# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1570338'
_audit_update_record             
;
2017-08-23 deposited with the CCDC.
2017-12-12 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            'C21 H22 N2 O2'
_chemical_formula_weight         334.40

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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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'

_cell_length_a                   10.467(2)
_cell_length_b                   6.9909(13)
_cell_length_c                   23.485(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1718.5(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5629
_cell_measurement_theta_min      3.4820
_cell_measurement_theta_max      25.8070

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_T_min  0.61530
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Micro-Focus (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       ω/q-scan
_diffrn_detector_area_resol_mean 15.9948
_diffrn_reflns_number            15729
_diffrn_reflns_av_unetI/netI     0.1060
_diffrn_reflns_av_R_equivalents  0.1491
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.040
_diffrn_reflns_theta_max         28.971
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.935
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.886
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             4042
_reflns_number_gt                2518
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.852
_reflns_Friedel_fraction_max     0.835
_reflns_Friedel_fraction_full    0.981

_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       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97

_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)+(0.2000P)²] 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       0.036(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 690 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   2.2(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4042
_refine_ls_number_parameters     228
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.1912
_refine_ls_R_factor_gt           0.1550
_refine_ls_wR_factor_ref         0.4130
_refine_ls_wR_factor_gt          0.3837
_refine_ls_goodness_of_fit_ref   1.336
_refine_ls_restrained_S_all      1.336
_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 0.2832(8) 0.7685(11) 0.4660(4) 0.0547(19) Uani 1 1 d . . . . .
H101 H 0.2282 0.8194 0.4858 0.082 Uiso 1 1 calc R U . . .
O2 O 0.5958(7) 0.5512(10) 0.5122(3) 0.0534(19) Uani 1 1 d . . . . .
H102 H 0.5387 0.5525 0.4882 0.080 Uiso 1 1 calc R U . . .
N1 N 0.3897(8) 0.4242(12) 0.4592(4) 0.0454(19) Uani 1 1 d . . . . .
N2 N 0.8038(8) 0.1260(13) 0.6394(4) 0.055(2) Uani 1 1 d D . . . .
C1 C 0.2269(10) 0.6452(15) 0.4288(5) 0.046(2) Uani 1 1 d . . . . .
C2 C 0.1237(9) 0.6929(15) 0.3965(5) 0.048(2) Uani 1 1 d . . . . .
H2A H 0.0911 0.8165 0.3982 0.057 Uiso 1 1 calc R U . . .
C3 C 0.0659(9) 0.5563(17) 0.3606(5) 0.051(3) Uani 1 1 d . . . . .
C4 C -0.0428(12) 0.601(2) 0.3258(5) 0.067(3) Uani 1 1 d . . . . .
H4 H -0.0773 0.7238 0.3262 0.080 Uiso 1 1 calc R U . . .
