# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_069
_database_code_depnum_ccdc_archive 'CCDC 1033762'
_audit_update_record             
;
2014-11-12 deposited with the CCDC.	2020-11-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H15 N O'
_chemical_formula_sum            'C11 H15 N O'
_chemical_formula_weight         177.24

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.418(2)
_cell_length_b                   6.5616(9)
_cell_length_c                   17.993(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.892(2)
_cell_angle_gamma                90.00
_cell_volume                     1931.3(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1072
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      23.55

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          .4
_exptl_crystal_size_mid          .4
_exptl_crystal_size_min          .1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.574865
_exptl_absorpt_correction_T_max  0.9
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10986
_diffrn_reflns_av_R_equivalents  0.0566
_diffrn_reflns_av_unetI/netI     0.0620
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.27
_diffrn_reflns_theta_max         25.05
_reflns_number_total             3401
_reflns_number_gt                1751
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0602P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3401
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1178
_refine_ls_R_factor_gt           0.0505
_refine_ls_wR_factor_ref         0.1383
_refine_ls_wR_factor_gt          0.1074
_refine_ls_goodness_of_fit_ref   0.964
_refine_ls_restrained_S_all      0.964
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5364(2) 0.2930(7) 0.66158(17) 0.0789(11) Uani 1 1 d . . .
H1C H 0.4896 0.2655 0.6304 0.095 Uiso 1 1 calc R . .
C2 C 0.54586(18) 0.4765(6) 0.69708(17) 0.0683(9) Uani 1 1 d . . .
H2C H 0.5038 0.5719 0.6923 0.082 Uiso 1 1 calc R . .
C3 C 0.5967(2) 0.1509(5) 0.67263(14) 0.0634(9) Uani 1 1 d . . .
H3 H 0.5891 0.0240 0.6500 0.076 Uiso 1 1 calc R . .
C4 C 0.61733(16) 0.5216(4) 0.74000(14) 0.0495(7) Uani 1 1 d . . .
H4 H 0.6233 0.6477 0.7634 0.059 Uiso 1 1 calc R . .
C5 C 0.66894(15) 0.1874(4) 0.71610(13) 0.0418(6) Uani 1 1 d . . .
C6 C 0.68038(14) 0.3806(4) 0.74856(12) 0.0358(6) Uani 1 1 d . . .
C7 C 0.72977(19) 0.0173(4) 0.73069(14) 0.0543(8) Uani 1 1 d . . .
H7 H 0.7081 -0.0987 0.7010 0.065 Uiso 1 1 calc R . .
C8 C 0.83101(14) 0.4214(4) 0.75831(13) 0.0417(6) Uani 1 1 d . . .
H8 H 0.8218 0.4745 0.7074 0.050 Uiso 1 1 calc R . .
C9 C 0.89186(15) 0.5595(5) 0.80284(15) 0.0638(8) Uani 1 1 d . . .
H9A H 0.8691 0.6938 0.8057 0.096 Uiso 1 1 calc R . .
H9B H 0.9417 0.5661 0.7786 0.096 Uiso 1 1 calc R . .
H9C H 0.9031 0.5056 0.8523 0.096 Uiso 1 1 calc R . .
C10 C 0.81374(18) 0.0587(4) 0.70577(16) 0.0632(9) Uani 1 1 d . . .
H10A H 0.8078 0.1127 0.6554 0.076 Uiso 1 1 calc R . .
H10B H 0.8431 -0.0692 0.7044 0.076 Uiso 1 1 calc R . .
C11 C 0.86430(16) 0.2066(4) 0.75512(15) 0.0569(8) Uani 1 1 d . . .
H11A H 0.9186 0.2134 0.7378 0.068 Uiso 1 1 calc R . .
H11B H 0.8699 0.1521 0.8054 0.068 Uiso 1 1 calc R . .
C12 C 0.95252(16) 0.2419(5) 0.54902(15) 0.0545(8) Uani 1 1 d . . .
H12 H 0.9924 0.1411 0.5540 0.065 Uiso 1 1 calc R . .
C13 C 0.96515(18) 0.4249(6) 0.58491(16) 0.0645(9) Uani 1 1 d . . .
H13 H 1.0132 0.4486 0.6148 0.077 Uiso 1 1 calc R . .
C14 C 0.88089(15) 0.2079(4) 0.50575(13) 0.0416(6) Uani 1 1 d . . .
H14 H 0.8731 0.0831 0.4817 0.050 Uiso 1 1 calc R . .
C15 C 0.9057(2) 0.5735(5) 0.57611(14) 0.0600(8) Uani 1 1 d . . .
H15 H 0.9146 0.6976 0.6004 0.072 Uiso 1 1 calc R . .
C16 C 0.81983(14) 0.3539(4) 0.49684(12) 0.0352(6) Uani 1 1 d . . .
C17 C 0.83254(16) 0.5436(4) 0.53193(13) 0.0441(7) Uani 1 1 d . . .
C18 C 0.7715(2) 0.7147(4) 0.52143(14) 0.0576(8) Uani 1 1 d . . .
H18 H 0.7930 0.8255 0.5539 0.069 Uiso 1 1 calc R . .
C19 C 0.68687(19) 0.6693(4) 0.54442(15) 0.0652(9) Uani 1 1 d . . .
H19A H 0.6575 0.7970 0.5472 0.078 Uiso 1 1 calc R . .
H19B H 0.6923 0.6109 0.5941 0.078 Uiso 1 1 calc R . .
C20 C 0.63585(17) 0.5260(4) 0.49331(15) 0.0589(8) Uani 1 1 d . . .
H20A H 0.6294 0.5864 0.4440 0.071 Uiso 1 1 calc R . .
H20B H 0.5819 0.5161 0.5112 0.071 Uiso 1 1 calc R . .
C21 C 0.66930(15) 0.3118(4) 0.48618(14) 0.0445(7) Uani 1 1 d . . .
H21 H 0.6788 0.2522 0.5361 0.053 Uiso 1 1 calc R . .
C22 C 0.60928(15) 0.1786(4) 0.43967(15) 0.0627(8) Uani 1 1 d . . .
H22A H 0.5994 0.2358 0.3906 0.094 Uiso 1 1 calc R . .
H22B H 0.5588 0.1714 0.4628 0.094 Uiso 1 1 calc R . .
H22C H 0.6316 0.0440 0.4361 0.094 Uiso 1 1 calc R . .
N1 N 0.75263(11) 0.4267(3) 0.79365(10) 0.0370(5) Uani 1 1 d . . .
H1A H 0.7468 0.5529 0.8120 0.044 Uiso 1 1 d R . .
N2 N 0.74755(11) 0.3135(3) 0.45062(10) 0.0380(5) Uani 1 1 d . . .
H2A H 0.7533 0.1903 0.4297 0.046 Uiso 1 1 d R . .
O1 O 0.73313(13) -0.0476(3) 0.80754(9) 0.0607(6) Uani 1 1 d . . .
H1 H 0.7376 0.0524 0.8349 0.091 Uiso 1 1 calc R . .
O2 O 0.76750(14) 0.7944(2) 0.44617(9) 0.0657(6) Uani 1 1 d . . .
H2 H 0.7589 0.7007 0.4163 0.099 Uiso 1 1 calc R . .


