# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_esser_jw49_a
_database_code_depnum_ccdc_archive 'CCDC 1570449'
loop_
_audit_author_name
_audit_author_address
'Daniel Kratzert' 'University of Freiburg'
_audit_update_record             
;
2017-08-23 deposited with the CCDC.	2019-09-30 downloaded from the CCDC.
;
_audit_creation_date             2017-08-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H14 N2 O2'
_chemical_formula_sum            'C17 H14 N2 O2'
_chemical_formula_weight         278.30
_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'
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                   8.4028(2)
_cell_length_b                   8.4685(2)
_cell_length_c                   18.8231(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.121(2)
_cell_angle_gamma                90
_cell_volume                     1339.18(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8559
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.117
_cell_measurement_theta_min      2.42
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.970
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.7001
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1494 before and 0.0380 after correction. The Ratio of minimum to maximum transmission is 0.9391. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark brown'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_recrystallization_method 
'The material was recrystallised from benzene by slow evaporation'
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            19413
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.127
_diffrn_reflns_theta_min         2.164
_diffrn_ambient_temperature      100.01
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_current           50
_diffrn_source_voltage           0.6
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2572
_reflns_number_total             2963
_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 V8.38A (Madison, 2016)'
_computing_data_collection       'Bruker AKEX2'
_computing_data_reduction        'SAINT V8.38A (Madison, 2016)'
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2963
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0365
_refine_ls_restrained_S_all      1.030
_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)+(0.0419P)²+0.6871P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0881
_refine_ls_wR_factor_ref         0.0926
_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:
 C4(H4), C5(H5), C6(H6), C7(H7), C11(H11), C12(H12), C13(H13), C14(H14)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.15181(10) 0.62120(11) 0.53022(4) 0.0177(2) Uani 1 1 d . . . . .
N1 N 0.37322(11) 0.83148(12) 0.60701(5) 0.0150(2) Uani 1 1 d . . . . .
C1 C 0.36212(13) 0.66435(14) 0.62000(6) 0.0134(2) Uani 1 1 d . . . . .
O2 O 0.43582(11) 0.66715(12) 0.74750(5) 0.0234(2) Uani 1 1 d . . . . .
N2 N 0.50293(11) 0.60079(12) 0.58468(5) 0.0143(2) Uani 1 1 d . . . . .
C2 C 0.35571(14) 0.61166(14) 0.69969(6) 0.0148(2) Uani 1 1 d . . . . .
C3 C 0.23589(13) 0.48342(14) 0.70371(6) 0.0139(2) Uani 1 1 d . . . . .
C4 C 0.20413(14) 0.38200(15) 0.75978(6) 0.0174(3) Uani 1 1 d . . . . .
H4 H 0.261810 0.389404 0.803570 0.021 Uiso 1 1 calc R . . . .
C5 C 0.08568(15) 0.26974(16) 0.74981(7) 0.0195(3) Uani 1 1 d . . . . .
H5 H 0.062652 0.198635 0.787271 0.023 Uiso 1 1 calc R . . . .
C6 C -0.00075(15) 0.25911(16) 0.68554(7) 0.0202(3) Uani 1 1 d . . . . .
H6 H -0.082025 0.181756 0.680335 0.024 Uiso 1 1 calc R . . . .
C7 C 0.03066(14) 0.36001(15) 0.62935(6) 0.0170(3) Uani 1 1 d . . . . .
H7 H -0.027854 0.353246 0.585755 0.020 Uiso 1 1 calc R . . . .
C9 C 0.20922(13) 0.58813(14) 0.58768(6) 0.0133(2) Uani 1 1 d . . . . .
C8 C 0.15056(13) 0.47104(14) 0.63915(6) 0.0135(2) Uani 1 1 d . . . . .
C10 C 0.52765(13) 0.86795(14) 0.58704(6) 0.0134(2) Uani 1 1 d . . . . .
C11 C 0.59914(14) 1.01218(15) 0.57693(6) 0.0159(2) Uani 1 1 d . . . . .
H11 H 0.543344 1.107954 0.584834 0.019 Uiso 1 1 calc R . . . .
C12 C 0.75787(15) 1.01273(16) 0.55445(6) 0.0185(3) Uani 1 1 d . . . . .
H12 H 0.809875 1.110510 0.546363 0.022 Uiso 1 1 calc R . . . .
C13 C 0.83916(14) 0.87316(16) 0.54398(6) 0.0187(3) Uani 1 1 d . . . . .
H13 H 0.946958 0.876672 0.529764 0.022 Uiso 1 1 calc R . . . .
C14 C 0.76529(14) 0.72566(15) 0.55398(6) 0.0157(2) Uani 1 1 d . . . . .
H14 H 0.821021 0.629596 0.546698 0.019 Uiso 1 1 calc R . . . .
C15 C 0.60860(14) 0.72639(14) 0.57480(6) 0.0134(2) Uani 1 1 d . . . . .
C16 C 0.56055(16) 0.44397(16) 0.60242(8) 0.0231(3) Uani 1 1 d . . . . .
H16A H 0.470839 0.370058 0.602855 0.035 Uiso 1 1 calc GR . . . .
H16B H 0.612601 0.445971 0.649464 0.035 Uiso 1 1 calc GR . . . .
H16C H 0.637162 0.409919 0.566944 0.035 Uiso 1 1 calc GR . . . .
C17 C 0.27131(15) 0.94306(16) 0.64249(7) 0.0205(3) Uani 1 1 d . . . . .
H17A H 0.266879 1.041787 0.615362 0.031 Uiso 1 1 calc GR . . . .
H17B H 0.314103 0.964118 0.690360 0.031 Uiso 1 1 calc GR . . . .
H17C H 0.163931 0.898824 0.645770 0.031 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
O1 C9 1.2086(14) . ?
N1 C1 1.4397(16) . ?
N1 C10 1.3927(15) . ?
N1 C17 1.4473(16) . ?
C1 N2 1.4705(15) . ?
C1 C2 1.5670(16) . ?
C1 C9 1.5513(16) . ?
O2 C2 1.2083(15) . ?
N2 C15 1.4003(15) . ?
N2 C16 1.4503(16) . ?
C2 C3 1.4838(17) . ?
C3 C4 1.3907(17) . ?
C3 C8 1.4028(15) . ?
C4 H4 0.9500 . ?
C4 C5 1.3864(18) . ?
C5 H5 0.9500 . ?
C5 C6 1.4017(18) . ?
C6 H6 0.9500 . ?
C6 C7 1.3890(18) . ?
C7 H7 0.9500 . ?
C7 C8 1.3878(17) . ?
C9 C8 1.4776(16) . ?
C10 C11 1.3761(17) . ?
C10 C15 1.3996(17) . ?
C11 H11 0.9500 . ?
C11 C12 1.4071(17) . ?
C12 H12 0.9500 . ?
C12 C13 1.3812(19) . ?
C13 H13 0.9500 . ?
C13 C14 1.4091(18) . ?
C14 H14 0.9500 . ?
C14 C15 1.3811(17) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

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 C17 121.50(10) . . ?
C10 N1 C1 109.13(10) . . ?
C10 N1 C17 122.86(10) . . ?
N1 C1 N2 103.16(9) . . ?
N1 C1 C2 116.50(10) . . ?
N1 C1 C9 113.48(10) . . ?
N2 C1 C2 111.81(9) . . ?
N2 C1 C9 109.75(9) . . ?
C9 C1 C2 102.31(9) . . ?
C15 N2 C1 107.45(9) . . ?
C15 N2 C16 121.09(10) . . ?
C16 N2 C1 119.94(10) . . ?
O2 C2 C1 124.97(11) . . ?
O2 C2 C3 127.98(11) . . ?
C3 C2 C1 107.05(9) . . ?
C4 C3 C2 129.14(11) . . ?
C4 C3 C8 120.59(11) . . ?
C8 C3 C2 110.27(10) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 C3 117.95(11) . . ?
C5 C4 H4 121.0 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.29(12) . . ?
C6 C5 H5 119.4 . . ?
C5 C6 H6 119.5 . . ?
C7 C6 C5 120.98(12) . . ?
C7 C6 H6 119.5 . . ?
C6 C7 H7 121.2 . . ?
C8 C7 C6 117.63(11) . . ?
C8 C7 H7 121.2 . . ?
O1 C9 C1 124.58(11) . . ?
O1 C9 C8 127.57(11) . . ?
C8 C9 C1 107.85(9) . . ?
C3 C8 C9 110.27(10) . . ?
C7 C8 C3 121.55(11) . . ?
C7 C8 C9 128.18(11) . . ?
N1 C10 C15 108.23(10) . . ?
C11 C10 N1 130.22(11) . . ?
C11 C10 C15 121.51(11) . . ?
C10 C11 H11 121.2 . . ?
C10 C11 C12 117.61(11) . . ?
C12 C11 H11 121.2 . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 120.96(12) . . ?
C13 C12 H12 119.5 . . ?
C12 C13 H13 119.4 . . ?
C12 C13 C14 121.27(11) . . ?
C14 C13 H13 119.4 . . ?
C13 C14 H14 121.3 . . ?
C15 C14 C13 117.32(11) . . ?
C15 C14 H14 121.3 . . ?
C10 C15 N2 108.50(10) . . ?
C14 C15 N2 130.15(11) . . ?
C14 C15 C10 121.30(11) . . ?
N2 C16 H16A 109.5 . . ?
N2 C16 H16B 109.5 . . ?
N2 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

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
O1 C9 C8 C3 -171.37(12) . . . . ?
O1 C9 C8 C7 9.2(2) . . . . ?
N1 C1 N2 C15 18.49(11) . . . . ?
N1 C1 N2 C16 162.17(10) . . . . ?
N1 C1 C2 O2 -41.59(17) . . . . ?
N1 C1 C2 C3 138.79(10) . . . . ?
N1 C1 C9 O1 39.84(16) . . . . ?
N1 C1 C9 C8 -140.39(10) . . . . ?
N1 C10 C11 C12 -178.18(11) . . . . ?
N1 C10 C15 N2 2.07(13) . . . . ?
N1 C10 C15 C14 179.88(10) . . . . ?
C1 N1 C10 C11 -172.06(12) . . . . ?
C1 N1 C10 C15 10.16(13) . . . . ?
C1 N2 C15 C10 -13.14(12) . . . . ?
C1 N2 C15 C14 169.31(11) . . . . ?
C1 C2 C3 C4 169.05(12) . . . . ?
C1 C2 C3 C8 -10.06(13) . . . . ?
C1 C9 C8 C3 8.86(13) . . . . ?
C1 C9 C8 C7 -170.55(12) . . . . ?
O2 C2 C3 C4 -10.6(2) . . . . ?
O2 C2 C3 C8 170.33(12) . . . . ?
N2 C1 C2 O2 76.67(15) . . . . ?
N2 C1 C2 C3 -102.95(11) . . . . ?
N2 C1 C9 O1 -74.97(14) . . . . ?
N2 C1 C9 C8 104.80(10) . . . . ?
C2 C1 N2 C15 -107.46(11) . . . . ?
C2 C1 N2 C16 36.22(15) . . . . ?
C2 C1 C9 O1 166.18(11) . . . . ?
C2 C1 C9 C8 -14.04(12) . . . . ?
C2 C3 C4 C5 -179.33(12) . . . . ?
C2 C3 C8 C7 -179.70(11) . . . . ?
C2 C3 C8 C9 0.84(13) . . . . ?
C3 C4 C5 C6 -0.55(19) . . . . ?
C4 C3 C8 C7 1.10(18) . . . . ?
C4 C3 C8 C9 -178.36(11) . . . . ?
C4 C5 C6 C7 0.6(2) . . . . ?
C5 C6 C7 C8 0.13(19) . . . . ?
C6 C7 C8 C3 -0.99(18) . . . . ?
C6 C7 C8 C9 178.37(12) . . . . ?
C9 C1 N2 C15 139.73(10) . . . . ?
C9 C1 N2 C16 -76.59(13) . . . . ?
C9 C1 C2 O2 -165.95(12) . . . . ?
C9 C1 C2 C3 14.43(12) . . . . ?
C8 C3 C4 C5 -0.30(18) . . . . ?
C10 N1 C1 N2 -17.45(12) . . . . ?
C10 N1 C1 C2 105.43(11) . . . . ?
C10 N1 C1 C9 -136.13(10) . . . . ?
C10 C11 C12 C13 -0.91(17) . . . . ?
C11 C10 C15 N2 -175.94(10) . . . . ?
C11 C10 C15 C14 1.87(17) . . . . ?
C11 C12 C13 C14 1.32(18) . . . . ?
C12 C13 C14 C15 -0.14(17) . . . . ?
C13 C14 C15 N2 175.85(11) . . . . ?
C13 C14 C15 C10 -1.43(17) . . . . ?
C15 C10 C11 C12 -0.66(17) . . . . ?
C16 N2 C15 C10 -156.32(11) . . . . ?
C16 N2 C15 C14 26.13(19) . . . . ?
C17 N1 C1 N2 -169.85(10) . . . . ?
C17 N1 C1 C2 -46.97(15) . . . . ?
C17 N1 C1 C9 71.47(13) . . . . ?
C17 N1 C10 C11 -20.11(19) . . . . ?
C17 N1 C10 C15 162.11(11) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems 800'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id JW_49
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_esser_jw73_a
_database_code_depnum_ccdc_archive 'CCDC 1573404'
loop_
_audit_author_name
_audit_author_address
'Daniel Kratzert' 'University of Freiburg'
_audit_update_record             
;
2017-09-08 deposited with the CCDC.	2019-09-30 downloaded from the CCDC.
;
_audit_creation_date             2017-09-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H18 N2 O2'
_chemical_formula_sum            'C23 H18 N2 O2'
_chemical_formula_weight         354.39
_chemical_absolute_configuration ad
_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'
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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
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'

