 
data_q27b 
  
_audit_creation_method            SHELXTL 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C10 H28 Cl2 N2 O2' 
_chemical_formula_weight          279.24 
  
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' 
 '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' 
 'Cl'  'Cl'   0.3639   0.7018 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
  
_symmetry_cell_setting            Monoclinic 
_symmetry_space_group_name_H-M    Cc 
  
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 'x, -y, z+1/2' 
 'x+1/2, y+1/2, z' 
 'x+1/2, -y+1/2, z+1/2' 
  
_cell_length_a                    21.0466(7) 
_cell_length_b                    5.8427(2) 
_cell_length_c                    12.7574(4) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  104.3700(10) 
_cell_angle_gamma                 90.00 
_cell_volume                      1519.68(9) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     100(2) 
_cell_measurement_reflns_used     4648 
_cell_measurement_theta_min       4.34 
_cell_measurement_theta_max       68.96 
  
_exptl_crystal_description        'Thin plate' 
_exptl_crystal_colour             colourless 
_exptl_crystal_size_max           0.13 
_exptl_crystal_size_mid           0.06 
_exptl_crystal_size_min           0.02 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.221 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              608 
_exptl_absorpt_coefficient_mu     3.777 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.791 
_exptl_absorpt_correction_T_max   1.000
_exptl_absorpt_process_details    ? 
  
_exptl_special_details 
; 
 ? 
; 
  
_diffrn_ambient_temperature       100(2) 
_diffrn_radiation_wavelength      1.54178 
_diffrn_radiation_type            CuK\a 
_diffrn_radiation_source          'Bruker MicroSTAR microfocus rotating anode' 
_diffrn_radiation_monochromator   'Helios multilayer x-ray optics' 
_diffrn_measurement_device_type   'Bruker APEX-II CCD' 
_diffrn_measurement_method        'φ and ω scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_reflns_number             4835 
_diffrn_reflns_av_R_equivalents   0.0227 
_diffrn_reflns_av_sigmaI/netI     0.0372 
_diffrn_reflns_limit_h_min        -24 
_diffrn_reflns_limit_h_max        24 
_diffrn_reflns_limit_k_min        -6 
_diffrn_reflns_limit_k_max        6 
_diffrn_reflns_limit_l_min        -15 
_diffrn_reflns_limit_l_max        14 
_diffrn_reflns_theta_min          4.34 
_diffrn_reflns_theta_max          69.06 
_reflns_number_total              2177 
_reflns_number_gt                 2167 
_reflns_threshold_expression      >2sigma(I) 
  
_computing_data_collection        'Bruker APEX2' 
_computing_cell_refinement        'Bruker SAINT' 
_computing_data_reduction         'Bruker SAINT' 
_computing_structure_solution     'Bruker SHELXTL' 
_computing_structure_refinement   'Bruker SHELXTL' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'Bruker SHELXTL' 
  
