#------------------------------------------------------------------------------
#$Date: 2016-03-26 13:38:20 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180230 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/16/7111638.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# 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_7111638
loop_
_publ_author_name
'Banert, Klaus'
'Hagedorn, Manfred'
'Wutke, Jens'
'Ecorchard, Petra'
'Schaarschmidt, Dieter'
'Lang, Heinrich'
_publ_section_title
;
 Elusive ethynyl azides: trapping by 1,3-dipolar cycloaddition and
 decomposition to cyanocarbenes
;
_journal_issue                   23
_journal_name_full               'Chemical Communications'
_journal_page_first              4058
_journal_paper_doi               10.1039/c0cc00079e
_journal_volume                  46
_journal_year                    2010
_chemical_formula_moiety         'C9 H10 N2 O S'
_chemical_formula_sum            'C9 H10 N2 O S'
_chemical_formula_weight         194.25
_chemical_name_systematic
;
?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.691(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.9633(2)
_cell_length_b                   5.10970(10)
_cell_length_c                   13.5723(4)
_cell_measurement_reflns_used    4537
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.9992
_cell_measurement_theta_min      3.0164
_cell_volume                     467.12(2)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.37 (release 24-10-2008 CrysAlis171 .NET)
(compiled Oct 24 2008,09:44:38)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.37 (release 24-10-2008 CrysAlis171 .NET)
(compiled Oct 24 2008,09:44:38)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.37 (release 24-10-2008 CrysAlis171 .NET)
(compiled Oct 24 2008,09:44:38)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Oxford Gemini S'
_diffrn_measurement_method       'ω scans'
_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  0.0227
_diffrn_reflns_av_sigmaI/netI    0.0265
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5452
_diffrn_reflns_theta_full        26.07
_diffrn_reflns_theta_max         26.07
_diffrn_reflns_theta_min         3.02
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 50
_diffrn_standards_interval_time  10
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.305
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cube
_exptl_crystal_F_000             204
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1816
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0250
_refine_ls_R_factor_gt           0.0233
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0418P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0586
_refine_ls_wR_factor_ref         0.0594
_reflns_number_gt                1729
_reflns_number_total             1816
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0cc00079esup1.cif
_cod_data_source_block           exp_045
_cod_database_code               7111638
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.4314(2) 0.0902(3) 0.24244(12) 0.0150(3) Uani 1 1 d .
H1A H 0.3090 0.0700 0.2620 0.023 Uiso 1 1 calc R
H1B H 0.4899 -0.0786 0.2392 0.023 Uiso 1 1 calc R
H1C H 0.4056 0.1726 0.1768 0.023 Uiso 1 1 calc R
C2 C 0.6499(2) 0.0930(3) 0.44382(12) 0.0154(3) Uani 1 1 d .
H2A H 0.5304 0.0637 0.4652 0.023 Uiso 1 1 calc R
H2B H 0.7452 0.1816 0.4969 0.023 Uiso 1 1 calc R
H2C H 0.7034 -0.0719 0.4298 0.023 Uiso 1 1 calc R
C3 C 0.8139(2) 0.3272(4) 0.30175(12) 0.0145(4) Uani 1 1 d .
C4 C 0.9841(2) 0.2102(3) 0.36387(13) 0.0150(4) Uani 1 1 d .
C5 C 0.8192(2) 0.4911(3) 0.21499(13) 0.0141(3) Uani 1 1 d .
C6 C 0.9990(3) 0.5880(3) 0.20048(13) 0.0168(4) Uani 1 1 d .
H6 H 1.1189 0.5491 0.2467 0.020 Uiso 1 1 calc R
C7 C 0.9941(2) 0.7412(4) 0.11676(13) 0.0195(4) Uani 1 1 d .
H7 H 1.1114 0.8056 0.1053 0.023 Uiso 1 1 calc R
C8 C 0.8136(2) 0.7994(4) 0.04947(12) 0.0219(3) Uani 1 1 d .
H8 H 0.8071 0.9024 -0.0078 0.026 Uiso 1 1 calc R
C9 C 0.6445(3) 0.7000(3) 0.07007(13) 0.0190(4) Uani 1 1 d .
H9 H 0.5232 0.7414 0.0255 0.023 Uiso 1 1 calc R
N1 N 1.1262(2) 0.1122(3) 0.41192(11) 0.0203(3) Uani 1 1 d .
N2 N 0.6432(2) 0.5473(3) 0.15012(10) 0.0156(3) Uani 1 1 d .
O1 O 0.49283(16) 0.5250(2) 0.34693(9) 0.0151(3) Uani 1 1 d .