_cell_length_a                   28.7181(8)
_cell_length_b                   16.0940(4)
_cell_length_c                   7.4702(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3452.65(16)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5756
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.284
_cell_measurement_theta_min      2.475
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.974
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1195 before and 0.0547 after correction. The Ratio of minimum to maximum transmission is 0.9384. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_av_unetI/netI     0.0525
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            36153
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.502
_diffrn_reflns_theta_min         1.418
_diffrn_ambient_temperature      99.98
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_current           50
_diffrn_source_voltage           0.6
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.800
_reflns_Friedel_fraction_full    0.966
_reflns_Friedel_fraction_max     0.931
_reflns_number_gt                6375
_reflns_number_total             7658
_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 V8.38A (Madison, 2016)'
_computing_data_collection       APEX2
_computing_data_reduction        'SAINT V8.38A (Madison, 2016)'
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 
;
 Flack x determined using 2335 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(6)
_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     491
_refine_ls_number_reflns         7658
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0470
_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)+(0.0409P)²+1.0480P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0946
_refine_ls_wR_factor_ref         0.1004
_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:
 C4(H4), C5(H5), C6(H6), C7(H7), C21'(H21'), C22'(H22'), C16'(H16'),
 C19'(H19'), C13(H13), C14'(H14'), C14(H14), C4'(H4'), C16(H16), C15(H15),
 C13'(H13'), C19(H19), C15'(H15'), C20'(H20'), C7'(H7'), C6'(H6'), C5'(H5'),
 C20(H20), C21(H21), C22(H22)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C10'(H10D,H10E,H10F), C11'(H11D,
 H11E,H11F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 -0.55800(7) -0.33748(12) -0.3015(3) 0.0245(5) Uani 1 1 d . . . . .
N1 N -0.66281(8) -0.31668(13) -0.3082(3) 0.0169(5) Uani 1 1 d . . . . .
C1 C -0.63699(10) -0.38997(16) -0.3629(4) 0.0168(6) Uani 1 1 d . . . . .
O2 O -0.69937(7) -0.49084(12) -0.2980(3) 0.0229(5) Uani 1 1 d . . . . .
N2 N -0.63413(8) -0.39684(14) -0.5575(3) 0.0180(5) Uani 1 1 d . . . . .
C2 C -0.58659(10) -0.39181(17) -0.2828(4) 0.0177(6) Uani 1 1 d . . . . .
O1' O -0.55778(7) -0.65645(12) -0.5618(3) 0.0258(5) Uani 1 1 d . . . . .
C3 C -0.58156(11) -0.46838(17) -0.1733(4) 0.0196(6) Uani 1 1 d . . . . .
O2' O -0.55331(8) -0.95094(12) -0.5185(3) 0.0297(6) Uani 1 1 d . . . . .
C4 C -0.54231(11) -0.49714(18) -0.0848(4) 0.0239(7) Uani 1 1 d . . . . .
H4 H -0.513707 -0.467576 -0.089413 0.029 Uiso 1 1 calc R . . . .
C5 C -0.54637(12) -0.57098(19) 0.0112(5) 0.0264(8) Uani 1 1 d . . . . .
H5 H -0.519973 -0.592589 0.072075 0.032 Uiso 1 1 calc R . . . .
N2' N -0.57697(8) -0.81065(14) -0.7753(3) 0.0181(5) Uani 1 1 d . . . . .
C6 C -0.58850(12) -0.61365(18) 0.0194(4) 0.0250(7) Uani 1 1 d . . . . .
H6 H -0.590492 -0.663403 0.087418 0.030 Uiso 1 1 calc R . . . .
C7 C -0.62745(11) -0.58487(17) -0.0696(4) 0.0217(7) Uani 1 1 d . . . . .
H7 H -0.656176 -0.613998 -0.063216 0.026 Uiso 1 1 calc R . . . .
N1' N -0.62167(9) -0.80662(15) -0.5028(3) 0.0197(6) Uani 1 1 d . . . . .
C8 C -0.62349(11) -0.51230(17) -0.1686(4) 0.0193(6) Uani 1 1 d . . . . .
C9 C -0.65962(10) -0.46857(17) -0.2758(4) 0.0175(6) Uani 1 1 d . . . . .
C23' C -0.65630(10) -0.75662(17) -0.5879(4) 0.0186(6) Uani 1 1 d . . . . .
C12' C -0.60732(11) -0.87318(17) -0.8481(4) 0.0189(6) Uani 1 1 d . . . . .
C2' C -0.54728(10) -0.72704(17) -0.5226(4) 0.0182(6) Uani 1 1 d . . . . .
C21' C -0.71403(11) -0.64798(18) -0.5789(5) 0.0225(7) Uani 1 1 d . . . . .
H21' H -0.727552 -0.601818 -0.519105 0.027 Uiso 1 1 calc R . . . .
C22' C -0.67623(11) -0.68837(18) -0.5042(5) 0.0211(7) Uani 1 1 d . . . . .
H22' H -0.663735 -0.669119 -0.393964 0.025 Uiso 1 1 calc R . . . .
C3' C -0.50869(11) -0.75356(18) -0.4072(4) 0.0202(7) Uani 1 1 d . . . . .
C16' C -0.68509(12) -0.91685(18) -0.9222(4) 0.0227(7) Uani 1 1 d . . . . .
H16' H -0.717817 -0.908684 -0.916739 0.027 Uiso 1 1 calc R . . . .
C17' C -0.65544(11) -0.85922(18) -0.8406(4) 0.0196(6) Uani 1 1 d . . . . .
C19' C -0.71192(11) -0.74225(18) -0.8266(4) 0.0220(7) Uani 1 1 d . . . . .
H19' H -0.723958 -0.759851 -0.938808 0.026 Uiso 1 1 calc R . . . .
C9' C -0.54621(11) -0.87765(18) -0.4963(4) 0.0208(7) Uani 1 1 d . . . . .
C1' C -0.57519(10) -0.80627(16) -0.5812(4) 0.0187(6) Uani 1 1 d . . . . .
C18' C -0.67455(11) -0.78454(18) -0.7522(4) 0.0206(7) Uani 1 1 d . . . . .
C10 C -0.66318(12) -0.30528(18) -0.1133(4) 0.0235(7) Uani 1 1 d . . . . .
H10A H -0.631885 -0.290113 -0.072431 0.035 Uiso 1 1 calc GR . . . .
H10B H -0.672796 -0.357164 -0.055384 0.035 Uiso 1 1 calc GR . . . .
H10C H -0.685107 -0.260964 -0.081839 0.035 Uiso 1 1 calc GR . . . .
C8' C -0.50780(11) -0.84025(18) -0.3909(4) 0.0218(7) Uani 1 1 d . . . . .
C12 C -0.67738(10) -0.39379(18) -0.6535(4) 0.0192(6) Uani 1 1 d . . . . .
C11 C -0.60176(11) -0.46184(18) -0.6185(4) 0.0221(7) Uani 1 1 d . . . . .
H11A H -0.613172 -0.516325 -0.579655 0.033 Uiso 1 1 calc GR . . . .
H11B H -0.570884 -0.451835 -0.566974 0.033 Uiso 1 1 calc GR . . . .
H11C H -0.599685 -0.460634 -0.749390 0.033 Uiso 1 1 calc GR . . . .
C10' C -0.62105(11) -0.80381(19) -0.3076(4) 0.0233(7) Uani 1 1 d . . . . .
H10D H -0.652956 -0.808170 -0.262023 0.035 Uiso 1 1 calc GR . . . .
H10E H -0.607319 -0.751175 -0.267981 0.035 Uiso 1 1 calc GR . . . .
H10F H -0.602450 -0.850187 -0.261596 0.035 Uiso 1 1 calc GR . . . .
C13 C -0.69371(11) -0.46195(18) -0.7481(4) 0.0201(7) Uani 1 1 d . . . . .
H13 H -0.677420 -0.513215 -0.741031 0.024 Uiso 1 1 calc R . . . .
C14' C -0.62020(12) -0.99823(18) -1.0184(4) 0.0257(7) Uani 1 1 d . . . . .
H14' H -0.608120 -1.045607 -1.078337 0.031 Uiso 1 1 calc R . . . .
C14 C -0.73342(11) -0.45642(18) -0.8526(4) 0.0222(7) Uani 1 1 d . . . . .
H14 H -0.743892 -0.503510 -0.917930 0.027 Uiso 1 1 calc R . . . .
C4' C -0.47615(11) -0.70479(19) -0.3191(5) 0.0260(7) Uani 1 1 d . . . . .
H4' H -0.476752 -0.645966 -0.329381 0.031 Uiso 1 1 calc R . . . .
C16 C -0.74138(11) -0.31447(18) -0.7691(4) 0.0207(7) Uani 1 1 d . . . . .
H16 H -0.758257 -0.263785 -0.775400 0.025 Uiso 1 1 calc R . . . .
C15 C -0.75773(11) -0.38292(18) -0.8622(4) 0.0220(7) Uani 1 1 d . . . . .
H15 H -0.785359 -0.379157 -0.931655 0.026 Uiso 1 1 calc R . . . .
C11' C -0.53063(11) -0.80648(18) -0.8572(4) 0.0232(7) Uani 1 1 d . . . . .
H11D H -0.533721 -0.806204 -0.987828 0.035 Uiso 1 1 calc GR . . . .
H11E H -0.512301 -0.854891 -0.820166 0.035 Uiso 1 1 calc GR . . . .
H11F H -0.514882 -0.755564 -0.818281 0.035 Uiso 1 1 calc GR . . . .
C17 C -0.70090(11) -0.31771(18) -0.6664(4) 0.0177(6) Uani 1 1 d . . . . .
C18 C -0.68176(10) -0.24157(17) -0.5828(4) 0.0179(6) Uani 1 1 d . . . . .
C13' C -0.59002(11) -0.94218(18) -0.9388(4) 0.0222(7) Uani 1 1 d . . . . .
H13' H -0.557358 -0.950860 -0.946087 0.027 Uiso 1 1 calc R . . . .
C19 C -0.68612(11) -0.16507(18) -0.6702(4) 0.0201(7) Uani 1 1 d . . . . .
H19 H -0.699929 -0.163549 -0.785694 0.024 Uiso 1 1 calc R . . . .
C15' C -0.66749(12) -0.98578(18) -1.0111(4) 0.0254(7) Uani 1 1 d . . . . .
H15' H -0.688046 -1.024165 -1.066699 0.031 Uiso 1 1 calc R . . . .
C20' C -0.73220(11) -0.67455(18) -0.7405(4) 0.0236(7) Uani 1 1 d . . . . .
H20' H -0.758186 -0.646987 -0.792080 0.028 Uiso 1 1 calc R . . . .
C7' C -0.47511(11) -0.87959(19) -0.2852(5) 0.0259(7) Uani 1 1 d . . . . .
H7' H -0.474880 -0.938334 -0.272783 0.031 Uiso 1 1 calc R . . . .
C6' C -0.44278(12) -0.8307(2) -0.1980(5) 0.0318(8) Uani 1 1 d . . . . .
H6' H -0.420023 -0.856449 -0.124289 0.038 Uiso 1 1 calc R . . . .
C5' C -0.44266(12) -0.7442(2) -0.2155(5) 0.0314(8) Uani 1 1 d . . . . .
H5' H -0.419528 -0.712278 -0.156208 0.038 Uiso 1 1 calc R . . . .
C20 C -0.67101(11) -0.09176(18) -0.5940(5) 0.0233(7) Uani 1 1 d . . . . .
H20 H -0.675178 -0.040477 -0.654908 0.028 Uiso 1 1 calc R . . . .
C21 C -0.64970(11) -0.09379(18) -0.4277(4) 0.0223(7) Uani 1 1 d . . . . .
H21 H -0.638734 -0.043846 -0.374682 0.027 Uiso 1 1 calc R . . . .
C22 C -0.64440(11) -0.16883(18) -0.3388(4) 0.0205(7) Uani 1 1 d . . . . .
H22 H -0.629211 -0.169913 -0.225903 0.025 Uiso 1 1 calc R . . . .
C23 C -0.66098(10) -0.24261(17) -0.4124(4) 0.0163(6) Uani 1 1 d . . . . .


_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 C2 1.208(3) . ?
N1 C1 1.452(3) . ?
N1 C10 1.467(4) . ?
N1 C23 1.425(4) . ?
C1 N2 1.460(4) . ?
C1 C2 1.567(4) . ?
C1 C9 1.564(4) . ?
O2 C9 1.208(3) . ?
N2 C12 1.435(4) . ?
N2 C11 1.472(4) . ?
C2 C3 1.486(4) . ?
O1' C2' 1.211(3) . ?
C3 C4 1.386(4) . ?
C3 C8 1.397(4) . ?
O2' C9' 1.208(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.393(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.393(5) . ?
N2' C12' 1.438(4) . ?
N2' C1' 1.452(4) . ?
N2' C11' 1.466(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.381(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.387(4) . ?
N1' C23' 1.429(4) . ?
N1' C1' 1.458(4) . ?
N1' C10' 1.459(4) . ?
C8 C9 1.488(4) . ?
C23' C22' 1.387(4) . ?
C23' C18' 1.408(4) . ?
C12' C17' 1.401(4) . ?
C12' C13' 1.392(4) . ?
C2' C3' 1.468(4) . ?
C2' C1' 1.568(4) . ?
C21' H21' 0.9500 . ?
C21' C22' 1.383(4) . ?
C21' C20' 1.382(5) . ?
C22' H22' 0.9500 . ?
C3' C8' 1.401(4) . ?
C3' C4' 1.386(4) . ?
C16' H16' 0.9500 . ?
C16' C17' 1.399(4) . ?
C16' C15' 1.388(4) . ?
C17' C18' 1.477(4) . ?
C19' H19' 0.9500 . ?
C19' C18' 1.387(4) . ?
C19' C20' 1.393(4) . ?
C9' C1' 1.554(4) . ?
C9' C8' 1.483(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C8' C7' 1.381(4) . ?
C12 C13 1.387(4) . ?
C12 C17 1.402(4) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C10' H10D 0.9800 . ?
C10' H10E 0.9800 . ?
C10' H10F 0.9800 . ?
C13 H13 0.9500 . ?
C13 C14 1.385(4) . ?
C14' H14' 0.9500 . ?
C14' C13' 1.385(4) . ?
C14' C15' 1.374(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.375(4) . ?
C4' H4' 0.9500 . ?
C4' C5' 1.388(5) . ?
C16 H16 0.9500 . ?
C16 C15 1.385(4) . ?
C16 C17 1.394(4) . ?
C15 H15 0.9500 . ?
C11' H11D 0.9800 . ?
C11' H11E 0.9800 . ?
C11' H11F 0.9800 . ?
C17 C18 1.481(4) . ?
C18 C19 1.399(4) . ?
C18 C23 1.406(4) . ?
C13' H13' 0.9500 . ?
C19 H19 0.9500 . ?
C19 C20 1.380(4) . ?
C15' H15' 0.9500 . ?
C20' H20' 0.9500 . ?
C7' H7' 0.9500 . ?
C7' C6' 1.380(5) . ?
C6' H6' 0.9500 . ?
C6' C5' 1.397(5) . ?
C5' H5' 0.9500 . ?
C20 H20 0.9500 . ?
C20 C21 1.385(5) . ?
C21 H21 0.9500 . ?
C21 C22 1.387(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.392(4) . ?