C5 C -0.0949(12) 0.462(2) 0.2922(6) 0.065(3) Uani 1 1 d . . . . .
H5 H -0.1672 0.4915 0.2709 0.078 Uiso 1 1 calc R U . . .
C6 C -0.0442(12) 0.281(2) 0.2887(5) 0.066(3) Uani 1 1 d . . . . .
H6 H -0.0822 0.1915 0.2646 0.079 Uiso 1 1 calc R U . . .
C7 C 0.0618(12) 0.228(2) 0.3201(5) 0.058(3) Uani 1 1 d . . . . .
H7 H 0.0949 0.1045 0.3175 0.070 Uiso 1 1 calc R U . . .
C8 C 0.1193(9) 0.3658(17) 0.3565(5) 0.049(2) Uani 1 1 d . . . . .
C9 C 0.2265(11) 0.3271(18) 0.3891(4) 0.051(2) Uani 1 1 d . . . . .
H9 H 0.2643 0.2069 0.3867 0.062 Uiso 1 1 calc R U . . .
C10 C 0.2783(10) 0.4622(14) 0.4247(4) 0.042(2) Uani 1 1 d . . . . .
C11 C 0.4260(10) 0.2551(14) 0.4763(5) 0.044(2) Uani 1 1 d . . . . .
H11 H 0.3806 0.1492 0.4635 0.053 Uiso 1 1 calc R U . . .
C12 C 0.5297(9) 0.2243(13) 0.5130(4) 0.040(2) Uani 1 1 d . . . . .
C13 C 0.6078(9) 0.3791(13) 0.5326(5) 0.041(2) Uani 1 1 d . . . . .
C14 C 0.7004(9) 0.3428(14) 0.5745(4) 0.042(2) Uani 1 1 d . . . . .
H14 H 0.7498 0.4440 0.5878 0.050 Uiso 1 1 calc R U . . .
C15 C 0.7209(10) 0.1600(14) 0.5970(5) 0.043(2) Uani 1 1 d . . . . .
C16 C 0.6490(10) 0.0010(15) 0.5721(4) 0.045(2) Uani 1 1 d . . . . .
H16 H 0.6666 -0.1243 0.5828 0.054 Uiso 1 1 calc R U . . .
C17 C 0.5569(9) 0.0383(14) 0.5335(4) 0.043(2) Uani 1 1 d . . . . .
H17 H 0.5088 -0.0634 0.5197 0.051 Uiso 1 1 calc R U . . .
C18 C 0.8738(10) 0.2831(17) 0.6666(5) 0.059(3) Uani 1 1 d D . . . .
H18A H 0.9016 0.3721 0.6374 0.070 Uiso 1 1 calc R U . . .
H18B H 0.9496 0.2317 0.6848 0.070 Uiso 1 1 calc R U . . .
C19 C 0.7971(16) 0.389(2) 0.7099(6) 0.079(4) Uani 1 1 d D . . . .
H19A H 0.8480 0.4895 0.7260 0.118 Uiso 1 1 calc R U . . .
H19B H 0.7229 0.4431 0.6920 0.118 Uiso 1 1 calc R U . . .
H19C H 0.7710 0.3025 0.7394 0.118 Uiso 1 1 calc R U . . .
C20 C 0.8266(11) -0.0670(16) 0.6633(4) 0.054(3) Uani 1 1 d D . . . .
H20A H 0.7475 -0.1392 0.6623 0.065 Uiso 1 1 calc R U . . .
H20B H 0.8523 -0.0548 0.7028 0.065 Uiso 1 1 calc R U . . .
C21 C 0.9278(12) -0.1753(19) 0.6313(7) 0.073(4) Uani 1 1 d D . . . .
H21A H 0.9392 -0.2991 0.6482 0.110 Uiso 1 1 calc R U . . .
H21B H 0.9020 -0.1902 0.5923 0.110 Uiso 1 1 calc R U . . .
H21C H 1.0069 -0.1058 0.6328 0.110 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 C1 1.363(14) . ?
O1 H101 0.8200 . ?
O2 C13 1.302(12) . ?
O2 H102 0.8200 . ?
N1 C11 1.305(13) . ?
N1 C10 1.445(13) . ?
N2 C15 1.341(14) . ?
N2 C18 1.466(14) . ?
N2 C20 1.481(14) . ?
C1 C2 1.360(15) . ?
C1 C10 1.391(14) . ?
C2 C3 1.411(16) . ?
C2 H2A 0.9300 . ?
C3 C4 1.435(16) . ?
C3 C8 1.447(16) . ?
C4 C5 1.364(19) . ?
C4 H4 0.9300 . ?
C5 C6 1.38(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.384(18) . ?
C6 H6 0.9300 . ?
C7 C8 1.423(15) . ?
C7 H7 0.9300 . ?
C8 C9 1.385(15) . ?
C9 C10 1.374(14) . ?
C9 H9 0.9300 . ?
C11 C12 1.403(14) . ?
C11 H11 0.9300 . ?
C12 C17 1.415(14) . ?
C12 C13 1.432(13) . ?
C13 C14 1.405(14) . ?
C14 C15 1.400(13) . ?
C14 H14 0.9300 . ?
C15 C16 1.465(15) . ?
C16 C17 1.348(15) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C19 1.493(17) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.504(13) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

