# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2008

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Andreas Lemmerer'
_publ_contact_author_email       ANDREAS.LEMMERER@GMAIL.COM

_publ_section_title              
;
Structural and melting point characterisation of six
chiral ammonium carboxylate salts
;
_publ_requested_category         FO
loop_
_publ_author_name
'Andreas Lemmerer'
'Susan Bourne'
'Manuel A Fernandes'

#\#CIF_1.1

# CIF produced by WinGX routine CIF_UPDATE
# Created on 2007-11-16 at 19:59:14
# Using CIFtbx version 2.6.2 16 Jun 1998

# Dictionary name : cif_core.dic
# Dictionary vers : 2.3
# Request file : c:\wingx\files\archive.dat
# CIF files read : 7ag418_a nonius

data_1
_database_code_depnum_ccdc_archive 'CCDC 691820'

_audit_creation_date             2008-07-28T18:18:15-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
((R)-1-phenylethylammonium) 2-naphthalenecarboxylate
;
_chemical_formula_moiety         'C8 H12 N, C11 H7 O2'
_chemical_formula_sum            'C19 H19 N O2'
_chemical_formula_weight         293.35
_chemical_absolute_configuration rm

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)
_symmetry_space_group_name_Hall  'P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   6.3682(13)
_cell_length_b                   14.511(3)
_cell_length_c                   17.457(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1613.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    15605
_cell_measurement_theta_min      0.41
_cell_measurement_theta_max      27.1

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 0 0.26
1 0 0 0.25
0 1 1 0.091
0 -1 -1 0.049
0 1 -1 0.081
0 -1 1 0.084

_exptl_special_details           
;
Numerical integration absorption corrections based on indexed
crystal faces
were applied using the XPREP routine (Bruker, 1999).
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'Bruker XPREP (Bruker, 1999)'
_exptl_absorpt_correction_T_min  0.961
_exptl_absorpt_correction_T_max  0.992

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       '2.0° ω and π scans'
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0854
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_number            14277
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.68
_diffrn_reflns_theta_max         25.5
_diffrn_reflns_theta_full        25.5
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_reflns_number_total             1745
_reflns_number_gt                1517
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        DENZO-SMN
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999)
;
_computing_publication_material  
;
WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2002)
;

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0973P)²+0.0176P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.035(8)
_refine_ls_number_reflns         1745
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0521
_refine_ls_wR_factor_ref         0.1334
_refine_ls_wR_factor_gt          0.1277
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details .
_refine_ls_abs_structure_Flack   .
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.057

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

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 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0292(4) 0.55450(16) 0.35805(12) 0.0342(6) Uani 1 1 d . . .
H1 H 0.1682 0.5598 0.3773 0.041 Uiso 1 1 calc R . .
C2 C -0.0749(4) 0.47242(16) 0.36554(12) 0.0307(5) Uani 1 1 d . . .
C3 C -0.2796(4) 0.46395(18) 0.33574(13) 0.0399(6) Uani 1 1 d . . .
H3 H -0.3531 0.4074 0.3411 0.048 Uiso 1 1 calc R . .
C4 C -0.3736(4) 0.5364(2) 0.29909(14) 0.0428(6) Uani 1 1 d . . .
H4 H -0.5102 0.5288 0.2781 0.051 Uiso 1 1 calc R . .
C4A C -0.2704(4) 0.62246(19) 0.29202(13) 0.0395(6) Uani 1 1 d . . .
C5 C -0.3649(6) 0.7006(2) 0.25694(15) 0.0538(8) Uani 1 1 d . . .
H5 H -0.502 0.6957 0.2359 0.065 Uiso 1 1 calc R . .
C6 C -0.2602(6) 0.7827(2) 0.25319(17) 0.0622(9) Uani 1 1 d . . .
H6 H -0.3249 0.8341 0.2292 0.075 Uiso 1 1 calc R . .
C7 C -0.0597(6) 0.7918(2) 0.28415(18) 0.0603(9) Uani 1 1 d . . .
H7 H 0.0103 0.8495 0.2818 0.072 Uiso 1 1 calc R . .
C8 C 0.0368(5) 0.71811(19) 0.31782(16) 0.0504(7) Uani 1 1 d . . .
H8 H 0.1739 0.725 0.3385 0.06 Uiso 1 1 calc R . .
C8A C -0.0653(4) 0.63153(16) 0.32226(13) 0.0358(6) Uani 1 1 d . . .
C9 C 0.0278(4) 0.39402(16) 0.40897(13) 0.0343(6) Uani 1 1 d . . .
O1 O -0.0945(3) 0.33073(12) 0.43257(12) 0.0478(5) Uani 1 1 d . . .
O2 O 0.2188(3) 0.39584(13) 0.41834(11) 0.0463(5) Uani 1 1 d . . .
C10 C 0.6395(4) 0.49089(19) 0.56202(14) 0.0416(6) Uani 1 1 d . . .
C11 C 0.5311(5) 0.54355(18) 0.50858(15) 0.0468(7) Uani 1 1 d . . .
H11 H 0.4027 0.5214 0.488 0.056 Uiso 1 1 calc R . .
C12 C 0.6088(7) 0.62803(19) 0.48514(18) 0.0597(9) Uani 1 1 d . . .
H12 H 0.5345 0.6631 0.448 0.072 Uiso 1 1 calc R . .
C13 C 0.7901(7) 0.6608(3) 0.5149(2) 0.0733(11) Uani 1 1 d . . .
H13 H 0.8433 0.7185 0.4981 0.088 Uiso 1 1 calc R . .
C14 C 0.8967(6) 0.6119(3) 0.5688(2) 0.0766(11) Uani 1 1 d . . .
H14 H 1.0217 0.6364 0.5905 0.092 Uiso 1 1 calc R . .
C15 C 0.8225(5) 0.5249(3) 0.59261(18) 0.0615(9) Uani 1 1 d . . .
H15 H 0.8984 0.4901 0.6295 0.074 Uiso 1 1 calc R . .
C16 C 0.5572(5) 0.39655(19) 0.58507(14) 0.0446(7) Uani 1 1 d . . .
H16 H 0.6628 0.3674 0.6199 0.053 Uiso 1 1 calc R . .
C17 C 0.3500(6) 0.3999(3) 0.62660(19) 0.0695(10) Uani 1 1 d . . .
H17A H 0.2433 0.4271 0.5931 0.104 Uiso 1 1 calc R . .
H17B H 0.3644 0.4375 0.6729 0.104 Uiso 1 1 calc R . .
H17C H 0.3076 0.3373 0.6408 0.104 Uiso 1 1 calc R . .
N1 N 0.5348(4) 0.33657(15) 0.51545(13) 0.0388(5) Uani 1 1 d . . .
H1A H 0.406(6) 0.358(2) 0.4828(19) 0.058 Uiso 1 1 d . . .
H1C H 0.502(5) 0.273(3) 0.5325(17) 0.058 Uiso 1 1 d . . .
H1B H 0.674(6) 0.337(2) 0.493(2) 0.058 Uiso 1 1 d . . .


#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.369(3) . ?
C1 C8A 1.415(3) . ?
C1 H1 0.95 . ?
C2 C3 1.409(4) . ?
C2 C9 1.515(3) . ?
C3 C4 1.369(4) . ?
C3 H3 0.95 . ?
C4 C4A 1.417(4) . ?
C4 H4 0.95 . ?
C4A C8A 1.415(4) . ?
C4A C5 1.422(4) . ?
C5 C6 1.367(5) . ?
C5 H5 0.95 . ?
C6 C7 1.393(5) . ?
C6 H6 0.95 . ?
C7 C8 1.366(4) . ?
C7 H7 0.95 . ?
C8 C8A 1.417(4) . ?
C8 H8 0.95 . ?
C9 O2 1.228(3) . ?
C9 O1 1.272(3) . ?
C10 C15 1.373(4) . ?
C10 C11 1.390(4) . ?
C10 C16 1.520(4) . ?
C11 C12 1.384(4) . ?
C11 H11 0.95 . ?
C12 C13 1.353(6) . ?
C12 H12 0.95 . ?
C13 C14 1.360(6) . ?
C13 H13 0.95 . ?
C14 C15 1.411(6) . ?
C14 H14 0.95 . ?
C15 H15 0.95 . ?
C16 N1 1.502(4) . ?
C16 C17 1.506(4) . ?
C16 H16 1 . ?
C17 H17A 0.98 . ?
C17 H17B 0.98 . ?
C17 H17C 0.98 . ?
N1 H1A 1.04(3) . ?
N1 H1C 0.99(4) . ?
N1 H1B 0.97(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
_geom_angle_publ_flag
C2 C1 C8A 121.6(2) . . ?
C2 C1 H1 119.2 . . ?
C8A C1 H1 119.2 . . ?
C1 C2 C3 119.2(2) . . ?
C1 C2 C9 119.5(2) . . ?
C3 C2 C9 121.2(2) . . ?
C4 C3 C2 120.7(2) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C4A 121.0(2) . . ?
C3 C4 H4 119.5 . . ?
C4A C4 H4 119.5 . . ?
C8A C4A C4 118.5(2) . . ?
C8A C4A C5 118.5(3) . . ?
C4 C4A C5 123.0(3) . . ?
C6 C5 C4A 120.6(3) . . ?
C6 C5 H5 119.7 . . ?
C4A C5 H5 119.7 . . ?
C5 C6 C7 120.8(3) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C8 C7 C6 120.3(3) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C8A 120.7(3) . . ?
C7 C8 H8 119.6 . . ?
C8A C8 H8 119.6 . . ?
C4A C8A C1 118.9(2) . . ?
C4A C8A C8 119.1(2) . . ?
C1 C8A C8 122.0(2) . . ?
O2 C9 O1 125.3(2) . . ?
O2 C9 C2 118.5(2) . . ?
O1 C9 C2 116.1(2) . . ?
C15 C10 C11 119.0(3) . . ?
C15 C10 C16 120.9(3) . . ?
C11 C10 C16 120.1(3) . . ?
C12 C11 C10 120.5(3) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C13 C12 C11 120.2(3) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 120.6(3) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C13 C14 C15 120.2(3) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C10 C15 C14 119.4(3) . . ?
C10 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
N1 C16 C17 109.0(3) . . ?
N1 C16 C10 109.9(2) . . ?
C17 C16 C10 113.6(3) . . ?
N1 C16 H16 108.1 . . ?
C17 C16 H16 108.1 . . ?
C10 C16 H16 108.1 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 N1 H1A 110.0(18) . . ?
C16 N1 H1C 108.3(18) . . ?
H1A N1 H1C 106(2) . . ?
C16 N1 H1B 104(2) . . ?
H1A N1 H1B 119(3) . . ?
H1C N1 H1B 109(3) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8A C1 C2 C3 1.1(3) . . . . ?
C8A C1 C2 C9 -175.95(19) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C9 C2 C3 C4 177.6(2) . . . . ?
C2 C3 C4 C4A -1.8(4) . . . . ?
C3 C4 C4A C8A 1.4(4) . . . . ?
C3 C4 C4A C5 -177.6(2) . . . . ?
C8A C4A C5 C6 -0.5(4) . . . . ?
C4 C4A C5 C6 178.5(3) . . . . ?
C4A C5 C6 C7 -0.5(4) . . . . ?
C5 C6 C7 C8 1.0(4) . . . . ?
C6 C7 C8 C8A -0.4(4) . . . . ?
C4 C4A C8A C1 0.3(3) . . . . ?
C5 C4A C8A C1 179.3(2) . . . . ?
C4 C4A C8A C8 -177.9(2) . . . . ?
C5 C4A C8A C8 1.1(3) . . . . ?
C2 C1 C8A C4A -1.5(3) . . . . ?
C2 C1 C8A C8 176.6(2) . . . . ?
C7 C8 C8A C4A -0.7(4) . . . . ?
C7 C8 C8A C1 -178.8(2) . . . . ?
C1 C2 C9 O2 -19.5(3) . . . . ?
C3 C2 C9 O2 163.5(2) . . . . ?
C1 C2 C9 O1 160.8(2) . . . . ?
C3 C2 C9 O1 -16.2(3) . . . . ?
C15 C10 C11 C12 1.5(4) . . . . ?
C16 C10 C11 C12 -177.6(3) . . . . ?
C10 C11 C12 C13 -0.9(4) . . . . ?
C11 C12 C13 C14 -0.8(5) . . . . ?
C12 C13 C14 C15 1.9(5) . . . . ?
C11 C10 C15 C14 -0.4(4) . . . . ?
C16 C10 C15 C14 178.7(3) . . . . ?
C13 C14 C15 C10 -1.3(5) . . . . ?
C15 C10 C16 N1 -122.1(3) . . . . ?
C11 C10 C16 N1 57.0(3) . . . . ?
C15 C10 C16 C17 115.5(3) . . . . ?
C11 C10 C16 C17 -65.4(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O2 1.04(3) 1.73(4) 2.768(3) 172(3) .
N1 H1C O1 0.99(4) 1.74(4) 2.719(3) 171(3) 3_556
N1 H1B O1 0.97(4) 1.82(4) 2.771(3) 168(3) 1_655
_chemical_name_common            
'((R)-1-phenylethylammonium) 2-naphthalenecarboxylate'

