#------------------------------------------------------------------------------
#$Date: 2016-03-24 01:32:20 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179534 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/03/4500358.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_4500358
loop_
_publ_author_name
'Nishiguchi, Noriaki'
'Sato, Tomohiro'
'Kinuta, Takafumi'
'Kuroda, Reiko'
'Matsubara, Yoshio'
'Imai, Yoshitane'
_publ_section_title
;
 Crystal Structures and Solid-State Optical Properties of Supramolecular
 Organic Fluorophore Composed of 1D Columnar Network Structure Consisting
 of Fluorescent 2-Naphthalenecarboxylic Acid
;
_journal_issue                   3
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              827
_journal_paper_doi               10.1021/cg101480x
_journal_volume                  11
_journal_year                    2011
_chemical_formula_sum            'C19 H19 N O2'
_chemical_formula_weight         293.35
_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                105.127(5)
_cell_angle_beta                 101.795(5)
_cell_angle_gamma                98.292(6)
_cell_formula_units_Z            2
_cell_length_a                   6.0867(19)
_cell_length_b                   10.568(3)
_cell_length_c                   12.745(4)
_cell_measurement_reflns_used    2601
_cell_measurement_temperature    115(2)
_cell_measurement_theta_max      27.88
_cell_measurement_theta_min      1.71
_cell_volume                     757.6(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      115(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.912
_diffrn_measurement_device_type  'Bruker APEX'
_diffrn_measurement_method       ω-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  0.0292
_diffrn_reflns_av_sigmaI/netI    0.0646
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4595
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.88
_diffrn_reflns_theta_min         1.71
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9917
_exptl_absorpt_correction_T_min  0.9596
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.512
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3268
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0861
_refine_ls_R_factor_gt           0.0708
_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)+(0.1281P)²+0.1908P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1877
_refine_ls_wR_factor_ref         0.2039
_reflns_number_gt                2601
_reflns_number_total             3268
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            cg101480x_si_001.cif
_cod_data_source_block           imai021_1
_cod_original_cell_volume        757.5(4)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4500358
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
C1 C 0.4223(3) 0.53188(19) 0.72254(17) 0.0166(4) Uani 1 1 d .
H1 H 0.2955 0.5365 0.7551 0.020 Uiso 1 1 calc R
C2 C 0.5998(3) 0.64122(19) 0.75536(16) 0.0171(4) Uani 1 1 d .
C3 C 0.7853(4) 0.63478(19) 0.70574(17) 0.0188(4) Uani 1 1 d .
H3 H 0.9089 0.7102 0.7284 0.023 Uiso 1 1 calc R
C4 C 0.7907(4) 0.5216(2) 0.62528(17) 0.0192(4) Uani 1 1 d .
H4 H 0.9167 0.5199 0.5920 0.023 Uiso 1 1 calc R
C5 C 0.6137(4) 0.2870(2) 0.51021(17) 0.0218(5) Uani 1 1 d .
H5 H 0.7377 0.2824 0.4756 0.026 Uiso 1 1 calc R
C6 C 0.4393(4) 0.1781(2) 0.48180(18) 0.0247(5) Uani 1 1 d .
H6 H 0.4431 0.0978 0.4278 0.030 Uiso 1 1 calc R
C7 C 0.2549(4) 0.1835(2) 0.53130(18) 0.0243(5) Uani 1 1 d .
H7 H 0.1344 0.1067 0.5104 0.029 Uiso 1 1 calc R
C8 C 0.2454(4) 0.2977(2) 0.60931(17) 0.0207(5) Uani 1 1 d .
H8 H 0.1188 0.3002 0.6422 0.025 Uiso 1 1 calc R
C9 C 0.4245(4) 0.41221(19) 0.64102(16) 0.0179(4) Uani 1 1 d .
C10 C 0.6108(4) 0.4067(2) 0.59085(17) 0.0186(4) Uani 1 1 d .
C11 C 0.5873(3) 0.76480(19) 0.84206(16) 0.0164(4) Uani 1 1 d .
O12 O 0.4208(2) 0.76220(13) 0.88448(12) 0.0207(4) Uani 1 1 d .
