# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 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_1
_database_code_depnum_ccdc_archive 'CCDC 1576743'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2019-06-19 deposited with the CCDC.	2019-06-20 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT910_1                   
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         30 Note  
RESPONSE: Due to the beam stopper
;
# end Validation Reply Form

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H18 N2 O7'
_chemical_formula_weight         458.41

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.6108(5)
_cell_length_b                   9.5147(7)
_cell_length_c                   17.1651(10)
_cell_angle_alpha                96.283(5)
_cell_angle_beta                 95.365(5)
_cell_angle_gamma                103.343(6)
_cell_volume                     1036.32(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3703
_cell_measurement_theta_min      4.82
_cell_measurement_theta_max      25.25

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             476
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
'D8 Quest (Photon II detector/ Chi and Kappa scans)'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11315
_diffrn_reflns_av_R_equivalents  0.0749
_diffrn_reflns_av_sigmaI/netI    0.0830
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.82
_diffrn_reflns_theta_max         25.25
_reflns_number_total             3703
_reflns_number_gt                2282
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0750P)²+0.0900P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3703
_refine_ls_number_parameters     310
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0995
_refine_ls_R_factor_gt           0.0569
_refine_ls_wR_factor_ref         0.1535
_refine_ls_wR_factor_gt          0.1309
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_restrained_S_all      0.978
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O7 O 0.5890(3) -0.0038(2) 0.42923(13) 0.0428(6) Uani 1 1 d . . .
O2 O 0.0280(3) 0.0206(2) 0.10600(11) 0.0255(5) Uani 1 1 d . . .
H2A H -0.004(4) -0.054(4) 0.0570(19) 0.038 Uiso 1 1 d . . .
O5 O 0.2252(3) 0.4357(2) 0.42526(12) 0.0369(6) Uani 1 1 d . . .
O6 O 0.1251(3) 0.2034(3) 0.38508(11) 0.0363(6) Uani 1 1 d . . .
O3 O 0.2595(3) 0.6991(2) 0.11146(12) 0.0319(5) Uani 1 1 d . . .
O4 O 0.3015(3) 0.7756(2) 0.23709(12) 0.0327(5) Uani 1 1 d . . .
O1 O 0.0626(3) 0.1786(2) 0.01730(11) 0.0263(5) Uani 1 1 d . . .
N2 N 0.1746(3) 0.3309(3) 0.37295(14) 0.0271(6) Uani 1 1 d . . .
N1 N 0.2610(3) 0.6787(3) 0.18124(15) 0.0249(6) Uani 1 1 d . . .
C1 C 0.8285(4) 0.8124(4) 0.3103(2) 0.0374(8) Uani 1 1 d . . .
H1 H 0.8646 0.9098 0.3326 0.045 Uiso 1 1 calc R . .
C2 C 0.8044(4) 0.7772(3) 0.22950(19) 0.0312(7) Uani 1 1 d . . .
H2 H 0.8248 0.8514 0.1978 0.037 Uiso 1 1 calc R . .
C3 C 0.7498(4) 0.6320(3) 0.19427(16) 0.0227(6) Uani 1 1 d . . .
C4 C 0.7213(4) 0.5895(4) 0.11063(17) 0.0285(7) Uani 1 1 d . . .
H4 H 0.7397 0.6614 0.0776 0.034 Uiso 1 1 calc R . .
C5 C 0.6687(4) 0.4486(3) 0.07837(16) 0.0266(7) Uani 1 1 d . . .
H5 H 0.6532 0.4258 0.0237 0.032 Uiso 1 1 calc R . .
C6 C 0.6363(4) 0.3333(3) 0.12605(15) 0.0214(6) Uani 1 1 d . . .
C7 C 0.5790(4) 0.1862(3) 0.09486(17) 0.0299(7) Uani 1 1 d . . .
H7 H 0.5616 0.1601 0.0404 0.036 Uiso 1 1 calc R . .
C8 C 0.5476(4) 0.0781(3) 0.14337(19) 0.0320(7) Uani 1 1 d . . .
H8 H 0.5085 -0.0193 0.1212 0.038 Uiso 1 1 calc R . .
C14 C 0.7995(4) 0.7042(4) 0.35889(18) 0.0332(8) Uani 1 1 d . . .
H14 H 0.8163 0.7299 0.4134 0.040 Uiso 1 1 calc R . .