###END

data_2
_database_code_depnum_ccdc_archive 'CCDC 691821'

_audit_creation_date             2008-07-28T18:27:54-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
((S)-1-phenylethylammonium) 2-naphthalenecarboxylate
;
_chemical_formula_moiety         'C8 H12 N, C11 H7 O2'
_chemical_formula_sum            'C19 H19 N O2'
_chemical_formula_weight         293.35
_chemical_absolute_configuration rm

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)
_symmetry_space_group_name_Hall  'P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   6.3709(13)
_cell_length_b                   14.513(3)
_cell_length_c                   17.445(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1612.9(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    16602
_cell_measurement_theta_min      0.21
_cell_measurement_theta_max      27.1

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.244
_exptl_crystal_size_min          0.135
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.25
-1 0 0 0.25
0 0 1 0.105
0 0 -1 0.139
0 1 0 0.067
0 -1 0 0.068

_exptl_special_details           
;
Numerical integration absorption corrections based on indexed
crystal faces
were applied using the XPREP routine (Bruker, 1999).
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'Bruker XPREP (Bruker, 1999)'
_exptl_absorpt_correction_T_min  0.9614
_exptl_absorpt_correction_T_max  0.987

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       '2.0° ω and π scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0648
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_number            15206
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_full        25.49
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_reflns_number_total             1749
_reflns_number_gt                1496
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        DENZO-SMN
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999)
;
_computing_publication_material  
;
WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2002)
;

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0657P)²+0.0592P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.031(4)
_refine_ls_number_reflns         1749
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.037
_refine_ls_wR_factor_ref         0.0968
_refine_ls_wR_factor_gt          0.0912
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details .
_refine_ls_abs_structure_Flack   .
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.039

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

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 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9711(3) 0.44549(13) 0.64174(11) 0.0347(4) Uani 1 1 d . . .
H1 H 0.8321 0.4403 0.6225 0.042 Uiso 1 1 calc R . .
C2 C 1.0750(3) 0.52741(12) 0.63420(10) 0.0317(4) Uani 1 1 d . . .
C3 C 1.2796(3) 0.53577(14) 0.66411(11) 0.0405(5) Uani 1 1 d . . .
H3 H 1.3533 0.5923 0.6587 0.049 Uiso 1 1 calc R . .
C4 C 1.3725(4) 0.46375(16) 0.70069(11) 0.0443(5) Uani 1 1 d . . .
H4 H 1.5087 0.4714 0.722 0.053 Uiso 1 1 calc R . .
C4A C 1.2702(4) 0.37769(14) 0.70764(11) 0.0403(5) Uani 1 1 d . . .
C5 C 1.3653(4) 0.29943(17) 0.74265(13) 0.0548(6) Uani 1 1 d . . .
H5 H 1.5027 0.3044 0.7634 0.066 Uiso 1 1 calc R . .
C6 C 1.2608(5) 0.21739(17) 0.74666(14) 0.0619(7) Uani 1 1 d . . .
H6 H 1.3255 0.166 0.7708 0.074 Uiso 1 1 calc R . .
C7 C 1.0602(5) 0.20840(16) 0.71566(15) 0.0609(7) Uani 1 1 d . . .
H7 H 0.9903 0.1507 0.718 0.073 Uiso 1 1 calc R . .
C8 C 0.9638(4) 0.28166(15) 0.68205(13) 0.0503(6) Uani 1 1 d . . .
H8 H 0.8267 0.2747 0.6614 0.06 Uiso 1 1 calc R . .
C8A C 1.0655(3) 0.36806(12) 0.67751(11) 0.0362(5) Uani 1 1 d . . .
C9 C 0.9731(3) 0.60601(12) 0.59120(11) 0.0349(5) Uani 1 1 d . . .
O1 O 1.0941(2) 0.66918(9) 0.56749(9) 0.0485(4) Uani 1 1 d . . .
O2 O 0.7809(2) 0.60392(10) 0.58144(9) 0.0458(4) Uani 1 1 d . . .
C10 C 0.3607(4) 0.50962(14) 0.43803(12) 0.0419(5) Uani 1 1 d . . .
C11 C 0.4676(4) 0.45642(14) 0.49144(13) 0.0475(6) Uani 1 1 d . . .
H11 H 0.5962 0.4782 0.5122 0.057 Uiso 1 1 calc R . .
C12 C 0.3892(5) 0.37224(15) 0.51464(14) 0.0599(7) Uani 1 1 d . . .
H12 H 0.4627 0.3374 0.5521 0.072 Uiso 1 1 calc R . .
C13 C 0.2111(6) 0.3391(2) 0.48497(18) 0.0730(9) Uani 1 1 d . . .
H13 H 0.1595 0.281 0.5014 0.088 Uiso 1 1 calc R . .
C14 C 0.1026(5) 0.3884(2) 0.43106(18) 0.0783(9) Uani 1 1 d . . .
H14 H -0.0229 0.364 0.4097 0.094 Uiso 1 1 calc R . .
C15 C 0.1771(4) 0.4750(2) 0.40727(15) 0.0609(7) Uani 1 1 d . . .
H15 H 0.1015 0.5096 0.3702 0.073 Uiso 1 1 calc R . .
C16 C 0.4431(4) 0.60359(15) 0.41511(12) 0.0456(5) Uani 1 1 d . . .
H16 H 0.3377 0.6328 0.3802 0.055 Uiso 1 1 calc R . .
C17 C 0.6502(5) 0.60012(19) 0.37363(16) 0.0684(8) Uani 1 1 d . . .
H17A H 0.7569 0.5731 0.4073 0.103 Uiso 1 1 calc R . .
H17B H 0.6926 0.6627 0.3592 0.103 Uiso 1 1 calc R . .
H17C H 0.636 0.5623 0.3274 0.103 Uiso 1 1 calc R . .
N1 N 0.4656(3) 0.66353(12) 0.48447(11) 0.0391(4) Uani 1 1 d . . .
H1A H 0.588(4) 0.6424(16) 0.5191(15) 0.059 Uiso 1 1 d . . .
H1B H 0.332(5) 0.6650(17) 0.5104(16) 0.059 Uiso 1 1 d . . .
H1C H 0.498(4) 0.7257(19) 0.4665(14) 0.059 Uiso 1 1 d . . .


#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.367(3) . ?
C1 C8A 1.419(3) . ?
C1 H1 0.95 . ?
C2 C3 1.409(3) . ?
C2 C9 1.512(3) . ?
C3 C4 1.360(3) . ?
C3 H3 0.95 . ?
C4 C4A 1.414(3) . ?
C4 H4 0.95 . ?
C4A C8A 1.413(3) . ?
C4A C5 1.425(3) . ?
C5 C6 1.366(4) . ?
C5 H5 0.95 . ?
C6 C7 1.394(4) . ?
C6 H6 0.95 . ?
C7 C8 1.361(3) . ?
C7 H7 0.95 . ?
C8 C8A 1.414(3) . ?
C8 H8 0.95 . ?
C9 O2 1.236(2) . ?
C9 O1 1.267(2) . ?
C10 C15 1.381(3) . ?
C10 C11 1.389(3) . ?
C10 C16 1.515(3) . ?
C11 C12 1.380(3) . ?
C11 H11 0.95 . ?
C12 C13 1.336(4) . ?
C12 H12 0.95 . ?
C13 C14 1.369(4) . ?
C13 H13 0.95 . ?
C14 C15 1.407(4) . ?
C14 H14 0.95 . ?
C15 H15 0.95 . ?
C16 N1 1.497(3) . ?
C16 C17 1.506(3) . ?
C16 H16 1 . ?
C17 H17A 0.98 . ?
C17 H17B 0.98 . ?
C17 H17C 0.98 . ?
N1 H1A 1.03(3) . ?
N1 H1B 0.96(3) . ?
N1 H1C 0.98(3) . ?

