# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_exp_4902
_audit_block_doi                 10.5517/ccdc.csd.cc1zkj02
_database_code_depnum_ccdc_archive 'CCDC 1834084'
_audit_update_record             
;
2018-04-02 deposited with the CCDC.
2018-11-28 downloaded from the CCDC.
;
_audit_creation_date             2017-04-14
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C H2 Cl2, C42 H36 N2 O6'
_chemical_formula_sum            'C43 H38 Cl2 N2 O6'
_chemical_formula_weight         749.65
_chemical_melting_point          ?
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 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   15.728(2)
_cell_length_b                   15.8995(14)
_cell_length_c                   15.969(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.226(17)
_cell_angle_gamma                90.00
_cell_volume                     3696.7(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4907
_cell_measurement_temperature    106.4
_cell_measurement_theta_max      29.4990
_cell_measurement_theta_min      2.9065
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93546
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_av_unetI/netI     0.0633
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            21001
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.91
_diffrn_ambient_temperature      106.4
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -4.00   22.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.3660   77.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega  -29.00   13.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.3660   37.0000  120.0000 42

#__ type_ start__ end____ width___ exp.time_
  3 omega  -38.00  -11.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       18.6785  -77.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
  4 omega   34.00   88.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       18.6785   37.0000   90.0000 54

#__ type_ start__ end____ width___ exp.time_
  5 omega    2.00   88.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       18.6785   40.0000 -171.0000 86

#__ type_ start__ end____ width___ exp.time_
  6 omega  -50.00    6.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       18.6785  -37.0000  -90.0000 56
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0469756000
_diffrn_orient_matrix_UB_12      0.0081608000
_diffrn_orient_matrix_UB_13      -0.0093558000
_diffrn_orient_matrix_UB_21      0.0121585000
_diffrn_orient_matrix_UB_22      0.0209118000
_diffrn_orient_matrix_UB_23      0.0421928000
_diffrn_orient_matrix_UB_31      0.0033364000
_diffrn_orient_matrix_UB_32      0.0386143000
_diffrn_orient_matrix_UB_33      -0.0208889000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                5301
_reflns_number_total             7261
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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-97 (Sheldrick, 1997)'
_computing_structure_solution    'A short history of SHELX (Sheldrick, 2007)'
_refine_diff_density_max         0.572
_refine_diff_density_min         -0.628
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     482
_refine_ls_number_reflns         7261
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0910
_refine_ls_R_factor_gt           0.0655
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0726P)²+4.2166P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1595
_refine_ls_wR_factor_ref         0.1755
_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
Cl1 Cl 0.45595(6) 0.97077(6) 0.08435(6) 0.0357(2) Uani 1 1 d . . .
Cl2 Cl 0.53805(8) 0.81166(7) 0.06223(9) 0.0571(3) Uani 1 1 d . . .
O2 O 0.44371(14) 0.59377(13) 0.14920(13) 0.0189(5) Uani 1 1 d . . .
C5 C 0.53452(19) 0.60729(18) -0.02677(19) 0.0161(6) Uani 1 1 d . . .
N2 N 0.29821(18) 0.58138(16) 0.36015(16) 0.0219(6) Uani 1 1 d . . .
O5 O 0.21084(13) 0.58952(12) -0.05753(13) 0.0172(4) Uani 1 1 d . . .
C16 C 0.3638(2) 0.60938(18) 0.16353(19) 0.0163(6) Uani 1 1 d . . .
O1 O 0.61836(13) 0.58922(13) -0.02940(13) 0.0187(5) Uani 1 1 d . . .
C18 C 0.2944(2) 0.60359(18) 0.27468(19) 0.0185(6) Uani 1 1 d . . .
C1 C 0.3789(2) 0.65197(18) -0.08920(19) 0.0175(6) Uani 1 1 d . . .
H1 H 0.3289 0.6722 -0.1380 0.021 Uiso 1 1 calc R . .
C3 C 0.4447(2) 0.60926(18) 0.06503(19) 0.0163(6) Uani 1 1 d . . .
C22 C 0.3453(2) 0.71760(19) -0.31022(19) 0.0183(6) Uani 1 1 d . . .
O4 O 0.27177(15) 0.58695(14) -0.37990(14) 0.0282(5) Uani 1 1 d . . .
C30 C 0.2343(2) 0.73562(18) -0.04335(18) 0.0159(6) Uani 1 1 d . . .
C6 C 0.4604(2) 0.63675(18) -0.10136(18) 0.0155(6) Uani 1 1 d . . .
N1 N 0.83048(17) 0.57749(16) -0.17424(17) 0.0210(6) Uani 1 1 d . . .
C13 C 0.5877(2) 0.64426(18) -0.2621(2) 0.0188(6) Uani 1 1 d . . .
H13 H 0.5438 0.6642 -0.3158 0.023 Uiso 1 1 calc R . .
C7 C 0.4670(2) 0.64923(18) -0.19278(19) 0.0163(6) Uani 1 1 d . . .
C2 C 0.3681(2) 0.63849(18) -0.00757(19) 0.0163(6) Uani 1 1 d . . .
C14 C 0.27755(19) 0.65331(18) 0.00119(19) 0.0164(6) Uani 1 1 d . . .
C29 C 0.1578(2) 0.71919(19) -0.12068(19) 0.0176(6) Uani 1 1 d . . .
C9 C 0.6313(2) 0.60288(18) -0.10953(19) 0.0171(6) Uani 1 1 d . . .
C27 C 0.2915(2) 0.7834(2) -0.3610(2) 0.0244(7) Uani 1 1 d . . .
H27 H 0.2370 0.7729 -0.4099 0.029 Uiso 1 1 calc R . .
O3 O 0.40266(13) 0.58643(12) -0.25651(13) 0.0188(5) Uani 1 1 d . . .
C10 C 0.7190(2) 0.58514(18) -0.1039(2) 0.0175(6) Uani 1 1 d . . .
H10 H 0.7622 0.5651 -0.0498 0.021 Uiso 1 1 calc R . .
C11 C 0.7439(2) 0.59691(18) -0.1788(2) 0.0182(6) Uani 1 1 d . . .
C4 C 0.5274(2) 0.59399(18) 0.05622(19) 0.0174(6) Uani 1 1 d . . .
