#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/43/1504364.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_1504364
loop_
_publ_author_name
'Liu, Y.'
'Tao, X.'
'Wang, F.'
'Dang, X.'
'Zou, D.'
'Ren, Y.'
'Jiang, M.'
_publ_section_title
;
 Aggregation-Induced Emissions of Fluorenonearylamine Derivatives: A New
 Kind of Materials for Nondoped Red Organic Light-Emitting Diodes
;
_journal_issue                   10
_journal_name_full               'Journal of Physical Chemistry C'
_journal_page_first              3975
_journal_paper_doi               10.1021/jp7117373
_journal_volume                  112
_journal_year                    2008
_chemical_formula_moiety         'C31 H21 N O'
_chemical_formula_sum            'C31 H21 N O'
_chemical_formula_weight         423.49
_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                90.000(5)
_cell_angle_beta                 115.041(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            4
_cell_length_a                   18.807(5)
_cell_length_b                   8.584(5)
_cell_length_c                   16.555(5)
_cell_measurement_reflns_used    1882
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.31
_cell_measurement_theta_min      3.21
_cell_volume                     2421.4(17)
_computing_cell_refinement       'APEX2 Software Suite (Bruker,2005)'
_computing_data_collection       'APEX2 Software Suite (Bruker,2005)'
_computing_data_reduction        'APEX2 Software Suite (Bruker,2005)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'WINGX (Farrugia,1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare,1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type
'Bruker APEX2 CCD area-detector diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0600
_diffrn_reflns_av_sigmaI/netI    0.0694
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18366
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         1.19
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  0.9956
_exptl_absorpt_correction_T_min  0.9689
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'APEX2 Software Suite (Bruker,2005)'
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.06
_refine_diff_density_max         2.888
_refine_diff_density_min         -0.699
_refine_diff_density_rms         0.256
_refine_ls_extinction_coef       0.045(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.496
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         5484
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.496
_refine_ls_R_factor_all          0.2410
_refine_ls_R_factor_gt           0.1645
_refine_ls_shift/su_max          0.035
_refine_ls_shift/su_mean         0.006
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4273
_refine_ls_wR_factor_ref         0.4718
_reflns_number_gt                2549
_reflns_number_total             5484
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jp7117373-file002.cif
_cod_data_source_block           liuyang
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P2(1)/c  '
_cod_database_code               1504364
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
C1 C 0.6603(4) 1.7361(7) 1.0467(4) 0.0568(16) Uani 1 1 d .
H1 H 0.6997 1.7907 1.0924 0.068 Uiso 1 1 calc R
C2 C 0.6059(4) 1.8167(7) 0.9758(5) 0.0599(17) Uani 1 1 d .
H2 H 0.6090 1.9247 0.9745 0.072 Uiso 1 1 calc R
C3 C 0.5460(3) 1.7395(7) 0.9056(4) 0.0553(16) Uani 1 1 d .
H3 H 0.5102 1.7940 0.8568 0.066 Uiso 1 1 calc R
C4 C 0.5416(3) 1.5782(6) 0.9111(3) 0.0428(13) Uani 1 1 d .
C5 C 0.5973(3) 1.4972(7) 0.9830(4) 0.0461(14) Uani 1 1 d .
C6 C 0.6579(3) 1.5753(8) 1.0517(4) 0.0576(17) Uani 1 1 d .
H6 H 0.6954 1.5211 1.0994 0.069 Uiso 1 1 calc R
C7 C 0.5804(3) 1.3310(7) 0.9712(4) 0.0479(14) Uani 1 1 d .
C8 C 0.5069(3) 1.3148(6) 0.8869(3) 0.0436(13) Uani 1 1 d .
C9 C 0.4851(3) 1.4641(6) 0.8502(4) 0.0448(13) Uani 1 1 d .
C10 C 0.4189(3) 1.4808(7) 0.7708(4) 0.0491(14) Uani 1 1 d .
H10 H 0.4049 1.5779 0.7436 0.059 Uiso 1 1 calc R
C11 C 0.3735(3) 1.3497(7) 0.7321(4) 0.0504(15) Uani 1 1 d .
H11 H 0.3289 1.3612 0.6788 0.061 Uiso 1 1 calc R
C12 C 0.3926(3) 1.2019(7) 0.7703(3) 0.0431(13) Uani 1 1 d .
