# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1027406'
_audit_update_record             
;
2014-10-02 deposited with the CCDC.
2015-06-29 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            rzg1463cb
_chemical_formula_moiety         ?
_chemical_formula_sum            'C41 H29 N2 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         565.66
_chemical_absolute_configuration ?

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   9.7022(3)
_cell_length_b                   14.1065(5)
_cell_length_c                   22.5755(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3089.78(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6358
_cell_measurement_theta_min      2.3108
_cell_measurement_theta_max      20.1346
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1188

_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_T_max  1.00

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            47889
_diffrn_reflns_av_R_equivalents  0.0608
_diffrn_reflns_av_sigmaI/netI    0.0441
_diffrn_reflns_theta_min         1.70
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26

_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.
;

_reflns_number_total             5471
_reflns_number_gt                3747
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0886
_refine_ls_R_factor_gt           0.0461
_refine_ls_wR_factor_gt          0.1103
_refine_ls_wR_factor_ref         0.1398
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_refine_ls_number_reflns         5471
_refine_ls_number_parameters     397
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0875P)²+0.0000P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.301
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.(2)

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'

_computing_data_collection       'Bruker Instrument Service v2010.9.0.0'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.1991(2) 0.08759(18) 0.04986(10) 0.0390(6) Uani d . 1 . .
C C2 0.1976(2) 0.12559(17) 0.10862(11) 0.0376(6) Uani d . 1 . .
C C3 0.2208(3) 0.06628(18) 0.15644(10) 0.0394(6) Uani d . 1 . .
C C4 0.2484(3) -0.03282(18) 0.14784(11) 0.0427(6) Uani d . 1 . .
C C5 0.2602(3) -0.06891(18) 0.09119(11) 0.0449(6) Uani d . 1 . .
C C6 0.2375(3) -0.00858(18) 0.04097(11) 0.0438(6) Uani d . 1 . .
C C7 0.1797(3) 0.22963(18) 0.11938(11) 0.0416(6) Uani d . 1 . .
C C8 0.2880(3) 0.29053(19) 0.10858(13) 0.0547(7) Uani d . 1 . .
H H8 0.3693 0.2673 0.0924 0.066 Uiso calc R 1 . .
C C9 0.2765(4) 0.3859(2) 0.12169(16) 0.0721(10) Uani d . 1 . .
H H9 0.3506 0.4262 0.1146 0.087 Uiso calc R 1 . .
C C10 0.1569(5) 0.4217(2) 0.14498(16) 0.0787(11) Uani d . 1 . .
H H10 0.15 0.4858 0.154 0.094 Uiso calc R 1 . .
C C11 0.0483(4) 0.3628(2) 0.15488(15) 0.0736(10) Uani d . 1 . .
H H11 -0.0337 0.3869 0.17 0.088 Uiso calc R 1 . .
C C12 0.0597(3) 0.2670(2) 0.14252(13) 0.0567(8) Uani d . 1 . .
H H12 -0.0147 0.2272 0.1499 0.068 Uiso calc R 1 . .
C C13 0.2152(3) 0.10714(18) 0.21776(11) 0.0435(6) Uani d . 1 . .
C C14 0.3162(3) 0.1693(2) 0.23652(13) 0.0575(8) Uani d . 1 . .
H H14 0.39 0.183 0.2117 0.069 Uiso calc R 1 . .
C C15 0.3089(4) 0.2116(2) 0.29183(15) 0.0732(10) Uani d . 1 . .
H H15 0.3773 0.2535 0.304 0.088 Uiso calc R 1 . .
C C16 0.2000(4) 0.1912(2) 0.32867(15) 0.0751(10) Uani d . 1 . .
H H16 0.1943 0.2195 0.3658 0.09 Uiso calc R 1 . .
C C17 0.1003(4) 0.1293(2) 0.31077(14) 0.0666(9) Uani d . 1 . .
H H17 0.0268 0.1157 0.3358 0.08 Uiso calc R 1 . .
C C18 0.1075(3) 0.0867(2) 0.25567(12) 0.0520(7) Uani d . 1 . .
H H18 0.0395 0.0441 0.2441 0.062 Uiso calc R 1 . .
C C19 0.2675(3) -0.09733(19) 0.20002(11) 0.0455(6) Uani d . 1 . .
C C20 0.3638(3) -0.0783(2) 0.24361(13) 0.0576(8) Uani d . 1 . .
H H20 0.4162 -0.0233 0.2413 0.069 Uiso calc R 1 . .
C C21 0.3835(4) -0.1397(3) 0.29050(15) 0.0717(10) Uani d . 1 . .
H H21 0.4487 -0.1257 0.3194 0.086 Uiso calc R 1 . .
C C22 0.3073(4) -0.2211(3) 0.29468(16) 0.0792(11) Uani d . 1 . .
H H22 0.3209 -0.2627 0.3261 0.095 Uiso calc R 1 . .
C C23 0.2112(4) -0.2404(2) 0.25229(15) 0.0703(9) Uani d . 1 . .
H H23 0.1592 -0.2956 0.255 0.084 Uiso calc R 1 . .
C C24 0.1902(3) -0.1795(2) 0.20573(13) 0.0557(7) Uani d . 1 . .
H H24 0.1231 -0.1936 0.1776 0.067 Uiso calc R 1 . .
C C25 0.2963(3) -0.17046(19) 0.07981(12) 0.0537(7) Uani d . 1 . .
C C26 0.2012(4) -0.2329(2) 0.05729(15) 0.0764(10) Uani d . 1 . .
H H26 0.1121 -0.2121 0.0494 0.092 Uiso calc R 1 . .
C C27 0.2365(6) -0.3266(3) 0.04624(19) 0.1045(14) Uani d . 1 . .
H H27 0.1718 -0.3687 0.031 0.125 Uiso calc R 1 . .
C C28 0.3698(6) -0.3564(3) 0.0584(2) 0.1076(16) Uani d . 1 . .
H H28 0.3945 -0.419 0.0514 0.129 Uiso calc R 1 . .
C C29 0.4625(5) -0.2962(3) 0.07994(17) 0.1009(14) Uani d . 1 . .
H H29 0.5514 -0.3175 0.0879 0.121 Uiso calc R 1 . .
C C30 0.4289(4) -0.2028(2) 0.09063(14) 0.0719(10) Uani d . 1 . .
H H30 0.4954 -0.1614 0.1051 0.086 Uiso calc R 1 . .
C C31 0.2543(3) -0.0408(2) -0.01740(12) 0.0580(8) Uani d . 1 . .
H H31 0.2847 -0.1023 -0.0245 0.07 Uiso calc R 1 . .
C C32 0.2260(4) 0.0181(2) -0.06347(13) 0.0699(9) Uani d . 1 . .
H H32 0.2413 -0.004 -0.1017 0.084 Uiso calc R 1 . .
N N1 0.1767(3) 0.10703(18) -0.05671(10) 0.0603(7) Uani d . 1 . .
C C33 0.1639(3) 0.14020(18) -0.00233(12) 0.0445(7) Uani d . 1 . .
C C35 0.0937(3) 0.2346(2) -0.00237(12) 0.0457(6) Uani d . 1 . .
N N2 0.1697(2) 0.30535(16) -0.02529(11) 0.0554(6) Uani d . 1 . .
C C37 0.1151(4) 0.4012(2) -0.03121(17) 0.0750(10) Uani d . 1 . .
H H37A 0.1274 0.4352 0.0058 0.09 Uiso calc R 1 . .
H H37B 0.0172 0.3983 -0.0397 0.09 Uiso calc R 1 . .
C C38 0.1871(3) 0.45252(18) -0.07978(13) 0.0482(7) Uani d . 1 . .
C C39 0.1270(4) 0.4656(3) -0.13441(18) 0.0852(11) Uani d . 1 . .
H H39 0.0389 0.4422 -0.1416 0.102 Uiso calc R 1 . .
C C40 0.1978(5) 0.5136(4) -0.17904(19) 0.1133(16) Uani d . 1 . .
H H40 0.1579 0.5208 -0.2162 0.136 Uiso calc R 1 . .
C C41 0.3225(5) 0.5492(3) -0.1684(2) 0.0965(14) Uani d . 1 . .
H H41 0.3667 0.5847 -0.1975 0.116 Uiso calc R 1 . .
C C42 0.3842(4) 0.5346(3) -0.1167(2) 0.0981(13) Uani d . 1 . .
H H42 0.4737 0.556 -0.1105 0.118 Uiso calc R 1 . .
C C43 0.3150(4) 0.4877(3) -0.07260(16) 0.0792(10) Uani d . 1 . .
H H43 0.3583 0.4799 -0.0362 0.095 Uiso calc R 1 . .
O O1 -0.02665(19) 0.24338(15) 0.01282(9) 0.0632(6) Uani d . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C6 . 1.421(3) ?
C1 C2 . 1.431(3) ?
C1 C33 . 1.434(4) ?
C2 C3 . 1.384(3) ?
C2 C7 . 1.498(3) ?
C3 C4 . 1.437(4) ?
C3 C13 . 1.501(3) ?
C4 C5 . 1.381(3) ?
C4 C19 . 1.500(4) ?
C5 C6 . 1.435(4) ?
C5 C25 . 1.497(4) ?
C6 C31 . 1.404(4) ?
C7 C8 . 1.379(4) ?
C7 C12 . 1.381(4) ?
C8 C9 . 1.382(4) ?
C8 H8 . 0.93 ?
C9 C10 . 1.370(5) ?
C9 H9 . 0.93 ?
C10 C11 . 1.360(5) ?
C10 H10 . 0.93 ?
C11 C12 . 1.384(4) ?
C11 H11 . 0.93 ?
C12 H12 . 0.93 ?
C13 C18 . 1.381(4) ?
C13 C14 . 1.382(4) ?
C14 C15 . 1.385(4) ?
C14 H14 . 0.93 ?
C15 C16 . 1.376(5) ?
C15 H15 . 0.93 ?
C16 C17 . 1.364(5) ?
C16 H16 . 0.93 ?
C17 C18 . 1.383(4) ?
C17 H17 . 0.93 ?
C18 H18 . 0.93 ?
C19 C20 . 1.383(4) ?
C19 C24 . 1.387(4) ?
C20 C21 . 1.381(5) ?
C20 H20 . 0.93 ?
C21 C22 . 1.369(5) ?
C21 H21 . 0.93 ?
C22 C23 . 1.363(5) ?
C22 H22 . 0.93 ?
C23 C24 . 1.372(4) ?
C23 H23 . 0.93 ?
C24 H24 . 0.93 ?
C25 C26 . 1.373(4) ?
C25 C30 . 1.387(5) ?
C26 C27 . 1.388(5) ?
C26 H26 . 0.93 ?
C27 C28 . 1.387(7) ?
C27 H27 . 0.93 ?
C28 C29 . 1.329(6) ?
C28 H28 . 0.93 ?
C29 C30 . 1.379(5) ?
C29 H29 . 0.93 ?
C30 H30 . 0.93 ?
C31 C32 . 1.360(4) ?
C31 H31 . 0.93 ?
C32 N1 . 1.351(4) ?
C32 H32 . 0.93 ?
N1 C33 . 1.320(3) ?
C33 C35 . 1.496(4) ?
C35 O1 . 1.223(3) ?
C35 N2 . 1.344(3) ?
N2 C37 . 1.459(4) ?
C37 C38 . 1.488(4) ?
C37 H37A . 0.97 ?
C37 H37B . 0.97 ?
C38 C43 . 1.347(4) ?
C38 C39 . 1.377(4) ?
C39 C40 . 1.395(6) ?
C39 H39 . 0.93 ?
C40 C41 . 1.331(6) ?
C40 H40 . 0.93 ?
C41 C42 . 1.328(6) ?
C41 H41 . 0.93 ?
C42 C43 . 1.372(6) ?
C42 H42 . 0.93 ?
C43 H43 . 0.93 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 C1 C2 . . 119.4(2) ?
C6 C1 C33 . . 116.1(2) ?
C2 C1 C33 . . 124.4(2) ?
C3 C2 C1 . . 119.7(2) ?
C3 C2 C7 . . 119.0(2) ?
C1 C2 C7 . . 121.2(2) ?
C2 C3 C4 . . 120.9(2) ?
C2 C3 C13 . . 118.8(2) ?
C4 C3 C13 . . 120.3(2) ?
C5 C4 C3 . . 120.0(2) ?
C5 C4 C19 . . 119.5(2) ?
C3 C4 C19 . . 120.5(2) ?
C4 C5 C6 . . 120.0(2) ?
C4 C5 C25 . . 122.1(2) ?
C6 C5 C25 . . 117.9(2) ?
C31 C6 C1 . . 118.2(2) ?
C31 C6 C5 . . 122.1(2) ?
C1 C6 C5 . . 119.7(2) ?
C8 C7 C12 . . 118.1(2) ?
C8 C7 C2 . . 119.6(2) ?
C12 C7 C2 . . 122.2(2) ?
C7 C8 C9 . . 120.5(3) ?
C7 C8 H8 . . 119.8 ?
C9 C8 H8 . . 119.8 ?
C10 C9 C8 . . 120.6(3) ?
C10 C9 H9 . . 119.7 ?
C8 C9 H9 . . 119.7 ?
C11 C10 C9 . . 119.6(3) ?
C11 C10 H10 . . 120.2 ?
C9 C10 H10 . . 120.2 ?
C10 C11 C12 . . 120.1(3) ?
C10 C11 H11 . . 120.0 ?
C12 C11 H11 . . 120.0 ?
C7 C12 C11 . . 121.1(3) ?
C7 C12 H12 . . 119.5 ?
C11 C12 H12 . . 119.5 ?
C18 C13 C14 . . 118.6(3) ?
C18 C13 C3 . . 121.3(2) ?
C14 C13 C3 . . 120.1(2) ?
C13 C14 C15 . . 120.9(3) ?
C13 C14 H14 . . 119.6 ?
C15 C14 H14 . . 119.6 ?
C16 C15 C14 . . 119.6(3) ?
C16 C15 H15 . . 120.2 ?
C14 C15 H15 . . 120.2 ?
C17 C16 C15 . . 120.0(3) ?
C17 C16 H16 . . 120.0 ?
C15 C16 H16 . . 120.0 ?
C16 C17 C18 . . 120.6(3) ?
C16 C17 H17 . . 119.7 ?
C18 C17 H17 . . 119.7 ?
C13 C18 C17 . . 120.3(3) ?
C13 C18 H18 . . 119.8 ?
C17 C18 H18 . . 119.8 ?
C20 C19 C24 . . 117.5(3) ?
C20 C19 C4 . . 121.6(3) ?
C24 C19 C4 . . 120.9(2) ?
C21 C20 C19 . . 121.2(3) ?
C21 C20 H20 . . 119.4 ?
C19 C20 H20 . . 119.4 ?
C22 C21 C20 . . 120.3(3) ?
C22 C21 H21 . . 119.9 ?
C20 C21 H21 . . 119.9 ?
C23 C22 C21 . . 119.2(3) ?
C23 C22 H22 . . 120.4 ?
C21 C22 H22 . . 120.4 ?
C22 C23 C24 . . 120.9(3) ?
C22 C23 H23 . . 119.5 ?
C24 C23 H23 . . 119.5 ?
C23 C24 C19 . . 120.9(3) ?
C23 C24 H24 . . 119.5 ?
C19 C24 H24 . . 119.5 ?
C26 C25 C30 . . 118.5(3) ?
C26 C25 C5 . . 121.3(3) ?
C30 C25 C5 . . 120.1(3) ?
C25 C26 C27 . . 120.8(4) ?
C25 C26 H26 . . 119.6 ?
C27 C26 H26 . . 119.6 ?
C28 C27 C26 . . 118.8(4) ?
C28 C27 H27 . . 120.6 ?
C26 C27 H27 . . 120.6 ?
C29 C28 C27 . . 120.7(4) ?
C29 C28 H28 . . 119.6 ?
C27 C28 H28 . . 119.6 ?
C28 C29 C30 . . 120.9(4) ?
C28 C29 H29 . . 119.5 ?
C30 C29 H29 . . 119.5 ?
C29 C30 C25 . . 120.2(4) ?
C29 C30 H30 . . 119.9 ?
C25 C30 H30 . . 119.9 ?
C32 C31 C6 . . 119.8(3) ?
C32 C31 H31 . . 120.1 ?
C6 C31 H31 . . 120.1 ?
N1 C32 C31 . . 123.6(3) ?
N1 C32 H32 . . 118.2 ?
C31 C32 H32 . . 118.2 ?
C33 N1 C32 . . 117.9(2) ?
N1 C33 C1 . . 124.0(2) ?
N1 C33 C35 . . 111.0(2) ?
C1 C33 C35 . . 124.7(2) ?
O1 C35 N2 . . 123.8(3) ?
O1 C35 C33 . . 121.6(2) ?
N2 C35 C33 . . 114.3(2) ?
C35 N2 C37 . . 121.6(2) ?
N2 C37 C38 . . 110.4(2) ?
N2 C37 H37A . . 109.6 ?
C38 C37 H37A . . 109.6 ?
N2 C37 H37B . . 109.6 ?
C38 C37 H37B . . 109.6 ?
H37A C37 H37B . . 108.1 ?
C43 C38 C39 . . 116.7(3) ?
C43 C38 C37 . . 121.5(3) ?
C39 C38 C37 . . 121.8(3) ?
C38 C39 C40 . . 120.2(3) ?
C38 C39 H39 . . 119.9 ?
C40 C39 H39 . . 119.9 ?
C41 C40 C39 . . 120.1(4) ?
C41 C40 H40 . . 120.0 ?
C39 C40 H40 . . 120.0 ?
C42 C41 C40 . . 120.6(4) ?
C42 C41 H41 . . 119.7 ?
C40 C41 H41 . . 119.7 ?
C41 C42 C43 . . 119.5(4) ?
C41 C42 H42 . . 120.3 ?
C43 C42 H42 . . 120.3 ?
C38 C43 C42 . . 122.8(4) ?
C38 C43 H43 . . 118.6 ?
C42 C43 H43 . . 118.6 ?

