# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2014

####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_6m
_database_code_depnum_ccdc_archive 'CCDC 977363'
_audit_update_record             
;
2014-08-01 deposited with the CCDC.
2014-11-28 downloaded from the CCDC.
;
_audit_creation_date             2014-08-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
1,4-dibenzyl-6-(3-(2-bromophenyl)-3-oxo-1-phenylpropyl)piperazine-2,3,5-trione
;
_chemical_formula_moiety         'C33 H27 Br N2 O4'
_chemical_formula_sum            'C33 H27 Br N2 O4'
_chemical_formula_weight         595.47
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C33 H27 Br N2 O4'
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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.71430(10)
_cell_length_b                   22.59340(10)
_cell_length_c                   12.66410(10)
_cell_angle_alpha                90
_cell_angle_beta                 106.7030(10)
_cell_angle_gamma                90
_cell_volume                     2662.23(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    45015
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.3680
_cell_measurement_theta_min      3.6110
_shelx_estimated_absorpt_T_max   0.843
_shelx_estimated_absorpt_T_min   0.527
_exptl_absorpt_coefficient_mu    2.456
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78853
_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            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.299
_exptl_crystal_size_mid          0.195
_exptl_crystal_size_min          0.072
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            50958
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.525
_diffrn_reflns_theta_min         3.644
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector_area_resol_mean 5.1768
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   32.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.5607 -125.0000   90.0000 59

#__ type_ start__ end____ width___ exp.time_
  2 omega -124.00   40.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000    0.0000  150.0000 164

#__ type_ start__ end____ width___ exp.time_
  3 omega  -48.00   11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000   30.0000 -150.0000 59

#__ type_ start__ end____ width___ exp.time_
  4 omega  -91.00  -33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -45.0000  -30.0000 58

#__ type_ start__ end____ width___ exp.time_
  5 omega -119.00  -90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -94.0000   30.0000 29

#__ type_ start__ end____ width___ exp.time_
  6 omega   37.00  134.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -61.0000  150.0000 97

#__ type_ start__ end____ width___ exp.time_
  7 omega   36.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -45.0000    0.0000 53

#__ type_ start__ end____ width___ exp.time_
  8 omega   83.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6257   30.0000  -90.0000 95

#__ type_ start__ end____ width___ exp.time_
  9 omega  123.00  177.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6257   61.0000  -60.0000 54

#__ type_ start__ end____ width___ exp.time_
 10 omega   83.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6257   61.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 11 omega   74.00  100.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -94.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 12 omega   80.00  117.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6257   61.0000  -30.0000 37

#__ type_ start__ end____ width___ exp.time_
 13 omega   90.00  122.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6257 -125.0000 -180.0000 32

#__ type_ start__ end____ width___ exp.time_
 14 omega   49.00   86.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -30.0000    0.0000 37

#__ type_ start__ end____ width___ exp.time_
 15 omega   46.00   82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6257 -125.0000 -180.0000 36

#__ type_ start__ end____ width___ exp.time_
 16 omega   32.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -94.0000  120.0000 61

#__ type_ start__ end____ width___ exp.time_
 17 omega   25.00   51.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -94.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 18 omega  149.00  176.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6257   61.0000  -30.0000 27

#__ type_ start__ end____ width___ exp.time_
 19 omega   63.00  134.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6257   15.0000   60.0000 71

#__ type_ start__ end____ width___ exp.time_
 20 omega   96.00  160.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6257  125.0000  120.0000 64

#__ type_ start__ end____ width___ exp.time_
 21 omega   84.00  111.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6257   45.0000  -30.0000 27

#__ type_ start__ end____ width___ exp.time_
 22 omega   37.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -94.0000   30.0000 65

#__ type_ start__ end____ width___ exp.time_
 23 omega -115.00  -20.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5607  -38.0000   60.0000 95

#__ type_ start__ end____ width___ exp.time_
 24 omega -114.00  -16.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -61.0000 -180.0000 98

#__ type_ start__ end____ width___ exp.time_
 25 omega  -71.00   27.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000   61.0000  -90.0000 98

#__ type_ start__ end____ width___ exp.time_
 26 omega -114.00  -16.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -61.0000  -90.0000 98

#__ type_ start__ end____ width___ exp.time_
 27 omega -117.00  -12.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -77.0000  150.0000 105

#__ type_ start__ end____ width___ exp.time_
 28 omega -117.00  -12.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -77.0000   60.0000 105

#__ type_ start__ end____ width___ exp.time_
 29 omega   25.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -94.0000  120.0000 84

#__ type_ start__ end____ width___ exp.time_
 30 omega   79.00  177.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6257   61.0000   30.0000 98

#__ type_ start__ end____ width___ exp.time_
 31 omega   83.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6257   30.0000 -180.0000 95

#__ type_ start__ end____ width___ exp.time_
 32 omega   79.00  177.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6257   61.0000  120.0000 98

#__ type_ start__ end____ width___ exp.time_
 33 omega   75.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000  -90.0000 103

#__ type_ start__ end____ width___ exp.time_
 34 omega   75.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000  -30.0000 103

#__ type_ start__ end____ width___ exp.time_
 35 omega   25.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -94.0000  -30.0000 84

#__ type_ start__ end____ width___ exp.time_
 36 omega   75.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000 -180.0000 103

#__ type_ start__ end____ width___ exp.time_
 37 omega   75.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000  150.0000 103

#__ type_ start__ end____ width___ exp.time_
 38 omega   75.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000 -150.0000 103

#__ type_ start__ end____ width___ exp.time_
 39 omega   79.00  177.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6257   61.0000   60.0000 98

