# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_20180621_1_naphthcyanohydrin
_database_code_depnum_ccdc_archive 'CCDC 2543998'
loop_
_audit_author_name
_audit_author_address
'Tsuneomi Kawasaki'
;Tokyo University of Science
Japan
;
_audit_update_record             
;
2026-04-06 deposited with the CCDC.	2026-06-18 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C12 H9 N O'
_chemical_formula_moiety         'C12 H9 N O'
_chemical_formula_weight         183.21
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      trigonal
_space_group_name_H-M_alt        'R 3:H'
_space_group_name_Hall           'R 3'
_space_group_IT_number           146
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -Y,+X-Y,+Z
3 -X+Y,-X,+Z
4 2/3+X,1/3+Y,1/3+Z
5 2/3-Y,1/3+X-Y,1/3+Z
6 2/3-X+Y,1/3-X,1/3+Z
7 1/3+X,2/3+Y,2/3+Z
8 1/3-Y,2/3+X-Y,2/3+Z
9 1/3-X+Y,2/3-X,2/3+Z
#------------------------------------------------------------------------------
_cell_length_a                   24.5800(13)
_cell_length_b                   24.5800(13)
_cell_length_c                   4.05490(12)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                120.0000
_cell_volume                     2121.65(17)
_cell_formula_units_Z            9
_cell_measurement_reflns_used    6859
_cell_measurement_theta_min      3.60
_cell_measurement_theta_max      68.19
_cell_measurement_temperature    123
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864.00
_exptl_absorpt_coefficient_mu    0.663
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.664
_exptl_absorpt_correction_T_max  0.936

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      123
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            6778
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_theta_max         68.197
_diffrn_reflns_theta_min         3.596
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_limit_l_max       4
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_point_group_measured_fraction_full 0.940
_reflns_number_total             1618
_reflns_number_gt                1579
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.890
_reflns_Friedel_fraction_max     0.886
_reflns_Friedel_fraction_full    0.885

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0267
_refine_ls_wR_factor_ref         0.0697
_refine_ls_wR_factor_gt          0.0694
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         1618
_refine_ls_number_parameters     128
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0483P)²+0.4115P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.10
_refine_diff_density_min         -0.16
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 717 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(8)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.48222(6) 0.69776(6) 0.8691(3) 0.0262(3) Uani 1 1 d . . . . .
H1 H 0.4498 0.6650 0.8066 0.031 Uiso 1 1 calc R U . . .
N2 N 0.40889(8) 0.77782(9) 0.6567(6) 0.0420(5) Uani 1 1 d . . . . .
C3 C 0.44758(9) 0.76528(9) 0.6515(5) 0.0280(4) Uani 1 1 d . . . . .
C4 C 0.49682(8) 0.74695(8) 0.6407(5) 0.0216(4) Uani 1 1 d . . . . .
H4 H 0.4980 0.7316 0.4138 0.026 Uiso 1 1 calc R U . . .
C5 C 0.56117(8) 0.80220(8) 0.7216(4) 0.0205(4) Uani 1 1 d . . . . .
C6 C 0.56743(9) 0.85288(8) 0.8963(4) 0.0246(4) Uani 1 1 d . . . . .
H6 H 0.5309 0.8534 0.9679 0.030 Uiso 1 1 calc R U . . .
C7 C 0.62722(10) 0.90414(9) 0.9712(5) 0.0294(4) Uani 1 1 d . . . . .
H7 H 0.6308 0.9387 1.0937 0.035 Uiso 1 1 calc R U . . .
C8 C 0.67984(9) 0.90403(8) 0.8680(5) 0.0297(5) Uani 1 1 d . . . . .
H8 H 0.7199 0.9389 0.9174 0.036 Uiso 1 1 calc R U . . .
C9 C 0.67587(8) 0.85263(8) 0.6876(5) 0.0257(4) Uani 1 1 d . . . . .
C10 C 0.61553(8) 0.80028(8) 0.6154(5) 0.0209(4) Uani 1 1 d . . . . .
C11 C 0.61287(8) 0.74923(9) 0.4394(5) 0.0245(4) Uani 1 1 d . . . . .
H11 H 0.5732 0.7134 0.3939 0.029 Uiso 1 1 calc R U . . .
C12 C 0.66633(9) 0.75066(9) 0.3339(5) 0.0299(4) Uani 1 1 d . . . . .
H12 H 0.6633 0.7162 0.2128 0.036 Uiso 1 1 calc R U . . .
C13 C 0.72564(9) 0.80252(10) 0.4026(5) 0.0335(5) Uani 1 1 d . . . . .
H13 H 0.7625 0.8030 0.3281 0.040 Uiso 1 1 calc R U . . .
C14 C 0.73033(9) 0.85217(10) 0.5762(5) 0.0317(5) Uani 1 1 d . . . . .
H14 H 0.7707 0.8870 0.6232 0.038 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXS Version 2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1.1 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.1.1'

