 
data_0117cc
 
_audit_creation_method            'SHELXL-2014/7'
_shelx_SHELXL_version_number      '2014/7'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C30 H36 Cl4 N8 O4' 
_chemical_formula_weight          714.47

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'Cl'  'Cl'   0.1484   0.1585
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       orthorhombic
_space_group_IT_number            29
_space_group_name_H-M_alt         'P c a 21'
_space_group_name_Hall            'P 2c -2ac'
 
_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.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, z+1/2'
 'x+1/2, -y, z'
 '-x+1/2, y, z+1/2'
 
_cell_length_a                    30.482(10)
_cell_length_b                    9.034(3)
_cell_length_c                    22.961(7)
_cell_angle_alpha                 90
_cell_angle_beta                  90
_cell_angle_gamma                 90
_cell_volume                      6323(4)
_cell_formula_units_Z             8
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used           26970
_cell_measurement_theta_min             1.1
_cell_measurement_theta_max             27.5

_exptl_absorpt_correction_type          'Multi-scan'
_exptl_absorpt_correction_T_max         1.000
_exptl_absorpt_correction_T_min         0.501

_diffrn_source                          'Rotating Anode'
_diffrn_radiation_monochromator         'Multilayer'
_diffrn_measurement_specimen_support    'Fiber'
_diffrn_detector                        'CCD'
_diffrn_measurement_device
;
AFC11 (Right): Eulerian 3 circle
;
_diffrn_measurement_device_type
;
Rigaku Saturn944+ (2x2 bin mode)
;
_diffrn_detector_area_resol_mean        22.2222
_diffrn_measurement_method              'profile data from ω-scans'

_exptl_absorpt_process_details
;
CrystalClear-SM Expert 2.1 b32 (Rigaku, 2014)
;



 
_exptl_crystal_description        prism

_exptl_crystal_colour             ?
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.501          
_exptl_crystal_F_000              2976
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.180
_exptl_crystal_size_mid           0.130
_exptl_crystal_size_min           0.100
_exptl_absorpt_coefficient_mu     0.426
_shelx_estimated_absorpt_T_min    0.927
_shelx_estimated_absorpt_T_max    0.959
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_reflns_number             19956
_diffrn_reflns_av_unetI/netI      0.0406
_diffrn_reflns_av_R_equivalents   0.0415
_diffrn_reflns_limit_h_min        -36
_diffrn_reflns_limit_h_max        34
_diffrn_reflns_limit_k_min        -10
_diffrn_reflns_limit_k_max        10
_diffrn_reflns_limit_l_min        -27
_diffrn_reflns_limit_l_max        20
_diffrn_reflns_theta_min          1.336
_diffrn_reflns_theta_max          24.995
_diffrn_reflns_theta_full         24.995
_diffrn_measured_fraction_theta_max   0.996
_diffrn_measured_fraction_theta_full  0.996
_diffrn_reflns_Laue_measured_fraction_max    0.996
_diffrn_reflns_Laue_measured_fraction_full   0.996
_diffrn_reflns_point_group_measured_fraction_max   0.859
_diffrn_reflns_point_group_measured_fraction_full  0.859
_reflns_number_total              9563
_reflns_number_gt                 9004
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.677
_reflns_Friedel_fraction_max      0.713
_reflns_Friedel_fraction_full     0.713
 
_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.
;
 
_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     ?
_computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0740P)²+2.8000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_abs_structure_details
;
 Flack x determined using 3402 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack    0.14(3)
_chemical_absolute_configuration  ?
_refine_ls_number_reflns          9563
_refine_ls_number_parameters      837
_refine_ls_number_restraints      745
_refine_ls_R_factor_all           0.0470
_refine_ls_R_factor_gt            0.0445
_refine_ls_wR_factor_ref          0.1198
_refine_ls_wR_factor_gt           0.1178
_refine_ls_goodness_of_fit_ref    1.031
_refine_ls_restrained_S_all       1.000
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_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
O1A O 0.22916(9) 0.5909(3) 0.50220(15) 0.0250(7) Uani 1 1 d . U . . .
O2A O 0.37195(9) 0.9470(3) 0.61888(15) 0.0270(7) Uani 1 1 d . U . . .
N1A N 0.27628(11) 0.7822(3) 0.48676(17) 0.0211(7) Uani 1 1 d . U . . .
N2A N 0.23749(11) 0.7776(3) 0.56692(18) 0.0213(8) Uani 1 1 d . U . . .
N3A N 0.29794(11) 0.9002(4) 0.61599(17) 0.0213(7) Uani 1 1 d . U . . .
N4A N 0.33483(10) 0.9168(4) 0.53403(17) 0.0192(7) Uani 1 1 d . U . . .
