# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_eg2101_3
_database_code_depnum_ccdc_archive 'CCDC 2114282'
loop_
_audit_author_name
_audit_author_address
'Benjamin S. Gelfand'
;University of Calgary
Canada
;
_audit_update_record             
;
2021-10-06 deposited with the CCDC.	2022-02-03 downloaded from the CCDC.
;
_audit_creation_date             2017-10-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H13 N O2'
_chemical_formula_sum            'C11 H13 N O2'
_chemical_formula_weight         191.22
_chemical_melting_point          373
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                   5.7936(2)
_cell_length_b                   9.1414(3)
_cell_length_c                   10.1254(3)
_cell_angle_alpha                106.962(2)
_cell_angle_beta                 92.401(2)
_cell_angle_gamma                105.495(2)
_cell_volume                     490.09(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6568
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.456
_cell_measurement_theta_min      3.700
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.972
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8540
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0601 before and 0.0476 after correction. The Ratio of minimum to maximum transmission is 0.8540. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             204
_exptl_crystal_size_max          0.324
_exptl_crystal_size_mid          0.198
_exptl_crystal_size_min          0.157
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            17186
_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         27.481
_diffrn_reflns_theta_min         3.681
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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                1845
_reflns_number_total             2256
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         2256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0359
_refine_ls_restrained_S_all      1.041
_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)+(0.0386P)²+0.1157P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0835
_refine_ls_wR_factor_ref         0.0909
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C006(H00A,H00B), C00B(H00D,H00E), C00C(H00F,H00G), C00D(H00H,H00I), C00E(H00J,
 H00K)
2.b Aromatic/amide H refined with riding coordinates:
 C008(H008), C00A(H00C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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
O001 O 0.23445(16) 0.13351(10) 0.47093(9) 0.0330(2) Uani 1 1 d . . . . .
O002 O 0.11427(17) -0.13167(10) 0.37023(10) 0.0344(2) Uani 1 1 d . . . . .
N003 N 0.5621(2) 0.65096(13) 0.15170(12) 0.0360(3) Uani 1 1 d . . . . .
C004 C 0.6519(2) 0.12900(13) 0.30634(12) 0.0257(3) Uani 1 1 d . . . . .
C005 C 0.6406(2) 0.57412(13) 0.20162(12) 0.0267(3) Uani 1 1 d . . . . .
C006 C 0.9855(2) 0.46028(14) 0.21984(13) 0.0281(3) Uani 1 1 d . . . . .
H00A H 1.0718 0.4396 0.2934 0.034 Uiso 1 1 calc R . . . .
H00B H 1.0810 0.5601 0.2094 0.034 Uiso 1 1 calc R . . . .
C007 C 0.7457(2) 0.47790(13) 0.26198(12) 0.0243(2) Uani 1 1 d . . . . .
C008 C 0.6221(2) 0.40410(13) 0.34438(12) 0.0251(2) Uani 1 1 d . . . . .
H008 H 0.4736 0.4208 0.3629 0.030 Uiso 1 1 calc R . . . .
C009 C 0.2643(2) 0.01248(13) 0.39003(11) 0.0265(3) Uani 1 1 d . . . . .
C00A C 0.4592(2) 0.00768(14) 0.30274(12) 0.0274(3) Uani 1 1 d . . . . .
H00C H 0.4476 -0.0906 0.2376 0.033 Uiso 1 1 calc R . . . .
C00B C 0.9603(2) 0.32496(14) 0.08337(13) 0.0307(3) Uani 1 1 d . . . . .
H00D H 0.9065 0.3574 0.0073 0.037 Uiso 1 1 calc R . . . .
H00E H 1.1186 0.3111 0.0690 0.037 Uiso 1 1 calc R . . . .
C00C C 0.7865(2) 0.16386(14) 0.07622(12) 0.0281(3) Uani 1 1 d . . . . .
H00F H 0.7998 0.0849 -0.0088 0.034 Uiso 1 1 calc R . . . .
H00G H 0.6232 0.1719 0.0694 0.034 Uiso 1 1 calc R . . . .
C00D C 0.8236(2) 0.10101(14) 0.19988(13) 0.0300(3) Uani 1 1 d . . . . .
H00H H 0.8038 -0.0129 0.1637 0.036 Uiso 1 1 calc R . . . .
H00I H 0.9880 0.1529 0.2458 0.036 Uiso 1 1 calc R . . . .
C00E C 0.7065(2) 0.29596(14) 0.40925(12) 0.0278(3) Uani 1 1 d . . . . .
H00J H 0.6264 0.2909 0.4907 0.033 Uiso 1 1 calc R . . . .
H00K H 0.8791 0.3392 0.4391 0.033 Uiso 1 1 calc R . . . .
