# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_20170522PY_liuxueke_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1552692'
_audit_update_record             
;
2017-05-27 deposited with the CCDC.
2017-09-04 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            '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           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   6.0777(7)
_cell_length_b                   22.245(3)
_cell_length_c                   11.8606(15)
_cell_angle_alpha                90
_cell_angle_beta                 96.163(2)
_cell_angle_gamma                90
_cell_volume                     1594.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1613
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      22.81
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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            8866
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.831
_diffrn_reflns_theta_max         25.006
_diffrn_reflns_theta_full        25.006
_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 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2802
_reflns_number_gt                1766
_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_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)+(0.1525P)²+0.8837P] 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         2802
_refine_ls_number_parameters     188
_refine_ls_number_restraints     60
_refine_ls_R_factor_all          0.1128
_refine_ls_R_factor_gt           0.0778
_refine_ls_wR_factor_ref         0.2740
_refine_ls_wR_factor_gt          0.2365
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.131
_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 -0.3444(6) 0.34220(19) 0.4197(3) 0.0643(11) Uani 1 1 d . . . . .
H1A H -0.3597 0.3675 0.4840 0.097 Uiso 1 1 calc R U . . .
H1B H -0.4839 0.3396 0.3736 0.097 Uiso 1 1 calc R U . . .
H1C H -0.2355 0.3590 0.3759 0.097 Uiso 1 1 calc R U . . .
C2 C -0.0825(6) 0.27796(16) 0.5243(3) 0.0490(9) Uani 1 1 d . . . . .
C3 C -0.0281(6) 0.21877(16) 0.5574(3) 0.0544(9) Uani 1 1 d . . . . .
H3 H -0.1234 0.1874 0.5342 0.065 Uiso 1 1 calc R U . . .
C4 C 0.1659(6) 0.20733(15) 0.6240(3) 0.0503(9) Uani 1 1 d . . . . .
H4 H 0.2030 0.1680 0.6445 0.060 Uiso 1 1 calc R U . . .
C5 C 0.3082(5) 0.25411(14) 0.6614(3) 0.0426(8) Uani 1 1 d . . . . .
C6 C 0.2521(5) 0.31358(14) 0.6306(3) 0.0410(8) Uani 1 1 d . . . . .
C7 C 0.0558(5) 0.32486(15) 0.5599(3) 0.0458(8) Uani 1 1 d . . . . .
H7 H 0.0193 0.3639 0.5372 0.055 Uiso 1 1 calc R U . . .
C8 C 0.5133(5) 0.24192(14) 0.7334(3) 0.0432(8) Uani 1 1 d . . . . .
C9 C 0.8417(6) 0.29329(16) 0.8375(3) 0.0536(9) Uani 1 1 d . . . . .
H9A H 0.9576 0.2763 0.7971 0.064 Uiso 1 1 calc R U . . .
H9B H 0.8323 0.2706 0.9066 0.064 Uiso 1 1 calc R U . . .
C10 C 0.8836(7) 0.35890(19) 0.8629(4) 0.0696(11) Uani 1 1 d . . . . .
H10A H 0.8511 0.3681 0.9393 0.084 Uiso 1 1 calc R U . . .
H10B H 1.0374 0.3686 0.8568 0.084 Uiso 1 1 calc R U . . .
C11 C 0.7356(6) 0.39459(16) 0.7783(3) 0.0580(10) Uani 1 1 d . . . . .
H11 H 0.8241 0.4029 0.7157 0.070 Uiso 1 1 calc R U . . .
C12 C 0.5619(5) 0.34964(14) 0.7321(3) 0.0449(8) Uani 1 1 d . . . . .
C13 C 0.7698(8) 0.5109(2) 0.7741(5) 0.0842(13) Uani 1 1 d . U . . .
C14 C 1.0079(9) 0.5100(3) 0.8189(6) 0.1150(17) Uani 1 1 d . U . . .
