#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:28:02 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178470 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/91/4029132.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_4029132
loop_
_publ_author_name
'Novakova, Veronika'
'Miletin, Miroslav'
'Filandrová, Tereza'
'Lenčo, Juraj'
'R°užička, Aleš'
'Zimcik, Petr'
_publ_section_title
;
 Role of steric hindrance in the newman-kwart rearrangement and in the
 synthesis and photophysical properties of arylsulfanyl
 tetrapyrazinoporphyrazines.
;
_journal_issue                   5
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2082
_journal_page_last               2093
_journal_paper_doi               10.1021/jo402791c
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C34 H42 N4 S2'
_chemical_formula_sum            'C34 H42 N4 S2'
_chemical_formula_weight         570.84
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           13
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yc'
_symmetry_space_group_name_H-M   'P 1 2/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
_cell_angle_beta                 123.062(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.2601(9)
_cell_length_b                   9.4289(6)
_cell_length_c                   16.6880(4)
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1
_cell_volume                     1616.76(19)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(1)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_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  0.0288
_diffrn_reflns_av_sigmaI/netI    0.0165
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            22706
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.16
_exptl_absorpt_coefficient_mu    0.193
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.173
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             612
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.53
_exptl_crystal_size_min          0.41
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3688
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0306
_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)+(0.0386P)²+0.6729P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0775
_refine_ls_wR_factor_ref         0.0857
_reflns_number_gt                3262
_reflns_number_total             3688
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            CCDC972475.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      'P 2/c'
_cod_database_code               4029132
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, 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
S1 S 0.37278(3) 0.33310(3) 0.148951(18) 0.01874(9) Uani 1 1 d .
C4 C 0.22265(10) 0.27145(11) 0.04619(8) 0.0185(2) Uani 1 1 d .
C1 C 0.44095(10) 0.17009(11) 0.20324(7) 0.0168(2) Uani 1 1 d .
C5 C 0.21991(12) 0.23316(12) -0.03715(8) 0.0214(2) Uani 1 1 d .
N1 N 0.38495(9) 0.05001(10) 0.15879(7) 0.0193(2) Uani 1 1 d .
C2 C 0.44345(11) -0.07130(11) 0.20491(8) 0.0186(2) Uani 1 1 d .
N2 N 0.34004(12) -0.30743(12) 0.11658(9) 0.0356(3) Uani 1 1 d .
C3 C 0.38412(11) -0.20227(13) 0.15528(8) 0.0235(2) Uani 1 1 d .
C6 C 0.10908(13) 0.16124(13) -0.10747(9) 0.0278(3) Uani 1 1 d .
H6 H 0.1040 0.1319 -0.1626 0.033 Uiso 1 1 d R
C9 C 0.11499(11) 0.25318(12) 0.05494(8) 0.0207(2) Uani 1 1 d .
C10 C 0.32386(12) 0.27510(14) -0.05826(9) 0.0256(3) Uani 1 1 d .
C13 C 0.33128(14) 0.43770(14) -0.05847(10) 0.0310(3) Uani 1 1 d .
H13A H 0.2464 0.4756 -0.1034 0.037 Uiso 1 1 d R
H13B H 0.3903 0.4659 -0.0765 0.037 Uiso 1 1 d R
H13C H 0.3618 0.4732 0.0043 0.037 Uiso 1 1 d R
C7 C 0.00665(13) 0.13310(14) -0.09783(9) 0.0305(3) Uani 1 1 d .
H7 H -0.0641 0.0810 -0.1447 0.037 Uiso 1 1 d R
C15 C 0.19884(13) 0.23353(15) 0.23338(9) 0.0299(3) Uani 1 1 d .
H15A H 0.2863 0.2656 0.2594 0.036 Uiso 1 1 d R
H15B H 0.1940 0.1332 0.2223 0.036 Uiso 1 1 d R
H15C H 0.1741 0.2538 0.2777 0.036 Uiso 1 1 d R
C8 C 0.00789(12) 0.18122(13) -0.01945(9) 0.0269(3) Uani 1 1 d .
H8 H -0.0643 0.1654 -0.0160 0.032 Uiso 1 1 d R
C14 C 0.10582(12) 0.31075(14) 0.13820(9) 0.0252(3) Uani 1 1 d .
C11 C 0.45922(14) 0.21022(17) 0.01102(10) 0.0344(3) Uani 1 1 d .
H11A H 0.5122 0.2224 -0.0146 0.041 Uiso 1 1 d R
H11B H 0.4501 0.1109 0.0187 0.041 Uiso 1 1 d R
H11C H 0.4997 0.2567 0.0720 0.041 Uiso 1 1 d R
C17 C 0.13059(15) 0.47108(15) 0.14997(10) 0.0337(3) Uani 1 1 d .
