# 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 2018

####################################################################### 
# 
# 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_p2w_a
_database_code_depnum_ccdc_archive 'CCDC 1577687'
_audit_update_record             
;
2018-02-13 deposited with the CCDC.
2018-03-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H23 N3 O2'
_chemical_formula_weight         361.43

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   10.3964(5)
_cell_length_b                   10.8708(5)
_cell_length_c                   17.5190(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1979.95(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9995
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      30.07

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   0.6317
_exptl_transmission_factor_max   0.7460
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Sheldrick, V2016/2)'
_exptl_absorpt_special_details   'Blessing, Acta Cryst. (1995) A51, 33-38'
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microsource
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            117330
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_av_R_equivalents  0.0669
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.278
_diffrn_reflns_theta_max         30.128
_diffrn_reflns_theta_full        30.128
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5839
_reflns_number_gt                5372
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.775
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.996

_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0515P)²+0.2264P] 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       .
_chemical_absolute_configuration syn
_refine_ls_number_reflns         5839
_refine_ls_number_parameters     258
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0345
_refine_ls_wR_factor_ref         0.0903
_refine_ls_wR_factor_gt          0.0870
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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
C1 C 0.45403(13) 0.04869(12) 0.72274(7) 0.0219(2) Uani 1 1 d . . . . .
C2 C 0.57264(14) 0.10189(15) 0.74294(8) 0.0274(3) Uani 1 1 d . . . . .
H2 H 0.611549 0.160382 0.709923 0.033 Uiso 1 1 calc R U . . .
C3 C 0.63318(15) 0.06987(17) 0.81043(9) 0.0338(3) Uani 1 1 d . . . . .
H3 H 0.713366 0.106508 0.823047 0.041 Uiso 1 1 calc R U . . .
C4 C 0.57829(17) -0.01532(16) 0.86016(9) 0.0358(3) Uani 1 1 d . . . . .
H4 H 0.621815 -0.038614 0.905600 0.043 Uiso 1 1 calc R U . . .
C5 C 0.46066(17) -0.06516(15) 0.84272(8) 0.0321(3) Uani 1 1 d . . . . .
H5 H 0.421835 -0.121502 0.877180 0.039 Uiso 1 1 calc R U . . .
C6 C 0.39650(14) -0.03415(13) 0.77456(8) 0.0254(3) Uani 1 1 d . . . . .
C7 C 0.27159(15) -0.08291(15) 0.75809(9) 0.0319(3) Uani 1 1 d . . . . .
H7 H 0.234500 -0.140457 0.792450 0.038 Uiso 1 1 calc R U . . .
C8 C 0.20484(14) -0.04967(15) 0.69524(9) 0.0322(3) Uani 1 1 d . . . . .
H8 H 0.120885 -0.081797 0.687445 0.039 Uiso 1 1 calc R U . . .
C9 C 0.25870(13) 0.03373(12) 0.63973(7) 0.0231(3) Uani 1 1 d . . . . .
C10 C 0.38688(12) 0.07710(12) 0.65224(7) 0.0206(2) Uani 1 1 d . . . . .
C11 C 0.45085(12) 0.13934(12) 0.59302(7) 0.0209(2) Uani 1 1 d . . . . .
H11 H 0.538570 0.160774 0.600364 0.025 Uiso 1 1 calc R U . . .
N12 N 0.39633(11) 0.16937(11) 0.52837(6) 0.0209(2) Uani 1 1 d . . . . .
H12 H 0.3137(19) 0.1467(17) 0.5249(10) 0.025(4) Uiso 1 1 d . . . . .
C13 C 0.46582(12) 0.21471(12) 0.46200(7) 0.0196(2) Uani 1 1 d . . . . .
H13 H 0.546987 0.256180 0.478617 0.023 Uiso 1 1 calc R U . . .
C14 C 0.37703(12) 0.30795(12) 0.42353(7) 0.0204(2) Uani 1 1 d . . . . .
N15 N 0.43314(11) 0.41253(11) 0.40282(7) 0.0259(2) Uani 1 1 d . . . . .
H15 H 0.517(2) 0.4217(18) 0.4058(11) 0.030(5) Uiso 1 1 d . . . . .
N16 N 0.36709(12) 0.49709(12) 0.35634(7) 0.0276(3) Uani 1 1 d . . . . .
H16 H 0.304(2) 0.4612(18) 0.3329(12) 0.032(5) Uiso 1 1 d . . . . .
C17 C 0.31936(14) 0.60338(13) 0.39421(8) 0.0262(3) Uani 1 1 d . . . . .
C18 C 0.21478(17) 0.66377(15) 0.36204(11) 0.0368(4) Uani 1 1 d . . . . .
H18 H 0.174578 0.631562 0.317633 0.044 Uiso 1 1 calc R U . . .
C19 C 0.1695(2) 0.77092(18) 0.39494(13) 0.0484(5) Uani 1 1 d . . . . .
H19 H 0.097903 0.812116 0.373004 0.058 Uiso 1 1 calc R U . . .
C20 C 0.2273(2) 0.81853(18) 0.45927(14) 0.0545(5) Uani 1 1 d . . . . .
H20 H 0.195832 0.892247 0.481616 0.065 Uiso 1 1 calc R U . . .
C21 C 0.3305(2) 0.7588(2) 0.49077(13) 0.0523(5) Uani 1 1 d . . . . .
H21 H 0.370013 0.791318 0.535298 0.063 Uiso 1 1 calc R U . . .
C22 C 0.37826(18) 0.65110(17) 0.45847(10) 0.0387(4) Uani 1 1 d . . . . .
H22 H 0.450518 0.610843 0.480326 0.046 Uiso 1 1 calc R U . . .
O23 O 0.19330(9) 0.06394(10) 0.58079(6) 0.0268(2) Uani 1 1 d . . . . .
C24 C 0.49778(14) 0.10782(13) 0.40689(8) 0.0270(3) Uani 1 1 d . . . . .
H24 H 0.415312 0.067639 0.391350 0.032 Uiso 1 1 calc R U . . .
C25 C 0.58127(19) 0.01197(17) 0.44660(11) 0.0426(4) Uani 1 1 d . . . . .
H25A H 0.603280 -0.053421 0.410385 0.064 Uiso 1 1 calc R U . . .
H25B H 0.533935 -0.023253 0.489761 0.064 Uiso 1 1 calc R U . . .
H25C H 0.660265 0.050968 0.465204 0.064 Uiso 1 1 calc R U . . .
C26 C 0.56434(19) 0.15620(18) 0.33504(9) 0.0397(4) Uani 1 1 d . . . . .
H26A H 0.645386 0.196193 0.349185 0.059 Uiso 1 1 calc R U . . .
H26B H 0.508238 0.215868 0.309544 0.059 Uiso 1 1 calc R U . . .
H26C H 0.582039 0.087530 0.300349 0.059 Uiso 1 1 calc R U . . .
O27 O 0.26323(9) 0.28309(10) 0.41146(6) 0.0276(2) 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
C1 C2 1.4073(19) . ?
C1 C6 1.4117(19) . ?
C1 C10 1.4520(17) . ?
C2 C3 1.3838(19) . ?
C2 H2 0.9500 . ?
C3 C4 1.394(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.372(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.4087(19) . ?
C5 H5 0.9500 . ?
C6 C7 1.432(2) . ?
C7 C8 1.351(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.4425(19) . ?
C8 H8 0.9500 . ?
C9 O23 1.2793(17) . ?
C9 C10 1.4305(18) . ?
C10 C11 1.4058(17) . ?
C11 N12 1.3078(17) . ?
C11 H11 0.9500 . ?
N12 C13 1.4549(15) . ?
N12 H12 0.895(19) . ?
C13 C14 1.5277(17) . ?
C13 C24 1.5468(18) . ?
C13 H13 1.0000 . ?
C14 O27 1.2320(16) . ?
C14 N15 1.3282(18) . ?
N15 N16 1.4070(16) . ?
N15 H15 0.88(2) . ?
N16 C17 1.4218(19) . ?
N16 H16 0.87(2) . ?
C17 C22 1.382(2) . ?
C17 C18 1.390(2) . ?
C18 C19 1.382(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.378(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.370(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.392(3) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C24 C25 1.524(2) . ?
C24 C26 1.530(2) . ?
C24 H24 1.0000 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?