H4 H 0.5778 0.5750 0.1054 0.021 Uiso 1 1 calc R . .
C17 C 0.3697(2) 0.59192(18) 0.25053(19) 0.0192(6) Uani 1 1 d . . .
H17 H 0.4247 0.5722 0.2932 0.023 Uiso 1 1 calc R . .
C34 C 0.1102(2) 0.7836(2) -0.1787(2) 0.0227(7) Uani 1 1 d . . .
H34 H 0.0594 0.7722 -0.2310 0.027 Uiso 1 1 calc R . .
O6 O 0.08429(14) 0.58683(14) -0.18453(14) 0.0247(5) Uani 1 1 d . . .
C15 C 0.2843(2) 0.64005(18) 0.09632(19) 0.0163(6) Uani 1 1 d . . .
C8 C 0.5625(2) 0.63233(18) -0.18772(19) 0.0166(6) Uani 1 1 d . . .
C23 C 0.4256(2) 0.73224(18) -0.23651(18) 0.0165(6) Uani 1 1 d . . .
C42 C 0.2176(2) 0.6909(2) 0.4148(2) 0.0292(8) Uani 1 1 d . . .
H42A H 0.2053 0.7258 0.3625 0.044 Uiso 1 1 calc R . .
H42B H 0.2750 0.7071 0.4609 0.044 Uiso 1 1 calc R . .
H42C H 0.1692 0.6975 0.4372 0.044 Uiso 1 1 calc R . .
C36 C 0.9398(2) 0.6291(2) -0.0233(2) 0.0290(8) Uani 1 1 d . . .
H36A H 0.9717 0.6671 -0.0480 0.043 Uiso 1 1 calc R . .
H36B H 0.9813 0.6087 0.0342 0.043 Uiso 1 1 calc R . .
H36C H 0.8897 0.6581 -0.0156 0.043 Uiso 1 1 calc R . .
C37 C 0.8577(2) 0.59128(19) -0.2505(2) 0.0217(7) Uani 1 1 d . . .
H37A H 0.8075 0.5750 -0.3057 0.026 Uiso 1 1 calc R . .
H37B H 0.9097 0.5553 -0.2440 0.026 Uiso 1 1 calc R . .
C19 C 0.2133(2) 0.63654(18) 0.20771(19) 0.0184(6) Uani 1 1 d . . .
H19 H 0.1620 0.6466 0.2218 0.022 Uiso 1 1 calc R . .
C12 C 0.6744(2) 0.62774(18) -0.2591(2) 0.0190(6) Uani 1 1 d . . .
H12 H 0.6878 0.6368 -0.3103 0.023 Uiso 1 1 calc R . .
C20 C 0.2098(2) 0.65375(19) 0.1223(2) 0.0193(6) Uani 1 1 d . . .
H20 H 0.1558 0.6754 0.0799 0.023 Uiso 1 1 calc R . .
C28 C 0.14341(19) 0.62729(19) -0.12807(18) 0.0163(6) Uani 1 1 d . . .
C38 C 0.8837(2) 0.6821(2) -0.2593(2) 0.0251(7) Uani 1 1 d . . .
H38A H 0.8311 0.7176 -0.2710 0.038 Uiso 1 1 calc R . .
H38B H 0.9046 0.6866 -0.3084 0.038 Uiso 1 1 calc R . .
H38C H 0.9319 0.6994 -0.2041 0.038 Uiso 1 1 calc R . .
C39 C 0.3858(2) 0.5576(2) 0.4308(2) 0.0260(7) Uani 1 1 d . . .
H39A H 0.4155 0.5164 0.4062 0.031 Uiso 1 1 calc R . .
H39B H 0.3736 0.5309 0.4797 0.031 Uiso 1 1 calc R . .
C33 C 0.1412(2) 0.8654(2) -0.1559(2) 0.0233(7) Uani 1 1 d . . .
H33 H 0.1105 0.9097 -0.1930 0.028 Uiso 1 1 calc R . .
C35 C 0.9028(2) 0.5552(2) -0.0878(2) 0.0243(7) Uani 1 1 d . . .
H35A H 0.9532 0.5297 -0.0995 0.029 Uiso 1 1 calc R . .
H35B H 0.8789 0.5133 -0.0582 0.029 Uiso 1 1 calc R . .
C21 C 0.3324(2) 0.62580(19) -0.32272(19) 0.0193(6) Uani 1 1 d . . .
C26 C 0.3219(2) 0.8646(2) -0.3360(2) 0.0273(7) Uani 1 1 d . . .
H26 H 0.2876 0.9098 -0.3686 0.033 Uiso 1 1 calc R . .
C32 C 0.2182(2) 0.8818(2) -0.0775(2) 0.0234(7) Uani 1 1 d . . .
H32 H 0.2382 0.9369 -0.0635 0.028 Uiso 1 1 calc R . .
C41 C 0.2225(2) 0.5995(2) 0.3893(2) 0.0239(7) Uani 1 1 d . . .
H41A H 0.2290 0.5643 0.4410 0.029 Uiso 1 1 calc R . .
H41B H 0.1652 0.5845 0.3408 0.029 Uiso 1 1 calc R . .
C40 C 0.4519(2) 0.6308(2) 0.4694(2) 0.0314(8) Uani 1 1 d . . .
H40A H 0.4601 0.6610 0.4210 0.047 Uiso 1 1 calc R . .
H40B H 0.5101 0.6095 0.5099 0.047 Uiso 1 1 calc R . .
H40C H 0.4271 0.6680 0.5018 0.047 Uiso 1 1 calc R . .
C31 C 0.2655(2) 0.81705(19) -0.0202(2) 0.0208(7) Uani 1 1 d . . .
H31 H 0.3165 0.8281 0.0320 0.025 Uiso 1 1 calc R . .
C43 C 0.5597(2) 0.9132(2) 0.1081(2) 0.0337(8) Uani 1 1 d . . .
H43A H 0.5986 0.9430 0.0831 0.040 Uiso 1 1 calc R . .
H43B H 0.5924 0.9094 0.1730 0.040 Uiso 1 1 calc R . .
C25 C 0.4039(2) 0.8795(2) -0.2623(2) 0.0264(7) Uani 1 1 d . . .
H25 H 0.4241 0.9344 -0.2473 0.032 Uiso 1 1 calc R . .
