# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_spiroindolopyrrole
_database_code_depnum_ccdc_archive 'CCDC 1432259'
_audit_update_record             
;
2015-10-20 deposited with the CCDC.
2016-01-11 downloaded from the CCDC.
;

_audit_creation_date             2012-12-14
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_chemical_name_common            ?
_chemical_name_systematic        spiroindolopyrrole
_chemical_formula_moiety         '0.5(C32 H24 Br N3 O3)'
_chemical_formula_sum            'C32 H24 Br N3 O3'
_chemical_formula_weight         578.44
_chemical_melting_point          431
_chemical_oxdiff_formula         'C32 H24 Br1 N3 O3'
_chemical_oxdiff_usercomment     '264 K, COLORLESS, PLATE'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   9.6198(8)
_cell_length_b                   11.1689(9)
_cell_length_c                   13.4682(6)
_cell_angle_alpha                113.744(6)
_cell_angle_beta                 93.929(5)
_cell_angle_gamma                90.612(7)
_cell_volume                     1320.30(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1990
_cell_measurement_temperature    251(18)
_cell_measurement_theta_max      29.2205
_cell_measurement_theta_min      2.5830
_exptl_absorpt_coefficient_mu    1.596
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57804
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       diamond
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.14
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0672
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7527
_diffrn_reflns_theta_full        29.29
_diffrn_reflns_theta_max         29.29
_diffrn_reflns_theta_min         2.59
_diffrn_ambient_temperature      251(18)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -18.00   25.00   1.0000   13.0900
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -99.0000  -30.0000 43

#__ type_ start__ end____ width___ exp.time_
  2 omega  -20.00   15.00   1.0000   13.0900
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -99.0000 -180.0000 35

#__ type_ start__ end____ width___ exp.time_
  3 omega  -88.00  -60.00   1.0000   13.0900
omega____ theta____ kappa____ phi______ frames
    -      -17.3397 -179.0000 -150.0000 28

#__ type_ start__ end____ width___ exp.time_
  4 omega  -46.00   76.00   1.0000   13.0900
omega____ theta____ kappa____ phi______ frames
    -       18.9803    0.0000    0.0000 122

#__ type_ start__ end____ width___ exp.time_
  5 omega  -90.00  -47.00   1.0000   13.0900
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -37.0000   60.0000 43
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0501839000
_diffrn_orient_matrix_UB_12      0.0482875000
_diffrn_orient_matrix_UB_13      0.0072354000
_diffrn_orient_matrix_UB_21      -0.0528061000
_diffrn_orient_matrix_UB_22      -0.0444515000
_diffrn_orient_matrix_UB_23      0.0006154000
_diffrn_orient_matrix_UB_31      0.0128416000
_diffrn_orient_matrix_UB_32      0.0226792000
_diffrn_orient_matrix_UB_33      0.0572590000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3260
_reflns_number_total             4868
_reflns_odcompleteness_completeness 81.35
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
2008). A64, 112-122
;
_computing_structure_solution    
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.550
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.883
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         4868
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0877
_refine_ls_R_factor_gt           0.0513
_refine_ls_restrained_S_all      0.883
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1299
_refine_ls_wR_factor_ref         0.1620
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.14676(5) 0.89210(5) 0.45844(4) 0.0632(2) Uani 1 1 d . . .
O2 O 0.8960(3) 0.2820(3) 0.1904(2) 0.0455(7) Uani 1 1 d . . .
O3 O 0.5774(3) 0.3810(3) 0.15951(19) 0.0386(7) Uani 1 1 d . . .
N4 N 0.6939(3) 0.6607(3) 0.2785(2) 0.0257(7) Uani 1 1 d . . .
C5 C 0.8729(3) 0.5121(3) 0.2254(2) 0.0264(8) Uani 1 1 d . . .
H5 H 0.9590 0.5473 0.2723 0.032 Uiso 1 1 calc R . .
N6 N 0.6076(3) 0.3957(3) 0.3340(2) 0.0328(8) Uani 1 1 d . . .
N7 N 0.8630(3) 0.3469(3) 0.0482(2) 0.0296(7) Uani 1 1 d . . .
C8 C 0.8510(3) 0.5751(3) 0.1437(2) 0.0267(8) Uani 1 1 d . . .
