# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_7NPy4
_database_code_depnum_ccdc_archive 'CCDC 1920050'
loop_
_audit_author_name
_audit_author_address
'Clara S. B. Gomes'
;LAQV REQUIMTE, FCT, Universidade NOVA de Lisboa
Portugal
;
_audit_update_record             
;
2019-05-31 deposited with the CCDC.	2019-10-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18  H20  N2  O2'
_chemical_formula_sum            'C18 H20 N2 O2'
_chemical_formula_weight         296.36

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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                   7.0060(6)
_cell_length_b                   18.2400(17)
_cell_length_c                   12.5016(11)
_cell_angle_alpha                90
_cell_angle_beta                 97.953(4)
_cell_angle_gamma                90
_cell_volume                     1582.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5050
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      31.31

_exptl_crystal_description       prism
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31778
_diffrn_reflns_av_unetI/netI     0.0647
_diffrn_reflns_av_R_equivalents  0.1313
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.161
_diffrn_reflns_theta_max         25.680
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2992
_reflns_number_gt                1795
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0889P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2992
_refine_ls_number_parameters     204
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1293
_refine_ls_R_factor_gt           0.0668
_refine_ls_wR_factor_ref         0.1706
_refine_ls_wR_factor_gt          0.1542
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.002
_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_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 0.1262(2) 0.30467(10) 0.48237(14) 0.0424(5) Uani 1 1 d . . . . .
O1 O 0.7142(3) 0.16243(10) 0.56617(14) 0.0536(6) Uani 1 1 d . . . . .
N2 N -0.1500(3) 0.44499(12) 0.74651(16) 0.0457(6) Uani 1 1 d . . . . .
N1 N 1.2873(3) 0.15088(12) 0.85078(16) 0.0395(6) Uani 1 1 d . . . . .
C18 C -0.2682(5) 0.52971(17) 0.5987(3) 0.0753(11) Uani 1 1 d . . . . .
H18A H -0.221312 0.569870 0.644634 0.113 Uiso 1 1 calc R U . . .
H18B H -0.383065 0.544454 0.552783 0.113 Uiso 1 1 calc R U . . .
H18C H -0.171720 0.515619 0.555195 0.113 Uiso 1 1 calc R U . . .
C17 C -0.3133(4) 0.46545(15) 0.6674(2) 0.0493(7) Uani 1 1 d . . . . .
H17A H -0.421522 0.477990 0.704637 0.059 Uiso 1 1 calc R U . . .
H17B H -0.350814 0.423790 0.620998 0.059 Uiso 1 1 calc R U . . .
C12 C -0.0020(3) 0.40314(13) 0.71899(19) 0.0333(6) Uani 1 1 d . . . . .
C13 C -0.0073(3) 0.37610(13) 0.61347(18) 0.0329(6) Uani 1 1 d . . . . .
H13 H -0.110283 0.388600 0.561486 0.040 Uiso 1 1 calc R U . . .
C14 C 0.1365(3) 0.33142(12) 0.58503(18) 0.0293(6) Uani 1 1 d . . . . .
C9 C 0.2969(3) 0.31177(12) 0.65983(18) 0.0300(6) Uani 1 1 d . . . . .
C8 C 0.4435(3) 0.26369(13) 0.63022(18) 0.0310(6) Uani 1 1 d . . . . .
H8 H 0.418549 0.242398 0.562127 0.037 Uiso 1 1 calc R U . . .
C7 C 0.6119(3) 0.24586(13) 0.6891(2) 0.0363(6) Uani 1 1 d . . . . .
H7 H 0.643759 0.267587 0.756453 0.044 Uiso 1 1 calc R U . . .
C6 C 0.7458(3) 0.19471(13) 0.65289(18) 0.0313(6) Uani 1 1 d . . . . .
C3 C 0.9331(3) 0.17963(12) 0.72473(17) 0.0263(5) Uani 1 1 d . . . . .
C4 C 0.9810(3) 0.21019(14) 0.82539(19) 0.0377(6) Uani 1 1 d . . . . .
H4 H 0.895098 0.241214 0.853560 0.045 Uiso 1 1 calc R U . . .
