# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 2017

####################################################################### 
# 
# 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_dp2nc-1
_database_code_depnum_ccdc_archive 'CCDC 1525969'
_audit_update_record             
;
2017-01-06 deposited with the CCDC.
2017-09-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C38 H27 Br2 N O2'
_chemical_formula_sum            'C38 H27 Br2 N O2'
_chemical_formula_weight         689.41

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C 2/c'

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

_cell_length_a                   19.610(2)
_cell_length_b                   15.469(2)
_cell_length_c                   20.516(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.135(11)
_cell_angle_gamma                90.00
_cell_volume                     5946.9(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    32349
_cell_measurement_theta_min      1.14
_cell_measurement_theta_max      25.0

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2784.0
_exptl_absorpt_coefficient_mu    2.763
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.905
_exptl_absorpt_correction_T_max  0.940
_exptl_absorpt_process_details   multi-scan

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  '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            32449
_diffrn_reflns_av_R_equivalents  0.0866
_diffrn_reflns_av_sigmaI/netI    0.0679
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.71
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5249
_reflns_number_gt                2232
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0361P] 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         5189
_refine_ls_number_parameters     388
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1421
_refine_ls_R_factor_gt           0.0436
_refine_ls_wR_factor_ref         0.1870
_refine_ls_wR_factor_gt          0.1186
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_restrained_S_all      0.985
_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
Br1 Br 1.03675(4) 0.47094(6) 1.14644(4) 0.1035(4) Uani 1 1 d . . .
Br2 Br 0.60101(4) 0.73897(6) 0.76864(4) 0.1072(4) Uani 1 1 d . . .
C13 C 0.5237(3) 0.4364(4) 0.6233(3) 0.0604(15) Uani 1 1 d . . .
C8 C 0.3551(3) 0.4597(5) 0.4733(3) 0.0676(17) Uani 1 1 d . . .
C9 C 0.4180(3) 0.4818(4) 0.5309(3) 0.0634(16) Uani 1 1 d . . .
C7 C 0.3940(3) 0.3091(5) 0.4804(3) 0.0674(16) Uani 1 1 d . . .
C17 C 0.4566(3) 0.3319(4) 0.5385(3) 0.0614(16) Uani 1 1 d . . .
C15 C 0.5603(3) 0.2889(4) 0.6277(3) 0.080(2) Uani 1 1 d . . .
H15 H 0.5926 0.2456 0.6478 0.096 Uiso 1 1 calc R . .
C12 C 0.5305(3) 0.5236(4) 0.6442(3) 0.0694(17) Uani 1 1 d . . .
H12 H 0.5677 0.5390 0.6823 0.083 Uiso 1 1 calc R . .
C16 C 0.5039(4) 0.2694(4) 0.5696(3) 0.083(2) Uani 1 1 d . . .
H16 H 0.4986 0.2135 0.5522 0.100 Uiso 1 1 calc R . .
C18 C 0.4649(3) 0.4164(4) 0.5638(3) 0.0561(15) Uani 1 1 d . . .
C14 C 0.5691(3) 0.3695(4) 0.6553(3) 0.0634(16) Uani 1 1 d . . .
C11 C 0.4847(4) 0.5861(4) 0.6108(3) 0.089(2) Uani 1 1 d . . .
H11 H 0.4915 0.6431 0.6256 0.106 Uiso 1 1 calc R . .
C10 C 0.4274(4) 0.5646(4) 0.5544(3) 0.086(2) Uani 1 1 d . . .
H10 H 0.3954 0.6072 0.5326 0.103 Uiso 1 1 calc R . .
C6 C 0.2002(4) 0.3513(5) 0.2811(3) 0.099(2) Uani 1 1 d . . .
H6A H 0.1925 0.3818 0.2382 0.119 Uiso 1 1 calc R . .
H6B H 0.2057 0.2903 0.2727 0.119 Uiso 1 1 calc R . .
C5 C 0.2684(3) 0.3845(5) 0.3320(3) 0.086(2) Uani 1 1 d . . .
H5A H 0.3091 0.3685 0.3168 0.103 Uiso 1 1 calc R . .
H5B H 0.2668 0.4471 0.3341 0.103 Uiso 1 1 calc R . .