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 C10 112.6(2) . . ?
C23 N1 C1 120.5(2) . . ?
C23 N1 C10 116.0(2) . . ?
N1 C1 N2 111.8(2) . . ?
N1 C1 C2 112.3(2) . . ?
N1 C1 C9 109.1(2) . . ?
N2 C1 C2 109.1(2) . . ?
N2 C1 C9 112.1(2) . . ?
C9 C1 C2 102.1(2) . . ?
C1 N2 C11 113.4(2) . . ?
C12 N2 C1 116.5(2) . . ?
C12 N2 C11 114.6(2) . . ?
O1 C2 C1 124.8(3) . . ?
O1 C2 C3 126.7(3) . . ?
C3 C2 C1 108.4(2) . . ?
C4 C3 C2 128.2(3) . . ?
C4 C3 C8 121.3(3) . . ?
C8 C3 C2 110.5(3) . . ?
C3 C4 H4 121.2 . . ?
C3 C4 C5 117.5(3) . . ?
C5 C4 H4 121.2 . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 121.1(3) . . ?
C6 C5 H5 119.5 . . ?
C12' N2' C1' 115.7(2) . . ?
C12' N2' C11' 115.1(2) . . ?
C1' N2' C11' 112.5(2) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 C5 121.1(3) . . ?
C7 C6 H6 119.4 . . ?
C6 C7 H7 120.9 . . ?
C6 C7 C8 118.2(3) . . ?
C8 C7 H7 120.9 . . ?
C23' N1' C1' 117.2(2) . . ?
C23' N1' C10' 115.8(3) . . ?
C1' N1' C10' 113.0(2) . . ?
C3 C8 C9 110.4(3) . . ?
C7 C8 C3 120.7(3) . . ?
C7 C8 C9 128.9(3) . . ?
O2 C9 C1 125.2(3) . . ?
O2 C9 C8 126.3(3) . . ?
C8 C9 C1 108.5(2) . . ?
C22' C23' N1' 122.2(3) . . ?
C22' C23' C18' 119.5(3) . . ?
C18' C23' N1' 117.9(3) . . ?
C17' C12' N2' 118.1(3) . . ?
C13' C12' N2' 121.7(3) . . ?
C13' C12' C17' 119.9(3) . . ?
O1' C2' C3' 127.1(3) . . ?
O1' C2' C1' 124.6(3) . . ?
C3' C2' C1' 108.3(2) . . ?
C22' C21' H21' 119.9 . . ?
C20' C21' H21' 119.9 . . ?
C20' C21' C22' 120.2(3) . . ?
C23' C22' H22' 119.5 . . ?
C21' C22' C23' 120.9(3) . . ?
C21' C22' H22' 119.5 . . ?
C8' C3' C2' 110.8(3) . . ?
C4' C3' C2' 128.6(3) . . ?
C4' C3' C8' 120.7(3) . . ?
C17' C16' H16' 119.4 . . ?
C15' C16' H16' 119.4 . . ?
C15' C16' C17' 121.1(3) . . ?
C12' C17' C18' 121.0(3) . . ?
C16' C17' C12' 118.5(3) . . ?
C16' C17' C18' 120.5(3) . . ?
C18' C19' H19' 119.3 . . ?
C18' C19' C20' 121.5(3) . . ?
C20' C19' H19' 119.3 . . ?
O2' C9' C1' 125.1(3) . . ?
O2' C9' C8' 126.5(3) . . ?
C8' C9' C1' 108.4(2) . . ?
N2' C1' N1' 111.6(2) . . ?
N2' C1' C2' 109.6(2) . . ?
N2' C1' C9' 113.0(2) . . ?
N1' C1' C2' 111.0(2) . . ?
N1' C1' C9' 108.9(2) . . ?
C9' C1' C2' 102.3(2) . . ?
C23' C18' C17' 120.7(3) . . ?
C19' C18' C23' 118.7(3) . . ?
C19' C18' C17' 120.5(3) . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C3' C8' C9' 110.2(3) . . ?
C7' C8' C3' 121.3(3) . . ?
C7' C8' C9' 128.6(3) . . ?
C13 C12 N2 121.4(3) . . ?
C13 C12 C17 119.5(3) . . ?
C17 C12 N2 118.8(3) . . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
N2 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1' C10' H10D 109.5 . . ?
N1' C10' H10E 109.5 . . ?
N1' C10' H10F 109.5 . . ?
H10D C10' H10E 109.5 . . ?
H10D C10' H10F 109.5 . . ?
H10E C10' H10F 109.5 . . ?
C12 C13 H13 119.5 . . ?
C14 C13 C12 121.0(3) . . ?
C14 C13 H13 119.5 . . ?
C13' C14' H14' 119.8 . . ?
C15' C14' H14' 119.8 . . ?
C15' C14' C13' 120.4(3) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.1(3) . . ?
C15 C14 H14 119.9 . . ?
C3' C4' H4' 120.9 . . ?
C3' C4' C5' 118.2(3) . . ?
C5' C4' H4' 120.9 . . ?
C15 C16 H16 119.0 . . ?
C15 C16 C17 122.0(3) . . ?
C17 C16 H16 119.0 . . ?
C14 C15 C16 119.1(3) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
N2' C11' H11D 109.5 . . ?
N2' C11' H11E 109.5 . . ?
N2' C11' H11F 109.5 . . ?
H11D C11' H11E 109.5 . . ?
H11D C11' H11F 109.5 . . ?
H11E C11' H11F 109.5 . . ?
C12 C17 C18 121.0(3) . . ?
C16 C17 C12 118.2(3) . . ?
C16 C17 C18 120.7(3) . . ?
C19 C18 C17 119.9(3) . . ?
C19 C18 C23 118.1(3) . . ?
C23 C18 C17 122.0(3) . . ?
C12' C13' H13' 119.8 . . ?
C14' C13' C12' 120.3(3) . . ?
C14' C13' H13' 119.8 . . ?
C18 C19 H19 118.9 . . ?
C20 C19 C18 122.1(3) . . ?
C20 C19 H19 118.9 . . ?
C16' C15' H15' 120.2 . . ?
C14' C15' C16' 119.7(3) . . ?
C14' C15' H15' 120.2 . . ?
C21' C20' C19' 119.2(3) . . ?
C21' C20' H20' 120.4 . . ?
C19' C20' H20' 120.4 . . ?
C8' C7' H7' 121.1 . . ?
C6' C7' C8' 117.8(3) . . ?
C6' C7' H7' 121.1 . . ?
C7' C6' H6' 119.2 . . ?
C7' C6' C5' 121.7(3) . . ?
C5' C6' H6' 119.2 . . ?
C4' C5' C6' 120.4(3) . . ?
C4' C5' H5' 119.8 . . ?
C6' C5' H5' 119.8 . . ?
C19 C20 H20 120.4 . . ?
C19 C20 C21 119.2(3) . . ?
C21 C20 H20 120.4 . . ?
C20 C21 H21 120.0 . . ?
C20 C21 C22 119.9(3) . . ?
C22 C21 H21 120.0 . . ?
C21 C22 H22 119.5 . . ?
C21 C22 C23 121.1(3) . . ?
C23 C22 H22 119.5 . . ?
C18 C23 N1 119.3(3) . . ?
C22 C23 N1 120.7(3) . . ?
C22 C23 C18 119.5(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_esser_jw344_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1900309'
_audit_update_record             
;
2019-02-28 deposited with the CCDC.	2019-09-30 downloaded from the CCDC.
;
_audit_creation_date             2019-02-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
# end Validation Reply Form
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
besser@oc.uni-freiburg.de
daniel.kratzert@ac.uni-freiburg.de
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H16 N2 O2'
_chemical_formula_sum            'C21 H16 N2 O2'
_chemical_formula_weight         328.36
_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'
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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   8.899(8)
_cell_length_b                   16.027(13)
_cell_length_c                   21.774(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3105(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3787
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.057
_cell_measurement_theta_min      2.539
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.990
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.4562
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1541 before and 0.0943 after correction. The Ratio of minimum to maximum transmission is 0.6122. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1376
_exptl_crystal_recrystallization_method 
'The material was recrystallised from CDCl3 by slow evaporation'
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1943
_diffrn_reflns_av_unetI/netI     0.0636
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            58408
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.131
_diffrn_reflns_theta_max         25.131
_diffrn_reflns_theta_min         1.871
_diffrn_ambient_temperature      100.01
_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       'fixed-chi two circle goniometer'
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           50
_diffrn_source_type              'Incoatec Mo I\ms'
_diffrn_source_voltage           0.6
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2017
_reflns_number_total             2769
_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 V8.38A (Madison, 2016)'
_computing_data_collection       'Bruker APEX2 software'
_computing_data_reduction        'SAINT V8.38A (Madison, 2016)'
_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 (Sheldrick, 2015)'
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2769
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1027
_refine_ls_R_factor_gt           0.0676
_refine_ls_restrained_S_all      1.104
_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)+(0.0425P)²+3.7364P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1251
_refine_ls_wR_factor_ref         0.1376
_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:
 C5(H5), C6(H6), C7(H7), C8(H8), C13(H13), C14(H14), C15(H15), C17(H17),
 C18(H18), C19(H19)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_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
O1 O 0.3995(2) 0.25078(14) 0.36384(11) 0.0305(6) Uani 1 1 d . . . . .
N1 N 0.5868(3) 0.41169(15) 0.34992(11) 0.0158(6) Uani 1 1 d . . . . .
C1 C 0.6264(3) 0.33514(18) 0.38260(13) 0.0159(7) Uani 1 1 d . . . . .
N2 N 0.6091(3) 0.34899(14) 0.44856(11) 0.0152(6) Uani 1 1 d . . . . .
O2 O 0.6030(2) 0.13141(12) 0.30574(9) 0.0212(5) Uani 1 1 d . . . . .
C2 C 0.5335(3) 0.26000(18) 0.35957(13) 0.0171(7) Uani 1 1 d . . . . .
C3 C 0.6406(3) 0.19686(18) 0.32904(13) 0.0161(7) Uani 1 1 d . . . . .
C4 C 0.7915(3) 0.23244(17) 0.33584(12) 0.0149(7) Uani 1 1 d . . . . .
C5 C 0.9272(3) 0.19900(18) 0.31661(13) 0.0171(7) Uani 1 1 d . . . . .
H5 H 0.930275 0.147607 0.294913 0.020 Uiso 1 1 calc R . . . .
C6 C 1.0579(3) 0.24198(19) 0.32967(13) 0.0183(7) Uani 1 1 d . . . . .
H6 H 1.152057 0.219823 0.317177 0.022 Uiso 1 1 calc R . . . .
C7 C 1.0523(3) 0.31778(19) 0.36111(13) 0.0193(7) Uani 1 1 d . . . . .
H7 H 1.142999 0.346533 0.370068 0.023 Uiso 1 1 calc R . . . .
C9 C 0.7850(3) 0.30828(18) 0.36709(12) 0.0140(6) Uani 1 1 d . . . . .
C8 C 0.9161(3) 0.35180(19) 0.37949(14) 0.0199(7) Uani 1 1 d . . . . .
H8 H 0.912825 0.403951 0.400191 0.024 Uiso 1 1 calc R . . . .
C10 C 0.6306(4) 0.4178(2) 0.28546(14) 0.0275(8) Uani 1 1 d . . . . .
H10A H 0.552125 0.393071 0.259677 0.041 Uiso 1 1 calc GR . . . .
H10B H 0.725324 0.387785 0.279068 0.041 Uiso 1 1 calc GR . . . .
H10C H 0.643901 0.476588 0.274374 0.041 Uiso 1 1 calc GR . . . .
C11 C 0.6721(4) 0.28659(19) 0.48969(14) 0.0225(7) Uani 1 1 d . . . . .
H11A H 0.595904 0.244184 0.498714 0.034 Uiso 1 1 calc GR . . . .
H11B H 0.703857 0.313434 0.527991 0.034 Uiso 1 1 calc GR . . . .
H11C H 0.759009 0.260134 0.470071 0.034 Uiso 1 1 calc GR . . . .
C12 C 0.4774(3) 0.38889(17) 0.46850(13) 0.0141(7) Uani 1 1 d . . . . .
C13 C 0.4296(3) 0.38386(18) 0.52863(14) 0.0182(7) Uani 1 1 d . . . . .
H13 H 0.484024 0.351115 0.557389 0.022 Uiso 1 1 calc R . . . .
C14 C 0.2998(3) 0.42732(18) 0.54735(14) 0.0201(7) Uani 1 1 d . . . . .
H14 H 0.269094 0.424536 0.589081 0.024 Uiso 1 1 calc R . . . .
C15 C 0.2174(3) 0.47329(18) 0.50684(14) 0.0192(7) Uani 1 1 d . . . . .
H15 H 0.127789 0.499983 0.520115 0.023 Uiso 1 1 calc R . . . .
C16 C 0.2647(3) 0.48139(17) 0.44519(13) 0.0171(7) Uani 1 1 d . . . . .
C17 C 0.1882(3) 0.53266(18) 0.40274(14) 0.0198(7) Uani 1 1 d . . . . .
H17 H 0.099440 0.561067 0.414960 0.024 Uiso 1 1 calc R . . . .
C18 C 0.2408(4) 0.54166(18) 0.34449(14) 0.0221(7) Uani 1 1 d . . . . .
H18 H 0.188204 0.576363 0.316406 0.027 Uiso 1 1 calc R . . . .
C19 C 0.3720(3) 0.50031(18) 0.32523(13) 0.0190(7) Uani 1 1 d . . . . .
H19 H 0.407095 0.507362 0.284362 0.023 Uiso 1 1 calc R . . . .
C20 C 0.4499(3) 0.44961(17) 0.36526(13) 0.0145(7) Uani 1 1 d . . . . .
C21 C 0.3965(3) 0.43908(17) 0.42602(13) 0.0138(6) Uani 1 1 d . . . . .


_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 C2 1.205(4) . ?
N1 C1 1.461(4) . ?
N1 C10 1.460(4) . ?
N1 C20 1.402(4) . ?
C1 N2 1.461(4) . ?
C1 C2 1.544(4) . ?
C1 C9 1.514(4) . ?
N2 C11 1.455(4) . ?
N2 C12 1.404(4) . ?
O2 C3 1.212(3) . ?
C2 C3 1.541(4) . ?
C3 C4 1.467(4) . ?
C4 C5 1.386(4) . ?
C4 C9 1.394(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.381(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.395(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.388(4) . ?
C9 C8 1.386(4) . ?
C8 H8 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.379(4) . ?
C12 C21 1.422(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.409(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.363(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.413(4) . ?
C16 C17 1.412(4) . ?
C16 C21 1.417(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.360(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.406(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.379(4) . ?
C20 C21 1.416(4) . ?

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 N1 C1 117.4(2) . . ?
C20 N1 C1 117.2(2) . . ?
C20 N1 C10 115.6(2) . . ?
N1 C1 N2 109.0(2) . . ?
N1 C1 C2 111.6(2) . . ?
N1 C1 C9 110.8(2) . . ?
N2 C1 C2 112.4(2) . . ?
N2 C1 C9 111.2(2) . . ?
C9 C1 C2 101.8(2) . . ?
C11 N2 C1 117.4(2) . . ?
C12 N2 C1 117.5(2) . . ?
C12 N2 C11 116.4(2) . . ?
O1 C2 C1 126.9(3) . . ?
O1 C2 C3 124.4(3) . . ?
C3 C2 C1 108.7(3) . . ?
O2 C3 C2 125.3(3) . . ?
O2 C3 C4 129.2(3) . . ?
C4 C3 C2 105.5(2) . . ?
C5 C4 C3 128.1(3) . . ?
C5 C4 C9 121.4(3) . . ?
C9 C4 C3 110.5(3) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 C4 118.6(3) . . ?
C6 C5 H5 120.7 . . ?
C5 C6 H6 119.8 . . ?
C5 C6 C7 120.3(3) . . ?
C7 C6 H6 119.8 . . ?
C6 C7 H7 119.5 . . ?
C8 C7 C6 121.0(3) . . ?
C8 C7 H7 119.5 . . ?
C4 C9 C1 113.3(2) . . ?
C8 C9 C1 126.8(3) . . ?
C8 C9 C4 119.9(3) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 C7 118.8(3) . . ?
C9 C8 H8 120.6 . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
N2 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C21 118.6(3) . . ?
C13 C12 N2 121.7(3) . . ?
C13 C12 C21 119.6(3) . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 119.9(3) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 119.3 . . ?
C15 C14 C13 121.4(3) . . ?
C15 C14 H14 119.3 . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.3(3) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C21 118.8(3) . . ?
C17 C16 C15 122.1(3) . . ?
C17 C16 C21 119.0(3) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.4(3) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 119.5 . . ?
C17 C18 C19 120.9(3) . . ?
C19 C18 H18 119.5 . . ?
C18 C19 H19 119.8 . . ?
C20 C19 C18 120.5(3) . . ?
C20 C19 H19 119.8 . . ?
N1 C20 C21 117.6(3) . . ?
C19 C20 N1 122.8(3) . . ?
C19 C20 C21 119.5(3) . . ?
C16 C21 C12 119.9(3) . . ?
C20 C21 C12 120.4(3) . . ?
C20 C21 C16 119.7(3) . . ?