O13 O 0.7466(2) 0.86775(13) 0.86670(12) 0.0206(4) Uani 1 1 d .
C21 C 1.1476(4) 1.1678(2) 0.84889(17) 0.0182(4) Uani 1 1 d .
C22 C 0.9148(4) 1.1402(2) 0.79612(18) 0.0231(5) Uani 1 1 d .
H22 H 0.8350 1.0499 0.7603 0.028 Uiso 1 1 calc R
C23 C 0.7989(4) 1.2434(2) 0.79542(19) 0.0257(5) Uani 1 1 d .
H23 H 0.6403 1.2239 0.7583 0.031 Uiso 1 1 calc R
C24 C 0.9133(4) 1.3748(2) 0.84860(19) 0.0256(5) Uani 1 1 d .
H24 H 0.8335 1.4457 0.8483 0.031 Uiso 1 1 calc R
C25 C 1.1431(4) 1.4027(2) 0.90192(18) 0.0262(5) Uani 1 1 d .
H25 H 1.2215 1.4930 0.9389 0.031 Uiso 1 1 calc R
C26 C 1.2611(4) 1.2998(2) 0.90200(18) 0.0225(5) Uani 1 1 d .
H26 H 1.4201 1.3199 0.9385 0.027 Uiso 1 1 calc R
C27 C 1.2805(4) 1.05698(19) 0.84562(17) 0.0192(4) Uani 1 1 d .
H27 H 1.4471 1.0992 0.8782 0.023 Uiso 1 1 calc R
C28 C 1.2517(4) 0.9670(2) 0.72766(18) 0.0262(5) Uani 1 1 d .
H28A H 1.3490 0.9010 0.7300 0.039 Uiso 1 1 calc R
H28B H 1.2967 1.0213 0.6809 0.039 Uiso 1 1 calc R
H28C H 1.0908 0.9204 0.6958 0.039 Uiso 1 1 calc R
N27 N 1.2094(3) 0.97246(16) 0.91527(14) 0.0171(4) Uani 1 1 d .
H27A H 1.2370 1.0244 0.9878 0.026 Uiso 1 1 calc R
H27B H 1.2910 0.9065 0.9122 0.026 Uiso 1 1 calc R
H27C H 1.0570 0.9351 0.8882 0.026 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
C2 C1 C9 121.26(18)
C1 C2 C3 119.23(18)
C1 C2 C11 118.68(18)
C3 C2 C11 122.08(18)
C4 C3 C2 120.95(19)
C3 C4 C10 120.92(18)
C6 C5 C10 120.25(19)
C5 C6 C7 120.6(2)
C8 C7 C6 120.9(2)
C7 C8 C9 119.86(19)
C10 C9 C8 119.24(18)
C10 C9 C1 119.23(19)
C8 C9 C1 121.54(19)
C5 C10 C9 119.18(19)
C5 C10 C4 122.41(18)
C9 C10 C4 118.40(18)
O12 C11 O13 123.57(18)
O12 C11 C2 118.58(18)
O13 C11 C2 117.83(17)
C26 C21 C22 119.16(18)
C26 C21 C27 119.52(19)
C22 C21 C27 121.28(18)
C23 C22 C21 120.4(2)
C24 C23 C22 120.1(2)
C25 C24 C23 119.77(19)
C24 C25 C26 120.5(2)
C21 C26 C25 120.1(2)
N27 C27 C21 110.74(15)
N27 C27 C28 108.61(16)
C21 C27 C28 112.95(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.371(3)
C1 C9 1.415(3)
C2 C3 1.404(3)
C2 C11 1.497(3)
C3 C4 1.367(3)
C4 C10 1.417(3)
C5 C6 1.362(3)
C5 C10 1.411(3)
C6 C7 1.396(3)
C7 C8 1.366(3)
C8 C9 1.414(3)
C9 C10 1.412(3)
C11 O12 1.243(2)
C11 O13 1.271(2)
C21 C26 1.386(3)
C21 C22 1.391(3)
C21 C27 1.513(3)
C22 C23 1.383(3)
C23 C24 1.382(3)
C24 C25 1.376(3)
C25 C26 1.387(3)
C27 N27 1.494(2)
C27 C28 1.514(3)
