# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_p
_audit_block_doi                 10.5517/cc13n99c
_database_code_depnum_ccdc_archive 'CCDC 1032402'
_audit_update_record             
;
2014-11-03 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H26 N2 O2'
_chemical_formula_sum            'C32 H26 N2 O2'
_chemical_formula_weight         470.55

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   18.889(2)
_cell_length_b                   7.1199(8)
_cell_length_c                   18.6541(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.646(11)
_cell_angle_gamma                90.00
_cell_volume                     2427.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1269
_cell_measurement_theta_min      3.5340
_cell_measurement_theta_max      26.4150

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             992
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.76000
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10153
_diffrn_reflns_av_R_equivalents  0.0611
_diffrn_reflns_av_sigmaI/netI    0.0840
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.07
_diffrn_reflns_theta_max         25.99
_reflns_number_total             4763
_reflns_number_gt                3338
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0780P)²+2.1035P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4763
_refine_ls_number_parameters     325
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1145
_refine_ls_R_factor_gt           0.0791
_refine_ls_wR_factor_ref         0.2093
_refine_ls_wR_factor_gt          0.1860
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.28991(13) 0.1967(4) 0.29932(13) 0.0238(6) Uani 1 1 d . . .
O1 O 0.36381(12) 0.6085(3) 0.03989(12) 0.0320(6) Uani 1 1 d . . .
O2 O 0.03559(12) 1.0279(3) 0.43286(14) 0.0379(6) Uani 1 1 d . . .
C11 C 0.17817(14) 0.3427(4) 0.29650(14) 0.0137(5) Uani 1 1 d U . .
H11 H 0.1274 0.3444 0.2804 0.016 Uiso 1 1 calc R . .
C41 C 0.16783(17) 0.6195(5) 0.37115(16) 0.0251(7) Uani 1 1 d . . .
C10 C 0.21429(17) 0.4799(5) 0.34581(17) 0.0269(7) Uani 1 1 d . . .
C43 C 0.04955(18) 0.7425(5) 0.37462(19) 0.0327(8) Uani 1 1 d . . .
H43 H -0.0011 0.7303 0.3620 0.039 Uiso 1 1 calc R . .
C31 C 0.24143(16) 0.2112(5) 0.12137(16) 0.0246(7) Uani 1 1 d . . .
C34 C 0.32634(16) 0.4701(5) 0.06603(17) 0.0273(7) Uani 1 1 d . . .
C8 C 0.33051(17) 0.3452(5) 0.34215(17) 0.0262(7) Uani 1 1 d . . .
C1 C 0.33990(16) 0.0610(4) 0.28807(16) 0.0230(7) Uani 1 1 d . . .
C22 C 0.19197(16) 0.0756(5) 0.14445(17) 0.0253(7) Uani 1 1 d U . .
C32 C 0.23816(17) 0.4034(5) 0.13563(16) 0.0254(7) Uani 1 1 d . . .
H32 H 0.2070 0.4463 0.1635 0.031 Uiso 1 1 calc R . .
C44 C 0.08166(17) 0.8968(5) 0.41536(17) 0.0276(7) Uani 1 1 d . . .
C33 C 0.28058(17) 0.5307(5) 0.10902(17) 0.0282(7) Uani 1 1 d . . .
H33 H 0.2785 0.6576 0.1200 0.034 Uiso 1 1 calc R . .
C6 C 0.41052(16) 0.1326(5) 0.32150(16) 0.0252(7) Uani 1 1 d . . .
C21 C 0.17656(16) 0.0805(4) 0.21492(16) 0.0235(7) Uani 1 1 d . . .
C12 C 0.21441(16) 0.2151(4) 0.27340(16) 0.0231(7) Uani 1 1 d U . .
C42 C 0.09165(18) 0.6067(5) 0.35252(18) 0.0307(8) Uani 1 1 d . . .
H42 H 0.0689 0.5050 0.3247 0.037 Uiso 1 1 calc R . .
C45 C 0.15670(18) 0.9110(5) 0.43535(18) 0.0319(8) Uani 1 1 d . . .
H45 H 0.1791 1.0126 0.4634 0.038 Uiso 1 1 calc R . .
C9 C 0.28870(17) 0.4861(5) 0.36512(18) 0.0287(8) Uani 1 1 d . . .
H9 H 0.3124 0.5851 0.3940 0.034 Uiso 1 1 calc R . .
C26 C 0.12628(17) -0.0458(5) 0.23106(18) 0.0291(8) Uani 1 1 d . . .
H26 H 0.1142 -0.0376 0.2763 0.035 Uiso 1 1 calc R . .
C46 C 0.19870(17) 0.7740(5) 0.41367(18) 0.0324(8) Uani 1 1 d . . .
H46 H 0.2494 0.7851 0.4279 0.039 Uiso 1 1 calc R . .
C2 C 0.33018(18) -0.1187(5) 0.25754(17) 0.0293(8) Uani 1 1 d . . .
H2 H 0.2836 -0.1668 0.2373 0.035 Uiso 1 1 calc R . .
C36 C 0.28881(18) 0.1535(5) 0.07961(19) 0.0330(8) Uani 1 1 d . . .
H36 H 0.2921 0.0263 0.0697 0.040 Uiso 1 1 calc R . .
C5 C 0.47215(17) 0.0209(5) 0.32158(17) 0.0280(7) Uani 1 1 d . . .
H5 H 0.5190 0.0650 0.3432 0.034 Uiso 1 1 calc R . .
C35 C 0.33152(19) 0.2800(5) 0.0521(2) 0.0351(8) Uani 1 1 d . . .
H35 H 0.3632 0.2376 0.0246 0.042 Uiso 1 1 calc R . .
C24 C 0.11037(17) -0.1933(5) 0.11339(19) 0.0309(8) Uani 1 1 d . . .
H24 H 0.0895 -0.2875 0.0802 0.037 Uiso 1 1 calc R . .
C4 C 0.46218(18) -0.1533(5) 0.28939(18) 0.0335(8) Uani 1 1 d . . .
H4 H 0.5026 -0.2265 0.2882 0.040 Uiso 1 1 calc R . .
N2 N 0.15807(17) -0.0636(5) 0.09401(18) 0.0475(9) Uani 1 1 d U . .
C25 C 0.09412(17) -0.1830(5) 0.18079(19) 0.0316(8) Uani 1 1 d . . .
H25 H 0.0615 -0.2680 0.1927 0.038 Uiso 1 1 calc R . .
C7 C 0.40369(17) 0.3091(5) 0.35461(17) 0.0268(7) Uani 1 1 d . . .
C52 C 0.0694(2) 1.1857(5) 0.4751(2) 0.0428(10) Uani 1 1 d . . .
H52A H 0.0324 1.2680 0.4842 0.064 Uiso 1 1 calc R . .
H52B H 0.0986 1.2520 0.4480 0.064 Uiso 1 1 calc R . .
H52C H 0.1001 1.1433 0.5214 0.064 Uiso 1 1 calc R . .
C13 C 0.46533(18) 0.4248(5) 0.3999(2) 0.0412(9) Uani 1 1 d . . .
H13A H 0.5112 0.3675 0.3993 0.062 Uiso 1 1 calc R . .
H13B H 0.4610 0.4321 0.4500 0.062 Uiso 1 1 calc R . .
H13C H 0.4632 0.5490 0.3794 0.062 Uiso 1 1 calc R . .
C3 C 0.39168(19) -0.2223(5) 0.25829(19) 0.0363(8) Uani 1 1 d . . .
H3 H 0.3863 -0.3419 0.2375 0.044 Uiso 1 1 calc R . .
C51 C 0.3996(2) 0.5535(6) -0.0153(2) 0.0440(10) Uani 1 1 d . . .
H51A H 0.4240 0.6602 -0.0297 0.066 Uiso 1 1 calc R . .
H51B H 0.3642 0.5058 -0.0577 0.066 Uiso 1 1 calc R . .
H51C H 0.4349 0.4575 0.0042 0.066 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C12 1.392(4) . ?
N1 C1 1.403(4) . ?
N1 C8 1.426(4) . ?
O1 C34 1.373(4) . ?
O1 C51 1.423(4) . ?
O2 C44 1.370(4) . ?
O2 C52 1.427(4) . ?
C11 C12 1.276(4) . ?
C11 C10 1.396(4) . ?
C41 C42 1.395(4) . ?
C41 C46 1.394(5) . ?
C41 C10 1.480(4) . ?
C10 C9 1.361(4) . ?
C43 C42 1.380(5) . ?
C43 C44 1.385(5) . ?
C31 C36 1.389(4) . ?
C31 C32 1.398(5) . ?
C31 C22 1.481(4) . ?
C34 C35 1.386(5) . ?
C34 C33 1.388(4) . ?
C8 C7 1.367(4) . ?
C8 C9 1.409(4) . ?
C1 C2 1.394(5) . ?
C1 C6 1.417(4) . ?
C22 N2 1.404(4) . ?
C22 C21 1.417(4) . ?
C32 C33 1.382(4) . ?
C44 C45 1.375(4) . ?
C6 C5 1.409(4) . ?
C6 C7 1.421(4) . ?
C21 C26 1.395(4) . ?
C21 C12 1.492(4) . ?
C45 C46 1.381(5) . ?
C26 C25 1.384(5) . ?
C2 C3 1.373(5) . ?
C36 C35 1.391(5) . ?
C5 C4 1.371(5) . ?
C24 C25 1.369(5) . ?
C24 N2 1.400(5) . ?
C4 C3 1.400(5) . ?
C7 C13 1.500(4) . ?

