# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1960650'
loop_
_audit_author_name
_audit_author_address
'Sheng-Jiao Yan'
;School of Chemical Science and Technology, Yunnan University
China
;
_audit_update_record             
;
2019-10-22 deposited with the CCDC.	2019-11-25 downloaded from the CCDC.
;
_audit_creation_date             2019-10-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H12 N2 O'
_chemical_formula_sum            'C9 H12 N2 O'
_chemical_formula_weight         164.21
_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/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                   6.4219(12)
_cell_length_b                   10.741(2)
_cell_length_c                   13.507(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.887(3)
_cell_angle_gamma                90
_cell_volume                     926.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    364
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      18.9892
_cell_measurement_theta_min      2.4276
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.979
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.981324
_exptl_absorpt_correction_T_min  0.401939
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2004/1 (Bruker,2004) was used for absorption correction. R(int) was 0.0536 before and 0.0345 after correction. The Ratio of minimum to maximum transmission is 0.4019. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.177
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0704
_diffrn_reflns_av_unetI/netI     0.0801
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5110
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        24.972
_diffrn_reflns_theta_max         24.972
_diffrn_reflns_theta_min         3.032
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 60
_diffrn_standards_number         1
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                783
_reflns_number_total             1621
_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       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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    'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_diff_density_max         0.123
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.034(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.900
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     113
_refine_ls_number_reflns         1621
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1226
_refine_ls_R_factor_gt           0.0500
_refine_ls_restrained_S_all      0.900
_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)+(0.0523P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1279
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(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:
 C2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.2448(3) 0.05880(15) -0.04904(12) 0.0641(6) Uani 1 1 d . . . . .
N1 N 0.1259(3) 0.09332(18) 0.10080(14) 0.0547(6) Uani 1 1 d . . . . .
H1 H 0.026954 0.039941 0.088176 0.066 Uiso 1 1 calc R . . . .
N2 N 0.6789(4) 0.2437(3) -0.07151(19) 0.1032(10) Uani 1 1 d . . . . .
C1 C 0.2633(4) 0.1081(2) 0.03327(19) 0.0506(7) Uani 1 1 d . . . . .
C2 C 0.4493(4) 0.1888(2) 0.07020(17) 0.0523(7) Uani 1 1 d . . . . .
H2 H 0.536316 0.139557 0.119546 0.063 Uiso 1 1 calc R . . . .
C3 C 0.3812(4) 0.3068(2) 0.12433(17) 0.0531(7) Uani 1 1 d . . . . .
C4 C 0.2527(4) 0.2595(2) 0.20419(17) 0.0577(7) Uani 1 1 d . . . . .
H4 H 0.258009 0.302158 0.264309 0.069 Uiso 1 1 calc R . . . .
C5 C 0.1337(4) 0.1599(3) 0.19143(17) 0.0512(7) Uani 1 1 d . . . . .
C6 C 0.5792(4) 0.2173(2) -0.0107(2) 0.0648(8) Uani 1 1 d . . . . .
C7 C 0.2466(4) 0.3899(2) 0.05046(19) 0.0746(9) Uani 1 1 d . . . . .
H7A H 0.322104 0.407830 -0.005645 0.112 Uiso 1 1 calc GR . . . .
H7B H 0.215000 0.466260 0.082653 0.112 Uiso 1 1 calc GR . . . .
H7C H 0.118763 0.347454 0.028226 0.112 Uiso 1 1 calc GR . . . .
C8 C 0.5745(4) 0.3771(3) 0.16979(19) 0.0798(10) Uani 1 1 d . . . . .
H8A H 0.653549 0.324959 0.217605 0.120 Uiso 1 1 calc GR . . . .
H8B H 0.531711 0.451082 0.202108 0.120 Uiso 1 1 calc GR . . . .
H8C H 0.659804 0.399601 0.118217 0.120 Uiso 1 1 calc GR . . . .
C9 C -0.0035(4) 0.1079(3) 0.26406(18) 0.0691(8) Uani 1 1 d . . . . .
H9A H -0.145503 0.104887 0.233967 0.104 Uiso 1 1 calc GR . . . .
H9B H 0.004316 0.159988 0.322084 0.104 Uiso 1 1 calc GR . . . .
H9C H 0.042389 0.025383 0.282844 0.104 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 C1 1.226(3) . ?
N1 H1 0.8600 . ?
N1 C1 1.342(3) . ?
