# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_ch16057
_database_code_depnum_ccdc_archive 'CCDC 1945018'
loop_
_audit_author_name
_audit_author_address
'Ting-Shen Kuo'
;National TAiwan Normal University
Taiwan
;
_audit_update_record             
;
2019-08-02 deposited with the CCDC.	2020-01-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H16 Br N O2'
_chemical_formula_sum            'C21 H16 Br N O2'
_chemical_formula_weight         394.26

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'
Br Br -0.2901 2.4595 '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                   8.9170(9)
_cell_length_b                   10.2917(9)
_cell_length_c                   11.1275(8)
_cell_angle_alpha                73.236(5)
_cell_angle_beta                 67.643(5)
_cell_angle_gamma                65.564(6)
_cell_volume                     849.34(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    3457
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      25.06

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             400
_exptl_absorpt_coefficient_mu    2.434
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3326
_exptl_absorpt_correction_T_max  0.5813
_exptl_absorpt_process_details   ?

_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  'Bruker APEX2'
_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            6699
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_sigmaI/netI    0.0492
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.20
_diffrn_reflns_theta_max         25.07
_reflns_number_total             2972
_reflns_number_gt                2478
_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)+(0.0664P)²+0.0000P] 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         2972
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0345
_refine_ls_wR_factor_ref         0.1128
_refine_ls_wR_factor_gt          0.0986
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_restrained_S_all      1.113
_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 0.2193(4) 0.1737(3) 0.6565(3) 0.0282(7) Uani 1 1 d . . .
C2 C 0.2885(4) 0.0589(4) 0.5879(3) 0.0376(9) Uani 1 1 d . . .
H2 H 0.3206 0.0761 0.4945 0.045 Uiso 1 1 calc R . .
C3 C 0.3109(4) -0.0787(4) 0.6535(4) 0.0432(10) Uani 1 1 d . . .
H3 H 0.3572 -0.1568 0.6058 0.052 Uiso 1 1 calc R . .
C4 C 0.2668(4) -0.1045(4) 0.7880(4) 0.0390(9) Uani 1 1 d . . .
H4 H 0.2845 -0.2007 0.8334 0.047 Uiso 1 1 calc R . .
C5 C 0.1963(4) 0.0093(3) 0.8580(3) 0.0299(7) Uani 1 1 d . . .
H5 H 0.1648 -0.0099 0.9513 0.036 Uiso 1 1 calc R . .
C6 C 0.1707(4) 0.1515(3) 0.7942(3) 0.0236(7) Uani 1 1 d . . .
C7 C 0.0897(4) 0.2733(3) 0.8763(3) 0.0240(7) Uani 1 1 d . . .
C8 C -0.0633(4) 0.3990(3) 0.8453(3) 0.0234(7) Uani 1 1 d . . .
