# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 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_VA6
_database_code_depnum_ccdc_archive 'CCDC 1525301'
_audit_update_record             
;
2017-01-02 deposited with the CCDC.
2017-01-23 downloaded from the CCDC.
;
_audit_creation_date             2016-05-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.16 svn.r3265 for OlexSys, GUI svn.r5155)
;
_shelxl_version_number           2014-3
_chemical_name_common            VA6
_chemical_name_systematic        
;
N-(2-hydroxy-5-chlorophenyl)-2-propylpentanamide
;
_chemical_formula_moiety         'C14 H20 Cl N O2'
_chemical_formula_sum            'C14 H20 Cl N O2'
_chemical_formula_weight         269.76
_chemical_melting_point          399
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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.0054(4)
_cell_length_b                   8.7908(4)
_cell_length_c                   19.4618(9)
_cell_angle_alpha                90
_cell_angle_beta                 102.377(3)
_cell_angle_gamma                90
_cell_volume                     1504.88(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    50
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      55.158
_cell_measurement_theta_min      6.314
_shelx_estimated_absorpt_T_max   0.971
_shelx_estimated_absorpt_T_min   0.934
_exptl_absorpt_coefficient_mu    0.249
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.830122
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS v.2.10 (Bruker,2003) was used for absorption correction.
R(int) was 0.0270 before and 0.0269 after correction.
The Ratio of minimum to maximum transmission is 0.8301.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'rectangular prism'
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
Crystal was obtained in a 1:4 ethyl acetate, hexanes solvent mixture
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10105
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.579
_diffrn_reflns_theta_min         3.157
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2430
_reflns_number_total             3348
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
;
HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.017(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3348
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0551
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0771P)²+0.3639P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1470
_refine_ls_wR_factor_ref         0.1633
_refine_special_details          
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(Cl1) ∼ Ueq, Uanis(C11A) ∼ Ueq, Uanis(C11B) ∼ Ueq: with sigma
of 0.1 and sigma for terminal atoms of 0.2
3.a Idealised Me refined as rotating group:
 C11A(H11A,H11B,H11C), C11B(H11D,H11E,H11F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
C11A C 1.0395(4) 0.1067(6) 0.3015(2) 0.1414(15) Uani 1 1 d . U . . .
H11A H 1.0873 0.2048 0.3050 0.212 Uiso 1 1 calc GR . . . .
H11B H 1.0684 0.0496 0.2643 0.212 Uiso 1 1 calc GR . . . .
H11C H 1.0714 0.0532 0.3452 0.212 Uiso 1 1 calc GR . . . .
C10A C 0.8702(3) 0.1259(4) 0.28577(17) 0.0903(8) Uani 1 1 d . . . . .
C9A C 0.8139(3) 0.2274(3) 0.33881(12) 0.0704(6) Uani 1 1 d . . . . .
C8 C 0.6422(2) 0.2353(2) 0.32608(9) 0.0543(5) Uani 1 1 d . . . . .
C9B C 0.5850(3) 0.3270(3) 0.38217(11) 0.0657(5) Uani 1 1 d . . . . .
C10B C 0.4124(3) 0.3343(4) 0.37076(16) 0.0842(7) Uani 1 1 d . . . . .
C11B C 0.3527(4) 0.4331(4) 0.4217(2) 0.1175(11) Uani 1 1 d . U . . .
H11D H 0.3912 0.3974 0.4688 0.176 Uiso 1 1 calc GR . . . .
H11E H 0.2437 0.4290 0.4113 0.176 Uiso 1 1 calc GR . . . .
H11F H 0.3851 0.5362 0.4177 0.176 Uiso 1 1 calc GR . . . .
C7 C 0.57728(19) 0.30494(18) 0.25494(9) 0.0479(4) Uani 1 1 d . . . . .
C2 C 0.3756(2) 0.27495(17) 0.14745(8) 0.0479(4) Uani 1 1 d . . . . .
C1 C 0.4262(2) 0.3598(2) 0.09657(9) 0.0529(4) Uani 1 1 d . . . . .
C6 C 0.3214(3) 0.4032(2) 0.03620(10) 0.0643(5) Uani 1 1 d . . . . .
C5 C 0.1721(3) 0.3612(3) 0.02580(11) 0.0724(6) Uani 1 1 d . . . . .
C4 C 0.1240(2) 0.2758(3) 0.07601(12) 0.0717(6) Uani 1 1 d . . . . .
C3 C 0.2240(2) 0.2328(2) 0.13668(10) 0.0606(5) Uani 1 1 d . . . . .
N1 N 0.47304(17) 0.22359(17) 0.21091(8) 0.0506(4) Uani 1 1 d . . . . .
O2 O 0.61702(15) 0.43373(12) 0.23897(6) 0.0556(4) Uani 1 1 d . . . . .
O1 O 0.57367(18) 0.3987(2) 0.10117(9) 0.0721(5) Uani 1 1 d . . . . .
Cl1 Cl -0.06661(8) 0.22548(13) 0.06423(5) 0.1314(4) Uani 1 1 d . U . . .