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
_geom_angle_publ_flag
C2 C1 C8A 121.72(17) . . ?
C2 C1 H1 119.1 . . ?
C8A C1 H1 119.1 . . ?
C1 C2 C3 119.16(17) . . ?
C1 C2 C9 119.73(17) . . ?
C3 C2 C9 121.06(17) . . ?
C4 C3 C2 120.67(19) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C4A 121.2(2) . . ?
C3 C4 H4 119.4 . . ?
C4A C4 H4 119.4 . . ?
C8A C4A C4 118.75(18) . . ?
C8A C4A C5 118.2(2) . . ?
C4 C4A C5 123.0(2) . . ?
C6 C5 C4A 120.6(2) . . ?
C6 C5 H5 119.7 . . ?
C4A C5 H5 119.7 . . ?
C5 C6 C7 120.6(2) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C8 C7 C6 120.5(2) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C8A 120.7(2) . . ?
C7 C8 H8 119.7 . . ?
C8A C8 H8 119.7 . . ?
C4A C8A C8 119.34(19) . . ?
C4A C8A C1 118.45(18) . . ?
C8 C8A C1 122.19(18) . . ?
O2 C9 O1 125.11(19) . . ?
O2 C9 C2 118.37(17) . . ?
O1 C9 C2 116.52(17) . . ?
C15 C10 C11 118.3(2) . . ?
C15 C10 C16 121.2(2) . . ?
C11 C10 C16 120.5(2) . . ?
C12 C11 C10 120.7(2) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C13 C12 C11 120.8(3) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 120.5(3) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C13 C14 C15 119.9(3) . . ?
C13 C14 H14 120 . . ?
C15 C14 H14 120 . . ?
C10 C15 C14 119.7(3) . . ?
C10 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
N1 C16 C17 108.9(2) . . ?
N1 C16 C10 110.06(17) . . ?
C17 C16 C10 113.6(2) . . ?
N1 C16 H16 108 . . ?
C17 C16 H16 108 . . ?
C10 C16 H16 108 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 N1 H1A 111.9(14) . . ?
C16 N1 H1B 107.9(16) . . ?
H1A N1 H1B 113(2) . . ?
C16 N1 H1C 107.3(14) . . ?
H1A N1 H1C 107.6(19) . . ?
H1B N1 H1C 108(2) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8A C1 C2 C3 -1.3(3) . . . . ?
C8A C1 C2 C9 176.11(16) . . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
C9 C2 C3 C4 -177.98(18) . . . . ?
C2 C3 C4 C4A 2.1(3) . . . . ?
C3 C4 C4A C8A -1.6(3) . . . . ?
C3 C4 C4A C5 177.3(2) . . . . ?
C8A C4A C5 C6 0.2(3) . . . . ?
C4 C4A C5 C6 -178.8(2) . . . . ?
C4A C5 C6 C7 0.8(4) . . . . ?
C5 C6 C7 C8 -1.1(4) . . . . ?
C6 C7 C8 C8A 0.4(3) . . . . ?
C4 C4A C8A C8 178.15(19) . . . . ?
C5 C4A C8A C8 -0.9(3) . . . . ?
C4 C4A C8A C1 -0.2(3) . . . . ?
C5 C4A C8A C1 -179.23(19) . . . . ?
C7 C8 C8A C4A 0.6(3) . . . . ?
C7 C8 C8A C1 178.9(2) . . . . ?
C2 C1 C8A C4A 1.7(3) . . . . ?
C2 C1 C8A C8 -176.62(18) . . . . ?
C1 C2 C9 O2 18.8(3) . . . . ?
C3 C2 C9 O2 -163.78(19) . . . . ?
C1 C2 C9 O1 -160.78(17) . . . . ?
C3 C2 C9 O1 16.6(3) . . . . ?
C15 C10 C11 C12 -1.7(3) . . . . ?
C16 C10 C11 C12 177.6(2) . . . . ?
C10 C11 C12 C13 1.5(4) . . . . ?
C11 C12 C13 C14 -0.2(4) . . . . ?
C12 C13 C14 C15 -0.8(4) . . . . ?
C11 C10 C15 C14 0.7(3) . . . . ?
C16 C10 C15 C14 -178.6(2) . . . . ?
C13 C14 C15 C10 0.6(4) . . . . ?
C15 C10 C16 N1 122.3(2) . . . . ?
C11 C10 C16 N1 -57.0(3) . . . . ?
C15 C10 C16 C17 -115.4(2) . . . . ?
C11 C10 C16 C17 65.3(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O2 1.03(3) 1.74(3) 2.765(2) 176(2) .
N1 H1B O1 0.96(3) 1.82(3) 2.776(3) 175(2) 1_455
N1 H1C O1 0.98(3) 1.75(3) 2.718(2) 171(2) 3_466
_chemical_name_common            
'((S)-1-phenylethylammonium) 2-naphthalenecarboxylate'

###END

data_3
_database_code_depnum_ccdc_archive 'CCDC 691822'

_audit_creation_date             2008-07-28T18:32:12-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
bis((RS)-1-phenylethylammonium) 26-naphthalenedicarboxylate
;
_chemical_formula_moiety         'C8 H12 N, C11 H7 O2'
_chemical_formula_sum            'C19 H19 N O2'
_chemical_formula_weight         293.35

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.1388(5)
_cell_length_b                   10.6194(5)
_cell_length_c                   12.8861(9)
_cell_angle_alpha                105.398(4)
_cell_angle_beta                 101.879(3)
_cell_angle_gamma                98.163(5)
_cell_volume                     775.14(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    17035
_cell_measurement_theta_min      0.41
_cell_measurement_theta_max      28.28

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.4
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             312
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.264
0 0 -1 0.16
1 0 0 0.25
-1 -8 12 0.099
2 1 -13 0.25
-1 2 4 0.269
-1 8 0 0.25
0 1 -1 0.239
-1 1 0 0.226
-6 -7 2 0.34

_exptl_special_details           
;
Numerical integration absorption corrections based on indexed
crystal faces
were applied using the XPREP routine (Bruker, 1999).
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'Bruker XPREP (Bruker, 1999)'
_exptl_absorpt_correction_T_min  0.961
_exptl_absorpt_correction_T_max  0.9803

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       '2.0° ω and π scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_number            14817
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.38
_diffrn_reflns_theta_max         25.5
_diffrn_reflns_theta_full        25.5
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_reflns_number_total             2849
_reflns_number_gt                2588
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        DENZO-SMN
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999)
;
_computing_publication_material  
;
WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2002)
;

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0510P)²+0.1709P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2849
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0349
_refine_ls_wR_factor_ref         0.0972
_refine_ls_wR_factor_gt          0.094
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.031

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

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 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.07642(17) 0.03190(10) 0.22281(8) 0.0214(2) Uani 1 1 d . . .
H1 H -0.2016 0.0364 0.2554 0.026 Uiso 1 1 calc R . .
C2 C 0.09932(17) 0.14092(10) 0.25549(8) 0.0201(2) Uani 1 1 d . . .
C3 C 0.28499(18) 0.13471(10) 0.20618(9) 0.0240(2) Uani 1 1 d . . .
H3 H 0.4076 0.2098 0.229 0.029 Uiso 1 1 calc R . .
C4 C 0.28961(18) 0.02162(11) 0.12587(9) 0.0251(2) Uani 1 1 d . . .
H4A H 0.4143 0.0198 0.0928 0.03 Uiso 1 1 calc R . .
C4A C 0.11120(18) -0.09268(10) 0.09144(8) 0.0233(2) Uani 1 1 d . . .
C5 C 0.1130(2) -0.21278(11) 0.01077(9) 0.0297(3) Uani 1 1 d . . .
H5 H 0.2357 -0.2175 -0.0236 0.036 Uiso 1 1 calc R . .
C6 C -0.0602(2) -0.32181(11) -0.01791(9) 0.0337(3) Uani 1 1 d . . .
H6 H -0.0563 -0.4019 -0.0716 0.04 Uiso 1 1 calc R . .
C7 C -0.2441(2) -0.31636(11) 0.03148(10) 0.0327(3) Uani 1 1 d . . .
H7 H -0.3636 -0.3927 0.0106 0.039 Uiso 1 1 calc R . .
C8 C -0.25242(19) -0.20208(11) 0.10939(9) 0.0274(2) Uani 1 1 d . . .
H8 H -0.3775 -0.1995 0.1422 0.033 Uiso 1 1 calc R . .
C8A C -0.07491(17) -0.08755(10) 0.14123(8) 0.0220(2) Uani 1 1 d . . .
C9 C 0.08888(17) 0.26544(10) 0.34257(8) 0.0206(2) Uani 1 1 d . . .
O1 O 0.24762(12) 0.36737(7) 0.36788(6) 0.0266(2) Uani 1 1 d . . .
O2 O -0.07805(12) 0.26288(7) 0.38428(6) 0.0269(2) Uani 1 1 d . . .
C10 C 0.64831(18) 0.66773(10) 0.34922(9) 0.0240(2) Uani 1 1 d . . .
C11 C 0.41672(19) 0.64061(11) 0.29692(10) 0.0302(3) Uani 1 1 d . . .
H11 H 0.3372 0.5507 0.2613 0.036 Uiso 1 1 calc R . .
C12 C 0.3016(2) 0.74391(12) 0.29647(10) 0.0343(3) Uani 1 1 d . . .
H12 H 0.1442 0.7245 0.26 0.041 Uiso 1 1 calc R . .
C13 C 0.4151(2) 0.87483(12) 0.34891(10) 0.0348(3) Uani 1 1 d . . .
H13 H 0.336 0.9455 0.3486 0.042 Uiso 1 1 calc R . .
C14 C 0.6440(2) 0.90272(12) 0.40182(10) 0.0351(3) Uani 1 1 d . . .
H14 H 0.7221 0.9927 0.4384 0.042 Uiso 1 1 calc R . .
C15 C 0.7606(2) 0.79961(11) 0.40182(9) 0.0291(3) Uani 1 1 d . . .
H15 H 0.9182 0.8196 0.4381 0.035 Uiso 1 1 calc R . .
C16 C 0.77979(17) 0.55673(10) 0.34559(9) 0.0241(2) Uani 1 1 d . . .
H16 H 0.945 0.5987 0.3778 0.029 Uiso 1 1 calc R . .
C17 C 0.7507(2) 0.46667(12) 0.22812(9) 0.0334(3) Uani 1 1 d . . .
H17A H 0.5906 0.4215 0.196 0.05 Uiso 1 1 calc R . .
H17B H 0.8452 0.3999 0.2303 0.05 Uiso 1 1 calc R . .
H17C H 0.7975 0.5205 0.1823 0.05 Uiso 1 1 calc R . .
N1 N 0.70974(15) 0.47275(9) 0.41505(7) 0.0215(2) Uani 1 1 d . . .
H1A H 0.550(2) 0.4312(13) 0.3907(11) 0.032 Uiso 1 1 d . . .
H1B H 0.732(2) 0.5269(13) 0.4902(12) 0.032 Uiso 1 1 d . . .
H1C H 0.791(2) 0.4038(13) 0.4114(11) 0.032 Uiso 1 1 d . . .


