 
data_A024_014
 
_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C15 H16 Cl3 N O5' 
_chemical_formula_weight          396.64

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       monoclinic
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 21/c'
_space_group_name_Hall            '-P 2ybc'
 
_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+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'
 
_cell_length_a                    9.7785(13)
_cell_length_b                    19.179(2)
_cell_length_c                    9.7311(12)
_cell_angle_alpha                 90
_cell_angle_beta                  100.022(5)
_cell_angle_gamma                 90
_cell_volume                      1797.2(4)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     27219
_cell_measurement_theta_min       2.998
_cell_measurement_theta_max       25.99
 
_exptl_crystal_description        needle
_exptl_crystal_colour             colorless
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.466          
_exptl_crystal_F_000              816
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.217
_exptl_crystal_size_mid           0.032
_exptl_crystal_size_min           0.025
_exptl_absorpt_coefficient_mu     0.534
_shelx_estimated_absorpt_T_min    0.893
_shelx_estimated_absorpt_T_max    0.987
_exptl_absorpt_correction_type    MULTI-SCAN
_exptl_absorpt_correction_T_min   0.6741
_exptl_absorpt_correction_T_max   0.7456
_exptl_absorpt_process_details    SADABS
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    'fine-focus sealed tube'
_diffrn_measurement_device_type   'Photon 100 CMOS detector'
_diffrn_measurement_method        'phi and omega scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             23813
_diffrn_reflns_av_unetI/netI      0.0989
_diffrn_reflns_av_R_equivalents   0.1858
_diffrn_reflns_limit_h_min        -12
_diffrn_reflns_limit_h_max        12
_diffrn_reflns_limit_k_min        -23
_diffrn_reflns_limit_k_max        23
_diffrn_reflns_limit_l_min        -12
_diffrn_reflns_limit_l_max        12
_diffrn_reflns_theta_min          2.998
_diffrn_reflns_theta_max          25.998
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.998
_diffrn_measured_fraction_theta_full  0.998
_diffrn_reflns_Laue_measured_fraction_max    0.998
_diffrn_reflns_Laue_measured_fraction_full   0.998
_diffrn_reflns_point_group_measured_fraction_max   0.998
_diffrn_reflns_point_group_measured_fraction_full  0.998
_reflns_number_total              3522
_reflns_number_gt                 2094
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_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 APEXx'
_computing_cell_refinement        'Bruker APEXx'
_computing_data_reduction         'Bruker SAINT'
_computing_structure_solution     SHELXS
_computing_structure_refinement   SHELXL
_computing_molecular_graphics     ORTEP
_computing_publication_material   CIFTAB
_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)+(0.0235P)²+1.9098P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          3522
_refine_ls_number_parameters      225
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1170
_refine_ls_R_factor_gt            0.0519
_refine_ls_wR_factor_ref          0.1005
_refine_ls_wR_factor_gt           0.0826
_refine_ls_goodness_of_fit_ref    1.012
_refine_ls_restrained_S_all       1.012
_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 0.72164(9) 0.37266(5) 0.13962(11) 0.0288(2) Uani 1 1 d . . . . .
Cl2 Cl 0.92378(10) 0.37345(6) 0.39344(11) 0.0363(3) Uani 1 1 d . . . . .
Cl3 Cl 1.00300(10) 0.32571(5) 0.13662(10) 0.0320(3) Uani 1 1 d . . . . .
C1 C 0.8668(3) 0.32814(19) 0.2347(4) 0.0221(9) Uani 1 1 d . . . . .
C2 C 0.8325(3) 0.25344(18) 0.2632(4) 0.0198(8) Uani 1 1 d . . . . .
H2A H 0.796674 0.229633 0.173965 0.024 Uiso 1 1 calc R U . . .
H2B H 0.917977 0.229006 0.307877 0.024 Uiso 1 1 calc R U . . .
O1 O 0.7308(2) 0.24979(13) 0.3526(2) 0.0208(6) Uani 1 1 d . . . . .
C3 C 0.5972(3) 0.23650(17) 0.2908(4) 0.0137(8) Uani 1 1 d . . . . .
O2 O 0.5594(2) 0.22653(12) 0.1674(2) 0.0186(6) Uani 1 1 d . . . . .
N1 N 0.5165(3) 0.23612(15) 0.3876(3) 0.0171(7) Uani 1 1 d . . . . .
H1N H 0.550(4) 0.2450(18) 0.471(4) 0.021 Uiso 1 1 d . U . . .
C4 C 0.3695(4) 0.22235(18) 0.3548(4) 0.0165(8) Uani 1 1 d . . . . .
H1C4 H 0.333(3) 0.2292(17) 0.255(4) 0.020 Uiso 1 1 d . U . . .
C5 C 0.2924(3) 0.27487(18) 0.4341(3) 0.0156(8) Uani 1 1 d . . . . .
O3 O 0.2248(2) 0.25343(12) 0.5191(2) 0.0217(6) Uani 1 1 d . . . . .
C6 C 0.3094(3) 0.35001(17) 0.4078(4) 0.0154(8) Uani 1 1 d . . . . .
C7 C 0.2705(4) 0.39789(18) 0.5020(4) 0.0205(9) Uani 1 1 d . . . . .
H7 H 0.233305 0.381553 0.580053 0.025 Uiso 1 1 calc R U . . .
C8 C 0.2852(4) 0.46839(19) 0.4833(4) 0.0236(9) Uani 1 1 d . . . . .
H8 H 0.258773 0.500067 0.549044 0.028 Uiso 1 1 calc R U . . .
C9 C 0.3386(4) 0.49409(18) 0.3693(4) 0.0230(9) Uani 1 1 d . . . . .
C10 C 0.3759(4) 0.44670(18) 0.2750(4) 0.0232(9) Uani 1 1 d . . . . .
H10 H 0.411434 0.463207 0.196107 0.028 Uiso 1 1 calc R U . . .
C11 C 0.3622(3) 0.37579(19) 0.2938(4) 0.0206(8) Uani 1 1 d . . . . .
H11 H 0.389234 0.344220 0.228172 0.025 Uiso 1 1 calc R U . . .
C12 C 0.3558(4) 0.57106(19) 0.3508(5) 0.0363(11) Uani 1 1 d . . . . .
H12A H 0.367777 0.580618 0.254625 0.055 Uiso 1 1 calc R U . . .
H12B H 0.437758 0.587366 0.415434 0.055 Uiso 1 1 calc R U . . .
H12C H 0.273197 0.595470 0.370105 0.055 Uiso 1 1 calc R U . . .
C13 C 0.3372(4) 0.14806(18) 0.3927(4) 0.0175(8) Uani 1 1 d . . . . .
O4 O 0.2058(2) 0.13110(12) 0.3400(2) 0.0214(6) Uani 1 1 d . . . . .
O5 O 0.4198(3) 0.10914(13) 0.4592(3) 0.0291(7) Uani 1 1 d . . . . .
C14 C 0.1645(4) 0.06086(19) 0.3717(4) 0.0310(10) Uani 1 1 d . . . . .
H14A H 0.174876 0.054298 0.473873 0.037 Uiso 1 1 calc R U . . .
H14B H 0.223247 0.026051 0.334359 0.037 Uiso 1 1 calc R U . . .
C15 C 0.0152(4) 0.0522(2) 0.3042(5) 0.0404(12) Uani 1 1 d . . . . .
H15A H -0.042353 0.085436 0.345248 0.061 Uiso 1 1 calc R U . . .
H15B H -0.015158 0.004590 0.319481 0.061 Uiso 1 1 calc R U . . .
H15C H 0.005685 0.061019 0.203749 0.061 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 C1 1.773(4) . ?
Cl2 C1 1.775(4) . ?
Cl3 C1 1.769(3) . ?
C1 C2 1.508(5) . ?
C2 O1 1.432(4) . ?
O1 C3 1.364(4) . ?
C3 O2 1.209(4) . ?
C3 N1 1.330(4) . ?
N1 C4 1.442(4) . ?
C4 C13 1.519(5) . ?
C4 C5 1.543(5) . ?
C5 O3 1.216(4) . ?
C5 C6 1.478(5) . ?
C6 C11 1.393(5) . ?
C6 C7 1.397(5) . ?
C7 C8 1.375(5) . ?
C8 C9 1.396(5) . ?
C9 C10 1.385(5) . ?
C9 C12 1.500(5) . ?
C10 C11 1.382(5) . ?
C13 O5 1.202(4) . ?
C13 O4 1.339(4) . ?
O4 C14 1.455(4) . ?
C14 C15 1.502(5) . ?
 