H9AA H 0.854(2) 0.325(2) 0.3384(9) 0.046(5) Uiso 1 1 d . . . . .
H8 H 0.603(2) 0.128(2) 0.3249(9) 0.052(5) Uiso 1 1 d . . . . .
H9BA H 0.628(3) 0.429(3) 0.3842(11) 0.071(6) Uiso 1 1 d . . . . .
H1 H 0.450(2) 0.143(2) 0.2268(10) 0.056(5) Uiso 1 1 d . . . . .
H9BB H 0.626(3) 0.281(2) 0.4267(13) 0.065(6) Uiso 1 1 d . . . . .
H6 H 0.362(3) 0.460(3) 0.0038(13) 0.079(7) Uiso 1 1 d . . . . .
H3 H 0.191(3) 0.174(3) 0.1722(12) 0.072(6) Uiso 1 1 d . . . . .
H9AB H 0.849(3) 0.186(3) 0.3858(15) 0.096(8) Uiso 1 1 d . . . . .
H5 H 0.104(3) 0.391(3) -0.0168(14) 0.093(8) Uiso 1 1 d . . . . .
H10C H 0.375(3) 0.232(3) 0.3730(15) 0.099(9) Uiso 1 1 d . . . . .
H10D H 0.365(4) 0.381(4) 0.3232(19) 0.124(11) Uiso 1 1 d . . . . .
H10A H 0.849(3) 0.176(3) 0.2377(16) 0.102(9) Uiso 1 1 d . . . . .
H10B H 0.831(3) 0.010(4) 0.2836(16) 0.119(10) Uiso 1 1 d . . . . .
H1A H 0.604(3) 0.412(3) 0.1352(14) 0.078(9) Uiso 1 1 d . . . . .


_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
C11A H11A 0.9600 . ?
C11A H11B 0.9600 . ?
C11A H11C 0.9600 . ?
C11A C10A 1.499(4) . ?
C10A C9A 1.530(4) . ?
C10A H10A 1.02(3) . ?
C10A H10B 1.08(3) . ?
C9A C8 1.514(3) . ?
C9A H9AA 0.929(19) . ?
C9A H9AB 0.97(3) . ?
C8 C9B 1.532(3) . ?
C8 C7 1.512(2) . ?
C8 H8 1.005(19) . ?
C9B C10B 1.524(3) . ?
C9B H9BA 0.97(2) . ?
C9B H9BB 0.96(2) . ?
C10B C11B 1.503(4) . ?
C10B H10C 0.96(3) . ?
C10B H10D 1.02(4) . ?
C11B H11D 0.9600 . ?
C11B H11E 0.9600 . ?
C11B H11F 0.9600 . ?
C7 N1 1.335(2) . ?
C7 O2 1.247(2) . ?
C2 C1 1.392(2) . ?
C2 C3 1.387(3) . ?
C2 N1 1.426(2) . ?
C1 C6 1.394(3) . ?
C1 O1 1.356(2) . ?
C6 C5 1.367(3) . ?
C6 H6 0.94(2) . ?
C5 C4 1.374(3) . ?
C5 H5 0.95(3) . ?
C4 C3 1.376(3) . ?
C4 Cl1 1.739(2) . ?
C3 H3 0.96(2) . ?
N1 H1 0.82(2) . ?
O1 H1A 0.67(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H11A C11A H11B 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
C10A C11A H11A 109.5 . . ?
C10A C11A H11B 109.5 . . ?
C10A C11A H11C 109.5 . . ?
C11A C10A C9A 113.4(3) . . ?
C11A C10A H10A 102.6(16) . . ?
C11A C10A H10B 102.4(17) . . ?
C9A C10A H10A 110.1(16) . . ?
C9A C10A H10B 115.1(17) . . ?
H10A C10A H10B 112(2) . . ?
C10A C9A H9AA 110.0(11) . . ?
C10A C9A H9AB 109.2(16) . . ?
C8 C9A C10A 112.98(19) . . ?
C8 C9A H9AA 110.2(11) . . ?
C8 C9A H9AB 106.5(16) . . ?
H9AA C9A H9AB 108(2) . . ?
C9A C8 C9B 113.25(17) . . ?
C9A C8 H8 107.4(10) . . ?
C9B C8 H8 110.0(10) . . ?
C7 C8 C9A 110.45(17) . . ?
C7 C8 C9B 108.42(15) . . ?
C7 C8 H8 107.2(10) . . ?
C8 C9B H9BA 108.6(13) . . ?
C8 C9B H9BB 107.4(13) . . ?
C10B C9B C8 113.97(18) . . ?
C10B C9B H9BA 110.9(13) . . ?
C10B C9B H9BB 109.6(13) . . ?
H9BA C9B H9BB 106.1(19) . . ?
C9B C10B H10C 108.2(18) . . ?
C9B C10B H10D 111.5(19) . . ?
C11B C10B C9B 115.2(3) . . ?
C11B C10B H10C 109.2(18) . . ?
C11B C10B H10D 103.0(19) . . ?
H10C C10B H10D 110(3) . . ?
C10B C11B H11D 109.5 . . ?