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

data_I
_database_code_depnum_ccdc_archive 'CCDC 1027407'
_audit_update_record             
;
2014-10-02 deposited with the CCDC.
2015-06-29 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            man666.01
_chemical_formula_moiety         ?
_chemical_formula_sum            'C41 H32 N2 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         568.69

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'

_cell_length_a                   9.7137(7)
_cell_length_b                   21.2283(15)
_cell_length_c                   30.357(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6259.8(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8678
_cell_measurement_theta_min      2.4019
_cell_measurement_theta_max      21.5387
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.060
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2400

_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_T_max  1.00

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            66559
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_av_sigmaI/netI    0.0328
_diffrn_reflns_theta_min         2.34
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_full        25.34
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36

_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.
;

_reflns_number_total             5720
_reflns_number_gt                3731
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0828
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_gt          0.1081
_refine_ls_wR_factor_ref         0.1271
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_number_reflns         5720
_refine_ls_number_parameters     397
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0631P)²+0.9271P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.172
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker Instrument Service v2010.9.0.0'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.28573(17) 0.20196(9) 0.33575(6) 0.0465(4) Uani d . 1 . .
C C2 0.19797(17) 0.24498(9) 0.30853(6) 0.0484(5) Uani d . 1 . .
C C3 0.1492(2) 0.22425(11) 0.26852(7) 0.0674(6) Uani d . 1 . .
H H3 0.1708 0.1842 0.2583 0.081 Uiso calc R 1 . .
C C4 0.0675(2) 0.26408(15) 0.24390(8) 0.0829(7) Uani d . 1 . .
H H4 0.0332 0.2514 0.2167 0.099 Uiso calc R 1 . .
C C5 0.0381(3) 0.32228(14) 0.26010(9) 0.0833(7) Uani d . 1 . .
H H5 -0.0175 0.3499 0.2443 0.1 Uiso calc R 1 . .
C C6 0.0916(2) 0.33959(11) 0.29999(9) 0.0759(7) Uani d . 1 . .
H H6 0.0713 0.3796 0.3106 0.091 Uiso calc R 1 . .
C C7 0.42695(17) 0.19061(8) 0.40166(6) 0.0435(4) Uani d . 1 . .
H H7A 0.4088 0.1457 0.4002 0.052 Uiso calc R 1 . .
H H7B 0.4178 0.2037 0.4321 0.052 Uiso calc R 1 . .
C C8 0.57269(16) 0.20340(8) 0.38606(5) 0.0374(4) Uani d . 1 . .
C C9 0.62024(17) 0.26611(8) 0.38400(5) 0.0407(4) Uani d . 1 . .
C C10 0.74467(18) 0.27947(8) 0.36384(6) 0.0478(5) Uani d . 1 . .
H H10 0.7764 0.3208 0.3629 0.057 Uiso calc R 1 . .
C C11 0.82206(19) 0.23199(9) 0.34516(6) 0.0534(5) Uani d . 1 . .
H H11 0.9033 0.2416 0.3304 0.064 Uiso calc R 1 . .
C C12 0.77891(18) 0.17061(9) 0.34838(6) 0.0496(5) Uani d . 1 . .
H H12 0.8328 0.1388 0.3362 0.059 Uiso calc R 1 . .
C C13 0.65613(17) 0.15482(8) 0.36946(5) 0.0403(4) Uani d . 1 . .
C C14 0.62679(17) 0.08629(8) 0.37574(5) 0.0411(4) Uani d . 1 . .
C C15 0.60412(18) 0.06383(8) 0.41625(6) 0.0447(4) Uani d . 1 . .
H H15 0.6013 0.094 0.4384 0.054 Uiso calc R 1 . .
C C16 0.58300(18) -0.00149(8) 0.43092(6) 0.0454(4) Uani d . 1 . .
C C17 0.6405(2) -0.02059(9) 0.47058(6) 0.0559(5) Uani d . 1 . .
H H17 0.6904 0.0083 0.4872 0.067 Uiso calc R 1 . .
C C18 0.6257(2) -0.08086(11) 0.48579(8) 0.0709(6) Uani d . 1 . .
H H18 0.6664 -0.0926 0.5123 0.085 Uiso calc R 1 . .
C C19 0.5516(3) -0.12365(11) 0.46238(9) 0.0800(7) Uani d . 1 . .
H H19 0.5423 -0.1647 0.4726 0.096 Uiso calc R 1 . .
C C20 0.4906(3) -0.10593(11) 0.42350(9) 0.0793(7) Uani d . 1 . .
H H20 0.4385 -0.135 0.4077 0.095 Uiso calc R 1 . .
C C21 0.5059(2) -0.04528(10) 0.40764(7) 0.0627(6) Uani d . 1 . .
H H21 0.4644 -0.0338 0.3812 0.075 Uiso calc R 1 . .
C C22 0.64606(18) 0.04558(8) 0.33610(6) 0.0445(4) Uani d . 1 . .
C C23 0.7414(2) -0.00228(10) 0.33618(7) 0.0684(6) Uani d . 1 . .
H H23 0.7915 -0.0105 0.3616 0.082 Uiso calc R 1 . .
C C24 0.7637(3) -0.03805(11) 0.29916(8) 0.0856(8) Uani d . 1 . .
H H24 0.829 -0.0701 0.2997 0.103 Uiso calc R 1 . .
C C25 0.6914(3) -0.02707(12) 0.26194(8) 0.0833(7) Uani d . 1 . .
H H25 0.7066 -0.0516 0.237 0.1 Uiso calc R 1 . .
C C26 0.5960(3) 0.02013(12) 0.26103(7) 0.0840(7) Uani d . 1 . .
H H26 0.5461 0.0278 0.2354 0.101 Uiso calc R 1 . .
C C27 0.5733(2) 0.05639(10) 0.29797(6) 0.0637(6) Uani d . 1 . .
H H27 0.5081 0.0885 0.2971 0.076 Uiso calc R 1 . .
C C28 0.54182(17) 0.31998(8) 0.40358(6) 0.0420(4) Uani d . 1 . .
C C29 0.50892(18) 0.31685(8) 0.45128(6) 0.0426(4) Uani d . 1 . .
C C30 0.3804(2) 0.33446(9) 0.46692(7) 0.0624(6) Uani d . 1 . .
H H30 0.3136 0.3489 0.4475 0.075 Uiso calc R 1 . .
C C31 0.3517(3) 0.33050(11) 0.51124(10) 0.0907(9) Uani d . 1 . .
H H31 0.2653 0.3423 0.5215 0.109 Uiso calc R 1 . .
C C32 0.4493(4) 0.30933(13) 0.54036(9) 0.0971(10) Uani d . 1 . .
H H32 0.4292 0.3069 0.5703 0.117 Uiso calc R 1 . .
C C33 0.5755(3) 0.29185(11) 0.52525(7) 0.0769(7) Uani d . 1 . .
H H33 0.642 0.2777 0.5449 0.092 Uiso calc R 1 . .
C C34 0.6052(2) 0.29496(9) 0.48114(6) 0.0533(5) Uani d . 1 . .
H H34 0.6913 0.2822 0.4712 0.064 Uiso calc R 1 . .
C C35 0.5099(2) 0.36936(8) 0.37818(6) 0.0508(5) Uani d . 1 . .
H H35 0.5237 0.3631 0.3482 0.061 Uiso calc R 1 . .
C C36 0.45674(19) 0.43184(8) 0.39004(6) 0.0484(5) Uani d . 1 . .
C C37 0.4998(2) 0.46400(9) 0.42724(6) 0.0580(5) Uani d . 1 . .
H H37 0.5585 0.4444 0.4472 0.07 Uiso calc R 1 . .
C C38 0.4566(3) 0.52484(10) 0.43505(8) 0.0723(6) Uani d . 1 . .
H H38 0.4862 0.5459 0.4602 0.087 Uiso calc R 1 . .
C C39 0.3703(3) 0.55448(10) 0.40606(9) 0.0775(7) Uani d . 1 . .
H H39 0.3418 0.5956 0.4114 0.093 Uiso calc R 1 . .
C C40 0.3263(3) 0.52365(11) 0.36934(9) 0.0812(7) Uani d . 1 . .
H H40 0.2671 0.5435 0.3497 0.097 Uiso calc R 1 . .
C C41 0.3697(2) 0.46300(10) 0.36152(7) 0.0684(6) Uani d . 1 . .
H H41 0.3395 0.4424 0.3363 0.082 Uiso calc R 1 . .
