# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_a
_audit_block_doi                 10.5517/ccdc.csd.cc215mrm
_database_code_depnum_ccdc_archive 'CCDC 1882250'
_audit_update_record             
;
2018-11-30 deposited with the CCDC.
2019-01-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H22 N2 O2'
_chemical_formula_weight         286.36

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   18.8452(14)
_cell_length_b                   5.9542(4)
_cell_length_c                   27.679(2)
_cell_angle_alpha                90
_cell_angle_beta                 103.868(2)
_cell_angle_gamma                90
_cell_volume                     3015.3(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9153
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      27.53

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_F_000             1232
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            36497
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         3.598
_diffrn_reflns_theta_max         27.536
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3460
_reflns_number_gt                2857
_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, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_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)+(0.1034P)²+1.6568P] 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         3460
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0522
_refine_ls_wR_factor_ref         0.1714
_refine_ls_wR_factor_gt          0.1608
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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
O1 O 0.09739(8) 0.9096(3) 0.65828(7) 0.0791(5) Uani 1 1 d . . . . .
O2 O 0.22552(8) 0.2886(2) 0.72018(5) 0.0568(4) Uani 1 1 d . . . . .
N1 N 0.39300(7) 0.0027(2) 0.55457(5) 0.0440(3) Uani 1 1 d . . . . .
N2 N 0.15063(7) 0.5885(2) 0.69496(5) 0.0411(3) Uani 1 1 d . . . . .
C1 C 0.47787(11) -0.2707(4) 0.54217(9) 0.0701(6) Uani 1 1 d . . . . .
H5 H 0.512257 -0.236414 0.522149 0.084 Uiso 1 1 calc R U . . .
H1 H 0.496355 -0.397852 0.563387 0.084 Uiso 1 1 calc R U . . .
C2 C 0.46830(9) -0.0700(4) 0.57330(7) 0.0553(5) Uani 1 1 d . . . . .
H6 H 0.477235 -0.111226 0.608143 0.066 Uiso 1 1 calc R U . . .
H7 H 0.501902 0.048898 0.569831 0.066 Uiso 1 1 calc R U . . .
C3 C 0.36143(8) 0.1508(3) 0.58199(5) 0.0367(3) Uani 1 1 d . . . . .
C4 C 0.28587(8) 0.1797(3) 0.57218(5) 0.0369(3) Uani 1 1 d . . . . .
H17 H 0.256190 0.100534 0.546028 0.044 Uiso 1 1 calc R U . . .
C5 C 0.25356(7) 0.3232(2) 0.60028(5) 0.0328(3) Uani 1 1 d . . . . .
C6 C 0.29686(7) 0.4468(2) 0.63951(5) 0.0321(3) Uani 1 1 d . . . . .
C7 C 0.26385(8) 0.5925(2) 0.67326(5) 0.0354(3) Uani 1 1 d . . . . .
H13 H 0.304601 0.648041 0.699543 0.043 Uiso 1 1 calc R U . . .
C8 C 0.21374(9) 0.4659(3) 0.69887(5) 0.0376(3) Uani 1 1 d . . . . .
C9 C 0.09329(11) 0.5214(4) 0.71889(9) 0.0675(6) Uani 1 1 d . . . . .
H10 H 0.084993 0.362734 0.714722 0.101 Uiso 1 1 calc R U . . .
H11 H 0.049096 0.600748 0.704036 0.101 Uiso 1 1 calc R U . . .
H2 H 0.107865 0.556387 0.753723 0.101 Uiso 1 1 calc R U . . .
C10 C 0.40435(10) -0.3241(4) 0.50943(8) 0.0586(5) Uani 1 1 d . . . . .
H3 H 0.393161 -0.482057 0.511878 0.070 Uiso 1 1 calc R U . . .
H4 H 0.403261 -0.289715 0.475004 0.070 Uiso 1 1 calc R U . . .
C11 C 0.40433(8) 0.2822(3) 0.61990(6) 0.0406(4) Uani 1 1 d . . . . .
H8 H 0.454962 0.271668 0.626274 0.049 Uiso 1 1 calc R U . . .
C12 C 0.37328(8) 0.4278(3) 0.64826(6) 0.0379(3) Uani 1 1 d . . . . .
C13 C 0.21869(9) 0.7993(3) 0.65108(7) 0.0425(4) Uani 1 1 d . . . . .
H12 H 0.244335 0.936647 0.663479 0.051 Uiso 1 1 calc R U . . .
H9 H 0.209311 0.798274 0.615054 0.051 Uiso 1 1 calc R U . . .
C14 C 0.14854(9) 0.7819(3) 0.66737(7) 0.0457(4) Uani 1 1 d . . . . .
C15 C 0.17099(8) 0.3301(3) 0.58786(6) 0.0418(4) Uani 1 1 d . . . . .
H15 H 0.152083 0.268738 0.555239 0.063 Uiso 1 1 calc R U . . .
