# 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_200513a
_database_code_depnum_ccdc_archive 'CCDC 2004708'
_audit_update_record             
;
2020-05-19 deposited with the CCDC.	2020-06-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_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 0.0181 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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.8025(4)
_cell_length_b                   6.6554(2)
_cell_length_c                   19.9584(8)
_cell_angle_alpha                90
_cell_angle_beta                 90.687(2)
_cell_angle_gamma                90
_cell_volume                     1567.63(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2505
_cell_measurement_theta_min      3.7350
_cell_measurement_theta_max      70.8460

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.660
_shelx_estimated_absorpt_T_min   0.890
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8905
_exptl_absorpt_correction_T_max  0.9741
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9039
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.745
_diffrn_reflns_theta_max         66.039
_diffrn_reflns_theta_full        66.039
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2724
_reflns_number_gt                1943
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0601P)²+0.0943P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0025(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2724
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0482
_refine_ls_wR_factor_ref         0.1363
_refine_ls_wR_factor_gt          0.1227
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.000
_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
N1 N 0.77222(15) 0.6699(2) 0.20659(8) 0.0477(5) Uani 1 1 d . . . . .
N2 N 1.06835(19) 0.7586(4) 0.49778(11) 0.0796(7) Uani 1 1 d . . . . .
O1 O 0.70808(14) 0.9933(2) 0.19072(8) 0.0629(5) Uani 1 1 d . . . . .
O2 O 0.40013(15) 0.4098(3) 0.07811(10) 0.0815(6) Uani 1 1 d . . . . .
C1 C 0.71768(17) 0.8214(3) 0.17179(10) 0.0453(5) Uani 1 1 d . . . . .
C2 C 0.67985(17) 0.7402(3) 0.10405(10) 0.0467(5) Uani 1 1 d . . . . .
C3 C 0.56767(17) 0.8267(3) 0.07825(10) 0.0452(5) Uani 1 1 d . . . . .
H3A H 0.5641 0.8057 0.0302 0.054 Uiso 1 1 calc R U . . .
H3B H 0.5691 0.9706 0.0858 0.054 Uiso 1 1 calc R U . . .
C4 C 0.45762(18) 0.7437(3) 0.10832(10) 0.0480(5) Uani 1 1 d . . . . .
C5 C 0.46799(19) 0.5168(3) 0.10691(11) 0.0534(6) Uani 1 1 d . . . . .
C6 C 0.5691(2) 0.4331(3) 0.14263(13) 0.0628(7) Uani 1 1 d . . . . .
H6A H 0.5681 0.2878 0.1387 0.075 Uiso 1 1 calc R U . . .
H6B H 0.5646 0.4665 0.1898 0.075 Uiso 1 1 calc R U . . .
C7 C 0.68071(19) 0.5120(3) 0.11544(11) 0.0550(6) Uani 1 1 d . . . . .
H7 H 0.6991 0.4426 0.0737 0.066 Uiso 1 1 calc R U . . .
C8 C 0.7763(2) 0.4833(3) 0.16664(12) 0.0625(7) Uani 1 1 d . . . . .
H8A H 0.7630 0.3662 0.1944 0.075 Uiso 1 1 calc R U . . .
H8B H 0.8488 0.4689 0.1448 0.075 Uiso 1 1 calc R U . . .
C9 C 0.7733(2) 0.8013(5) 0.05466(12) 0.0740(8) Uani 1 1 d . . . . .
H9A H 0.7780 0.9452 0.0525 0.111 Uiso 1 1 calc R U . . .
H9B H 0.7553 0.7491 0.0110 0.111 Uiso 1 1 calc R U . . .
H9C H 0.8447 0.7477 0.0697 0.111 Uiso 1 1 calc R U . . .
C10 C 0.4417(2) 0.8152(4) 0.18110(11) 0.0636(7) Uani 1 1 d . . . . .
H10A H 0.3754 0.7534 0.1993 0.095 Uiso 1 1 calc R U . . .
H10B H 0.4331 0.9586 0.1817 0.095 Uiso 1 1 calc R U . . .
H10C H 0.5069 0.7780 0.2076 0.095 Uiso 1 1 calc R U . . .
C11 C 0.3574(2) 0.8159(4) 0.06623(14) 0.0733(8) Uani 1 1 d . . . . .