#==============================================================================
# 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
O1 C4 1.419(2) . ?
O1 H1 0.8400 . ?
N2 C3 1.137(3) . ?
C3 C4 1.488(3) . ?
C4 C5 1.518(2) . ?
C4 H4 1.0000 . ?
C5 C6 1.373(2) . ?
C5 C10 1.427(3) . ?
C6 C7 1.410(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.361(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.420(3) . ?
C8 H8 0.9500 . ?
C9 C14 1.418(3) . ?
C9 C10 1.426(2) . ?
C10 C11 1.416(3) . ?
C11 C12 1.366(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.403(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.363(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?

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
C4 O1 H1 109.5 . . ?
N2 C3 C4 178.2(2) . . ?
O1 C4 C3 109.94(15) . . ?
O1 C4 C5 109.12(14) . . ?
C3 C4 C5 111.33(15) . . ?
O1 C4 H4 108.8 . . ?
C3 C4 H4 108.8 . . ?
C5 C4 H4 108.8 . . ?
C6 C5 C10 120.25(15) . . ?
C6 C5 C4 121.13(16) . . ?
C10 C5 C4 118.61(15) . . ?
C5 C6 C7 121.05(17) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C8 C7 C6 119.93(18) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C9 121.17(17) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C14 C9 C8 121.73(18) . . ?
C14 C9 C10 119.16(18) . . ?
C8 C9 C10 119.11(17) . . ?
C11 C10 C9 118.01(16) . . ?
C11 C10 C5 123.52(15) . . ?
C9 C10 C5 118.47(16) . . ?
C12 C11 C10 121.16(16) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 120.70(19) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C14 C13 C12 120.01(18) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C9 120.94(18) . . ?
C13 C14 H14 119.5 . . ?
C9 C14 H14 119.5 . . ?

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
O1 C4 C5 C6 -99.43(19) . . . . ?
C3 C4 C5 C6 22.1(2) . . . . ?
O1 C4 C5 C10 79.9(2) . . . . ?
C3 C4 C5 C10 -158.61(16) . . . . ?
C10 C5 C6 C7 0.7(3) . . . . ?
C4 C5 C6 C7 180.00(17) . . . . ?
C5 C6 C7 C8 0.4(3) . . . . ?
C6 C7 C8 C9 -0.7(3) . . . . ?
C7 C8 C9 C14 179.45(19) . . . . ?
C7 C8 C9 C10 -0.2(3) . . . . ?
C14 C9 C10 C11 1.2(2) . . . . ?
C8 C9 C10 C11 -179.10(17) . . . . ?
C14 C9 C10 C5 -178.35(18) . . . . ?
C8 C9 C10 C5 1.3(2) . . . . ?
C6 C5 C10 C11 178.88(17) . . . . ?
C4 C5 C10 C11 -0.4(3) . . . . ?
C6 C5 C10 C9 -1.6(2) . . . . ?
C4 C5 C10 C9 179.12(15) . . . . ?
C9 C10 C11 C12 -1.7(3) . . . . ?
C5 C10 C11 C12 177.81(18) . . . . ?
C10 C11 C12 C13 1.2(3) . . . . ?
C11 C12 C13 C14 0.0(3) . . . . ?
C12 C13 C14 C9 -0.5(3) . . . . ?
C8 C9 C14 C13 -179.82(18) . . . . ?
C10 C9 C14 C13 -0.1(3) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        2-Hydroxy-2-(naphthalen-1-yl)acetonitrile
_chemical_name_common            '1-naphthaldehyde cyanohydrin'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: toluene'
_chemical_properties_physical    Air-sensitive,toxic
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_20190422_amide_2
_database_code_depnum_ccdc_archive 'CCDC 2544005'
loop_
_audit_author_name
_audit_author_address
'Tsuneomi Kawasaki'
;Tokyo University of Science
Japan
;
_audit_update_record             
;
2026-04-06 deposited with the CCDC.	2026-06-18 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C12 H11 N O2'
_chemical_formula_moiety         'C12 H11 N O2'
_chemical_formula_weight         201.22
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
_space_group_IT_number           15
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
#------------------------------------------------------------------------------
_cell_length_a                   32.423(13)
_cell_length_b                   5.8134(17)
_cell_length_c                   11.070(4)
_cell_angle_alpha                90.0000
_cell_angle_beta                 105.377(16)
_cell_angle_gamma                90.0000
_cell_volume                     2011.9(12)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1137
_cell_measurement_theta_min      3.56
_cell_measurement_theta_max      27.43
_cell_measurement_temperature    293
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             848.00
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.849
_exptl_absorpt_correction_T_max  0.982