C24 C 0.4556(2) 0.81354(19) -0.2110(2) 0.0210(7) Uani 1 1 d . . .
H24 H 0.5090 0.8237 -0.1608 0.025 Uiso 1 1 calc R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C43 1.782(4) . ?
Cl2 C43 1.752(4) . ?
O2 C16 1.382(3) . ?
O2 C3 1.372(3) . ?
C5 O1 1.366(3) . ?
C5 C6 1.395(4) . ?
C5 C4 1.388(4) . ?
N2 C18 1.389(4) . ?
N2 C39 1.461(4) . ?
N2 C41 1.461(4) . ?
O5 C14 1.505(3) . ?
O5 C28 1.360(3) . ?
C16 C17 1.385(4) . ?
C16 C15 1.392(4) . ?
O1 C9 1.387(3) . ?
C18 C17 1.391(4) . ?
C18 C19 1.419(4) . ?
C1 H1 0.9300 . ?
C1 C6 1.388(4) . ?
C1 C2 1.393(4) . ?
C3 C2 1.398(4) . ?
C3 C4 1.382(4) . ?
C22 C27 1.395(4) . ?
C22 C23 1.382(4) . ?
C22 C21 1.477(4) . ?
O4 C21 1.211(4) . ?
C30 C14 1.522(4) . ?
C30 C29 1.385(4) . ?
C30 C31 1.384(4) . ?
C6 C7 1.515(4) . ?
N1 C11 1.370(4) . ?
N1 C37 1.453(4) . ?
N1 C35 1.462(4) . ?
C13 H13 0.9300 . ?
C13 C8 1.400(4) . ?
C13 C12 1.372(4) . ?
C7 O3 1.509(3) . ?
C7 C8 1.497(4) . ?
C7 C23 1.520(4) . ?
C2 C14 1.501(4) . ?
C14 C15 1.497(4) . ?
C29 C34 1.394(4) . ?
C29 C28 1.476(4) . ?
C9 C10 1.376(4) . ?
C9 C8 1.389(4) . ?
C27 H27 0.9300 . ?
C27 C26 1.383(5) . ?
O3 C21 1.359(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.405(4) . ?
C11 C12 1.422(4) . ?
C4 H4 0.9300 . ?
C17 H17 0.9300 . ?
C34 H34 0.9300 . ?
C34 C33 1.388(4) . ?
O6 C28 1.207(3) . ?
C15 C20 1.400(4) . ?
C23 C24 1.383(4) . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?
C42 C41 1.520(4) . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C36 C35 1.525(5) . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C37 C38 1.522(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.372(4) . ?
C12 H12 0.9300 . ?
C20 H20 0.9300 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C39 C40 1.527(5) . ?
C33 H33 0.9300 . ?
C33 C32 1.398(4) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C26 H26 0.9300 . ?
C26 C25 1.398(5) . ?
C32 H32 0.9300 . ?
C32 C31 1.391(4) . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
C31 H31 0.9300 . ?
C43 H43A 0.9700 . ?
C43 H43B 0.9700 . ?
C25 H25 0.9300 . ?
C25 C24 1.388(4) . ?
C24 H24 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
C3 O2 C16 118.6(2) . . ?
O1 C5 C6 123.3(2) . . ?
O1 C5 C4 115.1(2) . . ?
C4 C5 C6 121.6(3) . . ?
C18 N2 C39 120.1(3) . . ?
C18 N2 C41 121.7(3) . . ?
C41 N2 C39 116.6(2) . . ?
C28 O5 C14 111.1(2) . . ?
O2 C16 C17 114.2(2) . . ?
O2 C16 C15 122.9(2) . . ?
C17 C16 C15 122.9(3) . . ?
C5 O1 C9 118.4(2) . . ?
N2 C18 C17 120.9(3) . . ?
N2 C18 C19 121.8(3) . . ?
C17 C18 C19 117.3(3) . . ?
C6 C1 H1 118.3 . . ?
C6 C1 C2 123.3(3) . . ?
C2 C1 H1 118.3 . . ?
O2 C3 C2 123.1(3) . . ?
O2 C3 C4 115.4(2) . . ?
C4 C3 C2 121.6(3) . . ?
C27 C22 C21 129.8(3) . . ?
C23 C22 C27 121.7(3) . . ?
C23 C22 C21 108.4(3) . . ?
C29 C30 C14 109.8(2) . . ?
C31 C30 C14 129.0(3) . . ?
C31 C30 C29 121.0(3) . . ?
C5 C6 C7 121.8(3) . . ?
C1 C6 C5 117.2(3) . . ?
C1 C6 C7 121.0(2) . . ?
C11 N1 C37 121.6(2) . . ?
C11 N1 C35 120.4(2) . . ?
C37 N1 C35 117.3(2) . . ?
C8 C13 H13 118.6 . . ?
C12 C13 H13 118.6 . . ?
C12 C13 C8 122.8(3) . . ?
C6 C7 C23 112.5(2) . . ?
O3 C7 C6 106.9(2) . . ?
O3 C7 C23 101.7(2) . . ?
C8 C7 C6 110.9(2) . . ?
C8 C7 O3 108.7(2) . . ?
C8 C7 C23 115.3(2) . . ?
C1 C2 C3 117.1(3) . . ?
C1 C2 C14 121.2(3) . . ?
C3 C2 C14 121.7(2) . . ?
O5 C14 C30 101.8(2) . . ?
C2 C14 O5 107.4(2) . . ?
C2 C14 C30 111.3(2) . . ?
C15 C14 O5 107.6(2) . . ?
C15 C14 C30 116.3(2) . . ?
C15 C14 C2 111.5(2) . . ?
C30 C29 C34 121.4(3) . . ?
C30 C29 C28 108.2(3) . . ?
C34 C29 C28 130.3(3) . . ?
O1 C9 C8 123.1(3) . . ?
C10 C9 O1 113.6(2) . . ?
C10 C9 C8 123.3(3) . . ?
C22 C27 H27 121.1 . . ?
C26 C27 C22 117.7(3) . . ?
C26 C27 H27 121.1 . . ?
C21 O3 C7 111.1(2) . . ?
C9 C10 H10 119.6 . . ?
C9 C10 C11 120.8(3) . . ?
C11 C10 H10 119.6 . . ?
N1 C11 C10 121.1(3) . . ?
N1 C11 C12 122.4(3) . . ?