C1A C 0.24605(13) 0.7054(4) 0.5173(2) 0.0206(9) Uani 1 1 d . U . . .
C2A C 0.28939(13) 0.9134(4) 0.5165(2) 0.0192(8) Uani 1 1 d . U . . .
H2A H 0.2815 1.0037 0.4935 0.023 Uiso 1 1 calc R U . . .
C3A C 0.26389(12) 0.9071(4) 0.5730(2) 0.0197(8) Uani 1 1 d . U . . .
H3A H 0.2453 0.9974 0.5782 0.024 Uiso 1 1 calc R U . . .
C4A C 0.33835(13) 0.9252(4) 0.5922(2) 0.0206(9) Uani 1 1 d . U . . .
C5A C 0.28821(15) 0.7461(5) 0.4287(2) 0.0272(10) Uani 1 1 d . U . . .
H5A1 H 0.2738 0.6519 0.4178 0.033 Uiso 1 1 calc R U . . .
H5A2 H 0.3203 0.7300 0.4271 0.033 Uiso 1 1 calc R U . . .
C6A C 0.27625(14) 0.8608(4) 0.3850(2) 0.0224(9) Uani 1 1 d . U . . .
C7A C 0.30217(14) 0.8792(5) 0.3371(2) 0.0281(9) Uani 1 1 d . U . . .
H7A H 0.3277 0.8202 0.3322 0.034 Uiso 1 1 calc R U . . .
C8A C 0.29136(15) 0.9825(6) 0.2962(2) 0.0299(10) Uani 1 1 d . U . . .
H8A H 0.3090 0.9943 0.2624 0.036 Uiso 1 1 calc R U . . .
C9A C 0.25491(15) 1.0691(5) 0.3041(2) 0.0269(9) Uani 1 1 d . U . . .
H9A H 0.2477 1.1414 0.2756 0.032 Uiso 1 1 calc R U . . .
C10A C 0.22887(13) 1.0538(4) 0.35183(19) 0.0199(8) Uani 1 1 d . U . . .
C11A C 0.23938(13) 0.9472(4) 0.3917(2) 0.0211(9) Uani 1 1 d . U . . .
H11A H 0.2209 0.9326 0.4245 0.025 Uiso 1 1 calc R U . . .
C12A C 0.18987(14) 1.1525(5) 0.3614(2) 0.0228(9) Uani 1 1 d . U . . .
H12A H 0.1939 1.2446 0.3386 0.027 Uiso 1 1 calc R U . . .
H12B H 0.1633 1.1022 0.3466 0.027 Uiso 1 1 calc R U . . .
C13A C 0.28915(15) 0.9260(5) 0.6756(2) 0.0318(11) Uani 1 1 d . U . . .
H13A H 0.3169 0.9378 0.6967 0.048 Uiso 1 1 calc R U . . .
H13B H 0.2729 0.8418 0.6917 0.048 Uiso 1 1 calc R U . . .
H13C H 0.2716 1.0162 0.6797 0.048 Uiso 1 1 calc R U . . .
C14A C 0.36799(14) 0.9780(5) 0.4970(2) 0.0299(10) Uani 1 1 d . U . . .
H14A H 0.3622 1.0836 0.4909 0.045 Uiso 1 1 calc R U . . .
H14B H 0.3677 0.9266 0.4594 0.045 Uiso 1 1 calc R U . . .
H14C H 0.3968 0.9658 0.5153 0.045 Uiso 1 1 calc R U . . .
O1B O 0.12486(9) 1.0362(3) 0.43690(15) 0.0225(6) Uani 1 1 d . U . . .
O2B O 0.29472(9) 1.2512(3) 0.54474(15) 0.0252(7) Uani 1 1 d . U . . .
N1B N 0.15028(10) 1.1956(3) 0.50514(17) 0.0180(7) Uani 1 1 d . U . . .
N2B N 0.18326(10) 1.1900(3) 0.42065(16) 0.0180(7) Uani 1 1 d . U . . .
N3B N 0.25185(11) 1.2699(4) 0.46429(17) 0.0193(7) Uani 1 1 d . U . . .
N4B N 0.21926(11) 1.2676(4) 0.54906(17) 0.0204(7) Uani 1 1 d . U . . .
C1B C 0.15023(12) 1.1316(4) 0.4528(2) 0.0183(8) Uani 1 1 d . U . . .
C2B C 0.18436(12) 1.3054(4) 0.5102(2) 0.0181(8) Uani 1 1 d . U . . .
H2B H 0.1720 1.4053 0.5193 0.022 Uiso 1 1 calc R U . . .
C3B C 0.20673(13) 1.3034(4) 0.45102(19) 0.0181(8) Uani 1 1 d . U . . .