C1 C 0.1365(4) 0.3630(6) 0.3058(3) 0.105(3) Uani 1 1 d . . .
H1A H 0.1260 0.4242 0.3063 0.126 Uiso 1 1 calc R . .
H1B H 0.0957 0.3352 0.2740 0.126 Uiso 1 1 calc R . .
C2 C 0.1461(3) 0.3269(5) 0.3748(3) 0.094(2) Uani 1 1 d . . .
H2A H 0.1484 0.2644 0.3727 0.112 Uiso 1 1 calc R . .
H2B H 0.1051 0.3420 0.3898 0.112 Uiso 1 1 calc R . .
C4 C 0.2770(3) 0.3471(4) 0.4020(3) 0.0721(18) Uani 1 1 d . . .
H4 H 0.2809 0.2845 0.3969 0.087 Uiso 1 1 calc R . .
C3 C 0.2132(3) 0.3602(5) 0.4264(3) 0.089(2) Uani 1 1 d . . .
H3A H 0.2078 0.4213 0.4343 0.107 Uiso 1 1 calc R . .
H3B H 0.2202 0.3301 0.4693 0.107 Uiso 1 1 calc R . .
C19 C 0.6283(3) 0.3886(4) 0.7192(3) 0.0621(16) Uani 1 1 d . . .
C22 C 0.7386(3) 0.4253(4) 0.8380(3) 0.0649(16) Uani 1 1 d . . .
C23 C 0.7513(3) 0.4114(4) 0.7772(3) 0.082(2) Uani 1 1 d . . .
H23 H 0.7980 0.4136 0.7750 0.099 Uiso 1 1 calc R . .
C24 C 0.6965(3) 0.3939(5) 0.7184(3) 0.087(2) Uani 1 1 d . . .
H24 H 0.7071 0.3857 0.6775 0.104 Uiso 1 1 calc R . .
C21 C 0.6698(4) 0.4187(5) 0.8382(3) 0.100(2) Uani 1 1 d . . .
H21 H 0.6590 0.4266 0.8790 0.119 Uiso 1 1 calc R . .
C20 C 0.6150(4) 0.4004(6) 0.7797(4) 0.102(3) Uani 1 1 d . . .
H20 H 0.5685 0.3962 0.7820 0.123 Uiso 1 1 calc R . .
C25 C 0.7966(3) 0.4504(4) 0.8989(3) 0.0691(17) Uani 1 1 d . . .
H25 H 0.8286 0.4073 0.9200 0.083 Uiso 1 1 calc R . .
C26 C 0.8075(3) 0.5288(4) 0.9264(3) 0.0648(16) Uani 1 1 d . . .
C36 C 0.9681(3) 0.5386(5) 1.0831(3) 0.0774(19) Uani 1 1 d . . .
C37 C 0.9191(3) 0.5009(4) 1.0295(3) 0.0752(18) Uani 1 1 d . . .
H37 H 0.9207 0.4419 1.0216 0.090 Uiso 1 1 calc R . .
C32 C 0.8044(4) 0.6776(4) 0.9455(3) 0.081(2) Uani 1 1 d . . .
C33 C 0.8651(4) 0.6403(5) 0.9975(3) 0.081(2) Uani 1 1 d . . .
C28 C 0.7075(3) 0.6292(5) 0.8500(3) 0.0724(18) Uani 1 1 d . . .
H28 H 0.6831 0.5858 0.8211 0.087 Uiso 1 1 calc R . .
C38 C 0.8669(3) 0.5520(4) 0.9868(3) 0.0680(17) Uani 1 1 d . . .
C27 C 0.7683(3) 0.6100(4) 0.9030(3) 0.0656(16) Uani 1 1 d . . .
C29 C 0.6842(4) 0.7120(5) 0.8409(3) 0.0795(19) Uani 1 1 d . . .
C30 C 0.7184(4) 0.7781(5) 0.8816(4) 0.097(2) Uani 1 1 d . . .
H30 H 0.7009 0.8342 0.8738 0.116 Uiso 1 1 calc R . .
C31 C 0.7793(5) 0.7612(5) 0.9343(4) 0.109(3) Uani 1 1 d . . .
H31 H 0.8032 0.8059 0.9621 0.131 Uiso 1 1 calc R . .
