#------------------------------------------------------------------------------
#$Date: 2020-05-04 05:44:48 +0300 (Mon, 04 May 2020) $
#$Revision: 251472 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/82/4038229.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_4038229
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            'C17 H21 N2 O2 S'
_chemical_formula_weight         317.42
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                101.805(2)
_cell_angle_beta                 104.363(2)
_cell_angle_gamma                100.367(2)
_cell_formula_units_Z            2
_cell_length_a                   7.0032(2)
_cell_length_b                   10.8265(2)
_cell_length_c                   11.8966(2)
_cell_measurement_reflns_used    6626
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      60.3780
_cell_measurement_theta_min      3.7320
_cell_volume                     829.63(3)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.3405
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10161
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        53.543
_diffrn_reflns_theta_max         60.426
_diffrn_reflns_theta_min         3.739
_exptl_absorpt_coefficient_mu    1.165
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_description       Prism
_exptl_crystal_F_000             338
_refine_diff_density_max         0.474
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3686
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0556
_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)+(0.0886P)²+0.3585P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1592
_refine_ls_wR_factor_ref         0.1654
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3183
_reflns_number_total             3686
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00051_si_002.cif
_cod_data_source_block           1I2
_cod_depositor_comments
'Adding full bibliography for 4038227--4038237.cif.'
_cod_database_code               4038229
_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.
;
loop_
_space_group_symop_operation_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_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
S2 S 0.91326(7) 0.75904(5) 0.16042(5) 0.04745(19) Uani 1 1 d . . . . .
O21 O 0.9179(3) 0.77371(19) 0.04368(18) 0.0710(5) Uani 1 1 d . . . . .
O22 O 1.0994(3) 0.82118(18) 0.2539(2) 0.0773(6) Uani 1 1 d . . . . .
N1 N 0.7242(3) 0.80141(16) 0.19861(17) 0.0454(4) Uani 1 1 d . . . . .
N14 N 0.4749(3) 0.70822(18) 0.29116(15) 0.0464(4) Uani 1 1 d . . . . .
H14 H 0.3865 0.7542 0.2847 0.056 Uiso 1 1 d R U . . .
C11 C 0.6012(3) 0.97001(17) 0.10453(18) 0.0393(4) Uani 1 1 d . . . . .
C13 C 0.3937(3) 0.95764(19) 0.07371(19) 0.0429(4) Uani 1 1 d . . . . .
H13 H 0.3210 0.9295 0.1232 0.051 Uiso 1 1 calc R U . . .
C8 C 0.6311(3) 0.57397(19) 0.16610(16) 0.0384(4) Uani 1 1 d . . . . .
C9 C 0.5503(3) 0.69408(19) 0.18950(17) 0.0392(4) Uani 1 1 d . . . . .
H9 H 0.4390 0.6883 0.1185 0.047 Uiso 1 1 calc R U . . .
C12 C 0.2925(3) 0.98648(19) -0.02947(19) 0.0434(4) Uani 1 1 d . . . . .
H12 H 0.1526 0.9768 -0.0490 0.052 Uiso 1 1 calc R U . . .
C3 C 0.8233(3) 0.59619(19) 0.15384(18) 0.0419(4) Uani 1 1 d . . . . .
C10 C 0.7094(4) 0.9364(2) 0.21627(19) 0.0485(5) Uani 1 1 d . . . . .
H10A H 0.8456 0.9926 0.2484 0.058 Uiso 1 1 calc R U . . .
H10B H 0.6388 0.9549 0.2760 0.058 Uiso 1 1 calc R U . . .
C7 C 0.5301(3) 0.4482(2) 0.15601(18) 0.0475(5) Uani 1 1 d . . . . .
H7 H 0.3987 0.4308 0.1622 0.057 Uiso 1 1 calc R U . . .
C6 C 0.6271(4) 0.3489(2) 0.1365(2) 0.0546(6) Uani 1 1 d . . . . .
H6 H 0.5602 0.2641 0.1298 0.066 Uiso 1 1 calc R U . . .
C4 C 0.9242(4) 0.4978(2) 0.1350(2) 0.0535(5) Uani 1 1 d . . . . .
H4 H 1.0552 0.5153 0.1281 0.064 Uiso 1 1 calc R U . . .
C15 C 0.6134(4) 0.7484(3) 0.4132(2) 0.0590(6) Uani 1 1 d . . . . .
H15 H 0.7101 0.8290 0.4196 0.071 Uiso 1 1 calc R U . . .
C5 C 0.8230(4) 0.3739(2) 0.1268(2) 0.0576(6) Uani 1 1 d . . . . .
H5 H 0.8864 0.3060 0.1147 0.069 Uiso 1 1 calc R U . . .
C16 C 0.7346(7) 0.6572(4) 0.4502(3) 0.1005(13) Uani 1 1 d . . . . .
H16A H 0.8189 0.6422 0.3978 0.121 Uiso 1 1 calc R U . . .
H16B H 0.6437 0.5746 0.4414 0.121 Uiso 1 1 calc R U . . .
C20 C 0.4912(6) 0.7829(4) 0.4999(3) 0.0988(12) Uani 1 1 d . . . . .
H20A H 0.4239 0.8494 0.4787 0.119 Uiso 1 1 calc R U . . .
H20B H 0.3872 0.7066 0.4921 0.119 Uiso 1 1 calc R U . . .
C18 C 0.7439(8) 0.7432(5) 0.6652(3) 0.1193(16) Uani 1 1 d . . . . .
H18A H 0.6537 0.6641 0.6654 0.143 Uiso 1 1 calc R U . . .
H18B H 0.8340 0.7818 0.7463 0.143 Uiso 1 1 calc R U . . .