N1 C5 1.414(3) . ?
N2 C6 1.128(3) . ?
C1 C2 1.518(3) . ?
C2 H2 0.9800 . ?
C2 C3 1.548(3) . ?
C2 C6 1.473(3) . ?
C3 C4 1.512(3) . ?
C3 C7 1.537(3) . ?
C3 C8 1.527(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.316(3) . ?
C5 C9 1.493(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 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
C1 N1 H1 117.9 . . ?
C1 N1 C5 124.1(2) . . ?
C5 N1 H1 117.9 . . ?
O1 C1 N1 123.7(2) . . ?
O1 C1 C2 123.0(2) . . ?
N1 C1 C2 113.2(2) . . ?
C1 C2 H2 106.8 . . ?
C1 C2 C3 111.8(2) . . ?
C3 C2 H2 106.8 . . ?
C6 C2 C1 111.2(2) . . ?
C6 C2 H2 106.8 . . ?
C6 C2 C3 112.9(2) . . ?
C4 C3 C2 105.27(19) . . ?
C4 C3 C7 110.3(2) . . ?
C4 C3 C8 111.1(2) . . ?
C7 C3 C2 109.63(19) . . ?
C8 C3 C2 109.7(2) . . ?
C8 C3 C7 110.7(2) . . ?
C3 C4 H4 118.9 . . ?
C5 C4 C3 122.1(2) . . ?
C5 C4 H4 118.9 . . ?
N1 C5 C9 114.1(2) . . ?
C4 C5 N1 119.5(2) . . ?
C4 C5 C9 126.3(2) . . ?
N2 C6 C2 177.3(3) . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 C8 H8A 109.5 . . ?
C3 C8 H8B 109.5 . . ?
C3 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 C9 H9A 109.5 . . ?
C5 C9 H9B 109.5 . . ?
C5 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 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
O1 C1 C2 C3 137.5(2) . . . . ?
O1 C1 C2 C6 10.2(4) . . . . ?
N1 C1 C2 C3 -44.6(3) . . . . ?
N1 C1 C2 C6 -171.8(2) . . . . ?
C1 N1 C5 C4 14.3(4) . . . . ?
C1 N1 C5 C9 -166.7(2) . . . . ?
C1 C2 C3 C4 54.2(2) . . . . ?
C1 C2 C3 C7 -64.4(3) . . . . ?
C1 C2 C3 C8 173.8(2) . . . . ?
C2 C3 C4 C5 -33.8(3) . . . . ?
C3 C4 C5 N1 0.7(4) . . . . ?
C3 C4 C5 C9 -178.1(2) . . . . ?
C5 N1 C1 O1 -173.0(2) . . . . ?
C5 N1 C1 C2 9.1(3) . . . . ?
C6 C2 C3 C4 -179.5(2) . . . . ?
C6 C2 C3 C7 61.8(3) . . . . ?
C6 C2 C3 C8 -59.9(3) . . . . ?
C7 C3 C4 C5 84.4(3) . . . . ?
C8 C3 C4 C5 -152.5(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_180908ysj_0m
_database_code_depnum_ccdc_archive 'CCDC 1960651'
loop_
_audit_author_name
_audit_author_address
'Sheng-Jiao Yan'
;School of Chemical Science and Technology, Yunnan University
China
;
_audit_update_record             
;
2019-10-22 deposited with the CCDC.	2019-11-25 downloaded from the CCDC.
;
_audit_creation_date             2019-10-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H16 N2 O'
_chemical_formula_sum            'C15 H16 N2 O'
_chemical_formula_weight         240.30
_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 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 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                   7.3319(11)
_cell_length_b                   11.5409(16)
_cell_length_c                   16.169(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.147(2)
_cell_angle_gamma                90
_cell_volume                     1350.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1902
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      23.718
_cell_measurement_theta_min      2.178
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6809
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/3 (Bruker,2014/3) was used for absorption correction. wR2(int) was 0.0798 before and 0.0374 after correction. The Ratio of minimum to maximum transmission is 0.9132. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8001
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.783
_diffrn_reflns_theta_min         2.552
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '/w scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 60
_diffrn_standards_number         1
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2027
_reflns_number_total             3095
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         3095
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0473
_refine_ls_restrained_S_all      1.020
_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)+(0.0727P)²+0.0025P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1176
_refine_ls_wR_factor_ref         0.1354
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C15(H15)
2.d X=CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.e Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.45614(14) 0.59888(9) 0.56814(7) 0.0471(3) Uani 1 1 d . . . . .
