# Electronic Supplementary Material (ESI) for Green Chemistry.
# 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_mo_160743_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1527117'
_audit_update_record             
;
2017-01-12 deposited with the CCDC.
2017-05-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H17 N O3'
_chemical_formula_weight         307.33

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/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                   9.4992(7)
_cell_length_b                   12.0176(9)
_cell_length_c                   14.7148(11)
_cell_angle_alpha                90
_cell_angle_beta                 107.666(2)
_cell_angle_gamma                90
_cell_volume                     1600.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1817
_cell_measurement_theta_min      2.8396
_cell_measurement_theta_max      21.8739

_exptl_crystal_description       Lump
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8834
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_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 8.3333
_diffrn_reflns_number            13301
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.232
_diffrn_reflns_theta_max         26.457
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3284
_reflns_number_gt                1935
_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       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (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)+(0.0712P)²+0.5825P] 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         3284
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1079
_refine_ls_R_factor_gt           0.0588
_refine_ls_wR_factor_ref         0.1690
_refine_ls_wR_factor_gt          0.1424
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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 0.8188(3) 0.4046(2) 0.43500(18) 0.0485(6) Uani 1 1 d . . . . .
C2 C 0.8354(2) 0.3165(2) 0.50581(17) 0.0446(6) Uani 1 1 d . . . . .
C3 C 0.8687(3) 0.2081(2) 0.4823(2) 0.0590(7) Uani 1 1 d . . . . .
H3 H 0.8796 0.1939 0.4227 0.071 Uiso 1 1 calc R U . . .
C4 C 0.8852(3) 0.1239(2) 0.5470(2) 0.0668(8) Uani 1 1 d . . . . .
H4 H 0.9078 0.0524 0.5316 0.080 Uiso 1 1 calc R U . . .
C5 C 0.8681(3) 0.1449(2) 0.6356(2) 0.0623(8) Uani 1 1 d . . . . .
H5 H 0.8794 0.0872 0.6794 0.075 Uiso 1 1 calc R U . . .
C6 C 0.8349(3) 0.2491(2) 0.65950(19) 0.0521(6) Uani 1 1 d . . . . .
H6 H 0.8230 0.2617 0.7191 0.063 Uiso 1 1 calc R U . . .
C7 C 0.8185(2) 0.33765(19) 0.59486(17) 0.0422(6) Uani 1 1 d . . . . .
C8 C 0.7792(2) 0.44973(19) 0.61513(16) 0.0404(6) Uani 1 1 d . . . . .
C9 C 0.7614(2) 0.53112(18) 0.54892(16) 0.0399(5) Uani 1 1 d . . . . .
C10 C 0.7736(3) 0.5990(2) 0.39166(19) 0.0651(8) Uani 1 1 d . . . . .
H10A H 0.8313 0.5795 0.3506 0.098 Uiso 1 1 calc R U . . .
H10B H 0.8106 0.6669 0.4247 0.098 Uiso 1 1 calc R U . . .
H10C H 0.6723 0.6090 0.3542 0.098 Uiso 1 1 calc R U . . .
C11 C 0.7226(3) 0.64770(18) 0.56654(17) 0.0425(6) Uani 1 1 d . . . . .
C12 C 0.5807(3) 0.6878(2) 0.5274(2) 0.0564(7) Uani 1 1 d . . . . .
H12 H 0.5078 0.6415 0.4896 0.068 Uiso 1 1 calc R U . . .
C13 C 0.5466(3) 0.7958(2) 0.5439(2) 0.0669(8) Uani 1 1 d . . . . .
H13 H 0.4507 0.8220 0.5178 0.080 Uiso 1 1 calc R U . . .
C14 C 0.6542(3) 0.8650(2) 0.5991(2) 0.0696(8) Uani 1 1 d . . . . .
H14 H 0.6316 0.9382 0.6095 0.084 Uiso 1 1 calc R U . . .
