#------------------------------------------------------------------------------
#$Date: 2022-10-07 00:54:19 +0300 (Fri, 07 Oct 2022) $
#$Revision: 278381 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/08/7130816.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_7130816
loop_
_publ_author_name
'Fiorentino, Antonio'
'Sachini, Brian'
'Corra, Stefano'
'Credi, Alberto'
'Femoni, Cristina'
'Fraix, Aurore'
'Silvi, Serena'
_publ_section_title
;
 Acidochromism of donor-acceptor Stenhouse adducts in organic solvent.
;
_journal_issue                   80
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              11236
_journal_page_last               11239
_journal_paper_doi               10.1039/d2cc03761k
_journal_volume                  58
_journal_year                    2022
_chemical_formula_sum            'C16 H22 F3 N O8 S'
_chemical_formula_weight         445.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2022-06-22 deposited with the CCDC.	2022-08-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.285(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9554(8)
_cell_length_b                   21.609(2)
_cell_length_c                   10.7441(11)
_cell_measurement_reflns_used    9993
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.606
_cell_measurement_theta_min      2.319
_cell_volume                     2039.0(3)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.946
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_device_type  'CMOS AREA DETECTOR'
_diffrn_measurement_method       'OMEGA SCANS'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0701
_diffrn_reflns_av_unetI/netI     0.0454
_diffrn_reflns_Laue_measured_fraction_full 0.946
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            23362
_diffrn_reflns_point_group_measured_fraction_full 0.946
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        24.994
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_min         2.150
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_correction_T_min  0.960
_exptl_absorpt_correction_type   'EMPIRICAL SADABS'
_exptl_crystal_colour            'PALE COLOUR'
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_description       PRISMATIC
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_transmission_factor_max   0.750
_exptl_transmission_factor_min   0.450
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.231
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         3398
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.231
_refine_ls_R_factor_all          0.1063
_refine_ls_R_factor_gt           0.0915
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0001P)²+7.0199P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1852
_refine_ls_wR_factor_ref         0.1906
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2779
_reflns_number_total             3398
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc03761k2.cif
_cod_data_source_block           P21c_a
_cod_original_cell_volume        2039.0(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7130816
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.956
_shelx_estimated_absorpt_t_max   0.973
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9183(6) 0.1925(3) 0.8766(5) 0.0540(15) Uani 1 1 d . . . . .
H1A H 0.8748 0.2333 0.8687 0.081 Uiso 1 1 calc R U . . .
H1B H 1.0168 0.1936 0.8539 0.081 Uiso 1 1 calc R U . . .
H1C H 0.9285 0.1785 0.9626 0.081 Uiso 1 1 calc R U . . .
C2 C 0.8820(9) 0.0850(3) 0.7898(7) 0.081(2) Uani 1 1 d . . . . .
H2A H 0.8939 0.0674 0.8733 0.122 Uiso 1 1 calc R U . . .
H2B H 0.9793 0.0868 0.7651 0.122 Uiso 1 1 calc R U . . .
H2C H 0.8140 0.0597 0.7307 0.122 Uiso 1 1 calc R U . . .
C3 C 0.8173(7) 0.1493(3) 0.7903(5) 0.0475(14) Uani 1 1 d . . . . .
O4 O 0.6735(4) 0.14240(17) 0.8295(3) 0.0499(10) Uani 1 1 d . . . . .
C5 C 0.5657(6) 0.1848(2) 0.7978(4) 0.0386(12) Uani 1 1 d . . . . .
O6 O 0.4500(4) 0.18113(19) 0.8375(3) 0.0546(10) Uani 1 1 d . . . . .
C7 C 0.5933(5) 0.2352(2) 0.7087(4) 0.0309(10) Uani 1 1 d . . . . .
H7 H 0.6520 0.2676 0.7604 0.037 Uiso 1 1 calc R U . . .
C8 C 0.6896(6) 0.2124(2) 0.6163(4) 0.0395(12) Uani 1 1 d . . . . .
O9 O 0.6759(5) 0.23011(19) 0.5097(3) 0.0584(11) Uani 1 1 d . . . . .
