data_shelxl
_audit_creation_date               2023-12-05
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number       '2018/3'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         None
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_requested_journal            ?
_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. (2015). Acta Cryst. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic
;
 ? 
;
_chemical_formula_moiety           'C44 H28 N4, C H Cl3'
_chemical_formula_sum              'C45 H29 Cl3 N4'
_chemical_formula_weight           732.07
_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' 0.0181 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'
 'Cl' 'Cl' 0.3639 0.7018 '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'

_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             15
_space_group_name_H-M_alt          'C 1 2/c 1'
_space_group_name_Hall             '-C 2yc'
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'
 '-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                     23.783(15)
_cell_length_b                     5.771(3)
_cell_length_c                     26.322(15)
_cell_angle_alpha                  90
_cell_angle_beta                   108.62(2)
_cell_angle_gamma                  90
_cell_volume                       3424(3)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      1724
_cell_measurement_temperature      93(2)
_cell_measurement_theta_max        70.10
_cell_measurement_theta_min        25.40
_shelx_estimated_absorpt_T_max     0.947
_shelx_estimated_absorpt_T_min     0.638
_exptl_absorpt_coefficient_mu      2.743
_exptl_absorpt_correction_T_max    0.9472
_exptl_absorpt_correction_T_min    0.6380
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              colourless
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.420
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      'not measured'
_exptl_crystal_description         Prism
_exptl_crystal_F_000               1512
_exptl_crystal_size_max            0.18
_exptl_crystal_size_mid            0.03
_exptl_crystal_size_min            0.02
_exptl_special_details
;
 ? 
;
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0530
_diffrn_reflns_av_unetI/netI       0.0461
_diffrn_reflns_Laue_measured_fraction_full  0.992
_diffrn_reflns_Laue_measured_fraction_max  0.980
_diffrn_reflns_limit_h_max         26
_diffrn_reflns_limit_h_min         -28
_diffrn_reflns_limit_k_max         6
_diffrn_reflns_limit_k_min         -7
_diffrn_reflns_limit_l_max         32
_diffrn_reflns_limit_l_min         -32
_diffrn_reflns_number              14509
_diffrn_reflns_point_group_measured_fraction_full  0.992
_diffrn_reflns_point_group_measured_fraction_max  0.980
_diffrn_reflns_theta_full          67.687
_diffrn_reflns_theta_max           70.629
_diffrn_reflns_theta_min           3.923
_diffrn_ambient_temperature        93.15
_diffrn_detector                   'PLATUS 200K area detector'
_diffrn_detector_area_resol_mean   5.811
_diffrn_detector_type              'HPC area detector'
_diffrn_measured_fraction_theta_full  0.992
_diffrn_measured_fraction_theta_max  0.980
_diffrn_measurement_device         'four-circle diffractometer'
_diffrn_measurement_device_type    Rigaku_XtaLAB_P200_007
_diffrn_measurement_method         'ω scans'
_diffrn_radiation_monochromator    'multi-layer mirror optics'
_diffrn_radiation_probe            x-ray
_diffrn_radiation_type             CuK\a
_diffrn_radiation_wavelength       1.54187
_diffrn_source                     'rotating anode X-ray generator'
_diffrn_source_current             30.0
_diffrn_source_power               1.2
_diffrn_source_type                micromax007
_diffrn_source_voltage             40.0
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  2543
_reflns_number_total               3202
_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         'CrystalClear-SM Expert 2.1 b29'
_computing_data_collection         'CrystalClear-SM Expert 2.1 b29'
_computing_data_reduction          'CrystalClear-SM Expert 2.1 b29'
_computing_molecular_graphics      'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement    'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution      'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max           0.811
_refine_diff_density_min           -0.828
_refine_diff_density_rms           0.111
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.082
_refine_ls_hydrogen_treatment      mixed
_refine_ls_matrix_type             full
_refine_ls_number_parameters       243
_refine_ls_number_reflns           3202
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0932
_refine_ls_R_factor_gt             0.0805
_refine_ls_restrained_S_all        1.082
_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)+(0.0396P)²+53.0692P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1999
_refine_ls_wR_factor_ref           0.2071
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Fixed Sof: C1A(0.5) H1A(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C5(H5), C6(H6), C7(H7), C9(H9), C11(H11), C12(H12), C14(H14),
 C16(H16), C17(H17), C18(H18), C20(H20), C22(H22)
;
_atom_sites_solution_hydrogens     mixed
_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
 N1 N 0.5812(2) 1.0206(7) 0.44830(15) 0.0267(10) Uani 1 1 d . . . . .
