# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_solv_i
_database_code_depnum_ccdc_archive 'CCDC 1942397'
loop_
_audit_author_name
_audit_author_address
'Niklas Grabicki'
;Humboldt University
Germany
;
_audit_update_record             
;
2019-07-22 deposited with the CCDC.	2023-10-18 downloaded from the CCDC.
;
_audit_creation_date             2019-07-22
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C42 H24 F12 N2'
_chemical_formula_sum            'C42 H24 F12 N2'
_chemical_formula_weight         784.63
_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'
F F 0.0171 0.0103 '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'

_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                   5.5923(4)
_cell_length_b                   10.4164(7)
_cell_length_c                   14.6091(11)
_cell_angle_alpha                80.515(4)
_cell_angle_beta                 85.368(4)
_cell_angle_gamma                83.032(4)
_cell_volume                     831.56(10)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3743
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.102
_cell_measurement_theta_min      2.833
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.948
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6796
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1042 before and 0.0608 after correction.
The Ratio of minimum to maximum transmission is 0.9120.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             398
_exptl_crystal_preparation       Synthesis
_exptl_crystal_recrystallization_method 
'recrystalization from ortho-Dichlorobenzene'
_exptl_crystal_size_max          0.388
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.114
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0781
_diffrn_reflns_av_unetI/netI     0.0584
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_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            13993
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.372
_diffrn_reflns_theta_min         2.258
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2175
_reflns_number_total             3048
_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 (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 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         0.329
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.067
_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     253
_refine_ls_number_reflns         3048
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0875
_refine_ls_R_factor_gt           0.0547
_refine_ls_restrained_S_all      1.030
_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)+(0.0558P)²+0.6503P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1151
_refine_ls_wR_factor_ref         0.1280
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C21(H21), C2(H2), C3(H3), C5(H5), C6(H6), C13(H13), C20(H20), C10(H10),
 C9(H9), C17(H17), C12(H12), C18(H18)
;
_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
N1 N 0.7428(4) 0.5533(2) 0.09908(16) 0.0151(5) Uani 1 1 d . . . . .
C1 C 0.6204(5) 0.3718(2) 0.20544(18) 0.0129(6) Uani 1 1 d . . . . .
C16 C 0.8165(5) 0.6809(2) 0.07343(18) 0.0140(6) Uani 1 1 d . . . . .
C8 C 0.7775(5) 0.5596(2) 0.26638(18) 0.0134(6) Uani 1 1 d . . . . .
C21 C 1.0310(5) 0.6971(2) 0.02019(18) 0.0149(6) Uani 1 1 d . . . . .
H21 H 1.129359 0.622947 0.002737 0.018 Uiso 1 1 calc R . . . .
C19 C 0.9608(5) 0.9334(2) 0.01452(18) 0.0131(6) Uani 1 1 d . . . . .
C2 C 0.7068(5) 0.2762(3) 0.27709(19) 0.0157(6) Uani 1 1 d . . . . .
H2 H 0.831776 0.292829 0.312472 0.019 Uiso 1 1 calc R . . . .
C15 C 0.7195(5) 0.5010(2) 0.18466(19) 0.0134(6) Uani 1 1 d . . . . .
C3 C 0.6119(5) 0.1573(3) 0.29711(19) 0.0166(6) Uani 1 1 d . . . . .
H3 H 0.672977 0.091977 0.345452 0.020 Uiso 1 1 calc R . . . .
C5 C 0.3414(5) 0.2278(3) 0.17418(19) 0.0153(6) Uani 1 1 d . . . . .
H5 H 0.216409 0.210582 0.139053 0.018 Uiso 1 1 calc R . . . .
C6 C 0.4371(5) 0.3461(3) 0.15339(19) 0.0147(6) Uani 1 1 d . . . . .
H6 H 0.378510 0.410110 0.103791 0.018 Uiso 1 1 calc R . . . .
C13 C 0.6155(5) 0.5548(3) 0.34424(19) 0.0158(6) Uani 1 1 d . . . . .
H13 H 0.478216 0.508562 0.346723 0.019 Uiso 1 1 calc R . . . .
C14 C 0.8885(5) 0.7511(3) 0.49499(19) 0.0200(7) Uani 1 1 d . . . . .
C20 C 1.1016(5) 0.8212(2) -0.00748(18) 0.0149(6) Uani 1 1 d . . . . .
H20 H 1.250815 0.830377 -0.042593 0.018 Uiso 1 1 calc R . . . .
C10 C 1.0222(5) 0.6835(2) 0.34050(19) 0.0153(6) Uani 1 1 d . . . . .
H10 H 1.163075 0.726313 0.339683 0.018 Uiso 1 1 calc R . . . .
C9 C 0.9841(5) 0.6232(2) 0.26579(19) 0.0149(6) Uani 1 1 d . . . . .
H9 H 1.098795 0.625155 0.214077 0.018 Uiso 1 1 calc R . . . .
C17 C 0.6711(5) 0.7907(3) 0.09493(19) 0.0162(6) Uani 1 1 d . . . . .
H17 H 0.521983 0.781187 0.130062 0.019 Uiso 1 1 calc R . . . .
C11 C 0.8571(5) 0.6816(2) 0.41578(19) 0.0159(6) Uani 1 1 d . . . . .
C12 C 0.6526(5) 0.6167(3) 0.41809(19) 0.0167(6) Uani 1 1 d . . . . .
H12 H 0.538925 0.614856 0.470121 0.020 Uiso 1 1 calc R . . . .
C4 C 0.4275(5) 0.1341(3) 0.24623(19) 0.0156(6) Uani 1 1 d . . . . .
C18 C 0.7424(5) 0.9144(3) 0.06537(19) 0.0160(6) Uani 1 1 d . . . . .
H18 H 0.639399 0.988535 0.080181 0.019 Uiso 1 1 calc R . . . .
C7 C 0.3161(5) 0.0082(3) 0.27269(19) 0.0174(6) Uani 1 1 d . . . . .
F6 F 0.2016(3) -0.02234(16) 0.20341(12) 0.0311(5) Uani 1 1 d . . . . .
F4 F 0.4777(3) -0.09400(15) 0.29845(13) 0.0316(5) Uani 1 1 d . . . . .
F3 F 0.8275(3) 0.68180(18) 0.57756(11) 0.0319(5) Uani 1 1 d . . . . .
F5 F 0.1520(3) 0.01304(16) 0.34425(12) 0.0297(5) Uani 1 1 d . . . . .
F2 F 1.1157(3) 0.77642(18) 0.49908(12) 0.0316(5) Uani 1 1 d . . . . .
F1 F 0.7517(4) 0.86595(17) 0.48949(13) 0.0410(5) 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
N1 C16 1.421(3) . ?
N1 C15 1.282(3) . ?
C1 C2 1.393(4) . ?
C1 C15 1.493(3) . ?
C1 C6 1.400(4) . ?
C16 C21 1.388(4) . ?
C16 C17 1.386(4) . ?
C8 C15 1.501(4) . ?
C8 C13 1.394(4) . ?
C8 C9 1.399(4) . ?
C21 C20 1.385(4) . ?
C19 C19 1.490(5) 2_775 ?
C19 C20 1.396(4) . ?
C19 C18 1.395(4) . ?
C2 C3 1.385(4) . ?
C3 C4 1.385(4) . ?
C5 C6 1.382(4) . ?
C5 C4 1.386(4) . ?
C13 C12 1.386(4) . ?
C14 C11 1.495(4) . ?
C14 F3 1.341(3) . ?
C14 F2 1.336(3) . ?
C14 F1 1.334(3) . ?
C10 C9 1.388(4) . ?
C10 C11 1.377(4) . ?
C17 C18 1.385(4) . ?
C11 C12 1.393(4) . ?
C4 C7 1.499(4) . ?
C7 F6 1.340(3) . ?
C7 F4 1.335(3) . ?
C7 F5 1.338(3) . ?

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
C15 N1 C16 121.1(2) . . ?
C2 C1 C15 120.6(2) . . ?
C2 C1 C6 119.3(2) . . ?
C6 C1 C15 120.0(2) . . ?
C21 C16 N1 119.4(2) . . ?
C17 C16 N1 121.4(2) . . ?
C17 C16 C21 119.0(2) . . ?
C13 C8 C15 118.9(2) . . ?
C13 C8 C9 118.8(2) . . ?
C9 C8 C15 122.3(2) . . ?
C20 C21 C16 120.0(2) . . ?
C20 C19 C19 121.9(3) . 2_775 ?
C18 C19 C19 121.6(3) . 2_775 ?
C18 C19 C20 116.5(2) . . ?
C3 C2 C1 120.5(2) . . ?
N1 C15 C1 117.4(2) . . ?
N1 C15 C8 125.8(2) . . ?
C1 C15 C8 116.9(2) . . ?
