data_shelxl
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C18 H13 Cl N2 O4'
_chemical_formula_weight          356.75
_chemical_oxdiff_usercomment 'Imitiaz Khan sample UKN'

 
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'
 'Cl'  'Cl'   0.1484   0.1585
 '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'
 
_symmetry_space_group_name_H-M 'P 21 21 21'
_symmetry_cell_setting orthorhombic
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x+1/2, -y, z+1/2'
 '-x, y+1/2, -z+1/2'
 'x+1/2, -y+1/2, -z'
 
_cell_length_a                    6.6491(3)
_cell_length_b                    7.9627(6)
_cell_length_c                    30.621(5)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      1621.2(3)
_cell_formula_units_Z             4
_cell_measurement_temperature   130.00(10) 
_cell_measurement_reflns_used   3125
_cell_measurement_theta_min     2.8761
_cell_measurement_theta_max     29.1637
 
_exptl_crystal_description        rod
_exptl_crystal_colour             yellow
_exptl_crystal_size_max           0.6
_exptl_crystal_size_mid           0.17
_exptl_crystal_size_min           0.16
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.462
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              736
_exptl_absorpt_coefficient_mu     0.262
_exptl_absorpt_correction_T_min                   0.70706
_exptl_absorpt_correction_T_max                   1.00000
_exptl_absorpt_correction_type            'multi-scan'
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature 130.00(10) 
_diffrn_radiation_wavelength 0.7107
_diffrn_radiation_type 'Mo K\a'
_diffrn_radiation_source 'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator 'mirror'
_diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             5667
_diffrn_reflns_av_R_equivalents   0.0238
_diffrn_reflns_av_sigmaI/netI     0.0354
_diffrn_reflns_limit_h_min        -7
_diffrn_reflns_limit_h_max        7
_diffrn_reflns_limit_k_min        -7
_diffrn_reflns_limit_k_max        9
_diffrn_reflns_limit_l_min        -34
_diffrn_reflns_limit_l_max        36
_diffrn_reflns_theta_min          2.88
_diffrn_reflns_theta_max          24.99
_reflns_number_total              2678
_reflns_number_gt                 2478
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_structure_solution     ?
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
 
_refine_special_details
;
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F^2^, conventional R-factors R are based
 on F, with F set to zero for negative F^2^. The threshold expression of
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F^2^ are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
 
