#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/31/4513130.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_4513130
loop_
_publ_author_name
'Hisamatsu, Shugo'
'Masu, Hyuma'
'Takahashi, Masahiro'
'Kishikawa, Keiki'
'Kohmoto, Shigeo'
_publ_section_title
;
 Pairwise Packing of Anthracene Fluorophore: Hydrogen-Bonding-Assisted
 Dimer Emission in Solid State
;
_journal_issue                   5
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2291
_journal_paper_doi               10.1021/acs.cgd.5b00081
_journal_volume                  15
_journal_year                    2015
_chemical_formula_moiety         'C24 H28 N2 O4'
_chemical_formula_sum            'C24 H28 N2 O4'
_chemical_formula_weight         408.48
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 125.0430(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   25.558(2)
_cell_length_b                   5.7536(6)
_cell_length_c                   18.2559(18)
_cell_measurement_reflns_used    2702
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.33
_cell_measurement_theta_min      2.73
_cell_volume                     2197.9(4)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_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  0.0143
_diffrn_reflns_av_sigmaI/netI    0.0183
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5840
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.40
_diffrn_reflns_theta_min         1.95
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9834
_exptl_absorpt_correction_T_min  0.9703
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2461
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0363
_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)+(0.0538P)²+0.9754P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.1023
_reflns_number_gt                2111
_reflns_number_total             2461
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg5b00081_si_002.cif
_cod_data_source_block           15(a120927his1)
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 
;
_cod_original_sg_symbol_H-M      'C2/c  '
_cod_database_code               4513130
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
C7 C -0.02645(5) 0.3673(2) 0.03670(7) 0.0248(2) Uani 1 1 d .
C8 C -0.03980(5) 0.3070(2) -0.04908(7) 0.0246(2) Uani 1 1 d .
C5 C 0.07871(5) 0.58810(19) 0.24897(7) 0.0234(2) Uani 1 1 d .
C6 C 0.01317(5) 0.5577(2) 0.08384(7) 0.0250(2) Uani 1 1 d .
C9 C -0.07778(5) 0.1063(2) -0.09374(7) 0.0292(3) Uani 1 1 d .
H9 H -0.0868 0.0638 -0.1502 0.035 Uiso 1 1 calc R
C12 C -0.05289(5) 0.2243(2) 0.07193(7) 0.0291(3) Uani 1 1 d .
H12 H -0.0450 0.2626 0.1281 0.035 Uiso 1 1 calc R
C4 C 0.18586(5) 0.4204(2) 0.32563(7) 0.0248(2) Uani 1 1 d .
C3 C 0.17489(6) 0.2472(2) 0.37829(9) 0.0357(3) Uani 1 1 d .
H3A H 0.1588 0.3290 0.4087 0.054 Uiso 1 1 calc R
H3B H 0.2153 0.1697 0.4227 0.054 Uiso 1 1 calc R
H3C H 0.1435 0.1311 0.3374 0.054 Uiso 1 1 calc R
C11 C -0.08900(6) 0.0353(2) 0.02679(8) 0.0321(3) Uani 1 1 d .
H11 H -0.1061 -0.0568 0.0516 0.039 Uiso 1 1 calc R
C10 C -0.10144(6) -0.0258(2) -0.05718(8) 0.0322(3) Uani 1 1 d .
H10 H -0.1264 -0.1594 -0.0880 0.039 Uiso 1 1 calc R
C1 C 0.21881(6) 0.3043(2) 0.28759(8) 0.0336(3) Uani 1 1 d .
H1A H 0.1950 0.1645 0.2544 0.050 Uiso 1 1 calc R
H1B H 0.2625 0.2611 0.3366 0.050 Uiso 1 1 calc R
H1C H 0.2202 0.4123 0.2472 0.050 Uiso 1 1 calc R
C2 C 0.22285(6) 0.6319(2) 0.38024(9) 0.0366(3) Uani 1 1 d .
