 
data_C11H11Cl2NO3 
 
_audit_creation_method            'SHELXL-2016/6'
_shelx_SHELXL_version_number      '2016/6'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C11 H11 Cl2 N O3' 
_chemical_formula_sum
 'C11 H11 Cl2 N O3' 
_chemical_formula_weight          276.11

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'
 
_space_group_crystal_system       orthorhombic
_space_group_IT_number            19
_space_group_name_H-M_alt         'P 21 21 21'
_space_group_name_Hall            'P 2ac 2ab'
 
_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+1/2, -y, z+1/2'
 '-x, y+1/2, -z+1/2'
 'x+1/2, -y+1/2, -z'
 
_cell_length_a                    7.9241(7)
_cell_length_b                    9.4871(9)
_cell_length_c                    16.0357(14)
_cell_angle_alpha                 90
_cell_angle_beta                  90
_cell_angle_gamma                 90
_cell_volume                      1205.51(19)
_cell_formula_units_Z             4
_cell_measurement_temperature     100(2)
_cell_measurement_reflns_used     7177
_cell_measurement_theta_min       5.42
_cell_measurement_theta_max       70.77
 
_exptl_crystal_description        plate
_exptl_crystal_colour             colorless
_exptl_crystal_density_meas       'not measured' 
_exptl_crystal_density_method     none
_exptl_crystal_density_diffrn     1.521          
_exptl_crystal_F_000              568
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.320
_exptl_crystal_size_mid           0.220
_exptl_crystal_size_min           0.140
_exptl_absorpt_coefficient_mu     4.832
_shelx_estimated_absorpt_T_min    0.307
_shelx_estimated_absorpt_T_max    0.551
_exptl_absorpt_correction_type    'multi-scan' 
_exptl_absorpt_correction_T_min   0.5587
_exptl_absorpt_correction_T_max   0.7534
_exptl_absorpt_process_details
;
Sheldrick, G.M. (2014). SADABS. Bruker AXS Inc. Madison, WI USA.
;
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       100(2)
_diffrn_radiation_wavelength      1.54178
_diffrn_radiation_type            CuK\a
_diffrn_source                    'microfocus sealed tube'
_diffrn_source_type               'Incoatec I\uS'
_diffrn_radiation_monochromator   mirrors 
_diffrn_measurement_device_type   'Bruker Kappa DUO CCD diffractometer'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_detector_area_resol_mean  ? 
_diffrn_reflns_number             7863
_diffrn_reflns_av_unetI/netI      0.0334
_diffrn_reflns_av_R_equivalents   0.0286
_diffrn_reflns_limit_h_min        -7
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_l_min        -19
_diffrn_reflns_limit_l_max        19
_diffrn_reflns_theta_min          5.417
_diffrn_reflns_theta_max          70.756
_diffrn_reflns_theta_full         67.679
_diffrn_measured_fraction_theta_max   0.993
_diffrn_measured_fraction_theta_full  0.999
_diffrn_reflns_Laue_measured_fraction_max    0.993
_diffrn_reflns_Laue_measured_fraction_full   0.999
_diffrn_reflns_point_group_measured_fraction_max   0.993
_diffrn_reflns_point_group_measured_fraction_full  1.000
_reflns_number_total              2253
_reflns_number_gt                 2224
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.707
_reflns_Friedel_fraction_max      0.993
_reflns_Friedel_fraction_full     1.000
 