H3B H 0.2039 1.4011 0.4309 0.022 Uiso 1 1 calc R U . . .
C4B C 0.25870(13) 1.2648(4) 0.5213(2) 0.0193(8) Uani 1 1 d . U . . .
C5B C 0.11677(13) 1.1723(4) 0.5474(2) 0.0210(9) Uani 1 1 d . U . . .
H5B1 H 0.0894 1.1440 0.5271 0.025 Uiso 1 1 calc R U . . .
H5B2 H 0.1112 1.2665 0.5681 0.025 Uiso 1 1 calc R U . . .
C6B C 0.12781(12) 1.0553(4) 0.5911(2) 0.0191(8) Uani 1 1 d . U . . .
C7B C 0.10667(13) 1.0544(4) 0.6434(2) 0.0230(9) Uani 1 1 d . U . . .
H7B H 0.0852 1.1274 0.6518 0.028 Uiso 1 1 calc R U . . .
C8B C 0.11645(15) 0.9487(5) 0.6835(2) 0.0266(9) Uani 1 1 d . U . . .
H8B H 0.1010 0.9457 0.7194 0.032 Uiso 1 1 calc R U . . .
C9B C 0.14869(14) 0.8460(5) 0.6721(2) 0.0245(9) Uani 1 1 d . U . . .
H9B H 0.1561 0.7748 0.7009 0.029 Uiso 1 1 calc R U . . .
C10B C 0.17013(12) 0.8450(4) 0.6201(2) 0.0178(8) Uani 1 1 d . U . . .
C11B C 0.15919(12) 0.9497(4) 0.5794(2) 0.0183(8) Uani 1 1 d . U . . .
H11B H 0.1735 0.9495 0.5426 0.022 Uiso 1 1 calc R U . . .
C12B C 0.20466(13) 0.7312(4) 0.6079(2) 0.0215(9) Uani 1 1 d . U . . .
H12C H 0.2193 0.7049 0.6450 0.026 Uiso 1 1 calc R U . . .
H12D H 0.1903 0.6408 0.5928 0.026 Uiso 1 1 calc R U . . .
C13B C 0.28723(13) 1.3044(5) 0.4249(2) 0.0246(9) Uani 1 1 d . U . . .
H13D H 0.2816 1.4002 0.4063 0.037 Uiso 1 1 calc R U . . .
H13E H 0.2893 1.2273 0.3950 0.037 Uiso 1 1 calc R U . . .
H13F H 0.3149 1.3091 0.4467 0.037 Uiso 1 1 calc R U . . .
C14B C 0.21649(15) 1.2977(5) 0.6095(2) 0.0266(10) Uani 1 1 d . U . . .
H14D H 0.2449 1.2777 0.6278 0.040 Uiso 1 1 calc R U . . .
H14E H 0.1940 1.2344 0.6271 0.040 Uiso 1 1 calc R U . . .
H14F H 0.2086 1.4018 0.6153 0.040 Uiso 1 1 calc R U . . .
O1C O 0.51783(9) 0.9033(3) 0.49693(15) 0.0242(7) Uani 1 1 d . U . . .
O2C O 0.37226(9) 0.5525(4) 0.38564(16) 0.0287(7) Uani 1 1 d . U . . .
N1C N 0.46994(11) 0.7165(3) 0.51509(17) 0.0198(7) Uani 1 1 d . U . . .
N2C N 0.50752(10) 0.7135(3) 0.43399(17) 0.0181(7) Uani 1 1 d . U . . .
N3C N 0.44690(11) 0.5852(4) 0.38832(17) 0.0209(7) Uani 1 1 d . U . . .
N4C N 0.41001(11) 0.5856(4) 0.47005(17) 0.0204(7) Uani 1 1 d . U . . .
C1C C 0.50014(13) 0.7891(4) 0.4831(2) 0.0185(8) Uani 1 1 d . U . . .
C2C C 0.45521(12) 0.5840(4) 0.4878(2) 0.0184(8) Uani 1 1 d . U . . .
H2C H 0.4620 0.4949 0.5120 0.022 Uiso 1 1 calc R U . . .
C3C C 0.48109(12) 0.5833(4) 0.4307(2) 0.0173(8) Uani 1 1 d . U . . .
H3C H 0.4995 0.4922 0.4271 0.021 Uiso 1 1 calc R U . . .
C4C C 0.40630(13) 0.5716(4) 0.4122(2) 0.0198(8) Uani 1 1 d . U . . .
C5C C 0.45642(15) 0.7646(4) 0.5711(2) 0.0251(9) Uani 1 1 d . U . . .
H5C1 H 0.4246 0.7867 0.5699 0.030 Uiso 1 1 calc R U . . .
