# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_d24546
_database_code_depnum_ccdc_archive 'CCDC 2334143'
loop_
_audit_author_name
_audit_author_address
'Suresh Sundaram'
;National Taiwan Normal University
Taiwan
;
_audit_update_record             
;
2024-02-21 deposited with the CCDC.	2024-08-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H12 Br0 Cl N O'
_chemical_formula_sum            'C15 H12 Br0 Cl N O'
_chemical_formula_weight         257.71

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P c a 21'

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

_cell_length_a                   20.4024(11)
_cell_length_b                   8.0914(4)
_cell_length_c                   16.3490(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2699.0(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    5566
_cell_measurement_theta_min      2.353
_cell_measurement_theta_max      24.869

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1072
_exptl_absorpt_coefficient_mu    0.270
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8725
_exptl_absorpt_correction_T_max  0.9234
_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       'phi scan & omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19163
_diffrn_reflns_av_R_equivalents  0.0842
_diffrn_reflns_av_sigmaI/netI    0.0770
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.00
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4314
_reflns_number_gt                3401
_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)+(0.0592P)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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(7)
_refine_ls_number_reflns         4314
_refine_ls_number_parameters     325
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.1140
_refine_ls_wR_factor_gt          0.1049
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.004
_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 0.58996(14) 0.1700(4) 0.56694(19) 0.0316(7) Uani 1 1 d . . .
C2 C 0.60281(15) 0.0542(4) 0.63226(19) 0.0290(7) Uani 1 1 d . . .
C3 C 0.55187(18) 0.0306(4) 0.6966(2) 0.0341(8) Uani 1 1 d . . .
C4 C 0.53263(17) -0.1299(5) 0.7165(3) 0.0469(10) Uani 1 1 d . . .
H4 H 0.5527 -0.2218 0.6904 0.056 Uiso 1 1 calc R . .
C5 C 0.4838(2) -0.1548(5) 0.7747(3) 0.0598(12) Uani 1 1 d . . .
H5 H 0.4693 -0.2638 0.7866 0.072 Uiso 1 1 calc R . .
C6 C 0.4563(2) -0.0219(7) 0.8152(3) 0.0667(14) Uani 1 1 d . . .
H6 H 0.4229 -0.0396 0.8547 0.080 Uiso 1 1 calc R . .
C7 C 0.4769(2) 0.1345(6) 0.7984(2) 0.0578(11) Uani 1 1 d . . .
H7 H 0.4589 0.2251 0.8278 0.069 Uiso 1 1 calc R . .
C8 C 0.52403(18) 0.1626(5) 0.7389(2) 0.0440(9) Uani 1 1 d . . .
H8 H 0.5374 0.2725 0.7269 0.053 Uiso 1 1 calc R . .
C9 C 0.53037(14) 0.2412(3) 0.5538(2) 0.0319(7) Uani 1 1 d . . .
H9 H 0.4965 0.2111 0.5907 0.038 Uiso 1 1 calc R . .
C10 C 0.45226(13) 0.4254(3) 0.4897(2) 0.0340(7) Uani 1 1 d . . .
C11 C 0.41090(17) 0.4390(4) 0.5553(2) 0.0481(9) Uani 1 1 d . . .
H11 H 0.4239 0.3956 0.6068 0.058 Uiso 1 1 calc R . .
C12 C 0.3505(2) 0.5149(4) 0.5478(4) 0.0587(14) Uani 1 1 d . . .
H12 H 0.3220 0.5228 0.5936 0.070 Uiso 1 1 calc R . .
C13 C 0.33188(17) 0.5805(4) 0.4716(3) 0.0544(11) Uani 1 1 d . . .
H13 H 0.2906 0.6332 0.4654 0.065 Uiso 1 1 calc R . .
C14 C 0.37339(18) 0.5678(4) 0.4071(3) 0.0560(10) Uani 1 1 d . . .
H14 H 0.3608 0.6122 0.3557 0.067 Uiso 1 1 calc R . .
C15 C 0.4338(2) 0.4914(4) 0.4148(3) 0.0441(10) Uani 1 1 d . . .