H17A H 0.1197 0.5056 0.1993 0.040 Uiso 1 1 d R
H17B H 0.0699 0.5180 0.0909 0.040 Uiso 1 1 d R
H17C H 0.2177 0.4901 0.1671 0.040 Uiso 1 1 d R
C16 C -0.03258(14) 0.28968(19) 0.11630(11) 0.0390(3) Uani 1 1 d .
H16A H -0.0520 0.1902 0.1112 0.047 Uiso 1 1 d R
H16B H -0.0943 0.3358 0.0571 0.047 Uiso 1 1 d R
H16C H -0.0378 0.3301 0.1669 0.047 Uiso 1 1 d R
C12 C 0.28470(16) 0.22629(17) -0.15884(10) 0.0381(3) Uani 1 1 d .
H12A H 0.2018 0.2663 -0.2059 0.046 Uiso 1 1 d R
H12B H 0.2791 0.1247 -0.1623 0.046 Uiso 1 1 d R
H12C H 0.3491 0.2575 -0.1708 0.046 Uiso 1 1 d 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'
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
C1 S1 C4 99.29(5) . .
C9 C4 C5 123.03(10) . .
C9 C4 S1 117.95(8) . .
C5 C4 S1 118.83(9) . .
N1 C1 C1 121.08(6) . 2_655
N1 C1 S1 120.47(8) . .
C1 C1 S1 118.44(4) 2_655 .
C6 C5 C4 116.09(11) . .
C6 C5 C10 118.57(11) . .
C4 C5 C10 125.15(10) . .
C1 N1 C2 117.08(9) . .
N1 C2 C2 121.84(6) . 2_655
N1 C2 C3 117.03(10) . .
C2 C2 C3 121.13(6) 2_655 .
N2 C3 C2 178.30(13) . .
C7 C6 C5 121.86(12) . .
C7 C6 H6 119.1 . .
C5 C6 H6 119.1 . .
C8 C9 C4 116.44(11) . .
C8 C9 C14 118.30(11) . .
C4 C9 C14 125.23(10) . .
C13 C10 C11 110.94(11) . .
C13 C10 C12 106.19(11) . .
C11 C10 C12 105.46(11) . .
C13 C10 C5 108.23(10) . .
C11 C10 C5 114.31(10) . .
C12 C10 C5 111.42(11) . .
C10 C13 H13A 109.5 . .
C10 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C10 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C6 C7 C8 120.65(12) . .
C6 C7 H7 119.7 . .
C8 C7 H7 119.6 . .
C14 C15 H15A 109.5 . .
C14 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C14 C15 H15C 109.4 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C7 C8 C9 121.52(12) . .
C7 C8 H8 119.2 . .
C9 C8 H8 119.3 . .
C17 C14 C16 105.84(11) . .
C17 C14 C15 110.49(11) . .
C16 C14 C15 106.45(11) . .
C17 C14 C9 110.71(10) . .
C16 C14 C9 110.53(11) . .
C15 C14 C9 112.52(10) . .
C10 C11 H11A 109.4 . .
C10 C11 H11B 109.4 . .
H11A C11 H11B 109.5 . .
C10 C11 H11C 109.7 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C14 C17 H17A 109.5 . .
C14 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C14 C17 H17C 109.4 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
C14 C16 H16A 109.5 . .
C14 C16 H16B 109.4 . .
H16A C16 H16B 109.5 . .
C14 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
C10 C12 H12A 109.6 . .
C10 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C10 C12 H12C 109.4 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C1 1.7480(11) .
S1 C4 1.7951(11) .
C4 C9 1.4155(16) .
C4 C5 1.4195(16) .
C1 N1 1.3221(14) .
C1 C1 1.438(2) 2_655
C5 C6 1.3940(17) .
C5 C10 1.5474(18) .
N1 C2 1.3464(14) .
C2 C2 1.382(2) 2_655
C2 C3 1.4432(16) .
N2 C3 1.1451(17) .
C6 C7 1.376(2) .
C6 H6 0.9299 .
C9 C8 1.3954(17) .
C9 C14 1.5517(17) .
C10 C13 1.5360(18) .
C10 C11 1.5400(18) .
C10 C12 1.5429(17) .
C13 H13A 0.9599 .
C13 H13B 0.9600 .
C13 H13C 0.9600 .
C7 C8 1.3767(19) .
C7 H7 0.9300 .
C15 C14 1.5419(17) .
C15 H15A 0.9600 .
C15 H15B 0.9600 .
C15 H15C 0.9600 .
C8 H8 0.9299 .
C14 C17 1.5333(19) .
C14 C16 1.5413(18) .
C11 H11A 0.9601 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
C17 H17A 0.9600 .
C17 H17B 0.9600 .
C17 H17C 0.9601 .
C16 H16A 0.9600 .
C16 H16B 0.9601 .
C16 H16C 0.9600 .
C12 H12A 0.9600 .
C12 H12B 0.9599 .
C12 H12C 0.9601 .
