# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1534313'
_audit_update_record             
;
2017-02-23 deposited with the CCDC.
2018-05-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H24 N2 O2'
_chemical_formula_weight         348.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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                   14.8982(2)
_cell_length_b                   5.94960(10)
_cell_length_c                   21.2447(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.1390(10)
_cell_angle_gamma                90
_cell_volume                     1868.50(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    3791
_cell_measurement_theta_min      4.8280
_cell_measurement_theta_max      71.1510

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.631
_shelx_estimated_absorpt_T_min   0.824
_shelx_estimated_absorpt_T_max   0.858
_exptl_absorpt_correction_T_min  0.79205
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      291(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.2169
_diffrn_reflns_number            6476
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_av_R_equivalents  0.0143
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         4.194
_diffrn_reflns_theta_max         71.265
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3508
_reflns_number_gt                3094
_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       'CrysAlisPro (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-97

_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)+(0.0998P)²+0.8827P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3508
_refine_ls_number_parameters     236
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0632
_refine_ls_wR_factor_ref         0.1895
_refine_ls_wR_factor_gt          0.1837
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.075
_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
O2 O 0.65172(11) 0.6749(3) 0.47490(8) 0.0573(4) Uani 1 1 d . . . . .
N2 N 0.80660(11) 0.4226(3) 0.51105(7) 0.0427(4) Uani 1 1 d . . . . .
O1 O 0.45664(12) 0.2914(4) 0.31341(9) 0.0744(6) Uani 1 1 d . U . . .
N1 N 0.58353(13) 0.3848(3) 0.41991(10) 0.0581(5) Uani 1 1 d . . . . .
C17 C 0.78082(13) 0.3377(3) 0.56743(9) 0.0411(5) Uani 1 1 d . . . . .
C6 C 0.74899(12) 0.3726(3) 0.45214(8) 0.0388(4) Uani 1 1 d . . . . .
H6 H 0.7375 0.2103 0.4512 0.047 Uiso 1 1 calc R U . . .
C7 C 0.79404(13) 0.4315(3) 0.39361(9) 0.0412(4) Uani 1 1 d . . . . .
C8 C 0.87392(13) 0.2962(3) 0.37971(9) 0.0407(4) Uani 1 1 d . . . . .
C5 C 0.65688(13) 0.4920(3) 0.44959(9) 0.0426(5) Uani 1 1 d . . . . .
C14 C 0.76241(15) 0.5948(4) 0.35620(10) 0.0495(5) Uani 1 1 d . . . . .
C9 C 0.91821(15) 0.3491(4) 0.32767(10) 0.0531(5) Uani 1 1 d . . . . .
H9 H 0.8989 0.4716 0.3023 0.064 Uiso 1 1 calc R U . . .
C13 C 0.90569(15) 0.1150(4) 0.41709(11) 0.0528(5) Uani 1 1 d . . . . .
H13 H 0.8780 0.0782 0.4526 0.063 Uiso 1 1 calc R U . . .
C22 C 0.81075(16) 0.4405(4) 0.62525(10) 0.0550(6) Uani 1 1 d . . . . .
H22 H 0.8442 0.5727 0.6258 0.066 Uiso 1 1 calc R U . . .
C16 C 0.86163(17) 0.6237(4) 0.51423(11) 0.0573(6) Uani 1 1 d . . . . .
H16A H 0.8277 0.7478 0.5280 0.086 Uiso 1 1 calc R U . . .
H16B H 0.8786 0.6557 0.4730 0.086 Uiso 1 1 calc R U . . .
H16C H 0.9150 0.6011 0.5438 0.086 Uiso 1 1 calc R U . . .
C18 C 0.72837(16) 0.1439(4) 0.56931(12) 0.0566(6) Uani 1 1 d . . . . .
H18 H 0.7052 0.0730 0.5318 0.068 Uiso 1 1 calc R U . . .
C11 C 1.01973(16) 0.0397(5) 0.34980(12) 0.0611(6) Uani 1 1 d . . . . .
H11 H 1.0673 -0.0480 0.3392 0.073 Uiso 1 1 calc R U . . .
C12 C 0.97832(16) -0.0120(4) 0.40216(13) 0.0607(6) Uani 1 1 d . . . . .
H12 H 0.9990 -0.1328 0.4278 0.073 Uiso 1 1 calc R U . . .
C10 C 0.99043(16) 0.2220(5) 0.31324(11) 0.0623(7) Uani 1 1 d . . . . .
H10 H 1.0195 0.2602 0.2785 0.075 Uiso 1 1 calc R U . . .
C15 C 0.73243(19) 0.7587(5) 0.31919(11) 0.0644(7) Uani 1 1 d . . . . .
H15A H 0.7710 0.8747 0.3108 0.077 Uiso 1 1 calc R U . . .
H15B H 0.6723 0.7601 0.3011 0.077 Uiso 1 1 calc R U . . .
C21 C 0.7913(2) 0.3480(6) 0.68211(11) 0.0735(9) Uani 1 1 d . . . . .
H21 H 0.8126 0.4188 0.7201 0.088 Uiso 1 1 calc R U . . .