H8 H 0.9267 0.6390 0.1530 0.032 Uiso 1 1 calc R . .
C9 C 0.6939(4) 0.4703(4) 0.4291(3) 0.0311(9) Uani 1 1 d . . .
C10 C 0.8812(4) 0.3670(4) 0.1583(3) 0.0316(9) Uani 1 1 d . . .
O11 O 0.8319(3) 0.4669(3) -0.05431(19) 0.0413(7) Uani 1 1 d . . .
C12 C 0.7030(3) 0.7668(4) 0.1480(3) 0.0272(8) Uani 1 1 d . . .
C13 C 0.6335(3) 0.4304(3) 0.2515(3) 0.0280(8) Uani 1 1 d . . .
C14 C 0.7092(3) 0.6411(3) 0.1647(2) 0.0257(8) Uani 1 1 d . . .
H14 H 0.6354 0.5794 0.1172 0.031 Uiso 1 1 calc R . .
C15 C 0.7027(5) 0.4598(4) 0.5274(3) 0.0434(10) Uani 1 1 d . . .
H15 H 0.6475 0.3989 0.5395 0.052 Uiso 1 1 calc R . .
C16 C 0.5606(4) 0.7979(4) 0.4272(3) 0.0312(9) Uani 1 1 d . . .
H16 H 0.6438 0.8227 0.4710 0.037 Uiso 1 1 calc R . .
C17 C 0.5146(4) 0.2867(4) 0.3214(3) 0.0456(11) Uani 1 1 d . . .
H17A H 0.5685 0.2145 0.3204 0.068 Uiso 1 1 calc R . .
H17B H 0.4573 0.2608 0.2543 0.068 Uiso 1 1 calc R . .
H17C H 0.4564 0.3126 0.3811 0.068 Uiso 1 1 calc R . .
C18 C 0.7470(4) 0.9987(4) 0.2124(3) 0.0439(11) Uani 1 1 d . . .
H18 H 0.7778 1.0780 0.2682 0.053 Uiso 1 1 calc R . .
C19 C 0.3132(4) 0.7246(4) 0.2977(3) 0.0399(10) Uani 1 1 d . . .
H19 H 0.2297 0.6999 0.2543 0.048 Uiso 1 1 calc R . .
C20 C 0.4364(4) 0.6707(4) 0.2563(3) 0.0354(9) Uani 1 1 d . . .
H20 H 0.4350 0.6087 0.1850 0.043 Uiso 1 1 calc R . .
C21 C 0.7500(4) 0.8859(4) 0.2304(3) 0.0351(9) Uani 1 1 d . . .
H21 H 0.7836 0.8893 0.2979 0.042 Uiso 1 1 calc R . .
C22 C 0.8678(4) 0.6444(4) 0.4904(3) 0.0368(10) Uani 1 1 d . . .
H22 H 0.9230 0.7052 0.4782 0.044 Uiso 1 1 calc R . .
C23 C 0.5620(3) 0.7080(3) 0.3199(2) 0.0243(8) Uani 1 1 d . . .
C24 C 0.6539(4) 0.7641(4) 0.0488(3) 0.0356(10) Uani 1 1 d . . .
H24 H 0.6219 0.6853 -0.0071 0.043 Uiso 1 1 calc R . .
C25 C 0.6776(5) 0.0601(4) -0.1663(3) 0.0522(12) Uani 1 1 d . . .
H25 H 0.5876 0.0365 -0.1995 0.063 Uiso 1 1 calc R . .
C26 C 0.4379(4) 0.8512(4) 0.4698(3) 0.0348(9) Uani 1 1 d . . .
H26 H 0.4379 0.9105 0.5420 0.042 Uiso 1 1 calc R . .
C27 C 0.7737(4) 0.5620(3) 0.4102(2) 0.0274(8) Uani 1 1 d . . .
C28 C 0.8788(4) 0.6347(5) 0.5913(3) 0.0448(11) Uani 1 1 d . . .
H28 H 0.9414 0.6899 0.6471 0.054 Uiso 1 1 calc R . .
C29 C 0.7974(5) 0.5441(5) 0.6075(3) 0.0471(11) Uani 1 1 d . . .