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
O1 C2 C3 O2 0.3(5) . . . . ?
O1 C2 C3 C4 -178.5(3) . . . . ?
N1 C1 N2 C11 -167.6(2) . . . . ?
N1 C1 N2 C12 46.0(3) . . . . ?
N1 C1 C2 O1 -64.7(4) . . . . ?
N1 C1 C2 C3 115.0(3) . . . . ?
N1 C1 C9 C4 -115.1(3) . . . . ?
N1 C1 C9 C8 63.3(4) . . . . ?
N1 C20 C21 C12 -2.5(4) . . . . ?
N1 C20 C21 C16 175.2(2) . . . . ?
C1 N1 C20 C19 -154.7(3) . . . . ?
C1 N1 C20 C21 29.6(4) . . . . ?
C1 N2 C12 C13 161.1(3) . . . . ?
C1 N2 C12 C21 -22.2(4) . . . . ?
C1 C2 C3 O2 -179.3(3) . . . . ?
C1 C2 C3 C4 1.8(3) . . . . ?
C1 C9 C8 C7 -179.2(3) . . . . ?
N2 C1 C2 O1 58.1(4) . . . . ?
N2 C1 C2 C3 -122.2(2) . . . . ?
N2 C1 C9 C4 123.6(3) . . . . ?
N2 C1 C9 C8 -58.1(4) . . . . ?
N2 C12 C13 C14 177.7(2) . . . . ?
N2 C12 C21 C16 -178.8(2) . . . . ?
N2 C12 C21 C20 -1.2(4) . . . . ?
O2 C3 C4 C5 0.4(5) . . . . ?
O2 C3 C4 C9 -178.3(3) . . . . ?
C2 C1 N2 C11 68.2(3) . . . . ?
C2 C1 N2 C12 -78.3(3) . . . . ?
C2 C1 C9 C4 3.7(3) . . . . ?
C2 C1 C9 C8 -178.0(3) . . . . ?
C2 C3 C4 C5 179.2(3) . . . . ?
C2 C3 C4 C9 0.5(3) . . . . ?
C3 C4 C5 C6 -177.8(3) . . . . ?
C3 C4 C9 C1 -2.8(3) . . . . ?
C3 C4 C9 C8 178.8(3) . . . . ?
C4 C5 C6 C7 -0.5(4) . . . . ?
C4 C9 C8 C7 -1.0(4) . . . . ?
C5 C4 C9 C1 178.5(3) . . . . ?
C5 C4 C9 C8 0.0(4) . . . . ?
C5 C6 C7 C8 -0.5(4) . . . . ?
C6 C7 C8 C9 1.2(4) . . . . ?
C9 C1 N2 C11 -45.2(3) . . . . ?
C9 C1 N2 C12 168.3(2) . . . . ?
C9 C1 C2 O1 177.2(3) . . . . ?
C9 C1 C2 C3 -3.2(3) . . . . ?
C9 C4 C5 C6 0.8(4) . . . . ?
C10 N1 C1 N2 165.6(2) . . . . ?
C10 N1 C1 C2 -69.7(3) . . . . ?
C10 N1 C1 C9 43.0(3) . . . . ?
C10 N1 C20 C19 -9.7(4) . . . . ?
C10 N1 C20 C21 174.6(3) . . . . ?
C11 N2 C12 C13 14.3(4) . . . . ?
C11 N2 C12 C21 -169.0(3) . . . . ?
C12 C13 C14 C15 1.5(4) . . . . ?
C13 C12 C21 C16 -2.0(4) . . . . ?
C13 C12 C21 C20 175.6(3) . . . . ?
C13 C14 C15 C16 -2.9(4) . . . . ?
C14 C15 C16 C17 -175.8(3) . . . . ?
C14 C15 C16 C21 1.7(4) . . . . ?
C15 C16 C17 C18 177.2(3) . . . . ?
C15 C16 C21 C12 0.7(4) . . . . ?
C15 C16 C21 C20 -176.9(3) . . . . ?
C16 C17 C18 C19 0.0(4) . . . . ?
C17 C16 C21 C12 178.3(3) . . . . ?
C17 C16 C21 C20 0.7(4) . . . . ?
C17 C18 C19 C20 0.0(4) . . . . ?
C18 C19 C20 N1 -175.3(3) . . . . ?
C18 C19 C20 C21 0.3(4) . . . . ?
C19 C20 C21 C12 -178.3(3) . . . . ?
C19 C20 C21 C16 -0.7(4) . . . . ?
C20 N1 C1 N2 -50.0(3) . . . . ?
C20 N1 C1 C2 74.7(3) . . . . ?
C20 N1 C1 C9 -172.6(2) . . . . ?
C21 C12 C13 C14 1.0(4) . . . . ?
C21 C16 C17 C18 -0.4(4) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems 800'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_special_instructions 'No special instructions were received'
# start Validation Reply Form
_vrf_RINTA01_esser_jw344_0m_a    
;
PROBLEM: The value of Rint is greater than 0.18
RESPONSE: The crystal was of bad quality.
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_esser_jw137_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1851704'
_audit_update_record             
;
2018-06-26 deposited with the CCDC.	2019-09-30 downloaded from the CCDC.
;
_audit_creation_date             2018-06-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
besser@oc.uni-freiburg.de
daniel.kratzert@ac.uni-freiburg.de
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C35 H24 N4 O3)'
_chemical_formula_sum            'C70 H48 N8 O6'
_chemical_formula_weight         1097.16
_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'
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                   14.7127(13)
_cell_length_b                   13.2097(16)
_cell_length_c                   27.114(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.327(9)
_cell_angle_gamma                90
_cell_volume                     5226.6(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9322
_cell_measurement_temperature    100
_cell_measurement_theta_max      21.804
_cell_measurement_theta_min      2.162
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.990
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.7148
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0875 before and 0.0536 after correction. The Ratio of minimum to maximum transmission is 0.9592. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             2288
_exptl_crystal_recrystallization_method 
'The material was recrystallised from a mixture of DCM and methanol  by solvent layering'
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0587
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            80580
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.442
_diffrn_reflns_theta_min         1.395
_diffrn_ambient_temperature      100.01
_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 0.998
_diffrn_measurement_device       'fixed-chi two circle goniometer'
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           50
_diffrn_source_type              'Incoatec Mo I\ms'
_diffrn_source_voltage           0.6
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6571
_reflns_number_total             9634
_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 V8.38A (Madison, 2016)'
_computing_data_collection       'Bruker APEX2 software'
_computing_data_reduction        'SAINT V8.38A (Madison, 2016)'
_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         0.581
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     761
_refine_ls_number_reflns         9634
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0920
_refine_ls_R_factor_gt           0.0563
_refine_ls_restrained_S_all      1.061
_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)+(0.0646P)²+2.7610P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1316
_refine_ls_wR_factor_ref         0.1489
_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:
 C2(H2), C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C23A(H23A), C16(H16),
 C24A(H24A), C17(H17), C19(H19), C8A(H8A), C7A(H7A), C26A(H26A), C31A(H31A),
 C17A(H17A), C6A(H6A), C16A(H16A), C19A(H19A), C27A(H27A), C35A(H35A),
 C32A(H32A), C2A(H2A), C4A(H4A), C3A(H3A), C23(H23), C33A(H33A), C27(H27),
 C26(H26), C24(H24), C34A(H34A), C31(H31), C32(H32), C33(H33), C34(H34),
 C35(H35)
2.b Idealised Me refined as rotating group:
 C12(H12a,H12b,H12c), C13(H13a,H13b,H13c), C13A(H13d,H13e,H13f), C12A(H12d,
 H12e,H12f)
;
_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
O1 O 0.55629(11) 0.52570(13) 0.45811(6) 0.0357(4) Uani 1 1 d . . . . .
N1 N 0.57846(14) 0.30106(15) 0.42458(8) 0.0342(5) Uani 1 1 d . . . . .
C1 C 0.72200(16) 0.4276(2) 0.40600(9) 0.0352(6) Uani 1 1 d . . . . .
O3A O 1.01932(11) 0.26762(12) 0.36277(6) 0.0317(4) Uani 1 1 d . . . . .
O2 O 0.48626(11) 0.30822(14) 0.31948(6) 0.0388(4) Uani 1 1 d . . . . .
N2 N 0.63881(13) 0.42634(16) 0.37416(7) 0.0314(5) Uani 1 1 d . . . . .
C2 C 0.79487(18) 0.4869(3) 0.39642(10) 0.0486(8) Uani 1 1 d . . . . .
H2 H 0.788737 0.530317 0.368242 0.058 Uiso 1 1 calc R . . . .
C3 C 0.87819(19) 0.4835(3) 0.42816(11) 0.0580(9) Uani 1 1 d . . . . .
H3 H 0.927941 0.524427 0.420964 0.070 Uiso 1 1 calc R . . . .
O3 O -0.12595(10) 0.51625(12) 0.18712(5) 0.0277(4) Uani 1 1 d . . . . .
N3 N -0.19055(13) 0.53219(16) 0.25603(7) 0.0322(5) Uani 1 1 d . . . . .
C4 C 0.88891(19) 0.4229(3) 0.46884(11) 0.0562(9) Uani 1 1 d . . . . .
H4 H 0.945781 0.422068 0.489827 0.067 Uiso 1 1 calc R . . . .
N4 N -0.25949(14) 0.53427(16) 0.21517(8) 0.0346(5) Uani 1 1 d . . . . .
O2A O 0.42114(12) 0.48175(14) 0.24748(6) 0.0397(4) Uani 1 1 d . . . . .
C5 C 0.81603(19) 0.3607(2) 0.48031(10) 0.0448(7) Uani 1 1 d . . . . .
O1A O 0.34959(12) 0.34235(14) 0.08667(6) 0.0424(5) Uani 1 1 d . . . . .
C6 C 0.8244(2) 0.2954(3) 0.52162(11) 0.0563(9) Uani 1 1 d . . . . .
H6 H 0.880618 0.292202 0.543089 0.068 Uiso 1 1 calc R . . . .
N1A N 0.26695(13) 0.35816(15) 0.18855(7) 0.0306(5) Uani 1 1 d . . . . .
C7 C 0.7532(3) 0.2374(2) 0.53100(11) 0.0561(9) Uani 1 1 d . . . . .
H7 H 0.760438 0.193634 0.559041 0.067 Uiso 1 1 calc R . . . .
N4A N 1.15439(14) 0.25241(15) 0.33608(8) 0.0339(5) Uani 1 1 d . . . . .
C8 C 0.6684(2) 0.2398(2) 0.50029(10) 0.0474(7) Uani 1 1 d . . . . .
H8 H 0.618780 0.199467 0.508190 0.057 Uiso 1 1 calc R . . . .
N2A N 0.30701(14) 0.51407(16) 0.15175(7) 0.0337(5) Uani 1 1 d . . . . .
C9 C 0.65763(18) 0.3011(2) 0.45874(9) 0.0367(6) Uani 1 1 d . . . . .
N3A N 1.08595(14) 0.24782(15) 0.29492(7) 0.0335(5) Uani 1 1 d . . . . .
C23A C 0.81825(17) 0.26984(18) 0.20777(9) 0.0326(6) Uani 1 1 d . . . . .
H23A H 0.811017 0.269817 0.172448 0.039 Uiso 1 1 calc R . . . .
C9A C 0.18297(16) 0.35407(19) 0.15812(8) 0.0292(6) Uani 1 1 d . . . . .
C29A C 1.11195(16) 0.26483(18) 0.37485(9) 0.0305(6) Uani 1 1 d . . . . .
C28A C 1.00852(17) 0.25713(17) 0.31233(9) 0.0299(6) Uani 1 1 d . . . . .
C15A C 0.47638(16) 0.32150(18) 0.15103(9) 0.0308(6) Uani 1 1 d . . . . .
C18A C 0.64833(16) 0.29005(19) 0.20515(9) 0.0331(6) Uani 1 1 d . . . . .
C10 C 0.73156(17) 0.3637(2) 0.44847(9) 0.0345(6) Uani 1 1 d . . . . .
C1A C 0.22323(17) 0.51608(19) 0.12078(9) 0.0323(6) Uani 1 1 d . . . . .
C11 C 0.55808(15) 0.39244(19) 0.39498(9) 0.0291(6) Uani 1 1 d . . . . .
C22A C 0.74086(17) 0.27640(19) 0.23286(9) 0.0332(6) Uani 1 1 d . . . . .
C12 C 0.4994(2) 0.2477(2) 0.43957(11) 0.0489(8) Uani 1 1 d . . . . .
H12A H 0.516065 0.177173 0.447520 0.073 Uiso 1 1 calc GR . . . .
H12B H 0.448794 0.249416 0.412302 0.073 Uiso 1 1 calc GR . . . .
H12C H 0.480200 0.280610 0.468946 0.073 Uiso 1 1 calc GR . . . .
C14 C 0.51468(16) 0.47593(18) 0.42499(8) 0.0280(5) Uani 1 1 d . . . . .
C13 C 0.62231(18) 0.5125(2) 0.34022(9) 0.0372(6) Uani 1 1 d . . . . .
H13A H 0.626236 0.575591 0.359414 0.056 Uiso 1 1 calc GR . . . .
H13B H 0.561134 0.506590 0.321354 0.056 Uiso 1 1 calc GR . . . .
H13C H 0.668502 0.513085 0.317185 0.056 Uiso 1 1 calc GR . . . .
C14A C 0.38465(17) 0.35465(19) 0.12900(9) 0.0320(6) Uani 1 1 d . . . . .
C15 C 0.41706(16) 0.48488(17) 0.40466(8) 0.0259(5) Uani 1 1 d . . . . .
C30A C 1.14902(16) 0.27822(18) 0.42677(9) 0.0314(6) Uani 1 1 d . . . . .
C16 C 0.34776(16) 0.54022(18) 0.42257(9) 0.0301(6) Uani 1 1 d . . . . .
H16 H 0.358840 0.575938 0.453160 0.036 Uiso 1 1 calc R . . . .
C24A C 0.90465(17) 0.26343(18) 0.23387(9) 0.0328(6) Uani 1 1 d . . . . .
H24A H 0.956639 0.260167 0.216447 0.039 Uiso 1 1 calc R . . . .
C17 C 0.26270(16) 0.54178(18) 0.39473(9) 0.0307(6) Uani 1 1 d . . . . .
H17 H 0.214728 0.578583 0.406885 0.037 Uiso 1 1 calc R . . . .
C11A C 0.34039(16) 0.41551(19) 0.16945(9) 0.0312(6) Uani 1 1 d . . . . .
C18 C 0.24412(15) 0.49085(18) 0.34890(8) 0.0275(5) Uani 1 1 d . . . . .
C21A C 0.42207(17) 0.42764(19) 0.21112(9) 0.0325(6) Uani 1 1 d . . . . .
C19 C 0.31308(15) 0.43192(18) 0.33251(8) 0.0285(5) Uani 1 1 d . . . . .
H19 H 0.301784 0.394322 0.302483 0.034 Uiso 1 1 calc R . . . .
C10A C 0.15936(16) 0.43667(18) 0.12521(9) 0.0304(6) Uani 1 1 d . . . . .
C25A C 0.91632(16) 0.26170(18) 0.28536(9) 0.0304(6) Uani 1 1 d . . . . .
C8A C 0.12048(17) 0.27650(19) 0.16094(9) 0.0330(6) Uani 1 1 d . . . . .
H8A H 0.136230 0.220284 0.182173 0.040 Uiso 1 1 calc R . . . .
C5A C 0.07171(17) 0.4398(2) 0.09674(9) 0.0342(6) Uani 1 1 d . . . . .
C7A C 0.03377(17) 0.2809(2) 0.13243(9) 0.0370(6) Uani 1 1 d . . . . .
H7A H -0.008476 0.227197 0.134728 0.044 Uiso 1 1 calc R . . . .
C20A C 0.49913(16) 0.36555(19) 0.19805(9) 0.0319(6) Uani 1 1 d . . . . .
C26A C 0.84004(17) 0.2666(2) 0.31083(10) 0.0369(6) Uani 1 1 d . . . . .
H26A H 0.847480 0.264643 0.346142 0.044 Uiso 1 1 calc R . . . .
C31A C 1.24140(17) 0.2973(2) 0.44019(10) 0.0380(6) Uani 1 1 d . . . . .
H31A H 1.281507 0.300591 0.415409 0.046 Uiso 1 1 calc R . . . .
C17A C 0.62369(18) 0.2463(2) 0.15834(10) 0.0379(6) Uani 1 1 d . . . . .
H17A H 0.667014 0.204578 0.144868 0.046 Uiso 1 1 calc R . . . .
C13A C 0.37769(17) 0.5828(2) 0.13947(10) 0.0390(6) Uani 1 1 d . . . . .
H13D H 0.392337 0.567605 0.105995 0.059 Uiso 1 1 calc GR . . . .
H13E H 0.432789 0.574477 0.163552 0.059 Uiso 1 1 calc GR . . . .
H13F H 0.355706 0.652671 0.140573 0.059 Uiso 1 1 calc GR . . . .
C12A C 0.29440(18) 0.26755(19) 0.21822(9) 0.0355(6) Uani 1 1 d . . . . .
H12D H 0.248627 0.253192 0.240554 0.053 Uiso 1 1 calc GR . . . .
H12E H 0.354100 0.279317 0.237884 0.053 Uiso 1 1 calc GR . . . .
H12F H 0.298791 0.209731 0.196000 0.053 Uiso 1 1 calc GR . . . .
C6A C 0.00891(17) 0.3606(2) 0.10149(9) 0.0371(6) Uani 1 1 d . . . . .
H6A H -0.050582 0.362682 0.083187 0.045 Uiso 1 1 calc R . . . .
C16A C 0.53894(17) 0.2612(2) 0.13092(9) 0.0367(6) Uani 1 1 d . . . . .
H16A H 0.524135 0.230813 0.099152 0.044 Uiso 1 1 calc R . . . .
C19A C 0.58419(17) 0.3512(2) 0.22519(9) 0.0350(6) Uani 1 1 d . . . . .
H19A H 0.598962 0.382077 0.256833 0.042 Uiso 1 1 calc R . . . .
C27A C 0.75376(18) 0.2744(2) 0.28463(9) 0.0392(6) Uani 1 1 d . . . . .
H27A H 0.702023 0.278542 0.302224 0.047 Uiso 1 1 calc R . . . .
C35A C 1.09160(19) 0.2704(2) 0.46350(10) 0.0430(7) Uani 1 1 d . . . . .
H35A H 1.028033 0.257861 0.454651 0.052 Uiso 1 1 calc R . . . .
C32A C 1.27528(19) 0.3115(2) 0.48961(10) 0.0436(7) Uani 1 1 d . . . . .
H32A H 1.338154 0.327585 0.498596 0.052 Uiso 1 1 calc R . . . .
C20 C 0.39822(15) 0.42933(18) 0.36084(8) 0.0276(5) Uani 1 1 d . . . . .
C2A C 0.19960(19) 0.5930(2) 0.08721(10) 0.0412(7) Uani 1 1 d . . . . .
H2A H 0.242786 0.644662 0.082903 0.049 Uiso 1 1 calc R . . . .
C21 C 0.47954(16) 0.36894(19) 0.35213(9) 0.0304(6) Uani 1 1 d . . . . .
C4A C 0.04995(19) 0.5220(2) 0.06405(10) 0.0426(7) Uani 1 1 d . . . . .
H4A H -0.008958 0.525741 0.045174 0.051 Uiso 1 1 calc R . . . .
C22 C 0.15261(16) 0.49875(17) 0.31953(8) 0.0264(5) Uani 1 1 d . . . . .
C3A C 0.11278(19) 0.5957(2) 0.05942(10) 0.0456(7) Uani 1 1 d . . . . .
H3A H 0.097426 0.650031 0.036935 0.055 Uiso 1 1 calc R . . . .
C23 C 0.07376(16) 0.50684(18) 0.34343(9) 0.0295(6) Uani 1 1 d . . . . .
H23 H 0.079495 0.507266 0.378725 0.035 Uiso 1 1 calc R . . . .
C33A C 1.2186(2) 0.3027(2) 0.52568(11) 0.0490(8) Uani 1 1 d . . . . .
H33A H 1.242404 0.311402 0.559656 0.059 Uiso 1 1 calc R . . . .
C29 C -0.21871(16) 0.52497(18) 0.17591(9) 0.0287(5) Uani 1 1 d . . . . .
C28 C -0.11419(16) 0.52144(18) 0.23781(8) 0.0279(5) Uani 1 1 d . . . . .
C27 C 0.14184(16) 0.49786(18) 0.26755(9) 0.0287(5) Uani 1 1 d . . . . .
H27 H 0.194289 0.492240 0.250609 0.034 Uiso 1 1 calc R . . . .
C26 C 0.05594(16) 0.50506(18) 0.24052(9) 0.0286(6) Uani 1 1 d . . . . .
H26 H 0.049834 0.503981 0.205215 0.034 Uiso 1 1 calc R . . . .
C25 C -0.02180(16) 0.51388(17) 0.26462(8) 0.0273(5) Uani 1 1 d . . . . .
C24 C -0.01184(16) 0.51418(18) 0.31641(9) 0.0288(5) Uani 1 1 d . . . . .
H24 H -0.064485 0.519479 0.333215 0.035 Uiso 1 1 calc R . . . .
C34A C 1.1270(2) 0.2810(3) 0.51275(10) 0.0520(8) Uani 1 1 d . . . . .
H34A H 1.088147 0.273339 0.537922 0.062 Uiso 1 1 calc R . . . .
C30 C -0.25859(16) 0.52200(18) 0.12378(9) 0.0319(6) Uani 1 1 d . . . . .
C31 C -0.35300(18) 0.5080(2) 0.11201(10) 0.0385(6) Uani 1 1 d . . . . .
H31 H -0.390658 0.499289 0.137665 0.046 Uiso 1 1 calc R . . . .
C32 C -0.39115(19) 0.5070(2) 0.06268(10) 0.0420(7) Uani 1 1 d . . . . .
H32 H -0.455018 0.495381 0.054508 0.050 Uiso 1 1 calc R . . . .
C33 C -0.33758(19) 0.5226(2) 0.02529(10) 0.0411(7) Uani 1 1 d . . . . .
H33 H -0.365020 0.524224 -0.008372 0.049 Uiso 1 1 calc R . . . .
C34 C -0.24387(19) 0.5358(2) 0.03654(10) 0.0408(7) Uani 1 1 d . . . . .
H34 H -0.206773 0.545842 0.010734 0.049 Uiso 1 1 calc R . . . .
C35 C -0.20455(18) 0.53429(19) 0.08603(9) 0.0353(6) Uani 1 1 d . . . . .
H35 H -0.140114 0.541757 0.093946 0.042 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 C14 1.214(3) . ?
N1 C9 1.393(3) . ?
N1 C11 1.459(3) . ?
N1 C12 1.462(3) . ?
C1 N2 1.405(3) . ?
C1 C2 1.379(4) . ?
C1 C10 1.421(4) . ?
O3A C29A 1.361(3) . ?
O3A C28A 1.363(3) . ?
O2 C21 1.208(3) . ?
N2 C11 1.450(3) . ?
N2 C13 1.465(3) . ?
C2 C3 1.406(4) . ?
C3 C4 1.356(4) . ?
O3 C29 1.365(3) . ?
O3 C28 1.365(3) . ?
N3 N4 1.404(3) . ?
N3 C28 1.292(3) . ?
C4 C5 1.416(4) . ?
N4 C29 1.293(3) . ?
O2A C21A 1.219(3) . ?
C5 C6 1.407(4) . ?
C5 C10 1.421(4) . ?
O1A C14A 1.208(3) . ?
C6 C7 1.348(5) . ?
N1A C9A 1.396(3) . ?
N1A C11A 1.467(3) . ?
N1A C12A 1.470(3) . ?
C7 C8 1.410(4) . ?
N4A N3A 1.406(3) . ?
N4A C29A 1.300(3) . ?
C8 C9 1.380(4) . ?
N2A C1A 1.400(3) . ?
N2A C11A 1.451(3) . ?
N2A C13A 1.451(3) . ?
C9 C10 1.422(4) . ?
N3A C28A 1.293(3) . ?
C23A C22A 1.402(3) . ?
C23A C24A 1.376(3) . ?
C9A C10A 1.424(3) . ?
C9A C8A 1.385(3) . ?
C29A C30A 1.454(3) . ?
C28A C25A 1.458(3) . ?
C15A C14A 1.471(3) . ?
C15A C20A 1.403(3) . ?
C15A C16A 1.381(3) . ?
C18A C22A 1.480(3) . ?
C18A C17A 1.400(3) . ?
C18A C19A 1.403(3) . ?
C1A C10A 1.424(3) . ?
C1A C2A 1.379(4) . ?
C11 C14 1.555(3) . ?
C11 C21 1.562(3) . ?
C22A C27A 1.393(3) . ?
C14 C15 1.476(3) . ?
C14A C11A 1.567(3) . ?
C15 C16 1.391(3) . ?
C15 C20 1.394(3) . ?
C30A C31A 1.385(3) . ?
C30A C35A 1.389(4) . ?
C16 C17 1.377(3) . ?
C24A C25A 1.385(3) . ?
C17 C18 1.409(3) . ?
C11A C21A 1.549(3) . ?
C18 C19 1.396(3) . ?
C18 C22 1.478(3) . ?
C21A C20A 1.479(3) . ?
C19 C20 1.384(3) . ?
C10A C5A 1.417(3) . ?
C25A C26A 1.392(3) . ?
C8A C7A 1.406(3) . ?
C5A C6A 1.413(4) . ?
C5A C4A 1.412(4) . ?
C7A C6A 1.367(4) . ?
C20A C19A 1.382(3) . ?
C26A C27A 1.377(3) . ?
C31A C32A 1.382(4) . ?
C17A C16A 1.382(3) . ?
C35A C34A 1.377(4) . ?
C32A C33A 1.369(4) . ?
C20 C21 1.482(3) . ?
C2A C3A 1.398(4) . ?
C4A C3A 1.360(4) . ?
C22 C23 1.403(3) . ?
C22 C27 1.398(3) . ?
C23 C24 1.377(3) . ?
C33A C34A 1.378(4) . ?
C29 C30 1.460(3) . ?
C28 C25 1.461(3) . ?
C27 C26 1.381(3) . ?
C26 C25 1.393(3) . ?
C25 C24 1.393(3) . ?
C30 C31 1.397(3) . ?
C30 C35 1.383(4) . ?
C31 C32 1.383(4) . ?
C32 C33 1.377(4) . ?
C33 C34 1.385(4) . ?
C34 C35 1.392(4) . ?