H5C2 H 0.4719 0.8578 0.5806 0.030 Uiso 1 1 calc R U . . .
C6C C 0.46470(13) 0.6564(4) 0.6179(2) 0.0213(8) Uani 1 1 d . U . . .
C7C C 0.43656(14) 0.6490(5) 0.6637(2) 0.0254(9) Uani 1 1 d . U . . .
H7C H 0.4117 0.7125 0.6648 0.030 Uiso 1 1 calc R U . . .
C8C C 0.44355(15) 0.5516(5) 0.7079(2) 0.0296(10) Uani 1 1 d . U . . .
H8C H 0.4246 0.5498 0.7407 0.035 Uiso 1 1 calc R U . . .
C9C C 0.47862(15) 0.4555(5) 0.7044(2) 0.0262(9) Uani 1 1 d . U . . .
H9C H 0.4831 0.3850 0.7345 0.031 Uiso 1 1 calc R U . . .
C10C C 0.50689(13) 0.4595(4) 0.6587(2) 0.0222(9) Uani 1 1 d . U . . .
C11C C 0.50051(14) 0.5615(4) 0.6160(2) 0.0215(8) Uani 1 1 d . U . . .
H11C H 0.5207 0.5679 0.5845 0.026 Uiso 1 1 calc R U . . .
C12C C 0.54493(14) 0.3530(5) 0.6545(2) 0.0234(9) Uani 1 1 d . U . . .
H12E H 0.5711 0.3995 0.6723 0.028 Uiso 1 1 calc R U . . .
H12F H 0.5379 0.2631 0.6774 0.028 Uiso 1 1 calc R U . . .
C13C C 0.45495(16) 0.5654(6) 0.3287(2) 0.0316(10) Uani 1 1 d . U . . .
H13G H 0.4275 0.5395 0.3089 0.047 Uiso 1 1 calc R U . . .
H13H H 0.4763 0.4855 0.3233 0.047 Uiso 1 1 calc R U . . .
H13I H 0.4666 0.6573 0.3122 0.047 Uiso 1 1 calc R U . . .
C14C C 0.37616(14) 0.5312(5) 0.5082(2) 0.0286(10) Uani 1 1 d . U . . .
H14G H 0.3477 0.5366 0.4883 0.043 Uiso 1 1 calc R U . . .
H14H H 0.3753 0.5917 0.5436 0.043 Uiso 1 1 calc R U . . .
H14I H 0.3824 0.4281 0.5186 0.043 Uiso 1 1 calc R U . . .
O1D O 0.61428(9) 0.4645(3) 0.58428(15) 0.0233(7) Uani 1 1 d . U . . .
O2D O 0.44963(10) 0.2420(3) 0.46493(16) 0.0257(7) Uani 1 1 d . U . . .
N1D N 0.59156(10) 0.3032(3) 0.51507(17) 0.0183(7) Uani 1 1 d . U . . .
N2D N 0.55518(10) 0.3109(4) 0.59689(17) 0.0186(7) Uani 1 1 d . U . . .
N3D N 0.48866(11) 0.2290(4) 0.54857(17) 0.0204(7) Uani 1 1 d . U . . .
N4D N 0.52486(11) 0.2259(4) 0.46625(17) 0.0195(7) Uani 1 1 d . U . . .
C1D C 0.58959(12) 0.3686(4) 0.5671(2) 0.0190(8) Uani 1 1 d . U . . .
C2D C 0.55837(12) 0.1918(4) 0.5082(2) 0.0185(8) Uani 1 1 d . U . . .
H2D H 0.5715 0.0921 0.5011 0.022 Uiso 1 1 calc R U . . .
C3D C 0.53323(13) 0.1961(4) 0.5655(2) 0.0193(8) Uani 1 1 d . U . . .
H3D H 0.5351 0.0993 0.5865 0.023 Uiso 1 1 calc R U . . .
C4D C 0.48451(13) 0.2310(4) 0.4904(2) 0.0194(8) Uani 1 1 d . U . . .
C5D C 0.62723(12) 0.3222(4) 0.4756(2) 0.0204(8) Uani 1 1 d . U . . .
H5D1 H 0.6349 0.2249 0.4586 0.025 Uiso 1 1 calc R U . . .
H5D2 H 0.6531 0.3584 0.4975 0.025 Uiso 1 1 calc R U . . .
C6D C 0.61755(12) 0.4279(4) 0.4274(2) 0.0184(8) Uani 1 1 d . U . . .
C7D C 0.64032(14) 0.4158(5) 0.3765(2) 0.0237(9) Uani 1 1 d . U . . .
H7D H 0.6622 0.3417 0.3723 0.028 Uiso 1 1 calc R U . . .
