# Electronic Supplementary Material (ESI) for ChemComm.
# 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_d19507a
_database_code_depnum_ccdc_archive 'CCDC 1863729'
_audit_update_record             
;
2018-08-24 deposited with the CCDC.
2019-01-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H15 N O2'
_chemical_formula_sum            'C19 H15 N O2'
_chemical_formula_weight         289.32

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.2847(12)
_cell_length_b                   16.3302(19)
_cell_length_c                   9.0650(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.856(3)
_cell_angle_gamma                90.00
_cell_volume                     1413.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    4104
_cell_measurement_theta_min      2.469
_cell_measurement_theta_max      24.051

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9869
_exptl_absorpt_correction_T_max  0.9974
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14688
_diffrn_reflns_av_R_equivalents  0.0704
_diffrn_reflns_av_sigmaI/netI    0.0510
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.47
_diffrn_reflns_theta_max         25.15
_reflns_number_total             2503
_reflns_number_gt                1830
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0446P)²+2.1532P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.026(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2503
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1011
_refine_ls_R_factor_gt           0.0679
_refine_ls_wR_factor_ref         0.1621
_refine_ls_wR_factor_gt          0.1451
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8755(4) 0.4058(2) 0.1398(4) 0.0368(8) Uani 1 1 d . . .
H1 H 0.9637 0.3935 0.2202 0.044 Uiso 1 1 calc R . .
C2 C 0.7532(3) 0.39695(19) 0.1788(4) 0.0317(8) Uani 1 1 d . . .
C3 C 0.7553(3) 0.37932(19) 0.3295(4) 0.0301(7) Uani 1 1 d . . .
C4 C 0.8782(3) 0.35864(19) 0.4727(3) 0.0290(7) Uani 1 1 d . . .
C5 C 0.9468(3) 0.2855(2) 0.4755(4) 0.0357(8) Uani 1 1 d . . .
H5 H 0.9142 0.2504 0.3855 0.043 Uiso 1 1 calc R . .
C6 C 1.0620(4) 0.2626(2) 0.6069(4) 0.0413(9) Uani 1 1 d . . .
H6 H 1.1087 0.2124 0.6066 0.050 Uiso 1 1 calc R . .
C7 C 1.1087(4) 0.3127(2) 0.7380(4) 0.0412(9) Uani 1 1 d . . .
H7 H 1.1869 0.2969 0.8293 0.049 Uiso 1 1 calc R . .
C8 C 1.0421(4) 0.3856(2) 0.7369(4) 0.0487(10) Uani 1 1 d . . .
H8 H 1.0747 0.4203 0.8274 0.058 Uiso 1 1 calc R . .
C9 C 0.9274(4) 0.4090(2) 0.6043(4) 0.0427(9) Uani 1 1 d . . .
H9 H 0.8826 0.4599 0.6041 0.051 Uiso 1 1 calc R . .
C10 C 0.5588(3) 0.36763(18) 0.4380(3) 0.0287(7) Uani 1 1 d . . .
C11 C 0.6299(4) 0.3234(2) 0.5757(4) 0.0349(8) Uani 1 1 d . . .
H11 H 0.7201 0.3015 0.5938 0.042 Uiso 1 1 calc R . .
C12 C 0.5684(4) 0.3115(2) 0.6856(4) 0.0381(8) Uani 1 1 d . . .
H12 H 0.6182 0.2831 0.7815 0.046 Uiso 1 1 calc R . .
C13 C 0.4358(4) 0.3405(2) 0.6580(4) 0.0413(9) Uani 1 1 d . . .
H13 H 0.3941 0.3317 0.7342 0.050 Uiso 1 1 calc R . .
C14 C 0.3634(4) 0.3825(2) 0.5188(4) 0.0416(9) Uani 1 1 d . . .
H14 H 0.2712 0.4015 0.4994 0.050 Uiso 1 1 calc R . .
C15 C 0.4233(3) 0.3971(2) 0.4076(4) 0.0323(8) Uani 1 1 d . . .
C16 C 0.3466(3) 0.4444(2) 0.2563(4) 0.0398(9) Uani 1 1 d . . .
H16 H 0.3839 0.5016 0.2689 0.048 Uiso 1 1 calc R . .
C17 C 0.3772(3) 0.4025(2) 0.1219(4) 0.0350(8) Uani 1 1 d . . .
H17A H 0.3394 0.3460 0.1068 0.042 Uiso 1 1 calc R . .
H17B H 0.3314 0.4329 0.0214 0.042 Uiso 1 1 calc R . .
C18 C 0.5302(3) 0.40037(19) 0.1628(3) 0.0312(8) Uani 1 1 d . . .
C19 C 0.6110(3) 0.40996(19) 0.0761(4) 0.0332(8) Uani 1 1 d . . .
