#------------------------------------------------------------------------------
#$Date: 2015-09-06 02:40:34 +0300 (Sun, 06 Sep 2015) $
#$Revision: 154683 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/13/4031314.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_4031314
loop_
_publ_author_name
'Hayes, Colin O.'
'Bell, William K.'
'Cassidy, Benjamin R.'
'Willson, C. Grant'
_publ_section_title
;
 Synthesis and Characterization of a Two Stage, Nonlinear Photobase
 Generator.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7530
_journal_page_last               7535
_journal_paper_doi               10.1021/acs.joc.5b01078
_journal_volume                  80
_journal_year                    2015
_chemical_formula_sum            'C16 H10 N2 O S'
_chemical_formula_weight         278.32
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_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                99.62
_cell_angle_beta                 92.49
_cell_angle_gamma                91.05
_cell_formula_units_Z            2
_cell_length_a                   6.840
_cell_length_b                   8.619
_cell_length_c                   11.394
_cell_measurement_temperature    153(2)
_cell_volume                     661.427
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_sigmaI/netI    0.0998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3913
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.40
_exptl_absorpt_coefficient_mu    0.240
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             288
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.944
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2930
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.944
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0497
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0517P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1239
_refine_ls_wR_factor_ref         0.1279
_reflns_number_gt                1990
_reflns_number_total             2930
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b01078_si_001.cif
_cod_data_source_block           shelxl
_cod_depositor_comments          'Adding full bibliography for 4031314.cif.'
_cod_original_cell_volume        661.4
_cod_database_code               4031314
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
C1 C 0.6349(3) 0.4018(2) 0.08872(18) 0.0174(4) Uani 1 1 d .
C2 C 0.5204(3) 0.4900(2) 0.18461(18) 0.0176(5) Uani 1 1 d .
C3 C 0.3457(3) 0.3951(2) 0.20218(19) 0.0182(5) Uani 1 1 d .
C4 C 0.1932(3) 0.4329(3) 0.2788(2) 0.0241(5) Uani 1 1 d .
H4 H 0.1941 0.5324 0.3294 0.029 Uiso 1 1 calc R
C5 C 0.0400(3) 0.3252(3) 0.2812(2) 0.0272(5) Uani 1 1 d .
H5 H -0.0622 0.3513 0.3343 0.033 Uiso 1 1 calc R
C6 C 0.0352(3) 0.1800(3) 0.2066(2) 0.0273(5) Uani 1 1 d .
H6 H -0.0704 0.1077 0.2091 0.033 Uiso 1 1 calc R
C7 C 0.1830(3) 0.1400(3) 0.1287(2) 0.0250(5) Uani 1 1 d .
H7 H 0.1799 0.0407 0.0777 0.030 Uiso 1 1 calc R
C8 C 0.3359(3) 0.2476(2) 0.12677(19) 0.0202(5) Uani 1 1 d .
C9 C 0.5750(3) 0.6337(2) 0.24607(19) 0.0191(5) Uani 1 1 d .
C10 C 0.4704(3) 0.7234(2) 0.34877(19) 0.0187(5) Uani 1 1 d .
C11 C 0.3279(3) 0.8296(3) 0.3282(2) 0.0246(5) Uani 1 1 d .
H11 H 0.2943 0.8452 0.2493 0.030 Uiso 1 1 calc R
C12 C 0.2351(3) 0.9128(3) 0.4239(2) 0.0286(5) Uani 1 1 d .
H12 H 0.1361 0.9844 0.4100 0.034 Uiso 1 1 calc R
C13 C 0.2845(3) 0.8931(3) 0.5389(2) 0.0280(5) Uani 1 1 d .
H13 H 0.2208 0.9516 0.6038 0.034 Uiso 1 1 calc R
C14 C 0.4271(4) 0.7879(3) 0.5594(2) 0.0298(6) Uani 1 1 d .
H14 H 0.4615 0.7735 0.6385 0.036 Uiso 1 1 calc R
C15 C 0.5199(3) 0.7031(3) 0.4638(2) 0.0248(5) Uani 1 1 d .
H15 H 0.6179 0.6309 0.4777 0.030 Uiso 1 1 calc R
C16 C 0.7437(3) 0.7202(3) 0.2186(2) 0.0237(5) Uani 1 1 d .
N1 N 0.7939(3) 0.4534(2) 0.04993(16) 0.0201(4) Uani 1 1 d .
N2 N 0.8708(3) 0.8042(2) 0.2056(2) 0.0344(5) Uani 1 1 d .
O1 O 0.8623(2) 0.33744(19) -0.03947(14) 0.0260(4) Uani 1 1 d .
S1 S 0.53397(8) 0.21380(6) 0.03291(5) 0.02391(18) Uani 1 1 d .
