#------------------------------------------------------------------------------
#$Date: 2020-11-06 15:08:10 +0200 (Fri, 06 Nov 2020) $
#$Revision: 258952 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/76/7157655.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_7157655
loop_
_publ_author_name
'Kletskov, Alexey V.'
'Zatykina, Anastasya D.'
'Grudova, Mariya V.'
'Sinelshchikova, Anna A.'
'Grigoriev, Mikhail S.'
'Zaytsev, Vladimir P.'
'Gil, Diego M.'
'Novikov, Roman A.'
'Zubkov, Fedor I.'
'Frontera, Antonio'
_publ_section_title
;
 Raise the anchor! Synthesis, X-ray and NMR characterization of
 1,3,5-triazinanes with an axial tert-butyl group.
;
_journal_issue                   41
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              8386
_journal_page_last               8394
_journal_paper_doi               10.1039/d0ob01201g
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C19 H23 I2 N3 O4 S2'
_chemical_formula_sum            'C19 H23 I2 N3 O4 S2'
_chemical_formula_weight         675.32
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2019-12-03 deposited with the CCDC.	2020-08-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.4374(4)
_cell_length_b                   24.9622(6)
_cell_length_c                   6.1336(2)
_cell_measurement_reflns_used    9915
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.74
_cell_measurement_theta_min      2.64
_cell_volume                     2363.59(11)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            28130
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.995
_diffrn_reflns_theta_min         3.930
_exptl_absorpt_coefficient_mu    2.868
_exptl_absorpt_correction_T_max  0.626
_exptl_absorpt_correction_T_min  0.451
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.898
_exptl_crystal_description       fragment
_exptl_crystal_F_000             1312
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DMSO-d6'
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.420
_exptl_crystal_size_min          0.180
_refine_diff_density_max         1.132
_refine_diff_density_min         -0.783
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     142
_refine_ls_number_reflns         3510
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0383
_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)+(0.0258P)²+3.9448P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0815
_refine_ls_wR_factor_ref         0.0854
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2929
_reflns_number_total             3510
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ob01201g3.cif
_cod_data_source_block           AK118
_cod_depositor_comments
'Adding full bibliography for 7157649--7157656.cif.'
_cod_database_code               7157655
_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_min   0.328
_shelx_estimated_absorpt_t_max   0.626
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -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
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.66688(2) 0.47570(2) 0.81041(5) 0.05925(10) Uani 1 1 d . . . . .
S1 S 0.35303(6) 0.35147(4) 0.28140(15) 0.0501(2) Uani 1 1 d . . . . .
O1 O 0.27583(18) 0.38275(12) 0.3004(6) 0.0760(9) Uani 1 1 d . . . . .
O2 O 0.3866(2) 0.33656(11) 0.0727(4) 0.0679(8) Uani 1 1 d . . . . .
N1 N 0.2389(3) 0.250000 0.6608(6) 0.0452(8) Uani 1 2 d S T P . .
N3 N 0.33457(17) 0.29650(11) 0.4120(5) 0.0493(6) Uani 1 1 d . . . . .
C2 C 0.2912(2) 0.29700(17) 0.6294(6) 0.0596(10) Uani 1 1 d . . . . .
H2A H 0.334800 0.298797 0.743096 0.072 Uiso 1 1 calc R U . . .
H2B H 0.255020 0.328643 0.641153 0.072 Uiso 1 1 calc R U . . .
C4 C 0.3905(3) 0.250000 0.3832(9) 0.0522(11) Uani 1 2 d S T P . .
H4A H 0.416159 0.249999 0.238846 0.063 Uiso 1 2 calc R U P . .
H4B H 0.436594 0.250000 0.490753 0.063 Uiso 1 2 calc R U P . .
C5 C 0.1484(3) 0.250000 0.5746(7) 0.0414(9) Uani 1 2 d S T P . .
C6 C 0.1427(3) 0.250000 0.3259(8) 0.0558(13) Uani 1 2 d S T P . .
H6A H 0.083019 0.250000 0.282261 0.084 Uiso 1 2 calc R U P . .
H6B H 0.170821 0.281401 0.269634 0.084 Uiso 0.5 1 calc R U P . .
H6C H 0.170821 0.218599 0.269634 0.084 Uiso 0.5 1 calc R U P . .
C7 C 0.1020(3) 0.29915(17) 0.6646(7) 0.0676(11) Uani 1 1 d . . . . .
H7A H 0.043573 0.299906 0.611122 0.101 Uiso 1 1 calc R U . . .
H7B H 0.101394 0.297570 0.821019 0.101 Uiso 1 1 calc R U . . .
H7C H 0.131810 0.330940 0.618482 0.101 Uiso 1 1 calc R U . . .
C8 C 0.43635(18) 0.38637(11) 0.4195(5) 0.0371(6) Uani 1 1 d . . . . .
C9 C 0.41892(19) 0.41189(14) 0.6141(6) 0.0463(7) Uani 1 1 d . . . . .
H9A H 0.363129 0.411405 0.671277 0.056 Uiso 1 1 calc R U . . .
C10 C 0.4843(2) 0.43809(13) 0.7236(5) 0.0447(7) Uani 1 1 d . . . . .
H10A H 0.472886 0.455566 0.854416 0.054 Uiso 1 1 calc R U . . .
C11 C 0.56701(18) 0.43817(11) 0.6373(5) 0.0371(6) Uani 1 1 d . . . . .
C12 C 0.58446(19) 0.41357(13) 0.4412(6) 0.0468(7) Uani 1 1 d . . . . .
H12A H 0.639932 0.414659 0.382249 0.056 Uiso 1 1 calc R U . . .
C13 C 0.5184(2) 0.38723(14) 0.3332(5) 0.0480(7) Uani 1 1 d . . . . .