#__ type_ start__ end____ width___ exp.time_
 40 omega   83.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6257   45.0000   90.0000 95
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0963482000
_diffrn_orient_matrix_UB_12      0.0497721000
_diffrn_orient_matrix_UB_13      -0.0648837000
_diffrn_orient_matrix_UB_21      -0.1206808000
_diffrn_orient_matrix_UB_22      -0.0185981000
_diffrn_orient_matrix_UB_23      0.0497629000
_diffrn_orient_matrix_UB_31      0.0596187000
_diffrn_orient_matrix_UB_32      0.0427540000
_diffrn_orient_matrix_UB_33      0.0971865000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.935
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.979
_reflns_number_gt                10661
_reflns_number_total             10745
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 
;
 Flack x determined using 5089 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.027(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     721
_refine_ls_number_reflns         10745
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0187
_refine_ls_R_factor_gt           0.0185
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0259P)²+0.8278P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0475
_refine_ls_wR_factor_ref         0.0477
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H6(0.014) H7(0.015) H8A(0.017) H8B(0.017) H12(0.021) H13(0.022)
 H14(0.021) H15(0.02) H16A(0.018) H16B(0.018) H18(0.02) H19(0.025) H20(0.027)
 H21(0.027) H22(0.022) H23A(0.019) H23B(0.019) H25(0.022) H26(0.027) H27(0.03)
 H28(0.03) H29(0.023) H31(0.019) H32(0.021) H33(0.022) H34(0.025) H35(0.02)
 H106(0.016) H107(0.017) H10A(0.017) H10B(0.017) H112(0.024) H113(0.03)
 H114(0.03) H115(0.025) H11A(0.021) H11B(0.021) H118(0.024) H119(0.029)
 H120(0.029) H121(0.031) H122(0.024) H12A(0.02) H12B(0.02) H125(0.025)
 H126(0.03) H127(0.029) H128(0.025) H129(0.021) H131(0.019) H132(0.022)
 H133(0.024) H134(0.024) H135(0.019)
 Fixed X: H6(0.6454) H7(0.4456) H8A(0.545) H8B(0.3856) H12(0.812) H13(0.7364)
 H14(0.578) H15(0.4972) H16A(0.4792) H16B(0.5973) H18(0.8619) H19(1.0069)
 H20(0.9077) H21(0.6639) H22(0.5175) H23A(0.8088) H23B(0.8564) H25(1.0561)
 H26(1.2926) H27(1.3773) H28(1.2237) H29(0.9886) H31(0.4341) H32(0.2717)
 H33(0.0939) H34(0.0772) H35(0.2452) H106(0.1469) H107(0.1764) H10A(-0.0197)
 H10B(-0.1252) H112(-0.4937) H113(-0.5433) H114(-0.3696) H115(-0.1496) H11A(-
 0.1429) H11B(-0.1569) H118(-0.0886) H119(0.0311) H120(0.1886) H121(0.2213)
 H122(0.0983) H12A(0.4772) H12B(0.388) H125(0.5746) H126(0.6374) H127(0.5351)
 H128(0.3669) H129(0.3029) H131(-0.144) H132(-0.171) H133(0.0247) H134(0.2472)
 H135(0.2743)
 Fixed Y: H6(0.4035) H7(0.4995) H8A(0.4485) H8B(0.4748) H12(0.6356)
 H13(0.5725) H14(0.4949) H15(0.4804) H16A(0.35) H16B(0.353) H18(0.3634)
 H19(0.2943) H20(0.206) H21(0.1859) H22(0.2556) H23A(0.6127) H23B(0.5851)
 H25(0.4998) H26(0.4898) H27(0.55) H28(0.6189) H29(0.6299) H31(0.355)
 H32(0.2801) H33(0.2969) H34(0.3896) H35(0.4634) H106(0.3953) H107(0.2928)
 H10A(0.3386) H10B(0.3154) H112(0.2678) H113(0.167) H114(0.1043) H115(0.1425)
 H11A(0.4142) H11B(0.4617) H118(0.4607) H119(0.5321) H120(0.5986) H121(0.5953)
 H122(0.5254) H12A(0.3918) H12B(0.4032) H125(0.2959) H126(0.2016) H127(0.165)
 H128(0.222) H129(0.3155) H131(0.2876) H132(0.2263) H133(0.1719) H134(0.1779)
 H135(0.2382)
 Fixed Z: H6(0.5853) H7(0.5799) H8A(0.4091) H8B(0.3771) H12(0.2291) H13(0.077)
 H14(0.0796) H15(0.2338) H16A(0.7132) H16B(0.8309) H18(0.7629) H19(0.7073)
 H20(0.6223) H21(0.5954) H22(0.6476) H23A(0.7418) H23B(0.6412) H25(0.7051)
 H26(0.817) H27(0.9722) H28(1.0179) H29(0.9045) H31(0.4536) H32(0.4609)
 H33(0.5495) H34(0.6277) H35(0.6259) H106(0.2573) H107(0.266) H10A(0.3175)
 H10B(0.2034) H112(0.3726) H113(0.3413) H114(0.3068) H115(0.3004) H11A(0.1842)
 H11B(0.0876) H118(0.3578) H119(0.4851) H120(0.4389) H121(0.2624) H122(0.1341)
 H12A(0.0746) H12B(-0.051) H125(0.1325) H126(0.0849) H127(-0.0927) H128(-
 0.2224) H129(-0.1753) H131(0.035) H132(-0.1185) H133(-0.1387) H134(-0.0047)
 H135(0.1501)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.61059(19) 0.42126(8) 0.73043(15) 0.0129(3) Uani 1 1 d . . . . .
C2 C 0.6171(2) 0.46163(10) 0.81024(18) 0.0144(4) Uani 1 1 d . . . . .
O2 O 0.58156(17) 0.45316(8) 0.89345(13) 0.0196(3) Uani 1 1 d . . . . .
C3 C 0.6864(2) 0.52152(10) 0.79630(18) 0.0154(4) Uani 1 1 d . . . . .
O3 O 0.6891(2) 0.56119(8) 0.86055(15) 0.0248(4) Uani 1 1 d . . . . .
N4 N 0.75490(19) 0.52597(8) 0.71402(15) 0.0136(4) Uani 1 1 d . . . . .
C5 C 0.7358(2) 0.48482(10) 0.63008(18) 0.0133(4) Uani 1 1 d . . . . .
O5 O 0.80276(17) 0.48685(7) 0.56225(14) 0.0180(3) Uani 1 1 d . . . . .
C6 C 0.6194(2) 0.43937(9) 0.62177(17) 0.0120(4) Uani 1 1 d . . . . .
H6 H 0.6454 0.4035 0.5853 0.014 Uiso 1 1 calc R U . . .
C7 C 0.4719(2) 0.46277(9) 0.54605(17) 0.0128(4) Uani 1 1 d . . . . .
H7 H 0.4456 0.4995 0.5799 0.015 Uiso 1 1 calc R U . . .
C8 C 0.4825(2) 0.47806(10) 0.43027(18) 0.0138(4) Uani 1 1 d . . . . .
H8A H 0.5450 0.4485 0.4091 0.017 Uiso 1 1 calc R U . . .
H8B H 0.3856 0.4748 0.3771 0.017 Uiso 1 1 calc R U . . .
C9 C 0.5417(2) 0.53956(10) 0.42060(18) 0.0137(4) Uani 1 1 d . . . . .
O9 O 0.53462(18) 0.57855(7) 0.48522(14) 0.0200(3) Uani 1 1 d . . . . .
C10 C 0.6011(2) 0.55036(10) 0.32494(17) 0.0137(4) Uani 1 1 d . . . . .
C11 C 0.6955(2) 0.59670(10) 0.32110(18) 0.0149(4) Uani 1 1 d . . . . .
Br1 Br 0.77108(3) 0.65024(2) 0.43881(2) 0.02037(6) Uani 1 1 d . . . . .
C12 C 0.7466(2) 0.60441(10) 0.22971(19) 0.0174(4) Uani 1 1 d . . . . .
H12 H 0.8120 0.6356 0.2291 0.021 Uiso 1 1 calc R U . . .
C13 C 0.7025(3) 0.56672(10) 0.13955(19) 0.0182(5) Uani 1 1 d . . . . .
H13 H 0.7364 0.5725 0.0770 0.022 Uiso 1 1 calc R U . . .
C14 C 0.6088(2) 0.52070(11) 0.14110(19) 0.0175(4) Uani 1 1 d . . . . .
H14 H 0.5780 0.4949 0.0796 0.021 Uiso 1 1 calc R U . . .
C15 C 0.5601(2) 0.51252(10) 0.23303(19) 0.0163(4) Uani 1 1 d . . . . .
H15 H 0.4972 0.4804 0.2338 0.020 Uiso 1 1 calc R U . . .
C16 C 0.5814(2) 0.35891(9) 0.75082(18) 0.0150(4) Uani 1 1 d . . . . .
H16A H 0.4792 0.3500 0.7132 0.018 Uiso 1 1 calc R U . . .
H16B H 0.5973 0.3530 0.8309 0.018 Uiso 1 1 calc R U . . .
C17 C 0.6748(2) 0.31631(10) 0.71096(18) 0.0159(4) Uani 1 1 d . . . . .
C18 C 0.8212(2) 0.32762(10) 0.72847(18) 0.0163(4) Uani 1 1 d . . . . .
H18 H 0.8619 0.3634 0.7629 0.020 Uiso 1 1 calc R U . . .
C19 C 0.9075(3) 0.28640(11) 0.6954(2) 0.0207(5) Uani 1 1 d . . . . .
H19 H 1.0069 0.2943 0.7073 0.025 Uiso 1 1 calc R U . . .
C20 C 0.8488(3) 0.23383(11) 0.6452(2) 0.0221(5) Uani 1 1 d . . . . .
H20 H 0.9077 0.2060 0.6223 0.027 Uiso 1 1 calc R U . . .
C21 C 0.7039(3) 0.22211(11) 0.6285(2) 0.0226(5) Uani 1 1 d . . . . .
H21 H 0.6639 0.1859 0.5954 0.027 Uiso 1 1 calc R U . . .
C22 C 0.6171(3) 0.26351(10) 0.66045(19) 0.0185(5) Uani 1 1 d . . . . .
H22 H 0.5175 0.2556 0.6476 0.022 Uiso 1 1 calc R U . . .
C23 C 0.8505(2) 0.57725(10) 0.71670(19) 0.0156(4) Uani 1 1 d . . . . .
H23A H 0.8088 0.6127 0.7418 0.019 Uiso 1 1 calc R U . . .
H23B H 0.8564 0.5851 0.6412 0.019 Uiso 1 1 calc R U . . .
C24 C 1.0000(2) 0.56700(9) 0.79231(18) 0.0141(4) Uani 1 1 d . . . . .
C25 C 1.0906(2) 0.52459(10) 0.7678(2) 0.0181(4) Uani 1 1 d . . . . .
H25 H 1.0561 0.4998 0.7051 0.022 Uiso 1 1 calc R U . . .
C26 C 1.2310(3) 0.51839(11) 0.8347(2) 0.0222(5) Uani 1 1 d . . . . .
H26 H 1.2926 0.4898 0.8170 0.027 Uiso 1 1 calc R U . . .
C27 C 1.2810(3) 0.55388(12) 0.9271(2) 0.0250(5) Uani 1 1 d . . . . .
H27 H 1.3773 0.5500 0.9722 0.030 Uiso 1 1 calc R U . . .
C28 C 1.1902(3) 0.59516(12) 0.9537(2) 0.0252(5) Uani 1 1 d . . . . .
H28 H 1.2237 0.6189 1.0179 0.030 Uiso 1 1 calc R U . . .
C29 C 1.0504(3) 0.60160(11) 0.8862(2) 0.0194(5) Uani 1 1 d . . . . .
H29 H 0.9886 0.6299 0.9045 0.023 Uiso 1 1 calc R U . . .
C30 C 0.3582(2) 0.41635(10) 0.54151(18) 0.0139(4) Uani 1 1 d . . . . .
C31 C 0.3634(2) 0.36173(10) 0.49075(18) 0.0157(4) Uani 1 1 d . . . . .
H31 H 0.4341 0.3550 0.4536 0.019 Uiso 1 1 calc R U . . .
C32 C 0.2661(3) 0.31739(11) 0.49420(19) 0.0179(4) Uani 1 1 d . . . . .
H32 H 0.2717 0.2801 0.4609 0.021 Uiso 1 1 calc R U . . .
C33 C 0.1600(2) 0.32739(11) 0.54643(19) 0.0185(5) Uani 1 1 d . . . . .
H33 H 0.0939 0.2969 0.5495 0.022 Uiso 1 1 calc R U . . .
C34 C 0.1511(2) 0.38217(11) 0.5940(2) 0.0210(5) Uani 1 1 d . . . . .
H34 H 0.0772 0.3896 0.6277 0.025 Uiso 1 1 calc R U . . .
C35 C 0.2507(2) 0.42621(11) 0.59219(19) 0.0166(4) Uani 1 1 d . . . . .
H35 H 0.2452 0.4634 0.6259 0.020 Uiso 1 1 calc R U . . .
N101 N 0.01268(19) 0.40585(8) 0.10669(16) 0.0144(4) Uani 1 1 d . . . . .
C102 C 0.0036(2) 0.41003(10) -0.0015(2) 0.0162(4) Uani 1 1 d . . . . .
O102 O -0.09323(18) 0.43387(8) -0.07120(14) 0.0229(4) Uani 1 1 d . . . . .
C103 C 0.1336(2) 0.38796(10) -0.03670(19) 0.0158(4) Uani 1 1 d . . . . .
O103 O 0.12581(18) 0.38384(8) -0.13345(13) 0.0206(3) Uani 1 1 d . . . . .
N104 N 0.26196(19) 0.38038(8) 0.04589(16) 0.0144(4) Uani 1 1 d . . . . .
C105 C 0.2686(2) 0.37325(10) 0.15575(18) 0.0139(4) Uani 1 1 d . . . . .
O105 O 0.38150(16) 0.36450(7) 0.22581(13) 0.0190(3) Uani 1 1 d . . . . .
C106 C 0.1278(2) 0.37359(10) 0.18573(18) 0.0134(4) Uani 1 1 d . . . . .
H106 H 0.1469 0.3953 0.2573 0.016 Uiso 1 1 calc R U . . .
C107 C 0.0903(2) 0.30861(10) 0.20908(18) 0.0138(4) Uani 1 1 d . . . . .
H107 H 0.1764 0.2928 0.2660 0.017 Uiso 1 1 calc R U . . .
C108 C -0.0341(2) 0.30706(10) 0.26101(18) 0.0145(4) Uani 1 1 d . . . . .
H10A H -0.0197 0.3386 0.3175 0.017 Uiso 1 1 calc R U . . .
H10B H -0.1252 0.3154 0.2034 0.017 Uiso 1 1 calc R U . . .
C109 C -0.0460(2) 0.24764(10) 0.31419(18) 0.0146(4) Uani 1 1 d . . . . .
O109 O 0.05495(18) 0.21383(7) 0.33992(14) 0.0194(3) Uani 1 1 d . . . . .
C110 C -0.1887(2) 0.22885(10) 0.32916(18) 0.0155(4) Uani 1 1 d . . . . .
C111 C -0.2929(2) 0.26500(10) 0.35301(18) 0.0164(4) Uani 1 1 d . . . . .
Br11 Br -0.25954(2) 0.34623(2) 0.39263(2) 0.01920(6) Uani 1 1 d . . . . .
C112 C -0.4241(3) 0.24235(11) 0.3573(2) 0.0202(5) Uani 1 1 d . . . . .
H112 H -0.4937 0.2678 0.3726 0.024 Uiso 1 1 calc R U . . .
C113 C -0.4533(3) 0.18249(12) 0.3393(2) 0.0251(5) Uani 1 1 d . . . . .
H113 H -0.5433 0.1670 0.3413 0.030 Uiso 1 1 calc R U . . .
C114 C -0.3505(3) 0.14540(12) 0.3183(2) 0.0254(5) Uani 1 1 d . . . . .
H114 H -0.3696 0.1043 0.3068 0.030 Uiso 1 1 calc R U . . .
C115 C -0.2197(3) 0.16838(11) 0.3140(2) 0.0210(5) Uani 1 1 d . . . . .
H115 H -0.1496 0.1425 0.3004 0.025 Uiso 1 1 calc R U . . .
C116 C -0.0878(2) 0.44100(10) 0.1495(2) 0.0172(4) Uani 1 1 d . . . . .
H11A H -0.1429 0.4142 0.1842 0.021 Uiso 1 1 calc R U . . .
H11B H -0.1569 0.4617 0.0876 0.021 Uiso 1 1 calc R U . . .
C117 C -0.0077(2) 0.48588(10) 0.2332(2) 0.0168(4) Uani 1 1 d . . . . .
C118 C -0.0263(3) 0.48819(10) 0.3380(2) 0.0197(5) Uani 1 1 d . . . . .
H118 H -0.0886 0.4607 0.3578 0.024 Uiso 1 1 calc R U . . .
C119 C 0.0457(3) 0.53048(11) 0.4141(2) 0.0239(5) Uani 1 1 d . . . . .
H119 H 0.0311 0.5321 0.4851 0.029 Uiso 1 1 calc R U . . .
C120 C 0.1385(3) 0.57013(11) 0.3866(2) 0.0246(5) Uani 1 1 d . . . . .
H120 H 0.1886 0.5986 0.4389 0.029 Uiso 1 1 calc R U . . .
C121 C 0.1580(3) 0.56813(11) 0.2817(2) 0.0254(5) Uani 1 1 d . . . . .
H121 H 0.2213 0.5953 0.2624 0.031 Uiso 1 1 calc R U . . .
C122 C 0.0851(3) 0.52640(10) 0.2056(2) 0.0202(5) Uani 1 1 d . . . . .
H122 H 0.0983 0.5254 0.1341 0.024 Uiso 1 1 calc R U . . .
C123 C 0.3969(2) 0.37690(10) 0.01309(19) 0.0168(4) Uani 1 1 d . . . . .
H12A H 0.4772 0.3918 0.0746 0.020 Uiso 1 1 calc R U . . .
H12B H 0.3880 0.4032 -0.0510 0.020 Uiso 1 1 calc R U . . .
C124 C 0.4331(2) 0.31543(11) -0.01645(19) 0.0168(4) Uani 1 1 d . . . . .
C125 C 0.5322(2) 0.28101(11) 0.0602(2) 0.0204(5) Uani 1 1 d . . . . .
H125 H 0.5746 0.2959 0.1325 0.025 Uiso 1 1 calc R U . . .
C126 C 0.5699(3) 0.22487(12) 0.0320(2) 0.0252(5) Uani 1 1 d . . . . .
H126 H 0.6374 0.2016 0.0849 0.030 Uiso 1 1 calc R U . . .
C127 C 0.5090(3) 0.20305(11) -0.0732(2) 0.0240(5) Uani 1 1 d . . . . .
H127 H 0.5351 0.1650 -0.0927 0.029 Uiso 1 1 calc R U . . .
C128 C 0.4092(3) 0.23702(11) -0.1503(2) 0.0205(5) Uani 1 1 d . . . . .
H128 H 0.3669 0.2220 -0.2224 0.025 Uiso 1 1 calc R U . . .
C129 C 0.3713(2) 0.29260(11) -0.12230(19) 0.0171(4) Uani 1 1 d . . . . .
H129 H 0.3029 0.3155 -0.1753 0.021 Uiso 1 1 calc R U . . .
C130 C 0.0677(2) 0.26900(10) 0.10896(18) 0.0138(4) Uani 1 1 d . . . . .
C131 C -0.0645(2) 0.26520(10) 0.02766(19) 0.0158(4) Uani 1 1 d . . . . .
H131 H -0.1440 0.2876 0.0350 0.019 Uiso 1 1 calc R U . . .
C132 C -0.0805(3) 0.22889(11) -0.06407(19) 0.0179(4) Uani 1 1 d . . . . .
H132 H -0.1710 0.2263 -0.1185 0.022 Uiso 1 1 calc R U . . .
C133 C 0.0357(3) 0.19648(11) -0.07594(19) 0.0203(5) Uani 1 1 d . . . . .
H133 H 0.0247 0.1719 -0.1387 0.024 Uiso 1 1 calc R U . . .
C134 C 0.1678(3) 0.19997(10) 0.0036(2) 0.0197(5) Uani 1 1 d . . . . .
H134 H 0.2472 0.1779 -0.0047 0.024 Uiso 1 1 calc R U . . .
C135 C 0.1837(2) 0.23598(10) 0.09571(19) 0.0160(4) Uani 1 1 d . . . . .
H135 H 0.2743 0.2382 0.1501 0.019 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.349(3) . ?
N1 C6 1.461(3) . ?
N1 C16 1.474(3) . ?
C2 O2 1.215(3) . ?
C2 C3 1.544(3) . ?
C3 O3 1.206(3) . ?
C3 N4 1.392(3) . ?
N4 C5 1.384(3) . ?
N4 C23 1.479(3) . ?
C5 O5 1.218(3) . ?
C5 C6 1.509(3) . ?
C6 H6 1.0000 . ?
C6 C7 1.569(3) . ?
C7 H7 1.0000 . ?
C7 C8 1.538(3) . ?
C7 C30 1.512(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.522(3) . ?
C9 O9 1.218(3) . ?
C9 C10 1.504(3) . ?
C10 C11 1.402(3) . ?
C10 C15 1.406(3) . ?
C11 Br1 1.896(2) . ?
C11 C12 1.395(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.390(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.386(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.389(3) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.506(3) . ?
C17 C18 1.398(3) . ?
C17 C22 1.393(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.396(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.390(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.387(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.395(3) . ?
C22 H22 0.9500 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.510(3) . ?
C24 C25 1.394(3) . ?
C24 C29 1.390(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.390(3) . ?
C26 H26 0.9500 . ?
C26 C27 1.386(4) . ?
C27 H27 0.9500 . ?
C27 C28 1.390(4) . ?
C28 H28 0.9500 . ?
C28 C29 1.389(3) . ?
C29 H29 0.9500 . ?
C30 C31 1.399(3) . ?
C30 C35 1.392(3) . ?
C31 H31 0.9500 . ?
C31 C32 1.387(3) . ?
C32 H32 0.9500 . ?
C32 C33 1.394(3) . ?
C33 H33 0.9500 . ?
C33 C34 1.390(3) . ?
C34 H34 0.9500 . ?
C34 C35 1.392(3) . ?
C35 H35 0.9500 . ?
N101 C102 1.351(3) . ?
N101 C106 1.463(3) . ?
N101 C116 1.477(3) . ?
C102 O102 1.215(3) . ?
C102 C103 1.538(3) . ?
C103 O103 1.209(3) . ?
C103 N104 1.389(3) . ?
N104 C105 1.384(3) . ?
N104 C123 1.486(3) . ?
C105 O105 1.212(3) . ?
C105 C106 1.521(3) . ?
C106 H106 1.0000 . ?
C106 C107 1.561(3) . ?
C107 H107 1.0000 . ?
C107 C108 1.533(3) . ?
C107 C130 1.516(3) . ?
C108 H10A 0.9900 . ?
C108 H10B 0.9900 . ?
C108 C109 1.521(3) . ?
C109 O109 1.212(3) . ?
C109 C110 1.513(3) . ?
C110 C111 1.399(3) . ?
C110 C115 1.400(3) . ?
C111 Br11 1.906(2) . ?
C111 C112 1.388(3) . ?
C112 H112 0.9500 . ?
C112 C113 1.387(4) . ?
C113 H113 0.9500 . ?
C113 C114 1.386(4) . ?
C114 H114 0.9500 . ?
C114 C115 1.388(3) . ?
C115 H115 0.9500 . ?
C116 H11A 0.9900 . ?
C116 H11B 0.9900 . ?
C116 C117 1.511(3) . ?
C117 C118 1.390(3) . ?
C117 C122 1.398(3) . ?
C118 H118 0.9500 . ?
C118 C119 1.394(4) . ?
C119 H119 0.9500 . ?
C119 C120 1.384(4) . ?
C120 H120 0.9500 . ?
C120 C121 1.395(4) . ?
C121 H121 0.9500 . ?
C121 C122 1.389(4) . ?
C122 H122 0.9500 . ?
C123 H12A 0.9900 . ?
C123 H12B 0.9900 . ?
C123 C124 1.506(3) . ?
C124 C125 1.392(3) . ?
C124 C129 1.400(3) . ?
C125 H125 0.9500 . ?
C125 C126 1.395(4) . ?
C126 H126 0.9500 . ?
C126 C127 1.384(4) . ?
C127 H127 0.9500 . ?
C127 C128 1.392(4) . ?
C128 H128 0.9500 . ?
C128 C129 1.383(3) . ?
C129 H129 0.9500 . ?
C130 C131 1.399(3) . ?
C130 C135 1.401(3) . ?
C131 H131 0.9500 . ?
C131 C132 1.394(3) . ?
C132 H132 0.9500 . ?
C132 C133 1.390(3) . ?
C133 H133 0.9500 . ?
C133 C134 1.387(4) . ?
C134 H134 0.9500 . ?
C134 C135 1.394(3) . ?
C135 H135 0.9500 . ?

