data_a_a
_audit_creation_date               2022-09-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_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. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           '4(C23 H19 N O3)'
_chemical_formula_sum              'C92 H76 N4 O12'
_chemical_formula_weight           1429.56
_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' 0.0181 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'

_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                     5.00700(10)
_cell_length_b                     17.1218(4)
_cell_length_c                     21.1670(4)
_cell_angle_alpha                  90
_cell_angle_beta                   90
_cell_angle_gamma                  90
_cell_volume                       1814.62(7)
_cell_formula_units_Z              1
_cell_measurement_reflns_used      5546
_cell_measurement_temperature      273(2)
_cell_measurement_theta_max        64.71
_cell_measurement_theta_min        3.32
_shelx_estimated_absorpt_T_max     ?
_shelx_estimated_absorpt_T_min     ?
_exptl_absorpt_coefficient_mu      0.698
_exptl_absorpt_correction_T_max    0.7528
_exptl_absorpt_correction_T_min    0.6461
_exptl_absorpt_correction_type     'none'
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0838 before and 0.0569 after correction.
The Ratio of minimum to maximum transmission is 0.8583.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour             yellow
_exptl_crystal_density_diffrn      1.308
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         stick
_exptl_crystal_F_000               752
_exptl_crystal_size_max            ?
_exptl_crystal_size_mid            ?
_exptl_crystal_size_min            ?
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0458
_diffrn_reflns_av_unetI/netI       0.0328
_diffrn_reflns_Laue_measured_fraction_full  0.999
_diffrn_reflns_Laue_measured_fraction_max  0.999
_diffrn_reflns_limit_h_max         5
_diffrn_reflns_limit_h_min         -5
_diffrn_reflns_limit_k_max         20
_diffrn_reflns_limit_k_min         -20
_diffrn_reflns_limit_l_max         24
_diffrn_reflns_limit_l_min         -25
_diffrn_reflns_number              18792
_diffrn_reflns_point_group_measured_fraction_full  0.998
_diffrn_reflns_point_group_measured_fraction_max  0.998
_diffrn_reflns_theta_full          66.732
_diffrn_reflns_theta_max           66.732
_diffrn_reflns_theta_min           3.320
_diffrn_ambient_temperature        273.15
_diffrn_detector                   'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean   7.9
_diffrn_detector_type              'CCD area detector'
_diffrn_measured_fraction_theta_full  0.999
_diffrn_measured_fraction_theta_max  0.999
_diffrn_measurement_device         'three-circle diffractometer'
_diffrn_measurement_device_type    'Bruker SMART APEX2 area detector'
_diffrn_measurement_method         'ω and φ scans'
_diffrn_radiation_monochromator    'mirror optics'
_diffrn_radiation_probe            x-ray
_diffrn_radiation_type             CuK\a
_diffrn_radiation_wavelength       1.54178
_diffrn_source                     'microfocus sealed X-ray tube'
_diffrn_source_type                'Incoatec I\ms'
_diffrn_standards_number           0
_reflns_Friedel_coverage           0.689
_reflns_Friedel_fraction_full      0.998
_reflns_Friedel_fraction_max       0.998
_reflns_number_gt                  2311
_reflns_number_total               3196
_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 v8.37A (Bruker, 2015)'
_computing_data_collection         ?
_computing_data_reduction          'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics      'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement    'ShelXL (Sheldrick, 2015)'
_computing_structure_solution      'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max           0.176
_refine_diff_density_min           -0.265
_refine_diff_density_rms           0.079
_refine_ls_abs_structure_details
;
 Flack x determined using 770 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack     0.09(13)
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.011
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       244
_refine_ls_number_reflns           3196
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0763
_refine_ls_R_factor_gt             0.0584
_refine_ls_restrained_S_all        1.011
_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)+(0.0908P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1278
_refine_ls_wR_factor_ref           0.1415
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C16(H16), C3(H3), C12(H12), C5(H5), C11(H11), C23(H23), C19(H19),
 C21(H21), C2(H2), C6(H6), C20(H20), C22(H22), C1(H1A)
;
_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
 O1 O 0.7706(6) 0.34625(14) 0.61122(11) 0.0755(8) Uani 1 1 d . . . . .
