# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_cyanohydrin53
_database_code_depnum_ccdc_archive 'CCDC 2117047'
loop_
_audit_author_name
_audit_author_address
'Tsuneomi Kawasaki'
;Tokyo University of Science
Japan
;
_audit_update_record             
;
2021-10-21 deposited with the CCDC.	2022-11-15 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C9 H9 N O'
_chemical_formula_moiety         'C9 H9 N O'
_chemical_formula_weight         147.18
_chemical_melting_point          58.5-59.1
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,-Y,1/2+Z
3 1/2+X,1/2-Y,-Z
4 -X,1/2+Y,1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   7.99848(14)
_cell_length_b                   10.47849(19)
_cell_length_c                   18.8198(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     1577.33(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    17787
_cell_measurement_theta_min      4.22
_cell_measurement_theta_max      68.24
_cell_measurement_temperature    123
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624.00
_exptl_absorpt_coefficient_mu    0.656
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.687
_exptl_absorpt_correction_T_max  0.877

#==============================================================================
# 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            17919
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_theta_max         68.239
_diffrn_reflns_theta_min         4.699
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2888
_reflns_number_gt                2783
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.719
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.998

#==============================================================================
# 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          0.0384
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.1064
_refine_ls_wR_factor_gt          0.1055
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2888
_refine_ls_number_parameters     199
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0637P)²+0.4859P] 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         0.33
_refine_diff_density_min         -0.26
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 1140 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(5)

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)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 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)
;