N1 N 0.75927(15) 0.56569(10) 0.61576(7) 0.0359(3) Uani 1 1 d . . . . .
N2 N 0.4133(2) 0.86708(13) 0.47585(10) 0.0616(4) Uani 1 1 d . . . . .
C1 C 0.61817(19) 0.62006(12) 0.56485(9) 0.0345(3) Uani 1 1 d . . . . .
C2 C 0.95183(19) 0.58517(12) 0.61411(9) 0.0381(4) Uani 1 1 d . . . . .
C3 C 0.9929(2) 0.65801(14) 0.54285(11) 0.0468(4) Uani 1 1 d . . . . .
H3A H 0.982806 0.610312 0.492933 0.056 Uiso 1 1 calc R . . . .
H3B H 1.119265 0.685495 0.555485 0.056 Uiso 1 1 calc R . . . .
C4 C 0.8638(2) 0.76228(13) 0.52474(10) 0.0444(4) Uani 1 1 d . . . . .
C5 C 0.66913(18) 0.70819(12) 0.50186(9) 0.0369(3) Uani 1 1 d . . . . .
H5 H 0.667118 0.666964 0.448733 0.044 Uiso 1 1 calc R . . . .
C6 C 0.5229(2) 0.79656(14) 0.48759(10) 0.0428(4) Uani 1 1 d . . . . .
C7 C 0.8735(3) 0.84176(14) 0.60111(13) 0.0623(5) Uani 1 1 d . . . . .
H7A H 0.791153 0.906081 0.587630 0.093 Uiso 1 1 calc GR . . . .
H7B H 0.997509 0.869873 0.616572 0.093 Uiso 1 1 calc GR . . . .
H7C H 0.838067 0.799172 0.647015 0.093 Uiso 1 1 calc GR . . . .
C8 C 0.9109(3) 0.82989(18) 0.44944(14) 0.0749(6) Uani 1 1 d . . . . .
H8A H 0.897299 0.780160 0.401251 0.112 Uiso 1 1 calc GR . . . .
H8B H 1.036029 0.857073 0.461543 0.112 Uiso 1 1 calc GR . . . .
H8C H 0.828819 0.894821 0.438298 0.112 Uiso 1 1 calc GR . . . .
C9 C 1.0818(2) 0.53835(15) 0.67036(11) 0.0550(5) Uani 1 1 d . . . . .
H9A H 1.049194 0.491386 0.712415 0.066 Uiso 1 1 calc R . . . .
H9B H 1.205657 0.552416 0.667831 0.066 Uiso 1 1 calc R . . . .
C10 C 0.70718(19) 0.48434(12) 0.67604(9) 0.0359(3) Uani 1 1 d . . . . .
C11 C 0.7158(2) 0.36769(13) 0.66054(10) 0.0437(4) Uani 1 1 d . . . . .
H11 H 0.753988 0.341290 0.611706 0.052 Uiso 1 1 calc R . . . .
C12 C 0.6671(2) 0.28970(15) 0.71837(11) 0.0553(5) Uani 1 1 d . . . . .
H12 H 0.673778 0.210483 0.708732 0.066 Uiso 1 1 calc R . . . .
C13 C 0.6087(3) 0.32925(17) 0.79000(11) 0.0574(5) Uani 1 1 d . . . . .
H13 H 0.575466 0.276553 0.828494 0.069 Uiso 1 1 calc R . . . .
C14 C 0.5992(3) 0.44608(16) 0.80514(10) 0.0562(5) Uani 1 1 d . . . . .
H14 H 0.559022 0.472296 0.853562 0.067 Uiso 1 1 calc R . . . .
C15 C 0.6496(2) 0.52463(15) 0.74820(9) 0.0476(4) Uani 1 1 d . . . . .
H15 H 0.644783 0.603801 0.758353 0.057 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
O1 C1 1.2223(16) . ?
N1 C1 1.3678(18) . ?
N1 C2 1.4341(17) . ?
N1 C10 1.4477(17) . ?
N2 C6 1.138(2) . ?
C1 C5 1.5272(19) . ?
C2 C3 1.495(2) . ?
C2 C9 1.323(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.530(2) . ?
C4 C5 1.548(2) . ?
C4 C7 1.531(2) . ?
C4 C8 1.531(2) . ?