H11A H 0.3668 0.7738 0.0206 0.110 Uiso 1 1 calc R U . . .
H11B H 0.3533 0.9598 0.0680 0.110 Uiso 1 1 calc R U . . .
H11C H 0.2887 0.7595 0.0834 0.110 Uiso 1 1 calc R U . . .
C12 C 0.83271(17) 0.6891(3) 0.26756(10) 0.0461(5) Uani 1 1 d . . . . .
C13 C 0.8150(2) 0.8482(4) 0.31055(11) 0.0650(7) Uani 1 1 d . . . . .
H13 H 0.7620 0.9463 0.2993 0.078 Uiso 1 1 calc R U . . .
C14 C 0.8750(2) 0.8632(4) 0.36993(11) 0.0664(7) Uani 1 1 d . . . . .
H14 H 0.8624 0.9717 0.3982 0.080 Uiso 1 1 calc R U . . .
C15 C 0.95308(17) 0.7205(4) 0.38780(10) 0.0525(6) Uani 1 1 d . . . . .
C16 C 0.9701(2) 0.5607(4) 0.34553(14) 0.0818(9) Uani 1 1 d . . . . .
H16 H 1.0223 0.4619 0.3573 0.098 Uiso 1 1 calc R U . . .
C17 C 0.9107(2) 0.5450(4) 0.28594(13) 0.0758(8) Uani 1 1 d . . . . .
H17 H 0.9235 0.4360 0.2579 0.091 Uiso 1 1 calc R U . . .
C18 C 1.01713(19) 0.7396(4) 0.44962(12) 0.0597(6) 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
N1 C1 1.379(3) . ?
N1 C12 1.409(2) . ?
N1 C8 1.477(2) . ?
N2 C18 1.136(3) . ?
O1 C1 1.211(2) . ?
O2 C5 1.212(2) . ?
C1 C2 1.518(3) . ?
C2 C3 1.527(3) . ?
C2 C7 1.536(3) . ?
C2 C9 1.543(3) . ?
C3 C4 1.540(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.516(3) . ?
C4 C11 1.521(3) . ?
C4 C10 1.542(3) . ?
C5 C6 1.491(3) . ?
C6 C7 1.524(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.525(3) . ?
C7 H7 0.9800 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C17 1.376(3) . ?
C12 C13 1.381(3) . ?
C13 C14 1.377(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.367(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.373(3) . ?
C15 C18 1.445(3) . ?
C16 C17 1.377(3) . ?
C16 H16 0.9300 . ?
C17 H17 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 C12 126.67(17) . . ?
C1 N1 C8 111.15(16) . . ?
C12 N1 C8 121.53(16) . . ?
O1 C1 N1 125.36(18) . . ?
O1 C1 C2 125.91(19) . . ?
N1 C1 C2 108.59(17) . . ?
C1 C2 C3 114.25(18) . . ?
C1 C2 C7 102.64(16) . . ?
C3 C2 C7 115.25(17) . . ?
C1 C2 C9 105.69(17) . . ?
C3 C2 C9 107.98(17) . . ?
C7 C2 C9 110.6(2) . . ?
C2 C3 C4 117.74(17) . . ?
C2 C3 H3A 107.9 . . ?
C4 C3 H3A 107.9 . . ?
C2 C3 H3B 107.9 . . ?
C4 C3 H3B 107.9 . . ?
H3A C3 H3B 107.2 . . ?
C5 C4 C11 111.52(19) . . ?
C5 C4 C3 106.34(18) . . ?
C11 C4 C3 109.02(18) . . ?
C5 C4 C10 109.61(18) . . ?
C11 C4 C10 108.7(2) . . ?
C3 C4 C10 111.67(17) . . ?
O2 C5 C6 121.9(2) . . ?
O2 C5 C4 122.8(2) . . ?
C6 C5 C4 115.33(18) . . ?
C5 C6 C7 113.04(19) . . ?
C5 C6 H6A 109.0 . . ?
C7 C6 H6A 109.0 . . ?
C5 C6 H6B 109.0 . . ?
C7 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C6 C7 C8 110.7(2) . . ?
C6 C7 C2 112.93(18) . . ?
C8 C7 C2 103.11(17) . . ?
C6 C7 H7 110.0 . . ?
C8 C7 H7 110.0 . . ?