H19 H 0.5790 0.4230 -0.0338 0.040 Uiso 1 1 calc R . .
N1 N 0.6176(3) 0.38249(15) 0.3196(3) 0.0288(6) Uani 1 1 d . . .
O1 O 0.8745(3) 0.42809(16) 0.0106(3) 0.0493(7) Uani 1 1 d . . .
H1A H 0.1550 0.4948 0.1431 0.059 Uiso 1 1 d R . .
O2 O 0.2031(3) 0.44720(18) 0.2269(3) 0.0557(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 O1 1.222(4) . ?
C1 C2 1.435(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.388(4) . ?
C2 C19 1.427(4) . ?
C3 N1 1.386(4) . ?
C3 C4 1.475(4) . ?
C4 C9 1.380(4) . ?
C4 C5 1.383(4) . ?
C5 C6 1.383(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.374(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.372(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.388(5) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.391(4) . ?
C10 C15 1.402(4) . ?
C10 N1 1.436(4) . ?
C11 C12 1.378(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.375(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.384(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.384(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.514(4) . ?
C16 O2 1.399(4) . ?
C16 C17 1.529(5) . ?
C16 H16 1.0000 . ?
C17 C18 1.476(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.349(4) . ?
C18 N1 1.401(4) . ?
C19 H19 0.9500 . ?
O2 H1A 1.0707 . ?

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 C2 124.8(3) . . ?
O1 C1 H1 117.6 . . ?
C2 C1 H1 117.6 . . ?
C3 C2 C19 108.0(3) . . ?
C3 C2 C1 124.7(3) . . ?
C19 C2 C1 127.1(3) . . ?
N1 C3 C2 106.7(3) . . ?
N1 C3 C4 125.9(3) . . ?
C2 C3 C4 127.4(3) . . ?
C9 C4 C5 118.6(3) . . ?
C9 C4 C3 122.9(3) . . ?
C5 C4 C3 118.6(3) . . ?
C6 C5 C4 121.1(3) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C7 C6 C5 119.7(3) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C8 C7 C6 119.8(3) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C7 C8 C9 120.4(3) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C4 C9 C8 120.3(3) . . ?
C4 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C11 C10 C15 120.5(3) . . ?
C11 C10 N1 122.1(3) . . ?
C15 C10 N1 117.4(3) . . ?
C12 C11 C10 119.5(3) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C13 C12 C11 120.7(3) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 119.8(3) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C15 C14 C13 121.0(3) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C10 118.5(3) . . ?
C14 C15 C16 121.7(3) . . ?
C10 C15 C16 119.9(3) . . ?
O2 C16 C15 110.3(3) . . ?
O2 C16 C17 112.2(3) . . ?
C15 C16 C17 107.5(3) . . ?
O2 C16 H16 108.9 . . ?
C15 C16 H16 108.9 . . ?
C17 C16 H16 108.9 . . ?
C18 C17 C16 109.1(3) . . ?
C18 C17 H17A 109.9 . . ?
C16 C17 H17A 109.9 . . ?
C18 C17 H17B 109.9 . . ?
C16 C17 H17B 109.9 . . ?
H17A C17 H17B 108.3 . . ?
C19 C18 N1 108.2(3) . . ?
C19 C18 C17 132.9(3) . . ?
N1 C18 C17 118.8(3) . . ?
C18 C19 C2 107.9(3) . . ?
C18 C19 H19 126.1 . . ?
C2 C19 H19 126.1 . . ?
C3 N1 C18 109.2(2) . . ?
C3 N1 C10 130.5(2) . . ?
C18 N1 C10 120.3(3) . . ?
C16 O2 H1A 109.6 . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        25.15
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.960
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.055
####################################################################### 
# 
# 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_d20154b
_database_code_depnum_ccdc_archive 'CCDC 1863730'
_audit_update_record             
;
2018-08-24 deposited with the CCDC.
2019-01-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H17 N O3'
_chemical_formula_sum            'C22 H17 N O3'
_chemical_formula_weight         343.37

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.161(2)
_cell_length_b                   13.323(3)
_cell_length_c                   35.586(7)
_cell_angle_alpha                90.00(3)
_cell_angle_beta                 95.42(3)
_cell_angle_gamma                90.00(3)
_cell_volume                     3379.7(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    4999
_cell_measurement_theta_min      2.305
_cell_measurement_theta_max      25.01

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.68
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1440
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9413
_exptl_absorpt_correction_T_max  0.9982
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            31920
_diffrn_reflns_av_R_equivalents  0.0802
_diffrn_reflns_av_sigmaI/netI    0.0616
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         2.30
_diffrn_reflns_theta_max         25.01
_reflns_number_total             5915
_reflns_number_gt                3704
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2005)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0557P)²+0.7126P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5915
_refine_ls_number_parameters     471
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1005
_refine_ls_R_factor_gt           0.0501
_refine_ls_wR_factor_ref         0.1362
_refine_ls_wR_factor_gt          0.1086
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2025(4) 0.1545(2) 0.68378(7) 0.0420(7) Uani 1 1 d . . .