H15 H 0.4624 0.4841 0.3691 0.053 Uiso 1 1 calc R . .
C16 C 0.66133(14) 0.6658(3) 0.42879(18) 0.0300(7) Uani 1 1 d . . .
C17 C 0.64846(15) 0.5485(4) 0.36510(19) 0.0294(7) Uani 1 1 d . . .
C18 C 0.70077(19) 0.5173(3) 0.3021(2) 0.0318(8) Uani 1 1 d . . .
C19 C 0.71561(16) 0.3541(4) 0.2825(2) 0.0388(9) Uani 1 1 d . . .
H19 H 0.6922 0.2669 0.3082 0.047 Uiso 1 1 calc R . .
C20 C 0.76396(19) 0.3173(5) 0.2263(3) 0.0518(11) Uani 1 1 d . . .
H20 H 0.7741 0.2054 0.2139 0.062 Uiso 1 1 calc R . .
C21 C 0.7974(2) 0.4432(6) 0.1883(3) 0.0551(11) Uani 1 1 d . . .
H21 H 0.8310 0.4181 0.1501 0.066 Uiso 1 1 calc R . .
C22 C 0.78242(17) 0.6069(5) 0.2055(2) 0.0487(9) Uani 1 1 d . . .
H22 H 0.8052 0.6940 0.1790 0.058 Uiso 1 1 calc R . .
C23 C 0.73407(17) 0.6412(4) 0.2616(2) 0.0380(8) Uani 1 1 d . . .
H23 H 0.7233 0.7532 0.2728 0.046 Uiso 1 1 calc R . .
C24 C 0.72152(14) 0.7337(3) 0.44435(19) 0.0303(7) Uani 1 1 d . . .
H24 H 0.7563 0.7020 0.4091 0.036 Uiso 1 1 calc R . .
C25 C 0.79849(13) 0.9164(3) 0.51275(19) 0.0325(7) Uani 1 1 d . . .
C26 C 0.84233(17) 0.9297(4) 0.4489(2) 0.0456(8) Uani 1 1 d . . .
H26 H 0.8315 0.8885 0.3962 0.055 Uiso 1 1 calc R . .
C27 C 0.9024(2) 1.0041(4) 0.4631(4) 0.0541(13) Uani 1 1 d . . .
H27 H 0.9331 1.0107 0.4195 0.065 Uiso 1 1 calc R . .
C28 C 0.91856(17) 1.0668(4) 0.5357(3) 0.0584(12) Uani 1 1 d . . .
H28 H 0.9599 1.1183 0.5434 0.070 Uiso 1 1 calc R . .
C29 C 0.87455(17) 1.0561(4) 0.5996(3) 0.0535(10) Uani 1 1 d . . .
H29 H 0.8852 1.1021 0.6514 0.064 Uiso 1 1 calc R . .
C30 C 0.81536(19) 0.9789(4) 0.5881(3) 0.0441(10) Uani 1 1 d . . .
H30 H 0.7858 0.9684 0.6327 0.053 Uiso 1 1 calc R . .
N1 N 0.51416(11) 0.3474(3) 0.49560(17) 0.0322(6) Uani 1 1 d . . .
H1 H 0.5438 0.3710 0.4582 0.039 Uiso 1 1 calc R . .
N2 N 0.73633(10) 0.8401(3) 0.50405(16) 0.0318(6) Uani 1 1 d . . .
H2 H 0.7057 0.8641 0.5401 0.038 Uiso 1 1 calc R . .
O1 O 0.65453(12) -0.0270(3) 0.63598(16) 0.0382(6) Uani 1 1 d . . .
O2 O 0.59590(12) 0.4721(3) 0.36015(16) 0.0380(6) Uani 1 1 d . . .
Cl1 Cl 0.65391(3) 0.20934(9) 0.49958(5) 0.0401(2) Uani 1 1 d . . .
Cl2 Cl 0.59645(3) 0.71364(10) 0.49455(5) 0.0409(2) 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 C9 1.363(4) . ?
C1 C2 1.445(4) . ?
