# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_001
_database_code_depnum_ccdc_archive 'CCDC 1023075'
_audit_update_record             
;
2014-09-05 deposited with the CCDC.
2015-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H26 Br N O3'
_chemical_formula_sum            'C30 H26 Br N O3'
_chemical_formula_weight         528.42

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'

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

_cell_length_a                   8.6087(10)
_cell_length_b                   12.0564(13)
_cell_length_c                   13.9281(15)
_cell_angle_alpha                108.468(3)
_cell_angle_beta                 104.708(3)
_cell_angle_gamma                94.122(3)
_cell_volume                     1307.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8089
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      27.39

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            RED
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.3
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_exptl_absorpt_coefficient_mu    1.602
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         '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            19861
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_sigmaI/netI    0.0392
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.61
_diffrn_reflns_theta_max         27.48
_reflns_number_total             5999
_reflns_number_gt                3651
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5923
_refine_ls_number_parameters     318
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0933
_refine_ls_R_factor_gt           0.0514
_refine_ls_wR_factor_ref         0.1672
_refine_ls_wR_factor_gt          0.1409
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.59535(5) 0.59689(3) 0.31089(4) 0.1021(2) Uani 1 1 d . . .
O1 O 1.0526(2) 0.20079(17) 0.04582(16) 0.0643(5) Uani 1 1 d . . .
O2 O 0.9660(2) 0.33158(15) 0.16634(16) 0.0612(5) Uani 1 1 d . . .
O3 O 0.6400(2) 0.13789(15) 0.10548(15) 0.0601(5) Uani 1 1 d . . .
N1 N 0.7199(3) -0.02339(18) 0.00984(16) 0.0527(5) Uani 1 1 d . . .
H1A H 0.6229 -0.0534 -0.0314 0.063 Uiso 1 1 d R . .
H2A H 0.7995 -0.0606 0.0008 0.063 Uiso 1 1 d R . .
C1 C 1.4713(3) 0.4580(2) 0.3055(2) 0.0554(6) Uani 1 1 d . . .
C2 C 1.4873(3) 0.3491(3) 0.2418(2) 0.0610(7) Uani 1 1 d . . .
H2 H 1.5590 0.3427 0.2011 0.073 Uiso 1 1 calc R . .
C3 C 1.3954(3) 0.2491(2) 0.2393(2) 0.0552(6) Uani 1 1 d . . .
H3 H 1.4081 0.1750 0.1976 0.066 Uiso 1 1 calc R . .
C4 C 1.2853(3) 0.2558(2) 0.29642(19) 0.0445(5) Uani 1 1 d . . .
C5 C 1.2744(4) 0.3658(2) 0.3609(3) 0.0752(9) Uani 1 1 d . . .
H5 H 1.2032 0.3723 0.4019 0.090 Uiso 1 1 calc R . .
C6 C 1.3673(4) 0.4672(3) 0.3662(3) 0.0803(10) Uani 1 1 d . . .
H6 H 1.3590 0.5411 0.4107 0.096 Uiso 1 1 calc R . .
C7 C 1.1853(3) 0.1475(2) 0.29219(19) 0.0464(6) Uani 1 1 d . . .
C8 C 1.2343(3) 0.0784(2) 0.3487(2) 0.0516(6) Uani 1 1 d . . .
H8 H 1.3391 0.0883 0.3931 0.062 Uiso 1 1 calc R . .
C9 C 1.1001(3) -0.0151(2) 0.3315(2) 0.0478(6) Uani 1 1 d . . .
C10 C 0.9665(3) -0.0036(2) 0.26125(19) 0.0440(5) Uani 1 1 d . . .
C11 C 1.0127(3) 0.09738(19) 0.22835(19) 0.0435(5) Uani 1 1 d . . .
C12 C 1.1160(3) -0.0998(2) 0.3885(2) 0.0476(6) Uani 1 1 d . . .
C13 C 0.9868(3) -0.1422(2) 0.4173(2) 0.0530(6) Uani 1 1 d . . .
H13 H 0.8863 -0.1189 0.3984 0.064 Uiso 1 1 calc R . .