C15 C 0.7951(3) 0.8255(2) 0.6387(2) 0.0663(8) Uani 1 1 d . . . . .
H15 H 0.8677 0.8720 0.6765 0.080 Uiso 1 1 calc R U . . .
C16 C 0.8299(3) 0.7174(2) 0.62277(19) 0.0516(6) Uani 1 1 d . . . . .
H16 H 0.9257 0.6912 0.6499 0.062 Uiso 1 1 calc R U . . .
C17 C 0.7644(3) 0.4743(2) 0.71049(19) 0.0491(6) Uani 1 1 d . . . . .
C18 C 0.6221(6) 0.5598(5) 0.7978(3) 0.162(3) Uani 1 1 d . . . . .
H18A H 0.5824 0.5018 0.8289 0.194 Uiso 1 1 calc R U . . .
H18B H 0.7195 0.5791 0.8393 0.194 Uiso 1 1 calc R U . . .
C19 C 0.5343(8) 0.6495(5) 0.7848(4) 0.169(2) Uani 1 1 d . . . . .
H19A H 0.5724 0.7064 0.7529 0.254 Uiso 1 1 calc R U . . .
H19B H 0.5314 0.6766 0.8455 0.254 Uiso 1 1 calc R U . . .
H19C H 0.4364 0.6295 0.7465 0.254 Uiso 1 1 calc R U . . .
N1 N 0.7834(2) 0.50961(16) 0.46121(14) 0.0461(5) Uani 1 1 d . . . . .
O3 O 0.6349(2) 0.5168(2) 0.70603(15) 0.0842(7) Uani 1 1 d . . . . .
O1 O 0.8355(2) 0.39052(17) 0.35648(14) 0.0722(6) Uani 1 1 d . . . . .
O2 O 0.8603(2) 0.45631(17) 0.78449(13) 0.0701(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 O1 1.225(3) . ?
C1 N1 1.390(3) . ?
C1 C2 1.460(3) . ?
C2 C7 1.391(3) . ?
C2 C3 1.408(3) . ?
C3 C4 1.366(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.363(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.404(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.453(3) . ?
C8 C9 1.354(3) . ?
C8 C17 1.482(3) . ?
C9 N1 1.393(3) . ?
C9 C11 1.491(3) . ?
C10 N1 1.467(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.381(3) . ?
C11 C16 1.383(3) . ?
C12 C13 1.378(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.375(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.372(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.378(4) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 O2 1.208(3) . ?
C17 O3 1.315(3) . ?
C18 C19 1.340(6) . ?
C18 O3 1.484(5) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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
O1 C1 N1 119.9(2) . . ?
O1 C1 C2 123.7(2) . . ?
N1 C1 C2 116.3(2) . . ?
C7 C2 C3 120.0(2) . . ?
C7 C2 C1 121.4(2) . . ?
C3 C2 C1 118.6(2) . . ?
C4 C3 C2 120.1(3) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.0(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 120.8(3) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C7 120.5(3) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C2 C7 C6 118.6(2) . . ?
C2 C7 C8 118.2(2) . . ?
C6 C7 C8 123.1(2) . . ?
C9 C8 C7 120.4(2) . . ?
C9 C8 C17 120.7(2) . . ?
C7 C8 C17 118.9(2) . . ?
C8 C9 N1 120.8(2) . . ?
C8 C9 C11 122.5(2) . . ?
N1 C9 C11 116.7(2) . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C16 119.1(2) . . ?
C12 C11 C9 121.1(2) . . ?
C16 C11 C9 119.8(2) . . ?
C13 C12 C11 120.4(2) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C14 C13 C12 120.1(3) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C15 C14 C13 119.8(3) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 120.5(3) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C11 120.1(2) . . ?
C15 C16 H16 120.0 . . ?
C11 C16 H16 120.0 . . ?
O2 C17 O3 123.5(2) . . ?
O2 C17 C8 123.7(2) . . ?
O3 C17 C8 112.7(2) . . ?