#==============================================================================
# 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 0.3698(2) -0.06886(15) 0.77878(9) 0.0267(4) Uani 1 1 d . . . . .
H1 H 0.3411 -0.1440 0.7690 0.032 Uiso 1 1 calc R U . . .
O2 O 1.2334(2) 0.17468(16) 0.76948(9) 0.0282(4) Uani 1 1 d . . . . .
H2 H 1.2639 0.0988 0.7756 0.034 Uiso 1 1 calc R U . . .
N1 N 0.6510(3) 0.1625(2) 0.76473(12) 0.0311(5) Uani 1 1 d . . . . .
N2 N 0.9977(3) 0.4333(2) 0.77927(13) 0.0384(5) Uani 1 1 d . . . . .
C1 C 0.5703(3) -0.0954(2) 0.87624(12) 0.0213(5) Uani 1 1 d . . . . .
C2 C 0.5047(3) -0.0152(2) 0.92831(13) 0.0248(5) Uani 1 1 d . . . . .
H2A H 0.4455 0.0597 0.9151 0.030 Uiso 1 1 calc R U . . .
C3 C 0.5262(3) -0.0454(2) 0.99969(13) 0.0276(5) Uani 1 1 d . . . . .
H3 H 0.4816 0.0098 1.0350 0.033 Uiso 1 1 calc R U . . .
C4 C 0.6120(3) -0.1551(2) 1.02036(13) 0.0275(5) Uani 1 1 d . . . . .
C5 C 0.6768(3) -0.2337(2) 0.96760(14) 0.0285(5) Uani 1 1 d . . . . .
H5 H 0.7363 -0.3085 0.9807 0.034 Uiso 1 1 calc R U . . .
C6 C 0.6564(3) -0.2048(2) 0.89616(13) 0.0253(5) Uani 1 1 d . . . . .
H6 H 0.7012 -0.2599 0.8609 0.030 Uiso 1 1 calc R U . . .
C7 C 0.5424(3) -0.0668(2) 0.79796(12) 0.0230(5) Uani 1 1 d . . . . .
H7 H 0.6036 -0.1316 0.7689 0.028 Uiso 1 1 calc R U . . .
C8 C 0.6045(3) 0.0626(2) 0.77907(12) 0.0246(5) Uani 1 1 d . . . . .
C9 C 0.6363(4) -0.1871(3) 1.09777(14) 0.0404(7) Uani 1 1 d . . . . .
H9A H 0.5827 -0.1217 1.1272 0.048 Uiso 1 1 calc R U . . .
H9B H 0.5860 -0.2704 1.1079 0.048 Uiso 1 1 calc R U . . .
H9C H 0.7561 -0.1900 1.1085 0.048 Uiso 1 1 calc R U . . .
C10 C 1.0770(3) 0.1647(2) 0.88151(12) 0.0206(5) Uani 1 1 d . . . . .
C11 C 1.1660(3) 0.2412(2) 0.92884(13) 0.0257(5) Uani 1 1 d . . . . .
H11 H 1.2232 0.3146 0.9119 0.031 Uiso 1 1 calc R U . . .
C12 C 1.1717(3) 0.2105(2) 1.00068(13) 0.0284(5) Uani 1 1 d . . . . .
H12 H 1.2340 0.2626 1.0324 0.034 Uiso 1 1 calc R U . . .
C13 C 1.0869(3) 0.1041(2) 1.02660(13) 0.0273(5) Uani 1 1 d . . . . .
C14 C 0.9992(3) 0.0285(2) 0.97887(13) 0.0273(5) Uani 1 1 d . . . . .
H14 H 0.9414 -0.0448 0.9956 0.033 Uiso 1 1 calc R U . . .
C15 C 0.9947(3) 0.0582(2) 0.90706(12) 0.0242(5) Uani 1 1 d . . . . .
H15 H 0.9346 0.0049 0.8752 0.029 Uiso 1 1 calc R U . . .
C16 C 1.0913(4) 0.0722(3) 1.10482(13) 0.0391(7) Uani 1 1 d . . . . .
H16A H 1.1588 0.1358 1.1300 0.047 Uiso 1 1 calc R U . . .
H16B H 0.9772 0.0726 1.1238 0.047 Uiso 1 1 calc R U . . .
H16C H 1.1407 -0.0126 1.1114 0.047 Uiso 1 1 calc R U . . .
C17 C 1.0758(3) 0.1941(2) 0.80253(12) 0.0220(5) Uani 1 1 d . . . . .
H17 H 0.9910 0.1384 0.7788 0.026 Uiso 1 1 calc R U . . .
C18 C 1.0322(3) 0.3292(2) 0.78939(12) 0.0257(5) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_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
O1 C7 1.427(3) . ?
O1 H1 0.8400 . ?
O2 C17 1.420(3) . ?
O2 H2 0.8400 . ?
N1 C8 1.144(3) . ?
N2 C18 1.141(3) . ?
C1 C6 1.388(3) . ?
C1 C2 1.394(3) . ?
C1 C7 1.520(3) . ?
C2 C3 1.391(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.394(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(4) . ?
C4 C9 1.508(3) . ?
C5 C6 1.388(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.487(3) . ?
C7 H7 1.0000 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C15 1.382(3) . ?
C10 C11 1.394(3) . ?
C10 C17 1.518(3) . ?
C11 C12 1.390(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.394(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.388(4) . ?
C13 C16 1.510(3) . ?
C14 C15 1.387(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.479(3) . ?
C17 H17 1.0000 . ?