C10B C11B H11E 109.5 . . ?
C10B C11B H11F 109.5 . . ?
H11D C11B H11E 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
N1 C7 C8 116.84(15) . . ?
O2 C7 C8 121.37(15) . . ?
O2 C7 N1 121.76(15) . . ?
C1 C2 N1 123.45(16) . . ?
C3 C2 C1 119.83(16) . . ?
C3 C2 N1 116.70(16) . . ?
C2 C1 C6 118.73(18) . . ?
O1 C1 C2 123.60(16) . . ?
O1 C1 C6 117.62(17) . . ?
C1 C6 H6 115.1(15) . . ?
C5 C6 C1 121.20(19) . . ?
C5 C6 H6 123.7(15) . . ?
C6 C5 C4 119.49(19) . . ?
C6 C5 H5 118.5(16) . . ?
C4 C5 H5 122.0(16) . . ?
C5 C4 C3 120.8(2) . . ?
C5 C4 Cl1 119.86(16) . . ?
C3 C4 Cl1 119.28(18) . . ?
C2 C3 H3 118.7(14) . . ?
C4 C3 C2 119.89(19) . . ?
C4 C3 H3 121.4(14) . . ?
C7 N1 C2 127.13(15) . . ?
C7 N1 H1 115.0(14) . . ?
C2 N1 H1 116.2(14) . . ?
C1 O1 H1A 107(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
C11A C10A C9A C8 -175.1(3) . . . . ?
C10A C9A C8 C9B 175.7(2) . . . . ?
C10A C9A C8 C7 -62.5(2) . . . . ?
C9A C8 C9B C10B -179.2(2) . . . . ?
C9A C8 C7 N1 124.67(19) . . . . ?
C9A C8 C7 O2 -56.9(2) . . . . ?
C8 C9B C10B C11B -175.6(2) . . . . ?
C8 C7 N1 C2 167.24(17) . . . . ?
C9B C8 C7 N1 -110.69(18) . . . . ?
C9B C8 C7 O2 67.8(2) . . . . ?
C7 C8 C9B C10B 57.9(2) . . . . ?
C2 C1 C6 C5 -1.4(3) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C1 C2 N1 C7 46.8(3) . . . . ?
C1 C6 C5 C4 0.6(3) . . . . ?
C6 C5 C4 C3 0.3(4) . . . . ?
C6 C5 C4 Cl1 178.53(18) . . . . ?
C5 C4 C3 C2 -0.4(4) . . . . ?
C3 C2 C1 C6 1.3(3) . . . . ?
C3 C2 C1 O1 -176.31(18) . . . . ?
C3 C2 N1 C7 -134.9(2) . . . . ?
N1 C2 C1 C6 179.54(16) . . . . ?
N1 C2 C1 O1 1.9(3) . . . . ?
N1 C2 C3 C4 -178.77(18) . . . . ?
O2 C7 N1 C2 -11.2(3) . . . . ?
O1 C1 C6 C5 176.37(19) . . . . ?
Cl1 C4 C3 C2 -178.61(16) . . . . ?

####################################################################### 
# 
# 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_VA2
_database_code_depnum_ccdc_archive 'CCDC 1525302'
_audit_update_record             
;
2017-01-02 deposited with the CCDC.
2017-01-23 downloaded from the CCDC.
;
_audit_creation_date             2016-05-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.16 svn.r3265 for OlexSys, GUI svn.r5155)
;
_shelxl_version_number           2014-3
_chemical_name_common            VA2
_chemical_name_systematic        
;
N-(4-methyl-2-hydroxyphenyl)-2-propylpentanamide
;
_chemical_formula_moiety         'C15 H23 N O2'
_chemical_formula_sum            'C15 H23 N O2'
_chemical_formula_weight         249.34
_chemical_melting_point          342.15
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 0.0000 0.0000 '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 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_symmetry_Int_Tables_number      14
_cell_length_a                   8.9236(5)
_cell_length_b                   8.7861(4)
_cell_length_c                   19.7125(10)
_cell_angle_alpha                90
_cell_angle_beta                 102.535(3)
_cell_angle_gamma                90
_cell_volume                     1508.69(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    50
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      8.42
_cell_measurement_theta_min      56.80
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.986
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.577444
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS v.2.10 (Bruker,2003) was used for absorption correction.
R(int) was 0.0507 before and 0.0461 after correction.
The Ratio of minimum to maximum transmission is 0.5774.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.098
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'rectangular prism'
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.075
_exptl_special_details           
;
Crystal was obtained in a 1:4 ethyl acetate, hexanes solvent mixture
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1127
_diffrn_reflns_av_unetI/netI     0.0701
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.913
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            22042
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.400
_diffrn_reflns_theta_min         4.210
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.913
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1803
_reflns_number_total             3457
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        
;
HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.015(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         3457
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.1490
_refine_ls_R_factor_gt           0.0681
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0575P)²+0.4201P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1371
_refine_ls_wR_factor_ref         0.1690
_refine_special_details          
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C11B) ∼ Ueq, Uanis(C11A) ∼ Ueq, Uanis(C10B) ∼ Ueq,
Uanis(C10A) ∼ Ueq, Uanis(C12) ∼ Ueq: with sigma of 0.1 and sigma for
terminal atoms of 0.2
3.a Secondary CH2 refined with riding coordinates:
 C10B(H10A,H10B), C10A(H10C,H10D)
3.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C11B(H11A,H11B,H11C), C11A(H11D,H11E,H11F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
C12 C 1.0462(3) 0.7131(5) 0.43993(18) 0.1129(12) Uani 1 1 d . U . . .