C14 C 1.0058(3) -0.2183(2) 0.4735(2) 0.0560(7) Uani 1 1 d . . .
H14 H 0.9170 -0.2459 0.4910 0.067 Uiso 1 1 calc R . .
C15 C 1.1529(3) -0.2547(2) 0.5047(2) 0.0533(6) Uani 1 1 d . . .
C16 C 1.2823(3) -0.2122(2) 0.4762(2) 0.0600(7) Uani 1 1 d . . .
H16 H 1.3827 -0.2357 0.4953 0.072 Uiso 1 1 calc R . .
C17 C 1.2645(3) -0.1358(2) 0.4201(2) 0.0579(7) Uani 1 1 d . . .
H17 H 1.3536 -0.1078 0.4031 0.070 Uiso 1 1 calc R . .
C18 C 1.1703(5) -0.3365(3) 0.5676(3) 0.0772(9) Uani 1 1 d . . .
H18A H 1.1713 -0.2936 0.6388 0.116 Uiso 1 1 calc R . .
H18B H 1.2703 -0.3671 0.5683 0.116 Uiso 1 1 calc R . .
H18C H 1.0803 -0.4010 0.5357 0.116 Uiso 1 1 calc R . .
C19 C 0.8042(3) -0.0788(2) 0.21942(18) 0.0461(6) Uani 1 1 d . . .
C20 C 0.6685(3) -0.0336(3) 0.2441(2) 0.0610(7) Uani 1 1 d . . .
H20 H 0.6807 0.0444 0.2887 0.073 Uiso 1 1 calc R . .
C21 C 0.5168(4) -0.1037(4) 0.2030(3) 0.0796(10) Uani 1 1 d . . .
H21 H 0.4279 -0.0718 0.2197 0.096 Uiso 1 1 calc R . .
C22 C 0.4947(4) -0.2193(3) 0.1381(3) 0.0827(10) Uani 1 1 d . . .
C23 C 0.6284(5) -0.2641(3) 0.1152(3) 0.0828(11) Uani 1 1 d . . .
H23 H 0.6154 -0.3427 0.0718 0.099 Uiso 1 1 calc R . .
C24 C 0.7827(4) -0.1953(2) 0.1551(2) 0.0595(7) Uani 1 1 d . . .
H24 H 0.8711 -0.2281 0.1382 0.071 Uiso 1 1 calc R . .
C25 C 0.3274(5) -0.2951(5) 0.0926(5) 0.150(2) Uani 1 1 d . . .
H25A H 0.3203 -0.3535 0.1181 0.180 Uiso 1 1 d R . .
H25B H 0.3338 -0.3578 0.0274 0.180 Uiso 1 1 d R . .
H25C H 0.2446 -0.2558 0.0778 0.180 Uiso 1 1 d R . .
C26 C 0.9233(3) 0.13118(19) 0.15169(18) 0.0414(5) Uani 1 1 d . . .
C27 C 0.9898(3) 0.2241(2) 0.1159(2) 0.0450(6) Uani 1 1 d . . .
C28 C 1.0320(4) 0.4274(2) 0.1364(3) 0.0724(8) Uani 1 1 d . . .
H28A H 0.9870 0.4109 0.0611 0.087 Uiso 1 1 calc R . .
H28B H 1.1496 0.4349 0.1531 0.087 Uiso 1 1 calc R . .
C29 C 0.9855(6) 0.5379(3) 0.1975(4) 0.1235(17) Uani 1 1 d . . .
H29A H 0.8704 0.5352 0.1710 0.185 Uiso 1 1 calc R . .
H29B H 1.0430 0.6047 0.1903 0.185 Uiso 1 1 calc R . .
H29C H 1.0131 0.5456 0.2708 0.185 Uiso 1 1 calc R . .
C60 C 0.7464(3) 0.0800(2) 0.08739(19) 0.0442(5) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.890(2) . ?
O1 C27 1.200(3) . ?
O2 C27 1.322(3) . ?
O2 C28 1.471(3) . ?
O3 C60 1.220(3) . ?
N1 C60 1.324(3) . ?
N1 H1A 0.8597 . ?
N1 H2A 0.8598 . ?
C1 C6 1.367(4) . ?
C1 C2 1.371(4) . ?
C2 C3 1.379(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.375(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.371(4) . ?
C4 C7 1.488(3) . ?
C5 C6 1.383(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.337(4) . ?
C7 C11 1.491(3) . ?
C8 C9 1.471(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.355(4) . ?
C9 C12 1.473(3) . ?
C10 C19 1.478(3) . ?
C10 C11 1.492(3) . ?
C11 C26 1.342(3) . ?
C12 C17 1.390(4) . ?
C12 C13 1.391(4) . ?
C13 C14 1.375(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.381(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.391(4) . ?
C15 C18 1.504(4) . ?
C16 C17 1.376(4) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C24 1.375(3) . ?
C19 C20 1.399(4) . ?
C20 C21 1.379(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.368(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.373(6) . ?
C22 C25 1.514(5) . ?
C23 C24 1.391(4) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 H25A 0.8885 . ?
C25 H25B 0.9979 . ?
C25 H25C 0.9003 . ?
C26 C27 1.497(3) . ?
C26 C60 1.525(3) . ?
C28 C29 1.480(5) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?