C2 C3 C4 119.6(3) . . ?
C6 C5 C4 120.1(2) . . ?
C5 C6 C1 120.0(3) . . ?
C12 C13 C8 120.7(2) . . ?
F3 C14 C11 112.2(2) . . ?
F2 C14 C11 112.9(2) . . ?
F2 C14 F3 106.4(2) . . ?
F1 C14 C11 111.9(2) . . ?
F1 C14 F3 106.5(2) . . ?
F1 C14 F2 106.5(2) . . ?
C21 C20 C19 122.2(2) . . ?
C11 C10 C9 120.5(2) . . ?
C10 C9 C8 120.2(3) . . ?
C18 C17 C16 120.2(2) . . ?
C10 C11 C14 121.4(2) . . ?
C10 C11 C12 120.0(3) . . ?
C12 C11 C14 118.6(3) . . ?
C13 C12 C11 119.8(3) . . ?
C3 C4 C5 120.5(2) . . ?
C3 C4 C7 118.9(2) . . ?
C5 C4 C7 120.5(2) . . ?
C17 C18 C19 122.1(3) . . ?
F6 C7 C4 112.9(2) . . ?
F4 C7 C4 112.8(2) . . ?
F4 C7 F6 106.5(2) . . ?
F4 C7 F5 106.2(2) . . ?
F5 C7 C4 111.9(2) . . ?
F5 C7 F6 106.1(2) . . ?

_olex2_submission_original_sample_id MJE-04
_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_p-1_gni001b
_database_code_depnum_ccdc_archive 'CCDC 2240743'
loop_
_audit_author_name
_audit_author_address
'Oliver Dumele'
;Humboldt University Berlin
Germany
;
_audit_update_record             
;
2023-07-10 deposited with the CCDC.	2023-10-18 downloaded from the CCDC.
;
_audit_creation_date             2023-02-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C38 H28 N2'
_chemical_formula_sum            'C38 H28 N2'
_chemical_formula_weight         512.62
_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'

_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                   9.5460(18)
_cell_length_b                   15.907(3)
_cell_length_c                   18.545(4)
_cell_angle_alpha                88.246(4)
_cell_angle_beta                 81.362(4)
_cell_angle_gamma                89.566(4)
_cell_volume                     2782.8(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4723
_cell_measurement_temperature    100
_cell_measurement_theta_max      21.34
_cell_measurement_theta_min      2.22
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6334
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1161 before and 0.0844 after correction. The Ratio of minimum to maximum transmission is 0.8497. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1080
_exptl_crystal_preparation       synthetic
_exptl_crystal_recrystallization_method 'slow evaporation'
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.4000
_diffrn_reflns_av_unetI/netI     0.3408
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            86855
_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         26.552
_diffrn_reflns_theta_min         2.158
_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 0.995
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4041
_reflns_number_total             11521
_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 (2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (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    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     721
_refine_ls_number_reflns         11521
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.3014
_refine_ls_R_factor_gt           0.0955
_refine_ls_restrained_S_all      0.977
_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)+(0.0757P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1513
_refine_ls_wR_factor_ref         0.2133
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00G(H00G), C00I(H00I), C00J(H00J), C00N(H00N), C00O(H00O),
 C00P(H00P), C00R(H00R), C00S(H00S), C00U(H00U), C00V(H00V), C00W(H00W),
 C00X(H00X), C00Y(H00Y), C010(H010), C011(H011), C012(H012), C014(H014),
 C016(H016), C017(H017), C018(H018), C019(H019), C01A(H01A), C01B(H01B),
 C01C(H01C), C01D(H01D), C01E(H01E), C01F(H01F), C01G(H01G), C01H(H01H),
 C01I(H01I), C01J(H01J), C01K(H01K), C01L(H01L), C01M(H01M), C01N(H01N),
 C01O(H01O), C01P(H01P), C01Q(H01Q), C01R(H01R), C01S(H01S), C01T(H01T),
 C01U(H01U), C01W(H01W), C01X(H01X), C01Y(H01Y), C01Z(H01Z), C020(H020),
 C021(H021), C022(H022), C023(H023), C024(H024), C025(H025), C026(H026),
 C027(H027), C028(H028)
;
_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
N001 N 0.7615(4) 0.4947(2) 1.0521(2) 0.0215(10) Uani 1 1 d . . . . .
N002 N 0.6952(4) 0.2591(2) 0.5666(2) 0.0217(10) Uani 1 1 d . . . . .
N003 N 0.7457(4) 1.0166(2) 0.0677(2) 0.0284(11) Uani 1 1 d . . . . .
N004 N 0.8268(4) 0.7444(2) 0.5498(2) 0.0279(11) Uani 1 1 d . . . . .
C005 C 0.7222(5) 0.3607(3) 0.7725(2) 0.0156(11) Uani 1 1 d . . . . .
C006 C 0.7767(5) 0.8598(3) 0.3462(2) 0.0185(11) Uani 1 1 d . . . . .
C007 C 0.7506(5) 0.4540(3) 0.9858(2) 0.0192(11) Uani 1 1 d . . . . .
C008 C 0.6611(5) 0.3743(3) 1.1268(2) 0.0200(12) Uani 1 1 d . . . . .
C009 C 0.7047(5) 0.2993(3) 0.6327(2) 0.0177(11) Uani 1 1 d . . . . .
C00A C 0.7218(5) 0.2467(3) 0.4384(2) 0.0195(12) Uani 1 1 d . . . . .
C00B C 0.6593(5) 0.8441(3) 0.3992(2) 0.0235(12) Uani 1 1 d . . . . .
H00B H 0.567554 0.858487 0.388756 0.028 Uiso 1 1 calc R . . . .
C00C C 0.8059(5) 0.7869(3) 0.4833(3) 0.0234(12) Uani 1 1 d . . . . .
C00D C 0.7326(5) 0.3920(3) 0.8466(2) 0.0164(11) Uani 1 1 d . . . . .
C00E C 0.7128(5) 0.4620(3) 1.1156(3) 0.0206(12) Uani 1 1 d . . . . .
C00F C 0.7197(5) 0.5153(3) 1.1801(2) 0.0209(12) Uani 1 1 d . . . . .
C00G C 0.6439(5) 0.9240(3) 0.1693(3) 0.0272(13) Uani 1 1 d . . . . .
H00G H 0.564092 0.914048 0.145713 0.033 Uiso 1 1 calc R . . . .
C00H C 0.7212(5) 0.2971(3) 0.5045(2) 0.0188(11) Uani 1 1 d . . . . .
C00I C 0.8602(5) 0.4180(3) 0.8660(2) 0.0236(12) Uani 1 1 d . . . . .
H00I H 0.944276 0.413238 0.831781 0.028 Uiso 1 1 calc R . . . .
C00J C 0.5992(5) 0.3256(3) 0.7563(2) 0.0239(12) Uani 1 1 d . . . . .
H00J H 0.518193 0.322151 0.792908 0.029 Uiso 1 1 calc R . . . .
C00K C 0.7779(5) 0.8742(3) 0.6157(2) 0.0217(12) Uani 1 1 d . . . . .
C00L C 0.7656(5) 0.9010(3) 0.2743(2) 0.0210(12) Uani 1 1 d . . . . .
C00M C 0.8421(5) 0.7363(3) 0.6772(2) 0.0234(12) Uani 1 1 d . . . . .
C00N C 0.6136(5) 0.3961(3) 0.9008(2) 0.0231(12) Uani 1 1 d . . . . .
H00N H 0.524466 0.377982 0.890277 0.028 Uiso 1 1 calc R . . . .
C00O C 0.7265(5) 0.1509(3) 0.3141(3) 0.0296(13) Uani 1 1 d . . . . .
H00O H 0.729373 0.118193 0.271933 0.036 Uiso 1 1 calc R . . . .
C00P C 0.6227(5) 0.4258(3) 0.9690(2) 0.0238(12) Uani 1 1 d . . . . .
H00P H 0.540372 0.426989 1.004781 0.029 Uiso 1 1 calc R . . . .
C00Q C 0.8154(5) 0.7839(3) 0.6096(3) 0.0223(12) Uani 1 1 d . . . . .
C00R C 0.7619(5) 0.5981(3) 1.1700(3) 0.0260(13) Uani 1 1 d . . . . .
H00R H 0.783513 0.621303 1.121796 0.031 Uiso 1 1 calc R . . . .
C00S C 0.6507(5) 0.8872(3) 0.2373(2) 0.0267(13) Uani 1 1 d . . . . .
H00S H 0.575634 0.851806 0.259450 0.032 Uiso 1 1 calc R . . . .
C00T C 0.7791(5) 0.8820(3) 0.0063(2) 0.0260(13) Uani 1 1 d . . . . .
C00U C 0.8687(5) 0.4504(3) 0.9334(2) 0.0242(12) Uani 1 1 d . . . . .