C13 C 0.4630(3) 1.1859(7) 0.8488(4) 0.0457(14) Uani 1 1 d .
H13 H 0.4791 1.0882 0.8743 0.055 Uiso 1 1 calc R
C14 C 0.3420(3) 1.0660(7) 0.7327(4) 0.0464(14) Uani 1 1 d .
C15 C 0.2913(3) 1.0497(7) 0.6425(4) 0.0540(15) Uani 1 1 d .
H15 H 0.2903 1.1276 0.6029 0.065 Uiso 1 1 calc R
C16 C 0.2428(3) 0.9222(7) 0.6099(4) 0.0523(15) Uani 1 1 d .
H16 H 0.2098 0.9163 0.5494 0.063 Uiso 1 1 calc R
C17 C 0.2428(3) 0.8040(8) 0.6658(4) 0.0544(16) Uani 1 1 d .
C18 C 0.2937(3) 0.8158(7) 0.7569(4) 0.0500(15) Uani 1 1 d .
H18 H 0.2959 0.7353 0.7955 0.060 Uiso 1 1 calc R
C19 C 0.3390(3) 0.9420(7) 0.7886(4) 0.0481(14) Uani 1 1 d .
H19 H 0.3699 0.9489 0.8496 0.058 Uiso 1 1 calc R
C20 C 0.1697(3) 0.5805(8) 0.6888(4) 0.0608(17) Uani 1 1 d .
C21 C 0.1429(4) 0.6524(9) 0.7456(4) 0.0660(18) Uani 1 1 d .
H21 H 0.1396 0.7604 0.7467 0.079 Uiso 1 1 calc R
C22 C 0.1212(4) 0.5632(12) 0.7999(5) 0.080(2) Uani 1 1 d .
H22 H 0.1043 0.6116 0.8390 0.096 Uiso 1 1 calc R
C23 C 0.1240(6) 0.4055(14) 0.7978(6) 0.110(4) Uani 1 1 d .
H23 H 0.1091 0.3468 0.8353 0.132 Uiso 1 1 calc R
C24 C 0.1489(5) 0.3311(11) 0.7398(6) 0.089(3) Uani 1 1 d .
H24 H 0.1502 0.2230 0.7376 0.107 Uiso 1 1 calc R
C25 C 0.1712(4) 0.4182(9) 0.6868(5) 0.073(2) Uani 1 1 d .
H25 H 0.1879 0.3688 0.6479 0.088 Uiso 1 1 calc R
C26 C 0.1694(3) 0.6206(7) 0.5438(4) 0.0542(16) Uani 1 1 d .
C27 C 0.0902(4) 0.5840(9) 0.4928(4) 0.0675(19) Uani 1 1 d .
H27 H 0.0543 0.5943 0.5174 0.081 Uiso 1 1 calc R
C28 C 0.0656(5) 0.5331(10) 0.4067(5) 0.081(2) Uani 1 1 d .
H28 H 0.0133 0.5063 0.3738 0.098 Uiso 1 1 calc R
C29 C 0.1163(5) 0.5216(9) 0.3693(5) 0.082(2) Uani 1 1 d .
H29 H 0.0985 0.4887 0.3105 0.098 Uiso 1 1 calc R
C30 C 0.1956(5) 0.5584(8) 0.4179(5) 0.074(2) Uani 1 1 d .
H30 H 0.2304 0.5511 0.3915 0.088 Uiso 1 1 calc R
C31 C 0.2214(3) 0.6054(8) 0.5047(4) 0.0574(16) Uani 1 1 d .
H31 H 0.2743 0.6274 0.5379 0.069 Uiso 1 1 calc R
N1 N 0.1941(3) 0.6689(6) 0.6329(3) 0.0631(15) Uani 1 1 d .
O1 O 0.6172(2) 1.2219(5) 1.0206(3) 0.0628(13) Uani 1 1 d .
