# Electronic Supplementary Material (ESI) for MedChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_aw_3
_database_code_depnum_ccdc_archive 'CCDC 1832675'
_audit_update_record             
;
2018-03-26 deposited with the CCDC.
2018-09-21 downloaded from the CCDC.
;

_audit_creation_date             2018-03-26T21:33:57-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
R-(-)-2-(2,6-dimethylphenoxy)-N-(1-hydroxypropan-2-yl)acetamide
;
_chemical_formula_moiety         'C13 H19 N O3'
_chemical_formula_sum            'C13 H19 N O3'
_chemical_formula_weight         237.29
_chemical_absolute_configuration ad

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
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                   7.3307(4)
_cell_length_b                   20.5418(9)
_cell_length_c                   8.5970(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1294.59(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    10755
_cell_measurement_theta_min      4.283
_cell_measurement_theta_max      71.421

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

_exptl_crystal_description       prism
_exptl_crystal_size_max          0.557
_exptl_crystal_size_mid          0.267
_exptl_crystal_size_min          0.137
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_F_000             512
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -6 -5 0.0631
0 6 5 0.0742
0 1 0 0.0879
0 -1 0 0.1527
-4 1 3 0.1946
3 -1 1 0.226
0 -1 1 0.0939
0 1 -1 0.1051
1 -8 4 0.088

_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.7
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.767
_exptl_absorpt_correction_T_max  0.91
_shelx_estimated_absorpt_T_min   0.696
_shelx_estimated_absorpt_T_max   0.91

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

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3756
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      0.0393073
_diffrn_orient_matrix_ub_12      0.0697522
_diffrn_orient_matrix_ub_13      -0.0569339
_diffrn_orient_matrix_ub_21      0.0180619
_diffrn_orient_matrix_ub_22      0.0229841
_diffrn_orient_matrix_ub_23      0.1697151
_diffrn_orient_matrix_ub_31      0.2057612
_diffrn_orient_matrix_ub_32      -0.015308
_diffrn_orient_matrix_ub_33      -0.0040796
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_number            19025
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.305
_diffrn_reflns_theta_max         71.622
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.99
_reflns_number_total             2497
_reflns_number_gt                2452
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

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

_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)+(0.0968P)²+2.5980P] where P=(Fo²+2Fc²)/3'
_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       0.0067(18)
_refine_ls_number_reflns         2497
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0968
_refine_ls_R_factor_gt           0.0952
_refine_ls_wR_factor_ref         0.2388
_refine_ls_wR_factor_gt          0.237
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 982 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.21(11)
_refine_diff_density_max         0.621
_refine_diff_density_min         -0.4
_refine_diff_density_rms         0.082

