_655 .
C9 C8 C7 115.7(4) . 2_655
C9 C8 C7 113.0(4) . .
C7 C8 C7 90.5(4) 2_655 .
O1 C9 O2 125.2(5) . .
O1 C9 C8 123.8(5) . .
O2 C9 C8 110.7(4) . .
C11 C10 C15 119.2(5) . .
C12 C11 C10 120.6(4) . .
C12 C11 N2 120.3(4) . .
C10 C11 N2 119.1(5) . .
C11 C12 C13 119.3(4) . .
C14 C13 C12 121.4(5) . .
C15 C14 C13 117.7(5) . .
C15 C14 C16 123.4(4) . .
C13 C14 C16 118.9(5) . .
C14 C15 C10 121.8(5) . .
C17 C16 C14 127.3(5) . .
C16 C17 C18 124.1(6) . .
O3 C18 O4 122.6(5) . .
O3 C18 C17 124.6(6) . .
O4 C18 C17 112.8(5) . .
O6 S1 O8 110.5(3) . .
O6 S1 O5 109.9(2) . .
O8 S1 O5 108.4(2) . .
O6 S1 O7 110.0(2) . .
O8 S1 O7 107.1(2) . .
O5 S1 O7 111.0(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.350(7) .
C1 C6 1.369(6) .
C1 N1 1.469(5) .
C2 C3 1.397(6) .
C3 C4 1.390(6) .
C4 C5 1.369(7) .
C4 C7 1.514(6) .
C5 C6 1.370(6) .
C7 C8 1.537(7) 2_655
C7 C8 1.613(8) .
C8 C9 1.531(7) .
C8 C7 1.537(7) 2_655
C9 O1 1.194(6) .
C9 O2 1.319(6) .
C10 C11 1.381(7) .
C10 C15 1.378(7) .
C11 C12 1.363(7) .
C11 N2 1.462(6) .
C12 C13 1.385(7) .
C13 C14 1.386(7) .
C14 C15 1.375(7) .
C14 C16 1.462(7) .
C16 C17 1.326(7) .
C17 C18 1.468(7) .
C18 O3 1.192(6) .
C18 O4 1.313(7) .
O5 S1 1.460(3) .
O6 S1 1.454(4) .
O7 S1 1.465(3) .
O8 S1 1.462(4) .