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
 'calc w=1/[\s^2^(Fo^2^)+(0.0424P)^2^+0.1036P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      SHELXL
_refine_ls_extinction_coef        ?
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^'
_refine_ls_abs_structure_details
 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack    0.06(7)
_refine_ls_number_reflns          2678
_refine_ls_number_parameters      228
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0354
_refine_ls_R_factor_gt            0.0310
_refine_ls_wR_factor_ref          0.0819
_refine_ls_wR_factor_gt           0.0795
_refine_ls_goodness_of_fit_ref    1.122
_refine_ls_restrained_S_all       1.122
_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_symmetry_multiplicity
 _atom_site_calc_flag
 _atom_site_refinement_flags
 _atom_site_disorder_assembly
 _atom_site_disorder_group
C1 C 0.1931(3) 0.7457(3) 0.08976(7) 0.0172(5) Uani 1 1 d . . .
C2 C 0.2669(4) 0.7203(3) 0.13138(7) 0.0197(5) Uani 1 1 d . . .
H2 H 0.1956 0.7599 0.1554 0.024 Uiso 1 1 calc R . .
C3 C 0.4469(4) 0.6361(3) 0.13745(8) 0.0218(5) Uani 1 1 d . . .
H3 H 0.4972 0.6188 0.1654 0.026 Uiso 1 1 calc R . .
C4 C 0.5509(3) 0.5780(3) 0.10140(8) 0.0200(5) Uani 1 1 d . . .
C5 C 0.4797(3) 0.6041(3) 0.05958(8) 0.0211(5) Uani 1 1 d . . .
H5 H 0.5516 0.5655 0.0355 0.025 Uiso 1 1 calc R . .
C6 C 0.3007(4) 0.6883(3) 0.05401(7) 0.0209(5) Uani 1 1 d . . .
H6 H 0.2515 0.7067 0.0260 0.025 Uiso 1 1 calc R . .
C7 C 0.0031(3) 0.8353(3) 0.08111(7) 0.0176(5) Uani 1 1 d . . .
C8 C -0.2574(3) 0.9808(2) 0.11769(7) 0.0163(5) Uani 1 1 d . . .
C9 C -0.3878(3) 1.0313(3) 0.08612(7) 0.0170(5) Uani 1 1 d . . .
H9 H -0.3778 1.0164 0.0561 0.020 Uiso 1 1 calc R . .
C10 C -0.5409(3) 1.1113(3) 0.10969(7) 0.0183(5) Uani 1 1 d . . .
C11 C -0.2499(4) 0.9983(2) 0.19958(7) 0.0189(5) Uani 1 1 d . . .
C12 C -0.0540(4) 1.0409(3) 0.20862(7) 0.0242(5) Uani 1 1 d . . .
H12 H 0.0282 1.0875 0.1872 0.029 Uiso 1 1 calc R . .
C13 C 0.0179(4) 1.0126(3) 0.25046(8) 0.0299(6) Uani 1 1 d . . .
H13 H 0.1499 1.0409 0.2572 0.036 Uiso 1 1 calc R . .
C14 C -0.1021(4) 0.9436(3) 0.28205(8) 0.0334(6) Uani 1 1 d . . .
H14 H -0.0517 0.9266 0.3100 0.040 Uiso 1 1 calc R . .
C15 C -0.2989(4) 0.8992(3) 0.27233(8) 0.0321(6) Uani 1 1 d . . .
H15 H -0.3800 0.8506 0.2936 0.038 Uiso 1 1 calc R . .
C16 C -0.3738(4) 0.9274(3) 0.23086(8) 0.0267(6) Uani 1 1 d . . .
H16 H -0.5058 0.8991 0.2241 0.032 Uiso 1 1 calc R . .
C17 C -0.7257(4) 1.1913(3) 0.09295(7) 0.0194(5) Uani 1 1 d . . .
C18 C -0.9034(4) 1.2580(3) 0.02883(8) 0.0261(6) Uani 1 1 d . . .
H18A H -1.0228 1.2059 0.0401 0.039 Uiso 1 1 calc R . .
H18B H -0.8967 1.2412 -0.0022 0.039 Uiso 1 1 calc R . .
H18C H -0.9067 1.3762 0.0350 0.039 Uiso 1 1 calc R . .
N1 N -0.5094(3) 1.1092(2) 0.15258(6) 0.0197(4) Uani 1 1 d . . .
N2 N -0.3304(3) 1.0297(2) 0.15695(6) 0.0186(4) Uani 1 1 d . . .
Cl1 Cl 0.77443(9) 0.47053(7) 0.108846(19) 0.02688(17) Uani 1 1 d . . .
O1 O -0.0700(2) 0.8592(2) 0.04606(5) 0.0258(4) Uani 1 1 d . . .
O2 O -0.0813(2) 0.89195(19) 0.11892(5) 0.0199(4) Uani 1 1 d . . .
O3 O -0.7286(2) 1.18398(19) 0.04922(5) 0.0235(4) Uani 1 1 d . . .
O4 O -0.8552(2) 1.2538(2) 0.11474(6) 0.0292(4) Uani 1 1 d . . .
 