O10 O 0.7938(4) 0.16976(18) 0.6605(3) 0.0537(10) Uani 1 1 d . . . . .
C11 C 0.4463(5) 0.2651(2) 0.6393(4) 0.0361(11) Uani 1 1 d . . . . .
H11 H 0.4696 0.2891 0.5681 0.043 Uiso 1 1 calc R U . . .
C12 C 0.3267(6) 0.2163(3) 0.5857(5) 0.0506(14) Uani 1 1 d . . . . .
O13 O 0.3525(6) 0.1705(2) 0.5302(4) 0.0800(15) Uani 1 1 d . . . . .
C14 C 0.1845(7) 0.2348(3) 0.6192(6) 0.0664(18) Uani 1 1 d . . . . .
H14 H 0.0924 0.2142 0.5932 0.080 Uiso 1 1 calc R U . . .
C15 C 0.2023(6) 0.2842(3) 0.6907(6) 0.0617(18) Uani 1 1 d . . . . .
H15 H 0.1236 0.3029 0.7219 0.074 Uiso 1 1 calc R U . . .
C16 C 0.3637(5) 0.3076(2) 0.7172(5) 0.0425(13) Uani 1 1 d . . . . .
H16 H 0.4075 0.3024 0.8076 0.051 Uiso 1 1 calc R U . . .
N17 N 0.3696(5) 0.3749(2) 0.6818(4) 0.0436(11) Uani 1 1 d . . . . .
H17 H 0.4765 0.3853 0.6834 0.052 Uiso 1 1 calc R U . . .
C18 C 0.2817(6) 0.3888(3) 0.5498(5) 0.0500(14) Uani 1 1 d . . . . .
H18A H 0.2938 0.3546 0.4940 0.060 Uiso 1 1 calc R U . . .
H18B H 0.1743 0.3924 0.5521 0.060 Uiso 1 1 calc R U . . .
C19 C 0.3344(8) 0.4472(3) 0.4975(7) 0.083(2) Uani 1 1 d . . . . .
H19A H 0.3234 0.4811 0.5529 0.125 Uiso 1 1 calc R U . . .
H19B H 0.2741 0.4550 0.4148 0.125 Uiso 1 1 calc R U . . .
H19C H 0.4395 0.4432 0.4914 0.125 Uiso 1 1 calc R U . . .
C20 C 0.3151(8) 0.4155(3) 0.7788(6) 0.0672(18) Uani 1 1 d . . . . .
H20A H 0.2482 0.4472 0.7346 0.081 Uiso 1 1 calc R U . . .
H20B H 0.2562 0.3905 0.8266 0.081 Uiso 1 1 calc R U . . .
S20 S 0.83401(15) 0.39475(7) 0.71268(14) 0.0482(4) Uani 1 1 d . . . . .
C21 C 0.4360(10) 0.4448(5) 0.8655(9) 0.132(4) Uani 1 1 d . . . . .
H21A H 0.5143 0.4150 0.8956 0.198 Uiso 1 1 calc R U . . .
H21B H 0.3974 0.4612 0.9360 0.198 Uiso 1 1 calc R U . . .
H21C H 0.4775 0.4778 0.8230 0.198 Uiso 1 1 calc R U . . .
O21 O 0.8838(6) 0.3349(2) 0.7523(6) 0.0989(18) Uani 1 1 d . . . . .
O22 O 0.6735(5) 0.4007(3) 0.6756(5) 0.0840(15) Uani 1 1 d . . . . .
O23 O 0.9200(5) 0.4231(2) 0.6312(4) 0.0745(13) Uani 1 1 d . . . . .
C24 C 0.8778(7) 0.4409(4) 0.8562(6) 0.0650(18) Uani 1 1 d . . . . .
F25 F 0.8115(6) 0.4210(3) 0.9445(4) 0.1118(17) Uani 1 1 d . . . . .
F26 F 0.8301(7) 0.4979(2) 0.8342(5) 0.1175(18) Uani 1 1 d . . . . .
