#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:39:43 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178436 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/57/4025704.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_4025704
loop_
_publ_author_name
'Alan R. Katritzky'
'Mirna El Khatib'
'Oleg Bol'shakov'
'Levan Khelashvili'
'Peter J. Steel'
_publ_section_title
;
 Benzotriazol-1-yl-sulfonyl Azide for Diazotransfer and Preparation of
 Azidoacylbenzotriazoles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6532
_journal_page_last               6539
_journal_paper_doi               10.1021/jo101296s
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C6 H4 N6 O2 S'
_chemical_formula_sum            'C6 H4 N6 O2 S'
_chemical_formula_weight         224.21
_chemical_name_systematic
; 
 ? 
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.371(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.9024(9)
_cell_length_b                   12.0310(12)
_cell_length_c                   7.4151(5)
_cell_measurement_reflns_used    1178
_cell_measurement_temperature    108(2)
_cell_measurement_theta_max      26.341
_cell_measurement_theta_min      2.674
_cell_volume                     877.95(13)
_computing_cell_refinement       APEX
_computing_data_collection       APEX
_computing_data_reduction        APEX
_computing_molecular_graphics    XP
_computing_publication_material  CIFTAB
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      108(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0604
_diffrn_reflns_av_sigmaI/netI    0.0727
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            5254
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.67
_exptl_absorpt_coefficient_mu    0.358
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.860042
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.696
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.896
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1548
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.896
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0380
_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)+(0.0289P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0704
_refine_ls_wR_factor_ref         0.0756
_reflns_number_gt                1074
_reflns_number_total             1548
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101296s_si_002.cif
_cod_data_source_block           mao3
_cod_database_code               4025704
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_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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.65819(6) 0.52901(6) 0.21031(8) 0.01759(19) Uani 1 1 d . . .
N1 N 0.79669(19) 0.59418(18) 0.3080(2) 0.0175(5) Uani 1 1 d . . .
O1 O 0.70438(16) 0.42683(14) 0.1451(2) 0.0226(4) Uani 1 1 d . . .
O2 O 0.55802(16) 0.53742(15) 0.3316(2) 0.0235(5) Uani 1 1 d . . .
N2 N 0.7773(2) 0.69468(17) 0.3958(3) 0.0228(5) Uani 1 1 d . . .
N3 N 0.8952(2) 0.73729(18) 0.4456(3) 0.0226(5) Uani 1 1 d . . .
C3A C 0.9952(2) 0.6673(2) 0.3905(3) 0.0170(6) Uani 1 1 d . . .
N4 N 0.6136(2) 0.60437(18) 0.0249(3) 0.0203(5) Uani 1 1 d . . .
C4 C 1.1367(2) 0.6782(2) 0.4162(3) 0.0224(6) Uani 1 1 d . . .
H4 H 1.1794 0.7401 0.4786 0.027 Uiso 1 1 calc R . .
N5 N 0.5443(2) 0.6892(2) 0.0599(3) 0.0219(5) Uani 1 1 d . . .
C5 C 1.2108(3) 0.5952(2) 0.3469(3) 0.0230(6) Uani 1 1 d . . .
H5 H 1.3072 0.5999 0.3613 0.028 Uiso 1 1 calc R . .
C6 C 1.1480(2) 0.5033(2) 0.2550(3) 0.0220(7) Uani 1 1 d . . .
H6 H 1.2034 0.4482 0.2084 0.026 Uiso 1 1 calc R . .
N6 N 0.4819(2) 0.7656(2) 0.0754(3) 0.0358(7) Uani 1 1 d . . .
C7A C 0.9345(2) 0.5759(2) 0.3000(3) 0.0150(6) Uani 1 1 d . . .
C7 C 1.0089(2) 0.4907(2) 0.2303(3) 0.0181(6) Uani 1 1 d . . .
H7 H 0.9665 0.4282 0.1697 0.022 Uiso 1 1 calc R . .