H29 H 0.8061 0.5389 0.6749 0.057 Uiso 1 1 calc R . .
C30 C 0.6991(4) 0.9954(5) 0.1127(4) 0.0504(12) Uani 1 1 d . . .
H30 H 0.6987 1.0716 0.1004 0.060 Uiso 1 1 calc R . .
C31 C 0.9420(4) 0.1322(5) -0.0675(4) 0.0574(13) Uani 1 1 d . . .
H31 H 1.0323 0.1572 -0.0354 0.069 Uiso 1 1 calc R . .
C32 C 0.8388(4) 0.2177(3) -0.0374(3) 0.0308(9) Uani 1 1 d . . .
C33 C 0.6519(5) 0.8779(5) 0.0317(3) 0.0499(12) Uani 1 1 d . . .
H33 H 0.6182 0.8750 -0.0357 0.060 Uiso 1 1 calc R . .
C34 C 0.7805(5) -0.0267(5) -0.1982(4) 0.0597(14) Uani 1 1 d . . .
H34 H 0.7616 -0.1085 -0.2548 0.072 Uiso 1 1 calc R . .
C35 C 0.8478(3) 0.4615(4) 0.0332(3) 0.0296(8) Uani 1 1 d . . .
C36 C 0.7431(3) 0.5458(3) 0.2939(2) 0.0258(8) Uani 1 1 d . . .
C38 C 0.3154(4) 0.8149(4) 0.4034(3) 0.0345(9) Uani 1 1 d . . .
C39 C 0.9123(5) 0.0061(5) -0.1471(4) 0.0728(17) Uani 1 1 d . . .
H39 H 0.9812 -0.0552 -0.1653 0.087 Uiso 1 1 calc R . .
C1 C 0.7060(4) 0.1826(4) -0.0854(3) 0.0415(10) Uani 1 1 d . . .
H1 H 0.6353 0.2415 -0.0631 0.050 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
Br1 C38 1.898(4) . ?
O2 C10 1.198(4) . ?
O3 C13 1.218(4) . ?
N4 C14 1.476(4) . ?
N4 C23 1.440(4) . ?
N4 C36 1.460(5) . ?
C5 C8 1.532(5) . ?
C5 C10 1.511(5) . ?
C5 C36 1.562(4) . ?
N6 C9 1.415(4) . ?
N6 C13 1.353(4) . ?
N6 C17 1.449(4) . ?
N7 C10 1.405(4) . ?
N7 C32 1.444(4) . ?
N7 C35 1.381(5) . ?
C8 C14 1.545(5) . ?
C8 C35 1.516(4) . ?
C9 C15 1.372(5) . ?
C9 C27 1.387(5) . ?
O11 C35 1.204(4) . ?
C12 C14 1.510(5) . ?
C12 C21 1.391(5) . ?
C12 C24 1.375(5) . ?
C13 C36 1.548(4) . ?
C15 C29 1.382(6) . ?
C16 C23 1.389(4) . ?
C16 C26 1.382(5) . ?
C18 C21 1.376(5) . ?
C18 C30 1.375(6) . ?
C19 C20 1.383(5) . ?
C19 C38 1.373(5) . ?
C20 C23 1.389(5) . ?
C22 C27 1.371(5) . ?
C22 C28 1.403(5) . ?
C24 C33 1.380(6) . ?
C25 C34 1.360(6) . ?
C25 C1 1.373(5) . ?
C26 C38 1.381(5) . ?
C27 C36 1.510(5) . ?
C28 C29 1.368(6) . ?
C30 C33 1.373(6) . ?
C31 C32 1.351(6) . ?
C31 C39 1.396(6) . ?
C32 C1 1.370(5) . ?
C34 C39 1.372(7) . ?

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
C23 N4 C14 115.8(3) . . ?
C23 N4 C36 116.5(2) . . ?
C36 N4 C14 108.7(3) . . ?
C8 C5 C36 105.8(3) . . ?
C10 C5 C8 105.9(3) . . ?
C10 C5 C36 112.7(3) . . ?
C9 N6 C17 125.2(3) . . ?
C13 N6 C9 111.0(3) . . ?
C13 N6 C17 123.5(3) . . ?
C10 N7 C32 121.8(3) . . ?