loop_
 _atom_site_aniso_label
 _atom_site_aniso_U_11
 _atom_site_aniso_U_22
 _atom_site_aniso_U_33
 _atom_site_aniso_U_23
 _atom_site_aniso_U_13
 _atom_site_aniso_U_12
C1 0.0158(11) 0.0143(10) 0.0215(12) -0.0032(9) 0.0008(10) -0.0019(10)
C2 0.0208(12) 0.0213(11) 0.0169(11) -0.0007(9) 0.0049(10) -0.0022(12)
C3 0.0216(12) 0.0236(13) 0.0201(13) 0.0026(9) 0.0001(10) -0.0006(12)
C4 0.0168(11) 0.0150(11) 0.0282(14) 0.0023(9) 0.0004(10) -0.0011(10)
C5 0.0201(12) 0.0211(11) 0.0221(13) -0.0063(9) 0.0021(10) -0.0001(11)
C6 0.0223(12) 0.0211(11) 0.0192(12) -0.0027(9) -0.0011(10) -0.0024(11)
C7 0.0199(12) 0.0170(11) 0.0158(13) -0.0013(9) 0.0024(10) -0.0027(10)
C8 0.0172(11) 0.0152(10) 0.0165(11) -0.0021(8) 0.0003(10) -0.0002(11)
C9 0.0195(11) 0.0163(10) 0.0151(11) -0.0004(9) 0.0006(9) -0.0024(10)
C10 0.0184(11) 0.0182(10) 0.0184(13) 0.0016(9) 0.0021(10) -0.0042(10)
C11 0.0263(12) 0.0163(10) 0.0142(11) -0.0020(8) 0.0039(10) 0.0074(11)
C12 0.0282(13) 0.0249(12) 0.0193(12) -0.0031(10) -0.0020(10) 0.0028(12)
C13 0.0346(13) 0.0305(14) 0.0247(13) -0.0044(10) -0.0071(11) 0.0044(13)
C14 0.0528(17) 0.0285(13) 0.0189(14) -0.0022(11) -0.0059(13) 0.0106(14)
C15 0.0518(17) 0.0270(12) 0.0174(12) 0.0042(10) 0.0118(12) 0.0063(14)
C16 0.0287(13) 0.0262(13) 0.0252(14) -0.0006(10) 0.0048(11) 0.0043(12)
C17 0.0214(12) 0.0168(10) 0.0202(12) -0.0001(9) 0.0029(11) -0.0029(11)
C18 0.0221(13) 0.0288(12) 0.0274(13) 0.0048(11) -0.0059(11) -0.0006(12)
N1 0.0181(10) 0.0193(9) 0.0218(11) -0.0021(8) 0.0016(8) 0.0034(9)
N2 0.0190(10) 0.0195(9) 0.0171(10) 0.0006(8) -0.0010(8) 0.0038(9)
Cl1 0.0183(3) 0.0245(3) 0.0379(4) 0.0010(2) -0.0001(3) 0.0039(3)
O1 0.0244(9) 0.0383(9) 0.0146(9) -0.0024(7) 0.0000(8) 0.0067(8)
O2 0.0202(8) 0.0247(8) 0.0147(8) -0.0021(6) -0.0004(7) 0.0080(8)
O3 0.0200(8) 0.0301(8) 0.0206(8) 0.0012(6) -0.0009(8) 0.0060(8)
O4 0.0227(9) 0.0402(10) 0.0246(10) 0.0011(8) 0.0036(8) 0.0114(8)
 
_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
C1 C2 1.381(3) . ?
C1 C6 1.386(3) . ?
C1 C7 1.475(3) . ?
C2 C3 1.385(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.382(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(3) . ?
C4 Cl1 1.730(2) . ?
C5 C6 1.377(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.193(3) . ?
C7 O2 1.364(3) . ?
C8 N2 1.354(3) . ?
C8 C9 1.359(3) . ?
C8 O2 1.368(3) . ?
C9 C10 1.401(3) . ?
C9 H9 0.9300 . ?
C10 N1 1.330(3) . ?
C10 C17 1.476(3) . ?
C11 C12 1.374(3) . ?
C11 C16 1.384(3) . ?
C11 N2 1.433(3) . ?
C12 C13 1.386(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.369(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.388(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.382(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 O4 1.198(3) . ?
C17 O3 1.340(3) . ?
C18 O3 1.445(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
N1 N2 1.355(3) . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C2 C1 C6 119.8(2) . . ?
C2 C1 C7 122.8(2) . . ?
C6 C1 C7 117.4(2) . . ?
C1 C2 C3 120.2(2) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C2 119.2(2) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C5 C4 C3 121.2(2) . . ?
C5 C4 Cl1 119.43(18) . . ?
C3 C4 Cl1 119.34(18) . . ?
C6 C5 C4 119.0(2) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C5 C6 C1 120.6(2) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
O1 C7 O2 122.9(2) . . ?
O1 C7 C1 126.0(2) . . ?
O2 C7 C1 111.11(19) . . ?
N2 C8 C9 108.50(19) . . ?
N2 C8 O2 115.55(18) . . ?
C9 C8 O2 135.92(19) . . ?
C8 C9 C10 103.4(2) . . ?
C8 C9 H9 128.3 . . ?
C10 C9 H9 128.3 . . ?
N1 C10 C9 112.9(2) . . ?
N1 C10 C17 118.7(2) . . ?
C9 C10 C17 128.5(2) . . ?
C12 C11 C16 121.7(2) . . ?
C12 C11 N2 119.6(2) . . ?
C16 C11 N2 118.6(2) . . ?
C11 C12 C13 118.2(2) . . ?
C11 C12 H12 120.9 . . ?
C13 C12 H12 120.9 . . ?
C14 C13 C12 121.2(2) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C13 C14 C15 120.0(2) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C16 C15 C14 119.7(2) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C11 119.2(2) . . ?
C15 C16 H16 120.4 . . ?
C11 C16 H16 120.4 . . ?
O4 C17 O3 124.3(2) . . ?
O4 C17 C10 125.7(2) . . ?
O3 C17 C10 109.9(2) . . ?
O3 C18 H18A 109.5 . . ?
O3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C10 N1 N2 103.98(17) . . ?
N1 N2 C8 111.23(17) . . ?
N1 N2 C11 119.99(17) . . ?
C8 N2 C11 128.65(18) . . ?
C7 O2 C8 119.99(17) . . ?
C17 O3 C18 115.20(19) . . ?
 
