# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_CRL37138_399_1_2m_a
_database_code_depnum_ccdc_archive 'CCDC 1870838'
loop_
_audit_author_name
_audit_author_address
'Somaraju yugandhar'
;Tokyo institute of technology
India
;
_audit_update_record             
;
2018-09-29 deposited with the CCDC.	2019-06-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H14 Cl N O3'
_chemical_formula_weight         399.81

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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   11.1094(16)
_cell_length_b                   5.7150(8)
_cell_length_c                   15.077(2)
_cell_angle_alpha                90
_cell_angle_beta                 111.014(2)
_cell_angle_gamma                90
_cell_volume                     893.6(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    90
_cell_measurement_reflns_used    3581
_cell_measurement_theta_min      2.827
_cell_measurement_theta_max      28.603

_exptl_crystal_description       prism

_exptl_crystal_colour            yellow

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_F_000             412
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.054
_exptl_absorpt_coefficient_mu    0.242
_shelx_estimated_absorpt_T_min   0.893
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.959
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.333

_diffrn_reflns_number            5418
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_av_R_equivalents  0.0125
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.447
_diffrn_reflns_theta_max         29.081
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.909
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.909
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.815
_diffrn_reflns_point_group_measured_fraction_full 0.934
_reflns_number_total             3890
_reflns_number_gt                3743
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.635
_reflns_Friedel_fraction_max     0.700
_reflns_Friedel_fraction_full    0.856

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'

_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'

_computing_data_reduction        'SAINT (Bruker AXS, 2004)'

_computing_structure_solution    'SHELXT (Sheldrick, 2014)'

_computing_structure_refinement  'SHELXL-2016 (Sheldrick, 2016)'

_computing_molecular_graphics    'XSHELXle (Bruker AXS)'

_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'


_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'

_computing_publication_material  'XCIF (Bruker AXS, 2001)'


_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)+(0.0445P)²+0.1465P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1417 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3890
_refine_ls_number_parameters     262
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0290
_refine_ls_wR_factor_ref         0.0746
_refine_ls_wR_factor_gt          0.0737
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.08974(5) -0.06390(10) 0.73394(4) 0.02488(14) Uani 1 1 d . . . . .
O1 O 0.42606(13) 0.6634(3) 0.35821(10) 0.0161(3) Uani 1 1 d . . . . .
N1 N 0.15998(17) 0.0354(3) 0.31734(12) 0.0179(4) Uani 1 1 d . . . . .
C1 C 0.23654(19) 0.2514(4) 0.55826(14) 0.0179(4) Uani 1 1 d . . . . .
H1 H 0.281445 0.391829 0.556553 0.021 Uiso 1 1 calc R U . . .
C2 C 0.2015(2) 0.2036(4) 0.63702(15) 0.0184(4) Uani 1 1 d . . . . .
H2 H 0.220932 0.311400 0.688199 0.022 Uiso 1 1 calc R U . . .
O2 O 0.41387(14) 0.5955(3) 0.49947(10) 0.0198(3) Uani 1 1 d . . . . .
O3 O 0.18036(14) 0.1455(3) 0.23913(10) 0.0187(3) Uani 1 1 d . . . . .
C3 C 0.13828(19) -0.0034(4) 0.63868(14) 0.0174(4) Uani 1 1 d . . . . .
C4 C 0.1116(2) -0.1677(4) 0.56559(15) 0.0184(4) Uani 1 1 d . . . . .
H4 H 0.070481 -0.311437 0.568950 0.022 Uiso 1 1 calc R U . . .
C5 C 0.14622(19) -0.1175(4) 0.48821(15) 0.0173(4) Uani 1 1 d . . . . .
H5 H 0.129243 -0.228250 0.438226 0.021 Uiso 1 1 calc R U . . .
C6 C 0.20612(18) 0.0954(4) 0.48272(14) 0.0156(4) Uani 1 1 d . . . . .
C8 C 0.29031(19) 0.3517(4) 0.36874(14) 0.0134(4) Uani 1 1 d . . . . .
C7 C 0.22362(19) 0.1597(4) 0.39295(14) 0.0153(4) Uani 1 1 d . . . . .
C9 C 0.37707(18) 0.5366(4) 0.41755(14) 0.0152(4) Uani 1 1 d . . . . .
C10 C 0.38560(19) 0.6430(4) 0.26104(13) 0.0143(4) Uani 1 1 d . . . . .
C11 C 0.29599(19) 0.4830(4) 0.21271(13) 0.0155(4) Uani 1 1 d . . . . .
C12 C 0.25716(19) 0.3310(4) 0.27231(14) 0.0153(4) Uani 1 1 d . . . . .
C13 C 0.45652(18) 0.8084(4) 0.22243(14) 0.0145(4) Uani 1 1 d . . . . .
C14 C 0.50579(19) 1.0163(4) 0.27075(14) 0.0161(4) Uani 1 1 d . . . . .
H14 H 0.491871 1.052654 0.327808 0.019 Uiso 1 1 calc R U . . .
C15 C 0.57497(19) 1.1698(4) 0.23576(15) 0.0198(4) Uani 1 1 d . . . . .
H15 H 0.607582 1.311166 0.268797 0.024 Uiso 1 1 calc R U . . .
C16 C 0.5967(2) 1.1180(4) 0.15287(16) 0.0211(5) Uani 1 1 d . . . . .
H16 H 0.643884 1.223435 0.129009 0.025 Uiso 1 1 calc R U . . .
C17 C 0.5488(2) 0.9098(4) 0.10479(15) 0.0210(4) Uani 1 1 d . . . . .
H17 H 0.563800 0.873423 0.048122 0.025 Uiso 1 1 calc R U . . .
C18 C 0.47966(19) 0.7559(4) 0.13915(14) 0.0170(4) Uani 1 1 d . . . . .
H18 H 0.447760 0.614224 0.106144 0.020 Uiso 1 1 calc R U . . .
C19 C 0.23353(18) 0.4675(4) 0.10720(13) 0.0148(4) Uani 1 1 d . . . . .
C20 C 0.15685(19) 0.6528(4) 0.05728(14) 0.0170(4) Uani 1 1 d . . . . .
H20 H 0.146437 0.788072 0.090416 0.020 Uiso 1 1 calc R U . . .
C21 C 0.0957(2) 0.6393(4) -0.04091(15) 0.0198(4) Uani 1 1 d . . . . .
H21 H 0.043235 0.765050 -0.074648 0.024 Uiso 1 1 calc R U . . .
C22 C 0.11140(19) 0.4419(4) -0.08968(14) 0.0194(4) Uani 1 1 d . . . . .
H22 H 0.070569 0.433494 -0.156788 0.023 Uiso 1 1 calc R U . . .
C23 C 0.1869(2) 0.2573(4) -0.03998(15) 0.0188(4) Uani 1 1 d . . . . .
H23 H 0.197518 0.122353 -0.073253 0.023 Uiso 1 1 calc R U . . .
C24 C 0.24693(19) 0.2687(4) 0.05790(14) 0.0164(4) Uani 1 1 d . . . . .
H24 H 0.297362 0.140643 0.091523 0.020 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C3 1.740(2) . ?
O1 C10 1.375(2) . ?
O1 C9 1.404(2) . ?
N1 C7 1.314(3) . ?
N1 O3 1.424(2) . ?
C1 C6 1.390(3) . ?
C1 C2 1.403(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.380(3) . ?
C2 H2 0.9500 . ?
O2 C9 1.202(2) . ?
O3 C12 1.340(3) . ?
C3 C4 1.396(3) . ?
C4 C5 1.383(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.403(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.481(3) . ?
C8 C12 1.371(3) . ?
C8 C9 1.442(3) . ?
C8 C7 1.442(3) . ?
C10 C11 1.356(3) . ?
C10 C13 1.477(3) . ?
C11 C12 1.423(3) . ?
C11 C19 1.493(3) . ?
C13 C14 1.398(3) . ?
C13 C18 1.401(3) . ?
C14 C15 1.389(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.387(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.395(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.385(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C24 1.394(3) . ?
C19 C20 1.398(3) . ?
C20 C21 1.392(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.391(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.389(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.386(3) . ?
C23 H23 0.9500 . ?
C24 H24 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
C10 O1 C9 125.61(16) . . ?
C7 N1 O3 106.47(16) . . ?
C6 C1 C2 120.6(2) . . ?
C6 C1 H1 119.7 . . ?
C2 C1 H1 119.7 . . ?
C3 C2 C1 118.7(2) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C12 O3 N1 108.03(15) . . ?
C2 C3 C4 121.82(19) . . ?
C2 C3 Cl1 119.70(16) . . ?
C4 C3 Cl1 118.48(16) . . ?
C5 C4 C3 118.8(2) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 120.7(2) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 119.28(19) . . ?
C1 C6 C7 121.11(19) . . ?
C5 C6 C7 119.31(18) . . ?
C12 C8 C9 118.73(18) . . ?
C12 C8 C7 103.63(17) . . ?
C9 C8 C7 137.61(18) . . ?
N1 C7 C8 110.93(17) . . ?
N1 C7 C6 116.91(18) . . ?
C8 C7 C6 131.89(18) . . ?
O2 C9 O1 116.34(18) . . ?
O2 C9 C8 130.45(19) . . ?
O1 C9 C8 113.20(16) . . ?
C11 C10 O1 121.75(17) . . ?
C11 C10 C13 127.77(18) . . ?
O1 C10 C13 110.43(17) . . ?
C10 C11 C12 113.75(17) . . ?
C10 C11 C19 125.72(18) . . ?
C12 C11 C19 120.42(18) . . ?
O3 C12 C8 110.92(18) . . ?
O3 C12 C11 122.93(18) . . ?
C8 C12 C11 126.15(19) . . ?
C14 C13 C18 119.04(19) . . ?
C14 C13 C10 120.18(18) . . ?
C18 C13 C10 120.74(19) . . ?
C15 C14 C13 120.35(19) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C16 C15 C14 120.4(2) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 119.5(2) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C18 C17 C16 120.41(19) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C13 120.3(2) . . ?
C17 C18 H18 119.9 . . ?
C13 C18 H18 119.9 . . ?
C24 C19 C20 119.42(18) . . ?
C24 C19 C11 121.24(18) . . ?
C20 C19 C11 119.31(18) . . ?
C21 C20 C19 120.1(2) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C22 C21 C20 120.1(2) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C23 C22 C21 119.79(18) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C24 C23 C22 120.4(2) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C23 C24 C19 120.22(19) . . ?
C23 C24 H24 119.9 . . ?
C19 C24 H24 119.9 . . ?

_refine_diff_density_max         0.323
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_CRL37110_395_1_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1870841'
loop_
_audit_author_name
_audit_author_address
'Somaraju yugandhar'
;Tokyo institute of technology
Japan
;
_audit_update_record             
;
2018-09-29 deposited with the CCDC.	2019-06-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H16 Cl N'
_chemical_formula_weight         329.81

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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   10.8409(15)
_cell_length_b                   10.0705(14)
_cell_length_c                   15.263(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.756(2)
_cell_angle_gamma                90
_cell_volume                     1665.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    90
_cell_measurement_reflns_used    6381
_cell_measurement_theta_min      2.272
_cell_measurement_theta_max      29.0345

_exptl_crystal_description       plate

_exptl_crystal_colour            yellow

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.231
_shelx_estimated_absorpt_T_min   0.951
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.916
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.333

_diffrn_reflns_number            9711
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_av_R_equivalents  0.0134
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.272
_diffrn_reflns_theta_max         29.035
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.918
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.918
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4080
_reflns_number_gt                3653
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'

_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'

_computing_data_reduction        'SAINT (Bruker AXS, 2004)'

_computing_structure_solution    'SHELXT (Sheldrick, 2014)'

_computing_structure_refinement  'SHELXL-2016 (Sheldrick, 2016)'

_computing_molecular_graphics    'XSHELXle (Bruker AXS)'

_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'


_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'

_computing_publication_material  'XCIF (Bruker AXS, 2001)'