N N1 0.17122(17) 0.30225(8) 0.32465(6) 0.0605(4) Uani d . 1 . .
N N2 0.32639(14) 0.22409(7) 0.37485(5) 0.0467(4) Uani d . 1 . .
H H2 0.2924 0.2589 0.3844 0.056 Uiso calc R 1 . .
O O1 0.31777(16) 0.14979(7) 0.32228(5) 0.0715(4) Uani d . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 . 1.221(2) ?
C1 N2 . 1.336(2) ?
C1 C2 . 1.498(3) ?
C2 N1 . 1.336(2) ?
C2 C3 . 1.376(3) ?
C3 C4 . 1.379(3) ?
C3 H3 . 0.93 ?
C4 C5 . 1.360(3) ?
C4 H4 . 0.93 ?
C5 C6 . 1.368(3) ?
C5 H5 . 0.93 ?
C6 N1 . 1.337(3) ?
C6 H6 . 0.93 ?
C7 N2 . 1.456(2) ?
C7 C8 . 1.517(2) ?
C7 H7A . 0.97 ?
C7 H7B . 0.97 ?
C8 C13 . 1.405(2) ?
C8 C9 . 1.410(2) ?
C9 C10 . 1.384(2) ?
C9 C28 . 1.497(2) ?
C10 C11 . 1.379(3) ?
C10 H10 . 0.93 ?
C11 C12 . 1.372(3) ?
C11 H11 . 0.93 ?
C12 C13 . 1.394(2) ?
C12 H12 . 0.93 ?
C13 C14 . 1.495(2) ?
C14 C15 . 1.337(2) ?
C14 C22 . 1.493(2) ?
C15 C16 . 1.471(2) ?
C15 H15 . 0.93 ?
C16 C21 . 1.387(3) ?
C16 C17 . 1.388(3) ?
C17 C18 . 1.368(3) ?
C17 H17 . 0.93 ?
C18 C19 . 1.359(3) ?
C18 H18 . 0.93 ?
C19 C20 . 1.373(3) ?
C19 H19 . 0.93 ?
C20 C21 . 1.383(3) ?
C20 H20 . 0.93 ?
C21 H21 . 0.93 ?
C22 C23 . 1.375(3) ?
C22 C27 . 1.376(3) ?
C23 C24 . 1.374(3) ?
C23 H23 . 0.93 ?
C24 C25 . 1.350(3) ?
C24 H24 . 0.93 ?
C25 C26 . 1.366(3) ?
C25 H25 . 0.93 ?
C26 C27 . 1.378(3) ?
C26 H26 . 0.93 ?
C27 H27 . 0.93 ?
C28 C35 . 1.338(2) ?
C28 C29 . 1.484(2) ?
C29 C34 . 1.383(3) ?
C29 C30 . 1.387(3) ?
C30 C31 . 1.376(3) ?
C30 H30 . 0.93 ?
C31 C32 . 1.371(4) ?
C31 H31 . 0.93 ?
C32 C33 . 1.361(4) ?
C32 H32 . 0.93 ?
C33 C34 . 1.372(3) ?
C33 H33 . 0.93 ?
C34 H34 . 0.93 ?
C35 C36 . 1.468(3) ?
C35 H35 . 0.93 ?
C36 C41 . 1.379(3) ?
C36 C37 . 1.385(3) ?
C37 C38 . 1.379(3) ?
C37 H37 . 0.93 ?
C38 C39 . 1.369(3) ?
C38 H38 . 0.93 ?
C39 C40 . 1.361(3) ?
C39 H39 . 0.93 ?
C40 C41 . 1.375(3) ?
C40 H40 . 0.93 ?
C41 H41 . 0.93 ?
N2 H2 . 0.86 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 C1 N2 . . 122.76(18) ?
O1 C1 C2 . . 120.89(17) ?
N2 C1 C2 . . 116.35(16) ?
N1 C2 C3 . . 123.17(19) ?
N1 C2 C1 . . 117.62(17) ?
C3 C2 C1 . . 119.20(18) ?
C2 C3 C4 . . 118.7(2) ?
C2 C3 H3 . . 120.6 ?
C4 C3 H3 . . 120.6 ?
C5 C4 C3 . . 118.8(2) ?
C5 C4 H4 . . 120.6 ?
C3 C4 H4 . . 120.6 ?
C4 C5 C6 . . 119.0(2) ?
C4 C5 H5 . . 120.5 ?
C6 C5 H5 . . 120.5 ?
N1 C6 C5 . . 123.8(2) ?
N1 C6 H6 . . 118.1 ?
C5 C6 H6 . . 118.1 ?
N2 C7 C8 . . 111.36(13) ?
N2 C7 H7A . . 109.4 ?
C8 C7 H7A . . 109.4 ?
N2 C7 H7B . . 109.4 ?
C8 C7 H7B . . 109.4 ?
H7A C7 H7B . . 108.0 ?
C13 C8 C9 . . 119.20(15) ?
C13 C8 C7 . . 121.25(15) ?
C9 C8 C7 . . 119.23(15) ?
C10 C9 C8 . . 119.94(16) ?
C10 C9 C28 . . 117.59(15) ?
C8 C9 C28 . . 122.46(15) ?
C11 C10 C9 . . 120.52(16) ?
C11 C10 H10 . . 119.7 ?
C9 C10 H10 . . 119.7 ?
C12 C11 C10 . . 119.87(16) ?
C12 C11 H11 . . 120.1 ?
C10 C11 H11 . . 120.1 ?
C11 C12 C13 . . 121.49(17) ?
C11 C12 H12 . . 119.3 ?
C13 C12 H12 . . 119.3 ?
C12 C13 C8 . . 118.78(16) ?
C12 C13 C14 . . 117.10(15) ?
C8 C13 C14 . . 123.97(15) ?
C15 C14 C13 . . 119.71(15) ?
C15 C14 C22 . . 123.73(16) ?
C13 C14 C22 . . 115.90(14) ?
C14 C15 C16 . . 129.60(16) ?
C14 C15 H15 . . 115.2 ?
C16 C15 H15 . . 115.2 ?
C21 C16 C17 . . 117.61(18) ?
C21 C16 C15 . . 123.56(17) ?
C17 C16 C15 . . 118.81(17) ?
C18 C17 C16 . . 121.6(2) ?
C18 C17 H17 . . 119.2 ?
C16 C17 H17 . . 119.2 ?
C19 C18 C17 . . 120.3(2) ?
C19 C18 H18 . . 119.9 ?
C17 C18 H18 . . 119.9 ?
C18 C19 C20 . . 119.7(2) ?
C18 C19 H19 . . 120.2 ?
C20 C19 H19 . . 120.2 ?
C19 C20 C21 . . 120.5(2) ?
C19 C20 H20 . . 119.7 ?
C21 C20 H20 . . 119.7 ?
C20 C21 C16 . . 120.3(2) ?
C20 C21 H21 . . 119.8 ?
C16 C21 H21 . . 119.8 ?
C23 C22 C27 . . 118.11(17) ?
C23 C22 C14 . . 120.71(16) ?
C27 C22 C14 . . 121.13(16) ?
C24 C23 C22 . . 120.9(2) ?
C24 C23 H23 . . 119.6 ?
C22 C23 H23 . . 119.6 ?
C25 C24 C23 . . 120.5(2) ?
C25 C24 H24 . . 119.8 ?
C23 C24 H24 . . 119.8 ?
C24 C25 C26 . . 119.8(2) ?
C24 C25 H25 . . 120.1 ?
C26 C25 H25 . . 120.1 ?
C25 C26 C27 . . 120.2(2) ?
C25 C26 H26 . . 119.9 ?
C27 C26 H26 . . 119.9 ?
C22 C27 C26 . . 120.61(19) ?
C22 C27 H27 . . 119.7 ?
C26 C27 H27 . . 119.7 ?
C35 C28 C29 . . 123.20(16) ?
C35 C28 C9 . . 119.18(16) ?
C29 C28 C9 . . 117.57(14) ?
C34 C29 C30 . . 118.36(18) ?
C34 C29 C28 . . 120.58(16) ?
C30 C29 C28 . . 121.05(17) ?
C31 C30 C29 . . 120.0(2) ?
C31 C30 H30 . . 120.0 ?
C29 C30 H30 . . 120.0 ?
C32 C31 C30 . . 120.7(2) ?
C32 C31 H31 . . 119.7 ?
C30 C31 H31 . . 119.7 ?
C33 C32 C31 . . 119.6(2) ?
C33 C32 H32 . . 120.2 ?
C31 C32 H32 . . 120.2 ?
C32 C33 C34 . . 120.4(3) ?
C32 C33 H33 . . 119.8 ?
C34 C33 H33 . . 119.8 ?
C33 C34 C29 . . 120.9(2) ?
C33 C34 H34 . . 119.5 ?
C29 C34 H34 . . 119.5 ?
C28 C35 C36 . . 130.40(17) ?
C28 C35 H35 . . 114.8 ?
C36 C35 H35 . . 114.8 ?
C41 C36 C37 . . 117.45(18) ?
C41 C36 C35 . . 119.68(17) ?
C37 C36 C35 . . 122.62(17) ?
C38 C37 C36 . . 120.67(19) ?
C38 C37 H37 . . 119.7 ?
C36 C37 H37 . . 119.7 ?
C39 C38 C37 . . 120.4(2) ?
C39 C38 H38 . . 119.8 ?
C37 C38 H38 . . 119.8 ?
C40 C39 C38 . . 119.9(2) ?
C40 C39 H39 . . 120.1 ?
C38 C39 H39 . . 120.1 ?
C39 C40 C41 . . 119.7(2) ?
C39 C40 H40 . . 120.2 ?
C41 C40 H40 . . 120.2 ?
C40 C41 C36 . . 121.9(2) ?
C40 C41 H41 . . 119.0 ?
C36 C41 H41 . . 119.0 ?
C2 N1 C6 . . 116.56(19) ?
C1 N2 C7 . . 121.53(15) ?
C1 N2 H2 . . 119.2 ?
C7 N2 H2 . . 119.2 ?

####################################################################### 
# 
# 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_2fin
_database_code_depnum_ccdc_archive 'CCDC 1027408'
_audit_update_record             
;
2014-10-02 deposited with the CCDC.
2015-06-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H19 F3 N2 O'
_chemical_formula_sum            'C28 H19 F3 N2 O'
_chemical_formula_weight         456.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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
_symmetry_space_group_name_Hall  -P1

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

_cell_length_a                   9.7447(3)
_cell_length_b                   10.0599(3)
_cell_length_c                   12.2374(4)
_cell_angle_alpha                103.037(2)
_cell_angle_beta                 100.267(2)
_cell_angle_gamma                97.7300(10)
_cell_volume                     1130.74(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3225
_cell_measurement_theta_min      3.80
_cell_measurement_theta_max      65.38

