data_aa
_audit_creation_date               2018-07-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Bourhis, L.J., Dolomanov, O.V., Gildea, R.J., Howard, J.A.K., Puschmann, H.
 (2015). Acta Cryst. A71, 59-75.

Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122.
;
_chemical_name_common              ?
_chemical_name_systematic
;
 ? 
;
_chemical_formula_moiety           'C39 H30 Cl2 N4 O4'
_chemical_formula_sum              'C39 H30 Cl2 N4 O4'
_chemical_formula_weight           689.57
_chemical_melting_point            ?
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                     17.2491(10)
_cell_length_b                     20.1577(12)
_cell_length_c                     21.1430(11)
_cell_angle_alpha                  90.00
_cell_angle_beta                   90.00
_cell_angle_gamma                  90.00
_cell_volume                       7351.5(7)
_cell_formula_units_Z              8
_cell_measurement_reflns_used      9990
_cell_measurement_temperature      273(2)
_cell_measurement_theta_max        22.148
_cell_measurement_theta_min        2.260
_exptl_absorpt_coefficient_mu      0.221
_exptl_absorpt_correction_T_max    ?
_exptl_absorpt_correction_T_min    ?
_exptl_absorpt_correction_type     'none'
_exptl_absorpt_process_details     ?
_exptl_crystal_colour              colorless
_exptl_crystal_density_diffrn      1.246
_exptl_crystal_density_meas        .
_exptl_crystal_density_method      'not measured'
_exptl_crystal_description         block
_exptl_crystal_F_000               2864
_exptl_crystal_size_max            0.218
_exptl_crystal_size_mid            0.059
_exptl_crystal_size_min            0.013
_exptl_special_details
;
 ? 
;
_diffrn_reflns_av_R_equivalents    0.0659
_diffrn_reflns_av_unetI/netI       0.0414
_diffrn_reflns_limit_h_max         20
_diffrn_reflns_limit_h_min         -23
_diffrn_reflns_limit_k_max         26
_diffrn_reflns_limit_k_min         -25
_diffrn_reflns_limit_l_max         28
_diffrn_reflns_limit_l_min         -28
_diffrn_reflns_number              105458
_diffrn_reflns_theta_full          28.38
_diffrn_reflns_theta_max           28.38
_diffrn_reflns_theta_min           2.36
_diffrn_ambient_temperature        273.15
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.997
_diffrn_measured_fraction_theta_max  0.997
_diffrn_measurement_device_type    'CCD area detector'
_diffrn_measurement_method         'phi and omega scans'
_diffrn_radiation_monochromator    'graphite'
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     'fine-focus sealed tube'
_diffrn_standards_decay_%          ?
_diffrn_standards_interval_count   ?
_diffrn_standards_interval_time    ?
_diffrn_standards_number           ?
_reflns_number_gt                  5535
_reflns_number_total               9195
_reflns_threshold_expression       >2sigma(I)
_computing_cell_refinement         'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection         ?
_computing_data_reduction          'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics      'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement    'XL (Sheldrick, 2008)'
_computing_structure_solution      'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max           1.215
_refine_diff_density_min           -0.344
_refine_diff_density_rms           0.124
_refine_ls_extinction_coef         ?
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.117
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       445
_refine_ls_number_reflns           9195
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.1558
_refine_ls_R_factor_gt             0.0990
_refine_ls_restrained_S_all        1.117
_refine_ls_shift/su_max            0.000
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'calc w=1/[σ²(Fo²)+(0.1823P)²+2.7956P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.2808
_refine_ls_wR_factor_ref           0.3263
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C12(H12)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C13(H13), C17(H17), C18(H18), C19(H19), C22(H22), C24(H24), C26(H26),
 C28(H28), C29(H29), C30(H30), C31(H31), C32(H32), C34(H34), C35(H35), C36(H36),
  C38(H38), C39(H39)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C20(H20A,H20B,H20C), C37(H37A,H37B,H37C)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       iterative
_atom_sites_solution_secondary     difmap
loop_
  _atom_site_label
  _atom_site_type_symbol
  _atom_site_fract_x
  _atom_site_fract_y
  _atom_site_fract_z
  _atom_site_U_iso_or_equiv
  _atom_site_adp_type
  _atom_site_occupancy
  _atom_site_calc_flag
  _atom_site_disorder_assembly
  _atom_site_disorder_group
  _atom_site_refinement_flags_posn
 Cl2 Cl 0.51435(8) 0.10908(6) 0.52573(7) 0.0872(4) Uani 1 d . . .