C10 C11 C12 116.5(3) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 C5 119.3(3) . . ?
C3 C4 H4 120.4 . . ?
C16 C17 C18 120.7(3) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C29 C34 H34 121.1 . . ?
C33 C34 C29 117.8(3) . . ?
C33 C34 H34 121.1 . . ?
C16 C15 C14 122.0(3) . . ?
C16 C15 C20 115.8(3) . . ?
C20 C15 C14 122.2(3) . . ?
C13 C8 C7 122.0(3) . . ?
C9 C8 C13 115.7(3) . . ?
C9 C8 C7 122.3(3) . . ?
C22 C23 C7 109.9(3) . . ?
C22 C23 C24 120.6(3) . . ?
C24 C23 C7 129.6(3) . . ?
H42A C42 H42B 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
N1 C37 H37A 108.9 . . ?
N1 C37 H37B 108.9 . . ?
N1 C37 C38 113.3(2) . . ?
H37A C37 H37B 107.7 . . ?
C38 C37 H37A 108.9 . . ?
C38 C37 H37B 108.9 . . ?
C18 C19 H19 119.7 . . ?
C20 C19 C18 120.6(3) . . ?
C20 C19 H19 119.7 . . ?
C13 C12 C11 120.8(3) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C15 C20 H20 118.6 . . ?
C19 C20 C15 122.7(3) . . ?
C19 C20 H20 118.6 . . ?
O5 C28 C29 108.8(2) . . ?
O6 C28 O5 121.5(3) . . ?
O6 C28 C29 129.7(3) . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
N2 C39 H39A 108.6 . . ?
N2 C39 H39B 108.6 . . ?
N2 C39 C40 114.5(3) . . ?
H39A C39 H39B 107.6 . . ?
C40 C39 H39A 108.6 . . ?
C40 C39 H39B 108.6 . . ?
C34 C33 H33 119.7 . . ?
C34 C33 C32 120.6(3) . . ?
C32 C33 H33 119.7 . . ?
N1 C35 C36 114.3(3) . . ?
N1 C35 H35A 108.7 . . ?
N1 C35 H35B 108.7 . . ?
C36 C35 H35A 108.7 . . ?
C36 C35 H35B 108.7 . . ?
H35A C35 H35B 107.6 . . ?
O4 C21 C22 129.4(3) . . ?
O4 C21 O3 121.9(3) . . ?
O3 C21 C22 108.7(2) . . ?
C27 C26 H26 119.7 . . ?
C27 C26 C25 120.6(3) . . ?
C25 C26 H26 119.7 . . ?
C33 C32 H32 119.4 . . ?
C31 C32 C33 121.2(3) . . ?
C31 C32 H32 119.4 . . ?
N2 C41 C42 113.9(3) . . ?
N2 C41 H41A 108.8 . . ?
N2 C41 H41B 108.8 . . ?
C42 C41 H41A 108.8 . . ?
C42 C41 H41B 108.8 . . ?
H41A C41 H41B 107.7 . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C30 C31 C32 118.0(3) . . ?
C30 C31 H31 121.0 . . ?
C32 C31 H31 121.0 . . ?
Cl1 C43 H43A 109.3 . . ?
Cl1 C43 H43B 109.3 . . ?
Cl2 C43 Cl1 111.5(2) . . ?
Cl2 C43 H43A 109.3 . . ?
Cl2 C43 H43B 109.3 . . ?
H43A C43 H43B 108.0 . . ?
C26 C25 H25 119.4 . . ?
C24 C25 C26 121.1(3) . . ?
C24 C25 H25 119.4 . . ?
C23 C24 C25 118.2(3) . . ?
C23 C24 H24 120.9 . . ?
C25 C24 H24 120.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C16 C17 C18 -179.2(2) . . . . ?
O2 C16 C15 C14 4.0(4) . . . . ?
O2 C16 C15 C20 -179.0(3) . . . . ?
O2 C3 C2 C1 179.7(3) . . . . ?
O2 C3 C2 C14 -1.4(4) . . . . ?
O2 C3 C4 C5 179.5(2) . . . . ?
C5 O1 C9 C10 178.1(2) . . . . ?
C5 O1 C9 C8 -1.4(4) . . . . ?
C5 C6 C7 O3 114.0(3) . . . . ?
C5 C6 C7 C8 -4.3(4) . . . . ?
C5 C6 C7 C23 -135.1(3) . . . . ?
N2 C18 C17 C16 176.0(3) . . . . ?
N2 C18 C19 C20 -176.5(3) . . . . ?
O5 C14 C15 C16 111.4(3) . . . . ?
O5 C14 C15 C20 -65.4(3) . . . . ?
C16 O2 C3 C2 -1.4(4) . . . . ?
C16 O2 C3 C4 178.6(2) . . . . ?
C16 C15 C20 C19 -1.4(4) . . . . ?
O1 C5 C6 C1 179.5(3) . . . . ?
O1 C5 C6 C7 1.4(4) . . . . ?
O1 C5 C4 C3 -179.0(2) . . . . ?
O1 C9 C10 C11 -179.0(2) . . . . ?
O1 C9 C8 C13 178.7(3) . . . . ?
O1 C9 C8 C7 -2.0(4) . . . . ?
C18 N2 C39 C40 72.7(4) . . . . ?
C18 N2 C41 C42 -76.7(4) . . . . ?
C18 C19 C20 C15 0.1(5) . . . . ?
C1 C6 C7 O3 -64.1(3) . . . . ?
C1 C6 C7 C8 177.6(3) . . . . ?
C1 C6 C7 C23 46.8(4) . . . . ?
C1 C2 C14 O5 66.1(3) . . . . ?
C1 C2 C14 C30 -44.6(4) . . . . ?
C1 C2 C14 C15 -176.3(3) . . . . ?
C3 O2 C16 C17 -179.9(2) . . . . ?
C3 O2 C16 C15 0.1(4) . . . . ?
C3 C2 C14 O5 -112.8(3) . . . . ?
C3 C2 C14 C30 136.5(3) . . . . ?
C3 C2 C14 C15 4.8(4) . . . . ?
C22 C27 C26 C25 -0.1(5) . . . . ?
C22 C23 C24 C25 -1.2(4) . . . . ?
C30 C14 C15 C16 -135.2(3) . . . . ?