C1 Cl1 1.737(3) . ?
C2 O1 1.245(4) . ?
C2 C3 1.491(5) . ?
C3 C8 1.394(5) . ?
C3 C4 1.395(5) . ?
C4 C5 1.392(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.382(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.361(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.386(5) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 N1 1.324(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.369(5) . ?
C10 C15 1.388(5) . ?
C10 N1 1.415(3) . ?
C11 C12 1.382(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.407(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.356(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.384(5) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C24 1.369(4) . ?
C16 C17 1.433(4) . ?
C16 Cl2 1.749(3) . ?
C17 O2 1.240(3) . ?
C17 C18 1.505(5) . ?
C18 C23 1.380(5) . ?
C18 C19 1.392(4) . ?
C19 C20 1.381(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.375(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.388(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.375(5) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 N2 1.336(4) . ?
C24 H24 0.9500 . ?
C25 C30 1.375(5) . ?
C25 C26 1.378(4) . ?
C25 N2 1.418(3) . ?
C26 C27 1.385(5) . ?
C26 H26 0.9500 . ?
C27 C28 1.332(6) . ?
C27 H27 0.9500 . ?
C28 C29 1.380(6) . ?
C28 H28 0.9500 . ?
C29 C30 1.373(5) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
N1 H1 0.8800 . ?
N2 H2 0.8800 . ?

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
C9 C1 C2 123.6(3) . . ?
C9 C1 Cl1 119.5(2) . . ?
C2 C1 Cl1 116.8(2) . . ?
O1 C2 C1 122.2(3) . . ?
O1 C2 C3 119.3(3) . . ?
C1 C2 C3 118.5(3) . . ?
C8 C3 C4 118.9(4) . . ?
C8 C3 C2 122.5(3) . . ?
C4 C3 C2 118.7(3) . . ?
C5 C4 C3 119.7(4) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C6 C5 C4 120.3(4) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C7 C6 C5 120.1(4) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C8 120.6(4) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C7 C8 C3 120.3(4) . . ?
C7 C8 H8 119.8 . . ?
C3 C8 H8 119.8 . . ?
N1 C9 C1 127.7(3) . . ?
N1 C9 H9 116.2 . . ?
C1 C9 H9 116.2 . . ?
C11 C10 C15 119.5(3) . . ?
C11 C10 N1 122.2(3) . . ?
C15 C10 N1 118.3(3) . . ?
C10 C11 C12 121.1(4) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C11 C12 C13 119.1(4) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C14 C13 C12 119.4(4) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C13 C14 C15 121.3(4) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C14 C15 C10 119.6(4) . . ?
C14 C15 H15 120.2 . . ?
C10 C15 H15 120.2 . . ?
C24 C16 C17 124.4(3) . . ?
C24 C16 Cl2 118.4(2) . . ?
C17 C16 Cl2 117.0(2) . . ?
O2 C17 C16 122.4(3) . . ?
O2 C17 C18 119.0(3) . . ?
C16 C17 C18 118.6(3) . . ?
C23 C18 C19 118.2(4) . . ?
C23 C18 C17 123.8(3) . . ?
C19 C18 C17 118.1(3) . . ?
C20 C19 C18 120.8(4) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C21 C20 C19 119.7(3) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C20 C21 C22 120.4(4) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C23 C22 C21 119.1(4) . . ?
C23 C22 H22 120.5 . . ?
C21 C22 H22 120.5 . . ?
C22 C23 C18 121.7(3) . . ?
C22 C23 H23 119.1 . . ?
C18 C23 H23 119.1 . . ?
N2 C24 C16 126.7(3) . . ?
N2 C24 H24 116.7 . . ?
C16 C24 H24 116.7 . . ?
C30 C25 C26 119.2(3) . . ?
C30 C25 N2 118.3(3) . . ?
C26 C25 N2 122.6(3) . . ?
C25 C26 C27 118.8(4) . . ?
C25 C26 H26 120.6 . . ?
C27 C26 H26 120.6 . . ?
C28 C27 C26 122.3(4) . . ?
C28 C27 H27 118.9 . . ?
