# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_exp_605
_database_code_depnum_ccdc_archive 'CCDC 1023827'
_audit_update_record             
;
2014-09-11 deposited with the CCDC.
2016-04-29 downloaded from the CCDC.
;
_audit_creation_date             2014-09-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.06.27 svn.r2953 for OlexSys, GUI svn.r4874)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C67 H66 N4 O12'
_chemical_formula_sum            'C67 H66 N4 O12'
_chemical_formula_weight         1119.12
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_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'

_cell_length_a                   9.0356(2)
_cell_length_b                   10.3472(3)
_cell_length_c                   16.0067(5)
_cell_angle_alpha                97.804(3)
_cell_angle_beta                 104.923(2)
_cell_angle_gamma                100.186(2)
_cell_volume                     1397.13(7)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9891
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.1610
_cell_measurement_theta_min      4.3850
_exptl_absorpt_coefficient_mu    0.745
_exptl_absorpt_correction_T_max  0.849
_exptl_absorpt_correction_T_min  0.806
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             591.9
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14244
_diffrn_reflns_theta_full        73.05
_diffrn_reflns_theta_max         73.05
_diffrn_reflns_theta_min         4.42
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.0851
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -47.00  -18.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   38.0000   60.0000 29

#__ type_ start__ end____ width___ exp.time_
  2 omega  -56.00  -25.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   50.0000  -60.0000 31

#__ type_ start__ end____ width___ exp.time_
  3 omega  -13.00   16.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   38.0000   60.0000 29

#__ type_ start__ end____ width___ exp.time_
  4 omega -110.00  -67.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -64.0000  150.0000 43

#__ type_ start__ end____ width___ exp.time_
  5 omega  -71.00  -35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  178.0000  -30.0000 36

#__ type_ start__ end____ width___ exp.time_
  6 omega  -20.00   23.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   50.0000  -60.0000 43

#__ type_ start__ end____ width___ exp.time_
  7 omega -119.00  -74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  178.0000  -30.0000 45

#__ type_ start__ end____ width___ exp.time_
  8 omega   16.00  129.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   19.0000  -30.0000 113

#__ type_ start__ end____ width___ exp.time_
  9 omega  -16.00   82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -38.0000  150.0000 98

#__ type_ start__ end____ width___ exp.time_
 10 omega  -13.00   68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -57.0000    0.0000 81

#__ type_ start__ end____ width___ exp.time_
 11 omega   39.00   80.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000  120.0000 41

#__ type_ start__ end____ width___ exp.time_
 12 omega   30.00  113.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000 -125.0000 -180.0000 83

#__ type_ start__ end____ width___ exp.time_
 13 omega   30.00   87.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000 -125.0000    0.0000 57

#__ type_ start__ end____ width___ exp.time_
 14 omega   55.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -50.0000   90.0000 48

#__ type_ start__ end____ width___ exp.time_
 15 omega  149.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -12.0000 -150.0000 29

#__ type_ start__ end____ width___ exp.time_
 16 omega   41.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  150.0000 49

#__ type_ start__ end____ width___ exp.time_
 17 omega   59.00   92.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -25.0000  -30.0000 33

#__ type_ start__ end____ width___ exp.time_
 18 omega   50.00   76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -25.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 19 omega   40.00   84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -25.0000 -180.0000 44

#__ type_ start__ end____ width___ exp.time_
 20 omega   58.00   84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -50.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 21 omega  123.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   38.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 22 omega   59.00   84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  178.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
 23 omega   67.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -50.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 24 omega   69.00   95.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 25 omega   56.00   82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -12.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 26 omega  109.00  135.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -12.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 27 omega  104.00  130.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   25.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 28 omega   44.00   86.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -92.0000  -60.0000 42

#__ type_ start__ end____ width___ exp.time_
 29 omega   44.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000 -180.0000 72

#__ type_ start__ end____ width___ exp.time_
 30 omega   69.00  111.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  -90.0000 42

#__ type_ start__ end____ width___ exp.time_
 31 omega   42.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000   30.0000 35

#__ type_ start__ end____ width___ exp.time_
 32 omega   42.00   92.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -50.0000  150.0000 50

#__ type_ start__ end____ width___ exp.time_
 33 omega   39.00   92.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -25.0000 -120.0000 53

#__ type_ start__ end____ width___ exp.time_
 34 omega   49.00   74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -92.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
 35 omega   59.00  114.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000   90.0000 55

#__ type_ start__ end____ width___ exp.time_
 36 omega   52.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000  150.0000 51

#__ type_ start__ end____ width___ exp.time_
 37 omega   91.00  177.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   50.0000  -90.0000 86

#__ type_ start__ end____ width___ exp.time_
 38 omega   79.00  117.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -64.0000   30.0000 38

#__ type_ start__ end____ width___ exp.time_
 39 omega   82.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000    0.0000 34

#__ type_ start__ end____ width___ exp.time_
 40 omega   94.00  152.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   50.0000 -150.0000 58

#__ type_ start__ end____ width___ exp.time_
 41 omega   79.00  122.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   25.0000   60.0000 43

#__ type_ start__ end____ width___ exp.time_
 42 omega  133.00  159.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   25.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 43 omega   44.00   76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  -60.0000 32

#__ type_ start__ end____ width___ exp.time_
 44 omega   91.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
 45 omega   58.00   84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 46 omega   48.00   92.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000  -90.0000 44

#__ type_ start__ end____ width___ exp.time_
 47 omega   51.00  127.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -64.0000  -60.0000 76

#__ type_ start__ end____ width___ exp.time_
 48 omega   59.00   84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
 49 omega  123.00  173.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   64.0000  -60.0000 50