#----------------------------------------------------------------------------#
#                   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 0.0181 0.0091 '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 0.0311 0.018 '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'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.5057(6) 0.02312(18) 0.7825(5) 0.0421(11) Uani 1 d . .
O3 O 0.3010(6) 0.1702(2) 0.6546(7) 0.0595(15) Uani 1 d . .
O1 O -0.1469(6) 0.0645(3) 0.8118(8) 0.0626(15) Uani 1 d . .
C6 C 0.3327(7) 0.2372(3) 0.6639(6) 0.0331(12) Uani 1 d . .
N1 N 0.2134(7) 0.0553(3) 0.7560(7) 0.0474(14) Uani 1 d . .
C7 C 0.3595(8) 0.2690(3) 0.5248(7) 0.0439(15) Uani 1 d . .
C4 C 0.3904(8) 0.0649(3) 0.7458(7) 0.0396(13) Uani 1 d . .
C2 C 0.1219(8) -0.0026(3) 0.8134(7) 0.0380(13) Uani 1 d . .
H2 H 0.2056 -0.0254 0.8873 0.046 Uiso 1 calc . .
C5 C 0.4542(8) 0.1302(3) 0.6876(10) 0.0513(18) Uani 1 d . .
H5A H 0.5315 0.1514 0.7674 0.062 Uiso 1 calc . .
H5B H 0.5282 0.1245 0.5923 0.062 Uiso 1 calc . .
C1 C -0.0460(8) 0.0198(3) 0.9029(8) 0.0474(15) Uani 1 d . .
H1A H -0.1232 -0.0182 0.9288 0.057 Uiso 1 calc . .
H1B H -0.0081 0.0409 1.0013 0.057 Uiso 1 calc . .
C9 C 0.3776(10) 0.3644(4) 0.7090(11) 0.0567(19) Uani 1 d . .
H9 H 0.3952 0.4095 0.728 0.068 Uiso 1 calc . .
C11 C 0.3258(9) 0.2658(5) 0.8059(9) 0.065(2) Uani 1 d . .
C10 C 0.3490(11) 0.3275(5) 0.8254(15) 0.082(3) Uani 1 d . .
H10 H 0.3445 0.3456 0.9271 0.099 Uiso 1 calc . .
C3 C 0.0769(11) -0.0487(3) 0.6807(9) 0.0592(19) Uani 1 d . .
H3A H 0.1897 -0.0613 0.6272 0.089 Uiso 1 calc . .
H3B H -0.0048 -0.0269 0.607 0.089 Uiso 1 calc . .
H3C H 0.017 -0.0876 0.7221 0.089 Uiso 1 calc . .
C8 C 0.3853(9) 0.3419(5) 0.5491(14) 0.093(4) Uani 1 d . .
H8 H 0.4052 0.3709 0.4647 0.112 Uiso 1 calc . .
C13 C 0.3606(11) 0.2363(7) 0.3752(9) 0.105(5) Uani 1 d . .
H13A H 0.3827 0.2682 0.2926 0.157 Uiso 1 calc . .
H13B H 0.2424 0.2152 0.358 0.157 Uiso 1 calc . .
H13C H 0.4574 0.2034 0.3739 0.157 Uiso 1 calc . .
C12 C 0.2860(14) 0.2239(8) 0.9508(9) 0.125(6) Uani 1 d . .
H12A H 0.2693 0.1784 0.9195 0.187 Uiso 1 calc . .
H12B H 0.1747 0.2397 1.0015 0.187 Uiso 1 calc . .
H12C H 0.3886 0.2271 1.0235 0.187 Uiso 1 calc . .
H1N H 0.143(12) 0.087(4) 0.747(10) 0.07(3) Uiso 1 d . .
H1O H -0.259(17) 0.053(5) 0.781(16) 0.12(4) Uiso 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
O2 C4 1.245(7) . ?
O3 C6 1.398(7) . ?
O3 C5 1.419(7) . ?
O1 C1 1.414(7) . ?
C6 C11 1.356(9) . ?
C6 C7 1.377(8) . ?
N1 C4 1.315(8) . ?
N1 C2 1.452(7) . ?
C7 C13 1.451(12) . ?
C7 C8 1.524(13) . ?
C4 C5 1.507(8) . ?
C2 C3 1.520(9) . ?
C2 C1 1.522(9) . ?
C9 C10 1.272(14) . ?
C9 C8 1.451(15) . ?
C11 C10 1.291(13) . ?
C11 C12 1.541(15) . ?

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
C6 O3 C5 115.2(5) . . ?
C11 C6 C7 125.6(6) . . ?
C11 C6 O3 118.1(6) . . ?
C7 C6 O3 116.2(5) . . ?
C4 N1 C2 126.9(5) . . ?
C6 C7 C13 123.5(8) . . ?
C6 C7 C8 111.4(7) . . ?
C13 C7 C8 125.2(8) . . ?
O2 C4 N1 123.3(5) . . ?
O2 C4 C5 119.2(5) . . ?
N1 C4 C5 117.5(5) . . ?
N1 C2 C3 110.8(5) . . ?
N1 C2 C1 107.3(5) . . ?
C3 C2 C1 113.1(5) . . ?
O3 C5 C4 109.6(5) . . ?
O1 C1 C2 109.8(5) . . ?
C10 C9 C8 124.2(8) . . ?
C10 C11 C6 122.5(10) . . ?
C10 C11 C12 117.9(10) . . ?
C6 C11 C12 119.6(8) . . ?
C9 C10 C11 120.3(10) . . ?
C9 C8 C7 116.0(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 H1N O1 0.84(8) 2.25(9) 2.691(7) 113(7) .
O1 H1O O2 0.89(13) 1.83(12) 2.697(6) 163(12) 1_455
C9 H9 O2 0.95 2.45 3.372(8) 164.8 4_656
N1 H1N O1 0.84(8) 2.25(9) 2.691(7) 113(7) .
O1 H1O O2 0.89(13) 1.83(12) 2.697(6) 163(12) 1_455
N1 H1N O3 0.84(8) 2.20(9) 2.596(6) 109(7) .

