# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_exp_2848
_database_code_depnum_ccdc_archive 'CCDC 1536185'
_audit_update_record             
;
2017-03-06 deposited with the CCDC.	2021-08-24 downloaded from the CCDC.
;
_audit_creation_date             2017-03-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H15 N O2'
_chemical_formula_sum            'C13 H15 N O2'
_chemical_formula_weight         217.26
_chemical_melting_point          ?
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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.8238(3)
_cell_length_b                   14.8389(7)
_cell_length_c                   10.8490(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.975(3)
_cell_angle_gamma                90
_cell_volume                     1090.41(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1831
_cell_measurement_temperature    104.9
_cell_measurement_theta_max      29.5705
_cell_measurement_theta_min      3.2997
_shelx_estimated_absorpt_T_max   0.965
_shelx_estimated_absorpt_T_min   0.961
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99179
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.4
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4531
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         3.306
_diffrn_ambient_temperature      104.9
_diffrn_detector                 'Image Plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            'Rigaku IP'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   12.00   86.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       18.7335   77.0000   30.0000 74

#__ type_ start__ end____ width___ exp.time_
  2 omega   30.00   86.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       18.7335   37.0000    0.0000 56

#__ type_ start__ end____ width___ exp.time_
  3 omega  -33.00   21.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       18.7335  -77.0000 -120.0000 54

#__ type_ start__ end____ width___ exp.time_
  4 omega   51.00   81.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       18.7335   37.0000  -60.0000 30
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku R-AXIS SPIDER IP'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0238038000
_diffrn_orient_matrix_UB_12      -0.0408271000
_diffrn_orient_matrix_UB_13      0.0287347000
_diffrn_orient_matrix_UB_21      0.1013499000
_diffrn_orient_matrix_UB_22      -0.0069218000
_diffrn_orient_matrix_UB_23      0.0212208000
_diffrn_orient_matrix_UB_31      -0.0113643000
_diffrn_orient_matrix_UB_32      0.0238649000
_diffrn_orient_matrix_UB_33      0.0553574000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1817
_reflns_number_total             2146
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0396
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0381P)²+0.2959P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0877
_refine_ls_wR_factor_ref         0.0930
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Riding coordinates:
 N1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C13(H13A,H13B), C11(H11A,H11B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C6(H6)
;
_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
O2 O 0.15055(13) 0.89740(6) 0.05339(9) 0.0184(2) Uani 1 1 d . . . . .
O1 O -0.27248(13) 0.88350(6) 0.28276(8) 0.0159(2) Uani 1 1 d . . . . .
N1 N -0.12539(16) 0.95392(8) 0.12238(10) 0.0157(3) Uani 1 1 d . . . . .
H1 H -0.1396 0.9927 0.0631 0.019 Uiso 1 1 d R . . . .
C2 C 0.0551(2) 0.84142(9) 0.24441(12) 0.0158(3) Uani 1 1 d . . . . .
C4 C -0.0967(2) 0.77413(9) 0.41306(13) 0.0190(3) Uani 1 1 d . . . . .
H4 H -0.2075 0.7670 0.4574 0.023 Uiso 1 1 calc R . . . .
C9 C -0.1323(2) 1.03386(9) 0.32124(12) 0.0161(3) Uani 1 1 d . . . . .
H9A H -0.0067 1.0059 0.3575 0.019 Uiso 1 1 calc R . . . .
H9B H -0.1002 1.0902 0.2792 0.019 Uiso 1 1 calc R . . . .
C3 C -0.1037(2) 0.83375(9) 0.31356(12) 0.0159(3) Uani 1 1 d . . . . .
C10 C -0.2565(2) 1.05622(10) 0.42491(13) 0.0188(3) Uani 1 1 d . . . . .
H10A H -0.1847 1.0999 0.4828 0.023 Uiso 1 1 calc R . . . .
H10B H -0.2784 1.0008 0.4722 0.023 Uiso 1 1 calc R . . . .
C13 C -0.44242(19) 1.00560(10) 0.17589(12) 0.0165(3) Uani 1 1 d . . . . .
H13A H -0.5137 0.9594 0.1219 0.020 Uiso 1 1 calc R . . . .
H13B H -0.4264 1.0596 0.1244 0.020 Uiso 1 1 calc R . . . .
C5 C 0.0748(2) 0.72529(10) 0.44623(13) 0.0223(3) Uani 1 1 d . . . . .
H5 H 0.0815 0.6850 0.5146 0.027 Uiso 1 1 calc R . . . .
C1 C 0.03436(19) 0.90011(9) 0.13305(12) 0.0149(3) Uani 1 1 d . . . . .
C11 C -0.4554(2) 1.09606(10) 0.37199(13) 0.0195(3) Uani 1 1 d . . . . .
H11A H -0.4342 1.1538 0.3300 0.023 Uiso 1 1 calc R . . . .
H11B H -0.5356 1.1083 0.4403 0.023 Uiso 1 1 calc R . . . .
C7 C 0.2265(2) 0.79137(9) 0.27911(13) 0.0184(3) Uani 1 1 d . . . . .
H7 H 0.3356 0.7964 0.2328 0.022 Uiso 1 1 calc R . . . .
C12 C -0.5657(2) 1.03053(10) 0.27932(13) 0.0185(3) Uani 1 1 d . . . . .
H12A H -0.5984 0.9752 0.3235 0.022 Uiso 1 1 calc R . . . .
H12B H -0.6911 1.0585 0.2425 0.022 Uiso 1 1 calc R . . . .
C8 C -0.24000(19) 0.96962(9) 0.22575(12) 0.0146(3) Uani 1 1 d . . . . .
C6 C 0.2376(2) 0.73435(9) 0.38090(13) 0.0213(3) Uani 1 1 d . . . . .
H6 H 0.3553 0.7016 0.4060 0.026 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
O2 C1 1.2424(16) . ?
O1 C3 1.3748(16) . ?
O1 C8 1.4484(16) . ?
N1 H1 0.8600 . ?
N1 C1 1.3449(17) . ?
N1 C8 1.4617(16) . ?
C2 C3 1.3954(19) . ?
C2 C1 1.4820(19) . ?
C2 C7 1.3979(19) . ?
C4 H4 0.9500 . ?
C4 C3 1.3921(19) . ?
C4 C5 1.386(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.5248(18) . ?
C9 C8 1.5286(19) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.5268(19) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C12 1.5275(18) . ?
C13 C8 1.5180(18) . ?
C5 H5 0.9500 . ?
C5 C6 1.395(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.5294(19) . ?
C7 H7 0.9500 . ?
C7 C6 1.386(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C6 H6 0.9500 . ?