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
C9 N1 C11 117.5(2) . . ?
C9 N1 C12 116.3(2) . . ?
C11 N1 C12 115.9(2) . . ?
N2 C1 C10 118.6(2) . . ?
C2 C1 N2 121.9(2) . . ?
C2 C1 C10 119.5(2) . . ?
C29A O3A C28A 102.93(18) . . ?
C1 N2 C11 117.21(19) . . ?
C1 N2 C13 116.0(2) . . ?
C11 N2 C13 113.98(19) . . ?
C1 C2 C3 120.3(3) . . ?
C4 C3 C2 121.3(3) . . ?
C29 O3 C28 102.41(17) . . ?
C28 N3 N4 106.05(19) . . ?
C3 C4 C5 120.6(3) . . ?
C29 N4 N3 106.47(19) . . ?
C4 C5 C10 118.6(3) . . ?
C6 C5 C4 122.6(3) . . ?
C6 C5 C10 118.8(3) . . ?
C7 C6 C5 120.5(3) . . ?
C9A N1A C11A 116.58(19) . . ?
C9A N1A C12A 116.9(2) . . ?
C11A N1A C12A 116.77(19) . . ?
C6 C7 C8 121.7(3) . . ?
C29A N4A N3A 106.15(19) . . ?
C9 C8 C7 119.8(3) . . ?
C1A N2A C11A 116.8(2) . . ?
C1A N2A C13A 116.9(2) . . ?
C13A N2A C11A 114.51(19) . . ?
N1 C9 C10 117.8(2) . . ?
C8 C9 N1 122.8(3) . . ?
C8 C9 C10 119.3(3) . . ?
C28A N3A N4A 106.33(19) . . ?
C24A C23A C22A 120.6(2) . . ?
N1A C9A C10A 117.9(2) . . ?
C8A C9A N1A 122.6(2) . . ?
C8A C9A C10A 119.4(2) . . ?
O3A C29A C30A 118.0(2) . . ?
N4A C29A O3A 112.2(2) . . ?
N4A C29A C30A 129.7(2) . . ?
O3A C28A C25A 118.7(2) . . ?
N3A C28A O3A 112.4(2) . . ?
N3A C28A C25A 128.8(2) . . ?
C20A C15A C14A 110.2(2) . . ?
C16A C15A C14A 129.4(2) . . ?
C16A C15A C20A 120.3(2) . . ?
C17A C18A C22A 121.7(2) . . ?
C17A C18A C19A 118.7(2) . . ?
C19A C18A C22A 119.6(2) . . ?
C1 C10 C9 120.4(2) . . ?
C5 C10 C1 119.8(3) . . ?
C5 C10 C9 119.8(2) . . ?
N2A C1A C10A 118.4(2) . . ?
C2A C1A N2A 122.6(2) . . ?
C2A C1A C10A 119.0(2) . . ?
N1 C11 C14 111.60(18) . . ?
N1 C11 C21 108.99(19) . . ?
N2 C11 N1 110.40(19) . . ?
N2 C11 C14 113.34(19) . . ?
N2 C11 C21 109.69(18) . . ?
C14 C11 C21 102.48(18) . . ?
C23A C22A C18A 120.9(2) . . ?
C27A C22A C23A 118.3(2) . . ?
C27A C22A C18A 120.8(2) . . ?
O1 C14 C11 124.7(2) . . ?
O1 C14 C15 127.4(2) . . ?
C15 C14 C11 107.83(19) . . ?
O1A C14A C15A 127.2(2) . . ?
O1A C14A C11A 124.7(2) . . ?
C15A C14A C11A 108.07(19) . . ?
C16 C15 C14 129.3(2) . . ?
C16 C15 C20 120.0(2) . . ?
C20 C15 C14 110.8(2) . . ?
C31A C30A C29A 120.7(2) . . ?
C31A C30A C35A 119.4(2) . . ?
C35A C30A C29A 119.8(2) . . ?
C17 C16 C15 118.1(2) . . ?
C23A C24A C25A 120.5(2) . . ?
C16 C17 C18 122.5(2) . . ?
N1A C11A C14A 111.88(19) . . ?
N1A C11A C21A 109.49(19) . . ?
N2A C11A N1A 110.27(19) . . ?
N2A C11A C14A 112.47(19) . . ?
N2A C11A C21A 110.3(2) . . ?
C21A C11A C14A 102.16(19) . . ?
C17 C18 C22 120.2(2) . . ?
C19 C18 C17 118.7(2) . . ?
C19 C18 C22 121.1(2) . . ?
O2A C21A C11A 124.2(2) . . ?
O2A C21A C20A 127.4(2) . . ?
C20A C21A C11A 108.4(2) . . ?
C20 C19 C18 118.7(2) . . ?
C1A C10A C9A 120.4(2) . . ?
C5A C10A C9A 119.7(2) . . ?
C5A C10A C1A 119.8(2) . . ?
C24A C25A C28A 119.6(2) . . ?
C24A C25A C26A 119.7(2) . . ?
C26A C25A C28A 120.7(2) . . ?
C9A C8A C7A 120.1(2) . . ?
C6A C5A C10A 119.3(2) . . ?
C4A C5A C10A 118.8(2) . . ?
C4A C5A C6A 121.9(2) . . ?
C6A C7A C8A 121.5(2) . . ?
C15A C20A C21A 110.3(2) . . ?
C19A C20A C15A 121.5(2) . . ?
C19A C20A C21A 128.2(2) . . ?
C27A C26A C25A 119.7(2) . . ?
C32A C31A C30A 120.0(2) . . ?
C16A C17A C18A 122.7(2) . . ?
C7A C6A C5A 120.0(2) . . ?
C15A C16A C17A 118.1(2) . . ?
C20A C19A C18A 118.8(2) . . ?
C26A C27A C22A 121.3(2) . . ?
C34A C35A C30A 119.9(3) . . ?
C33A C32A C31A 120.3(3) . . ?
C15 C20 C21 110.0(2) . . ?
C19 C20 C15 121.8(2) . . ?
C19 C20 C21 128.1(2) . . ?
C1A C2A C3A 120.7(3) . . ?
O2 C21 C11 123.7(2) . . ?
O2 C21 C20 128.1(2) . . ?
C20 C21 C11 108.08(19) . . ?
C3A C4A C5A 120.4(3) . . ?
C23 C22 C18 120.4(2) . . ?
C27 C22 C18 121.4(2) . . ?
C27 C22 C23 118.2(2) . . ?
C4A C3A C2A 121.1(3) . . ?
C24 C23 C22 120.9(2) . . ?
C32A C33A C34A 120.1(3) . . ?
O3 C29 C30 118.7(2) . . ?
N4 C29 O3 112.4(2) . . ?
N4 C29 C30 128.9(2) . . ?
O3 C28 C25 119.2(2) . . ?
N3 C28 O3 112.7(2) . . ?
N3 C28 C25 128.1(2) . . ?
C26 C27 C22 120.9(2) . . ?
C27 C26 C25 120.5(2) . . ?
C26 C25 C28 122.7(2) . . ?
C26 C25 C24 119.1(2) . . ?
C24 C25 C28 118.2(2) . . ?
C23 C24 C25 120.5(2) . . ?
C35A C34A C33A 120.3(3) . . ?
C31 C30 C29 119.3(2) . . ?
C35 C30 C29 121.0(2) . . ?
C35 C30 C31 119.7(2) . . ?
C32 C31 C30 119.4(3) . . ?
C33 C32 C31 120.7(3) . . ?
C32 C33 C34 120.3(2) . . ?
C33 C34 C35 119.4(3) . . ?
C30 C35 C34 120.5(2) . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems 800'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_jw_74
_database_code_depnum_ccdc_archive 'CCDC 1582940'
loop_
_audit_author_name
_audit_author_address
'Daniel Kratzert' 'University of Freiburg'
_audit_update_record             
;
2017-10-30 deposited with the CCDC.	2019-09-30 downloaded from the CCDC.
;
_audit_creation_date             2017-10-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H16 N2 O2'
_chemical_formula_sum            'C21 H16 N2 O2'
_chemical_formula_weight         328.36
_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'
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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   16.5350(7)
_cell_length_b                   8.4288(4)
_cell_length_c                   22.1228(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3083.3(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7705
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.23
_cell_measurement_theta_min      2.22
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.967
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6167
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1620 before and 0.0701 after correction. The Ratio of minimum to maximum transmission is 0.8273. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1376
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'The material was recrystallised from a mixture of chloroform and n-hexane by solvent layering'
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            31576
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.458
_diffrn_reflns_theta_min         1.841
_diffrn_ambient_temperature      100.16
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'fixed-chi two circle goniometer'
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           50
_diffrn_source_type              'Incoatec Mo I\ms'
_diffrn_source_voltage           0.6
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2513
_reflns_number_total             3177
_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 V8.38A (Madison, 2016)'
_computing_data_collection       'Bruker APEXII'
_computing_data_reduction        'SAINT V8.38A (Madison, 2016)'
_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         0.362
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3177
_refine_ls_number_restraints     261
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0557
_refine_ls_restrained_S_all      1.045
_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)+(0.0704P)²+2.2213P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1381
_refine_ls_wR_factor_ref         0.1519
_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. Uiso/Uaniso restraints and constraints
C13 \\sim C14 \\sim C15 \\sim C16 \\sim C17 \\sim C18 \\sim C19: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C13, C14, C15, C16, C17, C18, C19
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
4.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C4(H4), C7(H7), C5(H5), C6(H6), C14(H14), C19(H19), C15(H15),
 C17(H17), C18(H18)
4.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C10(H10A,H10B,H10C)
;
_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
O1 O 0.48022(7) 0.18288(17) 0.52197(6) 0.0283(3) Uani 1 1 d . U . . .
N1 N 0.56859(9) 0.12107(18) 0.64465(7) 0.0211(4) Uani 1 1 d . U . . .
O2 O 0.71911(9) 0.3102(3) 0.62999(7) 0.0538(6) Uani 1 1 d . U . . .
N2 N 0.54504(11) 0.3943(2) 0.62108(8) 0.0308(4) Uani 1 1 d . U . . .
C9 C 0.55054(11) 0.1982(2) 0.53635(8) 0.0218(4) Uani 1 1 d . U . . .
C1 C 0.57997(10) 0.2469(2) 0.60055(8) 0.0216(4) Uani 1 1 d . U . . .
C12 C 0.49460(10) 0.1112(2) 0.67495(8) 0.0232(4) Uani 1 1 d . U . . .
C8 C 0.62233(11) 0.1815(2) 0.49694(8) 0.0239(4) Uani 1 1 d . U . . .
C21 C 0.44705(11) 0.2501(3) 0.67989(8) 0.0266(4) Uani 1 1 d . U . . .
C3 C 0.69202(11) 0.2304(2) 0.52744(9) 0.0268(4) Uani 1 1 d . U . . .
C20 C 0.47146(12) 0.3924(3) 0.65136(9) 0.0300(5) Uani 1 1 d . U . . .
C13 C 0.46924(12) -0.0269(3) 0.70279(9) 0.0333(5) Uani 1 1 d . U . . .
H13 H 0.499389 -0.121839 0.697529 0.040 Uiso 1 1 calc R . . . .
C4 C 0.76690(12) 0.2329(3) 0.49849(9) 0.0340(5) Uani 1 1 d . U . . .
H4 H 0.814037 0.268832 0.518874 0.041 Uiso 1 1 calc R . . . .
C2 C 0.67280(12) 0.2696(3) 0.59071(9) 0.0307(5) Uani 1 1 d . U . . .
C7 C 0.62645(12) 0.1282(3) 0.43792(9) 0.0321(5) Uani 1 1 d . U . . .
H7 H 0.579302 0.093292 0.417304 0.039 Uiso 1 1 calc R . . . .
C11 C 0.60959(13) -0.0267(3) 0.62991(9) 0.0316(5) Uani 1 1 d . U . . .
H11A H 0.577871 -0.085217 0.599845 0.047 Uiso 1 1 calc GR . . . .
H11B H 0.615212 -0.091169 0.666544 0.047 Uiso 1 1 calc GR . . . .
H11C H 0.663290 -0.003363 0.613418 0.047 Uiso 1 1 calc GR . . . .
C16 C 0.37525(11) 0.2463(3) 0.71569(9) 0.0423(6) Uani 1 1 d . U . . .
C5 C 0.77044(12) 0.1817(3) 0.43931(9) 0.0371(5) Uani 1 1 d . U . . .
H5 H 0.820643 0.183543 0.418437 0.045 Uiso 1 1 calc R . . . .
C6 C 0.70120(13) 0.1272(3) 0.40968(10) 0.0381(5) Uani 1 1 d . U . . .
H6 H 0.705463 0.088727 0.369440 0.046 Uiso 1 1 calc R . . . .
C14 C 0.39973(15) -0.0280(4) 0.73855(9) 0.0495(7) Uani 1 1 d . U . . .
H14 H 0.384222 -0.123216 0.758393 0.059 Uiso 1 1 calc R . . . .
C19 C 0.42404(16) 0.5271(3) 0.65779(11) 0.0483(6) Uani 1 1 d . U . . .
H19 H 0.438936 0.623558 0.638592 0.058 Uiso 1 1 calc R . . . .
C15 C 0.35395(14) 0.1038(4) 0.74553(10) 0.0538(7) Uani 1 1 d . U . . .
H15 H 0.307312 0.100716 0.770581 0.065 Uiso 1 1 calc R . . . .
C17 C 0.32914(15) 0.3840(5) 0.72166(12) 0.0608(8) Uani 1 1 d . U . . .
H17 H 0.281279 0.383112 0.745412 0.073 Uiso 1 1 calc R . . . .
C18 C 0.35273(16) 0.5183(4) 0.69360(12) 0.0627(8) Uani 1 1 d . U . . .
H18 H 0.320412 0.610822 0.697926 0.075 Uiso 1 1 calc R . . . .
C10 C 0.5660(2) 0.5348(3) 0.58652(13) 0.0598(8) Uani 1 1 d . U . . .
H10A H 0.618110 0.518139 0.566337 0.090 Uiso 1 1 calc GR . . . .
H10B H 0.570028 0.626159 0.613746 0.090 Uiso 1 1 calc GR . . . .
H10C H 0.524143 0.554890 0.556132 0.090 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
O1 C9 1.212(2) . ?
N1 C1 1.453(2) . ?
N1 C12 1.398(2) . ?
N1 C11 1.455(2) . ?
O2 C2 1.208(2) . ?
N2 C1 1.444(2) . ?
N2 C20 1.389(3) . ?
N2 C10 1.452(3) . ?
C9 C1 1.556(3) . ?
C9 C8 1.480(2) . ?
C1 C2 1.562(2) . ?
C12 C21 1.414(3) . ?
C12 C13 1.382(3) . ?
C8 C3 1.397(3) . ?
C8 C7 1.382(3) . ?
C21 C20 1.414(3) . ?
C21 C16 1.427(3) . ?
C3 C4 1.394(3) . ?
C3 C2 1.473(3) . ?
C20 C19 1.387(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.395(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.380(3) . ?
C7 H7 0.9500 . ?
C7 C6 1.385(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C16 C15 1.415(4) . ?
C16 C17 1.394(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.397(3) . ?
C6 H6 0.9500 . ?
C14 H14 0.9500 . ?
C14 C15 1.353(4) . ?
C19 H19 0.9500 . ?
C19 C18 1.422(4) . ?
C15 H15 0.9500 . ?
C17 H17 0.9500 . ?
C17 C18 1.349(5) . ?
C18 H18 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?