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
C12 N1 C1 133.0(3) . . ?
C12 N1 C8 118.9(3) . . ?
C1 N1 C8 107.9(2) . . ?
C34 O1 C51 116.2(3) . . ?
C44 O2 C52 116.4(2) . . ?
C12 C11 C10 120.4(3) . . ?
C42 C41 C46 116.7(3) . . ?
C42 C41 C10 122.3(3) . . ?
C46 C41 C10 121.0(3) . . ?
C9 C10 C11 119.8(3) . . ?
C9 C10 C41 123.3(3) . . ?
C11 C10 C41 116.7(3) . . ?
C42 C43 C44 121.0(3) . . ?
C36 C31 C32 117.5(3) . . ?
C36 C31 C22 120.9(3) . . ?
C32 C31 C22 121.4(3) . . ?
O1 C34 C35 124.5(3) . . ?
O1 C34 C33 115.7(3) . . ?
C35 C34 C33 119.7(3) . . ?
C7 C8 C9 134.6(3) . . ?
C7 C8 N1 109.5(3) . . ?
C9 C8 N1 115.8(3) . . ?
C2 C1 N1 132.0(3) . . ?
C2 C1 C6 121.5(3) . . ?
N1 C1 C6 106.3(3) . . ?
N2 C22 C21 118.2(3) . . ?
N2 C22 C31 118.7(3) . . ?
C21 C22 C31 123.1(3) . . ?
C33 C32 C31 121.0(3) . . ?
O2 C44 C45 124.0(3) . . ?
O2 C44 C43 117.0(3) . . ?
C45 C44 C43 119.0(3) . . ?
C32 C33 C34 120.4(3) . . ?
C5 C6 C1 118.9(3) . . ?
C5 C6 C7 131.6(3) . . ?
C1 C6 C7 109.3(3) . . ?
C26 C21 C22 119.7(3) . . ?
C26 C21 C12 118.9(3) . . ?
C22 C21 C12 121.4(3) . . ?
C11 C12 N1 122.7(3) . . ?
C11 C12 C21 120.4(3) . . ?
N1 C12 C21 116.9(3) . . ?
C43 C42 C41 121.1(3) . . ?
C44 C45 C46 119.9(3) . . ?
C10 C9 C8 121.1(3) . . ?
C25 C26 C21 121.0(3) . . ?
C45 C46 C41 122.3(3) . . ?
C3 C2 C1 117.7(3) . . ?
C31 C36 C35 122.1(3) . . ?
C4 C5 C6 119.2(3) . . ?
C34 C35 C36 119.2(3) . . ?
C25 C24 N2 120.6(3) . . ?
C5 C4 C3 120.7(3) . . ?
C24 N2 C22 120.4(3) . . ?
C24 C25 C26 119.9(3) . . ?
C8 C7 C6 106.9(3) . . ?
C8 C7 C13 126.9(3) . . ?
C6 C7 C13 126.0(3) . . ?
C2 C3 C4 121.9(3) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.685
_refine_diff_density_min         -0.615
_refine_diff_density_rms         0.063
####################################################################### 
# 
# 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_mon
_audit_block_doi                 10.5517/cc13n9bd
_database_code_depnum_ccdc_archive 'CCDC 1032403'
_audit_update_record             
;
2014-11-03 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C42 H30 N2'
_chemical_formula_sum            'C42 H30 N2'
_chemical_formula_weight         562.68

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   11.0719(10)
_cell_length_b                   11.9763(11)
_cell_length_c                   12.7664(9)
_cell_angle_alpha                95.060(7)
_cell_angle_beta                 92.632(6)
_cell_angle_gamma                117.362(9)
_cell_volume                     1490.4(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1672
_cell_measurement_theta_min      3.5220
_cell_measurement_theta_max      27.5330

