#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/16/1501626.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_1501626
loop_
_publ_author_name
'Philippe Brunet'
'Eric Demers'
'Thierry Maris'
'Gary D. Enright'
'James D. Wuest'
_publ_section_title
;
 Designing Permeable Molecular Crystals That React with External Agents To
 Give Crystalline Products
;
_journal_name_full               'Angewandte Chemie International Edition'
_journal_page_first              5303
_journal_page_last               5306
_journal_paper_doi               10.1002/anie.200352252
_journal_volume                  42
_journal_year                    2003
_chemical_formula_sum            'C46 H30 N12 S'
_chemical_formula_weight         782.88
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           88
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  '-I 4ad'
_symmetry_space_group_name_H-M   'I 41/a :2'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   23.233(16)
_cell_length_b                   23.233(16)
_cell_length_c                   16.274(17)
_cell_measurement_temperature    173(2)
_cell_volume                     8784(13)
_computing_cell_refinement       'Smart (Bruker, 1999)'
_computing_data_collection       'Smart (Bruker, 1999)'
_computing_data_reduction        'Saint (Bruker, 1999)'
_computing_molecular_graphics    'XP (Sheldrick, 1997)'
_computing_publication_material  'Platon (Spek, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Smart 1K'
_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  0.1523
_diffrn_reflns_av_sigmaI/netI    0.0875
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6088
_diffrn_reflns_theta_full        13.77
_diffrn_reflns_theta_max         13.77
_diffrn_reflns_theta_min         1.53
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  0.9823
_exptl_absorpt_correction_T_min  0.9650
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.184
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3248
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.097
_refine_ls_extinction_coef       0.0
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.766
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         688
_refine_ls_number_restraints     192
_refine_ls_restrained_S_all      1.744
_refine_ls_R_factor_all          0.2278
_refine_ls_R_factor_gt           0.1888
_refine_ls_shift/su_max          0.121
_refine_ls_shift/su_mean         0.025
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4321
_refine_ls_wR_factor_ref         0.4611
_reflns_number_gt                462
_reflns_number_total             688
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            deposit.cif
_cod_data_source_block           jiw278
_cod_original_cell_volume        8785(13)
_cod_original_sg_symbol_H-M      I41/a
_cod_database_code               1501626
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'
