#------------------------------------------------------------------------------
#$Date: 2020-05-04 05:44:48 +0300 (Mon, 04 May 2020) $
#$Revision: 251472 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/82/4038231.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_4038231
loop_
_publ_author_name
'Mao, Jialin'
'Hai, Yu'
'Ye, Hebo'
'You, Lei'
_publ_section_title
;
 Adaptive Covalent Networks Enabled by Dual Reactivity: The Evolution of
 Reversible Covalent Bonds, Their Molecular Assemblies, and Guest
 Recognition.
;
_journal_issue                   8
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5351
_journal_page_last               5361
_journal_paper_doi               10.1021/acs.joc.0c00051
_journal_volume                  85
_journal_year                    2020
_chemical_formula_sum            'C32 H32 N4 O6 S2'
_chemical_formula_weight         632.74
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_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
_cell_angle_alpha                94.656(4)
_cell_angle_beta                 107.814(4)
_cell_angle_gamma                103.627(5)
_cell_formula_units_Z            2
_cell_length_a                   9.7299(5)
_cell_length_b                   13.0223(7)
_cell_length_c                   13.4524(5)
_cell_measurement_reflns_used    8113
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      60.1270
_cell_measurement_theta_min      3.0210
_cell_volume                     1555.31(14)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.1186
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            6954
_diffrn_reflns_theta_full        27.68
_diffrn_reflns_theta_max         27.68
_diffrn_reflns_theta_min         1.61
_exptl_absorpt_coefficient_mu    0.222
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             664
_platon_squeeze_details
;
;
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.525
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.193
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         6954
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.193
_refine_ls_R_factor_all          0.1449
_refine_ls_R_factor_gt           0.0847
_refine_ls_shift/su_max          0.093
_refine_ls_shift/su_mean         0.021
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2986
_refine_ls_wR_factor_ref         0.3266
_reflns_number_gt                4550
_reflns_number_total             6954
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0c00051_si_002.cif
_cod_data_source_block           1D
_cod_depositor_comments
'Adding full bibliography for 4038227--4038237.cif.'
_cod_original_cell_volume        1555.31(13)
_cod_database_code               4038231
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
S1 S 0.90180(11) 0.74126(9) 0.33714(9) 0.0495(3) Uani 1 1 d . . .
S2 S 0.67721(10) 0.16890(9) -0.06291(7) 0.0434(3) Uani 1 1 d . . .
N1 N 0.7255(4) 0.2515(3) -0.1394(3) 0.0438(7) Uani 1 1 d . . .
N2 N 0.7565(4) 0.8604(3) 0.0865(3) 0.0494(8) Uani 1 1 d . . .
H2 H 0.6780 0.8785 0.0475 0.059 Uiso 1 1 calc R . .
O3 O 0.5778(3) 0.2024(3) -0.0169(2) 0.0583(8) Uani 1 1 d . . .
O4 O 0.6532(4) 0.4450(3) -0.4142(2) 0.0617(8) Uani 1 1 d . . .
O5 O 0.6976(3) 0.7975(3) -0.1347(3) 0.0626(9) Uani 1 1 d . . .
N6 N 0.7972(4) 0.7378(3) 0.2163(3) 0.0471(8) Uani 1 1 d . . .
O7 O 1.0062(3) 0.6794(3) 0.3395(3) 0.0691(9) Uani 1 1 d . . .
C8 C 0.7241(4) 0.1949(3) -0.2421(3) 0.0454(9) Uani 1 1 d . . .
H8 H 0.8262 0.1854 -0.2323 0.055 Uiso 1 1 calc R . .
N9 N 0.6843(4) 0.2502(3) -0.3291(3) 0.0520(9) Uani 1 1 d . . .
H9 H 0.7389 0.2615 -0.3707 0.062 Uiso 1 1 calc R . .
C10 C 0.5804(4) 0.0624(3) -0.1680(3) 0.0473(9) Uani 1 1 d . . .
O11 O 0.8047(4) 0.1467(3) 0.0099(2) 0.0646(9) Uani 1 1 d . . .
C12 C 0.6718(5) 0.6390(4) 0.1667(4) 0.0508(10) Uani 1 1 d . . .