C5 C 1.1569(4) 0.19448(15) 0.88401(19) 0.0429(7) Uani 1 1 d . . . . .
H5 H 1.186209 0.216033 0.951717 0.052 Uiso 1 1 calc R U . . .
C1 C 1.2393(4) 0.12080(15) 0.7541(2) 0.0454(7) Uani 1 1 d . . . . .
H1 H 1.327219 0.089401 0.728462 0.054 Uiso 1 1 calc R U . . .
C2 C 1.0674(3) 0.13339(14) 0.6898(2) 0.0404(7) Uani 1 1 d . . . . .
H2 H 1.041423 0.110740 0.622748 0.048 Uiso 1 1 calc R U . . .
C11 C 0.1580(4) 0.38382(13) 0.79435(19) 0.0396(7) Uani 1 1 d . . . . .
H11 H 0.167165 0.400849 0.864989 0.048 Uiso 1 1 calc R U . . .
C10 C 0.2997(3) 0.34033(13) 0.7646(2) 0.0374(6) Uani 1 1 d . . . . .
H10 H 0.403933 0.328879 0.816385 0.045 Uiso 1 1 calc R U . . .
C15 C -0.1436(4) 0.47811(15) 0.8533(2) 0.0525(8) Uani 1 1 d . . . . .
H15B H -0.202119 0.526350 0.845441 0.063 Uiso 1 1 calc R U . . .
H15A H -0.010004 0.484408 0.884612 0.063 Uiso 1 1 calc R U . . .
C16 C -0.2449(5) 0.4337(2) 0.9293(3) 0.0907(13) Uani 1 1 d . . . . .
H16C H -0.379121 0.429806 0.901158 0.136 Uiso 1 1 calc R U . . .
H16B H -0.231502 0.457383 0.998587 0.136 Uiso 1 1 calc R U . . .
H16A H -0.189015 0.385658 0.936940 0.136 Uiso 1 1 calc R U . . .
H20 H 0.012(6) 0.322(2) 0.438(3) 0.136 Uiso 1 1 d . U . . .


_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 C14 1.366(3) . ?
O2 H20 0.96(4) . ?
O1 C6 1.227(3) . ?
N2 C12 1.369(3) . ?
N2 C17 1.454(3) . ?
N2 C15 1.461(3) . ?
N1 C5 1.321(3) . ?
N1 C1 1.328(3) . ?
C18 C17 1.512(4) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C12 C13 1.404(3) . ?
C12 C11 1.406(3) . ?
C13 C14 1.380(3) . ?
C13 H13 0.9300 . ?
C14 C9 1.405(3) . ?
C9 C10 1.408(3) . ?
C9 C8 1.437(3) . ?
C8 C7 1.341(3) . ?
C8 H8 0.9300 . ?
C7 C6 1.439(3) . ?
C7 H7 0.9300 . ?
C6 C3 1.509(3) . ?
C3 C4 1.375(3) . ?
C3 C2 1.379(3) . ?
C4 C5 1.374(3) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C1 C2 1.371(3) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C11 C10 1.362(3) . ?
C11 H11 0.9300 . ?
C10 H10 0.9300 . ?
C15 C16 1.499(4) . ?
C15 H15B 0.9700 . ?
C15 H15A 0.9700 . ?
C16 H16C 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16A 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
C14 O2 H20 111(2) . . ?
C12 N2 C17 121.6(2) . . ?
C12 N2 C15 122.1(2) . . ?
C17 N2 C15 115.9(2) . . ?
C5 N1 C1 115.8(2) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N2 C17 C18 112.2(2) . . ?
N2 C17 H17A 109.2 . . ?
C18 C17 H17A 109.2 . . ?
N2 C17 H17B 109.2 . . ?
C18 C17 H17B 109.2 . . ?
H17A C17 H17B 107.9 . . ?
N2 C12 C13 120.6(2) . . ?
N2 C12 C11 122.2(2) . . ?
C13 C12 C11 117.2(2) . . ?
C14 C13 C12 121.6(2) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
O2 C14 C13 120.5(2) . . ?
O2 C14 C9 117.9(2) . . ?
C13 C14 C9 121.6(2) . . ?
C14 C9 C10 115.6(2) . . ?