H1 H 0.1981 0.1570 0.7104 0.050 Uiso 1 1 calc R . .
C2 C 0.1955(3) 0.24901(18) 0.66348(6) 0.0341(6) Uani 1 1 d . . .
C3 C 0.1878(3) 0.34275(18) 0.68000(6) 0.0321(6) Uani 1 1 d . . .
C4 C 0.1871(4) 0.36479(17) 0.72101(6) 0.0349(6) Uani 1 1 d . . .
C5 C 0.3526(4) 0.36437(19) 0.74451(7) 0.0447(7) Uani 1 1 d . . .
H5 H 0.4685 0.3508 0.7345 0.054 Uiso 1 1 calc R . .
C6 C 0.3482(5) 0.3839(2) 0.78268(7) 0.0545(8) Uani 1 1 d . . .
H6 H 0.4616 0.3836 0.7988 0.065 Uiso 1 1 calc R . .
C7 C 0.1811(5) 0.4037(2) 0.79742(7) 0.0524(8) Uani 1 1 d . . .
H7 H 0.1798 0.4175 0.8236 0.063 Uiso 1 1 calc R . .
C8 C 0.0162(5) 0.4034(2) 0.77427(7) 0.0518(8) Uani 1 1 d . . .
H8 H -0.0993 0.4169 0.7844 0.062 Uiso 1 1 calc R . .
C9 C 0.0191(4) 0.38341(19) 0.73618(7) 0.0439(7) Uani 1 1 d . . .
H9 H -0.0952 0.3824 0.7203 0.053 Uiso 1 1 calc R . .
C10 C 0.1678(3) 0.51978(17) 0.65300(6) 0.0299(6) Uani 1 1 d . . .
C11 C 0.1884(3) 0.57393(18) 0.68678(6) 0.0349(6) Uani 1 1 d . . .
H11 H 0.2103 0.5392 0.7101 0.042 Uiso 1 1 calc R . .
C12 C 0.1773(4) 0.67733(19) 0.68659(7) 0.0397(7) Uani 1 1 d . . .
H12 H 0.1906 0.7130 0.7098 0.048 Uiso 1 1 calc R . .
C13 C 0.1470(4) 0.72979(19) 0.65286(7) 0.0408(7) Uani 1 1 d . . .
H13 H 0.1384 0.8009 0.6529 0.049 Uiso 1 1 calc R . .
C14 C 0.1296(4) 0.67766(18) 0.61949(7) 0.0387(7) Uani 1 1 d . . .
H14 H 0.1091 0.7136 0.5964 0.046 Uiso 1 1 calc R . .
C15 C 0.1413(3) 0.57263(18) 0.61857(6) 0.0315(6) Uani 1 1 d . . .
C16 C 0.1335(3) 0.51956(18) 0.58332(6) 0.0334(6) Uani 1 1 d . . .
H16 H 0.1124 0.5563 0.5604 0.040 Uiso 1 1 calc R . .
C17 C 0.1552(3) 0.41930(18) 0.58174(6) 0.0296(6) Uani 1 1 d . . .
C18 C 0.1567(3) 0.37280(19) 0.54357(6) 0.0334(6) Uani 1 1 d . . .
C19 C 0.1513(4) 0.22300(18) 0.50780(6) 0.0392(7) Uani 1 1 d . . .
H19A H 0.2645 0.2436 0.4958 0.047 Uiso 1 1 calc R . .
H19B H 0.0391 0.2409 0.4907 0.047 Uiso 1 1 calc R . .
C20 C 0.1552(4) 0.1120(2) 0.51541(7) 0.0497(7) Uani 1 1 d . . .
H20A H 0.1646 0.0756 0.4917 0.075 Uiso 1 1 calc R . .
H20B H 0.0398 0.0922 0.5262 0.075 Uiso 1 1 calc R . .
H20C H 0.2638 0.0958 0.5332 0.075 Uiso 1 1 calc R . .
C21 C 0.1737(3) 0.36114(18) 0.61620(6) 0.0302(6) Uani 1 1 d . . .
C22 C 0.1880(3) 0.26081(18) 0.62382(6) 0.0309(6) Uani 1 1 d . . .
H22 H 0.1921 0.2085 0.6058 0.037 Uiso 1 1 calc R . .
C23 C 0.6854(4) 0.1634(2) 0.68920(7) 0.0447(7) Uani 1 1 d . . .
H23 H 0.6948 0.0924 0.6880 0.054 Uiso 1 1 calc R . .
