#------------------------------------------------------------------------------
#$Date: 2016-01-23 05:24:51 +0200 (Sat, 23 Jan 2016) $
#$Revision: 174802 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/85/7118574.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_7118574
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 N O9 S'
_chemical_formula_weight         428.43
_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                104.253(12)
_cell_angle_beta                 99.577(10)
_cell_angle_gamma                102.609(12)
_cell_formula_units_Z            2
_cell_length_a                   7.3066(9)
_cell_length_b                   10.5681(17)
_cell_length_c                   13.8909(16)
_cell_measurement_reflns_used    1356
_cell_measurement_temperature    298
_cell_measurement_theta_max      23.5400
_cell_measurement_theta_min      3.4340
_cell_volume                     986.7(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 0.828
_diffrn_measurement_details
;
  1 omega    0.00   76.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       17.6096   57.0000  150.0000 76

  2 omega  -20.00   86.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       17.6096   19.0000   90.0000 106

  3 omega  -25.00    0.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      -16.5159  -99.0000 -120.0000 25

  4 omega  -23.00   23.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      -16.5159  -99.0000    0.0000 46

  5 omega  -44.00   36.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       17.6096  -57.0000  -90.0000 80

  6 omega  -88.00  -51.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      -16.5159 -179.0000  120.0000 37