C19 C 0.7107(2) 0.0563(5) 0.62750(16) 0.0751(8) Uani 1 1 d . . . . .
H19 H 0.6767 -0.0744 0.6280 0.090 Uiso 1 1 calc R U . . .
C20 C 0.7420(2) 0.1569(6) 0.68357(13) 0.0783(9) Uani 1 1 d . . . . .
H20 H 0.7298 0.0960 0.7219 0.094 Uiso 1 1 calc R U . . .
C1 C 0.49501(16) 0.4934(6) 0.41200(14) 0.0717(8) Uani 1 1 d . . . . .
H1A H 0.4999 0.6432 0.4301 0.086 Uiso 1 1 calc R U . . .
H1B H 0.4531 0.4078 0.4340 0.086 Uiso 1 1 calc R U . . .
C3 C 0.5434(2) 0.1905(6) 0.32108(15) 0.0792(9) Uani 1 1 d . . . . .
H3A H 0.5844 0.2814 0.2997 0.095 Uiso 1 1 calc R U . . .
H3B H 0.5395 0.0435 0.3012 0.095 Uiso 1 1 calc R U . . .
C4 C 0.5807(2) 0.1657(5) 0.38823(16) 0.0789(9) Uani 1 1 d . . . . .
H4A H 0.5433 0.0629 0.4091 0.095 Uiso 1 1 calc R U . . .
H4B H 0.6412 0.1034 0.3912 0.095 Uiso 1 1 calc R U . . .
C2 C 0.4611(2) 0.5069(6) 0.34381(16) 0.0853(9) Uani 1 1 d . U . . .
H2A H 0.4013 0.5737 0.3389 0.102 Uiso 1 1 calc R U . . .
H2B H 0.5005 0.6044 0.3230 0.102 Uiso 1 1 calc R 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 C5 1.221(2) . ?
N2 C17 1.397(3) . ?
N2 C16 1.448(3) . ?
N2 C6 1.457(2) . ?
O1 C3 1.417(3) . ?
O1 C2 1.433(4) . ?
N1 C5 1.352(3) . ?
N1 C1 1.459(3) . ?
N1 C4 1.465(3) . ?
C17 C22 1.395(3) . ?
C17 C18 1.396(3) . ?
C6 C7 1.525(3) . ?
C6 C5 1.540(3) . ?
C6 H6 0.9800 . ?
C7 C14 1.306(3) . ?
C7 C8 1.496(3) . ?
C8 C13 1.387(3) . ?
C8 C9 1.392(3) . ?
C14 C15 1.296(3) . ?
C9 C10 1.380(3) . ?
C9 H9 0.9300 . ?
C13 C12 1.389(3) . ?
C13 H13 0.9300 . ?
C22 C21 1.391(4) . ?
C22 H22 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C18 C19 1.396(4) . ?
C18 H18 0.9300 . ?
C11 C12 1.372(4) . ?
C11 C10 1.373(4) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C10 H10 0.9300 . ?
C15 H15A 0.9300 . ?
C15 H15B 0.9300 . ?
C21 C20 1.356(5) . ?
C21 H21 0.9300 . ?
C19 C20 1.362(5) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C1 C2 1.476(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C3 C4 1.472(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 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
C17 N2 C16 118.25(17) . . ?
C17 N2 C6 117.85(16) . . ?
C16 N2 C6 118.59(16) . . ?
C3 O1 C2 109.7(2) . . ?
C5 N1 C1 120.7(2) . . ?
C5 N1 C4 127.6(2) . . ?
C1 N1 C4 111.5(2) . . ?
C22 C17 C18 117.1(2) . . ?
C22 C17 N2 120.3(2) . . ?
C18 C17 N2 122.51(19) . . ?
N2 C6 C7 112.41(15) . . ?
N2 C6 C5 111.29(15) . . ?
C7 C6 C5 110.22(15) . . ?
N2 C6 H6 107.6 . . ?
C7 C6 H6 107.6 . . ?
C5 C6 H6 107.6 . . ?
C14 C7 C8 121.06(18) . . ?
C14 C7 C6 120.35(18) . . ?
C8 C7 C6 118.59(17) . . ?
C13 C8 C9 117.96(19) . . ?
C13 C8 C7 121.90(18) . . ?
C9 C8 C7 120.14(18) . . ?
O2 C5 N1 122.33(19) . . ?
O2 C5 C6 120.03(18) . . ?
N1 C5 C6 117.63(17) . . ?
C15 C14 C7 179.0(3) . . ?
C10 C9 C8 120.8(2) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C8 C13 C12 120.8(2) . . ?
C8 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C21 C22 C17 120.9(3) . . ?
C21 C22 H22 119.6 . . ?
C17 C22 H22 119.6 . . ?
N2 C16 H16A 109.5 . . ?
N2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C19 C18 C17 120.1(3) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C12 C11 C10 119.5(2) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C11 C12 C13 120.3(2) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C11 C10 C9 120.6(2) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C14 C15 H15A 120.0 . . ?
C14 C15 H15B 120.0 . . ?
H15A C15 H15B 120.0 . . ?
C20 C21 C22 121.6(3) . . ?
C20 C21 H21 119.2 . . ?
C22 C21 H21 119.2 . . ?
C20 C19 C18 121.9(3) . . ?
C20 C19 H19 119.0 . . ?
C18 C19 H19 119.0 . . ?
C21 C20 C19 118.4(2) . . ?
C21 C20 H20 120.8 . . ?
C19 C20 H20 120.8 . . ?
N1 C1 C2 109.3(2) . . ?
N1 C1 H1A 109.8 . . ?
C2 C1 H1A 109.8 . . ?
N1 C1 H1B 109.8 . . ?
C2 C1 H1B 109.8 . . ?
H1A C1 H1B 108.3 . . ?
O1 C3 C4 112.5(3) . . ?
O1 C3 H3A 109.1 . . ?
C4 C3 H3A 109.1 . . ?
O1 C3 H3B 109.1 . . ?
C4 C3 H3B 109.1 . . ?
H3A C3 H3B 107.8 . . ?
N1 C4 C3 110.0(2) . . ?
N1 C4 H4A 109.7 . . ?
C3 C4 H4A 109.7 . . ?
N1 C4 H4B 109.7 . . ?
C3 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
O1 C2 C1 112.6(3) . . ?
O1 C2 H2A 109.1 . . ?
C1 C2 H2A 109.1 . . ?
O1 C2 H2B 109.1 . . ?
C1 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?

