#------------------------------------------------------------------------------
#$Date: 2016-03-26 18:13:32 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180417 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/86/7208621.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_7208621
loop_
_publ_author_name
'Xu, Zhenzhen'
'Liao, Qing'
'Wu, Yishi'
'Ren, Wenlu'
'Li, Wei'
'Liu, Libing'
'Wang, Shu'
'Gu, Zhanjun'
'Zhang, Haoli'
'Fu, Hongbing'
_publ_section_title
;
 Water-miscible organic J-aggregate nanoparticles as efficient two-photon
 fluorescent nano-probes for bio-imaging
;
_journal_issue                   34
_journal_name_full               'Journal of Materials Chemistry'
_journal_page_first              17737
_journal_paper_doi               10.1039/c2jm33081d
_journal_volume                  22
_journal_year                    2012
_chemical_formula_moiety         'C26 H20 N2 O2'
_chemical_formula_sum            'C26 H20 N2 O2'
_chemical_formula_weight         392.44
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 104.292(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.5110(15)
_cell_length_b                   14.954(3)
_cell_length_c                   8.4748(15)
_cell_measurement_reflns_used    425
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.22
_cell_measurement_theta_min      3.12
_cell_volume                     1045.2(3)
_computing_cell_refinement       'Rapid Auto Ver 2.30(Rigaku 1998)'
_computing_data_collection       'Rapid Auto Ver 2.30(Rigaku 1998)'
_computing_data_reduction        'Rapid Auto Ver 2.30(Rigaku 1998)'
_computing_molecular_graphics    'XP in Siemens SHELXTL (Sheldrick, 1994)'
_computing_publication_material  'SHELX97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku raxis Rapid IP Area Detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_av_sigmaI/netI    0.0438
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9978
_diffrn_reflns_theta_full        68.10
_diffrn_reflns_theta_max         68.10
_diffrn_reflns_theta_min         5.36
_exptl_absorpt_coefficient_mu    0.632
_exptl_absorpt_correction_T_max  0.8428
_exptl_absorpt_correction_T_min  0.6317
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS by T.Higashi Jun 3, 2003'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.120
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.040(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         1905
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0490
_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)+(0.0411P)²+0.2286P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1121
_refine_ls_wR_factor_ref         0.1224
_reflns_number_gt                1428
_reflns_number_total             1905
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2jm33081d.txt
_cod_data_source_block           a
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7208621
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
O1 O 0.99013(18) 0.82116(9) 0.07603(17) 0.0706(5) Uani 1 1 d .
N1 N 1.5308(3) 1.14234(14) -0.9770(2) 0.0870(7) Uani 1 1 d .
C1 C 1.4729(2) 1.12059(15) -0.8748(3) 0.0646(6) Uani 1 1 d .
C2 C 1.4002(2) 1.09403(14) -0.7459(2) 0.0541(5) Uani 1 1 d .
C3 C 1.3589(2) 1.00597(14) -0.7299(2) 0.0544(5) Uani 1 1 d .
H3A H 1.3782 0.9622 -0.8041 0.065 Uiso 1 1 calc R
C4 C 1.2896(2) 0.98186(13) -0.6057(2) 0.0528(5) Uani 1 1 d .
H4A H 1.2609 0.9211 -0.5959 0.063 Uiso 1 1 calc R
C5 C 1.2605(2) 1.04386(13) -0.4942(2) 0.0493(5) Uani 1 1 d .
C6 C 1.3041(2) 1.13243(14) -0.5123(2) 0.0605(6) Uani 1 1 d .
H6A H 1.2864 1.1762 -0.4373 0.073 Uiso 1 1 calc R
C7 C 1.3721(3) 1.15751(14) -0.6366(2) 0.0631(6) Uani 1 1 d .
H7A H 1.3999 1.2183 -0.6477 0.076 Uiso 1 1 calc R
C8 C 1.1872(2) 1.01396(13) -0.3643(2) 0.0536(5) Uani 1 1 d .
H8A H 1.1616 0.9521 -0.3641 0.064 Uiso 1 1 calc R
C9 C 1.1520(2) 1.06261(13) -0.2469(2) 0.0524(5) Uani 1 1 d .
H9A H 1.1783 1.1244 -0.2447 0.063 Uiso 1 1 calc R
C10 C 1.0767(2) 1.03010(13) -0.1206(2) 0.0474(5) Uani 1 1 d .
