#------------------------------------------------------------------------------
#$Date: 2016-03-22 12:08:14 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178936 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/65/4116553.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_4116553
loop_
_publ_author_name
'Seenichamy Jeyaprakash Narayanan'
'Bashyam Sridevi'
'Tavarekere K. Chandrashekar'
'Ashwani Vij'
'Raja Roy'
_publ_section_title
;
 Novel Core-Modified Expanded Porphyrins with meso-Aryl Substituents:
 Synthesis, Spectral and Structural Characterization
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9053
_journal_page_last               9068
_journal_paper_doi               10.1021/ja991472k
_journal_volume                  121
_journal_year                    1999
_chemical_formula_sum            'C66 H44 N6 S2'
_chemical_formula_weight         985.19
_chemical_name_common            'S2N4 Rubyrin'
_chemical_name_systematic
;

 ?

;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 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                90.00
_cell_angle_beta                 105.8160(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   29.0002(6)
_cell_length_b                   15.0991(4)
_cell_length_c                   11.9801(3)
_cell_measurement_temperature    213(2)
_cell_volume                     5047.2(2)
_computing_cell_refinement       'Siemens XSCANS'
_computing_data_collection       'Siemens XSCANS'
_computing_data_reduction        'Siemens SHELXTL'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      213(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_method       'ω scans'
_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  0.0701
_diffrn_reflns_av_sigmaI/netI    0.0639
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10690
_diffrn_reflns_theta_full        23.25
_diffrn_reflns_theta_max         23.25
_diffrn_reflns_theta_min         2.18
_exptl_absorpt_coefficient_mu    0.156
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'greenish bl'
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_description       Block
_exptl_crystal_F_000             2056
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.00051(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         3601
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0444
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0672P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1132
_refine_ls_wR_factor_ref         0.1210
_reflns_number_gt                2793
_reflns_number_total             3601
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja991472k_2.cif
_cod_data_source_block           JA991472K-123
_cod_database_code               4116553
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.595723(18) 0.35078(3) 0.80007(5) 0.0443(2) Uani 1 1 d . . .
N1 N 0.56284(7) 0.65339(12) 0.7349(2) 0.0442(5) Uani 1 1 d . . .
N1S N 0.79319(9) 0.34226(17) 1.4632(2) 0.0759(7) Uani 1 1 d . . .
C1S C 0.75581(8) 0.24470(15) 1.2846(2) 0.0549(6) Uani 1 1 d . . .
C2S C 0.70791(9) 0.21903(17) 1.2577(3) 0.0647(7) Uani 1 1 d . . .
H2SA H 0.6889 0.2345 1.3069 0.078 Uiso 1 1 calc R . .
C3S C 0.68899(10) 0.17120(19) 1.1593(3) 0.0826(10) Uani 1 1 d . . .
H3SA H 0.6565 0.1549 1.1392 0.099 Uiso 1 1 calc R . .
C4S C 0.71717(12) 0.1468(2) 1.0897(3) 0.0926(11) Uani 1 1 d . . .
H4SA H 0.7038 0.1131 1.0227 0.111 Uiso 1 1 calc R . .
C5S C 0.76502(12) 0.1709(2) 1.1161(3) 0.0948(11) Uani 1 1 d . . .
H5SA H 0.7841 0.1535 1.0677 0.114 Uiso 1 1 calc R . .
C6S C 0.78419(9) 0.22017(18) 1.2130(3) 0.0711(8) Uani 1 1 d . . .
H6SA H 0.8165 0.2375 1.2315 0.085 Uiso 1 1 calc R . .
C7S C 0.77620(9) 0.29777(17) 1.3853(3) 0.0577(7) Uani 1 1 d . . .
N2 N 0.50776(6) 0.74271(13) 0.55293(16) 0.0418(5) Uani 1 1 d . . .
C1 C 0.55270(7) 0.31677(13) 0.6762(2) 0.0409(5) Uani 1 1 d . . .
C2 C 0.52493(8) 0.39097(14) 0.6272(2) 0.0577(7) Uani 1 1 d . . .
H2A H 0.4988 0.3870 0.5606 0.069 Uiso 1 1 calc R . .
C3 C 0.53881(9) 0.46863(15) 0.6839(2) 0.0618(7) Uani 1 1 d . . .