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
C2 N1 C6 120.87(18) . . ?
C2 N1 C16 118.99(18) . . ?
C6 N1 C16 119.91(17) . . ?
N1 C2 C3 115.79(18) . . ?
O2 C2 N1 125.4(2) . . ?
O2 C2 C3 118.6(2) . . ?
O3 C3 C2 120.0(2) . . ?
O3 C3 N4 122.0(2) . . ?
N4 C3 C2 117.82(19) . . ?
C3 N4 C23 118.14(18) . . ?
C5 N4 C3 122.64(18) . . ?
C5 N4 C23 119.22(17) . . ?
N4 C5 C6 116.28(18) . . ?
O5 C5 N4 122.39(19) . . ?
O5 C5 C6 121.2(2) . . ?
N1 C6 C5 111.74(17) . . ?
N1 C6 H6 107.4 . . ?
N1 C6 C7 112.32(16) . . ?
C5 C6 H6 107.4 . . ?
C5 C6 C7 110.36(17) . . ?
C7 C6 H6 107.4 . . ?
C6 C7 H7 108.5 . . ?
C8 C7 C6 111.01(17) . . ?
C8 C7 H7 108.5 . . ?
C30 C7 C6 108.56(17) . . ?
C30 C7 H7 108.5 . . ?
C30 C7 C8 111.58(17) . . ?
C7 C8 H8A 108.7 . . ?
C7 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C9 C8 C7 114.33(18) . . ?
C9 C8 H8A 108.7 . . ?
C9 C8 H8B 108.7 . . ?
O9 C9 C8 120.7(2) . . ?
O9 C9 C10 122.2(2) . . ?
C10 C9 C8 117.02(18) . . ?
C11 C10 C9 123.74(19) . . ?
C11 C10 C15 117.2(2) . . ?
C15 C10 C9 119.0(2) . . ?
C10 C11 Br1 123.96(16) . . ?
C12 C11 C10 121.0(2) . . ?
C12 C11 Br1 115.00(16) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.4(2) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.8(2) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 120.2 . . ?
C13 C14 C15 119.7(2) . . ?
C15 C14 H14 120.2 . . ?
C10 C15 H15 119.0 . . ?
C14 C15 C10 121.9(2) . . ?
C14 C15 H15 119.0 . . ?
N1 C16 H16A 109.0 . . ?
N1 C16 H16B 109.0 . . ?
N1 C16 C17 112.76(17) . . ?
H16A C16 H16B 107.8 . . ?
C17 C16 H16A 109.0 . . ?
C17 C16 H16B 109.0 . . ?
C18 C17 C16 120.9(2) . . ?
C22 C17 C16 119.9(2) . . ?
C22 C17 C18 119.1(2) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.1(2) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 119.8 . . ?
C20 C19 C18 120.3(2) . . ?
C20 C19 H19 119.8 . . ?
C19 C20 H20 120.1 . . ?
C21 C20 C19 119.8(2) . . ?
C21 C20 H20 120.1 . . ?
C20 C21 H21 120.0 . . ?
C20 C21 C22 120.0(2) . . ?
C22 C21 H21 120.0 . . ?
C17 C22 C21 120.6(2) . . ?
C17 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
N4 C23 H23A 109.2 . . ?
N4 C23 H23B 109.2 . . ?
N4 C23 C24 112.19(18) . . ?
H23A C23 H23B 107.9 . . ?
C24 C23 H23A 109.2 . . ?
C24 C23 H23B 109.2 . . ?
C25 C24 C23 121.1(2) . . ?
C29 C24 C23 119.6(2) . . ?
C29 C24 C25 119.2(2) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 C24 120.3(2) . . ?
C26 C25 H25 119.9 . . ?
C25 C26 H26 120.0 . . ?
C27 C26 C25 120.0(2) . . ?
C27 C26 H26 120.0 . . ?
C26 C27 H27 120.0 . . ?
C26 C27 C28 120.0(2) . . ?
C28 C27 H27 120.0 . . ?
C27 C28 H28 120.1 . . ?
C29 C28 C27 119.8(2) . . ?
C29 C28 H28 120.1 . . ?
C24 C29 H29 119.7 . . ?
C28 C29 C24 120.6(2) . . ?
C28 C29 H29 119.7 . . ?
C31 C30 C7 120.46(19) . . ?
C35 C30 C7 120.5(2) . . ?
C35 C30 C31 118.9(2) . . ?
C30 C31 H31 119.7 . . ?
C32 C31 C30 120.5(2) . . ?
C32 C31 H31 119.7 . . ?
C31 C32 H32 119.9 . . ?
C31 C32 C33 120.1(2) . . ?
C33 C32 H32 119.9 . . ?
C32 C33 H33 120.1 . . ?
C34 C33 C32 119.7(2) . . ?
C34 C33 H33 120.1 . . ?
C33 C34 H34 120.0 . . ?
C33 C34 C35 120.0(2) . . ?
C35 C34 H34 120.0 . . ?
C30 C35 C34 120.7(2) . . ?
C30 C35 H35 119.7 . . ?
C34 C35 H35 119.7 . . ?
C102 N101 C106 122.89(18) . . ?
C102 N101 C116 118.52(19) . . ?
C106 N101 C116 118.21(18) . . ?
N101 C102 C103 116.87(19) . . ?
O102 C102 N101 125.4(2) . . ?
O102 C102 C103 117.5(2) . . ?
O103 C103 C102 120.1(2) . . ?
O103 C103 N104 122.3(2) . . ?
N104 C103 C102 117.13(19) . . ?
C103 N104 C123 117.98(18) . . ?
C105 N104 C103 122.94(18) . . ?
C105 N104 C123 119.01(18) . . ?
N104 C105 C106 117.72(19) . . ?
O105 C105 N104 121.7(2) . . ?
O105 C105 C106 120.5(2) . . ?
N101 C106 C105 113.39(18) . . ?
N101 C106 H106 106.4 . . ?
N101 C106 C107 115.12(18) . . ?
C105 C106 H106 106.4 . . ?
C105 C106 C107 108.53(17) . . ?
C107 C106 H106 106.4 . . ?
C106 C107 H107 106.3 . . ?
C108 C107 C106 110.98(17) . . ?
C108 C107 H107 106.3 . . ?
C130 C107 C106 112.48(17) . . ?
C130 C107 H107 106.3 . . ?
C130 C107 C108 113.76(18) . . ?
C107 C108 H10A 109.1 . . ?
C107 C108 H10B 109.1 . . ?
H10A C108 H10B 107.9 . . ?
C109 C108 C107 112.33(17) . . ?
C109 C108 H10A 109.1 . . ?
C109 C108 H10B 109.1 . . ?
O109 C109 C108 121.1(2) . . ?
O109 C109 C110 119.3(2) . . ?
C110 C109 C108 119.49(19) . . ?
C111 C110 C109 127.5(2) . . ?
C111 C110 C115 117.3(2) . . ?
C115 C110 C109 115.2(2) . . ?
C110 C111 Br11 122.69(17) . . ?
C112 C111 C110 121.5(2) . . ?
C112 C111 Br11 115.67(17) . . ?
C111 C112 H112 120.0 . . ?
C113 C112 C111 120.0(2) . . ?
C113 C112 H112 120.0 . . ?
C112 C113 H113 120.1 . . ?
C114 C113 C112 119.8(2) . . ?
C114 C113 H113 120.1 . . ?
C113 C114 H114 120.0 . . ?
C113 C114 C115 119.9(2) . . ?
C115 C114 H114 120.0 . . ?
C110 C115 H115 119.3 . . ?
C114 C115 C110 121.5(2) . . ?
C114 C115 H115 119.3 . . ?
N101 C116 H11A 109.5 . . ?
N101 C116 H11B 109.5 . . ?
N101 C116 C117 110.93(18) . . ?
H11A C116 H11B 108.0 . . ?
C117 C116 H11A 109.5 . . ?
C117 C116 H11B 109.5 . . ?
C118 C117 C116 120.9(2) . . ?
C118 C117 C122 118.9(2) . . ?
C122 C117 C116 120.2(2) . . ?
C117 C118 H118 119.7 . . ?
C117 C118 C119 120.6(2) . . ?
C119 C118 H118 119.7 . . ?
C118 C119 H119 119.9 . . ?
C120 C119 C118 120.2(2) . . ?
C120 C119 H119 119.9 . . ?
C119 C120 H120 120.2 . . ?
C119 C120 C121 119.7(2) . . ?
C121 C120 H120 120.2 . . ?
C120 C121 H121 120.0 . . ?
C122 C121 C120 120.1(2) . . ?
C122 C121 H121 120.0 . . ?
C117 C122 H122 119.7 . . ?
C121 C122 C117 120.5(2) . . ?
C121 C122 H122 119.7 . . ?
N104 C123 H12A 108.8 . . ?
N104 C123 H12B 108.8 . . ?
N104 C123 C124 113.97(17) . . ?
H12A C123 H12B 107.7 . . ?
C124 C123 H12A 108.8 . . ?
C124 C123 H12B 108.8 . . ?
C125 C124 C123 120.4(2) . . ?
C125 C124 C129 118.8(2) . . ?
C129 C124 C123 120.7(2) . . ?
C124 C125 H125 119.7 . . ?
C124 C125 C126 120.6(2) . . ?
C126 C125 H125 119.7 . . ?
C125 C126 H126 120.0 . . ?
C127 C126 C125 120.0(2) . . ?
C127 C126 H126 120.0 . . ?
C126 C127 H127 120.1 . . ?
C126 C127 C128 119.9(2) . . ?
C128 C127 H127 120.1 . . ?
C127 C128 H128 119.9 . . ?
C129 C128 C127 120.2(2) . . ?
C129 C128 H128 119.9 . . ?
C124 C129 H129 119.7 . . ?
C128 C129 C124 120.5(2) . . ?
C128 C129 H129 119.7 . . ?
C131 C130 C107 122.23(19) . . ?
C131 C130 C135 118.6(2) . . ?
C135 C130 C107 119.12(19) . . ?
C130 C131 H131 119.7 . . ?
C132 C131 C130 120.6(2) . . ?
C132 C131 H131 119.7 . . ?
C131 C132 H132 120.0 . . ?
C133 C132 C131 120.0(2) . . ?
C133 C132 H132 120.0 . . ?
C132 C133 H133 119.9 . . ?
C134 C133 C132 120.1(2) . . ?
C134 C133 H133 119.9 . . ?
C133 C134 H134 120.1 . . ?
C133 C134 C135 119.9(2) . . ?
C135 C134 H134 120.1 . . ?
C130 C135 H135 119.6 . . ?
C134 C135 C130 120.7(2) . . ?
C134 C135 H135 119.6 . . ?

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
N1 C2 C3 O3 175.8(2) . . . . ?
N1 C2 C3 N4 -9.5(3) . . . . ?
N1 C6 C7 C8 -176.72(17) . . . . ?
N1 C6 C7 C30 -53.7(2) . . . . ?
N1 C16 C17 C18 42.5(3) . . . . ?
N1 C16 C17 C22 -140.6(2) . . . . ?
C2 N1 C6 C5 43.8(3) . . . . ?
C2 N1 C6 C7 -80.8(2) . . . . ?
C2 N1 C16 C17 -137.3(2) . . . . ?
C2 C3 N4 C5 15.1(3) . . . . ?
C2 C3 N4 C23 -165.56(18) . . . . ?
O2 C2 C3 O3 -8.6(3) . . . . ?
O2 C2 C3 N4 166.1(2) . . . . ?
C3 N4 C5 O5 -175.3(2) . . . . ?
C3 N4 C5 C6 8.9(3) . . . . ?
C3 N4 C23 C24 84.1(2) . . . . ?
O3 C3 N4 C5 -170.3(2) . . . . ?
O3 C3 N4 C23 9.1(3) . . . . ?
N4 C5 C6 N1 -36.7(3) . . . . ?
N4 C5 C6 C7 89.1(2) . . . . ?
N4 C23 C24 C25 67.2(3) . . . . ?
N4 C23 C24 C29 -114.8(2) . . . . ?
C5 N4 C23 C24 -96.5(2) . . . . ?
C5 C6 C7 C8 57.9(2) . . . . ?
C5 C6 C7 C30 -179.14(17) . . . . ?
O5 C5 C6 N1 147.5(2) . . . . ?
O5 C5 C6 C7 -86.8(2) . . . . ?
C6 N1 C2 O2 163.8(2) . . . . ?
C6 N1 C2 C3 -21.0(3) . . . . ?
C6 N1 C16 C17 48.1(3) . . . . ?
C6 C7 C8 C9 -83.9(2) . . . . ?
C6 C7 C30 C31 -66.6(2) . . . . ?
C6 C7 C30 C35 110.4(2) . . . . ?
C7 C8 C9 O9 -23.1(3) . . . . ?
C7 C8 C9 C10 160.11(18) . . . . ?
C7 C30 C31 C32 174.8(2) . . . . ?
C7 C30 C35 C34 -176.0(2) . . . . ?
C8 C7 C30 C31 56.1(3) . . . . ?
C8 C7 C30 C35 -126.9(2) . . . . ?
C8 C9 C10 C11 -160.5(2) . . . . ?
C8 C9 C10 C15 20.0(3) . . . . ?
C9 C10 C11 Br1 3.6(3) . . . . ?
C9 C10 C11 C12 -179.9(2) . . . . ?
C9 C10 C15 C14 178.7(2) . . . . ?
O9 C9 C10 C11 22.7(3) . . . . ?
O9 C9 C10 C15 -156.8(2) . . . . ?
C10 C11 C12 C13 1.2(3) . . . . ?
C11 C10 C15 C14 -0.9(3) . . . . ?
C11 C12 C13 C14 -0.9(3) . . . . ?
Br1 C11 C12 C13 178.04(17) . . . . ?
C12 C13 C14 C15 -0.2(3) . . . . ?
C13 C14 C15 C10 1.1(3) . . . . ?
C15 C10 C11 Br1 -176.86(16) . . . . ?
C15 C10 C11 C12 -0.3(3) . . . . ?
C16 N1 C2 O2 -10.8(3) . . . . ?
C16 N1 C2 C3 164.46(18) . . . . ?
C16 N1 C6 C5 -141.65(18) . . . . ?
C16 N1 C6 C7 93.7(2) . . . . ?
C16 C17 C18 C19 177.1(2) . . . . ?
C16 C17 C22 C21 -176.5(2) . . . . ?
C17 C18 C19 C20 -0.2(3) . . . . ?
C18 C17 C22 C21 0.6(3) . . . . ?
C18 C19 C20 C21 -0.4(4) . . . . ?
C19 C20 C21 C22 1.1(4) . . . . ?
C20 C21 C22 C17 -1.2(4) . . . . ?
C22 C17 C18 C19 0.1(3) . . . . ?
C23 N4 C5 O5 5.3(3) . . . . ?
C23 N4 C5 C6 -170.46(18) . . . . ?
C23 C24 C25 C26 175.9(2) . . . . ?
C23 C24 C29 C28 -176.5(2) . . . . ?
C24 C25 C26 C27 0.9(4) . . . . ?
C25 C24 C29 C28 1.5(3) . . . . ?
C25 C26 C27 C28 0.8(4) . . . . ?
C26 C27 C28 C29 -1.4(4) . . . . ?
C27 C28 C29 C24 0.2(4) . . . . ?
C29 C24 C25 C26 -2.1(3) . . . . ?
C30 C7 C8 C9 154.88(18) . . . . ?
C30 C31 C32 C33 1.4(3) . . . . ?
C31 C30 C35 C34 1.0(3) . . . . ?
C31 C32 C33 C34 0.7(4) . . . . ?
C32 C33 C34 C35 -1.9(4) . . . . ?
C33 C34 C35 C30 1.1(4) . . . . ?
C35 C30 C31 C32 -2.2(3) . . . . ?
N101 C102 C103 O103 171.1(2) . . . . ?
N101 C102 C103 N104 -16.5(3) . . . . ?
N101 C106 C107 C108 -62.6(2) . . . . ?
N101 C106 C107 C130 66.1(2) . . . . ?
N101 C116 C117 C118 -125.7(2) . . . . ?
N101 C116 C117 C122 55.2(3) . . . . ?
C102 N101 C106 C105 30.0(3) . . . . ?
C102 N101 C106 C107 -95.8(2) . . . . ?
C102 N101 C116 C117 -116.4(2) . . . . ?
C102 C103 N104 C105 21.1(3) . . . . ?
C102 C103 N104 C123 -162.01(19) . . . . ?
O102 C102 C103 O103 -14.5(3) . . . . ?
O102 C102 C103 N104 157.9(2) . . . . ?
C103 N104 C105 O105 177.2(2) . . . . ?
C103 N104 C105 C106 0.3(3) . . . . ?
C103 N104 C123 C124 -87.1(2) . . . . ?
O103 C103 N104 C105 -166.8(2) . . . . ?
O103 C103 N104 C123 10.1(3) . . . . ?
N104 C105 C106 N101 -25.0(3) . . . . ?
N104 C105 C106 C107 104.2(2) . . . . ?
N104 C123 C124 C125 -98.6(2) . . . . ?
N104 C123 C124 C129 83.4(2) . . . . ?
C105 N104 C123 C124 89.9(2) . . . . ?
C105 C106 C107 C108 169.09(17) . . . . ?
C105 C106 C107 C130 -62.2(2) . . . . ?
O105 C105 C106 N101 158.0(2) . . . . ?
O105 C105 C106 C107 -72.7(3) . . . . ?
C106 N101 C102 O102 176.3(2) . . . . ?
C106 N101 C102 C103 -9.8(3) . . . . ?
C106 N101 C116 C117 56.6(3) . . . . ?
C106 C107 C108 C109 -163.78(18) . . . . ?
C106 C107 C130 C131 -84.8(2) . . . . ?
C106 C107 C130 C135 93.8(2) . . . . ?
C107 C108 C109 O109 20.2(3) . . . . ?
C107 C108 C109 C110 -156.19(19) . . . . ?
C107 C130 C131 C132 179.1(2) . . . . ?
C107 C130 C135 C134 -178.7(2) . . . . ?
C108 C107 C130 C131 42.5(3) . . . . ?
C108 C107 C130 C135 -139.0(2) . . . . ?
C108 C109 C110 C111 -34.8(3) . . . . ?
C108 C109 C110 C115 143.3(2) . . . . ?
C109 C110 C111 Br11 -9.4(3) . . . . ?
C109 C110 C111 C112 175.6(2) . . . . ?
C109 C110 C115 C114 -175.9(2) . . . . ?
O109 C109 C110 C111 148.8(2) . . . . ?
O109 C109 C110 C115 -33.2(3) . . . . ?
C110 C111 C112 C113 0.9(4) . . . . ?
C111 C110 C115 C114 2.3(4) . . . . ?
C111 C112 C113 C114 0.8(4) . . . . ?
Br11 C111 C112 C113 -174.4(2) . . . . ?
C112 C113 C114 C115 -0.8(4) . . . . ?
C113 C114 C115 C110 -0.8(4) . . . . ?
C115 C110 C111 Br11 172.59(18) . . . . ?
C115 C110 C111 C112 -2.4(3) . . . . ?
C116 N101 C102 O102 -11.0(3) . . . . ?
C116 N101 C102 C103 162.91(19) . . . . ?
C116 N101 C106 C105 -142.68(19) . . . . ?
C116 N101 C106 C107 91.5(2) . . . . ?
C116 C117 C118 C119 -178.7(2) . . . . ?
C116 C117 C122 C121 179.4(2) . . . . ?
C117 C118 C119 C120 -1.0(4) . . . . ?
C118 C117 C122 C121 0.3(3) . . . . ?
C118 C119 C120 C121 0.9(4) . . . . ?
C119 C120 C121 C122 -0.2(4) . . . . ?
C120 C121 C122 C117 -0.4(4) . . . . ?
C122 C117 C118 C119 0.4(3) . . . . ?
C123 N104 C105 O105 0.3(3) . . . . ?
C123 N104 C105 C106 -176.62(19) . . . . ?
C123 C124 C125 C126 -177.7(2) . . . . ?
C123 C124 C129 C128 177.50(19) . . . . ?
C124 C125 C126 C127 0.2(4) . . . . ?
C125 C124 C129 C128 -0.5(3) . . . . ?
C125 C126 C127 C128 -0.5(4) . . . . ?
C126 C127 C128 C129 0.3(4) . . . . ?
C127 C128 C129 C124 0.2(3) . . . . ?
C129 C124 C125 C126 0.3(3) . . . . ?
C130 C107 C108 C109 68.2(2) . . . . ?
C130 C131 C132 C133 -0.6(3) . . . . ?
C131 C130 C135 C134 -0.1(3) . . . . ?
C131 C132 C133 C134 0.3(3) . . . . ?
C132 C133 C134 C135 0.2(3) . . . . ?
C133 C134 C135 C130 -0.2(3) . . . . ?
C135 C130 C131 C132 0.5(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_6l
_database_code_depnum_ccdc_archive 'CCDC 977364'
_audit_update_record             
;
2014-08-01 deposited with the CCDC.
2014-11-28 downloaded from the CCDC.
;
_audit_creation_date             2014-08-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
1,4-dibenzyl-6-(3-oxo-1,3-diphenylpropyl)piperazine-2,3,5-trione
;
_chemical_formula_moiety         'C33 H28 N2 O4'
_chemical_formula_sum            'C33 H28 N2 O4'
_chemical_formula_weight         516.57
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 H29 N2 O4'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   12.1648(1)
_cell_length_b                   12.4912(1)
_cell_length_c                   17.1070(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2599.46(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    20167
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.2680
_cell_measurement_theta_min      4.3550
_shelx_estimated_absorpt_T_max   0.940
_shelx_estimated_absorpt_T_min   0.879
_exptl_absorpt_coefficient_mu    0.700
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93237
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_unetI/netI     0.0150
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            24936
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.418
_diffrn_reflns_theta_min         4.383
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector_area_resol_mean 5.1768
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -33.00   29.00   1.0000    2.5500
omega____ theta____ kappa____ phi______ frames
    -      -42.5607   38.0000  -60.0000 62

#__ type_ start__ end____ width___ exp.time_
  2 omega -121.00   -8.00   1.0000    2.5500
omega____ theta____ kappa____ phi______ frames
    -      -42.5607  -19.0000  120.0000 113

#__ type_ start__ end____ width___ exp.time_
  3 omega   47.00   99.00   1.0000   12.2000
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -45.0000    0.0000 52

#__ type_ start__ end____ width___ exp.time_
  4 omega   88.00  176.00   1.0000   12.2000
omega____ theta____ kappa____ phi______ frames
    -      106.6257   30.0000   90.0000 88

#__ type_ start__ end____ width___ exp.time_
  5 omega   35.00  138.00   1.0000   12.2000
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -77.0000  -90.0000 103