 O2 O 0.0662(7) 0.26917(15) 0.82736(11) 0.0784(8) Uani 1 1 d . . . . .
 N1 N 0.4236(7) 0.46305(16) 0.63591(12) 0.0661(8) Uani 1 1 d . . . . .
 H1 H 0.540675 0.441150 0.612037 0.079 Uiso 1 1 calc R . . . .
 O3 O 0.2055(9) 0.57700(18) 0.65222(14) 0.1071(12) Uani 1 1 d . . . . .
 C14 C 0.4454(8) 0.34260(18) 0.69493(14) 0.0551(8) Uani 1 1 d . . . . .
 C13 C 0.3279(8) 0.41719(19) 0.68601(15) 0.0592(9) Uani 1 1 d . . . . .
 C15 C 0.3477(8) 0.29507(19) 0.74319(14) 0.0576(9) Uani 1 1 d . . . . .
 C16 C 0.6719(8) 0.3146(2) 0.65697(16) 0.0618(9) Uani 1 1 d . . . . .
 H16 H 0.748062 0.267540 0.669366 0.074 Uiso 1 1 calc R . . . .
 C17 C 0.3563(9) 0.5372(2) 0.62010(16) 0.0694(11) Uani 1 1 d . . . . .
 C8 C 0.4098(8) 0.21178(19) 0.76301(14) 0.0601(9) Uani 1 1 d . . . . .
 H8 H 0.602915 0.203075 0.765833 0.072 Uiso 1 1 calc R . . . .
 C4 C 0.3946(8) 0.1417(2) 0.65576(16) 0.0620(10) Uani 1 1 d . . . . .
 C3 C 0.2990(9) 0.1832(2) 0.60400(16) 0.0692(10) Uani 1 1 d . . . . .
 H3 H 0.154063 0.216606 0.608934 0.083 Uiso 1 1 calc R . . . .
 C10 C 0.1442(9) 0.3223(2) 0.78169(15) 0.0639(10) Uani 1 1 d . . . . .
 C18 C 0.4749(9) 0.5676(2) 0.56069(16) 0.0654(10) Uani 1 1 d . . . . .
 C7 C 0.2750(9) 0.14987(19) 0.72027(16) 0.0677(10) Uani 1 1 d . . . . .
 H7A H 0.284175 0.099638 0.741345 0.081 Uiso 1 1 calc R . . . .
 H7B H 0.087795 0.163266 0.715702 0.081 Uiso 1 1 calc R . . . .
 C12 C 0.1241(9) 0.4420(2) 0.72603(17) 0.0699(11) Uani 1 1 d . . . . .
 H12 H 0.049308 0.491205 0.720168 0.084 Uiso 1 1 calc R . . . .
 C5 C 0.6111(9) 0.0919(2) 0.6460(2) 0.0777(12) Uani 1 1 d . . . . .
 H5 H 0.678926 0.063230 0.679677 0.093 Uiso 1 1 calc R . . . .
 C9 C 0.2794(10) 0.2116(2) 0.82915(16) 0.0747(11) Uani 1 1 d . . . . .
 H9A H 0.207988 0.160322 0.838817 0.090 Uiso 1 1 calc R . . . .
 H9B H 0.409747 0.225301 0.861188 0.090 Uiso 1 1 calc R . . . .
 C11 C 0.0304(10) 0.3948(2) 0.77446(18) 0.0748(12) Uani 1 1 d . . . . .
 H11 H -0.105115 0.411713 0.801213 0.090 Uiso 1 1 calc R . . . .
 C23 C 0.3673(11) 0.6364(2) 0.5368(2) 0.0814(13) Uani 1 1 d . . . . .
 H23 H 0.228422 0.660768 0.558271 0.098 Uiso 1 1 calc R . . . .
