#------------------------------------------------------------------------------
#$Date: 2016-02-21 01:03:34 +0100 (dom 21 de feb de 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/84/2238441.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_2238441
loop_
_publ_author_name
'Hsu, Gene C.'
'Singer, Laci M.'
'Cordes, David B.'
'Findlater, Michael'
_publ_section_title
;
 Thiophene-2-carbonyl azide
;
_journal_coeditor_code           TK5242
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1298
_journal_paper_doi               10.1107/S1600536813019740
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C5 H3 N3 O S'
_chemical_formula_moiety         'C5 H3 N3 O S'
_chemical_formula_sum            'C5 H3 N3 O S'
_chemical_formula_weight         153.16
_chemical_name_systematic
;
Thiophene-2-carbonyl azide
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 95.91(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.668(3)
_cell_length_b                   6.2153(12)
_cell_length_c                   16.400(3)
_cell_measurement_reflns_used    1494
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     1284.4(5)
_computing_cell_refinement       'COLLECT (Nonius, 1998)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction
;
DENZO and SCALEPACK (Otwinowski & Minor, 1997)
;
_computing_molecular_graphics
'SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008), enCIFer (Allen et al., 2004)
and publCIF
(Westrip, 2010)
;
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2013)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            2728
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.443
_diffrn_reflns_theta_min         2.497
_exptl_absorpt_coefficient_mu    0.425
_exptl_absorpt_correction_T_max  0.9390
_exptl_absorpt_correction_T_min  0.9198
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'(DENZO and SCALEPACK; Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.587
_refine_diff_density_min         -0.494
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         1459
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.127
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0499
_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)+(0.0659P)²+3.2530P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1447
_refine_ls_wR_factor_ref         0.1542
_reflns_number_gt                1152
_reflns_number_total             1459
_reflns_threshold_expression     I>2σ(I)
_iucr_refine_instructions_details
;
TITL try1 in C2/c
CELL  0.71073  12.6679   6.2153  16.4001   90.000   95.906   90.000
ZERR     8.00   0.0025   0.0012   0.0033    0.000    0.030    0.000
LATT   7
SYMM  - X,   Y, 1/2 - Z
SFAC  C    H    N    O    S
UNIT  40   24   24   8    8
MERG   2
FMAP   2
PLAN    5
SIZE     0.15   0.16   0.20
EQIV $1 x, -y, z+1/2
HTAB C4 O1_$1
HTAB C3 N3_$1
EQIV $2 x, y-1, z
HTAB C2 N1_$2
ACTA
BOND   $H
CONF
HTAB
L.S.  4
TEMP  -120.00
WGHT    0.065900    3.253000
FVAR       0.39673
C1    1    0.367624    0.037284    0.579264    11.00000    0.02493    0.02954 =
         0.02373   -0.00393    0.00390   -0.00111
C2    1    0.349410   -0.182741    0.598636    11.00000    0.02465    0.02256 =
         0.02482    0.00528    0.00618    0.00054
AFIX  43
H2    2    0.340102   -0.298818    0.560894    11.00000   -1.20000
AFIX   0
C3    1    0.347794   -0.195625    0.687297    11.00000    0.03585    0.03080 =
         0.03400    0.00793    0.00553   -0.00053
AFIX  43
H3    2    0.336849   -0.326655    0.715044    11.00000   -1.20000
AFIX   0
C4    1    0.363228   -0.004842    0.726753    11.00000    0.03640    0.04378 =
         0.02401    0.00262    0.00354    0.00340
AFIX  43
H4    2    0.364695    0.010512    0.784492    11.00000   -1.20000
AFIX   0
C5    1    0.376349    0.113272    0.495751    11.00000    0.02513    0.03113 =
         0.02553   -0.00277    0.00454   -0.00212
N1    3    0.394558    0.338616    0.493854    11.00000    0.04382    0.03356 =
         0.01957   -0.00025    0.00279   -0.00073
N2    3    0.399199    0.409266    0.422272    11.00000    0.03165    0.03346 =