C9 C -0.2160(4) 0.3990(4) 0.8416(3) 0.0333(8) Uani 1 1 d . . .
H9 H -0.2359 0.3110 0.8564 0.040 Uiso 1 1 calc R . .
C10 C -0.3394(4) 0.5309(4) 0.8158(3) 0.0376(9) Uani 1 1 d . . .
H10 H -0.4463 0.5337 0.8139 0.045 Uiso 1 1 calc R . .
C11 C -0.3090(5) 0.6593(4) 0.7925(3) 0.0374(9) Uani 1 1 d . . .
H11 H -0.3949 0.7485 0.7738 0.045 Uiso 1 1 calc R . .
C12 C -0.1560(4) 0.6590(3) 0.7961(3) 0.0291(7) Uani 1 1 d . . .
H12 H -0.1350 0.7466 0.7801 0.035 Uiso 1 1 calc R . .
C13 C -0.0348(4) 0.5274(3) 0.8236(3) 0.0228(7) Uani 1 1 d . . .
C14 C 0.1372(4) 0.4942(3) 0.8352(3) 0.0226(7) Uani 1 1 d . . .
C15 C 0.3713(4) 0.2751(4) 0.8884(3) 0.0268(7) Uani 1 1 d . . .
H15A H 0.3625 0.1867 0.9519 0.032 Uiso 1 1 calc R . .
H15B H 0.3824 0.3389 0.9338 0.032 Uiso 1 1 calc R . .
C16 C 0.5354(4) 0.2325(3) 0.7747(3) 0.0239(7) Uani 1 1 d . . .
C17 C 0.5585(4) 0.3225(3) 0.6561(3) 0.0291(7) Uani 1 1 d . . .
H17 H 0.4666 0.4084 0.6408 0.035 Uiso 1 1 calc R . .
C18 C 0.7172(5) 0.2875(4) 0.5581(3) 0.0372(8) Uani 1 1 d . . .
H18 H 0.7327 0.3492 0.4758 0.045 Uiso 1 1 calc R . .
C19 C 0.8507(5) 0.1640(4) 0.5808(4) 0.0414(9) Uani 1 1 d . . .
H19 H 0.9590 0.1406 0.5145 0.050 Uiso 1 1 calc R . .
C20 C 0.8270(4) 0.0747(4) 0.6992(4) 0.0414(9) Uani 1 1 d . . .
H20 H 0.9195 -0.0104 0.7150 0.050 Uiso 1 1 calc R . .
C21 C 0.6701(4) 0.1072(3) 0.7957(3) 0.0343(8) Uani 1 1 d . . .
H21 H 0.6544 0.0436 0.8768 0.041 Uiso 1 1 calc R . .
N1 N 0.2113(3) 0.3483(3) 0.8535(2) 0.0213(5) Uani 1 1 d . . .
O1 O 0.0478(3) 0.2093(2) 1.00821(18) 0.0272(5) Uani 1 1 d . . .
H1' H -0.0381 0.2767 1.0565 0.033 Uiso 1 1 d R . .
O2 O 0.2026(3) 0.5807(2) 0.8306(2) 0.0302(5) Uani 1 1 d . . .
Br1 Br 0.19017(5) 0.35960(4) 0.55313(3) 0.04041(17) 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 1.385(4) . ?
C1 C6 1.401(4) . ?
C1 Br1 1.897(3) . ?
C2 C3 1.363(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.369(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.395(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.528(4) . ?
C7 O1 1.399(3) . ?
C7 N1 1.485(4) . ?
C7 C8 1.515(4) . ?
C8 C9 1.378(4) . ?
C8 C13 1.385(4) . ?
C9 C10 1.384(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.390(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.378(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.377(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.475(4) . ?
C14 O2 1.231(3) . ?
C14 N1 1.356(4) . ?
C15 N1 1.455(4) . ?
C15 C16 1.521(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.373(4) . ?
C16 C21 1.385(4) . ?
C17 C18 1.397(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.374(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.370(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.378(5) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
O1 H1' 0.9049 . ?

