#------------------------------------------------------------------------------
#$Date: 2017-11-16 07:04:10 +0200 (Thu, 16 Nov 2017) $
#$Revision: 203230 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/67/7056753.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_7056753
loop_
_publ_author_name
'Soares, Maria I.L.'
'Manaia Nunes, Cláudio'
'Gomes, Clara S. B.'
'Pinho e Melo, Teresa M. V. D.'
'Fausto, Rui'
_publ_section_title
;
 Conformational Behaviour, Photochemistry and Flash Vacuum Pyrolysis of a
 2-(1H-Tetrazol-1-yl)thiophene
;
_journal_name_full               'New Journal of Chemistry'
_journal_paper_doi               10.1039/C7NJ02775C
_journal_year                    2017
_chemical_formula_moiety         'C7 H6 N4 O2 S'
_chemical_formula_sum            'C7 H6 N4 O2 S'
_chemical_formula_weight         210.22
_chemical_name_systematic
'Methyl 2-(1H-tetrazol-1-yl)thiophene-3-carboxylate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-11-13 deposited with the CCDC.
2017-11-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.936(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.9245(5)
_cell_length_b                   18.054(2)
_cell_length_c                   12.6455(15)
_cell_measurement_reflns_used    2657
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.39
_cell_measurement_theta_min      2.78
_cell_volume                     885.10(18)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP
_computing_publication_material  enCIFer
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    SIR2014
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5591
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.681
_diffrn_reflns_theta_min         2.784
_exptl_absorpt_coefficient_mu    0.343
_exptl_absorpt_correction_T_max  0.935
_exptl_absorpt_correction_T_min  0.904
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_description       prism
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         1710
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0347
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0600P)²+0.0548P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0909
_refine_ls_wR_factor_ref         0.0937
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1569
_reflns_number_total             1710
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7nj02775c2.cif
_cod_data_source_block           shelx
_cod_original_cell_volume        885.09(19)
_cod_database_code               7056753
_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.
;
_shelx_estimated_absorpt_t_min   0.904
_shelx_estimated_absorpt_t_max   0.935
loop_
_space_group_symop_operation_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_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
S1 S 0.87858(17) 0.18744(3) 0.33189(5) 0.03740(19) Uani 1 1 d . .
O13 O 0.3595(5) -0.05661(9) 0.30259(13) 0.0441(5) Uani 1 1 d . .
N6 N 0.5345(5) 0.14992(10) 0.13805(13) 0.0310(4) Uani 1 1 d . .
O12 O 0.2275(5) 0.00131(10) 0.14498(14) 0.0523(5) Uani 1 1 d . .
C11 C 0.3717(7) 0.00015(12) 0.23607(18) 0.0340(5) Uani 1 1 d . .
N8 N 0.3113(8) 0.22146(14) 0.01380(19) 0.0573(7) Uani 1 1 d . .
N9 N 0.4422(7) 0.16251(14) -0.03303(16) 0.0517(6) Uani 1 1 d . .
C2 C 0.6433(6) 0.12721(12) 0.24551(16) 0.0299(5) Uani 1 1 d . .
C5 C 0.9001(8) 0.12433(15) 0.43272(18) 0.0412(6) Uani 1 1 d . .
H5 H 1.0127 0.1328 0.5019 0.049 Uiso 1 1 calc R U
N7 N 0.3641(7) 0.21526(12) 0.11649(18) 0.0477(6) Uani 1 1 d . .
C4 C 0.7355(7) 0.06075(13) 0.40091(18) 0.0367(5) Uani 1 1 d . .
H4 H 0.7236 0.0206 0.4462 0.044 Uiso 1 1 calc R U
C3 C 0.5818(6) 0.06096(12) 0.29147(17) 0.0311(5) Uani 1 1 d . .
C10 C 0.5782(8) 0.11982(15) 0.04506(18) 0.0436(6) Uani 1 1 d . .
H10 H 0.6889 0.0751 0.0371 0.052 Uiso 1 1 calc R U
C14 C 0.1715(9) -0.12150(13) 0.2580(2) 0.0523(7) Uani 1 1 d . .
H14A H -0.0530 -0.1069 0.2228 0.079 Uiso 1 1 calc R U
H14C H 0.1477 -0.1557 0.3145 0.079 Uiso 1 1 calc R U
H14B H 0.2953 -0.1448 0.2073 0.079 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C5 S1 C2 90.68(12)
C11 O13 C14 116.24(19)
C10 N6 N7 107.7(2)
C10 N6 C2 131.8(2)
N7 N6 C2 120.45(18)
O12 C11 O13 124.1(2)
O12 C11 C3 125.8(2)
O13 C11 C3 110.09(19)
N7 N8 N9 111.0(2)
C10 N9 N8 105.8(2)
C3 C2 N6 127.8(2)
C3 C2 S1 113.50(16)
N6 C2 S1 118.72(16)
C4 C5 S1 112.39(18)
N8 N7 N6 105.9(2)
C5 C4 C3 113.6(2)
C2 C3 C4 109.9(2)
C2 C3 C11 124.7(2)
C4 C3 C11 125.4(2)
N9 C10 N6 109.6(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C5 1.702(2)
S1 C2 1.707(2)
O13 C11 1.331(3)
O13 C14 1.451(3)
N6 C10 1.330(3)
N6 N7 1.363(3)
N6 C2 1.420(3)
O12 C11 1.202(3)
C11 C3 1.482(3)
N8 N7 1.288(3)
N8 N9 1.357(3)
N9 C10 1.300(3)
C2 C3 1.368(3)
C5 C4 1.348(4)
C4 C3 1.421(3)
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
C14 O13 C11 O12 3.0(4)
C14 O13 C11 C3 -178.0(2)
N7 N8 N9 C10 -0.1(3)
C10 N6 C2 C3 -55.4(4)
N7 N6 C2 C3 127.8(3)
C10 N6 C2 S1 124.9(3)
N7 N6 C2 S1 -51.8(3)
C5 S1 C2 C3 0.0(2)
C5 S1 C2 N6 179.8(2)
C2 S1 C5 C4 0.1(2)
N9 N8 N7 N6 -0.2(3)
C10 N6 N7 N8 0.4(3)
C2 N6 N7 N8 177.9(2)
S1 C5 C4 C3 -0.2(3)
N6 C2 C3 C4 -179.9(2)
S1 C2 C3 C4 -0.2(3)
N6 C2 C3 C11 -2.5(4)
S1 C2 C3 C11 177.20(18)
C5 C4 C3 C2 0.2(3)
C5 C4 C3 C11 -177.1(2)
O12 C11 C3 C2 -0.7(4)
O13 C11 C3 C2 -179.7(2)
O12 C11 C3 C4 176.3(3)
O13 C11 C3 C4 -2.7(3)
N8 N9 C10 N6 0.3(3)
N7 N6 C10 N9 -0.5(3)
C2 N6 C10 N9 -177.6(2)
