data_19gtu356_ca_13_0m_a
_audit_creation_date               2019-10-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number       '2014/7'
_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.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C24 H16 Cl2 N2 O2'
_chemical_formula_sum              'C24 H16 Cl2 N2 O2'
_chemical_formula_weight           435.29
_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'
 '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'

_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        'monoclinic'
_space_group_IT_number             14
_space_group_name_H-M_alt          'P 1 21/c 1'
_space_group_name_Hall             '-P 2ybc'
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                     8.393(3)
_cell_length_b                     20.906(7)
_cell_length_c                     11.854(4)
_cell_angle_alpha                  90
_cell_angle_beta                   97.963(6)
_cell_angle_gamma                  90
_cell_volume                       2059.9(11)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      2468
_cell_measurement_temperature      296(2)
_cell_measurement_theta_max        26.64
_cell_measurement_theta_min        2.45
_shelx_estimated_absorpt_T_max     0.960
_shelx_estimated_absorpt_T_min     0.941
_exptl_absorpt_coefficient_mu      0.339
_exptl_absorpt_correction_T_max    0.7456
_exptl_absorpt_correction_T_min    0.6241
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0784 before and 0.0410 after correction.
The Ratio of minimum to maximum transmission is 0.8370.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              red
_exptl_crystal_colour_primary      red
_exptl_crystal_density_diffrn      1.404
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         block
_exptl_crystal_F_000               896
_exptl_crystal_size_max            0.18
_exptl_crystal_size_mid            0.15
_exptl_crystal_size_min            0.12
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0519
_diffrn_reflns_av_unetI/netI       0.0672
_diffrn_reflns_Laue_measured_fraction_full  0.993
_diffrn_reflns_Laue_measured_fraction_max  0.993
_diffrn_reflns_limit_h_max         9
_diffrn_reflns_limit_h_min         -9
_diffrn_reflns_limit_k_max         24
_diffrn_reflns_limit_k_min         -22
_diffrn_reflns_limit_l_max         11
_diffrn_reflns_limit_l_min         -14
_diffrn_reflns_number              8307
_diffrn_reflns_point_group_measured_fraction_full  0.993
_diffrn_reflns_point_group_measured_fraction_max  0.993
_diffrn_reflns_theta_full          25.026
_diffrn_reflns_theta_max           25.026
_diffrn_reflns_theta_min           1.948
_diffrn_ambient_temperature        296.15
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.993
_diffrn_measured_fraction_theta_max  0.993
_diffrn_measurement_device_type    'Bruker APEX-II CCD'
_diffrn_measurement_method         'φ and ω scans'
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     ?
_diffrn_standards_number           0
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  2211
_reflns_number_total               3593
_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.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection         ?
_computing_data_reduction          'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics      'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement    'XL (Sheldrick, 2008)'
_computing_structure_solution      'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max           0.218
_refine_diff_density_min           -0.213
_refine_diff_density_rms           0.045
_refine_ls_extinction_coef         0.0029(7)
_refine_ls_extinction_expression  
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_extinction_method       'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref     1.001
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       273
_refine_ls_number_reflns           3593
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0863
_refine_ls_R_factor_gt             0.0441
_refine_ls_restrained_S_all        1.001
_refine_ls_shift/su_max            0.001
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0471P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0958
_refine_ls_wR_factor_ref           0.1159
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C17(H17), C4(H4), C16(H16), C6(H6), C15(H15), C20(H20), C3(H3),
 C24(H24), C7(H7), C21(H21), C22(H22), C23(H23)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       dual
_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 0.61469(9) 0.50675(4) 0.87408(6) 0.0633(3) Uani 1 1 d . . . . .
 Cl2 Cl 0.86369(8) 0.56884(4) 0.73409(7) 0.0655(3) Uani 1 1 d . . . . .
 O1 O 0.3166(2) 0.47519(8) 0.71398(14) 0.0399(5) Uani 1 1 d . . . . .
 O2 O 0.7157(2) 0.61214(11) 0.51066(17) 0.0645(7) Uani 1 1 d . . . . .
 N1 N 0.2902(2) 0.57392(11) 0.78683(17) 0.0385(6) Uani 1 1 d . . . . .
 N2 N 0.2211(2) 0.52905(12) 0.85404(18) 0.0396(6) Uani 1 1 d . . . . .
 C8 C 0.2338(3) 0.47497(14) 0.8074(2) 0.0375(7) Uani 1 1 d . . . . .
