#------------------------------------------------------------------------------
#$Date: 2019-11-24 23:10:20 +0200 (Sun, 24 Nov 2019) $
#$Revision: 239695 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/70/4517013.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_4517013
loop_
_publ_author_name
'Mehrotra, Sonam'
'Raje, Sakthi'
'Jain, Anant Kumar'
'Angamuthu, Raja'
_publ_section_title
;
 Benzimidazolines Convert Sulfur Dioxide to Bisulfate at Room Temperature
 and Atmospheric Pressure Utilizing Aerial Oxygen
;
_journal_issue                   7
_journal_name_full               'ACS Sustainable Chemistry & Engineering'
_journal_page_first              6322
_journal_paper_doi               10.1021/acssuschemeng.7b01495
_journal_volume                  5
_journal_year                    2017
_chemical_formula_sum            'C20 H20 N5 O5 S'
_chemical_formula_weight         442.47
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        '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                64.0149(19)
_cell_angle_beta                 71.014(2)
_cell_angle_gamma                70.772(2)
_cell_formula_units_Z            4
_cell_length_a                   10.8743(8)
_cell_length_b                   12.9713(9)
_cell_length_c                   13.3718(10)
_cell_measurement_temperature    293(2)
_cell_volume                     1564.0(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0441
_diffrn_reflns_av_sigmaI/netI    0.0460
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            20542
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.98
_exptl_absorpt_coefficient_mu    0.265
_exptl_crystal_density_diffrn    1.879
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             924
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.557
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     423
_refine_ls_number_reflns         6143
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0439
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1279
_refine_ls_wR_factor_ref         0.1427
_reflns_number_gt                4853
_reflns_number_total             6143
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            sc7b01495_si_002.cif
_cod_data_source_block           6nova_0m
_cod_original_cell_volume        1564.1(2)
_cod_database_code               4517013
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
S2 S 0.71170(5) 0.72798(5) 0.65115(4) 0.01538(16) Uani 1 1 d .
S3 S 0.45486(5) 0.89523(5) 0.86005(4) 0.01625(16) Uani 1 1 d .
O12 O 0.46811(15) 0.76393(13) 0.88453(12) 0.0190(3) Uani 1 1 d .
H12 H 0.5421 0.7378 0.8521 0.029 Uiso 1 1 calc R
O7 O 0.69291(15) 0.68332(14) 0.77616(12) 0.0237(4) Uani 1 1 d .
O10 O 0.54056(16) 0.89951(13) 0.92098(13) 0.0256(4) Uani 1 1 d .
O11 O 0.31468(15) 0.93693(14) 0.90090(13) 0.0249(4) Uani 1 1 d .
O9 O 0.49566(15) 0.95399(13) 0.73669(12) 0.0209(4) Uani 1 1 d .
O8 O 0.60976(16) 0.70986(15) 0.61856(13) 0.0298(4) Uani 1 1 d .
O5 O 0.84610(16) 0.68618(14) 0.59845(13) 0.0259(4) Uani 1 1 d .
O1 O -0.18693(16) 0.07350(13) 0.88911(12) 0.0247(4) Uani 1 1 d .
H1 H -0.2295 0.0747 0.9519 0.037 Uiso 1 1 calc R
O2 O 0.62917(16) 0.69146(13) 0.06944(12) 0.0224(4) Uani 1 1 d .
H2 H 0.5958 0.7587 0.0316 0.034 Uiso 1 1 calc R
O6 O 0.69869(17) 0.86296(14) 0.60858(14) 0.0290(4) Uani 1 1 d .
H6 H 0.6261 0.8926 0.6398 0.044 Uiso 1 1 calc R
N4 N 0.73640(17) 0.43070(15) 0.16333(15) 0.0161(4) Uani 1 1 d .
N3 N 0.91857(17) 0.46040(15) 0.17192(14) 0.0152(4) Uani 1 1 d .
N2 N -0.06198(17) 0.01643(15) 0.67169(14) 0.0152(4) Uani 1 1 d .
N1 N 0.11922(17) 0.06134(15) 0.66207(14) 0.0155(4) Uani 1 1 d .
C25 C 0.7057(2) 0.58512(18) 0.23828(18) 0.0169(5) Uani 1 1 d .
C24 C 0.7852(2) 0.49395(18) 0.19175(17) 0.0150(5) Uani 1 1 d .
C10 C -0.0934(2) 0.19681(19) 0.70877(18) 0.0159(5) Uani 1 1 d .
C18 C 0.9683(2) 0.1999(2) 0.05772(18) 0.0211(5) Uani 1 1 d .
H18 H 0.9747 0.1406 0.0338 0.025 Uiso 1 1 calc R
C21 C 0.9577(2) 0.37115(18) 0.12908(17) 0.0163(5) Uani 1 1 d .
C26 C 0.6280(2) 0.68614(19) 0.17271(18) 0.0171(5) Uani 1 1 d .