C34 C 0.9171(4) 0.6785(5) 1.0507(4) 0.113(3) Uani 1 1 d . . .
H34 H 0.9175 0.7380 1.0570 0.136 Uiso 1 1 calc R . .
C35 C 0.9681(4) 0.6271(6) 1.0941(3) 0.103(3) Uani 1 1 d . . .
H35 H 1.0025 0.6517 1.1307 0.124 Uiso 1 1 calc R . .
N1 N 0.3446(2) 0.3738(3) 0.4533(2) 0.0621(13) Uani 1 1 d . . .
O1 O 0.3854(2) 0.2362(3) 0.4581(2) 0.0930(15) Uani 1 1 d . . .
O2 O 0.3127(2) 0.5156(3) 0.4450(2) 0.0902(14) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C36 1.887(6) . ?
Br2 C29 1.899(7) . ?
C13 C14 1.396(8) . ?
C13 C12 1.410(8) . ?
C13 C18 1.445(7) . ?
C8 O2 1.222(7) . ?
C8 N1 1.387(7) . ?
C8 C9 1.476(7) . ?
C9 C10 1.361(8) . ?
C9 C18 1.400(8) . ?
C7 O1 1.211(7) . ?
C7 N1 1.390(7) . ?
C7 C17 1.479(8) . ?
C17 C16 1.361(8) . ?
C17 C18 1.398(8) . ?
C15 C14 1.359(8) . ?
C15 C16 1.400(8) . ?
C12 C11 1.358(8) . ?
C14 C19 1.502(7) . ?
C11 C10 1.395(8) . ?
C6 C1 1.491(9) . ?
C6 C5 1.523(8) . ?
C5 C4 1.511(8) . ?
C1 C2 1.482(9) . ?
C2 C3 1.514(8) . ?
C4 N1 1.489(7) . ?
C4 C3 1.492(8) . ?
C19 C24 1.345(8) . ?
C19 C20 1.355(8) . ?
C22 C21 1.354(8) . ?
C22 C23 1.360(8) . ?
C22 C25 1.472(8) . ?
C23 C24 1.386(8) . ?
C21 C20 1.384(8) . ?
C25 C26 1.327(8) . ?
C26 C38 1.474(7) . ?
C26 C27 1.477(8) . ?
C36 C37 1.361(8) . ?
C36 C35 1.388(10) . ?
C37 C38 1.381(8) . ?
C32 C31 1.379(9) . ?
C32 C27 1.412(8) . ?
C32 C33 1.462(9) . ?
C33 C38 1.385(8) . ?
C33 C34 1.387(9) . ?
C28 C29 1.354(9) . ?
C28 C27 1.389(8) . ?
C29 C30 1.365(9) . ?
C30 C31 1.379(10) . ?
C34 C35 1.378(10) . ?

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
C14 C13 C12 125.2(5) . . ?
C14 C13 C18 118.5(5) . . ?
C12 C13 C18 116.2(5) . . ?
O2 C8 N1 121.1(5) . . ?
O2 C8 C9 120.5(6) . . ?
N1 C8 C9 118.4(5) . . ?
C10 C9 C18 120.5(5) . . ?
C10 C9 C8 119.8(6) . . ?
C18 C9 C8 119.6(5) . . ?
O1 C7 N1 121.1(5) . . ?
O1 C7 C17 121.1(6) . . ?
N1 C7 C17 117.7(6) . . ?
C16 C17 C18 120.1(5) . . ?
C16 C17 C7 119.8(6) . . ?
C18 C17 C7 120.0(5) . . ?
C14 C15 C16 121.5(6) . . ?
C11 C12 C13 122.6(5) . . ?
C17 C16 C15 120.3(6) . . ?
C17 C18 C9 120.6(5) . . ?
C17 C18 C13 119.4(5) . . ?
C9 C18 C13 120.0(5) . . ?
C15 C14 C13 120.0(5) . . ?
C15 C14 C19 121.0(5) . . ?
C13 C14 C19 119.0(5) . . ?
C12 C11 C10 120.0(6) . . ?
C9 C10 C11 120.7(6) . . ?
C1 C6 C5 112.4(6) . . ?
C4 C5 C6 110.6(6) . . ?