H002 H -0.007(3) -0.123(2) 0.4273(19) 0.066(5) Uiso 1 1 d . . . . .


_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
O001 C009 1.2290(14) . ?
O002 C009 1.3235(14) . ?
O002 H002 0.94(2) . ?
N003 C005 1.1465(15) . ?
C004 C00A 1.3377(17) . ?
C004 C00D 1.5107(17) . ?
C004 C00E 1.5171(16) . ?
C005 C007 1.4443(16) . ?
C006 H00A 0.9700 . ?
C006 H00B 0.9700 . ?
C006 C007 1.5062(16) . ?
C006 C00B 1.5330(17) . ?
C007 C008 1.3358(16) . ?
C008 H008 0.9300 . ?
C008 C00E 1.5029(16) . ?
C009 C00A 1.4645(17) . ?
C00A H00C 0.9300 . ?
C00B H00D 0.9700 . ?
C00B H00E 0.9700 . ?
C00B C00C 1.5255(16) . ?
C00C H00F 0.9700 . ?
C00C H00G 0.9700 . ?
C00C C00D 1.5516(16) . ?
C00D H00H 0.9700 . ?
C00D H00I 0.9700 . ?
C00E H00J 0.9700 . ?
C00E H00K 0.9700 . ?

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
C009 O002 H002 109.2(11) . . ?
C00A C004 C00D 118.68(11) . . ?
C00A C004 C00E 123.92(11) . . ?
C00D C004 C00E 117.38(10) . . ?
N003 C005 C007 178.23(13) . . ?
H00A C006 H00B 107.8 . . ?
C007 C006 H00A 109.0 . . ?
C007 C006 H00B 109.0 . . ?
C007 C006 C00B 112.87(9) . . ?
C00B C006 H00A 109.0 . . ?
C00B C006 H00B 109.0 . . ?
C005 C007 C006 116.60(10) . . ?
C008 C007 C005 119.17(10) . . ?
C008 C007 C006 124.13(11) . . ?
C007 C008 H008 117.8 . . ?
C007 C008 C00E 124.47(11) . . ?
C00E C008 H008 117.8 . . ?
O001 C009 O002 122.24(11) . . ?
O001 C009 C00A 125.80(11) . . ?
O002 C009 C00A 111.94(10) . . ?
C004 C00A C009 127.19(11) . . ?
C004 C00A H00C 116.4 . . ?
C009 C00A H00C 116.4 . . ?
C006 C00B H00D 108.4 . . ?
C006 C00B H00E 108.4 . . ?
H00D C00B H00E 107.5 . . ?
C00C C00B C006 115.32(10) . . ?
C00C C00B H00D 108.4 . . ?
C00C C00B H00E 108.4 . . ?
C00B C00C H00F 108.2 . . ?
C00B C00C H00G 108.2 . . ?
C00B C00C C00D 116.29(10) . . ?
H00F C00C H00G 107.4 . . ?
C00D C00C H00F 108.2 . . ?
C00D C00C H00G 108.2 . . ?
C004 C00D C00C 113.93(10) . . ?
C004 C00D H00H 108.8 . . ?
C004 C00D H00I 108.8 . . ?
C00C C00D H00H 108.8 . . ?
C00C C00D H00I 108.8 . . ?
H00H C00D H00I 107.7 . . ?
C004 C00E H00J 109.5 . . ?
C004 C00E H00K 109.5 . . ?
C008 C00E C004 110.73(9) . . ?
C008 C00E H00J 109.5 . . ?
C008 C00E H00K 109.5 . . ?
H00J C00E H00K 108.1 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
####################################################################### 
# 
# 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_l
_database_code_depnum_ccdc_archive 'CCDC 2114283'
loop_
_audit_author_name
_audit_author_address
'Benjamin S. Gelfand'
;University of Calgary
Canada
;
_audit_update_record             
;
2021-10-06 deposited with the CCDC.	2022-02-03 downloaded from the CCDC.
;
_audit_creation_date             2018-07-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H18 N2 O3'
_chemical_formula_sum            'C18 H18 N2 O3'
_chemical_formula_weight         310.34
_chemical_melting_point          484
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   5.3474(3)
_cell_length_b                   10.8303(7)
_cell_length_c                   13.5741(8)
_cell_angle_alpha                95.958(5)
_cell_angle_beta                 90.704(4)
_cell_angle_gamma                98.055(4)
_cell_volume                     773.88(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1320
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.7735
_cell_measurement_theta_min      3.2745
_shelx_estimated_absorpt_T_max   0.943
_shelx_estimated_absorpt_T_min   0.896
_exptl_absorpt_coefficient_mu    0.746
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6456
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0840 before and 0.0642 after correction.