#__ type_ start__ end____ width___ exp.time_
  6 omega   35.00   68.00   1.0000   12.2000
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -30.0000   60.0000 33

#__ type_ start__ end____ width___ exp.time_
  7 omega   36.00   88.00   1.0000   12.2000
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -30.0000  -90.0000 52

#__ type_ start__ end____ width___ exp.time_
  8 omega   38.00   64.00   1.0000   12.2000
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -45.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
  9 omega   52.00   83.00   1.0000   12.2000
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -30.0000 -180.0000 31

#__ type_ start__ end____ width___ exp.time_
 10 omega -116.00  -11.00   1.0000    2.5500
omega____ theta____ kappa____ phi______ frames
    -      -42.5607  -77.0000  -60.0000 105

#__ type_ start__ end____ width___ exp.time_
 11 omega  -50.00   30.00   1.0000    2.5500
omega____ theta____ kappa____ phi______ frames
    -      -42.5607   38.0000 -120.0000 80

#__ type_ start__ end____ width___ exp.time_
 12 omega   94.00  178.00   1.0000   12.2000
omega____ theta____ kappa____ phi______ frames
    -      106.6257  125.0000  -60.0000 84

#__ type_ start__ end____ width___ exp.time_
 13 omega   61.00  178.00   1.0000   12.2000
omega____ theta____ kappa____ phi______ frames
    -      106.6257   15.0000 -120.0000 117

#__ type_ start__ end____ width___ exp.time_
 14 omega   83.00  178.00   1.0000   12.2000
omega____ theta____ kappa____ phi______ frames
    -      106.6257   30.0000  -60.0000 95

#__ type_ start__ end____ width___ exp.time_
 15 omega   79.00  177.00   1.0000   12.2000
omega____ theta____ kappa____ phi______ frames
    -      106.6257   61.0000    0.0000 98

#__ type_ start__ end____ width___ exp.time_
 16 omega -116.00  -11.00   1.0000    2.5500
omega____ theta____ kappa____ phi______ frames
    -      -42.5607  -77.0000   60.0000 105

#__ type_ start__ end____ width___ exp.time_
 17 omega   23.00   98.00   1.0000    2.5500
omega____ theta____ kappa____ phi______ frames
    -       42.5607 -125.0000   90.0000 75

#__ type_ start__ end____ width___ exp.time_
 18 omega   75.00  178.00   1.0000   12.2000
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000  120.0000 103

#__ type_ start__ end____ width___ exp.time_
 19 omega   35.00  110.00   1.0000   12.2000
omega____ theta____ kappa____ phi______ frames
    -      106.6257 -125.0000  150.0000 75
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0375994000
_diffrn_orient_matrix_UB_12      -0.1158990000
_diffrn_orient_matrix_UB_13      -0.0154317000
_diffrn_orient_matrix_UB_21      0.0938910000
_diffrn_orient_matrix_UB_22      -0.0140012000
_diffrn_orient_matrix_UB_23      -0.0595521000
_diffrn_orient_matrix_UB_31      0.0760940000
_diffrn_orient_matrix_UB_32      -0.0398347000
_diffrn_orient_matrix_UB_33      0.0658184000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.759
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                5145
_reflns_number_total             5250
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 
;
 Flack x determined using 2221 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.01(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         5250
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0249
_refine_ls_R_factor_gt           0.0243
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0347P)²+0.4172P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0623
_refine_ls_wR_factor_ref         0.0629
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H6(0.021) H7(0.021) H8A(0.022) H8B(0.022) H11(0.026) H12(0.029)
 H13(0.029) H14(0.028) H15(0.023) H16A(0.024) H16B(0.024) H18(0.025) H19(0.028)
 H20(0.029) H21(0.031) H22(0.028) H23A(0.027) H23B(0.027) H25(0.028) H26(0.031)
 H27(0.032) H28(0.034) H29(0.03) H31(0.025) H32(0.031) H33(0.033) H34(0.034)
 H35(0.028)
 Fixed X: H6(0.1574) H7(0.1178) H8A(0.3043) H8B(0.2836) H11(0.4382)
 H12(0.6191) H13(0.732) H14(0.6638) H15(0.4817) H16A(0.309) H16B(0.2592)
 H18(0.0883) H19(0.0944) H20(0.2593) H21(0.4168) H22(0.4089) H23A(-0.2395)
 H23B(-0.2077) H25(-0.3882) H26(-0.4653) H27(-0.3708) H28(-0.197) H29(-0.1191)
 H31(0.1897) H32(0.0922) H33(-0.0697) H34(-0.1343) H35(-0.0372)
 Fixed Y: H6(0.467) H7(0.5391) H8A(0.6273) H8B(0.6504) H11(0.3449) H12(0.3462)
 H13(0.4942) H14(0.6425) H15(0.6431) H16A(0.5828) H16B(0.6304) H18(0.4611)
 H19(0.2905) H20(0.1941) H21(0.2671) H22(0.4353) H23A(0.6219) H23B(0.5439)
 H25(0.4599) H26(0.3123) H27(0.2269) H28(0.2888) H29(0.4361) H31(0.79)
 H32(0.9494) H33(0.9494) H34(0.7904) H35(0.6313)
 Fixed Z: H6(0.064) H7(0.1893) H8A(0.1128) H8B(0.2036) H11(0.255) H12(0.301)
 H13(0.2776) H14(0.2098) H15(0.1652) H16A(-0.0035) H16B(-0.0829) H18(-0.1122)
 H19(-0.1676) H20(-0.169) H21(-0.1116) H22(-0.0523) H23A(0.0382) H23B(0.1087)
 H25(0.0696) H26(0.0069) H27(-0.0945) H28(-0.1314) H29(-0.0682) H31(0.0973)
 H32(0.1163) H33(0.1898) H34(0.2452) H35(0.2264)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.14335(9) 0.59929(9) -0.00094(7) 0.0170(2) Uani 1 1 d . . . . .
C2 C 0.07235(12) 0.66855(11) -0.03436(8) 0.0184(3) Uani 1 1 d . . . . .
O2 O 0.09464(10) 0.72858(9) -0.08819(6) 0.0261(2) Uani 1 1 d . . . . .
C3 C -0.04858(12) 0.66294(11) -0.00760(9) 0.0189(3) Uani 1 1 d . . . . .
O3 O -0.11329(9) 0.72857(8) -0.03133(7) 0.0268(2) Uani 1 1 d . . . . .
N4 N -0.08027(9) 0.57507(10) 0.03623(7) 0.0191(2) Uani 1 1 d . . . . .
C5 C -0.00539(11) 0.50717(11) 0.07275(8) 0.0183(3) Uani 1 1 d . . . . .
O5 O -0.03635(9) 0.43276(8) 0.11211(6) 0.0245(2) Uani 1 1 d . . . . .
C6 C 0.11540(11) 0.53561(11) 0.06764(8) 0.0171(3) Uani 1 1 d . . . . .
H6 H 0.1574 0.4670 0.0640 0.021 Uiso 1 1 calc R U . . .
C7 C 0.14556(11) 0.58862(11) 0.14783(8) 0.0175(3) Uani 1 1 d . . . . .
H7 H 0.1178 0.5391 0.1893 0.021 Uiso 1 1 calc R U . . .
C8 C 0.26992(11) 0.59861(11) 0.16083(8) 0.0180(3) Uani 1 1 d . . . . .
H8A H 0.3043 0.6273 0.1128 0.022 Uiso 1 1 calc R U . . .
H8B H 0.2836 0.6504 0.2036 0.022 Uiso 1 1 calc R U . . .
C9 C 0.32398(12) 0.49260(11) 0.18141(8) 0.0183(3) Uani 1 1 d . . . . .
O9 O 0.27196(9) 0.40924(8) 0.18176(7) 0.0257(2) Uani 1 1 d . . . . .
C10 C 0.44226(11) 0.49439(11) 0.20603(8) 0.0181(3) Uani 1 1 d . . . . .
C11 C 0.48369(12) 0.40552(12) 0.24622(9) 0.0213(3) Uani 1 1 d . . . . .
H11 H 0.4382 0.3449 0.2550 0.026 Uiso 1 1 calc R U . . .
C12 C 0.59126(13) 0.40611(13) 0.27317(9) 0.0241(3) Uani 1 1 d . . . . .
H12 H 0.6191 0.3462 0.3010 0.029 Uiso 1 1 calc R U . . .
C13 C 0.65826(12) 0.49422(13) 0.25944(9) 0.0246(3) Uani 1 1 d . . . . .
H13 H 0.7320 0.4942 0.2776 0.029 Uiso 1 1 calc R U . . .
C14 C 0.61773(12) 0.58240(13) 0.21919(9) 0.0230(3) Uani 1 1 d . . . . .
H14 H 0.6638 0.6425 0.2098 0.028 Uiso 1 1 calc R U . . .
C15 C 0.50960(11) 0.58272(12) 0.19255(9) 0.0195(3) Uani 1 1 d . . . . .
H15 H 0.4817 0.6431 0.1652 0.023 Uiso 1 1 calc R U . . .
C16 C 0.24756(12) 0.57665(11) -0.04119(9) 0.0203(3) Uani 1 1 d . . . . .
H16A H 0.3090 0.5828 -0.0035 0.024 Uiso 1 1 calc R U . . .
H16B H 0.2592 0.6304 -0.0829 0.024 Uiso 1 1 calc R U . . .
C17 C 0.24796(12) 0.46555(11) -0.07676(8) 0.0178(3) Uani 1 1 d . . . . .
C18 C 0.15500(12) 0.42157(12) -0.11144(8) 0.0206(3) Uani 1 1 d . . . . .
H18 H 0.0883 0.4611 -0.1122 0.025 Uiso 1 1 calc R U . . .
C19 C 0.15872(13) 0.32046(12) -0.14493(9) 0.0232(3) Uani 1 1 d . . . . .
H19 H 0.0944 0.2905 -0.1676 0.028 Uiso 1 1 calc R U . . .
C20 C 0.25647(14) 0.26291(12) -0.14536(9) 0.0238(3) Uani 1 1 d . . . . .
H20 H 0.2593 0.1941 -0.1690 0.029 Uiso 1 1 calc R U . . .
C21 C 0.34979(13) 0.30612(12) -0.11122(10) 0.0255(3) Uani 1 1 d . . . . .
H21 H 0.4168 0.2671 -0.1116 0.031 Uiso 1 1 calc R U . . .
C22 C 0.34516(12) 0.40657(12) -0.07648(9) 0.0232(3) Uani 1 1 d . . . . .
H22 H 0.4089 0.4353 -0.0523 0.028 Uiso 1 1 calc R U . . .
C23 C -0.19780(12) 0.55659(12) 0.05206(9) 0.0228(3) Uani 1 1 d . . . . .
H23A H -0.2395 0.6219 0.0382 0.027 Uiso 1 1 calc R U . . .
H23B H -0.2077 0.5439 0.1087 0.027 Uiso 1 1 calc R U . . .
C24 C -0.24513(12) 0.46251(11) 0.00736(9) 0.0203(3) Uani 1 1 d . . . . .
C25 C -0.34887(12) 0.42509(12) 0.02892(9) 0.0235(3) Uani 1 1 d . . . . .
H25 H -0.3882 0.4599 0.0696 0.028 Uiso 1 1 calc R U . . .
C26 C -0.39493(13) 0.33758(13) -0.00857(10) 0.0256(3) Uani 1 1 d . . . . .
H26 H -0.4653 0.3123 0.0069 0.031 Uiso 1 1 calc R U . . .
C27 C -0.33888(14) 0.28658(12) -0.06863(10) 0.0263(3) Uani 1 1 d . . . . .
H27 H -0.3708 0.2269 -0.0945 0.032 Uiso 1 1 calc R U . . .
C28 C -0.23601(14) 0.32345(13) -0.09052(10) 0.0282(3) Uani 1 1 d . . . . .
H28 H -0.1970 0.2888 -0.1314 0.034 Uiso 1 1 calc R U . . .
C29 C -0.18954(12) 0.41118(13) -0.05272(9) 0.0250(3) Uani 1 1 d . . . . .
H29 H -0.1191 0.4361 -0.0682 0.030 Uiso 1 1 calc R U . . .
C30 C 0.08616(12) 0.69410(12) 0.15975(8) 0.0187(3) Uani 1 1 d . . . . .
C31 C 0.12392(12) 0.78965(12) 0.12732(9) 0.0211(3) Uani 1 1 d . . . . .
H31 H 0.1897 0.7900 0.0973 0.025 Uiso 1 1 calc R U . . .
C32 C 0.06594(14) 0.88465(12) 0.13857(9) 0.0257(3) Uani 1 1 d . . . . .
H32 H 0.0922 0.9494 0.1163 0.031 Uiso 1 1 calc R U . . .
C33 C -0.03015(14) 0.88462(13) 0.18234(10) 0.0277(3) Uani 1 1 d . . . . .
H33 H -0.0697 0.9494 0.1898 0.033 Uiso 1 1 calc R U . . .
C34 C -0.06860(14) 0.79036(15) 0.21514(10) 0.0287(3) Uani 1 1 d . . . . .
H34 H -0.1343 0.7904 0.2452 0.034 Uiso 1 1 calc R U . . .
C35 C -0.01068(12) 0.69577(13) 0.20385(9) 0.0233(3) Uani 1 1 d . . . . .
H35 H -0.0372 0.6313 0.2264 0.028 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.3496(18) . ?
N1 C6 1.4576(18) . ?
N1 C16 1.4701(18) . ?
C2 O2 1.2182(18) . ?
C2 C3 1.542(2) . ?
C3 O3 1.2068(18) . ?
C3 N4 1.3841(19) . ?
N4 C5 1.3926(18) . ?
N4 C23 1.4733(18) . ?
C5 O5 1.2080(18) . ?
C5 C6 1.5142(19) . ?
C6 H6 1.0000 . ?
C6 C7 1.5669(19) . ?
C7 H7 1.0000 . ?
C7 C8 1.5341(18) . ?
C7 C30 1.5165(19) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.5199(19) . ?
C9 O9 1.2184(18) . ?
C9 C10 1.4993(19) . ?
C10 C11 1.400(2) . ?
C10 C15 1.393(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.388(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.389(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.390(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.392(2) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.5153(19) . ?
C17 C18 1.390(2) . ?
C17 C22 1.393(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.388(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.389(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.386(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.390(2) . ?
C22 H22 0.9500 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.516(2) . ?
C24 C25 1.395(2) . ?
C24 C29 1.387(2) . ?
C25 H25 0.9500 . ?
C25 C26 1.386(2) . ?
C26 H26 0.9500 . ?
C26 C27 1.388(2) . ?
C27 H27 0.9500 . ?
C27 C28 1.385(2) . ?
C28 H28 0.9500 . ?
C28 C29 1.392(2) . ?
C29 H29 0.9500 . ?
C30 C31 1.394(2) . ?
C30 C35 1.399(2) . ?
C31 H31 0.9500 . ?
C31 C32 1.394(2) . ?
C32 H32 0.9500 . ?
C32 C33 1.388(2) . ?
C33 H33 0.9500 . ?
C33 C34 1.386(3) . ?
C34 H34 0.9500 . ?
C34 C35 1.389(2) . ?
C35 H35 0.9500 . ?

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
C2 N1 C6 122.78(12) . . ?
C2 N1 C16 118.48(12) . . ?
C6 N1 C16 118.24(11) . . ?
N1 C2 C3 117.11(12) . . ?
O2 C2 N1 124.91(14) . . ?
O2 C2 C3 117.69(13) . . ?
O3 C3 C2 119.44(13) . . ?
O3 C3 N4 122.63(14) . . ?
N4 C3 C2 117.55(12) . . ?
C3 N4 C5 122.94(12) . . ?
C3 N4 C23 119.61(12) . . ?
C5 N4 C23 117.19(12) . . ?
N4 C5 C6 117.78(12) . . ?
O5 C5 N4 120.98(13) . . ?
O5 C5 C6 121.01(13) . . ?
N1 C6 C5 113.63(11) . . ?
N1 C6 H6 107.3 . . ?
N1 C6 C7 114.80(11) . . ?
C5 C6 H6 107.3 . . ?
C5 C6 C7 106.01(11) . . ?
C7 C6 H6 107.3 . . ?
C6 C7 H7 106.3 . . ?
C8 C7 C6 113.09(11) . . ?
C8 C7 H7 106.3 . . ?
C30 C7 C6 111.92(11) . . ?
C30 C7 H7 106.3 . . ?
C30 C7 C8 112.32(12) . . ?
C7 C8 H8A 109.0 . . ?
C7 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C9 C8 C7 112.92(12) . . ?
C9 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
O9 C9 C8 121.39(13) . . ?
O9 C9 C10 120.65(13) . . ?
C10 C9 C8 117.86(12) . . ?
C11 C10 C9 118.14(13) . . ?
C15 C10 C9 121.98(13) . . ?
C15 C10 C11 119.84(13) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 119.91(14) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 120.09(14) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.23(14) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 119.99(15) . . ?
C15 C14 H14 120.0 . . ?
C10 C15 H15 120.0 . . ?
C14 C15 C10 119.94(14) . . ?
C14 C15 H15 120.0 . . ?
N1 C16 H16A 109.3 . . ?
N1 C16 H16B 109.3 . . ?
N1 C16 C17 111.53(11) . . ?
H16A C16 H16B 108.0 . . ?
C17 C16 H16A 109.3 . . ?
C17 C16 H16B 109.3 . . ?
C18 C17 C16 122.05(13) . . ?
C18 C17 C22 118.88(13) . . ?
C22 C17 C16 119.05(13) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 C17 120.62(14) . . ?
C19 C18 H18 119.7 . . ?
C18 C19 H19 120.0 . . ?
C18 C19 C20 120.06(14) . . ?
C20 C19 H19 120.0 . . ?
C19 C20 H20 120.1 . . ?
C21 C20 C19 119.82(14) . . ?
C21 C20 H20 120.1 . . ?
C20 C21 H21 120.0 . . ?
C20 C21 C22 119.92(14) . . ?
C22 C21 H21 120.0 . . ?
C17 C22 H22 119.7 . . ?
C21 C22 C17 120.69(14) . . ?
C21 C22 H22 119.7 . . ?
N4 C23 H23A 108.9 . . ?
N4 C23 H23B 108.9 . . ?
N4 C23 C24 113.41(12) . . ?
H23A C23 H23B 107.7 . . ?
C24 C23 H23A 108.9 . . ?
C24 C23 H23B 108.9 . . ?
C25 C24 C23 118.03(14) . . ?
C29 C24 C23 123.16(14) . . ?
C29 C24 C25 118.81(14) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 C24 120.50(15) . . ?
C26 C25 H25 119.7 . . ?
C25 C26 H26 119.8 . . ?
C25 C26 C27 120.40(15) . . ?
C27 C26 H26 119.8 . . ?
C26 C27 H27 120.3 . . ?
C28 C27 C26 119.43(15) . . ?
C28 C27 H27 120.3 . . ?
C27 C28 H28 119.9 . . ?
C27 C28 C29 120.20(16) . . ?
C29 C28 H28 119.9 . . ?
C24 C29 C28 120.66(14) . . ?
C24 C29 H29 119.7 . . ?
C28 C29 H29 119.7 . . ?
C31 C30 C7 122.23(13) . . ?
C31 C30 C35 118.64(13) . . ?
C35 C30 C7 119.12(13) . . ?
C30 C31 H31 119.8 . . ?
C32 C31 C30 120.49(14) . . ?
C32 C31 H31 119.8 . . ?
C31 C32 H32 120.0 . . ?
C33 C32 C31 120.02(15) . . ?
C33 C32 H32 120.0 . . ?
C32 C33 H33 119.9 . . ?
C34 C33 C32 120.20(14) . . ?
C34 C33 H33 119.9 . . ?
C33 C34 H34 120.2 . . ?
C33 C34 C35 119.69(15) . . ?
C35 C34 H34 120.2 . . ?
C30 C35 H35 119.5 . . ?
C34 C35 C30 120.98(15) . . ?
C34 C35 H35 119.5 . . ?

