#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:43:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/82/2208240.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_2208240
loop_
_publ_author_name
'Lyakhov, Alexander S.'
'Egorova, Natalia G. '
'Artamonova, Tatiana V.'
'Gaponik, Pavel N.'
'Koldobskii, Grigorii I.'
_publ_section_title
;
 5-Mesylmethoxy-1-(4-nitrophenyl)tetrazole
;
_journal_coeditor_code           AT6082
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o903
_journal_page_last               o905
_journal_paper_doi               10.1107/S1600536806003837
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C9 H9 N5 O5 S'
_chemical_formula_moiety         'C9 H9 N5 O5 S'
_chemical_formula_sum            'C9 H9 N5 O5 S'
_chemical_formula_weight         299.27
_chemical_name_systematic
;
5-Mesylmethoxy-1-(4-nitrophenyl)tetrazole
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.696(17)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.413(3)
_cell_length_b                   8.093(3)
_cell_length_c                   12.770(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      18.6
_cell_measurement_theta_min      14.8
_cell_volume                     1256.2(6)
_computing_cell_refinement       'R3m Software'
_computing_data_collection       'R3m Software (Nicolet, 1980)'
_computing_data_reduction        'R3m Software'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003)
;
_computing_publication_material  'SHELXL97 and PLATON'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1999)'
_diffrn_ambient_temperature      292(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Nicolet R3m four-circle'
_diffrn_measurement_method       ω/2θ
_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  0.0144
_diffrn_reflns_av_sigmaI/netI    0.0194
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3053
_diffrn_reflns_theta_full        27.58
_diffrn_reflns_theta_max         27.58
_diffrn_reflns_theta_min         1.68
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.287
_exptl_absorpt_correction_T_max  0.933
_exptl_absorpt_correction_T_min  0.885
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.320
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         2920
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0394
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.06P)²+0.3301P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1104
_refine_ls_wR_factor_ref         0.1193
_reflns_number_gt                2333
_reflns_number_total             2920
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at6082.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (7
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (9 times).

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (7
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (9 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2208240
_cod_database_fobs_code          2208240
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_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_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
S1 1.01559(4) 0.12883(6) 0.85348(4) 0.05077(16) Uani d . 1 S
O3 1.07668(11) -0.00527(18) 0.91067(11) 0.0608(4) Uani d . 1 O
O4 1.04308(14) 0.1843(2) 0.75575(13) 0.0746(5) Uani d . 1 O
N1 0.72002(12) 0.29950(19) 0.60690(11) 0.0466(3) Uani d . 1 N
N2 0.70247(15) 0.2471(2) 0.50318(12) 0.0630(5) Uani d . 1 N
N3 0.74825(17) 0.1049(3) 0.50404(14) 0.0702(5) Uani d . 1 N
N4 0.79718(15) 0.0583(2) 0.60541(13) 0.0620(4) Uani d . 1 N
C5 0.77867(14) 0.1804(2) 0.66563(14) 0.0480(4) Uani d . 1 C
O5 0.80806(11) 0.19224(17) 0.77134(9) 0.0560(3) Uani d . 1 O
C6 0.68264(13) 0.4576(2) 0.63270(13) 0.0442(4) Uani d . 1 C
C7 0.63760(17) 0.5621(3) 0.54982(14) 0.0564(5) Uani d . 1 C
H7 0.6277(19) 0.523(3) 0.477(2) 0.079(7) Uiso d . 1 H
C8 0.60233(18) 0.7163(3) 0.57186(15) 0.0568(5) Uani d . 1 C
H8 0.574(2) 0.788(3) 0.522(2) 0.079(7) Uiso d . 1 H
C9 0.61311(14) 0.7642(2) 0.67681(13) 0.0476(4) Uani d . 1 C
C10 0.65693(17) 0.6613(3) 0.75983(14) 0.0564(5) Uani d . 1 C
H10 0.657(2) 0.696(3) 0.8309(19) 0.073(7) Uiso d . 1 H
C11 0.69095(17) 0.5053(3) 0.73805(14) 0.0561(5) Uani d . 1 C
H11 0.7224(19) 0.429(3) 0.7972(19) 0.075(7) Uiso d . 1 H
N12 0.57836(14) 0.9301(2) 0.69993(13) 0.0590(4) Uani d . 1 N
O1 0.53584(15) 1.0187(2) 0.62637(13) 0.0787(5) Uani d . 1 O
O2 0.59597(19) 0.9764(3) 0.79146(13) 0.1055(8) Uani d . 1 O
C13 0.87550(15) 0.0626(2) 0.82517(15) 0.0498(4) Uani d . 1 C
H13A 0.8734(18) -0.036(3) 0.7837(18) 0.064(6) Uiso d . 1 H
H13B 0.8529(17) 0.043(3) 0.8935(18) 0.063(6) Uiso d . 1 H
C14 1.0160(2) 0.2969(3) 0.9394(2) 0.0701(6) Uani d . 1 C
H14A 0.9914 0.2616 1.0024 0.105 Uiso calc R 1 H
H14B 0.9676 0.3811 0.9038 0.105 Uiso calc R 1 H
H14C 1.0892 0.3405 0.9592 0.105 Uiso calc R 1 H
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_publ_flag
O4 S1 O3 119.08(10) ?
O4 S1 C14 109.41(11) ?
O3 S1 C14 109.59(11) ?
O4 S1 C13 108.19(10) ?
O3 S1 C13 105.57(9) ?