H14 H 0.154939 0.482836 0.588615 0.063 Uiso 1 1 calc R U . . .
H16 H 0.153500 0.243222 0.611833 0.063 Uiso 1 1 calc R U . . .
C16 C 0.42423(9) 0.5631(4) 0.68814(7) 0.0577(5) Uani 1 1 d . . . . .
H20 H 0.473880 0.534899 0.686803 0.087 Uiso 1 1 calc R U . . .
H18 H 0.417598 0.520266 0.720209 0.087 Uiso 1 1 calc R U . . .
H19 H 0.413600 0.720064 0.682765 0.087 Uiso 1 1 calc R U . . .
C17 C 0.34952(9) -0.1800(3) 0.52749(6) 0.0458(4) Uani 1 1 d . . . . .
H21 H 0.312349 -0.122792 0.499676 0.055 Uiso 1 1 calc R U . . .
H22 H 0.325998 -0.265172 0.549159 0.055 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
O1 C14 1.206(2) . ?
O2 C8 1.2038(19) . ?
N1 C3 1.3873(19) . ?
N1 C2 1.455(2) . ?
N1 C17 1.457(2) . ?
N2 C8 1.377(2) . ?
N2 C14 1.377(2) . ?
N2 C9 1.452(2) . ?
C1 C10 1.497(3) . ?
C1 C2 1.509(3) . ?
C1 H5 0.9700 . ?
C1 H1 0.9700 . ?
C2 H6 0.9700 . ?
C2 H7 0.9700 . ?
C3 C4 1.395(2) . ?
C3 C11 1.400(2) . ?
C4 C5 1.390(2) . ?
C4 H17 0.9300 . ?
C5 C6 1.401(2) . ?
C5 C15 1.5117(19) . ?
C6 C12 1.406(2) . ?
C6 C7 1.5135(19) . ?
C7 C8 1.511(2) . ?
C7 C13 1.538(2) . ?
C7 H13 0.9800 . ?
C9 H10 0.9600 . ?
C9 H11 0.9600 . ?
C9 H2 0.9600 . ?
C10 C17 1.517(2) . ?
C10 H3 0.9700 . ?
C10 H4 0.9700 . ?
C11 C12 1.390(2) . ?
C11 H8 0.9300 . ?
C12 C16 1.510(2) . ?
C13 C14 1.499(2) . ?
C13 H12 0.9700 . ?
C13 H9 0.9700 . ?
C15 H15 0.9600 . ?
C15 H14 0.9600 . ?
C15 H16 0.9600 . ?
C16 H20 0.9600 . ?
C16 H18 0.9600 . ?
C16 H19 0.9600 . ?
C17 H21 0.9700 . ?
C17 H22 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
C3 N1 C2 120.25(13) . . ?
C3 N1 C17 119.61(13) . . ?
C2 N1 C17 109.96(14) . . ?
C8 N2 C14 113.35(13) . . ?
C8 N2 C9 122.77(15) . . ?
C14 N2 C9 123.86(15) . . ?
C10 C1 C2 107.08(16) . . ?
C10 C1 H5 110.3 . . ?
C2 C1 H5 110.3 . . ?
C10 C1 H1 110.3 . . ?
C2 C1 H1 110.3 . . ?
H5 C1 H1 108.6 . . ?
N1 C2 C1 105.79(15) . . ?
N1 C2 H6 110.6 . . ?
C1 C2 H6 110.6 . . ?
N1 C2 H7 110.6 . . ?
C1 C2 H7 110.6 . . ?
H6 C2 H7 108.7 . . ?
N1 C3 C4 121.57(13) . . ?
N1 C3 C11 121.26(13) . . ?
C4 C3 C11 117.15(13) . . ?
C5 C4 C3 122.03(13) . . ?
C5 C4 H17 119.0 . . ?
C3 C4 H17 119.0 . . ?
C4 C5 C6 120.32(13) . . ?
C4 C5 C15 117.03(13) . . ?
C6 C5 C15 122.60(13) . . ?
C5 C6 C12 118.25(13) . . ?
C5 C6 C7 122.03(13) . . ?
C12 C6 C7 119.68(12) . . ?
C8 C7 C6 113.50(12) . . ?
C8 C7 C13 103.79(12) . . ?
C6 C7 C13 118.84(13) . . ?
C8 C7 H13 106.7 . . ?
C6 C7 H13 106.7 . . ?
C13 C7 H13 106.7 . . ?
O2 C8 N2 123.89(15) . . ?
O2 C8 C7 127.23(15) . . ?
N2 C8 C7 108.87(12) . . ?
N2 C9 H10 109.5 . . ?
N2 C9 H11 109.5 . . ?
H10 C9 H11 109.5 . . ?
N2 C9 H2 109.5 . . ?
H10 C9 H2 109.5 . . ?
H11 C9 H2 109.5 . . ?