C19 C18 O3 111.6(4) . . ?
C19 C18 H18A 109.3 . . ?
O3 C18 H18A 109.3 . . ?
C19 C18 H18B 109.3 . . ?
O3 C18 H18B 109.3 . . ?
H18A C18 H18B 108.0 . . ?
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 . . ?
C1 N1 C9 122.8(2) . . ?
C1 N1 C10 116.1(2) . . ?
C9 N1 C10 121.0(2) . . ?
C17 O3 C18 115.0(3) . . ?

_refine_diff_density_max         0.309
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.040

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_160602lt_0m
_database_code_depnum_ccdc_archive 'CCDC 1495728'
_audit_update_record             
;
2016-07-25 deposited with the CCDC.
2017-05-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H22 N2 O2'
_chemical_formula_weight         322.39

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'
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                   10.0712(6)
_cell_length_b                   9.0247(5)
_cell_length_c                   19.0587(9)
_cell_angle_alpha                90
_cell_angle_beta                 99.811(3)
_cell_angle_gamma                90
_cell_volume                     1706.90(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2971
_cell_measurement_theta_min      2.4793
_cell_measurement_theta_max      26.0574

_exptl_crystal_description       Lump
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8976
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(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 8.3333
_diffrn_reflns_number            14501
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.169
_diffrn_reflns_theta_max         26.406
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3493
_reflns_number_gt                2819
_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       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  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)+(0.0493P)²+0.5081P] 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         3493
_refine_ls_number_parameters     221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.1133
_refine_ls_wR_factor_gt          0.1059
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.001
_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 0.39731(10) 0.90587(11) 0.94738(5) 0.0243(3) Uani 1 1 d . . . . .
O2 O -0.20550(10) 0.71125(12) 0.93722(5) 0.0260(3) Uani 1 1 d . . . . .
N1 N -0.12120(12) 0.49312(14) 0.90294(6) 0.0196(3) Uani 1 1 d . . . . .
N2 N -0.14886(12) 0.22589(14) 0.80159(6) 0.0226(3) Uani 1 1 d . . . . .
C1 C 0.43928(16) 0.26681(17) 0.80587(8) 0.0268(4) Uani 1 1 d . . . . .
H1 H 0.5146 0.2231 0.7899 0.032 Uiso 1 1 calc R U . . .
C2 C 0.35562(15) 0.36264(18) 0.76185(8) 0.0253(4) Uani 1 1 d . . . . .
H9 H 0.3736 0.3845 0.7156 0.030 Uiso 1 1 calc R U . . .
C3 C 0.24606(15) 0.42646(17) 0.78505(7) 0.0233(3) Uani 1 1 d . . . . .
H10 H 0.1895 0.4925 0.7547 0.028 Uiso 1 1 calc R U . . .
C4 C 0.21759(14) 0.39485(15) 0.85266(7) 0.0179(3) Uani 1 1 d . . . . .
C5 C 0.10484(14) 0.47445(16) 0.87873(7) 0.0180(3) Uani 1 1 d . . . . .
C6 C 0.12906(14) 0.62647(16) 0.90210(6) 0.0174(3) Uani 1 1 d . . . . .
C7 C 0.25722(14) 0.69225(16) 0.90899(7) 0.0182(3) Uani 1 1 d . . . . .
H4 H 0.3304 0.6386 0.8959 0.022 Uiso 1 1 calc R U . . .
C8 C 0.27655(14) 0.83527(16) 0.93488(7) 0.0192(3) Uani 1 1 d . . . . .
C9 C 0.51099(15) 0.82852(19) 0.93047(8) 0.0272(4) Uani 1 1 d . . . . .
H2 H 0.5238 0.7363 0.9579 0.041 Uiso 1 1 calc R U . . .
H3 H 0.5915 0.8906 0.9424 0.041 Uiso 1 1 calc R U . . .
H22 H 0.4959 0.8055 0.8795 0.041 Uiso 1 1 calc R U . . .
