# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_d19548
_database_code_depnum_ccdc_archive 'CCDC 1894125'
_audit_update_record             
;
2019-01-28 deposited with the CCDC.	2019-05-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H17 N O'
_chemical_formula_sum            'C14 H17 N O'
_chemical_formula_weight         215.29

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                   7.469(3)
_cell_length_b                   7.941(4)
_cell_length_c                   19.929(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.051(14)
_cell_angle_gamma                90.00
_cell_volume                     1182.0(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    5554
_cell_measurement_theta_min      2.732
_cell_measurement_theta_max      24.977

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9524
_exptl_absorpt_correction_T_max  0.9917
_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            17667
_diffrn_reflns_av_R_equivalents  0.0855
_diffrn_reflns_av_sigmaI/netI    0.0457
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.73
_diffrn_reflns_theta_max         25.13
_reflns_number_total             2070
_reflns_number_gt                1553
_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)+(0.1144P)²+0.4146P] 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         2070
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0836
_refine_ls_R_factor_gt           0.0623
_refine_ls_wR_factor_ref         0.1940
_refine_ls_wR_factor_gt          0.1648
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.005
_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 0.5870(3) 0.2093(3) 0.28498(12) 0.0393(6) Uani 1 1 d . . .
H1 H 0.5880 0.0911 0.2777 0.047 Uiso 1 1 calc R . .
C2 C 0.6346(3) 0.2710(3) 0.35194(10) 0.0314(5) Uani 1 1 d . . .
C3 C 0.6810(3) 0.1620(3) 0.40342(11) 0.0316(6) Uani 1 1 d . . .
C4 C 0.6822(3) -0.0272(3) 0.39833(12) 0.0442(6) Uani 1 1 d . . .
H4A H 0.5915 -0.0740 0.4285 0.066 Uiso 1 1 calc R . .
H4B H 0.8006 -0.0699 0.4111 0.066 Uiso 1 1 calc R . .
H4C H 0.6555 -0.0607 0.3521 0.066 Uiso 1 1 calc R . .
C5 C 0.7295(3) 0.2312(3) 0.46641(10) 0.0313(5) Uani 1 1 d . . .
C6 C 0.6799(3) 0.5138(3) 0.42374(11) 0.0316(5) Uani 1 1 d . . .
H6 H 0.6779 0.6321 0.4308 0.038 Uiso 1 1 calc R . .
C7 C 0.6338(3) 0.4485(3) 0.36366(11) 0.0325(5) Uani 1 1 d . . .
H7 H 0.6000 0.5223 0.3283 0.039 Uiso 1 1 calc R . .
C8 C 0.7839(3) 0.1617(3) 0.52715(11) 0.0403(6) Uani 1 1 d . . .
H8 H 0.7966 0.0451 0.5368 0.048 Uiso 1 1 calc R . .
C9 C 0.8165(3) 0.2952(3) 0.57141(11) 0.0397(6) Uani 1 1 d . . .
H9 H 0.8554 0.2837 0.6166 0.048 Uiso 1 1 calc R . .
C10 C 0.7833(3) 0.4463(3) 0.53928(10) 0.0323(6) Uani 1 1 d . . .
C11 C 0.7957(3) 0.6232(3) 0.56235(11) 0.0337(5) Uani 1 1 d . . .
H11A H 0.6782 0.6785 0.5555 0.040 Uiso 1 1 calc R . .
H11B H 0.8845 0.6832 0.5343 0.040 Uiso 1 1 calc R . .
C12 C 0.8493(3) 0.6408(3) 0.63601(11) 0.0365(6) Uani 1 1 d . . .
H12A H 0.7609 0.5802 0.6641 0.044 Uiso 1 1 calc R . .
H12B H 0.9672 0.5864 0.6428 0.044 Uiso 1 1 calc R . .
C13 C 0.8604(3) 0.8219(3) 0.65946(11) 0.0393(6) Uani 1 1 d . . .
H13A H 0.7422 0.8762 0.6531 0.047 Uiso 1 1 calc R . .
H13B H 0.9482 0.8829 0.6313 0.047 Uiso 1 1 calc R . .
C14 C 0.9153(4) 0.8377(4) 0.73281(13) 0.0523(7) Uani 1 1 d . . .
H14A H 1.0333 0.7861 0.7393 0.078 Uiso 1 1 calc R . .
H14B H 0.8273 0.7800 0.7611 0.078 Uiso 1 1 calc R . .
H14C H 0.9208 0.9570 0.7453 0.078 Uiso 1 1 calc R . .
N1 N 0.7302(2) 0.4059(2) 0.47501(8) 0.0291(5) Uani 1 1 d . . .
O1 O 0.5463(3) 0.2991(2) 0.23820(8) 0.0541(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 1.212(3) . ?
C1 C2 1.465(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.386(3) . ?
C2 C7 1.429(3) . ?
C3 C5 1.417(3) . ?
C3 C4 1.505(3) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C8 1.391(3) . ?
C5 N1 1.397(3) . ?
C6 C7 1.349(3) . ?
C6 N1 1.385(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.400(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.382(3) . ?
C9 H9 0.9500 . ?
C10 N1 1.378(3) . ?
C10 C11 1.481(3) . ?
C11 C12 1.528(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.514(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.523(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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
O1 C1 C2 124.3(2) . . ?
O1 C1 H1 117.8 . . ?
C2 C1 H1 117.8 . . ?
C3 C2 C7 119.75(19) . . ?
C3 C2 C1 121.7(2) . . ?
C7 C2 C1 118.53(19) . . ?
C2 C3 C5 118.5(2) . . ?
C2 C3 C4 125.1(2) . . ?
C5 C3 C4 116.44(19) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C8 C5 N1 106.63(18) . . ?
C8 C5 C3 133.7(2) . . ?
N1 C5 C3 119.66(18) . . ?
C7 C6 N1 119.1(2) . . ?
C7 C6 H6 120.5 . . ?
N1 C6 H6 120.5 . . ?
C6 C7 C2 121.5(2) . . ?
C6 C7 H7 119.2 . . ?
C2 C7 H7 119.2 . . ?
C5 C8 C9 107.3(2) . . ?
C5 C8 H8 126.3 . . ?
C9 C8 H8 126.3 . . ?
C10 C9 C8 109.5(2) . . ?
C10 C9 H9 125.2 . . ?
C8 C9 H9 125.2 . . ?
N1 C10 C9 106.2(2) . . ?
N1 C10 C11 121.81(19) . . ?
C9 C10 C11 131.9(2) . . ?
C10 C11 C12 113.65(19) . . ?
C10 C11 H11A 108.8 . . ?
C12 C11 H11A 108.8 . . ?
C10 C11 H11B 108.8 . . ?
C12 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C13 C12 C11 113.42(19) . . ?
C13 C12 H12A 108.9 . . ?
C11 C12 H12A 108.9 . . ?
C13 C12 H12B 108.9 . . ?
C11 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C12 C13 C14 112.9(2) . . ?
C12 C13 H13A 109.0 . . ?
C14 C13 H13A 109.0 . . ?
C12 C13 H13B 109.0 . . ?
C14 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
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 . . ?
C10 N1 C6 128.2(2) . . ?
C10 N1 C5 110.25(17) . . ?
C6 N1 C5 121.50(18) . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        25.13
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.269
_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_d19746
_database_code_depnum_ccdc_archive 'CCDC 1894129'
_audit_update_record             
;
2019-01-28 deposited with the CCDC.	2019-05-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H21 N O'
_chemical_formula_sum            'C20 H21 N O'
_chemical_formula_weight         291.38

