#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/34/1503474.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_1503474
loop_
_publ_author_name
'Sakakura, Akira'
'Koshikari, Yoshiki'
'Akakura, Matsujiro'
'Ishihara, Kazuaki'
_publ_section_title
;
 Hydrophobic N,N-diarylammonium pyrosulfates as dehydrative condensation
 catalysts under aqueous conditions.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              30
_journal_page_last               33
_journal_paper_doi               10.1021/ol2027366
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C12 H13 N O4 S'
_chemical_formula_weight         267.29
_chemical_name_common            'diphenylammonium sulfate'
_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                61.113(2)
_cell_angle_beta                 78.878(6)
_cell_angle_gamma                64.120(9)
_cell_formula_units_Z            2
_cell_length_a                   8.5292(17)
_cell_length_b                   9.4437(18)
_cell_length_c                   9.5965(18)
_cell_measurement_temperature    173(2)
_cell_volume                     608.8(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scan'
_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  0.0208
_diffrn_reflns_av_sigmaI/netI    0.0356
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            4447
_diffrn_reflns_theta_full        28.33
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         2.69
_exptl_absorpt_coefficient_mu    0.272
_exptl_absorpt_correction_T_max  0.9476
_exptl_absorpt_correction_T_min  0.9476
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.700
_refine_diff_density_min         -1.104
_refine_diff_density_rms         0.288
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.252
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2974
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.252
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0602
_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/[?²(Fo²)+(0.0948P)²+0.1163P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1544
_refine_ls_wR_factor_ref         0.1567
_reflns_number_gt                2797
_reflns_number_total             2974
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol2027366_si_002.cif
_cod_data_source_block           kyd1
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1503474
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
_atom_site_refinement_flags
N1 N 0.56932(17) 0.30253(18) 0.36587(16) 0.0215(3) Uani 1 1 d .
H3 H 0.5823 0.4058 0.3331 0.026 Uiso 1 1 d R
H4 H 0.5682 0.2499 0.4753 0.026 Uiso 1 1 d R
C1 C 0.7232(2) 0.1861(2) 0.31682(19) 0.0208(3) Uani 1 1 d .
C2 C 0.8054(2) 0.0118(2) 0.4262(2) 0.0287(4) Uani 1 1 d .
H5 H 0.7624 -0.0324 0.5308 0.034 Uiso 1 1 calc R
C3 C 0.9524(3) -0.0975(2) 0.3797(2) 0.0347(4) Uani 1 1 d .
H6 H 1.0112 -0.2175 0.4533 0.042 Uiso 1 1 calc R
C4 C 1.0135(2) -0.0325(3) 0.2270(2) 0.0324(4) Uani 1 1 d .
H7 H 1.1136 -0.1082 0.1961 0.039 Uiso 1 1 calc R
C5 C 0.9293(2) 0.1423(3) 0.1190(2) 0.0323(4) Uani 1 1 d .
H8 H 0.9718 0.1862 0.0142 0.039 Uiso 1 1 calc R
C6 C 0.7823(2) 0.2541(2) 0.1634(2) 0.0279(4) Uani 1 1 d .
H9 H 0.7238 0.3743 0.0900 0.033 Uiso 1 1 calc R
C7 C 0.3980(2) 0.3483(2) 0.30676(18) 0.0208(3) Uani 1 1 d .
C8 C 0.3822(2) 0.2710(2) 0.2221(2) 0.0244(3) Uani 1 1 d .
H10 H 0.4822 0.1883 0.1986 0.029 Uiso 1 1 calc R
C9 C 0.2169(2) 0.3168(2) 0.1721(2) 0.0283(4) Uani 1 1 d .
H11 H 0.2037 0.2662 0.1126 0.034 Uiso 1 1 calc R
C10 C 0.0713(2) 0.4358(2) 0.2084(2) 0.0289(4) Uani 1 1 d .
H12 H -0.0414 0.4654 0.1750 0.035 Uiso 1 1 calc R
C11 C 0.0900(2) 0.5121(3) 0.2938(2) 0.0312(4) Uani 1 1 d .
H13 H -0.0097 0.5945 0.3178 0.037 Uiso 1 1 calc R
C12 C 0.2539(2) 0.4678(2) 0.3437(2) 0.0284(4) Uani 1 1 d .
H14 H 0.2675 0.5187 0.4027 0.034 Uiso 1 1 calc R
S1 S 0.45092(5) 0.22435(5) 0.78984(4) 0.02176(17) Uani 1 1 d .
O1 O 0.31070(18) 0.1558(2) 0.86943(19) 0.0381(3) Uani 1 1 d .