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.97868
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10217
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_sigmaI/netI    0.0527
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.22
_diffrn_reflns_theta_max         26.00
_reflns_number_total             5857
_reflns_number_gt                4454
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0562P)²+0.7408P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5857
_refine_ls_number_parameters     397
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0915
_refine_ls_R_factor_gt           0.0681
_refine_ls_wR_factor_ref         0.1634
_refine_ls_wR_factor_gt          0.1520
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_restrained_S_all      1.134
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C11 C 0.16374(19) 0.30279(18) 0.40339(15) 0.0124(4) Uani 1 1 d . . .
H11A H 0.0828 0.2507 0.4305 0.015 Uiso 1 1 calc R . .
C12 C 0.1991(2) 0.2615(2) 0.32057(19) 0.0256(5) Uani 1 1 d . . .
C10 C 0.2458(2) 0.4250(2) 0.45288(18) 0.0265(5) Uani 1 1 d . . .
C9 C 0.3649(2) 0.5039(2) 0.41492(18) 0.0272(5) Uani 1 1 d . . .
H9A H 0.4190 0.5851 0.4495 0.033 Uiso 1 1 calc R . .
C8 C 0.4059(2) 0.4614(2) 0.32253(18) 0.0259(5) Uani 1 1 d . . .
C31 C 0.0226(2) 0.5666(2) 0.81343(18) 0.0267(5) Uani 1 1 d . . .
C21 C 0.1906(2) 0.4635(2) 0.54523(18) 0.0270(5) Uani 1 1 d . . .
C42 C 0.0960(2) 0.0221(2) 0.30049(18) 0.0253(5) Uani 1 1 d . . .
C24 C 0.0803(2) 0.5320(2) 0.72064(19) 0.0279(5) Uani 1 1 d . . .
C54 C 0.3525(2) 0.0434(2) 0.57459(19) 0.0297(6) Uani 1 1 d . . .
C26 C 0.2707(2) 0.5718(2) 0.61646(19) 0.0316(6) Uani 1 1 d . . .
H26A H 0.3617 0.6223 0.6061 0.038 Uiso 1 1 calc R . .
C51 C 0.1861(2) 0.0273(2) 0.39292(19) 0.0272(5) Uani 1 1 d . . .
C32 C -0.1174(2) 0.5279(2) 0.81214(19) 0.0279(5) Uani 1 1 d . . .
H32A H -0.1747 0.4820 0.7514 0.033 Uiso 1 1 calc R . .
C56 C 0.1293(2) -0.0378(2) 0.4784(2) 0.0323(6) Uani 1 1 d . . .
H56A H 0.0353 -0.0885 0.4750 0.039 Uiso 1 1 calc R . .
C33 C -0.1726(3) 0.5562(2) 0.89898(19) 0.0308(6) Uani 1 1 d . . .
H33A H -0.2662 0.5288 0.8966 0.037 Uiso 1 1 calc R . .
C61 C 0.4398(3) 0.0547(2) 0.6713(2) 0.0313(6) Uani 1 1 d . . .
C55 C 0.2103(3) -0.0282(2) 0.5676(2) 0.0338(6) Uani 1 1 d . . .
H55A H 0.1694 -0.0702 0.6242 0.041 Uiso 1 1 calc R . .
C23 C 0.0014(3) 0.4241(2) 0.6491(2) 0.0334(6) Uani 1 1 d . . .
H23A H -0.0896 0.3734 0.6594 0.040 Uiso 1 1 calc R . .
C52 C 0.3280(2) 0.0963(2) 0.3986(2) 0.0303(6) Uani 1 1 d . . .
H52A H 0.3687 0.1382 0.3419 0.036 Uiso 1 1 calc R . .
C2 C 0.3303(2) 0.2045(2) 0.11028(19) 0.0305(6) Uani 1 1 d . . .
H2A H 0.2516 0.1301 0.1167 0.037 Uiso 1 1 calc R . .
C45 C 0.0157(2) 0.1254(2) 0.18026(19) 0.0300(6) Uani 1 1 d . . .
H45A H 0.0212 0.1993 0.1580 0.036 Uiso 1 1 calc R . .
C41 C 0.1040(2) 0.1326(2) 0.26497(17) 0.0240(5) Uani 1 1 d . . .
C53 C 0.4094(2) 0.1034(2) 0.4871(2) 0.0319(6) Uani 1 1 d . . .
H53A H 0.5039 0.1490 0.4884 0.038 Uiso 1 1 calc R . .
N2 N -0.0039(3) -0.0962(2) 0.2485(2) 0.0562(7) Uani 1 1 d . . .
C36 C 0.1056(2) 0.6375(2) 0.90545(19) 0.0305(6) Uani 1 1 d . . .
H36A H 0.1993 0.6655 0.9086 0.037 Uiso 1 1 calc R . .
C22 C 0.0550(2) 0.3907(2) 0.56339(19) 0.0323(6) Uani 1 1 d . . .
H22A H -0.0006 0.3183 0.5171 0.039 Uiso 1 1 calc R . .
C4 C 0.5262(3) 0.3243(3) 0.0167(2) 0.0368(6) Uani 1 1 d . . .
H4A H 0.5760 0.3274 -0.0407 0.044 Uiso 1 1 calc R . .
C44 C -0.0801(3) 0.0091(2) 0.1290(2) 0.0348(6) Uani 1 1 d . . .
H44A H -0.1375 0.0048 0.0716 0.042 Uiso 1 1 calc R . .
C3 C 0.4079(2) 0.2127(3) 0.0271(2) 0.0335(6) Uani 1 1 d . . .
H3A H 0.3811 0.1425 -0.0232 0.040 Uiso 1 1 calc R . .
C5 C 0.5700(3) 0.4295(3) 0.0900(2) 0.0361(6) Uani 1 1 d . . .
H5A H 0.6493 0.5030 0.0828 0.043 Uiso 1 1 calc R . .
C7 C 0.5129(2) 0.5177(2) 0.26250(19) 0.0287(5) Uani 1 1 d . . .
C35 C 0.0499(3) 0.6666(3) 0.9919(2) 0.0364(6) Uani 1 1 d . . .
H35A H 0.1067 0.7146 1.0523 0.044 Uiso 1 1 calc R . .
C43 C -0.0903(3) -0.1006(2) 0.1634(2) 0.0373(6) Uani 1 1 d . . .
H43A H -0.1557 -0.1787 0.1293 0.045 Uiso 1 1 calc R . .
C6 C 0.4937(2) 0.4249(2) 0.17617(19) 0.0278(5) Uani 1 1 d . . .
C34 C -0.0888(3) 0.6252(2) 0.9895(2) 0.0350(6) Uani 1 1 d . . .
H34A H -0.1258 0.6437 1.0484 0.042 Uiso 1 1 calc R . .
C66 C 0.3950(3) -0.0371(3) 0.7403(2) 0.0414(7) Uani 1 1 d . . .
H66A H 0.3084 -0.1062 0.7260 0.050 Uiso 1 1 calc R . .
C62 C 0.5684(3) 0.1574(3) 0.6974(2) 0.0485(8) Uani 1 1 d . . .
H62A H 0.6009 0.2215 0.6541 0.058 Uiso 1 1 calc R . .
C13 C 0.6289(3) 0.6496(2) 0.2838(2) 0.0409(7) Uani 1 1 d . . .
H13A H 0.6173 0.6921 0.3469 0.061 Uiso 1 1 calc R . .
H13B H 0.6302 0.6952 0.2253 0.061 Uiso 1 1 calc R . .
H13C H 0.7136 0.6461 0.2928 0.061 Uiso 1 1 calc R . .
C65 C 0.4760(3) -0.0281(3) 0.8293(2) 0.0470(7) Uani 1 1 d . . .
H65A H 0.4439 -0.0911 0.8737 0.056 Uiso 1 1 calc R . .
C64 C 0.6034(3) 0.0733(3) 0.8527(2) 0.0497(8) Uani 1 1 d . . .
H64A H 0.6583 0.0793 0.9126 0.060 Uiso 1 1 calc R . .
C63 C 0.6490(3) 0.1658(3) 0.7868(3) 0.0583(9) Uani 1 1 d . . .
H63A H 0.7352 0.2352 0.8024 0.070 Uiso 1 1 calc R . .
C25 C 0.2168(2) 0.6048(2) 0.7018(2) 0.0317(6) Uani 1 1 d . . .
H25A H 0.2725 0.6772 0.7480 0.038 Uiso 1 1 calc R . .
C1 C 0.3737(2) 0.3116(2) 0.18459(18) 0.0251(5) Uani 1 1 d . . .
N1 N 0.31815(18) 0.33473(18) 0.27557(15) 0.0246(4) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C11 C12 1.281(3) . ?
C11 C10 1.388(3) . ?
C12 N1 1.390(3) . ?
C12 C41 1.496(3) . ?
C10 C9 1.365(3) . ?
C10 C21 1.485(3) . ?
C9 C8 1.418(3) . ?
C8 C7 1.373(3) . ?
C8 N1 1.427(3) . ?
C31 C36 1.398(3) . ?
C31 C32 1.398(3) . ?
C31 C24 1.487(3) . ?
C21 C22 1.390(3) . ?
C21 C26 1.399(3) . ?
C42 C41 1.403(3) . ?
C42 N2 1.414(3) . ?
C42 C51 1.488(3) . ?
C24 C25 1.400(3) . ?
C24 C23 1.395(3) . ?
C54 C55 1.399(3) . ?
C54 C53 1.397(3) . ?
C54 C61 1.489(3) . ?
C26 C25 1.379(3) . ?
C51 C52 1.393(3) . ?
C51 C56 1.399(3) . ?
C32 C33 1.380(3) . ?
C56 C55 1.379(3) . ?
C33 C34 1.381(4) . ?
C61 C62 1.387(4) . ?
C61 C66 1.393(4) . ?
C23 C22 1.382(3) . ?
C52 C53 1.384(3) . ?
C2 C3 1.379(3) . ?
C2 C1 1.398(3) . ?
C45 C44 1.382(3) . ?
C45 C41 1.394(3) . ?
N2 C43 1.395(4) . ?
C36 C35 1.382(3) . ?
C4 C5 1.374(4) . ?
C4 C3 1.399(4) . ?
C44 C43 1.379(4) . ?
C5 C6 1.407(3) . ?
C7 C6 1.428(3) . ?
C7 C13 1.499(3) . ?
C35 C34 1.378(4) . ?
C6 C1 1.414(3) . ?
C66 C65 1.379(4) . ?
C62 C63 1.383(4) . ?
C65 C64 1.370(4) . ?
C64 C63 1.371(4) . ?
C1 N1 1.403(3) . ?