_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 C3 1.363(4) . ?
C1 C2 1.366(4) . ?
C2 C4 1.381(4) . ?
C3 C5 1.384(3) . ?
C4 C6 1.387(3) . ?
C5 C6 1.402(3) . ?
C5 C7 1.506(3) . ?
C6 N1 1.412(3) . ?
C7 O1 1.443(3) . ?
C7 C10 1.510(4) . ?
C8 N1 1.484(3) . ?
C8 C11 1.515(3) . ?
C8 C9 1.525(3) . ?
C10 C11 1.514(4) . ?
C12 C13 1.371(4) . ?
C12 C14 1.372(3) . ?
C13 C15 1.379(4) . ?
C14 C16 1.386(3) . ?
C15 C17 1.396(4) . ?
C16 C17 1.403(3) . ?
C16 N2 1.415(3) . ?
C17 C18 1.506(4) . ?
C18 O2 1.448(3) . ?
C18 C19 1.513(4) . ?
C19 C20 1.517(4) . ?
C20 C21 1.519(3) . ?
C21 N2 1.483(3) . ?
C21 C22 1.515(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
C3 C1 C2 118.9(3) . . ?
C1 C2 C4 120.5(3) . . ?
C1 C3 C5 122.7(3) . . ?
C2 C4 C6 120.7(3) . . ?
C3 C5 C6 118.0(3) . . ?
C3 C5 C7 119.6(3) . . ?
C6 C5 C7 122.3(2) . . ?
C4 C6 C5 119.0(2) . . ?
C4 C6 N1 120.2(2) . . ?
C5 C6 N1 120.6(2) . . ?
O1 C7 C5 110.9(2) . . ?
O1 C7 C10 112.1(2) . . ?
C5 C7 C10 115.1(2) . . ?
N1 C8 C11 111.5(2) . . ?
N1 C8 C9 108.3(2) . . ?
C11 C8 C9 110.5(2) . . ?
C7 C10 C11 114.2(2) . . ?
C10 C11 C8 115.9(2) . . ?
C13 C12 C14 119.8(3) . . ?
C12 C13 C15 119.2(3) . . ?
C12 C14 C16 122.0(3) . . ?
C13 C15 C17 122.2(3) . . ?
C14 C16 C17 118.9(2) . . ?
C14 C16 N2 120.1(2) . . ?
C17 C16 N2 121.0(2) . . ?
C15 C17 C16 117.9(3) . . ?
C15 C17 C18 119.8(3) . . ?
C16 C17 C18 122.2(2) . . ?
O2 C18 C17 111.3(2) . . ?
O2 C18 C19 110.9(2) . . ?
C17 C18 C19 115.8(2) . . ?
C18 C19 C20 115.4(2) . . ?
C19 C20 C21 116.1(2) . . ?
N2 C21 C22 108.2(2) . . ?
N2 C21 C20 111.2(2) . . ?
C22 C21 C20 111.0(2) . . ?
C6 N1 C8 117.76(18) . . ?
C16 N2 C21 117.50(18) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.036
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: PE/EtOAc'