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
C7 O1 H1 109.5 . . ?
C17 O2 H2 109.5 . . ?
C6 C1 C2 119.6(2) . . ?
C6 C1 C7 119.8(2) . . ?
C2 C1 C7 120.5(2) . . ?
C3 C2 C1 119.7(2) . . ?
C3 C2 H2A 120.1 . . ?
C1 C2 H2A 120.1 . . ?
C2 C3 C4 121.2(2) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 118.2(2) . . ?
C5 C4 C9 120.7(2) . . ?
C3 C4 C9 121.1(2) . . ?
C6 C5 C4 121.3(2) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C1 120.0(2) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
O1 C7 C8 106.04(18) . . ?
O1 C7 C1 112.60(19) . . ?
C8 C7 C1 111.24(19) . . ?
O1 C7 H7 109.0 . . ?
C8 C7 H7 109.0 . . ?
C1 C7 H7 109.0 . . ?
N1 C8 C7 179.4(3) . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C10 C11 119.0(2) . . ?
C15 C10 C17 120.1(2) . . ?
C11 C10 C17 120.8(2) . . ?
C12 C11 C10 120.3(2) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 120.6(2) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C14 C13 C12 118.4(2) . . ?
C14 C13 C16 121.1(2) . . ?
C12 C13 C16 120.5(2) . . ?
C15 C14 C13 121.0(2) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C10 C15 C14 120.5(2) . . ?
C10 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O2 C17 C18 105.84(19) . . ?
O2 C17 C10 113.25(19) . . ?
C18 C17 C10 111.04(19) . . ?
O2 C17 H17 108.9 . . ?
C18 C17 H17 108.9 . . ?
C10 C17 H17 108.9 . . ?
N2 C18 C17 179.6(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
C6 C1 C2 C3 0.1(3) . . . . ?
C7 C1 C2 C3 177.6(2) . . . . ?
C1 C2 C3 C4 -0.3(4) . . . . ?
C2 C3 C4 C5 0.4(4) . . . . ?
C2 C3 C4 C9 179.5(2) . . . . ?
C3 C4 C5 C6 -0.4(4) . . . . ?
C9 C4 C5 C6 -179.5(2) . . . . ?
C4 C5 C6 C1 0.3(4) . . . . ?
C2 C1 C6 C5 -0.1(3) . . . . ?
C7 C1 C6 C5 -177.6(2) . . . . ?
C6 C1 C7 O1 115.5(2) . . . . ?
C2 C1 C7 O1 -62.1(3) . . . . ?
C6 C1 C7 C8 -125.7(2) . . . . ?
C2 C1 C7 C8 56.8(3) . . . . ?
C15 C10 C11 C12 0.0(4) . . . . ?
C17 C10 C11 C12 -177.4(2) . . . . ?
C10 C11 C12 C13 -0.9(4) . . . . ?
C11 C12 C13 C14 1.1(4) . . . . ?
C11 C12 C13 C16 -179.1(2) . . . . ?
C12 C13 C14 C15 -0.4(4) . . . . ?
C16 C13 C14 C15 179.7(2) . . . . ?
C11 C10 C15 C14 0.6(4) . . . . ?
C17 C10 C15 C14 178.0(2) . . . . ?
C13 C14 C15 C10 -0.4(4) . . . . ?
C15 C10 C17 O2 -109.2(2) . . . . ?
C11 C10 C17 O2 68.1(3) . . . . ?
C15 C10 C17 C18 131.9(2) . . . . ?
C11 C10 C17 C18 -50.8(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
#==============================================================================
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: toluene'
####################################################################### 
# 
# 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_benzhydrylamine_aceticacid_salt
_database_code_depnum_ccdc_archive 'CCDC 2117487'
loop_
_audit_author_name
_audit_author_address
'Tsuneomi Kawasaki'
;Tokyo University of Science
Japan
;
_audit_update_record             
;
2021-10-24 deposited with the CCDC.	2022-11-15 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C15 H17 N O2'
_chemical_formula_moiety         'C15 H17 N O2'
_chemical_formula_weight         243.30
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'
_space_group_IT_number           43
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,+Z
3 1/4-X,1/4+Y,1/4+Z
4 1/4+X,1/4-Y,1/4+Z
5 +X,1/2+Y,1/2+Z
6 -X,1/2-Y,1/2+Z
7 1/4-X,3/4+Y,3/4+Z
8 1/4+X,3/4-Y,3/4+Z
9 1/2+X,+Y,1/2+Z
10 1/2-X,-Y,1/2+Z
11 3/4-X,1/4+Y,3/4+Z
12 3/4+X,1/4-Y,3/4+Z
13 1/2+X,1/2+Y,+Z
14 1/2-X,1/2-Y,+Z
15 3/4-X,3/4+Y,1/4+Z
16 3/4+X,3/4-Y,1/4+Z
#------------------------------------------------------------------------------
_cell_length_a                   17.4716(6)
_cell_length_b                   49.5734(18)
_cell_length_c                   5.8374(2)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     5056.0(3)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    11856
_cell_measurement_theta_min      3.56
_cell_measurement_theta_max      68.23
_cell_measurement_temperature    123
#------------------------------------------------------------------------------
_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2080.00
_exptl_absorpt_coefficient_mu    0.679
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.512
_exptl_absorpt_correction_T_max  0.934

#==============================================================================
# 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            13782
_diffrn_reflns_av_R_equivalents  0.0908
_diffrn_reflns_theta_max         68.237
_diffrn_reflns_theta_min         3.566
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -59
_diffrn_reflns_limit_k_max       59
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       6
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2295
_reflns_number_gt                1881
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.796
_reflns_Friedel_fraction_max     0.986
_reflns_Friedel_fraction_full    0.988