C10 C 0.02237(14) 0.70801(16) 0.92113(7) 0.0186(3) Uani 1 1 d . . . . .
C11 C 0.04327(15) 0.85600(17) 0.94355(7) 0.0211(3) Uani 1 1 d . . . . .
H5 H -0.0305 0.9128 0.9538 0.025 Uiso 1 1 calc R U . . .
C12 C 0.16792(15) 0.91902(16) 0.95079(7) 0.0219(3) Uani 1 1 d . . . . .
H6 H 0.1812 1.0187 0.9664 0.026 Uiso 1 1 calc R U . . .
C13 C -0.10907(14) 0.64187(17) 0.92088(7) 0.0199(3) Uani 1 1 d . . . . .
C14 C -0.01665(14) 0.41103(16) 0.88130(7) 0.0184(3) Uani 1 1 d . . . . .
C15 C 0.41255(16) 0.23506(17) 0.87328(8) 0.0271(4) Uani 1 1 d . . . . .
H8 H 0.4698 0.1697 0.9037 0.033 Uiso 1 1 calc R U . . .
C16 C 0.30221(15) 0.29872(16) 0.89640(8) 0.0225(3) Uani 1 1 d . . . . .
H7 H 0.2843 0.2764 0.9426 0.027 Uiso 1 1 calc R U . . .
C17 C -0.04511(15) 0.24948(16) 0.86476(7) 0.0210(3) Uani 1 1 d . . . . .
H18 H 0.0393 0.2005 0.8572 0.025 Uiso 1 1 calc R U . . .
H17 H -0.0746 0.2019 0.9063 0.025 Uiso 1 1 calc R U . . .
C18 C -0.20000(17) 0.07430(18) 0.80028(9) 0.0317(4) Uani 1 1 d . . . . .
H13 H -0.2690 0.0603 0.7579 0.048 Uiso 1 1 calc R U . . .
H11 H -0.2395 0.0563 0.8431 0.048 Uiso 1 1 calc R U . . .
H12 H -0.1258 0.0046 0.7990 0.048 Uiso 1 1 calc R U . . .
C19 C -0.09406(16) 0.25574(18) 0.73704(7) 0.0270(4) Uani 1 1 d . . . . .
H14 H -0.0225 0.1842 0.7330 0.040 Uiso 1 1 calc R U . . .
H15 H -0.0570 0.3564 0.7391 0.040 Uiso 1 1 calc R U . . .
H16 H -0.1658 0.2467 0.6955 0.040 Uiso 1 1 calc R U . . .
C20 C -0.25220(15) 0.42463(18) 0.90719(8) 0.0253(3) Uani 1 1 d . . . . .
H19 H -0.3032 0.4894 0.9342 0.038 Uiso 1 1 calc R U . . .
H20 H -0.2377 0.3285 0.9312 0.038 Uiso 1 1 calc R U . . .
H21 H -0.3030 0.4104 0.8590 0.038 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 C8 1.3576(17) . ?
O1 C9 1.4240(18) . ?
O2 C13 1.2391(17) . ?
N1 C13 1.3856(19) . ?
N1 C14 1.4055(18) . ?
N1 C20 1.4716(19) . ?
N2 C19 1.4568(19) . ?
N2 C18 1.4605(19) . ?
N2 C17 1.4690(17) . ?
C1 C2 1.386(2) . ?
C1 C15 1.387(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.382(2) . ?
C2 H9 0.9500 . ?
C3 C4 1.396(2) . ?
C3 H10 0.9500 . ?
C4 C16 1.390(2) . ?
C4 C5 1.498(2) . ?
C5 C14 1.359(2) . ?
C5 C6 1.450(2) . ?
C6 C10 1.400(2) . ?
C6 C7 1.406(2) . ?
C7 C8 1.384(2) . ?
C7 H4 0.9500 . ?
C8 C12 1.405(2) . ?
C9 H2 0.9800 . ?
C9 H3 0.9800 . ?