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
C16 N2 C17 C22 -2.5(3) . . . . ?
C6 N2 C17 C22 -156.41(18) . . . . ?
C16 N2 C17 C18 -179.5(2) . . . . ?
C6 N2 C17 C18 26.6(3) . . . . ?
C17 N2 C6 C7 -168.02(17) . . . . ?
C16 N2 C6 C7 38.2(2) . . . . ?
C17 N2 C6 C5 67.8(2) . . . . ?
C16 N2 C6 C5 -86.0(2) . . . . ?
N2 C6 C7 C14 -112.7(2) . . . . ?
C5 C6 C7 C14 12.1(3) . . . . ?
N2 C6 C7 C8 68.2(2) . . . . ?
C5 C6 C7 C8 -167.01(17) . . . . ?
C14 C7 C8 C13 -176.7(2) . . . . ?
C6 C7 C8 C13 2.4(3) . . . . ?
C14 C7 C8 C9 2.6(3) . . . . ?
C6 C7 C8 C9 -178.26(19) . . . . ?
C1 N1 C5 O2 5.4(4) . . . . ?
C4 N1 C5 O2 -179.6(3) . . . . ?
C1 N1 C5 C6 -176.0(2) . . . . ?
C4 N1 C5 C6 -1.1(4) . . . . ?
N2 C6 C5 O2 32.6(3) . . . . ?
C7 C6 C5 O2 -92.8(2) . . . . ?
N2 C6 C5 N1 -145.96(19) . . . . ?
C7 C6 C5 N1 88.6(2) . . . . ?
C13 C8 C9 C10 1.2(3) . . . . ?
C7 C8 C9 C10 -178.2(2) . . . . ?
C9 C8 C13 C12 -1.3(3) . . . . ?
C7 C8 C13 C12 178.1(2) . . . . ?
C18 C17 C22 C21 2.1(3) . . . . ?
N2 C17 C22 C21 -175.1(2) . . . . ?
C22 C17 C18 C19 -2.3(3) . . . . ?
N2 C17 C18 C19 174.8(2) . . . . ?
C10 C11 C12 C13 1.8(4) . . . . ?
C8 C13 C12 C11 -0.2(4) . . . . ?
C12 C11 C10 C9 -1.9(4) . . . . ?
C8 C9 C10 C11 0.4(4) . . . . ?
C17 C22 C21 C20 -0.7(4) . . . . ?
C17 C18 C19 C20 1.2(4) . . . . ?
C22 C21 C20 C19 -0.5(4) . . . . ?
C18 C19 C20 C21 0.3(4) . . . . ?
C5 N1 C1 C2 121.3(3) . . . . ?
C4 N1 C1 C2 -54.4(4) . . . . ?
C2 O1 C3 C4 57.5(4) . . . . ?
C5 N1 C4 C3 -120.8(3) . . . . ?
C1 N1 C4 C3 54.5(4) . . . . ?
O1 C3 C4 N1 -56.3(4) . . . . ?
C3 O1 C2 C1 -57.9(4) . . . . ?
N1 C1 C2 O1 56.5(4) . . . . ?

_refine_diff_density_max         0.664
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.049

_shelxl_version_number           2013-4