 C9 C 0.3776(3) 0.53878(13) 0.7040(2) 0.0359(6) Uani 1 1 d . . . . .
 C18 C 0.3312(3) 0.56181(12) 0.5839(2) 0.0357(6) Uani 1 1 d . . . . .
 C5 C 0.1707(3) 0.41361(14) 0.8393(2) 0.0400(7) Uani 1 1 d . . . . .
 C13 C 0.4443(3) 0.58395(13) 0.5171(2) 0.0376(6) Uani 1 1 d . . . . .
 C19 C 0.3614(3) 0.62869(13) 0.8434(2) 0.0391(7) Uani 1 1 d . . . . .
 C12 C 0.6166(3) 0.58878(14) 0.5649(2) 0.0424(7) Uani 1 1 d . . . . .
 C10 C 0.5578(3) 0.53852(14) 0.7414(2) 0.0402(7) Uani 1 1 d . . . . .
 C11 C 0.6643(3) 0.56365(13) 0.6808(2) 0.0396(7) Uani 1 1 d . . . . .
 C14 C 0.3934(4) 0.60448(14) 0.4065(2) 0.0485(8) Uani 1 1 d . . . . .
 H14 H 0.4684 0.6193 0.3618 0.058 Uiso 1 1 calc R . . . .
 C17 C 0.1700(3) 0.56090(14) 0.5385(2) 0.0481(8) Uani 1 1 d . . . . .
 H17 H 0.0938 0.5461 0.5822 0.058 Uiso 1 1 calc R . . . .
 C4 C 0.1895(3) 0.35880(15) 0.7769(3) 0.0482(8) Uani 1 1 d . . . . .
 H4 H 0.2438 0.3608 0.7138 0.058 Uiso 1 1 calc R . . . .
 C16 C 0.1224(4) 0.58168(15) 0.4295(2) 0.0550(8) Uani 1 1 d . . . . .
 H16 H 0.0137 0.5814 0.4000 0.066 Uiso 1 1 calc R . . . .
 C6 C 0.0892(3) 0.40916(16) 0.9337(2) 0.0552(8) Uani 1 1 d . . . . .
 H6 H 0.0742 0.4455 0.9763 0.066 Uiso 1 1 calc R . . . .
 C15 C 0.2336(4) 0.60309(15) 0.3627(2) 0.0550(8) Uani 1 1 d . . . . .
 H15 H 0.2003 0.6165 0.2884 0.066 Uiso 1 1 calc R . . . .
 C20 C 0.4208(4) 0.67695(15) 0.7810(3) 0.0579(9) Uani 1 1 d . . . . .
 H20 H 0.4090 0.6745 0.7020 0.069 Uiso 1 1 calc R . . . .
 C3 C 0.1283(4) 0.30148(16) 0.8078(3) 0.0608(9) Uani 1 1 d . . . . .
 H3 H 0.1410 0.2653 0.7644 0.073 Uiso 1 1 calc R . . . .
 C2 C 0.0483(4) 0.29616(17) 0.9020(3) 0.0611(9) Uani 1 1 d . . . . .
 C24 C 0.3717(4) 0.63583(16) 0.9597(3) 0.0656(9) Uani 1 1 d . . . . .
 H24 H 0.3269 0.6052 1.0027 0.079 Uiso 1 1 calc R . . . .
 C7 C 0.0308(4) 0.35107(19) 0.9639(3) 0.0664(10) Uani 1 1 d . . . . .
 H7 H -0.0219 0.3487 1.0278 0.080 Uiso 1 1 calc R . . . .
 C21 C 0.4975(4) 0.72876(17) 0.8367(4) 0.0788(11) Uani 1 1 d . . . . .
 H21 H 0.5402 0.7604 0.7945 0.095 Uiso 1 1 calc R . . . .
 C22 C 0.5119(5) 0.73444(19) 0.9508(4) 0.0862(12) Uani 1 1 d . . . . .
 H22 H 0.5646 0.7695 0.9872 0.103 Uiso 1 1 calc R . . . .
 C23 C 0.4483(5) 0.68827(18) 1.0124(3) 0.0878(13) Uani 1 1 d . . . . .
 H23 H 0.4567 0.6923 1.0912 0.105 Uiso 1 1 calc R . . . .
 C1 C -0.0183(5) 0.23261(18) 0.9365(4) 0.1000(14) Uani 1 1 d . . . . .
 H1A H -0.0701 0.2109 0.8699 0.150 Uiso 1 1 calc GR . . . .