;
_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  0.0366
_diffrn_reflns_av_sigmaI/netI    0.0944
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7514
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.27
_diffrn_reflns_theta_min         2.93
_exptl_absorpt_coefficient_mu    0.216
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91953
_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    1.442
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             450
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.549
_refine_diff_density_min         -0.461
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         4446
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.1600
_refine_ls_R_factor_gt           0.0776
_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)+(0.0923P)²+0.4284P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1814
_refine_ls_wR_factor_ref         0.2375
_reflns_number_gt                2143
_reflns_number_total             4446
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c5cc09412g2.cif
_cod_data_source_block           1H2SO4-H2O_2_88
_cod_original_cell_volume        986.7(2)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7118574
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 -0.4258(8) -0.1409(5) -0.4745(4) 0.0481(15) Uiso 0.884(10) 1 d P A 1
H7A H -0.5424 -0.2078 -0.4994 0.058 Uiso 0.884(10) 1 calc PR A 1
C8A C -0.3305(8) -0.1140(6) -0.5418(4) 0.0541(16) Uiso 0.884(10) 1 d P A 1
H8A H -0.2109 -0.0500 -0.5191 0.065 Uiso 0.884(10) 1 calc PR A 1
C7B C -0.495(7) -0.070(5) -0.459(4) 0.070(15) Uiso 0.116(10) 1 d P . 2
H7B H -0.5913 -0.1583 -0.4899 0.084 Uiso 0.116(10) 1 calc PR A 2
C8B C -0.400(8) -0.044(5) -0.532(4) 0.077(16) Uiso 0.116(10) 1 d P . 2
H8B H -0.2649 0.0013 -0.4977 0.092 Uiso 0.116(10) 1 calc PR A 2
C1 C -0.2655(7) 0.0353(4) -0.1533(3) 0.0470(10) Uani 1 1 d . . .
C2 C -0.4433(7) -0.0530(5) -0.1980(4) 0.0625(13) Uani 1 1 d . . .
H2 H -0.5293 -0.0763 -0.1587 0.075 Uiso 1 1 calc R . .
C3 C -0.1392(6) 0.0682(4) -0.2110(3) 0.0556(12) Uani 1 1 d . . .
H3 H -0.0186 0.1288 -0.1798 0.067 Uiso 1 1 calc R . .
C4 C -0.4922(7) -0.1069(5) -0.3026(4) 0.0654(14) Uani 1 1 d . A .
H4 H -0.6139 -0.1662 -0.3335 0.078 Uiso 1 1 calc R . .
C5 C -0.3686(6) -0.0766(4) -0.3631(3) 0.0486(11) Uani 1 1 d . . .
C6 C -0.1900(7) 0.0118(5) -0.3151(4) 0.0600(13) Uani 1 1 d . A .
H6 H -0.1023 0.0337 -0.3538 0.072 Uiso 1 1 calc R . .
C9 C -0.4039(8) -0.1801(5) -0.6517(4) 0.0587(12) Uani 1 1 d . . .
C10 C 0.1701(6) 0.4640(4) 0.7443(3) 0.0484(11) Uani 1 1 d . . .
C11 C 0.0210(7) 0.3639(5) 0.6744(4) 0.0599(13) Uani 1 1 d . . .
H11 H -0.0763 0.3139 0.6963 0.072 Uiso 1 1 calc R . .
C12 C 0.3117(7) 0.5395(5) 0.7126(4) 0.0595(13) Uani 1 1 d . . .
H12 H 0.4111 0.6083 0.7600 0.071 Uiso 1 1 calc R . .
C13 C 0.0165(7) 0.3380(5) 0.5714(3) 0.0571(12) Uani 1 1 d . . .
H13 H -0.0849 0.2706 0.5241 0.069 Uiso 1 1 calc R . .
C14 C 0.1609(6) 0.4111(4) 0.5376(3) 0.0482(11) Uani 1 1 d . . .
C15 C 0.3062(6) 0.5127(5) 0.6095(4) 0.0585(13) Uani 1 1 d . . .
H15 H 0.4027 0.5645 0.5882 0.070 Uiso 1 1 calc R . .
C16 C 0.1642(7) 0.3873(5) 0.4291(3) 0.0535(12) Uani 1 1 d . . .
H16 H 0.2604 0.4484 0.4145 0.064 Uiso 1 1 calc R . .
C17 C 0.0483(7) 0.2909(5) 0.3504(4) 0.0587(12) Uani 1 1 d . . .