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           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.7561(3)
_cell_length_b                   8.5826(5)
_cell_length_c                   14.0541(8)
_cell_angle_alpha                90.518(2)
_cell_angle_beta                 90.543(2)
_cell_angle_gamma                103.168(2)
_cell_volume                     793.41(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9943
_cell_measurement_theta_min      2.436
_cell_measurement_theta_max      25.029

_exptl_crystal_description       prism
_exptl_crystal_colour            red-brown
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.72
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             312
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9463
_exptl_absorpt_correction_T_max  0.9831
_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            17180
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_av_sigmaI/netI    0.0328
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.44
_diffrn_reflns_theta_max         25.06
_reflns_number_total             2745
_reflns_number_gt                2485
_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)+(0.0574P)²+0.2839P] 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       0.24(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2745
_refine_ls_number_parameters     204
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.1247
_refine_ls_wR_factor_gt          0.1205
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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 0.4951(2) 1.29842(18) 0.97836(11) 0.0394(4) Uani 1 1 d . . .
H1 H 0.5975 1.3905 0.9950 0.047 Uiso 1 1 calc R . .
C2 C 0.5501(2) 1.18440(16) 0.91138(9) 0.0301(3) Uani 1 1 d . . .
C3 C 0.7424(2) 1.21231(17) 0.87345(10) 0.0343(4) Uani 1 1 d . . .
C4 C 0.9089(3) 1.3583(2) 0.89408(13) 0.0480(4) Uani 1 1 d . . .
H4A H 1.0040 1.3763 0.8410 0.072 Uiso 1 1 calc R . .
H4B H 0.9815 1.3420 0.9525 0.072 Uiso 1 1 calc R . .
H4C H 0.8496 1.4516 0.9022 0.072 Uiso 1 1 calc R . .
C5 C 0.7883(2) 1.09412(19) 0.81104(11) 0.0387(4) Uani 1 1 d . . .
H5 H 0.9187 1.1132 0.7829 0.046 Uiso 1 1 calc R . .
C6 C 0.6535(2) 0.95666(18) 0.79063(10) 0.0364(4) Uani 1 1 d . . .
H6 H 0.6908 0.8798 0.7497 0.044 Uiso 1 1 calc R . .
C7 C 0.4024(2) 1.04162(16) 0.88727(9) 0.0288(3) Uani 1 1 d . . .
C8 C 0.2009(2) 0.98217(17) 0.90723(10) 0.0332(4) Uani 1 1 d . . .
H8 H 0.1186 1.0332 0.9455 0.040 Uiso 1 1 calc R . .
C9 C 0.1379(2) 0.83328(17) 0.86150(10) 0.0350(4) Uani 1 1 d . . .
H9 H 0.0047 0.7668 0.8634 0.042 Uiso 1 1 calc R . .
C10 C 0.2990(2) 0.79831(16) 0.81337(10) 0.0319(4) Uani 1 1 d . . .
C11 C 0.3099(2) 0.65794(16) 0.75455(10) 0.0333(4) Uani 1 1 d . . .
C12 C 0.4634(3) 0.57544(18) 0.76581(11) 0.0412(4) Uani 1 1 d . . .
H12 H 0.5663 0.6104 0.8129 0.049 Uiso 1 1 calc R . .
C13 C 0.4686(3) 0.44330(19) 0.70954(11) 0.0431(4) Uani 1 1 d . . .
H13 H 0.5757 0.3898 0.7190 0.052 Uiso 1 1 calc R . .
C14 C 0.3229(2) 0.38642(17) 0.63994(10) 0.0369(4) Uani 1 1 d . . .
C15 C 0.1660(2) 0.46639(19) 0.63148(11) 0.0427(4) Uani 1 1 d . . .
H15 H 0.0597 0.4284 0.5865 0.051 Uiso 1 1 calc R . .
C16 C 0.1604(2) 0.59955(18) 0.68663(11) 0.0397(4) Uani 1 1 d . . .
H16 H 0.0521 0.6520 0.6779 0.048 Uiso 1 1 calc R . .
C17 C 0.3327(3) 0.24021(18) 0.57821(11) 0.0419(4) Uani 1 1 d . . .
C18 C 0.5533(4) 0.2309(3) 0.5621(2) 0.0828(8) Uani 1 1 d . . .
H18A H 0.5564 0.1396 0.5202 0.124 Uiso 1 1 calc R . .
H18B H 0.6176 0.2172 0.6233 0.124 Uiso 1 1 calc R . .
H18C H 0.6272 0.3298 0.5325 0.124 Uiso 1 1 calc R . .
C19 C 0.2342(5) 0.2472(3) 0.48080(14) 0.0821(8) Uani 1 1 d . . .
H19A H 0.2981 0.3478 0.4499 0.123 Uiso 1 1 calc R . .
H19B H 0.0887 0.2414 0.4884 0.123 Uiso 1 1 calc R . .
H19C H 0.2527 0.1568 0.4414 0.123 Uiso 1 1 calc R . .
C20 C 0.2241(4) 0.0902(2) 0.62903(14) 0.0642(6) Uani 1 1 d . . .
H20A H 0.0795 0.0897 0.6343 0.096 Uiso 1 1 calc R . .
H20B H 0.2834 0.0883 0.6928 0.096 Uiso 1 1 calc R . .
H20C H 0.2394 -0.0044 0.5928 0.096 Uiso 1 1 calc R . .
N1 N 0.46268(17) 0.92654(13) 0.82847(8) 0.0290(3) Uani 1 1 d . . .
O1 O 0.32978(18) 1.28545(14) 1.01450(8) 0.0477(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 1.2137(19) . ?
C1 C2 1.462(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.380(2) . ?
C2 C7 1.429(2) . ?
C3 C5 1.423(2) . ?
C3 C4 1.505(2) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.342(2) . ?
C5 H5 0.9500 . ?
C6 N1 1.3697(18) . ?
C6 H6 0.9500 . ?
C7 C8 1.373(2) . ?
C7 N1 1.4138(17) . ?
C8 C9 1.400(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.375(2) . ?
C9 H9 0.9500 . ?
C10 N1 1.3842(18) . ?
C10 C11 1.4711(19) . ?
C11 C16 1.388(2) . ?
C11 C12 1.391(2) . ?
C12 C13 1.384(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.385(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.393(2) . ?
C14 C17 1.533(2) . ?
C15 C16 1.383(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C20 1.517(2) . ?
C17 C19 1.524(3) . ?
C17 C18 1.529(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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
O1 C1 C2 125.55(14) . . ?
O1 C1 H1 117.2 . . ?
C2 C1 H1 117.2 . . ?
C3 C2 C7 120.42(13) . . ?
C3 C2 C1 120.71(13) . . ?
C7 C2 C1 118.86(13) . . ?
C2 C3 C5 117.93(13) . . ?
C2 C3 C4 124.71(14) . . ?
C5 C3 C4 117.36(14) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C3 122.28(14) . . ?
C6 C5 H5 118.9 . . ?
C3 C5 H5 118.9 . . ?
C5 C6 N1 120.45(13) . . ?
C5 C6 H6 119.8 . . ?
N1 C6 H6 119.8 . . ?
C8 C7 N1 106.59(12) . . ?
C8 C7 C2 135.20(13) . . ?
N1 C7 C2 118.21(12) . . ?
C7 C8 C9 108.16(12) . . ?
C7 C8 H8 125.9 . . ?
C9 C8 H8 125.9 . . ?
C10 C9 C8 109.31(13) . . ?
C10 C9 H9 125.3 . . ?
C8 C9 H9 125.3 . . ?
C9 C10 N1 106.63(12) . . ?
C9 C10 C11 130.14(13) . . ?
N1 C10 C11 123.22(12) . . ?
C16 C11 C12 117.23(13) . . ?
C16 C11 C10 120.23(13) . . ?
C12 C11 C10 122.51(13) . . ?
C13 C12 C11 121.01(14) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C14 122.21(14) . . ?
C12 C13 H13 118.9 . . ?
C14 C13 H13 118.9 . . ?
C13 C14 C15 116.33(13) . . ?
C13 C14 C17 121.18(14) . . ?
C15 C14 C17 122.46(14) . . ?
C16 C15 C14 121.92(14) . . ?
C16 C15 H15 119.0 . . ?
C14 C15 H15 119.0 . . ?
C15 C16 C11 121.23(14) . . ?
C15 C16 H16 119.4 . . ?
C11 C16 H16 119.4 . . ?
C20 C17 C19 109.54(17) . . ?
C20 C17 C18 108.64(17) . . ?
C19 C17 C18 107.52(18) . . ?
C20 C17 C14 108.78(13) . . ?
C19 C17 C14 111.55(14) . . ?
C18 C17 C14 110.77(14) . . ?
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 . . ?
C6 N1 C10 129.94(12) . . ?
C6 N1 C7 120.56(12) . . ?
C10 N1 C7 109.32(11) . . ?