C24 C 0.6756(3) 0.21953(17) 0.65398(6) 0.0318(6) Uani 1 1 d . . .
C25 C 0.6794(3) 0.17617(17) 0.61865(6) 0.0304(6) Uani 1 1 d . . .
C26 C 0.6956(3) 0.06807(17) 0.61017(6) 0.0296(6) Uani 1 1 d . . .
C27 C 0.5458(4) 0.00344(19) 0.61330(6) 0.0390(7) Uani 1 1 d . . .
H27 H 0.4304 0.0292 0.6204 0.047 Uiso 1 1 calc R . .
C28 C 0.5629(4) -0.0982(2) 0.60624(7) 0.0476(7) Uani 1 1 d . . .
H28 H 0.4595 -0.1416 0.6087 0.057 Uiso 1 1 calc R . .
C29 C 0.7289(4) -0.13714(19) 0.59565(7) 0.0455(7) Uani 1 1 d . . .
H29 H 0.7391 -0.2066 0.5901 0.055 Uiso 1 1 calc R . .
C30 C 0.8796(4) -0.07363(19) 0.59320(7) 0.0420(7) Uani 1 1 d . . .
H30 H 0.9950 -0.0999 0.5863 0.050 Uiso 1 1 calc R . .
C31 C 0.8646(4) 0.02802(18) 0.60064(6) 0.0369(6) Uani 1 1 d . . .
H31 H 0.9701 0.0706 0.5992 0.044 Uiso 1 1 calc R . .
C32 C 0.6588(3) 0.25066(17) 0.55241(6) 0.0275(6) Uani 1 1 d . . .
C33 C 0.6457(3) 0.16104(18) 0.53174(6) 0.0331(6) Uani 1 1 d . . .
H33 H 0.6449 0.0983 0.5444 0.040 Uiso 1 1 calc R . .
C34 C 0.6338(4) 0.16443(19) 0.49275(6) 0.0377(6) Uani 1 1 d . . .
H34 H 0.6261 0.1034 0.4789 0.045 Uiso 1 1 calc R . .
C35 C 0.6330(3) 0.25427(19) 0.47358(6) 0.0366(6) Uani 1 1 d . . .
H35 H 0.6242 0.2552 0.4468 0.044 Uiso 1 1 calc R . .
C36 C 0.6451(3) 0.34265(18) 0.49361(6) 0.0341(6) Uani 1 1 d . . .
H36 H 0.6454 0.4046 0.4804 0.041 Uiso 1 1 calc R . .
C37 C 0.6570(3) 0.34296(17) 0.53310(6) 0.0289(6) Uani 1 1 d . . .
C38 C 0.6588(3) 0.43611(18) 0.55345(6) 0.0311(6) Uani 1 1 d . . .
H38 H 0.6609 0.4975 0.5399 0.037 Uiso 1 1 calc R . .
C39 C 0.6576(3) 0.43852(17) 0.59137(6) 0.0279(5) Uani 1 1 d . . .
C40 C 0.6498(3) 0.53975(18) 0.60932(7) 0.0328(6) Uani 1 1 d . . .
C41 C 0.6620(4) 0.63102(18) 0.66689(7) 0.0405(7) Uani 1 1 d . . .
H41A H 0.5399 0.6644 0.6601 0.049 Uiso 1 1 calc R . .
H41B H 0.7634 0.6762 0.6601 0.049 Uiso 1 1 calc R . .
C42 C 0.6853(4) 0.6078(2) 0.70828(7) 0.0528(8) Uani 1 1 d . . .
H42A H 0.5859 0.5617 0.7144 0.079 Uiso 1 1 calc R . .
H42B H 0.6774 0.6700 0.7227 0.079 Uiso 1 1 calc R . .
H42C H 0.8079 0.5763 0.7147 0.079 Uiso 1 1 calc R . .
C43 C 0.6630(3) 0.34639(16) 0.61247(6) 0.0278(5) Uani 1 1 d . . .
C44 C 0.6652(3) 0.32445(17) 0.65000(6) 0.0308(6) Uani 1 1 d . . .
H44 H 0.6607 0.3717 0.6699 0.037 Uiso 1 1 calc R . .
N1 N 0.1752(3) 0.41350(14) 0.65123(5) 0.0300(5) Uani 1 1 d . . .
N2 N 0.6705(3) 0.25373(13) 0.59259(5) 0.0278(5) Uani 1 1 d . . .
O1 O 0.2135(3) 0.07226(14) 0.66931(5) 0.0515(5) Uani 1 1 d . . .
O2 O 0.1669(3) 0.42079(13) 0.51520(4) 0.0499(5) Uani 1 1 d . . .
O3 O 0.1459(2) 0.27277(12) 0.54401(4) 0.0380(4) Uani 1 1 d . . .