S1 S 0.59618(5) 0.28635(7) 0.33319(3) 0.01089(10) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0153(8) 0.0140(8) 0.0142(9) -0.0008(7) 0.0008(6) -0.0010(7)
C2 0.0182(8) 0.0149(8) 0.0124(8) 0.0028(7) 0.0029(7) -0.0021(7)
C3 0.0113(7) 0.0179(10) 0.0146(8) 0.0014(7) 0.0041(6) 0.0008(7)
C4 0.0162(8) 0.0147(8) 0.0157(9) -0.0015(6) 0.0071(7) -0.0025(6)
C5 0.0163(8) 0.0118(8) 0.0152(8) -0.0029(6) 0.0059(7) 0.0005(6)
C6 0.0159(8) 0.0179(9) 0.0165(9) -0.0025(7) 0.0038(7) -0.0013(7)
C7 0.0224(8) 0.0186(11) 0.0207(9) -0.0051(7) 0.0115(7) -0.0068(7)
C8 0.0333(9) 0.0194(8) 0.0141(8) 0.0025(10) 0.0081(7) -0.0056(10)
C9 0.0224(8) 0.0190(9) 0.0138(9) 0.0007(6) 0.0014(7) -0.0016(7)
N1 0.0143(7) 0.0238(8) 0.0219(8) 0.0036(6) 0.0030(6) 0.0017(6)
N2 0.0162(7) 0.0170(7) 0.0130(7) 0.0015(6) 0.0023(6) -0.0005(6)
O1 0.0149(5) 0.0128(6) 0.0182(6) -0.0010(5) 0.0055(5) 0.0013(4)
S1 0.01072(16) 0.01010(17) 0.01178(18) 0.00003(18) 0.00270(12) 0.00007(16)
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
S1 C1 H1A 109.5
S1 C1 H1B 109.5
H1A C1 H1B 109.5
S1 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
S1 C2 H2A 109.5
S1 C2 H2B 109.5
H2A C2 H2B 109.5
S1 C2 H2C 109.5
H2A C2 H2C 109.5
H2B C2 H2C 109.5
C4 C3 C5 122.78(14)
C4 C3 S1 118.14(12)
C5 C3 S1 119.02(12)
N1 C4 C3 177.62(17)
N2 C5 C6 121.91(16)
N2 C5 C3 116.53(14)
C6 C5 C3 121.55(15)
C7 C6 C5 118.72(16)
C7 C6 H6 120.6
C5 C6 H6 120.6
C6 C7 C8 119.73(15)
C6 C7 H7 120.1
C8 C7 H7 120.1
C9 C8 C7 117.85(16)
C9 C8 H8 121.1
C7 C8 H8 121.1
N2 C9 C8 124.23(17)
N2 C9 H9 117.9
C8 C9 H9 117.9
C9 N2 C5 117.55(15)
O1 S1 C3 115.76(8)
O1 S1 C2 111.57(7)
C3 S1 C2 105.98(8)
O1 S1 C1 108.09(7)
C3 S1 C1 111.10(8)
C2 S1 C1 103.69(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 S1 1.7668(16)
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
C2 S1 1.7566(17)
C2 H2A 0.9600
C2 H2B 0.9600
C2 H2C 0.9600
C3 C4 1.402(2)
C3 C5 1.453(2)
C3 S1 1.6887(15)
C4 N1 1.152(2)
C5 N2 1.346(2)
C5 C6 1.406(2)
C6 C7 1.373(2)
C6 H6 0.9300
C7 C8 1.386(2)
C7 H7 0.9300
C8 C9 1.374(2)
C8 H8 0.9300
C9 N2 1.339(2)
C9 H9 0.9300
O1 S1 1.4520(12)
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 C3 C4 N1 -40(4)
S1 C3 C4 N1 143(4)
C4 C3 C5 N2 166.97(16)
S1 C3 C5 N2 -16.1(2)
C4 C3 C5 C6 -13.7(3)
S1 C3 C5 C6 163.21(13)
N2 C5 C6 C7 -1.0(3)
C3 C5 C6 C7 179.78(16)
C5 C6 C7 C8 0.8(3)
C6 C7 C8 C9 0.2(3)
C7 C8 C9 N2 -1.0(3)
C8 C9 N2 C5 0.9(3)
C6 C5 N2 C9 0.2(2)
C3 C5 N2 C9 179.45(15)
C4 C3 S1 O1 124.23(14)
C5 C3 S1 O1 -52.86(16)
C4 C3 S1 C2 -0.01(16)
C5 C3 S1 C2 -177.11(14)
C4 C3 S1 C1 -112.00(14)
C5 C3 S1 C1 70.90(16)