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
C12 C11 C10 120.3(2) . . ?
C11 C12 N1 122.7(2) . . ?
C11 C12 C41 118.9(2) . . ?
N1 C12 C41 118.2(2) . . ?
C9 C10 C11 121.3(2) . . ?
C9 C10 C21 123.5(2) . . ?
C11 C10 C21 115.1(2) . . ?
C10 C9 C8 119.7(2) . . ?
C7 C8 C9 133.9(2) . . ?
C7 C8 N1 109.6(2) . . ?
C9 C8 N1 116.5(2) . . ?
C36 C31 C32 117.5(2) . . ?
C36 C31 C24 121.5(2) . . ?
C32 C31 C24 121.0(2) . . ?
C22 C21 C26 117.7(2) . . ?
C22 C21 C10 120.0(2) . . ?
C26 C21 C10 122.3(2) . . ?
C41 C42 N2 118.4(2) . . ?
C41 C42 C51 121.6(2) . . ?
N2 C42 C51 120.0(2) . . ?
C25 C24 C23 116.9(2) . . ?
C25 C24 C31 121.6(2) . . ?
C23 C24 C31 121.5(2) . . ?
C55 C54 C53 117.3(2) . . ?
C55 C54 C61 121.3(2) . . ?
C53 C54 C61 121.4(2) . . ?
C25 C26 C21 121.0(2) . . ?
C52 C51 C56 117.6(2) . . ?
C52 C51 C42 122.2(2) . . ?
C56 C51 C42 120.2(2) . . ?
C33 C32 C31 121.5(2) . . ?
C55 C56 C51 121.2(2) . . ?
C32 C33 C34 120.0(2) . . ?
C62 C61 C66 117.0(2) . . ?
C62 C61 C54 121.7(2) . . ?
C66 C61 C54 121.3(2) . . ?
C56 C55 C54 121.3(2) . . ?
C22 C23 C24 121.7(2) . . ?
C53 C52 C51 121.1(2) . . ?
C3 C2 C1 117.8(2) . . ?
C44 C45 C41 120.5(2) . . ?
C42 C41 C45 120.6(2) . . ?
C42 C41 C12 121.9(2) . . ?
C45 C41 C12 117.4(2) . . ?
C52 C53 C54 121.4(2) . . ?
C43 N2 C42 119.8(2) . . ?
C35 C36 C31 120.8(2) . . ?
C23 C22 C21 121.1(2) . . ?
C5 C4 C3 121.0(2) . . ?
C43 C44 C45 119.8(2) . . ?
C2 C3 C4 121.4(2) . . ?
C4 C5 C6 119.3(2) . . ?
C8 C7 C6 106.5(2) . . ?
C8 C7 C13 127.1(2) . . ?
C6 C7 C13 126.4(2) . . ?
C36 C35 C34 120.6(2) . . ?
C44 C43 N2 121.0(2) . . ?
C1 C6 C5 118.8(2) . . ?
C1 C6 C7 109.4(2) . . ?
C5 C6 C7 131.7(2) . . ?
C35 C34 C33 119.6(2) . . ?
C65 C66 C61 121.6(3) . . ?
C61 C62 C63 121.1(3) . . ?
C66 C65 C64 120.4(3) . . ?
C63 C64 C65 119.1(3) . . ?
C64 C63 C62 120.8(3) . . ?
C26 C25 C24 121.6(2) . . ?
C2 C1 N1 131.9(2) . . ?
C2 C1 C6 121.7(2) . . ?
N1 C1 C6 106.5(2) . . ?
C12 N1 C1 132.5(2) . . ?
C12 N1 C8 119.50(19) . . ?
C1 N1 C8 107.99(18) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.571
_refine_diff_density_min         -0.696
_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_p
_audit_block_doi                 10.5517/cc13n9cf
_database_code_depnum_ccdc_archive 'CCDC 1032404'
_audit_update_record             
;
2014-11-03 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30.30 H25.60 Cl0.60 N4 O2 Rh'
_chemical_formula_sum            'C30.30 H25.60 Cl0.60 N4 O2 Rh'
_chemical_formula_weight         601.93

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Rh Rh -1.1178 0.9187 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic

_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   9.6401(19)
_cell_length_b                   11.069(2)
_cell_length_c                   12.562(3)
_cell_angle_alpha                82.69(3)
_cell_angle_beta                 77.98(3)
_cell_angle_gamma                83.72(3)
_cell_volume                     1295.6(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             613
_exptl_absorpt_coefficient_mu    0.757
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16782
_diffrn_reflns_av_R_equivalents  0.0616
_diffrn_reflns_av_sigmaI/netI    0.0566
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.30
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4565
_reflns_number_gt                3527
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0774P)²+5.5233P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0042(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4565
_refine_ls_number_parameters     362
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0505
_refine_ls_wR_factor_ref         0.1693
_refine_ls_wR_factor_gt          0.1225
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Rh1 Rh 0.52687(5) 0.77208(4) 0.76405(4) 0.0365(2) Uani 1 1 d . . .
O1 O 0.3494(5) 0.7377(4) 0.6844(4) 0.0476(11) Uani 1 1 d . . .
N1 N 0.7088(5) 0.8940(5) 0.5869(4) 0.0406(12) Uani 1 1 d . . .
C1 C 0.7016(7) 0.7766(5) 0.6507(5) 0.0404(15) Uani 1 1 d . . .
Cl1B Cl 0.2540(6) 1.4601(5) 0.6081(5) 0.0543(14) Uani 0.30 1 d P . .
Cl1A Cl 0.5507(8) 1.4957(7) 0.4995(6) 0.063(2) Uani 0.30 1 d P . .
C1S C 0.345(2) 1.5479(18) 0.530(2) 0.049(7) Uani 0.30 1 d P . .
H1SA H 0.2994 1.5777 0.4690 0.059 Uiso 0.30 1 calc PR . .
H1SB H 0.3544 1.6174 0.5673 0.059 Uiso 0.30 1 calc PR . .
O2 O 0.3031(5) 0.7728(4) 0.8613(4) 0.0465(11) Uani 1 1 d . . .
N2 N 0.5012(5) 0.9499(4) 0.7003(4) 0.0359(11) Uani 1 1 d . . .
C2 C 0.8183(7) 0.7048(6) 0.6100(5) 0.0409(15) Uani 1 1 d . . .
N3 N 0.6978(5) 0.6773(4) 0.9173(4) 0.0367(12) Uani 1 1 d . . .
C3 C 0.9021(7) 0.7738(6) 0.5176(5) 0.0377(14) Uani 1 1 d . . .
N4 N 0.5630(5) 0.5942(4) 0.8234(4) 0.0350(11) Uani 1 1 d . . .
C4 C 1.0291(7) 0.7445(6) 0.4480(6) 0.0464(16) Uani 1 1 d . . .
H4A H 1.0765 0.6672 0.4571 0.056 Uiso 1 1 calc R . .
C5 C 1.0855(8) 0.8298(7) 0.3649(6) 0.0487(17) Uani 1 1 d . . .
H5A H 1.1707 0.8099 0.3177 0.058 Uiso 1 1 calc R . .
C6 C 1.0149(7) 0.9458(7) 0.3517(6) 0.0497(17) Uani 1 1 d . . .
H6A H 1.0545 1.0028 0.2958 0.060 Uiso 1 1 calc R . .
C7 C 0.8872(7) 0.9786(6) 0.4196(5) 0.0430(15) Uani 1 1 d . . .
H7A H 0.8400 1.0559 0.4099 0.052 Uiso 1 1 calc R . .
C8 C 0.8323(6) 0.8910(6) 0.5032(5) 0.0373(14) Uani 1 1 d . . .
C9 C 0.8618(9) 0.5750(7) 0.6494(7) 0.060(2) Uani 1 1 d . . .
H9A H 0.7912 0.5462 0.7105 0.091 Uiso 1 1 calc R . .
H9B H 0.9518 0.5714 0.6716 0.091 Uiso 1 1 calc R . .
H9C H 0.8702 0.5245 0.5913 0.091 Uiso 1 1 calc R . .
C11 C 0.6007(7) 0.9844(6) 0.6122(5) 0.0389(14) Uani 1 1 d . . .
C12 C 0.5885(8) 1.1004(6) 0.5560(6) 0.0497(17) Uani 1 1 d . . .
H12A H 0.6568 1.1241 0.4951 0.060 Uiso 1 1 calc R . .
C103 C 0.7844(6) 0.8258(6) 0.9859(5) 0.0386(14) Uani 1 1 d . . .
C13 C 0.4727(8) 1.1798(6) 0.5929(6) 0.0535(19) Uani 1 1 d . . .
H13A H 0.4621 1.2577 0.5563 0.064 Uiso 1 1 calc R . .
C14 C 0.3728(8) 1.1439(6) 0.6835(6) 0.0511(18) Uani 1 1 d . . .
H14A H 0.2949 1.1969 0.7094 0.061 Uiso 1 1 calc R . .
C15 C 0.3911(7) 1.0292(6) 0.7340(6) 0.0455(16) Uani 1 1 d . . .
H15A H 0.3236 1.0045 0.7951 0.055 Uiso 1 1 calc R . .
C31 C 0.2599(7) 0.7498(6) 0.7766(6) 0.0462(17) Uani 1 1 d . . .
C41 C 0.1056(8) 0.7326(8) 0.7815(7) 0.066(2) Uani 1 1 d . . .
H41A H 0.0464 0.7949 0.8202 0.099 Uiso 1 1 calc R . .
H41B H 0.0842 0.6536 0.8190 0.099 Uiso 1 1 calc R . .
H41C H 0.0880 0.7382 0.7086 0.099 Uiso 1 1 calc R . .
C101 C 0.6450(7) 0.7934(6) 0.8655(5) 0.0397(15) Uani 1 1 d . . .
C102 C 0.6984(7) 0.8829(6) 0.9086(5) 0.0370(14) Uani 1 1 d . . .
C104 C 0.8682(7) 0.8739(7) 1.0443(5) 0.0482(17) Uani 1 1 d . . .
H10E H 0.8730 0.9580 1.0391 0.058 Uiso 1 1 calc R . .
C105 C 0.9444(8) 0.7964(8) 1.1100(6) 0.062(2) Uani 1 1 d . . .
H10F H 0.9990 0.8284 1.1509 0.074 Uiso 1 1 calc R . .
C106 C 0.9404(8) 0.6710(8) 1.1158(6) 0.060(2) Uani 1 1 d . . .
H10G H 0.9933 0.6200 1.1603 0.072 Uiso 1 1 calc R . .
C107 C 0.8597(7) 0.6198(7) 1.0571(6) 0.0476(16) Uani 1 1 d . . .
H10D H 0.8561 0.5356 1.0625 0.057 Uiso 1 1 calc R . .
C108 C 0.7844(7) 0.6982(6) 0.9900(5) 0.0411(15) Uani 1 1 d . . .
C109 C 0.6722(7) 1.0195(6) 0.8850(5) 0.0458(16) Uani 1 1 d . . .
H10A H 0.6027 1.0378 0.8393 0.069 Uiso 1 1 calc R . .
H10B H 0.7595 1.0530 0.8482 0.069 Uiso 1 1 calc R . .
H10C H 0.6377 1.0548 0.9526 0.069 Uiso 1 1 calc R . .
C111 C 0.5085(7) 0.5004(6) 0.7936(6) 0.0452(16) Uani 1 1 d . . .
H11A H 0.4478 0.5167 0.7439 0.054 Uiso 1 1 calc R . .
C112 C 0.5388(8) 0.3807(6) 0.8335(6) 0.0513(18) Uani 1 1 d . . .
H11D H 0.5015 0.3169 0.8104 0.062 Uiso 1 1 calc R . .
C113 C 0.6271(8) 0.3585(6) 0.9098(6) 0.0522(19) Uani 1 1 d . . .
H11B H 0.6474 0.2791 0.9401 0.063 Uiso 1 1 calc R . .
C114 C 0.6840(7) 0.4535(6) 0.9402(6) 0.0457(16) Uani 1 1 d . . .
H11C H 0.7446 0.4391 0.9900 0.055 Uiso 1 1 calc R . .
C115 C 0.6500(6) 0.5725(5) 0.8954(5) 0.0353(14) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Rh1 C101 1.927(7) . ?
Rh1 C1 1.967(7) . ?
Rh1 N4 2.035(5) . ?
Rh1 N2 2.037(5) . ?
Rh1 O1 2.241(5) . ?
Rh1 O2 2.246(5) . ?
Rh1 C31 2.582(7) . ?
O1 C31 1.305(8) . ?
N1 C11 1.379(8) . ?
N1 C8 1.416(8) . ?
N1 C1 1.438(8) . ?
C1 C2 1.351(9) . ?
Cl1B C1S 1.50(3) . ?
Cl1B Cl1A 2.141(9) 2_686 ?
Cl1A Cl1A 0.969(14) 2_686 ?
Cl1A C1S 1.08(2) 2_686 ?
Cl1A C1S 1.98(2) . ?
Cl1A Cl1B 2.141(9) 2_686 ?
C1S Cl1A 1.08(2) 2_686 ?
O2 C31 1.283(8) . ?
N2 C15 1.334(8) . ?
N2 C11 1.349(8) . ?
C2 C3 1.450(9) . ?
C2 C9 1.503(9) . ?
N3 C115 1.373(8) . ?
N3 C108 1.414(8) . ?
N3 C101 1.456(8) . ?
C3 C4 1.382(9) . ?
C3 C8 1.403(9) . ?
N4 C111 1.340(8) . ?
N4 C115 1.340(8) . ?
C4 C5 1.379(10) . ?
C5 C6 1.393(10) . ?
C6 C7 1.385(9) . ?
C7 C8 1.395(9) . ?
C11 C12 1.390(9) . ?
C12 C13 1.380(10) . ?
C103 C104 1.384(9) . ?
C103 C108 1.406(9) . ?
C103 C102 1.447(9) . ?
C13 C14 1.376(10) . ?
C14 C15 1.356(9) . ?
C31 C41 1.508(10) . ?
C101 C102 1.380(9) . ?
C102 C109 1.507(9) . ?
C104 C105 1.376(11) . ?
C105 C106 1.385(12) . ?
C106 C107 1.383(10) . ?
C107 C108 1.386(9) . ?
C111 C112 1.378(10) . ?
C112 C113 1.392(11) . ?
C113 C114 1.366(10) . ?
C114 C115 1.397(9) . ?