O4 O 0.6824(3) 0.20209(14) 0.72029(5) 0.0553(6) Uani 1 1 d . . .
O5 O 0.6283(3) 0.61696(13) 0.59190(5) 0.0522(5) Uani 1 1 d . . .
O6 O 0.6702(2) 0.53579(11) 0.64706(4) 0.0381(4) 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 1.216(3) . ?
C1 C2 1.450(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.384(3) . ?
C2 C22 1.416(3) . ?
C3 N1 1.388(3) . ?
C3 C4 1.489(3) . ?
C4 C5 1.384(4) . ?
C4 C9 1.387(3) . ?
C5 C6 1.387(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.376(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.375(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.383(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.397(3) . ?
C10 C15 1.410(3) . ?
C10 N1 1.419(3) . ?
C11 C12 1.380(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.388(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.371(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.402(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.437(3) . ?
C16 C17 1.347(3) . ?
C16 H16 0.9500 . ?
C17 C21 1.446(3) . ?
C17 C18 1.494(3) . ?
C18 O2 1.203(3) . ?
C18 O3 1.335(3) . ?
C19 O3 1.453(3) . ?
C19 C20 1.503(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.366(3) . ?
C21 N1 1.428(3) . ?
C22 H22 0.9500 . ?
C23 O4 1.222(3) . ?
C23 C24 1.455(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.386(3) . ?
C24 C44 1.406(3) . ?
C25 N2 1.386(3) . ?
C25 C26 1.478(3) . ?
C26 C27 1.388(3) . ?
C26 C31 1.394(3) . ?
C27 C28 1.385(3) . ?
C27 H27 0.9500 . ?
C28 C29 1.381(4) . ?
C28 H28 0.9500 . ?
C29 C30 1.381(4) . ?
C29 H29 0.9500 . ?
C30 C31 1.386(3) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C32 C33 1.401(3) . ?
C32 C37 1.408(3) . ?
C32 N2 1.425(3) . ?
C33 C34 1.383(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.377(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.375(3) . ?
C35 H35 0.9500 . ?
C36 C37 1.400(3) . ?
C36 H36 0.9500 . ?
C37 C38 1.436(3) . ?
C38 C39 1.351(3) . ?
C38 H38 0.9500 . ?
C39 C43 1.438(3) . ?
C39 C40 1.495(3) . ?
C40 O5 1.203(3) . ?
C40 O6 1.338(3) . ?
C41 O6 1.456(3) . ?
C41 C42 1.499(3) . ?
C41 H41A 0.9900 . ?
C41 H41B 0.9900 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C43 C44 1.365(3) . ?
C43 N2 1.426(3) . ?
C44 H44 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
O1 C1 C2 124.9(2) . . ?
O1 C1 H1 117.6 . . ?
C2 C1 H1 117.6 . . ?
C3 C2 C22 108.9(2) . . ?
C3 C2 C1 125.0(2) . . ?
C22 C2 C1 126.1(2) . . ?
C2 C3 N1 107.58(19) . . ?
C2 C3 C4 126.7(2) . . ?
N1 C3 C4 125.7(2) . . ?
C5 C4 C9 119.4(2) . . ?
C5 C4 C3 120.6(2) . . ?
C9 C4 C3 120.0(2) . . ?
C4 C5 C6 119.6(3) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C7 C6 C5 120.7(3) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C8 C7 C6 120.0(3) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C9 119.8(3) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C8 C9 C4 120.6(3) . . ?
C8 C9 H9 119.7 . . ?
C4 C9 H9 119.7 . . ?
C11 C10 C15 118.9(2) . . ?
C11 C10 N1 123.5(2) . . ?
C15 C10 N1 117.5(2) . . ?
C12 C11 C10 120.7(2) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 120.7(2) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C14 C13 C12 119.2(2) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C13 C14 C15 121.7(2) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 H14 119.2 . . ?
C14 C15 C10 118.8(2) . . ?
C14 C15 C16 120.9(2) . . ?
C10 C15 C16 120.3(2) . . ?
C17 C16 C15 122.0(2) . . ?
C17 C16 H16 119.0 . . ?
C15 C16 H16 119.0 . . ?
C16 C17 C21 119.8(2) . . ?
C16 C17 C18 117.4(2) . . ?
C21 C17 C18 122.8(2) . . ?
O2 C18 O3 123.2(2) . . ?
O2 C18 C17 123.3(2) . . ?
O3 C18 C17 113.5(2) . . ?
O3 C19 C20 106.90(19) . . ?
O3 C19 H19A 110.3 . . ?
C20 C19 H19A 110.3 . . ?
O3 C19 H19B 110.3 . . ?
C20 C19 H19B 110.3 . . ?