 Cl1 Cl 0.95836(10) 0.63025(10) 0.33730(7) 0.1129(6) Uani 1 d . . .
 O4 O 0.57815(13) 0.55996(12) 0.53419(11) 0.0473(6) Uani 1 d . . .
 O1 O 0.78948(14) 0.34604(12) 0.49508(11) 0.0501(6) Uani 1 d . . .
 N3 N 0.76275(16) 0.56611(15) 0.60142(14) 0.0469(7) Uani 1 d . . .
 C1 C 0.61959(17) 0.39321(16) 0.50595(14) 0.0370(7) Uani 1 d . . .
 H1 H 0.5728 0.4194 0.4977 0.044 Uiso 1 calc . . R
 C2 C 0.66064(18) 0.42423(16) 0.56354(14) 0.0381(7) Uani 1 d . . .
 H2 H 0.7041 0.3952 0.5748 0.046 Uiso 1 calc . . R
 C3 C 0.74422(19) 0.35728(17) 0.45210(15) 0.0405(7) Uani 1 d . . .
 C4 C 0.69579(17) 0.49107(15) 0.53748(14) 0.0369(7) Uani 1 d . . .
 N2 N 0.74082(17) 0.32577(15) 0.39534(13) 0.0494(7) Uani 1 d . . .
 N1 N 0.68102(17) 0.34965(16) 0.35593(14) 0.0516(8) Uani 1 d . . .
 C5 C 0.59522(18) 0.32196(16) 0.51193(14) 0.0394(7) Uani 1 d . . .
 C6 C 0.64325(18) 0.54973(16) 0.55308(14) 0.0378(7) Uani 1 d . . .
 N4 N 0.68512(15) 0.58898(14) 0.59237(14) 0.0454(7) Uani 1 d . . .
 C7 C 0.67885(17) 0.40792(16) 0.45098(14) 0.0379(7) Uani 1 d . . .
 C8 C 0.5330(2) 0.29850(18) 0.47670(17) 0.0482(8) Uani 1 d . . .
 H8 H 0.5071 0.3274 0.4497 0.058 Uiso 1 calc . . R
 C9 C 0.66168(19) 0.64893(16) 0.62327(15) 0.0412(7) Uani 1 d . . .
 C10 C 0.77023(18) 0.51154(16) 0.57027(15) 0.0415(7) Uani 1 d . . .
 C11 C 0.8443(2) 0.4754(2) 0.57203(18) 0.0543(9) Uani 1 d . . .
 H11A H 0.8801 0.4984 0.5990 0.082 Uiso 1 calc . . GR
 H11B H 0.8653 0.4726 0.5301 0.082 Uiso 1 calc . . GR
 H11C H 0.8358 0.4315 0.5882 0.082 Uiso 1 calc . . GR
 C12 C 0.69788(18) 0.48156(16) 0.46412(14) 0.0381(7) Uani 1 d . . .
 H12 H 0.6520 0.5055 0.4491 0.046 Uiso 1 calc . . R
 C13 C 0.5088(2) 0.2332(2) 0.4807(2) 0.0567(9) Uani 1 d . . .
 H13 H 0.4670 0.2185 0.4567 0.068 Uiso 1 calc . . R
 C14 C 0.64628(18) 0.39567(18) 0.38622(15) 0.0435(8) Uani 1 d . . .
 C15 C 0.76506(19) 0.51529(18) 0.43059(15) 0.0451(8) Uani 1 d . . .
 O3 O 0.7242(2) 0.43008(19) 0.68220(13) 0.0842(10) Uani 1 d . . .