C26 C27 H27 118.9 . . ?
C27 C28 C29 119.3(4) . . ?
C27 C28 H28 120.4 . . ?
C29 C28 H28 120.4 . . ?
C30 C29 C28 119.8(4) . . ?
C30 C29 H29 120.1 . . ?
C28 C29 H29 120.1 . . ?
C25 C30 C29 120.6(4) . . ?
C25 C30 H30 119.7 . . ?
C29 C30 H30 119.7 . . ?
C9 N1 C10 124.1(3) . . ?
C9 N1 H1 117.9 . . ?
C10 N1 H1 117.9 . . ?
C24 N2 C25 123.8(3) . . ?
C24 N2 H2 118.1 . . ?
C25 N2 H2 118.1 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.604
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.043
####################################################################### 
# 
# 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_d25025
_database_code_depnum_ccdc_archive 'CCDC 2360356'
loop_
_audit_author_name
_audit_author_address
'Suresh Sundaram'
;National Taiwan Normal University
Taiwan
;
_audit_update_record             
;
2024-06-04 deposited with the CCDC.	2024-08-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H18 Br2 N2 O2'
_chemical_formula_sum            'C24 H18 Br2 N2 O2'
_chemical_formula_weight         526.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   32.4571(15)
_cell_length_b                   13.4666(5)
_cell_length_c                   11.2783(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.33
_cell_angle_gamma                90.00
_cell_volume                     4622.4(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    6561
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      24.98

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2096
_exptl_absorpt_coefficient_mu    3.529
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5244
_exptl_absorpt_correction_T_max  0.9015
_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 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            23074
_diffrn_reflns_av_R_equivalents  0.0642
_diffrn_reflns_av_sigmaI/netI    0.0409
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         25.07
_reflns_number_total             4072
_reflns_number_gt                3449
_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)+(0.0869P)²+20.4408P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4072
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.1038
_refine_ls_wR_factor_gt          0.0960
_refine_ls_goodness_of_fit_ref   0.685
_refine_ls_restrained_S_all      0.685
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.48789(9) 0.3563(2) 0.5165(3) 0.0345(6) Uani 1 1 d . . .
C2 C 0.46542(9) 0.4304(2) 0.5522(3) 0.0335(6) Uani 1 1 d . . .
H2 H 0.4739 0.4503 0.6382 0.040 Uiso 1 1 calc R . .
C3 C 0.43009(9) 0.4758(2) 0.4602(3) 0.0309(6) Uani 1 1 d . . .
H3 H 0.4144 0.5271 0.4837 0.037 Uiso 1 1 calc R . .
C4 C 0.41754(9) 0.4470(2) 0.3343(3) 0.0298(6) Uani 1 1 d . . .
C5 C 0.44181(10) 0.3739(2) 0.3009(3) 0.0368(7) Uani 1 1 d . . .
H5 H 0.4341 0.3551 0.2148 0.044 Uiso 1 1 calc R . .
C6 C 0.47713(10) 0.3282(2) 0.3919(3) 0.0381(7) Uani 1 1 d . . .
H6 H 0.4936 0.2783 0.3686 0.046 Uiso 1 1 calc R . .
C7 C 0.37793(9) 0.4892(2) 0.2333(3) 0.0313(6) Uani 1 1 d . . .
C8 C 0.34966(9) 0.5629(2) 0.2709(3) 0.0317(6) Uani 1 1 d . . .
H8A H 0.3666 0.6247 0.3006 0.038 Uiso 1 1 calc R . .
H8B H 0.3421 0.5353 0.3421 0.038 Uiso 1 1 calc R . .
C9 C 0.30709(9) 0.5875(2) 0.1610(3) 0.0344(6) Uani 1 1 d . . .
H9 H 0.2936 0.5224 0.1254 0.041 Uiso 1 1 calc R . .
C10 C 0.27417(9) 0.6389(2) 0.2072(3) 0.0325(6) Uani 1 1 d . . .
C11 C 0.25105(9) 0.5765(2) 0.2648(3) 0.0388(7) Uani 1 1 d . . .