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472
_exptl_absorpt_coefficient_mu    0.827
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.848
_exptl_absorpt_correction_T_max  0.883
_exptl_absorpt_process_details   'SADABS (Bruker, 2006)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_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            6730
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_av_sigmaI/netI    0.0271
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.80
_diffrn_reflns_theta_max         66.68
_reflns_number_total             3427
_reflns_number_gt                2982
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX 2 (Bruker 2006)'
_computing_cell_refinement       'SAINT (Bruker 2006)'
_computing_data_reduction        'SAINT (Bruker 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Mercury 2.3 (Macrae et al, 2008)'
_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)+(0.0692P)²+0.4507P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0222(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3427
_refine_ls_number_parameters     308
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0489
_refine_ls_wR_factor_ref         0.1394
_refine_ls_wR_factor_gt          0.1334
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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 0.47100(17) 0.36826(15) 0.66041(13) 0.0552(4) Uani 1 1 d . . .
N1 N 0.38999(16) 0.56920(16) 0.65691(13) 0.0380(4) Uani 1 1 d . . .
N2 N 0.33441(19) 0.24627(17) 0.43859(15) 0.0493(4) Uani 1 1 d . . .
C1 C 0.4276(3) 0.6653(3) 0.97660(19) 0.0687(7) Uani 1 1 d . . .
H1 H 0.5097 0.7324 0.9975 0.082 Uiso 1 1 calc R . .
C2 C 0.3563(3) 0.6406(4) 1.0596(2) 0.0841(10) Uani 1 1 d . . .
H2 H 0.3912 0.6896 1.1360 0.101 Uiso 1 1 calc R . .
C3 C 0.2340(3) 0.5438(3) 1.0296(2) 0.0728(8) Uani 1 1 d . . .
H3 H 0.1845 0.5280 1.0852 0.087 Uiso 1 1 calc R . .
C4 C 0.1855(3) 0.4708(3) 0.9181(2) 0.0727(8) Uani 1 1 d . . .
H4 H 0.1028 0.4044 0.8976 0.087 Uiso 1 1 calc R . .
C5 C 0.2583(2) 0.4947(2) 0.83467(19) 0.0569(6) Uani 1 1 d . . .
H5 H 0.2245 0.4438 0.7587 0.068 Uiso 1 1 calc R . .
C6 C 0.3797(2) 0.5927(2) 0.86340(16) 0.0413(4) Uani 1 1 d . . .
C7 C 0.4660(2) 0.6233(2) 0.77759(16) 0.0407(4) Uani 1 1 d . . .
H7A H 0.4952 0.7230 0.7931 0.049 Uiso 1 1 calc R . .
H7B H 0.5512 0.5835 0.7888 0.049 Uiso 1 1 calc R . .
C8 C 0.4008(2) 0.4341(2) 0.60664(16) 0.0405(4) Uani 1 1 d . . .
C9 C 0.3231(2) 0.37777(19) 0.48644(16) 0.0392(4) Uani 1 1 d . . .
C10 C 0.24438(19) 0.45821(19) 0.42983(15) 0.0374(4) Uani 1 1 d . . .
C11 C 0.24145(19) 0.59893(19) 0.48845(15) 0.0373(4) Uani 1 1 d . . .
C12 C 0.31452(19) 0.65102(18) 0.59896(15) 0.0363(4) Uani 1 1 d . . .
C13 C 0.32477(19) 0.79954(19) 0.65932(16) 0.0394(4) Uani 1 1 d . . .
C14 C 0.3914(2) 0.9011(2) 0.61605(18) 0.0469(5) Uani 1 1 d . . .
H14 H 0.4313 0.8752 0.5526 0.056 Uiso 1 1 calc R . .
C15 C 0.3990(2) 1.0404(2) 0.6666(2) 0.0580(6) Uani 1 1 d . . .
H15 H 0.4430 1.1076 0.6366 0.070 Uiso 1 1 calc R . .
C16 C 0.3416(3) 1.0792(2) 0.7604(2) 0.0618(6) Uani 1 1 d . . .
H16 H 0.3466 1.1728 0.7941 0.074 Uiso 1 1 calc R . .
C17 C 0.2764(3) 0.9801(3) 0.8052(2) 0.0598(6) Uani 1 1 d . . .
H17 H 0.2391 1.0071 0.8699 0.072 Uiso 1 1 calc R . .
C18 C 0.2662(2) 0.8398(2) 0.75403(18) 0.0493(5) Uani 1 1 d . . .
H18 H 0.2200 0.7732 0.7833 0.059 Uiso 1 1 calc R . .
C19 C 0.1605(2) 0.68583(18) 0.42712(15) 0.0386(4) Uani 1 1 d . . .
C20 C 0.2040(2) 0.7244(2) 0.33442(17) 0.0454(5) Uani 1 1 d . . .
H20 H 0.2822 0.6941 0.3099 0.055 Uiso 1 1 calc R . .
C21 C 0.1312(3) 0.8076(2) 0.2788(2) 0.0566(6) Uani 1 1 d . . .
H21 H 0.1602 0.8325 0.2167 0.068 Uiso 1 1 calc R . .
C22 C 0.0160(3) 0.8540(3) 0.3147(2) 0.0629(6) Uani 1 1 d . . .
H22 H -0.0315 0.9113 0.2778 0.075 Uiso 1 1 calc R . .
C23 C -0.0289(2) 0.8152(3) 0.4056(2) 0.0613(6) Uani 1 1 d . . .
H23 H -0.1074 0.8455 0.4294 0.074 Uiso 1 1 calc R . .
C24 C 0.0427(2) 0.7314(2) 0.46105(19) 0.0494(5) Uani 1 1 d . . .
H24 H 0.0115 0.7052 0.5220 0.059 Uiso 1 1 calc R . .
C25 C 0.2663(2) 0.1911(2) 0.33100(19) 0.0537(5) Uani 1 1 d . . .
H25 H 0.2739 0.1009 0.2964 0.064 Uiso 1 1 calc R . .
C26 C 0.1834(2) 0.2613(2) 0.26634(17) 0.0467(5) Uani 1 1 d . . .
C27 C 0.1708(2) 0.3941(2) 0.31546(16) 0.0431(5) Uani 1 1 d . . .
H27 H 0.1145 0.4416 0.2742 0.052 Uiso 1 1 calc R . .
C28 C 0.1155(3) 0.1894(2) 0.14418(19) 0.0550(6) Uani 1 1 d . . .
F1 F 0.2044(2) 0.1910(3) 0.07616(13) 0.1130(8) Uani 1 1 d . . .
F2 F 0.0547(3) 0.06150(18) 0.12941(14) 0.1073(7) Uani 1 1 d . . .
F3 F 0.0120(2) 0.2502(2) 0.09976(14) 0.1035(7) 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
O1 C8 1.224(2) . ?
N1 C8 1.386(2) . ?
N1 C12 1.400(2) . ?
N1 C7 1.471(2) . ?
N2 C25 1.320(3) . ?
N2 C9 1.348(3) . ?
C1 C6 1.375(3) . ?
C1 C2 1.376(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.369(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.360(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.389(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.370(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.515(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.473(3) . ?
C9 C10 1.398(3) . ?
C10 C27 1.414(3) . ?
C10 C11 1.442(3) . ?
C11 C12 1.359(3) . ?
C11 C19 1.490(3) . ?
C12 C13 1.491(3) . ?
C13 C18 1.386(3) . ?
C13 C14 1.391(3) . ?
C14 C15 1.385(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.367(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.378(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.391(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C24 1.388(3) . ?
C19 C20 1.394(3) . ?
C20 C21 1.383(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.376(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.380(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.381(3) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 C26 1.398(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.367(3) . ?
C26 C28 1.492(3) . ?
C27 H27 0.9300 . ?
C28 F2 1.300(3) . ?
C28 F1 1.305(3) . ?
C28 F3 1.344(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
C8 N1 C12 123.68(15) . . ?
C8 N1 C7 114.95(16) . . ?
C12 N1 C7 121.36(15) . . ?
C25 N2 C9 117.17(19) . . ?
C6 C1 C2 121.3(2) . . ?
C6 C1 H1 119.3 . . ?
C2 C1 H1 119.3 . . ?
C3 C2 C1 119.9(2) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C4 C3 C2 119.6(2) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 120.5(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 120.5(2) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 118.30(19) . . ?
C5 C6 C7 123.52(17) . . ?
C1 C6 C7 118.16(18) . . ?
N1 C7 C6 114.05(15) . . ?
N1 C7 H7A 108.7 . . ?
C6 C7 H7A 108.7 . . ?
N1 C7 H7B 108.7 . . ?
C6 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
O1 C8 N1 121.02(18) . . ?
O1 C8 C9 123.46(18) . . ?
N1 C8 C9 115.52(17) . . ?
N2 C9 C10 124.38(18) . . ?
N2 C9 C8 114.92(18) . . ?
C10 C9 C8 120.69(17) . . ?
C9 C10 C27 116.56(17) . . ?
C9 C10 C11 119.89(17) . . ?
C27 C10 C11 123.55(18) . . ?
C12 C11 C10 119.24(17) . . ?
C12 C11 C19 120.88(16) . . ?
C10 C11 C19 119.88(16) . . ?
C11 C12 N1 120.93(16) . . ?
C11 C12 C13 120.94(17) . . ?
N1 C12 C13 118.01(16) . . ?
C18 C13 C14 119.00(19) . . ?
C18 C13 C12 122.51(18) . . ?
C14 C13 C12 118.45(17) . . ?
C15 C14 C13 120.6(2) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C14 120.0(2) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 120.3(2) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C16 C17 C18 120.2(2) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C13 C18 C17 119.9(2) . . ?
C13 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C24 C19 C20 118.71(19) . . ?
C24 C19 C11 121.46(17) . . ?
C20 C19 C11 119.83(17) . . ?
C21 C20 C19 120.05(19) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C22 C21 C20 120.6(2) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C21 C22 C23 119.8(2) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C22 C23 C24 120.0(2) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C23 C24 C19 120.8(2) . . ?
C23 C24 H24 119.6 . . ?
C19 C24 H24 119.6 . . ?
N2 C25 C26 123.42(19) . . ?
N2 C25 H25 118.3 . . ?
C26 C25 H25 118.3 . . ?
C27 C26 C25 119.30(19) . . ?
C27 C26 C28 122.3(2) . . ?
C25 C26 C28 118.39(19) . . ?
C26 C27 C10 119.14(19) . . ?
C26 C27 H27 120.4 . . ?
C10 C27 H27 120.4 . . ?
F2 C28 F1 108.3(2) . . ?
F2 C28 F3 104.6(2) . . ?
F1 C28 F3 104.1(2) . . ?
F2 C28 C26 113.64(19) . . ?
F1 C28 C26 112.58(19) . . ?
F3 C28 C26 112.85(19) . . ?

_diffrn_measured_fraction_theta_max 0.856
_diffrn_reflns_theta_full        66.68
_diffrn_measured_fraction_theta_full 0.856
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.039
####################################################################### 
# 
# 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_14fin
_database_code_depnum_ccdc_archive 'CCDC 1027409'
_audit_update_record             
;
2014-10-02 deposited with the CCDC.
2015-06-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H21 N O S'
_chemical_formula_sum            'C27 H21 N O S'
_chemical_formula_weight         407.51

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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)/n
_symmetry_space_group_name_Hall  -P2yn

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

_cell_length_a                   11.5129(3)
_cell_length_b                   21.7914(5)
_cell_length_c                   17.1772(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.718(2)
_cell_angle_gamma                90.00
_cell_volume                     4259.66(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    7173
_cell_measurement_theta_min      3.30
_cell_measurement_theta_max      62.71