_diffrn_measured_fraction_theta_max 0.977
_diffrn_reflns_theta_full        25.06
_diffrn_measured_fraction_theta_full 0.977
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.032
####################################################################### 
# 
# 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_d19220
_database_code_depnum_ccdc_archive 'CCDC 1894128'
_audit_update_record             
;
2019-01-28 deposited with the CCDC.	2019-05-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H10 Cl N O'
_chemical_formula_sum            'C15 H10 Cl N O'
_chemical_formula_weight         255.69

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'
Cl Cl 0.1484 0.1585 '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                   3.9037(4)
_cell_length_b                   39.676(5)
_cell_length_c                   7.6371(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.326(3)
_cell_angle_gamma                90.00
_cell_volume                     1170.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9507
_cell_measurement_theta_min      2.563
_cell_measurement_theta_max      25.016

_exptl_crystal_description       prism
_exptl_crystal_colour            red-orange
_exptl_crystal_size_max          0.66
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528
_exptl_absorpt_coefficient_mu    0.311
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8212
_exptl_absorpt_correction_T_max  0.9907
_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            15094
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_sigmaI/netI    0.0164
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -47
_diffrn_reflns_limit_k_max       47
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.74
_diffrn_reflns_theta_max         25.06
_reflns_number_total             2058
_reflns_number_gt                1897
_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)+(0.0636P)²+0.5797P] 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         2058
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1129
_refine_ls_wR_factor_gt          0.1100
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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 0.3383(5) 0.44881(5) 0.3551(2) 0.0304(4) Uani 1 1 d . . .
C2 C 0.3168(5) 0.45903(5) 0.5257(3) 0.0329(4) Uani 1 1 d . . .
H2 H 0.2346 0.4809 0.5480 0.040 Uiso 1 1 calc R . .
C3 C 0.4165(5) 0.43697(5) 0.6641(2) 0.0300(4) Uani 1 1 d . . .
H3 H 0.4036 0.4439 0.7820 0.036 Uiso 1 1 calc R . .
C4 C 0.5355(4) 0.40472(4) 0.6331(2) 0.0257(4) Uani 1 1 d . . .
C5 C 0.5586(4) 0.39536(4) 0.4594(2) 0.0277(4) Uani 1 1 d . . .
H5 H 0.6429 0.3736 0.4363 0.033 Uiso 1 1 calc R . .
C6 C 0.4609(5) 0.41726(5) 0.3199(2) 0.0306(4) Uani 1 1 d . . .
H6 H 0.4779 0.4107 0.2018 0.037 Uiso 1 1 calc R . .
C7 C 0.6468(4) 0.38271(4) 0.7849(2) 0.0257(4) Uani 1 1 d . . .
C8 C 0.8546(5) 0.39011(5) 0.9422(2) 0.0293(4) Uani 1 1 d . . .
H8 H 0.9611 0.4113 0.9716 0.035 Uiso 1 1 calc R . .
C9 C 0.8846(5) 0.36167(5) 1.0520(2) 0.0292(4) Uani 1 1 d . . .
H9 H 1.0153 0.3601 1.1668 0.035 Uiso 1 1 calc R . .
C10 C 0.6904(4) 0.33650(4) 0.9632(2) 0.0252(4) Uani 1 1 d . . .
C11 C 0.6050(5) 0.30265(4) 1.0035(2) 0.0283(4) Uani 1 1 d . . .
C12 C 0.7403(5) 0.28721(5) 1.1730(3) 0.0384(5) Uani 1 1 d . . .
H12 H 0.6741 0.2645 1.1899 0.046 Uiso 1 1 calc R . .
C13 C 0.3896(5) 0.28434(5) 0.8829(2) 0.0307(4) Uani 1 1 d . . .
H13 H 0.3334 0.2618 0.9099 0.037 Uiso 1 1 calc R . .
C14 C 0.2488(5) 0.29850(5) 0.7178(2) 0.0307(4) Uani 1 1 d . . .
H14 H 0.0992 0.2855 0.6347 0.037 Uiso 1 1 calc R . .
C15 C 0.3273(4) 0.33049(5) 0.6786(2) 0.0276(4) Uani 1 1 d . . .
H15 H 0.2309 0.3400 0.5682 0.033 Uiso 1 1 calc R . .
Cl1 Cl 0.20837(15) 0.476134(13) 0.17926(7) 0.0470(2) Uani 1 1 d . . .
N1 N 0.5446(4) 0.34944(4) 0.79667(18) 0.0236(3) Uani 1 1 d . . .
O1 O 0.9268(5) 0.30018(4) 1.2932(2) 0.0579(5) 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 1.379(3) . ?
C1 C6 1.380(3) . ?
C1 Cl1 1.7432(18) . ?
C2 C3 1.384(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.393(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.392(3) . ?
C4 C7 1.466(2) . ?
C5 C6 1.385(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.380(3) . ?
C7 N1 1.386(2) . ?
C8 C9 1.401(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.372(3) . ?
C9 H9 0.9500 . ?
C10 N1 1.412(2) . ?
C10 C11 1.428(3) . ?
C11 C13 1.363(3) . ?
C11 C12 1.460(3) . ?
C12 O1 1.202(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.417(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.349(3) . ?
C14 H14 0.9500 . ?
C15 N1 1.370(2) . ?
C15 H15 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
C2 C1 C6 121.42(17) . . ?
C2 C1 Cl1 119.61(14) . . ?
C6 C1 Cl1 118.97(15) . . ?
C1 C2 C3 119.10(17) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C2 C3 C4 121.00(17) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 118.43(16) . . ?
C5 C4 C7 122.79(15) . . ?
C3 C4 C7 118.71(16) . . ?
C6 C5 C4 121.11(16) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C1 C6 C5 118.93(17) . . ?
C1 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C8 C7 N1 106.54(15) . . ?
C8 C7 C4 129.13(16) . . ?
N1 C7 C4 124.30(15) . . ?
C7 C8 C9 109.71(16) . . ?
C7 C8 H8 125.1 . . ?
C9 C8 H8 125.1 . . ?
C10 C9 C8 107.33(16) . . ?
C10 C9 H9 126.3 . . ?
C8 C9 H9 126.3 . . ?
C9 C10 N1 107.61(15) . . ?
C9 C10 C11 135.00(16) . . ?
N1 C10 C11 117.36(15) . . ?
C13 C11 C10 119.73(16) . . ?
C13 C11 C12 118.93(17) . . ?
C10 C11 C12 121.33(17) . . ?
O1 C12 C11 126.81(19) . . ?
O1 C12 H12 116.6 . . ?
C11 C12 H12 116.6 . . ?
C11 C13 C14 120.78(17) . . ?
C11 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C15 C14 C13 119.93(17) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 N1 120.62(16) . . ?
C14 C15 H15 119.7 . . ?
N1 C15 H15 119.7 . . ?
C15 N1 C7 129.56(15) . . ?
C15 N1 C10 121.57(15) . . ?
C7 N1 C10 108.81(14) . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.06
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.502
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.049
####################################################################### 
# 
# 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 
# 
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# Please retain this information to preserve the provenance of 
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data_d19628
_database_code_depnum_ccdc_archive 'CCDC 1894126'
_audit_update_record             
;
2019-01-28 deposited with the CCDC.	2019-05-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H18 Cl N O'
_chemical_formula_sum            'C19 H18 Cl N O'
_chemical_formula_weight         311.79

