# Electronic Supplementary Material (ESI) for Green Chemistry.
# 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_aaaa
_database_code_depnum_ccdc_archive 'CCDC 1871679'
loop_
_audit_author_name
_audit_author_address
'Dong-Liang Mo'
;Guangxi Normal University
China
;
_audit_update_record             
;
2020-05-03 deposited with the CCDC.	2020-08-20 downloaded from the CCDC.
;
_audit_creation_date             2018-05-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H13 N O'
_chemical_formula_sum            'C13 H13 N O'
_chemical_formula_weight         199.24
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.923(3)
_cell_length_b                   8.454(4)
_cell_length_c                   10.773(5)
_cell_angle_alpha                78.722(6)
_cell_angle_beta                 76.248(6)
_cell_angle_gamma                86.236(6)
_cell_volume                     513.8(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4504
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      1.00000
_cell_measurement_theta_min      0.10312
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.10000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             212
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   1.00000
_exptl_transmission_factor_min   0.10000
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6136
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.461
_diffrn_reflns_theta_min         1.981
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1903
_reflns_number_total             2125
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.425
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2125
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0507
_refine_ls_restrained_S_all      1.082
_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)+(0.0764P)²+0.1226P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1390
_refine_ls_wR_factor_ref         0.1435
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C7(H7), C10(H10), C13(H13), C14(H14)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_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
O1 O 0.13484(19) 0.98563(14) 0.81236(11) 0.0533(3) Uani 1 1 d . . . . .
N2 N 0.2570(2) 0.84375(15) 1.05833(12) 0.0422(3) Uani 1 1 d . . . . .
H2 H 0.1266 0.8947 1.0776 0.051 Uiso 1 1 calc R . . . .
C3 C 0.5800(2) 0.73927(15) 0.94043(14) 0.0367(3) Uani 1 1 d . . . . .
C4 C 0.3788(2) 0.82954(16) 0.93505(14) 0.0377(3) Uani 1 1 d . . . . .
C5 C 0.7447(2) 0.70036(17) 0.82174(14) 0.0413(4) Uani 1 1 d . . . . .
H5A H 0.7130 0.5938 0.8099 0.050 Uiso 1 1 calc R . . . .
H5B H 0.9028 0.6993 0.8326 0.050 Uiso 1 1 calc R . . . .
C6 C 0.4676(3) 0.8569(2) 0.69535(15) 0.0485(4) Uani 1 1 d . . . . .
H6A H 0.4616 0.9442 0.6228 0.058 Uiso 1 1 calc R . . . .
H6B H 0.4079 0.7617 0.6774 0.058 Uiso 1 1 calc R . . . .
C7 C 0.3266(3) 0.74157(18) 1.27993(15) 0.0492(4) Uani 1 1 d . . . . .
H7 H 0.1885 0.7818 1.3257 0.059 Uiso 1 1 calc R . . . .
C8 C 0.3102(2) 0.90054(17) 0.81613(14) 0.0400(3) Uani 1 1 d . . . . .
C9 C 0.5853(2) 0.69702(15) 1.07412(14) 0.0381(3) Uani 1 1 d . . . . .
C10 C 0.7444(3) 0.61357(19) 1.14271(16) 0.0481(4) Uani 1 1 d . . . . .
H10 H 0.8816 0.5703 1.0987 0.058 Uiso 1 1 calc R . . . .
C11 C 0.3790(2) 0.76304(16) 1.14437(14) 0.0392(3) Uani 1 1 d . . . . .
C12 C 0.7210(3) 0.8239(2) 0.70214(15) 0.0475(4) Uani 1 1 d . . . . .
H12 H 0.7845 0.9253 0.7089 0.057 Uiso 1 1 calc R . . . .
C13 C 0.6946(3) 0.5969(2) 1.27502(17) 0.0569(4) Uani 1 1 d . . . . .
H13 H 0.8006 0.5434 1.3209 0.068 Uiso 1 1 calc R . . . .
C14 C 0.4866(3) 0.6589(2) 1.34291(16) 0.0567(4) Uani 1 1 d . . . . .
H14 H 0.4563 0.6436 1.4331 0.068 Uiso 1 1 calc R . . . .
C15 C 0.8630(3) 0.7732(3) 0.57742(17) 0.0642(5) Uani 1 1 d . . . . .
H15A H 1.0238 0.7613 0.5808 0.096 Uiso 1 1 calc GR . . . .
H15B H 0.8465 0.8541 0.5039 0.096 Uiso 1 1 calc GR . . . .
H15C H 0.8078 0.6723 0.5693 0.096 Uiso 1 1 calc GR . . . .


_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
O1 C8 1.2280(18) . ?
N2 C4 1.3764(19) . ?
N2 C11 1.3615(19) . ?
C3 C4 1.3792(19) . ?
C3 C5 1.4914(19) . ?
C3 C9 1.422(2) . ?
C4 C8 1.443(2) . ?
C5 C12 1.520(2) . ?
C6 C8 1.505(2) . ?
C6 C12 1.525(2) . ?
C7 C11 1.396(2) . ?
C7 C14 1.371(3) . ?
C9 C10 1.404(2) . ?
C9 C11 1.419(2) . ?
C10 C13 1.366(2) . ?
C12 C15 1.529(2) . ?
C13 C14 1.402(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
C11 N2 C4 108.00(12) . . ?
C4 C3 C5 122.44(13) . . ?
C4 C3 C9 106.40(12) . . ?
C9 C3 C5 131.16(12) . . ?
N2 C4 C3 110.34(13) . . ?
N2 C4 C8 125.39(13) . . ?
C3 C4 C8 124.26(13) . . ?
C3 C5 C12 110.73(12) . . ?
C8 C6 C12 115.05(13) . . ?
C14 C7 C11 117.42(15) . . ?
O1 C8 C4 123.63(14) . . ?
O1 C8 C6 122.02(14) . . ?
C4 C8 C6 114.32(12) . . ?
C10 C9 C3 134.54(14) . . ?
C10 C9 C11 118.93(14) . . ?
C11 C9 C3 106.51(12) . . ?
C13 C10 C9 119.03(15) . . ?
N2 C11 C7 129.65(14) . . ?
N2 C11 C9 108.74(13) . . ?
C7 C11 C9 121.61(14) . . ?
C5 C12 C6 111.98(13) . . ?
C5 C12 C15 111.39(13) . . ?
C6 C12 C15 110.80(14) . . ?
C10 C13 C14 121.14(16) . . ?
C7 C14 C13 121.81(16) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