H12A H 1.1126 0.7994 0.4519 0.169 Uiso 1 1 calc GR . . . .
H12B H 1.0652 0.6663 0.3986 0.169 Uiso 1 1 calc GR . . . .
H12C H 1.0657 0.6409 0.4774 0.169 Uiso 1 1 calc GR . . . .
C4 C 0.8812(3) 0.7645(3) 0.42720(13) 0.0717(7) Uani 1 1 d . . . . .
C5 C 0.8258(3) 0.8518(3) 0.47439(14) 0.0750(8) Uani 1 1 d . . . . .
C6 C 0.6759(3) 0.8972(3) 0.46306(13) 0.0681(7) Uani 1 1 d . . . . .
C1 C 0.5717(3) 0.8552(2) 0.40292(12) 0.0561(6) Uani 1 1 d . . . . .
C2 C 0.6250(2) 0.7693(2) 0.35370(10) 0.0507(5) Uani 1 1 d . . . . .
C3 C 0.7776(3) 0.7251(3) 0.36674(13) 0.0611(6) Uani 1 1 d . . . . .
C11B C 0.6433(5) 0.9290(4) 0.0802(2) 0.1295(14) Uani 1 1 d . U . . .
H11A H 0.5984 0.8967 0.0337 0.194 Uiso 1 1 calc GR . . . .
H11B H 0.7531 0.9219 0.0880 0.194 Uiso 1 1 calc GR . . . .
H11C H 0.6145 1.0326 0.0864 0.194 Uiso 1 1 calc GR . . . .
C10B C 0.5870(3) 0.8289(3) 0.13106(17) 0.0888(9) Uani 1 1 d . U . . .
H10A H 0.6281 0.8667 0.1776 0.107 Uiso 1 1 calc R . . . .
H10B H 0.6273 0.7272 0.1282 0.107 Uiso 1 1 calc R . . . .
C9B C 0.4138(3) 0.8191(3) 0.12013(15) 0.0691(7) Uani 1 1 d . . . . .
C8 C 0.3588(3) 0.7261(3) 0.17589(12) 0.0579(6) Uani 1 1 d . . . . .
C9A C 0.1857(3) 0.7147(4) 0.16329(15) 0.0732(8) Uani 1 1 d . . . . .
C10A C 0.1290(3) 0.6143(4) 0.21516(18) 0.0950(10) Uani 1 1 d . U . . .
H10C H 0.1786 0.5158 0.2164 0.114 Uiso 1 1 calc R . . . .
H10D H 0.1606 0.6593 0.2610 0.114 Uiso 1 1 calc R . . . .
C11A C -0.0391(4) 0.5907(6) 0.2004(2) 0.1431(16) Uani 1 1 d . U . . .
H11D H -0.0897 0.6871 0.2006 0.215 Uiso 1 1 calc GR . . . .
H11E H -0.0650 0.5260 0.2353 0.215 Uiso 1 1 calc GR . . . .
H11F H -0.0717 0.5438 0.1556 0.215 Uiso 1 1 calc GR . . . .
C7 C 0.4230(2) 0.7980(2) 0.24594(11) 0.0524(6) Uani 1 1 d . . . . .
N1 N 0.5286(2) 0.7178(2) 0.29024(9) 0.0536(5) Uani 1 1 d . . . . .
O1 O 0.4218(2) 0.8959(2) 0.39613(10) 0.0730(5) Uani 1 1 d . . . . .
O2 O 0.38129(17) 0.92699(16) 0.26071(8) 0.0594(5) Uani 1 1 d . . . . .
H8 H 0.405(2) 0.624(3) 0.1760(11) 0.059(6) Uiso 1 1 d . . . . .
H1 H 0.554(2) 0.635(2) 0.2750(10) 0.041(6) Uiso 1 1 d . . . . .
H3 H 0.807(2) 0.666(2) 0.3324(11) 0.053(6) Uiso 1 1 d . . . . .
H1A H 0.384(3) 0.909(3) 0.3496(17) 0.089(9) Uiso 1 1 d . . . . .
H5 H 0.893(3) 0.884(3) 0.5161(14) 0.074(7) Uiso 1 1 d . . . . .
H6 H 0.635(3) 0.957(3) 0.4968(15) 0.088(8) Uiso 1 1 d . . . . .
H9AA H 0.150(3) 0.670(3) 0.1161(14) 0.079(8) Uiso 1 1 d . . . . .
H9BA H 0.367(3) 0.919(3) 0.1177(13) 0.080(8) Uiso 1 1 d . . . . .