_exptl_crystal_description       Prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1712
_exptl_absorpt_coefficient_mu    1.481
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.736
_exptl_absorpt_correction_T_max  0.801
_exptl_absorpt_process_details   'SADABS (Bruker, 2006)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_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            32583
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_av_sigmaI/netI    0.0392
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.30
_diffrn_reflns_theta_max         67.25
_reflns_number_total             7102
_reflns_number_gt                4852
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX 2 (Bruker 2006)'
_computing_cell_refinement       'SAINT (Bruker 2006)'
_computing_data_reduction        'SAINT (Bruker 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Mercury 2.3 (Macrae et al, 2008)'
_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)+(0.0529P)²+0.8474P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00092(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         7102
_refine_ls_number_parameters     544
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0747
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.1261
_refine_ls_wR_factor_gt          0.1127
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1' S 0.79285(5) 0.04067(4) 0.92231(4) 0.0666(2) Uani 1 1 d . . .
N1' N 1.08593(16) -0.03259(9) 0.86413(11) 0.0500(5) Uani 1 1 d . . .
O1' O 0.90777(16) -0.07820(9) 0.87183(12) 0.0809(6) Uani 1 1 d . . .
C1' C 0.9697(2) -0.03194(12) 0.87964(14) 0.0553(6) Uani 1 1 d . . .
C2' C 0.93165(19) 0.02701(12) 0.90248(13) 0.0501(6) Uani 1 1 d . . .
C3' C 0.99840(18) 0.07965(11) 0.90634(13) 0.0466(5) Uani 1 1 d . . .
C4' C 1.11709(18) 0.07547(11) 0.89019(13) 0.0454(5) Uani 1 1 d . . .
C5' C 1.15715(18) 0.01993(11) 0.86966(13) 0.0437(5) Uani 1 1 d . . .
C6' C 0.8232(2) 0.11829(13) 0.93729(14) 0.0596(7) Uani 1 1 d . . .
C7' C 0.9343(2) 0.13171(12) 0.92676(14) 0.0573(6) Uani 1 1 d . . .
H7' H 0.9659 0.1710 0.9323 0.069 Uiso 1 1 calc R . .
C8' C 0.7300(2) 0.16046(15) 0.95849(18) 0.0818(9) Uani 1 1 d . . .
H8'1 H 0.7316 0.1601 1.0145 0.123 Uiso 1 1 calc R . .
H8'2 H 0.6544 0.1469 0.9330 0.123 Uiso 1 1 calc R . .
H8'3 H 0.7443 0.2014 0.9415 0.123 Uiso 1 1 calc R . .
C9' C 1.27862(18) 0.01320(11) 0.85067(13) 0.0467(5) Uani 1 1 d . . .
C10' C 1.3655(2) -0.01714(13) 0.90053(15) 0.0610(7) Uani 1 1 d . . .
H10' H 1.3477 -0.0354 0.9462 0.073 Uiso 1 1 calc R . .
C11' C 1.4784(2) -0.02053(16) 0.88316(18) 0.0790(9) Uani 1 1 d . . .
H11' H 1.5363 -0.0410 0.9171 0.095 Uiso 1 1 calc R . .
C12' C 1.5054(2) 0.00611(17) 0.81632(19) 0.0845(10) Uani 1 1 d . . .
H12' H 1.5814 0.0032 0.8043 0.101 Uiso 1 1 calc R . .
C13' C 1.4211(2) 0.03718(16) 0.76682(17) 0.0782(9) Uani 1 1 d . . .
H13' H 1.4402 0.0560 0.7218 0.094 Uiso 1 1 calc R . .
C14' C 1.3078(2) 0.04063(13) 0.78361(15) 0.0601(7) Uani 1 1 d . . .
H14' H 1.2506 0.0615 0.7496 0.072 Uiso 1 1 calc R . .
C15' C 1.1287(2) -0.09119(11) 0.83629(15) 0.0562(6) Uani 1 1 d . . .
H15A H 1.0790 -0.1242 0.8500 0.067 Uiso 1 1 calc R . .
H15B H 1.2077 -0.0986 0.8634 0.067 Uiso 1 1 calc R . .
C16' C 1.1302(2) -0.09256(10) 0.74918(14) 0.0504(6) Uani 1 1 d . . .
C17' C 1.2327(2) -0.10433(12) 0.71953(16) 0.0644(7) Uani 1 1 d . . .
H17' H 1.3018 -0.1115 0.7539 0.077 Uiso 1 1 calc R . .
C18' C 1.2336(3) -0.10558(14) 0.63934(18) 0.0765(8) Uani 1 1 d . . .
H18' H 1.3035 -0.1130 0.6201 0.092 Uiso 1 1 calc R . .
C19' C 1.1325(3) -0.09597(14) 0.58792(17) 0.0767(8) Uani 1 1 d . . .
H19' H 1.1332 -0.0976 0.5339 0.092 Uiso 1 1 calc R . .
C20' C 1.0302(2) -0.08390(15) 0.61647(18) 0.0780(9) Uani 1 1 d . . .
H20' H 0.9614 -0.0767 0.5817 0.094 Uiso 1 1 calc R . .
C21' C 1.0288(2) -0.08228(13) 0.69650(17) 0.0665(7) Uani 1 1 d . . .
H21' H 0.9587 -0.0742 0.7153 0.080 Uiso 1 1 calc R . .
C22' C 1.19499(19) 0.13046(11) 0.89681(14) 0.0503(6) Uani 1 1 d . . .
C23' C 1.1776(2) 0.17677(13) 0.84140(19) 0.0713(8) Uani 1 1 d . . .
H23' H 1.1135 0.1750 0.8014 0.086 Uiso 1 1 calc R . .
C24' C 1.2542(3) 0.22545(15) 0.8448(2) 0.0929(11) Uani 1 1 d . . .
H24' H 1.2418 0.2563 0.8071 0.112 Uiso 1 1 calc R . .
C25' C 1.3486(3) 0.22869(17) 0.9036(3) 0.1008(13) Uani 1 1 d . . .
H25' H 1.4001 0.2617 0.9059 0.121 Uiso 1 1 calc R . .
C26' C 1.3670(3) 0.18307(19) 0.9593(2) 0.0945(11) Uani 1 1 d . . .
H26' H 1.4317 0.1849 0.9988 0.113 Uiso 1 1 calc R . .
C27' C 1.2895(2) 0.13448(14) 0.95652(17) 0.0681(7) Uani 1 1 d . . .
H27' H 1.3010 0.1043 0.9952 0.082 Uiso 1 1 calc R . .
S1 S 0.19190(5) 0.18372(4) 0.59668(4) 0.0685(2) Uani 1 1 d . . .
N1 N -0.09500(16) 0.26405(9) 0.65466(11) 0.0491(5) Uani 1 1 d . . .
O1 O 0.08376(16) 0.30625(9) 0.64044(12) 0.0791(6) Uani 1 1 d . . .
C1 C 0.0204(2) 0.26050(13) 0.63853(14) 0.0556(6) Uani 1 1 d . . .
C2 C 0.05577(19) 0.19997(12) 0.62035(13) 0.0510(6) Uani 1 1 d . . .
C3 C -0.01258(18) 0.14835(11) 0.62185(12) 0.0460(5) Uani 1 1 d . . .
C4 C -0.13061(17) 0.15526(10) 0.63793(12) 0.0431(5) Uani 1 1 d . . .
C5 C -0.16822(18) 0.21257(10) 0.65317(12) 0.0435(5) Uani 1 1 d . . .
C6 C 0.1583(2) 0.10638(13) 0.58779(14) 0.0608(7) Uani 1 1 d . . .
C7 C 0.04820(19) 0.09462(12) 0.60323(14) 0.0544(6) Uani 1 1 d . . .
H7 H 0.0158 0.0555 0.6018 0.065 Uiso 1 1 calc R . .
C8 C 0.2461(2) 0.06205(15) 0.56411(18) 0.0834(9) Uani 1 1 d . . .
H8A H 0.2342 0.0224 0.5858 0.125 Uiso 1 1 calc R . .
H8B H 0.3241 0.0761 0.5836 0.125 Uiso 1 1 calc R . .
H8C H 0.2362 0.0593 0.5077 0.125 Uiso 1 1 calc R . .
C9 C -0.29108(18) 0.22298(11) 0.66781(14) 0.0479(6) Uani 1 1 d . . .
C10 C -0.3273(2) 0.19820(12) 0.73449(15) 0.0594(7) Uani 1 1 d . . .
H10 H -0.2744 0.1768 0.7709 0.071 Uiso 1 1 calc R . .
C11 C -0.4429(2) 0.20552(15) 0.74663(19) 0.0788(9) Uani 1 1 d . . .
H11 H -0.4677 0.1890 0.7912 0.095 Uiso 1 1 calc R . .
C12 C -0.5207(2) 0.23720(16) 0.6928(2) 0.0847(10) Uani 1 1 d . . .
H12 H -0.5977 0.2426 0.7017 0.102 Uiso 1 1 calc R . .
C13 C -0.4862(2) 0.26090(14) 0.6263(2) 0.0764(9) Uani 1 1 d . . .
H13 H -0.5401 0.2814 0.5895 0.092 Uiso 1 1 calc R . .
C14 C -0.3714(2) 0.25430(12) 0.61375(16) 0.0588(6) Uani 1 1 d . . .
H14 H -0.3477 0.2709 0.5688 0.071 Uiso 1 1 calc R . .
C15 C -0.1323(2) 0.32401(11) 0.68266(14) 0.0557(6) Uani 1 1 d . . .
H15C H -0.2115 0.3330 0.6572 0.067 Uiso 1 1 calc R . .
H15D H -0.0808 0.3559 0.6682 0.067 Uiso 1 1 calc R . .
C16 C -0.1289(2) 0.32419(10) 0.77051(14) 0.0504(6) Uani 1 1 d . . .
C17 C -0.2293(2) 0.33475(12) 0.80399(17) 0.0639(7) Uani 1 1 d . . .
H17 H -0.3002 0.3429 0.7719 0.077 Uiso 1 1 calc R . .
C18 C -0.2249(3) 0.33322(14) 0.88446(19) 0.0762(8) Uani 1 1 d . . .
H18 H -0.2928 0.3403 0.9063 0.091 Uiso 1 1 calc R . .
C19 C -0.1211(3) 0.32131(14) 0.93272(18) 0.0746(8) Uani 1 1 d . . .
H19 H -0.1186 0.3202 0.9871 0.090 Uiso 1 1 calc R . .
C20 C -0.0212(3) 0.31112(14) 0.90030(17) 0.0723(8) Uani 1 1 d . . .
H20 H 0.0494 0.3029 0.9327 0.087 Uiso 1 1 calc R . .
C21 C -0.0252(2) 0.31299(13) 0.82007(16) 0.0631(7) Uani 1 1 d . . .
H21 H 0.0433 0.3066 0.7987 0.076 Uiso 1 1 calc R . .
C22 C -0.20993(18) 0.10095(10) 0.63430(13) 0.0447(5) Uani 1 1 d . . .
C23 C -0.1855(2) 0.05330(12) 0.68785(16) 0.0584(6) Uani 1 1 d . . .
H23 H -0.1186 0.0551 0.7257 0.070 Uiso 1 1 calc R . .
C24 C -0.2596(2) 0.00316(13) 0.68543(18) 0.0695(8) Uani 1 1 d . . .
H24 H -0.2426 -0.0285 0.7217 0.083 Uiso 1 1 calc R . .
C25 C -0.3579(2) 0.00002(14) 0.6297(2) 0.0752(9) Uani 1 1 d . . .
H25 H -0.4075 -0.0338 0.6279 0.090 Uiso 1 1 calc R . .
C26 C -0.3833(2) 0.04699(14) 0.57620(19) 0.0719(8) Uani 1 1 d . . .
H26 H -0.4504 0.0450 0.5385 0.086 Uiso 1 1 calc R . .
C27 C -0.30935(19) 0.09713(12) 0.57837(15) 0.0551(6) Uani 1 1 d . . .
H27 H -0.3267 0.1286 0.5418 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
S1' C2' 1.710(2) . ?
S1' C6' 1.739(3) . ?
N1' C5' 1.403(3) . ?
N1' C1' 1.403(3) . ?
N1' C15' 1.474(3) . ?
O1' C1' 1.230(3) . ?
C1' C2' 1.431(3) . ?
C2' C3' 1.377(3) . ?
C3' C7' 1.426(3) . ?
C3' C4' 1.438(3) . ?
C4' C5' 1.361(3) . ?
C4' C22' 1.491(3) . ?
C5' C9' 1.491(3) . ?
C6' C7' 1.351(3) . ?
C6' C8' 1.499(3) . ?
C7' H7' 0.9300 . ?
C8' H8'1 0.9600 . ?
C8' H8'2 0.9600 . ?
C8' H8'3 0.9600 . ?
C9' C10' 1.383(3) . ?
C9' C14' 1.384(3) . ?
C10' C11' 1.379(3) . ?
C10' H10' 0.9300 . ?
C11' C12' 1.364(4) . ?
C11' H11' 0.9300 . ?
C12' C13' 1.369(4) . ?
C12' H12' 0.9300 . ?
C13' C14' 1.380(3) . ?
C13' H13' 0.9300 . ?
C14' H14' 0.9300 . ?
C15' C16' 1.499(3) . ?
C15' H15A 0.9700 . ?
C15' H15B 0.9700 . ?
C16' C17' 1.378(3) . ?
C16' C21' 1.383(3) . ?
C17' C18' 1.379(4) . ?
C17' H17' 0.9300 . ?
C18' C19' 1.366(4) . ?
C18' H18' 0.9300 . ?
C19' C20' 1.368(4) . ?
C19' H19' 0.9300 . ?
C20' C21' 1.378(4) . ?
C20' H20' 0.9300 . ?
C21' H21' 0.9300 . ?
C22' C27' 1.380(3) . ?
C22' C23' 1.381(4) . ?
C23' C24' 1.375(4) . ?
C23' H23' 0.9300 . ?
C24' C25' 1.368(5) . ?
C24' H24' 0.9300 . ?
C25' C26' 1.373(5) . ?
C25' H25' 0.9300 . ?
C26' C27' 1.381(4) . ?
C26' H26' 0.9300 . ?
C27' H27' 0.9300 . ?
S1 C2 1.715(2) . ?
S1 C6 1.731(3) . ?
N1 C1 1.400(3) . ?
N1 C5 1.401(3) . ?
N1 C15 1.478(3) . ?
O1 C1 1.233(3) . ?
C1 C2 1.429(3) . ?
C2 C3 1.375(3) . ?
C3 C7 1.425(3) . ?
C3 C4 1.435(3) . ?
C4 C5 1.360(3) . ?
C4 C22 1.490(3) . ?
C5 C9 1.491(3) . ?
C6 C7 1.358(3) . ?
C6 C8 1.498(4) . ?
C7 H7 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.387(3) . ?
C9 C14 1.387(3) . ?
C10 C11 1.387(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.372(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.367(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.378(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.504(3) . ?
C15 H15C 0.9700 . ?
C15 H15D 0.9700 . ?
C16 C21 1.379(3) . ?
C16 C17 1.386(3) . ?
C17 C18 1.376(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.371(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.371(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.372(4) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C27 1.381(3) . ?
C22 C23 1.387(3) . ?
C23 C24 1.383(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.369(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.377(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.382(3) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?