H14A H 1.0730 0.5484 0.8063 0.172 Uiso 1 1 calc R U . . .
H14B H 1.0828 0.4794 0.7806 0.172 Uiso 1 1 calc R U . . .
H14C H 1.0216 0.5016 0.8987 0.172 Uiso 1 1 calc R U . . .
C15 C 0.6572(10) 0.5617(3) 0.8300(6) 0.1130(16) Uani 1 1 d . U . . .
H15A H 0.6708 0.5555 0.9105 0.170 Uiso 1 1 calc R U . . .
H15B H 0.5034 0.5629 0.8013 0.170 Uiso 1 1 calc R U . . .
H15C H 0.7258 0.5992 0.8137 0.170 Uiso 1 1 calc R U . . .
C16 C 0.7401(13) 0.5224(3) 0.6499(6) 0.144 Uani 1 1 d . U . . .
H16A H 0.8217 0.5577 0.6333 0.216 Uiso 1 1 calc R U . . .
H16B H 0.5859 0.5285 0.6255 0.216 Uiso 1 1 calc R U . . .
H16C H 0.7934 0.4886 0.6107 0.216 Uiso 1 1 calc R U . . .
N1 N 0.3828(5) 0.36241(12) 0.6671(2) 0.0486(7) Uani 1 1 d . . . . .
N2 N 0.6283(4) 0.29355(12) 0.7662(2) 0.0450(7) Uani 1 1 d . . . . .
O1 O 0.5841(4) 0.19240(11) 0.7637(2) 0.0610(7) Uani 1 1 d . . . . .
C17 C 0.6493(9) 0.4540(2) 0.8111(5) 0.0906(14) Uani 1 1 d . U . . .
H17A H 0.6528 0.4549 0.8930 0.109 Uiso 1 1 calc R U . . .
H17B H 0.4953 0.4567 0.7800 0.109 Uiso 1 1 calc R U . . .
O2 O -0.2768(4) 0.28414(12) 0.4574(2) 0.0647(8) 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 O2 1.413(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 O2 1.357(4) . ?
C2 C7 1.377(5) . ?
C2 C3 1.403(5) . ?
C3 C4 1.371(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.395(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.405(4) . ?
C5 C8 1.459(5) . ?
C6 N1 1.387(4) . ?
C6 C7 1.405(5) . ?
C7 H7 0.9300 . ?
C8 O1 1.222(4) . ?
C8 N2 1.378(4) . ?
C9 N2 1.470(4) . ?
C9 C10 1.506(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.501(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C17 1.490(6) . ?
C11 C12 1.514(5) . ?
C11 H11 0.9800 . ?
C12 N1 1.296(4) . ?
C12 N2 1.360(4) . ?
C13 C16 1.487(8) . ?
C13 C14 1.487(7) . ?
C13 C15 1.511(7) . ?
C13 C17 1.550(7) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9700 . ?
C17 H17B 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
O2 C1 H1A 109.5 . . ?
O2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 C7 124.5(3) . . ?
O2 C2 C3 115.0(3) . . ?
C7 C2 C3 120.5(3) . . ?
C4 C3 C2 119.8(3) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 120.7(3) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C6 119.7(3) . . ?
C4 C5 C8 120.6(3) . . ?
C6 C5 C8 119.7(3) . . ?
N1 C6 C5 122.8(3) . . ?
N1 C6 C7 117.9(3) . . ?
C5 C6 C7 119.4(3) . . ?
C2 C7 C6 119.9(3) . . ?
C2 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
O1 C8 N2 121.1(3) . . ?
O1 C8 C5 126.2(3) . . ?
N2 C8 C5 112.7(3) . . ?
N2 C9 C10 103.4(3) . . ?
N2 C9 H9A 111.1 . . ?
C10 C9 H9A 111.1 . . ?
N2 C9 H9B 111.1 . . ?
C10 C9 H9B 111.1 . . ?