C9 H22 0.9800 . ?
C10 C11 1.407(2) . ?
C10 C13 1.451(2) . ?
C11 C12 1.364(2) . ?
C11 H5 0.9500 . ?
C12 H6 0.9500 . ?
C14 C17 1.509(2) . ?
C15 C16 1.388(2) . ?
C15 H8 0.9500 . ?
C16 H7 0.9500 . ?
C17 H18 0.9900 . ?
C17 H17 0.9900 . ?
C18 H13 0.9800 . ?
C18 H11 0.9800 . ?
C18 H12 0.9800 . ?
C19 H14 0.9800 . ?
C19 H15 0.9800 . ?
C19 H16 0.9800 . ?
C20 H19 0.9800 . ?
C20 H20 0.9800 . ?
C20 H21 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
C8 O1 C9 117.45(11) . . ?
C13 N1 C14 122.96(12) . . ?
C13 N1 C20 115.82(12) . . ?
C14 N1 C20 121.22(12) . . ?
C19 N2 C18 110.00(12) . . ?
C19 N2 C17 110.27(12) . . ?
C18 N2 C17 110.45(11) . . ?
C2 C1 C15 119.72(15) . . ?
C2 C1 H1 120.1 . . ?
C15 C1 H1 120.1 . . ?
C3 C2 C1 120.17(14) . . ?
C3 C2 H9 119.9 . . ?
C1 C2 H9 119.9 . . ?
C2 C3 C4 120.70(14) . . ?
C2 C3 H10 119.6 . . ?
C4 C3 H10 119.6 . . ?
C16 C4 C3 118.67(14) . . ?
C16 C4 C5 121.48(12) . . ?
C3 C4 C5 119.64(12) . . ?
C14 C5 C6 119.51(13) . . ?
C14 C5 C4 123.22(13) . . ?
C6 C5 C4 117.27(12) . . ?
C10 C6 C7 119.12(13) . . ?
C10 C6 C5 118.71(13) . . ?
C7 C6 C5 122.12(13) . . ?
C8 C7 C6 119.88(13) . . ?
C8 C7 H4 120.1 . . ?
C6 C7 H4 120.1 . . ?
O1 C8 C7 124.60(13) . . ?
O1 C8 C12 114.64(13) . . ?
C7 C8 C12 120.76(13) . . ?
O1 C9 H2 109.5 . . ?
O1 C9 H3 109.5 . . ?
H2 C9 H3 109.5 . . ?
O1 C9 H22 109.5 . . ?
H2 C9 H22 109.5 . . ?
H3 C9 H22 109.5 . . ?
C6 C10 C11 119.72(14) . . ?
C6 C10 C13 121.52(13) . . ?
C11 C10 C13 118.72(13) . . ?
C12 C11 C10 120.94(14) . . ?
C12 C11 H5 119.5 . . ?
C10 C11 H5 119.5 . . ?
C11 C12 C8 119.42(14) . . ?
C11 C12 H6 120.3 . . ?
C8 C12 H6 120.3 . . ?
O2 C13 N1 120.78(14) . . ?
O2 C13 C10 123.01(14) . . ?
N1 C13 C10 116.19(12) . . ?
C5 C14 N1 120.84(13) . . ?
C5 C14 C17 122.65(13) . . ?
N1 C14 C17 116.45(13) . . ?
C1 C15 C16 120.07(14) . . ?
C1 C15 H8 120.0 . . ?
C16 C15 H8 120.0 . . ?
C15 C16 C4 120.68(14) . . ?
C15 C16 H7 119.7 . . ?
C4 C16 H7 119.7 . . ?
N2 C17 C14 113.24(11) . . ?
N2 C17 H18 108.9 . . ?
C14 C17 H18 108.9 . . ?
N2 C17 H17 108.9 . . ?
C14 C17 H17 108.9 . . ?
H18 C17 H17 107.7 . . ?
N2 C18 H13 109.5 . . ?