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
C1 C 0.5000 0.7500 1.1250 0.054(4) Uani 1 4 d SDU . 1
C2 C 0.4626(4) 0.7845(3) 1.0678(4) 0.051(3) Uani 1 1 d GDU A 1
C3 C 0.3998(4) 0.7829(5) 1.0741(5) 0.060(3) Uani 1 1 d GDU A 1
H3 H 0.3815 0.7609 1.1158 0.071 Uiso 1 1 calc R A 1
C4 C 0.3676(4) 0.8143(3) 1.0179(5) 0.066(3) Uani 1 1 d DU A 1
H4 H 0.3269 0.8113 1.0212 0.079 Uiso 1 1 calc R A 1
C5 C 0.3903(2) 0.8498(5) 0.9572(7) 0.051(3) Uani 1 1 d DU A 1
C6 C 0.4500(2) 0.8474(4) 0.9543(7) 0.066(3) Uani 1 1 d DU A 1
H6 H 0.4679 0.8705 0.9134 0.079 Uiso 1 1 calc R A 1
C7 C 0.4869(4) 0.8154(4) 1.0036(5) 0.060(3) Uani 1 1 d DU A 1
H7 H 0.5272 0.8148 0.9937 0.071 Uiso 1 1 calc R A 1
N8 N 0.3491(7) 0.8767(7) 0.9027(10) 0.057(3) Uani 1 1 d U A 1
H8 H 0.3123 0.8701 0.9115 0.068 Uiso 1 1 calc R A 1
C9 C 0.3641(5) 0.9123(4) 0.8371(5) 0.054(4) Uani 1 1 d GDU A 1
N10 N 0.3166(4) 0.9336(5) 0.8043(7) 0.055(2) Uani 1 1 d GDU A 1
C11 C 0.3261(6) 0.9652(5) 0.7381(7) 0.062(4) Uani 1 1 d GDU A 1
N12 N 0.3782(7) 0.9754(5) 0.7043(6) 0.055(2) Uani 1 1 d GDU A 1
C13 C 0.4229(5) 0.9513(6) 0.7418(8) 0.057(4) Uani 1 1 d GDU A 1
N14 N 0.4184(5) 0.9151(5) 0.8079(7) 0.057(3) Uani 1 1 d GDU A 1
N20 N 0.2824(4) 0.9893(9) 0.6975(11) 0.114(3) Uani 1 1 d DU A 1
H20 H 0.2902 1.0006 0.6471 0.137 Uiso 1 1 calc . B 1
N30 N 0.4720(9) 0.9566(7) 0.7113(6) 0.114(3) Uani 1 1 d DU A 1
H30 H 0.5036 0.9456 0.7366 0.137 Uiso 1 1 calc . C 1
C21 C 0.2239(5) 0.9994(11) 0.7246(14) 0.226(15) Uani 1 1 d DU A 1
H21A H 0.2269 1.0083 0.7839 0.271 Uiso 1 1 calc R A 1
H21B H 0.2045 0.9616 0.7210 0.271 Uiso 1 1 calc R A 1
C22 C 0.1794(6) 1.0440(13) 0.6895(19) 0.226(15) Uani 1 1 d DU A 1
H22A H 0.1926 1.0818 0.7102 0.271 Uiso 1 1 calc R A 1
H22B H 0.1865 1.0445 0.6295 0.271 Uiso 1 1 calc R A 1
C23 C 0.1125(5) 1.0454(4) 0.6985(7) 0.40(4) Uani 1 1 d DU A 1
H23A H 0.0972 1.0841 0.6854 0.520 Uiso 1 1 calc R A 1
H23B H 0.1007 1.0349 0.7550 0.520 Uiso 1 1 calc R A 1
S24 S 0.0875(2) 0.9929(4) 0.6254(5) 0.31(2) Uani 0.470(15) 1 d PDU A 1
C251 C 0.0434(5) 0.9614(7) 0.5465(8) 0.168(3) Uani 0.23 1 d PDU A 1
H25A H 0.0694 0.9441 0.5052 0.201 Uiso 0.23 1 calc PR A 1
H25B H 0.0214 0.9294 0.5717 0.201 Uiso 0.23 1 calc PR A 1
C252 C 0.0192(4) 1.0180(10) 0.5872(9) 0.168(3) Uani 0.23 1 d PDU A 1
H25C H -0.0108 1.0051 0.6261 0.201 Uiso 0.23 1 calc PR A 1
H25D H 0.0198 1.0606 0.5890 0.201 Uiso 0.23 1 calc PR A 1
C26 C 0.0000 1.0000 0.5000 0.22(3) Uani 0.94(3) 2 d SPDU . 1
C31 C 0.4720(4) 0.9826(8) 0.6303(5) 0.26(3) Uani 0.470(15) 1 d PDU A 1
H31A H 0.5124 0.9811 0.6110 0.342 Uiso 0.470(15) 1 calc PR A 1
H31B H 0.4629 1.0237 0.6388 0.342 Uiso 0.470(15) 1 calc PR A 1
C32 C 0.4347(6) 0.9630(5) 0.5563(5) 0.26(3) Uani 0.470(15) 1 d PDU A 1
H32 H 0.4062 0.9337 0.5560 0.342 Uiso 0.47 1 calc P A 1
C33 C 0.4506(15) 0.9950(10) 0.4949(12) 0.21(4) Uani 0.470(15) 1 d PDU A 1
H33A H 0.4798 1.0232 0.5023 0.270 Uiso 0.47 1 calc P A 1