H00U H 0.956922 0.470495 0.943656 0.029 Uiso 1 1 calc R . . . .
C00V C 0.8703(5) 0.9544(3) 0.2400(2) 0.0260(12) Uani 1 1 d . . . . .
H00V H 0.949304 0.965483 0.263897 0.031 Uiso 1 1 calc R . . . .
C00W C 0.7519(5) 0.3087(3) 1.1068(2) 0.0230(12) Uani 1 1 d . . . . .
H00W H 0.847256 0.320614 1.086415 0.028 Uiso 1 1 calc R . . . .
C00X C 0.9222(6) 0.8005(3) 0.4313(3) 0.0323(14) Uani 1 1 d . . . . .
H00X H 1.013648 0.785080 0.441558 0.039 Uiso 1 1 calc R . . . .
C00Y C 0.5220(5) 0.3559(3) 1.1575(2) 0.0285(13) Uani 1 1 d . . . . .
H00Y H 0.457995 0.400172 1.172656 0.034 Uiso 1 1 calc R . . . .
C00Z C 0.7522(5) 0.9749(3) 0.1354(2) 0.0225(12) Uani 1 1 d . . . . .
C010 C 0.7734(5) 0.6482(3) 1.2290(3) 0.0265(13) Uani 1 1 d . . . . .
H010 H 0.804797 0.704722 1.221409 0.032 Uiso 1 1 calc R . . . .
C011 C 0.8357(5) 0.3654(3) 0.7163(2) 0.0257(13) Uani 1 1 d . . . . .
H011 H 0.921749 0.389947 0.725126 0.031 Uiso 1 1 calc R . . . .
C012 C 0.7077(5) 0.2841(3) 0.3712(2) 0.0293(13) Uani 1 1 d . . . . .
H012 H 0.695928 0.343340 0.367437 0.035 Uiso 1 1 calc R . . . .
C013 C 0.7538(5) 0.3880(3) 0.4926(2) 0.0233(12) Uani 1 1 d . . . . .
C014 C 0.5917(5) 0.2954(3) 0.6881(2) 0.0265(13) Uani 1 1 d . . . . .
H014 H 0.505563 0.271125 0.679109 0.032 Uiso 1 1 calc R . . . .
C015 C 0.7423(5) 1.0206(3) -0.0616(3) 0.0235(12) Uani 1 1 d . . . . .
C016 C 0.7557(5) 0.9798(3) -0.1271(3) 0.0302(13) Uani 1 1 d . . . . .
H016 H 0.766518 0.920378 -0.127999 0.036 Uiso 1 1 calc R . . . .
C017 C 0.9077(5) 0.8364(3) 0.3639(3) 0.0280(13) Uani 1 1 d . . . . .
H017 H 0.989874 0.845294 0.328784 0.034 Uiso 1 1 calc R . . . .
C018 C 0.6731(5) 0.8077(3) 0.4672(2) 0.0266(13) Uani 1 1 d . . . . .
H018 H 0.591352 0.797209 0.502345 0.032 Uiso 1 1 calc R . . . .
C019 C 0.8765(5) 0.4136(3) 0.4468(3) 0.0314(13) Uani 1 1 d . . . . .
H019 H 0.937920 0.372617 0.422700 0.038 Uiso 1 1 calc R . . . .
C01A C 0.6437(5) 0.8971(3) 0.6473(3) 0.0327(14) Uani 1 1 d . . . . .
H01A H 0.578054 0.855129 0.667885 0.039 Uiso 1 1 calc R . . . .
C01B C 0.8920(5) 0.7785(3) 0.7328(3) 0.0317(13) Uani 1 1 d . . . . .
H01B H 0.904595 0.837690 0.728756 0.038 Uiso 1 1 calc R . . . .
C01C C 0.8211(5) 0.6512(3) 0.6843(3) 0.0303(13) Uani 1 1 d . . . . .
H01C H 0.785598 0.622337 0.646828 0.036 Uiso 1 1 calc R . . . .
C01D C 0.7106(5) 0.2366(3) 0.3096(3) 0.0321(13) Uani 1 1 d . . . . .
H01D H 0.701546 0.263481 0.264058 0.038 Uiso 1 1 calc R . . . .
C01E C 0.7350(5) 0.1599(3) 0.4422(3) 0.0271(13) Uani 1 1 d . . . . .
H01E H 0.742022 0.132208 0.487617 0.032 Uiso 1 1 calc R . . . .
C01F C 0.7360(5) 1.1123(3) -0.1917(3) 0.0316(14) Uani 1 1 d . . . . .
H01F H 0.734843 1.143045 -0.236295 0.038 Uiso 1 1 calc R . . . .
C01G C 0.6981(6) 0.5335(3) 0.5167(3) 0.0324(14) Uani 1 1 d . . . . .
H01G H 0.636350 0.574662 0.540374 0.039 Uiso 1 1 calc R . . . .
C01H C 0.7214(5) 1.1078(3) -0.0616(3) 0.0310(13) Uani 1 1 d . . . . .
H01H H 0.707736 1.136239 -0.016770 0.037 Uiso 1 1 calc R . . . .
C01I C 0.8277(5) 0.3357(3) 0.6483(3) 0.0296(13) Uani 1 1 d . . . . .
H01I H 0.907854 0.340287 0.611220 0.036 Uiso 1 1 calc R . . . .
C01J C 0.7206(5) 1.1528(3) -0.1267(3) 0.0337(14) Uani 1 1 d . . . . .
H01J H 0.709279 1.212209 -0.126286 0.040 Uiso 1 1 calc R . . . .
C01K C 0.8339(6) 1.0207(3) 0.5921(3) 0.0334(14) Uani 1 1 d . . . . .
H01K H 0.900211 1.063135 0.573505 0.040 Uiso 1 1 calc R . . . .
C01L C 0.6655(5) 0.4493(3) 0.5272(2) 0.0287(13) Uani 1 1 d . . . . .
H01L H 0.581473 0.432851 0.558564 0.034 Uiso 1 1 calc R . . . .
C01M C 0.7083(6) 0.2259(3) 1.1156(2) 0.0296(13) Uani 1 1 d . . . . .
H01M H 0.773002 0.181483 1.101776 0.036 Uiso 1 1 calc R . . . .
C01N C 0.9232(5) 0.7347(3) 0.7939(3) 0.0381(15) Uani 1 1 d . . . . .
H01N H 0.958694 0.763521 0.831458 0.046 Uiso 1 1 calc R . . . .
C01O C 0.8508(5) 0.6071(3) 0.7453(3) 0.0388(15) Uani 1 1 d . . . . .
H01O H 0.835884 0.548025 0.749660 0.047 Uiso 1 1 calc R . . . .
C01P C 0.6839(5) 0.4828(3) 1.2508(2) 0.0298(13) Uani 1 1 d . . . . .
H01P H 0.652730 0.426280 1.258703 0.036 Uiso 1 1 calc R . . . .
C01Q C 0.7386(5) 0.6142(3) 1.2986(3) 0.0319(14) Uani 1 1 d . . . . .
H01Q H 0.745861 0.647890 1.339318 0.038 Uiso 1 1 calc R . . . .
C01R C 0.8209(6) 0.5581(3) 0.4718(3) 0.0363(14) Uani 1 1 d . . . . .
H01R H 0.844390 0.616020 0.465250 0.044 Uiso 1 1 calc R . . . .
C01S C 0.8646(5) 0.9921(3) 0.1725(3) 0.0290(13) Uani 1 1 d . . . . .
H01S H 0.937259 1.029673 0.151382 0.035 Uiso 1 1 calc R . . . .
C01T C 0.7380(5) 0.1133(3) 0.3803(3) 0.0311(13) Uani 1 1 d . . . . .
H01T H 0.748338 0.053929 0.383812 0.037 Uiso 1 1 calc R . . . .
C01U C 0.4771(6) 0.2733(3) 1.1659(3) 0.0339(14) Uani 1 1 d . . . . .
H01U H 0.381962 0.260849 1.186316 0.041 Uiso 1 1 calc R . . . .
C01V C 0.7517(5) 0.9738(3) 0.0091(3) 0.0253(12) Uani 1 1 d . . . . .
C01W C 0.8737(5) 0.9363(3) 0.5884(3) 0.0319(13) Uani 1 1 d . . . . .
H01W H 0.966876 0.921396 0.566928 0.038 Uiso 1 1 calc R . . . .
C01X C 0.9095(6) 0.4979(3) 0.4363(3) 0.0354(14) Uani 1 1 d . . . . .
H01X H 0.992945 0.514670 0.404722 0.042 Uiso 1 1 calc R . . . .
C01Y C 0.6785(6) 0.8253(3) -0.0096(2) 0.0331(14) Uani 1 1 d . . . . .