_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)+(0.0521P)²+0.7782P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4080
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0328
_refine_ls_wR_factor_ref         0.0988
_refine_ls_wR_factor_gt          0.0955
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.35725(3) 0.89559(3) 0.54570(2) 0.02078(9) Uani 1 1 d . . . . .
C1 C 0.38396(10) 0.64886(12) 0.61010(7) 0.0156(2) Uani 1 1 d . . . . .
H1 H 0.407634 0.690928 0.663730 0.019 Uiso 1 1 calc R U . . .
N1 N 0.38188(9) 0.23134(10) 0.58432(6) 0.0165(2) Uani 1 1 d . . . . .
C3 C 0.31554(11) 0.66564(12) 0.45692(8) 0.0177(2) Uani 1 1 d . . . . .
H3 H 0.293765 0.719717 0.407847 0.021 Uiso 1 1 calc R U . . .
C2 C 0.35243(10) 0.72359(12) 0.53778(8) 0.0163(2) Uani 1 1 d . . . . .
C4 C 0.31172(11) 0.52988(12) 0.45052(7) 0.0169(2) Uani 1 1 d . . . . .
H4 H 0.286201 0.489756 0.396630 0.020 Uiso 1 1 calc R U . . .
C5 C 0.34534(10) 0.44852(12) 0.52326(7) 0.0148(2) Uani 1 1 d . . . . .
C6 C 0.38101(10) 0.50822(11) 0.60435(7) 0.0140(2) Uani 1 1 d . . . . .
C7 C 0.41646(10) 0.42448(12) 0.67669(7) 0.0143(2) Uani 1 1 d . . . . .
C8 C 0.41528(10) 0.28849(12) 0.66356(7) 0.0149(2) Uani 1 1 d . . . . .
C9 C 0.34825(10) 0.30683(12) 0.51754(8) 0.0159(2) Uani 1 1 d . . . . .
C10 C 0.46026(10) 0.48763(11) 0.76061(7) 0.0145(2) Uani 1 1 d . . . . .
C11 C 0.37871(11) 0.55514(12) 0.81407(8) 0.0186(2) Uani 1 1 d . . . . .
H11 H 0.293621 0.560021 0.797569 0.022 Uiso 1 1 calc R U . . .
C12 C 0.42128(12) 0.61516(13) 0.89122(8) 0.0222(3) Uani 1 1 d . . . . .
H12 H 0.364971 0.659633 0.927607 0.027 Uiso 1 1 calc R U . . .
C13 C 0.54606(12) 0.61042(12) 0.91540(8) 0.0215(3) Uani 1 1 d . . . . .
H13 H 0.575031 0.651641 0.968105 0.026 Uiso 1 1 calc R U . . .
C14 C 0.62787(11) 0.54514(12) 0.86210(8) 0.0203(2) Uani 1 1 d . . . . .
H14 H 0.713239 0.542610 0.878045 0.024 Uiso 1 1 calc R U . . .
C15 C 0.58545(11) 0.48334(12) 0.78535(8) 0.0172(2) Uani 1 1 d . . . . .
H15 H 0.641915 0.437962 0.749563 0.021 Uiso 1 1 calc R U . . .
C16 C 0.45050(10) 0.18900(11) 0.73232(7) 0.0155(2) Uani 1 1 d . . . . .
C17 C 0.41367(11) 0.20029(12) 0.81911(8) 0.0189(2) Uani 1 1 d . . . . .
H17 H 0.369548 0.276695 0.836897 0.023 Uiso 1 1 calc R U . . .
C18 C 0.44134(12) 0.10014(13) 0.87960(8) 0.0222(3) Uani 1 1 d . . . . .
H18 H 0.415417 0.108329 0.938246 0.027 Uiso 1 1 calc R U . . .
C19 C 0.50666(12) -0.01164(13) 0.85455(9) 0.0237(3) Uani 1 1 d . . . . .
H19 H 0.525074 -0.079960 0.895832 0.028 Uiso 1 1 calc R U . . .
C20 C 0.54490(12) -0.02295(13) 0.76875(9) 0.0238(3) Uani 1 1 d . . . . .
H20 H 0.590476 -0.098693 0.751580 0.029 Uiso 1 1 calc R U . . .
C21 C 0.51670(11) 0.07616(12) 0.70799(8) 0.0194(2) Uani 1 1 d . . . . .
H21 H 0.542595 0.067250 0.649383 0.023 Uiso 1 1 calc R U . . .
C22 C 0.31196(12) 0.23758(13) 0.43306(8) 0.0214(3) Uani 1 1 d . . . . .
H22A H 0.359268 0.274656 0.385136 0.032 Uiso 1 1 calc R U . . .
H22B H 0.223606 0.250639 0.420478 0.032 Uiso 1 1 calc R U . . .
H22C H 0.329427 0.142423 0.438641 0.032 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C2 1.7370(13) . ?
C1 C2 1.3706(16) . ?
C1 C6 1.4193(16) . ?
C1 H1 0.9500 . ?
N1 C9 1.3142(15) . ?
N1 C8 1.3778(14) . ?
C3 C4 1.3712(17) . ?
C3 C2 1.4118(16) . ?
C3 H3 0.9500 . ?
C4 C5 1.4185(16) . ?
C4 H4 0.9500 . ?
C5 C6 1.4189(15) . ?
C5 C9 1.4299(16) . ?
C6 C7 1.4325(15) . ?
C7 C8 1.3840(16) . ?
C7 C10 1.4944(15) . ?
C8 C16 1.4921(15) . ?
C9 C22 1.5076(16) . ?
C10 C11 1.3979(16) . ?
C10 C15 1.3982(16) . ?
C11 C12 1.3897(17) . ?
C11 H11 0.9500 . ?
C12 C13 1.3921(19) . ?
C12 H12 0.9500 . ?
C13 C14 1.3874(18) . ?
C13 H13 0.9500 . ?
C14 C15 1.3921(16) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.3999(16) . ?
C16 C21 1.4001(17) . ?
C17 C18 1.3937(17) . ?
C17 H17 0.9500 . ?
C18 C19 1.3897(18) . ?
C18 H18 0.9500 . ?
C19 C20 1.3904(19) . ?
C19 H19 0.9500 . ?
C20 C21 1.3900(17) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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
C2 C1 C6 119.57(11) . . ?
C2 C1 H1 120.2 . . ?
C6 C1 H1 120.2 . . ?
C9 N1 C8 119.89(10) . . ?
C4 C3 C2 118.79(10) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C1 C2 C3 122.28(11) . . ?
C1 C2 Cl1 119.03(9) . . ?
C3 C2 Cl1 118.70(9) . . ?
C3 C4 C5 120.91(11) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C6 119.64(10) . . ?
C4 C5 C9 122.29(10) . . ?
C6 C5 C9 118.05(10) . . ?
C5 C6 C1 118.80(10) . . ?
C5 C6 C7 118.84(10) . . ?
C1 C6 C7 122.33(10) . . ?
C8 C7 C6 118.02(10) . . ?
C8 C7 C10 123.13(10) . . ?
C6 C7 C10 118.74(10) . . ?
N1 C8 C7 122.79(10) . . ?
N1 C8 C16 113.05(10) . . ?
C7 C8 C16 124.16(10) . . ?
N1 C9 C5 122.41(11) . . ?
N1 C9 C22 117.04(11) . . ?
C5 C9 C22 120.55(10) . . ?
C11 C10 C15 118.90(11) . . ?
C11 C10 C7 121.15(10) . . ?
C15 C10 C7 119.91(10) . . ?
C12 C11 C10 120.44(11) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 120.30(12) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C14 C13 C12 119.62(11) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C15 120.30(11) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C10 120.43(11) . . ?
C14 C15 H15 119.8 . . ?
C10 C15 H15 119.8 . . ?
C17 C16 C21 118.70(11) . . ?
C17 C16 C8 122.46(10) . . ?
C21 C16 C8 118.73(10) . . ?
C18 C17 C16 120.41(12) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C19 C18 C17 120.34(12) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C20 119.64(12) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C21 C20 C19 120.24(12) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C20 C21 C16 120.66(12) . . ?
C20 C21 H21 119.7 . . ?
C16 C21 H21 119.7 . . ?
C9 C22 H22A 109.5 . . ?
C9 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C9 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

_refine_diff_density_max         0.417
_refine_diff_density_min         -0.255
_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 
# 
# 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_CRL37140_398_1_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1870840'
loop_
_audit_author_name
_audit_author_address
'Somaraju yugandhar'
;Tokyo institute of technology
Japan
;
_audit_update_record             
;
2018-09-29 deposited with the CCDC.	2019-06-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H12 Cl N O3'
_chemical_formula_weight         337.75

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   7.1186(6)
_cell_length_b                   19.2065(17)
_cell_length_c                   21.5744(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2949.7(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    90
_cell_measurement_reflns_used    8568
_cell_measurement_theta_min      2.3215
_cell_measurement_theta_max      29.136

_exptl_crystal_description       prism

_exptl_crystal_colour            yellow

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_F_000             1392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.277
_shelx_estimated_absorpt_T_min   0.947
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.958
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.333

_diffrn_reflns_number            16602
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.888
_diffrn_reflns_theta_max         29.136
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3722
_reflns_number_gt                3299
_reflns_threshold_expression     'I > 2σ'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 '

_computing_cell_refinement       'APEX2 '

_computing_data_reduction        'SAINT (Bruker AXS, 2004)'

_computing_structure_solution    'SHELXT (Sheldrick, 2014)'

_computing_structure_refinement  'SHELXL-2016 (Sheldrick, 2016)'

_computing_molecular_graphics    'XSHELXle (Bruker AXS)'

_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'

_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'

_computing_publication_material  'XCIF (Bruker AXS, 2001)'


_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)+(0.0437P)²+1.5822P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3722
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0294
_refine_ls_wR_factor_ref         0.0829
_refine_ls_wR_factor_gt          0.0797
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.29471(4) 0.69119(2) 0.29136(2) 0.01766(9) Uani 1 1 d . . . . .
N1 N 0.53865(15) 0.35826(5) 0.29709(4) 0.0138(2) Uani 1 1 d . . . . .
O1 O 0.38084(12) 0.41252(4) 0.49104(4) 0.01485(18) Uani 1 1 d . . . . .
C1 C 0.45880(16) 0.51833(6) 0.37930(5) 0.0126(2) Uani 1 1 d . . . . .
H1 H 0.511124 0.506025 0.418299 0.015 Uiso 1 1 calc R U . . .
O2 O 0.42917(11) 0.29838(4) 0.49750(4) 0.01167(16) Uani 1 1 d . . . . .
C2 C 0.41791(16) 0.58761(6) 0.36620(5) 0.0133(2) Uani 1 1 d . . . . .
H2 H 0.443397 0.622910 0.395883 0.016 Uiso 1 1 calc R U . . .
O3 O 0.57571(12) 0.28958(4) 0.31868(4) 0.01334(17) Uani 1 1 d . . . . .
C3 C 0.33923(16) 0.60462(6) 0.30913(5) 0.0127(2) Uani 1 1 d . . . . .
C4 C 0.29576(16) 0.55379(6) 0.26559(5) 0.0141(2) Uani 1 1 d . . . . .
H4 H 0.238110 0.566016 0.227396 0.017 Uiso 1 1 calc R U . . .
C5 C 0.33801(16) 0.48491(6) 0.27887(5) 0.0135(2) Uani 1 1 d . . . . .
H5 H 0.309057 0.449640 0.249508 0.016 Uiso 1 1 calc R U . . .
C6 C 0.42297(15) 0.46687(6) 0.33516(5) 0.0114(2) Uani 1 1 d . . . . .
C7 C 0.47820(16) 0.39384(6) 0.34525(5) 0.0114(2) Uani 1 1 d . . . . .
C8 C 0.47549(15) 0.35111(6) 0.39953(5) 0.0106(2) Uani 1 1 d . . . . .
C9 C 0.42463(15) 0.36054(6) 0.46352(5) 0.0109(2) Uani 1 1 d . . . . .
C10 C 0.47981(15) 0.23383(6) 0.47430(5) 0.0110(2) Uani 1 1 d . . . . .
C11 C 0.54188(15) 0.22522(6) 0.41503(5) 0.0114(2) Uani 1 1 d . . . . .
C12 C 0.53362(15) 0.28727(6) 0.37928(5) 0.0112(2) Uani 1 1 d . . . . .
C13 C 0.62067(17) 0.15958(6) 0.38725(5) 0.0143(2) Uani 1 1 d . . . . .
H13A H 0.722362 0.171405 0.358496 0.021 Uiso 1 1 calc R U . . .
H13B H 0.521239 0.134861 0.364824 0.021 Uiso 1 1 calc R U . . .
H13C H 0.669740 0.129706 0.420325 0.021 Uiso 1 1 calc R U . . .
C14 C 0.46017(16) 0.17925(6) 0.52185(5) 0.0116(2) Uani 1 1 d . . . . .
C15 C 0.50325(16) 0.19329(6) 0.58397(5) 0.0138(2) Uani 1 1 d . . . . .
H15 H 0.540086 0.238894 0.595946 0.017 Uiso 1 1 calc R U . . .
C16 C 0.49233(17) 0.14081(7) 0.62814(5) 0.0167(2) Uani 1 1 d . . . . .
H16 H 0.523382 0.150432 0.670095 0.020 Uiso 1 1 calc R U . . .
C17 C 0.43599(17) 0.07417(7) 0.61100(6) 0.0174(2) Uani 1 1 d . . . . .
H17 H 0.431203 0.038108 0.641104 0.021 Uiso 1 1 calc R U . . .
C18 C 0.38663(17) 0.06027(6) 0.54983(6) 0.0164(2) Uani 1 1 d . . . . .
H18 H 0.344820 0.015076 0.538435 0.020 Uiso 1 1 calc R U . . .
C19 C 0.39850(16) 0.11249(6) 0.50541(5) 0.0139(2) Uani 1 1 d . . . . .
H19 H 0.364624 0.102871 0.463690 0.017 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C3 1.7356(11) . ?
N1 C7 1.3160(14) . ?
N1 O3 1.4236(12) . ?
O1 C9 1.2026(14) . ?
C1 C2 1.3912(16) . ?
C1 C6 1.3960(15) . ?
C1 H1 0.9500 . ?
O2 C10 1.3846(13) . ?
O2 C9 1.4014(13) . ?
C2 C3 1.3916(16) . ?
C2 H2 0.9500 . ?
O3 C12 1.3420(13) . ?
C3 C4 1.3897(16) . ?
C4 C5 1.3866(16) . ?
C4 H4 0.9500 . ?
C5 C6 1.4003(15) . ?
C5 H5 0.9500 . ?
C6 C7 1.4729(15) . ?
C7 C8 1.4300(15) . ?
C8 C12 1.3658(15) . ?
C8 C9 1.4388(15) . ?
C10 C11 1.3630(15) . ?
C10 C14 1.4734(15) . ?
C11 C12 1.4208(15) . ?
C11 C13 1.5044(15) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C19 1.4008(16) . ?
C14 C15 1.4012(16) . ?
C15 C16 1.3893(16) . ?
C15 H15 0.9500 . ?
C16 C17 1.3913(18) . ?
C16 H16 0.9500 . ?
C17 C18 1.3915(17) . ?
C17 H17 0.9500 . ?
C18 C19 1.3899(16) . ?
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
C7 N1 O3 106.46(9) . . ?
C2 C1 C6 120.03(10) . . ?
C2 C1 H1 120.0 . . ?
C6 C1 H1 120.0 . . ?
C10 O2 C9 125.43(9) . . ?
C1 C2 C3 119.23(10) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C12 O3 N1 107.94(8) . . ?
C4 C3 C2 121.53(10) . . ?
C4 C3 Cl1 118.88(9) . . ?
C2 C3 Cl1 119.59(9) . . ?
C5 C4 C3 118.83(10) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 120.59(11) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 119.70(10) . . ?
C1 C6 C7 121.64(10) . . ?
C5 C6 C7 118.63(10) . . ?
N1 C7 C8 110.66(10) . . ?
N1 C7 C6 117.72(10) . . ?
C8 C7 C6 131.61(10) . . ?
C12 C8 C7 104.44(9) . . ?
C12 C8 C9 119.74(10) . . ?
C7 C8 C9 135.79(10) . . ?
O1 C9 O2 117.07(10) . . ?
O1 C9 C8 130.05(10) . . ?
O2 C9 C8 112.88(9) . . ?
C11 C10 O2 122.15(10) . . ?
C11 C10 C14 126.69(10) . . ?
O2 C10 C14 111.15(9) . . ?
C10 C11 C12 113.20(10) . . ?
C10 C11 C13 126.61(10) . . ?
C12 C11 C13 120.14(10) . . ?
O3 C12 C8 110.46(10) . . ?
O3 C12 C11 123.18(10) . . ?
C8 C12 C11 126.30(10) . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C19 C14 C15 119.14(10) . . ?
C19 C14 C10 120.31(10) . . ?
C15 C14 C10 120.54(10) . . ?
C16 C15 C14 120.27(11) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 120.10(11) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C16 C17 C18 120.08(11) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C19 C18 C17 120.01(11) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C14 120.33(11) . . ?
C18 C19 H19 119.8 . . ?
C14 C19 H19 119.8 . . ?