H9AB H 0.139(3) 0.817(3) 0.1631(12) 0.063(7) Uiso 1 1 d . . . . .
H9BB H 0.371(3) 0.775(3) 0.0755(14) 0.076(8) Uiso 1 1 d . . . . .


_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
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C12 C4 1.508(4) . ?
C4 C5 1.378(4) . ?
C4 C3 1.384(3) . ?
C5 C6 1.367(4) . ?
C5 H5 0.95(3) . ?
C6 C1 1.388(3) . ?
C6 H6 0.98(3) . ?
C1 C2 1.392(3) . ?
C1 O1 1.362(3) . ?
C2 C3 1.386(3) . ?
C2 N1 1.429(3) . ?
C3 H3 0.94(2) . ?
C11B H11A 0.9600 . ?
C11B H11B 0.9600 . ?
C11B H11C 0.9600 . ?
C11B C10B 1.500(5) . ?
C10B H10A 0.9700 . ?
C10B H10B 0.9700 . ?
C10B C9B 1.516(4) . ?
C9B C8 1.533(4) . ?
C9B H9BA 0.97(3) . ?
C9B H9BB 0.96(3) . ?
C8 C9A 1.513(3) . ?
C8 C7 1.514(3) . ?
C8 H8 0.99(2) . ?
C9A C10A 1.518(4) . ?
C9A H9AA 0.99(3) . ?
C9A H9AB 0.99(2) . ?
C10A H10C 0.9700 . ?
C10A H10D 0.9700 . ?
C10A C11A 1.479(4) . ?
C11A H11D 0.9600 . ?
C11A H11E 0.9600 . ?
C11A H11F 0.9600 . ?
C7 N1 1.338(3) . ?
C7 O2 1.247(2) . ?
N1 H1 0.83(2) . ?
O1 H1A 0.91(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C4 C12 H12A 109.5 . . ?
C4 C12 H12B 109.5 . . ?
C4 C12 H12C 109.5 . . ?
C5 C4 C12 122.3(2) . . ?
C5 C4 C3 116.8(2) . . ?
C3 C4 C12 120.9(3) . . ?
C4 C5 H5 119.9(15) . . ?
C6 C5 C4 122.3(2) . . ?
C6 C5 H5 117.8(15) . . ?
C5 C6 C1 120.8(3) . . ?
C5 C6 H6 122.6(16) . . ?
C1 C6 H6 116.6(16) . . ?
C6 C1 C2 118.2(2) . . ?
O1 C1 C6 118.4(2) . . ?
O1 C1 C2 123.4(2) . . ?
C1 C2 N1 123.4(2) . . ?
C3 C2 C1 119.6(2) . . ?
C3 C2 N1 117.0(2) . . ?
C4 C3 C2 122.4(2) . . ?
C4 C3 H3 121.4(13) . . ?
C2 C3 H3 116.3(13) . . ?
H11A C11B H11B 109.5 . . ?
H11A C11B H11C 109.5 . . ?
H11B C11B H11C 109.5 . . ?
C10B C11B H11A 109.5 . . ?
C10B C11B H11B 109.5 . . ?
C10B C11B H11C 109.5 . . ?
C11B C10B H10A 108.6 . . ?
C11B C10B H10B 108.6 . . ?
C11B C10B C9B 114.7(3) . . ?
H10A C10B H10B 107.6 . . ?
C9B C10B H10A 108.6 . . ?
C9B C10B H10B 108.6 . . ?
C10B C9B C8 113.8(2) . . ?
C10B C9B H9BA 111.7(15) . . ?
C10B C9B H9BB 110.0(15) . . ?
C8 C9B H9BA 108.5(16) . . ?
C8 C9B H9BB 108.4(15) . . ?
H9BA C9B H9BB 104(2) . . ?
C9B C8 H8 106.7(13) . . ?
C9A C8 C9B 113.1(2) . . ?
C9A C8 C7 110.4(2) . . ?
C9A C8 H8 110.6(12) . . ?
C7 C8 C9B 108.34(19) . . ?
C7 C8 H8 107.5(12) . . ?
C8 C9A C10A 113.9(2) . . ?
C8 C9A H9AA 106.5(15) . . ?
C8 C9A H9AB 110.5(13) . . ?
C10A C9A H9AA 108.6(15) . . ?
C10A C9A H9AB 109.3(14) . . ?
H9AA C9A H9AB 108(2) . . ?
C9A C10A H10C 108.5 . . ?
C9A C10A H10D 108.5 . . ?
H10C C10A H10D 107.5 . . ?
C11A C10A C9A 114.9(3) . . ?
C11A C10A H10C 108.5 . . ?
C11A C10A H10D 108.5 . . ?
C10A C11A H11D 109.5 . . ?
C10A C11A H11E 109.5 . . ?
C10A C11A H11F 109.5 . . ?
H11D C11A H11E 109.5 . . ?
H11D C11A H11F 109.5 . . ?
H11E C11A H11F 109.5 . . ?
N1 C7 C8 116.7(2) . . ?
O2 C7 C8 121.28(19) . . ?
O2 C7 N1 122.0(2) . . ?
