#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/48/1504816.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_1504816
loop_
_publ_author_name
'Filimonov, Victor D.'
'Trusova, Marina'
'Postnikov, Pavel'
'Krasnokutskaya, Elena A.'
'Lee, Young Min'
'Hwang, Ho Yun'
'Kim, Hyunuk'
'Chi, Ki-Whan'
_publ_section_title
;
 Unusually stable, versatile, and pure arenediazonium tosylates: their
 preparation, structures, and synthetic applicability.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              3961
_journal_page_last               3964
_journal_paper_doi               10.1021/ol8013528
_journal_volume                  10
_journal_year                    2008
_chemical_formula_moiety         'C6 H4 N3 O2, C7 H7 O3 S'
_chemical_formula_sum            'C13 H11 N3 O5 S'
_chemical_formula_weight         321.31
_chemical_name_common            'o-nitrobenzenediazonium tosylate (9a)'
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                78.64(3)
_cell_angle_beta                 75.67(3)
_cell_angle_gamma                75.60(3)
_cell_formula_units_Z            2
_cell_length_a                   7.5090(15)
_cell_length_b                   7.5460(15)
_cell_length_c                   13.672(3)
_cell_measurement_reflns_used    2571
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      30.35
_cell_measurement_theta_min      3.22
_cell_volume                     719.4(3)
_computing_cell_refinement       HKL2000
_computing_data_collection       'Quantum 210'
_computing_data_reduction        HKL2000
_computing_molecular_graphics    'Materials Studio 4.1'
_computing_publication_material  'Materials Studio 4.1'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      90(2)
_diffrn_measured_fraction_theta_full 0.845
_diffrn_measured_fraction_theta_max 0.845
_diffrn_measurement_device_type  'Quantum 210'
_diffrn_measurement_method       \j-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         PAL_4A
_diffrn_radiation_type           'synchrotron radiation'
_diffrn_radiation_wavelength     0.80000
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0194
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            2571
_diffrn_reflns_theta_full        30.35
_diffrn_reflns_theta_max         30.35
_diffrn_reflns_theta_min         3.22
_exptl_absorpt_coefficient_mu    0.343
_exptl_absorpt_correction_T_max  0.9831
_exptl_absorpt_correction_T_min  0.9633
_exptl_absorpt_correction_type   semi-empirical
_exptl_absorpt_process_details   HKL2000
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.435
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         2571
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0392
_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)+(0.0958P)²+0.2094P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1220
_refine_ls_wR_factor_ref         0.1231
_reflns_number_gt                2511
_reflns_number_total             2571
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol8013528_si_001.cif
_cod_data_source_block           9a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        719.4(2)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1504816
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