H3A H 0.5232 0.5226 0.6590 0.074 Uiso 1 1 calc R . .
C4 C 0.57807(7) 0.46210(13) 0.7821(2) 0.0400(5) Uani 1 1 d . . .
C5 C 0.54918(7) 0.22810(13) 0.63657(19) 0.0383(5) Uani 1 1 d . . .
C6 C 0.57904(7) 0.15778(12) 0.7101(2) 0.0391(5) Uani 1 1 d . . .
C7 C 0.61351(7) 0.11188(14) 0.6716(2) 0.0490(6) Uani 1 1 d . . .
H7A H 0.6185 0.1264 0.5994 0.059 Uiso 1 1 calc R . .
C8 C 0.64037(8) 0.04574(15) 0.7374(3) 0.0571(7) Uani 1 1 d . . .
H8A H 0.6640 0.0164 0.7111 0.068 Uiso 1 1 calc R . .
C9 C 0.63258(8) 0.02271(15) 0.8416(3) 0.0629(8) Uani 1 1 d . . .
H9A H 0.6503 -0.0236 0.8857 0.076 Uiso 1 1 calc R . .
C10 C 0.59870(8) 0.06753(16) 0.8818(2) 0.0617(7) Uani 1 1 d . . .
H10A H 0.5937 0.0520 0.9535 0.074 Uiso 1 1 calc R . .
C11 C 0.57228(8) 0.13507(15) 0.8169(2) 0.0521(6) Uani 1 1 d . . .
H11A H 0.5496 0.1658 0.8451 0.062 Uiso 1 1 calc R . .
C12 C 0.60160(7) 0.52958(13) 0.8576(2) 0.0376(5) Uani 1 1 d . . .
C13 C 0.63996(7) 0.50551(13) 0.96364(19) 0.0383(5) Uani 1 1 d . . .
C14 C 0.63100(8) 0.44816(14) 1.0462(2) 0.0474(6) Uani 1 1 d . . .
H14A H 0.6004 0.4231 1.0346 0.057 Uiso 1 1 calc R . .
C15 C 0.66660(8) 0.42793(16) 1.1445(2) 0.0565(6) Uani 1 1 d . . .
H15A H 0.6602 0.3888 1.1995 0.068 Uiso 1 1 calc R . .
C16 C 0.71171(8) 0.46461(15) 1.1632(2) 0.0553(6) Uani 1 1 d . . .
H16A H 0.7357 0.4511 1.2314 0.066 Uiso 1 1 calc R . .
C17 C 0.72156(8) 0.52081(15) 1.0822(2) 0.0512(6) Uani 1 1 d . . .
H17A H 0.7524 0.5449 1.0942 0.061 Uiso 1 1 calc R . .
C18 C 0.68591(7) 0.54159(14) 0.9836(2) 0.0464(6) Uani 1 1 d . . .
H18A H 0.6926 0.5806 0.9288 0.056 Uiso 1 1 calc R . .
C19 C 0.59156(7) 0.62103(13) 0.8364(2) 0.0383(5) Uani 1 1 d . . .
C20 C 0.60918(7) 0.69513(13) 0.9095(2) 0.0434(6) Uani 1 1 d . . .
H20A H 0.6297 0.6927 0.9852 0.052 Uiso 1 1 calc R . .
C21 C 0.59089(7) 0.77063(14) 0.8500(2) 0.0438(6) Uani 1 1 d . . .
H21A H 0.5965 0.8293 0.8767 0.053 Uiso 1 1 calc R . .
C22 C 0.56184(7) 0.74276(13) 0.74081(19) 0.0413(5) Uani 1 1 d . . .
C23 C 0.53316(7) 0.78987(13) 0.6445(2) 0.0401(5) Uani 1 1 d . . .
C24 C 0.52371(8) 0.88109(14) 0.6214(2) 0.0506(6) Uani 1 1 d . . .
H24A H 0.5370 0.9287 0.6702 0.061 Uiso 1 1 calc R . .
C25 C 0.49161(8) 0.88633(14) 0.5147(2) 0.0489(6) Uani 1 1 d . . .
H25A H 0.4785 0.9387 0.4767 0.059 Uiso 1 1 calc R . .
C26 C 0.48144(7) 0.79882(13) 0.47071(19) 0.0387(5) Uani 1 1 d . . .