C2 N1 H1 115.7(13) . . ?
C7 N1 C2 127.56(19) . . ?
C7 N1 H1 115.3(13) . . ?
C1 O1 H1A 105.7(18) . . ?

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
C12 C4 C5 C6 -179.4(3) . . . . ?
C12 C4 C3 C2 179.4(3) . . . . ?
C4 C5 C6 C1 0.6(4) . . . . ?
C5 C4 C3 C2 -0.6(4) . . . . ?
C5 C6 C1 C2 -1.7(4) . . . . ?
C5 C6 C1 O1 176.2(2) . . . . ?
C6 C1 C2 C3 1.7(3) . . . . ?
C6 C1 C2 N1 179.3(2) . . . . ?
C1 C2 C3 C4 -0.6(4) . . . . ?
C1 C2 N1 C7 45.4(3) . . . . ?
C3 C4 C5 C6 0.5(4) . . . . ?
C3 C2 N1 C7 -137.0(2) . . . . ?
C11B C10B C9B C8 -175.6(3) . . . . ?
C10B C9B C8 C9A -178.8(2) . . . . ?
C10B C9B C8 C7 58.5(3) . . . . ?
C9B C8 C9A C10A 176.1(2) . . . . ?
C9B C8 C7 N1 -112.0(2) . . . . ?
C9B C8 C7 O2 66.6(3) . . . . ?
C8 C9A C10A C11A -175.0(3) . . . . ?
C8 C7 N1 C2 168.4(2) . . . . ?
C9A C8 C7 N1 123.7(2) . . . . ?
C9A C8 C7 O2 -57.7(3) . . . . ?
C7 C8 C9A C10A -62.4(3) . . . . ?
N1 C2 C3 C4 -178.3(2) . . . . ?
O1 C1 C2 C3 -176.1(2) . . . . ?
O1 C1 C2 N1 1.5(3) . . . . ?
O2 C7 N1 C2 -10.2(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_VA3
_database_code_depnum_ccdc_archive 'CCDC 1525303'
_audit_update_record             
;
2017-01-02 deposited with the CCDC.
2017-01-23 downloaded from the CCDC.
;
_audit_creation_date             2014-10-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874)
;
_shelxl_version_number           2014-3
_chemical_name_common            VA2
_chemical_name_systematic        
;
N-(5-methyl-2-hydroxyphenyl)-2-propylpentanamide
;
_chemical_formula_moiety         'C15 H23 N O2'
_chemical_formula_sum            'C15 H23 N O2'
_chemical_formula_weight         249.36
_chemical_melting_point          373.15
_chemical_absolute_configuration .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2

_symmetry_Int_Tables_number      19
_cell_length_a                   8.5924(17)
_cell_length_b                   12.938(3)
_cell_length_c                   14.250(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1584.1(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    50
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      8.42
_cell_measurement_theta_min      56.80
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.748388
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS v.2.10 (Bruker,2003) was used for absorption correction.
R(int) was 0.0353 before and 0.0316 after correction.
The Ratio of minimum to maximum transmission is 0.7484.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'dark yellow'
_exptl_crystal_density_diffrn    1.0455
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'rectangular prism'
_exptl_crystal_F_000             544.2481
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_special_details           
;
Crystal was obtained in a 1:4 ethyl acetate, hexanes solvent mixture
;
_diffrn_reflns_av_R_equivalents  0.0517
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            22986
_diffrn_reflns_theta_full        27.5545
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_min         4.87
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 0.9814
_diffrn_measured_fraction_theta_max 0.9782
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.979
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              16
_reflns_limit_k_min              -16
_reflns_limit_l_max              18
_reflns_limit_l_min              -18
_reflns_number_gt                2413
_reflns_number_total             3584
_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.
;
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        
;
HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2013)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.1860
_refine_diff_density_min         -0.1538
_refine_diff_density_rms         0.0355
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.6(10)
_refine_ls_d_res_high            0.7682
_refine_ls_d_res_low             4.1834
_refine_ls_goodness_of_fit_ref   1.0912
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    12
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3584
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.0939
_refine_ls_R_factor_gt           0.0558
_refine_ls_restrained_S_all      1.0864
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0527P)²+0.1098P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1151
_refine_ls_wR_factor_ref         0.1306
_refine_special_details          
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C12) ∼ Ueq, Uanis(C11a) ∼ Ueq, Uanis(C11b) ∼ Ueq, Uanis(C10a)
∼ Ueq, Uanis(C10b) ∼ Ueq: with sigma of 0.1 and sigma for terminal
atoms of 0.2
3.a Me refined with riding coordinates:
 C11b(H11a,H11b,H11c), C11a(H11d,H11e,H11f), C12(H12a,H12b,H12c)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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_refinement_flags_posn
_atom_site_refinement_flags_adp
C11b C 0.6797(5) 0.4379(2) 0.5597(2) 0.1401(12) Uani 1.000000 . U
H11a H 0.6933(5) 0.4328(2) 0.6264(2) 0.2101(18) Uiso 1.000000 R .
H11b H 0.6220(5) 0.3792(2) 0.5376(2) 0.2101(18) Uiso 1.000000 R .