_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        'APEX2 (Bruker, 2014)'
_computing_cell_refinement        'SAINT (Bruker, 2014)'
_computing_data_reduction         'SAINT (Bruker, 2014)'
_computing_structure_solution     'SHELXT 2016/6 (Sheldrick, 2016)'
_computing_structure_refinement   'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics     'Bruker SHELXTL'
_computing_publication_material   'Bruker SHELXTL'
_refine_special_details
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0250P)²+0.2549P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      dual
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack    0.036(15)
_chemical_absolute_configuration  ad
_refine_ls_number_reflns          2253
_refine_ls_number_parameters      159
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.0219
_refine_ls_R_factor_gt            0.0218
_refine_ls_wR_factor_ref          0.0562
_refine_ls_wR_factor_gt           0.0561
_refine_ls_goodness_of_fit_ref    1.068
_refine_ls_restrained_S_all       1.068
_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_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
Cl1 Cl -0.17887(6) 0.36945(5) 0.83669(3) 0.02481(14) Uani 1 1 d . . . . .
Cl2 Cl -0.06476(6) 0.44152(5) 0.67034(3) 0.02348(13) Uani 1 1 d . . . . .
O1 O 0.14008(19) 0.54765(14) 0.81671(8) 0.0190(3) Uani 1 1 d D . . . .
H1O H 0.184(4) 0.567(3) 0.8609(14) 0.034(8) Uiso 1 1 d D . . . .
O2 O 0.7228(2) 0.20179(16) 0.53607(10) 0.0282(4) Uani 1 1 d . . . . .
O3 O 0.6932(3) 0.41993(18) 0.49858(10) 0.0348(4) Uani 1 1 d . . . . .
N1 N 0.6552(3) 0.31857(18) 0.54233(10) 0.0222(4) Uani 1 1 d . . . . .
C1 C 0.4154(3) 0.3932(2) 0.98311(14) 0.0281(5) Uani 1 1 d . . . . .
H1A H 0.327892 0.412424 1.021955 0.034 Uiso 1 1 calc R U . . .
H1B H 0.529867 0.408679 0.998229 0.034 Uiso 1 1 calc R U . . .
C2 C 0.3782(3) 0.3452(2) 0.90838(13) 0.0198(4) Uani 1 1 d . . . . .
H2 H 0.468923 0.327168 0.871143 0.024 Uiso 1 1 calc R U . . .
C3 C 0.2020(3) 0.3169(2) 0.87779(13) 0.0181(4) Uani 1 1 d . . . . .
H3A H 0.120710 0.341076 0.922439 0.022 Uiso 1 1 calc R U . . .
H3B H 0.190086 0.215071 0.865659 0.022 Uiso 1 1 calc R U . . .
C4 C 0.1580(3) 0.40196(19) 0.79859(12) 0.0160(4) Uani 1 1 d . . . . .
C5 C -0.0117(3) 0.3493(2) 0.76382(12) 0.0174(4) Uani 1 1 d . . . . .
H5 H -0.000299 0.246833 0.750268 0.021 Uiso 1 1 calc R U . . .
C6 C 0.2899(3) 0.3797(2) 0.73039(11) 0.0154(4) Uani 1 1 d . . . . .
C7 C 0.3659(3) 0.4947(2) 0.69158(12) 0.0178(4) Uani 1 1 d . . . . .
H7 H 0.336382 0.587527 0.708334 0.021 Uiso 1 1 calc R U . . .
C8 C 0.4837(3) 0.4754(2) 0.62894(13) 0.0187(4) Uani 1 1 d . . . . .
H8 H 0.533840 0.553932 0.601753 0.022 Uiso 1 1 calc R U . . .
C9 C 0.5267(3) 0.3390(2) 0.60683(12) 0.0175(4) Uani 1 1 d . . . . .
C10 C 0.4532(3) 0.2224(2) 0.64356(12) 0.0184(4) Uani 1 1 d . . . . .
H10 H 0.484173 0.129839 0.626920 0.022 Uiso 1 1 calc R U . . .
C11 C 0.3337(3) 0.2435(2) 0.70505(12) 0.0175(4) Uani 1 1 d . . . . .
H11 H 0.280657 0.164606 0.730388 0.021 Uiso 1 1 calc R U . . .
 
 
_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 C5 1.777(2) . ?
Cl2 C5 1.786(2) . ?
O1 C4 1.419(2) . ?
O1 H1O 0.81(2) . ?
O2 N1 1.235(2) . ?
O3 N1 1.228(2) . ?
N1 C9 1.464(3) . ?
C1 C2 1.315(3) . ?
C1 H1A 0.9500 . ?
C1 H1B 0.9500 . ?
C2 C3 1.504(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.545(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C6 1.528(3) . ?
C4 C5 1.539(3) . ?
C5 H5 1.0000 . ?
C6 C7 1.393(3) . ?
C6 C11 1.398(3) . ?
C7 C8 1.383(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.385(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.382(3) . ?
C10 C11 1.382(3) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
 