H2 H 0.5054(12) 0.688(3) 0.560(3) 0.025(8) Uiso 0.54(3) 1 d P A 1
H1 H 0.5540(15) 0.633(3) 0.673(4) 0.025(8) Uiso 0.46(3) 1 d P A 2
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 93.49(10) . .
C22 N1 C19 109.1(2) . .
C6S C1S C2S 120.3(3) . .
C6S C1S C7S 119.3(2) . .
C2S C1S C7S 120.4(2) . .
C3S C2S C1S 119.2(3) . .
C2S C3S C4S 120.2(3) . .
C3S C4S C5S 121.2(3) . .
C6S C5S C4S 119.2(3) . .
C5S C6S C1S 119.9(3) . .
N1S C7S C1S 177.4(3) . .
C23 N2 C26 109.51(18) . .
C2 C1 C5 129.1(2) . .
C2 C1 S1 108.44(16) . .
C5 C1 S1 122.41(16) . .
C3 C2 C1 114.8(2) . .
C2 C3 C4 114.9(2) . .
C3 C4 C12 128.98(19) . .
C3 C4 S1 108.30(16) . .
C12 C4 S1 122.72(16) . .
C26 C5 C1 123.30(19) 5_666 .
C26 C5 C6 116.90(17) 5_666 .
C1 C5 C6 119.80(19) . .
C11 C6 C7 118.4(2) . .
C11 C6 C5 120.88(19) . .
C7 C6 C5 120.7(2) . .
C8 C7 C6 121.1(2) . .
C9 C8 C7 119.9(2) . .
C8 C9 C10 120.1(2) . .
C11 C10 C9 120.2(3) . .
C10 C11 C6 120.3(2) . .
C4 C12 C19 123.3(2) . .
C4 C12 C13 119.34(18) . .
C19 C12 C13 117.34(18) . .
C14 C13 C18 118.4(2) . .
C14 C13 C12 121.21(18) . .
C18 C13 C12 120.43(19) . .
C15 C14 C13 120.4(2) . .
C14 C15 C16 120.5(2) . .
C17 C16 C15 120.1(2) . .
C16 C17 C18 119.6(2) . .
C17 C18 C13 121.0(2) . .
N1 C19 C12 123.59(19) . .
N1 C19 C20 107.21(19) . .
C12 C19 C20 129.2(2) . .
C21 C20 C19 108.1(2) . .
C20 C21 C22 106.36(19) . .
N1 C22 C21 109.3(2) . .
N1 C22 C23 118.33(19) . .
C21 C22 C23 132.38(19) . .
N2 C23 C22 117.87(18) . .
N2 C23 C24 108.76(19) . .
C22 C23 C24 133.4(2) . .
C25 C24 C23 106.60(19) . .
C24 C25 C26 108.2(2) . .
N2 C26 C5 124.70(18) . 5_666
N2 C26 C25 106.88(19) . .
C5 C26 C25 128.41(19) 5_666 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C1 1.736(2) .
S1 C4 1.753(2) .
N1 C22 1.352(3) .
N1 C19 1.364(3) .
N1S C7S 1.146(3) .
C1S C6S 1.390(3) .
C1S C2S 1.393(3) .
C1S C7S 1.435(4) .
C2S C3S 1.364(4) .
C3S C4S 1.367(5) .
C4S C5S 1.385(4) .
C5S C6S 1.364(4) .
N2 C23 1.346(3) .
N2 C26 1.364(3) .
C1 C2 1.411(3) .
C1 C5 1.415(3) .
C2 C3 1.360(3) .
C3 C4 1.401(3) .
C4 C12 1.409(3) .
C5 C26 1.408(3) 5_666
C5 C6 1.496(3) .
C6 C11 1.389(3) .
C6 C7 1.394(3) .
C7 C8 1.375(3) .
C8 C9 1.372(4) .
C9 C10 1.383(4) .
C10 C11 1.381(3) .
C12 C19 1.420(3) .
C12 C13 1.488(3) .
C13 C14 1.391(3) .
C13 C18 1.399(3) .
C14 C15 1.372(3) .
C15 C16 1.381(3) .
C16 C17 1.376(3) .
C17 C18 1.378(3) .
C19 C20 1.427(3) .
C20 C21 1.372(3) .
C21 C22 1.414(3) .
C22 C23 1.416(3) .
C23 C24 1.417(3) .