 C16 C 0.6111(2) 0.43230(16) 0.62166(15) 0.0466(8) Uani 1 d . . .
 C17 C 0.6781(2) 0.70882(19) 0.59671(19) 0.0587(10) Uani 1 d . . .
 H17 H 0.7031 0.7109 0.5578 0.070 Uiso 1 calc . . R
 C18 C 0.6236(3) 0.6452(2) 0.68020(19) 0.0633(11) Uani 1 d . . .
 H18 H 0.6117 0.6043 0.6981 0.076 Uiso 1 calc . . R
 O2 O 0.6166(3) 0.4670(2) 0.72909(14) 0.1081(14) Uani 1 d . . .
 C19 C 0.8274(2) 0.4836(2) 0.4039(2) 0.0674(11) Uani 1 d . . .
 H19 H 0.8297 0.4375 0.4048 0.081 Uiso 1 calc . . R
 C20 C 0.5811(2) 0.4329(2) 0.35658(16) 0.0550(10) Uani 1 d . . .
 H20A H 0.5976 0.4773 0.3471 0.083 Uiso 1 calc . . GR
 H20B H 0.5380 0.4343 0.3853 0.083 Uiso 1 calc . . GR
 H20C H 0.5656 0.4111 0.3182 0.083 Uiso 1 calc . . GR
 C21 C 0.5465(2) 0.19080(19) 0.5201(2) 0.0585(10) Uani 1 d . . .
 C22 C 0.7645(3) 0.5832(2) 0.42725(19) 0.0630(10) Uani 1 d . . .
 H22 H 0.7226 0.6058 0.4445 0.076 Uiso 1 calc . . R
 C23 C 0.5334(2) 0.4300(2) 0.6215(2) 0.0625(11) Uani 1 d . . .
 C24 C 0.6205(2) 0.7631(2) 0.6843(2) 0.0596(10) Uani 1 d . . .
 H24 H 0.6069 0.8020 0.7051 0.072 Uiso 1 calc . . R
 C25 C 0.6500(3) 0.4457(2) 0.68345(18) 0.0659(11) Uani 1 d . . .
 C26 C 0.6033(3) 0.7037(2) 0.71041(19) 0.0686(12) Uani 1 d . . .
 H26 H 0.5776 0.7021 0.7490 0.082 Uiso 1 calc . . R
 C27 C 0.7922(2) 0.2776(2) 0.36892(19) 0.0592(10) Uani 1 d . . .
 C28 C 0.6081(3) 0.2116(2) 0.5564(2) 0.0689(12) Uani 1 d . . .
 H28 H 0.6331 0.1823 0.5836 0.083 Uiso 1 calc . . R
 C29 C 0.6323(2) 0.27680(19) 0.55152(19) 0.0590(10) Uani 1 d . . .
 H29 H 0.6746 0.2909 0.5753 0.071 Uiso 1 calc . . R
 C30 C 0.6577(3) 0.7663(2) 0.6276(2) 0.0684(11) Uani 1 d . . .
 H30 H 0.6693 0.8072 0.6098 0.082 Uiso 1 calc . . R
 C31 C 0.8229(3) 0.6193(3) 0.3996(2) 0.0785(14) Uani 1 d . . .
 H31 H 0.8209 0.6654 0.3987 0.094 Uiso 1 calc . . R
 C32 C 0.8870(3) 0.5192(3) 0.3754(2) 0.0784(13) Uani 1 d . . .
 H32 H 0.9290 0.4970 0.3577 0.094 Uiso 1 calc . . R
 C33 C 0.8839(3) 0.5860(3) 0.37362(18) 0.0687(12) Uani 1 d . . .
 C34 C 0.7776(3) 0.2527(3) 0.3102(2) 0.0921(18) Uani 1 d . . .
 H34 H 0.7337 0.2665 0.2882 0.111 Uiso 1 calc . . R
 C35 C 0.8924(4) 0.1872(4) 0.3147(3) 0.139(3) Uani 1 d . . .
 H35 H 0.9265 0.1573 0.2962 0.166 Uiso 1 calc . . R
 C36 C 0.8557(3) 0.2558(3) 0.4021(3) 0.0874(17) Uani 1 d . . .