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
C2 C1 C6 121.4(5)
C2 C1 H1 119.3
C6 C1 H1 119.3
C1 C2 C3 121.3(6)
C1 C2 H2 119.4
C3 C2 H2 119.4
C4 C3 C2 117.8(6)
C4 C3 H3 121.1
C2 C3 H3 121.1
C3 C4 C5 120.6(5)
C3 C4 C9 131.1(5)
C5 C4 C9 108.3(5)
C4 C5 C6 121.1(5)
C4 C5 C7 109.4(5)
C6 C5 C7 129.6(6)
C1 C6 C5 117.8(6)
C1 C6 H6 121.1
C5 C6 H6 121.1
O1 C7 C5 128.3(5)
O1 C7 C8 125.5(5)
C5 C7 C8 106.2(5)
C13 C8 C9 122.1(5)
C13 C8 C7 130.2(5)
C9 C8 C7 107.7(5)
C10 C9 C8 119.2(5)
C10 C9 C4 132.5(5)
C8 C9 C4 108.3(5)
C9 C10 C11 118.9(5)
C9 C10 H10 120.6
C11 C10 H10 120.6
C10 C11 C12 122.4(5)
C10 C11 H11 118.8
C12 C11 H11 118.8
C11 C12 C13 117.8(5)
C11 C12 C14 122.3(5)
C13 C12 C14 119.9(5)
C8 C13 C12 119.6(5)
C8 C13 H13 120.2
C12 C13 H13 120.2
C15 C14 C19 115.0(5)
C15 C14 C12 124.0(5)
C19 C14 C12 121.0(5)
C16 C15 C14 122.4(6)
C16 C15 H15 118.8
C14 C15 H15 118.8
C17 C16 C15 120.8(5)
C17 C16 H16 119.6
C15 C16 H16 119.6
C16 C17 C18 118.3(5)
C16 C17 N1 121.6(5)
C18 C17 N1 120.0(6)
C19 C18 C17 120.6(6)
C19 C18 H18 119.7
C17 C18 H18 119.7
C18 C19 C14 122.8(5)
C18 C19 H19 118.6
C14 C19 H19 118.6
C21 C20 C25 118.5(7)
C21 C20 N1 121.1(7)
C25 C20 N1 120.4(7)
C22 C21 C20 119.5(8)
C22 C21 H21 120.3
C20 C21 H21 120.3
C23 C22 C21 121.1(8)
C23 C22 H22 119.5
C21 C22 H22 119.5
C22 C23 C24 120.3(8)
C22 C23 H23 119.9
C24 C23 H23 119.8
C25 C24 C23 119.0(9)
C25 C24 H24 120.5
C23 C24 H24 120.5
C24 C25 C20 121.6(8)
C24 C25 H25 119.2
C20 C25 H25 119.2
C31 C26 C27 118.5(5)
C31 C26 N1 122.1(5)
C27 C26 N1 119.5(6)
C28 C27 C26 120.2(7)
C28 C27 H27 119.9
C26 C27 H27 119.9
C29 C28 C27 120.7(7)
C29 C28 H28 119.7
C27 C28 H28 119.7
C28 C29 C30 120.8(7)
C28 C29 H29 119.6
C30 C29 H29 119.6
C31 C30 C29 119.2(7)
C31 C30 H30 120.4
C29 C30 H30 120.4
C30 C31 C26 120.7(6)
C30 C31 H31 119.6
C26 C31 H31 119.6
C26 N1 C20 118.2(5)
C26 N1 C17 120.6(5)
C20 N1 C17 121.2(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.374(9)
C1 C6 1.385(9)
C1 H1 0.9300
C2 C3 1.397(8)
C2 H2 0.9300
C3 C4 1.392(8)
C3 H3 0.9300
C4 C5 1.394(8)
C4 C9 1.483(7)
C5 C6 1.395(8)
C5 C7 1.457(8)
C6 H6 0.9300
C7 O1 1.243(7)
C7 C8 1.497(8)
C8 C13 1.365(7)
C8 C9 1.404(8)
C9 C10 1.383(7)
C10 C11 1.394(8)
C10 H10 0.9300
C11 C12 1.395(8)
C11 H11 0.9300
C12 C13 1.415(7)
C12 C14 1.468(8)
C13 H13 0.9300
C14 C15 1.398(7)
C14 C19 1.426(8)
C15 C16 1.380(8)
C15 H15 0.9300
C16 C17 1.374(8)