_refine_diff_density_max         0.387
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_CRL37241_452_1_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1899700'
loop_
_audit_author_name
_audit_author_address
'Somaraju yugandhar'
;Tokyo institute of technology
India
;
_audit_update_record             
;
2019-02-26 deposited with the CCDC.	2019-06-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H16 Cl N O'
_chemical_formula_weight         357.82

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'

_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                   11.027(3)
_cell_length_b                   8.159(2)
_cell_length_c                   19.126(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.913(3)
_cell_angle_gamma                90
_cell_volume                     1718.5(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    90
_cell_measurement_reflns_used    3325
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      28.77

_exptl_crystal_description       clumn

_exptl_crystal_colour            colorless

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.317
_exptl_crystal_size_mid          0.032
_exptl_crystal_size_min          0.021
_exptl_absorpt_coefficient_mu    0.234
_shelx_estimated_absorpt_T_min   0.930
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.527
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.333

_diffrn_reflns_number            9886
_diffrn_reflns_av_unetI/netI     0.0630
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.849
_diffrn_reflns_theta_max         29.033
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.924
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4233
_reflns_number_gt                3088
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'

_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'

_computing_data_reduction        'SAINT (Bruker AXS, 2004)'

_computing_structure_solution    'SHELXT (Sheldrick, 2014)'

_computing_structure_refinement  'SHELXL-2016 (Sheldrick, 2016)'

_computing_molecular_graphics    'XSHELXle (Bruker AXS)'

_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'


_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'

_computing_publication_material  'XCIF (Bruker AXS, 2001)'


_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)+(0.0481P)²+0.5688P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4233
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1134
_refine_ls_wR_factor_gt          0.1016
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 1.05695(4) 0.81158(6) 0.55386(2) 0.02305(13) Uani 1 1 d . . . . .
N1 N 0.59135(14) 0.2736(2) 0.50623(8) 0.0227(3) Uani 1 1 d . . . . .
O1 O 0.49394(12) 0.19930(16) 0.46739(6) 0.0222(3) Uani 1 1 d . . . . .
C1 C 0.92816(16) 0.6950(2) 0.53111(9) 0.0192(4) Uani 1 1 d . . . . .
C2 C 0.89848(17) 0.5621(2) 0.57234(9) 0.0208(4) Uani 1 1 d . . . . .
H2 H 0.946504 0.536487 0.613543 0.025 Uiso 1 1 calc R U . . .
C3 C 0.79837(16) 0.4674(2) 0.55281(9) 0.0207(4) Uani 1 1 d . . . . .
H3 H 0.777041 0.377299 0.581142 0.025 Uiso 1 1 calc R U . . .
C4 C 0.72827(16) 0.5032(2) 0.49174(8) 0.0183(4) Uani 1 1 d . . . . .
C5 C 0.75911(17) 0.6388(2) 0.45207(9) 0.0223(4) Uani 1 1 d . . . . .
H5 H 0.711375 0.665057 0.410834 0.027 Uiso 1 1 calc R U . . .
C8 C 0.55351(16) 0.4096(2) 0.40415(9) 0.0188(4) Uani 1 1 d . . . . .
H8 H 0.559741 0.488530 0.367978 0.023 Uiso 1 1 calc R U . . .
C7 C 0.62575(16) 0.3983(2) 0.46789(9) 0.0184(4) Uani 1 1 d . . . . .
C6 C 0.85813(17) 0.7363(2) 0.47163(9) 0.0226(4) Uani 1 1 d . . . . .
H6 H 0.877530 0.829605 0.444685 0.027 Uiso 1 1 calc R U . . .
C9 C 0.47421(16) 0.2837(2) 0.40637(9) 0.0185(4) Uani 1 1 d . . . . .
C10 C 0.38096(16) 0.2236(2) 0.35582(9) 0.0185(4) Uani 1 1 d . . . . .
C11 C 0.30665(16) 0.0999(2) 0.37252(9) 0.0193(4) Uani 1 1 d . . . . .
H11 H 0.310718 0.068083 0.420369 0.023 Uiso 1 1 calc R U . . .
C12 C 0.22014(16) 0.0075(2) 0.32658(9) 0.0190(4) Uani 1 1 d . . . . .
C13 C 0.12901(17) -0.0834(2) 0.35709(9) 0.0221(4) Uani 1 1 d . . . . .
H13 H 0.121963 -0.079149 0.406358 0.027 Uiso 1 1 calc R U . . .
C14 C 0.04855(18) -0.1798(2) 0.31657(10) 0.0252(4) Uani 1 1 d . . . . .
H14 H -0.013728 -0.238666 0.338192 0.030 Uiso 1 1 calc R U . . .
C15 C 0.05891(16) -0.1902(2) 0.24478(10) 0.0236(4) Uani 1 1 d . . . . .
H15 H 0.004481 -0.256648 0.217099 0.028 Uiso 1 1 calc R U . . .
C16 C 0.14952(17) -0.1025(2) 0.21385(9) 0.0231(4) Uani 1 1 d . . . . .
H16 H 0.157333 -0.109557 0.164705 0.028 Uiso 1 1 calc R U . . .
C17 C 0.22883(17) -0.0048(2) 0.25388(9) 0.0212(4) Uani 1 1 d . . . . .
H17 H 0.290127 0.054835 0.231717 0.025 Uiso 1 1 calc R U . . .
C18 C 0.37883(16) 0.3056(2) 0.28561(9) 0.0178(4) Uani 1 1 d . . . . .
C19 C 0.28022(17) 0.4016(2) 0.26293(9) 0.0215(4) Uani 1 1 d . . . . .
H19 H 0.215959 0.420120 0.293236 0.026 Uiso 1 1 calc R U . . .
C20 C 0.27473(17) 0.4707(2) 0.19638(9) 0.0239(4) Uani 1 1 d . . . . .
H20 H 0.206902 0.535955 0.181487 0.029 Uiso 1 1 calc R U . . .
C21 C 0.36792(18) 0.4446(2) 0.15171(9) 0.0243(4) Uani 1 1 d . . . . .
H21 H 0.363802 0.490889 0.106082 0.029 Uiso 1 1 calc R U . . .
C22 C 0.46761(17) 0.3501(2) 0.17408(9) 0.0230(4) Uani 1 1 d . . . . .
H22 H 0.531569 0.331706 0.143557 0.028 Uiso 1 1 calc R U . . .
C23 C 0.47397(17) 0.2826(2) 0.24084(9) 0.0206(4) Uani 1 1 d . . . . .
H23 H 0.543189 0.220497 0.256190 0.025 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.7458(19) . ?
N1 C7 1.321(2) . ?
N1 O1 1.4113(19) . ?
O1 C9 1.363(2) . ?
C1 C6 1.384(2) . ?
C1 C2 1.390(3) . ?
C2 C3 1.383(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.398(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.394(3) . ?
C4 C7 1.472(3) . ?
C5 C6 1.386(3) . ?
C5 H5 0.9500 . ?
C8 C9 1.351(3) . ?
C8 C7 1.425(2) . ?
C8 H8 0.9500 . ?
C6 H6 0.9500 . ?
C9 C10 1.460(2) . ?
C10 C11 1.349(3) . ?
C10 C18 1.499(2) . ?
C11 C12 1.471(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.400(2) . ?
C12 C17 1.402(2) . ?
C13 C14 1.392(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.386(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.385(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.385(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.391(3) . ?
C18 C23 1.400(2) . ?
C19 C20 1.391(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.386(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.392(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.389(3) . ?
C22 H22 0.9500 . ?
C23 H23 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
C7 N1 O1 105.71(14) . . ?
C9 O1 N1 108.54(13) . . ?
C6 C1 C2 121.24(17) . . ?
C6 C1 Cl1 119.04(14) . . ?
C2 C1 Cl1 119.71(14) . . ?
C3 C2 C1 119.36(16) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 120.59(17) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 118.73(17) . . ?
C5 C4 C7 119.85(15) . . ?
C3 C4 C7 121.40(16) . . ?
C6 C5 C4 121.26(16) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C9 C8 C7 104.96(15) . . ?
C9 C8 H8 127.5 . . ?
C7 C8 H8 127.5 . . ?
N1 C7 C8 111.17(16) . . ?
N1 C7 C4 120.89(16) . . ?
C8 C7 C4 127.92(16) . . ?
C1 C6 C5 118.78(17) . . ?
C1 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
C8 C9 O1 109.61(15) . . ?
C8 C9 C10 132.03(16) . . ?
O1 C9 C10 118.30(16) . . ?
C11 C10 C9 120.68(16) . . ?
C11 C10 C18 124.33(16) . . ?
C9 C10 C18 114.95(16) . . ?
C10 C11 C12 128.69(16) . . ?
C10 C11 H11 115.7 . . ?
C12 C11 H11 115.7 . . ?
C13 C12 C17 117.52(16) . . ?
C13 C12 C11 118.66(16) . . ?
C17 C12 C11 123.65(16) . . ?
C14 C13 C12 121.20(17) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C15 C14 C13 120.26(18) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C16 C15 C14 119.27(17) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C17 C16 C15 120.65(17) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C12 121.09(17) . . ?
C16 C17 H17 119.5 . . ?
C12 C17 H17 119.5 . . ?
C19 C18 C23 118.88(16) . . ?
C19 C18 C10 120.45(15) . . ?
C23 C18 C10 120.64(16) . . ?
C20 C19 C18 120.69(17) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C21 C20 C19 120.19(18) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C20 C21 C22 119.63(17) . . ?
C20 C21 H21 120.2 . . ?
C22 C21 H21 120.2 . . ?
C23 C22 C21 120.28(17) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C22 C23 C18 120.30(17) . . ?
C22 C23 H23 119.9 . . ?
C18 C23 H23 119.9 . . ?

_refine_diff_density_max         0.429
_refine_diff_density_min         -0.396
_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_CRL371871_H
_database_code_depnum_ccdc_archive 'CCDC 1899699'
loop_
_audit_author_name
_audit_author_address
'Somaraju yugandhar'
;Tokyo institute of technology
India
;
_audit_update_record             
;
2019-02-26 deposited with the CCDC.	2019-06-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H14 Cl F6 N O'
_chemical_formula_weight         493.82

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   14.7536(19)
_cell_length_b                   6.9198(9)
_cell_length_c                   22.084(3)
_cell_angle_alpha                90
_cell_angle_beta                 108.867(2)
_cell_angle_gamma                90
_cell_volume                     2133.5(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    90
_cell_measurement_reflns_used    5355
_cell_measurement_theta_min      2.79
_cell_measurement_theta_max      29.95

_exptl_crystal_description       prism

_exptl_crystal_colour            colorless

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.537
_exptl_crystal_F_000             1000
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.250
_shelx_estimated_absorpt_T_min   0.963
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.947
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.333

_diffrn_reflns_number            12202
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_av_R_equivalents  0.0162
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.459
_diffrn_reflns_theta_max         29.058
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.919
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.919
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5256
_reflns_number_gt                4226
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'

_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'

_computing_data_reduction        'SAINT (Bruker AXS, 2004)'

_computing_structure_solution    'SHELXT (Sheldrick, 2014)'

_computing_structure_refinement  'SHELXL-2016 (Sheldrick, 2016)'

_computing_molecular_graphics    'XSHELXle (Bruker AXS)'

_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'


_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'

_computing_publication_material  'XCIF (Bruker AXS, 2001)'