#==============================================================================
# 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          0.0828
_refine_ls_R_factor_gt           0.0702
_refine_ls_wR_factor_ref         0.1891
_refine_ls_wR_factor_gt          0.1778
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2295
_refine_ls_number_parameters     163
_refine_ls_goodness_of_fit_ref   1.166
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0760P)²+12.5797P] 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         0.32
_refine_diff_density_min         -0.29
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 No quotients, so Flack parameter determined by classical intensity fit
;
_refine_ls_abs_structure_Flack   -0.3(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 0.8672(2) 0.13777(8) 0.7254(7) 0.0316(10) Uani 1 1 d . . . . .
O2 O 0.9498(2) 0.15130(8) 0.4594(7) 0.0332(10) Uani 1 1 d . . . . .
N1 N 0.9948(2) 0.14889(9) 0.0045(9) 0.0278(11) Uani 1 1 d . . . . .
H1A H 1.0290 0.1350 0.0027 0.033 Uiso 1 1 calc R U . . .
H1B H 0.9768 0.1512 0.1494 0.033 Uiso 1 1 calc R U . . .
H1C H 0.9551 0.1450 -0.0911 0.033 Uiso 1 1 calc R U . . .
C1 C 0.8830(3) 0.14565(11) 0.5239(10) 0.0276(13) Uani 1 1 d . . . . .
C2 C 1.0335(3) 0.17430(11) -0.0740(10) 0.0289(13) Uani 1 1 d . . . . .
H2 H 1.0502 0.1713 -0.2359 0.035 Uiso 1 1 calc R U . . .
C3 C 0.9791(3) 0.19825(11) -0.0747(10) 0.0273(13) Uani 1 1 d . . . . .
C4 C 0.9761(3) 0.21483(12) -0.2639(11) 0.0331(13) Uani 1 1 d . . . . .
H4 H 1.0050 0.2103 -0.3962 0.040 Uiso 1 1 calc R U . . .
C5 C 0.9318(3) 0.23809(12) -0.2655(12) 0.0379(15) Uani 1 1 d . . . . .
H5 H 0.9311 0.2495 -0.3964 0.046 Uiso 1 1 calc R U . . .
C6 C 0.8907(3) 0.22801(12) 0.1159(11) 0.0338(14) Uani 1 1 d . . . . .
H6 H 0.8608 0.2324 0.2464 0.041 Uiso 1 1 calc R U . . .
C7 C 0.9364(3) 0.20488(11) 0.1192(11) 0.0306(13) Uani 1 1 d . . . . .
H7 H 0.9384 0.1938 0.2519 0.037 Uiso 1 1 calc R U . . .
C8 C 1.1215(3) 0.16744(13) 0.2716(11) 0.0347(14) Uani 1 1 d . . . . .
H8 H 1.0869 0.1545 0.3319 0.042 Uiso 1 1 calc R U . . .
C9 C 0.8185(3) 0.14876(12) 0.3550(11) 0.0329(14) Uani 1 1 d . . . . .
H9A H 0.7701 0.1437 0.4284 0.039 Uiso 1 1 calc R U . . .
H9B H 0.8156 0.1676 0.3041 0.039 Uiso 1 1 calc R U . . .
H9C H 0.8276 0.1370 0.2226 0.039 Uiso 1 1 calc R U . . .
C10 C 1.1885(3) 0.17360(13) 0.3897(12) 0.0419(17) Uani 1 1 d . . . . .
H10 H 1.1998 0.1645 0.5287 0.050 Uiso 1 1 calc R U . . .
C11 C 1.1556(3) 0.19984(12) -0.0151(12) 0.0349(15) Uani 1 1 d . . . . .
H11 H 1.1446 0.2091 -0.1537 0.042 Uiso 1 1 calc R U . . .
C12 C 0.8885(3) 0.24448(12) -0.0730(12) 0.0374(15) Uani 1 1 d . . . . .
H12 H 0.8575 0.2602 -0.0722 0.045 Uiso 1 1 calc R U . . .
C13 C 1.1053(3) 0.18021(11) 0.0661(10) 0.0302(14) Uani 1 1 d . . . . .
C14 C 1.2216(3) 0.20584(13) 0.1062(13) 0.0421(17) Uani 1 1 d . . . . .
H14 H 1.2556 0.2192 0.0490 0.050 Uiso 1 1 calc R U . . .
C15 C 1.2388(3) 0.19282(13) 0.3078(13) 0.0431(17) Uani 1 1 d . . . . .
H15 H 1.2844 0.1970 0.3892 0.052 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    '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
O1 C1 1.270(7) . ?
O2 C1 1.258(7) . ?
N1 C2 1.502(7) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
C1 C9 1.506(8) . ?
C2 C3 1.521(7) . ?
C2 C13 1.526(8) . ?
C2 H2 1.0000 . ?
C3 C4 1.378(8) . ?
C3 C7 1.395(8) . ?
C4 C5 1.388(8) . ?
C4 H4 0.9500 . ?
C5 C12 1.392(9) . ?
C5 H5 0.9500 . ?
C6 C12 1.372(9) . ?
C6 C7 1.397(8) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C13 1.386(8) . ?
C8 C10 1.392(8) . ?
C8 H8 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C15 1.381(10) . ?
C10 H10 0.9500 . ?
C11 C14 1.386(9) . ?
C11 C13 1.394(8) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C14 C15 1.376(10) . ?
C14 H14 0.9500 . ?
C15 H15 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
C2 N1 H1A 109.5 . . ?
C2 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C2 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
O2 C1 O1 123.2(5) . . ?
O2 C1 C9 118.5(5) . . ?
O1 C1 C9 118.3(5) . . ?
N1 C2 C3 112.0(4) . . ?
N1 C2 C13 111.6(5) . . ?
C3 C2 C13 111.4(4) . . ?
N1 C2 H2 107.2 . . ?
C3 C2 H2 107.2 . . ?
C13 C2 H2 107.2 . . ?
C4 C3 C7 119.3(5) . . ?
C4 C3 C2 119.5(5) . . ?
C7 C3 C2 121.1(5) . . ?
C3 C4 C5 121.5(6) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C4 C5 C12 119.1(6) . . ?
C4 C5 H5 120.4 . . ?
C12 C5 H5 120.4 . . ?
C12 C6 C7 121.0(6) . . ?
C12 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C3 C7 C6 119.2(6) . . ?
C3 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C13 C8 C10 120.0(6) . . ?
C13 C8 H8 120.0 . . ?
C10 C8 H8 120.0 . . ?
C1 C9 H9A 109.5 . . ?
C1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C10 C8 121.0(7) . . ?
C15 C10 H10 119.5 . . ?
C8 C10 H10 119.5 . . ?
C14 C11 C13 120.0(6) . . ?
C14 C11 H11 120.0 . . ?
C13 C11 H11 120.0 . . ?
C6 C12 C5 119.9(6) . . ?
C6 C12 H12 120.1 . . ?
C5 C12 H12 120.1 . . ?
C8 C13 C11 119.0(5) . . ?
C8 C13 C2 123.0(5) . . ?
C11 C13 C2 118.0(5) . . ?
C15 C14 C11 121.2(6) . . ?
C15 C14 H14 119.4 . . ?
C11 C14 H14 119.4 . . ?
C14 C15 C10 118.8(6) . . ?
C14 C15 H15 120.6 . . ?
C10 C15 H15 120.6 . . ?