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
C27 O2 C28 115.7(2) . . ?
C60 N1 H1A 120.0 . . ?
C60 N1 H2A 120.1 . . ?
H1A N1 H2A 120.0 . . ?
C6 C1 C2 120.6(3) . . ?
C6 C1 Br1 119.5(2) . . ?
C2 C1 Br1 120.0(2) . . ?
C1 C2 C3 118.8(2) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C4 C3 C2 121.9(2) . . ?
C4 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
C5 C4 C3 117.8(2) . . ?
C5 C4 C7 120.6(2) . . ?
C3 C4 C7 121.5(2) . . ?
C4 C5 C6 121.3(3) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C5 119.5(3) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C8 C7 C4 125.5(2) . . ?
C8 C7 C11 107.1(2) . . ?
C4 C7 C11 127.4(2) . . ?
C7 C8 C9 110.9(2) . . ?
C7 C8 H8 124.5 . . ?
C9 C8 H8 124.5 . . ?
C10 C9 C12 128.7(2) . . ?
C10 C9 C8 108.4(2) . . ?
C12 C9 C8 122.9(2) . . ?
C9 C10 C19 127.4(2) . . ?
C9 C10 C11 107.8(2) . . ?
C19 C10 C11 124.7(2) . . ?
C26 C11 C10 127.7(2) . . ?
C26 C11 C7 126.5(2) . . ?
C10 C11 C7 105.6(2) . . ?
C17 C12 C13 117.4(2) . . ?
C17 C12 C9 120.7(2) . . ?
C13 C12 C9 121.9(2) . . ?
C14 C13 C12 120.9(2) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 121.9(3) . . ?
C13 C14 H14 119.0 . . ?
C15 C14 H14 119.0 . . ?
C14 C15 C16 117.3(2) . . ?
C14 C15 C18 120.6(3) . . ?
C16 C15 C18 122.1(3) . . ?
C17 C16 C15 121.2(3) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C16 C17 C12 121.3(3) . . ?
C16 C17 H17 119.3 . . ?
C12 C17 H17 119.3 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C24 C19 C20 118.2(2) . . ?
C24 C19 C10 120.8(2) . . ?
C20 C19 C10 121.0(2) . . ?
C21 C20 C19 120.7(3) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C22 C21 C20 121.2(3) . . ?
C22 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
C23 C22 C21 118.1(3) . . ?
C23 C22 C25 121.1(4) . . ?
C21 C22 C25 120.8(4) . . ?
C22 C23 C24 122.0(3) . . ?
C22 C23 H23 119.0 . . ?
C24 C23 H23 119.0 . . ?
C19 C24 C23 119.8(3) . . ?
C19 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C22 C25 H25A 112.3 . . ?
C22 C25 H25B 104.3 . . ?
H25A C25 H25B 85.4 . . ?
C22 C25 H25C 114.8 . . ?
H25A C25 H25C 123.0 . . ?
H25B C25 H25C 111.2 . . ?
C11 C26 C27 123.0(2) . . ?
C11 C26 C60 126.1(2) . . ?
C27 C26 C60 110.84(19) . . ?
O1 C27 O2 124.6(2) . . ?
O1 C27 C26 122.4(2) . . ?
O2 C27 C26 113.0(2) . . ?
O2 C28 C29 107.0(3) . . ?
O2 C28 H28A 110.3 . . ?
C29 C28 H28A 110.3 . . ?
O2 C28 H28B 110.3 . . ?
C29 C28 H28B 110.3 . . ?
H28A C28 H28B 108.6 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
O3 C60 N1 123.9(2) . . ?
O3 C60 C26 119.3(2) . . ?
N1 C60 C26 116.6(2) . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.710
_refine_diff_density_rms         0.080
####################################################################### 
# 
# 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_001
_database_code_depnum_ccdc_archive 'CCDC 1037660'
_audit_update_record             
;
2014-12-04 deposited with the CCDC.
2015-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C31 H29 N O5'
_chemical_formula_sum            'C31 H29 N O5'
_chemical_formula_weight         495.55