_refine_special_details 
; 
 Refinement of F² against ALL reflections except those that were flagged 
 by the user for being in the beamstop.  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)+(0.0369P)²+0.0473P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    difmap 
_refine_ls_hydrogen_treatment     refall 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_abs_structure_details 
 'Flack H D (1983), Acta Cryst. A39, 876-881' 
_refine_ls_abs_structure_Flack    0.041(10) 
_refine_ls_number_reflns          2177 
_refine_ls_number_parameters      257 
_refine_ls_number_restraints      2 
_refine_ls_R_factor_all           0.0240 
_refine_ls_R_factor_gt            0.0239 
_refine_ls_wR_factor_ref          0.0586 
_refine_ls_wR_factor_gt           0.0585 
_refine_ls_goodness_of_fit_ref    1.096 
_refine_ls_restrained_S_all       1.095 
_refine_ls_shift/su_max           0.001 
_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 
Cl1 Cl 0.375350(18) 0.56701(6) 0.38452(3) 0.02220(11) Uani 1 1 d . . . 
Cl2 Cl 0.62085(2) 0.27023(7) 0.61467(3) 0.02391(11) Uani 1 1 d . . . 
O O 0.31635(7) 0.0795(2) 0.60493(11) 0.0247(3) Uani 1 1 d . . . 
N1 N 0.20669(7) 0.3386(3) 0.43581(11) 0.0200(3) Uani 1 1 d . . . 
N2 N 0.45886(7) -0.0695(2) 0.65011(12) 0.0186(3) Uani 1 1 d . . . 
C1 C 0.24689(9) 0.4046(3) 0.54735(14) 0.0220(4) Uani 1 1 d . . . 
H1A H 0.2825(11) 0.473(4) 0.5343(17) 0.017(5) Uiso 1 1 d . . . 
H1B H 0.2229(11) 0.519(4) 0.5745(18) 0.021(5) Uiso 1 1 d . . . 
C2 C 0.26505(10) 0.2131(4) 0.62884(15) 0.0247(4) Uani 1 1 d . . . 
H2A H 0.2791(13) 0.284(4) 0.696(2) 0.029(6) Uiso 1 1 d . . . 
H2B H 0.2260(13) 0.109(5) 0.632(2) 0.034(7) Uiso 1 1 d . . . 
C3 C 0.34509(9) -0.0742(3) 0.68970(15) 0.0217(3) Uani 1 1 d . . . 
H3A H 0.3566(11) -0.011(4) 0.750(2) 0.023(5) Uiso 1 1 d . . . 
H3B H 0.3172(14) -0.178(5) 0.704(2) 0.034(6) Uiso 1 1 d . . . 
C4 C 0.39979(9) -0.2069(3) 0.66114(14) 0.0203(3) Uani 1 1 d . . . 
H4A H 0.4170(10) -0.313(4) 0.7156(18) 0.017(5) Uiso 1 1 d . . . 
H4B H 0.3831(12) -0.279(4) 0.596(2) 0.023(5) Uiso 1 1 d . . . 
C5 C 0.14177(9) 0.2405(3) 0.44021(16) 0.0259(4) Uani 1 1 d . . . 
H5A H 0.1225(12) 0.352(4) 0.4773(19) 0.026(5) Uiso 1 1 d . . . 
H5B H 0.1493(12) 0.112(4) 0.487(2) 0.026(5) Uiso 1 1 d . . . 
H5C H 0.1203(12) 0.205(4) 0.372(2) 0.023(5) Uiso 1 1 d . . . 
C6 C 0.19461(10) 0.5524(3) 0.36844(17) 0.0249(4) Uani 1 1 d . . . 
H6A H 0.1705(12) 0.514(5) 0.299(2) 0.024(6) Uiso 1 1 d . . . 
H6B H 0.2344(13) 0.622(4) 0.368(2) 0.030(6) Uiso 1 1 d . . . 
H6C H 0.1726(12) 0.659(5) 0.401(2) 0.025(5) Uiso 1 1 d . . . 
C7 C 0.24260(9) 0.1712(3) 0.38194(15) 0.0229(4) Uani 1 1 d . . . 
H7A H 0.2515(11) 0.041(4) 0.4238(18) 0.013(5) Uiso 1 1 d . . . 
H7B H 0.2188(13) 0.156(4) 0.310(2) 0.026(6) Uiso 1 1 d . . . 
H7C H 0.2825(14) 0.229(4) 0.381(2) 0.021(5) Uiso 1 1 d . . . 
C8 C 0.48465(9) 0.0806(3) 0.74658(16) 0.0242(4) Uani 1 1 d . . . 
H8B H 0.4933(11) -0.009(4) 0.803(2) 0.017(5) Uiso 1 1 d . . . 
H8C H 0.5224(13) 0.147(5) 0.736(2) 0.030(6) Uiso 1 1 d . . . 
H8A H 0.4497(13) 0.184(4) 0.749(2) 0.030(6) Uiso 1 1 d . . . 
C9 C 0.44371(9) 0.0752(3) 0.54940(16) 0.0251(4) Uani 1 1 d . . . 
H9A H 0.4239(14) -0.022(5) 0.490(2) 0.032(6) Uiso 1 1 d . . . 
H9B H 0.4155(14) 0.190(5) 0.554(2) 0.031(6) Uiso 1 1 d . . . 
H9C H 0.4863(12) 0.145(4) 0.5478(19) 0.029(6) Uiso 1 1 d . . . 
C10 C 0.51124(10) -0.2376(3) 0.64096(16) 0.0239(4) Uani 1 1 d . . . 
H10A H 0.4959(13) -0.332(5) 0.585(2) 0.031(6) Uiso 1 1 d . . . 
H10B H 0.5234(11) -0.330(4) 0.702(2) 0.022(5) Uiso 1 1 d . . . 
H10C H 0.5479(13) -0.161(5) 0.6303(19) 0.029(6) Uiso 1 1 d . . . 
O1W O 0.52158(8) 0.4259(3) 0.39091(13) 0.0306(3) Uani 1 1 d . . . 
H1W1 H 0.4807(14) 0.480(5) 0.398(2) 0.033(6) Uiso 1 1 d . . . 
H1W2 H 0.5419(16) 0.396(5) 0.448(3) 0.038(8) Uiso 1 1 d . . . 
  