C35 N7 C10 113.3(3) . . ?
C35 N7 C32 124.1(3) . . ?
C5 C8 C14 106.1(2) . . ?
C35 C8 C5 104.6(3) . . ?
C35 C8 C14 112.2(3) . . ?
C15 C9 N6 128.3(3) . . ?
C15 C9 C27 122.3(3) . . ?
C27 C9 N6 109.4(3) . . ?
O2 C10 C5 127.6(3) . . ?
O2 C10 N7 124.9(3) . . ?
N7 C10 C5 107.4(3) . . ?
C21 C12 C14 121.3(3) . . ?
C24 C12 C14 119.9(3) . . ?
C24 C12 C21 118.8(4) . . ?
O3 C13 N6 125.6(3) . . ?
O3 C13 C36 125.5(3) . . ?
N6 C13 C36 108.9(3) . . ?
N4 C14 C8 101.8(3) . . ?
N4 C14 C12 112.9(3) . . ?
C12 C14 C8 114.3(2) . . ?
C9 C15 C29 116.9(4) . . ?
C26 C16 C23 121.2(3) . . ?
C30 C18 C21 120.7(4) . . ?
C38 C19 C20 119.4(3) . . ?
C19 C20 C23 120.8(3) . . ?
C18 C21 C12 120.3(3) . . ?
C27 C22 C28 118.4(3) . . ?
C16 C23 N4 118.7(3) . . ?
C20 C23 N4 122.8(3) . . ?
C20 C23 C16 118.5(3) . . ?
C12 C24 C33 120.3(4) . . ?
C34 C25 C1 120.2(4) . . ?
C38 C26 C16 118.8(3) . . ?
C9 C27 C36 109.4(3) . . ?
C22 C27 C9 120.1(3) . . ?
C22 C27 C36 130.4(3) . . ?
C29 C28 C22 120.0(3) . . ?
C28 C29 C15 122.3(4) . . ?
C33 C30 C18 118.9(4) . . ?
C32 C31 C39 119.6(4) . . ?
C31 C32 N7 121.6(3) . . ?
C31 C32 C1 120.7(3) . . ?
C1 C32 N7 117.7(3) . . ?
C30 C33 C24 120.9(4) . . ?
C25 C34 C39 120.1(4) . . ?
N7 C35 C8 108.7(3) . . ?
O11 C35 N7 124.4(3) . . ?
O11 C35 C8 126.9(3) . . ?
N4 C36 C5 101.8(3) . . ?
N4 C36 C13 112.8(3) . . ?
N4 C36 C27 116.3(3) . . ?
C13 C36 C5 111.2(3) . . ?
C27 C36 C5 113.9(3) . . ?
C27 C36 C13 101.2(3) . . ?
C19 C38 Br1 119.2(3) . . ?
C19 C38 C26 121.2(3) . . ?
C26 C38 Br1 119.6(3) . . ?
C34 C39 C31 119.4(5) . . ?
C32 C1 C25 119.8(4) . . ?

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
####################################################################### 
# 
# 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. 
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#######################################################################

data_spiroindoloimidazolidine
_database_code_depnum_ccdc_archive 'CCDC 1432260'
_audit_update_record             
;
2016-01-09 deposited with the CCDC.
2016-01-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        imidazolidine
_chemical_name_common            spiroindoloimidazolidine
_chemical_formula_moiety         'C36 H31 N3 O3 S'
_chemical_formula_sum            'C36 H31 N3 O3 S'
_chemical_formula_weight         585.70

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/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                   13.4366(9)
_cell_length_b                   9.3183(6)
_cell_length_c                   23.8673(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.5620(10)
_cell_angle_gamma                90.00
_cell_volume                     2987.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    1990
_cell_measurement_theta_min      1.71
_cell_measurement_theta_max      28.27

_exptl_crystal_description       Diamonds
_exptl_crystal_colour            White
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1232
_exptl_absorpt_coefficient_mu    0.150
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.958
_exptl_absorpt_correction_T_max  0.973

_exptl_special_details           
; 
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      295(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  'BRUKER SMART APEX CCD DIFFRACTOMETER'
_diffrn_measurement_method       'OMEGA-PHI SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17160
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_sigmaI/netI    0.0333
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.71
_diffrn_reflns_theta_max         28.27
_reflns_number_total             6849
_reflns_number_gt                5427
_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    ORTEP
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0643P)²+1.0640P] 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         6849
_refine_ls_number_parameters     390
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0500
_refine_ls_wR_factor_ref         0.1412
_refine_ls_wR_factor_gt          0.1323
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.028
_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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S20 S 0.18235(3) 0.46529(5) 0.413573(17) 0.03867(13) Uani 1 d . . .