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '


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

_cell_length_a                   5.8328(6)
_cell_length_b                   11.8968(14)
_cell_length_c                   19.757(2)
_cell_angle_alpha                78.469(4)
_cell_angle_beta                 88.020(4)
_cell_angle_gamma                82.246(4)
_cell_volume                     1331.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296.15
_cell_measurement_reflns_used    8670
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      24.73

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             524
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296.15
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         '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            24435
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_av_sigmaI/netI    0.0337
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.87
_diffrn_reflns_theta_max         24.99
_reflns_number_total             4654
_reflns_number_gt                3297
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1001P)²+0.1391P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4649
_refine_ls_number_parameters     346
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.1447
_refine_ls_wR_factor_gt          0.1320
_refine_ls_goodness_of_fit_ref   0.937
_refine_ls_restrained_S_all      0.937
_refine_ls_shift/su_max          0.089
_refine_ls_shift/su_mean         0.002

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
O4 O 0.7295(2) 0.14758(11) 0.18112(7) 0.0593(4) Uani 1 1 d . . .
O3 O 0.6929(3) 0.49485(13) 0.07037(7) 0.0641(4) Uani 1 1 d . . .
O1 O -0.2070(2) 0.72754(13) 0.46738(7) 0.0657(4) Uani 1 1 d . . .
C2 C 0.6883(3) 0.31518(15) 0.30062(9) 0.0401(4) Uani 1 1 d . . .
C4 C 0.4101(3) 0.46866(15) 0.31252(9) 0.0425(4) Uani 1 1 d . . .
C1 C 0.6082(3) 0.37945(14) 0.23096(8) 0.0384(4) Uani 1 1 d . . .
C6 C 0.3287(3) 0.57554(15) 0.19006(8) 0.0394(4) Uani 1 1 d . . .
C5 C 0.4376(3) 0.47845(15) 0.24325(8) 0.0401(4) Uani 1 1 d . . .
O2 O 0.0280(3) 0.86412(12) 0.05160(8) 0.0721(5) Uani 1 1 d . . .
N1 N 0.4135(3) 0.38110(17) 0.07124(10) 0.0596(5) Uani 1 1 d . . .
C27 C 0.6636(3) 0.34891(15) 0.16976(9) 0.0403(4) Uani 1 1 d . . .
C29 C 0.8243(3) 0.24361(16) 0.16024(9) 0.0458(5) Uani 1 1 d . . .
C28 C 0.5859(3) 0.41790(16) 0.09932(9) 0.0447(5) Uani 1 1 d . . .
C15 C -0.0484(3) 0.66507(16) 0.43204(9) 0.0472(5) Uani 1 1 d . . .
C18 C 0.8621(3) 0.21149(15) 0.31813(9) 0.0400(4) Uani 1 1 d . . .
C9 C 0.1186(3) 0.76525(16) 0.09583(9) 0.0487(5) Uani 1 1 d . . .
C19 C 1.0854(3) 0.20641(16) 0.29099(10) 0.0462(5) Uani 1 1 d . . .
H19 H 1.1304 0.2718 0.2600 0.055 Uiso 1 1 calc R . .
C12 C 0.2519(3) 0.53951(15) 0.35190(9) 0.0439(4) Uani 1 1 d . . .
C11 C 0.1394(3) 0.56809(16) 0.15200(9) 0.0482(5) Uani 1 1 d . . .
H11 H 0.0789 0.4964 0.1584 0.058 Uiso 1 1 calc R . .
C3 C 0.5684(3) 0.36819(16) 0.34653(9) 0.0460(5) Uani 1 1 d . . .
H3 H 0.5834 0.3440 0.3952 0.055 Uiso 1 1 calc R . .
C16 C 0.1666(3) 0.61484(18) 0.45637(10) 0.0541(5) Uani 1 1 d . . .
H16 H 0.2144 0.6224 0.5006 0.065 Uiso 1 1 calc R . .
C17 C 0.3133(3) 0.55326(18) 0.41632(10) 0.0527(5) Uani 1 1 d . . .
H17 H 0.4617 0.5192 0.4338 0.063 Uiso 1 1 calc R . .
C10 C 0.0346(3) 0.66102(16) 0.10493(9) 0.0507(5) Uani 1 1 d . . .
H10 H -0.0945 0.6528 0.0791 0.061 Uiso 1 1 calc R . .
C20 C 1.2425(3) 0.10811(17) 0.30830(11) 0.0568(5) Uani 1 1 d . . .
H20 H 1.3933 0.1067 0.2884 0.068 Uiso 1 1 calc R . .
C14 C -0.1159(3) 0.65189(19) 0.36785(11) 0.0576(5) Uani 1 1 d . . .
H14 H -0.2651 0.6856 0.3509 0.069 Uiso 1 1 calc R . .
C7 C 0.4097(3) 0.68191(16) 0.17997(10) 0.0520(5) Uani 1 1 d . . .
H7 H 0.5395 0.6901 0.2055 0.062 Uiso 1 1 calc R . .
C21 C 1.1861(3) 0.01160(18) 0.35386(12) 0.0645(6) Uani 1 1 d . . .
C23 C 0.8076(3) 0.11585(16) 0.36547(10) 0.0505(5) Uani 1 1 d . . .
H23 H 0.6579 0.1176 0.3861 0.061 Uiso 1 1 calc R . .
C8 C 0.3073(4) 0.77523(17) 0.13425(12) 0.0599(6) Uani 1 1 d . . .
H8 H 0.3654 0.8474 0.1287 0.072 Uiso 1 1 calc R . .
C13 C 0.0305(3) 0.59084(18) 0.32872(10) 0.0547(5) Uani 1 1 d . . .
H13 H -0.0189 0.5829 0.2848 0.066 Uiso 1 1 calc R . .
C22 C 0.9667(4) 0.01820(18) 0.38314(12) 0.0620(6) Uani 1 1 d . . .
