#------------------------------------------------------------------------------
#$Date: 2016-03-26 13:39:38 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180231 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/17/7111751.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_7111751
loop_
_publ_author_name
'Bell, Toby D. M.'
'Bhosale, Sheshanath V.'
'Forsyth, Craig M.'
'Hayne, David'
'Ghiggino, Kenneth P.'
'Hutchison, James A.'
'Jani, Chintan H.'
'Langford, Steven J.'
'Lee, Marcia A.-P.'
'Woodward, Clint P.'
_publ_section_title
;
 Melt-induced fluorescent signature in a simple naphthalenediimide
;
_journal_issue                   27
_journal_name_full               'Chemical Communications'
_journal_page_first              4881
_journal_page_last               4883
_journal_paper_doi               10.1039/c0cc00865f
_journal_volume                  46
_journal_year                    2010
_chemical_formula_moiety         'C36 H34 N2 O12 S2'
_chemical_formula_sum            'C36 H34 N2 O12 S2'
_chemical_formula_weight         750.77
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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                95.651(5)
_cell_angle_beta                 95.316(5)
_cell_angle_gamma                93.561(5)
_cell_formula_units_Z            1
_cell_length_a                   4.8437(4)
_cell_length_b                   7.3713(8)
_cell_length_c                   23.573(2)
_cell_measurement_temperature    123(2)
_cell_volume                     831.81(13)
_computing_cell_refinement       'Bruker Apex2 v2.0 (Bruker AXS, 2005)'
_computing_data_collection       'Bruker Apex2 v2.0 (Bruker AXS, 2005)'
_computing_data_reduction        'Bruker Apex2 v2.0 (Bruker AXS, 2005)'
_computing_molecular_graphics    'X-Seed (Barbour, 2001)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker X8 Apex CCD'
_diffrn_measurement_method       'phi and omega 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  0.0309
_diffrn_reflns_av_sigmaI/netI    0.0311
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            12574
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.62
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.232
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3811
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0385
_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)+(0.0395P)²+0.4496P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.0978
_reflns_number_gt                3390
_reflns_number_total             3811
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0CC00865Fsup1.cif
_cod_data_source_block           a52_07
_cod_original_cell_volume        831.82(14)
_cod_database_code               7111751
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
S1 S 0.75901(8) 0.74675(6) 0.671953(18) 0.02571(12) Uani 1 1 d .
O1 O 1.5426(2) 1.14957(15) 0.92342(5) 0.0242(2) Uani 1 1 d .
O2 O 1.3503(2) 1.69548(15) 0.86026(5) 0.0241(2) Uani 1 1 d .
O3 O 1.2086(2) 1.18111(14) 0.78703(5) 0.0213(2) Uani 1 1 d .
O4 O 0.9815(2) 0.89565(15) 0.70397(5) 0.0240(2) Uani 1 1 d .
O5 O 0.6162(3) 0.84236(18) 0.62995(6) 0.0394(3) Uani 1 1 d .
O6 O 0.6118(3) 0.66371(17) 0.71347(6) 0.0357(3) Uani 1 1 d .
N1 N 1.4355(3) 1.41868(17) 0.88965(5) 0.0180(3) Uani 1 1 d .
C1 C 1.4154(3) 1.2868(2) 0.92787(6) 0.0177(3) Uani 1 1 d .
C2 C 1.2324(3) 1.32291(19) 0.97456(6) 0.0161(3) Uani 1 1 d .
C3 C 1.0883(3) 1.48433(19) 0.97814(6) 0.0154(3) Uani 1 1 d .
C4 C 1.1210(3) 1.61527(19) 0.93920(6) 0.0164(3) Uani 1 1 d .
C5 C 1.3085(3) 1.5844(2) 0.89359(6) 0.0182(3) Uani 1 1 d .
C6 C 1.2013(3) 1.1987(2) 1.01379(6) 0.0180(3) Uani 1 1 d .
H6 H 1.3010 1.0917 1.0117 0.022 Uiso 1 1 calc R
C7 C 0.9768(3) 1.7709(2) 0.94312(6) 0.0185(3) Uani 1 1 d .
H7 H 0.9983 1.8581 0.9165 0.022 Uiso 1 1 calc R
C8 C 1.5926(3) 1.3817(2) 0.83943(6) 0.0213(3) Uani 1 1 d .
H8A H 1.7094 1.2782 0.8452 0.026 Uiso 1 1 calc R
H8B H 1.7168 1.4904 0.8354 0.026 Uiso 1 1 calc R
C9 C 1.3950(3) 1.3356(2) 0.78511(6) 0.0227(3) Uani 1 1 d .
H9A H 1.2864 1.4424 0.7786 0.027 Uiso 1 1 calc R
H9B H 1.5056 1.3129 0.7522 0.027 Uiso 1 1 calc R
C10 C 1.3352(3) 1.0126(2) 0.77713(7) 0.0212(3) Uani 1 1 d .