O41 O 0.44400(9) 0.36418(13) 0.29902(5) 0.0456(3) Uani 1 d . . .
N1 N 0.50053(9) 0.13560(15) 0.31854(6) 0.0374(3) Uani 1 d . . .
N10 N 0.24855(9) 0.21604(15) 0.29044(5) 0.0348(3) Uani 1 d . . .
O42 O 0.25393(9) 0.49316(15) 0.45736(5) 0.0513(3) Uani 1 d . . .
O43 O 0.14263(9) 0.57986(14) 0.38031(6) 0.0509(3) Uani 1 d . . .
C3 C 0.32893(10) 0.17336(17) 0.32862(6) 0.0303(3) Uani 1 d . . .
N12 N 0.23742(9) 0.35846(15) 0.36882(5) 0.0349(3) Uani 1 d . . .
C4 C 0.35429(11) 0.01576(17) 0.33265(6) 0.0319(3) Uani 1 d . . .
C13 C 0.29200(11) 0.22813(17) 0.38613(6) 0.0332(3) Uani 1 d . . .
H13 H 0.2436 0.1587 0.3998 0.040 Uiso 1 calc R . .
C21 C 0.08182(12) 0.37496(18) 0.44381(7) 0.0378(4) Uani 1 d . . .
C9 C 0.45726(11) 0.00099(18) 0.32885(6) 0.0339(3) Uani 1 d . . .
C34 C 0.25383(11) 0.19551(18) 0.23218(6) 0.0355(3) Uani 1 d . . .
C2 C 0.43055(11) 0.24086(18) 0.31330(6) 0.0339(3) Uani 1 d . . .
C14 C 0.37332(12) 0.24514(19) 0.43073(6) 0.0386(4) Uani 1 d . . .
C28 C 0.08025(12) 0.3017(2) 0.31102(7) 0.0436(4) Uani 1 d . . .
C11 C 0.19080(11) 0.33630(18) 0.31200(6) 0.0356(3) Uani 1 d . . .
H11 H 0.2022 0.4215 0.2889 0.043 Uiso 1 calc R . .
C38 C 0.32090(14) 0.0741(2) 0.15198(7) 0.0461(4) Uani 1 d . . .
H38 H 0.3653 0.0078 0.1377 0.055 Uiso 1 calc R . .
C39 C 0.32007(12) 0.09772(18) 0.20914(7) 0.0378(4) Uani 1 d . . .
H39 H 0.3643 0.0478 0.2326 0.045 Uiso 1 calc R . .
C22 C -0.01491(13) 0.4159(2) 0.43000(8) 0.0460(4) Uani 1 d . . .
H22 H -0.0271 0.4908 0.4050 0.055 Uiso 1 calc R . .
C26 C 0.10032(14) 0.2657(2) 0.48226(7) 0.0457(4) Uani 1 d . . .
H26 H 0.1653 0.2402 0.4922 0.055 Uiso 1 calc R . .
C15 C 0.37717(16) 0.1473(2) 0.47420(8) 0.0541(5) Uani 1 d . . .
H15 H 0.3290 0.0759 0.4761 0.065 Uiso 1 calc R . .
C8 C 0.50325(13) -0.1311(2) 0.33142(7) 0.0441(4) Uani 1 d . . .
H8 H 0.5720 -0.1399 0.3295 0.053 Uiso 1 calc R . .
C19 C 0.44654(13) 0.3503(2) 0.42842(8) 0.0493(4) Uani 1 d . . .
H19 H 0.4439 0.4189 0.4001 0.059 Uiso 1 calc R . .
C6 C 0.34068(15) -0.2378(2) 0.34045(8) 0.0517(5) Uani 1 d . . .
H6 H 0.3019 -0.3198 0.3439 0.062 Uiso 1 calc R . .