H19A C19 H19B 108.6 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 N1 108.10(19) . . ?
C22 C21 C17 133.8(2) . . ?
N1 C21 C17 118.1(2) . . ?
C21 C22 C2 107.5(2) . . ?
C21 C22 H22 126.2 . . ?
C2 C22 H22 126.2 . . ?
O4 C23 C24 124.0(2) . . ?
O4 C23 H23 118.0 . . ?
C24 C23 H23 118.0 . . ?
C25 C24 C44 109.2(2) . . ?
C25 C24 C23 124.3(2) . . ?
C44 C24 C23 126.5(2) . . ?
N2 C25 C24 107.01(19) . . ?
N2 C25 C26 126.12(19) . . ?
C24 C25 C26 126.8(2) . . ?
C27 C26 C31 118.5(2) . . ?
C27 C26 C25 120.8(2) . . ?
C31 C26 C25 120.6(2) . . ?
C28 C27 C26 120.6(3) . . ?
C28 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
C29 C28 C27 120.7(3) . . ?
C29 C28 H28 119.7 . . ?
C27 C28 H28 119.7 . . ?
C30 C29 C28 119.0(2) . . ?
C30 C29 H29 120.5 . . ?
C28 C29 H29 120.5 . . ?
C29 C30 C31 120.8(3) . . ?
C29 C30 H30 119.6 . . ?
C31 C30 H30 119.6 . . ?
C30 C31 C26 120.3(2) . . ?
C30 C31 H31 119.8 . . ?
C26 C31 H31 119.8 . . ?
C33 C32 C37 119.40(19) . . ?
C33 C32 N2 123.1(2) . . ?
C37 C32 N2 117.49(19) . . ?
C34 C33 C32 119.6(2) . . ?
C34 C33 H33 120.2 . . ?
C32 C33 H33 120.2 . . ?
C35 C34 C33 121.5(2) . . ?
C35 C34 H34 119.3 . . ?
C33 C34 H34 119.3 . . ?
C36 C35 C34 119.4(2) . . ?
C36 C35 H35 120.3 . . ?
C34 C35 H35 120.3 . . ?
C35 C36 C37 121.2(2) . . ?
C35 C36 H36 119.4 . . ?
C37 C36 H36 119.4 . . ?
C36 C37 C32 119.0(2) . . ?
C36 C37 C38 120.4(2) . . ?
C32 C37 C38 120.61(19) . . ?
C39 C38 C37 121.6(2) . . ?
C39 C38 H38 119.2 . . ?
C37 C38 H38 119.2 . . ?
C38 C39 C43 120.0(2) . . ?
C38 C39 C40 116.9(2) . . ?
C43 C39 C40 123.17(19) . . ?
O5 C40 O6 123.2(2) . . ?
O5 C40 C39 124.0(2) . . ?
O6 C40 C39 112.8(2) . . ?
O6 C41 C42 106.9(2) . . ?
O6 C41 H41A 110.3 . . ?
C42 C41 H41A 110.3 . . ?
O6 C41 H41B 110.3 . . ?
C42 C41 H41B 110.3 . . ?
H41A C41 H41B 108.6 . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C44 C43 N2 107.61(19) . . ?
C44 C43 C39 133.7(2) . . ?
N2 C43 C39 118.69(18) . . ?
C43 C44 C24 107.9(2) . . ?
C43 C44 H44 126.1 . . ?
C24 C44 H44 126.1 . . ?
C3 N1 C10 130.17(18) . . ?
C3 N1 C21 107.87(19) . . ?
C10 N1 C21 121.96(18) . . ?
C25 N2 C32 130.14(18) . . ?
C25 N2 C43 108.34(17) . . ?
C32 N2 C43 121.42(18) . . ?
C18 O3 C19 116.03(18) . . ?
C40 O6 C41 116.53(18) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.045
####################################################################### 
# 
# 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_170932LT_0m
_database_code_depnum_ccdc_archive 'CCDC 1863731'
_audit_update_record             
;
2018-08-24 deposited with the CCDC.
2019-01-17 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 H15 N O2'
_chemical_formula_weight         289.32

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                   8.3810(3)
_cell_length_b                   13.1650(5)
_cell_length_c                   13.3041(5)
_cell_angle_alpha                90
_cell_angle_beta                 97.823(2)
_cell_angle_gamma                90
_cell_volume                     1454.26(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4235
_cell_measurement_theta_min      2.4530
_cell_measurement_theta_max      26.2603

_exptl_crystal_description       Lamellar
_exptl_crystal_colour            'Pale Orange'
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8947
_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            13024
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.186
_diffrn_reflns_theta_max         26.397
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2987
_reflns_number_gt                2475
_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    ?