H22 H 0.9250 -0.0458 0.4160 0.074 Uiso 1 1 calc R . .
C26 C -0.1358(4) 0.7483(2) 0.53127(11) 0.0727(7) Uani 1 1 d . . .
H26A H -0.1017 0.6745 0.5638 0.109 Uiso 1 1 calc R . .
H26B H -0.2599 0.7975 0.5502 0.109 Uiso 1 1 calc R . .
H26C H 0.0033 0.7872 0.5239 0.109 Uiso 1 1 calc R . .
C25 C -0.1704(4) 0.8594(2) 0.01327(12) 0.0733(7) Uani 1 1 d . . .
H25A H -0.1321 0.8042 -0.0174 0.110 Uiso 1 1 calc R . .
H25B H -0.2216 0.9363 -0.0143 0.110 Uiso 1 1 calc R . .
H25C H -0.2947 0.8345 0.0451 0.110 Uiso 1 1 calc R . .
C30 C 0.8686(5) 0.0409(2) 0.16982(15) 0.0865(8) Uani 1 1 d . . .
H30A H 0.8770 0.0394 0.1199 0.104 Uiso 1 1 calc R . .
H30B H 1.0279 0.0369 0.1867 0.104 Uiso 1 1 calc R . .
C24 C 1.3551(4) -0.0976(2) 0.3718(2) 0.1102(11) Uani 1 1 d . . .
H24A H 1.5135 -0.0785 0.3645 0.165 Uiso 1 1 calc R . .
H24B H 1.3276 -0.1513 0.3421 0.165 Uiso 1 1 calc R . .
H24C H 1.3339 -0.1338 0.4202 0.165 Uiso 1 1 calc R . .
C31 C 0.7611(7) -0.0569(2) 0.2070(2) 0.1196(12) Uani 1 1 d . . .
H31A H 0.7545 -0.0551 0.2564 0.179 Uiso 1 1 calc R . .
H31B H 0.8524 -0.1291 0.1998 0.179 Uiso 1 1 calc R . .
H31C H 0.6040 -0.0525 0.1897 0.179 Uiso 1 1 calc R . .
O5 O 1.0106(3) 0.24755(13) 0.13253(7) 0.0646(4) Uani 1 1 d . . .
H1A H 0.356(4) 0.414(2) 0.0326(14) 0.078(8) Uiso 1 1 d . . .
H1B H 0.318(4) 0.331(2) 0.0952(12) 0.071(7) Uiso 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
O4 C29 1.322(2) . ?
O4 C30 1.463(3) . ?
O3 C28 1.215(2) . ?
O1 C15 1.369(2) . ?
O1 C26 1.420(3) . ?
C2 C3 1.333(2) . ?
C2 C18 1.478(2) . ?
C2 C1 1.491(2) . ?
C4 C5 1.356(2) . ?
C4 C12 1.473(2) . ?
C4 C3 1.468(2) . ?
C1 C27 1.347(2) . ?
C1 C5 1.489(2) . ?
C6 C11 1.380(2) . ?
C6 C7 1.385(3) . ?
C6 C5 1.485(2) . ?
O2 C9 1.371(2) . ?
O2 C25 1.418(3) . ?
N1 C28 1.329(2) . ?
C27 C29 1.499(3) . ?
C27 C28 1.518(2) . ?
C29 O5 1.202(2) . ?
C15 C16 1.373(3) . ?
C15 C14 1.385(3) . ?
C18 C19 1.390(3) . ?
C18 C23 1.386(3) . ?
C9 C10 1.371(3) . ?
C9 C8 1.389(3) . ?
C19 C20 1.377(3) . ?
C12 C17 1.380(3) . ?
C12 C13 1.403(3) . ?
C11 C10 1.381(3) . ?
C16 C17 1.382(3) . ?
C20 C21 1.380(3) . ?
C14 C13 1.366(3) . ?
C7 C8 1.365(3) . ?
C21 C22 1.385(3) . ?
C21 C24 1.510(3) . ?
C23 C22 1.379(3) . ?
C30 C31 1.452(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C29 O4 C30 115.78(16) . . ?
C15 O1 C26 117.02(16) . . ?
C3 C2 C18 124.91(15) . . ?
C3 C2 C1 106.59(15) . . ?
C18 C2 C1 128.49(15) . . ?
C5 C4 C12 129.67(16) . . ?
C5 C4 C3 108.13(15) . . ?
C12 C4 C3 122.18(15) . . ?
C27 C1 C5 126.76(15) . . ?
C27 C1 C2 127.05(16) . . ?
C5 C1 C2 105.97(14) . . ?
C11 C6 C7 117.06(16) . . ?
C11 C6 C5 123.35(16) . . ?
C7 C6 C5 119.48(16) . . ?
C4 C5 C6 125.53(16) . . ?
C4 C5 C1 107.67(15) . . ?
C6 C5 C1 126.67(15) . . ?
C9 O2 C25 117.86(17) . . ?
C1 C27 C29 125.05(16) . . ?
C1 C27 C28 126.01(16) . . ?
C29 C27 C28 108.86(14) . . ?
O5 C29 O4 124.33(18) . . ?
O5 C29 C27 123.52(17) . . ?
O4 C29 C27 111.96(16) . . ?
O3 C28 N1 124.59(17) . . ?
O3 C28 C27 119.50(16) . . ?
N1 C28 C27 115.63(17) . . ?
O1 C15 C16 124.55(17) . . ?
O1 C15 C14 116.20(17) . . ?
C16 C15 C14 119.25(17) . . ?
C19 C18 C23 117.37(16) . . ?
C19 C18 C2 122.68(16) . . ?
C23 C18 C2 119.90(15) . . ?
O2 C9 C10 124.89(18) . . ?
O2 C9 C8 115.80(17) . . ?
C10 C9 C8 119.30(17) . . ?
C20 C19 C18 121.06(18) . . ?
C17 C12 C13 116.60(17) . . ?
C17 C12 C4 120.33(16) . . ?
C13 C12 C4 123.00(17) . . ?
C6 C11 C10 122.39(17) . . ?
C2 C3 C4 111.53(15) . . ?
C15 C16 C17 119.74(18) . . ?
C12 C17 C16 122.37(18) . . ?
C9 C10 C11 119.33(17) . . ?
C19 C20 C21 121.53(18) . . ?
C13 C14 C15 120.51(18) . . ?
C8 C7 C6 121.52(18) . . ?
C22 C21 C20 117.47(18) . . ?
C22 C21 C24 120.6(2) . . ?
C20 C21 C24 121.9(2) . . ?
C22 C23 C18 121.18(17) . . ?
C7 C8 C9 120.38(18) . . ?
C14 C13 C12 121.53(18) . . ?
C21 C22 C23 121.29(19) . . ?
C31 C30 O4 108.5(2) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.044
####################################################################### 
# 
# 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_001
_database_code_depnum_ccdc_archive 'CCDC 1040541'
_audit_update_record             
;
2014-12-21 deposited with the CCDC.
2015-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H26 Cl N O5'
_chemical_formula_weight         515.97