C30 C14 C15 C20 48.0(4) . . . . ?
C30 C29 C34 C33 -0.9(4) . . . . ?
C30 C29 C28 O5 -1.0(3) . . . . ?
C30 C29 C28 O6 179.1(3) . . . . ?
C6 C5 O1 C9 1.7(4) . . . . ?
C6 C5 C4 C3 0.8(4) . . . . ?
C6 C1 C2 C3 0.9(4) . . . . ?
C6 C1 C2 C14 -178.0(3) . . . . ?
C6 C7 O3 C21 114.7(2) . . . . ?
C6 C7 C8 C13 -176.2(3) . . . . ?
C6 C7 C8 C9 4.6(4) . . . . ?
C6 C7 C23 C22 -109.8(3) . . . . ?
C6 C7 C23 C24 68.1(4) . . . . ?
N1 C11 C12 C13 178.1(3) . . . . ?
C7 O3 C21 C22 1.5(3) . . . . ?
C7 O3 C21 O4 -178.3(3) . . . . ?
C7 C23 C24 C25 -178.9(3) . . . . ?
C2 C1 C6 C5 -0.7(4) . . . . ?
C2 C1 C6 C7 177.5(3) . . . . ?
C2 C3 C4 C5 -0.5(4) . . . . ?
C2 C14 C15 C16 -6.1(4) . . . . ?
C2 C14 C15 C20 177.1(3) . . . . ?
C14 O5 C28 C29 -1.8(3) . . . . ?
C14 O5 C28 O6 178.0(3) . . . . ?
C14 C30 C29 C34 -174.1(3) . . . . ?
C14 C30 C29 C28 3.4(3) . . . . ?
C14 C30 C31 C32 173.4(3) . . . . ?
C14 C15 C20 C19 175.6(3) . . . . ?
C29 C30 C14 O5 -4.2(3) . . . . ?
C29 C30 C14 C2 109.9(3) . . . . ?
C29 C30 C14 C15 -120.9(3) . . . . ?
C29 C30 C31 C32 -0.7(4) . . . . ?
C29 C34 C33 C32 0.6(4) . . . . ?
C9 C10 C11 N1 -178.5(3) . . . . ?
C9 C10 C11 C12 0.0(4) . . . . ?
C27 C22 C23 C7 177.8(3) . . . . ?
C27 C22 C23 C24 -0.4(4) . . . . ?
C27 C22 C21 O4 -0.3(5) . . . . ?
C27 C22 C21 O3 179.9(3) . . . . ?
C27 C26 C25 C24 -1.5(5) . . . . ?
O3 C7 C8 C13 66.6(3) . . . . ?
O3 C7 C8 C9 -112.6(3) . . . . ?
O3 C7 C23 C22 4.2(3) . . . . ?
O3 C7 C23 C24 -177.9(3) . . . . ?
C10 C9 C8 C13 -0.7(4) . . . . ?
C10 C9 C8 C7 178.5(3) . . . . ?
C10 C11 C12 C13 -0.4(4) . . . . ?
C11 N1 C37 C38 80.5(3) . . . . ?
C11 N1 C35 C36 -73.1(4) . . . . ?
C4 C5 O1 C9 -178.5(2) . . . . ?
C4 C5 C6 C1 -0.2(4) . . . . ?
C4 C5 C6 C7 -178.4(3) . . . . ?
C4 C3 C2 C1 -0.3(4) . . . . ?
C4 C3 C2 C14 178.6(3) . . . . ?
C17 C16 C15 C14 -176.0(3) . . . . ?
C17 C16 C15 C20 1.0(4) . . . . ?
C17 C18 C19 C20 1.6(4) . . . . ?
C34 C29 C28 O5 176.2(3) . . . . ?
C34 C29 C28 O6 -3.6(5) . . . . ?
C34 C33 C32 C31 -0.4(5) . . . . ?
C15 C16 C17 C18 0.8(4) . . . . ?
C8 C13 C12 C11 0.2(4) . . . . ?
C8 C7 O3 C21 -125.5(2) . . . . ?
C8 C7 C23 C22 121.6(3) . . . . ?
C8 C7 C23 C24 -60.5(4) . . . . ?
C8 C9 C10 C11 0.5(4) . . . . ?
C23 C22 C27 C26 1.1(5) . . . . ?
C23 C22 C21 O4 -178.9(3) . . . . ?
C23 C22 C21 O3 1.3(3) . . . . ?
C23 C7 O3 C21 -3.4(3) . . . . ?
C23 C7 C8 C13 -46.8(4) . . . . ?
C23 C7 C8 C9 134.0(3) . . . . ?
C37 N1 C11 C10 -178.5(3) . . . . ?
C37 N1 C11 C12 3.1(4) . . . . ?
C37 N1 C35 C36 97.2(3) . . . . ?
C19 C18 C17 C16 -2.1(4) . . . . ?
C12 C13 C8 C7 -178.9(3) . . . . ?
C12 C13 C8 C9 0.4(4) . . . . ?
C28 O5 C14 C30 3.6(3) . . . . ?
C28 O5 C14 C2 -113.5(2) . . . . ?
C28 O5 C14 C15 126.4(2) . . . . ?
C28 C29 C34 C33 -177.8(3) . . . . ?
C39 N2 C18 C17 9.6(4) . . . . ?
C39 N2 C18 C19 -172.4(3) . . . . ?
C39 N2 C41 C42 89.1(3) . . . . ?
C33 C32 C31 C30 0.4(5) . . . . ?
C35 N1 C11 C10 -8.6(4) . . . . ?
C35 N1 C11 C12 173.0(3) . . . . ?
C35 N1 C37 C38 -89.7(3) . . . . ?
C21 C22 C27 C26 -177.4(3) . . . . ?
C21 C22 C23 C7 -3.5(3) . . . . ?
C21 C22 C23 C24 178.3(3) . . . . ?
C26 C25 C24 C23 2.1(5) . . . . ?
C41 N2 C18 C17 174.9(3) . . . . ?
C41 N2 C18 C19 -7.0(4) . . . . ?
C41 N2 C39 C40 -93.4(3) . . . . ?
C31 C30 C14 O5 -178.8(3) . . . . ?
C31 C30 C14 C2 -64.6(4) . . . . ?
C31 C30 C14 C15 64.6(4) . . . . ?