_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)+(0.0442P)²+0.5967P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2987
_refine_ls_number_parameters     204
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_ref         0.1031
_refine_ls_wR_factor_gt          0.0957
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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 0.56239(12) 0.82257(8) -0.00643(8) 0.0319(3) Uani 1 1 d . . . . .
N1 N 0.12122(13) 0.75456(9) 0.15132(8) 0.0195(3) Uani 1 1 d . . . . .
C1 C 0.40769(18) 0.41334(12) 0.23278(12) 0.0308(4) Uani 1 1 d . . . . .
H1 H 0.4414 0.3473 0.2554 0.037 Uiso 1 1 calc R U . . .
C2 C 0.39203(17) 0.48925(11) 0.30254(12) 0.0264(3) Uani 1 1 d . . . . .
H12 H 0.4153 0.4755 0.3731 0.032 Uiso 1 1 calc R U . . .
C3 C 0.34229(16) 0.58552(11) 0.26949(11) 0.0228(3) Uani 1 1 d . . . . .
H13 H 0.3305 0.6373 0.3176 0.027 Uiso 1 1 calc R U . . .
C4 C 0.30954(15) 0.60672(10) 0.16614(10) 0.0201(3) Uani 1 1 d . . . . .
C5 C 0.26026(15) 0.70950(10) 0.13020(10) 0.0191(3) Uani 1 1 d . . . . .
C6 C 0.00306(15) 0.70813(10) 0.20517(10) 0.0199(3) Uani 1 1 d . . . . .
C7 C -0.09301(16) 0.63070(11) 0.15947(11) 0.0247(3) Uani 1 1 d . . . . .
H11 H -0.0782 0.6068 0.0940 0.030 Uiso 1 1 calc R U . . .
C8 C -0.21074(17) 0.58849(11) 0.21014(12) 0.0289(3) Uani 1 1 d . . . . .
H10 H -0.2760 0.5349 0.1795 0.035 Uiso 1 1 calc R U . . .
C9 C -0.23414(17) 0.62379(12) 0.30503(12) 0.0285(3) Uani 1 1 d . . . . .
H2 H -0.3161 0.5950 0.3388 0.034 Uiso 1 1 calc R U . . .
C10 C 0.37439(19) 0.43338(12) 0.13024(13) 0.0346(4) Uani 1 1 d . . . . .
H15 H 0.3842 0.3809 0.0825 0.042 Uiso 1 1 calc R U . . .
C11 C 0.32660(18) 0.52994(12) 0.09656(12) 0.0292(3) Uani 1 1 d . . . . .
H14 H 0.3055 0.5436 0.0259 0.035 Uiso 1 1 calc R U . . .
C12 C 0.10614(16) 0.85152(10) 0.10760(10) 0.0212(3) Uani 1 1 d . . . . .
C13 C 0.23698(16) 0.86695(11) 0.05973(10) 0.0217(3) Uani 1 1 d . . . . .
H4 H 0.2590 0.9264 0.0236 0.026 Uiso 1 1 calc R U . . .
C14 C 0.33587(16) 0.77842(10) 0.07305(10) 0.0205(3) Uani 1 1 d . . . . .
C15 C 0.49215(17) 0.76275(11) 0.04236(11) 0.0238(3) Uani 1 1 d . . . . .
H3 H 0.5452 0.7006 0.0617 0.029 Uiso 1 1 calc R U . . .
C16 C -0.03773(17) 0.91608(11) 0.11647(12) 0.0260(3) Uani 1 1 d . . . . .
H5 H -0.0260 0.9816 0.0832 0.039 Uiso 1 1 calc R U . . .
H6 H -0.0468 0.9273 0.1883 0.039 Uiso 1 1 calc R U . . .
H7 H -0.1349 0.8818 0.0837 0.039 Uiso 1 1 calc R U . . .
C17 C -0.13884(17) 0.70055(12) 0.35047(11) 0.0268(3) Uani 1 1 d . . . . .
H9 H -0.1556 0.7245 0.4156 0.032 Uiso 1 1 calc R U . . .
C18 C -0.01743(16) 0.74356(11) 0.30162(11) 0.0231(3) Uani 1 1 d . . . . .
C19 C 0.08510(19) 0.82304(13) 0.35333(13) 0.0336(4) Uani 1 1 d . . . . .
O2 O 0.05305(18) 0.87217(12) 0.42497(11) 0.0375(4) Uani 0.775(2) 1 d . . P A 1
H8 H 0.1850 0.8377 0.3290 0.045 Uiso 0.775 1 d . U P A 1
O2' O 0.2215(6) 0.8447(4) 0.3433(4) 0.0375(4) Uani 0.225(2) 1 d . . P A 2
H8' H 0.0441 0.8622 0.4050 0.045 Uiso 0.225 1 d . U P A 2


_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 C15 1.2215(17) . ?
N1 C5 1.3704(17) . ?