H01Y H 0.587717 0.844334 -0.018253 0.040 Uiso 1 1 calc R . . . .
C01Z C 0.7001(6) 1.0423(3) 0.6224(3) 0.0332(14) Uani 1 1 d . . . . .
H01Z H 0.672946 1.099891 0.624858 0.040 Uiso 1 1 calc R . . . .
C020 C 0.6936(6) 0.5329(3) 1.3098(3) 0.0374(15) Uani 1 1 d . . . . .
H020 H 0.669007 0.510539 1.358143 0.045 Uiso 1 1 calc R . . . .
C021 C 0.5705(6) 0.2086(3) 1.1445(3) 0.0351(14) Uani 1 1 d . . . . .
H021 H 0.538909 0.151938 1.149969 0.042 Uiso 1 1 calc R . . . .
C022 C 0.7532(5) 1.0260(4) -0.1911(3) 0.0368(14) Uani 1 1 d . . . . .
H022 H 0.763637 0.997699 -0.235940 0.044 Uiso 1 1 calc R . . . .
C023 C 0.6041(6) 0.9807(3) 0.6493(3) 0.0399(15) Uani 1 1 d . . . . .
H023 H 0.510161 0.995773 0.669397 0.048 Uiso 1 1 calc R . . . .
C024 C 0.9097(6) 0.8516(3) 0.0210(2) 0.0347(14) Uani 1 1 d . . . . .
H024 H 0.977796 0.889842 0.033131 0.042 Uiso 1 1 calc R . . . .
C025 C 0.9026(5) 0.6488(4) 0.8002(3) 0.0414(15) Uani 1 1 d . . . . .
H025 H 0.923800 0.618344 0.842142 0.050 Uiso 1 1 calc R . . . .
C026 C 0.7132(7) 0.7402(4) -0.0127(3) 0.0450(16) Uani 1 1 d . . . . .
H026 H 0.645238 0.701311 -0.023951 0.054 Uiso 1 1 calc R . . . .
C027 C 0.8420(7) 0.7115(4) 0.0002(3) 0.0481(17) Uani 1 1 d . . . . .
H027 H 0.863572 0.653188 -0.003286 0.058 Uiso 1 1 calc R . . . .
C028 C 0.9419(6) 0.7667(4) 0.0182(3) 0.0433(15) Uani 1 1 d . . . . .
H028 H 1.030953 0.746606 0.028491 0.052 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
N001 C007 1.425(5) . ?
N001 C00E 1.295(5) . ?
N002 C009 1.415(5) . ?
N002 C00H 1.275(5) . ?
N003 C00Z 1.412(5) . ?
N003 C01V 1.293(5) . ?
N004 C00C 1.428(5) . ?
N004 C00Q 1.280(5) . ?
C005 C00D 1.493(6) . ?
C005 C00J 1.380(6) . ?
C005 C011 1.387(6) . ?
C006 C00B 1.394(6) . ?
C006 C00L 1.485(6) . ?
C006 C017 1.385(6) . ?
C007 C00P 1.386(6) . ?
C007 C00U 1.376(6) . ?
C008 C00E 1.482(6) . ?
C008 C00W 1.375(6) . ?
C008 C00Y 1.393(6) . ?
C009 C014 1.374(6) . ?
C009 C01I 1.386(6) . ?
C00A C00H 1.483(6) . ?
C00A C012 1.389(6) . ?
C00A C01E 1.387(6) . ?
C00B H00B 0.9500 . ?
C00B C018 1.396(6) . ?
C00C C00X 1.371(6) . ?
C00C C018 1.381(6) . ?
C00D C00I 1.390(6) . ?
C00D C00N 1.402(6) . ?
C00E C00F 1.497(6) . ?
C00F C00R 1.378(6) . ?
C00F C01P 1.389(6) . ?
C00G H00G 0.9500 . ?
C00G C00S 1.385(6) . ?
C00G C00Z 1.381(6) . ?
C00H C013 1.485(6) . ?
C00I H00I 0.9500 . ?
C00I C00U 1.380(6) . ?
C00J H00J 0.9500 . ?
C00J C014 1.379(6) . ?
C00K C00Q 1.482(6) . ?
C00K C01A 1.378(6) . ?
C00K C01W 1.383(6) . ?
C00L C00S 1.400(6) . ?
C00L C00V 1.383(6) . ?
C00M C00Q 1.498(6) . ?
C00M C01B 1.391(6) . ?
C00M C01C 1.370(6) . ?
C00N H00N 0.9500 . ?
C00N C00P 1.378(6) . ?
C00O H00O 0.9500 . ?
C00O C01D 1.371(6) . ?
C00O C01T 1.368(6) . ?
C00P H00P 0.9500 . ?
C00R H00R 0.9500 . ?
C00R C010 1.391(6) . ?
C00S H00S 0.9500 . ?
C00T C01V 1.483(6) . ?
C00T C01Y 1.393(6) . ?
C00T C024 1.396(6) . ?
C00U H00U 0.9500 . ?
C00V H00V 0.9500 . ?
C00V C01S 1.380(6) . ?
C00W H00W 0.9500 . ?
C00W C01M 1.382(6) . ?
C00X H00X 0.9500 . ?
C00X C017 1.383(6) . ?
C00Y H00Y 0.9500 . ?
C00Y C01U 1.383(6) . ?
C00Z C01S 1.391(6) . ?
C010 H010 0.9500 . ?
C010 C01Q 1.378(6) . ?
C011 H011 0.9500 . ?
C011 C01I 1.373(6) . ?
C012 H012 0.9500 . ?
C012 C01D 1.386(6) . ?
C013 C019 1.394(6) . ?
C013 C01L 1.391(6) . ?
C014 H014 0.9500 . ?
C015 C016 1.383(6) . ?
C015 C01H 1.399(6) . ?
C015 C01V 1.502(6) . ?
C016 H016 0.9500 . ?
C016 C022 1.380(6) . ?
C017 H017 0.9500 . ?
C018 H018 0.9500 . ?
C019 H019 0.9500 . ?
C019 C01X 1.381(6) . ?
C01A H01A 0.9500 . ?
C01A C023 1.379(6) . ?
C01B H01B 0.9500 . ?
C01B C01N 1.382(6) . ?
C01C H01C 0.9500 . ?
C01C C01O 1.377(6) . ?
C01D H01D 0.9500 . ?
C01E H01E 0.9500 . ?
C01E C01T 1.381(6) . ?
C01F H01F 0.9500 . ?
C01F C01J 1.372(6) . ?
C01F C022 1.381(6) . ?
C01G H01G 0.9500 . ?
C01G C01L 1.379(6) . ?
C01G C01R 1.383(7) . ?
C01H H01H 0.9500 . ?
C01H C01J 1.385(6) . ?
C01I H01I 0.9500 . ?
C01J H01J 0.9500 . ?
C01K H01K 0.9500 . ?
C01K C01W 1.392(6) . ?
C01K C01Z 1.363(6) . ?
C01L H01L 0.9500 . ?
C01M H01M 0.9500 . ?
C01M C021 1.371(6) . ?
C01N H01N 0.9500 . ?
C01N C025 1.381(6) . ?
C01O H01O 0.9500 . ?
C01O C025 1.386(7) . ?
C01P H01P 0.9500 . ?
C01P C020 1.388(6) . ?
C01Q H01Q 0.9500 . ?
C01Q C020 1.367(6) . ?
C01R H01R 0.9500 . ?
C01R C01X 1.387(7) . ?
C01S H01S 0.9500 . ?
C01T H01T 0.9500 . ?
C01U H01U 0.9500 . ?
C01U C021 1.383(7) . ?
C01W H01W 0.9500 . ?
C01X H01X 0.9500 . ?
C01Y H01Y 0.9500 . ?
C01Y C026 1.391(7) . ?
C01Z H01Z 0.9500 . ?
C01Z C023 1.378(7) . ?
C020 H020 0.9500 . ?
C021 H021 0.9500 . ?
C022 H022 0.9500 . ?
C023 H023 0.9500 . ?
C024 H024 0.9500 . ?
C024 C028 1.383(6) . ?
C025 H025 0.9500 . ?
C026 H026 0.9500 . ?
C026 C027 1.361(7) . ?
C027 H027 0.9500 . ?
C027 C028 1.385(7) . ?
C028 H028 0.9500 . ?

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
C00E N001 C007 122.6(4) . . ?
C00H N002 C009 122.6(4) . . ?
C01V N003 C00Z 120.0(4) . . ?
C00Q N004 C00C 120.8(4) . . ?
C00J C005 C00D 121.8(4) . . ?
C00J C005 C011 116.5(4) . . ?
C011 C005 C00D 121.7(4) . . ?
C00B C006 C00L 122.8(4) . . ?
C017 C006 C00B 116.7(4) . . ?
