#------------------------------------------------------------------------------
#$Date: 2020-01-04 05:10:17 +0200 (Sat, 04 Jan 2020) $
#$Revision: 246542 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/72/4517206.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_4517206
loop_
_publ_author_name
'Botes, Delbert S.'
'Khorasani, Sanaz'
'Duminy, Welni'
'Levendis, Demetrius C.'
'Fernandes, Manuel A.'
_publ_section_title
;
 Supramolecular Inhibition of [4 + 2] Diels--Alder Reactions in
 Charge-Transfer Crystals
;
_journal_issue                   1
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              291
_journal_paper_doi               10.1021/acs.cgd.9b01167
_journal_volume                  20
_journal_year                    2019
_chemical_formula_moiety         'C22 H14 N2 O4 S2, C10 H8'
_chemical_formula_sum            'C32 H22 N2 O4 S2'
_chemical_formula_weight         562.63
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-08-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 118.2840(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   25.9145(6)
_cell_length_b                   6.79710(10)
_cell_length_c                   17.1675(4)
_cell_measurement_reflns_used    4382
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.04
_cell_measurement_theta_min      2.43
_cell_volume                     2662.91(10)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0682
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16355
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_min         1.785
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.243
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_description       needle
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.085
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3212
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.981
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0338
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0425P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0798
_refine_ls_wR_factor_ref         0.0876
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2271
_reflns_number_total             3212
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            Botes_CGD.cif
_cod_data_source_block           16db21_dblnap_0s
_cod_depositor_comments
'Adding full bibliography for 4517199--4517212.cif.'
_cod_database_code               4517206
_shelx_shelxl_version_number     2018/3
_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_max   0.980
_shelx_estimated_absorpt_t_min   0.911
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14), C15(H15),
 C16(H16)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
C1 C 0.47355(6) 0.67779(18) 0.65383(9) 0.0260(3) Uani 1 1 d .
C2 C 0.43746(6) 0.68745(19) 0.55537(10) 0.0302(3) Uani 1 1 d .
C3 C 0.37558(6) 0.68369(19) 0.61583(9) 0.0298(3) Uani 1 1 d .
C4 C 0.43736(6) 0.67686(19) 0.68916(9) 0.0268(3) Uani 1 1 d .
C5 C 0.32900(7) 0.6991(2) 0.44914(10) 0.0360(4) Uani 1 1 d .
H5A H 0.339644 0.780023 0.410949 0.043 Uiso 1 1 calc R
H5B H 0.296119 0.765209 0.452636 0.043 Uiso 1 1 calc R
C6 C 0.30901(6) 0.4995(2) 0.40737(9) 0.0305(3) Uani 1 1 d .
C7 C 0.26188(7) 0.4060(2) 0.40840(11) 0.0436(4) Uani 1 1 d .
H7 H 0.241822 0.467726 0.435943 0.052 Uiso 1 1 calc R
C8 C 0.24383(7) 0.2230(3) 0.36948(12) 0.0506(5) Uani 1 1 d .
H8 H 0.211609 0.159288 0.370767 0.061 Uiso 1 1 calc R
C9 C 0.27243(7) 0.1326(2) 0.32884(11) 0.0460(4) Uani 1 1 d .
H9 H 0.259615 0.007867 0.301458 0.055 Uiso 1 1 calc R
C10 C 0.31960(8) 0.2240(2) 0.32812(11) 0.0467(4) Uani 1 1 d .
H10 H 0.339607 0.161872 0.300601 0.056 Uiso 1 1 calc R
C11 C 0.33780(7) 0.4057(2) 0.36730(10) 0.0394(4) Uani 1 1 d .
H11 H 0.370537 0.467509 0.366862 0.047 Uiso 1 1 calc R
N1 N 0.37926(5) 0.68868(17) 0.53784(8) 0.0324(3) Uani 1 1 d .
O1 O 0.33131(4) 0.68559(14) 0.62235(7) 0.0375(3) Uani 1 1 d .
O2 O 0.45480(5) 0.69491(15) 0.50150(6) 0.0390(3) Uani 1 1 d .
S1 S 0.54983(2) 0.67243(5) 0.70159(2) 0.02902(11) Uani 1 1 d .
C12 C 0.52154(6) 0.17301(19) 0.73549(10) 0.0293(3) Uani 1 1 d .
C13 C 0.50300(7) 0.1747(2) 0.64351(10) 0.0376(4) Uani 1 1 d .
H13 H 0.531430 0.174168 0.623426 0.045 Uiso 1 1 calc R
C14 C 0.44520(8) 0.1771(2) 0.58368(10) 0.0441(4) Uani 1 1 d .
H14 H 0.433613 0.179741 0.522250 0.053 Uiso 1 1 calc R
C15 C 0.59773(7) 0.1758(2) 0.88822(11) 0.0449(4) Uani 1 1 d .
H15 H 0.638080 0.176719 0.930709 0.054 Uiso 1 1 calc R
C16 C 0.58165(6) 0.1732(2) 0.80017(11) 0.0369(4) Uani 1 1 d .
H16 H 0.610979 0.171454 0.781881 0.044 Uiso 1 1 calc R
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 S1 119.62(10) . .
C4 C1 C2 108.39(13) . .
C4 C1 S1 131.99(11) . .
N1 C2 C1 106.14(12) . .
O2 C2 C1 127.44(14) . .
O2 C2 N1 126.42(14) . .
N1 C3 C4 106.09(12) . .
O1 C3 C4 127.49(13) . .