 H36 H 0.8648 0.2706 0.4431 0.105 Uiso 1 calc . . R
 C37 C 0.7691(5) 0.4474(5) 0.7386(3) 0.146(3) Uani 1 d . . .
 H37A H 0.8230 0.4390 0.7310 0.220 Uiso 1 calc . . GR
 H37B H 0.7517 0.4211 0.7737 0.220 Uiso 1 calc . . GR
 H37C H 0.7618 0.4936 0.7481 0.220 Uiso 1 calc . . GR
 C38 C 0.9060(4) 0.2117(4) 0.3735(3) 0.122(3) Uani 1 d . . .
 H38 H 0.9503 0.1983 0.3951 0.146 Uiso 1 calc . . R
 C39 C 0.8270(4) 0.2076(4) 0.2832(3) 0.129(3) Uani 1 d . . .
 H39 H 0.8161 0.1907 0.2433 0.155 Uiso 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
 Cl2 C21 1.742(4) . ?
 Cl1 C33 1.743(4) . ?
 O4 C6 1.209(4) . ?
 O1 C3 1.219(4) . ?
 N3 N4 1.429(4) . ?
 N3 C10 1.288(4) . ?
 C1 C2 1.541(4) . ?
 C1 C5 1.502(4) . ?
 C1 C7 1.576(4) . ?
 C2 C4 1.577(4) . ?
 C2 C16 1.506(4) . ?
 C3 N2 1.359(4) . ?
 C3 C7 1.521(4) . ?
 C4 C6 1.526(4) . ?
 C4 C10 1.516(4) . ?
 C4 C12 1.563(4) . ?
 N2 N1 1.411(4) . ?
 N2 C27 1.429(4) . ?
 N1 C14 1.277(4) . ?
 C5 C8 1.389(4) . ?
 C5 C29 1.393(5) . ?
 C6 N4 1.356(4) . ?
 N4 C9 1.432(4) . ?
 C7 C12 1.545(4) . ?
 C7 C14 1.500(4) . ?
 C8 C13 1.384(5) . ?
 C9 C17 1.361(5) . ?
 C9 C18 1.373(5) . ?
 C10 C11 1.471(5) . ?
 C12 C15 1.519(4) . ?
 C13 C21 1.359(6) . ?
 C14 C20 1.490(5) . ?
 C15 C19 1.372(5) . ?
 C15 C22 1.370(5) . ?
 O3 C25 1.319(6) . ?
 O3 C37 1.464(6) . ?
 C16 C23 1.340(5) . ?
 C16 C25 1.493(5) . ?
 C17 C30 1.375(6) . ?
 C18 C26 1.387(6) . ?
 O2 C25 1.203(5) . ?
 C19 C32 1.392(6) . ?
 C21 C28 1.377(6) . ?
 C22 C31 1.374(6) . ?
 C24 C26 1.351(6) . ?
 C24 C30 1.360(6) . ?
 C27 C34 1.362(6) . ?
 C27 C36 1.373(6) . ?
 C28 C29 1.383(6) . ?
 C31 C33 1.364(7) . ?
 C32 C33 1.347(7) . ?
 C34 C39 1.370(7) . ?
 C35 C38 1.357(8) . ?
 C35 C39 1.373(8) . ?
 C36 C38 1.382(6) . ?

loop_
  _geom_angle_atom_site_label_1
  _geom_angle_atom_site_label_2
  _geom_angle_atom_site_label_3
  _geom_angle
  _geom_angle_site_symmetry_1
  _geom_angle_site_symmetry_3
  _geom_angle_publ_flag
 C10 N3 N4 107.5(3) . . ?
 C2 C1 C7 102.0(2) . . ?
 C5 C1 C2 116.8(3) . . ?
 C5 C1 C7 115.1(3) . . ?
 C1 C2 C4 104.3(2) . . ?
 C16 C2 C1 115.3(3) . . ?
 C16 C2 C4 114.3(3) . . ?
 O1 C3 N2 126.8(3) . . ?