#__ type_ start__ end____ width___ exp.time_
 50 omega  109.00  134.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
 51 omega  110.00  135.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -64.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
 52 omega   86.00  112.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   38.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 53 omega  111.00  136.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  178.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
 54 omega   71.00   97.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  178.0000 -180.0000 26
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0100358000
_diffrn_orient_matrix_UB_12      -0.0826464000
_diffrn_orient_matrix_UB_13      -0.0851891000
_diffrn_orient_matrix_UB_21      0.0974247000
_diffrn_orient_matrix_UB_22      0.1254480000
_diffrn_orient_matrix_UB_23      -0.0181119000
_diffrn_orient_matrix_UB_31      0.1521354000
_diffrn_orient_matrix_UB_32      -0.0343330000
_diffrn_orient_matrix_UB_33      0.0520577000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                7026
_reflns_number_total             11186
_reflns_odcompleteness_completeness 89.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.06(15)
_refine_ls_extinction_coef       0.0049(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     778
_refine_ls_number_reflns         7223
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0438
_refine_ls_restrained_S_all      1.036
_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)+(0.0836P)²+0.1013P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1189
_refine_ls_wR_factor_ref         0.1200
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Others
 Fixed Sof: C5(0.33333) C82(0.33333) C18(0.33333)
3.a Ternary CH refined with riding coordinates:
 C64(H64), C22(H22), C13(H13), C14(H14), C19(H19), C62(H62), C2(H2), C60(H60),
 C68(H68)
3.b Secondary CH2 refined with riding coordinates:
 C73(H73A,H73B), C72(H72A,H72B), C24(H24A,H24B), C61(H61A,H61B), C3(H3A,H3B),
 C21(H21A,H21B), C69(H69A,H69B), C23(H23A,H23B), C70(H70A,H70B), C16(H16A,H16B),
  C1(H1A,H1B), C76(H76A,H76B)
3.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C38(H38), C32(H32), C58(H58), C48(H48), C10(H10), C55(H55), C33(H33),
 C35(H35), C15(H15), C36(H36), C47(H47), C42(H42), C74(H74), C45(H45), C43(H43),
  C44(H44)
3.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C28(H28A,H28B,H28C), C78(H78A,H78B,H78C), C81(H81A,H81B,
 H81C)
3.e Idealised tetrahedral OH refined as rotating group:
 O51(H51), O50(H50), O52(H52)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O29 O -0.6844(2) -0.1050(2) -0.13492(12) 0.0588(5) Uani 1 d . . .
O51 O -0.2405(2) -0.2947(2) -0.57615(13) 0.0553(5) Uani 1 d . . .
H51 H -0.3146 -0.2769 -0.5597 0.083 Uiso 1 calc . . GR
N5 N -0.5805(2) -0.1425(2) -0.24863(12) 0.0410(4) Uani 1 d . . .
O75 O -1.0769(2) -0.9285(2) -0.00266(14) 0.0549(4) Uani 1 d . . .
N65 N -0.8710(2) -0.77550(19) -0.15671(13) 0.0406(4) Uani 1 d . . .
O50 O -0.7935(3) -0.2349(2) -0.8053(2) 0.0773(8) Uani 1 d . . .
H50 H -0.7384 -0.2726 -0.8292 0.116 Uiso 1 calc . . GR
O27 O -0.1775(3) 0.3315(2) -0.23673(15) 0.0613(5) Uani 1 d . . .
O25 O -0.2734(2) 0.3125(2) -0.10102(13) 0.0547(5) Uani 1 d . . .
O18 O -0.9001(3) -0.44358(19) -0.38528(14) 0.0566(5) Uani 1 d . . .
O79 O -0.9269(3) -0.96145(19) -0.26242(14) 0.0596(5) Uani 1 d . . .
N71 N -0.7797(2) -0.4636(2) 0.09686(14) 0.0458(5) Uani 1 d . . .
C39 C -0.3824(3) -0.1920(2) -0.78846(15) 0.0360(4) Uani 1 d . . .
O52 O -0.6077(3) -0.0427(2) -0.95800(13) 0.0664(6) Uani 1 d . . .
H52 H -0.6295 -0.0659 -1.0116 0.100 Uiso 1 calc . . GR
N20 N -0.4833(3) -0.2753(2) -0.51048(14) 0.0476(5) Uani 1 d . . .
O77 O -0.5389(3) -0.6180(2) -0.34035(14) 0.0626(5) Uani 1 d . . .
O80 O -0.3986(3) -0.4129(3) -0.21531(15) 0.0728(7) Uani 1 d . . .
C6 C -0.4717(3) -0.0198(2) -0.23444(15) 0.0407(5) Uani 1 d . . .
C31 C -0.5039(3) -0.1109(2) -0.91811(16) 0.0438(5) Uani 1 d . . .
C64 C -0.8740(3) -0.7179(2) -0.06654(14) 0.0370(4) Uani 1 d . . .
H64 H -0.9823 -0.7156 -0.0672 0.044 Uiso 1 calc . . R
C4 C -0.6933(3) -0.1693(3) -0.20773(16) 0.0451(5) Uani 1 d . . .
C40 C -0.5785(3) -0.0468(2) -0.78062(14) 0.0406(5) Uani 1 d . . .
C53 C -0.7737(3) -0.5713(2) -0.04698(15) 0.0385(5) Uani 1 d . . .
C7 C -0.4288(3) 0.0862(3) -0.16347(16) 0.0435(5) Uani 1 d . . .
H7 H -0.4673 0.0803 -0.1152 0.052 Uiso 1 calc . . R
C37 C -0.2593(3) -0.2761(2) -0.65991(16) 0.0440(5) Uani 1 d . . .
C30 C -0.4905(3) -0.1209(2) -0.83133(15) 0.0382(4) Uani 1 d . . .
C34 C -0.2859(3) -0.2484(2) -0.83435(16) 0.0388(5) Uani 1 d . . .
C38 C -0.3650(3) -0.2079(2) -0.70025(15) 0.0395(5) Uani 1 d . . .
H38 H -0.4265 -0.1713 -0.6692 0.047 Uiso 1 calc . . R
C9 C -0.2719(3) 0.2122(3) -0.24040(17) 0.0472(5) Uani 1 d . . .
C63 C -0.9308(3) -0.9072(2) -0.18999(17) 0.0459(5) Uani 1 d . . .
C54 C -0.7571(3) -0.6892(2) -0.18205(15) 0.0393(5) Uani 1 d . . .
C8 C -0.3271(3) 0.2011(3) -0.16681(17) 0.0455(5) Uani 1 d . . .
C22 C -0.5066(3) -0.1444(2) -0.46748(15) 0.0417(5) Uani 1 d . . .
H22 H -0.4310 -0.0715 -0.4769 0.050 Uiso 1 calc . . R
C59 C -0.6898(3) -0.5762(2) -0.11660(15) 0.0403(5) Uani 1 d . . .
C49 C -0.7200(3) -0.1059(3) -0.77220(17) 0.0482(5) Uani 1 d . . .
C11 C -0.4121(3) -0.0143(3) -0.30586(15) 0.0422(5) Uani 1 d . . .
C13 C -0.6045(3) -0.2180(2) -0.33877(14) 0.0378(4) Uani 1 d . . .
H13 H -0.5978 -0.3110 -0.3361 0.045 Uiso 1 calc . . R
C14 C -0.7699(3) -0.2139(2) -0.39156(15) 0.0397(5) Uani 1 d . . .
H14 H -0.7818 -0.1225 -0.3749 0.048 Uiso 1 calc . . R
C12 C -0.4644(3) -0.1471(2) -0.36815(15) 0.0399(5) Uani 1 d . . .
C41 C -0.5092(3) 0.0899(2) -0.73825(16) 0.0463(5) Uani 1 d . . .
C73 C -0.8809(3) -0.4712(2) -0.05680(17) 0.0459(5) Uani 1 d . . .
H73A H -0.8255 -0.3855 -0.0632 0.055 Uiso 1 calc . . R
H73B H -0.9733 -0.5049 -0.1071 0.055 Uiso 1 calc . . R
C19 C -0.7904(3) -0.2364(2) -0.49134(15) 0.0422(5) Uani 1 d . . .
H19 H -0.8963 -0.2281 -0.5217 0.051 Uiso 1 calc . . R
C62 C -0.8137(3) -0.8114(2) -0.00694(16) 0.0411(5) Uani 1 d . . .
H62 H -0.7250 -0.8357 -0.0251 0.049 Uiso 1 calc . . R
C32 C -0.4078(3) -0.1665(2) -0.96366(15) 0.0458(5) Uani 1 d . . .
H32 H -0.4176 -0.1582 -1.0219 0.055 Uiso 1 calc . . R
C72 C -0.9247(3) -0.4596(3) 0.02910(18) 0.0492(6) Uani 1 d . . .
H72A H -0.9567 -0.3762 0.0418 0.059 Uiso 1 calc . . R
H72B H -1.0097 -0.5334 0.0263 0.059 Uiso 1 calc . . R
C66 C -0.6733(3) -0.5217(2) 0.05096(15) 0.0417(5) Uani 1 d . . .
C57 C -0.5182(3) -0.5008(3) -0.20096(17) 0.0473(5) Uani 1 d . . .
C58 C -0.5688(3) -0.4809(2) -0.12606(16) 0.0450(5) Uani 1 d . . .
H58 H -0.5220 -0.4047 -0.0827 0.054 Uiso 1 calc . . R
C56 C -0.5928(3) -0.6130(3) -0.26832(17) 0.0472(5) Uani 1 d . . .
C2 C -0.8860(3) -0.3040(3) -0.35767(17) 0.0466(5) Uani 1 d . . .
H2 H -0.9896 -0.2828 -0.3765 0.056 Uiso 1 calc . . R
C17 C -0.7648(3) -0.3702(2) -0.53116(16) 0.0484(6) Uani 1 d . . .
C24 C -0.4110(4) -0.3424(3) -0.4388(2) 0.0543(6) Uani 1 d . . .
H24A H -0.3316 -0.3853 -0.4538 0.065 Uiso 1 calc . . R
H24B H -0.4899 -0.4090 -0.4276 0.065 Uiso 1 calc . . R
C67 C -0.8619(3) -0.6870(3) 0.13104(16) 0.0468(5) Uani 1 d . . .
C60 C -0.9418(3) -0.9409(2) -0.03161(18) 0.0470(5) Uani 1 d . . .
H60 H -0.8966 -1.0115 -0.0065 0.056 Uiso 1 calc . . R
C61 C -1.0059(3) -0.9859(2) -0.13286(19) 0.0496(6) Uani 1 d . . .
H61A H -0.9976 -1.0780 -0.1473 0.060 Uiso 1 calc . . R
H61B H -1.1168 -0.9853 -0.1496 0.060 Uiso 1 calc . . R
C48 C -0.8015(4) -0.0332(3) -0.72479(19) 0.0542(6) Uani 1 d . . .
H48 H -0.8992 -0.0746 -0.7212 0.065 Uiso 1 calc . . R
C3 C -0.8310(3) -0.2822(3) -0.25648(18) 0.0528(6) Uani 1 d . . .
H3A H -0.9193 -0.2685 -0.2351 0.063 Uiso 1 calc . . R
H3B H -0.8053 -0.3644 -0.2404 0.063 Uiso 1 calc . . R
C68 C -0.7463(3) -0.7437(3) 0.09032(16) 0.0454(5) Uani 1 d . . .
H68 H -0.7055 -0.8083 0.1243 0.055 Uiso 1 calc . . R
C21 C -0.6708(3) -0.1240(2) -0.50625(15) 0.0445(5) Uani 1 d . . .
H21A H -0.6901 -0.1248 -0.5688 0.053 Uiso 1 calc . . R
H21B H -0.6809 -0.0381 -0.4783 0.053 Uiso 1 calc . . R
C10 C -0.3108(3) 0.1023(3) -0.30873(16) 0.0459(5) Uani 1 d . . .
H10 H -0.2694 0.1067 -0.3561 0.055 Uiso 1 calc . . R
C46 C -0.5917(4) 0.1610(3) -0.68993(17) 0.0550(7) Uani 1 d . . .
C55 C -0.7122(3) -0.7090(3) -0.25913(17) 0.0464(5) Uani 1 d . . .
H55 H -0.7610 -0.7844 -0.3029 0.056 Uiso 1 calc . . R
C69 C -0.8148(3) -0.5381(3) 0.16485(18) 0.0517(6) Uani 1 d . . .
H69A H -0.8992 -0.5086 0.1837 0.062 Uiso 1 calc . . R
H69B H -0.7228 -0.5180 0.2156 0.062 Uiso 1 calc . . R
C33 C -0.3013(3) -0.2319(2) -0.92237(16) 0.0438(5) Uani 1 d . . .
H33 H -0.2372 -0.2665 -0.9525 0.053 Uiso 1 calc . . R
C35 C -0.1761(3) -0.3167(3) -0.78998(18) 0.0482(6) Uani 1 d . . .
H35 H -0.1124 -0.3527 -0.8196 0.058 Uiso 1 calc . . R
C23 C -0.3386(3) -0.2301(3) -0.35994(18) 0.0504(6) Uani 1 d . . .
H23A H -0.2402 -0.1783 -0.3630 0.060 Uiso 1 calc . . R
H23B H -0.3206 -0.2638 -0.3054 0.060 Uiso 1 calc . . R
C70 C -0.6095(3) -0.6284(3) 0.09578(16) 0.0470(5) Uani 1 d . . .
H70A H -0.5526 -0.5908 0.1570 0.056 Uiso 1 calc . . R
H70B H -0.5374 -0.6614 0.0672 0.056 Uiso 1 calc . . R
C15 C -0.8495(4) -0.4855(3) -0.5267(2) 0.0600(7) Uani 1 d . . .
H15 H -0.8334 -0.5642 -0.5549 0.072 Uiso 1 calc . . R