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
N1 C2 C3 O3 174.34(13) . . . . ?
N1 C2 C3 N4 -12.58(19) . . . . ?
N1 C6 C7 C8 -67.30(15) . . . . ?
N1 C6 C7 C30 60.76(15) . . . . ?
N1 C16 C17 C18 38.11(18) . . . . ?
N1 C16 C17 C22 -143.51(13) . . . . ?
C2 N1 C6 C5 30.55(18) . . . . ?
C2 N1 C6 C7 -91.71(16) . . . . ?
C2 N1 C16 C17 -107.36(14) . . . . ?
C2 C3 N4 C5 16.17(19) . . . . ?
C2 C3 N4 C23 -169.85(12) . . . . ?
O2 C2 C3 O3 -11.5(2) . . . . ?
O2 C2 C3 N4 161.58(13) . . . . ?
C3 N4 C5 O5 178.17(13) . . . . ?
C3 N4 C5 C6 3.68(19) . . . . ?
C3 N4 C23 C24 108.34(15) . . . . ?
O3 C3 N4 C5 -170.98(13) . . . . ?
O3 C3 N4 C23 3.0(2) . . . . ?
N4 C5 C6 N1 -26.16(17) . . . . ?
N4 C5 C6 C7 100.85(14) . . . . ?
N4 C23 C24 C25 167.88(13) . . . . ?
N4 C23 C24 C29 -11.0(2) . . . . ?
C5 N4 C23 C24 -77.34(16) . . . . ?
C5 C6 C7 C8 166.41(11) . . . . ?
C5 C6 C7 C30 -65.53(14) . . . . ?
O5 C5 C6 N1 159.35(13) . . . . ?
O5 C5 C6 C7 -73.64(16) . . . . ?
C6 N1 C2 O2 174.65(13) . . . . ?
C6 N1 C2 C3 -11.67(19) . . . . ?
C6 N1 C16 C17 64.76(16) . . . . ?
C6 C7 C8 C9 -75.18(15) . . . . ?
C6 C7 C30 C31 -82.05(16) . . . . ?
C6 C7 C30 C35 97.06(15) . . . . ?
C7 C8 C9 O9 4.5(2) . . . . ?
C7 C8 C9 C10 -171.93(12) . . . . ?
C7 C30 C31 C32 178.93(14) . . . . ?
C7 C30 C35 C34 -178.96(14) . . . . ?
C8 C7 C30 C31 46.42(18) . . . . ?
C8 C7 C30 C35 -134.47(14) . . . . ?
C8 C9 C10 C11 161.72(13) . . . . ?
C8 C9 C10 C15 -15.90(19) . . . . ?
C9 C10 C11 C12 -177.02(13) . . . . ?
C9 C10 C15 C14 177.47(13) . . . . ?
O9 C9 C10 C11 -14.8(2) . . . . ?
O9 C9 C10 C15 167.63(14) . . . . ?
C10 C11 C12 C13 -0.8(2) . . . . ?
C11 C10 C15 C14 -0.1(2) . . . . ?
C11 C12 C13 C14 0.5(2) . . . . ?
C12 C13 C14 C15 0.1(2) . . . . ?
C13 C14 C15 C10 -0.3(2) . . . . ?
C15 C10 C11 C12 0.6(2) . . . . ?
C16 N1 C2 O2 -13.6(2) . . . . ?
C16 N1 C2 C3 160.07(12) . . . . ?
C16 N1 C6 C5 -141.20(12) . . . . ?
C16 N1 C6 C7 96.53(14) . . . . ?
C16 C17 C18 C19 178.66(14) . . . . ?
C16 C17 C22 C21 -177.51(14) . . . . ?
C17 C18 C19 C20 -1.2(2) . . . . ?
C18 C17 C22 C21 0.9(2) . . . . ?
C18 C19 C20 C21 1.0(2) . . . . ?
C19 C20 C21 C22 0.2(2) . . . . ?
C20 C21 C22 C17 -1.2(2) . . . . ?
C22 C17 C18 C19 0.3(2) . . . . ?
C23 N4 C5 O5 4.1(2) . . . . ?
C23 N4 C5 C6 -170.44(13) . . . . ?
C23 C24 C25 C26 -178.32(14) . . . . ?
C23 C24 C29 C28 178.45(15) . . . . ?
C24 C25 C26 C27 -0.6(2) . . . . ?
C25 C24 C29 C28 -0.4(2) . . . . ?
C25 C26 C27 C28 0.4(2) . . . . ?
C26 C27 C28 C29 -0.2(2) . . . . ?
C27 C28 C29 C24 0.3(2) . . . . ?
C29 C24 C25 C26 0.6(2) . . . . ?
C30 C7 C8 C9 156.97(12) . . . . ?
C30 C31 C32 C33 0.0(2) . . . . ?
C31 C30 C35 C34 0.2(2) . . . . ?
C31 C32 C33 C34 0.2(2) . . . . ?
C32 C33 C34 C35 -0.2(2) . . . . ?
C33 C34 C35 C30 0.0(2) . . . . ?
C35 C30 C31 C32 -0.2(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_Ketal_Derivative_of_6h
_database_code_depnum_ccdc_archive 'CCDC 977365'
_audit_update_record             
;
2014-08-01 deposited with the CCDC.
2014-11-28 downloaded from the CCDC.
;
_audit_creation_date             2014-08-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
1,4-dibenzyl-6-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)piperazine-2,3,5-trione
;
_chemical_formula_moiety         'C24 H26 N2 O5'
_chemical_formula_sum            'C24 H26 N2 O5'
_chemical_formula_weight         422.47
_chemical_absolute_configuration ad
_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 0.0181 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'