C13 C 0.7452(4) 0.5567(3) 0.32696(16) 0.0238(7) Uani 1 1 d . . .
C15 C 0.7192(4) 0.5202(3) 0.24360(15) 0.0193(6) Uani 1 1 d . . .
C16 C 0.6630(4) 0.3708(3) 0.20958(15) 0.0196(6) Uani 1 1 d . . .
C9 C 0.5737(4) 0.1139(3) 0.22416(18) 0.0296(7) Uani 1 1 d . . .
H9 H 0.5529 0.0400 0.2560 0.036 Uiso 1 1 calc R . .
C10 C 0.6309(4) 0.2591(3) 0.25911(16) 0.0232(7) Uani 1 1 d . . .
C11 C 0.6594(4) 0.3017(4) 0.34335(17) 0.0293(7) Uani 1 1 d . . .
H11 H 0.6392 0.2298 0.3764 0.035 Uiso 1 1 calc R . .
C12 C 0.7140(4) 0.4418(4) 0.37541(17) 0.0282(7) Uani 1 1 d . . .
H12 H 0.7319 0.4651 0.4301 0.034 Uiso 1 1 calc R . .
C24 C 0.7138(5) 0.0488(4) 0.50183(19) 0.0419(9) Uani 1 1 d . . .
H24A H 0.8347 0.1237 0.4942 0.050 Uiso 1 1 calc R . .
H24B H 0.7638 -0.0299 0.5221 0.050 Uiso 1 1 calc R . .
C25 C 0.5941(6) 0.1101(4) 0.5600(2) 0.0497(10) Uani 1 1 d . . .
H25B H 0.6822 0.1427 0.6102 0.060 Uiso 1 1 calc R . .
H25A H 0.5537 0.1938 0.5418 0.060 Uiso 1 1 calc R . .
C23 C 0.0669(4) 0.1510(3) 0.08610(16) 0.0189(6) Uani 1 1 d . . .
C17 C 0.1174(4) 0.2716(3) 0.15310(16) 0.0204(6) Uani 1 1 d . . .
C18 C 0.1627(4) 0.4154(3) 0.13614(15) 0.0197(6) Uani 1 1 d . . .
H18 H 0.1591 0.4351 0.0842 0.024 Uiso 1 1 calc R . .
C19 C 0.2128(4) 0.5272(3) 0.19839(16) 0.0200(6) Uani 1 1 d . . .
C20 C 0.2184(4) 0.5028(3) 0.27628(16) 0.0224(6) Uani 1 1 d . . .
H20 H 0.2520 0.5797 0.3174 0.027 Uiso 1 1 calc R . .
C21 C 0.1718(4) 0.3596(3) 0.29054(15) 0.0214(6) Uani 1 1 d . . .
C22 C 0.1230(4) 0.2433(3) 0.23069(16) 0.0221(6) Uani 1 1 d . . .
H22 H 0.0946 0.1480 0.2422 0.027 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
O7 C24 1.402(4) . ?
O7 C25 1.428(4) 2_656 ?
O2 C23 1.298(3) . ?
O2 H2A 1.01(3) . ?
O5 N2 1.228(3) . ?
O6 N2 1.227(3) . ?
O3 N1 1.234(3) . ?
O4 N1 1.219(3) . ?
O1 C23 1.236(3) . ?
N2 C21 1.469(3) . ?
N1 C19 1.472(4) . ?
C1 C2 1.377(4) . ?
C1 C14 1.384(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.397(4) . ?
C2 H2 0.9300 . ?
C3 C15 1.421(4) . ?
C3 C4 1.431(4) . ?
C4 C5 1.345(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.428(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.394(4) . ?
C6 C16 1.423(4) . ?
C7 C8 1.384(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.376(4) . ?
C8 H8 0.9300 . ?
C14 C13 1.401(4) . ?
C14 H14 0.9300 . ?
C13 C15 1.420(4) . ?
C13 C12 1.434(4) . ?
C15 C16 1.426(4) . ?
C16 C10 1.423(4) . ?
C9 C10 1.395(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.441(4) . ?
C11 C12 1.338(4) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C24 C25 1.482(5) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 O7 1.428(4) 2_656 ?
C25 H25B 0.9700 . ?
C25 H25A 0.9700 . ?
C23 C17 1.488(4) . ?
C17 C22 1.386(4) . ?
C17 C18 1.400(4) . ?
C18 C19 1.380(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.380(4) . ?