C2 C1 C6 113.3(6) . . ?
C1 C2 C3 112.3(6) . . ?
N1 C4 C3 112.6(5) . . ?
N1 C4 C5 113.2(5) . . ?
C3 C4 C5 113.4(5) . . ?
C4 C3 C2 111.2(6) . . ?
C24 C19 C20 117.6(5) . . ?
C24 C19 C14 121.2(5) . . ?
C20 C19 C14 121.2(6) . . ?
C21 C22 C23 116.3(6) . . ?
C21 C22 C25 122.6(6) . . ?
C23 C22 C25 121.0(6) . . ?
C22 C23 C24 121.7(6) . . ?
C19 C24 C23 121.4(6) . . ?
C22 C21 C20 122.2(6) . . ?
C19 C20 C21 120.9(6) . . ?
C26 C25 C22 126.1(5) . . ?
C25 C26 C38 124.7(6) . . ?
C25 C26 C27 129.4(5) . . ?
C38 C26 C27 105.8(5) . . ?
C37 C36 C35 121.3(6) . . ?
C37 C36 Br1 120.7(6) . . ?
C35 C36 Br1 118.0(5) . . ?
C36 C37 C38 118.9(6) . . ?
C31 C32 C27 120.2(6) . . ?
C31 C32 C33 131.8(6) . . ?
C27 C32 C33 108.0(6) . . ?
C38 C33 C34 119.8(6) . . ?
C38 C33 C32 109.1(5) . . ?
C34 C33 C32 131.1(7) . . ?
C29 C28 C27 119.2(6) . . ?
C37 C38 C33 120.8(5) . . ?
C37 C38 C26 130.4(6) . . ?
C33 C38 C26 108.8(5) . . ?
C28 C27 C32 118.9(6) . . ?
C28 C27 C26 133.0(6) . . ?
C32 C27 C26 108.2(5) . . ?
C28 C29 C30 122.6(6) . . ?
C28 C29 Br2 119.5(5) . . ?
C30 C29 Br2 117.8(6) . . ?
C29 C30 C31 119.6(7) . . ?
C30 C31 C32 119.5(7) . . ?
C35 C34 C33 119.2(7) . . ?
C34 C35 C36 119.9(6) . . ?
C8 N1 C7 123.2(5) . . ?
C8 N1 C4 119.9(5) . . ?
C7 N1 C4 116.9(5) . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.490
_refine_diff_density_rms         0.054
####################################################################### 
# 
# 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_dp1nc-a
_database_code_depnum_ccdc_archive 'CCDC 1525968'
_audit_update_record             
;
2017-01-06 deposited with the CCDC.
2017-09-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C38 H29 N O2'
_chemical_formula_sum            'C38 H29 N O2'
_chemical_formula_weight         531.62

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

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

_cell_length_a                   11.2762(6)
_cell_length_b                   13.9376(8)
_cell_length_c                   17.8045(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.143(4)
_cell_angle_gamma                90.00
_cell_volume                     2745.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    26730
_cell_measurement_theta_min      1.14
_cell_measurement_theta_max      25.000

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1120.0
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_process_details   multi-scan

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  '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            26930
_diffrn_reflns_av_R_equivalents  0.0712
_diffrn_reflns_av_sigmaI/netI    0.0564
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.87
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4837
_reflns_number_gt                2525
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)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         4837
_refine_ls_number_parameters     370
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1213
_refine_ls_R_factor_gt           0.0545
_refine_ls_wR_factor_ref         0.1844
_refine_ls_wR_factor_gt          0.1472
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_restrained_S_all      0.978
_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
O2 O 0.86921(18) 0.70891(15) 0.25350(11) 0.0704(6) Uani 1 1 d . . .
O1 O 0.64829(19) 0.61233(18) 0.02533(12) 0.0866(7) Uani 1 1 d . . .
N1 N 0.75893(19) 0.66479(16) 0.13786(13) 0.0556(6) Uani 1 1 d . . .
C25 C 0.5657(2) 0.61510(18) 0.21113(15) 0.0475(7) Uani 1 1 d . . .
C24 C 0.5536(2) 0.6009(2) 0.13180(16) 0.0536(7) Uani 1 1 d . . .