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 121.1(3) . . ?
C2 C1 Br1 116.0(3) . . ?
C6 C1 Br1 122.9(2) . . ?
C3 C2 C1 120.4(3) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 120.1(3) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 120.1(3) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 121.3(3) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C1 116.9(3) . . ?
C5 C6 C7 119.2(3) . . ?
C1 C6 C7 123.9(3) . . ?
O1 C7 N1 109.2(2) . . ?
O1 C7 C8 111.5(2) . . ?
N1 C7 C8 101.0(2) . . ?
O1 C7 C6 106.7(2) . . ?
N1 C7 C6 111.8(2) . . ?
C8 C7 C6 116.5(2) . . ?
C9 C8 C13 120.8(3) . . ?
C9 C8 C7 129.5(3) . . ?
C13 C8 C7 109.7(3) . . ?
C8 C9 C10 118.0(3) . . ?
C8 C9 H9 121.0 . . ?
C10 C9 H9 121.0 . . ?
C9 C10 C11 120.9(3) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C12 C11 C10 121.0(3) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C13 C12 C11 117.8(3) . . ?
C13 C12 H12 121.1 . . ?
C11 C12 H12 121.1 . . ?
C12 C13 C8 121.6(3) . . ?
C12 C13 C14 129.8(3) . . ?
C8 C13 C14 108.7(3) . . ?
O2 C14 N1 125.7(3) . . ?
O2 C14 C13 127.4(3) . . ?
N1 C14 C13 106.9(2) . . ?
N1 C15 C16 115.9(2) . . ?
N1 C15 H15A 108.3 . . ?
C16 C15 H15A 108.3 . . ?
N1 C15 H15B 108.3 . . ?
C16 C15 H15B 108.3 . . ?
H15A C15 H15B 107.4 . . ?
C17 C16 C21 119.5(3) . . ?
C17 C16 C15 121.2(3) . . ?
C21 C16 C15 119.0(3) . . ?
C16 C17 C18 120.0(3) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C19 C18 C17 120.0(3) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C20 C19 C18 119.7(3) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C19 C20 C21 120.6(3) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C20 C21 C16 120.2(3) . . ?
C20 C21 H21 119.9 . . ?
C16 C21 H21 119.9 . . ?
C14 N1 C15 122.4(3) . . ?
C14 N1 C7 112.8(2) . . ?
C15 N1 C7 122.1(2) . . ?
C7 O1 H1' 108.8 . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        25.07
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.499
_refine_diff_density_rms         0.121
####################################################################### 
# 
# 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_a15070
_database_code_depnum_ccdc_archive 'CCDC 1945020'
loop_
_audit_author_name
_audit_author_address
'Ting-Shen Kuo'
;National TAiwan Normal University
Taiwan
;
_audit_update_record             
;
2019-08-02 deposited with the CCDC.	2020-01-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H13 Br Cl N O2'
_chemical_formula_sum            'C20 H13 Br Cl N O2'
_chemical_formula_weight         414.67