C11 C 1.0706(2) 0.93971(12) -0.0833(2) 0.0502(5) Uani 1 1 d .
H11A H 1.1194 0.8974 -0.1401 0.060 Uiso 1 1 calc R
C12 C 0.9961(2) 0.90977(12) 0.0335(2) 0.0499(5) Uani 1 1 d .
C13 C 1.0723(3) 0.75807(15) 0.0018(3) 0.0907(8) Uani 1 1 d .
H13A H 1.0591 0.6983 0.0440 0.136 Uiso 1 1 calc R
H13B H 1.1878 0.7732 0.0262 0.136 Uiso 1 1 calc R
H13C H 1.0270 0.7589 -0.1163 0.136 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C12 O1 C13 118.18(16) . .
N1 C1 C2 179.5(2) . .
C3 C2 C7 119.85(18) . .
C3 C2 C1 120.43(18) . .
C7 C2 C1 119.71(19) . .
C4 C3 C2 119.57(18) . .
C4 C3 H3A 120.2 . .
C2 C3 H3A 120.2 . .
C3 C4 C5 121.85(18) . .
C3 C4 H4A 119.1 . .
C5 C4 H4A 119.1 . .
C4 C5 C6 117.56(17) . .
C4 C5 C8 119.25(17) . .
C6 C5 C8 123.19(17) . .
C7 C6 C5 121.18(19) . .
C7 C6 H6A 119.4 . .
C5 C6 H6A 119.4 . .
C6 C7 C2 119.99(19) . .
C6 C7 H7A 120.0 . .
C2 C7 H7A 120.0 . .
C9 C8 C5 127.92(19) . .
C9 C8 H8A 116.0 . .
C5 C8 H8A 116.0 . .
C8 C9 C10 126.08(19) . .
C8 C9 H9A 117.0 . .
C10 C9 H9A 117.0 . .
C11 C10 C12 117.22(16) . 3_775
C11 C10 C9 122.52(17) . .
C12 C10 C9 120.25(17) 3_775 .
C12 C11 C10 121.94(17) . .
C12 C11 H11A 119.0 . .
C10 C11 H11A 119.0 . .
C11 C12 O1 123.68(17) . .
C11 C12 C10 120.84(17) . 3_775
O1 C12 C10 115.46(16) . 3_775
O1 C13 H13A 109.5 . .
O1 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
O1 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C12 1.377(2) .
O1 C13 1.411(2) .
N1 C1 1.144(2) .
C1 C2 1.438(3) .
C2 C3 1.378(3) .
C2 C7 1.388(3) .
C3 C4 1.375(2) .
C3 H3A 0.9500 .
C4 C5 1.389(2) .
C4 H4A 0.9500 .
C5 C6 1.394(3) .
C5 C8 1.464(2) .
C6 C7 1.373(2) .
C6 H6A 0.9500 .
C7 H7A 0.9500 .
C8 C9 1.325(2) .
C8 H8A 0.9500 .
C9 C10 1.460(2) .
C9 H9A 0.9500 .
C10 C11 1.392(2) .
C10 C12 1.401(2) 3_775
C11 C12 1.376(2) .
C11 H11A 0.9500 .
C12 C10 1.401(2) 3_775
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
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
N1 C1 C2 C3 177(100) . .
N1 C1 C2 C7 -3(29) . .
C7 C2 C3 C4 0.2(3) . .
C1 C2 C3 C4 179.91(17) . .
C2 C3 C4 C5 -0.4(3) . .
C3 C4 C5 C6 0.0(3) . .
C3 C4 C5 C8 -179.71(17) . .
C4 C5 C6 C7 0.5(3) . .
C8 C5 C6 C7 -179.76(18) . .
C5 C6 C7 C2 -0.7(3) . .
C3 C2 C7 C6 0.3(3) . .
C1 C2 C7 C6 -179.38(19) . .
C4 C5 C8 C9 179.28(19) . .
C6 C5 C8 C9 -0.5(3) . .
C5 C8 C9 C10 179.15(17) . .
C8 C9 C10 C11 17.1(3) . .
C8 C9 C10 C12 -161.62(19) . 3_775
C12 C10 C11 C12 0.3(3) 3_775 .
C9 C10 C11 C12 -178.51(16) . .
C10 C11 C12 O1 -178.75(17) . .
C10 C11 C12 C10 -0.3(3) . 3_775
C13 O1 C12 C11 3.4(3) . .
C13 O1 C12 C10 -175.12(19) . 3_775