C24 C25 1.363(3) .
C25 C26 1.423(3) .
C26 C5 1.408(3) 5_666
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C6S C1S C2S C3S -1.4(4) . .
C7S C1S C2S C3S 177.7(2) . .
C1S C2S C3S C4S 1.8(4) . .
C2S C3S C4S C5S -1.0(5) . .
C3S C4S C5S C6S -0.3(6) . .
C4S C5S C6S C1S 0.7(5) . .
C2S C1S C6S C5S 0.1(4) . .
C7S C1S C6S C5S -179.0(3) . .
C6S C1S C7S N1S 48(6) . .
C2S C1S C7S N1S -131(6) . .
C4 S1 C1 C2 -2.21(18) . .
C4 S1 C1 C5 177.03(18) . .
C5 C1 C2 C3 -177.2(2) . .
S1 C1 C2 C3 2.0(3) . .
C1 C2 C3 C4 -0.6(4) . .
C2 C3 C4 C12 178.6(2) . .
C2 C3 C4 S1 -1.1(3) . .
C1 S1 C4 C3 1.90(19) . .
C1 S1 C4 C12 -177.77(19) . .
C2 C1 C5 C26 7.0(4) . 5_666
S1 C1 C5 C26 -172.03(15) . 5_666
C2 C1 C5 C6 -173.1(2) . .
S1 C1 C5 C6 7.9(3) . .
C26 C5 C6 C11 -115.1(2) 5_666 .
C1 C5 C6 C11 65.0(3) . .
C26 C5 C6 C7 63.2(2) 5_666 .
C1 C5 C6 C7 -116.7(2) . .
C11 C6 C7 C8 -0.1(3) . .
C5 C6 C7 C8 -178.50(19) . .
C6 C7 C8 C9 1.5(3) . .
C7 C8 C9 C10 -1.8(4) . .
C8 C9 C10 C11 0.6(4) . .
C9 C10 C11 C6 0.9(4) . .
C7 C6 C11 C10 -1.1(3) . .
C5 C6 C11 C10 177.3(2) . .
C3 C4 C12 C19 -7.5(4) . .
S1 C4 C12 C19 172.08(15) . .
C3 C4 C12 C13 174.2(2) . .
S1 C4 C12 C13 -6.2(3) . .
C4 C12 C13 C14 -57.6(3) . .
C19 C12 C13 C14 124.0(2) . .
C4 C12 C13 C18 123.6(2) . .
C19 C12 C13 C18 -54.8(3) . .
C18 C13 C14 C15 0.0(3) . .
C12 C13 C14 C15 -178.9(2) . .
C13 C14 C15 C16 0.4(4) . .
C14 C15 C16 C17 -1.1(4) . .
C15 C16 C17 C18 1.3(4) . .
C16 C17 C18 C13 -0.8(4) . .
C14 C13 C18 C17 0.2(3) . .
C12 C13 C18 C17 179.1(2) . .
C22 N1 C19 C12 -177.94(19) . .
C22 N1 C19 C20 0.2(2) . .
C4 C12 C19 N1 -8.7(3) . .
C13 C12 C19 N1 169.62(18) . .
C4 C12 C19 C20 173.6(2) . .
C13 C12 C19 C20 -8.1(3) . .
N1 C19 C20 C21 -0.3(2) . .
C12 C19 C20 C21 177.7(2) . .
C19 C20 C21 C22 0.3(2) . .
C19 N1 C22 C21 0.0(2) . .
C19 N1 C22 C23 -178.81(17) . .
C20 C21 C22 N1 -0.2(2) . .
C20 C21 C22 C23 178.4(2) . .
C26 N2 C23 C22 178.21(17) . .
C26 N2 C23 C24 -0.7(2) . .
N1 C22 C23 N2 1.2(3) . .
C21 C22 C23 N2 -177.3(2) . .
N1 C22 C23 C24 179.7(2) . .
C21 C22 C23 C24 1.2(4) . .
N2 C23 C24 C25 0.8(2) . .
C22 C23 C24 C25 -177.8(2) . .
C23 C24 C25 C26 -0.6(2) . .
C23 N2 C26 C5 179.81(18) . 5_666
C23 N2 C26 C25 0.3(2) . .
C24 C25 C26 N2 0.2(2) . .
C24 C25 C26 C5 -179.3(2) . 5_666