C36 C -0.1618(3) -0.3308(3) -0.70547(19) 0.0508(6) Uani 1 d . . .
H36 H -0.0888 -0.3758 -0.6775 0.061 Uiso 1 calc . . R
C47 C -0.7382(4) 0.0955(3) -0.68491(19) 0.0573(7) Uani 1 d . . .
H47 H -0.7926 0.1417 -0.6536 0.069 Uiso 1 calc . . R
C42 C -0.3618(5) 0.1572(3) -0.7423(2) 0.0656(8) Uani 1 d . . .
H42 H -0.3063 0.1121 -0.7734 0.079 Uiso 1 calc . . R
C26 C -0.3355(4) 0.3076(3) -0.0283(2) 0.0615(7) Uani 1 d . . .
H26A H -0.4481 0.2847 -0.0491 0.092 Uiso 1 calc . . GR
H26B H -0.3016 0.3934 0.0103 0.092 Uiso 1 calc . . GR
H26C H -0.2988 0.2413 0.0031 0.092 Uiso 1 calc . . GR
C74 C -0.9956(4) -0.7616(3) 0.1324(2) 0.0564(6) Uani 1 d . . .
H74 H -1.0599 -0.7224 0.1601 0.068 Uiso 1 calc . . R
C16 C -0.9706(4) -0.4938(3) -0.4781(2) 0.0651(8) Uani 1 d . . .
H16A H -1.0464 -0.4423 -0.5012 0.078 Uiso 1 calc . . R
H16B H -1.0261 -0.5862 -0.4874 0.078 Uiso 1 calc . . R
C1 C -0.6309(4) -0.3593(3) -0.57204(19) 0.0565(7) Uani 1 d . . .
H1A H -0.6150 -0.4481 -0.5896 0.068 Uiso 1 calc . . R
H1B H -0.6584 -0.3211 -0.6245 0.068 Uiso 1 calc . . R
C28 C -0.1373(5) 0.3549(4) -0.3137(3) 0.0851(12) Uani 1 d . . .
H28A H -0.2312 0.3470 -0.3606 0.128 Uiso 1 calc . . GR
H28B H -0.0803 0.2904 -0.3300 0.128 Uiso 1 calc . . GR
H28C H -0.0729 0.4433 -0.3029 0.128 Uiso 1 calc . . GR
C78 C -0.6124(5) -0.7280(4) -0.4105(2) 0.0756(10) Uani 1 d . . .
H78A H -0.5653 -0.7198 -0.4575 0.113 Uiso 1 calc . . GR
H78B H -0.7223 -0.7293 -0.4316 0.113 Uiso 1 calc . . GR
H78C H -0.5995 -0.8095 -0.3902 0.113 Uiso 1 calc . . GR
C76 C -1.0474(5) -0.9072(3) 0.0911(2) 0.0657(8) Uani 1 d . . .
H76A H -0.9667 -0.9531 0.1160 0.079 Uiso 1 calc . . R
H76B H -1.1423 -0.9453 0.1048 0.079 Uiso 1 calc . . R
C45 C -0.5198(6) 0.2958(3) -0.6478(3) 0.0774(11) Uani 1 d . . .
H45 H -0.5713 0.3431 -0.6151 0.093 Uiso 1 calc . . R
C81 C -0.2665(4) -0.3620(4) -0.1480(3) 0.0765(10) Uani 1 d . . .
H81A H -0.1767 -0.3560 -0.1700 0.115 Uiso 1 calc . . GR
H81B H -0.2589 -0.4194 -0.1054 0.115 Uiso 1 calc . . GR
H81C H -0.2700 -0.2745 -0.1207 0.115 Uiso 1 calc . . GR
C43 C -0.2990(6) 0.2882(4) -0.7011(3) 0.0876(12) Uani 1 d . . .
H43 H -0.2020 0.3310 -0.7049 0.105 Uiso 1 calc . . R
C44 C -0.3789(7) 0.3574(3) -0.6538(3) 0.0941(15) Uani 1 d . . .
H44 H -0.3356 0.4461 -0.6261 0.113 Uiso 1 calc . . R
O1 O -1.0713(11) -0.9459(8) -0.5113(6) 0.221(4) Uani 1 d . . .
C5 C -1.019(3) -0.8773(13) -0.4369(10) 0.108(6) Uani 0.33 d . . .
C82 C -1.092(3) -0.994(3) -0.4399(12) 0.161(12) Uani 0.33 d . . .
C18 C -0.9485(16) -0.950(3) -0.4402(9) 0.109(6) Uani 0.33 d . . .
H66 H -0.588(3) -0.453(2) 0.0503(17) 0.030(6) Uiso 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
O29 C4 1.236(3) . ?
O51 C37 1.352(3) . ?
N5 C6 1.413(3) . ?
N5 C4 1.355(3) . ?
N5 C13 1.488(3) . ?
O75 C60 1.433(3) . ?
O75 C76 1.433(4) . ?
N65 C64 1.494(3) . ?
N65 C63 1.352(3) . ?
N65 C54 1.418(3) . ?
O50 C49 1.348(3) . ?
O27 C9 1.356(3) . ?
O27 C28 1.410(4) . ?
O25 C8 1.372(3) . ?
O25 C26 1.420(4) . ?
O18 C2 1.425(3) . ?
O18 C16 1.439(4) . ?
O79 C63 1.229(3) . ?
N71 C72 1.481(3) . ?
N71 C66 1.508(3) . ?
N71 C69 1.483(4) . ?
C39 C30 1.418(3) . ?
C39 C34 1.426(3) . ?
C39 C38 1.415(3) . ?
O52 C31 1.354(3) . ?
N20 C22 1.509(3) . ?
N20 C24 1.488(3) . ?
N20 C1 1.478(4) . ?
O77 C56 1.360(3) . ?
O77 C78 1.414(4) . ?
O80 C57 1.373(3) . ?
O80 C81 1.351(4) . ?
C6 C7 1.389(3) . ?
C6 C11 1.387(3) . ?
C31 C30 1.383(3) . ?
C31 C32 1.416(4) . ?
C64 C53 1.568(3) . ?
C64 C62 1.521(3) . ?
C4 C3 1.504(4) . ?
C40 C30 1.502(3) . ?
C40 C49 1.364(4) . ?
C40 C41 1.436(3) . ?
C53 C59 1.501(3) . ?
C53 C73 1.535(3) . ?
C53 C66 1.558(3) . ?
C7 C8 1.384(3) . ?
C37 C38 1.369(3) . ?
C37 C36 1.423(4) . ?
C34 C33 1.416(3) . ?
C34 C35 1.417(4) . ?
C9 C8 1.403(4) . ?
C9 C10 1.391(4) . ?
C63 C61 1.512(4) . ?
C54 C59 1.387(3) . ?
C54 C55 1.395(3) . ?
C22 C12 1.542(3) . ?
C22 C21 1.517(4) . ?
C59 C58 1.391(3) . ?
C49 C48 1.419(3) . ?
C11 C12 1.504(3) . ?
C11 C10 1.394(3) . ?
C13 C14 1.526(3) . ?
C13 C12 1.560(3) . ?
C14 C19 1.540(3) . ?
C14 C2 1.532(3) . ?
C12 C23 1.532(4) . ?
C41 C46 1.425(4) . ?
C41 C42 1.411(4) . ?
C73 C72 1.521(4) . ?
C19 C17 1.526(3) . ?
C19 C21 1.530(3) . ?
C62 C60 1.537(3) . ?
C62 C68 1.533(3) . ?
C32 C33 1.358(4) . ?
C66 C70 1.514(4) . ?
C57 C58 1.392(4) . ?
C57 C56 1.405(4) . ?
C56 C55 1.384(4) . ?
C2 C3 1.539(4) . ?
C17 C15 1.319(4) . ?
C17 C1 1.511(4) . ?
C24 C23 1.510(4) . ?
C67 C68 1.524(4) . ?
C67 C69 1.507(4) . ?
C67 C74 1.321(4) . ?
C60 C61 1.548(4) . ?
C48 C47 1.349(4) . ?
C68 C70 1.535(4) . ?
C46 C47 1.404(5) . ?
C46 C45 1.422(4) . ?
C35 C36 1.356(4) . ?
C15 C16 1.494(5) . ?
C42 C43 1.374(4) . ?
C74 C76 1.499(4) . ?
C45 C44 1.352(7) . ?
C43 C44 1.387(7) . ?
O1 C5 1.228(15) . ?
O1 C82 1.350(19) . ?
O1 C18 1.380(16) . ?
C5 C82 1.26(3) . ?
C5 C18 1.07(2) . ?
C82 C18 1.30(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N5 C13 109.41(18) . . ?
C4 N5 C6 126.5(2) . . ?
C4 N5 C13 119.2(2) . . ?
C60 O75 C76 114.1(2) . . ?
C63 N65 C64 120.0(2) . . ?
C63 N65 C54 126.8(2) . . ?
C54 N65 C64 109.69(17) . . ?
C9 O27 C28 117.8(2) . . ?
C8 O25 C26 115.7(2) . . ?
C2 O18 C16 115.1(2) . . ?
C72 N71 C66 108.19(19) . . ?
C72 N71 C69 111.8(2) . . ?
C69 N71 C66 112.7(2) . . ?
C30 C39 C34 119.7(2) . . ?
C38 C39 C30 122.1(2) . . ?
C38 C39 C34 118.2(2) . . ?
C24 N20 C22 107.37(19) . . ?
C1 N20 C22 112.2(2) . . ?
C1 N20 C24 113.0(2) . . ?
C56 O77 C78 117.2(2) . . ?
C81 O80 C57 118.4(2) . . ?
C7 C6 N5 128.2(2) . . ?
C11 C6 N5 109.8(2) . . ?
C11 C6 C7 121.9(2) . . ?
O52 C31 C30 118.5(2) . . ?
O52 C31 C32 120.5(2) . . ?
C30 C31 C32 121.0(2) . . ?
N65 C64 C53 104.48(18) . . ?
N65 C64 C62 106.35(18) . . ?
C62 C64 C53 117.14(19) . . ?
O29 C4 N5 122.4(2) . . ?
O29 C4 C3 121.8(2) . . ?
N5 C4 C3 115.9(2) . . ?
C49 C40 C30 122.2(2) . . ?
C49 C40 C41 119.1(2) . . ?
C41 C40 C30 118.6(2) . . ?
C59 C53 C64 102.20(17) . . ?
C59 C53 C73 111.6(2) . . ?
C59 C53 C66 118.14(19) . . ?
C73 C53 C64 110.46(19) . . ?
C73 C53 C66 100.92(19) . . ?
C66 C53 C64 113.72(19) . . ?
C8 C7 C6 117.9(2) . . ?
O51 C37 C38 122.9(2) . . ?
O51 C37 C36 116.6(2) . . ?
C38 C37 C36 120.5(2) . . ?
C39 C30 C40 120.2(2) . . ?
C31 C30 C39 119.3(2) . . ?
C31 C30 C40 120.2(2) . . ?
C33 C34 C39 118.7(2) . . ?
C33 C34 C35 122.3(2) . . ?
C35 C34 C39 119.0(2) . . ?
C37 C38 C39 121.1(2) . . ?
O27 C9 C8 115.5(2) . . ?
O27 C9 C10 125.0(2) . . ?
C10 C9 C8 119.4(2) . . ?
N65 C63 C61 115.9(2) . . ?
O79 C63 N65 123.1(2) . . ?
O79 C63 C61 121.0(2) . . ?
C59 C54 N65 109.6(2) . . ?
C59 C54 C55 122.5(2) . . ?
C55 C54 N65 127.9(2) . . ?
O25 C8 C7 124.2(2) . . ?
O25 C8 C9 114.5(2) . . ?
C7 C8 C9 121.4(2) . . ?
N20 C22 C12 105.27(19) . . ?
N20 C22 C21 112.0(2) . . ?
C21 C22 C12 114.2(2) . . ?
C54 C59 C53 111.51(19) . . ?
C54 C59 C58 119.1(2) . . ?
C58 C59 C53 129.1(2) . . ?
O50 C49 C40 124.8(2) . . ?
O50 C49 C48 114.1(3) . . ?
C40 C49 C48 121.1(2) . . ?
C6 C11 C12 110.7(2) . . ?
C6 C11 C10 119.5(2) . . ?
C10 C11 C12 129.7(2) . . ?
N5 C13 C14 105.89(18) . . ?
N5 C13 C12 104.24(18) . . ?
C14 C13 C12 117.43(18) . . ?
C13 C14 C19 112.11(19) . . ?
C13 C14 C2 107.48(19) . . ?
C2 C14 C19 118.34(19) . . ?
C22 C12 C13 113.55(19) . . ?
C11 C12 C22 117.00(18) . . ?
C11 C12 C13 102.05(19) . . ?
C11 C12 C23 113.9(2) . . ?
C23 C12 C22 100.68(19) . . ?
C23 C12 C13 110.04(19) . . ?
C46 C41 C40 119.0(3) . . ?
C42 C41 C40 122.5(2) . . ?
C42 C41 C46 118.4(2) . . ?
C72 C73 C53 102.9(2) . . ?
C17 C19 C14 115.33(19) . . ?
C17 C19 C21 108.6(2) . . ?
C21 C19 C14 106.55(18) . . ?
C64 C62 C60 106.96(19) . . ?
C64 C62 C68 113.31(19) . . ?
C68 C62 C60 118.5(2) . . ?
C33 C32 C31 120.0(2) . . ?
N71 C72 C73 104.8(2) . . ?
N71 C66 C53 105.20(19) . . ?
N71 C66 C70 111.0(2) . . ?
C70 C66 C53 114.80(19) . . ?
O80 C57 C58 123.3(2) . . ?
O80 C57 C56 116.1(2) . . ?
C58 C57 C56 120.5(2) . . ?
C59 C58 C57 119.4(2) . . ?
O77 C56 C57 115.2(2) . . ?
O77 C56 C55 124.3(2) . . ?
C55 C56 C57 120.5(2) . . ?
O18 C2 C14 114.3(2) . . ?
O18 C2 C3 104.0(2) . . ?
C14 C2 C3 110.5(2) . . ?
C15 C17 C19 122.1(3) . . ?
C15 C17 C1 123.3(3) . . ?
C1 C17 C19 114.5(2) . . ?
N20 C24 C23 104.1(2) . . ?
C69 C67 C68 114.4(2) . . ?
C74 C67 C68 122.5(2) . . ?
C74 C67 C69 123.0(3) . . ?
O75 C60 C62 114.1(2) . . ?
O75 C60 C61 105.0(2) . . ?
C62 C60 C61 110.7(2) . . ?
C63 C61 C60 118.5(2) . . ?
C47 C48 C49 120.4(3) . . ?
C4 C3 C2 118.2(2) . . ?
C62 C68 C70 106.6(2) . . ?
C67 C68 C62 115.0(2) . . ?
C67 C68 C70 108.4(2) . . ?
C22 C21 C19 109.09(18) . . ?
C9 C10 C11 119.6(2) . . ?
C47 C46 C41 119.2(2) . . ?
C47 C46 C45 122.9(3) . . ?
C45 C46 C41 117.9(3) . . ?
C56 C55 C54 117.9(2) . . ?
N71 C69 C67 112.0(2) . . ?
C32 C33 C34 121.2(2) . . ?
C36 C35 C34 121.7(2) . . ?
C24 C23 C12 102.2(2) . . ?
C66 C70 C68 109.3(2) . . ?
C17 C15 C16 122.3(3) . . ?
C35 C36 C37 119.4(2) . . ?
C48 C47 C46 121.1(2) . . ?
C43 C42 C41 121.1(3) . . ?
C67 C74 C76 122.3(3) . . ?
O18 C16 C15 111.2(3) . . ?
N20 C1 C17 111.9(2) . . ?
O75 C76 C74 112.1(2) . . ?
C44 C45 C46 122.0(3) . . ?
C42 C43 C44 120.6(4) . . ?
C45 C44 C43 120.0(3) . . ?
C5 O1 C82 58.2(13) . . ?
C5 O1 C18 48.0(12) . . ?
C82 O1 C18 56.9(14) . . ?
O1 C5 C82 65.7(11) . . ?
C18 C5 O1 73.5(13) . . ?
C18 C5 C82 67.3(19) . . ?
C5 C82 O1 56.1(12) . . ?
C5 C82 C18 49.4(15) . . ?
C18 C82 O1 62.8(12) . . ?
C5 C18 O1 58.6(10) . . ?
C5 C18 C82 63.3(19) . . ?
C82 C18 O1 60.4(11) . . ?

