#------------------------------------------------------------------------------
#$Date: 2023-12-01 08:54:15 +0100 (Fri 01 de Dec de 2023) $
#$Revision: 287926 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/72/7207221.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_7207221
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_absolute_configuration rm
_chemical_formula_sum            'C18 H17 N O2'
_chemical_formula_weight         279.33
_space_group_IT_number           4
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 110.434(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.607(2)
_cell_length_b                   5.9725(14)
_cell_length_c                   13.838(4)
_cell_measurement_reflns_used    3457
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.00
_cell_measurement_theta_min      3.14
_cell_volume                     744.0(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.950
_diffrn_measured_fraction_theta_max 0.829
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       w-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0326
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6098
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         31.00
_diffrn_reflns_theta_min         3.14
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.9919
_exptl_absorpt_correction_T_min  0.9605
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3609
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0463
_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)+(0.0700P)²+0.1830P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1182
_refine_ls_wR_factor_ref         0.1198
_reflns_number_gt                3457
_reflns_number_total             3609
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c1ce06262j.txt
_cod_data_source_block           imai813V2_2
_cod_original_cell_volume        744.1(3)
_cod_original_sg_symbol_H-M      P21
_cod_database_code               7207221
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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 1.00094(16) 0.4467(3) 0.30549(11) 0.0194(3) Uani 1 1 d .
H1 H 1.0149 0.3034 0.2805 0.023 Uiso 1 1 calc R
C2 C 0.86920(16) 0.5587(3) 0.25921(11) 0.0183(3) Uani 1 1 d .
C3 C 0.84850(16) 0.7725(3) 0.29611(12) 0.0200(3) Uani 1 1 d .
H3 H 0.7582 0.8510 0.2635 0.024 Uiso 1 1 calc R
C4 C 0.95735(18) 0.8679(3) 0.37846(12) 0.0217(3) Uani 1 1 d .
H4 H 0.9409 1.0108 0.4027 0.026 Uiso 1 1 calc R
C5 C 1.20866(19) 0.8500(3) 0.51323(12) 0.0246(3) Uani 1 1 d .
H5 H 1.1944 0.9914 0.5398 0.030 Uiso 1 1 calc R
C6 C 1.34098(19) 0.7367(3) 0.55778(13) 0.0300(4) Uani 1 1 d .
H6 H 1.4172 0.8003 0.6150 0.036 Uiso 1 1 calc R
C7 C 1.36367(19) 0.5264(3) 0.51876(13) 0.0301(4) Uani 1 1 d .
H7 H 1.4556 0.4507 0.5496 0.036 Uiso 1 1 calc R
C8 C 1.25446(17) 0.4302(3) 0.43685(12) 0.0238(3) Uani 1 1 d .
H8 H 1.2710 0.2887 0.4114 0.029 Uiso 1 1 calc R
C9 C 1.11655(16) 0.5422(3) 0.39006(11) 0.0193(3) Uani 1 1 d .
C10 C 1.09377(17) 0.7560(3) 0.42777(11) 0.0196(3) Uani 1 1 d .
C11 C 0.74776(17) 0.4497(3) 0.17091(12) 0.0216(3) Uani 1 1 d .
O12 O 0.76814(14) 0.2529(2) 0.14810(10) 0.0326(3) Uani 1 1 d .
O13 O 0.63139(12) 0.5655(2) 0.12630(9) 0.0259(3) Uani 1 1 d .
C21 C 0.26363(18) 0.2076(3) 0.10725(13) 0.0233(3) Uani 1 1 d .
C22 C 0.39971(18) 0.1007(3) 0.15211(13) 0.0271(3) Uani 1 1 d .
H22 H 0.4844 0.1533 0.1385 0.032 Uiso 1 1 calc R
C23 C 0.4128(2) -0.0829(3) 0.21682(14) 0.0307(4) Uani 1 1 d .
H23 H 0.5058 -0.1566 0.2460 0.037 Uiso 1 1 calc R
C24 C 0.2904(2) -0.1586(3) 0.23886(14) 0.0311(4) Uani 1 1 d .
H24 H 0.2998 -0.2824 0.2838 0.037 Uiso 1 1 calc R
C25 C 0.15486(19) -0.0526(3) 0.19494(13) 0.0297(4) Uani 1 1 d .
H25 H 0.0708 -0.1044 0.2095 0.036 Uiso 1 1 calc R
C26 C 0.14093(18) 0.1290(3) 0.12974(13) 0.0263(3) Uani 1 1 d .
H26 H 0.0474 0.2007 0.1001 0.032 Uiso 1 1 calc R
C27 C 0.24130(19) 0.4089(3) 0.03793(14) 0.0286(4) Uani 1 1 d .
H27A H 0.1435 0.3959 -0.0180 0.034 Uiso 1 1 calc R
H27B H 0.2389 0.5447 0.0783 0.034 Uiso 1 1 calc R
N27 N 0.35750(15) 0.4378(2) -0.00886(10) 0.0232(3) Uani 1 1 d .
H27C H 0.3626 0.3121 -0.0446 0.035 Uiso 1 1 calc R
H27D H 0.4468 0.4619 0.0418 0.035 Uiso 1 1 calc R
H27E H 0.3343 0.5572 -0.0524 0.035 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 121.03(14)
C1 C2 C3 119.53(13)
C1 C2 C11 119.48(13)
C3 C2 C11 120.98(13)
C4 C3 C2 120.79(14)
C3 C4 C10 120.84(14)
C6 C5 C10 120.25(16)
C5 C6 C7 120.39(15)
C8 C7 C6 120.76(16)
C7 C8 C9 120.07(16)
C1 C9 C8 121.46(14)
C1 C9 C10 119.03(13)
C8 C9 C10 119.50(14)
C4 C10 C5 122.24(15)
C4 C10 C9 118.76(13)
C5 C10 C9 119.00(14)
O12 C11 O13 125.15(14)
O12 C11 C2 117.69(14)
O13 C11 C2 117.16(14)
C22 C21 C26 118.66(15)
C22 C21 C27 123.60(14)
C26 C21 C27 117.72(15)
C21 C22 C23 120.54(15)
C24 C23 C22 120.23(17)
C25 C24 C23 119.59(17)
C24 C25 C26 120.39(16)
C25 C26 C21 120.59(16)
N27 C27 C21 114.16(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.376(2)
C1 C9 1.422(2)
C2 C3 1.415(2)
C2 C11 1.511(2)
C3 C4 1.373(2)
C4 C10 1.416(2)
C5 C6 1.381(2)
C5 C10 1.422(2)
C6 C7 1.414(3)
C7 C8 1.373(2)
C8 C9 1.422(2)
C9 C10 1.425(2)
C11 O12 1.250(2)
C11 O13 1.276(2)
C21 C22 1.391(2)
C21 C26 1.401(2)
C21 C27 1.506(2)
C22 C23 1.393(3)
C23 C24 1.389(2)
C24 C25 1.384(3)
C25 C26 1.387(3)
C27 N27 1.483(2)