H9A C9 H9B 109.1 . . ?
C11 C10 C9 107.6(3) . . ?
C11 C10 H10A 110.2 . . ?
C9 C10 H10A 110.2 . . ?
C11 C10 H10B 110.2 . . ?
C9 C10 H10B 110.2 . . ?
H10A C10 H10B 108.5 . . ?
C17 C11 C10 119.9(4) . . ?
C17 C11 C12 115.4(3) . . ?
C10 C11 C12 103.7(3) . . ?
C17 C11 H11 105.5 . . ?
C10 C11 H11 105.5 . . ?
C12 C11 H11 105.5 . . ?
N1 C12 N2 125.6(3) . . ?
N1 C12 C11 125.4(3) . . ?
N2 C12 C11 109.0(3) . . ?
C16 C13 C14 111.5(5) . . ?
C16 C13 C15 107.1(5) . . ?
C14 C13 C15 108.8(4) . . ?
C16 C13 C17 114.2(5) . . ?
C14 C13 C17 111.0(4) . . ?
C15 C13 C17 103.7(4) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C12 N1 C6 115.5(3) . . ?
C12 N2 C8 123.7(3) . . ?
C12 N2 C9 113.0(3) . . ?
C8 N2 C9 123.2(3) . . ?
C11 C17 C13 117.4(4) . . ?
C11 C17 H17A 107.9 . . ?
C13 C17 H17A 107.9 . . ?
C11 C17 H17B 107.9 . . ?
C13 C17 H17B 107.9 . . ?
H17A C17 H17B 107.2 . . ?
C2 O2 C1 118.9(3) . . ?

_refine_diff_density_max         0.831
_refine_diff_density_min         -0.523
_refine_diff_density_rms         0.058



####################################################################### 
# 
# 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_20170425PY_LXK_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1547405'
_audit_update_record             
;
2017-05-02 deposited with the CCDC.
2017-09-04 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            'C20 H22 N2 O'
_chemical_formula_weight         306.39

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'
Br Br -0.2901 2.4595 '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                   21.107(3)
_cell_length_b                   7.3437(11)
_cell_length_c                   21.914(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.993(5)
_cell_angle_gamma                90
_cell_volume                     3322.6(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4541
_cell_measurement_theta_min      2.94
_cell_measurement_theta_max      27.54
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_F_000             1312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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            11212
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.438
_diffrn_reflns_theta_max         25.006
_diffrn_reflns_theta_full        25.006
_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 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2932
_reflns_number_gt                2364
_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_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)+(0.1136P)²+8.8711P] 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       0.017(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2932
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0959
_refine_ls_R_factor_gt           0.0818
_refine_ls_wR_factor_ref         0.2278
_refine_ls_wR_factor_gt          0.2146
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_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 0.43012(13) 0.1454(4) 0.43246(13) 0.0259(7) Uani 1 1 d . . . . .
C2 C 0.36548(14) 0.0819(4) 0.41908(14) 0.0303(7) Uani 1 1 d . . . . .
H2 H 0.3479 0.0373 0.3795 0.036 Uiso 1 1 calc R U . . .
C3 C 0.32823(14) 0.0846(4) 0.46338(15) 0.0322(7) Uani 1 1 d . . . . .
H3 H 0.2860 0.0411 0.4539 0.039 Uiso 1 1 calc R U . . .
C4 C 0.35413(14) 0.1535(4) 0.52304(14) 0.0326(7) Uani 1 1 d . . . . .
H4 H 0.3286 0.1570 0.5528 0.039 Uiso 1 1 calc R U . . .
C5 C 0.41666(13) 0.2157(4) 0.53792(14) 0.0281(7) Uani 1 1 d . . . . .
H5 H 0.4332 0.2606 0.5777 0.034 Uiso 1 1 calc R U . . .
C6 C 0.45598(13) 0.2118(4) 0.49321(13) 0.0235(6) Uani 1 1 d . . . . .