N2 C18 H11 109.5 . . ?
H13 C18 H11 109.5 . . ?
N2 C18 H12 109.5 . . ?
H13 C18 H12 109.5 . . ?
H11 C18 H12 109.5 . . ?
N2 C19 H14 109.5 . . ?
N2 C19 H15 109.5 . . ?
H14 C19 H15 109.5 . . ?
N2 C19 H16 109.5 . . ?
H14 C19 H16 109.5 . . ?
H15 C19 H16 109.5 . . ?
N1 C20 H19 109.5 . . ?
N1 C20 H20 109.5 . . ?
H19 C20 H20 109.5 . . ?
N1 C20 H21 109.5 . . ?
H19 C20 H21 109.5 . . ?
H20 C20 H21 109.5 . . ?

_refine_diff_density_max         0.325
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.044

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_mo_150714lt_0m
_database_code_depnum_ccdc_archive 'CCDC 1495727'
_audit_update_record             
;
2016-07-25 deposited with the CCDC.
2017-05-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H17 N O'
_chemical_formula_weight         311.36

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   9.3178(12)
_cell_length_b                   9.5222(12)
_cell_length_c                   10.9385(14)
_cell_angle_alpha                68.404(3)
_cell_angle_beta                 66.038(3)
_cell_angle_gamma                66.642(3)
_cell_volume                     789.02(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5657
_cell_measurement_theta_min      2.5000
_cell_measurement_theta_max      26.4153

_exptl_crystal_description       lump
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_F_000             328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8621
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(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 8.3333
_diffrn_reflns_number            12357
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.102
_diffrn_reflns_theta_max         26.485
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3208
_reflns_number_gt                2778
_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       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  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)+(0.0439P)²+0.2622P] 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         3208
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.0944
_refine_ls_wR_factor_gt          0.0897
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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 1.27617(11) 0.72463(10) 0.13698(8) 0.0244(2) Uani 1 1 d . . . . .
N1 N 1.21684(11) 0.69127(11) 0.36809(9) 0.0165(2) Uani 1 1 d . . . . .
C1 C 1.24165(15) 0.61078(14) 0.85487(12) 0.0214(3) Uani 1 1 d . . . . .
H1 H 1.2643 0.5938 0.9373 0.026 Uiso 1 1 calc R U . . .
C2 C 1.17834(14) 0.50813(14) 0.84398(12) 0.0205(3) Uani 1 1 d . . . . .
H15 H 1.1608 0.4186 0.9179 0.025 Uiso 1 1 calc R U . . .
C3 C 1.14037(14) 0.53597(13) 0.72500(11) 0.0183(2) Uani 1 1 d . . . . .
H16 H 1.0963 0.4656 0.7182 0.022 Uiso 1 1 calc R U . . .
C4 C 1.16662(13) 0.66632(13) 0.61570(11) 0.0152(2) Uani 1 1 d . . . . .
C5 C 1.10299(14) 0.70632(12) 0.49757(11) 0.0151(2) Uani 1 1 d . . . . .
C6 C 0.93835(14) 0.75755(12) 0.51685(11) 0.0145(2) Uani 1 1 d . . . . .
C7 C 0.87863(14) 0.79895(12) 0.40089(11) 0.0152(2) Uani 1 1 d . . . . .
C8 C 0.99407(14) 0.79241(12) 0.26910(11) 0.0164(2) Uani 1 1 d . . . . .
C9 C 0.94034(16) 0.84014(13) 0.15299(11) 0.0203(3) Uani 1 1 d . . . . .
H9 H 1.0184 0.8365 0.0643 0.024 Uiso 1 1 calc R U . . .
C10 C 0.77509(16) 0.89214(14) 0.16750(12) 0.0227(3) Uani 1 1 d . . . . .
H2 H 0.7394 0.9251 0.0888 0.027 Uiso 1 1 calc R U . . .
C11 C 0.60643(14) 0.82158(14) 0.91548(11) 0.0200(3) Uani 1 1 d . . . . .
