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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
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data_sg783
_audit_creation_date             
;
'Tue Apr 15 17:14:35 2014'
;
_audit_creation_method           
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
(1R,2S,3R,5S)-6-(4-chlorophenyl)-1-hydroxy-2-isopropyl-3-(4-nitrophenyl)-8-oxa-6-azabicyclo[3.2.1]octan-7-one
_chemical_formula_moiety         '2(C21 H21 Cl N2 O5)'
_chemical_formula_sum            'C42 H42 Cl2 N4 O10'
_chemical_formula_weight         833.69
_chemical_absolute_configuration ad
_chemical_melting_point          471
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'
Cl Cl 0.3639 0.7018 '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'

_symmetry_space_group_name_H-M_alt 'P 21 21 21'
_cell_length_a                   7.85187(17)
_cell_length_b                   19.3756(4)
_cell_length_c                   26.7779(6)
_cell_angle_alpha                90.0
_cell_angle_beta                 90.0
_cell_angle_gamma                90.0
_cell_volume                     4073.84(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6029
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.6850
_cell_measurement_theta_min      4.8330
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.965
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73740
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1744
_exptl_crystal_size_max          .26
_exptl_crystal_size_mid          .18
_exptl_crystal_size_min          .06
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            12523
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.645
_diffrn_reflns_theta_min         4.013
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -70.00   -2.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5364  125.0000 -150.0000 68

#__ type_ start__ end____ width___ exp.time_
  2 omega  -70.00   19.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5364   77.0000   30.0000 89

#__ type_ start__ end____ width___ exp.time_
  3 omega   37.00   91.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      107.1501  -30.0000   90.0000 54

#__ type_ start__ end____ width___ exp.time_
  4 omega   49.00   98.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      107.1501  -45.0000    0.0000 49

#__ type_ start__ end____ width___ exp.time_
  5 omega   38.00  136.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      107.1501  -61.0000 -180.0000 98

#__ type_ start__ end____ width___ exp.time_
  6 omega   36.00   82.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      107.1501  -45.0000  -90.0000 46

#__ type_ start__ end____ width___ exp.time_
  7 omega   35.00  136.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      107.1501  -77.0000   90.0000 101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1536279000
_diffrn_orient_matrix_UB_12      -0.0485903000
_diffrn_orient_matrix_UB_13      -0.0071723000
_diffrn_orient_matrix_UB_21      -0.1020309000
_diffrn_orient_matrix_UB_22      0.0595979000
_diffrn_orient_matrix_UB_23      -0.0234472000
_diffrn_orient_matrix_UB_31      0.0670114000
_diffrn_orient_matrix_UB_32      -0.0201993000
_diffrn_orient_matrix_UB_33      -0.0520440000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.751
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.937
_reflns_number_gt                7073
_reflns_number_total             7842
_reflns_odcompleteness_completeness 98.94
_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 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Flack x determined using 2784 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.012(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     529
_refine_ls_number_reflns         7842
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0470
_refine_ls_restrained_S_all      1.033
_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)+(0.0771P)²+0.4594P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1299
_refine_ls_wR_factor_ref         0.1372
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C31(H31), C33(H33), C12(H12), C9(H9), C30(H30), C13(H13), C34(H34)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C32(H32A,H32B)
2.c Aromatic/amide H refined with riding coordinates:
 C42(H42), C20(H20), C21(H21), C41(H41), C38(H38), C17(H17), C39(H39), C2(H2A),
  C27(H27), C24(H24), C3(H3), C6(H6), C18(H18), C23(H23), C5(H5), C26(H26)
2.d Idealised Me refined as rotating group:
 C35(H35A,H35B,H35C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C36(H36A,H36B,
 H36C)
2.e Idealised tetrahedral OH refined as rotating group:
 O7(H7), O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
Cl1 Cl 0.3592(2) 0.77682(7) 0.68511(7) 0.1091(5) Uani 1 1 d . . . . .
Cl2 Cl 0.0306(4) 0.78271(8) 0.55850(7) 0.1332(8) Uani 1 1 d . . . . .
O1 O 0.7105(3) 0.46849(15) 0.51620(10) 0.0598(6) Uani 1 1 d . . . . .
O6 O -0.2434(3) 0.46865(14) 0.73308(10) 0.0584(6) Uani 1 1 d . . . . .
O8 O -0.0592(3) 0.43893(13) 0.61761(9) 0.0560(5) Uani 1 1 d . . . . .