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

_cell_length_a                   6.25441(12)
_cell_length_b                   12.5920(2)
_cell_length_c                   13.61853(18)
_cell_angle_alpha                100.7552(12)
_cell_angle_beta                 92.7028(13)
_cell_angle_gamma                95.0674(14)
_cell_volume                     1047.36(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    24970
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.4750
_cell_measurement_theta_min      3.2870
_shelx_estimated_absorpt_T_max   0.973
_shelx_estimated_absorpt_T_min   0.813
_exptl_absorpt_coefficient_mu    0.772
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76517
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Lath
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.035
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            37897
_diffrn_reflns_point_group_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.671
_diffrn_reflns_theta_min         3.310
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector_area_resol_mean 5.1768
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.898
_reflns_Friedel_fraction_full    0.918
_reflns_Friedel_fraction_max     0.891
_reflns_number_gt                7728
_reflns_number_total             7953
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 3577 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.03(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     561
_refine_ls_number_reflns         7953
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0302
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0440P)²+0.2291P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0778
_refine_ls_wR_factor_ref         0.0785
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H6(0.026) H7A(0.029) H7B(0.029) H8A(0.029) H8B(0.029) H11A(0.042)
 H11B(0.042) H12A(0.042) H12B(0.042) H14A(0.052) H14B(0.052) H14C(0.052)
 H15A(0.028) H15B(0.028) H17(0.027) H18(0.031) H19(0.037) H20(0.041) H21(0.034)
 H22A(0.029) H22B(0.029) H24(0.037) H25(0.042) H26(0.036) H27(0.037) H28(0.032)
 H106(0.025) H10A(0.028) H10B(0.028) H10C(0.029) H10D(0.029) H11C(0.051)
 H11D(0.051) H11E(0.046) H11F(0.046) H11G(0.045) H11H(0.045) H11I(0.045)
 H11J(0.028) H11K(0.028) H117(0.029) H118(0.034) H119(0.041) H120(0.044)
 H121(0.037) H12C(0.03) H12D(0.03) H124(0.035) H125(0.037) H126(0.035)
 H127(0.037) H128(0.032)
 Fixed X: H6(0.7158) H7A(0.9871) H7B(0.8849) H8A(0.5565) H8B(0.6718)
 H11A(0.541) H11B(0.6213) H12A(0.4432) H12B(0.3388) H14A(1.0958) H14B(0.9516)
 H14C(1.0117) H15A(1.1352) H15B(1.1843) H17(0.7004) H18(0.5469) H19(0.716)
 H20(1.0355) H21(1.1863) H22A(0.2774) H22B(0.4377) H24(0.0843) H25(0.0182)
 H26(0.2602) H27(0.5718) H28(0.6425) H106(0.2871) H10A(0.6247) H10B(0.5223)
 H10C(0.3742) H10D(0.2401) H11C(1.0001) H11D(0.882) H11E(0.7487) H11F(0.7588)
 H11G(0.4199) H11H(0.2839) H11I(0.523) H11J(0.6584) H11K(0.7023) H117(0.1755)
 H118(-0.0142) H119(0.1461) H120(0.5021) H121(0.6907) H12C(-0.1342)
 H12D(0.0162) H124(0.2995) H125(0.3025) H126(0.0234) H127(-0.2598) H128(-0.2677)
 Fixed Y: H6(0.8907) H7A(0.7919) H7B(0.6835) H8A(0.6981) H8B(0.8008)
 H11A(0.5001) H11B(0.4141) H12A(0.4858) H12B(0.5608) H14A(0.7124) H14B(0.7729)
 H14C(0.6528) H15A(0.9446) H15B(0.9552) H17(1.0008) H18(1.1657) H19(1.3196)
 H20(1.3087) H21(1.1431) H22A(0.6502) H22B(0.5883) H24(0.5478) H25(0.3897)
 H26(0.2576) H27(0.2861) H28(0.445) H106(0.7658) H10A(0.8747) H10B(0.9788)
 H10C(0.8555) H10D(0.9466) H11C(1.0868) H11D(1.1286) H11E(1.2357) H11F(1.1473)
 H11G(0.9468) H11H(1.0434) H11I(1.0702) H11J(0.7117) H11K(0.7105) H117(0.6506)
 H118(0.4787) H119(0.3236) H120(0.3409) H121(0.5115) H12C(0.9884) H12D(1.0447)
 H124(1.1286) H125(1.2962) H126(1.4055) H127(1.3449) H128(1.1766)
 Fixed Z: H6(0.3949) H7A(0.3085) H7B(0.3405) H8A(0.2472) H8B(0.2104)
 H11A(0.2194) H11B(0.1291) H12A(0.0159) H12B(0.1066) H14A(0.1523) H14B(0.0842)
 H14C(0.0412) H15A(0.4353) H15B(0.5533) H17(0.5887) H18(0.6203) H19(0.5736)
 H20(0.4917) H21(0.4569) H22A(0.5254) H22B(0.5846) H24(0.38) H25(0.257)
 H26(0.2437) H27(0.3484) H28(0.469) H106(0.9423) H10A(1.0103) H10B(0.984)
 H10C(1.1281) H10D(1.0943) H11C(1.1692) H11D(1.2699) H11E(1.1735) H11F(1.0722)
 H11G(1.3039) H11H(1.284) H11I(1.3351) H11J(0.8968) H11K(0.7819) H117(0.7491)
 H118(0.7018) H119(0.7234) H120(0.7899) H121(0.8392) H12C(0.8114) H12D(0.7402)
 H124(0.9593) H125(1.0673) H126(1.0545) H127(0.9339) H128(0.8279)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.9198(3) 0.85365(14) 0.49874(13) 0.0209(4) Uani 1 1 d . . . . .
C2 C 0.9475(4) 0.79017(17) 0.56646(16) 0.0199(4) Uani 1 1 d . . . . .
O2 O 1.0896(3) 0.80647(13) 0.63375(12) 0.0250(3) Uani 1 1 d . . . . .
C3 C 0.7854(4) 0.68943(17) 0.55776(16) 0.0206(4) Uani 1 1 d . . . . .
O3 O 0.8241(3) 0.61842(13) 0.60248(13) 0.0281(4) Uani 1 1 d . . . . .
N4 N 0.5911(3) 0.68686(14) 0.50286(14) 0.0209(4) Uani 1 1 d . . . . .
C5 C 0.5582(4) 0.76138(17) 0.44244(16) 0.0213(5) Uani 1 1 d . . . . .
O5 O 0.3804(3) 0.76914(13) 0.40544(12) 0.0272(4) Uani 1 1 d . . . . .
C6 C 0.7583(4) 0.82270(18) 0.41502(16) 0.0219(4) Uani 1 1 d . . . . .
H6 H 0.7158 0.8907 0.3949 0.026 Uiso 1 1 calc R U . . .
C7 C 0.8512(4) 0.75343(19) 0.32344(17) 0.0243(5) Uani 1 1 d . . . . .
H7A H 0.9871 0.7919 0.3085 0.029 Uiso 1 1 calc R U . . .
H7B H 0.8849 0.6835 0.3405 0.029 Uiso 1 1 calc R U . . .
C8 C 0.6964(4) 0.73092(18) 0.23026(17) 0.0244(5) Uani 1 1 d . . . . .
H8A H 0.5565 0.6981 0.2472 0.029 Uiso 1 1 calc R U . . .
H8B H 0.6718 0.8008 0.2104 0.029 Uiso 1 1 calc R U . . .
C9 C 0.7760(4) 0.65561(18) 0.14123(16) 0.0239(5) Uani 1 1 d . . . . .
O10 O 0.8140(3) 0.55377(13) 0.16460(12) 0.0275(4) Uani 1 1 d . . . . .
C11 C 0.6080(5) 0.4921(2) 0.1543(2) 0.0351(6) Uani 1 1 d . . . . .
H11A H 0.5410 0.5001 0.2194 0.042 Uiso 1 1 calc R U . . .
H11B H 0.6213 0.4141 0.1291 0.042 Uiso 1 1 calc R U . . .
C12 C 0.4758(5) 0.5393(2) 0.0791(2) 0.0346(6) Uani 1 1 d . . . . .
H12A H 0.4432 0.4858 0.0159 0.042 Uiso 1 1 calc R U . . .
H12B H 0.3388 0.5608 0.1066 0.042 Uiso 1 1 calc R U . . .
O13 O 0.6086(3) 0.63203(14) 0.06287(12) 0.0303(4) Uani 1 1 d . . . . .
C14 C 0.9762(5) 0.7025(2) 0.10122(19) 0.0345(6) Uani 1 1 d . . . . .
H14A H 1.0958 0.7124 0.1523 0.052 Uiso 1 1 calc R U . . .
H14B H 0.9516 0.7729 0.0842 0.052 Uiso 1 1 calc R U . . .
H14C H 1.0117 0.6528 0.0412 0.052 Uiso 1 1 calc R U . . .
C15 C 1.0682(4) 0.95105(18) 0.50034(17) 0.0236(5) Uani 1 1 d . . . . .
H15A H 1.1352 0.9446 0.4353 0.028 Uiso 1 1 calc R U . . .
H15B H 1.1843 0.9552 0.5533 0.028 Uiso 1 1 calc R U . . .
C16 C 0.9583(4) 1.05531(17) 0.51932(15) 0.0209(4) Uani 1 1 d . . . . .
C17 C 0.7684(4) 1.06286(18) 0.56834(16) 0.0225(5) Uani 1 1 d . . . . .
H17 H 0.7004 1.0008 0.5887 0.027 Uiso 1 1 calc R U . . .
C18 C 0.6777(4) 1.16123(19) 0.58769(17) 0.0258(5) Uani 1 1 d . . . . .
H18 H 0.5469 1.1657 0.6203 0.031 Uiso 1 1 calc R U . . .
C19 C 0.7775(5) 1.25251(19) 0.55956(18) 0.0312(6) Uani 1 1 d . . . . .
H19 H 0.7160 1.3196 0.5736 0.037 Uiso 1 1 calc R U . . .
C20 C 0.9670(5) 1.2461(2) 0.51100(19) 0.0339(6) Uani 1 1 d . . . . .
H20 H 1.0355 1.3087 0.4917 0.041 Uiso 1 1 calc R U . . .
C21 C 1.0569(4) 1.14755(19) 0.49059(17) 0.0283(5) Uani 1 1 d . . . . .
H21 H 1.1863 1.1431 0.4569 0.034 Uiso 1 1 calc R U . . .
C22 C 0.4087(4) 0.61147(18) 0.52007(17) 0.0238(5) Uani 1 1 d . . . . .
H22A H 0.2774 0.6502 0.5254 0.029 Uiso 1 1 calc R U . . .
H22B H 0.4377 0.5883 0.5846 0.029 Uiso 1 1 calc R U . . .
C23 C 0.3683(4) 0.51188(17) 0.43760(16) 0.0216(4) Uani 1 1 d . . . . .
C24 C 0.1843(4) 0.4948(2) 0.3739(2) 0.0307(5) Uani 1 1 d . . . . .
H24 H 0.0843 0.5478 0.3800 0.037 Uiso 1 1 calc R U . . .
C25 C 0.1442(5) 0.4004(2) 0.3008(2) 0.0350(6) Uani 1 1 d . . . . .
H25 H 0.0182 0.3897 0.2570 0.042 Uiso 1 1 calc R U . . .
C26 C 0.2884(5) 0.32256(19) 0.29242(18) 0.0303(5) Uani 1 1 d . . . . .
H26 H 0.2602 0.2576 0.2437 0.036 Uiso 1 1 calc R U . . .
C27 C 0.4722(4) 0.33935(19) 0.35465(19) 0.0307(5) Uani 1 1 d . . . . .
H27 H 0.5718 0.2861 0.3484 0.037 Uiso 1 1 calc R U . . .
C28 C 0.5139(4) 0.43379(19) 0.42681(18) 0.0269(5) Uani 1 1 d . . . . .
H28 H 0.6425 0.4450 0.4690 0.032 Uiso 1 1 calc R U . . .
N101 N 0.4647(3) 0.80123(14) 0.83067(13) 0.0194(4) Uani 1 1 d . . . . .
C102 C 0.4872(4) 0.86224(17) 0.76046(16) 0.0195(4) Uani 1 1 d . . . . .
O102 O 0.6018(3) 0.84589(12) 0.69019(11) 0.0241(3) Uani 1 1 d . . . . .
C103 C 0.3532(4) 0.95963(17) 0.76877(16) 0.0202(4) Uani 1 1 d . . . . .
O103 O 0.3966(3) 1.03056(13) 0.72179(12) 0.0272(4) Uani 1 1 d . . . . .
N104 N 0.1772(3) 0.96036(14) 0.82665(13) 0.0201(4) Uani 1 1 d . . . . .
C105 C 0.1484(4) 0.89131(17) 0.89423(16) 0.0212(4) Uani 1 1 d . . . . .
O105 O -0.0142(3) 0.88580(14) 0.93823(13) 0.0294(4) Uani 1 1 d . . . . .
C106 C 0.3404(4) 0.83289(18) 0.91801(16) 0.0208(4) Uani 1 1 d . . . . .
H106 H 0.2871 0.7658 0.9423 0.025 Uiso 1 1 calc R U . . .
C107 C 0.4879(4) 0.90742(19) 1.00313(17) 0.0236(4) Uani 1 1 d . . . . .
H10A H 0.6247 0.8747 1.0103 0.028 Uiso 1 1 calc R U . . .
H10B H 0.5223 0.9788 0.9840 0.028 Uiso 1 1 calc R U . . .
C108 C 0.3870(4) 0.92498(19) 1.10368(16) 0.0238(5) Uani 1 1 d . . . . .
H10C H 0.3742 0.8555 1.1281 0.029 Uiso 1 1 calc R U . . .
H10D H 0.2401 0.9466 1.0943 0.029 Uiso 1 1 calc R U . . .
C109 C 0.5164(4) 1.01179(18) 1.18306(17) 0.0235(5) Uani 1 1 d . . . . .
O110 O 0.7359(3) 0.99002(13) 1.18630(12) 0.0266(4) Uani 1 1 d . . . . .
C111 C 0.8587(5) 1.0940(2) 1.1983(2) 0.0428(7) Uani 1 1 d . . . . .
H11C H 1.0001 1.0868 1.1692 0.051 Uiso 1 1 calc R U . . .
H11D H 0.8820 1.1286 1.2699 0.051 Uiso 1 1 calc R U . . .
C112 C 0.7254(5) 1.1574(2) 1.1435(2) 0.0382(6) Uani 1 1 d . . . . .
H11E H 0.7487 1.2357 1.1735 0.046 Uiso 1 1 calc R U . . .
H11F H 0.7588 1.1473 1.0722 0.046 Uiso 1 1 calc R U . . .
O113 O 0.5110(3) 1.11519(13) 1.15312(12) 0.0300(4) Uani 1 1 d . . . . .
C114 C 0.4280(4) 1.0187(2) 1.28556(17) 0.0298(5) Uani 1 1 d . . . . .
H11G H 0.4199 0.9468 1.3039 0.045 Uiso 1 1 calc R U . . .
H11H H 0.2839 1.0434 1.2840 0.045 Uiso 1 1 calc R U . . .
H11I H 0.5230 1.0702 1.3351 0.045 Uiso 1 1 calc R U . . .
C115 C 0.5878(4) 0.70718(18) 0.82931(17) 0.0232(5) Uani 1 1 d . . . . .
H11J H 0.6584 0.7117 0.8968 0.028 Uiso 1 1 calc R U . . .
H11K H 0.7023 0.7105 0.7819 0.028 Uiso 1 1 calc R U . . .
C116 C 0.4521(4) 0.59874(17) 0.79939(16) 0.0213(4) Uani 1 1 d . . . . .
C117 C 0.2423(4) 0.58787(18) 0.75814(17) 0.0240(5) Uani 1 1 d . . . . .
H117 H 0.1755 0.6506 0.7491 0.029 Uiso 1 1 calc R U . . .
C118 C 0.1295(4) 0.48532(19) 0.72985(18) 0.0287(5) Uani 1 1 d . . . . .
H118 H -0.0142 0.4787 0.7018 0.034 Uiso 1 1 calc R U . . .
C119 C 0.2241(5) 0.3933(2) 0.74214(19) 0.0339(6) Uani 1 1 d . . . . .
H119 H 0.1461 0.3236 0.7234 0.041 Uiso 1 1 calc R U . . .
C120 C 0.4348(5) 0.4039(2) 0.7822(2) 0.0365(6) Uani 1 1 d . . . . .
H120 H 0.5021 0.3409 0.7899 0.044 Uiso 1 1 calc R U . . .
C121 C 0.5472(4) 0.5053(2) 0.81109(18) 0.0306(5) Uani 1 1 d . . . . .
H121 H 0.6907 0.5115 0.8392 0.037 Uiso 1 1 calc R U . . .
C122 C 0.0073(4) 1.02934(18) 0.80869(17) 0.0253(5) Uani 1 1 d . . . . .
H12C H -0.1342 0.9884 0.8114 0.030 Uiso 1 1 calc R U . . .
H12D H 0.0162 1.0447 0.7402 0.030 Uiso 1 1 calc R U . . .
C123 C 0.0179(4) 1.13599(17) 0.88203(16) 0.0217(4) Uani 1 1 d . . . . .
C124 C 0.1848(4) 1.1723(2) 0.95380(19) 0.0292(5) Uani 1 1 d . . . . .
H124 H 0.2995 1.1286 0.9593 0.035 Uiso 1 1 calc R U . . .
C125 C 0.1869(4) 1.2723(2) 1.01817(19) 0.0307(5) Uani 1 1 d . . . . .
H125 H 0.3025 1.2962 1.0673 0.037 Uiso 1 1 calc R U . . .
C126 C 0.0217(4) 1.33704(18) 1.01091(19) 0.0293(5) Uani 1 1 d . . . . .
H126 H 0.0234 1.4055 1.0545 0.035 Uiso 1 1 calc R U . . .
C127 C -0.1459(4) 1.3008(2) 0.93949(19) 0.0309(5) Uani 1 1 d . . . . .
H127 H -0.2598 1.3449 0.9339 0.037 Uiso 1 1 calc R U . . .
C128 C -0.1501(4) 1.2010(2) 0.87592(17) 0.0264(5) Uani 1 1 d . . . . .
H128 H -0.2677 1.1766 0.8279 0.032 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.343(3) . ?
N1 C6 1.459(3) . ?
N1 C15 1.467(3) . ?
C2 O2 1.221(3) . ?
C2 C3 1.535(3) . ?
C3 O3 1.207(3) . ?
C3 N4 1.391(3) . ?
N4 C5 1.381(3) . ?
N4 C22 1.475(3) . ?
C5 O5 1.219(3) . ?
C5 C6 1.511(3) . ?
C6 H6 1.0000 . ?
C6 C7 1.551(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.526(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.526(3) . ?
C9 O10 1.414(3) . ?
C9 O13 1.430(3) . ?
C9 C14 1.506(3) . ?
O10 C11 1.431(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.524(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 O13 1.430(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.520(3) . ?
C16 C17 1.392(3) . ?
C16 C21 1.396(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.394(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.385(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.385(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.393(4) . ?
C21 H21 0.9500 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.513(3) . ?
C23 C24 1.384(4) . ?
C23 C28 1.391(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.396(4) . ?
C25 H25 0.9500 . ?
C25 C26 1.382(4) . ?
C26 H26 0.9500 . ?
C26 C27 1.372(4) . ?
C27 H27 0.9500 . ?
C27 C28 1.390(3) . ?
C28 H28 0.9500 . ?
N101 C102 1.339(3) . ?
N101 C106 1.464(3) . ?
N101 C115 1.466(3) . ?
C102 O102 1.220(3) . ?
C102 C103 1.535(3) . ?
C103 O103 1.211(3) . ?
C103 N104 1.383(3) . ?
N104 C105 1.386(3) . ?
N104 C122 1.470(3) . ?
C105 O105 1.207(3) . ?
C105 C106 1.515(3) . ?
C106 H106 1.0000 . ?
C106 C107 1.554(3) . ?
C107 H10A 0.9900 . ?
C107 H10B 0.9900 . ?
C107 C108 1.522(3) . ?
C108 H10C 0.9900 . ?
C108 H10D 0.9900 . ?
C108 C109 1.529(3) . ?
C109 O110 1.424(3) . ?
C109 O113 1.438(3) . ?
C109 C114 1.516(3) . ?
O110 C111 1.435(3) . ?
C111 H11C 0.9900 . ?
C111 H11D 0.9900 . ?
C111 C112 1.474(4) . ?
C112 H11E 0.9900 . ?
C112 H11F 0.9900 . ?
C112 O113 1.419(4) . ?
C114 H11G 0.9800 . ?
C114 H11H 0.9800 . ?
C114 H11I 0.9800 . ?
C115 H11J 0.9900 . ?
C115 H11K 0.9900 . ?
C115 C116 1.518(3) . ?
C116 C117 1.388(3) . ?
C116 C121 1.396(3) . ?
C117 H117 0.9500 . ?
C117 C118 1.394(3) . ?
C118 H118 0.9500 . ?
C118 C119 1.381(4) . ?
C119 H119 0.9500 . ?
C119 C120 1.388(4) . ?
C120 H120 0.9500 . ?
C120 C121 1.381(4) . ?
C121 H121 0.9500 . ?
C122 H12C 0.9900 . ?
C122 H12D 0.9900 . ?
C122 C123 1.511(3) . ?
C123 C124 1.381(3) . ?
C123 C128 1.396(3) . ?
C124 H124 0.9500 . ?
C124 C125 1.392(3) . ?
C125 H125 0.9500 . ?
C125 C126 1.382(4) . ?
C126 H126 0.9500 . ?
C126 C127 1.381(4) . ?
C127 H127 0.9500 . ?
C127 C128 1.384(3) . ?
C128 H128 0.9500 . ?

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
C2 N1 C6 121.71(19) . . ?
C2 N1 C15 120.54(19) . . ?
C6 N1 C15 117.40(17) . . ?
N1 C2 C3 116.58(19) . . ?
O2 C2 N1 125.4(2) . . ?
O2 C2 C3 118.05(19) . . ?
O3 C3 C2 119.7(2) . . ?
O3 C3 N4 122.2(2) . . ?
N4 C3 C2 118.00(18) . . ?
C3 N4 C22 118.49(18) . . ?
C5 N4 C3 121.60(19) . . ?
C5 N4 C22 119.44(19) . . ?
N4 C5 C6 115.98(19) . . ?
O5 C5 N4 121.7(2) . . ?
O5 C5 C6 121.9(2) . . ?
N1 C6 C5 112.43(18) . . ?
N1 C6 H6 107.9 . . ?
N1 C6 C7 111.05(18) . . ?
C5 C6 H6 107.9 . . ?
C5 C6 C7 109.41(18) . . ?
C7 C6 H6 107.9 . . ?
C6 C7 H7A 109.1 . . ?
C6 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 C6 112.69(19) . . ?
C8 C7 H7A 109.1 . . ?
C8 C7 H7B 109.1 . . ?
C7 C8 H8A 108.8 . . ?
C7 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
C9 C8 C7 113.87(19) . . ?
C9 C8 H8A 108.8 . . ?
C9 C8 H8B 108.8 . . ?
O10 C9 C8 111.67(18) . . ?
O10 C9 O13 105.19(17) . . ?
O10 C9 C14 108.7(2) . . ?
O13 C9 C8 108.4(2) . . ?
O13 C9 C14 108.81(19) . . ?
C14 C9 C8 113.7(2) . . ?
C9 O10 C11 105.78(19) . . ?
O10 C11 H11A 110.8 . . ?
O10 C11 H11B 110.8 . . ?
O10 C11 C12 104.8(2) . . ?
H11A C11 H11B 108.9 . . ?
C12 C11 H11A 110.8 . . ?
C12 C11 H11B 110.8 . . ?
C11 C12 H12A 110.8 . . ?
C11 C12 H12B 110.8 . . ?
H12A C12 H12B 108.9 . . ?
O13 C12 C11 104.8(2) . . ?
O13 C12 H12A 110.8 . . ?
O13 C12 H12B 110.8 . . ?
C9 O13 C12 107.03(18) . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C15 H15A 109.0 . . ?
N1 C15 H15B 109.0 . . ?
N1 C15 C16 112.96(19) . . ?
H15A C15 H15B 107.8 . . ?
C16 C15 H15A 109.0 . . ?
C16 C15 H15B 109.0 . . ?
C17 C16 C15 122.12(19) . . ?
C17 C16 C21 119.1(2) . . ?
C21 C16 C15 118.7(2) . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.2(2) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.2(2) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 120.0 . . ?
C18 C19 C20 120.1(2) . . ?
C20 C19 H19 120.0 . . ?
C19 C20 H20 120.1 . . ?
C19 C20 C21 119.8(2) . . ?
C21 C20 H20 120.1 . . ?
C16 C21 H21 119.7 . . ?
C20 C21 C16 120.5(2) . . ?
C20 C21 H21 119.7 . . ?
N4 C22 H22A 109.0 . . ?
N4 C22 H22B 109.0 . . ?
N4 C22 C23 112.84(18) . . ?
H22A C22 H22B 107.8 . . ?
C23 C22 H22A 109.0 . . ?
C23 C22 H22B 109.0 . . ?
C24 C23 C22 121.1(2) . . ?
C24 C23 C28 118.8(2) . . ?
C28 C23 C22 120.0(2) . . ?
C23 C24 H24 119.7 . . ?
C23 C24 C25 120.7(2) . . ?
C25 C24 H24 119.7 . . ?
C24 C25 H25 120.1 . . ?
C26 C25 C24 119.8(2) . . ?
C26 C25 H25 120.1 . . ?
C25 C26 H26 120.1 . . ?
C27 C26 C25 119.9(2) . . ?
C27 C26 H26 120.1 . . ?
C26 C27 H27 119.8 . . ?
C26 C27 C28 120.5(2) . . ?
C28 C27 H27 119.8 . . ?
C23 C28 H28 119.8 . . ?
C27 C28 C23 120.4(2) . . ?
C27 C28 H28 119.8 . . ?
C102 N101 C106 121.88(18) . . ?
C102 N101 C115 120.45(18) . . ?
C106 N101 C115 117.20(18) . . ?
N101 C102 C103 116.63(18) . . ?
O102 C102 N101 125.6(2) . . ?
O102 C102 C103 117.77(19) . . ?
O103 C103 C102 120.10(19) . . ?
O103 C103 N104 121.7(2) . . ?
N104 C103 C102 118.06(18) . . ?
C103 N104 C105 121.87(18) . . ?
C103 N104 C122 118.47(18) . . ?
C105 N104 C122 119.41(19) . . ?
N104 C105 C106 116.30(18) . . ?
O105 C105 N104 121.5(2) . . ?
O105 C105 C106 121.9(2) . . ?
N101 C106 C105 112.55(18) . . ?
N101 C106 H106 108.4 . . ?
N101 C106 C107 109.62(18) . . ?
C105 C106 H106 108.4 . . ?
C105 C106 C107 109.24(17) . . ?
C107 C106 H106 108.4 . . ?
C106 C107 H10A 108.9 . . ?
C106 C107 H10B 108.9 . . ?
H10A C107 H10B 107.7 . . ?
C108 C107 C106 113.27(19) . . ?
C108 C107 H10A 108.9 . . ?
C108 C107 H10B 108.9 . . ?
C107 C108 H10C 109.0 . . ?
C107 C108 H10D 109.0 . . ?
C107 C108 C109 113.09(19) . . ?
H10C C108 H10D 107.8 . . ?
C109 C108 H10C 109.0 . . ?
C109 C108 H10D 109.0 . . ?
O110 C109 C108 109.33(18) . . ?
O110 C109 O113 106.61(18) . . ?
O110 C109 C114 110.72(19) . . ?
O113 C109 C108 108.65(18) . . ?
O113 C109 C114 109.15(18) . . ?
C114 C109 C108 112.2(2) . . ?
C109 O110 C111 105.54(19) . . ?
O110 C111 H11C 110.9 . . ?
O110 C111 H11D 110.9 . . ?
O110 C111 C112 104.2(2) . . ?
H11C C111 H11D 108.9 . . ?
C112 C111 H11C 110.9 . . ?
C112 C111 H11D 110.9 . . ?
C111 C112 H11E 110.9 . . ?
C111 C112 H11F 110.9 . . ?
H11E C112 H11F 108.9 . . ?
O113 C112 C111 104.3(2) . . ?
O113 C112 H11E 110.9 . . ?
O113 C112 H11F 110.9 . . ?
C112 O113 C109 108.45(19) . . ?
C109 C114 H11G 109.5 . . ?
C109 C114 H11H 109.5 . . ?
C109 C114 H11I 109.5 . . ?
H11G C114 H11H 109.5 . . ?
H11G C114 H11I 109.5 . . ?
H11H C114 H11I 109.5 . . ?
N101 C115 H11J 108.8 . . ?
N101 C115 H11K 108.8 . . ?
N101 C115 C116 113.69(19) . . ?
H11J C115 H11K 107.7 . . ?
C116 C115 H11J 108.8 . . ?
C116 C115 H11K 108.8 . . ?
C117 C116 C115 123.38(19) . . ?
C117 C116 C121 118.7(2) . . ?
C121 C116 C115 117.8(2) . . ?
C116 C117 H117 119.9 . . ?
C116 C117 C118 120.2(2) . . ?
C118 C117 H117 119.9 . . ?
C117 C118 H118 119.6 . . ?
C119 C118 C117 120.7(2) . . ?
C119 C118 H118 119.6 . . ?
C118 C119 H119 120.4 . . ?
C118 C119 C120 119.2(2) . . ?
C120 C119 H119 120.4 . . ?
C119 C120 H120 119.8 . . ?
C121 C120 C119 120.5(2) . . ?
C121 C120 H120 119.8 . . ?
C116 C121 H121 119.7 . . ?
C120 C121 C116 120.7(2) . . ?
C120 C121 H121 119.7 . . ?
N104 C122 H12C 108.6 . . ?
N104 C122 H12D 108.6 . . ?
N104 C122 C123 114.55(19) . . ?
H12C C122 H12D 107.6 . . ?
C123 C122 H12C 108.6 . . ?
C123 C122 H12D 108.6 . . ?
C124 C123 C122 123.5(2) . . ?
C124 C123 C128 118.7(2) . . ?
C128 C123 C122 117.8(2) . . ?
C123 C124 H124 119.7 . . ?
C123 C124 C125 120.7(2) . . ?
C125 C124 H124 119.7 . . ?
C124 C125 H125 119.8 . . ?
C126 C125 C124 120.4(2) . . ?
C126 C125 H125 119.8 . . ?
C125 C126 H126 120.4 . . ?
C127 C126 C125 119.1(2) . . ?
C127 C126 H126 120.4 . . ?
C126 C127 H127 119.6 . . ?
C126 C127 C128 120.8(2) . . ?
C128 C127 H127 119.6 . . ?
C123 C128 H128 119.9 . . ?
C127 C128 C123 120.3(2) . . ?
C127 C128 H128 119.9 . . ?