_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)+(0.0536P)²+1.0348P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5256
_refine_ls_number_parameters     335
_refine_ls_number_restraints     498
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.1151
_refine_ls_wR_factor_gt          0.1080
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.246
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.05284(3) 0.82117(6) 0.40316(2) 0.03041(12) Uani 1 1 d . U . . .
O1 O 0.51675(7) 0.72641(16) 0.47590(5) 0.0192(2) Uani 1 1 d . U . . .
N1 N 0.41826(9) 0.7370(2) 0.44145(6) 0.0195(3) Uani 1 1 d . U . . .
C1 C 0.07182(11) 0.8129(2) 0.42668(8) 0.0216(3) Uani 1 1 d . U . . .
C2 C 0.12470(11) 0.8310(2) 0.49067(8) 0.0236(3) Uani 1 1 d . U . . .
H2 H 0.093670 0.853264 0.521613 0.028 Uiso 1 1 calc R U . . .
C3 C 0.22383(11) 0.8161(2) 0.50921(7) 0.0216(3) Uani 1 1 d . U . . .
H3 H 0.260545 0.827205 0.553191 0.026 Uiso 1 1 calc R U . . .
C4 C 0.27011(10) 0.7852(2) 0.46423(7) 0.0174(3) Uani 1 1 d . U . . .
C5 C 0.21497(11) 0.7712(2) 0.39965(7) 0.0214(3) Uani 1 1 d . U . . .
H5 H 0.245732 0.752757 0.368365 0.026 Uiso 1 1 calc R U . . .
C6 C 0.11612(11) 0.7840(2) 0.38074(8) 0.0240(3) Uani 1 1 d . U . . .
H6 H 0.079029 0.773125 0.336829 0.029 Uiso 1 1 calc R U . . .
C7 C 0.37529(10) 0.7676(2) 0.48437(7) 0.0161(3) Uani 1 1 d . U . . .
C9 C 0.52872(10) 0.7515(2) 0.53907(6) 0.0161(3) Uani 1 1 d . U . . .
C8 C 0.44239(11) 0.7774(2) 0.54714(7) 0.0182(3) Uani 1 1 d . U . . .
H8 H 0.429529 0.797557 0.586122 0.022 Uiso 1 1 calc R U . . .
C10 C 0.62613(10) 0.7452(2) 0.58418(7) 0.0166(3) Uani 1 1 d . U . . .
C11 C 0.63042(10) 0.7587(2) 0.65286(7) 0.0173(3) Uani 1 1 d . U . . .
C12 C 0.61783(11) 0.9348(2) 0.67900(7) 0.0212(3) Uani 1 1 d . U . . .
H12 H 0.607043 1.048260 0.653420 0.025 Uiso 1 1 calc R U . . .
C13 C 0.62094(11) 0.9461(2) 0.74267(7) 0.0233(3) Uani 1 1 d . U . . .
H13 H 0.612221 1.066903 0.760484 0.028 Uiso 1 1 calc R U . . .
C14 C 0.63680(11) 0.7804(2) 0.77985(7) 0.0210(3) Uani 1 1 d . U . . .
C15 C 0.64774(13) 0.6034(3) 0.75382(8) 0.0288(4) Uani 1 1 d . U . . .
H15 H 0.657852 0.489930 0.779373 0.035 Uiso 1 1 calc R U . . .
C16 C 0.64389(13) 0.5921(2) 0.69016(8) 0.0274(4) Uani 1 1 d . U . . .
H16 H 0.650465 0.470507 0.672061 0.033 Uiso 1 1 calc R U . . .
C17 C 0.64033(13) 0.7917(3) 0.84845(8) 0.0288(4) Uani 1 1 d . U . . .
C18 C 0.70094(11) 0.7270(2) 0.56224(7) 0.0178(3) Uani 1 1 d . U . . .
H18 H 0.683949 0.717131 0.517033 0.021 Uiso 1 1 calc R U . . .
C19 C 0.80437(11) 0.7197(2) 0.59651(7) 0.0179(3) Uani 1 1 d . U . . .
C20 C 0.84717(11) 0.7497(3) 0.66254(7) 0.0252(3) Uani 1 1 d . U . . .
H20 H 0.808156 0.775565 0.688413 0.030 Uiso 1 1 calc R U . . .
C21 C 0.94565(12) 0.7417(3) 0.69022(8) 0.0277(4) Uani 1 1 d . U . . .
H21 H 0.973609 0.763257 0.734898 0.033 Uiso 1 1 calc R U . . .
C22 C 1.00420(11) 0.7027(2) 0.65347(7) 0.0218(3) Uani 1 1 d . U . . .
C23 C 0.96336(11) 0.6722(2) 0.58801(7) 0.0217(3) Uani 1 1 d . U . . .
H23 H 1.002809 0.644618 0.562563 0.026 Uiso 1 1 calc R U . . .
C24 C 0.86462(11) 0.6825(2) 0.56007(7) 0.0199(3) Uani 1 1 d . U . . .
H24 H 0.837205 0.663909 0.515209 0.024 Uiso 1 1 calc R U . . .
C25 C 1.11052(11) 0.6916(3) 0.68549(8) 0.0276(4) Uani 1 1 d . U . . .
F1 F 0.6237(4) 0.9591(5) 0.86713(15) 0.0794(14) Uani 0.557(4) 1 d . U P A 1
F2 F 0.5866(3) 0.6658(7) 0.86321(14) 0.0795(14) Uani 0.557(4) 1 d . U P A 1
F3 F 0.7285(2) 0.7453(8) 0.88800(11) 0.0741(12) Uani 0.557(4) 1 d . U P A 1
F7 F 0.5498(3) 0.8184(9) 0.85040(15) 0.0689(13) Uani 0.443(4) 1 d . U P A 2
F8 F 0.6676(5) 0.6418(6) 0.88151(16) 0.0793(15) Uani 0.443(4) 1 d . U P A 2
F9 F 0.6847(4) 0.9396(8) 0.8788(2) 0.0763(16) Uani 0.443(4) 1 d . U P A 2
F4 F 1.14326(8) 0.8314(2) 0.72901(6) 0.0473(3) Uani 1 1 d . U . . .
F5 F 1.13706(7) 0.52509(19) 0.71728(6) 0.0490(3) Uani 1 1 d . U . . .
F6 F 1.16004(7) 0.7043(2) 0.64467(5) 0.0423(3) Uani 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.7429(15) . ?
O1 C9 1.3596(17) . ?
O1 N1 1.4074(15) . ?
N1 C7 1.3168(19) . ?
C1 C2 1.381(2) . ?
C1 C6 1.388(2) . ?
C2 C3 1.389(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.392(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.398(2) . ?
C4 C7 1.475(2) . ?
C5 C6 1.384(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.4208(19) . ?
C9 C8 1.354(2) . ?
C9 C10 1.461(2) . ?
C8 H8 0.9500 . ?
C10 C18 1.347(2) . ?
C10 C11 1.5003(19) . ?
C11 C12 1.387(2) . ?
C11 C16 1.393(2) . ?
C12 C13 1.394(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.386(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.384(2) . ?
C14 C17 1.501(2) . ?
C15 C16 1.391(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 F8 1.257(4) . ?
C17 F1 1.280(3) . ?
C17 F9 1.281(4) . ?
C17 F2 1.289(3) . ?
C17 F3 1.350(3) . ?
C17 F7 1.363(4) . ?
C18 C19 1.469(2) . ?
C18 H18 0.9500 . ?
C19 C24 1.402(2) . ?
C19 C20 1.405(2) . ?
C20 C21 1.383(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.390(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.391(2) . ?
C22 C25 1.500(2) . ?
C23 C24 1.388(2) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 F6 1.3343(19) . ?
C25 F4 1.339(2) . ?
C25 F5 1.340(2) . ?

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 O1 N1 108.47(11) . . ?
C7 N1 O1 105.81(11) . . ?
C2 C1 C6 121.15(14) . . ?
C2 C1 Cl1 119.63(12) . . ?
C6 C1 Cl1 119.21(12) . . ?
C1 C2 C3 119.15(14) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C2 C3 C4 120.92(14) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C5 118.73(14) . . ?
C3 C4 C7 120.58(13) . . ?
C5 C4 C7 120.68(13) . . ?
C6 C5 C4 120.80(15) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C1 119.22(14) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
N1 C7 C8 111.35(13) . . ?
N1 C7 C4 120.06(13) . . ?
C8 C7 C4 128.58(13) . . ?
C8 C9 O1 109.65(12) . . ?
C8 C9 C10 132.40(13) . . ?
O1 C9 C10 117.94(12) . . ?
C9 C8 C7 104.71(13) . . ?
C9 C8 H8 127.6 . . ?
C7 C8 H8 127.6 . . ?
C18 C10 C9 119.83(13) . . ?
C18 C10 C11 126.71(13) . . ?
C9 C10 C11 113.46(12) . . ?
C12 C11 C16 119.59(13) . . ?
C12 C11 C10 120.52(13) . . ?
C16 C11 C10 119.85(14) . . ?
C11 C12 C13 120.27(14) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C14 C13 C12 119.70(15) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C15 C14 C13 120.41(14) . . ?
C15 C14 C17 119.66(15) . . ?
C13 C14 C17 119.92(15) . . ?
C14 C15 C16 119.81(15) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C15 C16 C11 120.19(15) . . ?
C15 C16 H16 119.9 . . ?
C11 C16 H16 119.9 . . ?
F8 C17 F9 110.0(4) . . ?
F1 C17 F2 109.4(3) . . ?
F1 C17 F3 104.6(3) . . ?
F2 C17 F3 102.6(3) . . ?
F8 C17 F7 103.1(4) . . ?
F9 C17 F7 102.5(3) . . ?
F8 C17 C14 116.3(2) . . ?
F1 C17 C14 115.2(2) . . ?
F9 C17 C14 114.5(2) . . ?
F2 C17 C14 113.35(18) . . ?
F3 C17 C14 110.64(17) . . ?
F7 C17 C14 108.94(19) . . ?
C10 C18 C19 130.81(14) . . ?
C10 C18 H18 114.6 . . ?
C19 C18 H18 114.6 . . ?
C24 C19 C20 117.86(14) . . ?
C24 C19 C18 117.15(13) . . ?
C20 C19 C18 124.98(14) . . ?
C21 C20 C19 120.55(15) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C20 C21 C22 120.80(15) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
C21 C22 C23 119.63(14) . . ?
C21 C22 C25 119.17(14) . . ?
C23 C22 C25 121.19(14) . . ?
C24 C23 C22 119.60(14) . . ?
C24 C23 H23 120.2 . . ?
C22 C23 H23 120.2 . . ?
C23 C24 C19 121.55(14) . . ?
C23 C24 H24 119.2 . . ?
C19 C24 H24 119.2 . . ?
F6 C25 F4 106.73(14) . . ?
F6 C25 F5 106.25(15) . . ?
F4 C25 F5 105.60(14) . . ?
F6 C25 C22 113.31(13) . . ?
F4 C25 C22 112.39(14) . . ?
F5 C25 C22 112.01(14) . . ?

_refine_diff_density_max         0.630
_refine_diff_density_min         -0.479
_refine_diff_density_rms         0.052

####################################################################### 
# 
# 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_CRL372583_429_1_0m_b
_database_code_depnum_ccdc_archive 'CCDC 1870842'
loop_
_audit_author_name
_audit_author_address
'Somaraju yugandhar'
;Tokyo institute of technology
Japan
;
_audit_update_record             
;
2018-09-29 deposited with the CCDC.	2019-06-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19.50 H25.50 Cl2 N Rh'
_chemical_formula_weight         447.72

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'
Rh Rh -1.1178 0.9187 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   8.4219(12)
_cell_length_b                   35.714(5)
_cell_length_c                   13.5618(19)
_cell_angle_alpha                90
_cell_angle_beta                 101.876(2)
_cell_angle_gamma                90
_cell_volume                     3991.8(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    90
_cell_measurement_reflns_used    9983
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      28.92

_exptl_crystal_description       column

_exptl_crystal_colour            yellow

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_F_000             1828
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    1.123
_shelx_estimated_absorpt_T_min   0.832
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.868
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.333

_diffrn_reflns_number            23471
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -46
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.534
_diffrn_reflns_theta_max         28.977
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.909
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.909
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.704
_diffrn_reflns_point_group_measured_fraction_full 0.803
_reflns_number_total             14947
_reflns_number_gt                13719
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.525
_reflns_Friedel_fraction_max     0.492
_reflns_Friedel_fraction_full    0.603

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'

_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'

_computing_data_reduction        'SAINT (Bruker AXS, 2004)'

_computing_structure_solution    'SHELXT (Sheldrick, 2014)'

_computing_structure_refinement  'SHELXL-2016 (Sheldrick, 2016)'

_computing_molecular_graphics    'XSHELXle (Bruker AXS)'

_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'


_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'

_computing_publication_material  'XCIF (Bruker AXS, 2001)'