O3 O 0.5231(3) 0.43830(12) 0.63053(9) 0.0565(5) Uani 1 1 d . . . . .
N1 N 0.5504(3) 0.52556(14) 0.57227(9) 0.0477(5) Uani 1 1 d . . . . .
O7 O -0.2638(3) 0.36503(14) 0.69194(11) 0.0659(7) Uani 1 1 d . . . . .
H7 H -0.3419 0.3803 0.6749 0.099 Uiso 1 1 calc GR . . . .
O2 O 0.7275(4) 0.36360(15) 0.55724(11) 0.0689(7) Uani 1 1 d . . . . .
H2 H 0.8105 0.3798 0.5717 0.103 Uiso 1 1 calc GR . . . .
N3 N -0.0975(3) 0.52807(14) 0.67426(10) 0.0480(5) Uani 1 1 d . . . . .
C7 C 0.5567(4) 0.45983(16) 0.58879(12) 0.0477(6) Uani 1 1 d . . . . .
C28 C -0.0974(4) 0.46114(17) 0.65856(12) 0.0479(6) Uani 1 1 d . . . . .
C22 C -0.0629(4) 0.58804(17) 0.64608(12) 0.0487(6) Uani 1 1 d . . . . .
C8 C 0.6195(4) 0.41563(18) 0.54412(13) 0.0522(7) Uani 1 1 d . . . . .
C10 C 0.3571(4) 0.44956(17) 0.49643(11) 0.0464(6) Uani 1 1 d . . . . .
H10 H 0.2872 0.4585 0.5260 0.056 Uiso 1 1 calc R . . . .
C31 C 0.1125(4) 0.45341(18) 0.74845(11) 0.0499(7) Uani 1 1 d . . . . .
H31 H 0.1828 0.4634 0.7191 0.060 Uiso 1 1 calc R . . . .
C29 C -0.1553(4) 0.41744(18) 0.70422(12) 0.0511(7) Uani 1 1 d . . . . .
C1 C 0.5010(4) 0.58501(17) 0.59956(12) 0.0474(6) Uani 1 1 d . . . . .
C37 C 0.2335(4) 0.44058(17) 0.79137(11) 0.0487(6) Uani 1 1 d . . . . .
N4 N 0.5808(6) 0.41128(18) 0.91058(13) 0.0719(9) Uani 1 1 d . . . . .
C33 C -0.1440(5) 0.52840(19) 0.72778(12) 0.0545(7) Uani 1 1 d . . . . .
H33 H -0.2088 0.5699 0.7366 0.065 Uiso 1 1 calc R . . . .
C40 C 0.4590(5) 0.42195(18) 0.86959(12) 0.0556(7) Uani 1 1 d . . . . .
C12 C 0.6048(4) 0.52685(19) 0.51944(12) 0.0523(7) Uani 1 1 d . . . . .
H12 H 0.6675 0.5692 0.5116 0.063 Uiso 1 1 calc R . . . .
C42 C 0.1784(5) 0.4138(2) 0.83702(12) 0.0569(8) Uani 1 1 d . . . . .
H42 H 0.0643 0.4023 0.8411 0.068 Uiso 1 1 calc R . . . .
O9 O 0.7286(5) 0.4293(2) 0.90422(14) 0.0915(10) Uani 1 1 d . . . . .
C16 C 0.2368(4) 0.43062(16) 0.45453(11) 0.0476(6) Uani 1 1 d . . . . .
C9 C 0.4779(4) 0.38891(17) 0.50957(12) 0.0501(7) Uani 1 1 d . . . . .
H9 H 0.5343 0.3762 0.4782 0.060 Uiso 1 1 calc R . . . .
C20 C -0.0513(5) 0.41694(19) 0.42419(14) 0.0577(8) Uani 1 1 d . . . . .
H20 H -0.1682 0.4197 0.4295 0.069 Uiso 1 1 calc R . . . .
C30 C -0.0021(4) 0.39099(17) 0.73468(12) 0.0507(7) Uani 1 1 d . . . . .
H30 H -0.0461 0.3713 0.7658 0.061 Uiso 1 1 calc R . . . .
N2 N -0.1078(6) 0.3808(2) 0.33852(15) 0.0797(11) Uani 1 1 d . . . . .
C21 C 0.0628(4) 0.43392(18) 0.46168(12) 0.0516(7) Uani 1 1 d . . . . .
H21 H 0.0211 0.4479 0.4926 0.062 Uiso 1 1 calc R . . . .
C41 C 0.2901(6) 0.4041(2) 0.87615(12) 0.0611(8) Uani 1 1 d . . . . .