C14 S1 C13 103.86(11) ?
C5 N1 N2 106.30(15) y
C5 N1 C6 133.03(15) y
N2 N1 C6 120.59(14) y
N3 N2 N1 106.70(15) y
N2 N3 N4 111.52(16) y
C5 N4 N3 104.61(16) y
N4 C5 O5 127.63(17) y
N4 C5 N1 110.86(16) y
O5 C5 N1 121.48(16) y
C5 O5 C13 116.71(15) ?
C7 C6 C11 120.86(18) ?
C7 C6 N1 118.27(15) ?
C11 C6 N1 120.87(15) ?
C8 C7 C6 119.78(17) ?
C8 C7 H7 120.9(15) ?
C6 C7 H7 119.2(15) ?
C7 C8 C9 119.00(17) ?
C7 C8 H8 123.1(17) ?
C9 C8 H8 117.9(17) ?
C10 C9 C8 121.81(18) ?
C10 C9 N12 119.34(16) ?
C8 C9 N12 118.84(16) ?
C9 C10 C11 119.37(17) ?
C9 C10 H10 118.6(15) ?
C11 C10 H10 121.8(15) ?
C10 C11 C6 119.14(17) ?
C10 C11 H11 120.5(14) ?
C6 C11 H11 120.4(14) ?
O2 N12 O1 122.15(19) ?
O2 N12 C9 118.66(17) ?
O1 N12 C9 119.15(17) ?
O5 C13 S1 109.20(13) ?
O5 C13 H13A 113.6(13) ?
S1 C13 H13A 106.2(13) ?
O5 C13 H13B 107.7(13) ?
S1 C13 H13B 108.2(12) ?
H13A C13 H13B 111.9(18) ?
S1 C14 H14A 109.5 ?
S1 C14 H14B 109.5 ?
H14A C14 H14B 109.5 ?
S1 C14 H14C 109.5 ?
H14A C14 H14C 109.5 ?
H14B C14 H14C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O4 1.4312(15) ?
S1 O3 1.4358(14) ?
S1 C14 1.747(2) ?
S1 C13 1.785(2) ?
N1 C5 1.342(2) y
N1 N2 1.366(2) y
N1 C6 1.422(2) y
N2 N3 1.282(3) y
N3 N4 1.367(2) y
N4 C5 1.301(2) y
C5 O5 1.328(2) y
O5 C13 1.428(2) ?
C6 C7 1.381(2) ?
C6 C11 1.383(2) ?
C7 C8 1.370(3) ?
C7 H7 0.96(3) ?
C8 C9 1.375(2) ?
C8 H8 0.88(3) ?
C9 C10 1.371(3) ?
C9 N12 1.459(3) ?
C10 C11 1.377(3) ?
C10 H10 0.95(2) ?
C11 H11 0.99(2) ?
N12 O2 1.204(2) ?
N12 O1 1.214(2) ?
C13 H13A 0.96(2) ?
C13 H13B 0.98(2) ?
C14 H14A 0.9600 ?
C14 H14B 0.9600 ?
C14 H14C 0.9600 ?
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
C7 H7 O2 4_575 0.96(3) 2.33(3) 3.249(3) 161(2)
C11 H11 N3 4_566 0.99(2) 2.61(2) 3.444(3) 141.6(18)
C13 H13A O4 2_746 0.96(2) 2.58(2) 3.448(3) 150.9(17)
C13 H13B O3 3_757 0.98(2) 2.49(2) 3.337(2) 143.6(16)
C14 H14A O3 3_757 0.96 2.58 3.385(3) 142
C14 H14C N4 2_756 0.96 2.50 3.274(3) 138
C11 H11 O5 . 0.99(2) 2.25(2) 2.909(2) 123.0(18)
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
C5 N1 N2 N3 0.5(2)
C6 N1 N2 N3 177.57(17)
N1 N2 N3 N4 -0.2(3)
N2 N3 N4 C5 -0.2(3)
N3 N4 C5 O5 178.54(19)
N3 N4 C5 N1 0.5(2)
N2 N1 C5 N4 -0.7(2)
C6 N1 C5 N4 -177.19(18)
N2 N1 C5 O5 -178.83(17)
C6 N1 C5 O5 4.7(3)
N4 C5 O5 C13 5.5(3)
N1 C5 O5 C13 -176.64(16)
C5 N1 C6 C7 170.18(19)
N2 N1 C6 C7 -5.9(2)
C5 N1 C6 C11 -10.0(3)
N2 N1 C6 C11 173.94(18)
C11 C6 C7 C8 1.1(3)
N1 C6 C7 C8 -179.00(18)
C6 C7 C8 C9 0.3(3)
C7 C8 C9 C10 -0.8(3)
C7 C8 C9 N12 178.27(18)
C8 C9 C10 C11 -0.2(3)
N12 C9 C10 C11 -179.23(19)
C9 C10 C11 C6 1.6(3)
C7 C6 C11 C10 -2.1(3)
N1 C6 C11 C10 178.04(18)
C10 C9 N12 O2 5.0(3)
C8 C9 N12 O2 -174.1(2)
C10 C9 N12 O1 -177.3(2)
C8 C9 N12 O1 3.6(3)
C5 O5 C13 S1 99.22(17)
O4 S1 C13 O5 -53.57(16)
O3 S1 C13 O5 177.92(12)
C14 S1 C13 O5 62.62(16)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21126427
2 PubChem 129741226