C7 C 0.52220(12) 0.2737(4) 0.50807(12) 0.0222(6) Uani 1 1 d . . . . .
C8 C 0.55882(13) 0.2719(4) 0.46168(13) 0.0248(7) Uani 1 1 d . . . . .
C9 C 0.53166(14) 0.2049(4) 0.40101(13) 0.0288(7) Uani 1 1 d . . . . .
H9 H 0.5565 0.2043 0.3705 0.035 Uiso 1 1 calc R U . . .
C10 C 0.46996(14) 0.1419(4) 0.38716(13) 0.0305(7) Uani 1 1 d . . . . .
H10 H 0.4533 0.0956 0.3476 0.037 Uiso 1 1 calc R U . . .
C11 C 0.62608(13) 0.3324(4) 0.47647(13) 0.0248(7) Uani 1 1 d . . . . .
C12 C 0.71354(13) 0.4309(4) 0.56662(13) 0.0286(7) Uani 1 1 d . . . . .
H12A H 0.7228 0.5534 0.5544 0.034 Uiso 1 1 calc R U . . .
H12B H 0.7445 0.3473 0.5549 0.034 Uiso 1 1 calc R U . . .
C13 C 0.71450(14) 0.4202(5) 0.63584(14) 0.0351(8) Uani 1 1 d . . . . .
H13A H 0.7321 0.3042 0.6525 0.042 Uiso 1 1 calc R U . . .
H13B H 0.7411 0.5169 0.6579 0.042 Uiso 1 1 calc R U . . .
C14 C 0.64529(14) 0.4402(5) 0.64356(14) 0.0360(8) Uani 1 1 d . . . . .
H14 H 0.6374 0.5715 0.6451 0.043 Uiso 1 1 calc R U . . .
C15 C 0.60719(13) 0.3764(4) 0.58089(13) 0.0251(7) Uani 1 1 d . . . . .
C16 C 0.62131(16) 0.3602(6) 0.69707(15) 0.0472(10) Uani 1 1 d . . . . .
H16A H 0.6333 0.2326 0.6991 0.057 Uiso 1 1 calc R U . . .
H16B H 0.5744 0.3645 0.6861 0.057 Uiso 1 1 calc R U . . .
C17 C 0.64104(15) 0.4348(5) 0.76254(14) 0.0383(8) Uani 1 1 d . . . . .
C18 C 0.6222(2) 0.6408(6) 0.76295(19) 0.0641(12) Uani 1 1 d . . . . .
H18A H 0.5766 0.6542 0.7468 0.096 Uiso 1 1 calc R U . . .
H18B H 0.6458 0.7083 0.7374 0.096 Uiso 1 1 calc R U . . .
H18C H 0.6328 0.6863 0.8049 0.096 Uiso 1 1 calc R U . . .
C19 C 0.71372(16) 0.4251(5) 0.78804(15) 0.0408(8) Uani 1 1 d . . . . .
H19A H 0.7231 0.4621 0.8310 0.061 Uiso 1 1 calc R U . . .
H19B H 0.7355 0.5046 0.7644 0.061 Uiso 1 1 calc R U . . .
H19C H 0.7284 0.3024 0.7849 0.061 Uiso 1 1 calc R U . . .
C20 C 0.6083(2) 0.3367(9) 0.8066(2) 0.0854(18) Uani 1 1 d . . . . .
H20A H 0.6108 0.2079 0.8000 0.128 Uiso 1 1 calc R U . . .
H20B H 0.5637 0.3731 0.7995 0.128 Uiso 1 1 calc R U . . .
H20C H 0.6292 0.3657 0.8486 0.128 Uiso 1 1 calc R U . . .
N1 N 0.64667(10) 0.3774(3) 0.53871(11) 0.0236(6) Uani 1 1 d . . . . .
