#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:53:29 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180403 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/72/7207220.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_7207220
loop_
_publ_author_name
'Kobayashi, Yuhei'
'Kinuta, Takafumi'
'Sato, Tomohiro'
'Harada, Takunori'
'Kuroda, Reiko'
'Matsubara, Yoshio'
'Imai, Yoshitane'
_publ_section_title
;
 Polymorphic supramolecular organic fluorophore composed of
 2-naphthalenecarboxylic acid and benzylamine
;
_journal_issue                   4
_journal_name_full               CrystEngComm
_journal_page_first              1468
_journal_paper_doi               10.1039/c1ce06262j
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C18 H17 N O2'
_chemical_formula_weight         279.33
_chemical_name_systematic
;
?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.2850(3)
_cell_length_b                   8.3874(4)
_cell_length_c                   27.2578(13)
_cell_measurement_reflns_used    1863
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      27.88
_cell_measurement_theta_min      1.49
_cell_volume                     1436.89(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      130(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'CCD area detector'
_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  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0170
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            12758
_diffrn_reflns_theta_full        27.88
_diffrn_reflns_theta_max         27.88
_diffrn_reflns_theta_min         1.49
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9834
_exptl_absorpt_correction_T_min  0.9631
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   10(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         1952
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0337
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0544P)²+0.2109P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0883
_refine_ls_wR_factor_ref         0.0896
_reflns_number_gt                1863
_reflns_number_total             1952
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ce06262j.txt
_cod_data_source_block           imai813V2_1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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)2(1)2(1)
_cod_database_code               7207220
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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 0.8962(2) -0.02622(19) 0.16737(5) 0.0186(3) Uani 1 1 d .
H1 H 1.0342 0.0177 0.1719 0.022 Uiso 1 1 calc R
C2 C 0.7990(2) -0.01322(18) 0.12253(5) 0.0172(3) Uani 1 1 d .
C3 C 0.5931(2) -0.07757(18) 0.11571(5) 0.0191(3) Uani 1 1 d .
H3 H 0.5245 -0.0666 0.0848 0.023 Uiso 1 1 calc R
C4 C 0.4919(3) -0.15540(19) 0.15313(5) 0.0210(3) Uani 1 1 d .
H4 H 0.3542 -0.1988 0.1479 0.025 Uiso 1 1 calc R
C5 C 0.4916(3) -0.2546(2) 0.23896(5) 0.0258(4) Uani 1 1 d .
H5 H 0.3558 -0.3020 0.2343 0.031 Uiso 1 1 calc R
C6 C 0.5904(3) -0.2663(2) 0.28353(6) 0.0288(4) Uani 1 1 d .
H6 H 0.5233 -0.3226 0.3095 0.035 Uiso 1 1 calc R
C7 C 0.7917(3) -0.1953(2) 0.29120(6) 0.0267(4) Uani 1 1 d .
H7 H 0.8575 -0.2025 0.3225 0.032 Uiso 1 1 calc R
C8 C 0.8922(3) -0.11647(19) 0.25406(5) 0.0229(3) Uani 1 1 d .
H8 H 1.0278 -0.0698 0.2596 0.027 Uiso 1 1 calc R
C9 C 0.7945(2) -0.10389(18) 0.20705(5) 0.0183(3) Uani 1 1 d .
C10 C 0.5901(3) -0.17210(19) 0.19967(5) 0.0194(3) Uani 1 1 d .
C11 C 0.9154(2) 0.06451(18) 0.08028(5) 0.0186(3) Uani 1 1 d .
O12 O 1.10781(18) 0.09470(16) 0.08577(4) 0.0286(3) Uani 1 1 d .
O13 O 0.80954(17) 0.09161(14) 0.04164(4) 0.0219(2) Uani 1 1 d .
C21 C 1.1603(2) 0.0305(2) -0.07852(5) 0.0213(3) Uani 1 1 d .
C22 C 1.2175(3) -0.0421(2) -0.03465(6) 0.0243(3) Uani 1 1 d .
H22 H 1.1320 -0.0273 -0.0063 0.029 Uiso 1 1 calc R
C23 C 1.3985(3) -0.1359(2) -0.03204(6) 0.0281(4) Uani 1 1 d .
H23 H 1.4380 -0.1833 -0.0017 0.034 Uiso 1 1 calc R
C24 C 1.5225(3) -0.1611(2) -0.07342(6) 0.0270(4) Uani 1 1 d .
H24 H 1.6454 -0.2268 -0.0716 0.032 Uiso 1 1 calc R
C25 C 1.4658(3) -0.0900(2) -0.11727(6) 0.0267(4) Uani 1 1 d .
H25 H 1.5499 -0.1068 -0.1458 0.032 Uiso 1 1 calc R
C26 C 1.2861(3) 0.0061(2) -0.11974(6) 0.0248(3) Uani 1 1 d .
H26 H 1.2489 0.0556 -0.1499 0.030 Uiso 1 1 calc R
C27 C 0.9601(3) 0.1279(2) -0.08313(6) 0.0261(4) Uani 1 1 d .
H27A H 0.9632 0.1857 -0.1148 0.031 Uiso 1 1 calc R
H27B H 0.8364 0.0549 -0.0838 0.031 Uiso 1 1 calc R
N28 N 0.9301(2) 0.24488(16) -0.04297(4) 0.0198(3) Uani 1 1 d .
H28A H 0.9082 0.1921 -0.0142 0.030 Uiso 1 1 calc R
H28B H 0.8154 0.3074 -0.0497 0.030 Uiso 1 1 calc R
H28C H 1.0483 0.3070 -0.0403 0.030 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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 121.14(14)
C1 C2 C3 119.63(13)
C1 C2 C11 119.87(13)
C3 C2 C11 120.46(13)
C4 C3 C2 120.65(14)
C3 C4 C10 120.78(14)
C6 C5 C10 120.51(16)
C5 C6 C7 120.49(15)
C8 C7 C6 120.56(15)
C7 C8 C9 120.27(16)
C1 C9 C10 119.05(13)
C1 C9 C8 121.82(14)
C10 C9 C8 119.14(14)
C5 C10 C4 122.28(14)
C5 C10 C9 119.00(14)
C4 C10 C9 118.72(13)
O12 C11 O13 125.02(14)
O12 C11 C2 117.78(14)
O13 C11 C2 117.19(13)
C22 C21 C26 118.98(15)
C22 C21 C27 121.74(14)
C26 C21 C27 119.21(14)
C23 C22 C21 120.38(15)
C22 C23 C24 120.42(15)
C25 C24 C23 119.49(16)
C24 C25 C26 120.12(15)
C21 C26 C25 120.59(15)
N28 C27 C21 113.83(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.3706(19)
C1 C9 1.415(2)
C2 C3 1.414(2)
C2 C11 1.5118(19)
C3 C4 1.368(2)
C4 C10 1.418(2)
C5 C6 1.368(2)
C5 C10 1.417(2)
C6 C7 1.414(3)
C7 C8 1.364(2)
C8 C9 1.4247(19)
C9 C10 1.421(2)
C11 O12 1.245(2)
C11 O13 1.2663(18)
C21 C22 1.389(2)
C21 C26 1.389(2)
C21 C27 1.506(2)
C22 C23 1.385(2)
C23 C24 1.387(2)
C24 C25 1.383(2)
C25 C26 1.389(2)
C27 N28 1.482(2)