_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)+(0.0311P)²+15.9065P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 4297 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.446(17)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         14947
_refine_ls_number_parameters     843
_refine_ls_number_restraints     1024
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0487
_refine_ls_wR_factor_ref         0.1058
_refine_ls_wR_factor_gt          0.1035
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_restrained_S_all      1.100
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1A N 1.0139(10) 0.3392(2) 0.6829(5) 0.0172(16) Uani 1 1 d . U . . .
H1A H 1.001161 0.361867 0.656780 0.021 Uiso 1 1 calc R U . . .
C1A C 1.2025(12) 0.3232(3) 0.5724(7) 0.025(2) Uani 1 1 d . U . . .
H1AA H 1.161652 0.308679 0.511114 0.038 Uiso 1 1 calc R U . . .
H1AB H 1.315296 0.316162 0.600163 0.038 Uiso 1 1 calc R U . . .
H1AC H 1.197210 0.349979 0.556018 0.038 Uiso 1 1 calc R U . . .
Cl1A Cl 0.6486(3) 0.30797(9) 0.69231(18) 0.0311(6) Uani 1 1 d . U . . .
Rh1A Rh 0.90453(8) 0.32441(2) 0.80006(4) 0.01623(16) Uani 1 1 d . U . . .
C2A C 1.0994(12) 0.3152(3) 0.6495(6) 0.0191(18) Uani 1 1 d . U . . .
C1H C 0.900(4) 0.5315(9) 0.899(2) 0.175(12) Uiso 1 1 d D U . . .
H1HA H 0.824264 0.543281 0.936129 0.263 Uiso 1 1 calc R U . . .
H1HB H 0.846749 0.509931 0.861384 0.263 Uiso 1 1 calc R U . . .
H1HC H 0.930574 0.549652 0.852405 0.263 Uiso 1 1 calc R U . . .
Cl2A Cl 1.0376(3) 0.16552(7) 0.83081(16) 0.0250(5) Uani 1 1 d . U . . .
C3A C 1.0976(12) 0.2779(3) 0.6943(6) 0.0170(17) Uani 1 1 d . U . . .
C2H C 1.067(3) 0.5170(9) 0.982(2) 0.163(9) Uiso 1 1 d D U . . .
H2HA H 1.118033 0.537687 1.025902 0.196 Uiso 1 1 calc R U . . .
H2HB H 1.042916 0.495989 1.023916 0.196 Uiso 1 1 calc R U . . .
C4A C 1.0014(11) 0.2751(3) 0.7658(6) 0.0145(17) Uani 1 1 d . U . . .
C3H C 1.185(3) 0.5032(9) 0.9023(19) 0.165(8) Uiso 1 1 d D U . . .
H3HA H 1.218834 0.524164 0.863437 0.198 Uiso 1 1 calc R U . . .
H3HB H 1.136104 0.482814 0.856632 0.198 Uiso 1 1 calc R U . . .
C5A C 0.9803(11) 0.2393(3) 0.8058(6) 0.0142(17) Uani 1 1 d . U . . .
H5A H 0.910476 0.236128 0.852006 0.017 Uiso 1 1 calc R U . . .
C4H C 1.333(3) 0.4884(10) 0.997(2) 0.176(9) Uiso 1 1 d D U . . .
H4HA H 1.297619 0.467476 1.035223 0.211 Uiso 1 1 calc R U . . .
H4HB H 1.377432 0.508947 1.043924 0.211 Uiso 1 1 calc R U . . .
C6A C 1.0616(12) 0.2093(3) 0.7775(6) 0.0187(18) Uani 1 1 d . U . . .
C5H C 1.465(4) 0.4745(11) 0.926(2) 0.192(10) Uiso 1 1 d D U . . .
H5HA H 1.498812 0.496017 0.889411 0.231 Uiso 1 1 calc R U . . .
H5HB H 1.414258 0.455428 0.876507 0.231 Uiso 1 1 calc R U . . .
C7A C 1.1666(13) 0.2124(3) 0.7106(6) 0.0213(19) Uani 1 1 d . U . . .
H7A H 1.226244 0.191407 0.695165 0.026 Uiso 1 1 calc R U . . .
C6H C 1.626(4) 0.4561(10) 1.007(3) 0.219(15) Uiso 1 1 d D U . . .
H6HA H 1.688245 0.440178 0.969778 0.328 Uiso 1 1 calc R U . . .
H6HB H 1.588199 0.441152 1.058094 0.328 Uiso 1 1 calc R U . . .
H6HC H 1.695773 0.476435 1.039934 0.328 Uiso 1 1 calc R U . . .
C8A C 1.1814(12) 0.2475(3) 0.6669(6) 0.0209(19) Uani 1 1 d . U . . .
H8A H 1.248288 0.250413 0.618916 0.025 Uiso 1 1 calc R U . . .
C9A C 1.0020(12) 0.3203(3) 0.9613(6) 0.0221(18) Uani 1 1 d . U . . .
C10A C 0.8307(12) 0.3254(3) 0.9449(6) 0.027(2) Uani 1 1 d . U . . .
C11A C 0.7928(14) 0.3622(3) 0.8995(7) 0.032(2) Uani 1 1 d . U . . .
C12A C 0.9314(15) 0.3784(3) 0.8832(7) 0.031(2) Uani 1 1 d . U . . .
C13A C 1.0667(13) 0.3515(3) 0.9171(7) 0.028(2) Uani 1 1 d . U . . .
C14A C 1.0933(14) 0.2883(4) 1.0146(7) 0.031(3) Uani 1 1 d . U . . .
H14A H 1.138971 0.295420 1.084504 0.046 Uiso 1 1 calc R U . . .
H14B H 1.181236 0.281346 0.980858 0.046 Uiso 1 1 calc R U . . .
H14C H 1.019939 0.266945 1.013892 0.046 Uiso 1 1 calc R U . . .
C15A C 0.7118(17) 0.3003(5) 0.9797(10) 0.055(4) Uani 1 1 d . U . . .
H15A H 0.683650 0.310760 1.040674 0.082 Uiso 1 1 calc R U . . .
H15B H 0.760009 0.275432 0.994607 0.082 Uiso 1 1 calc R U . . .
H15C H 0.613694 0.298216 0.926728 0.082 Uiso 1 1 calc R U . . .
C16A C 0.6243(18) 0.3776(5) 0.8783(9) 0.059(4) Uani 1 1 d . U . . .
H16A H 0.581282 0.377200 0.940119 0.089 Uiso 1 1 calc R U . . .
H16B H 0.555154 0.362274 0.826655 0.089 Uiso 1 1 calc R U . . .
H16C H 0.625884 0.403420 0.854044 0.089 Uiso 1 1 calc R U . . .
C17A C 0.956(2) 0.4163(4) 0.8393(8) 0.056(4) Uani 1 1 d . U . . .
H17A H 0.978327 0.434909 0.893561 0.084 Uiso 1 1 calc R U . . .
H17B H 0.857168 0.423477 0.790916 0.084 Uiso 1 1 calc R U . . .
H17C H 1.047257 0.415186 0.805045 0.084 Uiso 1 1 calc R U . . .
C18A C 1.2410(17) 0.3598(4) 0.9187(9) 0.049(3) Uani 1 1 d . U . . .
H18A H 1.282177 0.377533 0.973066 0.073 Uiso 1 1 calc R U . . .
H18B H 1.251354 0.370655 0.854037 0.073 Uiso 1 1 calc R U . . .
H18C H 1.303935 0.336518 0.930198 0.073 Uiso 1 1 calc R U . . .
C1B C 0.6981(12) 0.6768(3) 0.5525(7) 0.024(2) Uani 1 1 d . U . . .
H1BA H 0.814969 0.679726 0.578423 0.036 Uiso 1 1 calc R U . . .
H1BB H 0.663430 0.693695 0.495098 0.036 Uiso 1 1 calc R U . . .
H1BC H 0.674648 0.650887 0.530737 0.036 Uiso 1 1 calc R U . . .
N1B N 0.5185(9) 0.6608(2) 0.6649(5) 0.0151(15) Uani 1 1 d . U . . .
H1B H 0.500621 0.638798 0.635535 0.018 Uiso 1 1 calc R U . . .
Cl1B Cl 0.1565(3) 0.68991(9) 0.68426(18) 0.0293(6) Uani 1 1 d . U . . .
Rh1B Rh 0.42025(8) 0.67470(2) 0.78648(4) 0.01647(16) Uani 1 1 d . U . . .
C2B C 0.6096(10) 0.6861(3) 0.6327(6) 0.0134(16) Uani 1 1 d . U . . .
Cl2B Cl 0.5388(3) 0.83423(8) 0.81733(17) 0.0271(6) Uani 1 1 d . U . . .
C3B C 0.6037(11) 0.7227(3) 0.6775(6) 0.0147(16) Uani 1 1 d . U . . .
C4B C 0.5067(11) 0.7247(3) 0.7507(6) 0.0155(17) Uani 1 1 d . U . . .
C5B C 0.4859(12) 0.7592(3) 0.7915(6) 0.0189(18) Uani 1 1 d . U . . .
H5B H 0.418262 0.761599 0.839211 0.023 Uiso 1 1 calc R U . . .
C6B C 0.5643(12) 0.7908(3) 0.7630(6) 0.0188(18) Uani 1 1 d . U . . .
C7B C 0.6627(12) 0.7887(3) 0.6939(6) 0.0213(19) Uani 1 1 d . U . . .
H7B H 0.715547 0.810483 0.676368 0.026 Uiso 1 1 calc R U . . .
C8B C 0.6841(12) 0.7547(3) 0.6502(6) 0.0203(18) Uani 1 1 d . U . . .
H8B H 0.751912 0.752817 0.602435 0.024 Uiso 1 1 calc R U . . .
C9B C 0.3303(14) 0.6330(3) 0.8880(7) 0.031(2) Uani 1 1 d . U . . .
C10B C 0.3544(12) 0.6700(4) 0.9333(6) 0.028(2) Uani 1 1 d . U . . .
C11B C 0.5202(11) 0.6783(3) 0.9464(6) 0.0200(17) Uani 1 1 d . U . . .
C12B C 0.5982(13) 0.6487(3) 0.9032(6) 0.0244(19) Uani 1 1 d . U . . .
C13B C 0.4741(14) 0.6198(3) 0.8714(7) 0.030(2) Uani 1 1 d . U . . .
C14B C 0.1694(15) 0.6123(4) 0.8691(9) 0.046(3) Uani 1 1 d . U . . .
H14D H 0.147344 0.603430 0.933386 0.070 Uiso 1 1 calc R U . . .
H14E H 0.174691 0.590802 0.824887 0.070 Uiso 1 1 calc R U . . .
H14F H 0.082493 0.629185 0.836944 0.070 Uiso 1 1 calc R U . . .
C15B C 0.2245(16) 0.6920(5) 0.9687(9) 0.049(3) Uani 1 1 d . U . . .
H15D H 0.183304 0.677480 1.019414 0.074 Uiso 1 1 calc R U . . .
H15E H 0.135527 0.697220 0.911429 0.074 Uiso 1 1 calc R U . . .
H15F H 0.270009 0.715687 0.998478 0.074 Uiso 1 1 calc R U . . .
C16B C 0.6073(13) 0.7118(3) 1.0016(6) 0.024(2) Uani 1 1 d . U . . .
H16D H 0.640698 0.705959 1.073449 0.036 Uiso 1 1 calc R U . . .
H16E H 0.534216 0.733439 0.992756 0.036 Uiso 1 1 calc R U . . .
H16F H 0.703373 0.717628 0.974082 0.036 Uiso 1 1 calc R U . . .
C17B C 0.7720(14) 0.6451(4) 0.9017(8) 0.038(3) Uani 1 1 d . U . . .
H17D H 0.827216 0.631630 0.961985 0.057 Uiso 1 1 calc R U . . .
H17E H 0.819777 0.670116 0.900767 0.057 Uiso 1 1 calc R U . . .
H17F H 0.784531 0.631283 0.841417 0.057 Uiso 1 1 calc R U . . .
C18B C 0.5074(19) 0.5833(4) 0.8250(9) 0.049(3) Uani 1 1 d . U . . .
H18D H 0.546842 0.565006 0.878313 0.074 Uiso 1 1 calc R U . . .
H18E H 0.589816 0.586975 0.784327 0.074 Uiso 1 1 calc R U . . .
H18F H 0.407240 0.573947 0.781904 0.074 Uiso 1 1 calc R U . . .
C1C C 0.7950(15) 0.2920(3) 0.4452(8) 0.029(2) Uani 1 1 d . U . . .
H1CA H 0.729384 0.280181 0.385222 0.044 Uiso 1 1 calc R U . . .
H1CB H 0.752105 0.285099 0.504600 0.044 Uiso 1 1 calc R U . . .
H1CC H 0.907643 0.283523 0.453958 0.044 Uiso 1 1 calc R U . . .
N1C N 0.7347(10) 0.3561(2) 0.4928(5) 0.0185(16) Uani 1 1 d . U . . .
H1C H 0.701766 0.347052 0.545555 0.022 Uiso 1 1 calc R U . . .
