# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2017

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1566593'
_audit_update_record             
;
2017-08-03 deposited with the CCDC.
2017-10-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
'2-((1R,5R)-1-hydroxy-3-oxo-5-phenylcyclohexyl)pyridine 1-oxide'
_chemical_name_common            ?
_chemical_melting_point          418.15-420.15
_chemical_formula_moiety         283.31
_chemical_formula_sum            'C17 H17 N O3'
_chemical_formula_weight         283.31

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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   6.53370(10)
_cell_length_b                   8.45090(10)
_cell_length_c                   26.0879(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1440.46(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    289(2)
_cell_measurement_reflns_used    8745
_cell_measurement_theta_min      5.2300
_cell_measurement_theta_max      69.9050

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.330
_exptl_absorpt_coefficient_mu    0.729
_shelx_estimated_absorpt_T_min   0.749
_shelx_estimated_absorpt_T_max   0.795
_exptl_absorpt_correction_T_min  0.63802
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      289(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9149
_diffrn_reflns_number            12842
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.388
_diffrn_reflns_theta_max         70.055
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2674
_reflns_number_gt                2618
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.685
_reflns_Friedel_fraction_max     0.980
_reflns_Friedel_fraction_full    0.998

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro (Agilent Technologies)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-2013

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0619P)²+0.1503P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0205(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1055 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.01(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2674
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0324
_refine_ls_wR_factor_ref         0.0987
_refine_ls_wR_factor_gt          0.0876
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
O2 O 0.6522(2) 0.47216(16) 0.44876(5) 0.0453(4) Uani 1 1 d . . . . .
H2 H 0.7733 0.4466 0.4492 0.068 Uiso 1 1 calc R U . . .
O1 O 0.9251(2) 0.24251(19) 0.42719(7) 0.0558(4) Uani 1 1 d . . . . .
O3 O 0.1378(3) 0.6612(2) 0.41445(8) 0.0713(5) Uani 1 1 d . . . . .
C12 C 0.6160(3) 0.3951(2) 0.35887(7) 0.0390(4) Uani 1 1 d . . . . .
H12A H 0.7599 0.3682 0.3564 0.047 Uiso 1 1 calc R U . . .
H12B H 0.5405 0.3249 0.3363 0.047 Uiso 1 1 calc R U . . .
C11 C 0.5428(3) 0.3707(2) 0.41454(7) 0.0375(4) Uani 1 1 d . . . . .
N1 N 0.7700(2) 0.1441(2) 0.43275(6) 0.0432(4) Uani 1 1 d . . . . .
C7 C 0.5845(3) 0.5667(2) 0.34164(7) 0.0444(4) Uani 1 1 d . . . . .
H7 H 0.6550 0.6352 0.3663 0.053 Uiso 1 1 calc R U . . .
C10 C 0.3173(3) 0.4174(2) 0.41877(8) 0.0453(5) Uani 1 1 d . . . . .
H10A H 0.2353 0.3355 0.4027 0.054 Uiso 1 1 calc R U . . .
H10B H 0.2804 0.4207 0.4548 0.054 Uiso 1 1 calc R U . . .
C16 C 0.6573(4) -0.1166(3) 0.45081(8) 0.0574(6) Uani 1 1 d . . . . .
H16 H 0.6869 -0.2229 0.4564 0.069 Uiso 1 1 calc R U . . .
C14 C 0.4175(3) 0.0927(2) 0.44123(7) 0.0468(5) Uani 1 1 d . . . . .
H14 H 0.2827 0.1281 0.4415 0.056 Uiso 1 1 calc R U . . .
C13 C 0.5734(3) 0.1983(2) 0.43011(6) 0.0379(4) Uani 1 1 d . . . . .
C1 C 0.6783(3) 0.5958(2) 0.28934(8) 0.0472(5) Uani 1 1 d . . . . .
C17 C 0.8117(4) -0.0109(3) 0.44141(9) 0.0546(5) Uani 1 1 d . . . . .
H17 H 0.9466 -0.0458 0.4410 0.066 Uiso 1 1 calc R U . . .
C9 C 0.2626(3) 0.5736(3) 0.39490(9) 0.0504(5) Uani 1 1 d . . . . .
C15 C 0.4583(4) -0.0641(3) 0.45197(8) 0.0545(6) Uani 1 1 d . . . . .
H15 H 0.3523 -0.1334 0.4599 0.065 Uiso 1 1 calc R U . . .
C6 C 0.6021(5) 0.5254(3) 0.24544(9) 0.0660(7) Uani 1 1 d . . . . .
H6 H 0.4866 0.4614 0.2473 0.079 Uiso 1 1 calc R U . . .
C2 C 0.8487(4) 0.6917(3) 0.28492(10) 0.0632(6) Uani 1 1 d . . . . .
H2A H 0.9013 0.7407 0.3140 0.076 Uiso 1 1 calc R U . . .
C8 C 0.3556(4) 0.6075(3) 0.34348(9) 0.0594(6) Uani 1 1 d . . . . .
H8A H 0.3378 0.7188 0.3355 0.071 Uiso 1 1 calc R U . . .
H8B H 0.2841 0.5467 0.3175 0.071 Uiso 1 1 calc R U . . .
C5 C 0.6980(6) 0.5502(4) 0.19863(10) 0.0794(9) Uani 1 1 d . . . . .
H5 H 0.6456 0.5027 0.1693 0.095 Uiso 1 1 calc R U . . .
C3 C 0.9427(5) 0.7162(4) 0.23798(12) 0.0847(10) Uani 1 1 d . . . . .
H3 H 1.0564 0.7821 0.2357 0.102 Uiso 1 1 calc R U . . .
C4 C 0.8685(6) 0.6438(4) 0.19508(10) 0.0815(9) Uani 1 1 d . . . . .
H4 H 0.9333 0.6579 0.1637 0.098 Uiso 1 1 calc R U . . .