H12A H 0.5839 0.6584 0.1210 0.061 Uiso 1 1 calc R . .
H12B H 0.6425 0.6044 0.2229 0.061 Uiso 1 1 calc R . .
O13 O 0.8144(4) 0.7157(3) 0.4052(3) 0.0692(10) Uani 1 1 d . . .
C14 C 0.8387(5) 0.4236(4) 0.0874(4) 0.0614(12) Uani 1 1 d . . .
H14 H 0.8932 0.3768 0.1206 0.074 Uiso 1 1 calc R . .
C15 C 0.6817(5) 0.5598(3) -0.0053(3) 0.0491(9) Uani 1 1 d . . .
H15 H 0.6265 0.6061 -0.0386 0.059 Uiso 1 1 calc R . .
C16 C 1.1079(5) 0.9384(5) 0.4404(4) 0.0675(13) Uani 1 1 d . . .
H16 H 1.1595 0.9066 0.4961 0.081 Uiso 1 1 calc R . .
C17 C 0.7150(4) 0.5609(3) 0.1016(3) 0.0444(9) Uani 1 1 d . . .
C18 C 0.6952(5) 0.7116(4) -0.2020(3) 0.0497(10) Uani 1 1 d . . .
C19 C 0.5506(5) 0.2873(4) -0.3468(3) 0.0502(10) Uani 1 1 d . . .
H19A H 0.5588 0.3332 -0.2817 0.060 Uiso 1 1 calc R . .
H19B H 0.4614 0.2250 -0.3632 0.060 Uiso 1 1 calc R . .
C20 C 0.8002(5) 0.5992(4) -0.2886(4) 0.0575(11) Uani 1 1 d . . .
H20 H 0.8859 0.5842 -0.2996 0.069 Uiso 1 1 calc R . .
C21 C 0.9072(5) 0.9233(4) 0.2749(4) 0.0508(10) Uani 1 1 d . . .
C22 C 0.6159(4) 0.0862(3) -0.2563(3) 0.0478(9) Uani 1 1 d . . .
C23 C 0.8733(4) 0.8461(4) 0.0446(3) 0.0500(10) Uani 1 1 d . . .
H23A H 0.8801 0.7714 0.0444 0.060 Uiso 1 1 calc R . .
H23B H 0.9715 0.8946 0.0899 0.060 Uiso 1 1 calc R . .
C24 C 0.5359(5) 0.5539(4) -0.3273(3) 0.0569(11) Uani 1 1 d . . .
H24 H 0.4381 0.5083 -0.3644 0.068 Uiso 1 1 calc R . .
C25 C 0.6603(5) 0.5308(4) -0.3437(3) 0.0517(10) Uani 1 1 d . . .
C26 C 0.9843(5) 0.8779(4) 0.3560(4) 0.0526(10) Uani 1 1 d . . .
C27 C 0.8365(5) 0.8706(4) -0.0663(4) 0.0565(11) Uani 1 1 d . . .
H27A H 0.8282 0.9449 -0.0658 0.068 Uiso 1 1 calc R . .
H27B H 0.9185 0.8649 -0.0936 0.068 Uiso 1 1 calc R . .
C28 C 0.4827(5) -0.0322(4) -0.1653(4) 0.0632(12) Uani 1 1 d . . .
H28 H 0.4599 -0.0459 -0.1031 0.076 Uiso 1 1 calc R . .
C29 C 0.7730(4) 0.8441(3) 0.1925(3) 0.0475(9) Uani 1 1 d . . .
H29 H 0.6804 0.8507 0.2072 0.057 Uiso 1 1 calc R . .
C30 C 0.8068(4) 0.4232(3) -0.0193(3) 0.0454(9) Uani 1 1 d . . .
C31 C 0.8195(5) 0.6882(4) -0.2186(4) 0.0591(11) Uani 1 1 d . . .
H31 H 0.9175 0.7337 -0.1815 0.071 Uiso 1 1 calc R . .
C32 C 0.7271(5) 0.4925(4) -0.0648(3) 0.0522(10) Uani 1 1 d . . .