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF

####################################################################### 
# 
# 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_aw_5x
_database_code_depnum_ccdc_archive 'CCDC 1832677'
_audit_update_record             
;
2018-03-26 deposited with the CCDC.
2018-09-21 downloaded from the CCDC.
;

_audit_creation_date             2016-10-28T21:18:35-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
R,S-2-(2,6-dimethylphenoxy)-N-(2-hydroxybutyl)acetamide
;
_chemical_formula_moiety         'C12 H20 N O3'
_chemical_formula_sum            'C14 H20 N O3'
_chemical_formula_weight         250.31
_chemical_absolute_configuration syn

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_Int_Tables_number      33
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   21.4310(13)
_cell_length_b                   8.4830(18)
_cell_length_c                   7.516(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1366.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3105
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.485

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.09
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             540
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 0 0.075
1 0 0 0.01
0 0 1 0.11
0 0 -1 0.11
0 1 -1 0.12
0 1 1 0.12
0 -1 0 0.18
2 -1 -1 0.05

_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   '(DENZO-SMN; Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.6071
_exptl_absorpt_correction_T_max  1

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

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_ub_11      0.0764411
_diffrn_orient_matrix_ub_12      0.0950857
_diffrn_orient_matrix_ub_13      -0.0064939
_diffrn_orient_matrix_ub_21      -0.1080045
_diffrn_orient_matrix_ub_22      0.0687606
_diffrn_orient_matrix_ub_23      0.0013599
_diffrn_orient_matrix_ub_31      0.0139273
_diffrn_orient_matrix_ub_32      0.0113443
_diffrn_orient_matrix_ub_33      0.0461882
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_reflns_av_R_equivalents  0.0982
_diffrn_reflns_number            6398
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.311
_diffrn_reflns_theta_max         27.385
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.795
_diffrn_measured_fraction_theta_max 0.831
_diffrn_reflns_Laue_measured_fraction_full 0.795
_diffrn_reflns_Laue_measured_fraction_max 0.831
_diffrn_reflns_point_group_measured_fraction_full 0.718
_diffrn_reflns_point_group_measured_fraction_max 0.768
_reflns_number_total             2386
_reflns_number_gt                1782
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep (Johnson, 1976)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

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

_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)+(0.0785P)²+1.3585P] where P=(Fo²+2Fc²)/3'
_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       0.023(9)
_refine_ls_number_reflns         2386
_refine_ls_number_parameters     186
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1133
_refine_ls_R_factor_gt           0.0851
_refine_ls_wR_factor_ref         0.215
_refine_ls_wR_factor_gt          0.1979
_refine_ls_goodness_of_fit_gt    3.032
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 533 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -2.4(10)
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.056