C31 C30 C29 C34 0.9(4) . . . . ?
C31 C30 C29 C28 178.5(3) . . . . ?

####################################################################### 
# 
# 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_exp_5002
_audit_block_doi                 10.5517/ccdc.csd.cc1zkj13
_database_code_depnum_ccdc_archive 'CCDC 1834085'
_audit_update_record             
;
2018-04-02 deposited with the CCDC.
2018-11-28 downloaded from the CCDC.
;
_audit_creation_date             2017-06-02
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '2(C21 H18 N O3)'
_chemical_formula_sum            'C42 H36 N2 O6'
_chemical_formula_weight         664.73
_chemical_melting_point          ?
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y+1/2, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y, -z+1/2'
5 '-x, -y, -z'
6 'x-1/2, y-1/2, -z-1/2'
7 '-x-1/2, y-1/2, z'
8 'x, -y, z-1/2'

_cell_length_a                   14.6100(12)
_cell_length_b                   19.4506(11)
_cell_length_c                   12.1904(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3464.2(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1518
_cell_measurement_temperature    106.7
_cell_measurement_theta_max      29.1674
_cell_measurement_theta_min      2.9727
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98273
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1400
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.14
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0645
_diffrn_reflns_av_unetI/netI     0.0680
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11356
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.02
_diffrn_ambient_temperature      106.7
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -3.00   23.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.9046  -95.0000  104.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega  -20.00   13.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.9046  -77.0000   90.0000 33

#__ type_ start__ end____ width___ exp.time_
  3 omega   22.00   48.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       20.9827  -73.0000 -149.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega    4.00   90.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       20.9827   73.0000  -30.0000 86

#__ type_ start__ end____ width___ exp.time_
  5 omega  -48.00  -23.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       20.9827  -73.0000 -149.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0424025000
_diffrn_orient_matrix_UB_12      -0.0175686000
_diffrn_orient_matrix_UB_13      -0.0043996000
_diffrn_orient_matrix_UB_21      -0.0162484000
_diffrn_orient_matrix_UB_22      0.0174923000
_diffrn_orient_matrix_UB_23      0.0471915000
_diffrn_orient_matrix_UB_31      -0.0172212000
_diffrn_orient_matrix_UB_32      0.0267193000
_diffrn_orient_matrix_UB_33      -0.0337656000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2117
_reflns_number_total             3396
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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-97 (Sheldrick, 1997)'
_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_refine_diff_density_max         0.654
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         3396
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1465
_refine_ls_R_factor_gt           0.0952
_refine_ls_restrained_S_all      1.051
_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)+(0.0848P)²+6.4900P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2170
_refine_ls_wR_factor_ref         0.2502
_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
O1 O 0.14435(18) 0.20451(13) 0.3875(2) 0.0372(7) Uani 1 1 d . . .
O2 O 0.1484(2) 0.31743(14) 0.3613(3) 0.0509(9) Uani 1 1 d . . .
C9 C 0.0411(3) 0.11249(18) 0.3371(3) 0.0304(9) Uani 1 1 d . . .
O4 O 0.0839(2) 0.00170(13) 0.4133(2) 0.0542(9) Uani 1 1 d . . .
C12 C 0.0000 0.1461(3) 0.2500 0.0334(13) Uani 1 2 d S . .
H12 H 0.0000 0.1939 0.2500 0.040 Uiso 1 2 calc SR . .
C18 C 0.1828(3) 0.1310(2) 0.5975(3) 0.0394(10) Uani 1 1 d . . .
H18 H 0.1836 0.1783 0.6093 0.047 Uiso 1 1 calc R . .
C10 C 0.0427(3) 0.04077(19) 0.3337(3) 0.0375(10) Uani 1 1 d . . .
C7 C 0.0083(3) 0.19687(18) 0.4861(3) 0.0333(9) Uani 1 1 d . . .
C13 C 0.1331(3) 0.10575(18) 0.5085(3) 0.0322(9) Uani 1 1 d . . .
C11 C 0.0000 0.0046(3) 0.2500 0.0481(17) Uani 1 2 d S . .
H11 H 0.0000 -0.0432 0.2500 0.058 Uiso 1 2 calc SR . .
C8 C 0.0815(3) 0.15218(17) 0.4323(3) 0.0302(9) Uani 1 1 d . . .
C1 C 0.1094(3) 0.2696(2) 0.3977(4) 0.0401(10) Uani 1 1 d . . .
C16 C 0.2272(3) 0.0175(2) 0.6564(4) 0.0469(11) Uani 1 1 d . . .
C14 C 0.1321(3) 0.0354(2) 0.4970(3) 0.0416(11) Uani 1 1 d . . .
N1 N 0.2702(3) -0.02480(19) 0.7305(3) 0.0625(13) Uani 1 1 d . A .
C2 C 0.0222(3) 0.26478(19) 0.4586(4) 0.0384(10) Uani 1 1 d . . .
C17 C 0.2304(3) 0.0898(2) 0.6681(4) 0.0423(11) Uani 1 1 d . . .
H17 H 0.2650 0.1094 0.7240 0.051 Uiso 1 1 calc R . .
C15 C 0.1772(3) -0.0081(2) 0.5678(4) 0.0500(12) Uani 1 1 d . . .
H15 H 0.1744 -0.0553 0.5563 0.060 Uiso 1 1 calc R . .
C6 C -0.0666(3) 0.1775(2) 0.5486(3) 0.0470(11) Uani 1 1 d . . .
H6 H -0.0753 0.1320 0.5696 0.056 Uiso 1 1 calc R . .
C19 C 0.2632(4) -0.0993(3) 0.7195(4) 0.0673(15) Uani 1 1 d . . .
H19A H 0.2028 -0.1113 0.6928 0.081 Uiso 1 1 calc R . .
H19B H 0.2715 -0.1206 0.7908 0.081 Uiso 1 1 calc R . .
C5 C -0.1283(3) 0.2286(3) 0.5791(4) 0.0585(14) Uani 1 1 d . . .
H5 H -0.1787 0.2173 0.6221 0.070 Uiso 1 1 calc R . .
C3 C -0.0400(3) 0.3157(2) 0.4877(4) 0.0569(13) Uani 1 1 d . . .
H3 H -0.0308 0.3614 0.4683 0.068 Uiso 1 1 calc R . .