C8D C 0.63168(14) 0.5097(5) 0.3321(2) 0.0256(9) Uani 1 1 d . U . . .
H8D H 0.6475 0.5017 0.2966 0.031 Uiso 1 1 calc R U . . .
C9D C 0.59981(13) 0.6174(5) 0.3384(2) 0.0231(9) Uani 1 1 d . U . . .
H9D H 0.5938 0.6829 0.3070 0.028 Uiso 1 1 calc R U . . .
C10D C 0.57703(12) 0.6305(4) 0.38884(19) 0.0183(8) Uani 1 1 d . U . . .
C11D C 0.58664(12) 0.5381(4) 0.4336(2) 0.0168(8) Uani 1 1 d . U . . .
H11D H 0.5719 0.5496 0.4698 0.020 Uiso 1 1 calc R U . . .
C12D C 0.54264(13) 0.7496(4) 0.3948(2) 0.0199(9) Uani 1 1 d . U . . .
H12G H 0.5570 0.8415 0.4085 0.024 Uiso 1 1 calc R U . . .
H12H H 0.5301 0.7700 0.3558 0.024 Uiso 1 1 calc R U . . .
C13D C 0.45181(13) 0.1999(5) 0.5855(2) 0.0262(10) Uani 1 1 d . U . . .
H13J H 0.4246 0.2212 0.5644 0.039 Uiso 1 1 calc R U . . .
H13K H 0.4535 0.2629 0.6202 0.039 Uiso 1 1 calc R U . . .
H13L H 0.4521 0.0956 0.5973 0.039 Uiso 1 1 calc R U . . .
C14D C 0.53046(15) 0.1884(5) 0.4063(2) 0.0258(9) Uani 1 1 d . U . . .
H14J H 0.5017 0.1795 0.3877 0.039 Uiso 1 1 calc R U . . .
H14K H 0.5461 0.0940 0.4033 0.039 Uiso 1 1 calc R U . . .
H14L H 0.5474 0.2661 0.3869 0.039 Uiso 1 1 calc R U . . .
C41 C 0.32128(19) 0.4197(7) 0.2801(3) 0.0459(14) Uani 1 1 d . U . . .
H41A H 0.3200 0.3115 0.2866 0.055 Uiso 1 1 calc R U . . .
H41B H 0.3361 0.4651 0.3140 0.055 Uiso 1 1 calc R U . . .
C42 C 0.40353(18) 0.1034(6) 0.3596(3) 0.0387(12) Uani 1 1 d . U . . .
H42A H 0.3712 0.0944 0.3621 0.046 Uiso 1 1 calc R U . . .
H42B H 0.4138 0.1581 0.3943 0.046 Uiso 1 1 calc R U . . .
C43 C 0.34537(16) 1.3878(5) 0.6460(2) 0.0313(10) Uani 1 1 d . U . . .
H43A H 0.3347 1.3337 0.6112 0.038 Uiso 1 1 calc R U . . .
H43B H 0.3772 1.4061 0.6408 0.038 Uiso 1 1 calc R U . . .
C44 C 0.4299(2) 1.0216(8) 0.7253(3) 0.0547(16) Uani 1 1 d . U . . .
H44A H 0.4220 0.9699 0.6887 0.066 Uiso 1 1 calc R U . . .
H44B H 0.4207 1.1262 0.7216 0.066 Uiso 1 1 calc R U . . .
Cl41 Cl 0.35200(5) 0.45554(16) 0.21729(7) 0.0498(4) Uani 1 1 d . U . . .
Cl42 Cl 0.26797(6) 0.4893(2) 0.27476(11) 0.0731(6) Uani 1 1 d . U . . .
Cl43 Cl 0.42682(5) -0.07168(14) 0.35877(8) 0.0472(4) Uani 1 1 d . U . . .
Cl44 Cl 0.41740(7) 0.19971(16) 0.29784(8) 0.0633(5) Uani 1 1 d . U . . .
Cl45 Cl 0.33737(5) 1.27949(15) 0.70721(7) 0.0463(3) Uani 1 1 d . U . . .
Cl46 Cl 0.31843(4) 1.55414(14) 0.65108(8) 0.0507(4) Uani 1 1 d . U . . .
Cl47 Cl 0.40225(7) 0.9409(3) 0.78284(9) 0.0866(7) Uani 1 1 d . U . . .
Cl48 Cl 0.48626(6) 1.0135(3) 0.73508(14) 0.0973(9) Uani 1 1 d . 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
O1A C1A 1.206(5) . ?
O2A C4A 1.209(5) . ?
N1A C1A 1.350(6) . ?
N1A C2A 1.424(5) . ?
N1A C5A 1.421(6) . ?
N2A C1A 1.338(6) . ?
N2A C3A 1.426(5) . ?