#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.3715(15) . ?
C1 C8A 1.4189(15) . ?
C1 H1 0.95 . ?
C2 C3 1.4158(15) . ?
C2 C9 1.5091(14) . ?
C3 C4 1.3696(15) . ?
C3 H3 0.95 . ?
C4 C4A 1.4164(15) . ?
C4 H4A 0.95 . ?
C4A C5 1.4185(15) . ?
C4A C8A 1.4215(15) . ?
C5 C6 1.3672(17) . ?
C5 H5 0.95 . ?
C6 C7 1.4061(18) . ?
C6 H6 0.95 . ?
C7 C8 1.3694(16) . ?
C7 H7 0.95 . ?
C8 C8A 1.4176(15) . ?
C8 H8 0.95 . ?
C9 O2 1.2515(12) . ?
C9 O1 1.2688(12) . ?
C10 C15 1.3877(16) . ?
C10 C11 1.3945(16) . ?
C10 C16 1.5163(14) . ?
C11 C12 1.3871(16) . ?
C11 H11 0.95 . ?
C12 C13 1.3810(18) . ?
C12 H12 0.95 . ?
C13 C14 1.3810(19) . ?
C13 H13 0.95 . ?
C14 C15 1.3905(17) . ?
C14 H14 0.95 . ?
C15 H15 0.95 . ?
C16 N1 1.5016(13) . ?
C16 C17 1.5197(15) . ?
C16 H16 1 . ?
C17 H17A 0.98 . ?
C17 H17B 0.98 . ?
C17 H17C 0.98 . ?
N1 H1A 0.967(14) . ?
N1 H1B 0.956(14) . ?
N1 H1C 0.940(14) . ?

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
_geom_angle_publ_flag
C2 C1 C8A 121.30(10) . . ?
C2 C1 H1 119.4 . . ?
C8A C1 H1 119.4 . . ?
C1 C2 C3 119.41(9) . . ?
C1 C2 C9 119.08(9) . . ?
C3 C2 C9 121.51(9) . . ?
C4 C3 C2 120.68(9) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C4A 120.97(10) . . ?
C3 C4 H4A 119.5 . . ?
C4A C4 H4A 119.5 . . ?
C4 C4A C5 122.58(10) . . ?
C4 C4A C8A 118.66(9) . . ?
C5 C4A C8A 118.75(10) . . ?
C6 C5 C4A 120.59(10) . . ?
C6 C5 H5 119.7 . . ?
C4A C5 H5 119.7 . . ?
C5 C6 C7 120.50(10) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C8 C7 C6 120.65(10) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C8A 120.18(10) . . ?
C7 C8 H8 119.9 . . ?
C8A C8 H8 119.9 . . ?
C8 C8A C1 121.69(10) . . ?
C8 C8A C4A 119.33(10) . . ?
C1 C8A C4A 118.98(9) . . ?
O2 C9 O1 123.77(9) . . ?
O2 C9 C2 118.05(9) . . ?
O1 C9 C2 118.17(9) . . ?
C15 C10 C11 118.83(10) . . ?
C15 C10 C16 119.86(10) . . ?
C11 C10 C16 121.27(10) . . ?
C12 C11 C10 120.47(11) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C13 C12 C11 120.23(11) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C14 C13 C12 119.76(10) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C15 120.25(11) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C10 C15 C14 120.45(11) . . ?
C10 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
N1 C16 C10 110.80(8) . . ?
N1 C16 C17 108.88(9) . . ?
C10 C16 C17 112.93(9) . . ?
N1 C16 H16 108 . . ?
C10 C16 H16 108 . . ?
C17 C16 H16 108 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 N1 H1A 113.0(8) . . ?
C16 N1 H1B 110.4(8) . . ?
H1A N1 H1B 104.9(11) . . ?
C16 N1 H1C 109.9(8) . . ?
H1A N1 H1C 107.1(11) . . ?
H1B N1 H1C 111.3(11) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8A C1 C2 C3 0.59(15) . . . . ?
C8A C1 C2 C9 179.97(8) . . . . ?
C1 C2 C3 C4 0.51(15) . . . . ?
C9 C2 C3 C4 -178.85(9) . . . . ?
C2 C3 C4 C4A -1.11(16) . . . . ?
C3 C4 C4A C5 -178.23(10) . . . . ?
C3 C4 C4A C8A 0.59(15) . . . . ?
C4 C4A C5 C6 178.34(10) . . . . ?
C8A C4A C5 C6 -0.48(16) . . . . ?
C4A C5 C6 C7 0.51(17) . . . . ?
C5 C6 C7 C8 -0.26(18) . . . . ?
C6 C7 C8 C8A -0.02(17) . . . . ?
C7 C8 C8A C1 -179.09(10) . . . . ?
C7 C8 C8A C4A 0.04(15) . . . . ?
C2 C1 C8A C8 178.05(9) . . . . ?
C2 C1 C8A C4A -1.09(15) . . . . ?
C4 C4A C8A C8 -178.66(9) . . . . ?
C5 C4A C8A C8 0.20(15) . . . . ?
C4 C4A C8A C1 0.49(14) . . . . ?
C5 C4A C8A C1 179.36(9) . . . . ?
C1 C2 C9 O2 2.11(14) . . . . ?
C3 C2 C9 O2 -178.53(9) . . . . ?
C1 C2 C9 O1 -176.68(8) . . . . ?
C3 C2 C9 O1 2.68(14) . . . . ?
C15 C10 C11 C12 0.75(16) . . . . ?
C16 C10 C11 C12 -176.84(10) . . . . ?
C10 C11 C12 C13 -0.65(17) . . . . ?
C11 C12 C13 C14 0.07(17) . . . . ?
C12 C13 C14 C15 0.41(17) . . . . ?
C11 C10 C15 C14 -0.27(16) . . . . ?
C16 C10 C15 C14 177.36(9) . . . . ?
C13 C14 C15 C10 -0.31(17) . . . . ?
C15 C10 C16 N1 112.15(11) . . . . ?
C11 C10 C16 N1 -70.28(12) . . . . ?
C15 C10 C16 C17 -125.40(11) . . . . ?
C11 C10 C16 C17 52.17(13) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O1 0.97(1) 1.82(1) 2.774(1) 170.6(1) .
N1 H1B O1 0.96(1) 1.84(2) 2.797(1) 175.6(1) 2_666
N1 H1C O2 0.94(1) 1.79(1) 2.718(1) 171.8(1) 1_655
_chemical_name_common            
'bis((RS)-1-phenylethylammonium) 26-naphthalenedicarboxylate'

###END

data_4
_database_code_depnum_ccdc_archive 'CCDC 691823'

_audit_creation_date             2008-07-28T18:39:16-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
bis((R)-1-phenylethylammonium) naphthalene-2,6-dicarboxylate
;
_chemical_formula_moiety         'C12 H6 O4, 2(C8 H12 N)'
_chemical_formula_sum            'C28 H30 N2 O4'
_chemical_formula_weight         458.54
_chemical_absolute_configuration rm

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)
_symmetry_space_group_name_Hall  'P 2yb'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.6633(4)
_cell_length_b                   6.3731(3)
_cell_length_c                   19.7210(7)
_cell_angle_alpha                90
_cell_angle_beta                 96.041(2)
_cell_angle_gamma                90
_cell_volume                     1207.78(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    37785
_cell_measurement_theta_min      0.41
_cell_measurement_theta_max      28.28

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             488
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 1 0.089
1 0 1 0.17
4 1 7 0.152
1 -10 -8 0.291
-1 2 1 0.303
1 0 -7 0.027
-1 0 7 0.092
5 0 -1 0.132

_exptl_special_details           
;
Numerical integration absorption corrections based on indexed
crystal faces
were applied using the XPREP routine (Bruker, 1999).
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'Bruker XPREP (Bruker, 1999)'
_exptl_absorpt_correction_T_min  0.9526
_exptl_absorpt_correction_T_max  0.9919

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       '1.8° ω and π scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.067
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_number            32802
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.12
_diffrn_reflns_theta_max         25.5
_diffrn_reflns_theta_full        25.5
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_reflns_number_total             2456
_reflns_number_gt                2156
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        DENZO-SMN
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999)
;
_computing_publication_material  
;
WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2002)
;

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0564P)²+0.1265P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2456
_refine_ls_number_parameters     327
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_ref         0.0881
_refine_ls_wR_factor_gt          0.0813
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details .
_refine_ls_abs_structure_Flack   .
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.034