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
S1 0.0129(3) 0.0189(4) 0.0209(3) 0.0014(3) 0.0011(3) -0.0011(3)
N1 0.0128(11) 0.0177(13) 0.0220(10) -0.0029(10) 0.0017(9) 0.0008(9)
O1 0.0160(10) 0.0169(11) 0.0342(10) -0.0030(8) -0.0007(8) 0.0009(8)
O2 0.0163(10) 0.0307(12) 0.0246(9) 0.0035(9) 0.0069(8) -0.0007(9)
N2 0.0216(13) 0.0174(14) 0.0298(12) -0.0051(11) 0.0038(10) 0.0019(11)
N3 0.0213(13) 0.0189(14) 0.0266(12) -0.0026(10) -0.0018(10) -0.0006(11)
C3A 0.0161(14) 0.0187(16) 0.0154(12) 0.0021(12) -0.0023(11) -0.0022(12)
N4 0.0174(12) 0.0217(14) 0.0222(11) 0.0019(10) 0.0036(9) 0.0030(10)
C4 0.0226(15) 0.0203(17) 0.0230(14) 0.0023(12) -0.0032(12) -0.0071(13)
N5 0.0163(13) 0.0259(15) 0.0227(12) 0.0054(11) -0.0010(10) -0.0028(12)
C5 0.0125(14) 0.0303(18) 0.0259(13) 0.0054(13) 0.0000(12) -0.0040(13)
C6 0.0185(15) 0.0289(18) 0.0195(13) 0.0029(12) 0.0057(12) 0.0049(12)
N6 0.0326(15) 0.0305(17) 0.0449(15) 0.0088(13) 0.0061(12) 0.0118(13)
C7A 0.0120(13) 0.0198(16) 0.0130(11) 0.0032(11) -0.0002(10) 0.0003(12)
C7 0.0188(14) 0.0210(16) 0.0144(12) -0.0008(11) 0.0016(11) 0.0001(12)
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 123.73(11) . . ?
O2 S1 N4 110.24(10) . . ?
O1 S1 N4 104.90(10) . . ?
O2 S1 N1 106.86(10) . . ?
O1 S1 N1 105.92(10) . . ?
N4 S1 N1 103.39(11) . . ?
C7A N1 N2 110.08(19) . . ?
C7A N1 S1 131.98(17) . . ?
N2 N1 S1 117.31(16) . . ?
N3 N2 N1 108.07(19) . . ?
N2 N3 C3A 109.0(2) . . ?
C7A C3A N3 109.7(2) . . ?
C7A C3A C4 120.8(2) . . ?
N3 C3A C4 129.5(2) . . ?
N5 N4 S1 111.59(16) . . ?
C5 C4 C3A 116.7(2) . . ?
C5 C4 H4 121.6 . . ?
C3A C4 H4 121.6 . . ?
N6 N5 N4 174.2(3) . . ?
C4 C5 C6 121.8(2) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C7 C6 C5 122.2(2) . . ?
C7 C6 H6 118.9 . . ?
C5 C6 H6 118.9 . . ?
C3A C7A N1 103.2(2) . . ?
C3A C7A C7 122.9(2) . . ?
N1 C7A C7 133.9(2) . . ?
C6 C7 C7A 115.5(2) . . ?
C6 C7 H7 122.2 . . ?
C7A C7 H7 122.2 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.4147(16) . ?
S1 O1 1.4152(18) . ?
S1 N4 1.665(2) . ?
S1 N1 1.673(2) . ?
N1 C7A 1.390(3) . ?
N1 N2 1.397(3) . ?
N2 N3 1.291(3) . ?
N3 C3A 1.394(3) . ?
C3A C7A 1.390(3) . ?
C3A C4 1.400(3) . ?
N4 N5 1.273(3) . ?
C4 C5 1.373(3) . ?
C4 H4 0.9500 . ?
N5 N6 1.121(3) . ?
C5 C6 1.407(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.378(3) . ?
C6 H6 0.9500 . ?
C7A C7 1.394(3) . ?
C7 H7 0.9500 . ?