C40 C 0.60562(12) 0.1574(3) 0.30957(9) 0.0576(5) Uani 1 d . . .
H40A H 0.6164 0.2541 0.2972 0.086 Uiso 1 calc R . .
H40B H 0.6276 0.0916 0.2815 0.086 Uiso 1 calc R . .
H40C H 0.6425 0.1411 0.3440 0.086 Uiso 1 calc R . .
C5 C 0.29567(12) -0.10389(19) 0.33876(7) 0.0415(4) Uani 1 d . . .
H5 H 0.2271 -0.0952 0.3417 0.050 Uiso 1 calc R . .
C33 C 0.04615(14) 0.1705(2) 0.32950(9) 0.0565(5) Uani 1 d . . .
H33 H 0.0909 0.1015 0.3428 0.068 Uiso 1 calc R . .
C35 C 0.19086(17) 0.2686(3) 0.19519(8) 0.0629(6) Uani 1 d . . .
H35 H 0.1466 0.3359 0.2089 0.076 Uiso 1 calc R . .
C23 C -0.09325(14) 0.3439(2) 0.45391(9) 0.0531(5) Uani 1 d . . .
H23 H -0.1582 0.3709 0.4446 0.064 Uiso 1 calc R . .
C37 C 0.25796(17) 0.1460(3) 0.11594(8) 0.0638(6) Uani 1 d . . .
H37 H 0.2592 0.1298 0.0775 0.077 Uiso 1 calc R . .
C7 C 0.44281(15) -0.2501(2) 0.33701(8) 0.0530(5) Uani 1 d . . .
H7 H 0.4717 -0.3408 0.3385 0.064 Uiso 1 calc R . .
C24 C -0.07681(15) 0.2325(2) 0.49146(9) 0.0546(5) Uani 1 d . . .
C25 C 0.02077(16) 0.1956(2) 0.50549(8) 0.0534(5) Uani 1 d . . .
H25 H 0.0329 0.1219 0.5311 0.064 Uiso 1 calc R . .
C18 C 0.52342(15) 0.3528(3) 0.46830(9) 0.0669(6) Uani 1 d . . .
H18 H 0.5738 0.4207 0.4657 0.080 Uiso 1 calc R . .
C29 C 0.01287(15) 0.4031(3) 0.29071(9) 0.0656(6) Uani 1 d . . .
H29 H 0.0354 0.4919 0.2786 0.079 Uiso 1 calc R . .
C36 C 0.1928(2) 0.2429(3) 0.13795(9) 0.0806(8) Uani 1 d . . .
H36 H 0.1490 0.2924 0.1141 0.097 Uiso 1 calc R . .
C27 C -0.16339(19) 0.1541(3) 0.51634(13) 0.0822(8) Uani 1 d . . .
H27A H -0.1976 0.0998 0.4876 0.123 Uiso 1 calc R . .
H27B H -0.2084 0.2223 0.5320 0.123 Uiso 1 calc R . .
H27C H -0.1393 0.0904 0.5452 0.123 Uiso 1 calc R . .
C30 C -0.08757(18) 0.3724(4) 0.28845(12) 0.0954(11) Uani 1 d . . .
H30 H -0.1325 0.4400 0.2742 0.114 Uiso 1 calc R . .
C16 C 0.4525(2) 0.1549(3) 0.51524(9) 0.0769(7) Uani 1 d . . .
H16 H 0.4533 0.0911 0.5452 0.092 Uiso 1 calc R . .
C32 C -0.05525(17) 0.1423(3) 0.32815(12) 0.0847(9) Uani 1 d . . .
H32 H -0.0789 0.0553 0.3415 0.102 Uiso 1 calc R . .
C17 C 0.52575(19) 0.2567(3) 0.51138(10) 0.0780(8) Uani 1 d . . .
H17 H 0.5771 0.2602 0.5383 0.094 Uiso 1 calc R . .
C31 C -0.12108(17) 0.2438(5) 0.30696(14) 0.1069(13) Uani 1 d . . .
H31 H -0.1889 0.2239 0.3053 0.128 Uiso 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
S20 O42 1.4248(13) . ?
S20 O43 1.4255(14) . ?
S20 N12 1.6500(13) . ?