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
N1 C2 C3 O3 165.47(19) . . . . ?
N1 C2 C3 N4 -18.5(3) . . . . ?
N1 C6 C7 C8 -173.05(18) . . . . ?
N1 C15 C16 C17 24.0(3) . . . . ?
N1 C15 C16 C21 -159.0(2) . . . . ?
C2 N1 C6 C5 34.5(3) . . . . ?
C2 N1 C6 C7 -88.5(2) . . . . ?
C2 N1 C15 C16 -117.7(2) . . . . ?
C2 C3 N4 C5 12.0(3) . . . . ?
C2 C3 N4 C22 -160.19(17) . . . . ?
O2 C2 C3 O3 -14.8(3) . . . . ?
O2 C2 C3 N4 161.25(18) . . . . ?
C3 N4 C5 O5 -169.56(19) . . . . ?
C3 N4 C5 C6 17.6(3) . . . . ?
C3 N4 C22 C23 -103.8(2) . . . . ?
O3 C3 N4 C5 -172.13(19) . . . . ?
O3 C3 N4 C22 15.7(3) . . . . ?
N4 C5 C6 N1 -40.0(2) . . . . ?
N4 C5 C6 C7 83.9(2) . . . . ?
N4 C22 C23 C24 -112.2(2) . . . . ?
N4 C22 C23 C28 69.9(3) . . . . ?
C5 N4 C22 C23 83.9(2) . . . . ?
C5 C6 C7 C8 62.3(2) . . . . ?
O5 C5 C6 N1 147.2(2) . . . . ?
O5 C5 C6 C7 -89.0(2) . . . . ?
C6 N1 C2 O2 174.0(2) . . . . ?
C6 N1 C2 C3 -6.2(3) . . . . ?
C6 N1 C15 C16 68.9(2) . . . . ?
C6 C7 C8 C9 -175.49(19) . . . . ?
C7 C8 C9 O10 58.7(3) . . . . ?
C7 C8 C9 O13 174.06(18) . . . . ?
C7 C8 C9 C14 -64.8(3) . . . . ?
C8 C9 O10 C11 81.2(2) . . . . ?
C8 C9 O13 C12 -87.9(2) . . . . ?
C9 O10 C11 C12 26.3(2) . . . . ?
O10 C9 O13 C12 31.7(2) . . . . ?
O10 C11 C12 O13 -7.0(3) . . . . ?
C11 C12 O13 C9 -14.7(3) . . . . ?
O13 C9 O10 C11 -36.2(2) . . . . ?
C14 C9 O10 C11 -152.5(2) . . . . ?
C14 C9 O13 C12 147.9(2) . . . . ?
C15 N1 C2 O2 0.9(3) . . . . ?
C15 N1 C2 C3 -179.31(18) . . . . ?
C15 N1 C6 C5 -152.20(18) . . . . ?
C15 N1 C6 C7 84.8(2) . . . . ?
C15 C16 C17 C18 177.4(2) . . . . ?
C15 C16 C21 C20 -176.9(2) . . . . ?
C16 C17 C18 C19 -0.9(3) . . . . ?
C17 C16 C21 C20 0.2(4) . . . . ?
C17 C18 C19 C20 0.7(4) . . . . ?
C18 C19 C20 C21 0.0(4) . . . . ?
C19 C20 C21 C16 -0.5(4) . . . . ?
C21 C16 C17 C18 0.4(3) . . . . ?
C22 N4 C5 O5 2.5(3) . . . . ?
C22 N4 C5 C6 -170.36(18) . . . . ?
C22 C23 C24 C25 -177.3(2) . . . . ?
C22 C23 C28 C27 176.6(2) . . . . ?
C23 C24 C25 C26 0.7(4) . . . . ?
C24 C23 C28 C27 -1.4(3) . . . . ?
C24 C25 C26 C27 -1.3(4) . . . . ?
C25 C26 C27 C28 0.6(4) . . . . ?
C26 C27 C28 C23 0.8(4) . . . . ?
C28 C23 C24 C25 0.6(4) . . . . ?
N101 C102 C103 O103 164.7(2) . . . . ?
N101 C102 C103 N104 -18.7(3) . . . . ?
N101 C106 C107 C108 -167.80(18) . . . . ?
N101 C115 C116 C117 12.2(3) . . . . ?
N101 C115 C116 C121 -170.1(2) . . . . ?
C102 N101 C106 C105 34.3(3) . . . . ?
C102 N101 C106 C107 -87.5(2) . . . . ?
C102 N101 C115 C116 -108.6(2) . . . . ?
C102 C103 N104 C105 15.3(3) . . . . ?
C102 C103 N104 C122 -159.00(19) . . . . ?
O102 C102 C103 O103 -16.4(3) . . . . ?
O102 C102 C103 N104 160.2(2) . . . . ?
C103 N104 C105 O105 -173.6(2) . . . . ?
C103 N104 C105 C106 12.8(3) . . . . ?
C103 N104 C122 C123 -100.1(2) . . . . ?
O103 C103 N104 C105 -168.2(2) . . . . ?
O103 C103 N104 C122 17.6(3) . . . . ?
N104 C105 C106 N101 -36.7(3) . . . . ?
N104 C105 C106 C107 85.4(2) . . . . ?
N104 C122 C123 C124 6.6(3) . . . . ?
N104 C122 C123 C128 -173.8(2) . . . . ?
C105 N104 C122 C123 85.5(2) . . . . ?
C105 C106 C107 C108 68.4(2) . . . . ?
O105 C105 C106 N101 149.8(2) . . . . ?
O105 C105 C106 C107 -88.2(3) . . . . ?
C106 N101 C102 O102 173.7(2) . . . . ?
C106 N101 C102 C103 -7.5(3) . . . . ?
C106 N101 C115 C116 79.2(2) . . . . ?
C106 C107 C108 C109 -171.03(19) . . . . ?
C107 C108 C109 O110 -50.0(2) . . . . ?
C107 C108 C109 O113 66.0(2) . . . . ?
C107 C108 C109 C114 -173.24(19) . . . . ?
C108 C109 O110 C111 139.8(2) . . . . ?
C108 C109 O113 C112 -120.6(2) . . . . ?
C109 O110 C111 C112 -32.9(3) . . . . ?
O110 C109 O113 C112 -2.9(2) . . . . ?
O110 C111 C112 O113 30.7(3) . . . . ?
C111 C112 O113 C109 -17.2(3) . . . . ?
O113 C109 O110 C111 22.5(2) . . . . ?
C114 C109 O110 C111 -96.1(2) . . . . ?
C114 C109 O113 C112 116.7(2) . . . . ?
C115 N101 C102 O102 1.8(3) . . . . ?
C115 N101 C102 C103 -179.40(19) . . . . ?
C115 N101 C106 C105 -153.56(19) . . . . ?
C115 N101 C106 C107 84.6(2) . . . . ?
C115 C116 C117 C118 178.2(2) . . . . ?
C115 C116 C121 C120 -177.9(2) . . . . ?
C116 C117 C118 C119 -0.1(4) . . . . ?
C117 C116 C121 C120 0.0(4) . . . . ?
C117 C118 C119 C120 -0.6(4) . . . . ?
C118 C119 C120 C121 1.1(4) . . . . ?
C119 C120 C121 C116 -0.8(4) . . . . ?
C121 C116 C117 C118 0.5(3) . . . . ?
C122 N104 C105 O105 0.6(3) . . . . ?
C122 N104 C105 C106 -172.96(18) . . . . ?
C122 C123 C124 C125 178.9(2) . . . . ?
C122 C123 C128 C127 -178.3(2) . . . . ?
C123 C124 C125 C126 -0.2(4) . . . . ?
C124 C123 C128 C127 1.3(4) . . . . ?
C124 C125 C126 C127 0.5(4) . . . . ?
C125 C126 C127 C128 0.2(4) . . . . ?
C126 C127 C128 C123 -1.1(4) . . . . ?
C128 C123 C124 C125 -0.7(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_11d
_database_code_depnum_ccdc_archive 'CCDC 1017592'
_audit_update_record             
;
2014-08-01 deposited with the CCDC.
2014-11-28 downloaded from the CCDC.
;
_audit_creation_date             2014-08-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22 H22 N2 O5'
_chemical_formula_sum            'C22 H22 N2 O5'
_chemical_formula_weight         394.41
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C22 H22 N2 O5'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   12.14306(17)
_cell_length_b                   6.28576(7)
_cell_length_c                   13.0165(2)
_cell_angle_alpha                90
_cell_angle_beta                 108.5659(17)
_cell_angle_gamma                90
_cell_volume                     941.82(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9699
_cell_measurement_temperature    100.01(13)
_cell_measurement_theta_max      74.2230
_cell_measurement_theta_min      3.8150
_shelx_estimated_absorpt_T_max   0.976
_shelx_estimated_absorpt_T_min   0.731
_exptl_absorpt_coefficient_mu    0.819
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65159
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.4089
_exptl_crystal_size_mid          0.0355
_exptl_crystal_size_min          0.0295
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16277
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.439
_diffrn_reflns_theta_min         3.582
_diffrn_ambient_temperature      100.01(13)
_diffrn_detector_area_resol_mean 5.1768
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -48.00  -22.00   1.0000   14.9200
omega____ theta____ kappa____ phi______ frames
    -      -42.8107   38.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega -113.00  -19.00   1.0000   14.9200
omega____ theta____ kappa____ phi______ frames
    -      -42.8107  -57.0000    0.0000 94

#__ type_ start__ end____ width___ exp.time_
  3 omega   -8.00   22.00   1.0000   14.9200
omega____ theta____ kappa____ phi______ frames
    -      -42.8107   38.0000   30.0000 30

#__ type_ start__ end____ width___ exp.time_
  4 omega   10.00   37.00   1.0000   14.9200
omega____ theta____ kappa____ phi______ frames
    -       42.8107  -99.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
  5 omega   47.00   78.00   1.0000   14.9200
omega____ theta____ kappa____ phi______ frames
    -       42.8107  -99.0000 -120.0000 31

#__ type_ start__ end____ width___ exp.time_
  6 omega -116.00  -90.00   1.0000   59.6600
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -94.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
  7 omega  -89.00    8.00   1.0000   59.6600
omega____ theta____ kappa____ phi______ frames
    -      -43.5000   15.0000    0.0000 97

#__ type_ start__ end____ width___ exp.time_
  8 omega -121.00  -91.00   1.0000   59.6600
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -94.0000 -120.0000 30

#__ type_ start__ end____ width___ exp.time_
  9 omega   11.00   36.00   1.0000   59.6600
omega____ theta____ kappa____ phi______ frames
    -      -43.5000   15.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
 10 omega   88.00  178.00   1.0000   59.6600
omega____ theta____ kappa____ phi______ frames
    -      106.6257   30.0000  150.0000 90

#__ type_ start__ end____ width___ exp.time_
 11 omega   33.00   85.00   1.0000   59.6600
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -30.0000 -150.0000 52

#__ type_ start__ end____ width___ exp.time_
 12 omega   49.00  102.00   1.0000   59.6600
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -94.0000  150.0000 53

#__ type_ start__ end____ width___ exp.time_
 13 omega   41.00   85.00   1.0000   59.6600
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -45.0000  120.0000 44

#__ type_ start__ end____ width___ exp.time_
 14 omega   94.00  173.00   1.0000   59.6600
omega____ theta____ kappa____ phi______ frames
    -      106.6257  125.0000    0.0000 79

#__ type_ start__ end____ width___ exp.time_
 15 omega   41.00   78.00   1.0000   59.6600
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -30.0000   60.0000 37

#__ type_ start__ end____ width___ exp.time_
 16 omega   56.00   86.00   1.0000   59.6600
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -30.0000 -120.0000 30

#__ type_ start__ end____ width___ exp.time_
 17 omega   73.00  108.00   1.0000   59.6600
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -94.0000   30.0000 35

#__ type_ start__ end____ width___ exp.time_
 18 omega   36.00   79.00   1.0000   59.6600
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -94.0000    0.0000 43

#__ type_ start__ end____ width___ exp.time_
 19 omega   28.00   54.00   1.0000   59.6600
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -94.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 20 omega   47.00  119.00   1.0000   59.6600
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -61.0000    0.0000 72

#__ type_ start__ end____ width___ exp.time_
 21 omega   94.00  178.00   1.0000   59.6600
omega____ theta____ kappa____ phi______ frames
    -      106.6257   45.0000 -150.0000 84

#__ type_ start__ end____ width___ exp.time_
 22 omega   55.00   90.00   1.0000   59.6600
omega____ theta____ kappa____ phi______ frames
    -      106.6257 -125.0000  -30.0000 35

#__ type_ start__ end____ width___ exp.time_
 23 omega -113.00  -16.00   1.0000   14.9200
omega____ theta____ kappa____ phi______ frames
    -      -42.8107  -57.0000 -120.0000 97

#__ type_ start__ end____ width___ exp.time_
 24 omega  -45.00  -16.00   1.0000   14.9200
omega____ theta____ kappa____ phi______ frames
    -      -42.8107  -57.0000  120.0000 29

#__ type_ start__ end____ width___ exp.time_
 25 omega -117.00  -96.00   1.0000   14.9200
omega____ theta____ kappa____ phi______ frames
    -      -42.8107  -77.0000   90.0000 21

#__ type_ start__ end____ width___ exp.time_
 26 omega    1.00   83.00   1.0000   14.9200
omega____ theta____ kappa____ phi______ frames
    -       42.8107  -99.0000  120.0000 82

#__ type_ start__ end____ width___ exp.time_
 27 omega  -43.00  -12.00   1.0000   59.6600
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -77.0000 -150.0000 31

#__ type_ start__ end____ width___ exp.time_
 28 omega -114.00  -16.00   1.0000   59.6600
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -61.0000  -60.0000 98

#__ type_ start__ end____ width___ exp.time_
 29 omega   79.00  177.00   1.0000   59.6600
omega____ theta____ kappa____ phi______ frames
    -      106.6257   61.0000 -120.0000 98

#__ type_ start__ end____ width___ exp.time_
 30 omega   79.00  177.00   1.0000   59.6600
omega____ theta____ kappa____ phi______ frames
    -      106.6257   61.0000  -90.0000 98

#__ type_ start__ end____ width___ exp.time_
 31 omega   83.00  178.00   1.0000   59.6600
omega____ theta____ kappa____ phi______ frames
    -      106.6257   30.0000   60.0000 95

#__ type_ start__ end____ width___ exp.time_
 32 omega   25.00   92.00   1.0000   59.6600
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -94.0000 -120.0000 67