The Ratio of minimum to maximum transmission is 0.8567.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1799
_diffrn_reflns_av_unetI/netI     0.1145
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16188
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.201
_diffrn_reflns_theta_min         3.275
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1262
_reflns_number_total             2925
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.114
_refine_ls_extinction_coef       0.022(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2925
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1772
_refine_ls_R_factor_gt           0.0879
_refine_ls_restrained_S_all      1.004
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1897
_refine_ls_wR_factor_ref         0.2454
_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, All O(H) groups
2.a Riding coordinates:
 O3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C7(H7), C9(H9), C13(H13), C14(H14), C16(H16), C17(H17)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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 0.7303(7) 0.1126(4) 0.5412(3) 0.0676(11) Uani 1 1 d . . . . .
O2 O 1.2856(7) 0.0981(3) 0.0239(3) 0.0624(10) Uani 1 1 d . . . . .
O3 O 1.3882(6) -0.0510(3) 0.1133(3) 0.0616(10) Uani 1 1 d . . . . .
H3 H 1.5059 -0.0643 0.0537 0.074 Uiso 1 1 d R . . . .
N1 N -0.3409(8) 0.5900(4) 0.6483(3) 0.0658(13) Uani 1 1 d . . . . .
N2 N 0.6357(8) 0.2056(4) 0.4039(3) 0.0556(11) Uani 1 1 d . . . . .
H2 H 0.5408 0.2588 0.3839 0.067 Uiso 1 1 calc R . . . .
C1 C -0.0520(10) 0.4585(5) 0.7353(4) 0.0583(14) Uani 1 1 d . . . . .
C2 C -0.0170(11) 0.4939(5) 0.8460(4) 0.0631(15) Uani 1 1 d . . . . .
H2A H -0.1387 0.4371 0.8807 0.076 Uiso 1 1 calc R . . . .
H2B H -0.0555 0.5804 0.8623 0.076 Uiso 1 1 calc R . . . .
C3 C 0.2503(11) 0.4870(5) 0.8840(4) 0.0631(14) Uani 1 1 d . . . . .
H3A H 0.2851 0.5428 0.9466 0.076 Uiso 1 1 calc R . . . .
H3B H 0.3734 0.5174 0.8349 0.076 Uiso 1 1 calc R . . . .
C4 C 0.2863(11) 0.3528(5) 0.9022(4) 0.0661(15) Uani 1 1 d . . . . .
H4A H 0.4695 0.3482 0.9080 0.079 Uiso 1 1 calc R . . . .
H4B H 0.2107 0.3341 0.9662 0.079 Uiso 1 1 calc R . . . .
C5 C 0.1684(10) 0.2524(5) 0.8207(4) 0.0586(13) Uani 1 1 d . . . . .
H5A H 0.2376 0.1737 0.8284 0.070 Uiso 1 1 calc R . . . .
H5B H -0.0159 0.2362 0.8308 0.070 Uiso 1 1 calc R . . . .
C6 C 0.2106(10) 0.2843(5) 0.7164(4) 0.0545(13) Uani 1 1 d . . . . .
C7 C 0.0587(9) 0.3729(5) 0.6790(4) 0.0587(13) Uani 1 1 d . . . . .
H7 H 0.0367 0.3697 0.6092 0.070 Uiso 1 1 calc R . . . .
C8 C -0.2092(11) 0.5315(5) 0.6854(4) 0.0658(15) Uani 1 1 d . . . . .
C9 C 0.3680(9) 0.2272(5) 0.6567(4) 0.0575(13) Uani 1 1 d . . . . .
H9 H 0.4614 0.1696 0.6836 0.069 Uiso 1 1 calc R . . . .
C10 C 0.4056(10) 0.2490(5) 0.5499(4) 0.0604(14) Uani 1 1 d . . . . .
H10A H 0.4516 0.3401 0.5459 0.072 Uiso 1 1 calc R . . . .
H10B H 0.2436 0.2216 0.5127 0.072 Uiso 1 1 calc R . . . .
C11 C 0.6072(10) 0.1810(5) 0.5005(4) 0.0575(13) Uani 1 1 d . . . . .
C12 C 0.7941(9) 0.1582(5) 0.3326(4) 0.0536(13) Uani 1 1 d . . . . .
C13 C 0.9640(9) 0.0761(5) 0.3487(4) 0.0563(13) Uani 1 1 d . . . . .
H13 H 0.9787 0.0472 0.4119 0.068 Uiso 1 1 calc R . . . .
C14 C 1.1116(10) 0.0367(5) 0.2722(4) 0.0568(13) Uani 1 1 d . . . . .
H14 H 1.2240 -0.0214 0.2831 0.068 Uiso 1 1 calc R . . . .
C15 C 1.1001(9) 0.0797(4) 0.1798(4) 0.0519(12) Uani 1 1 d . . . . .