#----------------------------------------------------------------------------#
#                   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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.30695(18) 0.7404(6) 0.2943(6) 0.0323(10) Uani 1 d . .
O2 O 0.4574(2) 0.7300(7) 0.4960(6) 0.0392(12) Uani 1 d . .
N1 N 0.4250(2) 0.7162(9) 0.2112(7) 0.0374(14) Uani 1 d . .
C7 C 0.2447(2) 0.7062(8) 0.3381(8) 0.0286(12) Uani 1 d . .
C12 C 0.2034(3) 0.8326(8) 0.3614(8) 0.0317(13) Uani 1 d . .
C5 C 0.4155(3) 0.7288(8) 0.3846(9) 0.0309(13) Uani 1 d . .
C10 C 0.1218(3) 0.6420(9) 0.4112(9) 0.0363(14) Uani 1 d . .
H10 H 0.0803 0.6199 0.437 0.044 Uiso 1 calc . .
C11 C 0.1411(3) 0.7964(9) 0.3977(8) 0.0355(14) Uani 1 d . .
H11 H 0.1123 0.8774 0.413 0.043 Uiso 1 calc . .
C6 C 0.3481(3) 0.7382(9) 0.4446(8) 0.0342(14) Uani 1 d . .
H6A H 0.3385 0.6481 0.5191 0.041 Uiso 1 calc . .
H6B H 0.342 0.8329 0.5147 0.041 Uiso 1 calc . .
C14 C 0.2720(3) 0.4150(9) 0.3293(8) 0.0379(14) Uani 1 d . .
H14A H 0.2503 0.3167 0.3429 0.057 Uiso 1 calc . .
H14B H 0.304 0.423 0.4181 0.057 Uiso 1 calc . .
H14C H 0.2905 0.4198 0.2131 0.057 Uiso 1 calc . .
C9 C 0.1632(3) 0.5206(8) 0.3870(9) 0.0344(14) Uani 1 d . .
H9 H 0.1492 0.4171 0.3944 0.041 Uiso 1 calc . .
C13 C 0.2262(3) 0.9997(8) 0.3467(9) 0.0381(14) Uani 1 d . .
H13A H 0.2701 0.9998 0.3213 0.057 Uiso 1 calc . .
H13B H 0.2188 1.0537 0.4569 0.057 Uiso 1 calc . .
H13C H 0.2042 1.0523 0.2525 0.057 Uiso 1 calc . .
C8 C 0.2264(3) 0.5498(8) 0.3511(8) 0.0312(12) Uani 1 d . .
C4 C 0.4878(3) 0.7148(14) 0.1350(10) 0.064(3) Uani 1 d . .
H4A H 0.5066 0.6123 0.1544 0.077 Uiso 1 calc A 1
H4B H 0.5133 0.793 0.1948 0.077 Uiso 1 calc A 1
C2 C 0.5531(3) 0.7101(11) -0.1381(11) 0.051(2) Uani 1 d . .
H2A H 0.57 0.6185 -0.0776 0.061 Uiso 1 calc B 1
H2B H 0.5514 0.688 -0.2647 0.061 Uiso 1 calc B 1
C3 C 0.5921(5) 0.8492(11) -0.1039(14) 0.062(2) Uani 1 d . .
H3A H 0.6282 0.8462 -0.1795 0.093 Uiso 1 calc . .
H3B H 0.6051 0.8493 0.0184 0.093 Uiso 1 calc . .
H3C H 0.5686 0.943 -0.1281 0.093 Uiso 1 calc . .
C1A C 0.4863(7) 0.750(2) -0.065(2) 0.029(3) Uani 0.5 d C 1
H1A H 0.4787 0.8632 -0.0817 0.035 Uiso 0.5 calc C 1
O1A O 0.4377(4) 0.6636(14) -0.1524(13) 0.034(2) Uani 0.5 d C 1
H1OA H 0.4438 0.6843 -0.2616 0.051 Uiso 0.5 d C 1
C1B C 0.4906(6) 0.675(2) -0.040(2) 0.032(3) Uani 0.5 d C 2
H1B H 0.4822 0.5618 -0.0494 0.039 Uiso 0.5 calc C 2
O1B O 0.4445(6) 0.7557(16) -0.1385(15) 0.043(3) Uani 0.5 d C 2
H1OB H 0.4485 0.7479 -0.2507 0.065 Uiso 0.5 d C 2
H1 H 0.391(3) 0.716(8) 0.142(10) 0.021(17) Uiso 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
O3 C7 1.405(7) . ?
O3 C6 1.433(7) . ?
O2 C5 1.227(8) . ?
N1 C5 1.324(8) . ?
N1 C4 1.462(8) . ?
N1 H1 0.90(8) . ?
C7 C8 1.387(9) . ?
C7 C12 1.401(9) . ?
C12 C11 1.397(9) . ?
C12 C13 1.503(9) . ?
C5 C6 1.515(8) . ?
C10 C9 1.372(9) . ?
C10 C11 1.377(10) . ?
C10 H10 0.93 . ?
C11 H11 0.93 . ?
C6 H6A 0.97 . ?
C6 H6B 0.97 . ?
C14 C8 1.513(9) . ?
C14 H14A 0.96 . ?
C14 H14B 0.96 . ?
C14 H14C 0.96 . ?
C9 C8 1.401(8) . ?
C9 H9 0.93 . ?
C13 H13A 0.96 . ?
C13 H13B 0.96 . ?
C13 H13C 0.96 . ?
C4 C1B 1.357(18) . ?
C4 C1A 1.533(17) . ?
C4 H4A 0.97 . ?
C4 H4B 0.97 . ?
C2 C3 1.469(11) . ?
C2 C1B 1.560(15) . ?
C2 C1A 1.571(16) . ?
C2 H2A 0.97 . ?
C2 H2B 0.97 . ?
C3 H3A 0.96 . ?
C3 H3B 0.96 . ?
C3 H3C 0.96 . ?
C1A O1A 1.435(17) . ?
C1A H1A 0.98 . ?
O1A H1OA 0.85 . ?
C1B O1B 1.412(19) . ?
C1B H1B 0.98 . ?
O1B H1OB 0.85 . ?