H13A H 0.529569 0.370037 0.201649 0.058 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 0.0033 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'
I I -0.4742 1.8119 '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
O1 S1 O2 121.13(19) . . ?
O1 S1 N3 106.06(18) . . ?
O2 S1 N3 106.67(16) . . ?
O1 S1 C8 107.34(15) . . ?
O2 S1 C8 107.06(16) . . ?
N3 S1 C8 108.02(15) . . ?
C2 N1 C2 109.5(4) . 7_565 ?
C2 N1 C5 118.6(2) . . ?
C2 N1 C5 118.6(2) 7_565 . ?
C4 N3 C2 112.4(3) . . ?
C4 N3 S1 120.8(3) . . ?
C2 N3 S1 121.0(2) . . ?
N1 C2 N3 111.4(3) . . ?
N1 C2 H2A 109.4 . . ?
N3 C2 H2A 109.4 . . ?
N1 C2 H2B 109.4 . . ?
N3 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
N3 C4 N3 105.6(4) 7_565 . ?
N3 C4 H4A 110.6 7_565 . ?
N3 C4 H4A 110.6 . . ?
N3 C4 H4B 110.6 7_565 . ?
N3 C4 H4B 110.6 . . ?
H4A C4 H4B 108.8 . . ?
N1 C5 C7 108.1(3) . . ?
N1 C5 C7 108.1(3) . 7_565 ?
C7 C5 C7 107.2(4) . 7_565 ?
N1 C5 C6 114.0(4) . . ?
C7 C5 C6 109.6(3) . . ?
C7 C5 C6 109.6(3) 7_565 . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C13 C8 C9 120.4(3) . . ?
C13 C8 S1 119.6(2) . . ?
C9 C8 S1 120.0(2) . . ?
C10 C9 C8 119.9(3) . . ?
C10 C9 H9A 120.1 . . ?
C8 C9 H9A 120.1 . . ?
C9 C10 C11 119.4(3) . . ?
C9 C10 H10A 120.3 . . ?
C11 C10 H10A 120.3 . . ?
C12 C11 C10 121.0(3) . . ?
C12 C11 I1 119.9(2) . . ?
C10 C11 I1 119.1(2) . . ?
C11 C12 C13 119.1(3) . . ?
C11 C12 H12A 120.4 . . ?
C13 C12 H12A 120.4 . . ?
C8 C13 C12 120.2(3) . . ?
C8 C13 H13A 119.9 . . ?
C12 C13 H13A 119.9 . . ?
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
I1 C11 2.093(3) . ?
S1 O1 1.430(3) . ?
S1 O2 1.430(3) . ?
S1 N3 1.614(3) . ?
S1 C8 1.769(3) . ?
N1 C2 1.437(4) . ?
N1 C2 1.437(4) 7_565 ?
N1 C5 1.494(6) . ?
N3 C4 1.457(4) . ?
N3 C2 1.493(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C7 1.524(4) . ?
C5 C7 1.524(4) 7_565 ?
C5 C6 1.528(6) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C13 1.373(4) . ?
C8 C9 1.380(4) . ?
C9 C10 1.377(4) . ?
C9 H9A 0.9300 . ?
C10 C11 1.382(4) . ?
C10 H10A 0.9300 . ?
C11 C12 1.377(4) . ?
C12 C13 1.383(4) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C2 H2A O2 0.97 2.37 3.246(4) 149.9 1_556 yes
C12 H12A O1 0.93 2.51 3.394(4) 159.2 6_656 yes
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
O1 S1 N3 C4 165.0(3) . . . . ?
O2 S1 N3 C4 34.6(3) . . . . ?
C8 S1 N3 C4 -80.2(3) . . . . ?
O1 S1 N3 C2 -43.8(3) . . . . ?
O2 S1 N3 C2 -174.2(3) . . . . ?
C8 S1 N3 C2 71.0(3) . . . . ?
C2 N1 C2 N3 55.3(5) 7_565 . . . ?
C5 N1 C2 N3 -85.0(4) . . . . ?
C4 N3 C2 N1 -59.3(4) . . . . ?
S1 N3 C2 N1 147.3(3) . . . . ?
C2 N3 C4 N3 58.2(5) . . . 7_565 ?
S1 N3 C4 N3 -148.3(2) . . . 7_565 ?
C2 N1 C5 C7 -53.7(5) . . . . ?
C2 N1 C5 C7 169.5(3) 7_565 . . . ?
C2 N1 C5 C7 -169.5(3) . . . 7_565 ?
C2 N1 C5 C7 53.7(5) 7_565 . . 7_565 ?
C2 N1 C5 C6 68.4(3) . . . . ?
C2 N1 C5 C6 -68.4(3) 7_565 . . . ?
O1 S1 C8 C13 -141.0(3) . . . . ?
O2 S1 C8 C13 -9.5(3) . . . . ?
N3 S1 C8 C13 105.0(3) . . . . ?
O1 S1 C8 C9 39.9(3) . . . . ?
O2 S1 C8 C9 171.4(3) . . . . ?
N3 S1 C8 C9 -74.1(3) . . . . ?
C13 C8 C9 C10 -0.5(5) . . . . ?
S1 C8 C9 C10 178.7(3) . . . . ?
C8 C9 C10 C11 -0.4(5) . . . . ?
C9 C10 C11 C12 1.6(5) . . . . ?
C9 C10 C11 I1 -177.8(3) . . . . ?
C10 C11 C12 C13 -1.8(5) . . . . ?
I1 C11 C12 C13 177.5(3) . . . . ?
C9 C8 C13 C12 0.2(5) . . . . ?
S1 C8 C13 C12 -178.9(3) . . . . ?
C11 C12 C13 C8 0.9(5) . . . . ?