  
_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 
O C3 1.420(2) . ? 
O C2 1.426(2) . ? 
N1 C5 1.495(2) . ? 
N1 C6 1.502(2) . ? 
N1 C7 1.502(2) . ? 
N1 C1 1.514(2) . ? 
N2 C8 1.499(2) . ? 
N2 C10 1.503(2) . ? 
N2 C9 1.504(2) . ? 
N2 C4 1.516(2) . ? 
C1 C2 1.510(3) . ? 
C1 H1A 0.90(2) . ? 
C1 H1B 0.95(2) . ? 
C2 H2A 0.93(3) . ? 
C2 H2B 1.03(3) . ? 
C3 C4 1.506(2) . ? 
C3 H3A 0.83(3) . ? 
C3 H3B 0.89(3) . ? 
C4 H4A 0.93(2) . ? 
C4 H4B 0.92(3) . ? 
C5 H5A 0.95(3) . ? 
C5 H5B 0.95(3) . ? 
C5 H5C 0.90(3) . ? 
C6 H6A 0.93(3) . ? 
C6 H6B 0.93(3) . ? 
C6 H6C 0.94(3) . ? 
C7 H7A 0.92(2) . ? 
C7 H7B 0.93(3) . ? 
C7 H7C 0.91(3) . ? 
C8 H8B 0.87(3) . ? 
C8 H8C 0.92(3) . ? 
C8 H8A 0.96(3) . ? 
C9 H9A 0.95(3) . ? 
C9 H9B 0.91(3) . ? 
C9 H9C 0.99(3) . ? 
C10 H10A 0.90(3) . ? 
C10 H10B 0.93(3) . ? 
C10 H10C 0.93(3) . ? 
O1W H1W1 0.94(3) . ? 
O1W H1W2 0.77(4) . ? 
  