C5 H5 0.9800 . ?
C5 C6 1.471(2) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9300 . ?
C9 H9B 0.9300 . ?
C10 C11 1.373(2) . ?
C10 C15 1.3828(19) . ?
C11 H11 0.9300 . ?
C11 C12 1.385(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.375(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.374(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.383(2) . ?
C15 H15 0.9300 . ?

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
C1 N1 C2 124.72(12) . . ?
C1 N1 C10 116.58(11) . . ?
C2 N1 C10 118.69(11) . . ?
O1 C1 N1 121.97(13) . . ?
O1 C1 C5 120.31(13) . . ?
N1 C1 C5 117.71(12) . . ?
N1 C2 C3 114.95(13) . . ?
C9 C2 N1 121.77(14) . . ?
C9 C2 C3 123.24(14) . . ?
C2 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
C2 C3 C4 113.31(12) . . ?
H3A C3 H3B 107.7 . . ?
C4 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
C3 C4 C5 104.32(12) . . ?
C3 C4 C7 111.64(14) . . ?
C3 C4 C8 110.02(13) . . ?
C7 C4 C5 110.93(12) . . ?
C7 C4 C8 110.40(15) . . ?
C8 C4 C5 109.35(14) . . ?
C1 C5 C4 115.04(12) . . ?
C1 C5 H5 106.9 . . ?
C4 C5 H5 106.9 . . ?
C6 C5 C1 108.46(11) . . ?
C6 C5 C4 112.30(12) . . ?
C6 C5 H5 106.9 . . ?
N2 C6 C5 178.04(17) . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C2 C9 H9A 120.0 . . ?
C2 C9 H9B 120.0 . . ?
H9A C9 H9B 120.0 . . ?
C11 C10 N1 119.23(12) . . ?
C11 C10 C15 120.86(14) . . ?
C15 C10 N1 119.90(13) . . ?
C10 C11 H11 120.3 . . ?
C10 C11 C12 119.32(14) . . ?
C12 C11 H11 120.3 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.08(16) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.48(16) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.87(15) . . ?
C15 C14 H14 120.1 . . ?
C10 C15 C14 119.39(15) . . ?
C10 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?

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
O1 C1 C5 C4 157.45(13) . . . . ?
O1 C1 C5 C6 30.77(18) . . . . ?
N1 C1 C5 C4 -23.39(18) . . . . ?
N1 C1 C5 C6 -150.08(13) . . . . ?
N1 C2 C3 C4 41.80(19) . . . . ?
N1 C10 C11 C12 179.63(13) . . . . ?
N1 C10 C15 C14 179.66(14) . . . . ?
C1 N1 C2 C3 -8.8(2) . . . . ?
C1 N1 C2 C9 173.31(15) . . . . ?
C1 N1 C10 C11 102.87(16) . . . . ?
C1 N1 C10 C15 -77.12(17) . . . . ?
C2 N1 C1 O1 178.93(12) . . . . ?
C2 N1 C1 C5 -0.2(2) . . . . ?
C2 N1 C10 C11 -78.07(17) . . . . ?
C2 N1 C10 C15 101.93(16) . . . . ?
C2 C3 C4 C5 -61.00(17) . . . . ?
C2 C3 C4 C7 58.86(18) . . . . ?
C2 C3 C4 C8 -178.19(15) . . . . ?
C3 C4 C5 C1 51.48(16) . . . . ?
C3 C4 C5 C6 176.19(12) . . . . ?
C7 C4 C5 C1 -68.86(16) . . . . ?
C7 C4 C5 C6 55.84(17) . . . . ?
C8 C4 C5 C1 169.14(13) . . . . ?
C8 C4 C5 C6 -66.16(17) . . . . ?
C9 C2 C3 C4 -140.36(16) . . . . ?
C10 N1 C1 O1 -2.1(2) . . . . ?
C10 N1 C1 C5 178.78(11) . . . . ?
C10 N1 C2 C3 172.22(12) . . . . ?
C10 N1 C2 C9 -5.7(2) . . . . ?
C10 C11 C12 C13 0.7(2) . . . . ?
C11 C10 C15 C14 -0.3(2) . . . . ?
C11 C12 C13 C14 -0.4(3) . . . . ?
C12 C13 C14 C15 -0.4(3) . . . . ?
C13 C14 C15 C10 0.7(3) . . . . ?
C15 C10 C11 C12 -0.4(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