O1 C3 N1 126.42(14) . .
C1 C4 C3 108.62(12) . .
C1 C4 S1 132.17(11) . 2_656
C3 C4 S1 119.20(10) . 2_656
H5A C5 H5B 107.8 . .
C6 C5 H5A 109.0 . .
C6 C5 H5B 109.0 . .
N1 C5 H5A 109.0 . .
N1 C5 H5B 109.0 . .
N1 C5 C6 112.80(11) . .
C7 C6 C5 120.89(14) . .
C7 C6 C11 118.74(14) . .
C11 C6 C5 120.37(14) . .
C6 C7 H7 119.9 . .
C6 C7 C8 120.30(15) . .
C8 C7 H7 119.9 . .
C7 C8 H8 119.9 . .
C9 C8 C7 120.30(16) . .
C9 C8 H8 119.9 . .
C8 C9 H9 120.1 . .
C10 C9 C8 119.73(16) . .
C10 C9 H9 120.1 . .
C9 C10 H10 120.0 . .
C9 C10 C11 119.99(16) . .
C11 C10 H10 120.0 . .
C6 C11 H11 119.5 . .
C10 C11 C6 120.93(15) . .
C10 C11 H11 119.5 . .
C2 N1 C5 124.38(12) . .
C3 N1 C2 110.75(12) . .
C3 N1 C5 124.85(12) . .
C4 S1 C1 95.79(6) 2_656 .
C12 C12 C16 118.56(17) 2_656 .
C13 C12 C12 118.88(17) . 2_656
C13 C12 C16 122.56(14) . .
C12 C13 H13 119.5 . .
C14 C13 C12 120.91(15) . .
C14 C13 H13 119.5 . .
C13 C14 H14 119.7 . .
C13 C14 C15 120.60(15) . 2_656
C15 C14 H14 119.7 2_656 .
C14 C15 H15 119.9 2_656 .
C16 C15 C14 120.26(15) . 2_656
C16 C15 H15 119.9 . .
C12 C16 H16 119.6 . .
C15 C16 C12 120.79(15) . .
C15 C16 H16 119.6 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.496(2) .
C1 C4 1.3365(19) .
C1 S1 1.7451(14) .
C2 N1 1.3912(18) .
C2 O2 1.2056(17) .
C3 C4 1.4967(19) .
C3 N1 1.3871(18) .
C3 O1 1.2043(17) .
C4 S1 1.7432(14) 2_656
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C5 C6 1.507(2) .
C5 N1 1.4631(18) .
C6 C7 1.384(2) .
C6 C11 1.387(2) .
C7 H7 0.9500 .
C7 C8 1.384(2) .
C8 H8 0.9500 .
C8 C9 1.379(2) .
C9 H9 0.9500 .
C9 C10 1.377(2) .
C10 H10 0.9500 .
C10 C11 1.378(2) .
C11 H11 0.9500 .
C12 C12 1.422(3) 2_656
C12 C13 1.416(2) .
C12 C16 1.422(2) .
C13 H13 0.9500 .
C13 C14 1.357(2) .
C14 H14 0.9500 .
C14 C15 1.407(2) 2_656
C15 H15 0.9500 .
C15 C16 1.364(2) .
C16 H16 0.9500 .
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_4
C1 C2 N1 C3 0.89(14) . .
C1 C2 N1 C5 179.40(11) . .
C2 C1 C4 C3 0.59(14) . .
C2 C1 C4 S1 -178.53(10) . 2_656
C2 C1 S1 C4 176.67(10) . 2_656
C4 C1 C2 N1 -0.92(14) . .
C4 C1 C2 O2 178.34(13) . .
C4 C1 S1 C4 -2.56(12) . 2_656
C4 C3 N1 C2 -0.55(14) . .
C4 C3 N1 C5 -179.05(11) . .
C5 C6 C7 C8 179.75(14) . .
C5 C6 C11 C10 -179.35(13) . .
C6 C5 N1 C2 87.86(16) . .
C6 C5 N1 C3 -93.83(16) . .
C6 C7 C8 C9 -0.4(2) . .
C7 C6 C11 C10 0.8(2) . .
C7 C8 C9 C10 0.9(2) . .
C8 C9 C10 C11 -0.5(2) . .
C9 C10 C11 C6 -0.4(2) . .
C11 C6 C7 C8 -0.4(2) . .
N1 C3 C4 C1 -0.06(15) . .
N1 C3 C4 S1 179.19(9) . 2_656
N1 C5 C6 C7 98.82(16) . .
N1 C5 C6 C11 -80.98(17) . .
O1 C3 C4 C1 -179.70(13) . .
O1 C3 C4 S1 -0.45(19) . 2_656
O1 C3 N1 C2 179.10(13) . .
O1 C3 N1 C5 0.6(2) . .
O2 C2 N1 C3 -178.38(13) . .
O2 C2 N1 C5 0.1(2) . .
S1 C1 C2 N1 179.68(9) . .
S1 C1 C2 O2 -1.06(19) . .
S1 C1 C4 C3 179.89(10) . .
S1 C1 C4 S1 0.8(2) . 2_656
C12 C12 C13 C14 0.27(16) 2_656 .
C12 C12 C16 C15 -0.82(16) 2_656 .
C12 C13 C14 C15 -0.7(2) . 2_656
C13 C12 C16 C15 178.57(13) . .
C14 C15 C16 C12 0.4(2) 2_656 .
C16 C12 C13 C14 -179.12(13) . .