H41 H 0.2525 0.3860 0.9064 0.073 Uiso 1 1 calc R . . . .
C19 C 0.0126(5) 0.39588(18) 0.37902(13) 0.0577(8) Uani 1 1 d . . . . .
C11 C 0.4541(5) 0.51710(19) 0.48442(12) 0.0536(7) Uani 1 1 d . . . . .
H11A H 0.4943 0.5157 0.4502 0.064 Uiso 1 1 calc R . . . .
H11B H 0.3771 0.5560 0.4877 0.064 Uiso 1 1 calc R . . . .
O10 O 0.5300(7) 0.3860(2) 0.94873(12) 0.1039(13) Uani 1 1 d . . . . .
C38 C 0.4031(4) 0.45802(19) 0.78662(13) 0.0546(7) Uani 1 1 d . . . . .
H38 H 0.4415 0.4764 0.7566 0.066 Uiso 1 1 calc R . . . .
C4 C 0.4136(6) 0.7028(2) 0.65178(18) 0.0721(11) Uani 1 1 d . . . . .
O5 O -0.0505(7) 0.3658(3) 0.29774(14) 0.1122(14) Uani 1 1 d . . . . .
C32 C 0.0121(5) 0.52046(19) 0.76058(12) 0.0566(7) Uani 1 1 d . . . . .
H32A H -0.0228 0.5196 0.7953 0.068 Uiso 1 1 calc R . . . .
H32B H 0.0861 0.5600 0.7559 0.068 Uiso 1 1 calc R . . . .
C17 C 0.2971(5) 0.4095(2) 0.40784(14) 0.0641(9) Uani 1 1 d . . . . .
H17 H 0.4139 0.4073 0.4022 0.077 Uiso 1 1 calc R . . . .
C39 C 0.5178(5) 0.44895(19) 0.82545(13) 0.0568(7) Uani 1 1 d . . . . .
H39 H 0.6318 0.4609 0.8217 0.068 Uiso 1 1 calc R . . . .
C13 C 0.3775(6) 0.3238(2) 0.52628(16) 0.0646(9) Uani 1 1 d . . . . .
H13 H 0.2809 0.3210 0.5032 0.078 Uiso 1 1 calc R . . . .
C25 C -0.0094(7) 0.7071(2) 0.59189(18) 0.0778(12) Uani 1 1 d . . . . .
O4 O -0.2600(6) 0.3859(3) 0.34645(18) 0.1128(14) Uani 1 1 d . . . . .
C2 C 0.4567(6) 0.5815(2) 0.64947(14) 0.0632(9) Uani 1 1 d . . . . .
H2A H 0.4558 0.5392 0.6658 0.076 Uiso 1 1 calc R . . . .
C27 C -0.0883(7) 0.6524(2) 0.66710(16) 0.0746(12) Uani 1 1 d . . . . .
H27 H -0.1245 0.6557 0.7001 0.090 Uiso 1 1 calc R . . . .
C24 C 0.0173(7) 0.6445(2) 0.57024(16) 0.0794(12) Uani 1 1 d . . . . .
H24 H 0.0536 0.6421 0.5372 0.095 Uiso 1 1 calc R . . . .
C3 C 0.4140(6) 0.6407(2) 0.67507(16) 0.0728(11) Uani 1 1 d . . . . .
H3 H 0.3850 0.6380 0.7087 0.087 Uiso 1 1 calc R . . . .
C34 C 0.0927(6) 0.3319(2) 0.70567(16) 0.0679(10) Uani 1 1 d . . . . .
H34 H 0.0947 0.3444 0.6702 0.081 Uiso 1 1 calc R . . . .
C6 C 0.5005(7) 0.6487(2) 0.57624(15) 0.0694(10) Uani 1 1 d . . . . .
H6 H 0.5291 0.6520 0.5426 0.083 Uiso 1 1 calc R . . . .
C18 C 0.1856(6) 0.3919(2) 0.36990(14) 0.0666(9) Uani 1 1 d . . . . .
H18 H 0.2262 0.3777 0.3389 0.080 Uiso 1 1 calc R . . . .
C23 C -0.0090(6) 0.5846(2) 0.59676(15) 0.0683(10) Uani 1 1 d . . . . .
H23 H 0.0093 0.5420 0.5817 0.082 Uiso 1 1 calc R . . . .
C35 C 0.2729(8) 0.3184(3) 0.7218(2) 0.1011(19) Uani 1 1 d . . . . .