H2A H 0.2268 0.7416 0.3426 0.055 Uiso 1 1 calc R
H2B H 0.2655 0.5844 0.4308 0.055 Uiso 1 1 calc R
H2C H 0.2002 0.7067 0.4027 0.055 Uiso 1 1 calc R
N1 N 0.02405(4) 0.62109(18) 0.16722(6) 0.0270(2) Uani 1 1 d .
H1 H -0.0078 0.6877 0.1651 0.032 Uiso 1 1 calc R
O1 O 0.08489(4) 0.64256(15) 0.31833(5) 0.0290(2) Uani 1 1 d .
O2 O 0.12407(3) 0.49027(15) 0.24379(5) 0.0271(2) 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C6 C7 C12 122.32(10) . .
C6 C7 C8 119.49(10) . .
C12 C7 C8 118.17(10) . .
C6 C8 C9 122.61(10) 5_565 .
C6 C8 C7 118.96(10) 5_565 .
C9 C8 C7 118.38(10) . .
O1 C5 O2 125.29(10) . .
O1 C5 N1 123.03(10) . .
O2 C5 N1 111.68(9) . .
C7 C6 C8 121.54(10) . 5_565
C7 C6 N1 118.91(10) . .
C8 C6 N1 119.48(10) 5_565 .
C10 C9 C8 121.34(11) . .
C10 C9 H9 119.3 . .
C8 C9 H9 119.3 . .
C11 C12 C7 121.35(11) . .
C11 C12 H12 119.3 . .
C7 C12 H12 119.3 . .
O2 C4 C2 110.42(9) . .
O2 C4 C3 109.90(9) . .
C2 C4 C3 112.56(10) . .
O2 C4 C1 102.05(8) . .
C2 C4 C1 110.75(10) . .
C3 C4 C1 110.67(10) . .
C4 C3 H3A 109.5 . .
C4 C3 H3B 109.5 . .
H3A C3 H3B 109.5 . .
C4 C3 H3C 109.5 . .
H3A C3 H3C 109.5 . .
H3B C3 H3C 109.5 . .
C12 C11 C10 120.45(11) . .
C12 C11 H11 119.8 . .
C10 C11 H11 119.8 . .
C9 C10 C11 120.30(12) . .
C9 C10 H10 119.8 . .
C11 C10 H10 119.8 . .
C4 C1 H1A 109.5 . .
C4 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
C4 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
C4 C2 H2A 109.5 . .
C4 C2 H2B 109.5 . .
H2A C2 H2B 109.5 . .
C4 C2 H2C 109.5 . .
H2A C2 H2C 109.5 . .
H2B C2 H2C 109.5 . .
C5 N1 C6 125.93(9) . .
C5 N1 H1 117.0 . .
C6 N1 H1 117.0 . .
C5 O2 C4 120.61(8) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C7 C6 1.4019(17) .
C7 C12 1.4304(16) .
C7 C8 1.4408(14) .
C8 C6 1.4027(16) 5_565
C8 C9 1.4254(17) .
C5 O1 1.2235(13) .
C5 O2 1.3400(13) .
C5 N1 1.3493(14) .
C6 C8 1.4027(16) 5_565
C6 N1 1.4289(13) .
C9 C10 1.3608(17) .
C9 H9 0.9500 .
C12 C11 1.3566(18) .
C12 H12 0.9500 .
C4 O2 1.4758(12) .
C4 C2 1.5117(16) .
C4 C3 1.5185(16) .
C4 C1 1.5197(16) .
C3 H3A 0.9800 .
C3 H3B 0.9800 .
C3 H3C 0.9800 .
C11 C10 1.4195(17) .
C11 H11 0.9500 .
C10 H10 0.9500 .
C1 H1A 0.9800 .
C1 H1B 0.9800 .
C1 H1C 0.9800 .
C2 H2A 0.9800 .
C2 H2B 0.9800 .
C2 H2C 0.9800 .
N1 H1 0.8800 .