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 C11 114.46(15) . . ?
C12 N1 C1 118.59(15) . . ?
C12 N1 C11 117.68(16) . . ?
C1 N2 C10 116.15(17) . . ?
C20 N2 C1 119.48(16) . . ?
C20 N2 C10 118.2(2) . . ?
O1 C9 C1 124.56(16) . . ?
O1 C9 C8 127.22(17) . . ?
C8 C9 C1 108.17(14) . . ?
N1 C1 C9 112.31(15) . . ?
N1 C1 C2 108.07(15) . . ?
N2 C1 N1 111.42(14) . . ?
N2 C1 C9 112.90(15) . . ?
N2 C1 C2 109.36(16) . . ?
C9 C1 C2 102.26(14) . . ?
N1 C12 C21 118.34(17) . . ?
C13 C12 N1 121.95(19) . . ?
C13 C12 C21 119.61(18) . . ?
C3 C8 C9 110.43(16) . . ?
C7 C8 C9 128.82(17) . . ?
C7 C8 C3 120.74(17) . . ?
C12 C21 C16 119.1(2) . . ?
C20 C21 C12 120.58(17) . . ?
C20 C21 C16 120.3(2) . . ?
C8 C3 C2 110.31(16) . . ?
C4 C3 C8 121.00(18) . . ?
C4 C3 C2 128.67(18) . . ?
N2 C20 C21 118.37(17) . . ?
C19 C20 N2 122.4(2) . . ?
C19 C20 C21 119.1(2) . . ?
C12 C13 H13 119.7 . . ?
C12 C13 C14 120.5(2) . . ?
C14 C13 H13 119.7 . . ?
C3 C4 H4 121.0 . . ?
C5 C4 C3 117.96(18) . . ?
C5 C4 H4 121.0 . . ?
O2 C2 C1 123.88(18) . . ?
O2 C2 C3 127.63(18) . . ?
C3 C2 C1 108.48(16) . . ?
C8 C7 H7 120.9 . . ?
C8 C7 C6 118.17(19) . . ?
C6 C7 H7 120.9 . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C15 C16 C21 119.0(2) . . ?
C17 C16 C21 119.3(3) . . ?
C17 C16 C15 121.7(2) . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.89(18) . . ?
C6 C5 H5 119.6 . . ?
C7 C6 C5 121.17(19) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C13 C14 H14 119.3 . . ?
C15 C14 C13 121.3(2) . . ?
C15 C14 H14 119.3 . . ?
C20 C19 H19 120.5 . . ?
C20 C19 C18 118.9(3) . . ?
C18 C19 H19 120.5 . . ?
C16 C15 H15 119.9 . . ?
C14 C15 C16 120.3(2) . . ?
C14 C15 H15 119.9 . . ?
C16 C17 H17 120.1 . . ?
C18 C17 C16 119.8(2) . . ?
C18 C17 H17 120.1 . . ?
C19 C18 H18 118.7 . . ?
C17 C18 C19 122.6(2) . . ?
C17 C18 H18 118.7 . . ?
N2 C10 H10A 109.5 . . ?
N2 C10 H10B 109.5 . . ?
N2 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems 800'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_esser_jw136_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1856006'
_audit_update_record             
;
2018-07-16 deposited with the CCDC.	2019-09-30 downloaded from the CCDC.
;
_audit_creation_date             2018-07-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
daniel.kratzert@ac.uni-freiburg.de
besser@oc.uni-freiburg.de
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H19 N3 O2'
_chemical_formula_sum            'C28 H19 N3 O2'
_chemical_formula_weight         429.46
_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'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.360(5)
_cell_length_b                   9.772(4)
_cell_length_c                   13.225(6)
_cell_angle_alpha                79.646(11)
_cell_angle_beta                 71.931(19)
_cell_angle_gamma                81.249(16)
_cell_volume                     1004.9(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8694
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.491
_cell_measurement_theta_min      2.502
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7041
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0784 before and 0.0428 after correction. The Ratio of minimum to maximum transmission is 0.9443. 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    1.419
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             448
_exptl_crystal_recrystallization_method 
'The material was recrystallised from a mixture of DCM and methanol  by solvent layering'
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            25689
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.537
_diffrn_reflns_theta_min         1.636
_diffrn_ambient_temperature      99.96
_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 0.995
_diffrn_measurement_device       'fixed-chi two circle goniometer'
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           50
_diffrn_source_type              'Incoatec Mo I\ms'
_diffrn_source_voltage           0.6
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3897
_reflns_number_total             4614
_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 V8.38A (Madison, 2016)'
_computing_data_collection       'Bruker APEX2 software'
_computing_data_reduction        'SAINT V8.38A (Madison, 2016)'
_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         0.464
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         4614
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0511
_refine_ls_restrained_S_all      1.071
_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)+(0.0805P)²+0.4310P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1406
_refine_ls_wR_factor_ref         0.1468
_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:
 C4(H4), C7(H7), C6(H6), C11(H11), C12(H12), C14(H14), C15(H15), C20(H20),
 C21(H21), C22(H22), C24(H24), C25(H25), C26(H26)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_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
O1 O 0.37092(14) 0.47087(12) 0.42062(9) 0.0282(3) Uani 1 1 d . . . . .
N1 N 1.02427(18) -0.46190(14) 0.62519(11) 0.0254(3) Uani 1 1 d . . . . .
C1 C 0.50774(19) 0.59917(15) 0.24453(12) 0.0196(3) Uani 1 1 d . . . . .
O2 O 0.74035(15) 0.61413(12) 0.07394(9) 0.0281(3) Uani 1 1 d . . . . .
N2 N 0.52097(16) 0.72501(13) 0.28476(10) 0.0199(3) Uani 1 1 d . . . . .
C2 C 0.48747(19) 0.47505(16) 0.33955(12) 0.0203(3) Uani 1 1 d . . . . .
N3 N 0.36262(16) 0.61449(13) 0.20391(10) 0.0201(3) Uani 1 1 d . . . . .
C3 C 0.63401(18) 0.36828(15) 0.31002(12) 0.0186(3) Uani 1 1 d . . . . .
C4 C 0.66586(19) 0.24112(16) 0.37019(12) 0.0200(3) Uani 1 1 d . . . . .
H4 H 0.588438 0.212678 0.437824 0.024 Uiso 1 1 calc R . . . .
C5 C 0.81418(19) 0.15539(15) 0.32947(12) 0.0186(3) Uani 1 1 d . . . . .
C8 C 0.74418(19) 0.41271(15) 0.20953(12) 0.0188(3) Uani 1 1 d . . . . .
C7 C 0.89356(19) 0.32910(16) 0.16807(12) 0.0200(3) Uani 1 1 d . . . . .
H7 H 0.970218 0.357950 0.100232 0.024 Uiso 1 1 calc R . . . .
C6 C 0.92663(19) 0.20276(16) 0.22886(12) 0.0199(3) Uani 1 1 d . . . . .
H6 H 1.028692 0.145836 0.201934 0.024 Uiso 1 1 calc R . . . .
C9 C 0.67742(19) 0.54970(16) 0.16186(12) 0.0202(3) Uani 1 1 d . . . . .
C10 C 0.85436(19) 0.01815(15) 0.39136(12) 0.0188(3) Uani 1 1 d . . . . .
C11 C 0.78331(19) -0.00777(16) 0.50321(13) 0.0211(3) Uani 1 1 d . . . . .
H11 H 0.706304 0.062167 0.539347 0.025 Uiso 1 1 calc R . . . .
C12 C 0.82372(19) -0.13391(16) 0.56190(12) 0.0213(3) Uani 1 1 d . . . . .
H12 H 0.773516 -0.150633 0.637423 0.026 Uiso 1 1 calc R . . . .
C13 C 0.93912(19) -0.23635(15) 0.50888(12) 0.0193(3) Uani 1 1 d . . . . .
C14 C 1.01042(19) -0.21324(16) 0.39728(12) 0.0200(3) Uani 1 1 d . . . . .
H14 H 1.087997 -0.283009 0.361296 0.024 Uiso 1 1 calc R . . . .
C15 C 0.96659(19) -0.08732(16) 0.33978(12) 0.0199(3) Uani 1 1 d . . . . .
H15 H 1.013529 -0.072213 0.263920 0.024 Uiso 1 1 calc R . . . .
C16 C 0.98721(19) -0.36416(16) 0.57183(12) 0.0201(3) Uani 1 1 d . . . . .
C17 C 0.6584(2) 0.71141(17) 0.33376(13) 0.0245(3) Uani 1 1 d . . . . .
H17A H 0.764784 0.727836 0.277476 0.037 Uiso 1 1 calc GR . . . .
H17B H 0.668628 0.617007 0.373136 0.037 Uiso 1 1 calc GR . . . .
H17C H 0.633851 0.780274 0.383462 0.037 Uiso 1 1 calc GR . . . .
C18 C 0.3292(2) 0.48758(16) 0.17294(14) 0.0243(3) Uani 1 1 d . . . . .
H18A H 0.396750 0.479413 0.098672 0.036 Uiso 1 1 calc GR . . . .
H18B H 0.208758 0.492625 0.178632 0.036 Uiso 1 1 calc GR . . . .
H18C H 0.359582 0.405743 0.220769 0.036 Uiso 1 1 calc GR . . . .
C19 C 0.48676(18) 0.85500(15) 0.22703(12) 0.0186(3) Uani 1 1 d . . . . .
C20 C 0.5476(2) 0.97459(16) 0.23655(13) 0.0219(3) Uani 1 1 d . . . . .
H20 H 0.622010 0.968614 0.279154 0.026 Uiso 1 1 calc R . . . .
C21 C 0.4995(2) 1.10508(16) 0.18329(13) 0.0229(3) Uani 1 1 d . . . . .
H21 H 0.541545 1.186374 0.191148 0.028 Uiso 1 1 calc R . . . .
C22 C 0.3938(2) 1.11779(16) 0.12046(13) 0.0215(3) Uani 1 1 d . . . . .
H22 H 0.361220 1.207208 0.086406 0.026 Uiso 1 1 calc R . . . .
C23 C 0.33310(18) 0.99697(16) 0.10650(12) 0.0190(3) Uani 1 1 d . . . . .
C24 C 0.2269(2) 1.00460(16) 0.04011(12) 0.0219(3) Uani 1 1 d . . . . .
H24 H 0.193784 1.092439 0.004107 0.026 Uiso 1 1 calc R . . . .
C25 C 0.1719(2) 0.88540(17) 0.02787(13) 0.0235(3) Uani 1 1 d . . . . .
H25 H 0.100530 0.891834 -0.016794 0.028 Uiso 1 1 calc R . . . .
C26 C 0.2185(2) 0.75340(17) 0.07982(13) 0.0228(3) Uani 1 1 d . . . . .
H26 H 0.179475 0.672125 0.069372 0.027 Uiso 1 1 calc R . . . .
C27 C 0.32091(18) 0.74177(15) 0.14604(12) 0.0187(3) Uani 1 1 d . . . . .
C28 C 0.37999(18) 0.86426(15) 0.16015(12) 0.0179(3) Uani 1 1 d . . . . .