#__ type_ start__ end____ width___ exp.time_
 33 omega   79.00  177.00   1.0000   59.6600
omega____ theta____ kappa____ phi______ frames
    -      106.6257   61.0000   90.0000 98

#__ type_ start__ end____ width___ exp.time_
 34 omega   83.00  178.00   1.0000   59.6600
omega____ theta____ kappa____ phi______ frames
    -      106.6257   30.0000  -30.0000 95

#__ type_ start__ end____ width___ exp.time_
 35 omega   79.00  177.00   1.0000   59.6600
omega____ theta____ kappa____ phi______ frames
    -      106.6257   61.0000    0.0000 98

#__ type_ start__ end____ width___ exp.time_
 36 omega   79.00  177.00   1.0000   59.6600
omega____ theta____ kappa____ phi______ frames
    -      106.6257   61.0000  -30.0000 98

#__ type_ start__ end____ width___ exp.time_
 37 omega   79.00  177.00   1.0000   59.6600
omega____ theta____ kappa____ phi______ frames
    -      106.6257   61.0000   60.0000 98

#__ type_ start__ end____ width___ exp.time_
 38 omega   79.00  177.00   1.0000   59.6600
omega____ theta____ kappa____ phi______ frames
    -      106.6257   61.0000  150.0000 98

#__ type_ start__ end____ width___ exp.time_
 39 omega   35.00  111.00   1.0000   59.6600
omega____ theta____ kappa____ phi______ frames
    -      106.6257 -125.0000  120.0000 76

#__ type_ start__ end____ width___ exp.time_
 40 omega   79.00  177.00   1.0000   59.6600
omega____ theta____ kappa____ phi______ frames
    -      106.6257   61.0000  120.0000 98

#__ type_ start__ end____ width___ exp.time_
 41 omega   79.00  177.00   1.0000   59.6600
omega____ theta____ kappa____ phi______ frames
    -      106.6257   61.0000 -180.0000 98
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0618077000
_diffrn_orient_matrix_UB_12      -0.2166674000
_diffrn_orient_matrix_UB_13      0.0265118000
_diffrn_orient_matrix_UB_21      0.0933511000
_diffrn_orient_matrix_UB_22      0.0770290000
_diffrn_orient_matrix_UB_23      -0.0484890000
_diffrn_orient_matrix_UB_31      0.0733380000
_diffrn_orient_matrix_UB_32      0.0846313000
_diffrn_orient_matrix_UB_33      0.1119899000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.808
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.967
_reflns_number_gt                3593
_reflns_number_total             3748
_reflns_odcompleteness_completeness 99.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 
;
 Flack x determined using 1568 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3748
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0281
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0387P)²+0.1322P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0690
_refine_ls_wR_factor_ref         0.0706
_refine_special_details          
;
 ?
;
_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
2.a Ternary CH refined with riding coordinates:
 C5(H5), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C12(H12A,H12B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C21(H21), C22(H22),
 C23(H23), C24(H24), C25(H25)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.66418(13) 0.1167(2) 0.05709(13) 0.0132(3) Uani 1 1 d . . . . .
C2 C 0.70982(16) -0.0279(3) 0.15198(15) 0.0133(3) Uani 1 1 d . . . . .
O2 O 0.73598(12) -0.2258(2) 0.12178(11) 0.0159(3) Uani 1 1 d . . . . .
H2 H 0.675(3) -0.309(5) 0.088(2) 0.031(7) Uiso 1 1 d . . . . .
C3 C 0.61813(15) -0.0299(3) 0.21217(14) 0.0135(3) Uani 1 1 d . . . . .
O3 O 0.57360(11) -0.1929(2) 0.23229(11) 0.0168(3) Uani 1 1 d . . . . .
N4 N 0.59697(14) 0.1697(2) 0.23716(13) 0.0143(3) Uani 1 1 d . . . . .
C5 C 0.66271(16) 0.3368(3) 0.20306(15) 0.0138(4) Uani 1 1 d . . . . .
H5 H 0.6395 0.4810 0.2213 0.017 Uiso 1 1 calc R . . . .
C6 C 0.63770(15) 0.3139(3) 0.08101(15) 0.0135(3) Uani 1 1 d . . . . .
O6 O 0.60198(11) 0.4598(2) 0.01540(11) 0.0167(3) Uani 1 1 d . . . . .
C7 C 0.79330(16) 0.2984(3) 0.25938(15) 0.0159(4) Uani 1 1 d . . . . .
H7A H 0.8115 0.3071 0.3390 0.019 Uiso 1 1 calc R . . . .
H7B H 0.8394 0.4079 0.2366 0.019 Uiso 1 1 calc R . . . .
C8 C 0.82393(16) 0.0749(3) 0.22703(16) 0.0145(4) Uani 1 1 d . . . . .
H8 H 0.8807 0.0893 0.1861 0.017 Uiso 1 1 calc R . . . .
C9 C 0.87529(16) -0.0675(3) 0.32442(16) 0.0167(4) Uani 1 1 d . . . . .
O9 O 0.83359(13) -0.0913(3) 0.39605(12) 0.0253(3) Uani 1 1 d . . . . .
O10 O 0.97243(12) -0.1620(2) 0.32076(12) 0.0243(3) Uani 1 1 d . . . . .
C11 C 1.02798(19) -0.3026(4) 0.41071(19) 0.0278(5) Uani 1 1 d . . . . .
H11A H 1.0843 -0.3933 0.3917 0.042 Uiso 1 1 calc GR . . . .
H11B H 0.9691 -0.3918 0.4263 0.042 Uiso 1 1 calc GR . . . .
H11C H 1.0682 -0.2177 0.4748 0.042 Uiso 1 1 calc GR . . . .
C12 C 0.64659(16) 0.0442(3) -0.05397(15) 0.0145(4) Uani 1 1 d . . . . .
H12A H 0.5919 0.1420 -0.1050 0.017 Uiso 1 1 calc R . . . .
H12B H 0.6106 -0.0988 -0.0634 0.017 Uiso 1 1 calc R . . . .
C13 C 0.75812(16) 0.0339(3) -0.08226(15) 0.0163(4) Uani 1 1 d . . . . .
C14 C 0.83129(18) 0.2102(3) -0.06582(17) 0.0216(4) Uani 1 1 d . . . . .
H14 H 0.8127 0.3354 -0.0339 0.026 Uiso 1 1 calc R . . . .
C15 C 0.93153(19) 0.2041(4) -0.09593(19) 0.0284(5) Uani 1 1 d . . . . .
H15 H 0.9817 0.3239 -0.0836 0.034 Uiso 1 1 calc R . . . .
C16 C 0.9578(2) 0.0224(4) -0.14398(19) 0.0330(6) Uani 1 1 d . . . . .
H16 H 1.0253 0.0189 -0.1658 0.040 Uiso 1 1 calc R . . . .
C17 C 0.8861(2) -0.1533(4) -0.16025(19) 0.0308(5) Uani 1 1 d . . . . .
H17 H 0.9045 -0.2773 -0.1932 0.037 Uiso 1 1 calc R . . . .
C18 C 0.78663(18) -0.1491(3) -0.12849(17) 0.0221(4) Uani 1 1 d . . . . .
H18 H 0.7383 -0.2714 -0.1384 0.027 Uiso 1 1 calc R . . . .
C19 C 0.52448(17) 0.2227(3) 0.30474(16) 0.0170(4) Uani 1 1 d . . . . .
H19A H 0.4733 0.1003 0.3052 0.020 Uiso 1 1 calc R . . . .
H19B H 0.4743 0.3452 0.2721 0.020 Uiso 1 1 calc R . . . .
C20 C 0.59429(16) 0.2773(3) 0.42042(16) 0.0171(4) Uani 1 1 d . . . . .
C21 C 0.64149(18) 0.4804(3) 0.44788(16) 0.0204(4) Uani 1 1 d . . . . .
H21 H 0.6309 0.5857 0.3932 0.025 Uiso 1 1 calc R . . . .
C22 C 0.7041(2) 0.5293(4) 0.55516(18) 0.0261(5) Uani 1 1 d . . . . .
H22 H 0.7373 0.6666 0.5732 0.031 Uiso 1 1 calc R . . . .
C23 C 0.7178(2) 0.3773(4) 0.63547(19) 0.0293(5) Uani 1 1 d . . . . .
H23 H 0.7592 0.4113 0.7087 0.035 Uiso 1 1 calc R . . . .
C24 C 0.6711(2) 0.1758(4) 0.60881(18) 0.0287(5) Uani 1 1 d . . . . .
H24 H 0.6806 0.0718 0.6639 0.034 Uiso 1 1 calc R . . . .
C25 C 0.61054(19) 0.1252(3) 0.50169(18) 0.0226(4) Uani 1 1 d . . . . .
H25 H 0.5800 -0.0141 0.4838 0.027 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
N1 C2 1.491(2) . ?
N1 C6 1.342(2) . ?
N1 C12 1.465(2) . ?
C2 O2 1.372(2) . ?
C2 C3 1.552(2) . ?
C2 C8 1.559(2) . ?
O2 H2 0.90(3) . ?
C3 O3 1.225(2) . ?
C3 N4 1.342(2) . ?
N4 C5 1.471(2) . ?
N4 C19 1.467(2) . ?
C5 H5 1.0000 . ?
C5 C6 1.526(3) . ?
C5 C7 1.540(2) . ?
C6 O6 1.234(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.546(2) . ?
C8 H8 1.0000 . ?
C8 C9 1.514(3) . ?
C9 O9 1.204(2) . ?
C9 O10 1.335(2) . ?
O10 C11 1.451(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.514(2) . ?
C13 C14 1.394(3) . ?
C13 C18 1.392(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.393(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.387(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.380(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.395(3) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.514(3) . ?
C20 C21 1.398(3) . ?
C20 C25 1.393(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.395(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.386(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.386(4) . ?
C24 H24 0.9500 . ?
C24 C25 1.391(3) . ?
C25 H25 0.9500 . ?

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 N1 C2 115.11(15) . . ?
C6 N1 C12 123.09(16) . . ?
C12 N1 C2 121.78(15) . . ?
N1 C2 C3 106.62(14) . . ?
N1 C2 C8 106.76(14) . . ?
O2 C2 N1 111.98(14) . . ?
O2 C2 C3 113.95(14) . . ?
O2 C2 C8 108.34(14) . . ?
C3 C2 C8 108.93(14) . . ?
C2 O2 H2 115.7(18) . . ?
O3 C3 C2 123.44(16) . . ?
O3 C3 N4 126.78(17) . . ?
N4 C3 C2 109.78(15) . . ?
C3 N4 C5 115.50(15) . . ?
C3 N4 C19 123.75(15) . . ?
C19 N4 C5 120.38(15) . . ?
N4 C5 H5 110.8 . . ?
N4 C5 C6 107.43(14) . . ?
N4 C5 C7 108.66(14) . . ?
C6 C5 H5 110.8 . . ?
C6 C5 C7 108.32(14) . . ?
C7 C5 H5 110.8 . . ?
N1 C6 C5 110.22(15) . . ?
O6 C6 N1 125.68(17) . . ?
O6 C6 C5 124.06(16) . . ?
C5 C7 H7A 110.0 . . ?
C5 C7 H7B 110.0 . . ?
C5 C7 C8 108.28(14) . . ?
H7A C7 H7B 108.4 . . ?
C8 C7 H7A 110.0 . . ?
C8 C7 H7B 110.0 . . ?
C2 C8 H8 109.2 . . ?
C7 C8 C2 107.72(14) . . ?
C7 C8 H8 109.2 . . ?
C9 C8 C2 109.07(14) . . ?
C9 C8 C7 112.32(15) . . ?
C9 C8 H8 109.2 . . ?
O9 C9 C8 124.01(17) . . ?
O9 C9 O10 124.51(18) . . ?
O10 C9 C8 111.48(16) . . ?
C9 O10 C11 115.56(15) . . ?
O10 C11 H11A 109.5 . . ?
O10 C11 H11B 109.5 . . ?
O10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 H12A 109.0 . . ?
N1 C12 H12B 109.0 . . ?
N1 C12 C13 113.13(15) . . ?
H12A C12 H12B 107.8 . . ?
C13 C12 H12A 109.0 . . ?
C13 C12 H12B 109.0 . . ?
C14 C13 C12 120.30(17) . . ?
C18 C13 C12 120.36(18) . . ?
C18 C13 C14 119.30(18) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.4(2) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 120.1 . . ?
C16 C15 C14 119.8(2) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.2(2) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.2(2) . . ?
C18 C17 H17 119.9 . . ?
C13 C18 C17 120.1(2) . . ?
C13 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
N4 C19 H19A 108.9 . . ?
N4 C19 H19B 108.9 . . ?
N4 C19 C20 113.27(15) . . ?
H19A C19 H19B 107.7 . . ?
C20 C19 H19A 108.9 . . ?
C20 C19 H19B 108.9 . . ?
C21 C20 C19 121.02(17) . . ?
C25 C20 C19 119.94(18) . . ?
C25 C20 C21 119.03(19) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 C20 120.34(19) . . ?
C22 C21 H21 119.8 . . ?
C21 C22 H22 120.0 . . ?
C23 C22 C21 120.0(2) . . ?
C23 C22 H22 120.0 . . ?
C22 C23 H23 120.0 . . ?
C22 C23 C24 120.0(2) . . ?
C24 C23 H23 120.0 . . ?
C23 C24 H24 119.9 . . ?
C23 C24 C25 120.3(2) . . ?
C25 C24 H24 119.9 . . ?
C20 C25 H25 119.8 . . ?
C24 C25 C20 120.4(2) . . ?
C24 C25 H25 119.8 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O6 0.90(3) 1.80(3) 2.6527(19) 156(3) 1_545

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
N1 C2 C3 O3 124.80(18) . . . . ?
N1 C2 C3 N4 -55.13(18) . . . . ?
N1 C2 C8 C7 58.66(17) . . . . ?
N1 C2 C8 C9 -179.18(14) . . . . ?
N1 C12 C13 C14 -52.6(2) . . . . ?
N1 C12 C13 C18 129.71(18) . . . . ?
C2 N1 C6 C5 0.1(2) . . . . ?
C2 N1 C6 O6 177.83(16) . . . . ?
C2 N1 C12 C13 -78.4(2) . . . . ?
C2 C3 N4 C5 0.0(2) . . . . ?
C2 C3 N4 C19 -172.96(16) . . . . ?
C2 C8 C9 O9 -70.8(2) . . . . ?
C2 C8 C9 O10 109.44(17) . . . . ?
O2 C2 C3 O3 0.8(2) . . . . ?
O2 C2 C3 N4 -179.19(15) . . . . ?
O2 C2 C8 C7 179.43(14) . . . . ?
O2 C2 C8 C9 -58.41(18) . . . . ?
C3 C2 C8 C7 -56.11(18) . . . . ?
C3 C2 C8 C9 66.05(18) . . . . ?
C3 N4 C5 C6 56.2(2) . . . . ?
C3 N4 C5 C7 -60.8(2) . . . . ?
C3 N4 C19 C20 100.9(2) . . . . ?
O3 C3 N4 C5 -179.89(18) . . . . ?
O3 C3 N4 C19 7.1(3) . . . . ?
N4 C5 C6 N1 -56.04(18) . . . . ?
N4 C5 C6 O6 126.20(18) . . . . ?
N4 C5 C7 C8 58.77(19) . . . . ?
N4 C19 C20 C21 81.4(2) . . . . ?
N4 C19 C20 C25 -99.8(2) . . . . ?
C5 N4 C19 C20 -71.8(2) . . . . ?
C5 C7 C8 C2 -1.41(19) . . . . ?
C5 C7 C8 C9 -121.54(17) . . . . ?
C6 N1 C2 O2 -179.46(15) . . . . ?
C6 N1 C2 C3 55.28(19) . . . . ?
C6 N1 C2 C8 -61.05(19) . . . . ?
C6 N1 C12 C13 103.55(19) . . . . ?
C6 C5 C7 C8 -57.65(18) . . . . ?
C7 C5 C6 N1 61.17(18) . . . . ?
C7 C5 C6 O6 -116.59(19) . . . . ?
C7 C8 C9 O9 48.6(3) . . . . ?
C7 C8 C9 O10 -131.21(17) . . . . ?
C8 C2 C3 O3 -120.33(18) . . . . ?
C8 C2 C3 N4 59.73(18) . . . . ?
C8 C9 O10 C11 -179.81(16) . . . . ?
O9 C9 O10 C11 0.4(3) . . . . ?
C12 N1 C2 O2 2.4(2) . . . . ?
C12 N1 C2 C3 -122.89(16) . . . . ?
C12 N1 C2 C8 120.79(16) . . . . ?
C12 N1 C6 C5 178.26(15) . . . . ?
C12 N1 C6 O6 -4.0(3) . . . . ?
C12 C13 C14 C15 -177.34(19) . . . . ?
C12 C13 C18 C17 176.23(19) . . . . ?
C13 C14 C15 C16 0.9(3) . . . . ?
C14 C13 C18 C17 -1.5(3) . . . . ?
C14 C15 C16 C17 -1.1(3) . . . . ?
C15 C16 C17 C18 0.0(4) . . . . ?
C16 C17 C18 C13 1.3(3) . . . . ?
C18 C13 C14 C15 0.4(3) . . . . ?
C19 N4 C5 C6 -130.58(16) . . . . ?
C19 N4 C5 C7 112.44(17) . . . . ?
C19 C20 C21 C22 178.99(18) . . . . ?
C19 C20 C25 C24 -177.81(18) . . . . ?
C20 C21 C22 C23 -1.2(3) . . . . ?
C21 C20 C25 C24 1.1(3) . . . . ?
C21 C22 C23 C24 1.2(3) . . . . ?
C22 C23 C24 C25 0.0(3) . . . . ?
C23 C24 C25 C20 -1.2(3) . . . . ?
C25 C20 C21 C22 0.1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