 C1 C 0.6237(2) 0.9040(9) 0.43663(18) 0.0259(11) Uani 1 1 d . . . . .
 H1 H 0.661174 0.976750 0.443328 0.031 Uiso 1 1 calc R U . . .
 C2 C 0.6163(2) 0.6796(8) 0.41501(17) 0.0219(10) Uani 1 1 d . . . . .
 C3 C 0.5610(2) 0.5775(8) 0.40550(16) 0.0187(9) Uani 1 1 d . . . . .
 H3 H 0.553977 0.426586 0.390378 0.022 Uiso 1 1 calc R U . . .
 C4 C 0.5155(2) 0.6936(8) 0.41783(16) 0.0213(10) Uani 1 1 d . . . . .
 C5 C 0.5287(3) 0.9165(9) 0.43945(17) 0.0265(11) Uani 1 1 d . . . . .
 H5 H 0.498518 0.998606 0.448356 0.032 Uiso 1 1 calc R U . . .
 C6 C 0.3827(2) 0.4268(10) 0.44375(18) 0.0284(12) Uani 1 1 d . . . . .
 H6 H 0.365204 0.421246 0.471518 0.034 Uiso 1 1 calc R U . . .
 C7 C 0.4308(2) 0.5644(9) 0.44980(18) 0.0260(11) Uani 1 1 d . . . . .
 H7 H 0.445873 0.655535 0.481278 0.031 Uiso 1 1 calc R U . . .
 C8 C 0.4584(2) 0.5730(8) 0.40988(17) 0.0200(10) Uani 1 1 d . . . . .
 C9 C 0.4326(2) 0.4450(8) 0.36299(17) 0.0215(10) Uani 1 1 d . . . . .
 H9 H 0.449816 0.452972 0.335052 0.026 Uiso 1 1 calc R U . . .
 C10 C 0.3828(2) 0.3067(8) 0.35575(17) 0.0199(10) Uani 1 1 d . . . . .
 C11 C 0.3585(2) 0.2940(9) 0.39783(18) 0.0258(11) Uani 1 1 d . . . . .
 H11 H 0.325714 0.195097 0.394946 0.031 Uiso 1 1 calc R U . . .
 N2 N 0.3108(2) -0.1690(8) 0.25967(18) 0.0310(10) Uani 1 1 d . . . . .
 C12 C 0.3373(2) -0.0496(9) 0.3044(2) 0.0258(11) Uani 1 1 d . . . . .
 H12 H 0.343914 -0.125920 0.337809 0.031 Uiso 1 1 calc R U . . .
 C13 C 0.3558(2) 0.1809(9) 0.30514(18) 0.0210(10) Uani 1 1 d . . . . .
 C14 C 0.3466(2) 0.2898(8) 0.25563(17) 0.0192(9) Uani 1 1 d . . . . .
 H14 H 0.359632 0.444557 0.254230 0.023 Uiso 1 1 calc R U . . .
 C15 C 0.3182(2) 0.1699(8) 0.20833(18) 0.0206(10) Uani 1 1 d . . . . .
 C16 C 0.3014(2) -0.0579(9) 0.2128(2) 0.0267(11) Uani 1 1 d . . . . .
 H16 H 0.282010 -0.140260 0.180761 0.032 Uiso 1 1 calc R U . . .
 C17 C 0.2395(2) 0.3601(10) 0.06600(19) 0.0278(11) Uani 1 1 d . . . . .
 H17 H 0.202518 0.335900 0.038828 0.033 Uiso 1 1 calc R U . . .
 C18 C 0.2513(2) 0.2474(9) 0.11492(19) 0.0236(10) Uani 1 1 d . . . . .
 H18 H 0.222805 0.145135 0.120953 0.028 Uiso 1 1 calc R U . . .
 C19 C 0.3057(2) 0.2851(8) 0.15549(17) 0.0200(10) Uani 1 1 d . . . . .
 C20 C 0.3469(2) 0.4323(8) 0.14526(17) 0.0197(10) Uani 1 1 d . . . . .
 H20 H 0.383653 0.458356 0.172548 0.024 Uiso 1 1 calc R U . . .
 C21 C 0.3357(2) 0.5434(8) 0.09573(18) 0.0217(10) Uani 1 1 d . . . . .