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
C101 Rh1 C1 86.4(3) . . ?
C101 Rh1 N4 81.0(2) . . ?
C1 Rh1 N4 95.9(2) . . ?
C101 Rh1 N2 98.2(2) . . ?
C1 Rh1 N2 81.2(2) . . ?
N4 Rh1 N2 177.05(19) . . ?
C101 Rh1 O1 165.7(2) . . ?
C1 Rh1 O1 107.7(2) . . ?
N4 Rh1 O1 94.53(18) . . ?
N2 Rh1 O1 86.98(19) . . ?
C101 Rh1 O2 106.0(2) . . ?
C1 Rh1 O2 167.2(2) . . ?
N4 Rh1 O2 89.30(18) . . ?
N2 Rh1 O2 93.65(18) . . ?
O1 Rh1 O2 60.14(17) . . ?
C101 Rh1 C31 135.7(2) . . ?
C1 Rh1 C31 137.9(3) . . ?
N4 Rh1 C31 92.2(2) . . ?
N2 Rh1 C31 90.4(2) . . ?
O1 Rh1 C31 30.3(2) . . ?
O2 Rh1 C31 29.8(2) . . ?
C31 O1 Rh1 89.4(4) . . ?
C11 N1 C8 131.9(5) . . ?
C11 N1 C1 119.0(5) . . ?
C8 N1 C1 109.1(5) . . ?
C2 C1 N1 107.7(5) . . ?
C2 C1 Rh1 141.1(5) . . ?
N1 C1 Rh1 111.1(4) . . ?
C1S Cl1B Cl1A 28.1(7) . 2_686 ?
Cl1A Cl1A C1S 149.1(18) 2_686 2_686 ?
Cl1A Cl1A C1S 16.3(10) 2_686 . ?
C1S Cl1A C1S 165.4(8) 2_686 . ?
Cl1A Cl1A Cl1B 139.6(11) 2_686 2_686 ?
C1S Cl1A Cl1B 40.9(13) 2_686 2_686 ?
C1S Cl1A Cl1B 141.9(9) . 2_686 ?
Cl1A C1S Cl1B 111.0(16) 2_686 . ?
Cl1A C1S Cl1A 14.6(8) 2_686 . ?
Cl1B C1S Cl1A 115.2(12) . . ?
C31 O2 Rh1 89.8(4) . . ?
C15 N2 C11 119.1(5) . . ?
C15 N2 Rh1 125.3(4) . . ?
C11 N2 Rh1 115.4(4) . . ?
C1 C2 C3 108.7(6) . . ?
C1 C2 C9 128.5(6) . . ?
C3 C2 C9 122.9(6) . . ?
C115 N3 C108 132.1(5) . . ?
C115 N3 C101 117.9(5) . . ?
C108 N3 C101 109.8(5) . . ?
C4 C3 C8 119.3(6) . . ?
C4 C3 C2 132.4(6) . . ?
C8 C3 C2 108.3(5) . . ?
C111 N4 C115 119.5(5) . . ?
C111 N4 Rh1 124.5(4) . . ?
C115 N4 Rh1 116.0(4) . . ?
C5 C4 C3 120.0(6) . . ?
C4 C5 C6 120.0(6) . . ?
C7 C6 C5 121.7(6) . . ?
C6 C7 C8 117.3(6) . . ?
C7 C8 C3 121.7(6) . . ?
C7 C8 N1 132.2(6) . . ?
C3 C8 N1 106.2(5) . . ?
N2 C11 N1 113.1(5) . . ?
N2 C11 C12 120.8(6) . . ?
N1 C11 C12 126.2(6) . . ?
C13 C12 C11 118.5(6) . . ?
C104 C103 C108 119.5(6) . . ?
C104 C103 C102 131.8(6) . . ?
C108 C103 C102 108.5(5) . . ?
C14 C13 C12 120.2(6) . . ?
C15 C14 C13 118.2(7) . . ?
N2 C15 C14 123.2(6) . . ?
O2 C31 O1 120.7(6) . . ?
O2 C31 C41 121.1(7) . . ?
O1 C31 C41 118.2(7) . . ?
O2 C31 Rh1 60.5(3) . . ?
O1 C31 Rh1 60.2(3) . . ?
C41 C31 Rh1 177.8(6) . . ?
C102 C101 N3 106.0(6) . . ?
C102 C101 Rh1 141.8(5) . . ?
N3 C101 Rh1 112.2(4) . . ?
C101 C102 C103 109.2(6) . . ?
C101 C102 C109 127.7(6) . . ?
C103 C102 C109 123.1(5) . . ?
C105 C104 C103 119.4(7) . . ?
C104 C105 C106 120.5(7) . . ?
C107 C106 C105 121.6(7) . . ?
C106 C107 C108 117.7(7) . . ?
C107 C108 C103 121.2(6) . . ?
C107 C108 N3 132.4(6) . . ?
C103 C108 N3 106.4(6) . . ?
N4 C111 C112 122.6(7) . . ?
C111 C112 C113 117.8(6) . . ?
C114 C113 C112 120.0(6) . . ?
C113 C114 C115 119.1(7) . . ?
N4 C115 N3 112.8(5) . . ?
N4 C115 C114 120.9(6) . . ?
N3 C115 C114 126.3(6) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.901
_refine_diff_density_min         -0.964
_refine_diff_density_rms         0.141
####################################################################### 
# 
# 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_p
_audit_block_doi                 10.5517/cc13n9dg
_database_code_depnum_ccdc_archive 'CCDC 1032405'
_audit_update_record             
;
2014-11-03 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H21 Cl N2'
_chemical_formula_sum            'C30 H21 Cl N2'
_chemical_formula_weight         444.94