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'
Cl Cl 0.1484 0.1585 '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           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.3841(9)
_cell_length_b                   13.7451(15)
_cell_length_c                   14.1044(15)
_cell_angle_alpha                90.770(3)
_cell_angle_beta                 97.215(3)
_cell_angle_gamma                94.980(3)
_cell_volume                     1606.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    3291
_cell_measurement_theta_min      2.458
_cell_measurement_theta_max      24.467

_exptl_crystal_description       prism
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    0.239
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9274
_exptl_absorpt_correction_T_max  0.9976
_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            39950
_diffrn_reflns_av_R_equivalents  0.1459
_diffrn_reflns_av_sigmaI/netI    0.0963
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.46
_diffrn_reflns_theta_max         25.07
_reflns_number_total             5665
_reflns_number_gt                3273
_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)+(0.0564P)²+1.0699P] 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       0.0125(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5665
_refine_ls_number_parameters     400
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1365
_refine_ls_R_factor_gt           0.0641
_refine_ls_wR_factor_ref         0.1607
_refine_ls_wR_factor_gt          0.1312
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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 0.8502(4) 0.8849(3) 0.7803(3) 0.0463(10) Uani 1 1 d . . .
C2 C 0.8401(4) 0.7860(3) 0.7561(3) 0.0433(10) Uani 1 1 d . . .
H2 H 0.8436 0.7386 0.8044 0.052 Uiso 1 1 calc R . .
C3 C 0.8250(4) 0.7577(3) 0.6613(3) 0.0357(9) Uani 1 1 d . . .
H3 H 0.8189 0.6902 0.6446 0.043 Uiso 1 1 calc R . .
C4 C 0.8183(4) 0.8265(3) 0.5889(3) 0.0350(9) Uani 1 1 d . . .
C5 C 0.8252(4) 0.9248(3) 0.6158(3) 0.0421(10) Uani 1 1 d . . .
H5 H 0.8181 0.9724 0.5676 0.051 Uiso 1 1 calc R . .
C6 C 0.8420(4) 0.9547(3) 0.7100(3) 0.0466(10) Uani 1 1 d . . .
H6 H 0.8479 1.0221 0.7269 0.056 Uiso 1 1 calc R . .
C7 C 0.8174(4) 0.8011(3) 0.4884(3) 0.0348(9) Uani 1 1 d . . .
C8 C 0.8991(4) 0.8510(3) 0.4217(3) 0.0447(10) Uani 1 1 d . . .
H8 H 0.9629 0.9115 0.4336 0.054 Uiso 1 1 calc R . .
C9 C 0.8743(4) 0.8001(3) 0.3357(3) 0.0443(10) Uani 1 1 d . . .
H9 H 0.9185 0.8190 0.2792 0.053 Uiso 1 1 calc R . .
C10 C 0.7733(4) 0.7162(3) 0.3458(3) 0.0347(9) Uani 1 1 d . . .
C11 C 0.7097(4) 0.6373(3) 0.2842(2) 0.0345(9) Uani 1 1 d . . .
C12 C 0.7571(4) 0.6366(3) 0.1842(2) 0.0424(10) Uani 1 1 d . . .
H12A H 0.7717 0.5687 0.1651 0.051 Uiso 1 1 calc R . .
H12B H 0.8619 0.6758 0.1844 0.051 Uiso 1 1 calc R . .
C13 C 0.6326(4) 0.6771(3) 0.1113(3) 0.0494(11) Uani 1 1 d . . .
H13A H 0.6226 0.7462 0.1285 0.059 Uiso 1 1 calc R . .
H13B H 0.5265 0.6402 0.1138 0.059 Uiso 1 1 calc R . .
C14 C 0.6759(5) 0.6712(4) 0.0087(3) 0.0758(16) Uani 1 1 d . . .
H14A H 0.7819 0.7083 0.0065 0.091 Uiso 1 1 calc R . .
H14B H 0.6871 0.6021 -0.0079 0.091 Uiso 1 1 calc R . .
C15 C 0.5580(6) 0.7088(4) -0.0630(3) 0.0835(17) Uani 1 1 d . . .
H15A H 0.5910 0.7000 -0.1266 0.125 Uiso 1 1 calc R . .
H15B H 0.5516 0.7785 -0.0500 0.125 Uiso 1 1 calc R . .
H15C H 0.4520 0.6734 -0.0607 0.125 Uiso 1 1 calc R . .
C16 C 0.6029(4) 0.5674(3) 0.3167(2) 0.0352(9) Uani 1 1 d . . .
C17 C 0.5307(5) 0.4828(3) 0.2585(3) 0.0428(10) Uani 1 1 d . . .
H17 H 0.5606 0.4761 0.1961 0.051 Uiso 1 1 calc R . .
C18 C 0.5600(4) 0.5766(3) 0.4106(3) 0.0362(9) Uani 1 1 d . . .
H18 H 0.4822 0.5298 0.4312 0.043 Uiso 1 1 calc R . .
C19 C 0.6262(4) 0.6495(3) 0.4711(3) 0.0328(9) Uani 1 1 d . . .
H19 H 0.5968 0.6536 0.5338 0.039 Uiso 1 1 calc R . .
C20 C 0.8377(4) 0.3422(3) 0.9383(2) 0.0394(9) Uani 1 1 d . . .
C21 C 0.8246(4) 0.4075(3) 0.8655(3) 0.0416(10) Uani 1 1 d . . .
H21 H 0.8441 0.4756 0.8795 0.050 Uiso 1 1 calc R . .
C22 C 0.7831(4) 0.3744(3) 0.7715(3) 0.0356(9) Uani 1 1 d . . .
H22 H 0.7749 0.4201 0.7215 0.043 Uiso 1 1 calc R . .
C23 C 0.7532(4) 0.2745(3) 0.7498(2) 0.0334(9) Uani 1 1 d . . .
C24 C 0.7652(4) 0.2103(3) 0.8256(3) 0.0405(9) Uani 1 1 d . . .
H24 H 0.7439 0.1421 0.8126 0.049 Uiso 1 1 calc R . .
C25 C 0.8071(4) 0.2432(3) 0.9191(3) 0.0447(10) Uani 1 1 d . . .
H25 H 0.8149 0.1982 0.9696 0.054 Uiso 1 1 calc R . .
C26 C 0.7033(4) 0.2351(3) 0.6524(2) 0.0331(8) Uani 1 1 d . . .
C27 C 0.5957(4) 0.1544(3) 0.6242(3) 0.0368(9) Uani 1 1 d . . .
H27 H 0.5415 0.1133 0.6659 0.044 Uiso 1 1 calc R . .
C28 C 0.5798(4) 0.1434(3) 0.5255(3) 0.0377(9) Uani 1 1 d . . .
H28 H 0.5138 0.0935 0.4883 0.045 Uiso 1 1 calc R . .
C29 C 0.6768(4) 0.2175(3) 0.4907(2) 0.0316(8) Uani 1 1 d . . .
C30 C 0.7042(4) 0.2448(3) 0.3978(2) 0.0338(9) Uani 1 1 d . . .
C31 C 0.6120(4) 0.1844(3) 0.3153(3) 0.0412(10) Uani 1 1 d . . .
H31A H 0.5848 0.2281 0.2616 0.049 Uiso 1 1 calc R . .
H31B H 0.5093 0.1557 0.3352 0.049 Uiso 1 1 calc R . .
C32 C 0.7011(5) 0.1028(3) 0.2799(3) 0.0579(12) Uani 1 1 d . . .
H32A H 0.7215 0.0558 0.3317 0.069 Uiso 1 1 calc R . .
H32B H 0.8069 0.1303 0.2633 0.069 Uiso 1 1 calc R . .
C33 C 0.6054(6) 0.0490(4) 0.1923(4) 0.0757(15) Uani 1 1 d . . .
H33A H 0.5033 0.0187 0.2116 0.091 Uiso 1 1 calc R . .
H33B H 0.5765 0.0983 0.1440 0.091 Uiso 1 1 calc R . .
C34 C 0.6807(8) -0.0247(5) 0.1472(5) 0.128(3) Uani 1 1 d . . .
H34A H 0.6020 -0.0597 0.0985 0.192 Uiso 1 1 calc R . .
H34B H 0.7210 -0.0706 0.1951 0.192 Uiso 1 1 calc R . .
H34C H 0.7710 0.0056 0.1168 0.192 Uiso 1 1 calc R . .
C35 C 0.8133(4) 0.3238(3) 0.3871(2) 0.0346(9) Uani 1 1 d . . .
C36 C 0.8475(5) 0.3588(3) 0.2944(3) 0.0422(10) Uani 1 1 d . . .
H36 H 0.7931 0.3242 0.2392 0.051 Uiso 1 1 calc R . .
C37 C 0.8970(4) 0.3748(3) 0.4709(2) 0.0348(9) Uani 1 1 d . . .
H37 H 0.9750 0.4276 0.4635 0.042 Uiso 1 1 calc R . .
C38 C 0.8687(4) 0.3501(3) 0.5592(3) 0.0344(9) Uani 1 1 d . . .
H38 H 0.9264 0.3847 0.6134 0.041 Uiso 1 1 calc R . .
Cl1 Cl 0.87187(15) 0.92261(10) 0.89976(8) 0.0719(4) Uani 1 1 d . . .
Cl2 Cl 0.88958(12) 0.38335(9) 1.05583(7) 0.0569(3) Uani 1 1 d . . .