Cl1C Cl 0.9980(3) 0.42129(7) 0.56044(16) 0.0188(5) Uani 1 1 d . U . . .
Rh1C Rh 0.72641(8) 0.41304(2) 0.46407(5) 0.01400(15) Uani 1 1 d . U . . .
C2C C 0.7884(13) 0.3342(3) 0.4325(6) 0.0217(19) Uani 1 1 d . U . . .
Cl2C Cl 1.0438(4) 0.42243(11) 0.12603(19) 0.0454(9) Uani 1 1 d . U . . .
C3C C 0.8487(13) 0.3531(3) 0.3518(7) 0.024(2) Uani 1 1 d . U . . .
C4C C 0.8293(12) 0.3923(3) 0.3532(6) 0.0205(19) Uani 1 1 d . U . . .
C5C C 0.8907(12) 0.4131(4) 0.2828(6) 0.027(2) Uani 1 1 d . U . . .
H5C H 0.883856 0.439667 0.284129 0.032 Uiso 1 1 calc R U . . .
C6C C 0.9615(13) 0.3960(4) 0.2110(7) 0.027(2) Uani 1 1 d . U . . .
C7C C 0.9762(15) 0.3579(4) 0.2081(7) 0.034(2) Uani 1 1 d . U . . .
H7C H 1.024999 0.346467 0.158476 0.041 Uiso 1 1 calc R U . . .
C8C C 0.9184(13) 0.3356(4) 0.2794(7) 0.029(2) Uani 1 1 d . U . . .
H8C H 0.927044 0.309127 0.277911 0.035 Uiso 1 1 calc R U . . .
C9C C 0.4688(11) 0.4193(3) 0.4323(6) 0.0153(17) Uani 1 1 d . U . . .
C10C C 0.5365(11) 0.4436(3) 0.3665(6) 0.0145(17) Uani 1 1 d . U . . .
C11C C 0.6399(11) 0.4698(3) 0.4307(6) 0.0159(17) Uani 1 1 d . U . . .
C12C C 0.6272(12) 0.4632(3) 0.5338(7) 0.0193(19) Uani 1 1 d . U . . .
C13C C 0.5209(11) 0.4329(3) 0.5350(6) 0.0165(18) Uani 1 1 d . U . . .
C14C C 0.3451(13) 0.3894(3) 0.4003(7) 0.021(2) Uani 1 1 d . U . . .
H14G H 0.239916 0.397738 0.412410 0.031 Uiso 1 1 calc R U . . .
H14H H 0.378554 0.366547 0.439043 0.031 Uiso 1 1 calc R U . . .
H14I H 0.335567 0.384221 0.328307 0.031 Uiso 1 1 calc R U . . .
C15C C 0.4977(13) 0.4434(3) 0.2541(6) 0.023(2) Uani 1 1 d . U . . .
H15G H 0.408466 0.460857 0.229688 0.035 Uiso 1 1 calc R U . . .
H15H H 0.465612 0.418117 0.229878 0.035 Uiso 1 1 calc R U . . .
H15I H 0.593669 0.451143 0.228800 0.035 Uiso 1 1 calc R U . . .
C16C C 0.7323(13) 0.5026(3) 0.3961(8) 0.027(2) Uani 1 1 d . U . . .
H16G H 0.667137 0.525446 0.393214 0.040 Uiso 1 1 calc R U . . .
H16H H 0.753324 0.497175 0.329138 0.040 Uiso 1 1 calc R U . . .
H16I H 0.835585 0.506105 0.443922 0.040 Uiso 1 1 calc R U . . .
C17C C 0.7124(14) 0.4855(3) 0.6212(8) 0.028(2) Uani 1 1 d . U . . .
H17G H 0.679546 0.511752 0.611889 0.042 Uiso 1 1 calc R U . . .
H17H H 0.829870 0.483442 0.626475 0.042 Uiso 1 1 calc R U . . .
H17I H 0.683915 0.475861 0.683047 0.042 Uiso 1 1 calc R U . . .
C18C C 0.4618(12) 0.4158(4) 0.6233(6) 0.023(2) Uani 1 1 d . U . . .
H18G H 0.342954 0.415934 0.609432 0.034 Uiso 1 1 calc R U . . .
H18H H 0.503501 0.430362 0.684373 0.034 Uiso 1 1 calc R U . . .
H18I H 0.500948 0.389921 0.633253 0.034 Uiso 1 1 calc R U . . .
C1D C 0.2851(15) 0.7083(4) 0.4351(8) 0.031(2) Uani 1 1 d . U . . .
H1DA H 0.392902 0.718172 0.432820 0.047 Uiso 1 1 calc R U . . .
H1DB H 0.259240 0.714111 0.500665 0.047 Uiso 1 1 calc R U . . .
H1DC H 0.204098 0.719924 0.381513 0.047 Uiso 1 1 calc R U . . .
N1D N 0.2297(11) 0.6445(3) 0.4805(6) 0.0207(17) Uani 1 1 d . U . . .
H1D H 0.196403 0.653239 0.533439 0.025 Uiso 1 1 calc R U . . .
Cl1D Cl 0.4972(3) 0.57938(7) 0.54310(16) 0.0210(5) Uani 1 1 d . U . . .
Rh1D Rh 0.22302(8) 0.58797(2) 0.44998(5) 0.01490(15) Uani 1 1 d . U . . .
C2D C 0.2836(12) 0.6669(3) 0.4203(7) 0.024(2) Uani 1 1 d . U . . .
Cl2D Cl 0.5403(4) 0.58078(12) 0.11208(19) 0.0496(10) Uani 1 1 d . U . . .
C3D C 0.3388(12) 0.6483(3) 0.3380(6) 0.0209(18) Uani 1 1 d . U . . .
C4D C 0.3255(11) 0.6085(3) 0.3385(6) 0.0171(18) Uani 1 1 d . U . . .
C5D C 0.3859(12) 0.5878(4) 0.2670(7) 0.0254(19) Uani 1 1 d . U . . .
H5D H 0.378146 0.561314 0.264391 0.030 Uiso 1 1 calc R U . . .
C6D C 0.4589(14) 0.6080(4) 0.1987(7) 0.032(2) Uani 1 1 d . U . . .
C7D C 0.4727(15) 0.6463(4) 0.1976(7) 0.035(2) Uani 1 1 d . U . . .
H7D H 0.522464 0.658361 0.149371 0.042 Uiso 1 1 calc R U . . .
C8D C 0.4132(13) 0.6665(4) 0.2672(7) 0.032(2) Uani 1 1 d . U . . .
H8D H 0.421915 0.693038 0.267975 0.038 Uiso 1 1 calc R U . . .
C9D C -0.0356(11) 0.5804(3) 0.4176(6) 0.0146(17) Uani 1 1 d . U . . .
C10D C 0.0168(12) 0.5688(3) 0.5220(7) 0.0174(17) Uani 1 1 d . U . . .
C11D C 0.1248(12) 0.5388(3) 0.5232(7) 0.0172(17) Uani 1 1 d . U . . .
C12D C 0.1411(13) 0.5310(3) 0.4197(7) 0.0213(19) Uani 1 1 d . U . . .
C13D C 0.0338(11) 0.5555(3) 0.3545(6) 0.0151(17) Uani 1 1 d . U . . .
C14D C -0.1600(12) 0.6102(3) 0.3822(7) 0.021(2) Uani 1 1 d . U . . .
H14J H -0.265954 0.601820 0.392935 0.031 Uiso 1 1 calc R U . . .
H14K H -0.166532 0.614939 0.310349 0.031 Uiso 1 1 calc R U . . .
H14L H -0.128545 0.633257 0.420394 0.031 Uiso 1 1 calc R U . . .
C15D C -0.0395(12) 0.5850(3) 0.6095(7) 0.024(2) Uani 1 1 d . U . . .
H15J H -0.154422 0.579019 0.604434 0.036 Uiso 1 1 calc R U . . .
H15K H -0.025356 0.612232 0.609842 0.036 Uiso 1 1 calc R U . . .
H15L H 0.024217 0.574428 0.671908 0.036 Uiso 1 1 calc R U . . .
C16D C 0.2140(14) 0.5170(3) 0.6130(8) 0.028(2) Uani 1 1 d . U . . .
H16J H 0.165405 0.492129 0.613324 0.041 Uiso 1 1 calc R U . . .
H16K H 0.206162 0.530335 0.675001 0.041 Uiso 1 1 calc R U . . .
H16L H 0.328329 0.514539 0.608867 0.041 Uiso 1 1 calc R U . . .
C17D C 0.2269(15) 0.4986(4) 0.3893(8) 0.033(3) Uani 1 1 d . U . . .
H17J H 0.172348 0.475485 0.403086 0.049 Uiso 1 1 calc R U . . .
H17K H 0.339147 0.498397 0.427467 0.049 Uiso 1 1 calc R U . . .
H17L H 0.226394 0.500143 0.317097 0.049 Uiso 1 1 calc R U . . .
C18D C -0.0046(12) 0.5549(3) 0.2415(7) 0.025(2) Uani 1 1 d . U . . .
H18J H -0.109528 0.542559 0.217748 0.037 Uiso 1 1 calc R U . . .
H18K H 0.080184 0.541053 0.217148 0.037 Uiso 1 1 calc R U . . .
H18L H -0.009676 0.580586 0.215873 0.037 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1A C2A 1.263(13) . ?
N1A Rh1A 2.063(6) . ?
N1A H1A 0.8800 . ?
C1A C2A 1.517(11) . ?
C1A H1AA 0.9800 . ?
C1A H1AB 0.9800 . ?
C1A H1AC 0.9800 . ?
Cl1A Rh1A 2.414(3) . ?
Rh1A C4A 2.033(10) . ?
Rh1A C13A 2.105(10) . ?
Rh1A C9A 2.176(8) . ?
Rh1A C10A 2.179(8) . ?
Rh1A C12A 2.222(11) . ?
Rh1A C11A 2.247(9) . ?
C2A C3A 1.468(14) . ?
C1H C2H 1.694(17) . ?
C1H H1HA 0.9800 . ?
C1H H1HB 0.9800 . ?
C1H H1HC 0.9800 . ?
Cl2A C6A 1.752(10) . ?
C3A C8A 1.385(13) . ?
C3A C4A 1.389(11) . ?
C2H C3H 1.680(17) . ?
C2H H2HA 0.9900 . ?
C2H H2HB 0.9900 . ?
C4A C5A 1.415(13) . ?
C3H C4H 1.683(18) . ?
C3H H3HA 0.9900 . ?
C3H H3HB 0.9900 . ?
C5A C6A 1.368(14) . ?
C5A H5A 0.9500 . ?
C4H C5H 1.687(18) . ?
C4H H4HA 0.9900 . ?
C4H H4HB 0.9900 . ?
C6A C7A 1.395(13) . ?
C5H C6H 1.693(18) . ?
C5H H5HA 0.9900 . ?
C5H H5HB 0.9900 . ?
C7A C8A 1.403(14) . ?
C7A H7A 0.9500 . ?
C6H H6HA 0.9800 . ?
C6H H6HB 0.9800 . ?
C6H H6HC 0.9800 . ?
C8A H8A 0.9500 . ?
C9A C10A 1.425(13) . ?
C9A C13A 1.425(15) . ?
C9A C14A 1.481(15) . ?
C10A C11A 1.459(16) . ?
C10A C15A 1.491(16) . ?
C11A C12A 1.362(17) . ?
C11A C16A 1.494(16) . ?
C12A C13A 1.489(16) . ?
C12A C17A 1.509(18) . ?
C13A C18A 1.493(17) . ?
C14A H14A 0.9800 . ?
C14A H14B 0.9800 . ?
C14A H14C 0.9800 . ?
C15A H15A 0.9800 . ?
C15A H15B 0.9800 . ?
C15A H15C 0.9800 . ?
C16A H16A 0.9800 . ?
C16A H16B 0.9800 . ?
C16A H16C 0.9800 . ?
C17A H17A 0.9800 . ?
C17A H17B 0.9800 . ?
C17A H17C 0.9800 . ?
C18A H18A 0.9800 . ?
C18A H18B 0.9800 . ?
C18A H18C 0.9800 . ?
C1B C2B 1.478(11) . ?
C1B H1BA 0.9800 . ?
C1B H1BB 0.9800 . ?
C1B H1BC 0.9800 . ?
N1B C2B 1.318(11) . ?
N1B Rh1B 2.052(7) . ?
N1B H1B 0.8800 . ?
Cl1B Rh1B 2.425(3) . ?
Rh1B C4B 2.026(10) . ?
Rh1B C12B 2.154(10) . ?
Rh1B C11B 2.163(8) . ?
Rh1B C10B 2.180(8) . ?
Rh1B C9B 2.262(10) . ?
Rh1B C13B 2.271(11) . ?
C2B C3B 1.444(13) . ?
Cl2B C6B 1.749(10) . ?
C3B C4B 1.410(11) . ?
C3B C8B 1.418(13) . ?
C4B C5B 1.376(14) . ?
C5B C6B 1.401(14) . ?
C5B H5B 0.9500 . ?
C6B C7B 1.375(13) . ?
C7B C8B 1.378(14) . ?
C7B H7B 0.9500 . ?
C8B H8B 0.9500 . ?
C9B C13B 1.360(16) . ?
C9B C10B 1.455(17) . ?
C9B C14B 1.518(15) . ?
C10B C11B 1.402(13) . ?
C10B C15B 1.504(15) . ?
C11B C12B 1.433(14) . ?
C11B C16B 1.517(15) . ?
C12B C13B 1.468(16) . ?
C12B C17B 1.473(15) . ?
C13B C18B 1.501(17) . ?
C14B H14D 0.9800 . ?
C14B H14E 0.9800 . ?
C14B H14F 0.9800 . ?
C15B H15D 0.9800 . ?
C15B H15E 0.9800 . ?
C15B H15F 0.9800 . ?
C16B H16D 0.9800 . ?
C16B H16E 0.9800 . ?
C16B H16F 0.9800 . ?
C17B H17D 0.9800 . ?
C17B H17E 0.9800 . ?
C17B H17F 0.9800 . ?
C18B H18D 0.9800 . ?
C18B H18E 0.9800 . ?
C18B H18F 0.9800 . ?
C1C C2C 1.515(15) . ?
C1C H1CA 0.9800 . ?
C1C H1CB 0.9800 . ?
C1C H1CC 0.9800 . ?