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   8.8053(4)
_cell_length_b                   11.2771(10)
_cell_length_c                   12.0975(13)
_cell_angle_alpha                67.401(9)
_cell_angle_beta                 89.113(7)
_cell_angle_gamma                83.151(6)
_cell_volume                     1100.51(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3406
_cell_measurement_theta_min      3.9480
_cell_measurement_theta_max      30.0080

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.41053
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8275
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_sigmaI/netI    0.0533
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.42
_diffrn_reflns_theta_max         26.00
_reflns_number_total             4304
_reflns_number_gt                3521
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0852P)²+1.1871P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4304
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0630
_refine_ls_wR_factor_ref         0.1778
_refine_ls_wR_factor_gt          0.1664
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 1.14884(8) 0.37852(6) 0.10019(6) 0.0276(2) Uani 1 1 d . . .
N1 N 0.8305(2) 0.61229(19) 0.41087(19) 0.0171(5) Uani 1 1 d . . .
C1 C 0.7494(3) 0.5076(2) 0.4790(2) 0.0204(6) Uani 1 1 d . . .
N2 N 0.8970(3) 1.0013(3) 0.1455(3) 0.0379(7) Uani 1 1 d . . .
C2 C 0.7851(3) 0.4079(2) 0.4418(2) 0.0213(6) Uani 1 1 d . . .
H2B H 0.7467 0.3286 0.4719 0.026 Uiso 1 1 calc R . .
C3 C 0.8913(3) 0.4471(2) 0.3490(2) 0.0192(5) Uani 1 1 d . . .
C4 C 0.9642(3) 0.3852(2) 0.2780(2) 0.0214(6) Uani 1 1 d . . .
H4A H 0.9471 0.3017 0.2888 0.026 Uiso 1 1 calc R . .
C5 C 1.0607(3) 0.4502(3) 0.1930(2) 0.0217(6) Uani 1 1 d . . .
C6 C 1.0916(3) 0.5762(3) 0.1760(3) 0.0226(6) Uani 1 1 d . . .
H6A H 1.1589 0.6172 0.1177 0.027 Uiso 1 1 calc R . .
C7 C 1.0230(3) 0.6382(2) 0.2449(2) 0.0213(6) Uani 1 1 d . . .
H7A H 1.0443 0.7204 0.2351 0.026 Uiso 1 1 calc R . .
C8 C 0.9200(3) 0.5745(2) 0.3304(2) 0.0185(5) Uani 1 1 d . . .
C9 C 0.8033(3) 0.7279(2) 0.4271(2) 0.0186(5) Uani 1 1 d . . .
C10 C 0.7172(2) 0.7424(2) 0.5090(2) 0.0092(4) Uani 1 1 d . . .
H10A H 0.7054 0.8208 0.5189 0.011 Uiso 1 1 calc R . .
C11 C 0.6416(3) 0.6403(2) 0.5827(2) 0.0201(6) Uani 1 1 d . . .
C12 C 0.6539(3) 0.5262(2) 0.5677(2) 0.0202(6) Uani 1 1 d . . .
H12A H 0.5995 0.4603 0.6157 0.024 Uiso 1 1 calc R . .
C31 C 0.8731(3) 0.8408(2) 0.3429(2) 0.0180(5) Uani 1 1 d . . .
C32 C 0.8202(3) 0.9014(2) 0.2226(2) 0.0187(5) Uani 1 1 d . . .
C33 C 1.0194(3) 1.0417(3) 0.1883(3) 0.0243(6) Uani 1 1 d . . .
H33A H 1.0694 1.1079 0.1352 0.029 Uiso 1 1 calc R . .
C34 C 1.0688(3) 0.9858(2) 0.3081(3) 0.0228(6) Uani 1 1 d . . .
C35 C 0.9935(3) 0.8845(2) 0.3843(2) 0.0211(6) Uani 1 1 d . . .
H35A H 1.0244 0.8450 0.4647 0.025 Uiso 1 1 calc R . .
C36 C 1.2002(3) 1.0308(3) 0.3531(3) 0.0291(7) Uani 1 1 d . . .
H36A H 1.2155 0.9830 0.4379 0.044 Uiso 1 1 calc R . .
H36B H 1.1774 1.1214 0.3373 0.044 Uiso 1 1 calc R . .
H36C H 1.2914 1.0168 0.3131 0.044 Uiso 1 1 calc R . .
C41 C 0.5401(3) 0.6669(3) 0.6710(2) 0.0209(6) Uani 1 1 d . . .
C42 C 0.4982(3) 0.5677(3) 0.7724(2) 0.0252(6) Uani 1 1 d . . .
H42A H 0.5404 0.4829 0.7882 0.030 Uiso 1 1 calc R . .
C43 C 0.3946(3) 0.5927(3) 0.8505(3) 0.0286(7) Uani 1 1 d . . .
H43A H 0.3677 0.5251 0.9182 0.034 Uiso 1 1 calc R . .
C44 C 0.3315(3) 0.7186(3) 0.8272(3) 0.0287(6) Uani 1 1 d . . .
H44A H 0.2609 0.7357 0.8789 0.034 Uiso 1 1 calc R . .
C45 C 0.3731(3) 0.8192(3) 0.7273(3) 0.0284(6) Uani 1 1 d . . .
H45A H 0.3307 0.9037 0.7120 0.034 Uiso 1 1 calc R . .
C46 C 0.4777(3) 0.7942(3) 0.6502(3) 0.0252(6) Uani 1 1 d . . .
H46A H 0.5069 0.8624 0.5840 0.030 Uiso 1 1 calc R . .
C51 C 0.6849(3) 0.8626(2) 0.1784(2) 0.0205(6) Uani 1 1 d . . .
C52 C 0.6922(3) 0.8374(3) 0.0736(3) 0.0291(6) Uani 1 1 d . . .
H52A H 0.7836 0.8416 0.0333 0.035 Uiso 1 1 calc R . .
C53 C 0.5658(4) 0.8063(3) 0.0292(3) 0.0326(7) Uani 1 1 d . . .
H53A H 0.5722 0.7898 -0.0405 0.039 Uiso 1 1 calc R . .
C54 C 0.4294(3) 0.7997(3) 0.0885(3) 0.0311(7) Uani 1 1 d . . .
H54A H 0.3442 0.7788 0.0587 0.037 Uiso 1 1 calc R . .
C55 C 0.4197(3) 0.8242(3) 0.1924(3) 0.0290(7) Uani 1 1 d . . .
H55A H 0.3279 0.8202 0.2320 0.035 Uiso 1 1 calc R . .
C56 C 0.5472(3) 0.8547(2) 0.2373(3) 0.0232(6) Uani 1 1 d . . .
H56A H 0.5404 0.8701 0.3075 0.028 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C5 1.743(3) . ?
N1 C9 1.384(3) . ?
N1 C8 1.401(3) . ?
N1 C1 1.421(3) . ?
C1 C2 1.367(4) . ?
C1 C12 1.416(4) . ?
N2 C32 1.397(4) . ?
N2 C33 1.398(4) . ?
C2 C3 1.420(4) . ?
C3 C4 1.405(4) . ?
C3 C8 1.420(3) . ?
C4 C5 1.363(4) . ?
C5 C6 1.414(4) . ?
C6 C7 1.372(4) . ?
C7 C8 1.401(4) . ?
C9 C10 1.286(4) . ?
C9 C31 1.486(4) . ?
C10 C11 1.393(3) . ?
C11 C12 1.358(4) . ?
C11 C41 1.477(4) . ?
C31 C35 1.395(4) . ?
C31 C32 1.408(4) . ?
C32 C51 1.491(4) . ?
C33 C34 1.391(4) . ?
C34 C35 1.396(4) . ?
C34 C36 1.505(4) . ?
C41 C42 1.386(4) . ?
C41 C46 1.401(4) . ?
C42 C43 1.386(4) . ?
C43 C44 1.384(4) . ?
C44 C45 1.383(4) . ?
C45 C46 1.383(4) . ?
C51 C56 1.392(4) . ?
C51 C52 1.401(4) . ?
C52 C53 1.381(4) . ?
C53 C54 1.385(5) . ?
C54 C55 1.386(4) . ?
C55 C56 1.388(4) . ?