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
O29 C4 C3 C2 145.7(3) . . . . ?
O51 C37 C38 C39 -179.2(2) . . . . ?
O51 C37 C36 C35 179.3(3) . . . . ?
N5 C6 C7 C8 -175.5(2) . . . . ?
N5 C6 C11 C12 -8.2(3) . . . . ?
N5 C6 C11 C10 175.4(2) . . . . ?
N5 C4 C3 C2 -34.2(4) . . . . ?
N5 C13 C14 C19 157.28(18) . . . . ?
N5 C13 C14 C2 -71.0(2) . . . . ?
N5 C13 C12 C22 -145.7(2) . . . . ?
N5 C13 C12 C11 -18.9(2) . . . . ?
N5 C13 C12 C23 102.3(2) . . . . ?
O75 C60 C61 C63 127.6(2) . . . . ?
N65 C64 C53 C59 -15.2(2) . . . . ?
N65 C64 C53 C73 103.7(2) . . . . ?
N65 C64 C53 C66 -143.68(19) . . . . ?
N65 C64 C62 C60 -70.9(2) . . . . ?
N65 C64 C62 C68 156.68(19) . . . . ?
N65 C63 C61 C60 -30.5(4) . . . . ?
N65 C54 C59 C53 -8.3(3) . . . . ?
N65 C54 C59 C58 176.8(2) . . . . ?
N65 C54 C55 C56 -177.3(2) . . . . ?
O50 C49 C48 C47 177.2(3) . . . . ?
O27 C9 C8 O25 -1.6(3) . . . . ?
O27 C9 C8 C7 177.7(2) . . . . ?
O27 C9 C10 C11 -178.6(3) . . . . ?
O18 C2 C3 C4 131.4(3) . . . . ?
O79 C63 C61 C60 150.1(3) . . . . ?
N71 C66 C70 C68 62.3(2) . . . . ?
C39 C34 C33 C32 -1.4(3) . . . . ?
C39 C34 C35 C36 0.6(4) . . . . ?
O52 C31 C30 C39 180.0(2) . . . . ?
O52 C31 C30 C40 -5.6(4) . . . . ?
O52 C31 C32 C33 178.4(2) . . . . ?
N20 C22 C12 C11 155.4(2) . . . . ?
N20 C22 C12 C13 -86.0(2) . . . . ?
N20 C22 C12 C23 31.5(2) . . . . ?
N20 C22 C21 C19 61.0(2) . . . . ?
N20 C24 C23 C12 40.9(2) . . . . ?
O77 C56 C55 C54 -178.8(2) . . . . ?
O80 C57 C58 C59 -179.3(2) . . . . ?
O80 C57 C56 O77 -1.6(4) . . . . ?
O80 C57 C56 C55 178.5(2) . . . . ?
C6 N5 C4 O29 -23.3(4) . . . . ?
C6 N5 C4 C3 156.6(2) . . . . ?
C6 N5 C13 C14 -109.0(2) . . . . ?
C6 N5 C13 C12 15.5(2) . . . . ?
C6 C7 C8 O25 -179.1(2) . . . . ?
C6 C7 C8 C9 1.7(4) . . . . ?
C6 C11 C12 C22 141.6(2) . . . . ?
C6 C11 C12 C13 17.0(3) . . . . ?
C6 C11 C12 C23 -101.5(2) . . . . ?
C6 C11 C10 C9 -0.6(4) . . . . ?
C31 C32 C33 C34 1.3(4) . . . . ?
C64 N65 C63 O79 -177.4(3) . . . . ?
C64 N65 C63 C61 3.2(3) . . . . ?
C64 N65 C54 C59 -2.6(3) . . . . ?
C64 N65 C54 C55 176.7(2) . . . . ?
C64 C53 C59 C54 14.8(3) . . . . ?
C64 C53 C59 C58 -170.9(2) . . . . ?
C64 C53 C73 C72 78.8(2) . . . . ?
C64 C53 C66 N71 -87.6(2) . . . . ?
C64 C53 C66 C70 34.8(3) . . . . ?
C64 C62 C60 O75 -73.2(3) . . . . ?
C64 C62 C60 C61 44.9(3) . . . . ?
C64 C62 C68 C67 60.1(3) . . . . ?
C64 C62 C68 C70 -60.1(3) . . . . ?
C4 N5 C6 C7 17.7(4) . . . . ?
C4 N5 C6 C11 -160.0(2) . . . . ?
C4 N5 C13 C14 47.9(3) . . . . ?
C4 N5 C13 C12 172.4(2) . . . . ?
C40 C49 C48 C47 -1.8(4) . . . . ?
C40 C41 C46 C47 0.1(4) . . . . ?
C40 C41 C46 C45 179.3(3) . . . . ?
C40 C41 C42 C43 179.9(4) . . . . ?
C53 C64 C62 C60 172.76(19) . . . . ?
C53 C64 C62 C68 40.4(3) . . . . ?
C53 C59 C58 C57 -173.8(2) . . . . ?
C53 C73 C72 N71 38.0(2) . . . . ?
C53 C66 C70 C68 -56.9(3) . . . . ?
C7 C6 C11 C12 174.0(2) . . . . ?
C7 C6 C11 C10 -2.5(4) . . . . ?
C30 C39 C34 C33 -0.2(3) . . . . ?
C30 C39 C34 C35 178.7(2) . . . . ?
C30 C39 C38 C37 -179.6(2) . . . . ?
C30 C31 C32 C33 0.5(4) . . . . ?
C30 C40 C49 O50 1.9(4) . . . . ?
C30 C40 C49 C48 -179.3(2) . . . . ?
C30 C40 C41 C46 -179.9(2) . . . . ?
C30 C40 C41 C42 -0.1(4) . . . . ?
C34 C39 C30 C31 2.0(3) . . . . ?
C34 C39 C30 C40 -172.5(2) . . . . ?
C34 C39 C38 C37 -0.4(3) . . . . ?
C34 C35 C36 C37 0.2(4) . . . . ?
C38 C39 C30 C31 -178.9(2) . . . . ?
C38 C39 C30 C40 6.7(3) . . . . ?
C38 C39 C34 C33 -179.4(2) . . . . ?
C38 C39 C34 C35 -0.5(3) . . . . ?
C38 C37 C36 C35 -1.1(4) . . . . ?
C63 N65 C64 C53 171.9(2) . . . . ?
C63 N65 C64 C62 47.3(3) . . . . ?
C63 N65 C54 C59 -161.2(2) . . . . ?
C63 N65 C54 C55 18.1(4) . . . . ?
C54 N65 C64 C53 11.6(2) . . . . ?
C54 N65 C64 C62 -113.0(2) . . . . ?
C54 N65 C63 O79 -20.8(4) . . . . ?
C54 N65 C63 C61 159.9(2) . . . . ?
C54 C59 C58 C57 0.2(4) . . . . ?
C8 C9 C10 C11 4.1(4) . . . . ?
C22 N20 C24 C23 -20.9(3) . . . . ?
C22 N20 C1 C17 -48.4(3) . . . . ?
C22 C12 C23 C24 -44.2(2) . . . . ?
C59 C53 C73 C72 -168.17(18) . . . . ?
C59 C53 C66 N71 152.6(2) . . . . ?
C59 C53 C66 C70 -85.0(3) . . . . ?
C59 C54 C55 C56 1.9(4) . . . . ?
C49 C40 C30 C39 -89.4(3) . . . . ?
C49 C40 C30 C31 96.2(3) . . . . ?
C49 C40 C41 C46 -1.2(3) . . . . ?
C49 C40 C41 C42 178.6(3) . . . . ?
C49 C48 C47 C46 0.6(5) . . . . ?
C11 C6 C7 C8 1.9(4) . . . . ?
C11 C12 C23 C24 -170.30(19) . . . . ?
C13 N5 C6 C7 172.5(2) . . . . ?
C13 N5 C6 C11 -5.2(3) . . . . ?
C13 N5 C4 O29 -175.9(2) . . . . ?
C13 N5 C4 C3 3.9(3) . . . . ?
C13 C14 C19 C17 60.6(3) . . . . ?
C13 C14 C19 C21 -60.0(2) . . . . ?
C13 C14 C2 O18 -74.4(2) . . . . ?
C13 C14 C2 C3 42.5(3) . . . . ?
C13 C12 C23 C24 75.9(2) . . . . ?
C14 C13 C12 C22 -29.0(3) . . . . ?
C14 C13 C12 C11 97.8(2) . . . . ?
C14 C13 C12 C23 -140.9(2) . . . . ?
C14 C19 C17 C15 59.3(3) . . . . ?
C14 C19 C17 C1 -118.2(2) . . . . ?
C14 C19 C21 C22 68.7(2) . . . . ?
C14 C2 C3 C4 8.3(4) . . . . ?
C12 C22 C21 C19 -58.6(2) . . . . ?
C12 C11 C10 C9 -176.3(2) . . . . ?
C12 C13 C14 C19 41.4(3) . . . . ?
C12 C13 C14 C2 173.1(2) . . . . ?
C41 C40 C30 C39 89.3(3) . . . . ?
C41 C40 C30 C31 -85.1(3) . . . . ?
C41 C40 C49 O50 -176.8(3) . . . . ?
C41 C40 C49 C48 2.0(4) . . . . ?
C41 C46 C47 C48 0.2(4) . . . . ?
C41 C46 C45 C44 1.1(5) . . . . ?
C41 C42 C43 C44 0.5(7) . . . . ?
C73 C53 C59 C54 -103.3(2) . . . . ?
C73 C53 C59 C58 71.1(3) . . . . ?
C73 C53 C66 N71 30.7(2) . . . . ?
C73 C53 C66 C70 153.1(2) . . . . ?
C19 C14 C2 O18 53.8(3) . . . . ?
C19 C14 C2 C3 170.7(2) . . . . ?
C19 C17 C15 C16 -3.5(5) . . . . ?
C19 C17 C1 N20 52.4(3) . . . . ?
C62 C64 C53 C59 102.1(2) . . . . ?
C62 C64 C53 C73 -139.0(2) . . . . ?
C62 C64 C53 C66 -26.4(3) . . . . ?
C62 C60 C61 C63 4.1(3) . . . . ?
C62 C68 C70 C66 68.1(2) . . . . ?
C32 C31 C30 C39 -2.1(3) . . . . ?
C32 C31 C30 C40 172.3(2) . . . . ?
C72 N71 C66 C53 -8.0(2) . . . . ?
C72 N71 C66 C70 -132.8(2) . . . . ?
C72 N71 C69 C67 74.6(3) . . . . ?
C66 N71 C72 C73 -18.4(2) . . . . ?
C66 N71 C69 C67 -47.5(3) . . . . ?
C66 C53 C59 C54 140.4(2) . . . . ?
C66 C53 C59 C58 -45.3(4) . . . . ?
C66 C53 C73 C72 -41.8(2) . . . . ?
C57 C56 C55 C54 1.1(4) . . . . ?
C58 C57 C56 O77 176.5(2) . . . . ?
C58 C57 C56 C55 -3.4(4) . . . . ?
C56 C57 C58 C59 2.7(4) . . . . ?
C2 O18 C16 C15 89.6(3) . . . . ?
C2 C14 C19 C17 -65.4(3) . . . . ?
C2 C14 C19 C21 174.0(2) . . . . ?
C17 C19 C21 C22 -56.1(2) . . . . ?
C17 C15 C16 O18 -64.3(4) . . . . ?
C24 N20 C22 C12 -7.0(3) . . . . ?
C24 N20 C22 C21 -131.7(2) . . . . ?
C24 N20 C1 C17 73.1(3) . . . . ?
C67 C68 C70 C66 -56.2(2) . . . . ?
C67 C74 C76 O75 -65.0(4) . . . . ?
C60 O75 C76 C74 88.8(3) . . . . ?
C60 C62 C68 C67 -66.5(3) . . . . ?
C60 C62 C68 C70 173.4(2) . . . . ?
C68 C62 C60 O75 56.3(3) . . . . ?
C68 C62 C60 C61 174.4(2) . . . . ?
C68 C67 C69 N71 52.8(3) . . . . ?
C68 C67 C74 C76 -2.3(4) . . . . ?
C21 C22 C12 C11 -81.3(3) . . . . ?
C21 C22 C12 C13 37.2(3) . . . . ?
C21 C22 C12 C23 154.8(2) . . . . ?
C21 C19 C17 C15 178.7(3) . . . . ?
C21 C19 C17 C1 1.2(3) . . . . ?
C10 C9 C8 O25 176.0(2) . . . . ?
C10 C9 C8 C7 -4.7(4) . . . . ?
C10 C11 C12 C22 -42.4(4) . . . . ?
C10 C11 C12 C13 -167.0(3) . . . . ?
C10 C11 C12 C23 74.5(3) . . . . ?
C46 C41 C42 C43 -0.3(5) . . . . ?
C46 C45 C44 C43 -0.9(7) . . . . ?
C55 C54 C59 C53 172.4(2) . . . . ?
C55 C54 C59 C58 -2.6(4) . . . . ?
C69 N71 C72 C73 -143.0(2) . . . . ?
C69 N71 C66 C53 116.0(2) . . . . ?
C69 N71 C66 C70 -8.7(3) . . . . ?
C69 C67 C68 C62 -119.1(3) . . . . ?
C69 C67 C68 C70 0.1(3) . . . . ?
C69 C67 C74 C76 174.2(3) . . . . ?
C33 C34 C35 C36 179.5(2) . . . . ?
C35 C34 C33 C32 179.7(2) . . . . ?
C15 C17 C1 N20 -125.0(3) . . . . ?
C36 C37 C38 C39 1.2(4) . . . . ?
C47 C46 C45 C44 -179.7(4) . . . . ?
C42 C41 C46 C47 -179.8(3) . . . . ?
C42 C41 C46 C45 -0.5(4) . . . . ?
C42 C43 C44 C45 0.1(8) . . . . ?
C26 O25 C8 C7 -3.3(4) . . . . ?
C26 O25 C8 C9 176.0(3) . . . . ?
C74 C67 C68 C62 57.8(3) . . . . ?
C74 C67 C68 C70 176.9(3) . . . . ?
C74 C67 C69 N71 -124.0(3) . . . . ?
C16 O18 C2 C14 -67.3(3) . . . . ?
C16 O18 C2 C3 172.1(2) . . . . ?
C1 N20 C22 C12 117.7(2) . . . . ?
C1 N20 C22 C21 -7.0(3) . . . . ?
C1 N20 C24 C23 -145.1(2) . . . . ?
C1 C17 C15 C16 173.7(3) . . . . ?
C28 O27 C9 C8 -171.0(3) . . . . ?
C28 O27 C9 C10 11.6(5) . . . . ?
C78 O77 C56 C57 -178.9(3) . . . . ?
C78 O77 C56 C55 1.0(4) . . . . ?
C76 O75 C60 C62 -67.7(3) . . . . ?
C76 O75 C60 C61 171.0(2) . . . . ?
C45 C46 C47 C48 -179.0(3) . . . . ?
C81 O80 C57 C58 44.3(5) . . . . ?
C81 O80 C57 C56 -137.6(4) . . . . ?
O1 C5 C82 C18 81.4(15) . . . . ?
O1 C5 C18 C82 -70.0(11) . . . . ?
O1 C82 C18 C5 67.3(14) . . . . ?
C5 O1 C82 C18 -57.6(15) . . . . ?
C5 O1 C18 C82 75(2) . . . . ?
C5 C82 C18 O1 -67.3(14) . . . . ?
C82 O1 C5 C18 72(2) . . . . ?
C82 O1 C18 C5 -75(2) . . . . ?
C82 C5 C18 O1 70.0(11) . . . . ?
C18 O1 C5 C82 -72(2) . . . . ?
C18 O1 C82 C5 57.6(15) . . . . ?
C18 C5 C82 O1 -81.4(15) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.046 0.124 0.337 15.9 0.0 ?
2 0.640 0.162 0.494 14.1 0.2 ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: alcohol'
####################################################################### 
# 
# 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_726
_database_code_depnum_ccdc_archive 'CCDC 1041059'
_audit_update_record             
;
2014-12-27 deposited with the CCDC.
2016-04-29 downloaded from the CCDC.
;
_chemical_formula_moiety         'C31 H25 N O3'
_chemical_formula_sum            'C31 H25 N O3'
_chemical_formula_weight         459.52
_chemical_absolute_configuration unk
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2