H35A H 0.3384 0.3600 0.7188 0.152 Uiso 1 1 calc GR . . . .
H35B H 0.3218 0.2832 0.7011 0.152 Uiso 1 1 calc GR . . . .
H35C H 0.2737 0.3033 0.7560 0.152 Uiso 1 1 calc GR . . . .
C5 C 0.4579(8) 0.7077(2) 0.6025(2) 0.0825(13) Uani 1 1 d . . . . .
H5 H 0.4593 0.7504 0.5867 0.099 Uiso 1 1 calc R . . . .
C26 C -0.0608(9) 0.7118(2) 0.6399(2) 0.0889(15) Uani 1 1 d . . . . .
H26 H -0.0774 0.7548 0.6546 0.107 Uiso 1 1 calc R . . . .
C14 C 0.2988(9) 0.3271(3) 0.5770(2) 0.0976(17) Uani 1 1 d . . . . .
H14A H 0.3869 0.3284 0.6018 0.146 Uiso 1 1 calc GR . . . .
H14B H 0.2288 0.2872 0.5822 0.146 Uiso 1 1 calc GR . . . .
H14C H 0.2302 0.3680 0.5796 0.146 Uiso 1 1 calc GR . . . .
C15 C 0.4759(10) 0.2578(3) 0.5180(3) 0.109(2) Uani 1 1 d . . . . .
H15A H 0.5237 0.2580 0.4850 0.163 Uiso 1 1 calc GR . . . .
H15B H 0.4007 0.2191 0.5215 0.163 Uiso 1 1 calc GR . . . .
H15C H 0.5658 0.2545 0.5421 0.163 Uiso 1 1 calc GR . . . .
C36 C -0.0031(9) 0.2632(3) 0.7107(3) 0.120(2) Uani 1 1 d . . . . .
H36A H -0.0219 0.2533 0.7454 0.180 Uiso 1 1 calc GR . . . .
H36B H 0.0634 0.2269 0.6960 0.180 Uiso 1 1 calc GR . . . .
H36C H -0.1106 0.2664 0.6938 0.180 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C4 1.743(4) . ?
Cl2 C25 1.745(4) . ?
O1 C8 1.456(5) . ?
O1 C12 1.406(4) . ?
O6 C29 1.435(4) . ?
O6 C33 1.403(5) . ?
O8 C28 1.216(4) . ?
O3 C7 1.222(4) . ?
N1 C7 1.349(4) . ?
N1 C1 1.418(4) . ?
N1 C12 1.478(4) . ?
O7 H7 0.8200 . ?
O7 C29 1.365(4) . ?
O2 H2 0.8200 . ?
O2 C8 1.363(4) . ?
N3 C28 1.363(4) . ?
N3 C22 1.412(4) . ?
N3 C33 1.479(4) . ?
C7 C8 1.551(4) . ?
C28 C29 1.555(5) . ?
C22 C27 1.382(5) . ?
C22 C23 1.389(5) . ?
C8 C9 1.537(4) . ?
C10 H10 0.9800 . ?
C10 C16 1.512(4) . ?
C10 C9 1.551(4) . ?
C10 C11 1.548(5) . ?
C31 H31 0.9800 . ?
C31 C37 1.512(4) . ?
C31 C30 1.552(5) . ?
C31 C32 1.554(5) . ?
C29 C30 1.541(4) . ?
C1 C2 1.383(5) . ?
C1 C6 1.384(5) . ?
C37 C42 1.397(5) . ?
C37 C38 1.380(5) . ?
N4 C40 1.470(5) . ?
N4 O9 1.224(6) . ?
N4 O10 1.201(6) . ?
C33 H33 0.9800 . ?
C33 C32 1.516(5) . ?
C40 C41 1.382(6) . ?
C40 C39 1.372(5) . ?
C12 H12 0.9800 . ?
C12 C11 1.522(5) . ?
C42 H42 0.9300 . ?
C42 C41 1.379(5) . ?
C16 C21 1.381(5) . ?
C16 C17 1.398(5) . ?
C9 H9 0.9800 . ?
C9 C13 1.554(5) . ?
C20 H20 0.9300 . ?
C20 C21 1.386(5) . ?
C20 C19 1.372(6) . ?
C30 H30 0.9800 . ?
C30 C34 1.571(5) . ?
N2 C19 1.468(5) . ?
N2 O5 1.216(6) . ?
N2 O4 1.218(7) . ?
C21 H21 0.9300 . ?
C41 H41 0.9300 . ?