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
N1 C2 C3 C4 -132.4(5) . . . . ?
C13 C2 C3 C4 101.8(6) . . . . ?
N1 C2 C3 C7 52.5(7) . . . . ?
C13 C2 C3 C7 -73.3(6) . . . . ?
C7 C3 C4 C5 0.3(8) . . . . ?
C2 C3 C4 C5 -174.9(5) . . . . ?
C3 C4 C5 C12 -1.1(9) . . . . ?
C4 C3 C7 C6 0.9(8) . . . . ?
C2 C3 C7 C6 176.1(5) . . . . ?
C12 C6 C7 C3 -1.3(8) . . . . ?
C13 C8 C10 C15 1.4(9) . . . . ?
C7 C6 C12 C5 0.5(9) . . . . ?
C4 C5 C12 C6 0.7(9) . . . . ?
C10 C8 C13 C11 -2.2(9) . . . . ?
C10 C8 C13 C2 179.4(6) . . . . ?
C14 C11 C13 C8 1.6(8) . . . . ?
C14 C11 C13 C2 -179.9(5) . . . . ?
N1 C2 C13 C8 -14.3(7) . . . . ?
C3 C2 C13 C8 111.7(6) . . . . ?
N1 C2 C13 C11 167.2(5) . . . . ?
C3 C2 C13 C11 -66.8(7) . . . . ?
C13 C11 C14 C15 -0.3(9) . . . . ?
C11 C14 C15 C10 -0.5(9) . . . . ?
C8 C10 C15 C14 -0.1(9) . . . . ?