_cell_length_a                   9.0291(3)
_cell_length_b                   12.1317(4)
_cell_length_c                   21.5315(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2358.53(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    295
_exptl_absorpt_coefficient_mu    0.659
_exptl_crystal_density_diffrn    1.2941
_exptl_crystal_F_000             968.0
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            8159
_diffrn_reflns_theta_full        73.4053
_diffrn_reflns_theta_max         73.41
_diffrn_reflns_theta_min         4.11
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_radiation_wavelength     1.54184
_diffrn_ambient_temperature      295
_reflns_Friedel_coverage         0.726
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              15
_reflns_limit_k_min              -15
_reflns_limit_l_max              26
_reflns_limit_l_min              -26
_reflns_number_gt                3724
_reflns_number_total             4731
_reflns_threshold_expression     I>=2u(I)
_refine_diff_density_max         0.1720
_refine_diff_density_min         -0.2798
_refine_diff_density_rms         0.0639
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_d_res_high            0.8044
_refine_ls_d_res_low             10.7657
_refine_ls_goodness_of_fit_ref   0.8070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    39
_refine_ls_number_parameters     332
_refine_ls_number_reflns         4156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0467
_refine_ls_restrained_S_all      0.8070
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1170P)²+0.2462P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1346
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  {H25a,H25b} of C25, H6 of C6, H2 of C2, H3 of C3, H5 of C5, H28 of C28, H18
  of C18, H17 of C17, H15 of C15, H31 of C31, H12 of C12, H13 of C13, H16 of
  C16, H32 of C32, H35 of C35, H34 of C34, H33 of C33
 At 1.5 times of:
  {H29a,H29b,H29c} of C29
2.a Ternary CH refined with riding coordinates:
 C28(H28)
2.b Secondary CH2 refined with riding coordinates:
 C25(H25a,H25b)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C2(H2), C3(H3), C5(H5), C18(H18), C17(H17), C15(H15), C31(H31),
 C12(H12), C13(H13), C16(H16), C32(H32), C35(H35), C34(H34), C33(H33)
2.d Idealised Me refined as rotating group:
 C29(H29a,H29b,H29c)
;
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_refinement_flags_posn
O10 O -0.34183(19) -0.41632(13) -0.23622(7) 0.0457(4) Uani 1.000000 .
N26 N -0.15919(19) -0.37105(14) 0.00469(8) 0.0372(4) Uani 1.000000 .
O24 O -0.2175(2) -0.52911(13) 0.06769(7) 0.0498(4) Uani 1.000000 .
O8 O -0.3184(2) -0.60225(14) -0.26715(7) 0.0506(4) Uani 1.000000 .
C23 C -0.2208(2) -0.54893(15) -0.04453(9) 0.0337(4) Uani 1.000000 .
C25 C -0.1348(2) -0.44130(16) -0.04983(9) 0.0344(4) Uani 1.000000 .
H25a H -0.1660(2) -0.40231(16) -0.08693(9) 0.0413(5) Uiso 1.000000 R
H25b H -0.0300(2) -0.45731(16) -0.05374(9) 0.0413(5) Uiso 1.000000 R
C22 C -0.2759(2) -0.61069(15) -0.09641(10) 0.0332(4) Uani 1.000000 .
C1 C -0.2590(2) -0.58256(17) 0.01464(10) 0.0399(4) Uani 1.000000 .
C21 C -0.2485(2) -0.58335(15) -0.16059(9) 0.0333(4) Uani 1.000000 .
C4 C -0.3720(2) -0.70282(16) -0.08448(11) 0.0416(5) Uani 1.000000 .
C20 C -0.1395(2) -0.50002(16) -0.18401(9) 0.0354(4) Uani 1.000000 .
C19 C 0.0155(2) -0.50644(17) -0.17275(10) 0.0374(4) Uani 1.000000 .
C27 C -0.1242(3) -0.4315(2) 0.05861(11) 0.0445(5) Uani 1.000000 .
C6 C -0.4284(3) -0.72389(18) -0.19339(12) 0.0480(5) Uani 1.000000 .
H6 H -0.4808(3) -0.75775(18) -0.22532(12) 0.0576(6) Uiso 1.000000 R
C11 C -0.1921(3) -0.41868(19) -0.22229(10) 0.0417(5) Uani 1.000000 .
C2 C -0.3506(3) -0.67459(19) 0.02581(12) 0.0502(6) Uani 1.000000 .
H2 H -0.3734(3) -0.69501(19) 0.06633(12) 0.0602(7) Uiso 1.000000 R
C7 C -0.3332(2) -0.63504(17) -0.20554(10) 0.0395(4) Uani 1.000000 .
C3 C -0.4050(3) -0.73271(19) -0.02212(12) 0.0508(6) Uani 1.000000 .
H3 H -0.4651(3) -0.79344(19) -0.01442(12) 0.0609(7) Uiso 1.000000 R
C5 C -0.4421(2) -0.75915(18) -0.13380(13) 0.0481(5) Uani 1.000000 .
H5 H -0.4987(2) -0.82145(18) -0.12532(13) 0.0577(6) Uiso 1.000000 R
C29 C -0.3589(3) -0.2789(2) 0.06610(12) 0.0591(6) Uani 1.000000 .
H29a H -0.372(3) -0.3435(3) 0.0912(4) 0.0886(10) Uiso 1.000000 GR
H29b H -0.2875(13) -0.2312(16) 0.0853(5) 0.0886(10) Uiso 1.000000 GR
H29c H -0.4516(14) -0.2408(18) 0.06220(15) 0.0886(10) Uiso 1.000000 GR
C14 C 0.1093(3) -0.42151(19) -0.19655(11) 0.0462(5) Uani 1.000000 .
C28 C -0.3044(2) -0.31238(17) 0.00230(10) 0.0398(4) Uani 1.000000 .
H28 H -0.3774(2) -0.36285(17) -0.01569(10) 0.0478(5) Uiso 1.000000 R
C18 C 0.0823(2) -0.59241(18) -0.13790(11) 0.0430(5) Uani 1.000000 .
H18 H 0.0238(2) -0.64953(18) -0.12279(11) 0.0516(6) Uiso 1.000000 R
C17 C 0.2316(3) -0.5927(2) -0.12613(14) 0.0537(6) Uani 1.000000 .
H17 H 0.2729(3) -0.6490(2) -0.10247(14) 0.0645(7) Uiso 1.000000 R
C30 C -0.2858(3) -0.21589(19) -0.04207(12) 0.0468(5) Uani 1.000000 .
C15 C 0.2627(3) -0.4261(2) -0.18380(13) 0.0571(6) Uani 1.000000 .
H15 H 0.3240(3) -0.3710(2) -0.19938(13) 0.0685(8) Uiso 1.000000 R
C31 C -0.3289(4) -0.2249(3) -0.10378(13) 0.0639(7) Uani 1.000000 .
H31 H -0.3782(4) -0.2879(3) -0.11721(13) 0.0767(9) Uiso 1.000000 R
C12 C -0.1001(3) -0.3352(2) -0.24632(12) 0.0558(6) Uani 1.000000 .
H12 H -0.1396(3) -0.2800(2) -0.27121(12) 0.0669(8) Uiso 1.000000 R
C13 C 0.0474(3) -0.3360(2) -0.23285(13) 0.0587(7) Uani 1.000000 .
H13 H 0.1078(3) -0.2798(2) -0.24767(13) 0.0705(8) Uiso 1.000000 R
C16 C 0.3230(3) -0.5079(2) -0.14974(14) 0.0586(6) Uani 1.000000 .
H16 H 0.4243(3) -0.5085(2) -0.14182(14) 0.0703(8) Uiso 1.000000 R
C9 C -0.3821(3) -0.4972(3) -0.28021(12) 0.0556(6) Uani 1.000000 .
C32 C -0.2990(5) -0.1406(4) -0.14559(17) 0.0916(13) Uani 1.000000 .
H32 H -0.3240(5) -0.1492(4) -0.18721(17) 0.1099(16) Uiso 1.000000 R
C35 C -0.2179(3) -0.1192(2) -0.02244(17) 0.0660(8) Uani 1.000000 .
H35 H -0.1886(3) -0.1116(2) 0.01875(17) 0.0792(9) Uiso 1.000000 R
C34 C -0.1935(4) -0.0336(3) -0.0643(2) 0.0950(14) Uani 1.000000 .
H34 H -0.1505(4) 0.0318(3) -0.0508(2) 0.1140(16) Uiso 1.000000 R
C33 C -0.2335(5) -0.0457(4) -0.1262(2) 0.1010(15) Uani 1.000000 .
H33 H -0.2154(5) 0.0109(4) -0.1544(2) 0.1212(18) Uiso 1.000000 R
H9a H -0.495(3) -0.501(2) -0.2785(12) 0.053(8) Uiso 1.000000 .
H27a H -0.020(3) -0.4573(19) 0.0563(10) 0.034(6) Uiso 1.000000 .
H27b H -0.137(3) -0.389(2) 0.0972(12) 0.042(6) Uiso 1.000000 .
H9b H -0.332(3) -0.480(2) -0.3194(12) 0.050(7) Uiso 1.000000 .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O10 C11 1.385(3) .
O10 C9 1.411(3) .
N26 C25 1.467(2) .
N26 C27 1.409(3) .
N26 C28 1.493(3) .
O24 C1 1.366(3) .
O24 C27 1.466(3) .
O8 C7 1.391(3) .
O8 C9 1.426(3) .
C23 C25 1.523(2) .
C23 C22 1.434(3) .
C23 C1 1.382(3) .
C22 C21 1.443(3) .
C22 C4 1.438(3) .
C1 C2 1.410(3) .
C21 C20 1.498(3) .
C21 C7 1.384(3) .
C4 C3 1.422(3) .
C4 C5 1.413(3) .
C20 C19 1.423(3) .
C20 C11 1.371(3) .
C19 C14 1.428(3) .
C19 C18 1.419(3) .
C6 C7 1.403(3) .
C6 C5 1.358(4) .
C11 C12 1.408(3) .
C2 C3 1.343(4) .
C29 C28 1.515(3) .
C14 C15 1.414(4) .
C14 C13 1.414(4) .
C28 C30 1.520(3) .
C18 C17 1.372(3) .
C17 C16 1.414(4) .
C30 C31 1.389(4) .
C30 C35 1.389(4) .
C15 C16 1.349(4) .
C31 C32 1.389(4) .
C12 C13 1.362(4) .
C32 C33 1.361(7) .
C35 C34 1.393(5) .
C34 C33 1.389(6) .