N1C C2C 1.279(13) . ?
N1C Rh1C 2.070(9) . ?
N1C H1C 0.8800 . ?
Cl1C Rh1C 2.407(2) . ?
Rh1C C4C 2.025(9) . ?
Rh1C C9C 2.135(9) . ?
Rh1C C10C 2.151(9) . ?
Rh1C C11C 2.170(10) . ?
Rh1C C13C 2.261(9) . ?
Rh1C C12C 2.263(10) . ?
C2C C3C 1.464(15) . ?
Cl2C C6C 1.739(11) . ?
C3C C8C 1.392(13) . ?
C3C C4C 1.407(16) . ?
C4C C5C 1.391(15) . ?
C5C C6C 1.384(14) . ?
C5C H5C 0.9500 . ?
C6C C7C 1.369(18) . ?
C7C C8C 1.413(17) . ?
C7C H7C 0.9500 . ?
C8C H8C 0.9500 . ?
C9C C10C 1.442(12) . ?
C9C C13C 1.455(12) . ?
C9C C14C 1.494(13) . ?
C10C C11C 1.442(13) . ?
C10C C15C 1.493(11) . ?
C11C C12C 1.443(12) . ?
C11C C16C 1.532(14) . ?
C12C C13C 1.406(15) . ?
C12C C17C 1.484(14) . ?
C13C C18C 1.517(12) . ?
C14C H14G 0.9800 . ?
C14C H14H 0.9800 . ?
C14C H14I 0.9800 . ?
C15C H15G 0.9800 . ?
C15C H15H 0.9800 . ?
C15C H15I 0.9800 . ?
C16C H16G 0.9800 . ?
C16C H16H 0.9800 . ?
C16C H16I 0.9800 . ?
C17C H17G 0.9800 . ?
C17C H17H 0.9800 . ?
C17C H17I 0.9800 . ?
C18C H18G 0.9800 . ?
C18C H18H 0.9800 . ?
C18C H18I 0.9800 . ?
C1D C2D 1.493(17) . ?
C1D H1DA 0.9800 . ?
C1D H1DB 0.9800 . ?
C1D H1DC 0.9800 . ?
N1D C2D 1.290(13) . ?
N1D Rh1D 2.060(9) . ?
N1D H1D 0.8800 . ?
Cl1D Rh1D 2.412(2) . ?
Rh1D C4D 2.026(9) . ?
Rh1D C9D 2.149(9) . ?
Rh1D C12D 2.160(10) . ?
Rh1D C13D 2.171(10) . ?
Rh1D C11D 2.256(10) . ?
Rh1D C10D 2.267(9) . ?
C2D C3D 1.456(15) . ?
Cl2D C6D 1.768(12) . ?
C3D C8D 1.409(13) . ?
C3D C4D 1.425(15) . ?
C4D C5D 1.396(13) . ?
C5D C6D 1.409(14) . ?
C5D H5D 0.9500 . ?
C6D C7D 1.372(18) . ?
C7D C8D 1.364(18) . ?
C7D H7D 0.9500 . ?
C8D H8D 0.9500 . ?
C9D C13D 1.438(12) . ?
C9D C10D 1.453(12) . ?
C9D C14D 1.502(13) . ?
C10D C11D 1.403(14) . ?
C10D C15D 1.482(13) . ?
C11D C12D 1.465(12) . ?
C11D C16D 1.508(13) . ?
C12D C13D 1.426(14) . ?
C12D C17D 1.469(15) . ?
C13D C18D 1.499(12) . ?
C14D H14J 0.9800 . ?
C14D H14K 0.9800 . ?
C14D H14L 0.9800 . ?
C15D H15J 0.9800 . ?
C15D H15K 0.9800 . ?
C15D H15L 0.9800 . ?
C16D H16J 0.9800 . ?
C16D H16K 0.9800 . ?
C16D H16L 0.9800 . ?
C17D H17J 0.9800 . ?
C17D H17K 0.9800 . ?
C17D H17L 0.9800 . ?
C18D H18J 0.9800 . ?
C18D H18K 0.9800 . ?
C18D H18L 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
C2A N1A Rh1A 118.7(7) . . ?
C2A N1A H1A 120.6 . . ?
Rh1A N1A H1A 120.6 . . ?
C2A C1A H1AA 109.5 . . ?
C2A C1A H1AB 109.5 . . ?
H1AA C1A H1AB 109.5 . . ?
C2A C1A H1AC 109.5 . . ?
H1AA C1A H1AC 109.5 . . ?
H1AB C1A H1AC 109.5 . . ?
C4A Rh1A N1A 77.4(3) . . ?
C4A Rh1A C13A 110.0(4) . . ?
N1A Rh1A C13A 98.0(4) . . ?
C4A Rh1A C9A 94.9(4) . . ?
N1A Rh1A C9A 130.9(3) . . ?
C13A Rh1A C9A 38.8(4) . . ?
C4A Rh1A C10A 115.0(4) . . ?
N1A Rh1A C10A 161.0(4) . . ?
C13A Rh1A C10A 64.8(4) . . ?
C9A Rh1A C10A 38.2(3) . . ?
C4A Rh1A C12A 149.7(4) . . ?
N1A Rh1A C12A 98.8(4) . . ?
C13A Rh1A C12A 40.1(4) . . ?
C9A Rh1A C12A 64.6(4) . . ?
C10A Rh1A C12A 63.1(4) . . ?
C4A Rh1A C11A 153.4(4) . . ?
N1A Rh1A C11A 128.1(4) . . ?
C13A Rh1A C11A 63.8(4) . . ?
C9A Rh1A C11A 63.6(4) . . ?
C10A Rh1A C11A 38.5(4) . . ?
C12A Rh1A C11A 35.5(4) . . ?
C4A Rh1A Cl1A 90.1(3) . . ?
N1A Rh1A Cl1A 94.6(2) . . ?
C13A Rh1A Cl1A 158.2(3) . . ?
C9A Rh1A Cl1A 134.2(3) . . ?
C10A Rh1A Cl1A 99.5(3) . . ?
C12A Rh1A Cl1A 120.2(3) . . ?
C11A Rh1A Cl1A 94.4(3) . . ?
N1A C2A C3A 114.4(8) . . ?
N1A C2A C1A 124.7(10) . . ?
C3A C2A C1A 120.8(9) . . ?
C2H C1H H1HA 109.5 . . ?
C2H C1H H1HB 109.5 . . ?
H1HA C1H H1HB 109.5 . . ?
C2H C1H H1HC 109.5 . . ?
H1HA C1H H1HC 109.5 . . ?
H1HB C1H H1HC 109.5 . . ?
C8A C3A C4A 122.3(9) . . ?
C8A C3A C2A 123.5(8) . . ?
C4A C3A C2A 114.2(9) . . ?
C3H C2H C1H 101(2) . . ?
C3H C2H H2HA 111.6 . . ?
C1H C2H H2HA 111.6 . . ?
C3H C2H H2HB 111.6 . . ?
C1H C2H H2HB 111.6 . . ?
H2HA C2H H2HB 109.4 . . ?
C3A C4A C5A 117.9(9) . . ?
C3A C4A Rh1A 114.7(7) . . ?
C5A C4A Rh1A 127.3(6) . . ?
C2H C3H C4H 93(2) . . ?
C2H C3H H3HA 113.2 . . ?
C4H C3H H3HA 113.2 . . ?
C2H C3H H3HB 113.2 . . ?
C4H C3H H3HB 113.2 . . ?
H3HA C3H H3HB 110.6 . . ?
C6A C5A C4A 119.4(8) . . ?
C6A C5A H5A 120.3 . . ?
C4A C5A H5A 120.3 . . ?
C3H C4H C5H 97(2) . . ?
C3H C4H H4HA 112.3 . . ?
C5H C4H H4HA 112.3 . . ?
C3H C4H H4HB 112.3 . . ?
C5H C4H H4HB 112.3 . . ?
H4HA C4H H4HB 109.9 . . ?
C5A C6A C7A 122.8(9) . . ?
C5A C6A Cl2A 118.4(7) . . ?
C7A C6A Cl2A 118.8(8) . . ?
C4H C5H C6H 106(2) . . ?
C4H C5H H5HA 110.5 . . ?
C6H C5H H5HA 110.5 . . ?
C4H C5H H5HB 110.5 . . ?
C6H C5H H5HB 110.5 . . ?
H5HA C5H H5HB 108.7 . . ?
C6A C7A C8A 118.0(9) . . ?
C6A C7A H7A 121.0 . . ?
C8A C7A H7A 121.0 . . ?
C5H C6H H6HA 109.5 . . ?
C5H C6H H6HB 109.5 . . ?
H6HA C6H H6HB 109.5 . . ?
C5H C6H H6HC 109.5 . . ?
H6HA C6H H6HC 109.5 . . ?
H6HB C6H H6HC 109.5 . . ?
C3A C8A C7A 119.4(8) . . ?
C3A C8A H8A 120.3 . . ?
C7A C8A H8A 120.3 . . ?
C10A C9A C13A 107.3(9) . . ?
C10A C9A C14A 125.5(10) . . ?
C13A C9A C14A 127.2(10) . . ?
C10A C9A Rh1A 71.0(5) . . ?
C13A C9A Rh1A 67.9(5) . . ?
C14A C9A Rh1A 126.4(7) . . ?
C9A C10A C11A 107.8(10) . . ?
C9A C10A C15A 126.8(10) . . ?
C11A C10A C15A 124.9(10) . . ?
C9A C10A Rh1A 70.8(4) . . ?
C11A C10A Rh1A 73.3(5) . . ?
C15A C10A Rh1A 127.7(9) . . ?
C12A C11A C10A 109.4(9) . . ?
C12A C11A C16A 128.6(12) . . ?
C10A C11A C16A 122.0(11) . . ?
C12A C11A Rh1A 71.3(6) . . ?
C10A C11A Rh1A 68.3(5) . . ?
C16A C11A Rh1A 127.2(8) . . ?
C11A C12A C13A 107.6(10) . . ?
C11A C12A C17A 129.5(12) . . ?
C13A C12A C17A 122.9(12) . . ?
C11A C12A Rh1A 73.3(7) . . ?
C13A C12A Rh1A 65.7(6) . . ?
C17A C12A Rh1A 125.9(7) . . ?
C9A C13A C12A 107.4(9) . . ?
C9A C13A C18A 127.4(11) . . ?
C12A C13A C18A 124.4(11) . . ?
C9A C13A Rh1A 73.3(6) . . ?
C12A C13A Rh1A 74.1(6) . . ?
C18A C13A Rh1A 125.8(8) . . ?
C9A C14A H14A 109.5 . . ?
C9A C14A H14B 109.5 . . ?
H14A C14A H14B 109.5 . . ?
C9A C14A H14C 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
C10A C15A H15A 109.5 . . ?
C10A C15A H15B 109.5 . . ?
H15A C15A H15B 109.5 . . ?
C10A C15A H15C 109.5 . . ?
H15A C15A H15C 109.5 . . ?
H15B C15A H15C 109.5 . . ?
C11A C16A H16A 109.5 . . ?
C11A C16A H16B 109.5 . . ?
H16A C16A H16B 109.5 . . ?
C11A C16A H16C 109.5 . . ?
H16A C16A H16C 109.5 . . ?
H16B C16A H16C 109.5 . . ?
C12A C17A H17A 109.5 . . ?
C12A C17A H17B 109.5 . . ?
H17A C17A H17B 109.5 . . ?
C12A C17A H17C 109.5 . . ?
H17A C17A H17C 109.5 . . ?
H17B C17A H17C 109.5 . . ?
C13A C18A H18A 109.5 . . ?
C13A C18A H18B 109.5 . . ?
H18A C18A H18B 109.5 . . ?
C13A C18A H18C 109.5 . . ?
H18A C18A H18C 109.5 . . ?
H18B C18A H18C 109.5 . . ?
C2B C1B H1BA 109.5 . . ?
C2B C1B H1BB 109.5 . . ?
H1BA C1B H1BB 109.5 . . ?
C2B C1B H1BC 109.5 . . ?
H1BA C1B H1BC 109.5 . . ?
H1BB C1B H1BC 109.5 . . ?
C2B N1B Rh1B 117.3(6) . . ?
C2B N1B H1B 121.4 . . ?
Rh1B N1B H1B 121.3 . . ?
C4B Rh1B N1B 78.3(3) . . ?
C4B Rh1B C12B 109.1(4) . . ?
N1B Rh1B C12B 98.7(3) . . ?
C4B Rh1B C11B 95.9(4) . . ?
N1B Rh1B C11B 133.0(3) . . ?
C12B Rh1B C11B 38.8(4) . . ?
C4B Rh1B C10B 117.3(4) . . ?
N1B Rh1B C10B 159.3(4) . . ?
C12B Rh1B C10B 64.2(4) . . ?
C11B Rh1B C10B 37.7(3) . . ?
C4B Rh1B C9B 155.3(4) . . ?
N1B Rh1B C9B 124.8(4) . . ?
C12B Rh1B C9B 62.5(4) . . ?
C11B Rh1B C9B 62.6(4) . . ?
C10B Rh1B C9B 38.2(4) . . ?
C4B Rh1B C13B 147.0(4) . . ?
N1B Rh1B C13B 97.3(3) . . ?
C12B Rh1B C13B 38.6(4) . . ?
C11B Rh1B C13B 63.1(4) . . ?
C10B Rh1B C13B 62.1(4) . . ?
C9B Rh1B C13B 34.9(4) . . ?
C4B Rh1B Cl1B 89.9(3) . . ?
N1B Rh1B Cl1B 93.9(2) . . ?
C12B Rh1B Cl1B 159.0(3) . . ?
C11B Rh1B Cl1B 133.0(3) . . ?
C10B Rh1B Cl1B 99.4(3) . . ?
C9B Rh1B Cl1B 96.5(3) . . ?
C13B Rh1B Cl1B 123.2(3) . . ?
N1B C2B C3B 114.1(7) . . ?
N1B C2B C1B 120.4(9) . . ?
C3B C2B C1B 125.4(8) . . ?
C4B C3B C8B 121.2(9) . . ?
C4B C3B C2B 114.7(8) . . ?
C8B C3B C2B 124.0(7) . . ?
C5B C4B C3B 118.0(9) . . ?
C5B C4B Rh1B 127.7(7) . . ?
C3B C4B Rh1B 114.3(7) . . ?
C4B C5B C6B 120.2(8) . . ?
C4B C5B H5B 119.9 . . ?
C6B C5B H5B 119.9 . . ?
C7B C6B C5B 121.9(9) . . ?
C7B C6B Cl2B 118.6(8) . . ?
C5B C6B Cl2B 119.5(7) . . ?
C6B C7B C8B 119.4(9) . . ?
C6B C7B H7B 120.3 . . ?
C8B C7B H7B 120.3 . . ?
C7B C8B C3B 119.1(8) . . ?
C7B C8B H8B 120.4 . . ?
C3B C8B H8B 120.4 . . ?
C13B C9B C10B 109.4(10) . . ?
C13B C9B C14B 126.7(11) . . ?
C10B C9B C14B 123.8(11) . . ?
C13B C9B Rh1B 72.9(6) . . ?
C10B C9B Rh1B 67.9(5) . . ?
C14B C9B Rh1B 128.1(7) . . ?
C11B C10B C9B 107.1(9) . . ?
C11B C10B C15B 128.3(11) . . ?