H32 H 0.7033 0.4936 -0.1386 0.063 Uiso 1 1 calc R . .
C33 C 0.5548(5) 0.6432(4) -0.2571(4) 0.0544(11) Uani 1 1 d . . .
H33 H 0.4691 0.6583 -0.2461 0.065 Uiso 1 1 calc R . .
C34 C 0.7928(5) 0.4914(4) 0.1478(3) 0.0567(11) Uani 1 1 d . . .
H34 H 0.8150 0.4898 0.2214 0.068 Uiso 1 1 calc R . .
C35 C 0.9538(6) 1.0326(4) 0.2766(4) 0.0653(12) Uani 1 1 d . . .
H35 H 0.9026 1.0653 0.2216 0.078 Uiso 1 1 calc R . .
C36 C 0.5505(6) 0.0100(4) -0.3478(4) 0.0637(13) Uani 1 1 d . . .
H36 H 0.5729 0.0237 -0.4102 0.076 Uiso 1 1 calc R . .
C37 C 0.5317(6) 0.3501(4) -0.4375(4) 0.0602(12) Uani 1 1 d . . .
H37A H 0.5264 0.3044 -0.5019 0.072 Uiso 1 1 calc R . .
H37B H 0.4362 0.3700 -0.4523 0.072 Uiso 1 1 calc R . .
C38 C 0.8516(5) 0.3481(4) -0.0861(4) 0.0541(10) Uani 1 1 d . . .
H38A H 0.8834 0.3852 -0.1401 0.065 Uiso 1 1 calc R . .
H38B H 0.9379 0.3265 -0.0410 0.065 Uiso 1 1 calc R . .
C39 C 1.0768(7) 1.0929(5) 0.3605(5) 0.0770(16) Uani 1 1 d . . .
H39 H 1.1093 1.1681 0.3628 0.092 Uiso 1 1 calc R . .
C41 C 0.4196(6) -0.1061(4) -0.2578(5) 0.0751(15) Uani 1 1 d . . .
H41 H 0.3518 -0.1725 -0.2595 0.090 Uiso 1 1 calc R . .
C42 C 0.4537(6) -0.0848(4) -0.3472(5) 0.0739(15) Uani 1 1 d . . .
H42 H 0.4091 -0.1369 -0.4098 0.089 Uiso 1 1 calc R . .
C43 C 1.1525(6) 1.0479(5) 0.4396(5) 0.0778(16) Uani 1 1 d . . .
H43 H 1.2374 1.0920 0.4953 0.093 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
_geom_angle_publ_flag
O13 S1 O7 114.9(2) . . ?
O13 S1 N6 112.01(19) . . ?
O7 S1 N6 110.7(2) . . ?
O13 S1 C26 111.3(2) . . ?
O7 S1 C26 112.7(2) . . ?
N6 S1 C26 93.3(2) . . ?
O3 S2 O11 115.5(2) . . ?
O3 S2 N1 111.06(19) . . ?
O11 S2 N1 112.02(18) . . ?
O3 S2 C10 111.39(19) . . ?
O11 S2 C10 111.4(2) . . ?
N1 S2 C10 93.44(18) . . ?
C38 N1 C8 117.0(3) . . ?
C38 N1 S2 116.2(3) . . ?
C8 N1 S2 113.0(3) . . ?
C29 N2 C23 118.0(3) . . ?
C25 O4 C37 119.0(4) . . ?
C18 O5 C27 121.5(3) . . ?
C12 N6 C29 119.0(3) . . ?
C12 N6 S1 116.4(3) . . ?
C29 N6 S1 114.0(3) . . ?
N9 C8 N1 113.9(3) . . ?
N9 C8 C22 113.6(3) . . ?
N1 C8 C22 103.2(3) . . ?
C8 N9 C19 117.7(3) . . ?
C22 C10 C28 123.8(4) . . ?
C22 C10 S2 109.8(3) . . ?
C28 C10 S2 126.4(4) . . ?
N6 C12 C17 111.7(3) . . ?
C30 C14 C34 121.1(4) . . ?
C17 C15 C32 120.9(4) . . ?
C26 C16 C43 116.7(5) . . ?
