# Electronic Supplementary Material (ESI) for Green Chemistry.
# 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. 
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data_210115sf
_database_code_depnum_ccdc_archive 'CCDC 2068194'
_audit_update_record             
;
2021-03-05 deposited with the CCDC.	2022-08-01 downloaded from the CCDC.
;
_audit_creation_date             2021-01-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H24 N2 O2'
_chemical_formula_sum            'C22 H24 N2 O2'
_chemical_formula_weight         348.43
_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 0.0148 0.0070 '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 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 '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                   14.6248(3)
_cell_length_b                   11.8590(2)
_cell_length_c                   11.3672(2)
_cell_angle_alpha                90
_cell_angle_beta                 107.2710(10)
_cell_angle_gamma                90
_cell_volume                     1882.58(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9946
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      54.985
_cell_measurement_theta_min      2.753
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.965
_exptl_absorpt_coefficient_mu    0.403
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.4551
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.2000 before and 0.0797 after correction. The Ratio of minimum to maximum transmission is 0.6062. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0600
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            19598
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.963
_diffrn_reflns_theta_min         2.753
_diffrn_ambient_temperature      193.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3006
_reflns_number_total             3557
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3557
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0411
_refine_ls_restrained_S_all      1.048
_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)+(0.0502P)²+0.3821P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1089
_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 Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C10(H10), C11(H11), C13(H13), C14(H14), C18(H18), C19(H19), C20(H20),
 C21(H21), C22(H22)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_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 0.81068(7) 0.43339(9) 0.77458(9) 0.0464(3) Uani 1 1 d . . . . .
O2 O 0.70428(7) 0.41640(9) 0.03804(9) 0.0427(3) Uani 1 1 d . . . . .
N1 N 0.75229(7) 0.53398(9) 0.60004(9) 0.0303(3) Uani 1 1 d . . . . .
N2 N 1.00278(12) 0.69825(14) 0.37481(15) 0.0683(5) Uani 1 1 d . . . . .
C1 C 0.76325(8) 0.61206(11) 0.50802(11) 0.0276(3) Uani 1 1 d . . . . .
C2 C 0.78130(8) 0.71990(11) 0.53815(12) 0.0301(3) Uani 1 1 d . . . . .
H2 H 0.781313 0.740457 0.618926 0.036 Uiso 1 1 calc R . . . .
C3 C 0.80161(9) 0.81294(11) 0.46027(12) 0.0339(3) Uani 1 1 d . . . . .
H3A H 0.746267 0.865053 0.436710 0.041 Uiso 1 1 calc R . . . .
H3B H 0.809876 0.780524 0.383817 0.041 Uiso 1 1 calc R . . . .
C4 C 0.89167(10) 0.87887(12) 0.52812(13) 0.0375(3) Uani 1 1 d . . . . .
H4A H 0.882574 0.912107 0.603748 0.045 Uiso 1 1 calc R . . . .
H4B H 0.900321 0.941648 0.475011 0.045 Uiso 1 1 calc R . . . .
C5 C 0.98255(10) 0.80655(13) 0.56364(13) 0.0385(3) Uani 1 1 d . . . . .
H5A H 1.038864 0.855774 0.597837 0.046 Uiso 1 1 calc R . . . .
H5B H 0.979290 0.752499 0.628640 0.046 Uiso 1 1 calc R . . . .
C6 C 0.99478(11) 0.74459(13) 0.45881(14) 0.0420(3) Uani 1 1 d . . . . .
C7 C 0.82512(9) 0.49829(11) 0.69758(12) 0.0330(3) Uani 1 1 d . . . . .
C8 C 0.92429(10) 0.53967(13) 0.70753(13) 0.0392(3) Uani 1 1 d . . . . .
H8A H 0.934574 0.613109 0.748910 0.059 Uiso 1 1 calc GR . . . .
H8B H 0.931446 0.547301 0.624865 0.059 Uiso 1 1 calc GR . . . .
H8C H 0.971503 0.485577 0.755283 0.059 Uiso 1 1 calc GR . . . .
C9 C 0.74950(9) 0.56036(11) 0.38477(11) 0.0283(3) Uani 1 1 d . . . . .
C10 C 0.69107(9) 0.60985(11) 0.27771(12) 0.0310(3) Uani 1 1 d . . . . .
H10 H 0.660125 0.679315 0.282820 0.037 Uiso 1 1 calc R . . . .
C11 C 0.67743(9) 0.55968(12) 0.16450(12) 0.0329(3) Uani 1 1 d . . . . .
H11 H 0.636971 0.594536 0.092555 0.040 Uiso 1 1 calc R . . . .
C12 C 0.72241(9) 0.45854(12) 0.15487(12) 0.0316(3) Uani 1 1 d . . . . .
C13 C 0.78005(10) 0.40690(12) 0.26029(13) 0.0369(3) Uani 1 1 d . . . . .
H13 H 0.810795 0.337359 0.254865 0.044 Uiso 1 1 calc R . . . .
C14 C 0.79235(10) 0.45784(12) 0.37372(12) 0.0355(3) Uani 1 1 d . . . . .
H14 H 0.831137 0.421694 0.445912 0.043 Uiso 1 1 calc R . . . .
C15 C 0.76101(12) 0.32356(14) 0.02139(14) 0.0479(4) Uani 1 1 d . . . . .
H15A H 0.746980 0.307410 -0.066745 0.072 Uiso 1 1 calc GR . . . .
H15B H 0.746077 0.257110 0.063545 0.072 Uiso 1 1 calc GR . . . .
H15C H 0.829003 0.342286 0.055920 0.072 Uiso 1 1 calc GR . . . .
C16 C 0.65529(9) 0.48919(12) 0.58212(13) 0.0347(3) Uani 1 1 d . . . . .