C12 C 0.21735(10) 0.6170(2) 0.3158(3) 0.0366(7) Uani 1 1 d . . .
C13 C 0.22612(12) 0.6153(3) 0.4451(3) 0.0570(10) Uani 1 1 d . . .
H13 H 0.2545 0.5959 0.5001 0.068 Uiso 1 1 calc R . .
C14 C 0.19451(14) 0.6411(3) 0.4956(3) 0.0599(10) Uani 1 1 d . . .
H14 H 0.2009 0.6394 0.5845 0.072 Uiso 1 1 calc R . .
C15 C 0.15369(12) 0.6693(2) 0.4156(3) 0.0443(8) Uani 1 1 d . . .
C16 C 0.14397(11) 0.6732(3) 0.2871(3) 0.0461(8) Uani 1 1 d . . .
H16 H 0.1157 0.6936 0.2329 0.055 Uiso 1 1 calc R . .
C17 C 0.17595(10) 0.6470(3) 0.2376(3) 0.0422(7) Uani 1 1 d . . .
H17 H 0.1694 0.6497 0.1487 0.051 Uiso 1 1 calc R . .
C18 C 0.26600(9) 0.7392(2) 0.1986(3) 0.0335(6) Uani 1 1 d . . .
H18 H 0.2420 0.7592 0.2229 0.040 Uiso 1 1 calc R . .
C19 C 0.32490(10) 0.8124(2) 0.1325(3) 0.0344(6) Uani 1 1 d . . .
C20 C 0.34871(11) 0.8997(2) 0.1501(3) 0.0463(8) Uani 1 1 d . . .
H20 H 0.3388 0.9563 0.1830 0.056 Uiso 1 1 calc R . .
C21 C 0.38671(12) 0.9063(3) 0.1207(4) 0.0520(9) Uani 1 1 d . . .
H21 H 0.4024 0.9671 0.1317 0.062 Uiso 1 1 calc R . .
C22 C 0.40152(12) 0.8237(3) 0.0756(3) 0.0507(9) Uani 1 1 d . . .
H22 H 0.4278 0.8270 0.0564 0.061 Uiso 1 1 calc R . .
C23 C 0.37812(11) 0.7364(3) 0.0584(3) 0.0436(8) Uani 1 1 d . . .
H23 H 0.3888 0.6797 0.0279 0.052 Uiso 1 1 calc R . .
C24 C 0.33917(10) 0.7287(2) 0.0844(3) 0.0351(7) Uani 1 1 d . . .
Br1 Br 0.534928(10) 0.29111(2) 0.64261(3) 0.04358(13) Uani 1 1 d . . .
Br2 Br 0.109812(17) 0.69982(3) 0.48635(4) 0.06671(16) Uani 1 1 d . . .
N1 N 0.31398(8) 0.64140(18) 0.0564(2) 0.0383(6) Uani 1 1 d . . .
H1 H 0.3292 0.6021 0.0204 0.046 Uiso 1 1 d R . .
N2 N 0.28610(8) 0.81303(18) 0.1619(2) 0.0365(6) Uani 1 1 d . . .
H2A H 0.2732 0.8713 0.1550 0.044 Uiso 1 1 calc R . .
O1 O 0.36867(7) 0.46119(17) 0.12426(19) 0.0447(5) Uani 1 1 d . . .
O2 O 0.25873(8) 0.48558(16) 0.2803(3) 0.0530(6) Uani 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.376(4) . ?
C1 C6 1.379(4) . ?
C1 Br1 1.902(3) . ?
C2 C3 1.392(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.389(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(4) . ?
C4 C7 1.502(4) . ?
C5 C6 1.389(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O1 1.220(3) . ?
C7 C8 1.509(4) . ?
C8 C9 1.538(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N1 1.467(4) . ?
C9 C10 1.510(4) . ?
C9 H9 1.0000 . ?
C10 C18 1.373(4) . ?
C10 C11 1.425(4) . ?
C11 O2 1.249(4) . ?
C11 C12 1.504(4) . ?
C12 C13 1.385(5) . ?