C21 C 0.3584(2) 0.5570(2) 0.20293(16) 0.0568(7) Uani 1 1 d . . .
C26 C 0.4681(2) 0.59203(19) 0.24843(15) 0.0527(7) Uani 1 1 d . . .
C30 C 0.6741(2) 0.65125(19) 0.25456(15) 0.0504(7) Uani 1 1 d . . .
C31 C 0.7735(3) 0.6771(2) 0.21731(16) 0.0542(7) Uani 1 1 d . . .
C32 C 0.6550(3) 0.6256(2) 0.09354(18) 0.0619(8) Uani 1 1 d . . .
C29 C 0.6870(3) 0.6619(2) 0.33197(16) 0.0637(8) Uani 1 1 d . . .
H29 H 0.7583 0.6870 0.3601 0.076 Uiso 1 1 calc R . .
C18 C 0.2507(2) 0.5380(2) 0.23743(16) 0.0574(8) Uani 1 1 d . . .
C33 C 0.8608(2) 0.6940(2) 0.10069(16) 0.0618(8) Uani 1 1 d . . .
H33 H 0.9210 0.7229 0.1415 0.074 Uiso 1 1 calc R . .
C23 C 0.4504(3) 0.5632(2) 0.09124(17) 0.0688(9) Uani 1 1 d . . .
H23 H 0.4440 0.5517 0.0392 0.083 Uiso 1 1 calc R . .
C27 C 0.4882(3) 0.6015(2) 0.32869(16) 0.0617(8) Uani 1 1 d . . .
H27 H 0.4274 0.5841 0.3546 0.074 Uiso 1 1 calc R . .
C6 C -0.2434(3) 0.4212(2) 0.37444(18) 0.0651(8) Uani 1 1 d . . .
C22 C 0.3528(2) 0.5410(2) 0.12651(17) 0.0668(9) Uani 1 1 d . . .
H22 H 0.2829 0.5150 0.0974 0.080 Uiso 1 1 calc R . .
C7 C -0.1572(3) 0.4381(2) 0.32243(17) 0.0596(8) Uani 1 1 d . . .
C20 C 0.1048(2) 0.5913(2) 0.31086(17) 0.0634(8) Uani 1 1 d . . .
H20 H 0.0760 0.6396 0.3387 0.076 Uiso 1 1 calc R . .
C19 C 0.2030(2) 0.6097(2) 0.27800(17) 0.0640(8) Uani 1 1 d . . .
H19 H 0.2382 0.6703 0.2827 0.077 Uiso 1 1 calc R . .
C16 C 0.0944(2) 0.4325(2) 0.26316(17) 0.0646(8) Uani 1 1 d . . .
H16 H 0.0584 0.3722 0.2576 0.078 Uiso 1 1 calc R . .
C5 C -0.3495(3) 0.3814(2) 0.33342(18) 0.0657(8) Uani 1 1 d . . .
C15 C 0.0474(2) 0.5028(2) 0.30373(16) 0.0572(7) Uani 1 1 d . . .
C17 C 0.1943(2) 0.4504(2) 0.23077(17) 0.0653(8) Uani 1 1 d . . .
H17 H 0.2240 0.4017 0.2038 0.078 Uiso 1 1 calc R . .
C13 C -0.3367(3) 0.3718(2) 0.25310(19) 0.0624(8) Uani 1 1 d . . .
C8 C -0.2203(2) 0.4027(2) 0.24634(17) 0.0584(8) Uani 1 1 d . . .
C14 C -0.0526(2) 0.4847(2) 0.34368(17) 0.0629(8) Uani 1 1 d . . .
H14 H -0.0411 0.5103 0.3928 0.075 Uiso 1 1 calc R . .
C28 C 0.5943(3) 0.6355(2) 0.36881(17) 0.0707(9) Uani 1 1 d . . .
H28 H 0.6051 0.6411 0.4217 0.085 Uiso 1 1 calc R . .
C4 C -0.4449(3) 0.3581(3) 0.3696(2) 0.0907(11) Uani 1 1 d . . .
H4 H -0.5159 0.3316 0.3422 0.109 Uiso 1 1 calc R . .
C34 C 0.9236(3) 0.6104(2) 0.0721(2) 0.0856(11) Uani 1 1 d . . .