H11c H 0.7797(5) 0.4395(2) 0.5296(2) 0.2101(18) Uiso 1.000000 R .
C10b C 0.5911(4) 0.5365(2) 0.5365(2) 0.1004(8) Uani 1.000000 . U
C9b C 0.5644(3) 0.55076(18) 0.43220(17) 0.0824(6) Uani 1.000000 . .
C8 C 0.4714(3) 0.64718(15) 0.40703(15) 0.0716(5) Uani 1.000000 . .
C9a C 0.4431(4) 0.6574(2) 0.30243(16) 0.0866(7) Uani 1.000000 . .
C10a C 0.3429(4) 0.7499(2) 0.27451(18) 0.1037(8) Uani 1.000000 . U
C11a C 0.3024(6) 0.7519(3) 0.1712(2) 0.1512(14) Uani 1.000000 . U
H11d H 0.2396(6) 0.8115(3) 0.1580(2) 0.227(2) Uiso 1.000000 R .
H11e H 0.3963(6) 0.7549(3) 0.1348(2) 0.227(2) Uiso 1.000000 R .
H11f H 0.2456(6) 0.6904(3) 0.1552(2) 0.227(2) Uiso 1.000000 R .
C7 C 0.5534(2) 0.74290(14) 0.44185(12) 0.0624(4) Uani 1.000000 . .
C2 C 0.5310(2) 0.89494(13) 0.54646(13) 0.0642(5) Uani 1.000000 . .
C3 C 0.4958(3) 0.90963(17) 0.63982(14) 0.0777(6) Uani 1.000000 . .
C4 C 0.5399(4) 0.99844(19) 0.68538(17) 0.0924(7) Uani 1.000000 . .
C5 C 0.6210(3) 1.07468(17) 0.63982(16) 0.0907(7) Uani 1.000000 . .
C6 C 0.6552(3) 1.06036(16) 0.54713(17) 0.0856(6) Uani 1.000000 . .
C1 C 0.6117(2) 0.97194(14) 0.49903(14) 0.0720(5) Uani 1.000000 . .
C12 C 0.6708(6) 1.1725(2) 0.6904(2) 0.1436(14) Uani 1.000000 . U
H12a H 0.6372(6) 1.1695(2) 0.7546(2) 0.215(2) Uiso 1.000000 R .
H12b H 0.7821(6) 1.1786(2) 0.6882(2) 0.215(2) Uiso 1.000000 R .
H12c H 0.6245(6) 1.2314(2) 0.6604(2) 0.215(2) Uiso 1.000000 R .
N1 N 0.4768(2) 0.80298(12) 0.50212(12) 0.0659(4) Uani 1.000000 . .
O2 O 0.68704(15) 0.76470(10) 0.41418(9) 0.0703(4) Uani 1.000000 . .
O1 O 0.6474(2) 0.96581(13) 0.40582(11) 0.0960(5) Uani 1.000000 . .
H3 H 0.434(2) 0.8561(15) 0.6719(12) 0.059(5) Uiso 1.000000 . .
H4 H 0.514(3) 1.0031(18) 0.751(2) 0.092(6) Uiso 1.000000 . .
H8 H 0.373(2) 0.6444(15) 0.4362(14) 0.073(5) Uiso 1.000000 . .
H6 H 0.716(3) 1.1090(18) 0.5145(17) 0.091(7) Uiso 1.000000 . .
H9ba H 0.510(3) 0.4914(17) 0.4019(16) 0.090(7) Uiso 1.000000 . .
H1a H 0.677(4) 0.891(2) 0.394(2) 0.122(9) Uiso 1.000000 . .
H9bb H 0.666(3) 0.5537(19) 0.3963(16) 0.099(7) Uiso 1.000000 . .
H9aa H 0.539(2) 0.6616(14) 0.2728(12) 0.058(5) Uiso 1.000000 . .
H9ab H 0.398(3) 0.596(2) 0.2829(17) 0.105(8) Uiso 1.000000 . .
H10c H 0.233(5) 0.747(3) 0.330(3) 0.167(13) Uiso 1.000000 . .
H1 H 0.395(3) 0.7825(16) 0.5253(14) 0.072(6) Uiso 1.000000 . .
H10d H 0.390(4) 0.814(3) 0.292(2) 0.126(10) Uiso 1.000000 . .
H10a H 0.643(4) 0.604(3) 0.565(2) 0.132(10) Uiso 1.000000 . .
H10b H 0.497(4) 0.530(2) 0.572(2) 0.117(10) Uiso 1.000000 . .


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
C11b H11a 0.9600 . ?
C11b H11b 0.9600 . ?
C11b H11c 0.9600 . ?
C11b C10b 1.522(4) . ?
C10b C9b 1.515(4) . ?
C10b H10a 1.06(3) . ?
C10b H10b 0.96(3) . ?
C9b C8 1.524(3) . ?
C9b H9ba 1.00(2) . ?
C9b H9bb 1.01(3) . ?
C8 C9a 1.516(3) . ?
C8 C7 1.509(3) . ?
