#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:18:11 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178777 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/31/4103140.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_4103140
loop_
_publ_author_name
'Seong-Jun Yoon'
'Jong Won Chung'
'Johannes Gierschner'
'Kil Suk Kim'
'Moon-Gun Choi'
'Dongho Kim'
'Soo Young Park'
_publ_section_title
;
 Multistimuli Two-Color Luminescence Switching via Different Slip-Stacking
 of Highly Fluorescent Molecular Sheets
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13675
_journal_page_last               13683
_journal_paper_doi               10.1021/ja1044665
_journal_volume                  132
_journal_year                    2010
_chemical_formula_sum            'C32 H32 N2 O2'
_chemical_formula_weight         476.60
_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                96.945(4)
_cell_angle_beta                 102.309(4)
_cell_angle_gamma                91.532(4)
_cell_formula_units_Z            1
_cell_length_a                   7.6944(19)
_cell_length_b                   8.914(2)
_cell_length_c                   9.926(3)
_cell_measurement_temperature    273(2)
_cell_volume                     659.3(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.896
_diffrn_measured_fraction_theta_max 0.896
_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  0.0350
_diffrn_reflns_av_sigmaI/netI    0.0805
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5406
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         2.31
_exptl_absorpt_coefficient_mu    0.075
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             254
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.07(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2947
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0618
_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)+(0.0812P)²+0.0774P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1809
_refine_ls_wR_factor_ref         0.1938
_reflns_number_gt                2320
_reflns_number_total             2947
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja1044665_si_003.cif
_cod_data_source_block           875
_cod_database_code               4103140
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
O1 O 0.37504(15) 0.94283(11) 0.78984(11) 0.0659(4) Uani 1 1 d .
C10 C 0.3870(2) 0.77159(16) 0.95141(16) 0.0604(4) Uani 1 1 d .
H10 H 0.4667 0.8395 1.0152 0.072 Uiso 1 1 calc R
C5 C 0.31971(19) 0.80713(15) 0.81956(16) 0.0553(4) Uani 1 1 d .
C12 C 0.05577(18) 0.27445(15) 0.88362(14) 0.0508(4) Uani 1 1 d .
C14 C 0.02873(18) 0.13488(15) 0.94451(14) 0.0500(4) Uani 1 1 d .
C8 C 0.21635(19) 0.53137(15) 0.89648(15) 0.0530(4) Uani 1 1 d .
C4 C 0.2957(2) 0.98606(17) 0.65799(18) 0.0656(4) Uani 1 1 d .
H4A H 0.1678 0.9891 0.6487 0.079 Uiso 1 1 calc R
H4B H 0.3183 0.9120 0.5846 0.079 Uiso 1 1 calc R
C11 C 0.17195(19) 0.39109(16) 0.94471(15) 0.0539(4) Uani 1 1 d .
H11 H 0.2348 0.3796 1.0336 0.065 Uiso 1 1 calc R
C9 C 0.3370(2) 0.63668(16) 0.98877(15) 0.0577(4) Uani 1 1 d .
H9 H 0.3844 0.6143 1.0779 0.069 Uiso 1 1 calc R
C3 C 0.3708(2) 1.13793(17) 0.64400(18) 0.0651(4) Uani 1 1 d .
H3A H 0.4991 1.1354 0.6560 0.078 Uiso 1 1 calc R
H3B H 0.3455 1.2123 0.7162 0.078 Uiso 1 1 calc R
C15 C -0.1043(2) 0.02664(18) 0.87794(17) 0.0696(5) Uani 1 1 d .
H15 H -0.1768 0.0434 0.7939 0.084 Uiso 1 1 calc R
C7 C 0.1523(2) 0.57009(18) 0.76381(17) 0.0711(5) Uani 1 1 d .
H7 H 0.0732 0.5025 0.6993 0.085 Uiso 1 1 calc R
C6 C 0.2018(2) 0.70447(18) 0.72519(17) 0.0717(5) Uani 1 1 d .
H6 H 0.1564 0.7269 0.6357 0.086 Uiso 1 1 calc R
C16 C 0.1329(2) 0.10398(18) 1.06854(17) 0.0689(5) Uani 1 1 d .
H16 H 0.2242 0.1732 1.1166 0.083 Uiso 1 1 calc R
C13 C -0.0564(2) 0.27977(18) 0.74949(17) 0.0704(5) Uani 1 1 d .
