 
data_xr126
 
_audit_creation_method            'SHELXL-2016/4'
_shelx_SHELXL_version_number      '2016/4'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C10 H18 N O, Cl'
_chemical_formula_sum             'C10 H18 Cl N O' 
_chemical_formula_weight          203.70

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            33
_space_group_name_H-M_alt         'P n a 21'
_space_group_name_Hall            'P 2c -2n'
 
_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+1/2, z'
 '-x+1/2, y+1/2, z+1/2'
 
_cell_length_a                    24.981(5)
_cell_length_b                    7.1333(13)
_cell_length_c                    12.150(2)
_cell_angle_alpha                 90
_cell_angle_beta                  90
_cell_angle_gamma                 90
_cell_volume                      2165.0(7)
_cell_formula_units_Z             8
_cell_measurement_temperature     296(2)
_cell_measurement_reflns_used     1009
_cell_measurement_theta_min       2.97
_cell_measurement_theta_max       19.63
_exptl_crystal_description        'block'
_exptl_crystal_colour             'colourless'
_exptl_crystal_density_diffrn     1.250          
_exptl_crystal_F_000              880
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.280
_exptl_crystal_size_mid           0.250
_exptl_crystal_size_min           0.210
_exptl_absorpt_coefficient_mu     0.316
_shelx_estimated_absorpt_T_min    0.917
_shelx_estimated_absorpt_T_max    0.937
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.79
_exptl_absorpt_correction_T_max   0.94
_exptl_absorpt_process_details    SADABS
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       296(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'sealed tube'
_diffrn_radiation_monochromator   'graphite'
_diffrn_measurement_device_type   'CCD area detector'
_diffrn_measurement_method        'omega scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             23892
_diffrn_reflns_av_unetI/netI      0.0425
_diffrn_reflns_av_R_equivalents   0.0572
_diffrn_reflns_limit_h_min        -29
_diffrn_reflns_limit_h_max        29
_diffrn_reflns_limit_k_min        -8
_diffrn_reflns_limit_k_max        8
_diffrn_reflns_limit_l_min        -14
_diffrn_reflns_limit_l_max        14
_diffrn_reflns_theta_min          1.630
_diffrn_reflns_theta_max          25.249
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   1.000
_diffrn_measured_fraction_theta_full  1.000
_diffrn_reflns_Laue_measured_fraction_max    1.000
_diffrn_reflns_Laue_measured_fraction_full   1.000
_diffrn_reflns_point_group_measured_fraction_max   0.996
_diffrn_reflns_point_group_measured_fraction_full  0.996
_reflns_number_total              3907
_reflns_number_gt                 2709
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.894
_reflns_Friedel_fraction_max      0.991
_reflns_Friedel_fraction_full     0.991
 
_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      'Bruker SMART'
_computing_cell_refinement      'Bruker SMART'
_computing_data_reduction       'Bruker SAINT'
_computing_structure_solution   'Bruker SHELXTL'
_computing_structure_refinement 'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics   'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_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)+(0.1097P)²+0.7137P] 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 976 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack    0.45(4)
_chemical_absolute_configuration  ?
_refine_ls_number_reflns          3907
_refine_ls_number_parameters      235
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.1006
_refine_ls_R_factor_gt            0.0677
_refine_ls_wR_factor_ref          0.1958
_refine_ls_wR_factor_gt           0.1717
_refine_ls_goodness_of_fit_ref    1.051
_refine_ls_restrained_S_all       1.051
_refine_ls_shift/su_max           0.010
_refine_ls_shift/su_mean          0.002
 