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

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

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

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

_cell_length_a                   19.841(5)
_cell_length_b                   14.847(4)
_cell_length_c                   8.918(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.596(6)
_cell_angle_gamma                90
_cell_volume                     2626.9(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2919
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      20.51

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_F_000             1080
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.3
_exptl_absorpt_coefficient_mu    0.186
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24139
_diffrn_reflns_av_unetI/netI     0.1929
_diffrn_reflns_av_R_equivalents  0.1707
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.053
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.969
_reflns_number_total             4612
_reflns_number_gt                1924
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0280P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4612
_refine_ls_number_parameters     348
_refine_ls_number_restraints     29
_refine_ls_R_factor_all          0.2109
_refine_ls_R_factor_gt           0.0678
_refine_ls_wR_factor_ref         0.1094
_refine_ls_wR_factor_gt          0.0883
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.53387(5) -0.26940(8) 0.66398(13) 0.0719(4) Uani 1 1 d . . . . .
O1 O 0.29180(12) 0.53811(16) 0.4438(3) 0.0482(8) Uani 1 1 d . . . . .
O2 O 0.12931(11) 0.09864(17) 0.6143(3) 0.0461(7) Uani 1 1 d . . . . .
O3 O 0.10728(14) -0.09603(19) 0.4453(3) 0.0692(10) Uani 1 1 d . . . . .
O4 O 0.16772(12) -0.07789(18) 0.2352(4) 0.0559(8) Uani 1 1 d . U . . .
O5 O 0.24674(13) -0.22586(17) 0.4533(3) 0.0576(9) Uani 1 1 d . . . . .
N1 N 0.25122(13) -0.15987(19) 0.6816(4) 0.0486(10) Uani 1 1 d . . . . .
H1A H 0.2577 -0.2119 0.7266 0.058 Uiso 1 1 d R U . . .
H1B H 0.2491 -0.1101 0.7347 0.058 Uiso 1 1 d R U . . .
C1 C 0.47572(17) -0.1842(3) 0.6234(5) 0.0421(12) Uani 1 1 d . . . . .
C2 C 0.47210(18) -0.1113(3) 0.7157(5) 0.0492(12) Uani 1 1 d . . . . .
H2 H 0.5008 -0.1060 0.7983 0.059 Uiso 1 1 calc R U . . .
C3 C 0.42416(18) -0.0443(2) 0.6837(4) 0.0432(11) Uani 1 1 d . . . . .
H3 H 0.4208 0.0054 0.7467 0.052 Uiso 1 1 calc R U . . .
C4 C 0.38189(17) -0.0511(3) 0.5598(4) 0.0325(10) Uani 1 1 d . . . . .
C5 C 0.38940(18) -0.1254(3) 0.4673(4) 0.0449(11) Uani 1 1 d . . . . .
H5 H 0.3626 -0.1303 0.3815 0.054 Uiso 1 1 calc R U . . .
C6 C 0.43564(19) -0.1920(3) 0.4994(5) 0.0461(12) Uani 1 1 d . . . . .
H6 H 0.4394 -0.2419 0.4370 0.055 Uiso 1 1 calc R U . . .
C7 C 0.33189(17) 0.0203(3) 0.5256(4) 0.0292(10) Uani 1 1 d . . . . .
C8 C 0.26174(17) 0.0073(2) 0.4669(4) 0.0264(9) Uani 1 1 d . . . . .
C9 C 0.23719(17) 0.0989(2) 0.4256(4) 0.0252(9) Uani 1 1 d . . . . .
C10 C 0.28600(17) 0.1588(2) 0.4651(4) 0.0272(9) Uani 1 1 d . . . . .
C11 C 0.34449(17) 0.1085(2) 0.5235(4) 0.0338(10) Uani 1 1 d . . . . .
H11 H 0.3848 0.1348 0.5548 0.041 Uiso 1 1 calc R U . . .
C12 C 0.28554(17) 0.2580(2) 0.4610(4) 0.0250(9) Uani 1 1 d . . . . .
C13 C 0.32548(16) 0.3051(2) 0.5622(4) 0.0351(10) Uani 1 1 d . . . . .
H13 H 0.3509 0.2729 0.6320 0.042 Uiso 1 1 calc R U . . .
C14 C 0.32906(17) 0.3977(3) 0.5637(4) 0.0378(10) Uani 1 1 d . . . . .
H14 H 0.3557 0.4275 0.6344 0.045 Uiso 1 1 calc R U . . .
C15 C 0.29233(18) 0.4453(2) 0.4584(4) 0.0325(10) Uani 1 1 d . . . . .
C16 C 0.25217(17) 0.4007(2) 0.3553(4) 0.0355(10) Uani 1 1 d . . . . .
H16 H 0.2276 0.4333 0.2844 0.043 Uiso 1 1 calc R U . . .
C17 C 0.24829(17) 0.3079(3) 0.3569(4) 0.0334(10) Uani 1 1 d . . . . .
H17 H 0.2206 0.2784 0.2879 0.040 Uiso 1 1 calc R U . . .