H3 H 0.5353 0.8343 1.0046 0.024 Uiso 1 1 calc R U . . .
C12 C 0.70849(14) 0.91771(13) 0.83593(11) 0.0187(2) Uani 1 1 d . . . . .
H17 H 0.7061 0.9972 0.8701 0.022 Uiso 1 1 calc R U . . .
C13 C 0.81419(14) 0.89750(13) 0.70614(11) 0.0156(2) Uani 1 1 d . . . . .
H4 H 0.8833 0.9639 0.6520 0.019 Uiso 1 1 calc R U . . .
C14 C 0.81985(13) 0.78066(12) 0.65454(11) 0.0148(2) Uani 1 1 d . . . . .
C15 C 0.71507(14) 0.68662(13) 0.73461(11) 0.0176(2) Uani 1 1 d . . . . .
H6 H 0.7162 0.6078 0.7003 0.021 Uiso 1 1 calc R U . . .
C16 C 0.60870(14) 0.70684(14) 0.86439(11) 0.0199(3) Uani 1 1 d . . . . .
H5 H 0.5377 0.6421 0.9179 0.024 Uiso 1 1 calc R U . . .
C17 C 0.65957(15) 0.89648(14) 0.29823(12) 0.0211(3) Uani 1 1 d . . . . .
H8 H 0.5457 0.9310 0.3078 0.025 Uiso 1 1 calc R U . . .
C18 C 0.70979(15) 0.85099(13) 0.41319(11) 0.0179(2) Uani 1 1 d . . . . .
H7 H 0.6303 0.8547 0.5013 0.021 Uiso 1 1 calc R U . . .
C19 C 1.17112(15) 0.73554(13) 0.24983(11) 0.0174(2) Uani 1 1 d . . . . .
C20 C 1.39377(14) 0.62481(15) 0.35160(13) 0.0245(3) Uani 1 1 d . . . . .
H12 H 1.4506 0.5870 0.2671 0.037 Uiso 1 1 calc R U . . .
H10 H 1.4115 0.5366 0.4313 0.037 Uiso 1 1 calc R U . . .
H11 H 1.4370 0.7065 0.3455 0.037 Uiso 1 1 calc R U . . .
C21 C 1.27201(15) 0.73883(14) 0.74470(13) 0.0223(3) Uani 1 1 d . . . . .
H14 H 1.3180 0.8079 0.7511 0.027 Uiso 1 1 calc R U . . .
C22 C 1.23527(14) 0.76620(13) 0.62531(12) 0.0193(3) Uani 1 1 d . . . . .
H13 H 1.2571 0.8534 0.5501 0.023 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 C19 1.2349(14) . ?
N1 C19 1.3915(14) . ?
N1 C5 1.4001(14) . ?
N1 C20 1.4718(15) . ?
C1 C2 1.3848(17) . ?
C1 C21 1.3906(17) . ?
C1 H1 0.9500 . ?
C2 C3 1.3910(16) . ?
C2 H15 0.9500 . ?
C3 C4 1.3931(16) . ?
C3 H16 0.9500 . ?
C4 C22 1.3912(16) . ?
C4 C5 1.4991(15) . ?
C5 C6 1.3621(16) . ?
C6 C7 1.4510(15) . ?
C6 C14 1.4955(14) . ?
C7 C8 1.4116(15) . ?
C7 C18 1.4133(16) . ?
C8 C9 1.4077(16) . ?
C8 C19 1.4671(17) . ?
C9 C10 1.3769(18) . ?
C9 H9 0.9500 . ?
C10 C17 1.4011(17) . ?
C10 H2 0.9500 . ?
C11 C16 1.3884(17) . ?
C11 C12 1.3897(17) . ?
C11 H3 0.9500 . ?
C12 C13 1.3921(15) . ?
C12 H17 0.9500 . ?
C13 C14 1.3967(15) . ?
C13 H4 0.9500 . ?