C20 C21 1.381(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.381(4) . ?
C22 H22 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C24 O7 C25 110.1(2) . 2_656 ?
C23 O2 H2A 109.7(17) . . ?
O6 N2 O5 124.2(2) . . ?
O6 N2 C21 117.8(2) . . ?
O5 N2 C21 118.0(3) . . ?
O4 N1 O3 124.5(2) . . ?
O4 N1 C19 117.7(2) . . ?
O3 N1 C19 117.9(2) . . ?
C2 C1 C14 120.7(3) . . ?
C2 C1 H1 119.7 . . ?
C14 C1 H1 119.7 . . ?
C1 C2 C3 121.1(3) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C2 C3 C15 118.7(3) . . ?
C2 C3 C4 123.3(3) . . ?
C15 C3 C4 118.0(3) . . ?
C5 C4 C3 122.0(3) . . ?
C5 C4 H4 119.0 . . ?
C3 C4 H4 119.0 . . ?
C4 C5 C6 121.6(3) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C7 C6 C16 118.4(2) . . ?
C7 C6 C5 123.3(3) . . ?
C16 C6 C5 118.3(3) . . ?
C8 C7 C6 121.3(3) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C9 C8 C7 120.5(3) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C1 C14 C13 120.8(3) . . ?
C1 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C13 C15 118.6(3) . . ?
C14 C13 C12 122.4(3) . . ?
C15 C13 C12 119.1(3) . . ?
C13 C15 C3 120.2(3) . . ?
C13 C15 C16 119.7(2) . . ?
C3 C15 C16 120.1(2) . . ?
C10 C16 C6 120.0(3) . . ?
C10 C16 C15 120.0(2) . . ?
C6 C16 C15 120.0(2) . . ?
C8 C9 C10 121.1(3) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C9 C10 C16 118.8(3) . . ?
C9 C10 C11 123.1(3) . . ?
C16 C10 C11 118.2(3) . . ?
C12 C11 C10 121.9(3) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C11 C12 C13 121.1(3) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
O7 C24 C25 111.0(3) . . ?
O7 C24 H24A 109.4 . . ?
C25 C24 H24A 109.4 . . ?
O7 C24 H24B 109.4 . . ?
C25 C24 H24B 109.4 . . ?
H24A C24 H24B 108.0 . . ?
O7 C25 C24 111.0(3) 2_656 . ?
O7 C25 H25B 109.4 2_656 . ?
C24 C25 H25B 109.4 . . ?
O7 C25 H25A 109.4 2_656 . ?
C24 C25 H25A 109.4 . . ?
H25B C25 H25A 108.0 . . ?
O1 C23 O2 124.6(2) . . ?
O1 C23 C17 120.2(2) . . ?
O2 C23 C17 115.2(2) . . ?
C22 C17 C18 120.4(2) . . ?
C22 C17 C23 121.1(2) . . ?
C18 C17 C23 118.4(2) . . ?
C19 C18 C17 118.4(2) . . ?
C19 C18 H18 120.8 . . ?
C17 C18 H18 120.8 . . ?
C18 C19 C20 122.7(3) . . ?
C18 C19 N1 118.8(2) . . ?
C20 C19 N1 118.5(2) . . ?
C19 C20 C21 117.2(3) . . ?
C19 C20 H20 121.4 . . ?
C21 C20 H20 121.4 . . ?
C20 C21 C22 122.7(3) . . ?
C20 C21 N2 118.2(3) . . ?
C22 C21 N2 119.1(3) . . ?
C21 C22 C17 118.6(3) . . ?
C21 C22 H22 120.7 . . ?
C17 C22 H22 120.7 . . ?

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
C14 C1 C2 C3 0.1(4) . . . . ?
C1 C2 C3 C15 0.0(4) . . . . ?
C1 C2 C3 C4 179.5(2) . . . . ?
C2 C3 C4 C5 180.0(2) . . . . ?
C15 C3 C4 C5 -0.5(4) . . . . ?
C3 C4 C5 C6 0.6(4) . . . . ?
C4 C5 C6 C7 179.1(2) . . . . ?
C4 C5 C6 C16 -0.6(4) . . . . ?
C16 C6 C7 C8 0.3(4) . . . . ?
C5 C6 C7 C8 -179.5(2) . . . . ?
C6 C7 C8 C9 -0.4(4) . . . . ?
C2 C1 C14 C13 0.0(4) . . . . ?