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' S1' C6' 91.49(12) . . ?
C5' N1' C1' 122.9(2) . . ?
C5' N1' C15' 120.52(19) . . ?
C1' N1' C15' 116.5(2) . . ?
O1' C1' N1' 121.6(2) . . ?
O1' C1' C2' 124.7(2) . . ?
N1' C1' C2' 113.7(2) . . ?
C3' C2' C1' 124.7(2) . . ?
C3' C2' S1' 112.15(19) . . ?
C1' C2' S1' 123.04(18) . . ?
C2' C3' C7' 111.7(2) . . ?
C2' C3' C4' 118.5(2) . . ?
C7' C3' C4' 129.8(2) . . ?
C5' C4' C3' 118.4(2) . . ?
C5' C4' C22' 120.74(19) . . ?
C3' C4' C22' 120.8(2) . . ?
C4' C5' N1' 121.71(19) . . ?
C4' C5' C9' 120.7(2) . . ?
N1' C5' C9' 117.6(2) . . ?
C7' C6' C8' 128.8(3) . . ?
C7' C6' S1' 111.3(2) . . ?
C8' C6' S1' 119.8(2) . . ?
C6' C7' C3' 113.4(2) . . ?
C6' C7' H7' 123.3 . . ?
C3' C7' H7' 123.3 . . ?
C6' C8' H8'1 109.5 . . ?
C6' C8' H8'2 109.5 . . ?
H8'1 C8' H8'2 109.5 . . ?
C6' C8' H8'3 109.5 . . ?
H8'1 C8' H8'3 109.5 . . ?
H8'2 C8' H8'3 109.5 . . ?
C10' C9' C14' 118.6(2) . . ?
C10' C9' C5' 121.8(2) . . ?
C14' C9' C5' 119.6(2) . . ?
C11' C10' C9' 120.6(3) . . ?
C11' C10' H10' 119.7 . . ?
C9' C10' H10' 119.7 . . ?
C12' C11' C10' 120.1(3) . . ?
C12' C11' H11' 119.9 . . ?
C10' C11' H11' 119.9 . . ?
C11' C12' C13' 120.2(3) . . ?
C11' C12' H12' 119.9 . . ?
C13' C12' H12' 119.9 . . ?
C12' C13' C14' 120.1(3) . . ?
C12' C13' H13' 120.0 . . ?
C14' C13' H13' 120.0 . . ?
C13' C14' C9' 120.4(2) . . ?
C13' C14' H14' 119.8 . . ?
C9' C14' H14' 119.8 . . ?
N1' C15' C16' 113.33(19) . . ?
N1' C15' H15A 108.9 . . ?
C16' C15' H15A 108.9 . . ?
N1' C15' H15B 108.9 . . ?
C16' C15' H15B 108.9 . . ?
H15A C15' H15B 107.7 . . ?
C17' C16' C21' 118.3(2) . . ?
C17' C16' C15' 120.8(2) . . ?
C21' C16' C15' 120.9(2) . . ?
C16' C17' C18' 120.6(2) . . ?
C16' C17' H17' 119.7 . . ?
C18' C17' H17' 119.7 . . ?
C19' C18' C17' 120.5(3) . . ?
C19' C18' H18' 119.7 . . ?
C17' C18' H18' 119.7 . . ?
C18' C19' C20' 119.5(3) . . ?
C18' C19' H19' 120.2 . . ?
C20' C19' H19' 120.2 . . ?
C19' C20' C21' 120.3(3) . . ?
C19' C20' H20' 119.9 . . ?
C21' C20' H20' 119.9 . . ?
C20' C21' C16' 120.8(2) . . ?
C20' C21' H21' 119.6 . . ?
C16' C21' H21' 119.6 . . ?
C27' C22' C23' 118.8(2) . . ?
C27' C22' C4' 120.3(2) . . ?
C23' C22' C4' 120.8(2) . . ?
C24' C23' C22' 120.6(3) . . ?
C24' C23' H23' 119.7 . . ?
C22' C23' H23' 119.7 . . ?
C25' C24' C23' 120.3(3) . . ?
C25' C24' H24' 119.9 . . ?
C23' C24' H24' 119.9 . . ?
C24' C25' C26' 119.9(3) . . ?
C24' C25' H25' 120.1 . . ?
C26' C25' H25' 120.1 . . ?
C25' C26' C27' 120.0(3) . . ?
C25' C26' H26' 120.0 . . ?
C27' C26' H26' 120.0 . . ?
C22' C27' C26' 120.4(3) . . ?
C22' C27' H27' 119.8 . . ?
C26' C27' H27' 119.8 . . ?
C2 S1 C6 91.25(12) . . ?
C1 N1 C5 122.6(2) . . ?
C1 N1 C15 116.39(19) . . ?
C5 N1 C15 120.66(18) . . ?
O1 C1 N1 121.7(3) . . ?
O1 C1 C2 124.4(2) . . ?
N1 C1 C2 113.9(2) . . ?
C3 C2 C1 124.6(2) . . ?
C3 C2 S1 112.44(19) . . ?
C1 C2 S1 122.93(18) . . ?
C2 C3 C7 111.5(2) . . ?
C2 C3 C4 118.6(2) . . ?
C7 C3 C4 129.9(2) . . ?
C5 C4 C3 118.1(2) . . ?
C5 C4 C22 121.75(19) . . ?
C3 C4 C22 120.0(2) . . ?
C4 C5 N1 122.04(19) . . ?
C4 C5 C9 120.66(19) . . ?
N1 C5 C9 117.3(2) . . ?
C7 C6 C8 128.3(3) . . ?
C7 C6 S1 111.7(2) . . ?
C8 C6 S1 120.0(2) . . ?
C6 C7 C3 113.2(2) . . ?
C6 C7 H7 123.4 . . ?
C3 C7 H7 123.4 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C14 119.4(2) . . ?
C10 C9 C5 119.5(2) . . ?
C14 C9 C5 121.0(2) . . ?
C9 C10 C11 119.7(3) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C12 C11 C10 120.0(3) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C13 C12 C11 120.7(3) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 119.9(3) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C13 C14 C9 120.3(3) . . ?
C13 C14 H14 119.8 . . ?
C9 C14 H14 119.8 . . ?
N1 C15 C16 111.36(19) . . ?
N1 C15 H15C 109.4 . . ?
C16 C15 H15C 109.4 . . ?
N1 C15 H15D 109.4 . . ?
C16 C15 H15D 109.4 . . ?
H15C C15 H15D 108.0 . . ?
C21 C16 C17 118.1(2) . . ?
C21 C16 C15 120.5(2) . . ?
C17 C16 C15 121.4(2) . . ?
C18 C17 C16 120.4(3) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C19 C18 C17 120.6(3) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C20 C19 C18 119.5(3) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C19 C20 C21 120.0(3) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C20 C21 C16 121.3(2) . . ?
C20 C21 H21 119.3 . . ?
C16 C21 H21 119.3 . . ?
C27 C22 C23 118.7(2) . . ?
C27 C22 C4 121.0(2) . . ?
C23 C22 C4 120.3(2) . . ?
C24 C23 C22 120.6(3) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C25 C24 C23 120.1(3) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C25 C26 119.9(3) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C25 C26 C27 120.1(3) . . ?
C25 C26 H26 119.9 . . ?
C27 C26 H26 119.9 . . ?
C22 C27 C26 120.6(3) . . ?
C22 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?

_diffrn_measured_fraction_theta_max 0.929
_diffrn_reflns_theta_full        67.25
_diffrn_measured_fraction_theta_full 0.929
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.036
####################################################################### 
# 
# 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_14fin
_database_code_depnum_ccdc_archive 'CCDC 1027410'
_audit_update_record             
;
2014-10-02 deposited with the CCDC.
2015-06-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C42 H34 N2 O'
_chemical_formula_sum            'C42 H34 N2 O'
_chemical_formula_weight         582.71

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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)/n
_symmetry_space_group_name_Hall  -P2yn

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

_cell_length_a                   7.8222(3)
_cell_length_b                   19.2845(6)
_cell_length_c                   21.7791(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.329(2)
_cell_angle_gamma                90.00
_cell_volume                     3232.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    6686
_cell_measurement_theta_min      3.08
_cell_measurement_theta_max      65.54