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
C9 O10 C11 112.48(19) . .
C27 N26 C25 108.84(16) . .
C28 N26 C25 112.41(15) . .
C28 N26 C27 118.29(18) . .
C27 O24 C1 115.45(16) . .
C9 O8 C7 113.87(18) . .
C22 C23 C25 124.49(17) . .
C1 C23 C25 116.73(17) . .
C1 C23 C22 118.49(17) . .
C23 C25 N26 111.19(16) . .
C21 C22 C23 124.50(17) . .
C4 C22 C23 118.46(19) . .
C4 C22 C21 116.95(19) . .
C23 C1 O24 124.21(18) . .
C2 C1 O24 113.23(19) . .
C2 C1 C23 122.5(2) . .
C20 C21 C22 126.17(17) . .
C7 C21 C22 118.10(18) . .
C7 C21 C20 115.69(18) . .
C3 C4 C22 119.5(2) . .
C5 C4 C22 120.8(2) . .
C5 C4 C3 119.5(2) . .
C19 C20 C21 123.51(18) . .
C11 C20 C21 117.42(19) . .
C11 C20 C19 118.86(19) . .
C14 C19 C20 118.8(2) . .
C18 C19 C20 123.23(19) . .
C18 C19 C14 117.9(2) . .
O24 C27 N26 113.66(17) . .
C5 C6 C7 118.3(2) . .
C20 C11 O10 118.9(2) . .
C12 C11 O10 118.8(2) . .
C12 C11 C20 122.3(2) . .
C3 C2 C1 119.9(2) . .
C21 C7 O8 118.9(2) . .
C6 C7 O8 117.1(2) . .
C6 C7 C21 123.8(2) . .
C2 C3 C4 121.0(2) . .
C6 C5 C4 121.1(2) . .
C15 C14 C19 118.9(2) . .
C13 C14 C19 119.5(2) . .
C13 C14 C15 121.6(2) . .
C29 C28 N26 112.47(18) . .
C30 C28 N26 106.98(17) . .
C30 C28 C29 113.55(19) . .
C17 C18 C19 121.1(2) . .
C16 C17 C18 120.4(2) . .
C31 C30 C28 120.6(2) . .
C35 C30 C28 120.5(2) . .
C35 C30 C31 118.8(3) . .
C16 C15 C14 122.0(2) . .
C32 C31 C30 120.5(4) . .
C13 C12 C11 119.6(2) . .
C12 C13 C14 120.6(2) . .
C15 C16 C17 119.7(2) . .
O8 C9 O10 112.66(19) . .
C33 C32 C31 120.6(4) . .
C34 C35 C30 120.2(3) . .
C33 C34 C35 120.1(4) . .
C34 C33 C32 119.8(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_689
_database_code_depnum_ccdc_archive 'CCDC 1453552'
_audit_update_record             
;
2016-02-16 deposited with the CCDC.
2016-04-29 downloaded from the CCDC.
;
_chemical_formula_moiety         'C22 H16 O3'
_chemical_formula_sum            'C22 H16 O3'
_chemical_formula_weight         328.35
_chemical_absolute_configuration unk
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z