C1 C10 C17 106.58(15) . . ?
C1 C10 H3 110.4 . . ?
C17 C10 H3 110.4 . . ?
C1 C10 H4 110.4 . . ?
C17 C10 H4 110.4 . . ?
H3 C10 H4 108.6 . . ?
C12 C11 C3 121.76(14) . . ?
C12 C11 H8 119.1 . . ?
C3 C11 H8 119.1 . . ?
C11 C12 C6 120.36(13) . . ?
C11 C12 C16 117.75(14) . . ?
C6 C12 C16 121.89(14) . . ?
C14 C13 C7 105.54(13) . . ?
C14 C13 H12 110.6 . . ?
C7 C13 H12 110.6 . . ?
C14 C13 H9 110.6 . . ?
C7 C13 H9 110.6 . . ?
H12 C13 H9 108.8 . . ?
O1 C14 N2 123.96(16) . . ?
O1 C14 C13 127.71(16) . . ?
N2 C14 C13 108.33(13) . . ?
C5 C15 H15 109.5 . . ?
C5 C15 H14 109.5 . . ?
H15 C15 H14 109.5 . . ?
C5 C15 H16 109.5 . . ?
H15 C15 H16 109.5 . . ?
H14 C15 H16 109.5 . . ?
C12 C16 H20 109.5 . . ?
C12 C16 H18 109.5 . . ?
H20 C16 H18 109.5 . . ?
C12 C16 H19 109.5 . . ?
H20 C16 H19 109.5 . . ?
H18 C16 H19 109.5 . . ?
N1 C17 C10 104.37(13) . . ?
N1 C17 H21 110.9 . . ?
C10 C17 H21 110.9 . . ?
N1 C17 H22 110.9 . . ?
C10 C17 H22 110.9 . . ?
H21 C17 H22 108.9 . . ?

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
C3 N1 C2 C1 165.39(17) . . . . ?
C17 N1 C2 C1 20.3(2) . . . . ?
C10 C1 C2 N1 -6.0(3) . . . . ?
C2 N1 C3 C4 -163.38(16) . . . . ?
C17 N1 C3 C4 -21.6(2) . . . . ?
C2 N1 C3 C11 18.3(2) . . . . ?
C17 N1 C3 C11 160.16(16) . . . . ?
N1 C3 C4 C5 178.26(14) . . . . ?
C11 C3 C4 C5 -3.4(2) . . . . ?
C3 C4 C5 C6 0.8(2) . . . . ?
C3 C4 C5 C15 -176.61(14) . . . . ?
C4 C5 C6 C12 2.4(2) . . . . ?
C15 C5 C6 C12 179.61(14) . . . . ?
C4 C5 C6 C7 -175.70(13) . . . . ?
C15 C5 C6 C7 1.5(2) . . . . ?
C5 C6 C7 C8 57.00(18) . . . . ?
C12 C6 C7 C8 -121.05(15) . . . . ?
C5 C6 C7 C13 -65.43(19) . . . . ?
C12 C6 C7 C13 116.52(16) . . . . ?
C14 N2 C8 O2 -177.85(16) . . . . ?
C9 N2 C8 O2 3.7(3) . . . . ?
C14 N2 C8 C7 3.12(18) . . . . ?
C9 N2 C8 C7 -175.32(17) . . . . ?
C6 C7 C8 O2 47.2(2) . . . . ?
C13 C7 C8 O2 177.59(16) . . . . ?
C6 C7 C8 N2 -133.85(13) . . . . ?
C13 C7 C8 N2 -3.43(16) . . . . ?
C2 C1 C10 C17 -9.4(3) . . . . ?
N1 C3 C11 C12 -178.72(15) . . . . ?
C4 C3 C11 C12 2.9(2) . . . . ?
C3 C11 C12 C6 0.1(2) . . . . ?
C3 C11 C12 C16 -179.74(17) . . . . ?
C5 C6 C12 C11 -2.8(2) . . . . ?
C7 C6 C12 C11 175.31(14) . . . . ?
C5 C6 C12 C16 177.06(16) . . . . ?
C7 C6 C12 C16 -4.8(2) . . . . ?
C8 C7 C13 C14 2.56(17) . . . . ?
C6 C7 C13 C14 129.71(15) . . . . ?
C8 N2 C14 O1 177.87(19) . . . . ?
C9 N2 C14 O1 -3.7(3) . . . . ?
C8 N2 C14 C13 -1.4(2) . . . . ?
C9 N2 C14 C13 177.05(17) . . . . ?
C7 C13 C14 O1 179.9(2) . . . . ?
C7 C13 C14 N2 -0.91(19) . . . . ?
C3 N1 C17 C10 -171.32(15) . . . . ?
C2 N1 C17 C10 -25.9(2) . . . . ?
C1 C10 C17 N1 21.2(2) . . . . ?

_refine_diff_density_max         0.253
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.039