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'

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

_cell_length_a                   25.659(3)
_cell_length_b                   8.0570(7)
_cell_length_c                   18.4834(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.978(4)
_cell_angle_gamma                90.00
_cell_volume                     3463.7(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    2660
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      23.87

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1664
_exptl_absorpt_coefficient_mu    2.541
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4150
_exptl_absorpt_correction_T_max  0.7018
_exptl_absorpt_process_details   ?

_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  'Bruker APEX2'
_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            9036
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_sigmaI/netI    0.0545
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.32
_diffrn_reflns_theta_max         25.11
_reflns_number_total             3052
_reflns_number_gt                2289
_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)+(0.0482P)²+0.0000P] 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         3052
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.0965
_refine_ls_wR_factor_gt          0.0874
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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
Br1 Br 0.056703(17) 0.37676(4) 0.97523(2) 0.04404(16) Uani 1 1 d . . .
C1 C 0.03781(15) 0.1637(4) 0.92542(18) 0.0287(8) Uani 1 1 d . . .
C2 C -0.01762(16) 0.1081(4) 0.9083(2) 0.0409(9) Uani 1 1 d . . .
H2 H -0.0430 0.1742 0.9215 0.049 Uiso 1 1 calc R . .
C3 C -0.03518(17) -0.0437(5) 0.8719(2) 0.0521(11) Uani 1 1 d . . .
H3 H -0.0728 -0.0831 0.8604 0.063 Uiso 1 1 calc R . .
C4 C 0.00144(18) -0.1383(5) 0.8523(2) 0.0503(11) Uani 1 1 d . . .
H4 H -0.0108 -0.2427 0.8268 0.060 Uiso 1 1 calc R . .
C5 C 0.05600(16) -0.0814(4) 0.8695(2) 0.0383(9) Uani 1 1 d . . .
H5 H 0.0808 -0.1483 0.8554 0.046 Uiso 1 1 calc R . .
C6 C 0.07629(14) 0.0702(4) 0.90691(18) 0.0244(7) Uani 1 1 d . . .
C7 C 0.13714(14) 0.1259(3) 0.92372(17) 0.0210(7) Uani 1 1 d . . .
C8 C 0.17831(13) 0.0544(4) 1.07312(17) 0.0206(7) Uani 1 1 d . . .
C9 C 0.17160(15) -0.1156(3) 1.0590(2) 0.0297(8) Uani 1 1 d . . .
H9 H 0.1622 -0.1578 1.0070 0.036 Uiso 1 1 calc R . .
C10 C 0.17859(15) -0.2231(4) 1.1207(2) 0.0350(9) Uani 1 1 d . . .
H10 H 0.1736 -0.3390 1.1106 0.042 Uiso 1 1 calc R . .
C11 C 0.19264(15) -0.1645(4) 1.1969(2) 0.0353(9) Uani 1 1 d . . .
H11 H 0.1981 -0.2392 1.2392 0.042 Uiso 1 1 calc R . .
C12 C 0.19860(15) 0.0047(4) 1.2105(2) 0.0358(9) Uani 1 1 d . . .
H12 H 0.2079 0.0459 1.2626 0.043 Uiso 1 1 calc R . .
C13 C 0.19122(14) 0.1152(4) 1.14949(19) 0.0276(8) Uani 1 1 d . . .
H13 H 0.1949 0.2312 1.1596 0.033 Uiso 1 1 calc R . .
C14 C 0.19795(13) 0.3206(4) 1.02002(18) 0.0212(7) Uani 1 1 d . . .
C15 C 0.17713(14) 0.3968(3) 0.93965(18) 0.0224(7) Uani 1 1 d . . .
C16 C 0.18957(15) 0.5503(4) 0.9184(2) 0.0286(8) Uani 1 1 d . . .
H16 H 0.2144 0.6252 0.9575 0.034 Uiso 1 1 calc R . .
C17 C 0.16478(17) 0.5924(4) 0.8383(2) 0.0349(9) Uani 1 1 d . . .
H17 H 0.1725 0.6973 0.8215 0.042 Uiso 1 1 calc R . .
C18 C 0.12850(15) 0.4802(4) 0.78256(19) 0.0278(8) Uani 1 1 d . . .
C19 C 0.11522(14) 0.3258(4) 0.80404(18) 0.0260(8) Uani 1 1 d . . .
H19 H 0.0901 0.2507 0.7655 0.031 Uiso 1 1 calc R . .
C20 C 0.14043(13) 0.2878(3) 0.88393(18) 0.0213(7) Uani 1 1 d . . .
Cl1 Cl 0.09979(5) 0.53407(11) 0.68206(5) 0.0444(3) Uani 1 1 d . . .
N1 N 0.17226(11) 0.1668(3) 1.00989(14) 0.0199(6) Uani 1 1 d . . .
O1 O 0.16340(9) -0.0023(2) 0.89897(12) 0.0247(5) Uani 1 1 d . . .
H1' H 0.1985 0.0349 0.9040 0.030 Uiso 1 1 d R . .
O2 O 0.23175(10) 0.3812(2) 1.08357(13) 0.0277(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
Br1 C1 1.911(3) . ?
C1 C6 1.395(4) . ?
C1 C2 1.394(5) . ?
C2 C3 1.376(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.373(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.376(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.392(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.525(4) . ?
C7 O1 1.410(3) . ?
C7 N1 1.498(4) . ?
C7 C20 1.517(4) . ?
C8 C9 1.392(4) . ?
C8 C13 1.396(4) . ?
C8 N1 1.434(4) . ?
C9 C10 1.383(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.380(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.383(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.385(4) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 O2 1.229(4) . ?
C14 N1 1.379(4) . ?
C14 C15 1.483(4) . ?
C15 C16 1.375(4) . ?
C15 C20 1.378(4) . ?
C16 C17 1.385(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.391(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.391(4) . ?
C18 Cl1 1.740(3) . ?
C19 C20 1.373(4) . ?
C19 H19 0.9500 . ?
O1 H1' 0.9163 . ?