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      293
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 14.629
_diffrn_reflns_number            13662
_diffrn_reflns_av_R_equivalents  0.1154
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_min         3.565
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2307
_reflns_number_gt                990
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1689
_refine_ls_R_factor_gt           0.0648
_refine_ls_wR_factor_ref         0.1927
_refine_ls_wR_factor_gt          0.1434
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2307
_refine_ls_number_parameters     136
_refine_ls_goodness_of_fit_ref   0.961
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0862P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.18
_refine_diff_density_min         -0.19
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O16 O 0.05844(7) 0.4969(4) -0.17650(19) 0.0754(8) Uani 1 1 d . . . . .
H16 H 0.0374 0.4221 -0.2128 0.091 Uiso 1 1 calc R U . . .
O17 O 0.01222(8) 0.1832(5) -0.1112(2) 0.0952(10) Uani 1 1 d . . . . .
N10 N 0.04087(8) 0.2128(5) 0.0973(2) 0.0648(8) Uani 1 1 d . . . . .
H10A H 0.0249 0.1048 0.1130 0.078 Uiso 1 1 calc R U . . .
H10B H 0.0589 0.2807 0.1578 0.078 Uiso 1 1 calc R U . . .
C1 C 0.18302(9) 0.2486(5) 0.0565(2) 0.0470(7) Uani 1 1 d . . . . .
C2 C 0.13841(9) 0.2607(5) -0.0092(2) 0.0459(7) Uani 1 1 d . . . . .
C3 C 0.11301(9) 0.4409(5) 0.0231(3) 0.0484(7) Uani 1 1 d . . . . .
C4 C 0.12204(10) 0.0893(5) -0.1024(3) 0.0558(8) Uani 1 1 d . . . . .
H4 H 0.0932 0.0908 -0.1450 0.067 Uiso 1 1 calc R U . . .
C5 C 0.20043(10) 0.4108(6) 0.1530(3) 0.0583(8) Uani 1 1 d . . . . .
H5 H 0.2293 0.4030 0.1958 0.070 Uiso 1 1 calc R U . . .
C7 C 0.03762(9) 0.2744(6) -0.0199(3) 0.0570(8) Uani 1 1 d . . . . .
C8 C 0.19168(12) -0.0844(6) -0.0671(3) 0.0664(9) Uani 1 1 d . . . . .
H8 H 0.2090 -0.1972 -0.0875 0.080 Uiso 1 1 calc R U . . .
C9 C 0.17541(10) 0.5767(6) 0.1831(3) 0.0589(9) Uani 1 1 d . . . . .
H9 H 0.1870 0.6800 0.2472 0.071 Uiso 1 1 calc R U . . .
C12 C 0.06569(9) 0.4702(6) -0.0442(3) 0.0566(8) Uani 1 1 d . . . . .
H12 H 0.0559 0.6116 -0.0123 0.068 Uiso 1 1 calc R U . . .
C13 C 0.14796(11) -0.0763(6) -0.1300(3) 0.0655(9) Uani 1 1 d . . . . .
H13 H 0.1365 -0.1852 -0.1912 0.079 Uiso 1 1 calc R U . . .
C14 C 0.13176(9) 0.5927(5) 0.1175(3) 0.0541(8) Uani 1 1 d . . . . .
H14 H 0.1152 0.7089 0.1384 0.065 Uiso 1 1 calc R U . . .
C15 C 0.20866(10) 0.0728(6) 0.0238(3) 0.0591(9) Uani 1 1 d . . . . .
H15 H 0.2376 0.0652 0.0653 0.071 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1.1 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.1.1'

#==============================================================================
# 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
O16 C12 1.429(3) . ?
O16 H16 0.8200 . ?
O17 C7 1.240(3) . ?
N10 C7 1.324(4) . ?
N10 H10A 0.8600 . ?
N10 H10B 0.8600 . ?
C1 C15 1.423(4) . ?
C1 C5 1.425(4) . ?
C1 C2 1.438(4) . ?
C2 C4 1.431(4) . ?
C2 C3 1.435(4) . ?
C3 C14 1.380(4) . ?
C3 C12 1.527(4) . ?
C4 C13 1.365(4) . ?
C4 H4 0.9300 . ?
C5 C9 1.358(4) . ?
C5 H5 0.9300 . ?
C7 C12 1.525(4) . ?
C8 C15 1.363(4) . ?
C8 C13 1.405(5) . ?
C8 H8 0.9300 . ?
C9 C14 1.412(4) . ?
C9 H9 0.9300 . ?
C12 H12 0.9800 . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?