F27 F 1.0238(5) 0.4435(3) 0.8988(5) 0.139(2) Uani 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'
F F 0.0171 0.0103 '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
_geom_angle_publ_flag
C3 C1 H1A 109.5 . . ?
C3 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C3 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O10 C3 O4 110.3(4) . . ?
O10 C3 C1 111.4(5) . . ?
O4 C3 C1 110.6(4) . . ?
O10 C3 C2 105.3(4) . . ?
O4 C3 C2 105.8(5) . . ?
C1 C3 C2 113.2(5) . . ?
C5 O4 C3 120.1(4) . . ?
O6 C5 O4 119.9(5) . . ?
O6 C5 C7 122.5(5) . . ?
O4 C5 C7 117.6(4) . . ?
C5 C7 C8 111.5(4) . . ?
C5 C7 C11 112.7(4) . . ?
C8 C7 C11 111.4(4) . . ?
C5 C7 H7 107.0 . . ?
C8 C7 H7 107.0 . . ?
C11 C7 H7 107.0 . . ?
O9 C8 O10 119.9(5) . . ?
O9 C8 C7 124.0(5) . . ?
O10 C8 C7 116.1(4) . . ?
C8 O10 C3 121.2(4) . . ?
C7 C11 C16 116.8(4) . . ?
C7 C11 C12 111.4(4) . . ?
C16 C11 C12 104.0(4) . . ?
C7 C11 H11 108.1 . . ?
C16 C11 H11 108.1 . . ?
C12 C11 H11 108.1 . . ?
O13 C12 C14 128.0(6) . . ?
O13 C12 C11 124.4(5) . . ?
C14 C12 C11 107.5(5) . . ?
C15 C14 C12 111.1(6) . . ?
C15 C14 H14 124.5 . . ?
C12 C14 H14 124.5 . . ?
C14 C15 C16 112.8(5) . . ?
C14 C15 H15 123.6 . . ?
C16 C15 H15 123.6 . . ?
C15 C16 N17 110.9(4) . . ?
C15 C16 C11 104.2(5) . . ?
N17 C16 C11 113.4(4) . . ?
C15 C16 H16 109.4 . . ?
N17 C16 H16 109.4 . . ?
C11 C16 H16 109.4 . . ?
C16 N17 C18 113.0(4) . . ?
C16 N17 C20 110.7(4) . . ?
C18 N17 C20 110.6(4) . . ?
C16 N17 H17 107.4 . . ?
C18 N17 H17 107.4 . . ?
C20 N17 H17 107.4 . . ?
C19 C18 N17 112.0(5) . . ?
C19 C18 H18A 109.2 . . ?
N17 C18 H18A 109.2 . . ?
C19 C18 H18B 109.2 . . ?
N17 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 N17 113.6(6) . . ?
C21 C20 H20A 108.8 . . ?
N17 C20 H20A 108.8 . . ?
C21 C20 H20B 108.8 . . ?
N17 C20 H20B 108.8 . . ?
H20A C20 H20B 107.7 . . ?
O21 S20 O23 114.0(3) . . ?
O21 S20 O22 114.3(3) . . ?
O23 S20 O22 115.5(3) . . ?
O21 S20 C24 104.2(4) . . ?
O23 S20 C24 103.6(3) . . ?
O22 S20 C24 103.1(3) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
F25 C24 F27 109.4(6) . . ?
F25 C24 F26 105.4(6) . . ?
F27 C24 F26 107.0(7) . . ?
F25 C24 S20 112.9(5) . . ?
F27 C24 S20 111.1(5) . . ?
F26 C24 S20 110.8(5) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C3 1.491(8) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.505(8) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 O10 1.439(6) . ?
C3 O4 1.439(7) . ?
O4 C5 1.326(6) . ?
C5 O6 1.199(6) . ?
C5 C7 1.502(7) . ?
C7 C8 1.519(6) . ?
C7 C11 1.524(6) . ?
C7 H7 0.9800 . ?
C8 O9 1.191(5) . ?
C8 O10 1.331(6) . ?
C11 C16 1.527(7) . ?
C11 C12 1.533(7) . ?
C11 H11 0.9800 . ?