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
C4 O1 H1O 111(2) . . ?
O3 N1 O2 123.38(19) . . ?
O3 N1 C9 118.04(17) . . ?
O2 N1 C9 118.56(17) . . ?
C2 C1 H1A 120.0 . . ?
C2 C1 H1B 120.0 . . ?
H1A C1 H1B 120.0 . . ?
C1 C2 C3 124.5(2) . . ?
C1 C2 H2 117.7 . . ?
C3 C2 H2 117.7 . . ?
C2 C3 C4 112.61(17) . . ?
C2 C3 H3A 109.1 . . ?
C4 C3 H3A 109.1 . . ?
C2 C3 H3B 109.1 . . ?
C4 C3 H3B 109.1 . . ?
H3A C3 H3B 107.8 . . ?
O1 C4 C6 110.48(15) . . ?
O1 C4 C5 107.64(16) . . ?
C6 C4 C5 107.08(16) . . ?
O1 C4 C3 111.28(16) . . ?
C6 C4 C3 111.20(16) . . ?
C5 C4 C3 109.00(16) . . ?
C4 C5 Cl1 112.22(14) . . ?
C4 C5 Cl2 110.52(14) . . ?
Cl1 C5 Cl2 108.90(11) . . ?
C4 C5 H5 108.4 . . ?
Cl1 C5 H5 108.4 . . ?
Cl2 C5 H5 108.4 . . ?
C7 C6 C11 119.13(18) . . ?
C7 C6 C4 120.46(17) . . ?
C11 C6 C4 120.40(17) . . ?
C8 C7 C6 120.83(18) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C9 118.40(19) . . ?
C7 C8 H8 120.8 . . ?
C9 C8 H8 120.8 . . ?
C10 C9 C8 122.36(19) . . ?
C10 C9 N1 119.21(18) . . ?
C8 C9 N1 118.43(18) . . ?
C11 C10 C9 118.48(18) . . ?
C11 C10 H10 120.8 . . ?
C9 C10 H10 120.8 . . ?
C10 C11 C6 120.77(18) . . ?
C10 C11 H11 119.6 . . ?
C6 C11 H11 119.6 . . ?
 
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
C1 C2 C3 C4 121.8(2) . . . . ?
C2 C3 C4 O1 -70.5(2) . . . . ?
C2 C3 C4 C6 53.1(2) . . . . ?
C2 C3 C4 C5 170.96(16) . . . . ?
O1 C4 C5 Cl1 -60.93(18) . . . . ?
C6 C4 C5 Cl1 -179.73(13) . . . . ?
C3 C4 C5 Cl1 59.88(18) . . . . ?
O1 C4 C5 Cl2 60.83(17) . . . . ?
C6 C4 C5 Cl2 -57.97(17) . . . . ?
C3 C4 C5 Cl2 -178.36(13) . . . . ?
O1 C4 C6 C7 -4.0(3) . . . . ?
C5 C4 C6 C7 112.94(19) . . . . ?
C3 C4 C6 C7 -128.09(19) . . . . ?
O1 C4 C6 C11 177.19(17) . . . . ?
C5 C4 C6 C11 -65.9(2) . . . . ?
C3 C4 C6 C11 53.1(2) . . . . ?
C11 C6 C7 C8 -0.3(3) . . . . ?
C4 C6 C7 C8 -179.07(18) . . . . ?
C6 C7 C8 C9 -1.2(3) . . . . ?
C7 C8 C9 C10 1.7(3) . . . . ?
C7 C8 C9 N1 -178.15(18) . . . . ?
O3 N1 C9 C10 165.0(2) . . . . ?
O2 N1 C9 C10 -16.8(3) . . . . ?
O3 N1 C9 C8 -15.1(3) . . . . ?
O2 N1 C9 C8 163.1(2) . . . . ?
C8 C9 C10 C11 -0.6(3) . . . . ?
N1 C9 C10 C11 179.21(18) . . . . ?
C9 C10 C11 C6 -0.9(3) . . . . ?
C7 C6 C11 C10 1.4(3) . . . . ?
C4 C6 C11 C10 -179.83(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 
O1 H1O O2  0.81(2) 2.21(2) 2.982(2) 158(3) 3_656
 
_refine_diff_density_max    0.299
_refine_diff_density_min   -0.161
_refine_diff_density_rms    0.046