C14 C15 1.3941(16) . ?
C15 C16 1.3934(16) . ?
C15 H6 0.9500 . ?
C16 H5 0.9500 . ?
C17 C18 1.3800(16) . ?
C17 H8 0.9500 . ?
C18 H7 0.9500 . ?
C20 H12 0.9800 . ?
C20 H10 0.9800 . ?
C20 H11 0.9800 . ?
C21 C22 1.3902(16) . ?
C21 H14 0.9500 . ?
C22 H13 0.9500 . ?

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
C19 N1 C5 122.87(9) . . ?
C19 N1 C20 116.53(9) . . ?
C5 N1 C20 120.59(9) . . ?
C2 C1 C21 119.73(11) . . ?
C2 C1 H1 120.1 . . ?
C21 C1 H1 120.1 . . ?
C1 C2 C3 120.07(11) . . ?
C1 C2 H15 120.0 . . ?
C3 C2 H15 120.0 . . ?
C2 C3 C4 120.43(11) . . ?
C2 C3 H16 119.8 . . ?
C4 C3 H16 119.8 . . ?
C22 C4 C3 119.28(10) . . ?
C22 C4 C5 121.14(10) . . ?
C3 C4 C5 119.22(10) . . ?
C6 C5 N1 121.48(10) . . ?
C6 C5 C4 120.24(9) . . ?
N1 C5 C4 118.28(10) . . ?
C5 C6 C7 119.61(10) . . ?
C5 C6 C14 120.25(9) . . ?
C7 C6 C14 120.04(10) . . ?
C8 C7 C18 118.54(10) . . ?
C8 C7 C6 118.55(10) . . ?
C18 C7 C6 122.87(10) . . ?
C9 C8 C7 120.10(11) . . ?
C9 C8 C19 118.64(10) . . ?
C7 C8 C19 121.26(10) . . ?
C10 C9 C8 120.22(11) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C17 120.11(10) . . ?
C9 C10 H2 119.9 . . ?
C17 C10 H2 119.9 . . ?
C16 C11 C12 119.83(10) . . ?
C16 C11 H3 120.1 . . ?
C12 C11 H3 120.1 . . ?
C11 C12 C13 120.01(11) . . ?
C11 C12 H17 120.0 . . ?
C13 C12 H17 120.0 . . ?
C12 C13 C14 120.75(11) . . ?
C12 C13 H4 119.6 . . ?
C14 C13 H4 119.6 . . ?
C15 C14 C13 118.61(10) . . ?
C15 C14 C6 121.57(10) . . ?
C13 C14 C6 119.81(10) . . ?
C16 C15 C14 120.80(11) . . ?
C16 C15 H6 119.6 . . ?
C14 C15 H6 119.6 . . ?
C11 C16 C15 119.99(11) . . ?
C11 C16 H5 120.0 . . ?
C15 C16 H5 120.0 . . ?
C18 C17 C10 120.53(11) . . ?
C18 C17 H8 119.7 . . ?
C10 C17 H8 119.7 . . ?
C17 C18 C7 120.49(11) . . ?
C17 C18 H7 119.8 . . ?
C7 C18 H7 119.8 . . ?
O1 C19 N1 120.59(11) . . ?
O1 C19 C8 123.36(10) . . ?
N1 C19 C8 116.04(9) . . ?
N1 C20 H12 109.5 . . ?
N1 C20 H10 109.5 . . ?
H12 C20 H10 109.5 . . ?
N1 C20 H11 109.5 . . ?
H12 C20 H11 109.5 . . ?
H10 C20 H11 109.5 . . ?
C22 C21 C1 120.26(11) . . ?
C22 C21 H14 119.9 . . ?
C1 C21 H14 119.9 . . ?
C21 C22 C4 120.18(11) . . ?
C21 C22 H13 119.9 . . ?
C4 C22 H13 119.9 . . ?

_refine_diff_density_max         0.277
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.036

_shelxl_version_number           2014/6