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 N1 C8 132.7(2) . . ?
C9 N1 C1 119.3(2) . . ?
C8 N1 C1 107.8(2) . . ?
C2 C1 C12 134.3(3) . . ?
C2 C1 N1 109.3(2) . . ?
C12 C1 N1 116.4(2) . . ?
C32 N2 C33 120.5(3) . . ?
C1 C2 C3 107.7(2) . . ?
C4 C3 C8 119.4(2) . . ?
C4 C3 C2 132.3(2) . . ?
C8 C3 C2 108.3(2) . . ?
C5 C4 C3 118.5(2) . . ?
C4 C5 C6 122.2(2) . . ?
C4 C5 Cl1 119.9(2) . . ?
C6 C5 Cl1 118.0(2) . . ?
C7 C6 C5 120.4(3) . . ?
C6 C7 C8 118.3(2) . . ?
N1 C8 C7 131.9(2) . . ?
N1 C8 C3 106.9(2) . . ?
C7 C8 C3 121.1(2) . . ?
C10 C9 N1 123.0(2) . . ?
C10 C9 C31 119.1(2) . . ?
N1 C9 C31 117.9(2) . . ?
C9 C10 C11 119.7(2) . . ?
C12 C11 C10 121.1(2) . . ?
C12 C11 C41 122.6(2) . . ?
C10 C11 C41 116.2(2) . . ?
C11 C12 C1 120.1(2) . . ?
C35 C31 C32 120.5(2) . . ?
C35 C31 C9 119.0(2) . . ?
C32 C31 C9 120.5(2) . . ?
N2 C32 C31 118.0(2) . . ?
N2 C32 C51 120.5(2) . . ?
C31 C32 C51 121.5(2) . . ?
C34 C33 N2 122.0(3) . . ?
C33 C34 C35 117.3(2) . . ?
C33 C34 C36 121.4(2) . . ?
C35 C34 C36 121.3(3) . . ?
C31 C35 C34 121.7(3) . . ?
C42 C41 C46 118.5(3) . . ?
C42 C41 C11 121.5(2) . . ?
C46 C41 C11 120.0(2) . . ?
C41 C42 C43 121.1(3) . . ?
C44 C43 C42 119.7(3) . . ?
C45 C44 C43 120.1(3) . . ?
C46 C45 C44 120.2(3) . . ?
C45 C46 C41 120.4(3) . . ?
C56 C51 C52 118.3(3) . . ?
C56 C51 C32 121.2(2) . . ?
C52 C51 C32 120.5(2) . . ?
C53 C52 C51 120.9(3) . . ?
C52 C53 C54 119.9(3) . . ?
C53 C54 C55 120.1(3) . . ?
C54 C55 C56 119.9(3) . . ?
C55 C56 C51 120.8(3) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.758
_refine_diff_density_min         -0.815
_refine_diff_density_rms         0.074

####################################################################### 
# 
# 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_tl20140907-2
_audit_block_doi                 10.5517/cc13n9fh
_database_code_depnum_ccdc_archive 'CCDC 1032406'
_audit_update_record             
;
2014-11-03 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H26 N2 O'
_chemical_formula_weight         454.55