N1 N -0.1482(3) 0.2776(2) 0.64320(19) 0.1164(8) Uani 1 1 d .
C2 C 0.2913(3) 1.1836(2) 0.5028(2) 0.0860(6) Uani 1 1 d .
H2A H 0.3150 1.1072 0.4317 0.103 Uiso 1 1 calc R
H2B H 0.1631 1.1854 0.4920 0.103 Uiso 1 1 calc R
C1 C 0.3607(4) 1.3345(2) 0.4791(3) 0.1066(8) Uani 1 1 d .
H1A H 0.3445 1.4103 0.5521 0.160 Uiso 1 1 calc R
H1B H 0.2970 1.3594 0.3912 0.160 Uiso 1 1 calc R
H1C H 0.4852 1.3306 0.4789 0.160 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'
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
C5 O1 C4 117.52(11) .
C9 C10 C5 120.24(13) .
C9 C10 H10 119.9 .
C5 C10 H10 119.9 .
O1 C5 C10 117.03(13) .
O1 C5 C6 123.69(14) .
C10 C5 C6 119.27(14) .
C11 C12 C13 120.47(13) .
C11 C12 C14 125.36(13) .
C13 C12 C14 114.16(11) .
C16 C14 C15 116.44(13) .
C16 C14 C12 122.73(12) .
C15 C14 C12 120.84(13) .
C7 C8 C9 116.41(13) .
C7 C8 C11 125.48(13) .
C9 C8 C11 118.09(13) .
O1 C4 C3 110.14(13) .
O1 C4 H4A 109.6 .
C3 C4 H4A 109.6 .
O1 C4 H4B 109.6 .
C3 C4 H4B 109.6 .
H4A C4 H4B 108.1 .
C12 C11 C8 131.41(13) .
C12 C11 H11 114.3 .
C8 C11 H11 114.3 .
C10 C9 C8 121.89(13) .
C10 C9 H9 119.1 .
C8 C9 H9 119.1 .
C4 C3 C2 110.77(14) .
C4 C3 H3A 109.5 .
C2 C3 H3A 109.5 .
C4 C3 H3B 109.5 .
C2 C3 H3B 109.5 .
H3A C3 H3B 108.1 .
C16 C15 C14 122.33(14) 2_557
C16 C15 H15 118.8 2_557
C14 C15 H15 118.8 .
C6 C7 C8 122.19(13) .
C6 C7 H7 118.9 .
C8 C7 H7 118.9 .
C7 C6 C5 119.98(14) .
C7 C6 H6 120.0 .
C5 C6 H6 120.0 .
C15 C16 C14 121.23(13) 2_557
C15 C16 H16 119.4 2_557
C14 C16 H16 119.4 .
N1 C13 C12 176.94(16) .
C1 C2 C3 114.39(18) .
C1 C2 H2A 108.7 .
C3 C2 H2A 108.7 .
C1 C2 H2B 108.7 .
C3 C2 H2B 108.7 .
H2A C2 H2B 107.6 .
C2 C1 H1A 109.5 .
C2 C1 H1B 109.5 .
H1A C1 H1B 109.5 .
C2 C1 H1C 109.5 .
H1A C1 H1C 109.5 .
H1B C1 H1C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C5 1.3579(17) .
O1 C4 1.4239(19) .
C10 C9 1.370(2) .
C10 C5 1.379(2) .
C10 H10 0.9300 .
C5 C6 1.387(2) .
C12 C11 1.347(2) .
C12 C13 1.431(2) .
C12 C14 1.4758(19) .
C14 C16 1.381(2) .
C14 C15 1.386(2) .
C8 C7 1.392(2) .
C8 C9 1.4017(19) .
C8 C11 1.4496(19) .
C4 C3 1.491(2) .
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C11 H11 0.9300 .
C9 H9 0.9300 .
C3 C2 1.513(3) .
C3 H3A 0.9700 .
C3 H3B 0.9700 .
C15 C16 1.368(2) 2_557
C15 H15 0.9300 .
C7 C6 1.370(2) .
C7 H7 0.9300 .
C6 H6 0.9300 .
C16 C15 1.368(2) 2_557
C16 H16 0.9300 .
C13 N1 1.135(2) .
C2 C1 1.497(3) .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C1 H1A 0.9600 .
C1 H1B 0.9600 .
C1 H1C 0.9600 .