C18 C 0.16769(18) 0.1179(2) 0.3704(5) 0.0283(10) Uani 1 1 d . . . . .
C19 C 0.15417(19) 0.1371(2) 0.2206(5) 0.0387(11) Uani 1 1 d . . . . .
H19 H 0.1895 0.1362 0.1529 0.046 Uiso 1 1 calc R U . . .
C20 C 0.0898(2) 0.1574(3) 0.1687(5) 0.0547(13) Uani 1 1 d . . . . .
H20 H 0.0821 0.1715 0.0684 0.066 Uiso 1 1 calc R U . . .
C21 C 0.0376(2) 0.1563(3) 0.2692(6) 0.0552(13) Uani 1 1 d . . . . .
H21 H -0.0059 0.1692 0.2356 0.066 Uiso 1 1 calc R U . . .
C22 C 0.0483(2) 0.1365(3) 0.4174(5) 0.0499(12) Uani 1 1 d . . . . .
H22 H 0.0124 0.1353 0.4835 0.060 Uiso 1 1 calc R U . . .
C23 C 0.1134(2) 0.1181(2) 0.4686(5) 0.0349(10) Uani 1 1 d . . . . .
C24 C 0.0749(2) 0.0840(3) 0.7152(4) 0.0758(15) Uani 1 1 d . . . . .
H24A H 0.0487 0.1382 0.7233 0.114 Uiso 1 1 calc R U . . .
H24B H 0.0925 0.0680 0.8122 0.114 Uiso 1 1 calc R U . . .
H24C H 0.0468 0.0362 0.6779 0.114 Uiso 1 1 calc R U . . .
C25 C 0.22595(17) -0.0692(2) 0.4633(4) 0.0285(10) Uani 1 1 d . . . . .
C26 C 0.1586(2) -0.0810(2) 0.3831(6) 0.0378(11) Uani 1 1 d . . . . .
C27 C 0.1068(2) -0.0911(4) 0.1426(6) 0.0921(18) Uani 1 1 d . U . . .
H27A H 0.0811 -0.1414 0.1816 0.111 Uiso 0.481(17) 1 calc R U P A 1
H27B H 0.0788 -0.0377 0.1479 0.111 Uiso 0.481(17) 1 calc R U P A 1
H27C H 0.0675 -0.0765 0.2017 0.111 Uiso 0.519(17) 1 calc R U P A 2
H27D H 0.1079 -0.0499 0.0582 0.111 Uiso 0.519(17) 1 calc R U P A 2
C28 C 0.1226(7) -0.1073(16) -0.0013(15) 0.103(7) Uani 0.481(17) 1 d . U P A 1
H28A H 0.1482 -0.0577 -0.0398 0.154 Uiso 0.481(17) 1 calc R U P A 1
H28B H 0.0821 -0.1145 -0.0596 0.154 Uiso 0.481(17) 1 calc R U P A 1
H28C H 0.1490 -0.1614 -0.0069 0.154 Uiso 0.481(17) 1 calc R U P A 1
C28' C 0.1007(6) -0.1762(10) 0.091(2) 0.104(7) Uani 0.519(17) 1 d . U P A 2
H28D H 0.1413 -0.1931 0.0403 0.155 Uiso 0.519(17) 1 calc R U P A 2
H28E H 0.0633 -0.1795 0.0219 0.155 Uiso 0.519(17) 1 calc R U P A 2
H28F H 0.0933 -0.2164 0.1732 0.155 Uiso 0.519(17) 1 calc R U P A 2
C29 C 0.24437(17) -0.1588(3) 0.5327(5) 0.0365(10) Uani 1 1 d . . . . .
C30 C 0.32777(19) 0.5878(2) 0.5549(4) 0.0619(13) Uani 1 1 d . . . . .
H30A H 0.3115 0.5721 0.6524 0.093 Uiso 1 1 calc R U . . .
H30B H 0.3212 0.6511 0.5381 0.093 Uiso 1 1 calc R U . . .
H30C H 0.3749 0.5739 0.5491 0.093 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.747(4) . ?
O1 C15 1.384(4) . ?
O1 C30 1.422(4) . ?
O2 C23 1.365(4) . ?
O2 C24 1.430(4) . ?
O3 C26 1.187(4) . ?
O4 C26 1.334(4) . ?
O4 C27 1.470(4) . ?
O5 C29 1.223(4) . ?
N1 C29 1.334(4) . ?
N1 H1A 0.8786 . ?
N1 H1B 0.8790 . ?
C1 C6 1.360(5) . ?
C1 C2 1.363(5) . ?
C2 C3 1.404(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.384(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.386(4) . ?
C4 C7 1.482(4) . ?
C5 C6 1.378(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C11 1.334(4) . ?
C7 C8 1.494(4) . ?
C8 C25 1.340(4) . ?
C8 C9 1.488(4) . ?
C9 C10 1.359(4) . ?
C9 C18 1.487(4) . ?
C10 C11 1.470(4) . ?
C10 C12 1.474(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.384(4) . ?
C12 C17 1.395(4) . ?
C13 C14 1.377(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.378(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.380(4) . ?
C16 C17 1.380(4) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C19 1.389(4) . ?
C18 C23 1.396(4) . ?
C19 C20 1.387(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.378(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.369(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.392(4) . ?
C22 H22 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C29 1.510(5) . ?
C25 C26 1.519(5) . ?
C27 C28 1.346(12) . ?
C27 C28' 1.350(11) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C27 H27C 0.9700 . ?
C27 H27D 0.9700 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C28' H28D 0.9600 . ?
C28' H28E 0.9600 . ?
C28' H28F 0.9600 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?