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 
C3 O C2 112.67(14) . . ? 
C5 N1 C6 108.28(14) . . ? 
C5 N1 C7 109.63(14) . . ? 
C6 N1 C7 108.20(13) . . ? 
C5 N1 C1 111.41(14) . . ? 
C6 N1 C1 107.56(14) . . ? 
C7 N1 C1 111.62(13) . . ? 
C8 N2 C10 108.86(14) . . ? 
C8 N2 C9 109.23(13) . . ? 
C10 N2 C9 107.76(14) . . ? 
C8 N2 C4 111.83(14) . . ? 
C10 N2 C4 107.18(13) . . ? 
C9 N2 C4 111.84(13) . . ? 
C2 C1 N1 116.44(15) . . ? 
C2 C1 H1A 112.0(14) . . ? 
N1 C1 H1A 103.6(14) . . ? 
C2 C1 H1B 109.6(14) . . ? 
N1 C1 H1B 107.3(14) . . ? 
H1A C1 H1B 107(2) . . ? 
O C2 C1 109.52(15) . . ? 
O C2 H2A 110.8(17) . . ? 
C1 C2 H2A 105.7(16) . . ? 
O C2 H2B 109.8(15) . . ? 
C1 C2 H2B 113.5(15) . . ? 
H2A C2 H2B 107(2) . . ? 
O C3 C4 110.36(15) . . ? 
O C3 H3A 113.2(17) . . ? 
C4 C3 H3A 112.8(16) . . ? 
O C3 H3B 114.0(18) . . ? 
C4 C3 H3B 106.3(19) . . ? 
H3A C3 H3B 100(2) . . ? 
C3 C4 N2 116.34(14) . . ? 
C3 C4 H4A 109.9(13) . . ? 
N2 C4 H4A 104.2(13) . . ? 
C3 C4 H4B 108.1(15) . . ? 
N2 C4 H4B 107.4(16) . . ? 
H4A C4 H4B 110.9(19) . . ? 
N1 C5 H5A 105.2(15) . . ? 
N1 C5 H5B 108.4(15) . . ? 
H5A C5 H5B 105(2) . . ? 
N1 C5 H5C 107.2(15) . . ? 
H5A C5 H5C 118(2) . . ? 
H5B C5 H5C 113.1(19) . . ? 
N1 C6 H6A 108.7(16) . . ? 
N1 C6 H6B 110.0(16) . . ? 
H6A C6 H6B 112(2) . . ? 
N1 C6 H6C 109.4(15) . . ? 
H6A C6 H6C 112(2) . . ? 
H6B C6 H6C 105(2) . . ? 
N1 C7 H7A 109.0(13) . . ? 
N1 C7 H7B 107.6(15) . . ? 
H7A C7 H7B 118.2(19) . . ? 
N1 C7 H7C 109.6(14) . . ? 
H7A C7 H7C 105(2) . . ? 
H7B C7 H7C 107(2) . . ? 
N2 C8 H8B 106.7(15) . . ? 
N2 C8 H8C 105.9(16) . . ? 
H8B C8 H8C 111(2) . . ? 
N2 C8 H8A 105.7(16) . . ? 
H8B C8 H8A 111(2) . . ? 
H8C C8 H8A 116(2) . . ? 
N2 C9 H9A 107.4(17) . . ? 
N2 C9 H9B 111.5(16) . . ? 
H9A C9 H9B 109(2) . . ? 
N2 C9 H9C 104.3(14) . . ? 
H9A C9 H9C 117(2) . . ? 
H9B C9 H9C 108(2) . . ? 
N2 C10 H10A 109.8(17) . . ? 
N2 C10 H10B 111.6(14) . . ? 
H10A C10 H10B 106(2) . . ? 
N2 C10 H10C 110.4(16) . . ? 
H10A C10 H10C 109(2) . . ? 
H10B C10 H10C 109.7(19) . . ? 
H1W1 O1W H1W2 107(3) . . ? 
  
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 
C5 N1 C1 C2 61.74(19) . . . . ? 
C6 N1 C1 C2 -179.73(15) . . . . ? 
C7 N1 C1 C2 -61.19(19) . . . . ? 
C3 O C2 C1 168.05(14) . . . . ? 
N1 C1 C2 O 75.38(19) . . . . ? 
C2 O C3 C4 -178.78(14) . . . . ? 
O C3 C4 N2 64.95(19) . . . . ? 
C8 N2 C4 C3 51.12(19) . . . . ? 
C10 N2 C4 C3 170.34(15) . . . . ? 
C9 N2 C4 C3 -71.76(19) . . . . ? 
  
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 
O1W H1W1 Cl1  0.94(3) 2.24(3) 3.1675(17) 169(2) . 
O1W H1W2 Cl2  0.77(4) 2.46(4) 3.2220(17) 170(3) . 
  
_diffrn_measured_fraction_theta_max    0.933 
_diffrn_reflns_theta_full              69.06 
_diffrn_measured_fraction_theta_full   0.933 
_refine_diff_density_max    0.272 
_refine_diff_density_min   -0.147 
_refine_diff_density_rms    0.045 
