data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C21 H24 Cl2 N4 O4'
_chemical_formula_weight          467.34
 
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'
 
_symmetry_cell_setting            Triclinic
_symmetry_space_group_name_H-M    P-1
_symmetry_space_group_name_hall   '-P 1'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    6.5051(13)
_cell_length_b                    10.758(2)
_cell_length_c                    16.079(3)
_cell_angle_alpha                 100.36(3)
_cell_angle_beta                  101.24(3)
_cell_angle_gamma                 93.97(3)
_cell_volume                      1079.3(4)
_cell_formula_units_Z             2
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     9455
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       34.34
 
_exptl_crystal_description        needle
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.40
_exptl_crystal_size_mid           0.04
_exptl_crystal_size_min           0.02
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.438
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              488
_exptl_absorpt_coefficient_mu     0.337
_exptl_absorpt_correction_type    Empirical
_exptl_absorpt_correction_T_min   0.8769
_exptl_absorpt_correction_T_max   0.9933
_exptl_absorpt_process_details    'SORTAV (R. H. Blessing, 1995, 1997)'
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       150(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   'Nonius KappaCCD Area Detector'
_diffrn_measurement_method        'Phi and Omega scans to fill Ewald Sphere'
_diffrn_detector_area_resol_mean  9.091
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             20953
_diffrn_reflns_av_R_equivalents   0.0728
_diffrn_reflns_av_sigmaI/netI     0.0622
_diffrn_reflns_limit_h_min        -8
_diffrn_reflns_limit_h_max        8
_diffrn_reflns_limit_k_min        -13
_diffrn_reflns_limit_k_max        13
_diffrn_reflns_limit_l_min        -20
_diffrn_reflns_limit_l_max        20
_diffrn_reflns_theta_min          2.95
_diffrn_reflns_theta_max          27.50
_reflns_number_total              4955
_reflns_number_gt                 3418
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        
;
'DENZO (Otwinowski and Minor, 1997) & COLLECT (Hooft, 1998) '
;
_computing_cell_refinement        'DENZO, COLLECT'
_computing_data_reduction         'DENZO, COLLECT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     'CAMERON (Watkin, Pearce 1995)'
_computing_publication_material   SHELXL-97
 
_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.
;
 
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
 'calc w=1/[σ²(Fo²)+(0.0618P)²+0.0000P] where P=(Fo²+2Fc²)/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        0.011(2)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          4955
_refine_ls_number_parameters      283
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0767
_refine_ls_R_factor_gt            0.0449
_refine_ls_wR_factor_ref          0.1182
_refine_ls_wR_factor_gt           0.1053
_refine_ls_goodness_of_fit_ref    1.035
_refine_ls_restrained_S_all       1.035
_refine_ls_shift/su_max           0.009
_refine_ls_shift/su_mean          0.001
 