 H1B H -0.0949 0.2401 0.9881 0.150 Uiso 1 1 calc GR . . . .
 H1C H 0.0681 0.2067 0.9732 0.150 Uiso 1 1 calc GR . . . .


_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 C10 1.713(3) . ?
 Cl2 C11 1.708(3) . ?
 O1 C8 1.386(3) . ?
 O1 C9 1.435(3) . ?
 O2 C12 1.222(3) . ?
 N1 N2 1.407(3) . ?
 N1 C9 1.497(3) . ?
 N1 C19 1.416(3) . ?
 N2 C8 1.269(3) . ?
 C8 C5 1.458(4) . ?
 C9 C18 1.503(3) . ?
 C9 C10 1.516(4) . ?
 C18 C13 1.396(3) . ?
 C18 C17 1.385(3) . ?
 C5 C4 1.384(4) . ?
 C5 C6 1.393(4) . ?
 C13 C12 1.481(4) . ?
 C13 C14 1.390(4) . ?
 C19 C20 1.384(4) . ?
 C19 C24 1.377(4) . ?
 C12 C11 1.474(4) . ?
 C10 C11 1.330(3) . ?
 C14 C15 1.369(4) . ?
 C17 C16 1.370(4) . ?
 C4 C3 1.373(4) . ?
 C16 C15 1.379(4) . ?
 C6 C7 1.376(4) . ?
 C20 C21 1.381(4) . ?
 C3 C2 1.385(4) . ?
 C2 C7 1.381(5) . ?
 C2 C1 1.519(5) . ?
 C24 C23 1.376(5) . ?
 C21 C22 1.347(5) . ?
 C22 C23 1.363(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
 C8 O1 C9 107.0(2) . . ?
 N2 N1 C9 108.8(2) . . ?
 N2 N1 C19 116.8(2) . . ?
 C19 N1 C9 119.7(2) . . ?
 C8 N2 N1 106.3(2) . . ?
 O1 C8 C5 116.8(2) . . ?
 N2 C8 O1 115.2(2) . . ?
 N2 C8 C5 128.0(2) . . ?
 O1 C9 N1 100.84(18) . . ?
 O1 C9 C18 109.0(2) . . ?
 O1 C9 C10 109.0(2) . . ?
 N1 C9 C18 112.2(2) . . ?
 N1 C9 C10 111.7(2) . . ?
 C18 C9 C10 113.3(2) . . ?
 C13 C18 C9 122.4(2) . . ?
 C17 C18 C9 118.3(2) . . ?
 C17 C18 C13 119.3(2) . . ?
 C4 C5 C8 121.2(2) . . ?
 C4 C5 C6 118.6(3) . . ?
 C6 C5 C8 120.2(3) . . ?
 C18 C13 C12 120.7(2) . . ?
 C14 C13 C18 119.5(3) . . ?
 C14 C13 C12 119.7(2) . . ?
 C20 C19 N1 119.7(2) . . ?
 C24 C19 N1 121.7(3) . . ?
 C24 C19 C20 118.6(3) . . ?
 O2 C12 C13 121.7(3) . . ?
 O2 C12 C11 121.1(3) . . ?
 C11 C12 C13 117.2(2) . . ?
 C9 C10 Cl1 114.19(18) . . ?
 C11 C10 Cl1 121.7(2) . . ?
 C11 C10 C9 124.0(2) . . ?
 C12 C11 Cl2 116.61(19) . . ?
 C10 C11 Cl2 121.5(2) . . ?
 C10 C11 C12 121.8(2) . . ?
 C15 C14 C13 120.5(3) . . ?
 C16 C17 C18 120.2(3) . . ?
 C3 C4 C5 120.4(3) . . ?
 C17 C16 C15 120.8(3) . . ?
 C7 C6 C5 120.0(3) . . ?
 C14 C15 C16 119.7(3) . . ?
 C21 C20 C19 119.7(3) . . ?
 C4 C3 C2 121.8(3) . . ?
 C3 C2 C1 121.6(4) . . ?
 C7 C2 C3 117.4(3) . . ?
 C7 C2 C1 120.9(3) . . ?
 C23 C24 C19 120.1(3) . . ?
 C6 C7 C2 121.8(3) . . ?
 C22 C21 C20 121.3(4) . . ?
 C21 C22 C23 119.3(4) . . ?
 C22 C23 C24 120.9(4) . . ?

_olex2_submission_special_instructions  'No special instructions were received'