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

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 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.07025(18) 0.5860(4) 0.81689(9) 0.0219(4) Uani 1 1 d . . .
H1 H 0.0533 0.7252 0.8312 0.026 Uiso 1 1 calc R . .
C2 C 0.18024(18) 0.4755(4) 0.84910(9) 0.0219(5) Uani 1 1 d . . .
C3 C 0.2038(2) 0.2664(4) 0.82889(10) 0.0256(5) Uani 1 1 d . . .
H3 H 0.2776 0.1878 0.8522 0.031 Uiso 1 1 calc R . .
C4 C 0.12149(19) 0.1767(4) 0.77618(10) 0.0265(5) Uani 1 1 d . . .
H4 H 0.1397 0.037 0.7628 0.032 Uiso 1 1 calc R . .
C4A C 0.00922(18) 0.2891(4) 0.74108(9) 0.0221(5) Uani 1 1 d . . .
C5 C -0.0776(2) 0.2003(4) 0.68622(9) 0.0244(5) Uani 1 1 d . . .
H5 H -0.0601 0.0614 0.6719 0.029 Uiso 1 1 calc R . .
C6 C -0.1868(2) 0.3112(4) 0.65335(9) 0.0244(5) Uani 1 1 d . . .
C7 C -0.2136(2) 0.5173(4) 0.67506(10) 0.0273(5) Uani 1 1 d . . .
H7 H -0.2887 0.5946 0.6523 0.033 Uiso 1 1 calc R . .
C8 C -0.1330(2) 0.6069(4) 0.72831(9) 0.0266(5) Uani 1 1 d . . .
H8 H -0.1537 0.7447 0.7426 0.032 Uiso 1 1 calc R . .
C8A C -0.01844(18) 0.4964(4) 0.76280(9) 0.0211(5) Uani 1 1 d . . .
C9 C 0.2797(2) 0.5809(4) 0.90297(10) 0.0232(5) Uani 1 1 d . . .
C9A C -0.2782(2) 0.2078(4) 0.59589(10) 0.0274(5) Uani 1 1 d . . .
O1 O 0.37032(14) 0.4675(3) 0.93629(7) 0.0296(4) Uani 1 1 d . . .
O2 O 0.26950(16) 0.7749(3) 0.90950(8) 0.0373(4) Uani 1 1 d . . .
O3 O -0.36561(14) 0.3210(3) 0.56059(7) 0.0316(4) Uani 1 1 d . . .
O4 O -0.2627(2) 0.0171(3) 0.58685(9) 0.0541(5) Uani 1 1 d . . .
C10 C 0.28751(19) 0.2799(4) 1.09714(9) 0.0255(5) Uani 1 1 d . . .
C11 C 0.1824(2) 0.4279(4) 1.09566(11) 0.0348(5) Uani 1 1 d . . .
H11 H 0.1004 0.4096 1.0652 0.042 Uiso 1 1 calc R . .
C12 C 0.1943(3) 0.6017(4) 1.13763(12) 0.0392(6) Uani 1 1 d . . .
H12 H 0.1205 0.7006 1.1359 0.047 Uiso 1 1 calc R . .
C13 C 0.3119(2) 0.6331(5) 1.18192(12) 0.0421(6) Uani 1 1 d . . .
H13 H 0.3195 0.7517 1.2113 0.05 Uiso 1 1 calc R . .
C14 C 0.4183(3) 0.4896(5) 1.18301(13) 0.0491(7) Uani 1 1 d . . .
H14 H 0.5012 0.5118 1.2125 0.059 Uiso 1 1 calc R . .
C15 C 0.4066(2) 0.3134(5) 1.14176(11) 0.0392(6) Uani 1 1 d . . .
H15 H 0.4805 0.2146 1.144 0.047 Uiso 1 1 calc R . .
C16 C 0.27370(19) 0.0820(4) 1.05426(10) 0.0277(5) Uani 1 1 d . . .
H16 H 0.2988 -0.0396 1.0852 0.033 Uiso 1 1 calc R . .
C17 C 0.1284(2) 0.0426(5) 1.01909(12) 0.0435(6) Uani 1 1 d . . .
H17A H 0.1045 0.1526 0.9851 0.065 Uiso 1 1 calc R . .
H17B H 0.0612 0.0443 1.053 0.065 Uiso 1 1 calc R . .
H17C H 0.1258 -0.0944 0.9965 0.065 Uiso 1 1 calc R . .
N1 N 0.37292(17) 0.0837(3) 1.00054(8) 0.0241(4) Uani 1 1 d . . .
H1A H 0.366(2) 0.218(5) 0.9749(12) 0.036 Uiso 1 1 d . . .
H1C H 0.351(2) -0.028(5) 0.9680(12) 0.036 Uiso 1 1 d . . .
H1B H 0.461(2) 0.062(4) 1.0206(10) 0.036 Uiso 1 1 d . . .
C18 C -0.2903(2) -0.1505(4) 0.39709(10) 0.0317(5) Uani 1 1 d . . .
C19 C -0.2039(3) 0.0233(4) 0.40423(12) 0.0419(6) Uani 1 1 d . . .
H19 H -0.1361 0.0335 0.4426 0.05 Uiso 1 1 calc R . .
C20 C -0.2150(3) 0.1825(5) 0.35608(13) 0.0486(7) Uani 1 1 d . . .
H20 H -0.1548 0.3004 0.3616 0.058 Uiso 1 1 calc R . .
C21 C -0.3126(3) 0.1707(5) 0.30049(14) 0.0507(7) Uani 1 1 d . . .
H21 H -0.3203 0.2796 0.2674 0.061 Uiso 1 1 calc R . .
C22 C -0.3995(3) -0.0012(6) 0.29320(13) 0.0575(8) Uani 1 1 d . . .
H22 H -0.468 -0.0099 0.255 0.069 Uiso 1 1 calc R . .
C23 C -0.3881(2) -0.1604(5) 0.34062(11) 0.0448(6) Uani 1 1 d . . .
H23 H -0.4481 -0.2786 0.3345 0.054 Uiso 1 1 calc R . .
C24 C -0.2807(2) -0.3279(4) 0.44804(11) 0.0322(5) Uani 1 1 d . . .
H24 H -0.3142 -0.4583 0.4233 0.039 Uiso 1 1 calc R . .
C25 C -0.1347(2) -0.3716(5) 0.48284(13) 0.0453(7) Uani 1 1 d . . .
H25A H -0.1053 -0.2551 0.5135 0.068 Uiso 1 1 calc R . .
H25B H -0.0696 -0.3857 0.4482 0.068 Uiso 1 1 calc R . .
H25C H -0.1356 -0.5019 0.5092 0.068 Uiso 1 1 calc R . .
N2 N -0.37508(18) -0.2862(4) 0.50209(9) 0.0263(4) Uani 1 1 d . . .
H2A H -0.352(3) -0.170(5) 0.5291(13) 0.039 Uiso 1 1 d . . .
H2C H -0.376(3) -0.406(5) 0.5308(13) 0.039 Uiso 1 1 d . . .
H2B H -0.468(2) -0.273(4) 0.4805(11) 0.039 Uiso 1 1 d . . .


#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.374(3) . ?
C1 C8A 1.416(2) . ?
C1 H1 0.95 . ?
C2 C3 1.416(3) . ?
C2 C9 1.513(3) . ?
C3 C4 1.366(3) . ?
C3 H3 0.95 . ?
C4 C4A 1.418(3) . ?
C4 H4 0.95 . ?
C4A C5 1.416(3) . ?
C4A C8A 1.423(3) . ?
C5 C6 1.375(3) . ?
C5 H5 0.95 . ?
C6 C7 1.414(4) . ?
C6 C9A 1.513(3) . ?
C7 C8 1.365(3) . ?
C7 H7 0.95 . ?
C8 C8A 1.423(3) . ?
C8 H8 0.95 . ?
C9 O2 1.248(3) . ?
C9 O1 1.265(3) . ?
C9A O4 1.240(3) . ?
C9A O3 1.263(3) . ?
C10 C11 1.385(3) . ?
C10 C15 1.390(3) . ?
C10 C16 1.516(3) . ?
C11 C12 1.380(4) . ?
C11 H11 0.95 . ?
C12 C13 1.373(3) . ?
C12 H12 0.95 . ?
C13 C14 1.374(4) . ?
C13 H13 0.95 . ?
C14 C15 1.385(4) . ?
C14 H14 0.95 . ?
C15 H15 0.95 . ?
C16 N1 1.502(3) . ?
C16 C17 1.520(3) . ?
C16 H16 1 . ?
C17 H17A 0.98 . ?
C17 H17B 0.98 . ?
C17 H17C 0.98 . ?
N1 H1A 0.99(3) . ?
N1 H1C 0.97(3) . ?
N1 H1B 0.91(2) . ?
C18 C23 1.384(3) . ?
C18 C19 1.385(3) . ?
C18 C24 1.509(3) . ?
C19 C20 1.386(4) . ?
C19 H19 0.95 . ?
C20 C21 1.371(4) . ?
C20 H20 0.95 . ?
C21 C22 1.379(4) . ?
C21 H21 0.95 . ?
C22 C23 1.376(4) . ?
C22 H22 0.95 . ?
C23 H23 0.95 . ?
C24 N2 1.498(3) . ?
C24 C25 1.528(3) . ?
C24 H24 1 . ?
C25 H25A 0.98 . ?
C25 H25B 0.98 . ?
C25 H25C 0.98 . ?
N2 H2A 0.92(3) . ?
N2 H2C 0.95(3) . ?
N2 H2B 0.95(2) . ?

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
_geom_angle_publ_flag
C2 C1 C8A 121.3(2) . . ?
C2 C1 H1 119.4 . . ?
C8A C1 H1 119.4 . . ?
C1 C2 C3 119.45(19) . . ?
C1 C2 C9 120.0(2) . . ?
C3 C2 C9 120.42(19) . . ?
C4 C3 C2 120.7(2) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C4A 120.9(2) . . ?
C3 C4 H4 119.5 . . ?
C4A C4 H4 119.5 . . ?
C5 C4A C4 122.2(2) . . ?
C5 C4A C8A 119.10(17) . . ?
C4 C4A C8A 118.73(17) . . ?
C6 C5 C4A 121.2(2) . . ?
C6 C5 H5 119.4 . . ?
C4A C5 H5 119.4 . . ?
C5 C6 C7 119.40(19) . . ?
C5 C6 C9A 119.2(2) . . ?
C7 C6 C9A 121.4(2) . . ?
C8 C7 C6 120.9(2) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C7 C8 C8A 120.9(2) . . ?
C7 C8 H8 119.6 . . ?
C8A C8 H8 119.6 . . ?
C1 C8A C4A 118.89(16) . . ?
C1 C8A C8 122.6(2) . . ?
C4A C8A C8 118.48(17) . . ?
O2 C9 O1 124.7(2) . . ?
O2 C9 C2 117.45(19) . . ?
O1 C9 C2 117.7(2) . . ?
O4 C9A O3 124.4(2) . . ?
O4 C9A C6 117.7(2) . . ?
O3 C9A C6 117.9(2) . . ?
C11 C10 C15 117.7(2) . . ?
C11 C10 C16 122.25(18) . . ?
C15 C10 C16 120.0(2) . . ?
C12 C11 C10 121.3(2) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C13 C12 C11 120.7(2) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 118.7(2) . . ?
C12 C13 H13 120.6 . . ?
C14 C13 H13 120.6 . . ?
C13 C14 C15 121.1(2) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C14 C15 C10 120.5(2) . . ?
C14 C15 H15 119.8 . . ?
C10 C15 H15 119.8 . . ?
N1 C16 C10 111.26(18) . . ?
N1 C16 C17 107.87(16) . . ?
C10 C16 C17 114.51(19) . . ?
N1 C16 H16 107.6 . . ?
C10 C16 H16 107.6 . . ?
C17 C16 H16 107.6 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 N1 H1A 110.5(14) . . ?
C16 N1 H1C 110.5(14) . . ?
H1A N1 H1C 107.2(19) . . ?
C16 N1 H1B 109.3(12) . . ?
H1A N1 H1B 111(2) . . ?
H1C N1 H1B 108(2) . . ?
C23 C18 C19 118.1(2) . . ?
C23 C18 C24 119.4(2) . . ?
C19 C18 C24 122.51(19) . . ?
C18 C19 C20 120.9(2) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
C21 C20 C19 120.3(3) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C21 C22 119.2(3) . . ?
C20 C21 H21 120.4 . . ?
C22 C21 H21 120.4 . . ?
C23 C22 C21 120.7(2) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C22 C23 C18 120.8(3) . . ?
C22 C23 H23 119.6 . . ?
C18 C23 H23 119.6 . . ?
N2 C24 C18 109.97(19) . . ?
N2 C24 C25 108.38(17) . . ?
C18 C24 C25 115.1(2) . . ?
N2 C24 H24 107.7 . . ?
C18 C24 H24 107.7 . . ?
C25 C24 H24 107.7 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 N2 H2A 114.9(16) . . ?
C24 N2 H2C 108.9(16) . . ?
H2A N2 H2C 108(2) . . ?
C24 N2 H2B 108.1(12) . . ?
H2A N2 H2B 111(2) . . ?
H2C N2 H2B 106(2) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8A C1 C2 C3 -1.4(3) . . . . ?
C8A C1 C2 C9 175.28(17) . . . . ?
C1 C2 C3 C4 2.4(3) . . . . ?
C9 C2 C3 C4 -174.23(18) . . . . ?
C2 C3 C4 C4A -1.0(3) . . . . ?
C3 C4 C4A C5 179.90(18) . . . . ?
C3 C4 C4A C8A -1.4(3) . . . . ?
C4 C4A C5 C6 179.31(19) . . . . ?
C8A C4A C5 C6 0.7(3) . . . . ?
C4A C5 C6 C7 -0.5(3) . . . . ?
C4A C5 C6 C9A -178.85(18) . . . . ?
C5 C6 C7 C8 -0.3(3) . . . . ?
C9A C6 C7 C8 177.98(19) . . . . ?
C6 C7 C8 C8A 1.0(3) . . . . ?
C2 C1 C8A C4A -1.0(3) . . . . ?
C2 C1 C8A C8 -179.87(18) . . . . ?
C5 C4A C8A C1 -178.87(19) . . . . ?
C4 C4A C8A C1 2.4(3) . . . . ?
C5 C4A C8A C8 0.0(3) . . . . ?
C4 C4A C8A C8 -178.7(2) . . . . ?
C7 C8 C8A C1 178.01(18) . . . . ?
C7 C8 C8A C4A -0.8(3) . . . . ?
C1 C2 C9 O2 -10.0(3) . . . . ?
C3 C2 C9 O2 166.6(2) . . . . ?
C1 C2 C9 O1 172.64(17) . . . . ?
C3 C2 C9 O1 -10.7(3) . . . . ?
C5 C6 C9A O4 9.7(3) . . . . ?
C7 C6 C9A O4 -168.6(2) . . . . ?
C5 C6 C9A O3 -170.65(19) . . . . ?
C7 C6 C9A O3 11.0(3) . . . . ?
C15 C10 C11 C12 -0.8(3) . . . . ?
C16 C10 C11 C12 176.7(2) . . . . ?
C10 C11 C12 C13 0.4(4) . . . . ?
C11 C12 C13 C14 0.9(4) . . . . ?
C12 C13 C14 C15 -1.7(4) . . . . ?
C13 C14 C15 C10 1.3(4) . . . . ?
C11 C10 C15 C14 0.0(3) . . . . ?
C16 C10 C15 C14 -177.6(2) . . . . ?
C11 C10 C16 N1 113.0(2) . . . . ?
C15 C10 C16 N1 -69.5(2) . . . . ?
C11 C10 C16 C17 -9.6(3) . . . . ?
C15 C10 C16 C17 167.9(2) . . . . ?
C23 C18 C19 C20 -0.1(4) . . . . ?
C24 C18 C19 C20 179.5(2) . . . . ?
C18 C19 C20 C21 0.3(4) . . . . ?
C19 C20 C21 C22 0.1(4) . . . . ?
C20 C21 C22 C23 -0.6(4) . . . . ?
C21 C22 C23 C18 0.7(4) . . . . ?
C19 C18 C23 C22 -0.4(4) . . . . ?
C24 C18 C23 C22 180.0(2) . . . . ?
C23 C18 C24 N2 -89.8(2) . . . . ?
C19 C18 C24 N2 90.6(3) . . . . ?
C23 C18 C24 C25 147.4(2) . . . . ?
C19 C18 C24 C25 -32.2(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O1 0.99(3) 1.77(3) 2.754(3) 173(2) .
N1 H1C O2 0.97(3) 1.83(3) 2.778(2) 167(2) 1_545
N1 H1B O1 0.91(2) 1.86(2) 2.758(2) 169(3) 2_647
N2 H2A O4 0.92(3) 1.80(3) 2.707(3) 165(2) .
N2 H2C O3 0.95(3) 1.84(3) 2.754(3) 161(2) 1_545
N2 H2B O3 0.95(2) 1.83(2) 2.761(2) 166(3) 2_446
_chemical_name_common            
'bis((R)-1-phenylethylammonium) naphthalene-2,6-dicarboxylate'