C17 C 0.8697(8) 0.7096(5) 0.5805(3) 0.1226(17) Uani 1 1 d . . . . .
H17A H 0.9395 0.6448 0.6033 0.147 Uiso 1 1 calc R U . . .
H17B H 0.9716 0.7868 0.5875 0.147 Uiso 1 1 calc R U . . .
C19 C 0.6258(10) 0.8322(5) 0.6302(3) 0.140(2) Uani 1 1 d . . . . .
H19A H 0.7167 0.9153 0.6404 0.168 Uiso 1 1 calc R U . . .
H19B H 0.5409 0.8459 0.6825 0.168 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0150 0.0070 '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 0.0250 0.0140 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0410 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2920 0.4240 '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
O22 S2 O21 114.17(13) . . ?
O22 S2 N1 110.48(11) . . ?
O21 S2 N1 113.10(10) . . ?
O22 S2 C3 113.49(11) . . ?
O21 S2 C3 110.55(11) . . ?
N1 S2 C3 93.31(9) . . ?
C10 N1 C9 122.01(16) . . ?
C10 N1 S2 120.24(14) . . ?
C9 N1 S2 116.54(13) . . ?
C9 N14 C15 120.97(17) . . ?
C9 N14 H14 110.5 . . ?
C15 N14 H14 110.2 . . ?
C13 C11 C12 118.47(18) . 2_675 ?
C13 C11 C10 120.57(18) . . ?
C12 C11 C10 120.96(19) 2_675 . ?
C11 C13 C12 121.05(18) . . ?
C11 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C3 C8 C7 119.04(19) . . ?
C3 C8 C9 114.73(17) . . ?
C7 C8 C9 126.23(18) . . ?
N14 C9 N1 115.04(16) . . ?
N14 C9 C8 113.20(16) . . ?
N1 C9 C8 103.40(14) . . ?
N14 C9 H9 108.3 . . ?
N1 C9 H9 108.3 . . ?
C8 C9 H9 108.3 . . ?
C13 C12 C11 120.47(19) . 2_675 ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 2_675 . ?
C8 C3 C4 122.8(2) . . ?
C8 C3 S2 110.86(15) . . ?
C4 C3 S2 126.33(17) . . ?
N1 C10 C11 114.85(17) . . ?
N1 C10 H10A 108.6 . . ?
C11 C10 H10A 108.6 . . ?
N1 C10 H10B 108.6 . . ?
C11 C10 H10B 108.6 . . ?
H10A C10 H10B 107.5 . . ?
C6 C7 C8 119.1(2) . . ?
C6 C7 H7 120.5 . . ?
C8 C7 H7 120.5 . . ?
C7 C6 C5 120.9(2) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C5 C4 C3 117.4(2) . . ?
C5 C4 H4 121.3 . . ?
C3 C4 H4 121.3 . . ?
N14 C15 C16 117.1(2) . . ?
N14 C15 C20 108.0(2) . . ?
C16 C15 C20 110.7(3) . . ?
N14 C15 H15 106.8 . . ?
C16 C15 H15 106.8 . . ?
C20 C15 H15 106.8 . . ?
C4 C5 C6 120.7(2) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C15 C16 C17 111.8(3) . . ?
C15 C16 H16A 109.3 . . ?
C17 C16 H16A 109.3 . . ?
C15 C16 H16B 109.3 . . ?
C17 C16 H16B 109.3 . . ?
H16A C16 H16B 107.9 . . ?
C19 C20 C15 111.8(3) . . ?
C19 C20 H20A 109.2 . . ?
C15 C20 H20A 109.2 . . ?
C19 C20 H20B 109.2 . . ?
C15 C20 H20B 109.2 . . ?
H20A C20 H20B 107.9 . . ?
C19 C18 C17 111.8(4) . . ?
C19 C18 H18A 109.3 . . ?
C17 C18 H18A 109.3 . . ?
C19 C18 H18B 109.3 . . ?
C17 C18 H18B 109.3 . . ?
H18A C18 H18B 107.9 . . ?
C18 C17 C16 110.9(4) . . ?
C18 C17 H17A 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C18 C17 H17B 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 108.1 . . ?
C18 C19 C20 112.5(3) . . ?
C18 C19 H19A 109.1 . . ?
C20 C19 H19A 109.1 . . ?
C18 C19 H19B 109.1 . . ?
C20 C19 H19B 109.1 . . ?
H19A C19 H19B 107.8 . . ?
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
S2 O22 1.4311(19) . ?
S2 O21 1.4373(19) . ?
S2 N1 1.6127(17) . ?
S2 C3 1.741(2) . ?
N1 C10 1.460(2) . ?
N1 C9 1.490(2) . ?
N14 C9 1.427(2) . ?
N14 C15 1.459(3) . ?
N14 H14 0.8600 . ?
C11 C13 1.382(3) . ?
C11 C12 1.396(3) 2_675 ?
C11 C10 1.507(3) . ?
C13 C12 1.383(3) . ?
C13 H13 0.9300 . ?
C8 C3 1.374(3) . ?
C8 C7 1.383(3) . ?
C8 C9 1.511(3) . ?
C9 H9 0.9800 . ?
C12 C11 1.396(3) 2_675 ?
C12 H12 0.9300 . ?
C3 C4 1.391(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C7 C6 1.383(3) . ?
C7 H7 0.9300 . ?
C6 C5 1.388(4) . ?
C6 H6 0.9300 . ?
C4 C5 1.371(3) . ?
C4 H4 0.9300 . ?
C15 C16 1.477(4) . ?
C15 C20 1.527(4) . ?
C15 H15 0.9800 . ?
C5 H5 0.9300 . ?
C16 C17 1.530(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C20 C19 1.526(5) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C18 C19 1.438(6) . ?
C18 C17 1.526(6) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