N1 N 0.7378(3) 0.7190(2) 0.44106(19) 0.0299(7) Uani 1 1 d . . .
N2 N 0.7542(3) 0.2736(2) 0.57062(19) 0.0299(7) Uani 1 1 d . . .
O1 O 0.4350(3) 0.4203(2) 0.28408(19) 0.0568(8) Uani 1 1 d . . .
O2 O 0.9409(3) 0.4293(2) 0.28204(18) 0.0528(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 C2 1.389(5) . ?
C1 C6 1.389(6) . ?
C1 Cl1 1.739(4) . ?
C2 C3 1.375(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.400(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.393(5) . ?
C4 C7 1.454(5) . ?
C5 C6 1.373(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N1 1.378(4) . ?
C7 C8 1.387(5) . ?
C8 C9 1.376(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.390(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.405(5) . ?
C10 N1 1.412(4) . ?
C11 C16 1.379(5) . ?
C11 C12 1.513(5) . ?
C12 C13 1.518(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.538(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.456(6) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C18 1.423(5) . ?
C16 C17 1.456(5) . ?
C17 O1 1.214(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.342(5) . ?
C18 H18 0.9500 . ?
C19 N1 1.386(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.373(5) . ?
C20 C25 1.379(5) . ?
C20 Cl2 1.734(4) . ?
C21 C22 1.387(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.397(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.395(5) . ?
C23 C26 1.467(5) . ?
C24 C25 1.381(5) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 N2 1.375(4) . ?
C26 C27 1.388(5) . ?
C27 C28 1.387(5) . ?
C27 H27 0.9500 . ?
C28 C29 1.382(5) . ?
C28 H28 0.9500 . ?
C29 C30 1.409(5) . ?
C29 N2 1.412(4) . ?
C30 C35 1.381(5) . ?
C30 C31 1.508(5) . ?
C31 C32 1.513(5) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.530(6) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.423(7) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 C37 1.437(5) . ?
C35 C36 1.453(5) . ?
C36 O2 1.221(4) . ?
C36 H36 0.9500 . ?
C37 C38 1.339(5) . ?
C37 H37 0.9500 . ?
C38 N2 1.386(4) . ?
C38 H38 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
C2 C1 C6 120.7(4) . . ?
C2 C1 Cl1 120.1(3) . . ?
C6 C1 Cl1 119.1(3) . . ?
C3 C2 C1 119.3(4) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 121.3(4) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 117.9(4) . . ?
C5 C4 C7 118.6(3) . . ?
C3 C4 C7 123.4(3) . . ?
C6 C5 C4 121.8(4) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 C1 119.1(4) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 106.0(3) . . ?
N1 C7 C4 126.1(3) . . ?
C8 C7 C4 127.9(3) . . ?
C9 C8 C7 110.0(3) . . ?
C9 C8 H8 125.0 . . ?
C7 C8 H8 125.0 . . ?
C8 C9 C10 108.1(3) . . ?
C8 C9 H9 125.9 . . ?
C10 C9 H9 125.9 . . ?
C9 C10 C11 133.8(4) . . ?
C9 C10 N1 106.0(3) . . ?
C11 C10 N1 120.2(3) . . ?
C16 C11 C10 118.4(3) . . ?
C16 C11 C12 123.8(3) . . ?
C10 C11 C12 117.7(3) . . ?
C11 C12 C13 112.7(3) . . ?
C11 C12 H12A 109.1 . . ?
C13 C12 H12A 109.1 . . ?
C11 C12 H12B 109.1 . . ?
C13 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
C12 C13 C14 112.8(3) . . ?
C12 C13 H13A 109.0 . . ?
C14 C13 H13A 109.0 . . ?
C12 C13 H13B 109.0 . . ?
C14 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C15 C14 C13 114.1(4) . . ?
C15 C14 H14A 108.7 . . ?
C13 C14 H14A 108.7 . . ?
C15 C14 H14B 108.7 . . ?
C13 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C11 C16 C18 119.7(3) . . ?
C11 C16 C17 122.6(3) . . ?
C18 C16 C17 117.7(3) . . ?
O1 C17 C16 124.5(4) . . ?
O1 C17 H17 117.7 . . ?
C16 C17 H17 117.7 . . ?
C19 C18 C16 121.9(3) . . ?
C19 C18 H18 119.1 . . ?
C16 C18 H18 119.1 . . ?
C18 C19 N1 119.4(3) . . ?
C18 C19 H19 120.3 . . ?
N1 C19 H19 120.3 . . ?
C21 C20 C25 120.4(3) . . ?
C21 C20 Cl2 120.4(3) . . ?
C25 C20 Cl2 119.2(3) . . ?
C20 C21 C22 120.3(4) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C21 C22 C23 120.5(3) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C24 C23 C22 117.7(3) . . ?
C24 C23 C26 119.1(3) . . ?
C22 C23 C26 123.1(3) . . ?
C25 C24 C23 121.7(4) . . ?
C25 C24 H24 119.1 . . ?
C23 C24 H24 119.1 . . ?
C20 C25 C24 119.3(4) . . ?
C20 C25 H25 120.3 . . ?
C24 C25 H25 120.3 . . ?
N2 C26 C27 106.9(3) . . ?
N2 C26 C23 125.6(3) . . ?
C27 C26 C23 127.6(3) . . ?
C28 C27 C26 109.1(3) . . ?
C28 C27 H27 125.4 . . ?
C26 C27 H27 125.4 . . ?
C29 C28 C27 108.1(3) . . ?
C29 C28 H28 126.0 . . ?
C27 C28 H28 126.0 . . ?
C28 C29 C30 133.3(3) . . ?
C28 C29 N2 106.7(3) . . ?
C30 C29 N2 120.0(3) . . ?
C35 C30 C29 118.8(3) . . ?
C35 C30 C31 123.9(3) . . ?
C29 C30 C31 117.3(3) . . ?
C30 C31 C32 114.6(3) . . ?
C30 C31 H31A 108.6 . . ?
C32 C31 H31A 108.6 . . ?
C30 C31 H31B 108.6 . . ?
C32 C31 H31B 108.6 . . ?
H31A C31 H31B 107.6 . . ?
C31 C32 C33 111.8(4) . . ?
C31 C32 H32A 109.3 . . ?
C33 C32 H32A 109.3 . . ?
C31 C32 H32B 109.3 . . ?
C33 C32 H32B 109.3 . . ?
H32A C32 H32B 107.9 . . ?
C34 C33 C32 117.6(5) . . ?
C34 C33 H33A 107.9 . . ?
C32 C33 H33A 107.9 . . ?
C34 C33 H33B 107.9 . . ?
C32 C33 H33B 107.9 . . ?
H33A C33 H33B 107.2 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C30 C35 C37 119.1(3) . . ?
C30 C35 C36 122.9(3) . . ?
C37 C35 C36 117.9(3) . . ?
O2 C36 C35 124.9(4) . . ?
O2 C36 H36 117.6 . . ?
C35 C36 H36 117.6 . . ?
C38 C37 C35 122.1(3) . . ?
C38 C37 H37 119.0 . . ?
C35 C37 H37 119.0 . . ?
C37 C38 N2 119.3(3) . . ?
C37 C38 H38 120.3 . . ?
N2 C38 H38 120.3 . . ?
C7 N1 C19 129.9(3) . . ?
C7 N1 C10 109.8(3) . . ?
C19 N1 C10 120.0(3) . . ?
C26 N2 C38 130.3(3) . . ?
C26 N2 C29 109.1(3) . . ?
C38 N2 C29 120.4(3) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.07
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.652
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.054
####################################################################### 
# 
# 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_190231lt_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1913325'
loop_
_audit_author_name
_audit_author_address
'Pei-Ling Chen'
;National Tsing Hua University
Taiwan
;
_audit_update_record             
;
2019-05-01 deposited with the CCDC.	2019-05-21 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            'C21 H18 Cl N O3'
_chemical_formula_weight         367.81