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
C6 C1 C2 C3 -0.7(3) . . . . ?
C7 C1 C2 C3 -179.63(19) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C2 C3 C4 C5 0.7(3) . . . . ?
C2 C3 C4 Cl1 -179.26(16) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
Cl1 C4 C5 C6 179.34(16) . . . . ?
C4 C5 C6 C1 -0.1(3) . . . . ?
C2 C1 C6 C5 0.8(3) . . . . ?
C7 C1 C6 C5 179.77(19) . . . . ?
C2 C1 C7 O1 -178.9(2) . . . . ?
C6 C1 C7 O1 2.2(3) . . . . ?
C2 C1 C7 O2 2.1(3) . . . . ?
C6 C1 C7 O2 -176.90(19) . . . . ?
N2 C8 C9 C10 -0.4(2) . . . . ?
O2 C8 C9 C10 177.3(2) . . . . ?
C8 C9 C10 N1 -0.7(2) . . . . ?
C8 C9 C10 C17 -179.6(2) . . . . ?
C16 C11 C12 C13 -0.6(3) . . . . ?
N2 C11 C12 C13 178.5(2) . . . . ?
C11 C12 C13 C14 0.2(3) . . . . ?
C12 C13 C14 C15 0.6(4) . . . . ?
C13 C14 C15 C16 -1.0(4) . . . . ?
C14 C15 C16 C11 0.6(3) . . . . ?
C12 C11 C16 C15 0.2(3) . . . . ?
N2 C11 C16 C15 -178.89(19) . . . . ?
N1 C10 C17 O4 -1.2(3) . . . . ?
C9 C10 C17 O4 177.6(2) . . . . ?
N1 C10 C17 O3 178.78(19) . . . . ?
C9 C10 C17 O3 -2.4(3) . . . . ?
C9 C10 N1 N2 1.4(2) . . . . ?
C17 C10 N1 N2 -179.59(18) . . . . ?
C10 N1 N2 C8 -1.6(2) . . . . ?
C10 N1 N2 C11 -177.73(18) . . . . ?
C9 C8 N2 N1 1.3(2) . . . . ?
O2 C8 N2 N1 -176.95(16) . . . . ?
C9 C8 N2 C11 177.0(2) . . . . ?
O2 C8 N2 C11 -1.2(3) . . . . ?
C12 C11 N2 N1 -130.6(2) . . . . ?
C16 C11 N2 N1 48.5(3) . . . . ?
C12 C11 N2 C8 54.0(3) . . . . ?
C16 C11 N2 C8 -126.9(2) . . . . ?
O1 C7 O2 C8 -0.1(3) . . . . ?
C1 C7 O2 C8 178.98(16) . . . . ?
N2 C8 O2 C7 179.20(18) . . . . ?
C9 C8 O2 C7 1.6(3) . . . . ?
O4 C17 O3 C18 -0.2(3) . . . . ?
C10 C17 O3 C18 179.80(17) . . . . ?
 
_diffrn_measured_fraction_theta_max    0.998
_diffrn_reflns_theta_full              24.99
_diffrn_measured_fraction_theta_full   0.998
_refine_diff_density_max    0.175
_refine_diff_density_min   -0.201
_refine_diff_density_rms    0.041