_cell_length_a                   9.9608(3)
_cell_length_b                   9.4348(3)
_cell_length_c                   10.0343(3)
_cell_angle_alpha                90
_cell_angle_beta                 113.748(4)
_cell_angle_gamma                90
_cell_measurement_temperature    293
_cell_measurement_reflns_used    4973
_cell_measurement_theta_max      71.1090
_cell_measurement_theta_min      4.6320
_cell_volume                     863.16(5)
_cell_formula_units_Z            2
_exptl_crystal_colour            colorless
_exptl_crystal_description       plate
_exptl_absorpt_coefficient_mu    0.672
_exptl_crystal_density_diffrn    1.2633
_exptl_crystal_F_000             344.0
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9817
_diffrn_reflns_theta_full        73.0988
_diffrn_reflns_theta_max         73.10
_diffrn_reflns_theta_min         4.81
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.9893
_diffrn_measured_fraction_theta_max 0.9893
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_radiation_wavelength     1.54184
_reflns_Friedel_coverage         0.702
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              9
_reflns_limit_k_min              -11
_reflns_limit_l_max              12
_reflns_limit_l_min              -12
_reflns_number_gt                2763
_reflns_number_total             2967
_reflns_threshold_expression     I>=2u(I)
_refine_diff_density_max         0.1607
_refine_diff_density_min         -0.1510
_refine_diff_density_rms         0.0304
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_d_res_high            0.8057
_refine_ls_d_res_low             9.1847
_refine_ls_goodness_of_fit_ref   0.6369
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    29
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3453
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0366
_refine_ls_restrained_S_all      0.6369
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1299P)²+0.2307P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1175
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  H19 of C19, H4 of C4, H22 of C22, H3 of C3, H11 of C11, H12 of C12, H25 of
  C25, H23 of C23, {H15a,H15b} of C15, H16 of C16, H17 of C17, H24 of C24
 At 1.5 times of:
  {H21a,H21b,H21c} of C21
2.a Secondary CH2 refined with riding coordinates:
 C15(H15a,H15b)
2.b Aromatic/amide H refined with riding coordinates:
 C19(H19), C4(H4), C22(H22), C3(H3), C11(H11), C12(H12), C25(H25), C23(H23),
 C16(H16), C17(H17), C24(H24)
2.c Idealised Me refined as rotating group:
 C21(H21a,H21b,H21c)
;
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_refinement_flags_posn
O1 O 0.18467(14) 0.55509(16) 0.22712(16) 0.0575(3) Uani 1.000000 .
O14 O 0.16503(13) 0.80300(16) 0.21311(16) 0.0568(4) Uani 1.000000 .
C7 C 0.41451(17) 0.65207(19) 0.25188(17) 0.0424(4) Uani 1.000000 .
O20 O 0.89866(14) 0.85578(18) 0.34774(19) 0.0700(5) Uani 1.000000 .
C8 C 0.33278(17) 0.72687(18) 0.11209(18) 0.0425(4) Uani 1.000000 .
C6 C 0.56857(17) 0.6673(2) 0.33661(17) 0.0430(4) Uani 1.000000 .
C2 C 0.33576(19) 0.5662(2) 0.30523(19) 0.0485(4) Uani 1.000000 .
C19 C 0.65650(17) 0.7622(2) 0.29717(18) 0.0463(4) Uani 1.000000 .
H19 H 0.61346(17) 0.8196(2) 0.21556(18) 0.0555(5) Uiso 1.000000 R
C13 C 0.20648(18) 0.7978(2) 0.0969(2) 0.0488(4) Uani 1.000000 .
C9 C 0.37268(18) 0.72208(19) -0.00911(18) 0.0454(4) Uani 1.000000 .
C4 C 0.5479(2) 0.4945(3) 0.5102(2) 0.0606(5) Uani 1.000000 .
H4 H 0.5923(2) 0.4396(3) 0.5935(2) 0.0727(6) Uiso 1.000000 R
C18 C 0.80471(18) 0.7701(2) 0.3786(2) 0.0533(5) Uani 1.000000 .
C22 C 0.4896(2) 0.6391(2) -0.0116(2) 0.0529(4) Uani 1.000000 .
H22 H 0.5432(2) 0.5831(2) 0.0685(2) 0.0635(5) Uiso 1.000000 R
C3 C 0.4006(2) 0.4856(2) 0.4328(2) 0.0593(5) Uani 1.000000 .
H3 H 0.3437(2) 0.4270(2) 0.4638(2) 0.0712(6) Uiso 1.000000 R
C10 C 0.2875(2) 0.8009(2) -0.1373(2) 0.0548(4) Uani 1.000000 .
C5 C 0.6344(2) 0.5858(2) 0.46612(19) 0.0520(4) Uani 1.000000 .
C11 C 0.1620(2) 0.8752(2) -0.1426(2) 0.0658(6) Uani 1.000000 .
H11 H 0.1069(2) 0.9273(2) -0.2254(2) 0.0790(7) Uiso 1.000000 R
C12 C 0.1204(2) 0.8720(2) -0.0297(2) 0.0619(5) Uani 1.000000 .
H12 H 0.0357(2) 0.9185(2) -0.0362(2) 0.0743(6) Uiso 1.000000 R
C25 C 0.3297(3) 0.7994(3) -0.2561(2) 0.0708(6) Uani 1.000000 .
H25 H 0.2760(3) 0.8521(3) -0.3388(2) 0.0850(7) Uiso 1.000000 R
C23 C 0.5257(3) 0.6394(3) -0.1298(3) 0.0665(6) Uani 1.000000 .
H23 H 0.6032(3) 0.5840(3) -0.1292(3) 0.0799(7) Uiso 1.000000 R
C21 C 0.8384(2) 0.9382(3) 0.2199(3) 0.0776(7) Uani 1.000000 .
H21a H 0.791(2) 0.8773(3) 0.1376(4) 0.1165(11) Uiso 1.000000 GR
H21b H 0.7683(18) 1.0035(16) 0.2281(10) 0.1165(11) Uiso 1.000000 GR
H21c H 0.9153(4) 0.9900(18) 0.2069(13) 0.1165(11) Uiso 1.000000 GR
C15 C 0.1080(2) 0.6751(3) 0.2416(3) 0.0667(6) Uani 1.000000 .
H15a H 0.0058(2) 0.6667(3) 0.1750(3) 0.0800(7) Uiso 1.000000 R
H15b H 0.1120(2) 0.6780(3) 0.3398(3) 0.0800(7) Uiso 1.000000 R
C16 C 0.7881(2) 0.5987(3) 0.5472(2) 0.0661(6) Uani 1.000000 .
H16 H 0.8330(2) 0.5454(3) 0.6316(2) 0.0793(7) Uiso 1.000000 R
C17 C 0.8709(2) 0.6865(3) 0.5050(2) 0.0685(6) Uani 1.000000 .
H17 H 0.9715(2) 0.6919(3) 0.5593(2) 0.0823(7) Uiso 1.000000 R
C24 C 0.4455(3) 0.7236(3) -0.2522(3) 0.0785(7) Uani 1.000000 .
H24 H 0.4728(3) 0.7266(3) -0.3305(3) 0.0942(9) Uiso 1.000000 R