C12 C17 1.387(4) . ?
C13 C14 1.380(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.372(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.372(5) . ?
C15 Br2 1.904(3) . ?
C16 C17 1.385(4) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 N2 1.332(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.383(5) . ?
C19 C24 1.398(4) . ?
C19 N2 1.410(4) . ?
C20 C21 1.387(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.378(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.376(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.397(4) . ?
C23 H23 0.9500 . ?
C24 N1 1.404(4) . ?
N1 H1 0.9092 . ?
N2 H2A 0.8800 . ?

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 121.7(3) . . ?
C2 C1 Br1 119.1(2) . . ?
C6 C1 Br1 119.2(2) . . ?
C1 C2 C3 118.9(3) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C4 C3 C2 120.8(3) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C5 C4 C3 118.8(3) . . ?
C5 C4 C7 118.6(3) . . ?
C3 C4 C7 122.6(2) . . ?
C4 C5 C6 120.9(3) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 118.8(3) . . ?
C1 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
O1 C7 C4 119.6(3) . . ?
O1 C7 C8 121.7(3) . . ?
C4 C7 C8 118.7(2) . . ?
C7 C8 C9 112.3(2) . . ?
C7 C8 H8A 109.1 . . ?
C9 C8 H8A 109.1 . . ?
C7 C8 H8B 109.1 . . ?
C9 C8 H8B 109.1 . . ?
H8A C8 H8B 107.9 . . ?
N1 C9 C10 112.0(2) . . ?
N1 C9 C8 114.2(2) . . ?
C10 C9 C8 111.5(2) . . ?
N1 C9 H9 106.2 . . ?
C10 C9 H9 106.2 . . ?
C8 C9 H9 106.2 . . ?
C18 C10 C11 119.5(3) . . ?
C18 C10 C9 124.7(3) . . ?
C11 C10 C9 115.8(2) . . ?
O2 C11 C10 122.1(3) . . ?
O2 C11 C12 116.0(3) . . ?
C10 C11 C12 121.9(3) . . ?
C13 C12 C17 118.3(3) . . ?
C13 C12 C11 119.0(3) . . ?
C17 C12 C11 122.4(3) . . ?
C14 C13 C12 121.3(3) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C13 C14 C15 119.0(3) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
C16 C15 C14 121.4(3) . . ?
C16 C15 Br2 120.2(3) . . ?
C14 C15 Br2 118.4(3) . . ?
C15 C16 C17 119.1(3) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C12 C17 C16 120.9(3) . . ?
C12 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
N2 C18 C10 130.7(3) . . ?
N2 C18 H18 114.6 . . ?
C10 C18 H18 114.6 . . ?
C20 C19 C24 119.8(3) . . ?
C20 C19 N2 117.5(3) . . ?
C24 C19 N2 122.7(3) . . ?
C21 C20 C19 121.3(3) . . ?
C21 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C20 C21 C22 119.4(3) . . ?
C20 C21 H21 120.3 . . ?
C22 C21 H21 120.3 . . ?
C23 C22 C21 119.7(3) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C22 C23 C24 122.0(3) . . ?
C22 C23 H23 119.0 . . ?
C24 C23 H23 119.0 . . ?
C19 C24 N1 121.1(3) . . ?
C19 C24 C23 117.9(3) . . ?
N1 C24 C23 120.9(3) . . ?
C24 N1 C9 118.2(2) . . ?
C24 N1 H1 103.0 . . ?
C9 N1 H1 109.2 . . ?
C18 N2 C19 130.0(2) . . ?
C18 N2 H2A 115.0 . . ?