C16 C 0.8419(2) 0.35207(19) 0.12460(17) 0.0157(5) Uani 1 1 d .
C6 C 0.1599(2) -0.03952(18) 0.63599(17) 0.0153(5) Uani 1 1 d .
C13 C -0.2435(2) 0.39470(19) 0.75627(19) 0.0205(5) Uani 1 1 d .
H13 H -0.2938 0.4612 0.7725 0.025 Uiso 1 1 calc R
C8 C -0.2034(2) 0.0206(2) 0.68796(18) 0.0190(5) Uani 1 1 d .
H8A H -0.2311 -0.0396 0.7590 0.029 Uiso 1 1 calc R
H8B H -0.2160 0.0080 0.6267 0.029 Uiso 1 1 calc R
H8C H -0.2555 0.0962 0.6888 0.029 Uiso 1 1 calc R
C15 C -0.0815(2) 0.30912(19) 0.62804(18) 0.0199(5) Uani 1 1 d .
H15 H -0.0226 0.3172 0.5581 0.024 Uiso 1 1 calc R
C1 C 0.0442(2) -0.06690(18) 0.64108(17) 0.0159(5) Uani 1 1 d .
C27 C 0.5563(2) 0.7741(2) 0.21515(19) 0.0213(5) Uani 1 1 d .
H27 H 0.5064 0.8427 0.1710 0.026 Uiso 1 1 calc R
C19 C 1.0850(2) 0.2213(2) 0.06027(18) 0.0209(5) Uani 1 1 d .
H19 H 1.1667 0.1762 0.0371 0.025 Uiso 1 1 calc R
C11 C -0.1821(2) 0.18458(19) 0.81469(18) 0.0175(5) Uani 1 1 d .
C7 C 0.2085(2) 0.12148(19) 0.66792(19) 0.0189(5) Uani 1 1 d .
H7A H 0.2261 0.1849 0.5965 0.028 Uiso 1 1 calc R
H7B H 0.2908 0.0668 0.6835 0.028 Uiso 1 1 calc R
H7C H 0.1669 0.1521 0.7275 0.028 Uiso 1 1 calc R
C30 C 0.7076(2) 0.5725(2) 0.34723(18) 0.0207(5) Uani 1 1 d .
H30 H 0.7590 0.5051 0.3912 0.025 Uiso 1 1 calc R
C9 C -0.0138(2) 0.09278(19) 0.68269(17) 0.0148(4) Uani 1 1 d .
C3 C 0.1725(2) -0.22635(19) 0.58643(18) 0.0220(5) Uani 1 1 d .
H3 H 0.1797 -0.2891 0.5671 0.026 Uiso 1 1 calc R
C5 C 0.2856(2) -0.10768(19) 0.60984(18) 0.0200(5) Uani 1 1 d .
H5 H 0.3628 -0.0909 0.6091 0.024 Uiso 1 1 calc R
C22 C 1.0099(2) 0.51169(19) 0.18718(19) 0.0190(5) Uani 1 1 d .
H22A H 0.9642 0.5874 0.1911 0.028 Uiso 1 1 calc R
H22B H 1.0849 0.5201 0.1240 0.028 Uiso 1 1 calc R
H22C H 1.0403 0.4611 0.2565 0.028 Uiso 1 1 calc R
C20 C 1.0832(2) 0.30674(19) 0.09593(17) 0.0186(5) Uani 1 1 d .
H20 H 1.1610 0.3205 0.0977 0.022 Uiso 1 1 calc R
C12 C -0.2567(2) 0.28406(19) 0.83731(18) 0.0195(5) Uani 1 1 d .
H12A H -0.3160 0.2769 0.9070 0.023 Uiso 1 1 calc R
C23 C 0.5957(2) 0.4390(2) 0.1746(2) 0.0218(5) Uani 1 1 d .
H23A H 0.5420 0.4810 0.2236 0.033 Uiso 1 1 calc R
H23B H 0.5789 0.3614 0.2066 0.033 Uiso 1 1 calc R
H23C H 0.5736 0.4800 0.1009 0.033 Uiso 1 1 calc R
C29 C 0.6342(2) 0.6588(2) 0.38976(19) 0.0242(5) Uani 1 1 d .
H29 H 0.6345 0.6497 0.4626 0.029 Uiso 1 1 calc R
C2 C 0.0474(2) -0.16097(19) 0.61540(17) 0.0193(5) Uani 1 1 d .
H2A H -0.0300 -0.1786 0.6176 0.023 Uiso 1 1 calc R
C28 C 0.5592(2) 0.7601(2) 0.3223(2) 0.0232(5) Uani 1 1 d .
H28 H 0.5103 0.8192 0.3503 0.028 Uiso 1 1 calc R
C14 C -0.1563(2) 0.4076(2) 0.65139(19) 0.0221(5) Uani 1 1 d .