N2 N 0.54686(11) 0.3302(3) 0.56862(10) 0.0256(6) Uani 1 1 d . . . . .
O1 O 0.66313(9) 0.3423(3) 0.43994(9) 0.0326(6) 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 1.414(4) . ?
C1 C6 1.416(4) . ?
C1 C10 1.428(4) . ?
C2 C3 1.370(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.402(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.370(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.410(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.441(4) . ?
C7 N2 1.385(4) . ?
C7 C8 1.399(4) . ?
C8 C9 1.422(4) . ?
C8 C11 1.458(4) . ?
C9 C10 1.356(4) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 O1 1.232(3) . ?
C11 N1 1.383(4) . ?
C12 N1 1.470(3) . ?
C12 C13 1.515(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.512(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C16 1.491(4) . ?
C14 C15 1.514(4) . ?
C14 H14 0.9800 . ?
C15 N2 1.291(3) . ?
C15 N1 1.367(3) . ?
C16 C17 1.511(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C20 1.485(5) . ?
C17 C19 1.521(5) . ?
C17 C18 1.564(6) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
C2 C1 C6 118.4(3) . . ?
C2 C1 C10 122.1(3) . . ?
C6 C1 C10 119.5(3) . . ?
C3 C2 C1 121.3(3) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 119.7(3) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 120.8(3) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 120.3(3) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 119.5(3) . . ?
C5 C6 C7 121.3(3) . . ?
C1 C6 C7 119.1(2) . . ?
N2 C7 C8 123.0(2) . . ?
N2 C7 C6 117.7(2) . . ?
C8 C7 C6 119.3(2) . . ?
C7 C8 C9 120.4(3) . . ?
C7 C8 C11 119.6(3) . . ?
C9 C8 C11 119.9(2) . . ?
C10 C9 C8 120.6(3) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C1 121.0(3) . . ?
C9 C10 H10 119.5 . . ?
C1 C10 H10 119.5 . . ?
O1 C11 N1 121.0(3) . . ?
O1 C11 C8 126.4(3) . . ?
N1 C11 C8 112.6(2) . . ?
N1 C12 C13 102.4(2) . . ?
N1 C12 H12A 111.3 . . ?
C13 C12 H12A 111.3 . . ?
N1 C12 H12B 111.3 . . ?
C13 C12 H12B 111.3 . . ?
H12A C12 H12B 109.2 . . ?
C14 C13 C12 107.1(2) . . ?
C14 C13 H13A 110.3 . . ?
C12 C13 H13A 110.3 . . ?
C14 C13 H13B 110.3 . . ?
C12 C13 H13B 110.3 . . ?
H13A C13 H13B 108.5 . . ?
C16 C14 C13 122.9(3) . . ?
C16 C14 C15 112.9(3) . . ?
C13 C14 C15 102.2(2) . . ?
C16 C14 H14 105.9 . . ?
C13 C14 H14 105.9 . . ?
C15 C14 H14 105.9 . . ?
N2 C15 N1 125.0(3) . . ?
N2 C15 C14 125.8(2) . . ?
N1 C15 C14 109.2(2) . . ?
C14 C16 C17 122.2(3) . . ?
C14 C16 H16A 106.8 . . ?
C17 C16 H16A 106.8 . . ?
C14 C16 H16B 106.8 . . ?
C17 C16 H16B 106.8 . . ?
H16A C16 H16B 106.6 . . ?
C20 C17 C16 111.6(3) . . ?
C20 C17 C19 108.0(3) . . ?
C16 C17 C19 112.9(3) . . ?
C20 C17 C18 108.2(4) . . ?
C16 C17 C18 109.6(3) . . ?
C19 C17 C18 106.3(3) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C15 N1 C11 123.7(2) . . ?
C15 N1 C12 112.8(2) . . ?
C11 N1 C12 123.5(2) . . ?
C15 N2 C7 115.9(2) . . ?

_refine_diff_density_max         0.779
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.143