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 O3 C6 113.4(4) . . ?
C5 N1 C4 121.9(5) . . ?
C5 N1 H1 117(5) . . ?
C4 N1 H1 121(5) . . ?
C8 C7 C12 123.0(5) . . ?
C8 C7 O3 118.9(5) . . ?
C12 C7 O3 118.1(6) . . ?
C11 C12 C7 117.3(6) . . ?
C11 C12 C13 122.2(6) . . ?
C7 C12 C13 120.5(6) . . ?
O2 C5 N1 124.0(6) . . ?
O2 C5 C6 119.6(6) . . ?
N1 C5 C6 116.4(5) . . ?
C9 C10 C11 120.6(6) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C10 C11 C12 120.7(6) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
O3 C6 C5 110.6(5) . . ?
O3 C6 H6A 109.5 . . ?
C5 C6 H6A 109.5 . . ?
O3 C6 H6B 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
C8 C14 H14A 109.5 . . ?
C8 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C8 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C10 C9 C8 121.2(6) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C7 C8 C9 117.1(6) . . ?
C7 C8 C14 122.2(5) . . ?
C9 C8 C14 120.7(6) . . ?
C1B C4 N1 114.9(8) . . ?
N1 C4 C1A 111.3(7) . . ?
N1 C4 H4A 109.4 . . ?
C1A C4 H4A 109.4 . . ?
N1 C4 H4B 109.4 . . ?
C1A C4 H4B 109.4 . . ?
H4A C4 H4B 108 . . ?
C3 C2 C1B 124.0(9) . . ?
C3 C2 C1A 106.4(9) . . ?
C3 C2 H2A 110.4 . . ?
C1A C2 H2A 110.4 . . ?
C3 C2 H2B 110.4 . . ?
C1A C2 H2B 110.4 . . ?
H2A C2 H2B 108.6 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O1A C1A C4 111.3(12) . . ?
O1A C1A C2 113.0(12) . . ?
C4 C1A C2 106.4(11) . . ?
O1A C1A H1A 108.7 . . ?
C4 C1A H1A 108.7 . . ?
C2 C1A H1A 108.7 . . ?
C1A O1A H1OA 103 . . ?
C4 C1B O1B 111.0(13) . . ?
C4 C1B C2 116.7(12) . . ?
O1B C1B C2 105.0(13) . . ?
C4 C1B H1B 107.9 . . ?
O1B C1B H1B 107.9 . . ?
C2 C1B H1B 107.9 . . ?
C1B O1B H1OB 114.4 . . ?

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
O1A H1OA O2 0.85 1.89 2.735(11) 180 1_554
O1B H1OB O2 0.85 1.92 2.769(12) 179.8 1_554
N1 H1 O3 0.90(8) 2.14(7) 2.614(7) 112(6) .