H10A H 1.4472 0.9872 0.8124 0.025 Uiso 1 1 calc R
H10B H 1.4601 1.0202 0.7464 0.025 Uiso 1 1 calc R
C11 C 1.1118(3) 0.8626(2) 0.75999(6) 0.0214(3) Uani 1 1 d .
H11A H 1.1924 0.7423 0.7578 0.026 Uiso 1 1 calc R
H11B H 0.9732 0.8640 0.7883 0.026 Uiso 1 1 calc R
C12 C 0.9494(3) 0.5808(2) 0.63785(7) 0.0219(3) Uani 1 1 d .
C13 C 0.9744(4) 0.4133(2) 0.65884(7) 0.0274(4) Uani 1 1 d .
H13 H 0.8925 0.3878 0.6926 0.033 Uiso 1 1 calc R
C14 C 1.1202(4) 0.2826(2) 0.63022(7) 0.0298(4) Uani 1 1 d .
H14 H 1.1381 0.1676 0.6447 0.036 Uiso 1 1 calc R
C15 C 1.2403(3) 0.3175(2) 0.58081(7) 0.0284(4) Uani 1 1 d .
C16 C 1.2123(4) 0.4870(2) 0.56104(7) 0.0300(4) Uani 1 1 d .
H16 H 1.2949 0.5132 0.5275 0.036 Uiso 1 1 calc R
C17 C 1.0679(3) 0.6191(2) 0.58880(7) 0.0277(4) Uani 1 1 d .
H17 H 1.0502 0.7343 0.5744 0.033 Uiso 1 1 calc R
C18 C 1.3941(4) 0.1753(3) 0.54892(9) 0.0425(5) Uani 1 1 d .
H18A H 1.3976 0.0659 0.5694 0.064 Uiso 1 1 calc R
H18B H 1.5849 0.2239 0.5463 0.064 Uiso 1 1 calc R
H18C H 1.2998 0.1434 0.5103 0.064 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O5 S1 O6 120.58(9) . .
O5 S1 O4 103.35(7) . .
O6 S1 O4 108.72(7) . .
O5 S1 C12 109.35(8) . .
O6 S1 C12 108.21(8) . .
O4 S1 C12 105.62(7) . .
C9 O3 C10 112.76(12) . .
C11 O4 S1 118.14(9) . .
C1 N1 C5 125.05(12) . .
C1 N1 C8 118.85(12) . .
C5 N1 C8 116.06(12) . .
O1 C1 N1 121.53(13) . .
O1 C1 C2 121.80(13) . .
N1 C1 C2 116.66(12) . .
C6 C2 C3 120.03(13) . .
C6 C2 C1 120.04(13) . .
C3 C2 C1 119.93(13) . .
C4 C3 C3 119.40(16) . 2_787
C4 C3 C2 121.10(13) . .
C3 C3 C2 119.49(16) 2_787 .
C7 C4 C3 120.18(13) . .
C7 C4 C5 120.08(13) . .
C3 C4 C5 119.73(13) . .
O2 C5 N1 120.44(14) . .
O2 C5 C4 122.20(14) . .
N1 C5 C4 117.35(13) . .
C2 C6 C7 120.41(13) . 2_787
C4 C7 C6 120.47(13) . 2_787
N1 C8 C9 110.60(12) . .
O3 C9 C8 113.53(12) . .
O3 C10 C11 108.77(12) . .
O4 C11 C10 106.80(12) . .
C13 C12 C17 120.74(15) . .
C13 C12 S1 120.55(12) . .
C17 C12 S1 118.70(13) . .
C12 C13 C14 119.41(15) . .
C15 C14 C13 120.97(16) . .
C16 C15 C14 118.16(16) . .
C16 C15 C18 120.55(16) . .
C14 C15 C18 121.29(17) . .
C17 C16 C15 121.87(16) . .
C16 C17 C12 118.85(16) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O5 1.4235(14) .
S1 O6 1.4262(13) .
S1 O4 1.5730(12) .
S1 C12 1.7543(16) .
O1 C1 1.2171(18) .
O2 C5 1.2103(18) .
O3 C9 1.4157(18) .
O3 C10 1.4275(18) .
O4 C11 1.4594(18) .
N1 C1 1.3942(19) .
N1 C5 1.4003(19) .
N1 C8 1.4778(18) .
C1 C2 1.490(2) .
C2 C6 1.375(2) .
C2 C3 1.416(2) .
C3 C4 1.408(2) .
C3 C3 1.410(3) 2_787
C4 C7 1.379(2) .
C4 C5 1.480(2) .
C6 C7 1.403(2) 2_787
C7 C6 1.403(2) 2_787
C8 C9 1.522(2) .
C10 C11 1.496(2) .
C12 C13 1.383(2) .
C12 C17 1.383(2) .
C13 C14 1.388(2) .
C14 C15 1.388(2) .
C15 C16 1.386(3) .
C15 C18 1.504(2) .
C16 C17 1.382(2) .