C19 N2 H2A 115.0 . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.07
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.546
_refine_diff_density_min         -1.033
_refine_diff_density_rms         0.064
####################################################################### 
# 
# 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_d25152
_database_code_depnum_ccdc_archive 'CCDC 2370736'
loop_
_audit_author_name
_audit_author_address
'Suresh Sundaram'
;National Taiwan Normal University
Taiwan
;
_audit_update_record             
;
2024-07-15 deposited with the CCDC.	2024-08-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H18 Cl N O'
_chemical_formula_sum            'C18 H18 Cl N O'
_chemical_formula_weight         299.78

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/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                   9.9614(6)
_cell_length_b                   15.4727(9)
_cell_length_c                   11.3672(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.434(2)
_cell_angle_gamma                90.00
_cell_volume                     1652.20(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    4682
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      24.09

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8880
_exptl_absorpt_correction_T_max  0.9931
_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 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            34591
_diffrn_reflns_av_R_equivalents  0.0954
_diffrn_reflns_av_sigmaI/netI    0.0411
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         25.05
_reflns_number_total             2917
_reflns_number_gt                2321
_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)+(0.0538P)²+1.2015P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2917
_refine_ls_number_parameters     186
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0576
_refine_ls_wR_factor_ref         0.1516
_refine_ls_wR_factor_gt          0.1394
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_restrained_S_all      1.149
_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 0.7205(3) 0.30885(16) 0.5493(2) 0.0381(6) Uani 1 1 d . . .
C2 C 0.8520(3) 0.30164(17) 0.6519(2) 0.0444(7) Uani 1 1 d . . .
C3 C 0.9277(3) 0.38251(17) 0.7097(2) 0.0381(6) Uani 1 1 d . . .
C4 C 0.8590(3) 0.44540(17) 0.7549(3) 0.0445(7) Uani 1 1 d . . .
H4 H 0.7607 0.4394 0.7440 0.053 Uiso 1 1 calc R . .
C5 C 0.9330(4) 0.5167(2) 0.8158(3) 0.0624(9) Uani 1 1 d . . .
H5 H 0.8859 0.5593 0.8479 0.075 Uiso 1 1 calc R . .
C6 C 1.0738(4) 0.5262(2) 0.8300(3) 0.0738(11) Uani 1 1 d . . .
H6 H 1.1244 0.5755 0.8719 0.089 Uiso 1 1 calc R . .
C7 C 1.1423(4) 0.4650(3) 0.7840(4) 0.0736(11) Uani 1 1 d . . .
H7 H 1.2398 0.4725 0.7928 0.088 Uiso 1 1 calc R . .
C8 C 1.0706(3) 0.3926(2) 0.7252(3) 0.0562(8) Uani 1 1 d . . .
H8 H 1.1192 0.3497 0.6952 0.067 Uiso 1 1 calc R . .
C9 C 0.6803(2) 0.38181(15) 0.4814(2) 0.0330(5) Uani 1 1 d . . .
H9 H 0.7360 0.4319 0.5124 0.040 Uiso 1 1 calc R . .
C10 C 0.5352(2) 0.47120(15) 0.3113(2) 0.0309(5) Uani 1 1 d . . .
C11 C 0.4675(3) 0.47195(17) 0.1837(2) 0.0371(6) Uani 1 1 d . . .
H11 H 0.4410 0.4191 0.1396 0.044 Uiso 1 1 calc R . .
C12 C 0.4383(3) 0.54977(18) 0.1199(3) 0.0451(7) Uani 1 1 d . . .
H12 H 0.3920 0.5492 0.0321 0.054 Uiso 1 1 calc R . .
C13 C 0.4745(3) 0.62805(18) 0.1804(3) 0.0474(7) Uani 1 1 d . . .
C14 C 0.4426(4) 0.7129(2) 0.1071(4) 0.0738(11) Uani 1 1 d . . .
H14 H 0.4295 0.6950 0.0195 0.089 Uiso 1 1 calc R . .
C15 C 0.3085(5) 0.7495(3) 0.0995(6) 0.1222(15) Uani 1 1 d . . .
H15A H 0.2940 0.8033 0.0513 0.183 Uiso 1 1 calc R . .
H15B H 0.3073 0.7618 0.1837 0.183 Uiso 1 1 calc R . .
H15C H 0.2323 0.7086 0.0582 0.183 Uiso 1 1 calc R . .
C16 C 0.5641(5) 0.7713(3) 0.1387(6) 0.1222(15) Uani 1 1 d . . .
H16A H 0.5381 0.8237 0.0877 0.183 Uiso 1 1 calc R . .