 C19 C 0.6823(10) 0.5327(2) 0.52809(18) 0.0747(11) Uani 1 1 d . . . . .
 H19 H 0.755887 0.486349 0.543044 0.090 Uiso 1 1 calc R . . . .
 C21 C 0.6677(12) 0.6338(3) 0.45038(19) 0.0852(14) Uani 1 1 d . . . . .
 H21 H 0.731471 0.655651 0.413094 0.102 Uiso 1 1 calc R . . . .
 C2 C 0.4171(11) 0.1753(3) 0.54527(18) 0.0829(13) Uani 1 1 d . . . . .
 H2 H 0.352213 0.203932 0.511217 0.099 Uiso 1 1 calc R . . . .
 C6 C 0.7262(11) 0.0847(3) 0.5870(3) 0.0931(14) Uani 1 1 d . . . . .
 H6 H 0.871325 0.051614 0.581210 0.112 Uiso 1 1 calc R . . . .
 C20 C 0.7813(11) 0.5663(2) 0.47311(19) 0.0849(13) Uani 1 1 d . . . . .
 H20 H 0.923529 0.543293 0.451831 0.102 Uiso 1 1 calc R . . . .
 C22 C 0.4634(11) 0.6689(3) 0.4817(2) 0.0882(13) Uani 1 1 d . . . . .
 H22 H 0.388727 0.714752 0.466047 0.106 Uiso 1 1 calc R . . . .
 C1 C 0.6265(12) 0.1264(3) 0.5370(2) 0.0945(16) Uani 1 1 d . . . . .
 H1A H 0.703009 0.120937 0.497180 0.113 Uiso 1 1 calc R . . . .


_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
 O1 C16 1.214(4) . ?
 O2 C10 1.384(4) . ?
 O2 C9 1.453(5) . ?
 N1 H1 0.8600 . ?
 N1 C13 1.404(4) . ?
 N1 C17 1.356(5) . ?
 O3 C17 1.223(5) . ?
 C14 C13 1.419(5) . ?
 C14 C15 1.395(4) . ?
 C14 C16 1.470(5) . ?
 C13 C12 1.393(5) . ?
 C15 C8 1.519(5) . ?
 C15 C10 1.386(5) . ?
 C16 H16 0.9300 . ?
 C17 C18 1.485(5) . ?
 C8 H8 0.9800 . ?
 C8 C7 1.548(5) . ?
 C8 C9 1.545(5) . ?
 C4 C3 1.391(5) . ?
 C4 C7 1.497(5) . ?
 C4 C5 1.394(6) . ?
 C3 H3 0.9300 . ?
 C3 C2 1.383(5) . ?
 C10 C11 1.374(6) . ?
 C18 C23 1.389(5) . ?
 C18 C19 1.383(6) . ?
 C7 H7A 0.9700 . ?
 C7 H7B 0.9700 . ?
 C12 H12 0.9300 . ?
 C12 C11 1.387(5) . ?
 C5 H5 0.9300 . ?
 C5 C6 1.381(6) . ?
 C9 H9A 0.9700 . ?
 C9 H9B 0.9700 . ?
 C11 H11 0.9300 . ?
 C23 H23 0.9300 . ?
 C23 C22 1.379(6) . ?
 C19 H19 0.9300 . ?
 C19 C20 1.390(5) . ?
 C21 H21 0.9300 . ?
 C21 C20 1.375(6) . ?
 C21 C22 1.360(7) . ?
 C2 H2 0.9300 . ?
 C2 C1 1.354(8) . ?
 C6 H6 0.9300 . ?
 C6 C1 1.370(7) . ?
 C20 H20 0.9300 . ?
 C22 H22 0.9300 . ?
 C1 H1A 0.9300 . ?

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
 C10 O2 C9 104.9(3) . . ?
 C13 N1 H1 115.6 . . ?
 C17 N1 H1 115.6 . . ?
 C17 N1 C13 128.7(3) . . ?
 C13 C14 C16 122.7(3) . . ?