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
C15 O1 C30 116.6(3) . . ?
C23 O2 C24 117.5(3) . . ?
C26 O4 C27 115.6(4) . . ?
C29 N1 H1A 118.6 . . ?
C29 N1 H1B 121.4 . . ?
H1A N1 H1B 120.0 . . ?
C6 C1 C2 121.7(4) . . ?
C6 C1 Cl1 119.1(4) . . ?
C2 C1 Cl1 119.3(4) . . ?
C1 C2 C3 118.7(4) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C4 C3 C2 120.9(4) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 117.8(3) . . ?
C3 C4 C7 120.7(4) . . ?
C5 C4 C7 121.5(3) . . ?
C6 C5 C4 121.5(4) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C1 C6 C5 119.4(4) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C11 C7 C4 125.5(3) . . ?
C11 C7 C8 107.2(3) . . ?
C4 C7 C8 126.8(3) . . ?
C25 C8 C9 126.6(3) . . ?
C25 C8 C7 127.5(3) . . ?
C9 C8 C7 105.7(3) . . ?
C10 C9 C8 107.6(3) . . ?
C10 C9 C18 128.1(3) . . ?
C8 C9 C18 123.8(3) . . ?
C9 C10 C11 108.5(3) . . ?
C9 C10 C12 130.1(3) . . ?
C11 C10 C12 121.4(3) . . ?
C7 C11 C10 110.8(3) . . ?
C7 C11 H11 124.6 . . ?
C10 C11 H11 124.6 . . ?
C13 C12 C17 117.5(3) . . ?
C13 C12 C10 119.1(3) . . ?
C17 C12 C10 123.4(3) . . ?
C14 C13 C12 122.7(3) . . ?
C14 C13 H13 118.6 . . ?
C12 C13 H13 118.6 . . ?
C13 C14 C15 118.6(4) . . ?
C13 C14 H14 120.7 . . ?
C15 C14 H14 120.7 . . ?
C14 C15 C16 120.4(3) . . ?
C14 C15 O1 125.3(4) . . ?
C16 C15 O1 114.3(4) . . ?
C15 C16 C17 120.3(3) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C16 C17 C12 120.6(3) . . ?
C16 C17 H17 119.7 . . ?
C12 C17 H17 119.7 . . ?
C19 C18 C23 117.4(3) . . ?
C19 C18 C9 121.8(3) . . ?
C23 C18 C9 120.8(4) . . ?
C20 C19 C18 122.3(4) . . ?
C20 C19 H19 118.9 . . ?
C18 C19 H19 118.9 . . ?
C21 C20 C19 118.5(4) . . ?
C21 C20 H20 120.8 . . ?
C19 C20 H20 120.8 . . ?
C22 C21 C20 121.3(4) . . ?
C22 C21 H21 119.3 . . ?
C20 C21 H21 119.3 . . ?
C21 C22 C23 119.6(4) . . ?
C21 C22 H22 120.2 . . ?
C23 C22 H22 120.2 . . ?
O2 C23 C22 123.9(4) . . ?
O2 C23 C18 115.1(4) . . ?
C22 C23 C18 120.9(4) . . ?
O2 C24 H24A 109.5 . . ?
O2 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O2 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C8 C25 C29 127.6(3) . . ?
C8 C25 C26 124.9(3) . . ?
C29 C25 C26 107.4(3) . . ?
O3 C26 O4 126.5(4) . . ?
O3 C26 C25 123.8(4) . . ?
O4 C26 C25 109.6(4) . . ?
C28 C27 O4 111.1(7) . . ?
C28' C27 O4 112.8(6) . . ?
C28 C27 H27A 109.4 . . ?
O4 C27 H27A 109.4 . . ?
C28 C27 H27B 109.4 . . ?
O4 C27 H27B 109.4 . . ?
H27A C27 H27B 108.0 . . ?
C28' C27 H27C 109.0 . . ?
O4 C27 H27C 109.0 . . ?
C28' C27 H27D 109.0 . . ?
O4 C27 H27D 109.0 . . ?
H27C C27 H27D 107.8 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C27 C28' H28D 109.5 . . ?
C27 C28' H28E 109.5 . . ?
H28D C28' H28E 109.5 . . ?
C27 C28' H28F 109.5 . . ?
H28D C28' H28F 109.5 . . ?
H28E C28' H28F 109.5 . . ?
O5 C29 N1 124.2(4) . . ?
O5 C29 C25 119.4(4) . . ?
N1 C29 C25 116.1(4) . . ?
O1 C30 H30A 109.5 . . ?
O1 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
O1 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?

_refine_diff_density_max         0.196
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.051

_shelxl_version_number           2014/6