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_aw_4
_database_code_depnum_ccdc_archive 'CCDC 1832676'
_audit_update_record             
;
2018-03-26 deposited with the CCDC.
2018-09-21 downloaded from the CCDC.
;

_audit_creation_date             2018-03-26T17:20:34-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
S-(+)-2-(2,6-dimethylphenoxy)-N-(1-hydroxypropan-2-yl)acetamide
;
_chemical_formula_moiety         'C13 H19 N O3'
_chemical_formula_sum            'C13 H19 N O3'
_chemical_formula_weight         237.29
_chemical_absolute_configuration ad

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
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                   7.3182(8)
_cell_length_b                   20.524(2)
_cell_length_c                   8.5965(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1291.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5104
_cell_measurement_theta_min      4.3053
_cell_measurement_theta_max      72.3484

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

_exptl_crystal_description       prism
_exptl_crystal_size_max          0.338
_exptl_crystal_size_mid          0.215
_exptl_crystal_size_min          0.101
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_F_000             512
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.702
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.59531
_exptl_absorpt_correction_T_max  1

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

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_detector_area_resol_mean 10.3756
_diffrn_orient_matrix_ub_11      0.060916
_diffrn_orient_matrix_ub_12      -0.1191942
_diffrn_orient_matrix_ub_13      0.0517419
_diffrn_orient_matrix_ub_21      0.1132858
_diffrn_orient_matrix_ub_22      -0.0863284
_diffrn_orient_matrix_ub_23      -0.0517324
_diffrn_orient_matrix_ub_31      0.1662466
_diffrn_orient_matrix_ub_32      0.1025826
_diffrn_orient_matrix_ub_33      0.0166478
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0741
_diffrn_reflns_av_unetI/netI     0.0614
_diffrn_reflns_number            18683
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.308
_diffrn_reflns_theta_max         72.531
_diffrn_reflns_theta_full        67.68
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.981
_reflns_number_total             2497
_reflns_number_gt                2237
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

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

_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)+(0.1039P)²+1.9885P] where P=(Fo²+2Fc²)/3'
_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       0.0066(19)
_refine_ls_number_reflns         2497
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0998
_refine_ls_R_factor_gt           0.0913
_refine_ls_wR_factor_ref         0.2408
_refine_ls_wR_factor_gt          0.2315
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 849 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.12(18)
_refine_diff_density_max         0.543
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.081