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
C2 C1 C6 118.14(12) . . ?
C2 C1 C10 123.22(12) . . ?
C6 C1 C10 118.62(12) . . ?
C3 C2 C1 120.66(14) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 121.00(15) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 119.22(14) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 121.09(14) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 119.81(13) . . ?
C5 C6 C7 120.77(14) . . ?
C1 C6 C7 119.39(13) . . ?
C8 C7 C6 122.08(13) . . ?
C8 C7 H7 119.0 . . ?
C6 C7 H7 119.0 . . ?
C7 C8 C9 121.21(13) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
O23 C9 C10 122.29(12) . . ?
O23 C9 C8 119.95(12) . . ?
C10 C9 C8 117.74(12) . . ?
C11 C10 C9 119.10(11) . . ?
C11 C10 C1 120.18(12) . . ?
C9 C10 C1 120.53(11) . . ?
N12 C11 C10 123.65(12) . . ?
N12 C11 H11 118.2 . . ?
C10 C11 H11 118.2 . . ?
C11 N12 C13 124.15(11) . . ?
C11 N12 H12 114.0(12) . . ?
C13 N12 H12 121.0(12) . . ?
N12 C13 C14 106.10(10) . . ?
N12 C13 C24 110.55(11) . . ?
C14 C13 C24 110.66(10) . . ?
N12 C13 H13 109.8 . . ?
C14 C13 H13 109.8 . . ?
C24 C13 H13 109.8 . . ?
O27 C14 N15 124.24(12) . . ?
O27 C14 C13 120.69(12) . . ?
N15 C14 C13 115.03(11) . . ?
C14 N15 N16 120.19(12) . . ?
C14 N15 H15 121.1(13) . . ?
N16 N15 H15 116.4(13) . . ?
N15 N16 C17 115.55(12) . . ?
N15 N16 H16 110.5(13) . . ?
C17 N16 H16 108.7(13) . . ?
C22 C17 C18 119.98(15) . . ?
C22 C17 N16 122.03(14) . . ?
C18 C17 N16 117.89(14) . . ?
C19 C18 C17 119.70(17) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C20 C19 C18 120.60(18) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C21 C20 C19 119.52(18) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C20 C21 C22 120.95(19) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 H21 119.5 . . ?
C17 C22 C21 119.25(17) . . ?
C17 C22 H22 120.4 . . ?
C21 C22 H22 120.4 . . ?
C25 C24 C26 110.67(13) . . ?
C25 C24 C13 110.54(12) . . ?
C26 C24 C13 110.64(12) . . ?
C25 C24 H24 108.3 . . ?
C26 C24 H24 108.3 . . ?
C13 C24 H24 108.3 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 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
O23 C9 C10 C11 -9.9(2) . . . . ?
C9 C10 C11 N12 5.8(2) . . . . ?
N12 C13 C14 O27 -47.73(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N12 H12 O23 0.895(19) 1.827(19) 2.5714(15) 139.1(16) . yes
N15 H15 O23 0.88(2) 1.85(2) 2.7319(16) 175.8(19) 4_556 yes

_refine_diff_density_max         0.239
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.043