C9B C10B C15B 124.2(10) . . ?
C11B C10B Rh1B 70.5(4) . . ?
C9B C10B Rh1B 73.9(5) . . ?
C15B C10B Rh1B 126.2(8) . . ?
C10B C11B C12B 108.7(9) . . ?
C10B C11B C16B 126.7(9) . . ?
C12B C11B C16B 124.6(9) . . ?
C10B C11B Rh1B 71.8(5) . . ?
C12B C11B Rh1B 70.3(5) . . ?
C16B C11B Rh1B 126.2(7) . . ?
C11B C12B C13B 106.3(9) . . ?
C11B C12B C17B 127.6(10) . . ?
C13B C12B C17B 125.7(10) . . ?
C11B C12B Rh1B 71.0(5) . . ?
C13B C12B Rh1B 75.0(6) . . ?
C17B C12B Rh1B 124.7(7) . . ?
C9B C13B C12B 108.2(10) . . ?
C9B C13B C18B 128.3(11) . . ?
C12B C13B C18B 123.4(11) . . ?
C9B C13B Rh1B 72.2(7) . . ?
C12B C13B Rh1B 66.4(6) . . ?
C18B C13B Rh1B 125.0(7) . . ?
C9B C14B H14D 109.5 . . ?
C9B C14B H14E 109.5 . . ?
H14D C14B H14E 109.5 . . ?
C9B C14B H14F 109.5 . . ?
H14D C14B H14F 109.5 . . ?
H14E C14B H14F 109.5 . . ?
C10B C15B H15D 109.5 . . ?
C10B C15B H15E 109.5 . . ?
H15D C15B H15E 109.5 . . ?
C10B C15B H15F 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 109.5 . . ?
C11B C16B H16D 109.5 . . ?
C11B C16B H16E 109.5 . . ?
H16D C16B H16E 109.5 . . ?
C11B C16B H16F 109.5 . . ?
H16D C16B H16F 109.5 . . ?
H16E C16B H16F 109.5 . . ?
C12B C17B H17D 109.5 . . ?
C12B C17B H17E 109.5 . . ?
H17D C17B H17E 109.5 . . ?
C12B C17B H17F 109.5 . . ?
H17D C17B H17F 109.5 . . ?
H17E C17B H17F 109.5 . . ?
C13B C18B H18D 109.5 . . ?
C13B C18B H18E 109.5 . . ?
H18D C18B H18E 109.5 . . ?
C13B C18B H18F 109.5 . . ?
H18D C18B H18F 109.5 . . ?
H18E C18B H18F 109.5 . . ?
C2C C1C H1CA 109.5 . . ?
C2C C1C H1CB 109.5 . . ?
H1CA C1C H1CB 109.5 . . ?
C2C C1C H1CC 109.5 . . ?
H1CA C1C H1CC 109.5 . . ?
H1CB C1C H1CC 109.5 . . ?
C2C N1C Rh1C 118.9(7) . . ?
C2C N1C H1C 120.6 . . ?
Rh1C N1C H1C 120.6 . . ?
C4C Rh1C N1C 77.1(4) . . ?
C4C Rh1C C9C 117.5(4) . . ?
N1C Rh1C C9C 97.7(3) . . ?
C4C Rh1C C10C 96.1(4) . . ?
N1C Rh1C C10C 127.3(4) . . ?
C9C Rh1C C10C 39.3(3) . . ?
C4C Rh1C C11C 111.4(4) . . ?
N1C Rh1C C11C 162.6(3) . . ?
C9C Rh1C C11C 64.9(4) . . ?
C10C Rh1C C11C 39.0(4) . . ?
C4C Rh1C C13C 156.0(4) . . ?
N1C Rh1C C13C 103.2(4) . . ?
C9C Rh1C C13C 38.5(3) . . ?
C10C Rh1C C13C 64.2(3) . . ?
C11C Rh1C C13C 62.7(3) . . ?
C4C Rh1C C12C 148.3(4) . . ?
N1C Rh1C C12C 134.4(3) . . ?
C9C Rh1C C12C 63.5(4) . . ?
C10C Rh1C C12C 64.1(3) . . ?
C11C Rh1C C12C 37.9(3) . . ?
C13C Rh1C C12C 36.2(4) . . ?
C4C Rh1C Cl1C 86.8(3) . . ?
N1C Rh1C Cl1C 91.5(2) . . ?
C9C Rh1C Cl1C 155.4(2) . . ?
C10C Rh1C Cl1C 140.8(3) . . ?
C11C Rh1C Cl1C 103.9(3) . . ?
C13C Rh1C Cl1C 117.1(2) . . ?
C12C Rh1C Cl1C 93.9(3) . . ?
N1C C2C C3C 114.7(10) . . ?
N1C C2C C1C 122.9(9) . . ?
C3C C2C C1C 122.3(9) . . ?
C8C C3C C4C 121.5(10) . . ?
C8C C3C C2C 125.5(11) . . ?
C4C C3C C2C 113.0(8) . . ?
C5C C4C C3C 117.5(9) . . ?
C5C C4C Rh1C 126.1(9) . . ?
C3C C4C Rh1C 116.2(7) . . ?
C6C C5C C4C 121.4(13) . . ?
C6C C5C H5C 119.3 . . ?
C4C C5C H5C 119.3 . . ?
C7C C6C C5C 120.9(11) . . ?
C7C C6C Cl2C 118.0(8) . . ?
C5C C6C Cl2C 121.0(10) . . ?
C6C C7C C8C 119.6(9) . . ?
C6C C7C H7C 120.2 . . ?
C8C C7C H7C 120.2 . . ?
C3C C8C C7C 119.0(12) . . ?
C3C C8C H8C 120.5 . . ?
C7C C8C H8C 120.5 . . ?
C10C C9C C13C 108.2(8) . . ?
C10C C9C C14C 126.2(8) . . ?
C13C C9C C14C 124.9(8) . . ?
C10C C9C Rh1C 70.9(5) . . ?
C13C C9C Rh1C 75.4(5) . . ?
C14C C9C Rh1C 127.0(7) . . ?
C11C C10C C9C 106.5(7) . . ?
C11C C10C C15C 126.7(8) . . ?
C9C C10C C15C 126.7(9) . . ?
C11C C10C Rh1C 71.2(5) . . ?
C9C C10C Rh1C 69.8(5) . . ?
C15C C10C Rh1C 127.2(7) . . ?
C10C C11C C12C 108.8(8) . . ?
C10C C11C C16C 126.4(8) . . ?
C12C C11C C16C 124.4(9) . . ?
C10C C11C Rh1C 69.8(5) . . ?
C12C C11C Rh1C 74.5(6) . . ?
C16C C11C Rh1C 127.4(7) . . ?
C13C C12C C11C 108.2(8) . . ?
C13C C12C C17C 127.3(9) . . ?
C11C C12C C17C 124.5(10) . . ?
C13C C12C Rh1C 71.8(5) . . ?
C11C C12C Rh1C 67.6(5) . . ?
C17C C12C Rh1C 126.8(7) . . ?
C12C C13C C9C 108.2(8) . . ?
C12C C13C C18C 129.3(8) . . ?
C9C C13C C18C 122.5(9) . . ?
C12C C13C Rh1C 72.0(5) . . ?
C9C C13C Rh1C 66.1(4) . . ?
C18C C13C Rh1C 127.8(7) . . ?
C9C C14C H14G 109.5 . . ?
C9C C14C H14H 109.5 . . ?
H14G C14C H14H 109.5 . . ?
C9C C14C H14I 109.5 . . ?
H14G C14C H14I 109.5 . . ?
H14H C14C H14I 109.5 . . ?
C10C C15C H15G 109.5 . . ?
C10C C15C H15H 109.5 . . ?
H15G C15C H15H 109.5 . . ?
C10C C15C H15I 109.5 . . ?
H15G C15C H15I 109.5 . . ?
H15H C15C H15I 109.5 . . ?
C11C C16C H16G 109.5 . . ?
C11C C16C H16H 109.5 . . ?
H16G C16C H16H 109.5 . . ?
C11C C16C H16I 109.5 . . ?
H16G C16C H16I 109.5 . . ?
H16H C16C H16I 109.5 . . ?
C12C C17C H17G 109.5 . . ?
C12C C17C H17H 109.5 . . ?
H17G C17C H17H 109.5 . . ?
C12C C17C H17I 109.5 . . ?
H17G C17C H17I 109.5 . . ?
H17H C17C H17I 109.5 . . ?
C13C C18C H18G 109.5 . . ?
C13C C18C H18H 109.5 . . ?
H18G C18C H18H 109.5 . . ?
C13C C18C H18I 109.5 . . ?
H18G C18C H18I 109.5 . . ?
H18H C18C H18I 109.5 . . ?
C2D C1D H1DA 109.5 . . ?
C2D C1D H1DB 109.5 . . ?
H1DA C1D H1DB 109.5 . . ?
C2D C1D H1DC 109.5 . . ?
H1DA C1D H1DC 109.5 . . ?
H1DB C1D H1DC 109.5 . . ?
C2D N1D Rh1D 118.6(7) . . ?
C2D N1D H1D 120.7 . . ?
Rh1D N1D H1D 120.7 . . ?
C4D Rh1D N1D 78.3(4) . . ?
C4D Rh1D C9D 117.6(3) . . ?
N1D Rh1D C9D 98.6(4) . . ?
C4D Rh1D C12D 111.5(4) . . ?
N1D Rh1D C12D 162.9(4) . . ?
C9D Rh1D C12D 64.6(4) . . ?
C4D Rh1D C13D 97.0(3) . . ?
N1D Rh1D C13D 129.0(4) . . ?
C9D Rh1D C13D 38.9(3) . . ?
C12D Rh1D C13D 38.4(4) . . ?
C4D Rh1D C11D 149.4(4) . . ?
N1D Rh1D C11D 132.2(3) . . ?
C9D Rh1D C11D 62.8(3) . . ?
C12D Rh1D C11D 38.7(3) . . ?
C13D Rh1D C11D 63.7(3) . . ?
C4D Rh1D C10D 155.9(3) . . ?
N1D Rh1D C10D 101.6(3) . . ?
C9D Rh1D C10D 38.3(3) . . ?
C12D Rh1D C10D 63.5(3) . . ?
C13D Rh1D C10D 64.0(3) . . ?
C11D Rh1D C10D 36.1(3) . . ?
C4D Rh1D Cl1D 85.9(3) . . ?
N1D Rh1D Cl1D 92.1(2) . . ?
C9D Rh1D Cl1D 155.7(2) . . ?
C12D Rh1D Cl1D 102.3(3) . . ?
C13D Rh1D Cl1D 138.6(3) . . ?
C11D Rh1D Cl1D 93.9(2) . . ?
C10D Rh1D Cl1D 118.2(2) . . ?
N1D C2D C3D 114.3(10) . . ?
N1D C2D C1D 121.6(10) . . ?
C3D C2D C1D 124.1(9) . . ?
C8D C3D C4D 120.7(10) . . ?
C8D C3D C2D 124.6(11) . . ?
C4D C3D C2D 114.4(8) . . ?
C5D C4D C3D 118.9(9) . . ?
C5D C4D Rh1D 126.9(8) . . ?
C3D C4D Rh1D 114.3(6) . . ?
C4D C5D C6D 117.3(12) . . ?
C4D C5D H5D 121.4 . . ?
C6D C5D H5D 121.4 . . ?
C7D C6D C5D 124.4(11) . . ?
C7D C6D Cl2D 119.6(8) . . ?
C5D C6D Cl2D 116.0(10) . . ?
C8D C7D C6D 118.5(10) . . ?
C8D C7D H7D 120.8 . . ?
C6D C7D H7D 120.8 . . ?
C7D C8D C3D 120.3(12) . . ?
C7D C8D H8D 119.9 . . ?
C3D C8D H8D 119.9 . . ?
C13D C9D C10D 109.0(8) . . ?
C13D C9D C14D 126.2(7) . . ?
C10D C9D C14D 124.4(8) . . ?
C13D C9D Rh1D 71.4(5) . . ?
C10D C9D Rh1D 75.2(5) . . ?
C14D C9D Rh1D 125.9(7) . . ?
C11D C10D C9D 107.1(8) . . ?
C11D C10D C15D 127.0(9) . . ?
C9D C10D C15D 125.9(9) . . ?
C11D C10D Rh1D 71.5(5) . . ?
C9D C10D Rh1D 66.4(5) . . ?
C15D C10D Rh1D 128.8(7) . . ?
C10D C11D C12D 108.8(8) . . ?
C10D C11D C16D 128.1(9) . . ?
C12D C11D C16D 123.1(9) . . ?
C10D C11D Rh1D 72.4(5) . . ?
C12D C11D Rh1D 67.1(5) . . ?
C16D C11D Rh1D 126.1(7) . . ?
C13D C12D C11D 107.8(8) . . ?
C13D C12D C17D 126.5(9) . . ?
C11D C12D C17D 124.5(9) . . ?
C13D C12D Rh1D 71.2(6) . . ?
C11D C12D Rh1D 74.2(6) . . ?
C17D C12D Rh1D 129.8(8) . . ?
C12D C13D C9D 107.0(7) . . ?
C12D C13D C18D 126.9(8) . . ?
C9D C13D C18D 126.1(9) . . ?
C12D C13D Rh1D 70.3(6) . . ?
C9D C13D Rh1D 69.7(5) . . ?
C18D C13D Rh1D 126.5(7) . . ?
C9D C14D H14J 109.5 . . ?
C9D C14D H14K 109.5 . . ?
H14J C14D H14K 109.5 . . ?
C9D C14D H14L 109.5 . . ?
H14J C14D H14L 109.5 . . ?
H14K C14D H14L 109.5 . . ?
C10D C15D H15J 109.5 . . ?
C10D C15D H15K 109.5 . . ?
H15J C15D H15K 109.5 . . ?
C10D C15D H15L 109.5 . . ?
H15J C15D H15L 109.5 . . ?
H15K C15D H15L 109.5 . . ?
C11D C16D H16J 109.5 . . ?
C11D C16D H16K 109.5 . . ?
H16J C16D H16K 109.5 . . ?
C11D C16D H16L 109.5 . . ?
H16J C16D H16L 109.5 . . ?
H16K C16D H16L 109.5 . . ?
C12D C17D H17J 109.5 . . ?
C12D C17D H17K 109.5 . . ?
H17J C17D H17K 109.5 . . ?
C12D C17D H17L 109.5 . . ?
H17J C17D H17L 109.5 . . ?
H17K C17D H17L 109.5 . . ?
C13D C18D H18J 109.5 . . ?
C13D C18D H18K 109.5 . . ?
H18J C18D H18K 109.5 . . ?
C13D C18D H18L 109.5 . . ?
H18J C18D H18L 109.5 . . ?
H18K C18D H18L 109.5 . . ?

_refine_diff_density_max         1.377
_refine_diff_density_min         -1.453
_refine_diff_density_rms         0.129