C017 C006 C00L 120.4(4) . . ?
C00P C007 N001 122.5(4) . . ?
C00U C007 N001 118.5(4) . . ?
C00U C007 C00P 118.6(4) . . ?
C00W C008 C00E 119.7(4) . . ?
C00W C008 C00Y 118.5(4) . . ?
C00Y C008 C00E 121.7(4) . . ?
C014 C009 N002 119.2(4) . . ?
C014 C009 C01I 116.8(4) . . ?
C01I C009 N002 123.6(4) . . ?
C012 C00A C00H 121.7(4) . . ?
C01E C00A C00H 120.7(4) . . ?
C01E C00A C012 117.6(4) . . ?
C006 C00B H00B 119.1 . . ?
C006 C00B C018 121.7(4) . . ?
C018 C00B H00B 119.1 . . ?
C00X C00C N004 117.9(4) . . ?
C00X C00C C018 119.3(5) . . ?
C018 C00C N004 122.6(5) . . ?
C00I C00D C005 122.2(4) . . ?
C00I C00D C00N 116.2(4) . . ?
C00N C00D C005 121.6(4) . . ?
N001 C00E C008 123.3(4) . . ?
N001 C00E C00F 116.7(4) . . ?
C008 C00E C00F 119.8(4) . . ?
C00R C00F C00E 120.1(4) . . ?
C00R C00F C01P 118.9(4) . . ?
C01P C00F C00E 121.0(5) . . ?
C00S C00G H00G 119.7 . . ?
C00Z C00G H00G 119.7 . . ?
C00Z C00G C00S 120.5(4) . . ?
N002 C00H C00A 117.9(4) . . ?
N002 C00H C013 125.2(4) . . ?
C00A C00H C013 116.9(4) . . ?
C00D C00I H00I 118.9 . . ?
C00U C00I C00D 122.2(4) . . ?
C00U C00I H00I 118.9 . . ?
C005 C00J H00J 119.4 . . ?
C014 C00J C005 121.3(4) . . ?
C014 C00J H00J 119.4 . . ?
C01A C00K C00Q 119.5(4) . . ?
C01A C00K C01W 119.1(5) . . ?
C01W C00K C00Q 121.4(4) . . ?
C00S C00L C006 122.2(4) . . ?
C00V C00L C006 121.2(4) . . ?
C00V C00L C00S 116.6(4) . . ?
C01B C00M C00Q 119.9(5) . . ?
C01C C00M C00Q 120.8(5) . . ?
C01C C00M C01B 119.3(5) . . ?
C00D C00N H00N 119.2 . . ?
C00P C00N C00D 121.7(4) . . ?
C00P C00N H00N 119.2 . . ?
C01D C00O H00O 120.5 . . ?
C01T C00O H00O 120.5 . . ?
C01T C00O C01D 119.0(5) . . ?
C007 C00P H00P 119.6 . . ?
C00N C00P C007 120.7(4) . . ?
C00N C00P H00P 119.6 . . ?
N004 C00Q C00K 123.7(4) . . ?
N004 C00Q C00M 118.3(4) . . ?
C00K C00Q C00M 118.0(4) . . ?
C00F C00R H00R 119.4 . . ?
C00F C00R C010 121.2(5) . . ?
C010 C00R H00R 119.4 . . ?
C00G C00S C00L 121.6(5) . . ?
C00G C00S H00S 119.2 . . ?
C00L C00S H00S 119.2 . . ?
C01Y C00T C01V 122.2(5) . . ?
C01Y C00T C024 119.0(5) . . ?
C024 C00T C01V 118.7(4) . . ?
C007 C00U C00I 120.5(4) . . ?
C007 C00U H00U 119.7 . . ?
C00I C00U H00U 119.7 . . ?
C00L C00V H00V 118.7 . . ?
C01S C00V C00L 122.6(5) . . ?
C01S C00V H00V 118.7 . . ?
C008 C00W H00W 119.1 . . ?
C008 C00W C01M 121.8(5) . . ?
C01M C00W H00W 119.1 . . ?
C00C C00X H00X 119.7 . . ?
C00C C00X C017 120.6(5) . . ?
C017 C00X H00X 119.7 . . ?
C008 C00Y H00Y 120.0 . . ?
C01U C00Y C008 120.0(5) . . ?
C01U C00Y H00Y 120.0 . . ?
C00G C00Z N003 122.0(4) . . ?
C00G C00Z C01S 118.8(4) . . ?
C01S C00Z N003 118.9(4) . . ?
C00R C010 H010 120.6 . . ?
C01Q C010 C00R 118.8(5) . . ?
C01Q C010 H010 120.6 . . ?
C005 C011 H011 119.0 . . ?
C01I C011 C005 122.0(5) . . ?
C01I C011 H011 119.0 . . ?
C00A C012 H012 119.4 . . ?
C01D C012 C00A 121.2(5) . . ?
C01D C012 H012 119.4 . . ?
C019 C013 C00H 120.0(4) . . ?
C01L C013 C00H 121.5(4) . . ?
C01L C013 C019 118.6(5) . . ?
C009 C014 C00J 122.1(4) . . ?
C009 C014 H014 118.9 . . ?
C00J C014 H014 118.9 . . ?
C016 C015 C01H 119.1(5) . . ?
C016 C015 C01V 121.6(5) . . ?
C01H C015 C01V 119.4(4) . . ?
C015 C016 H016 120.3 . . ?
C022 C016 C015 119.4(5) . . ?
C022 C016 H016 120.3 . . ?
C006 C017 H017 119.1 . . ?
C00X C017 C006 121.9(5) . . ?
C00X C017 H017 119.1 . . ?
C00B C018 H018 120.1 . . ?
C00C C018 C00B 119.7(5) . . ?
C00C C018 H018 120.1 . . ?
C013 C019 H019 119.7 . . ?
C01X C019 C013 120.6(5) . . ?
C01X C019 H019 119.7 . . ?
C00K C01A H01A 119.8 . . ?
C00K C01A C023 120.3(5) . . ?
C023 C01A H01A 119.8 . . ?
C00M C01B H01B 119.8 . . ?
C01N C01B C00M 120.4(5) . . ?
C01N C01B H01B 119.8 . . ?
C00M C01C H01C 119.6 . . ?
C00M C01C C01O 120.8(5) . . ?
C01O C01C H01C 119.6 . . ?
C00O C01D C012 120.2(5) . . ?
C00O C01D H01D 119.9 . . ?
C012 C01D H01D 119.9 . . ?
C00A C01E H01E 119.7 . . ?
C01T C01E C00A 120.5(5) . . ?
C01T C01E H01E 119.7 . . ?
C01J C01F H01F 120.6 . . ?
C01J C01F C022 118.9(5) . . ?
C022 C01F H01F 120.6 . . ?
C01L C01G H01G 120.0 . . ?
C01L C01G C01R 120.0(5) . . ?
C01R C01G H01G 120.0 . . ?
C015 C01H H01H 119.8 . . ?
C01J C01H C015 120.3(5) . . ?
C01J C01H H01H 119.8 . . ?
C009 C01I H01I 119.4 . . ?
C011 C01I C009 121.2(5) . . ?
C011 C01I H01I 119.4 . . ?
C01F C01J C01H 120.5(5) . . ?
C01F C01J H01J 119.8 . . ?
C01H C01J H01J 119.8 . . ?
C01W C01K H01K 120.0 . . ?
C01Z C01K H01K 120.0 . . ?
C01Z C01K C01W 120.1(5) . . ?
C013 C01L H01L 119.5 . . ?
C01G C01L C013 120.9(5) . . ?
C01G C01L H01L 119.5 . . ?
C00W C01M H01M 120.4 . . ?
C021 C01M C00W 119.1(5) . . ?
C021 C01M H01M 120.4 . . ?
C01B C01N H01N 120.2 . . ?
C01B C01N C025 119.7(5) . . ?
C025 C01N H01N 120.2 . . ?
C01C C01O H01O 120.0 . . ?
C01C C01O C025 119.9(5) . . ?
C025 C01O H01O 120.0 . . ?
C00F C01P H01P 119.9 . . ?
C020 C01P C00F 120.1(5) . . ?
C020 C01P H01P 119.9 . . ?
C010 C01Q H01Q 119.6 . . ?
C020 C01Q C010 120.9(5) . . ?
C020 C01Q H01Q 119.6 . . ?
C01G C01R H01R 120.1 . . ?
C01G C01R C01X 119.8(5) . . ?
C01X C01R H01R 120.1 . . ?
C00V C01S C00Z 119.9(5) . . ?
C00V C01S H01S 120.1 . . ?
C00Z C01S H01S 120.1 . . ?
C00O C01T C01E 121.3(5) . . ?
C00O C01T H01T 119.3 . . ?
C01E C01T H01T 119.3 . . ?
C00Y C01U H01U 119.9 . . ?