H34A H 0.8668 0.5761 0.0335 0.103 Uiso 1 1 calc R . .
H34B H 0.9517 0.5666 0.1141 0.103 Uiso 1 1 calc R . .
C12 C -0.4194(3) 0.3416(2) 0.1907(2) 0.0714(9) Uani 1 1 d . . .
H12 H -0.4966 0.3225 0.1957 0.086 Uiso 1 1 calc R . .
C1 C -0.2313(3) 0.4373(3) 0.45239(19) 0.0857(11) Uani 1 1 d . . .
H1 H -0.1601 0.4634 0.4800 0.103 Uiso 1 1 calc R . .
C10 C -0.2715(3) 0.3685(3) 0.1132(2) 0.0815(10) Uani 1 1 d . . .
H10 H -0.2492 0.3658 0.0656 0.098 Uiso 1 1 calc R . .
C9 C -0.1899(3) 0.4007(2) 0.17517(19) 0.0691(9) Uani 1 1 d . . .
H9 H -0.1138 0.4213 0.1692 0.083 Uiso 1 1 calc R . .
C38 C 0.8275(3) 0.7714(2) 0.04226(18) 0.0742(9) Uani 1 1 d . . .
H38A H 0.7955 0.8261 0.0656 0.089 Uiso 1 1 calc R . .
H38B H 0.7649 0.7481 0.0011 0.089 Uiso 1 1 calc R . .
C37 C 0.9362(3) 0.8022(2) 0.01018(19) 0.0799(10) Uani 1 1 d . . .
H37A H 0.9112 0.8493 -0.0299 0.096 Uiso 1 1 calc R . .
H37B H 0.9944 0.8326 0.0504 0.096 Uiso 1 1 calc R . .
C11 C -0.3849(3) 0.3401(3) 0.1200(2) 0.0859(10) Uani 1 1 d . . .
H11 H -0.4394 0.3198 0.0769 0.103 Uiso 1 1 calc R . .
C2 C -0.3243(4) 0.4148(3) 0.4887(2) 0.1060(13) Uani 1 1 d . . .
H2 H -0.3166 0.4257 0.5410 0.127 Uiso 1 1 calc R . .
C3 C -0.4312(4) 0.3752(3) 0.4465(3) 0.1142(15) Uani 1 1 d . . .
H3 H -0.4942 0.3603 0.4714 0.137 Uiso 1 1 calc R . .
C36 C 0.9956(3) 0.7198(3) -0.0218(2) 0.0964(12) Uani 1 1 d . . .
H36A H 1.0672 0.7422 -0.0392 0.116 Uiso 1 1 calc R . .
H36B H 0.9405 0.6931 -0.0655 0.116 Uiso 1 1 calc R . .
C35 C 1.0302(3) 0.6433(3) 0.0381(2) 0.0988(12) Uani 1 1 d . . .
H35A H 1.0926 0.6681 0.0787 0.119 Uiso 1 1 calc R . .
H35B H 1.0633 0.5887 0.0154 0.119 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
O2 C31 1.228(3) . ?
O1 C32 1.216(3) . ?
N1 C32 1.392(4) . ?
N1 C31 1.403(3) . ?
N1 C33 1.489(3) . ?
C25 C24 1.406(4) . ?
C25 C30 1.407(4) . ?
C25 C26 1.428(3) . ?
C24 C23 1.351(4) . ?
C24 C32 1.480(4) . ?
C21 C22 1.368(4) . ?
C21 C26 1.428(4) . ?
C21 C18 1.486(3) . ?
C26 C27 1.409(4) . ?
C30 C29 1.366(4) . ?
C30 C31 1.454(3) . ?
C29 C28 1.387(4) . ?
C18 C17 1.371(4) . ?
C18 C19 1.400(4) . ?
C33 C38 1.495(4) . ?
C33 C34 1.502(4) . ?
C23 C22 1.403(4) . ?
C27 C28 1.354(4) . ?
C6 C1 1.386(4) . ?
C6 C5 1.391(4) . ?
C6 C7 1.485(4) . ?
C7 C14 1.335(4) . ?
C7 C8 1.488(4) . ?
C20 C19 1.373(3) . ?
C20 C15 1.387(4) . ?
C16 C17 1.384(4) . ?