S20 C21 1.7628(16) . ?
O41 C2 1.213(2) . ?
N1 C2 1.362(2) . ?
N1 C9 1.407(2) . ?
N1 C40 1.448(2) . ?
N10 C34 1.4074(19) . ?
N10 C3 1.4496(18) . ?
N10 C11 1.464(2) . ?
C3 C4 1.510(2) . ?
C3 C2 1.556(2) . ?
C3 C13 1.558(2) . ?
N12 C13 1.472(2) . ?
N12 C11 1.4925(19) . ?
C4 C5 1.375(2) . ?
C4 C9 1.396(2) . ?
C13 C14 1.513(2) . ?
C13 H13 0.9800 . ?
C21 C22 1.386(2) . ?
C21 C26 1.388(3) . ?
C9 C8 1.378(2) . ?
C34 C35 1.385(2) . ?
C34 C39 1.397(2) . ?
C14 C15 1.381(3) . ?
C14 C19 1.391(3) . ?
C28 C33 1.382(3) . ?
C28 C29 1.387(3) . ?
C28 C11 1.519(2) . ?
C11 H11 0.9800 . ?
C38 C37 1.365(3) . ?
C38 C39 1.382(2) . ?
C38 H38 0.9300 . ?
C39 H39 0.9300 . ?
C22 C23 1.384(3) . ?
C22 H22 0.9300 . ?
C26 C25 1.382(3) . ?
C26 H26 0.9300 . ?
C15 C16 1.391(3) . ?
C15 H15 0.9300 . ?
C8 C7 1.383(3) . ?
C8 H8 0.9300 . ?
C19 C18 1.386(3) . ?
C19 H19 0.9300 . ?
C6 C7 1.382(3) . ?
C6 C5 1.386(3) . ?
C6 H6 0.9300 . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
C5 H5 0.9300 . ?
C33 C32 1.387(3) . ?
C33 H33 0.9300 . ?
C35 C36 1.388(3) . ?
C35 H35 0.9300 . ?
C23 C24 1.385(3) . ?
C23 H23 0.9300 . ?
C37 C36 1.373(3) . ?
C37 H37 0.9300 . ?
C7 H7 0.9300 . ?
C24 C25 1.388(3) . ?
C24 C27 1.509(3) . ?
C25 H25 0.9300 . ?
C18 C17 1.363(4) . ?
C18 H18 0.9300 . ?
C29 C30 1.379(4) . ?
C29 H29 0.9300 . ?
C36 H36 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C30 C31 1.358(5) . ?
C30 H30 0.9300 . ?
C16 C17 1.372(4) . ?
C16 H16 0.9300 . ?
C32 C31 1.381(5) . ?
C32 H32 0.9300 . ?
C17 H17 0.9300 . ?
C31 H31 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
O42 S20 O43 120.47(8) . . ?
O42 S20 N12 106.22(7) . . ?
O43 S20 N12 105.01(7) . . ?
O42 S20 C21 107.23(8) . . ?
O43 S20 C21 107.83(8) . . ?
N12 S20 C21 109.82(7) . . ?
C2 N1 C9 111.74(12) . . ?
C2 N1 C40 123.96(15) . . ?
C9 N1 C40 124.08(15) . . ?
C34 N10 C3 121.81(12) . . ?
C34 N10 C11 119.51(13) . . ?
C3 N10 C11 112.45(12) . . ?
N10 C3 C4 118.02(13) . . ?
N10 C3 C2 112.63(12) . . ?
C4 C3 C2 102.13(12) . . ?
N10 C3 C13 102.37(11) . . ?
C4 C3 C13 109.83(12) . . ?
C2 C3 C13 112.16(12) . . ?
C13 N12 C11 109.54(12) . . ?
C13 N12 S20 123.01(10) . . ?
C11 N12 S20 119.16(10) . . ?
C5 C4 C9 119.90(15) . . ?
C5 C4 C3 131.79(14) . . ?
C9 C4 C3 108.31(13) . . ?
N12 C13 C14 117.12(13) . . ?
N12 C13 C3 101.02(12) . . ?
C14 C13 C3 114.39(12) . . ?
N12 C13 H13 107.9 . . ?
C14 C13 H13 107.9 . . ?
C3 C13 H13 107.9 . . ?