N2A C12B 1.436(6) . ?
N3A C4A 1.366(6) . ?
N3A C3A 1.434(6) . ?
N3A C13A 1.413(7) . ?
N4A C4A 1.343(6) . ?
N4A C2A 1.443(5) . ?
N4A C14A 1.432(6) . ?
C2A C3A 1.514(6) . ?
C5A C6A 1.486(7) . ?
C6A C11A 1.377(6) . ?
C6A C7A 1.365(7) . ?
C7A C8A 1.364(7) . ?
C8A C9A 1.371(7) . ?
C9A C10A 1.361(7) . ?
C10A C11A 1.366(6) . ?
C10A C12A 1.503(6) . ?
C12A N2B 1.416(6) . ?
O1B C1B 1.214(5) . ?
O2B C4B 1.229(5) . ?
N1B C1B 1.335(6) . ?
N1B C5B 1.425(6) . ?
N1B C2B 1.441(5) . ?
N2B C1B 1.355(5) . ?
N2B C3B 1.431(5) . ?
N3B C4B 1.325(6) . ?
N3B C3B 1.441(5) . ?
N3B C13B 1.441(6) . ?
N4B C4B 1.361(6) . ?
N4B C14B 1.416(6) . ?
N4B C2B 1.429(5) . ?
C2B C3B 1.521(6) . ?
C5B C6B 1.496(6) . ?
C6B C11B 1.377(5) . ?
C6B C7B 1.362(6) . ?
C7B C8B 1.360(6) . ?
C8B C9B 1.376(6) . ?
C9B C10B 1.362(7) . ?
C10B C11B 1.370(6) . ?
C10B C12B 1.498(5) . ?
O1C C1C 1.207(5) . ?
O2C C4C 1.216(5) . ?
N1C C1C 1.348(5) . ?
N1C C2C 1.424(5) . ?
N1C C5C 1.418(6) . ?
N2C C1C 1.337(6) . ?
N2C C3C 1.428(5) . ?
N2C C12D 1.437(5) . ?
N3C C4C 1.359(5) . ?
N3C C3C 1.426(6) . ?
N3C C13C 1.403(6) . ?
N4C C4C 1.339(6) . ?
N4C C14C 1.440(6) . ?
N4C C2C 1.437(5) . ?
C2C C3C 1.530(6) . ?
C5C C6C 1.476(6) . ?
C6C C11C 1.388(6) . ?
C6C C7C 1.358(7) . ?
C7C C8C 1.360(7) . ?
C8C C9C 1.380(6) . ?
C9C C10C 1.357(7) . ?
C10C C11C 1.360(6) . ?
C10C C12C 1.510(6) . ?
C12C N2D 1.412(6) . ?
O1D C1D 1.214(5) . ?
O2D C4D 1.218(5) . ?
N1D C1D 1.334(6) . ?
N1D C2D 1.435(5) . ?
N1D C5D 1.426(6) . ?
N2D C1D 1.356(5) . ?
N2D C3D 1.429(5) . ?
N3D C4D 1.342(6) . ?
N3D C3D 1.444(5) . ?
N3D C13D 1.432(6) . ?
N4D C4D 1.350(6) . ?
N4D C14D 1.427(6) . ?
N4D C2D 1.438(5) . ?
C2D C3D 1.522(6) . ?
C5D C6D 1.490(6) . ?
C6D C11D 1.378(5) . ?
C6D C7D 1.364(6) . ?
C7D C8D 1.353(7) . ?
C8D C9D 1.382(6) . ?
C9D C10D 1.356(6) . ?
C10D C11D 1.356(6) . ?
C10D C12D 1.508(5) . ?
C41 Cl42 1.747(6) . ?
C41 Cl41 1.749(7) . ?
C42 Cl44 1.717(6) . ?
C42 Cl43 1.733(5) . ?
C43 Cl45 1.730(5) . ?
C43 Cl46 1.717(5) . ?
C44 Cl48 1.735(7) . ?
C44 Cl47 1.728(8) . ?
 
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
C1A N1A C2A 111.7(4) . . ?
C1A N1A C5A 123.0(4) . . ?
C2A N1A C5A 124.7(4) . . ?
C1A N2A C3A 111.9(4) . . ?
C1A N2A C12B 123.4(3) . . ?
C3A N2A C12B 124.6(4) . . ?
C4A N3A C3A 111.8(4) . . ?
C4A N3A C13A 122.0(4) . . ?
C3A N3A C13A 121.5(4) . . ?
C4A N4A C2A 110.8(3) . . ?
C4A N4A C14A 120.9(4) . . ?
C2A N4A C14A 121.3(4) . . ?
O1A C1A N2A 125.4(4) . . ?