C4 C -0.1157(3) 0.2955(3) 0.5465(5) 0.0651(15) Uani 1 1 d . . .
H4 H -0.1596 0.3282 0.5647 0.078 Uiso 1 1 calc R . .
C21 C 0.3252(5) 0.0032(3) 0.8199(5) 0.087(2) Uani 1 1 d . . .
H21A H 0.3676 0.0345 0.7845 0.104 Uiso 0.475(9) 1 calc PR A 1
H21B H 0.2833 0.0320 0.8610 0.104 Uiso 0.475(9) 1 calc PR A 1
H21C H 0.2967 0.0457 0.8435 0.104 Uiso 0.525(9) 1 calc PR A 2
H21D H 0.3216 -0.0287 0.8809 0.104 Uiso 0.525(9) 1 calc PR A 2
C20 C 0.3331(5) -0.1255(4) 0.6428(5) 0.111(3) Uani 1 1 d . . .
H20A H 0.3274 -0.1022 0.5737 0.167 Uiso 1 1 calc R . .
H20B H 0.3243 -0.1739 0.6321 0.167 Uiso 1 1 calc R . .
H20C H 0.3929 -0.1174 0.6726 0.167 Uiso 1 1 calc R . .
C22 C 0.3744(10) -0.0284(8) 0.8951(14) 0.104(4) Uani 0.475(9) 1 d P A 1
H22A H 0.3346 -0.0525 0.9445 0.155 Uiso 0.475(9) 1 calc PR A 1
H22B H 0.4095 0.0049 0.9354 0.155 Uiso 0.475(9) 1 calc PR A 1
H22C H 0.4150 -0.0605 0.8604 0.155 Uiso 0.475(9) 1 calc PR A 1
C23 C 0.4200(9) 0.0172(8) 0.8001(13) 0.104(4) Uani 0.525(9) 1 d P A 2
H23A H 0.4502 -0.0243 0.7773 0.155 Uiso 0.525(9) 1 calc PR A 2
H23B H 0.4479 0.0340 0.8661 0.155 Uiso 0.525(9) 1 calc PR A 2
H23C H 0.4255 0.0512 0.7434 0.155 Uiso 0.525(9) 1 calc PR A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.476(4) . ?
O1 C1 1.371(5) . ?
O2 C1 1.177(5) . ?
C9 C12 1.384(4) . ?
C9 C10 1.396(5) . ?
C9 C8 1.514(5) . ?
O4 C10 1.371(4) . ?
O4 C14 1.402(5) . ?
C12 C9 1.384(4) 4 ?
C12 H12 0.9300 . ?
C18 H18 0.9300 . ?
C18 C13 1.395(5) . ?
C18 C17 1.366(6) . ?
C10 C11 1.388(5) . ?
C7 C8 1.527(5) . ?
C7 C2 1.378(5) . ?
C7 C6 1.385(6) . ?
C13 C8 1.499(5) . ?
C13 C14 1.377(5) . ?
C11 C10 1.388(5) 4 ?
C11 H11 0.9300 . ?
C1 C2 1.478(6) . ?
C16 N1 1.374(5) . ?
C16 C17 1.415(6) . ?
C16 C15 1.395(6) . ?
C14 C15 1.376(6) . ?
N1 C19 1.458(6) . ?
N1 C21 1.459(7) . ?
C2 C3 1.389(6) . ?
C17 H17 0.9300 . ?
C15 H15 0.9300 . ?
C6 H6 0.9300 . ?
C6 C5 1.393(7) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.475(8) . ?
C5 H5 0.9300 . ?
C5 C4 1.373(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.375(7) . ?
C4 H4 0.9300 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 H21C 0.9700 . ?
C21 H21D 0.9700 . ?
C21 C22 1.318(15) . ?
C21 C23 1.432(15) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 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
C1 O1 C8 111.8(3) . . ?
C12 C9 C10 117.2(3) . . ?
C12 C9 C8 121.1(3) . . ?
C10 C9 C8 121.7(3) . . ?
C10 O4 C14 118.4(3) . . ?
C9 C12 C9 123.6(5) 4 . ?
C9 C12 H12 118.2 . . ?
C9 C12 H12 118.2 4 . ?
C13 C18 H18 118.4 . . ?
C17 C18 H18 118.4 . . ?
C17 C18 C13 123.2(4) . . ?
O4 C10 C9 122.7(3) . . ?
O4 C10 C11 115.9(3) . . ?
C11 C10 C9 121.4(4) . . ?
C2 C7 C8 109.8(3) . . ?
C2 C7 C6 120.7(4) . . ?
C6 C7 C8 129.4(4) . . ?
C18 C13 C8 122.1(3) . . ?
C14 C13 C18 115.8(3) . . ?
C14 C13 C8 122.1(3) . . ?
C10 C11 C10 119.1(5) . 4 ?
C10 C11 H11 120.5 4 . ?
C10 C11 H11 120.5 . . ?
O1 C8 C9 108.1(3) . . ?
O1 C8 C7 101.7(3) . . ?
O1 C8 C13 109.4(3) . . ?
C9 C8 C7 110.2(3) . . ?
C13 C8 C9 111.4(3) . . ?
C13 C8 C7 115.4(3) . . ?
O1 C1 C2 107.9(3) . . ?
O2 C1 O1 121.0(4) . . ?
O2 C1 C2 131.1(4) . . ?
N1 C16 C17 120.9(4) . . ?
N1 C16 C15 122.4(4) . . ?
C15 C16 C17 116.7(4) . . ?
C13 C14 O4 123.0(3) . . ?
C15 C14 O4 114.3(3) . . ?
C15 C14 C13 122.8(4) . . ?
C16 N1 C19 120.1(4) . . ?
C16 N1 C21 121.3(4) . . ?
C19 N1 C21 118.5(4) . . ?
C7 C2 C1 108.1(3) . . ?
C7 C2 C3 121.6(4) . . ?
C3 C2 C1 130.3(4) . . ?
C18 C17 C16 120.2(4) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C16 C15 H15 119.4 . . ?
C14 C15 C16 121.2(4) . . ?
C14 C15 H15 119.4 . . ?
C7 C6 H6 121.2 . . ?
C7 C6 C5 117.7(4) . . ?
C5 C6 H6 121.2 . . ?
N1 C19 H19A 109.5 . . ?