###END

data_5
_database_code_depnum_ccdc_archive 'CCDC 691824'

_audit_creation_date             2008-07-28T18:48:28-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
bis((S)1-phenylethylammonium) 2,6-naphthalenedicarboxylate
;
_chemical_formula_moiety         'C12 H6 O4, 2(C8 H12 N)'
_chemical_formula_sum            'C28 H30 N2 O4'
_chemical_formula_weight         458.54
_chemical_absolute_configuration rm

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)
_symmetry_space_group_name_Hall  'P 2yb'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.6656(12)
_cell_length_b                   6.3707(9)
_cell_length_c                   19.708(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.025(7)
_cell_angle_gamma                90
_cell_volume                     1206.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    15524
_cell_measurement_theta_min      0.81
_cell_measurement_theta_max      27.1

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             488
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.061
0 0 1 0.017
0 -1 0 0.156
0 1 0 0.116
1 0 0 0.02
-1 0 0 0.02

_exptl_special_details           
;
Numerical integration absorption corrections based on indexed
crystal faces
were applied using the XPREP routine (Bruker, 1999).
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'Bruker XPREP (Bruker, 1999)'
_exptl_absorpt_correction_T_min  0.943
_exptl_absorpt_correction_T_max  0.996

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       '1.5° ω and π scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.1662
_diffrn_reflns_av_unetI/netI     0.1065
_diffrn_reflns_number            21242
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.12
_diffrn_reflns_theta_max         25.5
_diffrn_reflns_theta_full        25.5
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_reflns_number_total             2441
_reflns_number_gt                1497
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        DENZO-SMN
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999)
;
_computing_publication_material  
;
WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2002)
;

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0000P)²+0.4221P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2441
_refine_ls_number_parameters     327
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1241
_refine_ls_R_factor_gt           0.0579
_refine_ls_wR_factor_ref         0.1167
_refine_ls_wR_factor_gt          0.0942
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details .
_refine_ls_abs_structure_Flack   .
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.05

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

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 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9300(5) 0.4137(8) 0.1832(2) 0.0280(13) Uani 1 1 d . . .
H1 H 0.9468 0.2744 0.1689 0.034 Uiso 1 1 calc R . .
C2 C 0.8202(5) 0.5243(9) 0.1512(2) 0.0271(13) Uani 1 1 d . . .
C3 C 0.7966(5) 0.7345(9) 0.1716(2) 0.0320(13) Uani 1 1 d . . .
H3 H 0.7225 0.8134 0.1486 0.038 Uiso 1 1 calc R . .
C4 C 0.8792(5) 0.8228(9) 0.2237(2) 0.0326(14) Uani 1 1 d . . .
H4 H 0.8616 0.963 0.2368 0.039 Uiso 1 1 calc R . .
C4A C 0.9910(4) 0.7111(8) 0.2590(2) 0.0272(12) Uani 1 1 d . . .
C5 C 1.0782(5) 0.7995(8) 0.3138(2) 0.0308(14) Uani 1 1 d . . .
H5 H 1.0619 0.9391 0.3278 0.037 Uiso 1 1 calc R . .
C6 C 1.1867(5) 0.6866(9) 0.3473(2) 0.0308(13) Uani 1 1 d . . .
C7 C 1.2140(5) 0.4842(10) 0.3250(3) 0.0345(14) Uani 1 1 d . . .
H7 H 1.2904 0.408 0.3471 0.041 Uiso 1 1 calc R . .
C8 C 1.1326(5) 0.3933(8) 0.2718(2) 0.0331(14) Uani 1 1 d . . .
H8 H 1.1527 0.2547 0.2579 0.04 Uiso 1 1 calc R . .
C8A C 1.0186(5) 0.5039(9) 0.2372(2) 0.0265(13) Uani 1 1 d . . .
C9 C 0.7199(5) 0.4191(9) 0.0970(3) 0.0288(14) Uani 1 1 d . . .
C9A C 1.2772(6) 0.7924(10) 0.4038(3) 0.0361(16) Uani 1 1 d . . .
O1 O 0.6298(3) 0.5318(6) 0.06383(16) 0.0366(10) Uani 1 1 d . . .
O2 O 0.7305(3) 0.2242(6) 0.09068(18) 0.0438(10) Uani 1 1 d . . .
O3 O 1.3660(3) 0.6798(6) 0.43947(16) 0.0386(10) Uani 1 1 d . . .
O4 O 1.2628(4) 0.9840(7) 0.4133(2) 0.0602(13) Uani 1 1 d . . .
C10 C 0.7132(4) 0.7201(8) -0.0974(2) 0.0312(11) Uani 1 1 d . . .
C11 C 0.8180(5) 0.5740(8) -0.0959(2) 0.0401(13) Uani 1 1 d . . .
H11 H 0.9 0.5935 -0.0655 0.048 Uiso 1 1 calc R . .
C12 C 0.8063(6) 0.3976(9) -0.1381(3) 0.0416(15) Uani 1 1 d . . .
H12 H 0.8803 0.299 -0.1365 0.05 Uiso 1 1 calc R . .
C13 C 0.6888(6) 0.3671(11) -0.1814(3) 0.0540(18) Uani 1 1 d . . .
H13 H 0.681 0.2481 -0.2107 0.065 Uiso 1 1 calc R . .
C14 C 0.5819(5) 0.5087(10) -0.1827(3) 0.0558(16) Uani 1 1 d . . .
H14 H 0.4988 0.4855 -0.212 0.067 Uiso 1 1 calc R . .
C15 C 0.5945(5) 0.6890(9) -0.1409(2) 0.0455(13) Uani 1 1 d . . .
H15 H 0.5211 0.7886 -0.1428 0.055 Uiso 1 1 calc R . .
C16 C 0.7263(5) 0.9187(8) -0.0543(2) 0.0320(13) Uani 1 1 d . . .
H16 H 0.702 1.0406 -0.0853 0.038 Uiso 1 1 calc R . .
C17 C 0.8710(5) 0.9560(10) -0.0190(3) 0.0485(16) Uani 1 1 d . . .
H17A H 0.8758 1.0964 0.0014 0.073 Uiso 1 1 calc R . .
H17B H 0.9391 0.9452 -0.0524 0.073 Uiso 1 1 calc R . .
H17C H 0.8918 0.8504 0.0168 0.073 Uiso 1 1 calc R . .
N1 N 0.6264(5) 0.9174(7) -0.0008(2) 0.0289(11) Uani 1 1 d . . .
H1A H 0.638(5) 0.783(8) 0.025(2) 0.043 Uiso 1 1 d . . .
H1B H 0.520(5) 0.927(8) -0.024(2) 0.043 Uiso 1 1 d . . .
H1C H 0.649(5) 1.019(9) 0.031(2) 0.043 Uiso 1 1 d . . .
C18 C 1.2906(5) 1.1507(8) 0.6033(2) 0.0396(13) Uani 1 1 d . . .
C19 C 1.2041(5) 0.9761(9) 0.5956(3) 0.0489(14) Uani 1 1 d . . .
H19 H 1.1372 0.965 0.5569 0.059 Uiso 1 1 calc R . .
C20 C 1.2151(6) 0.8176(11) 0.6444(3) 0.0577(19) Uani 1 1 d . . .
H20 H 1.154 0.7006 0.6395 0.069 Uiso 1 1 calc R . .
C21 C 1.3127(6) 0.8292(11) 0.6991(3) 0.0500(17) Uani 1 1 d . . .
H21 H 1.3204 0.7195 0.7319 0.06 Uiso 1 1 calc R . .
C22 C 1.4002(6) 0.9987(12) 0.7070(3) 0.0628(18) Uani 1 1 d . . .
H22 H 1.4689 1.0059 0.7451 0.075 Uiso 1 1 calc R . .
C23 C 1.3883(5) 1.1598(10) 0.6594(2) 0.0502(15) Uani 1 1 d . . .
H23 H 1.4484 1.2778 0.6655 0.06 Uiso 1 1 calc R . .
C24 C 1.2802(5) 1.3288(9) 0.5520(3) 0.0360(14) Uani 1 1 d . . .
H24 H 1.3138 1.4595 0.5766 0.043 Uiso 1 1 calc R . .
C25 C 1.1348(5) 1.3722(9) 0.5174(3) 0.0511(16) Uani 1 1 d . . .
H25A H 1.135 1.5044 0.492 0.077 Uiso 1 1 calc R . .
H25B H 1.0694 1.3826 0.552 0.077 Uiso 1 1 calc R . .
H25C H 1.1063 1.2574 0.4859 0.077 Uiso 1 1 calc R . .
N2 N 1.3750(5) 1.2858(8) 0.4981(2) 0.0301(12) Uani 1 1 d . . .
H2A H 1.356(5) 1.144(9) 0.465(2) 0.045 Uiso 1 1 d . . .
H2B H 1.482(5) 1.251(8) 0.523(2) 0.045 Uiso 1 1 d . . .
H2C H 1.372(5) 1.392(8) 0.469(3) 0.045 Uiso 1 1 d . . .