C00Y C01U C021 120.1(5) . . ?
C021 C01U H01U 119.9 . . ?
N003 C01V C00T 123.9(4) . . ?
N003 C01V C015 118.3(4) . . ?
C00T C01V C015 117.6(4) . . ?
C00K C01W C01K 120.2(5) . . ?
C00K C01W H01W 119.9 . . ?
C01K C01W H01W 119.9 . . ?
C019 C01X C01R 120.1(5) . . ?
C019 C01X H01X 120.0 . . ?
C01R C01X H01X 120.0 . . ?
C00T C01Y H01Y 120.6 . . ?
C026 C01Y C00T 118.8(5) . . ?
C026 C01Y H01Y 120.6 . . ?
C01K C01Z H01Z 120.1 . . ?
C01K C01Z C023 119.9(5) . . ?
C023 C01Z H01Z 120.1 . . ?
C01P C020 H020 120.0 . . ?
C01Q C020 C01P 120.1(5) . . ?
C01Q C020 H020 120.0 . . ?
C01M C021 C01U 120.3(5) . . ?
C01M C021 H021 119.8 . . ?
C01U C021 H021 119.8 . . ?
C016 C022 C01F 121.8(5) . . ?
C016 C022 H022 119.1 . . ?
C01F C022 H022 119.1 . . ?
C01A C023 H023 119.8 . . ?
C01Z C023 C01A 120.4(5) . . ?
C01Z C023 H023 119.8 . . ?
C00T C024 H024 119.4 . . ?
C028 C024 C00T 121.3(5) . . ?
C028 C024 H024 119.4 . . ?
C01N C025 C01O 119.9(5) . . ?
C01N C025 H025 120.1 . . ?
C01O C025 H025 120.1 . . ?
C01Y C026 H026 119.2 . . ?
C027 C026 C01Y 121.6(5) . . ?
C027 C026 H026 119.2 . . ?
C026 C027 H027 119.8 . . ?
C026 C027 C028 120.3(6) . . ?
C028 C027 H027 119.8 . . ?
C024 C028 C027 118.9(6) . . ?
C024 C028 H028 120.6 . . ?
C027 C028 H028 120.6 . . ?


_olex2_exptl_crystal_mounting_method 'in oil in plastic loop'
_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_mo_od_man22
_database_code_depnum_ccdc_archive 'CCDC 2240744'
loop_
_audit_author_name
_audit_author_address
'Oliver Dumele'
;Humboldt University Berlin
Germany
;
_audit_update_record             
;
2023-07-31 deposited with the CCDC.	2023-10-18 downloaded from the CCDC.
;
# Added during the CSD deposition process: Monday 31 July 2023 02:15 PM
# end Validation Reply Form

# start Validation Reply Form
_vrf_THETM01_mo_od_man22         
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
RESPONSE: Crystal diffracted weakly at resolution lower than 0.85 \%A. No crystal with better quality was present in the sample. 
;
_vrf_RINTA01_mo_od_man22         
;
PROBLEM: The value of Rint is greater than 0.12
RESPONSE: due to low crystal quality
;
# Added during the CSD deposition process: Monday 31 July 2023 02:13 PM
# end Validation Reply Form

_audit_creation_date             2023-07-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            'Benzidine(bisfluorenone imine)'
_chemical_name_systematic        MAN-20
_chemical_formula_moiety         'C38 H24 N2'
_chemical_formula_sum            'C38 H24 N2'
_chemical_formula_weight         508.59
_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'

_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                   17.0198(7)
_cell_length_b                   10.7650(5)
_cell_length_c                   29.1185(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5335.0(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2107
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.02
_cell_measurement_theta_min      2.34
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6539
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1053 before and 0.0724 after correction.
The Ratio of minimum to maximum transmission is 0.8772.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             2128
_exptl_crystal_preparation       synthetic
_exptl_crystal_recrystallization_method evaporation
_exptl_crystal_size_max          0.409
_exptl_crystal_size_mid          0.173
_exptl_crystal_size_min          0.058
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1406
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            111228
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        23.250
_diffrn_reflns_theta_max         23.250
_diffrn_reflns_theta_min         1.841
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2818
_reflns_number_total             3824
_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 V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.126
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         3824
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0475
_refine_ls_restrained_S_all      1.035
_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)+(0.0699P)²+1.3832P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1162
_refine_ls_wR_factor_ref         0.1331
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C7(H7), C10(H10), C11(H11), C19(H19), C21(H21), C22(H22),
 C23(H23), C24(H24), C25(H25), C26(H26), C27(H27), C28(H28), C29(H29), C30(H30),
  C31(H31), C32(H32), C33(H33), C34(H34), C35(H35), C36(H36), C37(H37), C38(H38)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.29854(11) 0.22583(19) 0.73659(6) 0.0500(5) Uani 1 1 d . . . . .
N2 N 0.37768(12) 0.75116(19) 0.46094(6) 0.0520(5) Uani 1 1 d . . . . .
C1 C 0.32898(13) 0.5218(2) 0.57535(7) 0.0406(5) Uani 1 1 d . . . . .
C2 C 0.36415(13) 0.3352(2) 0.62208(7) 0.0435(6) Uani 1 1 d . . . . .
H2 H 0.397893 0.309169 0.597936 0.052 Uiso 1 1 calc R . . . .
C3 C 0.32001(12) 0.4437(2) 0.61658(7) 0.0387(5) Uani 1 1 d . . . . .
C4 C 0.31098(12) 0.3000(2) 0.69736(7) 0.0436(6) Uani 1 1 d . . . . .
C5 C 0.35941(13) 0.6751(2) 0.49910(7) 0.0453(6) Uani 1 1 d . . . . .
C6 C 0.36007(13) 0.2650(2) 0.66144(7) 0.0449(6) Uani 1 1 d . . . . .
H6 H 0.391041 0.191941 0.664129 0.054 Uiso 1 1 calc R . . . .
C7 C 0.26444(13) 0.4050(2) 0.69183(7) 0.0453(6) Uani 1 1 d . . . . .
H7 H 0.228622 0.428127 0.715345 0.054 Uiso 1 1 calc R . . . .
C8 C 0.51165(13) 0.8116(2) 0.49263(7) 0.0436(6) Uani 1 1 d . . . . .
C9 C 0.46939(13) 0.1195(2) 0.79851(7) 0.0460(6) Uani 1 1 d . . . . .
C10 C 0.26979(12) 0.4759(2) 0.65250(7) 0.0433(6) Uani 1 1 d . . . . .
H10 H 0.238451 0.548584 0.649816 0.052 Uiso 1 1 calc R . . . .
C11 C 0.31267(14) 0.6490(2) 0.57609(8) 0.0483(6) Uani 1 1 d . . . . .
H11 H 0.291674 0.684890 0.603248 0.058 Uiso 1 1 calc R . . . .
C12 C 0.44047(13) 0.1987(2) 0.76404(7) 0.0439(6) Uani 1 1 d . . . . .
C13 C 0.40368(14) 0.0532(2) 0.82004(7) 0.0467(6) Uani 1 1 d . . . . .
C14 C 0.44364(14) 0.8076(2) 0.45988(7) 0.0452(6) Uani 1 1 d . . . . .
C15 C 0.46715(14) 0.8872(2) 0.42049(7) 0.0458(6) Uani 1 1 d . . . . .
C16 C 0.35325(13) 0.1816(2) 0.76194(7) 0.0454(6) Uani 1 1 d . . . . .
C17 C 0.33414(13) 0.0912(2) 0.79862(7) 0.0474(6) Uani 1 1 d . . . . .
C18 C 0.56933(14) 0.8889(2) 0.47370(8) 0.0471(6) Uani 1 1 d . . . . .
C19 C 0.35614(14) 0.4734(2) 0.53389(7) 0.0514(6) Uani 1 1 d . . . . .
H19 H 0.364842 0.386533 0.531399 0.062 Uiso 1 1 calc R . . . .
C20 C 0.54153(14) 0.9372(2) 0.42917(7) 0.0471(6) Uani 1 1 d . . . . .
C21 C 0.37075(16) 0.5482(2) 0.49639(8) 0.0546(7) Uani 1 1 d . . . . .
H21 H 0.388729 0.512222 0.468517 0.066 Uiso 1 1 calc R . . . .
C22 C 0.32622(15) 0.7238(2) 0.53846(8) 0.0518(6) Uani 1 1 d . . . . .
H22 H 0.312656 0.809394 0.539622 0.062 Uiso 1 1 calc R . . . .
C23 C 0.52450(15) 0.7533(2) 0.53439(7) 0.0521(6) Uani 1 1 d . . . . .
H23 H 0.485502 0.700880 0.547427 0.062 Uiso 1 1 calc R . . . .