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   p_1_21/c_1
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.9489(5)
_cell_length_b                   17.1959(6)
_cell_length_c                   14.4905(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.121(6)
_cell_angle_gamma                90.00
_cell_volume                     2342.26(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             960
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71000
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10431
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_sigmaI/netI    0.0337
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.80
_diffrn_reflns_theta_max         26.00
_reflns_number_total             4431
_reflns_number_gt                3659
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4431
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1082
_refine_ls_R_factor_gt           0.0927
_refine_ls_wR_factor_ref         0.3157
_refine_ls_wR_factor_gt          0.3069
_refine_ls_goodness_of_fit_ref   2.317
_refine_ls_restrained_S_all      2.317
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4790(3) 0.64714(16) 0.2199(2) 0.0471(8) Uani 1 1 d . . .
N1 N 1.0402(3) 0.29890(14) 0.51912(19) 0.0256(7) Uani 1 1 d . . .
C1 C 1.0999(3) 0.35435(17) 0.4715(2) 0.0242(7) Uani 1 1 d . . .
N2 N 0.7917(4) 0.1823(2) 0.6930(3) 0.0481(9) Uani 1 1 d . . .
C2 C 1.2392(3) 0.33513(18) 0.4843(2) 0.0243(7) Uani 1 1 d . . .
C3 C 1.2693(4) 0.26591(18) 0.5419(2) 0.0279(8) Uani 1 1 d . . .
C4 C 1.3919(4) 0.22026(19) 0.5757(3) 0.0311(8) Uani 1 1 d . . .
H4A H 1.4742 0.2343 0.5626 0.037 Uiso 1 1 calc R . .
C5 C 1.3890(4) 0.1533(2) 0.6293(3) 0.0354(9) Uani 1 1 d . . .
H5A H 1.4686 0.1213 0.6503 0.042 Uiso 1 1 calc R . .
C6 C 1.2652(4) 0.1342(2) 0.6518(3) 0.0363(9) Uani 1 1 d . . .
H6A H 1.2660 0.0901 0.6890 0.044 Uiso 1 1 calc R . .
C7 C 1.1442(4) 0.17818(19) 0.6208(3) 0.0305(8) Uani 1 1 d . . .
H7A H 1.0634 0.1647 0.6361 0.037 Uiso 1 1 calc R . .
C8 C 1.1467(3) 0.24416(18) 0.5653(2) 0.0267(8) Uani 1 1 d . . .
C9 C 0.8982(4) 0.30404(18) 0.5093(2) 0.0276(8) Uani 1 1 d . . .
C10 C 0.8161(3) 0.35847(16) 0.4614(2) 0.0173(6) Uani 1 1 d . . .
H10A H 0.7202 0.3585 0.4556 0.021 Uiso 1 1 calc R . .
C11 C 0.8712(3) 0.41739(18) 0.4182(2) 0.0245(7) Uani 1 1 d . . .
C12 C 1.0099(3) 0.41508(18) 0.4222(2) 0.0261(7) Uani 1 1 d . . .
H12A H 1.0455 0.4540 0.3920 0.031 Uiso 1 1 calc R . .
C13 C 1.3428(4) 0.3781(2) 0.4477(3) 0.0341(9) Uani 1 1 d . . .
H13A H 1.2970 0.4228 0.4111 0.051 Uiso 1 1 calc R . .
H13B H 1.3752 0.3445 0.4065 0.051 Uiso 1 1 calc R . .
H13C H 1.4225 0.3946 0.5022 0.051 Uiso 1 1 calc R . .
C21 C 0.7696(4) 0.47773(18) 0.3668(2) 0.0260(7) Uani 1 1 d . . .
C22 C 0.8140(4) 0.54345(18) 0.3268(2) 0.0285(8) Uani 1 1 d . . .
H22A H 0.9100 0.5494 0.3344 0.034 Uiso 1 1 calc R . .
C23 C 0.7185(4) 0.59954(19) 0.2764(3) 0.0320(8) Uani 1 1 d . . .
H23A H 0.7508 0.6415 0.2489 0.038 Uiso 1 1 calc R . .
C24 C 0.5767(4) 0.59403(19) 0.2663(3) 0.0339(8) Uani 1 1 d . . .
C25 C 0.5300(4) 0.5284(2) 0.3064(3) 0.0392(9) Uani 1 1 d . . .
H25A H 0.4343 0.5234 0.3000 0.047 Uiso 1 1 calc R . .
C26 C 0.6251(4) 0.4720(2) 0.3549(3) 0.0332(8) Uani 1 1 d . . .
H26A H 0.5923 0.4291 0.3802 0.040 Uiso 1 1 calc R . .
C31 C 0.8378(3) 0.24027(19) 0.5554(3) 0.0300(8) Uani 1 1 d . . .
C32 C 0.7912(4) 0.1744(2) 0.5022(3) 0.0355(9) Uani 1 1 d . . .
H32A H 0.7926 0.1718 0.4384 0.043 Uiso 1 1 calc R . .
C33 C 0.7409(4) 0.1101(2) 0.5417(3) 0.0380(9) Uani 1 1 d . . .
C34 C 0.7456(4) 0.1162(2) 0.6384(3) 0.0370(9) Uani 1 1 d . . .
H34A H 0.7165 0.0740 0.6672 0.044 Uiso 1 1 calc R . .
C35 C 0.8384(3) 0.2470(2) 0.6529(3) 0.0315(9) Uani 1 1 d . . .
C41 C 0.8882(4) 0.31691(19) 0.7131(3) 0.0329(9) Uani 1 1 d . . .
C42 C 0.9963(4) 0.3128(2) 0.8028(3) 0.0375(9) Uani 1 1 d . . .
H42A H 1.0406 0.2652 0.8235 0.045 Uiso 1 1 calc R . .
C43 C 1.0400(5) 0.3772(2) 0.8622(3) 0.0415(10) Uani 1 1 d . . .
H43A H 1.1125 0.3722 0.9217 0.050 Uiso 1 1 calc R . .
C44 C 0.9767(5) 0.4494(2) 0.8340(3) 0.0440(10) Uani 1 1 d . . .
H44A H 1.0060 0.4930 0.8734 0.053 Uiso 1 1 calc R . .
C45 C 0.8682(4) 0.4540(2) 0.7448(3) 0.0380(9) Uani 1 1 d . . .
H45A H 0.8241 0.5017 0.7248 0.046 Uiso 1 1 calc R . .
C46 C 0.8236(4) 0.3901(2) 0.6848(3) 0.0353(9) Uani 1 1 d . . .
H46A H 0.7506 0.3954 0.6255 0.042 Uiso 1 1 calc R . .
C51 C 0.5240(5) 0.7120(2) 0.1763(3) 0.0490(10) Uani 1 1 d . . .
H51A H 0.4440 0.7451 0.1459 0.074 Uiso 1 1 calc R . .
H51D H 0.5635 0.6940 0.1279 0.074 Uiso 1 1 calc R . .
H51B H 0.5949 0.7407 0.2256 0.074 Uiso 1 1 calc R . .
C61 C 0.6879(5) 0.0386(2) 0.4817(4) 0.0527(11) Uani 1 1 d . . .
H61A H 0.6589 0.0008 0.5202 0.079 Uiso 1 1 calc R . .
H61B H 0.7625 0.0173 0.4610 0.079 Uiso 1 1 calc R . .
H61C H 0.6082 0.0519 0.4255 0.079 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C24 1.342(4) . ?
O1 C51 1.425(4) . ?
N1 C9 1.376(4) . ?
N1 C8 1.411(4) . ?
N1 C1 1.416(4) . ?
C1 C2 1.377(4) . ?
C1 C12 1.408(5) . ?
N2 C34 1.375(5) . ?
N2 C35 1.402(4) . ?
C2 C3 1.428(4) . ?
C2 C13 1.499(4) . ?
C3 C4 1.398(5) . ?
C3 C8 1.419(4) . ?
C4 C5 1.395(5) . ?
C5 C6 1.412(5) . ?
C6 C7 1.367(5) . ?
C7 C8 1.396(4) . ?
C9 C10 1.286(4) . ?
C9 C31 1.507(4) . ?
C10 C11 1.394(4) . ?
C11 C12 1.363(4) . ?
C11 C21 1.469(5) . ?
C21 C26 1.394(5) . ?
C21 C22 1.405(4) . ?
C22 C23 1.383(5) . ?
C23 C24 1.374(5) . ?
C24 C25 1.416(5) . ?
C25 C26 1.376(5) . ?
C31 C32 1.363(5) . ?
C31 C35 1.417(5) . ?
C32 C33 1.411(5) . ?
C33 C34 1.389(5) . ?
C33 C61 1.498(6) . ?
C35 C41 1.473(5) . ?
C41 C42 1.391(5) . ?
C41 C46 1.412(5) . ?
C42 C43 1.382(6) . ?
C43 C44 1.393(5) . ?
C44 C45 1.388(6) . ?
C45 C46 1.381(5) . ?

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
C24 O1 C51 118.3(3) . . ?
C9 N1 C8 132.7(3) . . ?
C9 N1 C1 119.1(3) . . ?
C8 N1 C1 108.1(2) . . ?
C2 C1 C12 133.7(3) . . ?
C2 C1 N1 109.7(3) . . ?
C12 C1 N1 116.7(3) . . ?
C34 N2 C35 120.7(3) . . ?
C1 C2 C3 106.7(3) . . ?
C1 C2 C13 127.8(3) . . ?
C3 C2 C13 125.5(3) . . ?
C4 C3 C8 119.2(3) . . ?
C4 C3 C2 131.7(3) . . ?
C8 C3 C2 109.1(3) . . ?
C5 C4 C3 118.9(3) . . ?
C4 C5 C6 120.0(3) . . ?
C7 C6 C5 122.5(3) . . ?
C6 C7 C8 117.3(3) . . ?
C7 C8 N1 131.5(3) . . ?
C7 C8 C3 122.1(3) . . ?
N1 C8 C3 106.3(3) . . ?
C10 C9 N1 123.5(3) . . ?
C10 C9 C31 119.6(3) . . ?
N1 C9 C31 116.9(3) . . ?
C9 C10 C11 119.9(3) . . ?
C12 C11 C10 120.1(3) . . ?
C12 C11 C21 124.1(3) . . ?
C10 C11 C21 115.8(3) . . ?
C11 C12 C1 120.6(3) . . ?
C26 C21 C22 117.1(3) . . ?
C26 C21 C11 121.5(3) . . ?
C22 C21 C11 121.3(3) . . ?
C23 C22 C21 121.7(3) . . ?
C24 C23 C22 120.8(3) . . ?
O1 C24 C23 123.8(3) . . ?
O1 C24 C25 117.8(3) . . ?
C23 C24 C25 118.4(3) . . ?
C26 C25 C24 120.5(3) . . ?
C25 C26 C21 121.5(3) . . ?
C32 C31 C35 121.4(3) . . ?
C32 C31 C9 117.7(3) . . ?
C35 C31 C9 120.7(3) . . ?
C31 C32 C33 121.5(3) . . ?
C34 C33 C32 116.7(3) . . ?
C34 C33 C61 122.5(3) . . ?
C32 C33 C61 120.8(3) . . ?
N2 C34 C33 122.6(3) . . ?
N2 C35 C31 117.1(3) . . ?
N2 C35 C41 119.7(3) . . ?
C31 C35 C41 123.2(3) . . ?
C42 C41 C46 117.2(3) . . ?
C42 C41 C35 121.2(3) . . ?
C46 C41 C35 121.5(3) . . ?
C43 C42 C41 122.0(3) . . ?
C42 C43 C44 120.9(4) . . ?
C45 C44 C43 117.5(4) . . ?
C46 C45 C44 122.2(3) . . ?
C45 C46 C41 120.3(4) . . ?

_diffrn_measured_fraction_theta_max 0.960
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.960
_refine_diff_density_max         0.914
_refine_diff_density_min         -0.678
_refine_diff_density_rms         0.078