#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.371(6) . ?
C1 C8A 1.416(6) . ?
C1 H1 0.95 . ?
C2 C3 1.424(8) . ?
C2 C9 1.520(6) . ?
C3 C4 1.354(7) . ?
C3 H3 0.95 . ?
C4 C4A 1.415(6) . ?
C4 H4 0.95 . ?
C4A C5 1.415(6) . ?
C4A C8A 1.422(5) . ?
C5 C6 1.381(6) . ?
C5 H5 0.95 . ?
C6 C7 1.396(8) . ?
C6 C9A 1.501(7) . ?
C7 C8 1.371(7) . ?
C7 H7 0.95 . ?
C8 C8A 1.421(6) . ?
C8 H8 0.95 . ?
C9 O2 1.254(7) . ?
C9 O1 1.258(6) . ?
C9A O4 1.245(7) . ?
C9A O3 1.273(6) . ?
C10 C15 1.372(6) . ?
C10 C11 1.373(6) . ?
C10 C16 1.522(7) . ?
C11 C12 1.395(7) . ?
C11 H11 0.95 . ?
C12 C13 1.362(8) . ?
C12 H12 0.95 . ?
C13 C14 1.370(8) . ?
C13 H13 0.95 . ?
C14 C15 1.412(8) . ?
C14 H14 0.95 . ?
C15 H15 0.95 . ?
C16 N1 1.503(6) . ?
C16 C17 1.514(6) . ?
C16 H16 1 . ?
C17 H17A 0.98 . ?
C17 H17B 0.98 . ?
C17 H17C 0.98 . ?
N1 H1A 1.00(5) . ?
N1 H1B 1.08(5) . ?
N1 H1C 0.91(5) . ?
C18 C23 1.377(6) . ?
C18 C19 1.391(7) . ?
C18 C24 1.516(7) . ?
C19 C20 1.391(8) . ?
C19 H19 0.95 . ?
C20 C21 1.357(8) . ?
C20 H20 0.95 . ?
C21 C22 1.370(8) . ?
C21 H21 0.95 . ?
C22 C23 1.387(8) . ?
C22 H22 0.95 . ?
C23 H23 0.95 . ?
C24 N2 1.499(6) . ?
C24 C25 1.522(7) . ?
C24 H24 1 . ?
C25 H25A 0.98 . ?
C25 H25B 0.98 . ?
C25 H25C 0.98 . ?
N2 H2A 1.12(5) . ?
N2 H2B 1.12(5) . ?
N2 H2C 0.89(5) . ?

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
_geom_angle_publ_flag
C2 C1 C8A 121.0(5) . . ?
C2 C1 H1 119.5 . . ?
C8A C1 H1 119.5 . . ?
C1 C2 C3 119.5(5) . . ?
C1 C2 C9 120.2(5) . . ?
C3 C2 C9 120.3(5) . . ?
C4 C3 C2 120.4(5) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C4A 121.6(5) . . ?
C3 C4 H4 119.2 . . ?
C4A C4 H4 119.2 . . ?
C4 C4A C5 122.6(5) . . ?
C4 C4A C8A 118.4(4) . . ?
C5 C4A C8A 119.0(4) . . ?
C6 C5 C4A 121.3(5) . . ?
C6 C5 H5 119.4 . . ?
C4A C5 H5 119.4 . . ?
C5 C6 C7 119.3(5) . . ?
C5 C6 C9A 118.3(5) . . ?
C7 C6 C9A 122.3(5) . . ?
C8 C7 C6 121.2(5) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C7 C8 C8A 120.8(5) . . ?
C7 C8 H8 119.6 . . ?
C8A C8 H8 119.6 . . ?
C1 C8A C8 122.5(5) . . ?
C1 C8A C4A 119.1(4) . . ?
C8 C8A C4A 118.4(4) . . ?
O2 C9 O1 125.0(5) . . ?
O2 C9 C2 117.0(5) . . ?
O1 C9 C2 118.0(5) . . ?
O4 C9A O3 123.3(5) . . ?
O4 C9A C6 119.1(5) . . ?
O3 C9A C6 117.6(5) . . ?
C15 C10 C11 118.9(5) . . ?
C15 C10 C16 118.9(4) . . ?
C11 C10 C16 122.2(4) . . ?
C10 C11 C12 121.3(5) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C13 C12 C11 119.9(5) . . ?
C13 C12 H12 120 . . ?
C11 C12 H12 120 . . ?
C12 C13 C14 119.7(6) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C13 C14 C15 120.4(5) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C10 C15 C14 119.8(5) . . ?
C10 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
N1 C16 C17 108.0(4) . . ?
N1 C16 C10 111.4(4) . . ?
C17 C16 C10 113.9(4) . . ?
N1 C16 H16 107.8 . . ?
C17 C16 H16 107.8 . . ?
C10 C16 H16 107.8 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 N1 H1A 109(3) . . ?
C16 N1 H1B 110(2) . . ?
H1A N1 H1B 109(4) . . ?
C16 N1 H1C 111(3) . . ?
H1A N1 H1C 104(4) . . ?
H1B N1 H1C 114(4) . . ?
C23 C18 C19 118.4(5) . . ?
C23 C18 C24 119.7(5) . . ?
C19 C18 C24 121.9(5) . . ?
C18 C19 C20 120.2(5) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C21 C20 C19 120.4(6) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C21 C22 120.1(6) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C21 C22 C23 120.0(5) . . ?
C21 C22 H22 120 . . ?
C23 C22 H22 120 . . ?
C18 C23 C22 120.8(5) . . ?
C18 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
N2 C24 C18 109.4(4) . . ?
N2 C24 C25 108.7(4) . . ?
C18 C24 C25 115.4(5) . . ?
N2 C24 H24 107.7 . . ?
C18 C24 H24 107.7 . . ?
C25 C24 H24 107.7 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 N2 H2A 119(2) . . ?
C24 N2 H2B 109(2) . . ?
H2A N2 H2B 101(3) . . ?
C24 N2 H2C 110(3) . . ?
H2A N2 H2C 103(4) . . ?
H2B N2 H2C 113(4) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8A C1 C2 C3 1.3(7) . . . . ?
C8A C1 C2 C9 -175.4(4) . . . . ?
C1 C2 C3 C4 -2.1(7) . . . . ?
C9 C2 C3 C4 174.6(4) . . . . ?
C2 C3 C4 C4A 0.3(8) . . . . ?
C3 C4 C4A C5 -179.7(5) . . . . ?
C3 C4 C4A C8A 2.1(7) . . . . ?
C4 C4A C5 C6 -179.9(5) . . . . ?
C8A C4A C5 C6 -1.7(7) . . . . ?
C4A C5 C6 C7 2.4(7) . . . . ?
C4A C5 C6 C9A 178.5(4) . . . . ?
C5 C6 C7 C8 -1.9(8) . . . . ?
C9A C6 C7 C8 -177.8(5) . . . . ?
C6 C7 C8 C8A 0.7(8) . . . . ?
C2 C1 C8A C8 179.5(5) . . . . ?
C2 C1 C8A C4A 1.2(6) . . . . ?
C7 C8 C8A C1 -178.3(4) . . . . ?
C7 C8 C8A C4A 0.0(7) . . . . ?
C4 C4A C8A C1 -2.9(5) . . . . ?
C5 C4A C8A C1 178.9(5) . . . . ?
C4 C4A C8A C8 178.8(5) . . . . ?
C5 C4A C8A C8 0.5(6) . . . . ?
C1 C2 C9 O2 10.0(7) . . . . ?
C3 C2 C9 O2 -166.6(5) . . . . ?
C1 C2 C9 O1 -172.5(4) . . . . ?
C3 C2 C9 O1 10.9(7) . . . . ?
C5 C6 C9A O4 -8.5(8) . . . . ?
C7 C6 C9A O4 167.4(5) . . . . ?
C5 C6 C9A O3 171.8(5) . . . . ?
C7 C6 C9A O3 -12.3(8) . . . . ?
C15 C10 C11 C12 0.8(7) . . . . ?
C16 C10 C11 C12 -177.1(5) . . . . ?
C10 C11 C12 C13 -0.5(8) . . . . ?
C11 C12 C13 C14 -0.8(9) . . . . ?
C12 C13 C14 C15 1.9(9) . . . . ?
C11 C10 C15 C14 0.3(7) . . . . ?
C16 C10 C15 C14 178.2(5) . . . . ?
C13 C14 C15 C10 -1.6(8) . . . . ?
C15 C10 C16 N1 68.7(6) . . . . ?
C11 C10 C16 N1 -113.4(5) . . . . ?
C15 C10 C16 C17 -168.8(5) . . . . ?
C11 C10 C16 C17 9.1(7) . . . . ?
C23 C18 C19 C20 1.3(8) . . . . ?
C24 C18 C19 C20 -178.8(5) . . . . ?
C18 C19 C20 C21 -1.7(9) . . . . ?
C19 C20 C21 C22 0.8(9) . . . . ?
C20 C21 C22 C23 0.5(9) . . . . ?
C19 C18 C23 C22 0.0(8) . . . . ?
C24 C18 C23 C22 -179.9(5) . . . . ?
C21 C22 C23 C18 -0.9(9) . . . . ?
C23 C18 C24 N2 89.5(5) . . . . ?
C19 C18 C24 N2 -90.4(6) . . . . ?
C23 C18 C24 C25 -147.6(5) . . . . ?
C19 C18 C24 C25 32.4(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O1 1.00(5) 1.77(5) 2.766(6) 170(4) .
N1 H1B O1 1.08(5) 1.71(5) 2.749(5) 160(4) 2_655
N1 H1C O2 0.91(5) 1.87(5) 2.776(6) 169(4) 1_565
N2 H2A O4 1.12(5) 1.64(5) 2.699(6) 156(4) .
N2 H2B O3 1.12(5) 1.64(5) 2.756(6) 175(4) 2_856
N2 H2C O3 0.89(5) 1.92(5) 2.760(6) 156(5) 1_565
_chemical_name_common            
'bis((S)1-phenylethylammonium) 2,6-naphthalenedicarboxylate'