C2 C7 H7 110.0 . . ?
N1 C8 C7 103.17(17) . . ?
N1 C8 H8A 111.1 . . ?
C7 C8 H8A 111.1 . . ?
N1 C8 H8B 111.1 . . ?
C7 C8 H8B 111.1 . . ?
H8A C8 H8B 109.1 . . ?
C2 C9 H9A 109.5 . . ?
C2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C4 C10 H10A 109.5 . . ?
C4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C4 C11 H11A 109.5 . . ?
C4 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C4 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C17 C12 C13 118.3(2) . . ?
C17 C12 N1 119.84(19) . . ?
C13 C12 N1 121.82(18) . . ?
C14 C13 C12 120.7(2) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C15 C14 C13 120.8(2) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C16 118.7(2) . . ?
C14 C15 C18 120.4(2) . . ?
C16 C15 C18 120.9(2) . . ?
C15 C16 C17 120.9(2) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C12 C17 C16 120.6(2) . . ?
C12 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
N2 C18 C15 178.5(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
C12 N1 C1 O1 -4.6(4) . . . . ?
C8 N1 C1 O1 -175.3(2) . . . . ?
C12 N1 C1 C2 171.24(19) . . . . ?
C8 N1 C1 C2 0.5(2) . . . . ?
O1 C1 C2 C3 -38.8(3) . . . . ?
N1 C1 C2 C3 145.43(18) . . . . ?
O1 C1 C2 C7 -164.3(2) . . . . ?
N1 C1 C2 C7 19.9(2) . . . . ?
O1 C1 C2 C9 79.8(3) . . . . ?
N1 C1 C2 C9 -96.0(2) . . . . ?
C1 C2 C3 C4 -77.8(2) . . . . ?
C7 C2 C3 C4 40.7(3) . . . . ?
C9 C2 C3 C4 164.91(19) . . . . ?
C2 C3 C4 C5 -47.9(2) . . . . ?
C2 C3 C4 C11 -168.21(18) . . . . ?
C2 C3 C4 C10 71.7(3) . . . . ?
C11 C4 C5 O2 -3.4(3) . . . . ?
C3 C4 C5 O2 -122.2(2) . . . . ?
C10 C4 C5 O2 117.0(2) . . . . ?
C11 C4 C5 C6 175.6(2) . . . . ?
C3 C4 C5 C6 56.8(2) . . . . ?
C10 C4 C5 C6 -64.0(3) . . . . ?
O2 C5 C6 C7 120.5(2) . . . . ?
C4 C5 C6 C7 -58.5(3) . . . . ?
C5 C6 C7 C8 160.30(18) . . . . ?
C5 C6 C7 C2 45.3(3) . . . . ?
C1 C2 C7 C6 87.9(2) . . . . ?
C3 C2 C7 C6 -37.0(3) . . . . ?
C9 C2 C7 C6 -159.77(19) . . . . ?
C1 C2 C7 C8 -31.6(2) . . . . ?
C3 C2 C7 C8 -156.47(19) . . . . ?
C9 C2 C7 C8 80.7(2) . . . . ?
C1 N1 C8 C7 -20.9(3) . . . . ?
C12 N1 C8 C7 167.78(19) . . . . ?
C6 C7 C8 N1 -89.0(2) . . . . ?
C2 C7 C8 N1 32.1(2) . . . . ?
C1 N1 C12 C17 -159.8(2) . . . . ?
C8 N1 C12 C17 10.0(3) . . . . ?
C1 N1 C12 C13 21.1(3) . . . . ?
C8 N1 C12 C13 -169.0(2) . . . . ?
C17 C12 C13 C14 0.8(4) . . . . ?
N1 C12 C13 C14 179.8(2) . . . . ?
C12 C13 C14 C15 -0.3(4) . . . . ?
C13 C14 C15 C16 -0.4(4) . . . . ?
C13 C14 C15 C18 178.8(2) . . . . ?
C14 C15 C16 C17 0.7(4) . . . . ?
C18 C15 C16 C17 -178.6(3) . . . . ?
C13 C12 C17 C16 -0.5(4) . . . . ?
N1 C12 C17 C16 -179.6(3) . . . . ?
C15 C16 C17 C12 -0.2(5) . . . . ?

_refine_diff_density_max         0.155
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.036