N1 C19 H19B 109.5 . . ?
N1 C19 C20 110.7(5) . . ?
H19A C19 H19B 108.1 . . ?
C20 C19 H19A 109.5 . . ?
C20 C19 H19B 109.5 . . ?
C6 C5 H5 119.6 . . ?
C4 C5 C6 120.8(4) . . ?
C4 C5 H5 119.6 . . ?
C2 C3 H3 121.4 . . ?
C4 C3 C2 117.1(5) . . ?
C4 C3 H3 121.4 . . ?
C5 C4 C3 122.0(5) . . ?
C5 C4 H4 119.0 . . ?
C3 C4 H4 119.0 . . ?
N1 C21 H21A 104.7 . . ?
N1 C21 H21B 104.7 . . ?
N1 C21 H21C 107.7 . . ?
N1 C21 H21D 107.7 . . ?
H21A C21 H21B 105.7 . . ?
H21A C21 H21C 82.6 . . ?
H21A C21 H21D 141.0 . . ?
H21B C21 H21C 23.4 . . ?
H21B C21 H21D 86.5 . . ?
H21C C21 H21D 107.1 . . ?
C22 C21 N1 130.3(9) . . ?
C22 C21 H21A 104.7 . . ?
C22 C21 H21B 104.7 . . ?
C22 C21 H21C 115.1 . . ?
C22 C21 H21D 36.7 . . ?
C22 C21 C23 71.2(9) . . ?
C23 C21 N1 118.5(8) . . ?
C23 C21 H21A 35.7 . . ?
C23 C21 H21B 126.1 . . ?
C23 C21 H21C 107.7 . . ?
C23 C21 H21D 107.7 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C7 1.7(5) . . . . ?
O1 C1 C2 C3 -178.4(4) . . . . ?
O2 C1 C2 C7 -178.0(5) . . . . ?
O2 C1 C2 C3 1.9(9) . . . . ?
C9 C10 C11 C10 2.0(3) . . . 4 ?
O4 C10 C11 C10 -179.7(4) . . . 4 ?
O4 C14 C15 C16 -179.0(4) . . . . ?
C12 C9 C10 O4 177.9(3) . . . . ?
C12 C9 C10 C11 -3.9(6) . . . . ?
C12 C9 C8 O1 -52.0(4) . . . . ?
C12 C9 C8 C7 58.3(4) . . . . ?
C12 C9 C8 C13 -172.2(3) . . . . ?
C18 C13 C8 O1 55.2(5) . . . . ?
C18 C13 C8 C9 174.7(4) . . . . ?
C18 C13 C8 C7 -58.7(5) . . . . ?
C18 C13 C14 O4 178.7(4) . . . . ?
C18 C13 C14 C15 -0.3(7) . . . . ?
C10 C9 C12 C9 1.9(3) . . . 4 ?
C10 C9 C8 O1 128.6(4) . . . . ?
C10 C9 C8 C7 -121.1(4) . . . . ?
C10 C9 C8 C13 8.4(5) . . . . ?
C10 O4 C14 C13 6.1(7) . . . . ?
C10 O4 C14 C15 -174.9(4) . . . . ?
C7 C2 C3 C4 0.8(7) . . . . ?
C7 C6 C5 C4 1.0(7) . . . . ?
C13 C18 C17 C16 -3.3(7) . . . . ?
C13 C14 C15 C16 0.0(8) . . . . ?
C8 O1 C1 O2 -176.2(4) . . . . ?
C8 O1 C1 C2 4.1(4) . . . . ?
C8 C9 C12 C9 -177.5(4) . . . 4 ?
C8 C9 C10 O4 -2.6(6) . . . . ?
C8 C9 C10 C11 175.5(3) . . . . ?
C8 C7 C2 C1 -6.5(4) . . . . ?
C8 C7 C2 C3 173.6(4) . . . . ?
C8 C7 C6 C5 -173.8(4) . . . . ?
C8 C13 C14 O4 0.6(7) . . . . ?
C8 C13 C14 C15 -178.4(4) . . . . ?
C1 O1 C8 C9 108.5(3) . . . . ?
C1 O1 C8 C7 -7.5(4) . . . . ?
C1 O1 C8 C13 -130.1(3) . . . . ?
C1 C2 C3 C4 -179.1(5) . . . . ?
C16 N1 C19 C20 85.0(6) . . . . ?
C16 N1 C21 C22 -176.6(11) . . . . ?
C16 N1 C21 C23 -87.7(9) . . . . ?
C14 O4 C10 C9 -5.0(6) . . . . ?
C14 O4 C10 C11 176.8(3) . . . . ?
C14 C13 C8 O1 -126.8(4) . . . . ?
C14 C13 C8 C9 -7.4(5) . . . . ?
C14 C13 C8 C7 119.3(4) . . . . ?
N1 C16 C17 C18 -176.2(5) . . . . ?
N1 C16 C15 C14 177.7(5) . . . . ?
C2 C7 C8 O1 8.5(4) . . . . ?
C2 C7 C8 C9 -106.0(4) . . . . ?
C2 C7 C8 C13 126.8(4) . . . . ?
C2 C7 C6 C5 2.2(6) . . . . ?
C2 C3 C4 C5 2.4(8) . . . . ?
C17 C18 C13 C8 -180.0(4) . . . . ?
C17 C18 C13 C14 1.9(6) . . . . ?
C17 C16 N1 C19 177.6(5) . . . . ?
C17 C16 N1 C21 -3.7(8) . . . . ?
C17 C16 C15 C14 -1.3(7) . . . . ?
C15 C16 N1 C19 -1.3(8) . . . . ?
C15 C16 N1 C21 177.4(5) . . . . ?
C15 C16 C17 C18 2.8(7) . . . . ?
C6 C7 C8 O1 -175.2(4) . . . . ?
C6 C7 C8 C9 70.3(5) . . . . ?
C6 C7 C8 C13 -56.9(5) . . . . ?
C6 C7 C2 C1 176.8(4) . . . . ?
C6 C7 C2 C3 -3.1(6) . . . . ?
C6 C5 C4 C3 -3.4(8) . . . . ?
C19 N1 C21 C22 2.1(14) . . . . ?
C19 N1 C21 C23 91.0(9) . . . . ?
C21 N1 C19 C20 -93.7(6) . . . . ?