         0.02661   -0.00262    0.00023   -0.00348
N3    3    0.404386    0.487897    0.361246    11.00000    0.04614    0.04496 =
         0.02862    0.00394    0.00050   -0.01089
O1    4    0.369275   -0.000273    0.435379    11.00000    0.05191    0.03815 =
         0.02547   -0.00719    0.00800   -0.00858
S1    5    0.379495    0.201649    0.663197    11.00000    0.04865    0.03181 =
         0.02748   -0.00179    0.00361   -0.00278
HKLF 4
REM  try1 in C2/c
REM R1 =  0.0499 for    1152 Fo > 4sig(Fo)  and  0.0656 for all    1459 data
REM     91 parameters refined using      0 restraints
END
WGHT      0.0659      3.2529
REM Instructions for potential hydrogen bonds
HTAB C2 N1_$2
HTAB C3 N3_$1
HTAB C4 O1_$1
REM Highest difference peak  0.587,  deepest hole -0.494,  1-sigma level  0.078
Q1    1   0.3484 -0.1810  0.6277  11.00000  0.05    0.59
Q2    1   0.3538 -0.1110  0.5904  11.00000  0.05    0.58
Q3    1   0.3460 -0.2111  0.5766  11.00000  0.05    0.57
Q4    1   0.3708  0.3934  0.6702  11.00000  0.05    0.35
Q5    1   0.3678  0.1173  0.6086  11.00000  0.05    0.32
;
_cod_data_source_file            tk5242.cif
_cod_data_source_block           I
_cod_original_cell_volume        1284.4(4)
_cod_database_code               2238441
_cod_database_fobs_code          2238441
#BEGIN Tags that were not found in dictionaries:
_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   0.920
_shelx_estimated_absorpt_t_max   0.939
_shelxl_version_number           2.013
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
C C1 0.3676(2) 0.0373(4) 0.57926(15) 0.0260(6) Uani d 1
C C2 0.3494(2) -0.1827(4) 0.59864(15) 0.0238(6) Uani d 1
H H2 0.3401 -0.2988 0.5609 0.029 Uiso calc 1
C C3 0.3478(2) -0.1956(5) 0.68730(18) 0.0334(7) Uani d 1
H H3 0.3368 -0.3267 0.7150 0.040 Uiso calc 1
C C4 0.3632(2) -0.0048(5) 0.72675(17) 0.0347(7) Uani d 1
H H4 0.3647 0.0105 0.7845 0.042 Uiso calc 1
C C5 0.3763(2) 0.1133(5) 0.49575(15) 0.0271(6) Uani d 1
N N1 0.3946(2) 0.3386(4) 0.49385(13) 0.0323(6) Uani d 1
N N2 0.39920(19) 0.4093(4) 0.42227(13) 0.0308(6) Uani d 1
N N3 0.4044(2) 0.4879(5) 0.36125(15) 0.0401(7) Uani d 1
O O1 0.36928(17) -0.0003(4) 0.43538(12) 0.0382(5) Uani d 1
S S1 0.37950(6) 0.20165(12) 0.66320(4) 0.0360(3) Uani d 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C1 0.0249(13) 0.0295(14) 0.0237(12) -0.0011(11) 0.0039(10) -0.0039(10)
C2 0.0247(13) 0.0226(13) 0.0248(12) 0.0005(10) 0.0062(10) 0.0053(10)
C3 0.0358(16) 0.0308(16) 0.0340(15) -0.0005(12) 0.0055(12) 0.0079(12)
C4 0.0364(16) 0.0438(18) 0.0240(13) 0.0034(14) 0.0035(11) 0.0026(12)
C5 0.0251(13) 0.0311(15) 0.0255(13) -0.0021(11) 0.0045(10) -0.0028(11)
N1 0.0438(14) 0.0336(13) 0.0196(11) -0.0007(11) 0.0028(9) -0.0002(9)
N2 0.0317(13) 0.0335(14) 0.0266(12) -0.0035(10) 0.0002(9) -0.0026(10)
N3 0.0461(16) 0.0450(16) 0.0286(13) -0.0109(13) 0.0005(10) 0.0039(12)
O1 0.0519(14) 0.0382(12) 0.0255(10) -0.0086(10) 0.0080(8) -0.0072(9)
S1 0.0487(5) 0.0318(4) 0.0275(4) -0.0028(3) 0.0036(3) -0.0018(3)
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
C2 C1 C5 123.1(2)
C2 C1 S1 113.34(19)
C5 C1 S1 123.5(2)
C1 C2 C3 107.1(2)
C1 C2 H2 126.5
C3 C2 H2 126.5
C4 C3 C2 114.3(3)
C4 C3 H3 122.8
C2 C3 H3 122.8
C3 C4 S1 113.2(2)
C3 C4 H4 123.4
S1 C4 H4 123.4
O1 C5 N1 123.7(2)
O1 C5 C1 124.8(3)
N1 C5 C1 111.5(2)
N2 N1 C5 112.8(2)
N3 N2 N1 174.5(3)
C4 S1 C1 92.11(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.428(4)
C1 C5 1.464(4)
C1 S1 1.708(3)
C2 C3 1.459(4)
C2 H2 0.9500
C3 C4 1.355(4)
C3 H3 0.9500
C4 S1 1.679(3)
C4 H4 0.9500
C5 O1 1.212(3)
C5 N1 1.420(4)
N1 N2 1.260(3)
N2 N3 1.122(3)
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
C2 H2 N1 1_545 0.95 2.63 3.512(4) 155
C3 H3 N3 6_556 0.95 2.66 3.396(4) 135
C4 H4 O1 6_556 0.95 2.47 3.415(4) 173
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 C1 C2 C3 178.9(2)
S1 C1 C2 C3 -0.5(3)
C1 C2 C3 C4 0.0(3)
C2 C3 C4 S1 0.5(4)
C2 C1 C5 O1 -0.1(4)
S1 C1 C5 O1 179.2(2)
C2 C1 C5 N1 -179.9(2)
S1 C1 C5 N1 -0.6(3)
O1 C5 N1 N2 2.1(4)
C1 C5 N1 N2 -178.0(2)
C3 C4 S1 C1 -0.7(3)
C2 C1 S1 C4 0.7(2)
C5 C1 S1 C4 -178.7(2)