C24 C 0.49223(14) 0.2733(2) 0.73967(8) 0.0526(6) Uani 1 1 d . . . . .
H24 H 0.473292 0.329459 0.717063 0.063 Uiso 1 1 calc R . . . .
C25 C 0.54924(14) 0.1125(3) 0.80729(9) 0.0586(7) Uani 1 1 d . . . . .
H25 H 0.568808 0.058878 0.830548 0.070 Uiso 1 1 calc R . . . .
C26 C 0.63962(15) 0.9075(3) 0.49632(9) 0.0596(7) Uani 1 1 d . . . . .
H26 H 0.678885 0.959727 0.483488 0.072 Uiso 1 1 calc R . . . .
C27 C 0.42787(16) 0.9131(2) 0.38043(8) 0.0590(7) Uani 1 1 d . . . . .
H27 H 0.377596 0.878023 0.374681 0.071 Uiso 1 1 calc R . . . .
C28 C 0.57569(16) 1.0159(2) 0.39736(8) 0.0587(7) Uani 1 1 d . . . . .
H28 H 0.625947 1.051203 0.402982 0.070 Uiso 1 1 calc R . . . .
C29 C 0.59524(16) 0.7727(3) 0.55677(9) 0.0632(7) Uani 1 1 d . . . . .
H29 H 0.604850 0.733226 0.585407 0.076 Uiso 1 1 calc R . . . .
C30 C 0.59987(15) 0.1846(3) 0.78167(9) 0.0605(7) Uani 1 1 d . . . . .
H30 H 0.654860 0.178821 0.786846 0.073 Uiso 1 1 calc R . . . .
C31 C 0.40107(16) -0.0355(2) 0.85440(8) 0.0585(7) Uani 1 1 d . . . . .
H31 H 0.447793 -0.061626 0.869397 0.070 Uiso 1 1 calc R . . . .
C32 C 0.57200(15) 0.2648(3) 0.74879(9) 0.0586(7) Uani 1 1 d . . . . .
H32 H 0.607864 0.314999 0.732055 0.070 Uiso 1 1 calc R . . . .
C33 C 0.26271(15) 0.0408(3) 0.81067(8) 0.0643(8) Uani 1 1 d . . . . .
H33 H 0.215774 0.066806 0.795854 0.077 Uiso 1 1 calc R . . . .
C34 C 0.65201(16) 0.8490(3) 0.53784(9) 0.0684(8) Uani 1 1 d . . . . .
H34 H 0.700209 0.861284 0.553648 0.082 Uiso 1 1 calc R . . . .
C35 C 0.53553(19) 1.0425(3) 0.35726(9) 0.0677(8) Uani 1 1 d . . . . .
H35 H 0.558409 1.097067 0.335365 0.081 Uiso 1 1 calc R . . . .
C36 C 0.46265(18) 0.9911(3) 0.34851(9) 0.0678(8) Uani 1 1 d . . . . .
H36 H 0.436334 1.009267 0.320538 0.081 Uiso 1 1 calc R . . . .
C37 C 0.32907(18) -0.0852(3) 0.86647(8) 0.0673(8) Uani 1 1 d . . . . .
H37 H 0.326528 -0.145915 0.890110 0.081 Uiso 1 1 calc R . . . .
C38 C 0.26076(17) -0.0483(3) 0.84476(9) 0.0729(8) Uani 1 1 d . . . . .
H38 H 0.212038 -0.084512 0.853361 0.087 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
N1 C4 1.410(3) . ?
N1 C16 1.280(3) . ?
N2 C5 1.415(3) . ?
N2 C14 1.277(3) . ?
C1 C3 1.474(3) . ?
C1 C11 1.397(3) . ?
C1 C19 1.394(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.399(3) . ?
C2 C6 1.374(3) . ?
C3 C10 1.395(3) . ?
C4 C6 1.391(3) . ?
C4 C7 1.389(3) . ?
C5 C21 1.381(3) . ?
C5 C22 1.382(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C7 C10 1.380(3) . ?
C8 C14 1.501(3) . ?
C8 C18 1.400(3) . ?
C8 C23 1.386(3) . ?
C9 C12 1.406(3) . ?
C9 C13 1.467(3) . ?
C9 C25 1.385(3) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C11 C22 1.380(3) . ?
C12 C16 1.497(3) . ?
C12 C24 1.387(3) . ?
C13 C17 1.399(3) . ?
C13 C31 1.384(3) . ?
C14 C15 1.487(3) . ?
C15 C20 1.398(3) . ?
C15 C27 1.373(3) . ?
C16 C17 1.481(3) . ?
C17 C33 1.377(3) . ?
C18 C20 1.474(3) . ?
C18 C26 1.380(3) . ?
C19 H19 0.9500 . ?
C19 C21 1.379(3) . ?
C20 C28 1.384(3) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C23 C29 1.385(3) . ?
C24 H24 0.9500 . ?
C24 C32 1.386(3) . ?
C25 H25 0.9500 . ?
C25 C30 1.379(3) . ?
C26 H26 0.9500 . ?
C26 C34 1.379(4) . ?
C27 H27 0.9500 . ?
C27 C36 1.385(3) . ?
C28 H28 0.9500 . ?
C28 C35 1.383(4) . ?
C29 H29 0.9500 . ?
C29 C34 1.383(4) . ?
C30 H30 0.9500 . ?
C30 C32 1.373(4) . ?
C31 H31 0.9500 . ?
C31 C37 1.383(4) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
C33 C38 1.381(3) . ?
C34 H34 0.9500 . ?
C35 H35 0.9500 . ?
C35 C36 1.382(4) . ?
C36 H36 0.9500 . ?
C37 H37 0.9500 . ?
C37 C38 1.382(4) . ?
C38 H38 0.9500 . ?

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
C16 N1 C4 124.7(2) . . ?
C14 N2 C5 119.19(19) . . ?
C11 C1 C3 121.73(19) . . ?
C19 C1 C3 121.8(2) . . ?
C19 C1 C11 116.5(2) . . ?
C3 C2 H2 119.1 . . ?
C6 C2 H2 119.1 . . ?
C6 C2 C3 121.9(2) . . ?
C2 C3 C1 120.97(19) . . ?
C10 C3 C1 122.2(2) . . ?
C10 C3 C2 116.79(19) . . ?
C6 C4 N1 123.1(2) . . ?
C7 C4 N1 118.0(2) . . ?
C7 C4 C6 118.4(2) . . ?
C21 C5 N2 119.8(2) . . ?
C21 C5 C22 118.7(2) . . ?
C22 C5 N2 121.4(2) . . ?
C2 C6 C4 120.6(2) . . ?
C2 C6 H6 119.7 . . ?
C4 C6 H6 119.7 . . ?
C4 C7 H7 119.7 . . ?
C10 C7 C4 120.6(2) . . ?
C10 C7 H7 119.7 . . ?
C18 C8 C14 107.93(19) . . ?
C23 C8 C14 131.8(2) . . ?
C23 C8 C18 120.3(2) . . ?
C12 C9 C13 109.45(19) . . ?
C25 C9 C12 120.6(2) . . ?
C25 C9 C13 130.0(2) . . ?
C3 C10 H10 119.1 . . ?
C7 C10 C3 121.7(2) . . ?
C7 C10 H10 119.1 . . ?
C1 C11 H11 119.1 . . ?
C22 C11 C1 121.8(2) . . ?
C22 C11 H11 119.1 . . ?
C9 C12 C16 107.57(19) . . ?
C24 C12 C9 119.6(2) . . ?
C24 C12 C16 132.8(2) . . ?
C17 C13 C9 108.19(19) . . ?
C31 C13 C9 132.0(2) . . ?
C31 C13 C17 119.8(2) . . ?
N2 C14 C8 132.6(2) . . ?
N2 C14 C15 122.0(2) . . ?
C15 C14 C8 105.4(2) . . ?
C20 C15 C14 109.0(2) . . ?
C27 C15 C14 129.9(2) . . ?
C27 C15 C20 121.1(2) . . ?
N1 C16 C12 134.4(2) . . ?
N1 C16 C17 120.0(2) . . ?
C17 C16 C12 105.60(18) . . ?
C13 C17 C16 109.1(2) . . ?
C33 C17 C13 121.2(2) . . ?
C33 C17 C16 129.5(2) . . ?
C8 C18 C20 109.3(2) . . ?
C26 C18 C8 120.4(2) . . ?
C26 C18 C20 130.3(2) . . ?
C1 C19 H19 119.1 . . ?
C21 C19 C1 121.8(2) . . ?
C21 C19 H19 119.1 . . ?
C15 C20 C18 108.3(2) . . ?
C28 C20 C15 119.7(2) . . ?
C28 C20 C18 132.0(2) . . ?
C5 C21 H21 119.8 . . ?
C19 C21 C5 120.4(2) . . ?
C19 C21 H21 119.8 . . ?