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 Cl3 106.6(2) . . ?
C2 C1 Cl1 111.7(2) . . ?
Cl3 C1 Cl1 109.9(2) . . ?
C2 C1 Cl2 110.6(3) . . ?
Cl3 C1 Cl2 109.30(19) . . ?
Cl1 C1 Cl2 108.7(2) . . ?
O1 C2 C1 111.0(3) . . ?
C3 O1 C2 117.0(3) . . ?
O2 C3 N1 125.9(3) . . ?
O2 C3 O1 124.8(3) . . ?
N1 C3 O1 109.2(3) . . ?
C3 N1 C4 122.4(3) . . ?
N1 C4 C13 111.1(3) . . ?
N1 C4 C5 109.0(3) . . ?
C13 C4 C5 110.5(3) . . ?
O3 C5 C6 122.6(3) . . ?
O3 C5 C4 119.3(3) . . ?
C6 C5 C4 118.0(3) . . ?
C11 C6 C7 118.1(3) . . ?
C11 C6 C5 123.5(3) . . ?
C7 C6 C5 118.4(3) . . ?
C8 C7 C6 120.8(3) . . ?
C7 C8 C9 121.0(3) . . ?
C10 C9 C8 118.3(3) . . ?
C10 C9 C12 121.2(4) . . ?
C8 C9 C12 120.6(4) . . ?
C11 C10 C9 121.0(4) . . ?
C10 C11 C6 120.8(3) . . ?
O5 C13 O4 124.4(3) . . ?
O5 C13 C4 124.4(3) . . ?
O4 C13 C4 111.2(3) . . ?
C13 O4 C14 115.3(3) . . ?
O4 C14 C15 107.1(3) . . ?
 
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 
 _geom_hbond_publ_flag
N1 H1N O2  0.84(3) 1.97(4) 2.775(4) 160(3) 4_566 yes
 
_refine_diff_density_max    0.391
_refine_diff_density_min   -0.348
_refine_diff_density_rms    0.085


