C14 C9 C8 121.2(2) . . ?
C10 C9 C8 123.2(2) . . ?
C7 C8 C9 127.8(2) . . ?
C7 C8 H8 116.1 . . ?
C9 C8 H8 116.1 . . ?
C8 C7 C6 123.2(2) . . ?
C8 C7 H7 118.4 . . ?
C6 C7 H7 118.4 . . ?
O1 C6 C7 122.9(2) . . ?
O1 C6 C3 118.3(2) . . ?
C7 C6 C3 118.8(2) . . ?
C4 C3 C2 116.5(2) . . ?
C4 C3 C6 123.6(2) . . ?
C2 C3 C6 119.9(2) . . ?
C5 C4 C3 119.4(2) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
N1 C5 C4 124.5(2) . . ?
N1 C5 H5 117.8 . . ?
C4 C5 H5 117.8 . . ?
N1 C1 C2 123.8(2) . . ?
N1 C1 H1 118.1 . . ?
C2 C1 H1 118.1 . . ?
C1 C2 C3 120.0(2) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C10 C11 C12 120.5(2) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C11 C10 C9 123.6(2) . . ?
C11 C10 H10 118.2 . . ?
C9 C10 H10 118.2 . . ?
N2 C15 C16 113.5(2) . . ?
N2 C15 H15B 108.9 . . ?
C16 C15 H15B 108.9 . . ?
N2 C15 H15A 108.9 . . ?
C16 C15 H15A 108.9 . . ?
H15B C15 H15A 107.7 . . ?
C15 C16 H16C 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16C C16 H16B 109.5 . . ?
C15 C16 H16A 109.5 . . ?
H16C C16 H16A 109.5 . . ?
H16B C16 H16A 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
C12 N2 C17 C18 -80.2(3) . . . . ?
C15 N2 C17 C18 93.5(3) . . . . ?
C17 N2 C12 C13 -2.5(4) . . . . ?
C15 N2 C12 C13 -175.8(2) . . . . ?
C17 N2 C12 C11 179.1(2) . . . . ?
C15 N2 C12 C11 5.8(4) . . . . ?
N2 C12 C13 C14 -177.4(2) . . . . ?
C11 C12 C13 C14 1.1(3) . . . . ?
C12 C13 C14 O2 178.8(2) . . . . ?
C12 C13 C14 C9 -1.1(3) . . . . ?
O2 C14 C9 C10 -179.5(2) . . . . ?
C13 C14 C9 C10 0.3(3) . . . . ?
O2 C14 C9 C8 -1.4(3) . . . . ?
C13 C14 C9 C8 178.4(2) . . . . ?
C14 C9 C8 C7 173.1(2) . . . . ?
C10 C9 C8 C7 -9.0(4) . . . . ?
C9 C8 C7 C6 177.6(2) . . . . ?
C8 C7 C6 O1 -1.4(4) . . . . ?
C8 C7 C6 C3 178.9(2) . . . . ?
O1 C6 C3 C4 -177.3(2) . . . . ?
C7 C6 C3 C4 2.4(3) . . . . ?
O1 C6 C3 C2 3.2(3) . . . . ?
C7 C6 C3 C2 -177.1(2) . . . . ?
C2 C3 C4 C5 1.0(3) . . . . ?
C6 C3 C4 C5 -178.5(2) . . . . ?
C1 N1 C5 C4 -0.5(4) . . . . ?
C3 C4 C5 N1 -0.3(4) . . . . ?
C5 N1 C1 C2 0.6(4) . . . . ?
N1 C1 C2 C3 0.1(4) . . . . ?
C4 C3 C2 C1 -0.9(3) . . . . ?
C6 C3 C2 C1 178.7(2) . . . . ?
N2 C12 C11 C10 178.1(2) . . . . ?
C13 C12 C11 C10 -0.3(3) . . . . ?
C12 C11 C10 C9 -0.4(4) . . . . ?
C14 C9 C10 C11 0.5(4) . . . . ?
C8 C9 C10 C11 -177.6(2) . . . . ?
C12 N2 C15 C16 -96.5(3) . . . . ?
C17 N2 C15 C16 89.9(3) . . . . ?

_refine_diff_density_max         0.250
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.053