C22 C21 C26 120.59(16) . . ?
C22 C21 S20 119.70(14) . . ?
C26 C21 S20 119.69(13) . . ?
C8 C9 C4 121.96(15) . . ?
C8 C9 N1 128.11(14) . . ?
C4 C9 N1 109.79(13) . . ?
C35 C34 C39 117.03(15) . . ?
C35 C34 N10 121.10(15) . . ?
C39 C34 N10 121.83(14) . . ?
O41 C2 N1 126.86(14) . . ?
O41 C2 C3 125.96(14) . . ?
N1 C2 C3 107.18(13) . . ?
C15 C14 C19 118.86(16) . . ?
C15 C14 C13 118.10(16) . . ?
C19 C14 C13 122.96(15) . . ?
C33 C28 C29 119.68(18) . . ?
C33 C28 C11 121.01(16) . . ?
C29 C28 C11 119.30(19) . . ?
N10 C11 N12 102.23(11) . . ?
N10 C11 C28 111.06(14) . . ?
N12 C11 C28 115.42(12) . . ?
N10 C11 H11 109.3 . . ?
N12 C11 H11 109.3 . . ?
C28 C11 H11 109.3 . . ?
C37 C38 C39 121.48(18) . . ?
C37 C38 H38 119.3 . . ?
C39 C38 H38 119.3 . . ?
C38 C39 C34 120.97(16) . . ?
C38 C39 H39 119.5 . . ?
C34 C39 H39 119.5 . . ?
C23 C22 C21 119.18(18) . . ?
C23 C22 H22 120.4 . . ?
C21 C22 H22 120.4 . . ?
C25 C26 C21 119.05(17) . . ?
C25 C26 H26 120.5 . . ?
C21 C26 H26 120.5 . . ?
C14 C15 C16 120.5(2) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C9 C8 C7 117.17(16) . . ?
C9 C8 H8 121.4 . . ?
C7 C8 H8 121.4 . . ?
C18 C19 C14 120.0(2) . . ?
C18 C19 H19 120.0 . . ?
C14 C19 H19 120.0 . . ?
C7 C6 C5 120.43(17) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
N1 C40 H40A 109.5 . . ?
N1 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
N1 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C4 C5 C6 118.81(15) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C28 C33 C32 119.6(2) . . ?
C28 C33 H33 120.2 . . ?
C32 C33 H33 120.2 . . ?
C34 C35 C36 121.0(2) . . ?
C34 C35 H35 119.5 . . ?
C36 C35 H35 119.5 . . ?
C22 C23 C24 121.34(18) . . ?
C22 C23 H23 119.3 . . ?
C24 C23 H23 119.3 . . ?
C38 C37 C36 118.19(18) . . ?
C38 C37 H37 120.9 . . ?
C36 C37 H37 120.9 . . ?
C6 C7 C8 121.71(18) . . ?
C6 C7 H7 119.1 . . ?
C8 C7 H7 119.1 . . ?
C23 C24 C25 118.37(17) . . ?
C23 C24 C27 120.4(2) . . ?
C25 C24 C27 121.2(2) . . ?
C26 C25 C24 121.44(19) . . ?
C26 C25 H25 119.3 . . ?
C24 C25 H25 119.3 . . ?
C17 C18 C19 120.5(2) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C30 C29 C28 120.1(3) . . ?
C30 C29 H29 120.0 . . ?
C28 C29 H29 120.0 . . ?
C37 C36 C35 121.3(2) . . ?
C37 C36 H36 119.4 . . ?
C35 C36 H36 119.4 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C31 C30 C29 120.2(3) . . ?
C31 C30 H30 119.9 . . ?
C29 C30 H30 119.9 . . ?
C17 C16 C15 119.8(2) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C31 C32 C33 119.8(3) . . ?
C31 C32 H32 120.1 . . ?
C33 C32 H32 120.1 . . ?
C18 C17 C16 120.2(2) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C30 C31 C32 120.6(2) . . ?
C30 C31 H31 119.7 . . ?
C32 C31 H31 119.7 . . ?

_diffrn_measured_fraction_theta_max 0.98
_diffrn_reflns_theta_full        28.27
_diffrn_measured_fraction_theta_full 0.98
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.046