H17 H -0.0465 0.2263 0.3627 0.070 Uiso 1 1 calc R . .
C18 C 0.0592(7) 0.2786(5) 0.2437(4) 0.0586(13) Uani 1 1 d . . .
N1 N -0.2100(8) 0.0931(5) -0.0423(3) 0.0530(10) Uani 1 1 d . . .
N2 N 0.1800(7) 0.4865(5) 0.8537(3) 0.0533(10) Uani 1 1 d . . .
O1 O -0.2801(5) -0.1379(4) -0.7043(3) 0.0725(11) Uani 1 1 d . A .
O2 O -0.5550(5) -0.2627(4) -0.6894(3) 0.0791(11) Uani 1 1 d . A .
O3 O 0.2242(6) 0.3498(5) 0.2356(3) 0.0913(15) Uani 1 1 d . . .
O4 O -0.0680(6) 0.2126(5) 0.1721(3) 0.0962(14) Uani 1 1 d . . .
O5 O 0.5529(5) 0.2551(3) 0.0330(3) 0.0652(9) Uani 1 1 d . . .
O6 O 0.3497(5) 0.2899(3) -0.1072(2) 0.0580(9) Uani 1 1 d . . .
O7 O 0.2230(6) 0.1303(4) -0.0239(3) 0.1158(18) Uani 1 1 d . . .
O8 O 0.3105(7) 0.3649(4) 0.0605(3) 0.0994(14) Uani 1 1 d . . .
S1 S 0.35942(17) 0.25658(11) -0.01021(8) 0.0500(4) Uani 1 1 d . . .
O1W O 0.1849(7) 0.5979(6) 0.1102(4) 0.0820(13) Uani 1 1 d . . .
H1W H 0.266(15) 0.643(10) 0.169(8) 0.20(5) Uiso 1 1 d . . .
H2W H 0.218(7) 0.538(5) 0.098(4) 0.043(17) Uiso 1 1 d . . .
H1X H -0.356(10) -0.195(7) -0.778(6) 0.15(3) Uiso 1 1 d . . .
H3X H 0.19(2) 0.332(13) 0.183(9) 0.26(7) Uiso 1 1 d . . .
H1NA H -0.278(8) 0.158(6) -0.024(4) 0.10(2) Uiso 1 1 d . . .
H1NB H -0.086(9) 0.135(5) -0.025(4) 0.08(2) Uiso 1 1 d . . .
H2NA H 0.037(7) 0.476(4) 0.867(3) 0.066(14) Uiso 1 1 d . . .
H1NC H -0.215(8) 0.024(6) -0.012(4) 0.081(18) Uiso 1 1 d . . .
H2NC H 0.254(8) 0.570(6) 0.887(4) 0.078(17) Uiso 1 1 d . . .
H2NB H 0.210(9) 0.426(6) 0.878(5) 0.10(2) 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 C5 127.1(5) . .
C7A C8A C9 122.8(5) . .
C8B C7B C5 115(4) . .
C8B C7B C8B 91(4) . 2_454
C5 C7B C8B 126(4) . 2_454
C7B C8B C7B 89(4) . 2_454
C7B C8B C9 123(4) . .
C7B C8B C9 120(4) 2_454 .
C3 C1 C2 120.7(4) . .
C3 C1 N1 120.0(4) . .
C2 C1 N1 119.3(4) . .
C1 C2 C4 118.3(5) . .
C1 C3 C6 120.0(4) . .
C5 C4 C2 122.6(4) . .
C4 C5 C6 117.3(4) . .
C4 C5 C7A 120.4(4) . .
C6 C5 C7A 122.3(4) . .
C4 C5 C7B 105.5(18) . .
C6 C5 C7B 124.2(19) . .
C7A C5 C7B 38.5(17) . .
C3 C6 C5 121.1(5) . .
O2 C9 O1 124.0(5) . .
O2 C9 C8A 124.4(5) . .
O1 C9 C8A 111.6(5) . .
O2 C9 C8B 114.8(17) . .
O1 C9 C8B 113.5(16) . .
C8A C9 C8B 30.5(17) . .
C12 C10 C11 120.4(4) . .
C12 C10 N2 120.0(4) . .
C11 C10 N2 119.6(4) . .
C10 C11 C13 119.7(5) . .
C10 C12 C15 119.5(4) . .
C11 C13 C14 120.9(4) . .
C15 C14 C13 118.0(4) . .
C15 C14 C16 118.8(4) . .
C13 C14 C16 123.3(4) . .
C14 C15 C12 121.5(5) . .
C17 C16 C14 128.1(5) . .
C16 C17 C18 124.0(5) . .
O4 C18 O3 123.1(5) . .
O4 C18 C17 123.9(5) . .
O3 C18 C17 113.0(5) . .
O7 S1 O5 111.4(2) . .
O7 S1 O8 109.1(3) . .
O5 S1 O8 107.8(2) . .
O7 S1 O6 110.6(2) . .
O5 S1 O6 110.9(2) . .
O8 S1 O6 106.9(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C7A C8A 1.305(7) .
C7A C5 1.474(6) .
C8A C9 1.465(7) .
C7B C8B 1.36(6) .
C7B C5 1.52(5) .
C7B C8B 1.58(8) 2_454
C8B C7B 1.58(8) 2_454
C8B C9 1.90(5) .
C1 C3 1.363(6) .
C1 C2 1.364(6) .
C1 N1 1.461(6) .
C2 C4 1.377(6) .
C3 C6 1.373(6) .
C4 C5 1.372(6) .
C5 C6 1.375(6) .
C9 O2 1.190(5) .
C9 O1 1.325(6) .
C10 C12 1.366(6) .
C10 C11 1.374(6) .
C10 N2 1.465(6) .
C11 C13 1.383(6) .
C12 C15 1.381(6) .
C13 C14 1.385(6) .
C14 C15 1.379(6) .
C14 C16 1.470(6) .
C16 C17 1.310(6) .
C17 C18 1.473(7) .
C18 O4 1.185(5) .
C18 O3 1.313(7) .
O5 S1 1.446(3) .
O6 S1 1.468(3) .
O7 S1 1.428(4) .
O8 S1 1.465(4) .