C16 C15 1.383(4) . ?
C5 C4 1.394(4) . ?
C5 C13 1.471(4) . ?
C15 C14 1.467(3) . ?
C13 C12 1.371(4) . ?
C13 C8 1.409(4) . ?
C8 C9 1.376(4) . ?
C4 C3 1.370(5) . ?
C34 C35 1.517(4) . ?
C12 C11 1.389(4) . ?
C1 C2 1.371(4) . ?
C10 C11 1.366(4) . ?
C10 C9 1.369(4) . ?
C38 C37 1.512(4) . ?
C37 C36 1.497(5) . ?
C2 C3 1.405(5) . ?
C36 C35 1.505(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C32 N1 C31 122.8(2) . . ?
C32 N1 C33 119.5(2) . . ?
C31 N1 C33 117.7(2) . . ?
C24 C25 C30 120.5(2) . . ?
C24 C25 C26 120.1(2) . . ?
C30 C25 C26 119.4(2) . . ?
C23 C24 C25 119.9(2) . . ?
C23 C24 C32 120.4(3) . . ?
C25 C24 C32 119.7(3) . . ?
C22 C21 C26 119.2(2) . . ?
C22 C21 C18 119.9(3) . . ?
C26 C21 C18 120.9(2) . . ?
C27 C26 C21 124.0(2) . . ?
C27 C26 C25 117.6(3) . . ?
C21 C26 C25 118.3(2) . . ?
C29 C30 C25 120.3(2) . . ?
C29 C30 C31 119.5(3) . . ?
C25 C30 C31 120.2(2) . . ?
O2 C31 N1 119.6(2) . . ?
O2 C31 C30 121.8(3) . . ?
N1 C31 C30 118.6(2) . . ?
O1 C32 N1 120.6(2) . . ?
O1 C32 C24 121.3(3) . . ?
N1 C32 C24 118.1(3) . . ?
C30 C29 C28 120.4(3) . . ?
C17 C18 C19 117.5(2) . . ?
C17 C18 C21 121.7(3) . . ?
C19 C18 C21 120.8(3) . . ?
N1 C33 C38 113.2(2) . . ?
N1 C33 C34 113.1(2) . . ?
C38 C33 C34 113.3(2) . . ?
C24 C23 C22 121.0(3) . . ?
C28 C27 C26 121.3(3) . . ?
C1 C6 C5 119.9(3) . . ?
C1 C6 C7 130.4(3) . . ?
C5 C6 C7 109.6(3) . . ?
C21 C22 C23 121.3(3) . . ?
C14 C7 C6 123.3(3) . . ?
C14 C7 C8 131.3(3) . . ?
C6 C7 C8 105.0(3) . . ?
C19 C20 C15 121.8(3) . . ?
C20 C19 C18 120.6(3) . . ?
C17 C16 C15 121.0(3) . . ?
C6 C5 C4 120.8(3) . . ?
C6 C5 C13 108.1(2) . . ?
C4 C5 C13 131.1(3) . . ?
C16 C15 C20 117.3(3) . . ?
C16 C15 C14 122.6(3) . . ?
C20 C15 C14 119.8(3) . . ?
C18 C17 C16 121.7(3) . . ?
C12 C13 C8 121.6(3) . . ?
C12 C13 C5 129.5(3) . . ?
C8 C13 C5 108.9(3) . . ?
C9 C8 C13 118.4(3) . . ?
C9 C8 C7 133.2(3) . . ?
C13 C8 C7 108.3(3) . . ?
C7 C14 C15 131.8(3) . . ?
C27 C28 C29 120.9(3) . . ?
C3 C4 C5 118.3(4) . . ?
C33 C34 C35 111.2(3) . . ?
C13 C12 C11 118.3(3) . . ?
C2 C1 C6 119.9(3) . . ?
C11 C10 C9 121.2(3) . . ?
C10 C9 C8 120.0(3) . . ?
C33 C38 C37 110.8(2) . . ?
C36 C37 C38 112.4(3) . . ?
C10 C11 C12 120.5(3) . . ?
C1 C2 C3 119.6(4) . . ?
C4 C3 C2 121.5(3) . . ?
C37 C36 C35 110.3(3) . . ?
C36 C35 C34 112.4(3) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.034