C12 O13 1.201(7) . ?
C12 C14 1.446(9) . ?
C14 C15 1.306(9) . ?
C14 H14 0.9300 . ?
C15 C16 1.505(8) . ?
C15 H15 0.9300 . ?
C16 N17 1.508(7) . ?
C16 H16 0.9800 . ?
N17 C18 1.511(6) . ?
N17 C20 1.514(7) . ?
N17 H17 0.9800 . ?
C18 C19 1.496(8) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.430(9) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
S20 O21 1.407(5) . ?
S20 O23 1.413(4) . ?
S20 O22 1.421(4) . ?
S20 C24 1.813(7) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C24 F25 1.288(7) . ?
C24 F27 1.299(7) . ?
C24 F26 1.311(8) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O10 C3 O4 C5 -42.7(6) . . . . ?
C1 C3 O4 C5 80.9(5) . . . . ?
C2 C3 O4 C5 -156.2(5) . . . . ?
C3 O4 C5 O6 -175.1(5) . . . . ?
C3 O4 C5 C7 6.8(6) . . . . ?
O6 C5 C7 C8 -146.6(5) . . . . ?
O4 C5 C7 C8 31.4(6) . . . . ?
O6 C5 C7 C11 -20.6(6) . . . . ?
O4 C5 C7 C11 157.5(4) . . . . ?
C5 C7 C8 O9 146.4(5) . . . . ?
C11 C7 C8 O9 19.6(7) . . . . ?
C5 C7 C8 O10 -33.3(6) . . . . ?
C11 C7 C8 O10 -160.0(4) . . . . ?
O9 C8 O10 C3 177.5(5) . . . . ?
C7 C8 O10 C3 -2.9(7) . . . . ?
O4 C3 O10 C8 40.6(7) . . . . ?
C1 C3 O10 C8 -82.6(6) . . . . ?
C2 C3 O10 C8 154.4(5) . . . . ?
C5 C7 C11 C16 72.6(5) . . . . ?
C8 C7 C11 C16 -161.2(4) . . . . ?
C5 C7 C11 C12 -46.6(5) . . . . ?
C8 C7 C11 C12 79.5(5) . . . . ?
C7 C11 C12 O13 -44.8(7) . . . . ?
C16 C11 C12 O13 -171.5(5) . . . . ?
C7 C11 C12 C14 132.9(5) . . . . ?
C16 C11 C12 C14 6.2(5) . . . . ?
O13 C12 C14 C15 173.4(6) . . . . ?
C11 C12 C14 C15 -4.2(7) . . . . ?
C12 C14 C15 C16 0.2(7) . . . . ?
C14 C15 C16 N17 126.1(5) . . . . ?
C14 C15 C16 C11 3.9(6) . . . . ?
C7 C11 C16 C15 -129.1(4) . . . . ?
C12 C11 C16 C15 -5.9(5) . . . . ?
C7 C11 C16 N17 110.3(5) . . . . ?
C12 C11 C16 N17 -126.5(4) . . . . ?
C15 C16 N17 C18 -49.8(6) . . . . ?
C11 C16 N17 C18 66.9(5) . . . . ?
C15 C16 N17 C20 74.9(6) . . . . ?
C11 C16 N17 C20 -168.3(4) . . . . ?
C16 N17 C18 C19 -158.3(5) . . . . ?
C20 N17 C18 C19 77.0(6) . . . . ?
C16 N17 C20 C21 102.2(8) . . . . ?
C18 N17 C20 C21 -131.8(7) . . . . ?
O21 S20 C24 F25 -59.0(6) . . . . ?
O23 S20 C24 F25 -178.5(5) . . . . ?
O22 S20 C24 F25 60.7(6) . . . . ?
O21 S20 C24 F27 64.4(6) . . . . ?
O23 S20 C24 F27 -55.2(6) . . . . ?
O22 S20 C24 F27 -175.9(6) . . . . ?
O21 S20 C24 F26 -176.9(5) . . . . ?
O23 S20 C24 F26 63.6(5) . . . . ?
O22 S20 C24 F26 -57.2(6) . . . . ?