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
C6 C1 C2 122.0(3) . . ?
C6 C1 Br1 122.8(2) . . ?
C2 C1 Br1 115.2(3) . . ?
C3 C2 C1 119.3(4) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C4 C3 C2 120.2(4) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 119.8(4) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 122.5(4) . . ?
C4 C5 H5 118.7 . . ?
C6 C5 H5 118.7 . . ?
C5 C6 C1 116.2(3) . . ?
C5 C6 C7 119.7(3) . . ?
C1 C6 C7 124.1(3) . . ?
O1 C7 N1 110.5(2) . . ?
O1 C7 C20 109.9(2) . . ?
N1 C7 C20 101.2(2) . . ?
O1 C7 C6 107.9(2) . . ?
N1 C7 C6 112.7(2) . . ?
C20 C7 C6 114.6(3) . . ?
C9 C8 C13 119.5(3) . . ?
C9 C8 N1 120.4(3) . . ?
C13 C8 N1 120.0(3) . . ?
C10 C9 C8 119.9(3) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C11 C10 C9 120.9(3) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C12 119.0(3) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
C11 C12 C13 121.3(3) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C12 C13 C8 119.3(3) . . ?
C12 C13 H13 120.3 . . ?
C8 C13 H13 120.3 . . ?
O2 C14 N1 126.2(3) . . ?
O2 C14 C15 127.1(3) . . ?
N1 C14 C15 106.7(3) . . ?
C16 C15 C20 121.8(3) . . ?
C16 C15 C14 129.0(3) . . ?
C20 C15 C14 109.1(2) . . ?
C15 C16 C17 117.9(3) . . ?
C15 C16 H16 121.0 . . ?
C17 C16 H16 121.0 . . ?
C16 C17 C18 119.6(3) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C17 C18 C19 122.5(3) . . ?
C17 C18 Cl1 118.5(2) . . ?
C19 C18 Cl1 118.9(2) . . ?
C20 C19 C18 116.5(3) . . ?
C20 C19 H19 121.8 . . ?
C18 C19 H19 121.8 . . ?
C19 C20 C15 121.6(3) . . ?
C19 C20 C7 128.0(3) . . ?
C15 C20 C7 110.3(3) . . ?
C14 N1 C8 125.1(3) . . ?
C14 N1 C7 112.4(2) . . ?
C8 N1 C7 122.5(2) . . ?
C7 O1 H1' 108.2 . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.11
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.686
_refine_diff_density_rms         0.096
####################################################################### 
# 
# 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_ch15498
_database_code_depnum_ccdc_archive 'CCDC 1945019'
loop_
_audit_author_name
_audit_author_address
'Ting-Shen Kuo'
;National TAiwan Normal University
Taiwan
;
_audit_update_record             
;
2019-08-02 deposited with the CCDC.	2020-01-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H17 N O2'
_chemical_formula_sum            'C21 H17 N O2'
_chemical_formula_weight         315.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   9.7191(17)
_cell_length_b                   10.2939(19)
_cell_length_c                   10.630(2)
_cell_angle_alpha                61.607(6)
_cell_angle_beta                 63.029(5)
_cell_angle_gamma                87.604(6)
_cell_volume                     813.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    1654
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      23.57

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             332
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9748
_exptl_absorpt_correction_T_max  0.9950
_exptl_absorpt_process_details   ?