O1A C1A N1A 125.6(4) . . ?
N2A C1A N1A 108.9(3) . . ?
N4A C2A N1A 114.9(3) . . ?
N4A C2A C3A 104.7(3) . . ?
N1A C2A C3A 103.6(3) . . ?
N2A C3A N3A 116.1(4) . . ?
N2A C3A C2A 103.7(3) . . ?
N3A C3A C2A 102.7(3) . . ?
O2A C4A N4A 125.5(4) . . ?
O2A C4A N3A 126.1(5) . . ?
N4A C4A N3A 108.4(4) . . ?
N1A C5A C6A 114.2(4) . . ?
C11A C6A C7A 119.5(4) . . ?
C11A C6A C5A 121.4(4) . . ?
C7A C6A C5A 119.1(4) . . ?
C8A C7A C6A 119.9(4) . . ?
C7A C8A C9A 119.7(5) . . ?
C10A C9A C8A 121.4(5) . . ?
C11A C10A C9A 118.4(4) . . ?
C11A C10A C12A 120.4(4) . . ?
C9A C10A C12A 121.2(4) . . ?
C6A C11A C10A 121.1(4) . . ?
N2B C12A C10A 113.3(4) . . ?
C1B N1B C5B 123.3(3) . . ?
C1B N1B C2B 111.9(3) . . ?
C5B N1B C2B 124.3(4) . . ?
C1B N2B C3B 112.7(4) . . ?
C1B N2B C12A 122.4(3) . . ?
C3B N2B C12A 124.6(4) . . ?
C4B N3B C3B 111.5(3) . . ?
C4B N3B C13B 120.6(4) . . ?
C3B N3B C13B 122.4(4) . . ?
C4B N4B C14B 121.0(4) . . ?
C4B N4B C2B 111.7(4) . . ?
C14B N4B C2B 121.4(4) . . ?
O1B C1B N2B 125.9(4) . . ?
O1B C1B N1B 125.4(4) . . ?
N2B C1B N1B 108.7(3) . . ?
N1B C2B N4B 115.0(3) . . ?
N1B C2B C3B 104.0(3) . . ?
N4B C2B C3B 102.8(3) . . ?
N3B C3B N2B 115.5(3) . . ?
N3B C3B C2B 104.0(3) . . ?
N2B C3B C2B 102.7(3) . . ?
O2B C4B N3B 125.2(4) . . ?
O2B C4B N4B 125.8(4) . . ?
N3B C4B N4B 108.8(4) . . ?
N1B C5B C6B 113.6(3) . . ?
C11B C6B C7B 119.8(4) . . ?
C11B C6B C5B 121.0(4) . . ?
C7B C6B C5B 119.3(4) . . ?
C8B C7B C6B 119.8(4) . . ?
C9B C8B C7B 120.0(4) . . ?
C8B C9B C10B 120.9(4) . . ?
C11B C10B C9B 118.5(4) . . ?
C11B C10B C12B 121.2(4) . . ?
C9B C10B C12B 120.4(4) . . ?
C6B C11B C10B 120.9(4) . . ?
N2A C12B C10B 114.3(3) . . ?
C1C N1C C2C 112.6(4) . . ?
C1C N1C C5C 122.9(4) . . ?
C2C N1C C5C 124.4(4) . . ?
C1C N2C C3C 111.7(3) . . ?
C1C N2C C12D 122.6(3) . . ?
C3C N2C C12D 125.1(4) . . ?
C4C N3C C3C 112.9(4) . . ?
C4C N3C C13C 122.8(4) . . ?
C3C N3C C13C 122.5(4) . . ?
C4C N4C C14C 120.7(4) . . ?
C4C N4C C2C 111.2(3) . . ?
C14C N4C C2C 120.7(4) . . ?
O1C C1C N1C 125.3(4) . . ?
O1C C1C N2C 125.7(4) . . ?
N1C C1C N2C 109.0(3) . . ?
N4C C2C N1C 114.7(3) . . ?
N4C C2C C3C 104.6(3) . . ?
N1C C2C C3C 102.6(3) . . ?
N3C C3C N2C 116.0(3) . . ?
N3C C3C C2C 102.0(3) . . ?
N2C C3C C2C 104.0(3) . . ?
O2C C4C N3C 126.0(4) . . ?
O2C C4C N4C 125.6(4) . . ?
N3C C4C N4C 108.3(4) . . ?
N1C C5C C6C 114.1(3) . . ?
C11C C6C C7C 119.5(4) . . ?
C11C C6C C5C 121.3(4) . . ?
C7C C6C C5C 119.2(4) . . ?
C6C C7C C8C 120.7(4) . . ?
C9C C8C C7C 119.0(4) . . ?
