data_kckd1054_0m_a
_audit_creation_date               2020-10-07
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number       '2018/3'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C11 H8 Cl2 O3'
_chemical_formula_sum              'C11 H8 Cl2 O3'
_chemical_formula_weight           259.07
_chemical_absolute_configuration   unk
_chemical_melting_point            ?
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'
 'Cl' 'Cl' 0.1484 0.1585 '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'

_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.
;
_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'
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                     9.0147(3)
_cell_length_b                     10.9941(5)
_cell_length_c                     11.1906(5)
_cell_angle_alpha                  90
_cell_angle_beta                   90
_cell_angle_gamma                  90
_cell_volume                       1109.08(8)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      9952
_cell_measurement_temperature      296.15
_cell_measurement_theta_max        29.253
_cell_measurement_theta_min        2.901
_shelx_estimated_absorpt_T_max     0.856
_shelx_estimated_absorpt_T_min     0.838
_exptl_absorpt_coefficient_mu      0.572
_exptl_absorpt_correction_T_max    0.7461
_exptl_absorpt_correction_T_min    0.6953
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0533 before and 0.0497 after correction.
The Ratio of minimum to maximum transmission is 0.9319.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              colourless
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.552
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         block
_exptl_crystal_F_000               528
_exptl_crystal_size_max            0.32
_exptl_crystal_size_mid            0.32
_exptl_crystal_size_min            0.28
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0307
_diffrn_reflns_av_unetI/netI       0.0137
_diffrn_reflns_Laue_measured_fraction_full  0.983
_diffrn_reflns_Laue_measured_fraction_max  0.989
_diffrn_reflns_limit_h_max         11
_diffrn_reflns_limit_h_min         -12
_diffrn_reflns_limit_k_max         15
_diffrn_reflns_limit_k_min         -15
_diffrn_reflns_limit_l_max         15
_diffrn_reflns_limit_l_min         -15
_diffrn_reflns_number              36194
_diffrn_reflns_point_group_measured_fraction_full  0.987
_diffrn_reflns_point_group_measured_fraction_max  0.991
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           30.479
_diffrn_reflns_theta_min           2.902
_diffrn_ambient_temperature        296.15
_diffrn_detector                   'Bruker PHOTON 200 area detector'
_diffrn_detector_area_resol_mean   7.39
_diffrn_detector_type              'PHOTON II area detector'
_diffrn_measured_fraction_theta_full  0.983
_diffrn_measured_fraction_theta_max  0.989
_diffrn_measurement_device         'four-circle KAPPA diffractometer'
_diffrn_measurement_device_type    'BRUKER D8 QUEST CMOS PHOTON II'
_diffrn_measurement_method         'φ and ω scans'
_diffrn_radiation_collimation      '0.5 mm'
_diffrn_radiation_monochromator    graphite
_diffrn_radiation_probe            x-ray
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_radiation_xray_symbol      K-L~3~
_diffrn_source                     'sealed x-ray tube'
_diffrn_source_current             30.0
_diffrn_source_power               1.5
_diffrn_source_target              Mo
_diffrn_source_type                Mo
_diffrn_source_voltage             50.0
_diffrn_standards_number           0
_reflns_Friedel_coverage           0.749
_reflns_Friedel_fraction_full      0.992
_reflns_Friedel_fraction_max       0.993
_reflns_number_gt                  3065
_reflns_number_total               3344
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'SAINT V8.40A (?, 2016)'
_computing_data_collection         ?
_computing_data_reduction          'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics      'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement    'XL  (Sheldrick, 2008)'
_computing_structure_solution      'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max           0.226
_refine_diff_density_min           -0.222
_refine_diff_density_rms           0.035
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack     0.42(7)
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.037
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       146
_refine_ls_number_reflns           3344
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0349
_refine_ls_R_factor_gt             0.0305
_refine_ls_restrained_S_all        1.037
_refine_ls_shift/su_max            0.000
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0427P)²+0.1457P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0796
_refine_ls_wR_factor_ref           0.0827
_refine_special_details
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.58(7)
 0.42(7)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       ?
_atom_sites_solution_secondary     ?
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 0.82421(6) 0.58212(6) 0.58467(6) 0.05999(16) Uani 1 1 d . . . . .
 Cl2 Cl 0.65138(8) 0.36697(5) 0.54824(5) 0.06016(17) Uani 1 1 d . . . . .
 O1 O 0.38983(16) 0.51994(16) 0.58180(13) 0.0543(4) Uani 1 1 d . . . . .