C19 C18 1.382(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C38 H38 0.9300 . ?
C38 C39 1.387(5) . ?
C4 C3 1.355(7) . ?
C4 C5 1.368(7) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C17 H17 0.9300 . ?
C17 C18 1.384(6) . ?
C39 H39 0.9300 . ?
C13 H13 0.9800 . ?
C13 C14 1.493(7) . ?
C13 C15 1.510(7) . ?
C25 C24 1.361(7) . ?
C25 C26 1.351(7) . ?
C2 H2A 0.9300 . ?
C2 C3 1.377(6) . ?
C27 H27 0.9300 . ?
C27 C26 1.379(7) . ?
C24 H24 0.9300 . ?
C24 C23 1.375(6) . ?
C3 H3 0.9300 . ?
C34 H34 0.9800 . ?
C34 C35 1.503(7) . ?
C34 C36 1.535(8) . ?
C6 H6 0.9300 . ?
C6 C5 1.382(6) . ?
C18 H18 0.9300 . ?
C23 H23 0.9300 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C5 H5 0.9300 . ?
C26 H26 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 O1 C8 104.1(2) . . ?
C33 O6 C29 104.3(2) . . ?
C7 N1 C1 127.4(3) . . ?
C7 N1 C12 108.6(3) . . ?
C1 N1 C12 124.0(3) . . ?
C29 O7 H7 109.5 . . ?
C8 O2 H2 109.5 . . ?
C28 N3 C22 128.2(3) . . ?
C28 N3 C33 107.6(3) . . ?
C22 N3 C33 124.2(3) . . ?
O3 C7 N1 127.9(3) . . ?
O3 C7 C8 125.8(3) . . ?
N1 C7 C8 106.3(3) . . ?
O8 C28 N3 127.9(3) . . ?
O8 C28 C29 126.1(3) . . ?
N3 C28 C29 106.0(3) . . ?
C27 C22 N3 119.8(3) . . ?
C27 C22 C23 118.3(3) . . ?
C23 C22 N3 121.8(3) . . ?
O1 C8 C7 99.4(3) . . ?
O1 C8 C9 106.5(3) . . ?
O2 C8 O1 110.3(3) . . ?
O2 C8 C7 114.0(3) . . ?
O2 C8 C9 110.9(3) . . ?
C9 C8 C7 114.8(3) . . ?
C16 C10 H10 107.1 . . ?
C16 C10 C9 111.5(3) . . ?
C16 C10 C11 111.0(3) . . ?
C9 C10 H10 107.1 . . ?
C11 C10 H10 107.1 . . ?
C11 C10 C9 112.8(3) . . ?
C37 C31 H31 106.8 . . ?
C37 C31 C30 114.6(3) . . ?
C37 C31 C32 107.3(3) . . ?
C30 C31 H31 106.8 . . ?
C30 C31 C32 114.0(3) . . ?
C32 C31 H31 106.8 . . ?
O6 C29 C28 100.8(3) . . ?
O6 C29 C30 108.7(3) . . ?
O7 C29 O6 110.1(3) . . ?
O7 C29 C28 113.4(3) . . ?
O7 C29 C30 111.5(3) . . ?
C30 C29 C28 111.7(3) . . ?
C2 C1 N1 121.8(3) . . ?
C2 C1 C6 118.6(3) . . ?
C6 C1 N1 119.5(3) . . ?
C42 C37 C31 122.1(3) . . ?
C38 C37 C31 119.7(3) . . ?
C38 C37 C42 118.1(3) . . ?
O9 N4 C40 118.2(4) . . ?
O10 N4 C40 118.5(4) . . ?
O10 N4 O9 123.3(4) . . ?
O6 C33 N3 103.4(3) . . ?
O6 C33 H33 111.3 . . ?
O6 C33 C32 107.9(3) . . ?
N3 C33 H33 111.3 . . ?
N3 C33 C32 111.2(3) . . ?
C32 C33 H33 111.3 . . ?
C41 C40 N4 119.6(3) . . ?
C39 C40 N4 118.5(4) . . ?
C39 C40 C41 121.8(3) . . ?
O1 C12 N1 102.5(3) . . ?
O1 C12 H12 111.3 . . ?
O1 C12 C11 108.8(3) . . ?
N1 C12 H12 111.3 . . ?
N1 C12 C11 111.3(3) . . ?
C11 C12 H12 111.3 . . ?
C37 C42 H42 119.4 . . ?
C41 C42 C37 121.2(3) . . ?
C41 C42 H42 119.4 . . ?