C16 H16 0.9300
C17 C18 1.407(8)
C17 N1 1.434(8)
C18 C19 1.341(8)
C18 H18 0.9300
C19 H19 0.9300
C20 C21 1.386(9)
C20 C25 1.394(10)
C20 N1 1.414(8)
C21 C22 1.368(10)
C21 H21 0.9300
C22 C23 1.356(13)
C22 H22 0.9300
C23 C24 1.389(14)
C23 H23 0.9300
C24 C25 1.347(11)
C24 H24 0.9300
C25 H25 0.9300
C26 C31 1.389(8)
C26 C27 1.402(8)
C26 N1 1.409(7)
C27 C28 1.371(9)
C27 H27 0.9300
C28 C29 1.341(11)
C28 H28 0.9300
C29 C30 1.399(11)
C29 H29 0.9300
C30 C31 1.369(9)
C30 H30 0.9300
C31 H31 0.9300
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
C6 C1 C2 C3 -0.3(10)
C1 C2 C3 C4 2.0(9)
C2 C3 C4 C5 -2.4(8)
C2 C3 C4 C9 178.4(5)
C3 C4 C5 C6 1.1(8)
C9 C4 C5 C6 -179.5(5)
C3 C4 C5 C7 -178.5(5)
C9 C4 C5 C7 0.9(6)
C2 C1 C6 C5 -1.1(9)
C4 C5 C6 C1 0.7(9)
C7 C5 C6 C1 -179.8(6)
C4 C5 C7 O1 179.3(6)
C6 C5 C7 O1 -0.3(10)
C4 C5 C7 C8 -2.2(6)
C6 C5 C7 C8 178.3(6)
O1 C7 C8 C13 3.8(10)
C5 C7 C8 C13 -174.9(5)
O1 C7 C8 C9 -178.7(5)
C5 C7 C8 C9 2.6(6)
C13 C8 C9 C10 -3.0(8)
C7 C8 C9 C10 179.3(5)
C13 C8 C9 C4 175.6(5)
C7 C8 C9 C4 -2.2(6)
C3 C4 C9 C10 -1.6(10)
C5 C4 C9 C10 179.1(6)
C3 C4 C9 C8 -179.9(6)
C5 C4 C9 C8 0.8(6)
C8 C9 C10 C11 3.4(8)
C4 C9 C10 C11 -174.8(5)
C9 C10 C11 C12 -0.4(9)
C10 C11 C12 C13 -3.1(8)
C10 C11 C12 C14 175.8(5)
C9 C8 C13 C12 -0.6(8)
C7 C8 C13 C12 176.6(5)
C11 C12 C13 C8 3.6(8)
C14 C12 C13 C8 -175.4(5)
C11 C12 C14 C15 27.8(8)
C13 C12 C14 C15 -153.3(5)
C11 C12 C14 C19 -149.5(6)
C13 C12 C14 C19 29.4(8)
C19 C14 C15 C16 -0.7(8)
C12 C14 C15 C16 -178.1(6)
C14 C15 C16 C17 -0.3(9)
C15 C16 C17 C18 -0.4(9)
C15 C16 C17 N1 -178.6(6)
C16 C17 C18 C19 2.3(9)
N1 C17 C18 C19 -179.4(5)
C17 C18 C19 C14 -3.5(9)
C15 C14 C19 C18 2.6(8)
C12 C14 C19 C18 -179.9(5)
C25 C20 C21 C22 2.2(10)
N1 C20 C21 C22 -178.7(6)
C20 C21 C22 C23 -1.4(11)
C21 C22 C23 C24 -0.1(13)
C22 C23 C24 C25 0.8(13)
C23 C24 C25 C20 0.0(12)
C21 C20 C25 C24 -1.5(10)
N1 C20 C25 C24 179.4(6)
C31 C26 C27 C28 0.7(10)
N1 C26 C27 C28 -178.4(7)
C26 C27 C28 C29 -1.8(12)
C27 C28 C29 C30 1.2(13)
C28 C29 C30 C31 0.6(11)
C29 C30 C31 C26 -1.7(10)
C27 C26 C31 C30 1.1(10)
N1 C26 C31 C30 -179.9(6)
C31 C26 N1 C20 -131.1(7)
C27 C26 N1 C20 47.9(9)
C31 C26 N1 C17 48.8(9)
C27 C26 N1 C17 -132.3(7)
C21 C20 N1 C26 -136.2(6)
C25 C20 N1 C26 42.9(9)
C21 C20 N1 C17 44.0(9)
C25 C20 N1 C17 -136.9(6)
C16 C17 N1 C26 25.5(9)
C18 C17 N1 C26 -152.7(6)
C16 C17 N1 C20 -154.7(6)
C18 C17 N1 C20 27.1(9)