 O2 O 0.2241(2) 0.4393(2) 0.4561(2) 0.0808(6) Uani 1 1 d . . . . .
 O3 O 0.51718(19) 0.68503(15) 0.65934(14) 0.0548(4) Uani 1 1 d . . . . .
 C1 C 0.3283(3) 0.5044(2) 0.4710(2) 0.0537(5) Uani 1 1 d . . . . .
 C2 C 0.4124(2) 0.5812(2) 0.38677(18) 0.0471(4) Uani 1 1 d . . . . .
 C3 C 0.3882(3) 0.6004(3) 0.2659(2) 0.0638(6) Uani 1 1 d . . . . .
 H3 H 0.312170 0.560901 0.225218 0.077 Uiso 1 1 calc R U . . .
 C4 C 0.4813(4) 0.6801(3) 0.2090(2) 0.0730(8) Uani 1 1 d . . . . .
 H4 H 0.470006 0.693590 0.127463 0.088 Uiso 1 1 calc R U . . .
 C5 C 0.5919(4) 0.7410(2) 0.2705(3) 0.0688(7) Uani 1 1 d . . . . .
 H5 H 0.651339 0.796229 0.229589 0.083 Uiso 1 1 calc R U . . .
 C6 C 0.6167(3) 0.72189(19) 0.3915(2) 0.0544(5) Uani 1 1 d . . . . .
 H6 H 0.691343 0.762691 0.432572 0.065 Uiso 1 1 calc R U . . .
 C7 C 0.5246(2) 0.63894(18) 0.44809(16) 0.0418(4) Uani 1 1 d . . . . .
 C8 C 0.5237(2) 0.59469(18) 0.57461(17) 0.0419(4) Uani 1 1 d . . . . .
 C9 C 0.6514(2) 0.51138(16) 0.61740(17) 0.0437(4) Uani 1 1 d . . . . .
 C10 C 0.6254(3) 0.5104(2) 0.75176(19) 0.0605(6) Uani 1 1 d . . . . .
 H10A H 0.551271 0.450635 0.774057 0.073 Uiso 1 1 calc R U . . .
 H10B H 0.716430 0.494288 0.795136 0.073 Uiso 1 1 calc R U . . .
 C11 C 0.5705(3) 0.6390(3) 0.7738(2) 0.0622(6) Uani 1 1 d . . . . .
 H11A H 0.490913 0.638830 0.832152 0.075 Uiso 1 1 calc R U . . .
 H11B H 0.650436 0.689670 0.803658 0.075 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 C9 1.779(2) . ?
 Cl2 C9 1.7662(18) . ?
 O1 C1 1.369(3) . ?
 O1 C8 1.462(2) . ?
 O2 C1 1.193(3) . ?
 O3 C8 1.374(2) . ?
 O3 C11 1.459(3) . ?
 C1 C2 1.475(3) . ?
 C2 C3 1.386(3) . ?
 C2 C7 1.377(3) . ?
 C3 H3 0.9300 . ?
 C3 C4 1.371(4) . ?
 C4 H4 0.9300 . ?
 C4 C5 1.384(5) . ?
 C5 H5 0.9300 . ?
 C5 C6 1.389(4) . ?
 C6 H6 0.9300 . ?
 C6 C7 1.386(3) . ?
 C7 C8 1.497(3) . ?
 C8 C9 1.547(3) . ?
 C9 C10 1.522(3) . ?
 C10 H10A 0.9700 . ?
 C10 H10B 0.9700 . ?
 C10 C11 1.518(4) . ?
 C11 H11A 0.9700 . ?
 C11 H11B 0.9700 . ?

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
 C1 O1 C8 110.77(16) . . ?
 C8 O3 C11 109.95(17) . . ?
 O1 C1 C2 107.42(18) . . ?
 O2 C1 O1 121.4(2) . . ?
 O2 C1 C2 131.2(2) . . ?
 C3 C2 C1 129.0(2) . . ?
 C7 C2 C1 108.82(17) . . ?
 C7 C2 C3 122.1(2) . . ?
 C2 C3 H3 121.5 . . ?
 C4 C3 C2 117.0(3) . . ?
 C4 C3 H3 121.5 . . ?
 C3 C4 H4 119.3 . . ?
 C3 C4 C5 121.3(2) . . ?
 C5 C4 H4 119.3 . . ?
 C4 C5 H5 119.1 . . ?
 C4 C5 C6 121.8(3) . . ?
 C6 C5 H5 119.1 . . ?
 C5 C6 H6 121.7 . . ?
 C7 C6 C5 116.6(2) . . ?
 C7 C6 H6 121.7 . . ?