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
C12 O16 H16 109.5 . . ?
C7 N10 H10A 120.0 . . ?
C7 N10 H10B 120.0 . . ?
H10A N10 H10B 120.0 . . ?
C15 C1 C5 121.6(3) . . ?
C15 C1 C2 118.9(3) . . ?
C5 C1 C2 119.5(3) . . ?
C4 C2 C3 124.1(3) . . ?
C4 C2 C1 117.5(3) . . ?
C3 C2 C1 118.4(3) . . ?
C14 C3 C2 119.3(3) . . ?
C14 C3 C12 118.8(3) . . ?
C2 C3 C12 121.9(3) . . ?
C13 C4 C2 121.3(3) . . ?
C13 C4 H4 119.3 . . ?
C2 C4 H4 119.3 . . ?
C9 C5 C1 120.7(3) . . ?
C9 C5 H5 119.6 . . ?
C1 C5 H5 119.6 . . ?
O17 C7 N10 123.1(3) . . ?
O17 C7 C12 118.3(3) . . ?
N10 C7 C12 118.6(3) . . ?
C15 C8 C13 120.0(3) . . ?
C15 C8 H8 120.0 . . ?
C13 C8 H8 120.0 . . ?
C5 C9 C14 120.2(3) . . ?
C5 C9 H9 119.9 . . ?
C14 C9 H9 119.9 . . ?
O16 C12 C7 108.5(2) . . ?
O16 C12 C3 112.5(2) . . ?
C7 C12 C3 113.6(3) . . ?
O16 C12 H12 107.3 . . ?
C7 C12 H12 107.3 . . ?
C3 C12 H12 107.3 . . ?
C4 C13 C8 120.9(3) . . ?
C4 C13 H13 119.6 . . ?
C8 C13 H13 119.6 . . ?
C3 C14 C9 121.9(3) . . ?
C3 C14 H14 119.1 . . ?
C9 C14 H14 119.1 . . ?
C8 C15 C1 121.4(3) . . ?
C8 C15 H15 119.3 . . ?
C1 C15 H15 119.3 . . ?

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
C15 C1 C2 C4 1.7(4) . . . . ?
C5 C1 C2 C4 -177.9(3) . . . . ?
C15 C1 C2 C3 -179.0(2) . . . . ?
C5 C1 C2 C3 1.4(4) . . . . ?
C4 C2 C3 C14 177.8(3) . . . . ?
C1 C2 C3 C14 -1.5(4) . . . . ?
C4 C2 C3 C12 -2.3(4) . . . . ?
C1 C2 C3 C12 178.4(2) . . . . ?
C3 C2 C4 C13 179.2(3) . . . . ?
C1 C2 C4 C13 -1.5(4) . . . . ?
C15 C1 C5 C9 -179.7(3) . . . . ?
C2 C1 C5 C9 -0.2(4) . . . . ?
C1 C5 C9 C14 -1.0(5) . . . . ?
O17 C7 C12 O16 -4.6(4) . . . . ?
N10 C7 C12 O16 176.8(3) . . . . ?
O17 C7 C12 C3 -130.5(3) . . . . ?
N10 C7 C12 C3 50.8(4) . . . . ?
C14 C3 C12 O16 123.1(3) . . . . ?
C2 C3 C12 O16 -56.8(4) . . . . ?
C14 C3 C12 C7 -113.1(3) . . . . ?
C2 C3 C12 C7 67.0(3) . . . . ?
C2 C4 C13 C8 0.3(5) . . . . ?
C15 C8 C13 C4 0.7(5) . . . . ?
C2 C3 C14 C9 0.3(4) . . . . ?
C12 C3 C14 C9 -179.6(3) . . . . ?
C5 C9 C14 C3 1.0(5) . . . . ?
C13 C8 C15 C1 -0.5(5) . . . . ?
C5 C1 C15 C8 178.8(3) . . . . ?
C2 C1 C15 C8 -0.7(4) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        2-Hydroxy-2-(naphthalen-1-yl)acetamide
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: MeOH/toluene'