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'
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'
Cl Cl 0.1484 0.1585 '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'

_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                   13.421(2)
_cell_length_b                   9.1933(15)
_cell_length_c                   14.5321(18)
_cell_angle_alpha                90
_cell_angle_beta                 91.484(4)
_cell_angle_gamma                90
_cell_volume                     1792.4(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4966
_cell_measurement_theta_min      2.6219
_cell_measurement_theta_max      26.4290

_exptl_crystal_description       tabullar
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.234
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6583
_exptl_absorpt_correction_T_max  0.7454
_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            9874
_diffrn_reflns_av_unetI/netI     0.0521
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.518
_diffrn_reflns_theta_max         26.446
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3700
_reflns_number_gt                2693
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.06(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3700
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1943
_refine_ls_R_factor_gt           0.1746
_refine_ls_wR_factor_ref         0.5549
_refine_ls_wR_factor_gt          0.4876
_refine_ls_goodness_of_fit_ref   2.432
_refine_ls_restrained_S_all      2.432
_refine_ls_shift/su_max          0.002
_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 0.8515(4) 0.6420(7) 0.2817(5) 0.0464(16) Uani 1 1 d . . . . .
C2 C 0.8424(4) 0.6637(7) 0.3763(5) 0.0493(17) Uani 1 1 d . . . . .
C3 C 0.7419(4) 0.6835(7) 0.3969(5) 0.0478(16) Uani 1 1 d . . . . .
H3 H 0.7161 0.7000 0.4562 0.057 Uiso 1 1 calc R U . . .
C4 C 0.6876(4) 0.6749(6) 0.3163(4) 0.0399(14) Uani 1 1 d . . . . .
C5 C 0.5845(4) 0.6772(6) 0.2911(4) 0.0387(14) Uani 1 1 d . . . . .
C6 C 0.5546(4) 0.6686(6) 0.1984(4) 0.0407(14) Uani 1 1 d . . . . .
C7 C 0.6286(4) 0.6509(7) 0.1301(4) 0.0446(15) Uani 1 1 d . . . . .
H7 H 0.6088 0.6452 0.0670 0.053 Uiso 1 1 calc R U . . .
C8 C 0.7269(4) 0.6421(7) 0.1546(4) 0.0458(15) Uani 1 1 d . . . . .
H8 H 0.7753 0.6291 0.1087 0.055 Uiso 1 1 calc R U . . .
C9 C 0.9360(4) 0.6126(7) 0.2230(5) 0.0488(16) Uani 1 1 d . . . . .
H9 H 0.9597 0.6975 0.1865 0.059 Uiso 1 1 calc R U . . .
C10 C 0.9450(4) 0.4665(8) 0.1768(5) 0.0580(19) Uani 1 1 d . . . . .
H10A H 0.8935 0.3926 0.1893 0.070 Uiso 1 1 calc R U . . .
H10B H 0.9710 0.4643 0.1137 0.070 Uiso 1 1 calc R U . . .
C11 C 1.0162(5) 0.5060(8) 0.2539(5) 0.0552(17) Uani 1 1 d . . . . .
H11A H 1.0859 0.5283 0.2382 0.066 Uiso 1 1 calc R U . . .
H11B H 1.0083 0.4565 0.3138 0.066 Uiso 1 1 calc R U . . .
C12 C 0.9245(5) 0.6672(8) 0.4438(5) 0.0560(18) Uani 1 1 d . . . . .
H12 H 0.9899 0.6477 0.4234 0.067 Uiso 1 1 calc R U . . .
C13 C 0.5138(4) 0.6748(6) 0.3685(4) 0.0422(15) Uani 1 1 d . . . . .
C14 C 0.3639(5) 0.5723(11) 0.4242(6) 0.070(2) Uani 1 1 d . . . . .
H14A H 0.3625 0.6628 0.4610 0.084 Uiso 1 1 calc R U . . .
H14B H 0.3800 0.4898 0.4659 0.084 Uiso 1 1 calc R U . . .
C15 C 0.2656(5) 0.5481(10) 0.3755(5) 0.063(2) Uani 1 1 d . . . . .
H15A H 0.2501 0.6317 0.3359 0.095 Uiso 1 1 calc R U . . .
H15B H 0.2135 0.5369 0.4210 0.095 Uiso 1 1 calc R U . . .
H15C H 0.2690 0.4599 0.3379 0.095 Uiso 1 1 calc R U . . .
C16 C 0.4488(4) 0.6797(6) 0.1683(5) 0.0437(15) Uani 1 1 d . . . . .
C17 C 0.3912(5) 0.7961(6) 0.1952(5) 0.0464(15) Uani 1 1 d . . . . .
H17 H 0.4193 0.8685 0.2346 0.056 Uiso 1 1 calc R U . . .
C18 C 0.2921(5) 0.8080(7) 0.1649(5) 0.0492(16) Uani 1 1 d . . . . .
H18 H 0.2527 0.8884 0.1831 0.059 Uiso 1 1 calc R U . . .
C19 C 0.2522(4) 0.7027(7) 0.1089(5) 0.0454(15) Uani 1 1 d . . . . .
C20 C 0.3082(5) 0.5859(7) 0.0793(4) 0.0505(16) Uani 1 1 d . . . . .
H20 H 0.2795 0.5145 0.0395 0.061 Uiso 1 1 calc R U . . .
C21 C 0.4073(5) 0.5752(7) 0.1093(5) 0.0550(17) Uani 1 1 d . . . . .
H21 H 0.4469 0.4961 0.0894 0.066 Uiso 1 1 calc R U . . .
Cl1 Cl 0.12919(11) 0.7196(2) 0.06862(13) 0.0575(9) Uani 1 1 d . . . . .
