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#$Date: 2022-01-15 04:35:15 +0200 (Sat, 15 Jan 2022) $
#$Revision: 272050 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/40/2244006.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2244006
loop_
_publ_author_name
'Schultheiss, Nate'
'Holtsclaw, Jeremy'
'Zeller, Matthias'
_publ_section_title
;
 An orthorhombic polymorph of 2-(1,3,5-dithiazinan-5-yl)ethanol or
 MEA-dithiazine
;
_journal_coeditor_code           HB8010
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2056989022000342
_journal_volume                  78
_journal_year                    2022
_chemical_formula_iupac          'C5 H11 N O S2'
_chemical_formula_moiety         'C5 H11 N O S2'
_chemical_formula_sum            'C5 H11 N O S2'
_chemical_formula_weight         165.27
_chemical_name_common            MEA-dithiazine
_chemical_name_systematic
;
2-(1,3,5-Dithiazinan-5-yl)ethanol
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.5828(4)
_cell_length_b                   8.8467(3)
_cell_length_c                   17.6400(8)
_cell_measurement_reflns_used    9803
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      33.1422
_cell_measurement_theta_min      2.3092
_cell_volume                     1495.45(11)
_computing_cell_refinement
;
SAINT (Bruker, 2019)
;
_computing_data_collection
;
APEX3 (Bruker, 2019)
;
_computing_data_reduction
;
SAINT (Bruker, 2019)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2020)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015),
shelXle (Hübschle et al., 2011)
;
_computing_structure_solution
;
SHELXS (Sheldrick, 2008)
;
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 7.4074
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
;
Bruker AXS D8 Quest diffractometer with PhotonII charge-integrating pixel
array detector (CPAD)
;
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'Triumph curved graphite crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_unetI/netI     0.0139
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            60184
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.166
_diffrn_reflns_theta_min         3.139
_diffrn_source                   'fine focus sealed tube X-ray source'
_diffrn_source_current           30
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.631
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.6894
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.280
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.206
_refine_ls_extinction_coef       0.0043(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL-2018/3 (Sheldrick, 2015)
;
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     86
_refine_ls_number_reflns         2857
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0209
_refine_ls_R_factor_gt           0.0184
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0247P)²+0.3304P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0519
_refine_ls_wR_factor_ref         0.0528
_reflns_number_gt                2609
_reflns_number_total             2857
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb8010sup1.cif
_cod_data_source_block           150K
_cod_database_code               2244006
_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   0.782
_shelx_estimated_absorpt_t_max   0.843
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.49529(2) 0.46751(2) 0.67098(2) 0.01985(5) Uani d 1 . .
S S2 0.24939(2) 0.25649(2) 0.68835(2) 0.01846(5) Uani d 1 . .
O O1 0.35020(6) 0.04378(6) 0.45260(3) 0.02346(11) Uani d 1 . .
H H1 0.4068(14) -0.0193(14) 0.4443(7) 0.035 Uiso d 1 . .
N N1 0.46380(6) 0.20571(6) 0.58421(3) 0.01538(10) Uani d 1 . .
C C1 0.38115(7) 0.36827(8) 0.73583(4) 0.01980(12) Uani d 1 . .
H H1A 0.438074 0.301055 0.768347 0.024 Uiso calc 1 . .
H H1B 0.334562 0.442853 0.769154 0.024 Uiso calc 1 . .
C C2 0.36757(7) 0.13153(7) 0.63564(4) 0.01697(11) Uani d 1 . .
H H2A 0.422566 0.072117 0.672647 0.020 Uiso calc 1 . .
H H2B 0.310423 0.059314 0.606076 0.020 Uiso calc 1 . .
C C3 0.56527(7) 0.30023(8) 0.62278(4) 0.01882(12) Uani d 1 . .
H H3A 0.635243 0.334132 0.585154 0.023 Uiso calc 1 . .
H H3B 0.614675 0.237470 0.660711 0.023 Uiso calc 1 . .