_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 C2 1.204(2) . ?
N1 C16 1.144(2) . ?
C1 N2 1.456(2) . ?
C1 C2 1.569(2) . ?
C1 N3 1.450(2) . ?
C1 C9 1.569(2) . ?
O2 C9 1.2179(19) . ?
N2 C17 1.464(2) . ?
N2 C19 1.3980(19) . ?
C2 C3 1.484(2) . ?
N3 C18 1.464(2) . ?
N3 C27 1.3948(19) . ?
C3 C4 1.387(2) . ?
C3 C8 1.399(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.400(2) . ?
C5 C6 1.415(2) . ?
C5 C10 1.490(2) . ?
C8 C7 1.398(2) . ?
C8 C9 1.479(2) . ?
C7 H7 0.9500 . ?
C7 C6 1.387(2) . ?
C6 H6 0.9500 . ?
C10 C11 1.404(2) . ?
C10 C15 1.403(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.389(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.401(2) . ?
C13 C14 1.400(2) . ?
C13 C16 1.448(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.388(2) . ?
C15 H15 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.383(2) . ?
C19 C28 1.422(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.407(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.369(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.416(2) . ?
C23 C24 1.416(2) . ?
C23 C28 1.423(2) . ?
C24 H24 0.9500 . ?
C24 C25 1.368(2) . ?
C25 H25 0.9500 . ?
C25 C26 1.408(2) . ?
C26 H26 0.9500 . ?
C26 C27 1.383(2) . ?
C27 C28 1.424(2) . ?

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
N2 C1 C2 108.29(12) . . ?
N2 C1 C9 111.94(13) . . ?
C2 C1 C9 102.62(11) . . ?
N3 C1 N2 111.77(12) . . ?
N3 C1 C2 108.58(12) . . ?
N3 C1 C9 113.09(13) . . ?
C1 N2 C17 113.90(12) . . ?
C19 N2 C1 118.50(12) . . ?
C19 N2 C17 116.96(13) . . ?
O1 C2 C1 124.28(13) . . ?
O1 C2 C3 127.82(14) . . ?
C3 C2 C1 107.89(12) . . ?
C1 N3 C18 115.25(12) . . ?
C27 N3 C1 119.25(13) . . ?
C27 N3 C18 117.05(13) . . ?
C4 C3 C2 127.26(14) . . ?
C4 C3 C8 122.12(14) . . ?
C8 C3 C2 110.62(13) . . ?
C3 C4 H4 120.6 . . ?
C3 C4 C5 118.82(14) . . ?
C5 C4 H4 120.6 . . ?
C4 C5 C6 118.59(13) . . ?
C4 C5 C10 120.81(14) . . ?
C6 C5 C10 120.59(13) . . ?
C3 C8 C9 110.85(13) . . ?
C7 C8 C3 119.84(13) . . ?
C7 C8 C9 129.32(14) . . ?
C8 C7 H7 121.0 . . ?
C6 C7 C8 118.07(14) . . ?
C6 C7 H7 121.0 . . ?
C5 C6 H6 118.7 . . ?
C7 C6 C5 122.54(14) . . ?
C7 C6 H6 118.7 . . ?
O2 C9 C1 125.07(14) . . ?
O2 C9 C8 126.95(14) . . ?
C8 C9 C1 107.97(12) . . ?
C11 C10 C5 120.72(14) . . ?
C15 C10 C5 120.93(14) . . ?
C15 C10 C11 118.33(13) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 C10 121.10(14) . . ?
C12 C11 H11 119.4 . . ?
C11 C12 H12 120.3 . . ?
C11 C12 C13 119.49(14) . . ?
C13 C12 H12 120.3 . . ?
C12 C13 C16 118.86(14) . . ?
C14 C13 C12 120.38(13) . . ?
C14 C13 C16 120.73(14) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 C13 119.30(14) . . ?
C15 C14 H14 120.4 . . ?
C10 C15 H15 119.3 . . ?
C14 C15 C10 121.38(14) . . ?
C14 C15 H15 119.3 . . ?
N1 C16 C13 177.00(16) . . ?
N2 C17 H17A 109.5 . . ?
N2 C17 H17B 109.5 . . ?
N2 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N3 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
N3 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N2 C19 C28 118.36(13) . . ?
C20 C19 N2 122.08(14) . . ?
C20 C19 C28 119.51(13) . . ?
C19 C20 H20 119.9 . . ?
C19 C20 C21 120.18(15) . . ?
C21 C20 H20 119.9 . . ?
C20 C21 H21 119.2 . . ?
C22 C21 C20 121.64(15) . . ?
C22 C21 H21 119.2 . . ?
C21 C22 H22 120.2 . . ?
C21 C22 C23 119.64(14) . . ?
C23 C22 H22 120.2 . . ?
C22 C23 C24 121.62(14) . . ?
C22 C23 C28 119.41(14) . . ?
C24 C23 C28 118.97(14) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 C23 119.95(14) . . ?
C25 C24 H24 120.0 . . ?
C24 C25 H25 119.2 . . ?
C24 C25 C26 121.61(15) . . ?
C26 C25 H25 119.2 . . ?
C25 C26 H26 119.9 . . ?
C27 C26 C25 120.16(15) . . ?
C27 C26 H26 119.9 . . ?
N3 C27 C28 118.34(13) . . ?
C26 C27 N3 122.23(14) . . ?
C26 C27 C28 119.36(13) . . ?
C19 C28 C23 119.59(14) . . ?
C19 C28 C27 120.48(13) . . ?
C23 C28 C27 119.94(14) . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems 800'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_esser_jw222_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1855187'
_audit_update_record             
;
2018-07-11 deposited with the CCDC.	2019-09-30 downloaded from the CCDC.
;
_audit_creation_date             2018-07-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
besser@oc.uni-freiburg.de
daniel.kratzert@ac.uni-freiburg.de
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H16 Br2 N2 O2'
_chemical_formula_sum            'C23 H16 Br2 N2 O2'
_chemical_formula_weight         512.20
_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'
Br Br -0.2901 2.4595 '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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.667(4)
_cell_length_b                   9.231(3)
_cell_length_c                   15.139(4)
_cell_angle_alpha                90
_cell_angle_beta                 107.187(8)
_cell_angle_gamma                90
_cell_volume                     1958.2(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9961
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.532
_cell_measurement_theta_min      2.622
_shelx_estimated_absorpt_T_max   0.681
_shelx_estimated_absorpt_T_min   0.399
_exptl_absorpt_coefficient_mu    4.163
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5345
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0881 before and 0.0342 after correction. The Ratio of minimum to maximum transmission is 0.7169. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.737
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1016
_exptl_crystal_recrystallization_method 
'The material was recrystallised from a mixture of DCM and methanol  by solvent layering'
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            21928
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         1.699
_diffrn_ambient_temperature      100.03
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'fixed-chi two circle goniometer'
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           50
_diffrn_source_type              'Incoatec Mo I\ms'
_diffrn_source_voltage           0.6
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4043
_reflns_number_total             4475
_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 V8.38A (Madison, 2016)'
_computing_data_collection       'Bruker APEX2 software'
_computing_data_reduction        'SAINT V8.38A (Madison, 2016)'
_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         0.462
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4475
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0254
_refine_ls_R_factor_gt           0.0212
_refine_ls_restrained_S_all      1.052
_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)+(0.0216P)²+1.6088P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0497
_refine_ls_wR_factor_ref         0.0510
_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:
 C4(H4), C5(H5), C6(H6), C7(H7), C13(H13), C14(H14), C16(H16), C19(H19),
 C21(H21), C22(H22)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_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
Br1 Br 0.20369(2) 1.21202(2) 0.72712(2) 0.01891(5) Uani 1 1 d . . . . .
Br2 Br 0.64669(2) 0.85062(2) 0.59955(2) 0.01730(5) Uani 1 1 d . . . . .
O1 O 0.28745(8) 0.56223(14) 0.33950(8) 0.0141(2) Uani 1 1 d . . . . .
O2 O 0.02489(9) 0.64095(13) 0.45689(8) 0.0158(3) Uani 1 1 d . . . . .
N1 N 0.18566(10) 0.79638(15) 0.40854(9) 0.0105(3) Uani 1 1 d . . . . .
N2 N 0.24301(10) 0.61025(15) 0.52479(9) 0.0105(3) Uani 1 1 d . . . . .
C1 C 0.18265(11) 0.64299(18) 0.43056(11) 0.0102(3) Uani 1 1 d . . . . .
C2 C 0.21243(12) 0.55004(18) 0.35701(11) 0.0114(3) Uani 1 1 d . . . . .
C3 C 0.13596(12) 0.44288(19) 0.31759(11) 0.0125(3) Uani 1 1 d . . . . .
C4 C 0.13353(13) 0.3345(2) 0.25287(12) 0.0175(4) Uani 1 1 d . . . . .
H4 H 0.184582 0.322407 0.226853 0.021 Uiso 1 1 calc R . . . .
C5 C 0.05412(14) 0.2451(2) 0.22769(13) 0.0210(4) Uani 1 1 d . . . . .
H5 H 0.050621 0.170476 0.183580 0.025 Uiso 1 1 calc R . . . .
C6 C -0.02155(14) 0.2629(2) 0.26648(13) 0.0216(4) Uani 1 1 d . . . . .
H6 H -0.074599 0.198957 0.248925 0.026 Uiso 1 1 calc R . . . .
C7 C -0.01988(13) 0.3723(2) 0.32984(12) 0.0172(4) Uani 1 1 d . . . . .
H7 H -0.071247 0.385104 0.355342 0.021 Uiso 1 1 calc R . . . .
C8 C 0.05976(12) 0.46261(19) 0.35475(11) 0.0133(3) Uani 1 1 d . . . . .
C9 C 0.07942(12) 0.58655(19) 0.42006(11) 0.0120(3) Uani 1 1 d . . . . .
C10 C 0.12191(13) 0.8331(2) 0.31645(11) 0.0157(4) Uani 1 1 d . . . . .
H10A H 0.134938 0.932317 0.300511 0.024 Uiso 1 1 calc GR . . . .
H10B H 0.055377 0.825761 0.316857 0.024 Uiso 1 1 calc GR . . . .
H10C H 0.132929 0.765793 0.270608 0.024 Uiso 1 1 calc GR . . . .
C11 C 0.23262(13) 0.46158(19) 0.55515(12) 0.0150(3) Uani 1 1 d . . . . .
H11A H 0.165479 0.443040 0.550095 0.023 Uiso 1 1 calc GR . . . .
H11B H 0.271477 0.449601 0.619605 0.023 Uiso 1 1 calc GR . . . .
H11C H 0.253989 0.392956 0.516011 0.023 Uiso 1 1 calc GR . . . .
C12 C 0.18828(12) 0.89859(18) 0.47989(11) 0.0107(3) Uani 1 1 d . . . . .
C13 C 0.11537(12) 0.99781(19) 0.47435(12) 0.0144(3) Uani 1 1 d . . . . .
H13 H 0.061032 0.998447 0.421266 0.017 Uiso 1 1 calc R . . . .
C14 C 0.12090(13) 1.0963(2) 0.54558(12) 0.0157(4) Uani 1 1 d . . . . .
H14 H 0.070945 1.163951 0.541263 0.019 Uiso 1 1 calc R . . . .
C15 C 0.20036(13) 1.09402(19) 0.62269(11) 0.0139(3) Uani 1 1 d . . . . .
C16 C 0.27688(12) 1.00352(19) 0.62706(11) 0.0123(3) Uani 1 1 d . . . . .
H16 H 0.332517 1.007534 0.678768 0.015 Uiso 1 1 calc R . . . .
C17 C 0.27187(12) 0.90648(18) 0.55519(11) 0.0107(3) Uani 1 1 d . . . . .
C18 C 0.35420(12) 0.81165(19) 0.55878(11) 0.0109(3) Uani 1 1 d . . . . .
C19 C 0.44609(12) 0.86843(19) 0.57721(11) 0.0125(3) Uani 1 1 d . . . . .
H19 H 0.456299 0.970031 0.583362 0.015 Uiso 1 1 calc R . . . .
C20 C 0.52247(12) 0.7748(2) 0.58647(11) 0.0131(3) Uani 1 1 d . . . . .
C21 C 0.50977(12) 0.6260(2) 0.58451(11) 0.0146(3) Uani 1 1 d . . . . .
H21 H 0.563261 0.562911 0.596808 0.018 Uiso 1 1 calc R . . . .
C22 C 0.41786(12) 0.5698(2) 0.56433(11) 0.0137(3) Uani 1 1 d . . . . .
H22 H 0.408746 0.467853 0.562465 0.016 Uiso 1 1 calc R . . . .
C23 C 0.33920(12) 0.66124(19) 0.54686(11) 0.0109(3) Uani 1 1 d . . . . .


_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
Br1 C15 1.9086(17) . ?
Br2 C20 1.9067(18) . ?
O1 C2 1.211(2) . ?
O2 C9 1.211(2) . ?
N1 C1 1.458(2) . ?
N1 C10 1.471(2) . ?
N1 C12 1.426(2) . ?
N2 C1 1.471(2) . ?
N2 C11 1.470(2) . ?
N2 C23 1.430(2) . ?
C1 C2 1.567(2) . ?
C1 C9 1.564(2) . ?
C2 C3 1.482(2) . ?
C3 C4 1.393(2) . ?
C3 C8 1.403(2) . ?
C4 C5 1.386(3) . ?
C5 C6 1.410(3) . ?
C6 C7 1.388(3) . ?
C7 C8 1.393(3) . ?
C8 C9 1.484(2) . ?
C12 C13 1.392(2) . ?
C12 C17 1.408(2) . ?
C13 C14 1.395(2) . ?
C14 C15 1.385(2) . ?
C15 C16 1.385(2) . ?
C16 C17 1.394(2) . ?
C17 C18 1.479(2) . ?
C18 C19 1.395(2) . ?
C18 C23 1.409(2) . ?
C19 C20 1.389(2) . ?
C20 C21 1.385(3) . ?
C21 C22 1.391(3) . ?
C22 C23 1.390(2) . ?