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 O1 H101 109.5 . . ?
C13 O2 H102 109.5 . . ?
C11 N1 C10 125.1(9) . . ?
C15 N2 C18 120.9(9) . . ?
C15 N2 C20 123.2(9) . . ?
C18 N2 C20 115.9(9) . . ?
C2 C1 O1 123.1(10) . . ?
C2 C1 C10 119.6(10) . . ?
O1 C1 C10 117.3(9) . . ?
C1 C2 C3 120.5(10) . . ?
C1 C2 H2A 119.7 . . ?
C3 C2 H2A 119.7 . . ?
C2 C3 C4 122.2(11) . . ?
C2 C3 C8 119.8(9) . . ?
C4 C3 C8 118.0(11) . . ?
C5 C4 C3 119.4(13) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 122.5(12) . . ?
C4 C5 H5 118.8 . . ?
C6 C5 H5 118.8 . . ?
C5 C6 C7 121.4(12) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C6 C7 C8 118.6(12) . . ?
C6 C7 H7 120.7 . . ?
C8 C7 H7 120.7 . . ?
C9 C8 C7 122.8(11) . . ?
C9 C8 C3 117.2(10) . . ?
C7 C8 C3 120.1(10) . . ?
C10 C9 C8 121.4(11) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C9 C10 C1 121.5(10) . . ?
C9 C10 N1 122.2(9) . . ?
C1 C10 N1 116.3(8) . . ?
N1 C11 C12 123.6(9) . . ?
N1 C11 H11 118.2 . . ?
C12 C11 H11 118.2 . . ?
C11 C12 C17 120.4(8) . . ?
C11 C12 C13 121.5(8) . . ?
C17 C12 C13 118.1(9) . . ?
O2 C13 C14 119.5(9) . . ?
O2 C13 C12 121.7(9) . . ?
C14 C13 C12 118.8(9) . . ?
C15 C14 C13 122.4(9) . . ?
C15 C14 H14 118.8 . . ?
C13 C14 H14 118.8 . . ?
N2 C15 C14 122.8(9) . . ?
N2 C15 C16 119.7(9) . . ?
C14 C15 C16 117.6(9) . . ?
C17 C16 C15 119.3(9) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C16 C17 C12 123.4(9) . . ?
C16 C17 H17 118.3 . . ?
C12 C17 H17 118.3 . . ?
N2 C18 C19 113.5(10) . . ?
N2 C18 H18A 108.9 . . ?
C19 C18 H18A 108.9 . . ?
N2 C18 H18B 108.9 . . ?
C19 C18 H18B 108.9 . . ?
H18A C18 H18B 107.7 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N2 C20 C21 112.5(9) . . ?
N2 C20 H20A 109.1 . . ?
C21 C20 H20A 109.1 . . ?
N2 C20 H20B 109.1 . . ?
C21 C20 H20B 109.1 . . ?
H20A C20 H20B 107.8 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
O1 C1 C2 C3 -177.1(9) . . . . ?
C10 C1 C2 C3 2.3(15) . . . . ?
C1 C2 C3 C4 -179.8(10) . . . . ?
C1 C2 C3 C8 -2.1(16) . . . . ?
C2 C3 C4 C5 -179.6(11) . . . . ?
C8 C3 C4 C5 2.7(17) . . . . ?
C3 C4 C5 C6 -2(2) . . . . ?
C4 C5 C6 C7 1(2) . . . . ?
C5 C6 C7 C8 -0.3(19) . . . . ?
C6 C7 C8 C9 -179.2(11) . . . . ?
C6 C7 C8 C3 0.7(16) . . . . ?
C2 C3 C8 C9 0.2(15) . . . . ?
C4 C3 C8 C9 178.0(10) . . . . ?
C2 C3 C8 C7 -179.7(10) . . . . ?
C4 C3 C8 C7 -1.9(15) . . . . ?
C7 C8 C9 C10 -178.6(10) . . . . ?
C3 C8 C9 C10 1.5(15) . . . . ?
C8 C9 C10 C1 -1.4(16) . . . . ?
C8 C9 C10 N1 179.7(10) . . . . ?
C2 C1 C10 C9 -0.6(15) . . . . ?
O1 C1 C10 C9 178.8(10) . . . . ?
C2 C1 C10 N1 178.4(9) . . . . ?
O1 C1 C10 N1 -2.2(13) . . . . ?
C11 N1 C10 C9 -25.2(15) . . . . ?
C11 N1 C10 C1 155.9(10) . . . . ?
C10 N1 C11 C12 -175.4(9) . . . . ?
N1 C11 C12 C17 174.8(10) . . . . ?
N1 C11 C12 C13 -2.8(15) . . . . ?
C11 C12 C13 O2 -8.3(15) . . . . ?
C17 C12 C13 O2 174.1(10) . . . . ?
C11 C12 C13 C14 172.4(9) . . . . ?
C17 C12 C13 C14 -5.2(14) . . . . ?
O2 C13 C14 C15 -178.0(10) . . . . ?
C12 C13 C14 C15 1.3(14) . . . . ?
C18 N2 C15 C14 3.0(15) . . . . ?
C20 N2 C15 C14 -179.7(10) . . . . ?
C18 N2 C15 C16 -177.8(10) . . . . ?
C20 N2 C15 C16 -0.5(15) . . . . ?
C13 C14 C15 N2 -176.0(10) . . . . ?
C13 C14 C15 C16 4.8(14) . . . . ?
N2 C15 C16 C17 173.5(9) . . . . ?
C14 C15 C16 C17 -7.3(14) . . . . ?
C15 C16 C17 C12 3.6(15) . . . . ?
C11 C12 C17 C16 -174.9(9) . . . . ?
C13 C12 C17 C16 2.7(15) . . . . ?
C15 N2 C18 C19 80.1(15) . . . . ?
C20 N2 C18 C19 -97.4(12) . . . . ?
C15 N2 C20 C21 87.4(14) . . . . ?
C18 N2 C20 C21 -95.2(13) . . . . ?

_refine_diff_density_max         0.675
_refine_diff_density_min         -0.486
_refine_diff_density_rms         0.163