H14 H -0.1485 0.4821 0.5975 0.027 Uiso 1 1 calc R
C17 C 0.8438(2) 0.26457(19) 0.08966(18) 0.0195(5) Uani 1 1 d .
H17 H 0.7660 0.2507 0.0880 0.023 Uiso 1 1 calc R
C4 C 0.2895(2) -0.2013(2) 0.58515(18) 0.0221(5) Uani 1 1 d .
H4 H 0.3715 -0.2492 0.5672 0.026 Uiso 1 1 calc R
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
O8 S2 O5 115.23(10)
O8 S2 O7 111.48(10)
O5 S2 O7 111.59(9)
O8 S2 O6 107.90(10)
O5 S2 O6 103.69(9)
O7 S2 O6 106.17(9)
O11 S3 O10 113.61(9)
O11 S3 O9 111.64(9)
O10 S3 O9 112.04(9)
O11 S3 O12 104.15(9)
O10 S3 O12 107.48(9)
O9 S3 O12 107.32(9)
C24 N4 C16 108.69(18)
C24 N4 C23 126.17(18)
C16 N4 C23 125.10(18)
C24 N3 C21 108.57(17)
C24 N3 C22 126.32(18)
C21 N3 C22 125.06(18)
C9 N2 C1 108.71(17)
C9 N2 C8 125.82(18)
C1 N2 C8 125.46(18)
C9 N1 C6 108.90(17)
C9 N1 C7 125.76(18)
C6 N1 C7 125.33(18)
C26 C25 C30 119.54(19)
C26 C25 C24 119.59(19)
C30 C25 C24 120.86(19)
N4 C24 N3 109.32(18)
N4 C24 C25 125.53(19)
N3 C24 C25 125.15(19)
C15 C10 C11 119.8(2)
C15 C10 C9 119.98(19)
C11 C10 C9 120.27(19)
C17 C18 C19 121.8(2)
C16 C21 C20 122.1(2)
C16 C21 N3 106.51(18)
C20 C21 N3 131.4(2)
O2 C26 C27 124.1(2)
O2 C26 C25 116.30(18)
C27 C26 C25 119.6(2)
C21 C16 N4 106.91(18)
C21 C16 C17 122.0(2)
N4 C16 C17 131.1(2)
C1 C6 C5 121.9(2)
C1 C6 N1 106.24(18)
C5 C6 N1 131.9(2)
C12 C13 C14 121.0(2)
C14 C15 C10 120.5(2)
N2 C1 C6 106.86(18)
N2 C1 C2 131.1(2)
C6 C1 C2 122.0(2)
C28 C27 C26 120.0(2)
C20 C19 C18 122.3(2)
O1 C11 C12 124.18(19)
O1 C11 C10 116.54(19)
C12 C11 C10 119.3(2)
C29 C30 C25 120.6(2)
N1 C9 N2 109.28(18)
N1 C9 C10 125.10(19)
N2 C9 C10 125.58(19)
C2 C3 C4 122.3(2)
C4 C5 C6 116.4(2)
C19 C20 C21 115.8(2)
C11 C12 C13 120.1(2)
C30 C29 C28 119.1(2)
C3 C2 C1 115.8(2)
C27 C28 C29 121.1(2)
C15 C14 C13 119.3(2)
C18 C17 C16 115.9(2)
C5 C4 C3 121.6(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S2 O8 1.4315(16)
S2 O5 1.4385(16)
S2 O7 1.4761(15)
S2 O6 1.5574(16)
S3 O11 1.4452(16)
S3 O10 1.4502(16)
S3 O9 1.4640(15)
S3 O12 1.5521(15)
O1 C11 1.352(3)
O2 C26 1.348(2)
N4 C24 1.338(3)
N4 C16 1.390(3)
N4 C23 1.460(3)
N3 C24 1.341(3)
N3 C21 1.396(3)
N3 C22 1.468(3)
N2 C9 1.341(3)
N2 C1 1.388(3)
N2 C8 1.467(3)
N1 C9 1.336(3)
N1 C6 1.395(3)
N1 C7 1.469(3)
C25 C26 1.395(3)
C25 C30 1.399(3)
C25 C24 1.468(3)
C10 C15 1.400(3)
C10 C11 1.406(3)
C10 C9 1.462(3)
C18 C17 1.381(3)
C18 C19 1.399(3)
C21 C16 1.385(3)
C21 C20 1.392(3)
C26 C27 1.388(3)
C16 C17 1.397(3)
C6 C1 1.390(3)
C6 C5 1.391(3)
C13 C12 1.388(3)
C13 C14 1.388(3)
C15 C14 1.375(3)
C1 C2 1.393(3)
C27 C28 1.372(3)
C19 C20 1.378(3)
C11 C12 1.381(3)
C30 C29 1.374(3)
C3 C2 1.381(3)
C3 C4 1.406(3)
C5 C4 1.376(3)
C29 C28 1.393(3)