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
C1 C 0.4903(4) 0.4675(11) 0.3676(7) 0.069(2) Uani 1 1 d . . . . .
H1A H 0.485492 0.346581 0.332414 0.083 Uiso 1 1 calc R U . . .
H1B H 0.523802 0.465510 0.407950 0.083 Uiso 1 1 calc R U . . .
C2 C 0.4913(3) 0.6237(9) 0.2806(6) 0.0487(17) Uani 1 1 d . . . . .
C3 C 0.4678(3) 0.7848(11) 0.3498(6) 0.0478(18) Uani 1 1 d . . . . .
C4 C 0.4283(4) 0.6905(12) 0.4249(8) 0.075(2) Uani 1 1 d . . . . .
H4A H 0.426505 0.754987 0.495097 0.090 Uiso 1 1 calc R U . . .
H4B H 0.392934 0.689539 0.392099 0.090 Uiso 1 1 calc R U . . .
C5 C 0.5482(3) 0.6811(10) 0.2526(7) 0.057(2) Uani 1 1 d . . . . .
H5A H 0.571922 0.573370 0.253941 0.068 Uiso 1 1 calc R U . . .
H5B H 0.549805 0.738152 0.180234 0.068 Uiso 1 1 calc R U . . .
C6 C 0.5170(3) 0.8595(11) 0.4101(8) 0.068(2) Uani 1 1 d . . . . .
H6A H 0.513783 0.993546 0.421984 0.082 Uiso 1 1 calc R U . . .
H6B H 0.520897 0.798286 0.480902 0.082 Uiso 1 1 calc R U . . .
C7 C 0.4572(3) 0.5683(12) 0.1825(7) 0.067(2) Uani 1 1 d . . . . .
H7A H 0.426016 0.500006 0.208119 0.080 Uiso 1 1 calc R U . . .
H7B H 0.477646 0.485391 0.135147 0.080 Uiso 1 1 calc R U . . .
C8 C 0.4389(4) 0.7387(15) 0.1161(8) 0.079(3) Uani 1 1 d . . . . .
H8A H 0.469957 0.799122 0.083713 0.095 Uiso 1 1 calc R U . . .
H8B H 0.415866 0.697441 0.056617 0.095 Uiso 1 1 calc R U . . .
C9 C 0.4092(3) 0.8786(13) 0.1863(8) 0.078(2) Uani 1 1 d . . . . .
H9A H 0.398312 0.984582 0.141534 0.093 Uiso 1 1 calc R U . . .
H9B H 0.377233 0.820731 0.216333 0.093 Uiso 1 1 calc R U . . .
C10 C 0.4446(3) 0.9449(10) 0.2785(7) 0.066(2) Uani 1 1 d . . . . .
H10A H 0.424227 1.028434 0.325486 0.079 Uiso 1 1 calc R U . . .
H10B H 0.474048 1.016306 0.247573 0.079 Uiso 1 1 calc R U . . .
C11 C 0.3166(4) 0.3337(14) 0.2959(9) 0.091(3) Uani 1 1 d . . . . .
H11A H 0.351917 0.343807 0.328643 0.110 Uiso 1 1 calc R U . . .
H11B H 0.319197 0.262963 0.227899 0.110 Uiso 1 1 calc R U . . .
C12 C 0.2783(3) 0.2464(11) 0.3727(7) 0.0496(19) Uani 1 1 d . . . . .
C13 C 0.2534(3) 0.4018(9) 0.4399(6) 0.0478(16) Uani 1 1 d . . . . .
C14 C 0.2518(5) 0.5559(15) 0.3471(9) 0.096(3) Uani 1 1 d . . . . .
H14A H 0.217919 0.550900 0.308044 0.116 Uiso 1 1 calc R U . . .
H14B H 0.255747 0.679771 0.378961 0.116 Uiso 1 1 calc R U . . .
C15 C 0.2309(3) 0.1554(11) 0.3165(8) 0.071(2) Uani 1 1 d . . . . .
H15A H 0.225480 0.209114 0.244035 0.085 Uiso 1 1 calc R U . . .
H15B H 0.236709 0.021653 0.308631 0.085 Uiso 1 1 calc R U . . .
C16 C 0.1986(3) 0.3367(10) 0.4710(7) 0.065(2) Uani 1 1 d . . . . .
H16A H 0.173415 0.440218 0.469368 0.078 Uiso 1 1 calc R U . . .
H16B H 0.198720 0.283102 0.544405 0.078 Uiso 1 1 calc R U . . .
C17 C 0.3061(4) 0.0952(14) 0.4458(9) 0.081(3) Uani 1 1 d . . . . .
H17A H 0.278921 0.017809 0.480153 0.097 Uiso 1 1 calc R U . . .
H17B H 0.327825 0.014835 0.399363 0.097 Uiso 1 1 calc R U . . .
C18 C 0.3410(4) 0.1785(15) 0.5339(10) 0.095(4) Uani 1 1 d . . . . .
H18A H 0.354594 0.079417 0.580798 0.114 Uiso 1 1 calc R U . . .
H18B H 0.371263 0.241187 0.500142 0.114 Uiso 1 1 calc R U . . .
C19 C 0.3110(5) 0.3118(18) 0.5999(9) 0.103(4) Uani 1 1 d . . . . .
H19A H 0.334375 0.363233 0.656096 0.123 Uiso 1 1 calc R U . . .
H19B H 0.281966 0.246921 0.636625 0.123 Uiso 1 1 calc R U . . .
C20 C 0.2868(3) 0.4811(15) 0.5274(8) 0.090(3) Uani 1 1 d . . . . .
H20A H 0.265466 0.563088 0.573646 0.108 Uiso 1 1 calc R U . . .
H20B H 0.315616 0.554233 0.495553 0.108 Uiso 1 1 calc R U . . .
CL1 Cl 0.09501(8) 0.3140(2) 0.22955(16) 0.0657(6) Uani 1 1 d . . . . .
CL2 Cl 0.14936(8) 0.8265(2) 0.49735(17) 0.0676(6) Uani 1 1 d . . . . .
N1 N 0.5635(2) 0.8178(8) 0.3386(6) 0.0625(19) Uani 1 1 d . . . . .
H1C H 0.590012 0.771165 0.379120 0.075 Uiso 1 1 calc R U . . .
H1D H 0.574992 0.922997 0.307196 0.075 Uiso 1 1 calc R U . . .
N2 N 0.1838(2) 0.1917(7) 0.3874(6) 0.0593(17) Uani 1 1 d . . . . .
H2A H 0.173869 0.086404 0.420924 0.071 Uiso 1 1 calc R U . . .
H2B H 0.156580 0.232227 0.346661 0.071 Uiso 1 1 calc R U . . .
O1 O 0.4478(3) 0.5039(9) 0.4390(6) 0.092(2) Uani 1 1 d . . . . .
O2 O 0.2931(3) 0.5192(12) 0.2769(7) 0.116(3) Uani 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
C1 O1 1.396(10) . ?
C1 C2 1.536(10) . ?
C2 C7 1.518(11) . ?
C2 C5 1.519(10) . ?
C2 C3 1.540(10) . ?
C3 C4 1.503(12) . ?
C3 C6 1.525(11) . ?
C3 C10 1.545(11) . ?
C4 O1 1.427(10) . ?
C5 N1 1.479(11) . ?
C6 N1 1.480(11) . ?
C7 C8 1.529(13) . ?
C8 C9 1.508(14) . ?
C9 C10 1.505(12) . ?
C11 O2 1.467(12) . ?
C11 C12 1.475(12) . ?
C12 C13 1.511(10) . ?
C12 C15 1.513(11) . ?
C12 C17 1.561(13) . ?
C13 C20 1.465(11) . ?
C13 C16 1.494(10) . ?
C13 C14 1.575(12) . ?
C14 O2 1.364(11) . ?
C15 N2 1.479(10) . ?
C16 N2 1.497(10) . ?
C17 C18 1.501(14) . ?
C18 C19 1.451(14) . ?
C19 C20 1.613(15) . ?
 