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

#==============================================================================
# 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
#==============================================================================
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: ether'
####################################################################### 
# 
# 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_cyanohydrin30
_database_code_depnum_ccdc_archive 'CCDC 2204872'
loop_
_audit_author_name
_audit_author_address
'Tsuneomi Kawasaki'
;Tokyo University of Science
Japan
;
_audit_update_record             
;
2022-09-02 deposited with the CCDC.	2022-11-15 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C9 H9 N O'
_chemical_formula_moiety         'C9 H9 N O'
_chemical_formula_weight         147.18
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,-Y,1/2+Z
3 1/2+X,1/2-Y,-Z
4 -X,1/2+Y,1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   7.99688(14)
_cell_length_b                   10.47544(19)
_cell_length_c                   18.8109(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     1575.81(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    18079
_cell_measurement_theta_min      4.22
_cell_measurement_theta_max      68.25
_cell_measurement_temperature    123
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.600
_exptl_crystal_size_min          0.500
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624.00
_exptl_absorpt_coefficient_mu    0.657
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.545
_exptl_absorpt_correction_T_max  0.720

#==============================================================================
# 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            17671
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_theta_max         68.247
_diffrn_reflns_theta_min         4.702
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2881
_reflns_number_gt                2853
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.719
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.998

#==============================================================================
# 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          0.0412
_refine_ls_R_factor_gt           0.0408
_refine_ls_wR_factor_ref         0.1166
_refine_ls_wR_factor_gt          0.1163
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2881
_refine_ls_number_parameters     199
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0736P)²+0.4379P] 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         0.33
_refine_diff_density_min         -0.31
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 1187 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(5)

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)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 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)
;