H16A H 0.660233 0.415085 0.623647 0.042 Uiso 1 1 calc R . . . .
H16B H 0.624353 0.476954 0.492992 0.042 Uiso 1 1 calc R . . . .
C17 C 0.59267(9) 0.56563(12) 0.63121(12) 0.0324(3) Uani 1 1 d . . . . .
C18 C 0.57774(10) 0.54390(14) 0.74395(14) 0.0413(3) Uani 1 1 d . . . . .
H18 H 0.609139 0.481942 0.792252 0.050 Uiso 1 1 calc R . . . .
C19 C 0.51721(11) 0.61202(15) 0.78680(15) 0.0510(4) Uani 1 1 d . . . . .
H19 H 0.506954 0.595833 0.863757 0.061 Uiso 1 1 calc R . . . .
C20 C 0.47202(11) 0.70277(15) 0.71855(17) 0.0523(4) Uani 1 1 d . . . . .
H20 H 0.430276 0.748764 0.747900 0.063 Uiso 1 1 calc R . . . .
C21 C 0.48761(10) 0.72667(14) 0.60732(16) 0.0477(4) Uani 1 1 d . . . . .
H21 H 0.457544 0.790150 0.560695 0.057 Uiso 1 1 calc R . . . .
C22 C 0.54715(9) 0.65812(13) 0.56340(13) 0.0385(3) Uani 1 1 d . . . . .
H22 H 0.556924 0.674525 0.486220 0.046 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 C7 1.2300(16) . ?
O2 C12 1.3692(15) . ?
O2 C15 1.4246(18) . ?
N1 C1 1.4411(16) . ?
N1 C7 1.3571(17) . ?
N1 C16 1.4713(16) . ?
N2 C6 1.137(2) . ?
C1 C2 1.3299(19) . ?
C1 C9 1.4873(17) . ?
C2 H2 0.9500 . ?
C2 C3 1.4985(18) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.5289(19) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.532(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.455(2) . ?
C7 C8 1.5032(19) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.3921(18) . ?
C9 C14 1.3904(19) . ?
C10 H10 0.9500 . ?
C10 C11 1.3775(18) . ?
C11 H11 0.9500 . ?
C11 C12 1.388(2) . ?
C12 C13 1.3863(19) . ?
C13 H13 0.9500 . ?
C13 C14 1.3864(19) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.5083(19) . ?
C17 C18 1.3866(19) . ?
C17 C22 1.391(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.389(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.376(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.379(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.388(2) . ?
C22 H22 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
C12 O2 C15 117.27(11) . . ?
C1 N1 C16 116.22(10) . . ?
C7 N1 C1 124.33(11) . . ?
C7 N1 C16 119.42(11) . . ?
N1 C1 C9 113.94(11) . . ?
C2 C1 N1 119.16(11) . . ?
C2 C1 C9 126.87(12) . . ?
C1 C2 H2 116.0 . . ?
C1 C2 C3 127.95(12) . . ?
C3 C2 H2 116.0 . . ?
C2 C3 H3A 109.3 . . ?
C2 C3 H3B 109.3 . . ?
C2 C3 C4 111.76(11) . . ?
H3A C3 H3B 107.9 . . ?
C4 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
C3 C4 H4A 108.9 . . ?
C3 C4 H4B 108.9 . . ?
C3 C4 C5 113.38(11) . . ?
H4A C4 H4B 107.7 . . ?
C5 C4 H4A 108.9 . . ?
C5 C4 H4B 108.9 . . ?
C4 C5 H5A 109.2 . . ?
C4 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
C6 C5 C4 112.01(12) . . ?
C6 C5 H5A 109.2 . . ?
C6 C5 H5B 109.2 . . ?
N2 C6 C5 178.14(17) . . ?
O1 C7 N1 121.17(12) . . ?
O1 C7 C8 121.09(12) . . ?
N1 C7 C8 117.73(12) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C1 121.73(12) . . ?
C14 C9 C1 120.47(11) . . ?
C14 C9 C10 117.76(12) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 121.04(12) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.43(12) . . ?
C12 C11 H11 119.8 . . ?
O2 C12 C11 115.61(12) . . ?
O2 C12 C13 124.76(12) . . ?
C13 C12 C11 119.63(12) . . ?
C12 C13 H13 120.4 . . ?
C12 C13 C14 119.28(13) . . ?
C14 C13 H13 120.4 . . ?
C9 C14 H14 119.1 . . ?
C13 C14 C9 121.83(12) . . ?
C13 C14 H14 119.1 . . ?
O2 C15 H15A 109.5 . . ?
O2 C15 H15B 109.5 . . ?
O2 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C16 H16A 108.9 . . ?
N1 C16 H16B 108.9 . . ?
N1 C16 C17 113.47(11) . . ?
H16A C16 H16B 107.7 . . ?
C17 C16 H16A 108.9 . . ?
C17 C16 H16B 108.9 . . ?
C18 C17 C16 120.65(13) . . ?
C18 C17 C22 118.54(13) . . ?
C22 C17 C16 120.80(12) . . ?
C17 C18 H18 119.7 . . ?
C17 C18 C19 120.51(15) . . ?
C19 C18 H18 119.7 . . ?
C18 C19 H19 119.8 . . ?
C20 C19 C18 120.44(15) . . ?
C20 C19 H19 119.8 . . ?
C19 C20 H20 120.2 . . ?
C19 C20 C21 119.69(15) . . ?
C21 C20 H20 120.2 . . ?
C20 C21 H21 120.0 . . ?
C20 C21 C22 120.09(16) . . ?
C22 C21 H21 120.0 . . ?
C17 C22 H22 119.6 . . ?
C21 C22 C17 120.70(14) . . ?
C21 C22 H22 119.6 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