 C2 C7 C6 121.03(19) . . ?
 C2 C7 C8 108.53(17) . . ?
 C6 C7 C8 130.44(19) . . ?
 O1 C8 C7 103.82(15) . . ?
 O1 C8 C9 105.33(16) . . ?
 O3 C8 O1 109.43(16) . . ?
 O3 C8 C7 114.70(17) . . ?
 O3 C8 C9 104.26(15) . . ?
 C7 C8 C9 118.77(16) . . ?
 Cl2 C9 Cl1 107.64(11) . . ?
 C8 C9 Cl1 109.20(13) . . ?
 C8 C9 Cl2 113.35(13) . . ?
 C10 C9 Cl1 109.97(16) . . ?
 C10 C9 Cl2 115.26(16) . . ?
 C10 C9 C8 101.24(18) . . ?
 C9 C10 H10A 111.4 . . ?
 C9 C10 H10B 111.4 . . ?
 H10A C10 H10B 109.3 . . ?
 C11 C10 C9 101.81(19) . . ?
 C11 C10 H10A 111.4 . . ?
 C11 C10 H10B 111.4 . . ?
 O3 C11 C10 106.71(17) . . ?
 O3 C11 H11A 110.4 . . ?
 O3 C11 H11B 110.4 . . ?
 C10 C11 H11A 110.4 . . ?
 C10 C11 H11B 110.4 . . ?
 H11A C11 H11B 108.6 . . ?

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
 Cl1 C9 C10 C11 80.1(2) . . . . ?
 Cl2 C9 C10 C11 -158.03(17) . . . . ?
 O1 C1 C2 C3 -176.9(2) . . . . ?
 O1 C1 C2 C7 1.4(2) . . . . ?
 O1 C8 C9 Cl1 168.55(12) . . . . ?
 O1 C8 C9 Cl2 48.56(18) . . . . ?
 O1 C8 C9 C10 -75.48(19) . . . . ?
 O2 C1 C2 C3 2.2(4) . . . . ?
 O2 C1 C2 C7 -179.6(3) . . . . ?
 O3 C8 C9 Cl1 -76.26(16) . . . . ?
 O3 C8 C9 Cl2 163.74(14) . . . . ?
 O3 C8 C9 C10 39.7(2) . . . . ?
 C1 O1 C8 O3 131.07(19) . . . . ?
 C1 O1 C8 C7 8.2(2) . . . . ?
 C1 O1 C8 C9 -117.37(18) . . . . ?
 C1 C2 C3 C4 178.0(2) . . . . ?
 C1 C2 C7 C6 -176.74(19) . . . . ?
 C1 C2 C7 C8 3.8(2) . . . . ?
 C2 C3 C4 C5 -1.6(4) . . . . ?
 C2 C7 C8 O1 -7.1(2) . . . . ?
 C2 C7 C8 O3 -126.49(19) . . . . ?
 C2 C7 C8 C9 109.33(19) . . . . ?
 C3 C2 C7 C6 1.7(3) . . . . ?
 C3 C2 C7 C8 -177.8(2) . . . . ?
 C3 C4 C5 C6 1.8(4) . . . . ?
 C4 C5 C6 C7 -0.2(4) . . . . ?
 C5 C6 C7 C2 -1.5(3) . . . . ?
 C5 C6 C7 C8 177.9(2) . . . . ?
 C6 C7 C8 O1 173.4(2) . . . . ?
 C6 C7 C8 O3 54.1(3) . . . . ?
 C6 C7 C8 C9 -70.1(3) . . . . ?
 C7 C2 C3 C4 -0.1(3) . . . . ?
 C7 C8 C9 Cl1 52.88(19) . . . . ?
 C7 C8 C9 Cl2 -67.1(2) . . . . ?
 C7 C8 C9 C10 168.85(18) . . . . ?
 C8 O1 C1 O2 174.7(2) . . . . ?
 C8 O1 C1 C2 -6.1(2) . . . . ?
 C8 O3 C11 C10 4.7(3) . . . . ?
 C8 C9 C10 C11 -35.3(2) . . . . ?
 C9 C10 C11 O3 20.5(3) . . . . ?
 C11 O3 C8 O1 84.5(2) . . . . ?
 C11 O3 C8 C7 -159.31(18) . . . . ?
 C11 O3 C8 C9 -27.8(2) . . . . ?

_olex2_submission_special_instructions  'No special instructions were received'
loop_
  _twin_individual_id
  _twin_individual_mass_fraction_refined
 1 0.58(7)
 2 0.42(7)