N1 N 0.7566(3) 0.6523(5) 0.2465(4) 0.0438(13) Uani 1 1 d . . . . .
O1 O 0.4384(3) 0.5836(5) 0.3514(3) 0.0536(13) Uani 1 1 d . . . . .
O2 O 0.5265(3) 0.7413(5) 0.4388(3) 0.0545(14) Uani 1 1 d . . . . .
O3 O 0.9137(4) 0.6938(7) 0.5250(4) 0.0645(15) 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 N1 1.363(8) . ?
C1 C2 1.398(10) . ?
C1 C9 1.461(8) . ?
C2 C3 1.401(9) . ?
C2 C12 1.456(9) . ?
C3 C4 1.365(9) . ?
C3 H3 0.9500 . ?
C4 N1 1.406(8) . ?
C4 C5 1.422(8) . ?
C5 C6 1.399(8) . ?
C5 C13 1.490(8) . ?
C6 C7 1.432(8) . ?
C6 C16 1.479(8) . ?
C7 C8 1.360(8) . ?
C7 H7 0.9500 . ?
C8 N1 1.388(8) . ?
C8 H8 0.9500 . ?
C9 C10 1.508(10) . ?
C9 C11 1.516(9) . ?
C9 H9 1.0000 . ?
C10 C11 1.497(9) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 O3 1.218(9) . ?
C12 H12 0.9500 . ?
C13 O2 1.199(8) . ?
C13 O1 1.333(7) . ?
C14 O1 1.478(8) . ?
C14 C15 1.497(10) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.382(8) . ?
C16 C21 1.393(9) . ?
C17 C18 1.394(9) . ?
C17 H17 0.9500 . ?
C18 C19 1.365(10) . ?
C18 H18 0.9500 . ?
C19 C20 1.385(9) . ?
C19 Cl1 1.744(6) . ?
C20 C21 1.392(9) . ?
C20 H20 0.9500 . ?
C21 H21 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
N1 C1 C2 104.7(5) . . ?
N1 C1 C9 121.7(6) . . ?
C2 C1 C9 133.5(6) . . ?
C1 C2 C3 109.7(6) . . ?
C1 C2 C12 125.6(6) . . ?
C3 C2 C12 124.7(7) . . ?
C4 C3 C2 107.8(6) . . ?
C4 C3 H3 126.1 . . ?
C2 C3 H3 126.1 . . ?
C3 C4 N1 106.3(5) . . ?
C3 C4 C5 135.6(6) . . ?
N1 C4 C5 118.1(5) . . ?
C6 C5 C4 120.1(5) . . ?
C6 C5 C13 123.6(5) . . ?
C4 C5 C13 116.1(5) . . ?
C5 C6 C7 119.1(6) . . ?
C5 C6 C16 122.1(6) . . ?
C7 C6 C16 118.8(5) . . ?
C8 C7 C6 120.8(6) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 N1 120.0(5) . . ?
C7 C8 H8 120.0 . . ?
N1 C8 H8 120.0 . . ?
C1 C9 C10 119.8(5) . . ?
C1 C9 C11 120.2(6) . . ?
C10 C9 C11 59.3(4) . . ?
C1 C9 H9 115.3 . . ?
C10 C9 H9 115.3 . . ?
C11 C9 H9 115.3 . . ?
C11 C10 C9 60.6(4) . . ?
C11 C10 H10A 117.7 . . ?
C9 C10 H10A 117.7 . . ?
C11 C10 H10B 117.7 . . ?
C9 C10 H10B 117.7 . . ?
H10A C10 H10B 114.8 . . ?
C10 C11 C9 60.1(4) . . ?
C10 C11 H11A 117.8 . . ?
C9 C11 H11A 117.8 . . ?
C10 C11 H11B 117.8 . . ?
C9 C11 H11B 117.8 . . ?
H11A C11 H11B 114.9 . . ?
O3 C12 C2 123.4(7) . . ?
O3 C12 H12 118.3 . . ?
C2 C12 H12 118.3 . . ?
O2 C13 O1 124.7(6) . . ?
O2 C13 C5 123.8(5) . . ?
O1 C13 C5 111.4(5) . . ?
O1 C14 C15 106.0(6) . . ?
O1 C14 H14A 110.5 . . ?
C15 C14 H14A 110.5 . . ?
O1 C14 H14B 110.5 . . ?
C15 C14 H14B 110.5 . . ?
H14A C14 H14B 108.7 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C21 119.3(6) . . ?
C17 C16 C6 120.6(6) . . ?
C21 C16 C6 120.0(5) . . ?
C16 C17 C18 120.5(6) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C19 C18 C17 119.3(6) . . ?
C19 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C18 C19 C20 121.8(6) . . ?
C18 C19 Cl1 119.4(5) . . ?
C20 C19 Cl1 118.8(5) . . ?
C19 C20 C21 118.6(6) . . ?
C19 C20 H20 120.7 . . ?
C21 C20 H20 120.7 . . ?
C20 C21 C16 120.5(6) . . ?
C20 C21 H21 119.8 . . ?
C16 C21 H21 119.8 . . ?
C1 N1 C8 126.7(5) . . ?
C1 N1 C4 111.5(5) . . ?
C8 N1 C4 121.8(5) . . ?
C13 O1 C14 115.8(5) . . ?

_refine_diff_density_max         1.805
_refine_diff_density_min         -2.806
_refine_diff_density_rms         0.206

_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_d19599
_database_code_depnum_ccdc_archive 'CCDC 1894127'
_audit_update_record             
;
2019-01-28 deposited with the CCDC.	2019-05-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H19 N O'
_chemical_formula_sum            'C19 H19 N O'
_chemical_formula_weight         277.35

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/n'

loop_
_symmetry_equiv_pos_as_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                   9.2570(3)
_cell_length_b                   14.9320(3)
_cell_length_c                   11.4194(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.5890(10)
_cell_angle_gamma                90.00
_cell_volume                     1487.09(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    8521
_cell_measurement_theta_min      2.464
_cell_measurement_theta_max      25.027