C8 H8 0.94(2) . ?
C9a C10a 1.527(4) . ?
C9a H9aa 0.93(2) . ?
C9a H9ab 0.93(3) . ?
C10a C11a 1.513(4) . ?
C10a H10c 1.23(4) . ?
C10a H10d 0.96(3) . ?
C11a H11d 0.9600 . ?
C11a H11e 0.9600 . ?
C11a H11f 0.9600 . ?
C7 N1 1.333(2) . ?
C7 O2 1.246(2) . ?
C2 C3 1.378(3) . ?
C2 C1 1.389(3) . ?
C2 N1 1.425(2) . ?
C3 C4 1.373(3) . ?
C3 H3 0.985(19) . ?
C4 C5 1.371(4) . ?
C4 H4 0.97(3) . ?
C5 C6 1.366(3) . ?
C5 C12 1.518(3) . ?
C6 C1 1.385(3) . ?
C6 H6 0.94(2) . ?
C1 O1 1.365(3) . ?
C12 H12a 0.9600 . ?
C12 H12b 0.9600 . ?
C12 H12c 0.9600 . ?
N1 H1 0.82(2) . ?
O1 H1a 1.02(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H11b C11b H11a 109.5 . . ?
H11c C11b H11a 109.5 . . ?
H11c C11b H11b 109.5 . . ?
C10b C11b H11a 109.5 . . ?
C10b C11b H11b 109.5 . . ?
C10b C11b H11c 109.5 . . ?
C9b C10b C11b 113.0(2) . . ?
H10a C10b C11b 113.2(17) . . ?
H10a C10b C9b 110.2(16) . . ?
H10b C10b C11b 103.9(17) . . ?
H10b C10b C9b 113.3(18) . . ?
H10b C10b H10a 103(2) . . ?
C8 C9b C10b 114.2(2) . . ?
H9ba C9b C10b 113.7(13) . . ?
H9ba C9b C8 106.6(13) . . ?
H9bb C9b C10b 111.8(13) . . ?
H9bb C9b C8 107.6(14) . . ?
H9bb C9b H9ba 102.2(19) . . ?
C9a C8 C9b 112.74(19) . . ?
C7 C8 C9b 110.45(17) . . ?
C7 C8 C9a 109.09(18) . . ?
H8 C8 C9b 109.6(12) . . ?
H8 C8 C9a 107.1(12) . . ?
H8 C8 C7 107.8(12) . . ?
C10a C9a C8 114.5(2) . . ?
H9aa C9a C8 108.0(11) . . ?
H9aa C9a C10a 109.6(11) . . ?
H9ab C9a C8 106.6(15) . . ?
H9ab C9a C10a 111.2(17) . . ?
H9ab C9a H9aa 106(2) . . ?
C11a C10a C9a 113.4(3) . . ?
H10c C10a C9a 104.2(17) . . ?
H10c C10a C11a 116.5(17) . . ?
H10d C10a C9a 111.7(19) . . ?
H10d C10a C11a 110.0(17) . . ?
H10d C10a H10c 100(2) . . ?
H11d C11a C10a 109.5 . . ?
H11e C11a C10a 109.5 . . ?
H11e C11a H11d 109.5 . . ?
H11f C11a C10a 109.5 . . ?
H11f C11a H11d 109.5 . . ?
H11f C11a H11e 109.5 . . ?
N1 C7 C8 117.37(16) . . ?
O2 C7 C8 120.81(17) . . ?
O2 C7 N1 121.82(17) . . ?
C1 C2 C3 118.73(18) . . ?
N1 C2 C3 118.12(18) . . ?
N1 C2 C1 123.10(17) . . ?
C4 C3 C2 120.8(2) . . ?
H3 C3 C2 118.0(10) . . ?
H3 C3 C4 121.2(10) . . ?
C5 C4 C3 121.2(2) . . ?
H4 C4 C3 116.6(14) . . ?
H4 C4 C5 122.1(14) . . ?
C6 C5 C4 118.0(2) . . ?
C12 C5 C4 121.2(2) . . ?
C12 C5 C6 120.8(3) . . ?
C1 C6 C5 122.2(2) . . ?
H6 C6 C5 120.5(14) . . ?
H6 C6 C1 117.2(14) . . ?
C6 C1 C2 119.09(19) . . ?
O1 C1 C2 122.94(17) . . ?
O1 C1 C6 117.95(19) . . ?
H12a C12 C5 109.5 . . ?
H12b C12 C5 109.5 . . ?
H12b C12 H12a 109.5 . . ?
H12c C12 C5 109.5 . . ?
H12c C12 H12a 109.5 . . ?
H12c C12 H12b 109.5 . . ?
C2 N1 C7 127.65(17) . . ?
H1 N1 C7 119.6(14) . . ?
H1 N1 C2 111.8(14) . . ?
H1a O1 C1 105.9(16) . . ?


loop_
_restr_U_iso_atom_site_label
_restr_U_iso_weight_param
C11b 0.1000
C10b 0.1000
C10a 0.1000
C11a 0.1000
C12 0.1000