_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
O2 C11 1.429(2) . ?
O2 H2 0.8200 . ?
O1 N1 1.319(2) . ?
O3 C9 1.213(3) . ?
C12 C7 1.532(3) . ?
C12 C11 1.543(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C11 C13 1.525(3) . ?
C11 C10 1.529(3) . ?
N1 C17 1.357(3) . ?
N1 C13 1.366(2) . ?
C7 C1 1.516(3) . ?
C7 C8 1.536(3) . ?
C7 H7 0.9800 . ?
C10 C9 1.503(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C16 C17 1.369(3) . ?
C16 C15 1.375(4) . ?
C16 H16 0.9300 . ?
C14 C15 1.381(3) . ?
C14 C13 1.385(3) . ?
C14 H14 0.9300 . ?
C1 C2 1.382(3) . ?
C1 C6 1.383(3) . ?
C17 H17 0.9300 . ?
C9 C8 1.500(3) . ?
C15 H15 0.9300 . ?
C6 C5 1.388(4) . ?
C6 H6 0.9300 . ?
C2 C3 1.386(4) . ?
C2 H2A 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C5 C4 1.369(5) . ?
C5 H5 0.9300 . ?
C3 C4 1.365(5) . ?
C3 H3 0.9300 . ?
C4 H4 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
C11 O2 H2 109.5 . . ?
C7 C12 C11 111.17(15) . . ?
C7 C12 H12A 109.4 . . ?
C11 C12 H12A 109.4 . . ?
C7 C12 H12B 109.4 . . ?
C11 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
O2 C11 C13 109.94(14) . . ?
O2 C11 C10 106.37(15) . . ?
C13 C11 C10 110.69(15) . . ?
O2 C11 C12 110.67(15) . . ?
C13 C11 C12 109.74(14) . . ?
C10 C11 C12 109.39(16) . . ?
O1 N1 C17 118.22(18) . . ?
O1 N1 C13 120.37(16) . . ?
C17 N1 C13 121.41(18) . . ?
C1 C7 C12 111.33(16) . . ?
C1 C7 C8 112.66(18) . . ?
C12 C7 C8 109.53(17) . . ?
C1 C7 H7 107.7 . . ?
C12 C7 H7 107.7 . . ?
C8 C7 H7 107.7 . . ?
C9 C10 C11 115.20(17) . . ?
C9 C10 H10A 108.5 . . ?
C11 C10 H10A 108.5 . . ?
C9 C10 H10B 108.5 . . ?
C11 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
C17 C16 C15 119.3(2) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C15 C14 C13 121.3(2) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
N1 C13 C14 117.71(17) . . ?
N1 C13 C11 117.20(16) . . ?
C14 C13 C11 125.08(18) . . ?
C2 C1 C6 118.2(2) . . ?
C2 C1 C7 119.75(19) . . ?
C6 C1 C7 122.0(2) . . ?
N1 C17 C16 120.8(2) . . ?
N1 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
O3 C9 C8 122.1(2) . . ?
O3 C9 C10 121.4(2) . . ?
C8 C9 C10 116.22(18) . . ?
C16 C15 C14 119.2(2) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C1 C6 C5 120.1(3) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C1 C2 C3 121.2(3) . . ?
C1 C2 H2A 119.4 . . ?
C3 C2 H2A 119.4 . . ?
C9 C8 C7 112.30(19) . . ?
C9 C8 H8A 109.1 . . ?
C7 C8 H8A 109.1 . . ?
C9 C8 H8B 109.1 . . ?
C7 C8 H8B 109.1 . . ?
H8A C8 H8B 107.9 . . ?
C4 C5 C6 120.9(3) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C4 C3 C2 120.0(3) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 119.5(2) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?