C15 C17 C34 118.4(4) . . ?
C15 C17 C12 120.3(4) . . ?
C34 C17 C12 121.2(4) . . ?
O5 C18 C33 115.5(4) . . ?
O5 C18 C31 126.1(4) . . ?
C33 C18 C31 118.4(4) . . ?
N9 C19 C37 110.2(3) . . ?
C31 C20 C25 122.0(4) . . ?
C26 C21 C35 119.5(4) . . ?
C26 C21 C29 114.0(4) . . ?
C35 C21 C29 126.5(4) . . ?
C10 C22 C36 118.0(4) . . ?
C10 C22 C8 115.1(4) . . ?
C36 C22 C8 126.9(4) . . ?
N2 C23 C27 109.3(3) . . ?
C33 C24 C25 119.7(4) . . ?
O4 C25 C20 117.3(4) . . ?
O4 C25 C24 124.3(4) . . ?
C20 C25 C24 118.4(4) . . ?
C21 C26 C16 122.3(5) . . ?
C21 C26 S1 110.7(3) . . ?
C16 C26 S1 127.0(4) . . ?
O5 C27 C23 110.7(4) . . ?
C41 C28 C10 116.6(5) . . ?
N2 C29 N6 114.9(3) . . ?
N2 C29 C21 113.9(3) . . ?
N6 C29 C21 102.9(3) . . ?
C14 C30 C32 117.8(4) . . ?
C14 C30 C38 121.7(4) . . ?
C32 C30 C38 120.5(4) . . ?
C20 C31 C18 119.7(4) . . ?
C15 C32 C30 121.3(4) . . ?
C24 C33 C18 121.7(4) . . ?
C17 C34 C14 120.5(4) . . ?
C21 C35 C39 118.3(5) . . ?
C42 C36 C22 119.4(5) . . ?
O4 C37 C19 111.6(4) . . ?
N1 C38 C30 111.0(3) . . ?
C43 C39 C35 122.0(6) . . ?
C28 C41 C42 120.9(5) . . ?
C41 C42 C36 121.2(5) . . ?
C39 C43 C16 121.2(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
S1 O13 1.437(3) . ?
S1 O7 1.433(3) . ?
S1 N6 1.623(4) . ?
S1 C26 1.734(5) . ?
S2 O3 1.425(3) . ?
S2 O11 1.433(3) . ?
S2 N1 1.635(3) . ?
S2 C10 1.749(5) . ?
N1 C38 1.479(5) . ?
N1 C8 1.506(5) . ?
N2 C29 1.424(5) . ?
N2 C23 1.456(5) . ?
O4 C25 1.381(6) . ?
O4 C37 1.430(6) . ?
O5 C18 1.372(5) . ?
O5 C27 1.438(6) . ?
N6 C12 1.488(5) . ?
N6 C29 1.501(5) . ?
C8 N9 1.424(5) . ?
C8 C22 1.509(6) . ?
N9 C19 1.452(5) . ?
C10 C22 1.373(6) . ?
C10 C28 1.378(6) . ?
C12 C17 1.503(6) . ?
C14 C30 1.372(6) . ?
C14 C34 1.390(6) . ?
C15 C17 1.372(6) . ?
C15 C32 1.374(6) . ?
C16 C26 1.389(7) . ?
C16 C43 1.391(9) . ?
C17 C34 1.380(6) . ?
C18 C33 1.382(6) . ?
C18 C31 1.391(6) . ?
C19 C37 1.513(6) . ?
C20 C31 1.370(7) . ?
C20 C25 1.379(7) . ?
C21 C26 1.384(6) . ?
C21 C35 1.385(7) . ?
C21 C29 1.513(6) . ?
C22 C36 1.389(6) . ?
C23 C27 1.503(6) . ?
C24 C33 1.376(7) . ?
C24 C25 1.389(6) . ?
C28 C41 1.382(8) . ?
C30 C32 1.386(6) . ?
C30 C38 1.500(6) . ?
C35 C39 1.381(8) . ?
C36 C42 1.368(8) . ?
C39 C43 1.358(9) . ?
C41 C42 1.374(8) . ?
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.500 0.500 122 33 ' '