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
Cl1 Cl 0.30440(8) 0.51320(5) 0.19550(3) 0.04251(17) Uani 1 1 d . . .
Cl2 Cl -0.08978(8) 0.61425(5) 0.21983(4) 0.04547(18) Uani 1 1 d . . .
O1 O 0.88159(19) 0.27677(12) 0.32131(8) 0.0302(3) Uani 1 1 d . . .
O2 O 0.35705(17) 0.08752(12) 0.41881(8) 0.0293(3) Uani 1 1 d . . .
O3 O 0.38103(18) -0.39405(12) 0.42034(8) 0.0314(3) Uani 1 1 d . . .
O4 O 0.99900(17) -0.17137(12) 0.42186(8) 0.0271(3) Uani 1 1 d . . .
N1 N 0.7568(2) 0.01996(15) 0.19686(9) 0.0250(3) Uani 1 1 d . . .
N2 N 0.6727(2) -0.13425(14) 0.27327(9) 0.0212(3) Uani 1 1 d . . .
N3 N 0.5844(2) 0.19674(14) 0.35897(9) 0.0233(3) Uani 1 1 d . . .
N4 N 0.7145(2) -0.30847(14) 0.42209(9) 0.0217(3) Uani 1 1 d . . .
C1 C 0.6757(3) 0.2209(2) 0.10452(12) 0.0371(5) Uani 1 1 d . . .
H1 H 0.5861 0.2003 0.1413 0.044 Uiso 1 1 calc R . .
C2 C 0.6267(4) 0.3120(2) 0.05583(13) 0.0464(6) Uani 1 1 d . . .
H2 H 0.5039 0.3539 0.0593 0.056 Uiso 1 1 calc R . .
C3 C 0.7546(5) 0.3426(2) 0.00228(14) 0.0553(7) Uani 1 1 d . . .
H3 H 0.7214 0.4063 -0.0306 0.066 Uiso 1 1 calc R . .
C4 C 0.9293(5) 0.2812(3) -0.00351(14) 0.0586(7) Uani 1 1 d . . .
H4 H 1.0169 0.3019 -0.0410 0.070 Uiso 1 1 calc R . .
C5 C 0.9801(4) 0.1891(2) 0.04477(13) 0.0438(6) Uani 1 1 d . . .
H5 H 1.1016 0.1464 0.0398 0.053 Uiso 1 1 calc R . .
C6 C 0.8549(3) 0.15873(19) 0.10030(12) 0.0325(5) Uani 1 1 d . . .
C7 C 0.9231(3) 0.0665(2) 0.15839(12) 0.0309(4) Uani 1 1 d . . .
H7A H 0.9736 -0.0068 0.1243 0.037 Uiso 1 1 calc R . .
H7B H 1.0429 0.1090 0.2052 0.037 Uiso 1 1 calc R . .
C8 C 0.5995(3) -0.07803(19) 0.14014(12) 0.0321(5) Uani 1 1 d . . .
H8A H 0.6663 -0.1462 0.1086 0.039 Uiso 1 1 calc R . .
H8B H 0.5009 -0.0419 0.0981 0.039 Uiso 1 1 calc R . .
C9 C 0.4897(3) -0.12602(19) 0.20479(11) 0.0286(4) Uani 1 1 d . . .
H9A H 0.3952 -0.0653 0.2262 0.034 Uiso 1 1 calc R . .
H9B H 0.4081 -0.2101 0.1800 0.034 Uiso 1 1 calc R . .
C10 C 0.8351(2) -0.03212(17) 0.27382(11) 0.0218(4) Uani 1 1 d . . .
H10 H 0.9721 -0.0673 0.2701 0.026 Uiso 1 1 calc R . .
C11 C 0.8596(2) 0.06758(16) 0.36003(10) 0.0198(4) Uani 1 1 d . . .
H11 H 1.0064 0.0787 0.3955 0.024 Uiso 1 1 calc R . .
C12 C 0.7869(3) 0.19166(17) 0.34316(11) 0.0222(4) Uani 1 1 d . . .
C13 C 0.4569(3) 0.29989(19) 0.34472(13) 0.0333(5) Uani 1 1 d . . .
H13A H 0.3083 0.2657 0.3246 0.050 Uiso 1 1 calc R . .
H13B H 0.5024 0.3416 0.3010 0.050 Uiso 1 1 calc R . .
H13C H 0.4741 0.3618 0.3990 0.050 Uiso 1 1 calc R . .
C14 C 0.5230(2) 0.09855(17) 0.39561(10) 0.0212(4) Uani 1 1 d . . .
C15 C 0.6993(2) 0.01433(16) 0.40656(11) 0.0191(4) Uani 1 1 d . . .
H15 H 0.7635 0.0217 0.4693 0.023 Uiso 1 1 calc R . .
C16 C 0.6428(2) -0.12670(16) 0.36180(10) 0.0191(4) Uani 1 1 d . . .
C17 C 0.4369(2) -0.19653(17) 0.36993(11) 0.0224(4) Uani 1 1 d . . .
H17A H 0.3665 -0.1413 0.4094 0.027 Uiso 1 1 calc R . .
H17B H 0.3398 -0.2219 0.3127 0.027 Uiso 1 1 calc R . .
C18 C 0.4965(2) -0.31140(17) 0.40561(11) 0.0224(4) Uani 1 1 d . . .