H16B H 0.6440 0.7427 0.1226 0.183 Uiso 1 1 calc R . .
H16C H 0.5918 0.7869 0.2272 0.183 Uiso 1 1 calc R . .
C17 C 0.5382(3) 0.62625(17) 0.3092(3) 0.0452(7) Uani 1 1 d . . .
H17 H 0.5619 0.6792 0.3535 0.054 Uiso 1 1 calc R . .
C18 C 0.5679(3) 0.54920(16) 0.3747(2) 0.0369(6) Uani 1 1 d . . .
H18 H 0.6107 0.5497 0.4629 0.044 Uiso 1 1 calc R . .
Cl1 Cl 0.62237(10) 0.21485(4) 0.49960(7) 0.0620(3) Uani 1 1 d . . .
N1 N 0.5705(2) 0.39128(13) 0.37514(18) 0.0348(5) Uani 1 1 d . . .
H1 H 0.5179 0.3458 0.3435 0.042 Uiso 1 1 calc R . .
O1 O 0.9035(3) 0.23089(13) 0.6924(2) 0.0749(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 C9 1.351(3) . ?
C1 C2 1.440(4) . ?
C1 Cl1 1.738(3) . ?
C2 O1 1.232(3) . ?
C2 C3 1.496(4) . ?
C3 C8 1.384(4) . ?
C3 C4 1.383(4) . ?
C4 C5 1.378(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.366(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.368(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.375(5) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 N1 1.341(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.382(3) . ?
C10 C18 1.387(3) . ?
C10 N1 1.417(3) . ?
C11 C12 1.385(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.380(4) . ?
C12 H12 0.9500 . ?
C13 C17 1.389(4) . ?
C13 C14 1.530(4) . ?
C14 C15 1.427(6) . ?
C14 C16 1.457(6) . ?
C14 H14 1.0000 . ?
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 C18 1.384(4) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
N1 H1 0.8800 . ?

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
C9 C1 C2 123.0(2) . . ?
C9 C1 Cl1 119.10(19) . . ?
C2 C1 Cl1 117.38(19) . . ?
O1 C2 C1 121.7(3) . . ?
O1 C2 C3 119.5(2) . . ?
C1 C2 C3 118.8(2) . . ?
C8 C3 C4 119.2(3) . . ?
C8 C3 C2 119.9(3) . . ?
C4 C3 C2 120.8(2) . . ?
C5 C4 C3 120.1(3) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C6 C5 C4 120.2(3) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C7 C6 C5 120.2(3) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C8 120.3(3) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C7 C8 C3 119.9(3) . . ?
C7 C8 H8 120.0 . . ?
C3 C8 H8 120.0 . . ?
N1 C9 C1 127.1(2) . . ?
N1 C9 H9 116.4 . . ?
C1 C9 H9 116.4 . . ?
C11 C10 C18 119.1(2) . . ?
C11 C10 N1 119.7(2) . . ?
C18 C10 N1 121.2(2) . . ?
C10 C11 C12 120.1(2) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C13 C12 C11 121.8(2) . . ?
C13 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
C12 C13 C17 117.4(2) . . ?
C12 C13 C14 120.6(3) . . ?
C17 C13 C14 122.0(3) . . ?
C15 C14 C16 116.9(4) . . ?
C15 C14 C13 113.3(3) . . ?
C16 C14 C13 113.2(3) . . ?
C15 C14 H14 103.9 . . ?
C16 C14 H14 103.9 . . ?
C13 C14 H14 103.9 . . ?
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 . . ?
C18 C17 C13 121.7(3) . . ?
C18 C17 H17 119.2 . . ?
C13 C17 H17 119.2 . . ?
C17 C18 C10 119.9(2) . . ?
C17 C18 H18 120.0 . . ?
C10 C18 H18 120.0 . . ?
C9 N1 C10 123.1(2) . . ?
C9 N1 H1 118.5 . . ?
C10 N1 H1 118.5 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.503
_refine_diff_density_min         -0.540
_refine_diff_density_rms         0.052