#==============================================================================
# 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 0.1301(2) 0.56883(15) 0.22140(9) 0.0249(4) Uani 1 1 d . . . . .
H1 H 0.1709 0.6407 0.2117 0.030 Uiso 1 1 calc R U . . .
O20 O 0.2666(2) 0.32529(16) 0.23058(9) 0.0266(4) Uani 1 1 d . . . . .
H20 H 0.2456 0.4038 0.2323 0.032 Uiso 1 1 calc R U . . .
N22 N -0.1507(3) 0.3374(2) 0.23521(12) 0.0293(5) Uani 1 1 d . . . . .
N23 N 0.5024(3) 0.0669(2) 0.22068(13) 0.0369(6) Uani 1 1 d . . . . .
C2 C 0.4229(3) 0.3352(2) 0.11854(12) 0.0193(5) Uani 1 1 d . . . . .
C3 C 0.5055(3) 0.4417(2) 0.09299(12) 0.0223(5) Uani 1 1 d . . . . .
H3 H 0.5662 0.4947 0.1248 0.027 Uiso 1 1 calc R U . . .
C5 C -0.0048(3) 0.5151(2) 0.07164(13) 0.0237(5) Uani 1 1 d . . . . .
H5 H 0.0540 0.4400 0.0848 0.028 Uiso 1 1 calc R U . . .
C6 C 0.5006(3) 0.4717(2) 0.02109(13) 0.0256(5) Uani 1 1 d . . . . .
H6 H 0.5580 0.5452 0.0044 0.031 Uiso 1 1 calc R U . . .
C7 C 0.3284(3) 0.2895(2) -0.00072(13) 0.0269(5) Uani 1 1 d . . . . .
H7 H 0.2664 0.2373 -0.0325 0.032 Uiso 1 1 calc R U . . .
C8 C -0.1768(3) 0.7336(2) 0.03235(14) 0.0272(5) Uani 1 1 d . . . . .
H8 H -0.2364 0.8085 0.0193 0.033 Uiso 1 1 calc R U . . .
C9 C -0.0260(3) 0.5455(2) 0.00028(13) 0.0259(5) Uani 1 1 d . . . . .
H9 H 0.0191 0.4905 -0.0350 0.031 Uiso 1 1 calc R U . . .
C10 C -0.0703(3) 0.5953(2) 0.12377(12) 0.0198(5) Uani 1 1 d . . . . .
C11 C 0.3338(3) 0.2588(2) 0.07117(13) 0.0242(5) Uani 1 1 d . . . . .
H11 H 0.2764 0.1855 0.0881 0.029 Uiso 1 1 calc R U . . .
C12 C -0.1563(3) 0.7049(2) 0.10380(13) 0.0241(5) Uani 1 1 d . . . . .
H12 H -0.2009 0.7601 0.1391 0.029 Uiso 1 1 calc R U . . .
C13 C 0.4243(3) 0.3061(2) 0.19745(12) 0.0207(5) Uani 1 1 d . . . . .
H13 H 0.5091 0.3619 0.2211 0.025 Uiso 1 1 calc R U . . .
C14 C 0.4132(3) 0.3961(2) -0.02668(13) 0.0260(5) Uani 1 1 d . . . . .
C15 C -0.1121(3) 0.6552(2) -0.02048(13) 0.0258(5) Uani 1 1 d . . . . .
C16 C -0.1043(3) 0.4374(2) 0.22076(12) 0.0230(5) Uani 1 1 d . . . . .
C17 C 0.4679(3) 0.1708(2) 0.21081(12) 0.0244(5) Uani 1 1 d . . . . .
C18 C 0.4088(4) 0.4278(3) -0.10481(13) 0.0380(7) Uani 1 1 d . . . . .
H18A H 0.3415 0.3641 -0.1300 0.046 Uiso 1 1 calc R U . . .
H18B H 0.3592 0.5126 -0.1114 0.046 Uiso 1 1 calc R U . . .
H18C H 0.5229 0.4276 -0.1238 0.046 Uiso 1 1 calc R U . . .
C19 C -0.1363(4) 0.6870(3) -0.09774(14) 0.0383(7) Uani 1 1 d . . . . .
H19A H -0.0826 0.6216 -0.1271 0.046 Uiso 1 1 calc R U . . .
H19B H -0.2561 0.6900 -0.1086 0.046 Uiso 1 1 calc R U . . .
H19C H -0.0859 0.7704 -0.1079 0.046 Uiso 1 1 calc R U . . .
C21 C -0.0424(3) 0.5669(2) 0.20206(12) 0.0215(5) Uani 1 1 d . . . . .
H21 H -0.1038 0.6316 0.2312 0.026 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    '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
O1 C21 1.426(3) . ?
O1 H1 0.8400 . ?
O20 C13 1.421(3) . ?
O20 H20 0.8400 . ?
N22 C16 1.144(3) . ?
N23 C17 1.138(3) . ?
C2 C3 1.382(3) . ?
C2 C11 1.394(3) . ?
C2 C13 1.515(3) . ?
C3 C6 1.389(3) . ?
C3 H3 0.9500 . ?
C5 C9 1.390(3) . ?
C5 C10 1.393(3) . ?
C5 H5 0.9500 . ?
C6 C14 1.387(4) . ?
C6 H6 0.9500 . ?
C7 C11 1.391(4) . ?
C7 C14 1.394(4) . ?
C7 H7 0.9500 . ?
C8 C12 1.387(3) . ?
C8 C15 1.389(4) . ?
C8 H8 0.9500 . ?
C9 C15 1.396(4) . ?
C9 H9 0.9500 . ?
C10 C12 1.389(3) . ?
C10 C21 1.519(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C17 1.481(3) . ?
C13 H13 1.0000 . ?
C14 C18 1.507(3) . ?
C15 C19 1.504(3) . ?
C16 C21 1.486(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C21 H21 1.0000 . ?

