# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_cd16181
_audit_block_doi                 10.5517/ccdc.csd.cc1lx1cx
_database_code_depnum_ccdc_archive 'CCDC 1486709'
_audit_update_record             
;
2016-06-20 deposited with the CCDC.
2016-08-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
'2-(((propan-2-ylideneamino)oxy)methyl)phenyl benzoate'
_chemical_name_common            ?
_chemical_melting_point          345
_chemical_formula_moiety         ?
_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 0.0033 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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   12.049(3)
_cell_length_b                   7.1678(19)
_cell_length_c                   35.147(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3035.4(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1417
_cell_measurement_theta_min      4.636
_cell_measurement_theta_max      41.738

_exptl_crystal_description       prismatic
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_F_000             1200
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6359
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16093
_diffrn_reflns_av_unetI/netI     0.0625
_diffrn_reflns_av_R_equivalents  0.0783
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         2.049
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2827
_reflns_number_gt                1835
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          ', column chromatography'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0851P)²+0.2721P] 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       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2827
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0913
_refine_ls_R_factor_gt           0.0553
_refine_ls_wR_factor_ref         0.1661
_refine_ls_wR_factor_gt          0.1462
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.002
_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
N1 N 0.15668(16) 1.1464(3) 0.41713(5) 0.0564(6) Uani 1 1 d . . . . .
O1 O 0.09298(13) 1.1366(3) 0.38295(5) 0.0620(5) Uani 1 1 d . . . . .
O2 O -0.08599(12) 0.8213(3) 0.35668(4) 0.0587(5) Uani 1 1 d . . . . .
O3 O -0.26550(14) 0.8826(3) 0.34589(4) 0.0697(6) Uani 1 1 d . . . . .
C1 C -0.0214(2) 1.1599(4) 0.39309(8) 0.0679(8) Uani 1 1 d . . . . .
H1A H -0.0645 1.1790 0.3701 0.082 Uiso 1 1 calc R U . . .
H1B H -0.0288 1.2710 0.4086 0.082 Uiso 1 1 calc R U . . .
C2 C -0.06831(17) 0.9971(4) 0.41434(7) 0.0546(7) Uani 1 1 d . . . . .
C3 C -0.07784(19) 1.0009(5) 0.45384(7) 0.0741(9) Uani 1 1 d . . . . .
H3 H -0.0570 1.1077 0.4671 0.089 Uiso 1 1 calc R U . . .
C4 C -0.1175(2) 0.8495(7) 0.47359(8) 0.0918(12) Uani 1 1 d . . . . .
H4 H -0.1225 0.8541 0.5000 0.110 Uiso 1 1 calc R U . . .
C5 C -0.1497(2) 0.6921(6) 0.45463(8) 0.0901(12) Uani 1 1 d . . . . .
H5 H -0.1764 0.5899 0.4681 0.108 Uiso 1 1 calc R U . . .
C6 C -0.1427(2) 0.6847(5) 0.41554(8) 0.0726(8) Uani 1 1 d . . . . .
H6 H -0.1658 0.5787 0.4025 0.087 Uiso 1 1 calc R U . . .
C7 C -0.10135(17) 0.8346(4) 0.39617(6) 0.0525(7) Uani 1 1 d . . . . .
C8 C -0.17583(18) 0.8428(3) 0.33396(6) 0.0482(6) Uani 1 1 d . . . . .
C9 C -0.14818(18) 0.8115(3) 0.29348(6) 0.0435(6) Uani 1 1 d . . . . .
C10 C -0.22587(19) 0.8606(3) 0.26616(6) 0.0518(6) Uani 1 1 d . . . . .
H10 H -0.2933 0.9122 0.2736 0.062 Uiso 1 1 calc R U . . .
C11 C -0.2040(2) 0.8335(4) 0.22834(7) 0.0642(7) Uani 1 1 d . . . . .
H11 H -0.2566 0.8670 0.2102 0.077 Uiso 1 1 calc R U . . .
C12 C -0.1043(2) 0.7567(4) 0.21704(7) 0.0668(8) Uani 1 1 d . . . . .
H12 H -0.0896 0.7381 0.1913 0.080 Uiso 1 1 calc R U . . .
C13 C -0.0269(2) 0.7080(4) 0.24387(7) 0.0615(7) Uani 1 1 d . . . . .
H13 H 0.0403 0.6562 0.2363 0.074 Uiso 1 1 calc R U . . .
C14 C -0.04792(18) 0.7349(3) 0.28198(6) 0.0509(6) Uani 1 1 d . . . . .
H14 H 0.0051 0.7018 0.3000 0.061 Uiso 1 1 calc R U . . .
C15 C 0.2601(2) 1.1369(3) 0.41027(6) 0.0534(6) Uani 1 1 d . . . . .
C16 C 0.3352(2) 1.1466(5) 0.44394(8) 0.0740(8) Uani 1 1 d . . . . .
H16A H 0.2916 1.1579 0.4667 0.111 Uiso 1 1 calc R U . . .
H16B H 0.3831 1.2529 0.4416 0.111 Uiso 1 1 calc R U . . .
H16C H 0.3791 1.0350 0.4452 0.111 Uiso 1 1 calc R U . . .
C17 C 0.3130(2) 1.1184(4) 0.37207(7) 0.0716(8) Uani 1 1 d . . . . .
H17A H 0.2564 1.1115 0.3529 0.107 Uiso 1 1 calc R U . . .
H17B H 0.3571 1.0070 0.3714 0.107 Uiso 1 1 calc R U . . .
H17C H 0.3594 1.2248 0.3674 0.107 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
N1 C15 1.271(3) . ?
N1 O1 1.427(2) . ?
O1 C1 1.433(3) . ?
O2 C8 1.354(3) . ?
O2 C7 1.403(3) . ?
O3 C8 1.194(3) . ?
C1 C2 1.497(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C7 1.387(4) . ?
C2 C3 1.393(3) . ?
C3 C4 1.374(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.366(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.378(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.366(4) . ?
C6 H6 0.9300 . ?
C8 C9 1.478(3) . ?
C9 C14 1.387(3) . ?
C9 C10 1.386(3) . ?
C10 C11 1.369(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.381(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.371(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.377(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.491(3) . ?
C15 C17 1.492(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