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.52
_exptl_crystal_size_min          0.38
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9573
_exptl_absorpt_correction_T_max  0.9717
_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            16035
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_av_sigmaI/netI    0.0289
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.46
_diffrn_reflns_theta_max         25.06
_reflns_number_total             2600
_reflns_number_gt                2281
_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)+(0.0408P)²+0.5930P] 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       0.035(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2600
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_ref         0.1028
_refine_ls_wR_factor_gt          0.0977
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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 0.54897(18) 0.15711(10) 0.33015(17) 0.0422(4) Uani 1 1 d . . .
H1 H 0.5776 0.1164 0.3980 0.051 Uiso 1 1 calc R . .
C2 C 0.56564(15) 0.25278(9) 0.36042(13) 0.0310(3) Uani 1 1 d . . .
C3 C 0.61601(16) 0.27824(10) 0.48231(14) 0.0364(4) Uani 1 1 d . . .
H3 H 0.6411 0.2338 0.5455 0.044 Uiso 1 1 calc R . .
C4 C 0.63132(17) 0.36971(10) 0.51586(13) 0.0347(4) Uani 1 1 d . . .
H4 H 0.6669 0.3865 0.6010 0.042 Uiso 1 1 calc R . .
C5 C 0.59516(15) 0.43306(9) 0.42641(12) 0.0288(3) Uani 1 1 d . . .
H5 H 0.6053 0.4946 0.4490 0.035 Uiso 1 1 calc R . .
C6 C 0.52647(14) 0.31898(8) 0.26454(13) 0.0266(3) Uani 1 1 d . . .
C7 C 0.46883(16) 0.31868(9) 0.13714(13) 0.0310(3) Uani 1 1 d . . .
H7 H 0.4474 0.2672 0.0852 0.037 Uiso 1 1 calc R . .
C8 C 0.44721(16) 0.40823(9) 0.09744(13) 0.0310(3) Uani 1 1 d . . .
H8 H 0.4069 0.4273 0.0133 0.037 Uiso 1 1 calc R . .
C9 C 0.49336(14) 0.46383(9) 0.19885(12) 0.0261(3) Uani 1 1 d . . .
C10 C 0.49108(15) 0.56229(9) 0.20628(12) 0.0259(3) Uani 1 1 d . . .
C11 C 0.62060(16) 0.61252(9) 0.26893(14) 0.0327(3) Uani 1 1 d . . .
H11 H 0.7144 0.5828 0.3112 0.039 Uiso 1 1 calc R . .
C12 C 0.61493(16) 0.70512(9) 0.27064(14) 0.0328(3) Uani 1 1 d . . .
H12 H 0.7053 0.7375 0.3143 0.039 Uiso 1 1 calc R . .
C13 C 0.48050(14) 0.75220(9) 0.21021(12) 0.0258(3) Uani 1 1 d . . .
C14 C 0.47763(15) 0.85494(9) 0.20727(12) 0.0283(3) Uani 1 1 d . . .
C15 C 0.5902(2) 0.89399(10) 0.32657(17) 0.0511(5) Uani 1 1 d . . .
H15A H 0.6950 0.8770 0.3334 0.077 Uiso 1 1 calc R . .
H15B H 0.5666 0.8707 0.3983 0.077 Uiso 1 1 calc R . .
H15C H 0.5813 0.9594 0.3246 0.077 Uiso 1 1 calc R . .
C16 C 0.5237(2) 0.88568(11) 0.09753(17) 0.0514(5) Uani 1 1 d . . .
H16A H 0.4486 0.8638 0.0200 0.077 Uiso 1 1 calc R . .
H16B H 0.6252 0.8617 0.1059 0.077 Uiso 1 1 calc R . .
H16C H 0.5268 0.9513 0.0961 0.077 Uiso 1 1 calc R . .
C17 C 0.31883(18) 0.89182(10) 0.19209(18) 0.0462(4) Uani 1 1 d . . .
H17A H 0.3227 0.9574 0.1948 0.069 Uiso 1 1 calc R . .
H17B H 0.2855 0.8695 0.2596 0.069 Uiso 1 1 calc R . .
H17C H 0.2461 0.8723 0.1121 0.069 Uiso 1 1 calc R . .
C18 C 0.35199(16) 0.70134(9) 0.14747(13) 0.0335(3) Uani 1 1 d . . .
H18 H 0.2584 0.7310 0.1045 0.040 Uiso 1 1 calc R . .
C19 C 0.35678(16) 0.60869(9) 0.14588(13) 0.0326(3) Uani 1 1 d . . .
H19 H 0.2664 0.5762 0.1026 0.039 Uiso 1 1 calc R . .
N1 N 0.54383(12) 0.40948(7) 0.30297(10) 0.0244(3) Uani 1 1 d . . .
O1 O 0.50238(14) 0.12522(7) 0.22730(12) 0.0528(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 1.205(2) . ?
C1 C2 1.466(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.365(2) . ?
C2 C6 1.4287(19) . ?
C3 C4 1.413(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.3495(19) . ?
C4 H4 0.9500 . ?
C5 N1 1.3738(17) . ?
C5 H5 0.9500 . ?
C6 C7 1.371(2) . ?
C6 N1 1.4133(16) . ?
C7 C8 1.4045(19) . ?
C7 H7 0.9500 . ?
C8 C9 1.3715(19) . ?
C8 H8 0.9500 . ?
C9 N1 1.3849(16) . ?
C9 C10 1.4733(18) . ?
C10 C19 1.3879(19) . ?
C10 C11 1.3917(19) . ?
C11 C12 1.3840(19) . ?
C11 H11 0.9500 . ?
C12 C13 1.3940(19) . ?
C12 H12 0.9500 . ?
C13 C18 1.3906(19) . ?
C13 C14 1.5345(18) . ?
C14 C16 1.524(2) . ?
C14 C17 1.5242(19) . ?
C14 C15 1.526(2) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.3844(19) . ?
C18 H18 0.9500 . ?
C19 H19 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 126.15(15) . . ?
O1 C1 H1 116.9 . . ?
C2 C1 H1 116.9 . . ?
C3 C2 C6 120.05(12) . . ?
C3 C2 C1 119.00(13) . . ?
C6 C2 C1 120.93(13) . . ?
C2 C3 C4 120.97(13) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 119.70(13) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 N1 120.65(12) . . ?
C4 C5 H5 119.7 . . ?
N1 C5 H5 119.7 . . ?
C7 C6 N1 107.20(11) . . ?
C7 C6 C2 135.99(12) . . ?
N1 C6 C2 116.77(12) . . ?
C6 C7 C8 107.58(12) . . ?
C6 C7 H7 126.2 . . ?
C8 C7 H7 126.2 . . ?
C9 C8 C7 109.47(12) . . ?
C9 C8 H8 125.3 . . ?
C7 C8 H8 125.3 . . ?
C8 C9 N1 106.87(11) . . ?
C8 C9 C10 130.26(12) . . ?
N1 C9 C10 122.86(11) . . ?
C19 C10 C11 117.40(12) . . ?
C19 C10 C9 119.82(12) . . ?
C11 C10 C9 122.75(12) . . ?
C12 C11 C10 121.03(12) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C13 121.91(12) . . ?
C11 C12 H12 119.0 . . ?
C13 C12 H12 119.0 . . ?
C18 C13 C12 116.56(12) . . ?
C18 C13 C14 121.95(11) . . ?
C12 C13 C14 121.40(11) . . ?
C16 C14 C17 108.82(13) . . ?
C16 C14 C15 108.88(14) . . ?
C17 C14 C15 107.90(13) . . ?
C16 C14 C13 108.16(11) . . ?
C17 C14 C13 111.88(11) . . ?
C15 C14 C13 111.15(11) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C13 121.79(13) . . ?
C19 C18 H18 119.1 . . ?
C13 C18 H18 119.1 . . ?
C18 C19 C10 121.31(13) . . ?
C18 C19 H19 119.3 . . ?
C10 C19 H19 119.3 . . ?
C5 N1 C9 129.18(11) . . ?
C5 N1 C6 121.85(11) . . ?
C9 N1 C6 108.86(11) . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        25.06
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.032