N1 C12 1.4013(17) . ?
N1 C6 1.4356(17) . ?
C1 C10 1.380(2) . ?
C1 C2 1.382(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.387(2) . ?
C2 H12 0.9500 . ?
C3 C4 1.3933(19) . ?
C3 H13 0.9500 . ?
C4 C11 1.391(2) . ?
C4 C5 1.4752(19) . ?
C5 C14 1.3907(19) . ?
C6 C7 1.387(2) . ?
C6 C18 1.3976(19) . ?
C7 C8 1.385(2) . ?
C7 H11 0.9500 . ?
C8 C9 1.384(2) . ?
C8 H10 0.9500 . ?
C9 C17 1.376(2) . ?
C9 H2 0.9500 . ?
C10 C11 1.389(2) . ?
C10 H15 0.9500 . ?
C11 H14 0.9500 . ?
C12 C13 1.3563(19) . ?
C12 C16 1.4930(19) . ?
C13 C14 1.4271(19) . ?
C13 H4 0.9500 . ?
C14 C15 1.4388(19) . ?
C15 H3 0.9500 . ?
C16 H5 0.9800 . ?
C16 H6 0.9800 . ?
C16 H7 0.9800 . ?
C17 C18 1.399(2) . ?
C17 H9 0.9500 . ?
C18 C19 1.465(2) . ?
C19 O2' 1.203(5) . ?
C19 O2 1.212(2) . ?
C19 H8 0.9569 . ?
C19 H8' 0.9597 . ?

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
C5 N1 C12 109.90(11) . . ?
C5 N1 C6 125.56(11) . . ?
C12 N1 C6 124.45(11) . . ?
C10 C1 C2 120.04(14) . . ?
C10 C1 H1 120.0 . . ?
C2 C1 H1 120.0 . . ?
C1 C2 C3 119.99(14) . . ?
C1 C2 H12 120.0 . . ?
C3 C2 H12 120.0 . . ?
C2 C3 C4 120.42(13) . . ?
C2 C3 H13 119.8 . . ?
C4 C3 H13 119.8 . . ?
C11 C4 C3 119.13(13) . . ?
C11 C4 C5 120.03(13) . . ?
C3 C4 C5 120.83(12) . . ?
N1 C5 C14 107.04(12) . . ?
N1 C5 C4 122.62(12) . . ?
C14 C5 C4 130.34(12) . . ?
C7 C6 C18 120.74(13) . . ?
C7 C6 N1 119.53(12) . . ?
C18 C6 N1 119.70(12) . . ?
C8 C7 C6 119.41(14) . . ?
C8 C7 H11 120.3 . . ?
C6 C7 H11 120.3 . . ?
C9 C8 C7 120.54(14) . . ?
C9 C8 H10 119.7 . . ?
C7 C8 H10 119.7 . . ?
C17 C9 C8 120.10(13) . . ?
C17 C9 H2 119.9 . . ?
C8 C9 H2 119.9 . . ?
C1 C10 C11 120.30(15) . . ?
C1 C10 H15 119.9 . . ?
C11 C10 H15 119.9 . . ?
C10 C11 C4 120.12(14) . . ?
C10 C11 H14 119.9 . . ?
C4 C11 H14 119.9 . . ?
C13 C12 N1 107.35(12) . . ?
C13 C12 C16 131.70(13) . . ?
N1 C12 C16 120.93(12) . . ?
C12 C13 C14 108.20(12) . . ?
C12 C13 H4 125.9 . . ?
C14 C13 H4 125.9 . . ?
C5 C14 C13 107.49(12) . . ?
C5 C14 C15 124.17(13) . . ?
C13 C14 C15 128.14(13) . . ?
O1 C15 C14 125.56(14) . . ?
O1 C15 H3 117.2 . . ?
C14 C15 H3 117.2 . . ?
C12 C16 H5 109.5 . . ?
C12 C16 H6 109.5 . . ?
H5 C16 H6 109.5 . . ?
C12 C16 H7 109.5 . . ?
H5 C16 H7 109.5 . . ?
H6 C16 H7 109.5 . . ?
C9 C17 C18 120.55(14) . . ?
C9 C17 H9 119.7 . . ?
C18 C17 H9 119.7 . . ?
C6 C18 C17 118.64(13) . . ?
C6 C18 C19 122.15(13) . . ?
C17 C18 C19 119.21(13) . . ?
O2' C19 C18 128.5(3) . . ?
O2 C19 C18 124.89(15) . . ?
O2 C19 H8 117.1 . . ?
C18 C19 H8 118.0 . . ?
O2' C19 H8' 113.0 . . ?
C18 C19 H8' 118.4 . . ?

_refine_diff_density_max         0.251
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.041

_shelxl_version_number           2014/6