C21 C16 C10 120.3(3) . . ?
C21 C16 C17 118.2(3) . . ?
C17 C16 C10 121.5(3) . . ?
C8 C9 C10 108.9(3) . . ?
C8 C9 H9 105.8 . . ?
C8 C9 C13 117.9(3) . . ?
C10 C9 H9 105.8 . . ?
C10 C9 C13 111.8(3) . . ?
C13 C9 H9 105.8 . . ?
C21 C20 H20 120.9 . . ?
C19 C20 H20 120.9 . . ?
C19 C20 C21 118.2(3) . . ?
C31 C30 H30 107.8 . . ?
C31 C30 C34 114.2(3) . . ?
C29 C30 C31 108.6(3) . . ?
C29 C30 H30 107.8 . . ?
C29 C30 C34 110.5(3) . . ?
C34 C30 H30 107.8 . . ?
O5 N2 C19 118.2(5) . . ?
O5 N2 O4 122.6(4) . . ?
O4 N2 C19 119.1(4) . . ?
C16 C21 C20 121.9(3) . . ?
C16 C21 H21 119.1 . . ?
C20 C21 H21 119.1 . . ?
C40 C41 H41 120.7 . . ?
C42 C41 C40 118.7(3) . . ?
C42 C41 H41 120.7 . . ?
C20 C19 N2 118.3(4) . . ?
C20 C19 C18 122.2(3) . . ?
C18 C19 N2 119.4(4) . . ?
C10 C11 H11A 109.4 . . ?
C10 C11 H11B 109.4 . . ?
C12 C11 C10 111.1(3) . . ?
C12 C11 H11A 109.4 . . ?
C12 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C37 C38 H38 119.1 . . ?
C37 C38 C39 121.8(3) . . ?
C39 C38 H38 119.1 . . ?
C3 C4 Cl1 119.7(4) . . ?
C3 C4 C5 120.3(4) . . ?
C5 C4 Cl1 119.9(4) . . ?
C31 C32 H32A 109.2 . . ?
C31 C32 H32B 109.2 . . ?
C33 C32 C31 112.0(3) . . ?
C33 C32 H32A 109.2 . . ?
C33 C32 H32B 109.2 . . ?
H32A C32 H32B 107.9 . . ?
C16 C17 H17 119.5 . . ?
C18 C17 C16 120.9(3) . . ?
C18 C17 H17 119.5 . . ?
C40 C39 C38 118.4(3) . . ?
C40 C39 H39 120.8 . . ?
C38 C39 H39 120.8 . . ?
C9 C13 H13 104.8 . . ?
C14 C13 C9 115.9(3) . . ?
C14 C13 H13 104.8 . . ?
C14 C13 C15 112.5(5) . . ?
C15 C13 C9 112.7(4) . . ?
C15 C13 H13 104.8 . . ?
C24 C25 Cl2 120.2(4) . . ?
C26 C25 Cl2 119.0(4) . . ?
C26 C25 C24 120.8(4) . . ?
C1 C2 H2A 119.9 . . ?
C3 C2 C1 120.1(4) . . ?
C3 C2 H2A 119.9 . . ?
C22 C27 H27 119.5 . . ?
C26 C27 C22 121.1(4) . . ?
C26 C27 H27 119.5 . . ?
C25 C24 H24 119.7 . . ?
C25 C24 C23 120.6(4) . . ?
C23 C24 H24 119.7 . . ?
C4 C3 C2 120.7(4) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C30 C34 H34 107.9 . . ?
C35 C34 C30 115.5(4) . . ?
C35 C34 H34 107.9 . . ?
C35 C34 C36 106.5(5) . . ?
C36 C34 C30 110.9(4) . . ?
C36 C34 H34 107.9 . . ?
C1 C6 H6 119.7 . . ?
C5 C6 C1 120.5(4) . . ?
C5 C6 H6 119.7 . . ?
C19 C18 C17 118.6(3) . . ?
C19 C18 H18 120.7 . . ?
C17 C18 H18 120.7 . . ?
C22 C23 H23 120.1 . . ?
C24 C23 C22 119.8(4) . . ?
C24 C23 H23 120.1 . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C4 C5 C6 119.7(4) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C25 C26 C27 119.5(4) . . ?
C25 C26 H26 120.3 . . ?
C27 C26 H26 120.3 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C34 C36 H36A 109.5 . . ?
C34 C36 H36B 109.5 . . ?
C34 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
_database_code_depnum_ccdc_archive 'CCDC 1015393'