H1 H 0.3538 0.0487 0.9299 0.057 Uiso 1 1 d R
O2 O 0.55163(19) 0.14216(18) 0.68956(16) 0.0350(3) Uani 1 1 d .
O3 O 0.36378(18) 0.41451(17) 0.70226(18) 0.0334(3) Uani 1 1 d .
O4 O 0.56508(18) 0.17768(19) 0.91866(16) 0.0332(3) Uani 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 0.0033 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
C1 N1 C7 117.05(12)
C1 N1 H3 108.0
C7 N1 H3 108.0
C1 N1 H4 108.1
C7 N1 H4 108.1
H3 N1 H4 107.2
C2 C1 C6 122.10(15)
C2 C1 N1 118.70(14)
C6 C1 N1 119.19(15)
C1 C2 C3 118.46(16)
C1 C2 H5 120.8
C3 C2 H5 120.8
C4 C3 C2 120.44(17)
C4 C3 H6 119.8
C2 C3 H6 119.8
C3 C4 C5 120.25(16)
C3 C4 H7 119.9
C5 C4 H7 119.9
C4 C5 C6 120.23(16)
C4 C5 H8 119.9
C6 C5 H8 119.9
C1 C6 C5 118.52(16)
C1 C6 H9 120.7
C5 C6 H9 120.7
C8 C7 C12 121.71(15)
C8 C7 N1 121.21(14)
C12 C7 N1 117.06(14)
C7 C8 C9 118.60(15)
C7 C8 H10 120.7
C9 C8 H10 120.7
C10 C9 C8 120.45(16)
C10 C9 H11 119.8
C8 C9 H11 119.8
C9 C10 C11 120.02(16)
C9 C10 H12 120.0
C11 C10 H12 120.0
C12 C11 C10 119.98(16)
C12 C11 H13 120.0
C10 C11 H13 120.0
C11 C12 C7 119.23(16)
C11 C12 H14 120.4
C7 C12 H14 120.4
O2 S1 O3 113.03(8)
O2 S1 O4 110.07(8)
O3 S1 O4 109.74(8)
O2 S1 O1 109.67(9)
O3 S1 O1 106.83(8)
O4 S1 O1 107.30(9)
S1 O1 H1 111.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.4684(19)
N1 C7 1.475(2)
N1 H3 0.9200
N1 H4 0.9199
C1 C2 1.382(2)
C1 C6 1.384(2)
C2 C3 1.392(2)
C2 H5 0.9500
C3 C4 1.382(3)
C3 H6 0.9500
C4 C5 1.383(3)
C4 H7 0.9500
C5 C6 1.393(2)
C5 H8 0.9500
C6 H9 0.9500
C7 C8 1.383(2)
C7 C12 1.385(2)
C8 C9 1.390(2)
C8 H10 0.9500
C9 C10 1.386(2)
C9 H11 0.9500
C10 C11 1.392(3)
C10 H12 0.9500
C11 C12 1.383(2)
C11 H13 0.9500
C12 H14 0.9500
S1 O2 1.4447(13)
S1 O3 1.4496(13)
S1 O4 1.4946(13)
S1 O1 1.5096(14)
O1 H1 0.8277
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H3 O3 0.92 1.81 2.719(2) 169.7 2_666
N1 H3 S1 0.92 2.99 3.8988(16) 168.6 2_666
N1 H4 O2 0.92 1.81 2.7274(19) 175.3 .
N1 H4 S1 0.92 2.92 3.7791(16) 156.6 .
O1 H1 O4 0.83 1.80 2.628(2) 172.9 2_657
O1 H1 S1 0.83 2.82 3.5447(17) 147.8 2_657
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
C7 N1 C1 C2 -104.75(17)
C7 N1 C1 C6 75.70(19)
C6 C1 C2 C3 0.3(3)
N1 C1 C2 C3 -179.25(17)
C1 C2 C3 C4 -0.4(3)
C2 C3 C4 C5 0.3(3)
C3 C4 C5 C6 0.0(3)
C2 C1 C6 C5 0.0(3)
N1 C1 C6 C5 179.50(15)
C4 C5 C6 C1 -0.1(3)
C1 N1 C7 C8 6.2(2)
C1 N1 C7 C12 -175.61(14)
C12 C7 C8 C9 0.6(3)
N1 C7 C8 C9 178.78(15)
C7 C8 C9 C10 -0.8(3)
C8 C9 C10 C11 0.8(3)
C9 C10 C11 C12 -0.6(3)
C10 C11 C12 C7 0.4(3)
C8 C7 C12 C11 -0.5(3)
N1 C7 C12 C11 -178.68(16)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 11002