_exptl_crystal_description       Prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1232
_exptl_absorpt_coefficient_mu    0.550
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.876
_exptl_absorpt_correction_T_max  0.906
_exptl_absorpt_process_details   'SADABS (Bruker, 2006)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_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            18931
_diffrn_reflns_av_R_equivalents  0.0590
_diffrn_reflns_av_sigmaI/netI    0.0523
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.08
_diffrn_reflns_theta_max         66.81
_reflns_number_total             5386
_reflns_number_gt                4319
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX 2 (Bruker 2006)'
_computing_cell_refinement       'SAINT (Bruker 2006)'
_computing_data_reduction        'SAINT (Bruker 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Mercury 2.3 (Macrae et al, 2008)'
_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)+(0.0614P)²+0.4637P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0019(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5386
_refine_ls_number_parameters     407
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0467
_refine_ls_wR_factor_ref         0.1323
_refine_ls_wR_factor_gt          0.1235
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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 0.2277(2) 0.22366(8) 0.06953(7) 0.0778(4) Uani 1 1 d . . .
N1 N 0.35544(19) 0.31082(7) 0.12930(7) 0.0545(4) Uani 1 1 d . . .
H1 H 0.3655 0.3313 0.1649 0.065 Uiso 1 1 calc R . .
N2 N 0.1844(2) 0.27416(9) 0.22197(8) 0.0705(5) Uani 1 1 d . . .
C1 C 0.76269(19) 0.33802(7) 0.05639(7) 0.0398(3) Uani 1 1 d . . .
C2 C 0.87665(19) 0.39441(7) 0.07255(7) 0.0424(3) Uani 1 1 d . . .
C3 C 0.9908(2) 0.41344(8) 0.03321(8) 0.0509(4) Uani 1 1 d . . .
H3 H 1.0691 0.4494 0.0449 0.061 Uiso 1 1 calc R . .
C4 C 0.9895(2) 0.37988(9) -0.02268(9) 0.0559(4) Uani 1 1 d . . .
H4 H 1.0662 0.3931 -0.0486 0.067 Uiso 1 1 calc R . .
C5 C 0.8738(2) 0.32660(8) -0.03992(8) 0.0517(4) Uani 1 1 d . . .
H5 H 0.8707 0.3048 -0.0782 0.062 Uiso 1 1 calc R . .
C6 C 0.7613(2) 0.30476(7) -0.00093(7) 0.0423(3) Uani 1 1 d . . .
C7 C 0.6408(2) 0.24555(8) -0.02282(8) 0.0451(4) Uani 1 1 d . . .
C8 C 0.6978(2) 0.17518(8) 0.00107(8) 0.0490(4) Uani 1 1 d . . .
C9 C 0.8602(3) 0.15041(9) -0.00402(9) 0.0598(5) Uani 1 1 d . . .
H9 H 0.9354 0.1782 -0.0218 0.072 Uiso 1 1 calc R . .
C10 C 0.9123(3) 0.08462(11) 0.01713(12) 0.0803(7) Uani 1 1 d . . .
H10 H 1.0215 0.0683 0.0130 0.096 Uiso 1 1 calc R . .
C11 C 0.8036(4) 0.04365(10) 0.04405(13) 0.0912(8) Uani 1 1 d . . .
H11 H 0.8387 -0.0005 0.0581 0.109 Uiso 1 1 calc R . .
C12 C 0.6429(4) 0.06785(10) 0.05030(12) 0.0872(8) Uani 1 1 d . . .
H12 H 0.5697 0.0400 0.0690 0.105 Uiso 1 1 calc R . .
C13 C 0.5882(3) 0.13337(9) 0.02906(9) 0.0642(5) Uani 1 1 d . . .
H13 H 0.4789 0.1494 0.0335 0.077 Uiso 1 1 calc R . .
C14 C 0.4956(2) 0.25850(8) -0.06357(8) 0.0511(4) Uani 1 1 d . . .
H14 H 0.4733 0.3053 -0.0716 0.061 Uiso 1 1 calc R . .
C15 C 0.3647(2) 0.21129(10) -0.09797(8) 0.0579(5) Uani 1 1 d . . .
C16 C 0.3994(3) 0.14355(10) -0.11433(9) 0.0683(5) Uani 1 1 d . . .
H16 H 0.5099 0.1252 -0.1012 0.082 Uiso 1 1 calc R . .
C17 C 0.2736(4) 0.10342(14) -0.14942(11) 0.0888(8) Uani 1 1 d . . .
H17 H 0.2992 0.0583 -0.1599 0.107 Uiso 1 1 calc R . .
C18 C 0.1110(4) 0.1296(2) -0.16897(14) 0.1180(12) Uani 1 1 d . . .
H18 H 0.0250 0.1018 -0.1916 0.142 Uiso 1 1 calc R . .
C19 C 0.0737(3) 0.1968(2) -0.15540(17) 0.1392(16) Uani 1 1 d . . .
H19 H -0.0365 0.2149 -0.1698 0.167 Uiso 1 1 calc R . .
C20 C 0.2008(3) 0.23788(16) -0.12018(13) 0.0960(9) Uani 1 1 d . . .
H20 H 0.1756 0.2836 -0.1114 0.115 Uiso 1 1 calc R . .
C21 C 0.8772(2) 0.43691(7) 0.13028(8) 0.0441(4) Uani 1 1 d . . .
C22 C 0.7143(2) 0.47536(7) 0.13396(7) 0.0428(4) Uani 1 1 d . . .
C23 C 0.6257(2) 0.51141(8) 0.08298(8) 0.0490(4) Uani 1 1 d . . .
H23 H 0.6707 0.5127 0.0463 0.059 Uiso 1 1 calc R . .
C24 C 0.4718(3) 0.54546(9) 0.08566(9) 0.0593(5) Uani 1 1 d . . .
H24 H 0.4140 0.5693 0.0509 0.071 Uiso 1 1 calc R . .
C25 C 0.4038(3) 0.54403(10) 0.13998(11) 0.0677(5) Uani 1 1 d . . .
H25 H 0.3003 0.5669 0.1420 0.081 Uiso 1 1 calc R . .
C26 C 0.4898(3) 0.50857(11) 0.19092(10) 0.0678(5) Uani 1 1 d . . .
H26 H 0.4446 0.5077 0.2276 0.081 Uiso 1 1 calc R . .
C27 C 0.6431(2) 0.47419(9) 0.18817(8) 0.0551(4) Uani 1 1 d . . .
H27 H 0.6995 0.4500 0.2229 0.066 Uiso 1 1 calc R . .
C28 C 1.0219(2) 0.44098(9) 0.17351(9) 0.0540(4) Uani 1 1 d . . .
H28 H 1.1116 0.4115 0.1675 0.065 Uiso 1 1 calc R . .
C29 C 1.0594(2) 0.48561(10) 0.22937(9) 0.0567(4) Uani 1 1 d . . .
C30 C 1.0103(3) 0.55530(11) 0.22860(11) 0.0729(6) Uani 1 1 d . . .
H30 H 0.9469 0.5746 0.1924 0.087 Uiso 1 1 calc R . .
C31 C 1.0560(3) 0.59589(14) 0.28195(15) 0.0933(8) Uani 1 1 d . . .
H31 H 1.0231 0.6423 0.2813 0.112 Uiso 1 1 calc R . .
C32 C 1.1493(4) 0.56767(17) 0.33547(13) 0.0981(9) Uani 1 1 d . . .
H32 H 1.1788 0.5950 0.3710 0.118 Uiso 1 1 calc R . .
C33 C 1.1992(3) 0.49975(16) 0.33686(11) 0.0880(7) Uani 1 1 d . . .
H33 H 1.2624 0.4808 0.3732 0.106 Uiso 1 1 calc R . .
C34 C 1.1550(3) 0.45933(12) 0.28386(10) 0.0714(5) Uani 1 1 d . . .
H34 H 1.1906 0.4133 0.2850 0.086 Uiso 1 1 calc R . .
C35 C 0.6473(2) 0.31231(8) 0.10061(8) 0.0441(4) Uani 1 1 d . . .
H35A H 0.6955 0.3280 0.1424 0.053 Uiso 1 1 calc R . .
H35B H 0.6497 0.2620 0.1010 0.053 Uiso 1 1 calc R . .
C36 C 0.4580(2) 0.33617(9) 0.08447(9) 0.0512(4) Uani 1 1 d . . .
H36A H 0.4542 0.3864 0.0836 0.061 Uiso 1 1 calc R . .
H36B H 0.4075 0.3195 0.0432 0.061 Uiso 1 1 calc R . .
C37 C 0.2468(2) 0.25737(8) 0.11768(8) 0.0493(4) Uani 1 1 d . . .
C38 C 0.1449(2) 0.23999(8) 0.16838(8) 0.0501(4) Uani 1 1 d . . .
C39 C 0.0181(3) 0.19019(10) 0.15751(10) 0.0658(5) Uani 1 1 d . . .
H39 H -0.0066 0.1679 0.1191 0.079 Uiso 1 1 calc R . .
C40 C -0.0725(3) 0.17360(13) 0.20431(12) 0.0812(7) Uani 1 1 d . . .
H40 H -0.1588 0.1398 0.1982 0.097 Uiso 1 1 calc R . .
C41 C -0.0330(4) 0.20755(15) 0.25934(13) 0.0936(8) Uani 1 1 d . . .
H41 H -0.0924 0.1978 0.2917 0.112 Uiso 1 1 calc R . .
C42 C 0.0953(4) 0.25632(15) 0.26667(12) 0.0943(8) Uani 1 1 d . . .
H42 H 0.1226 0.2786 0.3051 0.113 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 C37 1.220(2) . ?
N1 C37 1.331(2) . ?
N1 C36 1.455(2) . ?
N1 H1 0.8600 . ?
N2 C38 1.328(2) . ?
N2 C42 1.340(3) . ?
C1 C6 1.402(2) . ?
C1 C2 1.410(2) . ?
C1 C35 1.517(2) . ?
C2 C3 1.393(2) . ?
C2 C21 1.500(2) . ?
C3 C4 1.377(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.393(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.503(2) . ?
C7 C14 1.334(2) . ?
C7 C8 1.492(2) . ?
C8 C9 1.380(3) . ?
C8 C13 1.394(2) . ?
C9 C10 1.386(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.367(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.370(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.387(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.471(3) . ?
C14 H14 0.9300 . ?
C15 C20 1.385(3) . ?
C15 C16 1.394(3) . ?
C16 C17 1.372(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.364(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.373(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.389(4) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C28 1.339(2) . ?
C21 C22 1.489(2) . ?
C22 C23 1.386(2) . ?
C22 C27 1.393(2) . ?
C23 C24 1.382(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.382(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.373(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.381(3) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 C29 1.476(3) . ?
C28 H28 0.9300 . ?
C29 C34 1.381(3) . ?
C29 C30 1.397(3) . ?
C30 C31 1.393(3) . ?
C30 H30 0.9300 . ?
C31 C32 1.372(4) . ?
C31 H31 0.9300 . ?
C32 C33 1.365(4) . ?
C32 H32 0.9300 . ?
C33 C34 1.385(3) . ?
C33 H33 0.9300 . ?
C34 H34 0.9300 . ?
C35 C36 1.530(2) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C37 C38 1.510(2) . ?
C38 C39 1.371(3) . ?
C39 C40 1.379(3) . ?
C39 H39 0.9300 . ?
C40 C41 1.352(4) . ?
C40 H40 0.9300 . ?
C41 C42 1.364(4) . ?
C41 H41 0.9300 . ?
C42 H42 0.9300 . ?

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
C37 N1 C36 122.87(15) . . ?
C37 N1 H1 118.6 . . ?
C36 N1 H1 118.6 . . ?
C38 N2 C42 116.24(19) . . ?
C6 C1 C2 118.59(14) . . ?
C6 C1 C35 120.38(13) . . ?
C2 C1 C35 121.01(14) . . ?
C3 C2 C1 119.73(14) . . ?
C3 C2 C21 117.75(14) . . ?
C1 C2 C21 122.49(13) . . ?
C4 C3 C2 121.06(15) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C5 C4 C3 119.51(15) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 121.04(16) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 119.99(14) . . ?
C5 C6 C7 117.72(14) . . ?
C1 C6 C7 122.29(13) . . ?
C14 C7 C8 124.58(15) . . ?
C14 C7 C6 118.67(14) . . ?
C8 C7 C6 116.70(14) . . ?
C9 C8 C13 118.81(16) . . ?
C9 C8 C7 120.54(15) . . ?
C13 C8 C7 120.65(16) . . ?
C8 C9 C10 120.68(19) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C11 C10 C9 120.2(2) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 119.8(2) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C11 C12 C13 120.7(2) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C12 C13 C8 119.7(2) . . ?
C12 C13 H13 120.1 . . ?
C8 C13 H13 120.1 . . ?
C7 C14 C15 130.92(16) . . ?
C7 C14 H14 114.5 . . ?
C15 C14 H14 114.5 . . ?
C20 C15 C16 117.9(2) . . ?
C20 C15 C14 117.70(19) . . ?
C16 C15 C14 124.09(18) . . ?
C17 C16 C15 121.2(2) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C18 C17 C16 120.1(3) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 120.3(2) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C18 C19 C20 119.9(3) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C15 C20 C19 120.5(3) . . ?
C15 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C28 C21 C22 123.84(15) . . ?
C28 C21 C2 119.77(14) . . ?
C22 C21 C2 116.32(14) . . ?
C23 C22 C27 117.94(15) . . ?
C23 C22 C21 121.12(14) . . ?
C27 C22 C21 120.90(15) . . ?
C24 C23 C22 121.28(16) . . ?
C24 C23 H23 119.4 . . ?
C22 C23 H23 119.4 . . ?
C23 C24 C25 119.92(18) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C26 C25 C24 119.57(17) . . ?
C26 C25 H25 120.2 . . ?
C24 C25 H25 120.2 . . ?
C25 C26 C27 120.54(18) . . ?
C25 C26 H26 119.7 . . ?
C27 C26 H26 119.7 . . ?
C26 C27 C22 120.75(17) . . ?
C26 C27 H27 119.6 . . ?
C22 C27 H27 119.6 . . ?
C21 C28 C29 129.17(16) . . ?
C21 C28 H28 115.4 . . ?
C29 C28 H28 115.4 . . ?
C34 C29 C30 117.96(19) . . ?
C34 C29 C28 119.42(18) . . ?
C30 C29 C28 122.52(18) . . ?
C31 C30 C29 120.1(2) . . ?
C31 C30 H30 120.0 . . ?
C29 C30 H30 120.0 . . ?
C32 C31 C30 120.2(2) . . ?
C32 C31 H31 119.9 . . ?
C30 C31 H31 119.9 . . ?
C33 C32 C31 120.4(2) . . ?
C33 C32 H32 119.8 . . ?
C31 C32 H32 119.8 . . ?
C32 C33 C34 119.6(3) . . ?
C32 C33 H33 120.2 . . ?
C34 C33 H33 120.2 . . ?
C29 C34 C33 121.7(2) . . ?
C29 C34 H34 119.1 . . ?
C33 C34 H34 119.1 . . ?
C1 C35 C36 114.67(13) . . ?
C1 C35 H35A 108.6 . . ?
C36 C35 H35A 108.6 . . ?
C1 C35 H35B 108.6 . . ?
C36 C35 H35B 108.6 . . ?
H35A C35 H35B 107.6 . . ?
N1 C36 C35 111.84(14) . . ?
N1 C36 H36A 109.2 . . ?
C35 C36 H36A 109.2 . . ?
N1 C36 H36B 109.2 . . ?
C35 C36 H36B 109.2 . . ?
H36A C36 H36B 107.9 . . ?
O1 C37 N1 123.47(16) . . ?
O1 C37 C38 120.73(15) . . ?
N1 C37 C38 115.80(15) . . ?
N2 C38 C39 123.13(17) . . ?
N2 C38 C37 117.57(15) . . ?
C39 C38 C37 119.30(16) . . ?
C38 C39 C40 119.1(2) . . ?
C38 C39 H39 120.4 . . ?
C40 C39 H39 120.4 . . ?
C41 C40 C39 118.5(2) . . ?
C41 C40 H40 120.8 . . ?
C39 C40 H40 120.8 . . ?
C40 C41 C42 119.0(2) . . ?
C40 C41 H41 120.5 . . ?
C42 C41 H41 120.5 . . ?
N2 C42 C41 124.0(2) . . ?
N2 C42 H42 118.0 . . ?
C41 C42 H42 118.0 . . ?