C8C C9C C10C 121.4(5) . . ?
C9C C10C C11C 119.0(4) . . ?
C9C C10C C12C 121.3(4) . . ?
C11C C10C C12C 119.7(4) . . ?
C6C C11C C10C 120.5(4) . . ?
N2D C12C C10C 113.6(4) . . ?
C1D N1D C2D 112.1(4) . . ?
C1D N1D C5D 123.4(3) . . ?
C2D N1D C5D 123.5(4) . . ?
C1D N2D C3D 112.7(4) . . ?
C1D N2D C12C 122.7(3) . . ?
C3D N2D C12C 124.4(4) . . ?
C4D N3D C3D 111.1(3) . . ?
C4D N3D C13D 121.2(4) . . ?
C3D N3D C13D 122.7(4) . . ?
C4D N4D C14D 120.8(4) . . ?
C4D N4D C2D 112.3(4) . . ?
C14D N4D C2D 120.7(4) . . ?
O1D C1D N1D 125.4(4) . . ?
O1D C1D N2D 126.2(4) . . ?
N1D C1D N2D 108.4(3) . . ?
N1D C2D N4D 115.1(3) . . ?
N1D C2D C3D 104.0(3) . . ?
N4D C2D C3D 102.5(3) . . ?
N3D C3D N2D 115.3(3) . . ?
N3D C3D C2D 104.2(3) . . ?
N2D C3D C2D 102.6(3) . . ?
O2D C4D N3D 124.1(4) . . ?
O2D C4D N4D 127.0(4) . . ?
N3D C4D N4D 108.8(3) . . ?
N1D C5D C6D 113.5(3) . . ?
C11D C6D C7D 119.6(4) . . ?
C11D C6D C5D 121.4(4) . . ?
C7D C6D C5D 119.0(4) . . ?
C8D C7D C6D 119.8(4) . . ?
C7D C8D C9D 120.0(4) . . ?
C8D C9D C10D 120.7(4) . . ?
C11D C10D C9D 118.9(4) . . ?
C11D C10D C12D 121.4(4) . . ?
C9D C10D C12D 119.7(4) . . ?
C6D C11D C10D 120.9(4) . . ?
N2C C12D C10D 114.4(3) . . ?
Cl42 C41 Cl41 112.0(3) . . ?
Cl44 C42 Cl43 110.7(3) . . ?
Cl45 C43 Cl46 111.8(3) . . ?
Cl48 C44 Cl47 111.4(4) . . ?
 
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 
C2A H2A O2B  1.00 2.56 3.124(5) 115.7 .
C2A H2A N3B  1.00 2.66 3.622(5) 162.4 .
C3A H3A N4B  1.00 2.65 3.572(5) 152.9 .
C5A H5A2 O2C  0.99 2.45 3.256(5) 138.6 .
C12A H12B Cl47  0.99 2.87 3.846(5) 167.9 4_554
C14A H14B Cl43  0.98 2.93 3.673(5) 133.3 1_565
C2B H2B O1D  1.00 2.59 3.431(5) 141.9 3_475
C5B H5B1 O1C  0.99 2.33 3.302(5) 168.0 3_475
C5B H5B2 O1D  0.99 2.46 3.390(5) 156.2 3_475
C12B H12D O1D  0.99 2.51 3.318(5) 138.5 3_465
C2C H2C O2D  1.00 2.56 3.138(5) 116.9 .
C2C H2C N3D  1.00 2.67 3.643(5) 164.1 .
C3C H3C N4D  1.00 2.68 3.587(5) 150.7 .
C5C H5C1 O2A  0.99 2.44 3.248(5) 138.7 .
C12C H12E Cl41  0.99 2.88 3.865(5) 176.4 2_665
C13C H13I Cl43  0.98 2.93 3.459(5) 114.5 1_565
C2D H2D O1B  1.00 2.48 3.322(5) 141.4 3_565
C2D H2D O1C  1.00 2.37 2.897(5) 112.3 1_545
C5D H5D1 O1B  0.99 2.43 3.359(5) 155.9 3_565
C5D H5D2 O1A  0.99 2.37 3.263(5) 150.1 3_565
C12D H12G O1B  0.99 2.43 3.311(5) 147.3 3_575
C41 H41B O2C  0.99 2.13 3.119(7) 175.5 .
C42 H42B O2D  0.99 2.10 3.065(6) 165.8 .
C43 H43A O2B  0.99 2.09 3.051(6) 162.8 .
C44 H44A O2A  0.99 2.22 3.088(7) 145.3 .
C44 H44B Cl45  0.99 2.91 3.681(7) 135.3 .
 
_refine_diff_density_max    0.473
_refine_diff_density_min   -0.469
_refine_diff_density_rms    0.066