_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  'Bruker APEX2'
_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            7092
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_sigmaI/netI    0.0648
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.38
_diffrn_reflns_theta_max         25.07
_reflns_number_total             2860
_reflns_number_gt                1878
_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)+(0.0752P)²+0.0556P] 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         2860
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0879
_refine_ls_R_factor_gt           0.0500
_refine_ls_wR_factor_ref         0.1546
_refine_ls_wR_factor_gt          0.1208
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_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 1.0432(3) 1.0576(3) 0.1102(3) 0.0255(6) Uani 1 1 d . . .
C2 C 1.1340(3) 0.9372(3) 0.1262(3) 0.0253(6) Uani 1 1 d . . .
C3 C 1.2941(3) 0.9483(3) 0.0365(3) 0.0340(7) Uani 1 1 d . . .
H3 H 1.3651 1.0440 -0.0460 0.041 Uiso 1 1 calc R . .
C4 C 1.3473(3) 0.8157(4) 0.0707(4) 0.0402(7) Uani 1 1 d . . .
H4 H 1.4570 0.8199 0.0119 0.048 Uiso 1 1 calc R . .
C5 C 1.2421(3) 0.6758(3) 0.1904(4) 0.0407(7) Uani 1 1 d . . .
H5 H 1.2808 0.5858 0.2100 0.049 Uiso 1 1 calc R . .
C6 C 1.0827(3) 0.6656(3) 0.2810(3) 0.0338(7) Uani 1 1 d . . .
H6 H 1.0113 0.5700 0.3632 0.041 Uiso 1 1 calc R . .
C7 C 1.0298(3) 0.7985(3) 0.2488(3) 0.0248(6) Uani 1 1 d . . .
C8 C 0.8634(3) 0.8216(3) 0.3292(3) 0.0245(6) Uani 1 1 d . . .
C9 C 0.7983(3) 0.7697(3) 0.5099(3) 0.0251(6) Uani 1 1 d . . .
C10 C 0.8983(3) 0.7927(3) 0.5610(3) 0.0347(7) Uani 1 1 d . . .
H10 H 1.0076 0.8371 0.4840 0.042 Uiso 1 1 calc R . .
C11 C 0.8413(3) 0.7522(3) 0.7223(3) 0.0392(7) Uani 1 1 d . . .
H11 H 0.9113 0.7661 0.7568 0.047 Uiso 1 1 calc R . .
C12 C 0.6821(3) 0.6913(3) 0.8336(3) 0.0383(7) Uani 1 1 d . . .
H12 H 0.6420 0.6646 0.9445 0.046 Uiso 1 1 calc R . .
C13 C 0.5818(3) 0.6693(3) 0.7839(3) 0.0355(7) Uani 1 1 d . . .
H13 H 0.4721 0.6277 0.8608 0.043 Uiso 1 1 calc R . .
C14 C 0.6390(3) 0.7074(3) 0.6224(3) 0.0283(6) Uani 1 1 d . . .
H14 H 0.5691 0.6907 0.5891 0.034 Uiso 1 1 calc R . .
C15 C 0.7625(3) 1.0700(3) 0.2465(3) 0.0301(6) Uani 1 1 d . . .
H15A H 0.6611 0.9939 0.3184 0.036 Uiso 1 1 calc R . .
H15B H 0.7719 1.1326 0.1366 0.036 Uiso 1 1 calc R . .
C16 C 0.7554(2) 1.1713(3) 0.3152(3) 0.0257(6) Uani 1 1 d . . .
C17 C 0.6927(3) 1.1128(3) 0.4822(3) 0.0310(6) Uani 1 1 d . . .
H17 H 0.6599 1.0063 0.5555 0.037 Uiso 1 1 calc R . .
C18 C 0.6775(3) 1.2082(3) 0.5426(4) 0.0391(7) Uani 1 1 d . . .
H18 H 0.6339 1.1667 0.6574 0.047 Uiso 1 1 calc R . .
C19 C 0.7248(3) 1.3626(3) 0.4386(4) 0.0443(8) Uani 1 1 d . . .
H19 H 0.7133 1.4278 0.4811 0.053 Uiso 1 1 calc R . .
C20 C 0.7891(3) 1.4219(3) 0.2715(4) 0.0440(8) Uani 1 1 d . . .
H20 H 0.8229 1.5284 0.1983 0.053 Uiso 1 1 calc R . .
C21 C 0.8043(3) 1.3267(3) 0.2112(3) 0.0365(7) Uani 1 1 d . . .
H21 H 0.8491 1.3684 0.0961 0.044 Uiso 1 1 calc R . .
N1 N 0.8919(2) 0.9902(2) 0.2308(2) 0.0246(5) Uani 1 1 d . . .
O1 O 1.09267(19) 1.1937(2) 0.0037(2) 0.0343(5) Uani 1 1 d . . .
O2 O 0.75403(17) 0.75215(18) 0.3159(2) 0.0310(5) Uani 1 1 d . . .
H2' H 0.8063 0.7730 0.2073 0.037 Uiso 1 1 d R . .