H33B H 0.4330 0.9903 0.4426 0.270 Uiso 0.47 1 calc P A 1
C40 C 0.097(4) 0.942(4) 0.609(6) 0.250 Uiso 0.530(15) 1 d P A 2
C41 C 0.059(4) 0.991(4) 0.489(6) 0.250 Uiso 0.530(15) 1 d P A 2
C42 C 0.054(4) 1.016(4) 0.558(6) 0.250 Uiso 0.530(15) 1 d P A 2
C43 C 0.519(4) 0.942(4) 0.585(5) 0.250 Uiso 0.530(15) 1 d P A 2
C44 C 0.516(4) 0.989(4) 0.631(6) 0.250 Uiso 0.530(15) 1 d P A 2
C45 C 0.497(4) 0.940(4) 0.476(5) 0.250 Uiso 0.530(15) 1 d P A 2
C46 C 0.113(4) 0.954(4) 0.521(6) 0.250 Uiso 0.530(15) 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
_geom_angle_publ_flag
C2 C1 C2 112.5(3) 15_567 6_564 y
C2 C1 C2 112.5(3) 15_567 . y
C2 C1 C2 103.6(6) 6_564 . y
C2 C1 C2 103.6(6) 15_567 12_768 y
C2 C1 C2 112.5(3) 6_564 12_768 y
C2 C1 C2 112.5(3) . 12_768 y
C7 C2 C3 118.1(7) . . y
C7 C2 C1 120.4(7) . . y
C3 C2 C1 121.2(4) . . y
C4 C3 C2 118.6(8) . . y
C3 C4 C5 125.1(9) . . y
C4 C5 C6 112.3(9) . . y
C4 C5 N8 116.2(8) . . y
C6 C5 N8 131.0(10) . . y
C7 C6 C5 128.2(9) . . y
C2 C7 C6 117.4(9) . . y
C9 N8 C5 124.1(13) . . y
N10 C9 N14 128.2 . . y
N10 C9 N8 108.9(11) . . y
N14 C9 N8 122.2(10) . . y
C9 N10 C11 113.5 . . y
N10 C11 N20 120.6(12) . . y
N10 C11 N12 125.4 . . y
N20 C11 N12 114.0(12) . . y
C13 N12 C11 116.1 . . y
N30 C13 N12 119.4(12) . . y
N30 C13 N14 116.2(12) . . y
N12 C13 N14 124.0 . . y
C9 N14 C13 112.3 . . y
C11 N20 C21 129.2(18) . . y
C13 N30 C31 113.6(15) . . y
N20 C21 C22 127.9(18) . . y
C23 C22 C21 129.4(18) . . y
C22 C23 S24 104.2(14) . . y
C23 S24 C251 158.8(8) . . y
C23 S24 C252 107.1(9) . . y
C251 S24 C252 52.0(9) . . y
C26 C251 S24 118.9(9) . . y
C26 C252 S24 119.0(10) . . y
C252 C26 C252 180.000(4) . 9_576 y
C252 C26 C251 118.7(8) . 9_576 y
C252 C26 C251 61.3(8) 9_576 9_576 y
C252 C26 C251 61.3(8) . . y
C252 C26 C251 118.7(8) 9_576 . y
C251 C26 C251 180.000(5) 9_576 . y
N30 C31 C32 125.8(12) . . y
C33 C32 C31 105.7(16) . . y
C42 C41 C46 91(8) . . y
C44 C43 C45 123(8) . . y
C40 C46 C41 102(8) . . y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.505(8) 15_567 y
C1 C2 1.505(8) 6_564 y
C1 C2 1.505(7) . y
C1 C2 1.505(8) 12_768 y
C2 C7 1.389(5) . y
C2 C3 1.4625 . y
C3 C4 1.389(5) . y
C4 C5 1.390(5) . y
C5 C6 1.390(5) . y
C5 N8 1.447(17) . y
C6 C7 1.389(5) . y
N8 C9 1.394(17) . y
C9 N10 1.3210 . y
C9 N14 1.3512 . y
N10 C11 1.3220 . y
C11 N20 1.335(18) . y
C11 N12 1.3497 . y
N12 C13 1.3285 . y
C13 N30 1.25(2) . y
C13 N14 1.3694 . y
N20 C21 1.448(10) . y
N30 C31 1.450(10) . y
C21 C22 1.571(19) . y
C22 C23 1.561(16) . y
C23 S24 1.800(6) . y
S24 C251 1.800(6) . y
S24 C252 1.800(6) . y
C251 C26 1.547(14) . y
C252 C26 1.545(16) . y
C26 C252 1.545(16) 9_576 y
C26 C251 1.547(14) 9_576 y
C31 C32 1.550(6) . y
C32 C33 1.300(6) . y
C40 C46 1.50(12) . y
C41 C42 1.27(12) . y
C41 C46 1.61(12) . y
C43 C44 1.32(11) . y
C43 C45 1.84(11) . y
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
N8 H8 N12 0.88 2.14 3.00(3) 165.6 8_354
N20 H20 N10 0.88 2.24 3.05(4) 152.8 7_554