C19 C 0.8312(3) -0.40343(19) 0.45858(13) 0.0325(5) Uani 1 1 d . . .
H19A H 0.8340 -0.4762 0.4125 0.049 Uiso 1 1 calc R . .
H19B H 0.7625 -0.4318 0.5020 0.049 Uiso 1 1 calc R . .
H19C H 0.9758 -0.3663 0.4858 0.049 Uiso 1 1 calc R . .
C20 C 0.8112(2) -0.20131(17) 0.40519(10) 0.0202(4) Uani 1 1 d . . .
C21 C 0.0657(3) 0.4886(2) 0.23010(14) 0.0382(5) Uani 1 1 d . . .
H21A H -0.0148 0.4084 0.1953 0.046 Uiso 1 1 calc R . .
H21B H 0.0977 0.4796 0.2914 0.046 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
Cl1 C21 1.767(2) . ?
Cl2 C21 1.756(2) . ?
O1 C12 1.210(2) . ?
O2 C14 1.2137(19) . ?
O3 C18 1.210(2) . ?
O4 C20 1.2062(19) . ?
N1 C7 1.450(2) . ?
N1 C8 1.460(2) . ?
N1 C10 1.466(2) . ?
N2 C16 1.463(2) . ?
N2 C10 1.468(2) . ?
N2 C9 1.475(2) . ?
N3 C14 1.371(2) . ?
N3 C12 1.392(2) . ?
N3 C13 1.455(2) . ?
N4 C20 1.370(2) . ?
N4 C18 1.388(2) . ?
N4 C19 1.454(2) . ?
C1 C2 1.377(3) . ?
C1 C6 1.391(3) . ?
C2 C3 1.373(3) . ?
C3 C4 1.364(4) . ?
C4 C5 1.384(3) . ?
C5 C6 1.385(3) . ?
C6 C7 1.512(3) . ?
C8 C9 1.513(3) . ?
C10 C11 1.566(2) . ?
C11 C12 1.499(2) . ?
C11 C15 1.533(2) . ?
C14 C15 1.513(2) . ?
C15 C16 1.543(2) . ?
C16 C17 1.530(2) . ?
C16 C20 1.535(2) . ?
C17 C18 1.497(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
C7 N1 C8 115.84(14) . . ?
C7 N1 C10 113.40(14) . . ?
C8 N1 C10 105.78(14) . . ?
C16 N2 C10 108.14(13) . . ?
C16 N2 C9 118.78(12) . . ?
C10 N2 C9 107.19(13) . . ?
C14 N3 C12 112.73(14) . . ?
C14 N3 C13 123.10(14) . . ?
C12 N3 C13 124.01(15) . . ?
C20 N4 C18 112.61(15) . . ?
C20 N4 C19 122.79(14) . . ?
C18 N4 C19 124.49(15) . . ?
C2 C1 C6 120.6(2) . . ?
C3 C2 C1 120.3(2) . . ?
C4 C3 C2 119.8(2) . . ?
C3 C4 C5 120.6(2) . . ?
C4 C5 C6 120.4(2) . . ?
C5 C6 C1 118.3(2) . . ?
C5 C6 C7 119.64(19) . . ?
C1 C6 C7 121.93(17) . . ?
N1 C7 C6 113.48(15) . . ?
N1 C8 C9 101.25(14) . . ?
N2 C9 C8 100.56(13) . . ?
N1 C10 N2 105.18(13) . . ?
N1 C10 C11 112.78(14) . . ?
N2 C10 C11 107.91(13) . . ?
C12 C11 C15 104.91(13) . . ?
C12 C11 C10 111.40(14) . . ?
C15 C11 C10 104.41(13) . . ?
O1 C12 N3 123.47(17) . . ?
O1 C12 C11 128.49(15) . . ?
N3 C12 C11 108.02(14) . . ?
O2 C14 N3 124.01(16) . . ?
O2 C14 C15 126.98(16) . . ?
N3 C14 C15 108.91(13) . . ?
C14 C15 C11 103.87(14) . . ?
C14 C15 C16 116.11(13) . . ?
C11 C15 C16 105.37(13) . . ?
N2 C16 C17 115.12(13) . . ?
N2 C16 C20 105.93(13) . . ?
C17 C16 C20 102.87(13) . . ?
N2 C16 C15 105.97(14) . . ?
C17 C16 C15 118.82(14) . . ?
C20 C16 C15 107.13(13) . . ?
C18 C17 C16 106.12(13) . . ?
O3 C18 N4 123.52(17) . . ?
O3 C18 C17 127.92(15) . . ?
N4 C18 C17 108.54(14) . . ?
O4 C20 N4 124.98(16) . . ?
O4 C20 C16 125.87(16) . . ?
N4 C20 C16 109.15(13) . . ?
Cl2 C21 Cl1 112.02(12) . . ?
 
_diffrn_measured_fraction_theta_max    0.998
_diffrn_reflns_theta_full              27.50
_diffrn_measured_fraction_theta_full   0.998
_refine_diff_density_max    0.291
_refine_diff_density_min   -0.335
_refine_diff_density_rms    0.059