H1O H 0.970(5) 0.377(4) -0.054(3) 0.093(14) 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 0.0033 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
N1 C1 C2 124.97(19)
N1 C1 S1 122.20(16)
C2 C1 S1 112.82(15)
C9 C2 C3 126.9(2)
C9 C2 C1 123.8(2)
C3 C2 C1 109.35(18)
C4 C3 C8 117.95(19)
C4 C3 C2 129.4(2)
C8 C3 C2 112.62(19)
C5 C4 C3 120.2(2)
C5 C4 H4 119.9
C3 C4 H4 119.9
C6 C5 C4 120.6(2)
C6 C5 H5 119.7
C4 C5 H5 119.7
C7 C6 C5 120.5(2)
C7 C6 H6 119.7
C5 C6 H6 119.7
C6 C7 C8 118.7(2)
C6 C7 H7 120.6
C8 C7 H7 120.6
C7 C8 C3 122.0(2)
C7 C8 S1 124.01(18)
C3 C8 S1 113.98(16)
C2 C9 C16 122.7(2)
C2 C9 C10 125.7(2)
C16 C9 C10 111.60(18)
C15 C10 C11 119.9(2)
C15 C10 C9 119.96(18)
C11 C10 C9 120.15(19)
C12 C11 C10 119.4(2)
C12 C11 H11 120.3
C10 C11 H11 120.3
C13 C12 C11 120.9(2)
C13 C12 H12 119.6
C11 C12 H12 119.6
C12 C13 C14 119.7(2)
C12 C13 H13 120.1
C14 C13 H13 120.1
C13 C14 C15 119.7(2)
C13 C14 H14 120.2
C15 C14 H14 120.2
C10 C15 C14 120.4(2)
C10 C15 H15 119.8
C14 C15 H15 119.8
N2 C16 C9 171.9(2)
C1 N1 O1 109.02(17)
N1 O1 H1O 102(2)
C1 S1 C8 91.15(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.290(3)
C1 C2 1.484(3)
C1 S1 1.756(2)
C2 C9 1.355(3)
C2 C3 1.476(3)
C3 C4 1.397(3)
C3 C8 1.409(3)
C4 C5 1.391(3)
C4 H4 0.9500
C5 C6 1.389(3)
C5 H5 0.9500
C6 C7 1.385(3)
C6 H6 0.9500
C7 C8 1.389(3)
C7 H7 0.9500
C8 S1 1.761(2)
C9 C16 1.436(3)
C9 C10 1.506(3)
C10 C15 1.379(3)
C10 C11 1.388(3)
C11 C12 1.386(3)
C11 H11 0.9500
C12 C13 1.378(3)
C12 H12 0.9500
C13 C14 1.383(3)
C13 H13 0.9500
C14 C15 1.391(3)
C14 H14 0.9500
C15 H15 0.9500
C16 N2 1.151(3)
N1 O1 1.405(2)
O1 H1O 0.84(4)
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
O1 H1O N1 0.84(4) 2.15(4) 2.956(2) 160(3) 2_765
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
N1 C1 C2 C9 -2.7(3)
S1 C1 C2 C9 176.14(16)
N1 C1 C2 C3 178.51(18)
S1 C1 C2 C3 -2.6(2)
C9 C2 C3 C4 4.2(3)
C1 C2 C3 C4 -177.12(19)
C9 C2 C3 C8 -177.46(19)
C1 C2 C3 C8 1.3(2)
C8 C3 C4 C5 1.4(3)
C2 C3 C4 C5 179.75(19)
C3 C4 C5 C6 -0.8(3)
C4 C5 C6 C7 0.1(3)
C5 C6 C7 C8 0.1(3)
C6 C7 C8 C3 0.6(3)
C6 C7 C8 S1 179.99(15)
C4 C3 C8 C7 -1.3(3)
C2 C3 C8 C7 -179.93(18)
C4 C3 C8 S1 179.21(15)
C2 C3 C8 S1 0.6(2)
C3 C2 C9 C16 -177.10(18)
C1 C2 C9 C16 4.4(3)
C3 C2 C9 C10 2.4(3)
C1 C2 C9 C10 -176.13(18)
C2 C9 C10 C15 89.7(3)
C16 C9 C10 C15 -90.7(2)
C2 C9 C10 C11 -92.0(3)
C16 C9 C10 C11 87.6(2)
C15 C10 C11 C12 -0.8(3)
C9 C10 C11 C12 -179.1(2)
C10 C11 C12 C13 1.0(4)
C11 C12 C13 C14 -0.7(4)
C12 C13 C14 C15 0.2(4)
C11 C10 C15 C14 0.4(3)
C9 C10 C15 C14 178.6(2)
C13 C14 C15 C10 -0.1(4)
C2 C9 C16 N2 169.2(17)
C10 C9 C16 N2 -10.4(19)
C2 C1 N1 O1 179.19(17)
S1 C1 N1 O1 0.4(2)
N1 C1 S1 C8 -178.55(17)
C2 C1 S1 C8 2.55(15)
C7 C8 S1 C1 178.73(18)
C3 C8 S1 C1 -1.84(16)