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 C10 112.77(13) . . ?
C12 N1 C1 117.72(13) . . ?
C12 N1 C10 115.64(14) . . ?
C11 N2 C1 114.01(13) . . ?
C23 N2 C1 115.37(13) . . ?
C23 N2 C11 114.87(13) . . ?
N1 C1 N2 111.78(13) . . ?
N1 C1 C2 109.61(13) . . ?
N1 C1 C9 113.19(13) . . ?
N2 C1 C2 111.25(13) . . ?
N2 C1 C9 108.50(13) . . ?
C9 C1 C2 102.13(13) . . ?
O1 C2 C1 124.54(15) . . ?
O1 C2 C3 127.04(15) . . ?
C3 C2 C1 108.35(14) . . ?
C4 C3 C2 128.40(16) . . ?
C4 C3 C8 121.14(16) . . ?
C8 C3 C2 110.46(15) . . ?
C5 C4 C3 117.76(17) . . ?
C4 C5 C6 121.10(17) . . ?
C7 C6 C5 121.17(17) . . ?
C6 C7 C8 117.68(17) . . ?
C3 C8 C9 110.26(15) . . ?
C7 C8 C3 121.13(16) . . ?
C7 C8 C9 128.61(16) . . ?
O2 C9 C1 124.49(15) . . ?
O2 C9 C8 127.01(16) . . ?
C8 C9 C1 108.43(14) . . ?
C13 C12 N1 122.79(15) . . ?
C13 C12 C17 118.98(15) . . ?
C17 C12 N1 118.01(14) . . ?
C12 C13 C14 120.97(16) . . ?
C15 C14 C13 118.95(16) . . ?
C14 C15 Br1 119.91(13) . . ?
C14 C15 C16 121.19(15) . . ?
C16 C15 Br1 118.86(13) . . ?
C15 C16 C17 119.68(15) . . ?
C12 C17 C18 120.35(15) . . ?
C16 C17 C12 119.83(15) . . ?
C16 C17 C18 119.82(15) . . ?
C19 C18 C17 120.98(15) . . ?
C19 C18 C23 120.05(15) . . ?
C23 C18 C17 118.92(15) . . ?
C20 C19 C18 119.27(16) . . ?
C19 C20 Br2 119.95(14) . . ?
C21 C20 Br2 118.99(13) . . ?
C21 C20 C19 121.05(16) . . ?
C20 C21 C22 119.30(16) . . ?
C23 C22 C21 120.76(17) . . ?
C18 C23 N2 117.40(15) . . ?
C22 C23 N2 123.41(16) . . ?
C22 C23 C18 118.98(16) . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems 800'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_esser_jw307_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1898124'
_audit_update_record             
;
2019-02-19 deposited with the CCDC.	2019-09-30 downloaded from the CCDC.
;
_audit_creation_date             2019-02-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
daniel.kratzert@ac.uni-freiburg.de
besser@oc.uni-freiburg.de
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H18 N2 O2'
_chemical_formula_sum            'C25 H18 N2 O2'
_chemical_formula_weight         378.41
_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'
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      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   18.714(3)
_cell_length_b                   15.974(3)
_cell_length_c                   12.0964(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3616.1(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4577
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.099
_cell_measurement_theta_min      2.178
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.991
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7044
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0791 before and 0.0518 after correction. The Ratio of minimum to maximum transmission is 0.9447. 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    1.390
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1584
_exptl_crystal_recrystallization_method 
'The material was recrystallised from a mixture of CCl4 and MeOH  by solvent layering'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            28900
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.486
_diffrn_reflns_theta_min         1.676
_diffrn_ambient_temperature      99.99
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'fixed-chi two circle goniometer'
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           50
_diffrn_source_type              'Incoatec Mo I\ms'
_diffrn_source_voltage           0.6
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3172
_reflns_number_total             4129
_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 V8.38A (Madison, 2016)'
_computing_data_collection       'Bruker APEX2 software'
_computing_data_reduction        'SAINT V8.38A (Madison, 2016)'
_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 (Sheldrick, 2015)'
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4129
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0423
_refine_ls_restrained_S_all      1.028
_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)+(0.0452P)²+1.9498P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0983
_refine_ls_wR_factor_ref         0.1090
_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:
 C4(H4), C7(H7), C6(H6), C8(H8), C9(H9), C11(H11), C15(H15), C16(H16),
 C17(H17), C19(H19), C20(H20), C21(H21)
2.b Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C25(H25A,H25B,H25C)
;
_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
O1 O 0.54474(6) 0.61204(7) 0.60435(9) 0.0225(3) Uani 1 1 d . . . . .
N1 N 0.70447(7) 0.64963(8) 0.58737(10) 0.0172(3) Uani 1 1 d . . . . .
C1 C 0.66791(8) 0.60243(9) 0.67369(12) 0.0159(3) Uani 1 1 d . . . . .
N2 N 0.66338(6) 0.65274(8) 0.77417(10) 0.0155(3) Uani 1 1 d . . . . .
O2 O 0.77181(6) 0.52078(7) 0.73305(9) 0.0220(3) Uani 1 1 d . . . . .
C2 C 0.59368(8) 0.56865(9) 0.63628(12) 0.0162(3) Uani 1 1 d . . . . .
C3 C 0.59488(8) 0.47633(9) 0.64477(12) 0.0152(3) Uani 1 1 d . . . . .
C4 C 0.54154(8) 0.42013(9) 0.62075(12) 0.0165(3) Uani 1 1 d . . . . .
H4 H 0.495952 0.439300 0.597252 0.020 Uiso 1 1 calc R . . . .
C5 C 0.55523(8) 0.33327(9) 0.63140(12) 0.0163(3) Uani 1 1 d . . . . .
C7 C 0.51767(9) 0.18880(10) 0.61377(13) 0.0221(3) Uani 1 1 d . . . . .
H7 H 0.482075 0.148670 0.595704 0.026 Uiso 1 1 calc R . . . .
C6 C 0.50257(9) 0.27244(10) 0.60460(12) 0.0197(3) Uani 1 1 d . . . . .
H6 H 0.456670 0.289873 0.580193 0.024 Uiso 1 1 calc R . . . .
C8 C 0.58559(9) 0.16164(10) 0.64981(13) 0.0232(4) Uani 1 1 d . . . . .
H8 H 0.595267 0.103427 0.655673 0.028 Uiso 1 1 calc R . . . .
C9 C 0.63762(9) 0.21844(10) 0.67639(13) 0.0203(3) Uani 1 1 d . . . . .
H9 H 0.682987 0.199205 0.700832 0.024 Uiso 1 1 calc R . . . .
C10 C 0.62458(8) 0.30556(10) 0.66787(12) 0.0171(3) Uani 1 1 d . . . . .
C11 C 0.67832(8) 0.36512(10) 0.69230(12) 0.0170(3) Uani 1 1 d . . . . .
H11 H 0.724188 0.347442 0.716524 0.020 Uiso 1 1 calc R . . . .
C12 C 0.66332(8) 0.44862(9) 0.68056(12) 0.0156(3) Uani 1 1 d . . . . .
C13 C 0.71066(8) 0.52128(9) 0.70012(12) 0.0161(3) Uani 1 1 d . . . . .
C14 C 0.68267(8) 0.73256(10) 0.56946(12) 0.0178(3) Uani 1 1 d . . . . .
C15 C 0.69622(8) 0.77465(10) 0.47191(13) 0.0218(3) Uani 1 1 d . . . . .
H15 H 0.718948 0.746406 0.412404 0.026 Uiso 1 1 calc R . . . .
C16 C 0.67643(9) 0.85949(10) 0.46032(14) 0.0240(4) Uani 1 1 d . . . . .
H16 H 0.686594 0.887924 0.393167 0.029 Uiso 1 1 calc R . . . .
C17 C 0.64291(8) 0.90138(10) 0.54398(14) 0.0224(3) Uani 1 1 d . . . . .
H17 H 0.629493 0.958249 0.534082 0.027 Uiso 1 1 calc R . . . .
C18 C 0.62797(8) 0.86052(10) 0.64571(13) 0.0193(3) Uani 1 1 d . . . . .
C19 C 0.59462(8) 0.90205(10) 0.73518(14) 0.0230(3) Uani 1 1 d . . . . .
H19 H 0.580406 0.958852 0.727550 0.028 Uiso 1 1 calc R . . . .
C20 C 0.58275(9) 0.86106(10) 0.83227(14) 0.0242(4) Uani 1 1 d . . . . .
H20 H 0.560232 0.889846 0.891506 0.029 Uiso 1 1 calc R . . . .
C21 C 0.60321(8) 0.77684(10) 0.84659(13) 0.0213(3) Uani 1 1 d . . . . .
H21 H 0.594053 0.749227 0.914691 0.026 Uiso 1 1 calc R . . . .
C22 C 0.63660(8) 0.73452(9) 0.76144(12) 0.0163(3) Uani 1 1 d . . . . .
C23 C 0.64870(8) 0.77555(9) 0.65864(12) 0.0165(3) Uani 1 1 d . . . . .
C24 C 0.63969(8) 0.60754(9) 0.87325(12) 0.0189(3) Uani 1 1 d . . . . .
H24A H 0.587376 0.604782 0.874195 0.028 Uiso 1 1 calc GR . . . .
H24B H 0.656528 0.636980 0.939383 0.028 Uiso 1 1 calc GR . . . .
H24C H 0.659339 0.550679 0.872332 0.028 Uiso 1 1 calc GR . . . .
C25 C 0.72807(9) 0.60214(10) 0.49082(13) 0.0235(4) Uani 1 1 d . . . . .
H25A H 0.689735 0.600945 0.435639 0.035 Uiso 1 1 calc GR . . . .
H25B H 0.739818 0.544789 0.513099 0.035 Uiso 1 1 calc GR . . . .
H25C H 0.770474 0.628842 0.458941 0.035 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
O1 C2 1.2118(18) . ?
N1 C1 1.4583(19) . ?
N1 C14 1.403(2) . ?
N1 C25 1.4610(19) . ?
C1 N2 1.4596(19) . ?
C1 C2 1.557(2) . ?
C1 C13 1.557(2) . ?
N2 C22 1.4075(19) . ?
N2 C24 1.4678(19) . ?
O2 C13 1.2117(18) . ?
C2 C3 1.479(2) . ?
C3 C4 1.374(2) . ?
C3 C12 1.423(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.417(2) . ?
C5 C6 1.421(2) . ?
C5 C10 1.441(2) . ?
C7 H7 0.9500 . ?
C7 C6 1.370(2) . ?
C7 C8 1.412(2) . ?
C6 H6 0.9500 . ?
C8 H8 0.9500 . ?
C8 C9 1.369(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.417(2) . ?
C10 C11 1.416(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.370(2) . ?
C12 C13 1.479(2) . ?
C14 C15 1.382(2) . ?
C14 C23 1.428(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.412(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.366(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.421(2) . ?
C18 C19 1.415(2) . ?
C18 C23 1.420(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.363(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.409(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.382(2) . ?
C22 C23 1.424(2) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?

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 C25 116.47(12) . . ?
C14 N1 C1 117.54(12) . . ?
C14 N1 C25 117.05(12) . . ?
N1 C1 N2 109.81(12) . . ?
N1 C1 C2 112.93(12) . . ?
N1 C1 C13 109.66(12) . . ?
N2 C1 C2 112.39(12) . . ?
N2 C1 C13 108.50(12) . . ?
C13 C1 C2 103.27(12) . . ?
C1 N2 C24 115.26(12) . . ?
C22 N2 C1 116.14(12) . . ?
C22 N2 C24 116.00(12) . . ?
O1 C2 C1 124.65(13) . . ?
O1 C2 C3 127.16(14) . . ?
C3 C2 C1 108.17(12) . . ?
C4 C3 C2 128.77(14) . . ?
C4 C3 C12 121.02(14) . . ?
C12 C3 C2 110.19(13) . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.30(14) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 C6 121.56(14) . . ?
C4 C5 C10 119.45(13) . . ?
C6 C5 C10 118.98(14) . . ?
C6 C7 H7 119.7 . . ?
C6 C7 C8 120.69(15) . . ?
C8 C7 H7 119.7 . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.34(15) . . ?
C7 C6 H6 119.8 . . ?
C7 C8 H8 119.7 . . ?
C9 C8 C7 120.60(15) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 H9 119.6 . . ?
C8 C9 C10 120.75(15) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 C5 118.65(14) . . ?
C11 C10 C5 119.83(14) . . ?
C11 C10 C9 121.51(14) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 C10 119.15(14) . . ?
C12 C11 H11 120.4 . . ?
C3 C12 C13 110.11(13) . . ?
C11 C12 C3 121.25(14) . . ?
C11 C12 C13 128.64(14) . . ?
O2 C13 C1 123.95(14) . . ?
O2 C13 C12 127.81(14) . . ?
C12 C13 C1 108.22(12) . . ?
N1 C14 C23 117.83(13) . . ?
C15 C14 N1 122.55(14) . . ?
C15 C14 C23 119.53(14) . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.24(15) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 119.4 . . ?
C17 C16 C15 121.15(15) . . ?
C17 C16 H16 119.4 . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C18 120.46(15) . . ?
C18 C17 H17 119.8 . . ?
C19 C18 C17 122.28(15) . . ?
C19 C18 C23 118.98(14) . . ?
C23 C18 C17 118.73(14) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 C18 120.39(15) . . ?
C20 C19 H19 119.8 . . ?
C19 C20 H20 119.3 . . ?
C19 C20 C21 121.35(15) . . ?
C21 C20 H20 119.3 . . ?
C20 C21 H21 120.1 . . ?
C22 C21 C20 119.89(15) . . ?
C22 C21 H21 120.1 . . ?
N2 C22 C23 117.79(13) . . ?
C21 C22 N2 122.25(14) . . ?
C21 C22 C23 119.86(14) . . ?
C18 C23 C14 119.86(14) . . ?
C18 C23 C22 119.52(14) . . ?
C22 C23 C14 120.61(14) . . ?
N2 C24 H24A 109.5 . . ?
N2 C24 H24B 109.5 . . ?
N2 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N1 C25 H25A 109.5 . . ?
N1 C25 H25B 109.5 . . ?
N1 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

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
O1 C2 C3 C4 -1.2(3) . . . . ?
O1 C2 C3 C12 177.05(15) . . . . ?
N1 C1 N2 C22 50.22(16) . . . . ?
N1 C1 N2 C24 -169.29(12) . . . . ?
N1 C1 C2 O1 -58.95(19) . . . . ?
N1 C1 C2 C3 119.94(13) . . . . ?
N1 C1 C13 O2 59.86(19) . . . . ?
N1 C1 C13 C12 -121.46(13) . . . . ?
N1 C14 C15 C16 -176.66(14) . . . . ?
N1 C14 C23 C18 177.79(13) . . . . ?
N1 C14 C23 C22 -1.0(2) . . . . ?
C1 N1 C14 C15 -159.58(14) . . . . ?
C1 N1 C14 C23 23.90(19) . . . . ?
C1 N2 C22 C21 153.85(14) . . . . ?
C1 N2 C22 C23 -29.90(18) . . . . ?
C1 C2 C3 C4 179.90(14) . . . . ?
C1 C2 C3 C12 -1.81(16) . . . . ?
N2 C1 C2 O1 65.95(19) . . . . ?
N2 C1 C2 C3 -115.16(13) . . . . ?
N2 C1 C13 O2 -60.07(18) . . . . ?
N2 C1 C13 C12 118.60(13) . . . . ?
N2 C22 C23 C14 4.1(2) . . . . ?
N2 C22 C23 C18 -174.65(13) . . . . ?
C2 C1 N2 C22 -76.37(15) . . . . ?
C2 C1 N2 C24 64.11(16) . . . . ?
C2 C1 C13 O2 -179.52(14) . . . . ?
C2 C1 C13 C12 -0.85(15) . . . . ?
C2 C3 C4 C5 177.83(14) . . . . ?
C2 C3 C12 C11 -178.46(13) . . . . ?
C2 C3 C12 C13 1.26(17) . . . . ?
C3 C4 C5 C6 -178.18(14) . . . . ?
C3 C4 C5 C10 0.4(2) . . . . ?
C3 C12 C13 C1 -0.21(16) . . . . ?
C3 C12 C13 O2 178.40(15) . . . . ?
C4 C3 C12 C11 0.0(2) . . . . ?
C4 C3 C12 C13 179.71(13) . . . . ?
C4 C5 C6 C7 178.82(14) . . . . ?
C4 C5 C10 C9 -179.05(13) . . . . ?
C4 C5 C10 C11 -0.2(2) . . . . ?
C5 C10 C11 C12 -0.1(2) . . . . ?
C7 C8 C9 C10 -0.3(2) . . . . ?
C6 C5 C10 C9 -0.4(2) . . . . ?
C6 C5 C10 C11 178.42(13) . . . . ?
C6 C7 C8 C9 0.1(2) . . . . ?
C8 C7 C6 C5 -0.1(2) . . . . ?
C8 C9 C10 C5 0.5(2) . . . . ?
C8 C9 C10 C11 -178.37(14) . . . . ?
C9 C10 C11 C12 178.70(14) . . . . ?
C10 C5 C6 C7 0.2(2) . . . . ?
C10 C11 C12 C3 0.2(2) . . . . ?
C10 C11 C12 C13 -179.45(14) . . . . ?
C11 C12 C13 C1 179.50(14) . . . . ?
C11 C12 C13 O2 -1.9(3) . . . . ?
C12 C3 C4 C5 -0.3(2) . . . . ?
C13 C1 N2 C22 170.07(12) . . . . ?
C13 C1 N2 C24 -49.45(16) . . . . ?
C13 C1 C2 O1 -177.32(14) . . . . ?
C13 C1 C2 C3 1.57(15) . . . . ?
C14 N1 C1 N2 -47.38(17) . . . . ?
C14 N1 C1 C2 78.91(16) . . . . ?
C14 N1 C1 C13 -166.52(12) . . . . ?
C14 C15 C16 C17 -0.8(2) . . . . ?
C15 C14 C23 C18 1.2(2) . . . . ?
C15 C14 C23 C22 -177.60(14) . . . . ?
C15 C16 C17 C18 0.8(2) . . . . ?
C16 C17 C18 C19 178.75(15) . . . . ?
C16 C17 C18 C23 0.2(2) . . . . ?
C17 C18 C19 C20 -178.47(15) . . . . ?
C17 C18 C23 C14 -1.1(2) . . . . ?
C17 C18 C23 C22 177.64(14) . . . . ?
C18 C19 C20 C21 0.1(3) . . . . ?
C19 C18 C23 C14 -179.78(14) . . . . ?
C19 C18 C23 C22 -1.0(2) . . . . ?
C19 C20 C21 C22 0.6(2) . . . . ?
C20 C21 C22 N2 174.69(14) . . . . ?
C20 C21 C22 C23 -1.5(2) . . . . ?
C21 C22 C23 C14 -179.54(14) . . . . ?
C21 C22 C23 C18 1.7(2) . . . . ?
C23 C14 C15 C16 -0.2(2) . . . . ?
C23 C18 C19 C20 0.1(2) . . . . ?
C24 N2 C22 C21 13.7(2) . . . . ?
C24 N2 C22 C23 -170.09(13) . . . . ?
C25 N1 C1 N2 166.26(12) . . . . ?
C25 N1 C1 C2 -67.45(17) . . . . ?
C25 N1 C1 C13 47.13(17) . . . . ?
C25 N1 C14 C15 -13.4(2) . . . . ?
C25 N1 C14 C23 170.06(13) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems 800'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_special_instructions 'No special instructions were received'