#----------------------------------------------------------------------------#
#                   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 0.0181 0.0091 '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 0.0311 0.018 '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'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.0452(8) 0.9803(3) 0.0977(8) 0.0522(16) Uani 1 d . .
H1A H 1.0081 0.9597 0.0012 0.063 Uiso 1 calc . .
H1B H 1.1208 1.0176 0.0723 0.063 Uiso 1 calc . .
C2 C 0.8776(8) 1.0027(3) 0.1862(7) 0.0427(13) Uani 1 d . .
H2 H 0.7953 1.0251 0.1138 0.051 Uiso 1 calc . .
C3 C 0.9220(11) 1.0486(3) 0.3198(9) 0.0630(19) Uani 1 d . .
H3A H 0.9818 1.0868 0.28 0.094 Uiso 1 calc . .
H3B H 1.0011 1.027 0.3924 0.094 Uiso 1 calc . .
H3C H 0.811 1.0611 0.3714 0.094 Uiso 1 calc . .
C4 C 0.6100(8) 0.9351(3) 0.2537(8) 0.0442(14) Uani 1 d . .
C5 C 0.5456(8) 0.8696(3) 0.3106(11) 0.0573(19) Uani 1 d . .
H5A H 0.4717 0.8751 0.4034 0.069 Uiso 1 calc . .
H5B H 0.4709 0.849 0.2315 0.069 Uiso 1 calc . .
C6 C 0.6673(7) 0.7629(3) 0.3362(6) 0.0367(12) Uani 1 d . .
C7 C 0.6409(7) 0.7309(3) 0.4748(7) 0.0477(15) Uani 1 d . .
C8 C 0.6142(9) 0.6588(5) 0.4539(14) 0.098(4) Uani 1 d . .
H8 H 0.5947 0.6308 0.5374 0.118 Uiso 1 calc . .
C9 C 0.6212(10) 0.6355(3) 0.2909(11) 0.0607(19) Uani 1 d . .
H9 H 0.6025 0.5913 0.2725 0.073 Uiso 1 calc . .
C10 C 0.6512(11) 0.6722(5) 0.1747(14) 0.085(3) Uani 1 d . .
H10 H 0.657 0.6544 0.0754 0.102 Uiso 1 calc . .
C11 C 0.6738(9) 0.7341(5) 0.1933(9) 0.069(2) Uani 1 d . .
C12 C 0.7140(14) 0.7762(9) 0.0496(9) 0.134(6) Uani 1 d . .
H12A H 0.7275 0.8208 0.0806 0.2 Uiso 1 calc . .
H12B H 0.6148 0.7725 -0.0229 0.2 Uiso 1 calc . .
H12C H 0.8249 0.7615 0.0013 0.2 Uiso 1 calc . .
C13 C 0.6403(11) 0.7642(7) 0.6241(9) 0.107(4) Uani 1 d . .
H13A H 0.6198 0.7332 0.7058 0.161 Uiso 1 calc . .
H13B H 0.5448 0.7963 0.6252 0.161 Uiso 1 calc . .
H13C H 0.7561 0.7853 0.6398 0.161 Uiso 1 calc . .
N1 N 0.7866(7) 0.9445(2) 0.2445(7) 0.0521(14) Uani 1 d . .
O1 O 1.1471(6) 0.9356(3) 0.1885(8) 0.0664(15) Uani 1 d . .
O2 O 0.4943(5) 0.97661(18) 0.2173(5) 0.0475(11) Uani 1 d . .
O3 O 0.6997(6) 0.8296(2) 0.3448(7) 0.0652(15) Uani 1 d . .
H1N H 0.861(11) 0.909(4) 0.256(9) 0.07(2) Uiso 1 d . .
H1O H 1.248(16) 0.950(5) 0.213(15) 0.11(4) Uiso 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 O1 1.417(7) . ?
C1 C2 1.515(9) . ?
C2 N1 1.457(7) . ?
C2 C3 1.521(9) . ?
C4 O2 1.242(7) . ?
C4 N1 1.309(8) . ?
C4 C5 1.505(8) . ?
C5 O3 1.426(7) . ?
C6 C11 1.364(9) . ?
C6 C7 1.374(8) . ?
C6 O3 1.391(7) . ?
C7 C13 1.455(11) . ?
C7 C8 1.502(13) . ?
C8 C9 1.482(15) . ?
C9 C10 1.271(13) . ?
C10 C11 1.291(13) . ?
C11 C12 1.536(15) . ?

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
O1 C1 C2 110.3(5) . . ?
N1 C2 C1 107.1(5) . . ?
N1 C2 C3 110.3(5) . . ?
C1 C2 C3 113.2(5) . . ?
O2 C4 N1 123.8(5) . . ?
O2 C4 C5 118.7(5) . . ?
N1 C4 C5 117.5(5) . . ?
O3 C5 C4 109.5(5) . . ?
C11 C6 C7 125.4(6) . . ?
C11 C6 O3 117.9(6) . . ?
C7 C6 O3 116.6(6) . . ?
C6 C7 C13 122.7(8) . . ?
C6 C7 C8 112.6(7) . . ?
C13 C7 C8 124.7(8) . . ?
C9 C8 C7 115.3(7) . . ?
C10 C9 C8 123.8(8) . . ?
C9 C10 C11 120.6(10) . . ?
C10 C11 C6 122.2(9) . . ?
C10 C11 C12 118.6(9) . . ?
C6 C11 C12 119.2(8) . . ?
C4 N1 C2 126.4(5) . . ?
C6 O3 C5 114.9(4) . . ?

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 H1N O1 0.91(8) 2.24(8) 2.688(7) 110(6) .
O1 H1O O2 0.82(12) 1.89(11) 2.688(6) 166(13) 1_655
C9 H9 O2 0.93 2.46 3.369(8) 165.7 4_645
N1 H1N O3 0.91(8) 2.16(8) 2.591(6) 108(6) .

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF

_shelxl_version_number           2013-4