C16 C 0.9301(9) 0.1623(4) 0.1635(4) 0.0548(13) Uani 1 1 d . . . . .
H16 H 0.9196 0.1926 0.1005 0.066 Uiso 1 1 calc R . . . .
C17 C 0.7769(9) 0.2003(5) 0.2385(4) 0.0566(13) Uani 1 1 d . . . . .
H17 H 0.6588 0.2553 0.2264 0.068 Uiso 1 1 calc R . . . .
C18 C 1.2648(10) 0.0408(5) 0.1003(4) 0.0569(13) Uani 1 1 d . . . . .


_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 C11 1.225(6) . ?
O2 C18 1.261(6) . ?
O3 H3 1.0418 . ?
O3 C18 1.294(5) . ?
N1 C8 1.155(7) . ?
N2 H2 0.8800 . ?
N2 C11 1.371(6) . ?
N2 C12 1.399(5) . ?
C1 C2 1.514(7) . ?
C1 C7 1.346(6) . ?
C1 C8 1.441(7) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.528(7) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.537(7) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.531(7) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.504(6) . ?
C6 C7 1.466(6) . ?
C6 C9 1.344(6) . ?
C7 H7 0.9500 . ?
C9 H9 0.9500 . ?
C9 C10 1.504(6) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.514(6) . ?
C12 C13 1.388(6) . ?
C12 C17 1.407(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.380(6) . ?
C14 H14 0.9500 . ?
C14 C15 1.385(7) . ?
C15 C16 1.393(6) . ?
C15 C18 1.467(6) . ?
C16 H16 0.9500 . ?
C16 C17 1.380(6) . ?
C17 H17 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
C18 O3 H3 109.1 . . ?
C11 N2 H2 115.4 . . ?
C11 N2 C12 129.2(4) . . ?
C12 N2 H2 115.4 . . ?
C7 C1 C2 127.3(5) . . ?
C7 C1 C8 117.4(5) . . ?
C8 C1 C2 115.2(4) . . ?
C1 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
C1 C2 C3 113.0(4) . . ?
H2A C2 H2B 107.8 . . ?
C3 C2 H2A 109.0 . . ?
C3 C2 H2B 109.0 . . ?
C2 C3 H3A 109.2 . . ?
C2 C3 H3B 109.2 . . ?
C2 C3 C4 112.0(5) . . ?
H3A C3 H3B 107.9 . . ?
C4 C3 H3A 109.2 . . ?
C4 C3 H3B 109.2 . . ?
C3 C4 H4A 108.8 . . ?
C3 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
C5 C4 C3 113.8(5) . . ?
C5 C4 H4A 108.8 . . ?
C5 C4 H4B 108.8 . . ?
C4 C5 H5A 108.4 . . ?
C4 C5 H5B 108.4 . . ?
H5A C5 H5B 107.5 . . ?
C6 C5 C4 115.4(5) . . ?
C6 C5 H5A 108.4 . . ?
C6 C5 H5B 108.4 . . ?
C7 C6 C5 117.6(4) . . ?
C9 C6 C5 121.6(5) . . ?
C9 C6 C7 120.6(5) . . ?
C1 C7 C6 125.4(5) . . ?
C1 C7 H7 117.3 . . ?
C6 C7 H7 117.3 . . ?
N1 C8 C1 177.5(6) . . ?
C6 C9 H9 118.0 . . ?
C6 C9 C10 124.1(5) . . ?
C10 C9 H9 118.0 . . ?
C9 C10 H10A 108.8 . . ?
C9 C10 H10B 108.8 . . ?
C9 C10 C11 114.0(4) . . ?
H10A C10 H10B 107.6 . . ?
C11 C10 H10A 108.8 . . ?
C11 C10 H10B 108.8 . . ?
O1 C11 N2 123.9(5) . . ?
O1 C11 C10 124.7(5) . . ?
N2 C11 C10 111.4(4) . . ?
N2 C12 C17 115.7(4) . . ?
C13 C12 N2 125.1(5) . . ?
C13 C12 C17 119.1(5) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.6(5) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 H14 119.2 . . ?
C13 C14 C15 121.7(5) . . ?
C15 C14 H14 119.2 . . ?
C14 C15 C16 118.8(5) . . ?
C14 C15 C18 121.2(5) . . ?
C16 C15 C18 120.0(5) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.2(5) . . ?
C17 C16 H16 119.9 . . ?
C12 C17 H17 119.7 . . ?
C16 C17 C12 120.5(5) . . ?
C16 C17 H17 119.7 . . ?
O2 C18 O3 122.6(5) . . ?
O2 C18 C15 119.9(5) . . ?
O3 C18 C15 117.4(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