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
C15 N1 O1 111.40(19) . . ?
N1 O1 C1 107.58(17) . . ?
C8 O2 C7 118.04(16) . . ?
O1 C1 C2 113.3(2) . . ?
O1 C1 H1A 108.9 . . ?
C2 C1 H1A 108.9 . . ?
O1 C1 H1B 108.9 . . ?
C2 C1 H1B 108.9 . . ?
H1A C1 H1B 107.7 . . ?
C7 C2 C3 116.9(3) . . ?
C7 C2 C1 122.2(2) . . ?
C3 C2 C1 120.9(3) . . ?
C4 C3 C2 121.1(3) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C5 C4 C3 120.3(3) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.1(3) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C7 C6 C5 119.3(3) . . ?
C7 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C6 C7 C2 122.4(2) . . ?
C6 C7 O2 119.2(2) . . ?
C2 C7 O2 118.3(2) . . ?
O3 C8 O2 122.9(2) . . ?
O3 C8 C9 125.3(2) . . ?
O2 C8 C9 111.73(18) . . ?
C14 C9 C10 119.1(2) . . ?
C14 C9 C8 122.5(2) . . ?
C10 C9 C8 118.4(2) . . ?
C11 C10 C9 120.5(2) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 120.2(2) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C13 C12 C11 119.7(2) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 120.6(2) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C13 C14 C9 119.9(2) . . ?
C13 C14 H14 120.0 . . ?
C9 C14 H14 120.0 . . ?
N1 C15 C16 116.2(2) . . ?
N1 C15 C17 126.4(2) . . ?
C16 C15 C17 117.4(2) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 N1 O1 C1 -176.5(2) . . . . ?
N1 O1 C1 C2 -70.0(3) . . . . ?
O1 C1 C2 C7 -79.0(3) . . . . ?
O1 C1 C2 C3 99.2(3) . . . . ?
C7 C2 C3 C4 0.4(3) . . . . ?
C1 C2 C3 C4 -177.9(2) . . . . ?
C2 C3 C4 C5 -0.7(4) . . . . ?
C3 C4 C5 C6 -0.1(5) . . . . ?
C4 C5 C6 C7 1.2(4) . . . . ?
C5 C6 C7 C2 -1.6(4) . . . . ?
C5 C6 C7 O2 175.0(2) . . . . ?
C3 C2 C7 C6 0.7(3) . . . . ?
C1 C2 C7 C6 179.0(2) . . . . ?
C3 C2 C7 O2 -175.8(2) . . . . ?
C1 C2 C7 O2 2.5(3) . . . . ?
C8 O2 C7 C6 79.8(3) . . . . ?
C8 O2 C7 C2 -103.6(2) . . . . ?
C7 O2 C8 O3 4.3(3) . . . . ?
C7 O2 C8 C9 -175.8(2) . . . . ?
O3 C8 C9 C14 -168.7(2) . . . . ?
O2 C8 C9 C14 11.5(3) . . . . ?
O3 C8 C9 C10 11.2(4) . . . . ?
O2 C8 C9 C10 -168.7(2) . . . . ?
C14 C9 C10 C11 0.1(3) . . . . ?
C8 C9 C10 C11 -179.8(2) . . . . ?
C9 C10 C11 C12 0.1(4) . . . . ?
C10 C11 C12 C13 -0.2(4) . . . . ?
C11 C12 C13 C14 0.0(4) . . . . ?
C12 C13 C14 C9 0.2(4) . . . . ?
C10 C9 C14 C13 -0.2(3) . . . . ?
C8 C9 C14 C13 179.6(2) . . . . ?
O1 N1 C15 C16 179.8(2) . . . . ?
O1 N1 C15 C17 0.1(4) . . . . ?

_refine_diff_density_max         0.172
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.043

_shelxl_version_number           2013-4



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method dichloromethane
_chemical_properties_physical    ', Moisture-sensitive'
_exptl_crystal_preparation       ', white solid'