###END

data_6
_database_code_depnum_ccdc_archive 'CCDC 691825'

_audit_creation_date             2008-07-28T18:56:06-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
bis((RS)-1-phenylethylammonium) naphthalenedicarboxylate
;
_chemical_formula_moiety         'C12 H6 O4, 2(C8 H12 N)'
_chemical_formula_sum            'C28 H30 N2 O4'
_chemical_formula_weight         458.54

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.1211(5)
_cell_length_b                   9.6478(8)
_cell_length_c                   10.5813(11)
_cell_angle_alpha                94.483(4)
_cell_angle_beta                 98.503(4)
_cell_angle_gamma                103.126(5)
_cell_volume                     597.80(9)
_cell_formula_units_Z            1
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    8221
_cell_measurement_theta_min      0.21
_cell_measurement_theta_max      27.1

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.301
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.083
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             244
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.079
0 -1 0 0.171
1 0 0 0.121
-1 0 0 0.18
0 -2 3 0.075
0 2 -3 0.008

_exptl_special_details           
;
Numerical integration absorption corrections based on indexed
crystal faces
were applied using the XPREP routine (Bruker, 1999).
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'Bruker XPREP (Bruker, 1999)'
_exptl_absorpt_correction_T_min  0.9731
_exptl_absorpt_correction_T_max  0.9929

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       '1.5° ω and π scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0788
_diffrn_reflns_av_unetI/netI     0.0668
_diffrn_reflns_number            7594
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.62
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_full        25.49
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_reflns_number_total             2192
_reflns_number_gt                1521
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        DENZO-SMN
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999)
;
_computing_publication_material  
;
WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2002)
;

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0427P)²+0.1827P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.097(14)
_refine_ls_number_reflns         2192
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0822
_refine_ls_R_factor_gt           0.0504
_refine_ls_wR_factor_ref         0.1192
_refine_ls_wR_factor_gt          0.1051
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.043

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.0876(3) 0.3579(2) 0.90326(18) 0.0268(5) Uani 1 1 d . . .
H1 H 1.2117 0.3137 0.9059 0.032 Uiso 1 1 calc R . .
C2 C 0.9075(3) 0.3149(2) 0.80377(18) 0.0249(5) Uani 1 1 d . . .
C3 C 0.7230(3) 0.3814(2) 0.80014(19) 0.0292(5) Uani 1 1 d . . .
H3 H 0.5966 0.3512 0.732 0.035 Uiso 1 1 calc R . .
C4 C 1.2757(3) 0.5118(2) 1.10678(19) 0.0295(5) Uani 1 1 d . . .
H4 H 1.3996 0.4672 1.1122 0.035 Uiso 1 1 calc R . .
C4A C 1.0926(3) 0.4667(2) 1.00239(18) 0.0258(5) Uani 1 1 d . . .
C9 C 0.9104(3) 0.1999(2) 0.69971(18) 0.0266(5) Uani 1 1 d . . .
O1 O 0.7483(2) 0.16698(15) 0.60556(13) 0.0336(4) Uani 1 1 d . . .
O2 O 1.0766(2) 0.14258(15) 0.71030(13) 0.0332(4) Uani 1 1 d . . .
C10 C 0.3498(4) 0.2016(2) 0.2972(2) 0.0341(5) Uani 1 1 d . . .
C11 C 0.5761(4) 0.2738(3) 0.3150(2) 0.0393(6) Uani 1 1 d . . .
H11 H 0.6495 0.3229 0.3969 0.047 Uiso 1 1 calc R . .
C12 C 0.6977(4) 0.2751(3) 0.2135(2) 0.0449(6) Uani 1 1 d . . .
H12 H 0.8531 0.3258 0.2264 0.054 Uiso 1 1 calc R . .
C13 C 0.5937(5) 0.2033(3) 0.0948(2) 0.0474(6) Uani 1 1 d . . .
H13 H 0.6769 0.204 0.0257 0.057 Uiso 1 1 calc R . .
C14 C 0.3683(5) 0.1305(3) 0.0764(2) 0.0466(6) Uani 1 1 d . . .
H14 H 0.2957 0.0806 -0.0054 0.056 Uiso 1 1 calc R . .
C15 C 0.2470(4) 0.1299(2) 0.1774(2) 0.0404(6) Uani 1 1 d . . .
H15 H 0.0914 0.0795 0.164 0.048 Uiso 1 1 calc R . .
C16 C 0.2114(4) 0.2017(2) 0.4045(2) 0.0339(5) Uani 1 1 d . . .
H16 H 0.0484 0.1569 0.367 0.041 Uiso 1 1 calc R . .
C17 C 0.2256(4) 0.3506(2) 0.4691(2) 0.0416(6) Uani 1 1 d . . .
H17A H 0.1157 0.3444 0.5283 0.062 Uiso 1 1 calc R . .
H17B H 0.1906 0.4123 0.4034 0.062 Uiso 1 1 calc R . .
H17C H 0.3797 0.3912 0.5171 0.062 Uiso 1 1 calc R . .
N1 N 0.2864(3) 0.1125(2) 0.50478(17) 0.0288(4) Uani 1 1 d . . .
H1A H 0.443(5) 0.146(3) 0.542(2) 0.043 Uiso 1 1 d . . .
H1B H 0.262(4) 0.012(3) 0.468(2) 0.043 Uiso 1 1 d . . .
H1C H 0.206(4) 0.119(3) 0.573(2) 0.043 Uiso 1 1 d . . .


#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.370(3) . ?
C1 C4A 1.417(3) . ?
C1 H1 0.95 . ?
C2 C3 1.417(3) . ?
C2 C9 1.506(3) . ?
C3 C4 1.367(3) 2_767 ?
C3 H3 0.95 . ?
C4 C3 1.367(3) 2_767 ?
C4 C4A 1.415(3) . ?
C4 H4 0.95 . ?
C4A C4A 1.421(4) 2_767 ?
C9 O2 1.259(2) . ?
C9 O1 1.262(2) . ?
C10 C11 1.380(3) . ?
C10 C15 1.383(3) . ?
C10 C16 1.513(3) . ?
C11 C12 1.393(3) . ?
C11 H11 0.95 . ?
C12 C13 1.375(4) . ?
C12 H12 0.95 . ?
C13 C14 1.376(4) . ?
C13 H13 0.95 . ?
C14 C15 1.388(3) . ?
C14 H14 0.95 . ?
C15 H15 0.95 . ?
C16 N1 1.502(3) . ?
C16 C17 1.521(3) . ?
C16 H16 1 . ?
C17 H17A 0.98 . ?
C17 H17B 0.98 . ?
C17 H17C 0.98 . ?
N1 H1A 0.95(3) . ?
N1 H1B 0.98(3) . ?
N1 H1C 0.94(3) . ?

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
_geom_angle_publ_flag
C2 C1 C4A 121.42(17) . . ?
C2 C1 H1 119.3 . . ?
C4A C1 H1 119.3 . . ?
C1 C2 C3 119.08(18) . . ?
C1 C2 C9 119.63(17) . . ?
C3 C2 C9 121.29(17) . . ?
C4 C3 C2 120.94(18) 2_767 . ?
C4 C3 H3 119.5 2_767 . ?
C2 C3 H3 119.5 . . ?
C3 C4 C4A 120.94(18) 2_767 . ?
C3 C4 H4 119.5 2_767 . ?
C4A C4 H4 119.5 . . ?
C4 C4A C1 122.39(17) . . ?
C4 C4A C4A 118.5(2) . 2_767 ?
C1 C4A C4A 119.1(2) . 2_767 ?
O2 C9 O1 123.24(18) . . ?
O2 C9 C2 118.15(17) . . ?
O1 C9 C2 118.60(17) . . ?
C11 C10 C15 118.8(2) . . ?
C11 C10 C16 121.69(19) . . ?
C15 C10 C16 119.5(2) . . ?
C10 C11 C12 120.5(2) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C13 C12 C11 120.2(2) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 119.7(2) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C13 C14 C15 120.1(2) . . ?
C13 C14 H14 120 . . ?
C15 C14 H14 120 . . ?
C10 C15 C14 120.8(2) . . ?
C10 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
N1 C16 C10 110.11(16) . . ?
N1 C16 C17 108.84(18) . . ?
C10 C16 C17 113.65(18) . . ?
N1 C16 H16 108 . . ?
C10 C16 H16 108 . . ?
C17 C16 H16 108 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 N1 H1A 113.0(15) . . ?
C16 N1 H1B 110.6(14) . . ?
H1A N1 H1B 108(2) . . ?
C16 N1 H1C 108.9(14) . . ?
H1A N1 H1C 106(2) . . ?
H1B N1 H1C 111(2) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4A C1 C2 C3 0.2(3) . . . . ?
C4A C1 C2 C9 179.36(18) . . . . ?
C1 C2 C3 C4 0.8(3) . . . 2_767 ?
C9 C2 C3 C4 -178.33(18) . . . 2_767 ?
C3 C4 C4A C1 179.0(2) 2_767 . . . ?
C3 C4 C4A C4A -1.1(3) 2_767 . . 2_767 ?
C2 C1 C4A C4 179.35(19) . . . . ?
C2 C1 C4A C4A -0.5(3) . . . 2_767 ?
C1 C2 C9 O2 2.6(3) . . . . ?
C3 C2 C9 O2 -178.22(18) . . . . ?
C1 C2 C9 O1 -176.46(18) . . . . ?
C3 C2 C9 O1 2.7(3) . . . . ?
C15 C10 C11 C12 0.5(3) . . . . ?
C16 C10 C11 C12 -178.2(2) . . . . ?
C10 C11 C12 C13 -0.5(3) . . . . ?
C11 C12 C13 C14 0.2(3) . . . . ?
C12 C13 C14 C15 0.1(3) . . . . ?
C11 C10 C15 C14 -0.2(3) . . . . ?
C16 C10 C15 C14 178.6(2) . . . . ?
C13 C14 C15 C10 -0.1(3) . . . . ?
C11 C10 C16 N1 -71.2(2) . . . . ?
C15 C10 C16 N1 110.0(2) . . . . ?
C11 C10 C16 C17 51.2(3) . . . . ?
C15 C10 C16 C17 -127.6(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O1 0.95(3) 1.85(3) 2.784(2) 167(2) .
N1 H1B O1 0.98(3) 1.82(3) 2.802(2) 173(2) 2_656
N1 H1C O2 0.94(3) 1.78(3) 2.713(2) 174(2) 1_455
_chemical_name_common            
'bis((RS)-1-phenylethylammonium) naphthalenedicarboxylate'