 C15 C14 C13 118.5(3) . . ?
 C15 C14 C16 118.7(3) . . ?
 N1 C13 C14 117.5(3) . . ?
 C12 C13 N1 122.6(3) . . ?
 C12 C13 C14 119.9(3) . . ?
 C14 C15 C8 132.7(3) . . ?
 C10 C15 C14 119.5(3) . . ?
 C10 C15 C8 107.7(3) . . ?
 O1 C16 C14 127.2(3) . . ?
 O1 C16 H16 116.4 . . ?
 C14 C16 H16 116.4 . . ?
 N1 C17 C18 116.0(3) . . ?
 O3 C17 N1 122.5(4) . . ?
 O3 C17 C18 121.5(3) . . ?
 C15 C8 H8 111.2 . . ?
 C15 C8 C7 113.1(3) . . ?
 C15 C8 C9 99.5(3) . . ?
 C7 C8 H8 111.2 . . ?
 C9 C8 H8 111.2 . . ?
 C9 C8 C7 110.1(3) . . ?
 C3 C4 C7 122.2(4) . . ?
 C3 C4 C5 117.6(4) . . ?
 C5 C4 C7 120.2(4) . . ?
 C4 C3 H3 119.6 . . ?
 C2 C3 C4 120.7(4) . . ?
 C2 C3 H3 119.6 . . ?
 O2 C10 C15 113.4(3) . . ?
 C11 C10 O2 123.7(4) . . ?
 C11 C10 C15 122.9(3) . . ?
 C23 C18 C17 116.7(4) . . ?
 C19 C18 C17 124.8(4) . . ?
 C19 C18 C23 118.4(4) . . ?
 C8 C7 H7A 108.5 . . ?
 C8 C7 H7B 108.5 . . ?
 C4 C7 C8 115.0(3) . . ?
 C4 C7 H7A 108.5 . . ?
 C4 C7 H7B 108.5 . . ?
 H7A C7 H7B 107.5 . . ?
 C13 C12 H12 119.4 . . ?
 C11 C12 C13 121.3(4) . . ?
 C11 C12 H12 119.4 . . ?
 C4 C5 H5 119.6 . . ?
 C6 C5 C4 120.9(4) . . ?
 C6 C5 H5 119.6 . . ?
 O2 C9 C8 106.6(3) . . ?
 O2 C9 H9A 110.4 . . ?
 O2 C9 H9B 110.4 . . ?
 C8 C9 H9A 110.4 . . ?
 C8 C9 H9B 110.4 . . ?
 H9A C9 H9B 108.6 . . ?
 C10 C11 C12 117.9(4) . . ?
 C10 C11 H11 121.0 . . ?
 C12 C11 H11 121.0 . . ?
 C18 C23 H23 119.5 . . ?
 C22 C23 C18 121.0(5) . . ?
 C22 C23 H23 119.5 . . ?
 C18 C19 H19 119.8 . . ?
 C18 C19 C20 120.4(4) . . ?
 C20 C19 H19 119.8 . . ?
 C20 C21 H21 119.6 . . ?
 C22 C21 H21 119.6 . . ?
 C22 C21 C20 120.8(4) . . ?
 C3 C2 H2 119.7 . . ?
 C1 C2 C3 120.5(4) . . ?
 C1 C2 H2 119.7 . . ?
 C5 C6 H6 120.0 . . ?
 C1 C6 C5 120.0(5) . . ?
 C1 C6 H6 120.0 . . ?
 C19 C20 H20 120.2 . . ?
 C21 C20 C19 119.6(5) . . ?
 C21 C20 H20 120.2 . . ?
 C23 C22 H22 120.1 . . ?
 C21 C22 C23 119.7(4) . . ?
 C21 C22 H22 120.1 . . ?
 C2 C1 C6 120.3(4) . . ?
 C2 C1 H1A 119.9 . . ?
 C6 C1 H1A 119.9 . . ?

_olex2_submission_special_instructions  'No special instructions were received'