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C2 1.393(2) .
O1 C15 1.406(3) .
O14 C13 1.385(2) .
O14 C15 1.411(3) .
C7 C8 1.486(2) .
C7 C6 1.431(2) .
C7 C2 1.377(2) .
O20 C18 1.363(3) .
O20 C21 1.411(3) .
C8 C13 1.378(2) .
C8 C9 1.424(2) .
C6 C19 1.416(2) .
C6 C5 1.422(2) .
C2 C3 1.404(3) .
C19 C18 1.371(2) .
C13 C12 1.401(3) .
C9 C22 1.412(3) .
C9 C10 1.431(2) .
C4 C3 1.358(3) .
C4 C5 1.410(3) .
C18 C17 1.411(3) .
C22 C23 1.370(3) .
C10 C11 1.416(3) .
C10 C25 1.414(3) .
C5 C16 1.420(3) .
C11 C12 1.354(3) .
C25 C24 1.345(4) .
C23 C24 1.410(4) .
C16 C17 1.352(4) .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C15 O1 C2 112.94(15) . .
C15 O14 C13 114.89(16) . .
C6 C7 C8 124.20(15) . .
C2 C7 C8 117.70(14) . .
C2 C7 C6 118.07(15) . .
C21 O20 C18 117.00(14) . .
C13 C8 C7 117.61(15) . .
C9 C8 C7 123.76(14) . .
C9 C8 C13 118.51(15) . .
C19 C6 C7 122.23(15) . .
C5 C6 C7 118.57(16) . .
C5 C6 C19 119.19(15) . .
C7 C2 O1 118.77(16) . .
C3 C2 O1 117.92(17) . .
C3 C2 C7 123.29(17) . .
C18 C19 C6 120.42(17) . .
C8 C13 O14 119.50(16) . .
C12 C13 O14 117.70(16) . .
C12 C13 C8 122.71(18) . .
C22 C9 C8 123.28(16) . .
C10 C9 C8 118.85(16) . .
C10 C9 C22 117.83(16) . .
C5 C4 C3 120.96(18) . .
C19 C18 O20 124.73(18) . .
C17 C18 O20 114.86(16) . .
C17 C18 C19 120.40(19) . .
C23 C22 C9 121.3(2) . .
C4 C3 C2 118.82(18) . .
C11 C10 C9 119.10(18) . .
C25 C10 C9 118.83(19) . .
C25 C10 C11 122.06(19) . .
C4 C5 C6 120.11(17) . .
C16 C5 C6 118.10(19) . .
C16 C5 C4 121.79(19) . .
C12 C11 C10 121.34(18) . .
C11 C12 C13 119.28(18) . .
C24 C25 C10 121.6(2) . .
C24 C23 C22 120.1(2) . .
O14 C15 O1 112.82(14) . .
C17 C16 C5 121.72(19) . .
C16 C17 C18 120.08(17) . .
C23 C24 C25 120.2(2) . .

_chemical_melting_point          411
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane'