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
C21 O1 H1 109.5 . . ?
C13 O20 H20 109.5 . . ?
C3 C2 C11 119.0(2) . . ?
C3 C2 C13 120.0(2) . . ?
C11 C2 C13 120.9(2) . . ?
C2 C3 C6 120.5(2) . . ?
C2 C3 H3 119.7 . . ?
C6 C3 H3 119.7 . . ?
C9 C5 C10 119.7(2) . . ?
C9 C5 H5 120.1 . . ?
C10 C5 H5 120.1 . . ?
C14 C6 C3 121.0(2) . . ?
C14 C6 H6 119.5 . . ?
C3 C6 H6 119.5 . . ?
C11 C7 C14 120.7(2) . . ?
C11 C7 H7 119.7 . . ?
C14 C7 H7 119.7 . . ?
C12 C8 C15 121.4(2) . . ?
C12 C8 H8 119.3 . . ?
C15 C8 H8 119.3 . . ?
C5 C9 C15 121.2(2) . . ?
C5 C9 H9 119.4 . . ?
C15 C9 H9 119.4 . . ?
C12 C10 C5 119.6(2) . . ?
C12 C10 C21 119.8(2) . . ?
C5 C10 C21 120.6(2) . . ?
C7 C11 C2 120.3(2) . . ?
C7 C11 H11 119.8 . . ?
C2 C11 H11 119.8 . . ?
C8 C12 C10 120.0(2) . . ?
C8 C12 H12 120.0 . . ?
C10 C12 H12 120.0 . . ?
O20 C13 C17 105.67(19) . . ?
O20 C13 C2 113.25(18) . . ?
C17 C13 C2 111.14(19) . . ?
O20 C13 H13 108.9 . . ?
C17 C13 H13 108.9 . . ?
C2 C13 H13 108.9 . . ?
C6 C14 C7 118.4(2) . . ?
C6 C14 C18 121.1(2) . . ?
C7 C14 C18 120.5(2) . . ?
C8 C15 C9 118.1(2) . . ?
C8 C15 C19 120.8(2) . . ?
C9 C15 C19 121.1(2) . . ?
N22 C16 C21 179.5(3) . . ?
N23 C17 C13 179.5(3) . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C15 C19 H19A 109.5 . . ?
C15 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C15 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O1 C21 C16 105.95(18) . . ?
O1 C21 C10 112.75(18) . . ?
C16 C21 C10 111.06(19) . . ?
O1 C21 H21 109.0 . . ?
C16 C21 H21 109.0 . . ?
C10 C21 H21 109.0 . . ?

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
C11 C2 C3 C6 -0.3(3) . . . . ?
C13 C2 C3 C6 -177.9(2) . . . . ?
C2 C3 C6 C14 -0.1(4) . . . . ?
C10 C5 C9 C15 -0.1(4) . . . . ?
C9 C5 C10 C12 0.0(3) . . . . ?
C9 C5 C10 C21 -177.4(2) . . . . ?
C14 C7 C11 C2 0.7(4) . . . . ?
C3 C2 C11 C7 0.0(3) . . . . ?
C13 C2 C11 C7 177.5(2) . . . . ?
C15 C8 C12 C10 -0.4(4) . . . . ?
C5 C10 C12 C8 0.2(3) . . . . ?
C21 C10 C12 C8 177.7(2) . . . . ?
C3 C2 C13 O20 109.5(2) . . . . ?
C11 C2 C13 O20 -68.0(3) . . . . ?
C3 C2 C13 C17 -131.8(2) . . . . ?
C11 C2 C13 C17 50.8(3) . . . . ?
C3 C6 C14 C7 0.7(4) . . . . ?
C3 C6 C14 C18 -179.5(2) . . . . ?
C11 C7 C14 C6 -1.0(4) . . . . ?
C11 C7 C14 C18 179.2(2) . . . . ?
C12 C8 C15 C9 0.3(4) . . . . ?
C12 C8 C15 C19 179.6(2) . . . . ?
C5 C9 C15 C8 -0.1(4) . . . . ?
C5 C9 C15 C19 -179.4(2) . . . . ?
C12 C10 C21 O1 -115.4(2) . . . . ?
C5 C10 C21 O1 62.1(3) . . . . ?
C12 C10 C21 C16 125.9(2) . . . . ?
C5 C10 C21 C16 -56.7(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        'p-tolualdehyde cyanohydrin'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