_diffrn_measured_fraction_theta_max 0.937
_diffrn_reflns_theta_full        66.81
_diffrn_measured_fraction_theta_full 0.937
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.034
####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1027411'
_audit_update_record             
;
2014-10-02 deposited with the CCDC.
2015-06-29 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            man615_LT
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H23 N2 O Rh'
_chemical_formula_iupac          ?
_chemical_formula_weight         422.32

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   7.9626(2)
_cell_length_b                   12.2907(4)
_cell_length_c                   18.1403(5)
_cell_angle_alpha                90
_cell_angle_beta                 102.5790(10)
_cell_angle_gamma                90
_cell_volume                     1732.70(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8116
_cell_measurement_theta_min      2.6243
_cell_measurement_theta_max      25.4012
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prismatic
_exptl_crystal_colour            'clear orange'
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.190
_exptl_crystal_density_diffrn    1.619
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864

_exptl_absorpt_coefficient_mu    0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_correction_T_min  0.76
_exptl_absorpt_correction_T_max  0.83

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            15283
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_sigmaI/netI    0.0210
_diffrn_reflns_theta_min         2.02
_diffrn_reflns_theta_max         25.36
_diffrn_reflns_theta_full        25.36
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21

_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.
;

_reflns_number_total             3180
_reflns_number_gt                2903
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0303
_refine_ls_wR_factor_gt          0.0733
_refine_ls_wR_factor_ref         0.0766
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_number_reflns         3180
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0327P)²+3.9264P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.041
_refine_diff_density_min         -0.873
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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

_computing_data_collection       'Bruker Instrument Service v2010.9.0.0'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.3915(4) 0.5057(2) 0.06922(16) 0.0217(6) Uani d . 1 . .
H H1 0.2975 0.4829 0.0305 0.026 Uiso calc R 1 . .
C C2 0.4995(4) 0.4278(3) 0.10852(17) 0.0250(6) Uani d . 1 . .
H H2 0.4818 0.3529 0.0962 0.03 Uiso calc R 1 . .
C C3 0.6348(4) 0.4603(3) 0.16645(19) 0.0300(7) Uani d . 1 . .
H H3 0.7086 0.4081 0.1957 0.036 Uiso calc R 1 . .
C C4 0.6594(4) 0.5704(3) 0.18054(18) 0.0284(7) Uani d . 1 . .
H H4 0.7518 0.5948 0.2194 0.034 Uiso calc R 1 . .
C C5 0.5489(4) 0.6447(2) 0.13786(16) 0.0213(6) Uani d . 1 . .
C C6 0.5759(4) 0.7657(2) 0.14771(17) 0.0216(6) Uani d . 1 . .
C C7 0.4989(4) 0.9422(2) 0.10221(16) 0.0222(6) Uani d . 1 . .
H H7A 0.4469 0.9741 0.0524 0.027 Uiso calc R 1 . .
H H7B 0.625 0.952 0.1104 0.027 Uiso calc R 1 . .
C C8 0.4363(4) 1.0068(2) 0.16221(15) 0.0201(6) Uani d . 1 . .
C C9 0.4650(3) 1.1188(2) 0.16566(16) 0.0211(6) Uani d . 1 . .
H H9 0.519 1.1522 0.1297 0.025 Uiso calc R 1 . .
C C10 0.4161(4) 1.1823(3) 0.22069(17) 0.0248(6) Uani d . 1 . .
H H10 0.4383 1.2583 0.2227 0.03 Uiso calc R 1 . .
C C11 0.3351(4) 1.1346(3) 0.27248(17) 0.0286(7) Uani d . 1 . .
H H11 0.3014 1.1775 0.3103 0.034 Uiso calc R 1 . .
C C12 0.3033(5) 1.0237(3) 0.26886(19) 0.0349(8) Uani d . 1 . .
H H12 0.2461 0.9908 0.304 0.042 Uiso calc R 1 . .
C C13 0.3541(4) 0.9600(3) 0.21427(17) 0.0286(7) Uani d . 1 . .
H H13 0.3324 0.8839 0.2126 0.034 Uiso calc R 1 . .
C C14 0.0260(4) 0.6521(3) 0.0178(2) 0.0383(9) Uani d . 1 . .
H H14 0.0381 0.5802 0.0443 0.046 Uiso calc R 1 . .
C C15 -0.1193(5) 0.7219(4) 0.0344(4) 0.0734(18) Uani d . 1 . .
H H15A -0.2273 0.7008 -0.001 0.088 Uiso calc R 1 . .
H H15B -0.1332 0.7048 0.0861 0.088 Uiso calc R 1 . .
C C16 -0.0979(4) 0.8385(3) 0.0290(2) 0.0409(9) Uani d . 1 . .
H H16A -0.1333 0.8734 0.0724 0.049 Uiso calc R 1 . .
H H16B -0.1768 0.8646 -0.0175 0.049 Uiso calc R 1 . .
C C17 0.0839(4) 0.8764(3) 0.02766(19) 0.0276(7) Uani d . 1 . .
H H17 0.1267 0.938 0.0628 0.033 Uiso calc R 1 . .
C C18 0.1524(4) 0.8733(3) -0.03662(17) 0.0293(7) Uani d . 1 . .
H H18 0.2367 0.9328 -0.0388 0.035 Uiso calc R 1 . .
C C19 0.0589(5) 0.8329(4) -0.1138(2) 0.0540(12) Uani d . 1 . .
H H19A -0.0443 0.8788 -0.1313 0.065 Uiso calc R 1 . .
H H19B 0.1351 0.8434 -0.1497 0.065 Uiso calc R 1 . .
C C20 0.0047(8) 0.7192(4) -0.1172(2) 0.088(2) Uani d . 1 . .
H H20A 0.0338 0.6853 -0.1623 0.106 Uiso calc R 1 . .
H H20B -0.122 0.7168 -0.1239 0.106 Uiso calc R 1 . .
C C21 0.0844(5) 0.6519(3) -0.04862(19) 0.0402(10) Uani d . 1 . .
H H21 0.131 0.5802 -0.0609 0.048 Uiso calc R 1 . .
N N1 0.4134(3) 0.6125(2) 0.08333(13) 0.0186(5) Uani d . 1 . .
N N2 0.4626(3) 0.8254(2) 0.09864(13) 0.0197(5) Uani d . 1 . .
O O1 0.6979(3) 0.79927(19) 0.19706(12) 0.0297(5) Uani d . 1 . .
Rh Rh1 0.25693(3) 0.742597(18) 0.035829(12) 0.01794(10) Uani d . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . 1.341(4) ?
C1 C2 . 1.378(4) ?
C1 H1 . 0.95 ?
C2 C3 . 1.390(4) ?
C2 H2 . 0.95 ?
C3 C4 . 1.382(5) ?
C3 H3 . 0.95 ?
C4 C5 . 1.382(4) ?
C4 H4 . 0.95 ?
C5 N1 . 1.354(4) ?
C5 C6 . 1.509(4) ?
C6 O1 . 1.239(4) ?
C6 N2 . 1.339(4) ?
C7 N2 . 1.463(4) ?
C7 C8 . 1.517(4) ?
C7 H7A . 0.99 ?
C7 H7B . 0.99 ?
C8 C13 . 1.386(4) ?
C8 C9 . 1.394(4) ?
C9 C10 . 1.388(4) ?
C9 H9 . 0.95 ?
C10 C11 . 1.381(4) ?
C10 H10 . 0.95 ?
C11 C12 . 1.386(5) ?
C11 H11 . 0.95 ?
C12 C13 . 1.390(5) ?
C12 H12 . 0.95 ?
C13 H13 . 0.95 ?
C14 C21 . 1.384(5) ?
C14 C15 . 1.522(5) ?
C14 Rh1 . 2.113(3) ?
C14 H14 . 1.0 ?
C15 C16 . 1.450(6) ?
C15 H15A . 0.99 ?
C15 H15B . 0.99 ?
C16 C17 . 1.526(4) ?
C16 H16A . 0.99 ?
C16 H16B . 0.99 ?
C17 C18 . 1.391(4) ?
C17 Rh1 . 2.130(3) ?
C17 H17 . 1.0 ?
C18 C19 . 1.519(5) ?
C18 Rh1 . 2.127(3) ?
C18 H18 . 1.0 ?
C19 C20 . 1.459(7) ?
C19 H19A . 0.99 ?
C19 H19B . 0.99 ?
C20 C21 . 1.514(5) ?
C20 H20A . 0.99 ?
C20 H20B . 0.99 ?
C21 Rh1 . 2.135(3) ?
C21 H21 . 1.0 ?
N1 Rh1 . 2.094(2) ?
N2 Rh1 . 2.050(2) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 C2 . . 122.7(3) ?
N1 C1 H1 . . 118.6 ?
C2 C1 H1 . . 118.6 ?
C1 C2 C3 . . 119.0(3) ?
C1 C2 H2 . . 120.5 ?
C3 C2 H2 . . 120.5 ?
C4 C3 C2 . . 118.5(3) ?
C4 C3 H3 . . 120.8 ?
C2 C3 H3 . . 120.8 ?
C3 C4 C5 . . 119.7(3) ?
C3 C4 H4 . . 120.1 ?
C5 C4 H4 . . 120.1 ?
N1 C5 C4 . . 121.7(3) ?
N1 C5 C6 . . 116.4(3) ?
C4 C5 C6 . . 121.9(3) ?
O1 C6 N2 . . 127.3(3) ?
O1 C6 C5 . . 118.9(3) ?
N2 C6 C5 . . 113.8(3) ?
N2 C7 C8 . . 117.0(2) ?
N2 C7 H7A . . 108.1 ?
C8 C7 H7A . . 108.1 ?
N2 C7 H7B . . 108.1 ?
C8 C7 H7B . . 108.1 ?
H7A C7 H7B . . 107.3 ?
C13 C8 C9 . . 118.4(3) ?
C13 C8 C7 . . 123.3(3) ?
C9 C8 C7 . . 118.2(3) ?
C10 C9 C8 . . 121.2(3) ?
C10 C9 H9 . . 119.4 ?
C8 C9 H9 . . 119.4 ?
C11 C10 C9 . . 119.7(3) ?
C11 C10 H10 . . 120.1 ?
C9 C10 H10 . . 120.1 ?
C10 C11 C12 . . 119.6(3) ?
C10 C11 H11 . . 120.2 ?
C12 C11 H11 . . 120.2 ?
C13 C12 C11 . . 120.6(3) ?
C13 C12 H12 . . 119.7 ?
C11 C12 H12 . . 119.7 ?
C12 C13 C8 . . 120.4(3) ?
C12 C13 H13 . . 119.8 ?
C8 C13 H13 . . 119.8 ?
C21 C14 C15 . . 126.0(4) ?
C21 C14 Rh1 . . 71.9(2) ?
C15 C14 Rh1 . . 110.2(2) ?
C21 C14 H14 . . 113.7 ?
C15 C14 H14 . . 113.7 ?
Rh1 C14 H14 . . 113.7 ?
C16 C15 C14 . . 116.0(4) ?
C16 C15 H15A . . 108.3 ?
C14 C15 H15A . . 108.3 ?
C16 C15 H15B . . 108.3 ?
C14 C15 H15B . . 108.3 ?
H15A C15 H15B . . 107.4 ?
C15 C16 C17 . . 115.4(3) ?
C15 C16 H16A . . 108.4 ?
C17 C16 H16A . . 108.4 ?
C15 C16 H16B . . 108.4 ?
C17 C16 H16B . . 108.4 ?
H16A C16 H16B . . 107.5 ?
C18 C17 C16 . . 123.4(3) ?
C18 C17 Rh1 . . 70.79(18) ?
C16 C17 Rh1 . . 111.4(2) ?
C18 C17 H17 . . 114.5 ?
C16 C17 H17 . . 114.5 ?
Rh1 C17 H17 . . 114.5 ?
C17 C18 C19 . . 125.4(3) ?
C17 C18 Rh1 . . 71.06(17) ?
C19 C18 Rh1 . . 111.7(3) ?
C17 C18 H18 . . 113.7 ?
C19 C18 H18 . . 113.7 ?
Rh1 C18 H18 . . 113.7 ?
C20 C19 C18 . . 115.6(3) ?
C20 C19 H19A . . 108.4 ?
C18 C19 H19A . . 108.4 ?
C20 C19 H19B . . 108.4 ?
C18 C19 H19B . . 108.4 ?
H19A C19 H19B . . 107.4 ?
C19 C20 C21 . . 114.9(3) ?
C19 C20 H20A . . 108.5 ?
C21 C20 H20A . . 108.5 ?
C19 C20 H20B . . 108.5 ?
C21 C20 H20B . . 108.5 ?
H20A C20 H20B . . 107.5 ?
C14 C21 C20 . . 123.7(4) ?
C14 C21 Rh1 . . 70.12(18) ?
C20 C21 Rh1 . . 113.2(3) ?
C14 C21 H21 . . 114.1 ?
C20 C21 H21 . . 114.1 ?
Rh1 C21 H21 . . 114.1 ?
C1 N1 C5 . . 118.4(3) ?
C1 N1 Rh1 . . 128.86(19) ?
C5 N1 Rh1 . . 112.70(19) ?
C6 N2 C7 . . 114.2(2) ?
C6 N2 Rh1 . . 116.0(2) ?
C7 N2 Rh1 . . 129.61(19) ?
N2 Rh1 N1 . . 79.53(9) ?
N2 Rh1 C14 . . 155.53(13) ?
N1 Rh1 C14 . . 94.67(12) ?
N2 Rh1 C18 . . 97.27(11) ?
N1 Rh1 C18 . . 161.58(11) ?
C14 Rh1 C18 . . 95.27(14) ?
N2 Rh1 C17 . . 94.70(11) ?
N1 Rh1 C17 . . 159.44(11) ?
C14 Rh1 C17 . . 82.41(13) ?
C18 Rh1 C17 . . 38.15(12) ?
N2 Rh1 C21 . . 165.71(13) ?
N1 Rh1 C21 . . 97.41(11) ?
C14 Rh1 C21 . . 38.01(15) ?
C18 Rh1 C21 . . 81.18(13) ?
C17 Rh1 C21 . . 92.74(13) ?