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
C7 C12 C11 O2 -59.3(2) . . . . ?
C7 C12 C11 C13 179.16(16) . . . . ?
C7 C12 C11 C10 57.5(2) . . . . ?
C11 C12 C7 C1 173.42(16) . . . . ?
C11 C12 C7 C8 -61.3(2) . . . . ?
O2 C11 C10 C9 71.9(2) . . . . ?
C13 C11 C10 C9 -168.68(16) . . . . ?
C12 C11 C10 C9 -47.6(2) . . . . ?
O1 N1 C13 C14 -173.78(18) . . . . ?
C17 N1 C13 C14 5.8(3) . . . . ?
O1 N1 C13 C11 6.9(2) . . . . ?
C17 N1 C13 C11 -173.57(18) . . . . ?
C15 C14 C13 N1 -3.3(3) . . . . ?
C15 C14 C13 C11 175.97(18) . . . . ?
O2 C11 C13 N1 -56.9(2) . . . . ?
C10 C11 C13 N1 -174.14(16) . . . . ?
C12 C11 C13 N1 65.0(2) . . . . ?
O2 C11 C13 C14 123.76(19) . . . . ?
C10 C11 C13 C14 6.5(2) . . . . ?
C12 C11 C13 C14 -114.30(19) . . . . ?
C12 C7 C1 C2 -111.1(2) . . . . ?
C8 C7 C1 C2 125.4(2) . . . . ?
C12 C7 C1 C6 67.0(3) . . . . ?
C8 C7 C1 C6 -56.5(3) . . . . ?
O1 N1 C17 C16 175.7(2) . . . . ?
C13 N1 C17 C16 -3.9(3) . . . . ?
C15 C16 C17 N1 -0.7(4) . . . . ?
C11 C10 C9 O3 -142.6(2) . . . . ?
C11 C10 C9 C8 43.0(3) . . . . ?
C17 C16 C15 C14 3.0(3) . . . . ?
C13 C14 C15 C16 -1.0(3) . . . . ?
C2 C1 C6 C5 0.8(4) . . . . ?
C7 C1 C6 C5 -177.3(2) . . . . ?
C6 C1 C2 C3 -0.5(4) . . . . ?
C7 C1 C2 C3 177.6(2) . . . . ?
O3 C9 C8 C7 140.3(2) . . . . ?
C10 C9 C8 C7 -45.3(3) . . . . ?
C1 C7 C8 C9 178.25(19) . . . . ?
C12 C7 C8 C9 53.8(3) . . . . ?
C1 C6 C5 C4 0.1(4) . . . . ?
C1 C2 C3 C4 -0.7(5) . . . . ?
C2 C3 C4 C5 1.6(5) . . . . ?
C6 C5 C4 C3 -1.4(5) . . . . ?

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
O2 H2 O1 0.82 2.07 2.695(2) 132.6 .

_refine_diff_density_max         0.268
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.097

_shelxl_version_number           2013-4



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: petroleum ether and THF'