 C22 C 0.2809(2) 0.5072(9) 0.05640(17) 0.0233(11) Uani 1 1 d . . . . .
 H22 H 0.271993 0.584174 0.022846 0.028 Uiso 1 1 calc R U . . .
 C1A C 0.5219(5) 0.9121(18) 0.2478(4) 0.027(2) Uani 0.5 1 d . . P A -1
 H1A H 0.561(5) 0.91(2) 0.243(4) 0.032 Uiso 0.5 1 d . U P B -1
 Cl1A Cl 0.52606(8) 1.0466(2) 0.30740(5) 0.0486(5) Uani 1 1 d . . . . .
 Cl2A Cl 0.500000 0.6143(3) 0.250000 0.0335(5) Uani 1 2 d S T P . .


_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
 N1 C1 1.329(7) . ?
 N1 C5 1.337(7) . ?
 C1 C2 1.403(7) . ?
 C2 C3 1.391(7) . ?
 C2 C21 1.486(7) 2_655 ?
 C3 C4 1.395(7) . ?
 C4 C5 1.401(7) . ?
 C4 C8 1.480(7) . ?
 C6 C7 1.359(8) . ?
 C6 C11 1.391(7) . ?
 C7 C8 1.407(6) . ?
 C8 C9 1.401(6) . ?
 C9 C10 1.391(7) . ?
 C10 C11 1.405(6) . ?
 C10 C13 1.472(6) . ?
 N2 C12 1.336(7) . ?
 N2 C16 1.343(7) . ?
 C12 C13 1.400(7) . ?
 C13 C14 1.400(6) . ?
 C14 C15 1.396(6) . ?
 C15 C16 1.390(7) . ?
 C15 C19 1.483(6) . ?
 C17 C18 1.389(7) . ?
 C17 C22 1.383(7) . ?
 C18 C19 1.406(6) . ?
 C19 C20 1.386(7) . ?
 C20 C21 1.400(6) . ?
 C21 C22 1.397(7) . ?
 C1A Cl1A 1.724(10) . ?
 C1A Cl2A 1.802(10) . ?

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 N1 C5 117.9(4) . . ?
 N1 C1 C2 123.8(5) . . ?
 C1 C2 C21 124.2(5) . 2_655 ?
 C3 C2 C1 116.9(5) . . ?
 C3 C2 C21 118.9(4) . 2_655 ?
 C2 C3 C4 120.9(4) . . ?
 C3 C4 C5 116.5(5) . . ?
 C3 C4 C8 119.0(4) . . ?
 C5 C4 C8 124.4(4) . . ?
 N1 C5 C4 124.0(5) . . ?
 C7 C6 C11 121.5(4) . . ?
 C6 C7 C8 120.6(5) . . ?
 C7 C8 C4 122.5(4) . . ?
 C9 C8 C4 119.8(4) . . ?
 C9 C8 C7 117.5(5) . . ?
 C10 C9 C8 122.6(4) . . ?
 C9 C10 C11 117.9(4) . . ?
 C9 C10 C13 120.9(4) . . ?
 C11 C10 C13 121.2(4) . . ?
 C6 C11 C10 119.8(5) . . ?
 C12 N2 C16 117.2(4) . . ?
 N2 C12 C13 124.0(5) . . ?
 C12 C13 C10 121.7(4) . . ?
 C12 C13 C14 117.3(4) . . ?
 C14 C13 C10 121.0(4) . . ?
 C15 C14 C13 119.7(4) . . ?
 C14 C15 C19 120.6(4) . . ?
 C16 C15 C14 117.6(4) . . ?
 C16 C15 C19 121.8(4) . . ?
 N2 C16 C15 124.1(5) . . ?
 C22 C17 C18 120.8(4) . . ?
 C17 C18 C19 119.8(5) . . ?
 C18 C19 C15 120.2(4) . . ?
 C20 C19 C15 120.9(4) . . ?
 C20 C19 C18 118.8(4) . . ?
 C19 C20 C21 121.7(4) . . ?
 C20 C21 C2 119.3(4) . 2_655 ?
 C22 C21 C2 122.0(4) . 2_655 ?
 C22 C21 C20 118.5(5) . . ?
 C17 C22 C21 120.4(4) . . ?
 Cl1A C1A Cl2A 109.5(5) . . ?

_olex2_submission_special_instructions  'No special instructions were received'