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
O1 C1 C2 107.7(7) . . ?
C7 C2 C5 114.8(7) . . ?
C7 C2 C1 110.0(6) . . ?
C5 C2 C1 111.4(7) . . ?
C7 C2 C3 114.2(6) . . ?
C5 C2 C3 106.1(6) . . ?
C1 C2 C3 99.2(6) . . ?
C4 C3 C6 113.2(8) . . ?
C4 C3 C2 104.3(6) . . ?
C6 C3 C2 102.5(6) . . ?
C4 C3 C10 115.1(7) . . ?
C6 C3 C10 108.2(6) . . ?
C2 C3 C10 112.8(7) . . ?
O1 C4 C3 105.5(7) . . ?
N1 C5 C2 105.1(6) . . ?
N1 C6 C3 106.2(6) . . ?
C2 C7 C8 112.0(7) . . ?
C9 C8 C7 112.0(8) . . ?
C10 C9 C8 109.8(7) . . ?
C9 C10 C3 114.0(6) . . ?
O2 C11 C12 102.7(7) . . ?
C11 C12 C13 107.4(7) . . ?
C11 C12 C15 113.8(8) . . ?
C13 C12 C15 103.7(6) . . ?
C11 C12 C17 111.3(7) . . ?
C13 C12 C17 112.5(7) . . ?
C15 C12 C17 108.0(7) . . ?
C20 C13 C16 117.2(7) . . ?
C20 C13 C12 116.2(7) . . ?
C16 C13 C12 106.6(6) . . ?
C20 C13 C14 105.4(7) . . ?
C16 C13 C14 112.0(7) . . ?
C12 C13 C14 97.8(7) . . ?
O2 C14 C13 107.1(7) . . ?
N2 C15 C12 106.5(6) . . ?
C13 C16 N2 105.6(6) . . ?
C18 C17 C12 113.0(8) . . ?
C19 C18 C17 110.8(8) . . ?
C18 C19 C20 112.5(9) . . ?
C13 C20 C19 108.7(8) . . ?
C6 N1 C5 110.2(6) . . ?
C15 N2 C16 108.7(5) . . ?
C1 O1 C4 111.0(6) . . ?
C14 O2 C11 112.2(8) . . ?
 
_refine_diff_density_max    0.528
_refine_diff_density_min   -0.222
_refine_diff_density_rms    0.061