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 O1 C8 114.23(10) . . ?
C1 N1 H1 118.6 . . ?
C1 N1 C8 122.15(11) . . ?
C8 N1 H1 116.4 . . ?
C3 C2 C1 118.86(12) . . ?
C3 C2 C7 119.38(12) . . ?
C7 C2 C1 121.72(13) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C5 C4 C3 118.80(13) . . ?
H9A C9 H9B 107.9 . . ?
C10 C9 H9A 109.3 . . ?
C10 C9 H9B 109.3 . . ?
C10 C9 C8 111.79(11) . . ?
C8 C9 H9A 109.3 . . ?
C8 C9 H9B 109.3 . . ?
O1 C3 C2 120.52(12) . . ?
O1 C3 C4 118.58(12) . . ?
C4 C3 C2 120.88(13) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 C11 110.80(11) . . ?
H10A C10 H10B 108.1 . . ?
C11 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
H13A C13 H13B 107.8 . . ?
C12 C13 H13A 109.1 . . ?
C12 C13 H13B 109.1 . . ?
C8 C13 H13A 109.1 . . ?
C8 C13 H13B 109.1 . . ?
C8 C13 C12 112.46(11) . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.13(13) . . ?
C6 C5 H5 119.4 . . ?
O2 C1 N1 122.57(12) . . ?
O2 C1 C2 122.83(12) . . ?
N1 C1 C2 114.54(12) . . ?
C10 C11 H11A 109.6 . . ?
C10 C11 H11B 109.6 . . ?
C10 C11 C12 110.19(11) . . ?
H11A C11 H11B 108.1 . . ?
C12 C11 H11A 109.6 . . ?
C12 C11 H11B 109.6 . . ?
C2 C7 H7 119.9 . . ?
C6 C7 C2 120.13(14) . . ?
C6 C7 H7 119.9 . . ?
C13 C12 C11 111.45(11) . . ?
C13 C12 H12A 109.3 . . ?
C13 C12 H12B 109.3 . . ?
C11 C12 H12A 109.3 . . ?
C11 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
O1 C8 N1 108.11(10) . . ?
O1 C8 C9 110.29(10) . . ?
O1 C8 C13 106.42(10) . . ?
N1 C8 C9 111.19(11) . . ?
N1 C8 C13 109.34(11) . . ?
C13 C8 C9 111.33(11) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 C5 119.59(13) . . ?
C7 C6 H6 120.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C7 C6 C5 1.8(2) . . . . ?
C4 C5 C6 C7 -1.7(2) . . . . ?
C9 C10 C11 C12 57.43(15) . . . . ?
C3 O1 C8 N1 51.70(13) . . . . ?
C3 O1 C8 C9 -70.06(13) . . . . ?
C3 O1 C8 C13 169.06(10) . . . . ?
C3 C2 C1 O2 -165.49(12) . . . . ?
C3 C2 C1 N1 11.81(18) . . . . ?
C3 C2 C7 C6 0.4(2) . . . . ?
C3 C4 C5 C6 -0.7(2) . . . . ?
C10 C9 C8 O1 -64.19(14) . . . . ?
C10 C9 C8 N1 175.89(10) . . . . ?
C10 C9 C8 C13 53.71(15) . . . . ?
C10 C11 C12 C13 -56.08(15) . . . . ?
C5 C4 C3 O1 -178.58(12) . . . . ?
C5 C4 C3 C2 3.0(2) . . . . ?
C1 N1 C8 O1 -45.74(15) . . . . ?
C1 N1 C8 C9 75.46(15) . . . . ?
C1 N1 C8 C13 -161.21(12) . . . . ?
C1 C2 C3 O1 -3.44(19) . . . . ?
C1 C2 C3 C4 174.95(12) . . . . ?
C1 C2 C7 C6 -177.34(12) . . . . ?
C7 C2 C3 O1 178.79(11) . . . . ?
C7 C2 C3 C4 -2.8(2) . . . . ?
C7 C2 C1 O2 12.2(2) . . . . ?
C7 C2 C1 N1 -170.48(12) . . . . ?
C12 C13 C8 O1 67.84(13) . . . . ?
C12 C13 C8 N1 -175.62(11) . . . . ?
C12 C13 C8 C9 -52.37(15) . . . . ?
C8 O1 C3 C2 -30.19(16) . . . . ?
C8 O1 C3 C4 151.38(11) . . . . ?
C8 N1 C1 O2 -168.22(12) . . . . ?
C8 N1 C1 C2 14.47(17) . . . . ?
C8 C9 C10 C11 -56.65(15) . . . . ?
C8 C13 C12 C11 54.10(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