_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 1.237(3) . ?
C1 N1 1.348(3) . ?
C1 C2 1.479(3) . ?
C2 C3 1.381(3) . ?
C2 C7 1.385(3) . ?
C3 C4 1.380(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.392(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.380(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.381(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.520(3) . ?
C8 O2 1.399(3) . ?
C8 N1 1.494(3) . ?
C8 C9 1.524(3) . ?
C9 C14 1.383(3) . ?
C9 C10 1.385(3) . ?
C10 C11 1.377(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.379(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.371(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.387(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 N1 1.461(3) . ?
C15 C16 1.517(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C21 1.383(3) . ?
C16 C17 1.384(3) . ?
C17 C18 1.378(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.374(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.383(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.376(4) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
O2 H2' 0.9370 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 N1 125.5(2) . . ?
O1 C1 C2 127.5(2) . . ?
N1 C1 C2 107.0(2) . . ?
C3 C2 C7 121.7(2) . . ?
C3 C2 C1 129.6(2) . . ?
C7 C2 C1 108.68(19) . . ?
C4 C3 C2 117.8(2) . . ?
C4 C3 H3 121.1 . . ?
C2 C3 H3 121.1 . . ?
C3 C4 C5 120.7(2) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 121.2(3) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C7 118.0(3) . . ?
C5 C6 H6 121.0 . . ?
C7 C6 H6 121.0 . . ?
C6 C7 C2 120.6(2) . . ?
C6 C7 C8 129.5(2) . . ?
C2 C7 C8 109.9(2) . . ?
O2 C8 N1 110.92(19) . . ?
O2 C8 C7 113.54(19) . . ?
N1 C8 C7 100.61(17) . . ?
O2 C8 C9 108.50(17) . . ?
N1 C8 C9 109.84(19) . . ?
C7 C8 C9 113.23(19) . . ?
C14 C9 C10 119.2(2) . . ?
C14 C9 C8 121.1(2) . . ?
C10 C9 C8 119.6(2) . . ?
C11 C10 C9 120.8(2) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 119.8(3) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C13 C12 C11 119.9(3) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 120.5(2) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C9 C14 C13 119.8(2) . . ?
C9 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
N1 C15 C16 115.5(2) . . ?
N1 C15 H15A 108.4 . . ?
C16 C15 H15A 108.4 . . ?
N1 C15 H15B 108.4 . . ?
C16 C15 H15B 108.4 . . ?
H15A C15 H15B 107.5 . . ?
C21 C16 C17 118.5(2) . . ?
C21 C16 C15 119.8(2) . . ?
C17 C16 C15 121.6(2) . . ?
C18 C17 C16 120.4(3) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C19 C18 C17 120.8(3) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C18 C19 C20 119.2(3) . . ?
C18 C19 H19 120.4 . . ?
C20 C19 H19 120.4 . . ?
C21 C20 C19 120.0(3) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C16 121.1(3) . . ?
C20 C21 H21 119.5 . . ?
C16 C21 H21 119.5 . . ?
C1 N1 C15 123.3(2) . . ?
C1 N1 C8 113.55(18) . . ?
C15 N1 C8 122.31(18) . . ?
C8 O2 H2' 105.3 . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        25.07
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.059