 O1 C3 C7 127.7(3) . . ?
 N2 C3 C7 105.5(3) . . ?
 C6 C4 C2 111.0(2) . . ?
 C6 C4 C12 108.9(2) . . ?
 C10 C4 C2 113.5(3) . . ?
 C10 C4 C6 101.1(2) . . ?
 C10 C4 C12 117.9(3) . . ?
 C12 C4 C2 104.5(2) . . ?
 C3 N2 N1 113.2(3) . . ?
 C3 N2 C27 129.5(3) . . ?
 N1 N2 C27 117.0(3) . . ?
 C14 N1 N2 107.1(3) . . ?
 C8 C5 C1 119.8(3) . . ?
 C8 C5 C29 117.1(3) . . ?
 C29 C5 C1 123.2(3) . . ?
 O4 C6 C4 127.8(3) . . ?
 O4 C6 N4 126.7(3) . . ?
 N4 C6 C4 105.6(3) . . ?
 N3 N4 C9 118.4(3) . . ?
 C6 N4 N3 113.1(3) . . ?
 C6 N4 C9 128.4(3) . . ?
 C3 C7 C1 110.1(2) . . ?
 C3 C7 C12 119.0(3) . . ?
 C12 C7 C1 100.7(2) . . ?
 C14 C7 C1 113.5(2) . . ?
 C14 C7 C3 100.5(2) . . ?
 C14 C7 C12 113.7(3) . . ?
 C13 C8 C5 121.6(3) . . ?
 C17 C9 N4 120.1(3) . . ?
 C17 C9 C18 120.7(3) . . ?
 C18 C9 N4 119.2(3) . . ?
 N3 C10 C4 112.4(3) . . ?
 N3 C10 C11 119.8(3) . . ?
 C11 C10 C4 127.7(3) . . ?
 C7 C12 C4 106.9(2) . . ?
 C15 C12 C4 115.2(3) . . ?
 C15 C12 C7 120.5(3) . . ?
 C21 C13 C8 119.4(3) . . ?
 N1 C14 C7 113.7(3) . . ?
 N1 C14 C20 120.6(3) . . ?
 C20 C14 C7 125.7(3) . . ?
 C19 C15 C12 125.5(3) . . ?
 C22 C15 C12 117.8(3) . . ?
 C22 C15 C19 116.7(4) . . ?
 C25 O3 C37 116.1(5) . . ?
 C23 C16 C2 124.1(3) . . ?
 C23 C16 C25 117.3(4) . . ?
 C25 C16 C2 118.6(3) . . ?
 C9 C17 C30 119.8(4) . . ?
 C9 C18 C26 118.5(4) . . ?
 C15 C19 C32 121.1(4) . . ?
 C13 C21 Cl2 119.0(3) . . ?
 C13 C21 C28 121.3(4) . . ?
 C28 C21 Cl2 119.7(3) . . ?
 C15 C22 C31 123.2(4) . . ?
 C26 C24 C30 120.3(4) . . ?
 O3 C25 C16 112.1(4) . . ?
 O2 C25 O3 124.4(4) . . ?
 O2 C25 C16 123.5(5) . . ?
 C24 C26 C18 120.7(4) . . ?
 C34 C27 N2 119.4(3) . . ?
 C34 C27 C36 119.7(4) . . ?
 C36 C27 N2 120.8(4) . . ?
 C21 C28 C29 118.8(4) . . ?
 C28 C29 C5 121.8(3) . . ?
 C24 C30 C17 120.0(4) . . ?
 C33 C31 C22 118.3(5) . . ?
 C33 C32 C19 119.9(5) . . ?
 C31 C33 Cl1 119.6(4) . . ?
 C32 C33 Cl1 119.6(4) . . ?
 C32 C33 C31 120.8(4) . . ?
 C27 C34 C39 120.5(5) . . ?
 C38 C35 C39 118.5(5) . . ?
 C27 C36 C38 118.8(5) . . ?
 C35 C38 C36 121.7(5) . . ?
 C34 C39 C35 120.5(5) . . ?

_olex2_submission_special_instructions  'No special instructions were received'