C C4 0.39690(8) 0.27738(7) 0.51799(4) 0.01898(12) Uani d 1 . .
H H4A 0.436105 0.379919 0.510816 0.023 Uiso calc 1 . .
H H4B 0.295599 0.287903 0.527660 0.023 Uiso calc 1 . .
C C5 0.41878(7) 0.18614(8) 0.44649(4) 0.01854(12) Uani d 1 . .
H H5A 0.381227 0.242363 0.402461 0.022 Uiso calc 1 . .
H H5B 0.519867 0.170101 0.438174 0.022 Uiso calc 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 S1 C3 . . 97.04(3) ?
C1 S2 C2 . . 97.65(3) ?
C5 O1 H1 . . 107.0(9) ?
C2 N1 C3 . . 113.16(5) ?
C2 N1 C4 . . 114.41(5) ?
C3 N1 C4 . . 114.49(5) ?
S2 C1 S1 . . 113.22(4) ?
S2 C1 H1A . . 108.9 ?
S1 C1 H1A . . 108.9 ?
S2 C1 H1B . . 108.9 ?
S1 C1 H1B . . 108.9 ?
H1A C1 H1B . . 107.7 ?
N1 C2 S2 . . 115.88(4) ?
N1 C2 H2A . . 108.3 ?
S2 C2 H2A . . 108.3 ?
N1 C2 H2B . . 108.3 ?
S2 C2 H2B . . 108.3 ?
H2A C2 H2B . . 107.4 ?
N1 C3 S1 . . 115.93(5) ?
N1 C3 H3A . . 108.3 ?
S1 C3 H3A . . 108.3 ?
N1 C3 H3B . . 108.3 ?
S1 C3 H3B . . 108.3 ?
H3A C3 H3B . . 107.4 ?
N1 C4 C5 . . 111.76(5) ?
N1 C4 H4A . . 109.3 ?
C5 C4 H4A . . 109.3 ?
N1 C4 H4B . . 109.3 ?
C5 C4 H4B . . 109.3 ?
H4A C4 H4B . . 107.9 ?
O1 C5 C4 . . 110.17(5) ?
O1 C5 H5A . . 109.6 ?
C4 C5 H5A . . 109.6 ?
O1 C5 H5B . . 109.6 ?
C4 C5 H5B . . 109.6 ?
H5A C5 H5B . . 108.1 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C1 . 1.8100(7) ?
S1 C3 . 1.8338(7) ?
S2 C1 . 1.8093(7) ?
S2 C2 . 1.8355(7) ?
O1 C5 . 1.4247(9) ?
O1 H1 . 0.792(13) ?
N1 C2 . 1.4505(8) ?
N1 C3 . 1.4517(9) ?
N1 C4 . 1.4758(8) ?
C1 H1A . 0.9900 ?
C1 H1B . 0.9900 ?
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C4 C5 . 1.5120(9) ?
C4 H4A . 0.9900 ?
C4 H4B . 0.9900 ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1 N1 5_656 0.792(13) 2.124(13) 2.9103(8) 172.3(13) yes
C3 H3A O1 4_556 0.99 2.42 3.3359(9) 154 yes
C2 H2A S1 3_646 0.99 3.01 3.9330(7) 155 yes
C3 H3B S2 6_657 0.99 2.96 3.7899(7) 142 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 S2 C1 S1 . . . . 60.15(4) y
C3 S1 C1 S2 . . . . -60.52(4) y
C3 N1 C2 S2 . . . . 65.52(6) y
C4 N1 C2 S2 . . . . -68.05(6) y
C1 S2 C2 N1 . . . . -58.98(5) y
C2 N1 C3 S1 . . . . -66.53(6) y
C4 N1 C3 S1 . . . . 67.01(7) y
C1 S1 C3 N1 . . . . 60.35(5) y
C2 N1 C4 C5 . . . . -104.74(6) y
C3 N1 C4 C5 . . . . 122.32(6) y
N1 C4 C5 O1 . . . . 65.09(7) y

_cod_database_fobs_code 2244006