C5 C22 H22 119.8 . . ?
C11 C22 C5 120.3(2) . . ?
C11 C22 H22 119.8 . . ?
C8 C23 H23 120.6 . . ?
C29 C23 C8 118.8(2) . . ?
C29 C23 H23 120.6 . . ?
C12 C24 H24 120.5 . . ?
C32 C24 C12 119.0(2) . . ?
C32 C24 H24 120.5 . . ?
C9 C25 H25 120.6 . . ?
C30 C25 C9 118.8(2) . . ?
C30 C25 H25 120.6 . . ?
C18 C26 H26 120.5 . . ?
C34 C26 C18 119.0(2) . . ?
C34 C26 H26 120.5 . . ?
C15 C27 H27 120.5 . . ?
C15 C27 C36 119.0(3) . . ?
C36 C27 H27 120.5 . . ?
C20 C28 H28 120.5 . . ?
C35 C28 C20 119.0(3) . . ?
C35 C28 H28 120.5 . . ?
C23 C29 H29 119.7 . . ?
C34 C29 C23 120.6(2) . . ?
C34 C29 H29 119.7 . . ?
C25 C30 H30 119.5 . . ?
C32 C30 C25 121.0(2) . . ?
C32 C30 H30 119.5 . . ?
C13 C31 H31 120.7 . . ?
C37 C31 C13 118.7(2) . . ?
C37 C31 H31 120.7 . . ?
C24 C32 H32 119.5 . . ?
C30 C32 C24 120.9(2) . . ?
C30 C32 H32 119.5 . . ?
C17 C33 H33 120.7 . . ?
C17 C33 C38 118.6(2) . . ?
C38 C33 H33 120.7 . . ?
C26 C34 C29 120.9(2) . . ?
C26 C34 H34 119.5 . . ?
C29 C34 H34 119.5 . . ?
C28 C35 H35 119.5 . . ?
C36 C35 C28 121.1(2) . . ?
C36 C35 H35 119.5 . . ?
C27 C36 H36 119.9 . . ?
C35 C36 C27 120.2(3) . . ?
C35 C36 H36 119.9 . . ?
C31 C37 H37 119.4 . . ?
C38 C37 C31 121.2(2) . . ?
C38 C37 H37 119.4 . . ?
C33 C38 C37 120.6(3) . . ?
C33 C38 H38 119.7 . . ?
C37 C38 H38 119.7 . . ?

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
N1 C4 C6 C2 173.7(2) . . . . ?
N1 C4 C7 C10 -175.1(2) . . . . ?
N1 C16 C17 C13 177.6(2) . . . . ?
N1 C16 C17 C33 1.4(4) . . . . ?
N2 C5 C21 C19 177.4(2) . . . . ?
N2 C5 C22 C11 -176.6(2) . . . . ?
N2 C14 C15 C20 179.5(2) . . . . ?
N2 C14 C15 C27 -1.2(4) . . . . ?
C1 C3 C10 C7 -177.1(2) . . . . ?
C1 C11 C22 C5 -2.4(4) . . . . ?
C1 C19 C21 C5 0.6(4) . . . . ?
C2 C3 C10 C7 0.7(3) . . . . ?
C3 C1 C11 C22 175.4(2) . . . . ?
C3 C1 C19 C21 -174.5(2) . . . . ?
C3 C2 C6 C4 0.3(3) . . . . ?
C4 N1 C16 C12 7.5(4) . . . . ?
C4 N1 C16 C17 -171.8(2) . . . . ?
C4 C7 C10 C3 1.7(3) . . . . ?
C5 N2 C14 C8 0.0(4) . . . . ?
C5 N2 C14 C15 178.9(2) . . . . ?
C6 C2 C3 C1 176.1(2) . . . . ?
C6 C2 C3 C10 -1.7(3) . . . . ?
C6 C4 C7 C10 -3.1(3) . . . . ?
C7 C4 C6 C2 2.1(3) . . . . ?
C8 C14 C15 C20 -1.4(2) . . . . ?
C8 C14 C15 C27 177.9(2) . . . . ?
C8 C18 C20 C15 -1.1(3) . . . . ?
C8 C18 C20 C28 179.9(2) . . . . ?
C8 C18 C26 C34 -0.2(4) . . . . ?
C8 C23 C29 C34 0.0(4) . . . . ?
C9 C12 C16 N1 -177.3(3) . . . . ?
C9 C12 C16 C17 2.1(2) . . . . ?
C9 C12 C24 C32 2.3(3) . . . . ?
C9 C13 C17 C16 1.1(3) . . . . ?
C9 C13 C17 C33 177.6(2) . . . . ?
C9 C13 C31 C37 -177.5(3) . . . . ?
C9 C25 C30 C32 1.7(4) . . . . ?
C11 C1 C3 C2 -153.6(2) . . . . ?
C11 C1 C3 C10 24.1(3) . . . . ?
C11 C1 C19 C21 3.8(3) . . . . ?
C12 C9 C13 C17 0.3(3) . . . . ?
C12 C9 C13 C31 178.5(2) . . . . ?
C12 C9 C25 C30 0.1(4) . . . . ?
C12 C16 C17 C13 -1.9(3) . . . . ?
C12 C16 C17 C33 -178.1(3) . . . . ?
C12 C24 C32 C30 -0.5(4) . . . . ?
C13 C9 C12 C16 -1.5(2) . . . . ?
C13 C9 C12 C24 178.5(2) . . . . ?
C13 C9 C25 C30 179.4(2) . . . . ?
C13 C17 C33 C38 0.3(4) . . . . ?
C13 C31 C37 C38 0.3(4) . . . . ?
C14 N2 C5 C21 -97.9(3) . . . . ?
C14 N2 C5 C22 85.7(3) . . . . ?
C14 C8 C18 C20 0.2(2) . . . . ?
C14 C8 C18 C26 -178.6(2) . . . . ?
C14 C8 C23 C29 178.4(2) . . . . ?
C14 C15 C20 C18 1.5(2) . . . . ?
C14 C15 C20 C28 -179.4(2) . . . . ?
C14 C15 C27 C36 -179.9(2) . . . . ?
C15 C20 C28 C35 -0.7(3) . . . . ?
C15 C27 C36 C35 -0.5(4) . . . . ?
C16 N1 C4 C6 53.0(3) . . . . ?
C16 N1 C4 C7 -135.4(2) . . . . ?
C16 C12 C24 C32 -177.7(2) . . . . ?
C16 C17 C33 C38 176.1(2) . . . . ?
C17 C13 C31 C37 0.5(4) . . . . ?
C17 C33 C38 C37 0.5(4) . . . . ?
C18 C8 C14 N2 179.7(2) . . . . ?
C18 C8 C14 C15 0.7(2) . . . . ?
C18 C8 C23 C29 -0.2(3) . . . . ?
C18 C20 C28 C35 178.2(2) . . . . ?
C18 C26 C34 C29 0.0(4) . . . . ?
C19 C1 C3 C2 24.7(3) . . . . ?
C19 C1 C3 C10 -157.6(2) . . . . ?
C19 C1 C11 C22 -3.0(3) . . . . ?
C20 C15 C27 C36 -0.7(4) . . . . ?
C20 C18 C26 C34 -178.7(2) . . . . ?
C20 C28 C35 C36 -0.5(4) . . . . ?
C21 C5 C22 C11 6.9(4) . . . . ?
C22 C5 C21 C19 -6.1(4) . . . . ?
C23 C8 C14 N2 1.1(4) . . . . ?
C23 C8 C14 C15 -178.0(2) . . . . ?
C23 C8 C18 C20 179.1(2) . . . . ?
C23 C8 C18 C26 0.2(3) . . . . ?
C23 C29 C34 C26 0.0(4) . . . . ?
C24 C12 C16 N1 2.7(5) . . . . ?
C24 C12 C16 C17 -177.9(2) . . . . ?
C25 C9 C12 C16 177.9(2) . . . . ?
C25 C9 C12 C24 -2.1(3) . . . . ?
C25 C9 C13 C17 -179.1(2) . . . . ?
C25 C9 C13 C31 -0.9(4) . . . . ?
C25 C30 C32 C24 -1.5(4) . . . . ?
C26 C18 C20 C15 177.6(2) . . . . ?
C26 C18 C20 C28 -1.4(4) . . . . ?
C27 C15 C20 C18 -177.9(2) . . . . ?
C27 C15 C20 C28 1.3(3) . . . . ?
C28 C35 C36 C27 1.1(4) . . . . ?
C31 C13 C17 C16 -177.4(2) . . . . ?
C31 C13 C17 C33 -0.8(4) . . . . ?
C31 C37 C38 C33 -0.8(5) . . . . ?


_olex2_submission_original_sample_id MAN-22
_olex2_submission_special_instructions 'No special instructions were received'