C1 C14 C13 C15 -0.4(4) . . . . ?
C1 C14 C13 C12 180.0(2) . . . . ?
C14 C13 C15 C3 0.5(3) . . . . ?
C12 C13 C15 C3 -179.8(2) . . . . ?
C14 C13 C15 C16 -179.7(2) . . . . ?
C12 C13 C15 C16 -0.1(3) . . . . ?
C2 C3 C15 C13 -0.3(3) . . . . ?
C4 C3 C15 C13 -179.9(2) . . . . ?
C2 C3 C15 C16 179.9(2) . . . . ?
C4 C3 C15 C16 0.3(3) . . . . ?
C7 C6 C16 C10 -0.1(3) . . . . ?
C5 C6 C16 C10 179.7(2) . . . . ?
C7 C6 C16 C15 -179.3(2) . . . . ?
C5 C6 C16 C15 0.4(3) . . . . ?
C13 C15 C16 C10 0.7(3) . . . . ?
C3 C15 C16 C10 -179.5(2) . . . . ?
C13 C15 C16 C6 179.9(2) . . . . ?
C3 C15 C16 C6 -0.3(3) . . . . ?
C7 C8 C9 C10 0.4(4) . . . . ?
C8 C9 C10 C16 -0.2(4) . . . . ?
C8 C9 C10 C11 179.8(2) . . . . ?
C6 C16 C10 C9 0.1(3) . . . . ?
C15 C16 C10 C9 179.3(2) . . . . ?
C6 C16 C10 C11 -179.9(2) . . . . ?
C15 C16 C10 C11 -0.7(3) . . . . ?
C9 C10 C11 C12 -179.9(3) . . . . ?
C16 C10 C11 C12 0.1(4) . . . . ?
C10 C11 C12 C13 0.5(4) . . . . ?
C14 C13 C12 C11 179.1(2) . . . . ?
C15 C13 C12 C11 -0.5(4) . . . . ?
C25 O7 C24 C25 -56.7(4) 2_656 . . . ?
O7 C24 C25 O7 57.2(4) . . . 2_656 ?
O1 C23 C17 C22 -180.0(2) . . . . ?
O2 C23 C17 C22 0.5(3) . . . . ?
O1 C23 C17 C18 -1.0(3) . . . . ?
O2 C23 C17 C18 179.5(2) . . . . ?
C22 C17 C18 C19 0.0(3) . . . . ?
C23 C17 C18 C19 -179.0(2) . . . . ?
C17 C18 C19 C20 -0.5(3) . . . . ?
C17 C18 C19 N1 179.9(2) . . . . ?
O4 N1 C19 C18 178.8(2) . . . . ?
O3 N1 C19 C18 -1.8(3) . . . . ?
O4 N1 C19 C20 -0.7(3) . . . . ?
O3 N1 C19 C20 178.7(2) . . . . ?
C18 C19 C20 C21 0.2(4) . . . . ?
N1 C19 C20 C21 179.8(2) . . . . ?
C19 C20 C21 C22 0.6(4) . . . . ?
C19 C20 C21 N2 -179.4(2) . . . . ?
O6 N2 C21 C20 177.2(2) . . . . ?
O5 N2 C21 C20 -2.4(3) . . . . ?
O6 N2 C21 C22 -2.8(3) . . . . ?
O5 N2 C21 C22 177.6(2) . . . . ?
C20 C21 C22 C17 -1.1(4) . . . . ?
N2 C21 C22 C17 178.9(2) . . . . ?
C18 C17 C22 C21 0.8(3) . . . . ?
C23 C17 C22 C21 179.7(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.057


####################################################################### 
# 
# 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_Aminopyrene
_database_code_depnum_ccdc_archive 'CCDC 1909045'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2019-06-19 deposited with the CCDC.	2019-06-20 downloaded from the CCDC.