S1 S 0.27816(5) 0.45109(5) 0.34868(2) 0.01919(17) Uani 1 1 d
O1 O 0.9129(2) 0.5710(2) -0.09508(9) 0.0351(3) Uani 1 1 d
O2 O 1.14230(19) 0.37217(17) -0.17092(9) 0.0306(3) Uani 1 1 d
O3 O 0.13433(16) 0.57989(15) 0.30097(8) 0.0222(3) Uani 1 1 d
O4 O 0.2019(2) 0.31597(17) 0.42900(9) 0.0313(3) Uani 1 1 d
O5 O 0.39832(17) 0.54397(19) 0.38021(10) 0.0324(3) Uani 1 1 d
N1 N 1.0405(2) 0.5267(2) -0.16643(10) 0.0247(3) Uani 1 1 d
N2 N 1.24354(19) 0.44291(18) -0.36611(10) 0.0210(3) Uani 1 1 d
N3 N 1.2998(2) 0.3035(2) -0.38661(11) 0.0270(3) Uani 1 1 d
C1 C 1.1795(2) 0.6274(2) -0.34884(11) 0.0185(3) Uani 1 1 d
C2 C 1.2163(2) 0.7611(2) -0.43198(11) 0.0213(4) Uani 1 1 d
C3 C 1.1487(3) 0.9447(2) -0.41758(12) 0.0241(4) Uani 1 1 d
C4 C 1.0438(3) 0.9906(2) -0.32374(13) 0.0260(4) Uani 1 1 d
C5 C 1.0080(2) 0.8534(2) -0.24142(12) 0.0243(4) Uani 1 1 d
C6 C 1.0765(2) 0.6710(2) -0.25311(11) 0.0201(3) Uani 1 1 d
C7 C 0.7471(3) 0.0360(3) 0.00023(14) 0.0380(5) Uani 1 1 d
C8 C 0.6388(2) 0.1361(3) 0.08960(12) 0.0272(4) Uani 1 1 d
C9 C 0.6197(3) 0.3258(3) 0.08203(12) 0.0274(4) Uani 1 1 d
C10 C 0.5119(2) 0.4219(2) 0.16142(12) 0.0240(4) Uani 1 1 d
C11 C 0.4253(2) 0.3249(2) 0.25072(11) 0.0193(3) Uani 1 1 d
C12 C 0.4473(2) 0.1343(2) 0.26076(12) 0.0234(4) Uani 1 1 d
C13 C 0.5532(3) 0.0410(2) 0.17983(13) 0.0276(4) Uani 1 1 d
H2 H 1.279(3) 0.727(3) -0.4943(17) 0.031(5) Uiso 1 1 d
H3 H 1.166(3) 1.036(3) -0.4700(17) 0.032(5) Uiso 1 1 d
H4 H 1.001(4) 1.114(4) -0.3140(18) 0.044(6) Uiso 1 1 d
H5 H 0.938(3) 0.880(3) -0.1729(16) 0.033(5) Uiso 1 1 d
H7A H 0.668(4) 0.043(4) -0.045(2) 0.065(8) Uiso 1 1 d
H7B H 0.817(4) -0.077(4) 0.022(2) 0.059(8) Uiso 1 1 d
H7C H 0.835(4) 0.116(4) -0.049(2) 0.053(7) Uiso 1 1 d
H9 H 0.680(3) 0.393(3) 0.0194(16) 0.031(5) Uiso 1 1 d
H10 H 0.497(3) 0.557(3) 0.1523(14) 0.020(4) Uiso 1 1 d
H12 H 0.393(3) 0.063(3) 0.3243(15) 0.027(5) Uiso 1 1 d
H13 H 0.565(3) -0.095(3) 0.1901(16) 0.034(5) Uiso 1 1 d
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C -0.0020 0.0021 '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 -0.0031 0.0043 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O -0.0042 0.0079 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1265 0.1577 '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
O4 S1 O3 112.64(8)
O4 S1 O5 113.33(8)
O3 S1 O5 112.60(8)
O4 S1 C11 106.27(7)
O3 S1 C11 105.16(7)
O5 S1 C11 106.04(7)
O1 N1 O2 125.45(15)
O1 N1 C6 117.01(15)
O2 N1 C6 117.54(13)
N3 N2 C1 174.80(16)
C2 C1 C6 122.69(14)
C2 C1 N2 116.45(13)
C6 C1 N2 120.80(14)
C1 C2 C3 117.50(14)
C2 C3 C4 120.64(15)
C3 C4 C5 120.71(15)
C6 C5 C4 119.77(14)
C5 C6 C1 118.67(14)
C5 C6 N1 119.84(13)
C1 C6 N1 121.49(14)
C9 C8 C13 118.79(15)
C9 C8 C7 120.34(16)
C13 C8 C7 120.86(17)
C8 C9 C10 121.16(15)
C11 C10 C9 119.30(15)
C12 C11 C10 120.33(14)
C12 C11 S1 120.91(11)
C10 C11 S1 118.70(12)
C11 C12 C13 119.54(15)
C8 C13 C12 120.85(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O4 1.4532(13)
S1 O3 1.4537(14)
S1 O5 1.4551(12)
S1 C11 1.7796(16)
O1 N1 1.220(2)
O2 N1 1.229(2)
N1 C6 1.4636(19)
N2 N3 1.095(2)
N2 C1 1.402(2)
C1 C2 1.385(2)
C1 C6 1.401(2)
C2 C3 1.387(2)
C3 C4 1.388(2)
C4 C5 1.393(2)
C5 C6 1.371(2)
C7 C8 1.513(2)
C8 C9 1.389(3)
C8 C13 1.392(2)
C9 C10 1.393(2)
C10 C11 1.393(2)
C11 C12 1.389(2)
C12 C13 1.395(2)