;

_audit_creation_date             2019-02-25
_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         
'2(C7 H4 N2 O6), 0.5(C6 H14 N2 O2), 2(C16 H11 N)'
_chemical_formula_sum            'C49 H37 N7 O13'
_chemical_formula_weight         931.85
_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   10.1503(3)
_cell_length_b                   11.2758(3)
_cell_length_c                   35.8393(11)
_cell_angle_alpha                90
_cell_angle_beta                 93.409(3)
_cell_angle_gamma                90
_cell_volume                     4094.6(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    33899
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.60
_cell_measurement_theta_min      1.14
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1936
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0787
_diffrn_reflns_av_unetI/netI     0.0547
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            24101
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.049
_diffrn_reflns_theta_max         25.049
_diffrn_reflns_theta_min         1.138
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  
'D8 Quest (Photon II detector/ Chi and Kappa scans)'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2491
_reflns_number_total             3610
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.512
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         3610
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0888
_refine_ls_R_factor_gt           0.0567
_refine_ls_restrained_S_all      1.047
_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)+(0.0577P)²+8.5615P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1308
_refine_ls_wR_factor_ref         0.1532
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Others
 Fixed Sof: C34(0.5) H34A(0.5) C36(0.5) H36A(0.5) H36B(0.5) H36C(0.5) C37(0.5)
 H36D(0.5) H34B(0.5) H34C(0.5)
3.a Me refined with riding coordinates:
 C36(H36A,H36B,H36C), C37(H36D,H34B,H34C)
3.b Aromatic/amide H refined with riding coordinates:
 C22(H22), C24(H24), C26(H26), C34(H34A), C3(H3), C4(H4), C8(H8), C9(H9),
 C13(H13), C14(H14), C15(H15), C16(H16), C17(H17)
3.c X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
3.d Idealised tetrahedral OH refined as rotating group:
 O18(H18)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O18 O 0.5450(2) 1.00533(17) 0.54821(5) 0.0260(5) Uani 1 1 d . . . . .
H18 H 0.543573 1.041252 0.528294 0.039 Uiso 1 1 calc GR . . . .
O19 O 0.4621(2) 0.85990(17) 0.51150(5) 0.0269(5) Uani 1 1 d . . . . .
O27 O 0.3443(2) 0.48598(18) 0.56897(6) 0.0330(6) Uani 1 1 d . . . . .
O28 O 0.3760(2) 0.46118(19) 0.62881(6) 0.0427(6) Uani 1 1 d . . . . .
O30 O 0.6364(2) 0.9332(2) 0.68015(6) 0.0381(6) Uani 1 1 d . . . . .
O31 O 0.6065(2) 0.7590(2) 0.70370(6) 0.0369(6) Uani 1 1 d . . . . .
N29 N 0.3837(2) 0.5196(2) 0.60005(8) 0.0276(6) Uani 1 1 d . . . . .
N32 N 0.6000(2) 0.8298(2) 0.67750(7) 0.0281(6) Uani 1 1 d . . . . .
C20 C 0.5009(3) 0.9001(2) 0.54259(8) 0.0203(6) Uani 1 1 d . . . . .
C21 C 0.4982(3) 0.8228(2) 0.57610(7) 0.0189(6) Uani 1 1 d . . . . .
C22 C 0.5484(3) 0.8624(3) 0.61076(8) 0.0210(7) Uani 1 1 d . . . . .
H22 H 0.583115 0.938419 0.613488 0.025 Uiso 1 1 calc R . . . .
C23 C 0.5459(3) 0.7875(3) 0.64109(7) 0.0212(7) Uani 1 1 d . . . . .
C24 C 0.4939(3) 0.6751(3) 0.63843(8) 0.0229(7) Uani 1 1 d . . . . .
H24 H 0.492465 0.625729 0.659199 0.027 Uiso 1 1 calc R . . . .
C25 C 0.4441(3) 0.6385(2) 0.60381(8) 0.0207(7) Uani 1 1 d . . . . .
C26 C 0.4447(3) 0.7093(2) 0.57242(8) 0.0203(7) Uani 1 1 d . . . . .
H26 H 0.410356 0.681945 0.549369 0.024 Uiso 1 1 calc R . . . .
O33 O 0.000000 0.6947(3) 0.750000 0.0458(9) Uani 1 2 d S T P . .
N35 N 0.000000 0.8961(3) 0.750000 0.0296(9) Uani 1 2 d S T P . .
C34 C -0.0428(6) 0.7940(5) 0.73405(17) 0.0275(14) Uani 0.5 1 d . . . . .
H34A H -0.099919 0.793547 0.712772 0.033 Uiso 0.5 1 calc R . . . .
C36 C -0.0474(7) 1.0097(6) 0.73444(19) 0.0386(17) Uani 0.5 1 d . . . . .
H36A H -0.007965 1.073535 0.748857 0.058 Uiso 0.5 1 calc R . . . .
H36B H -0.023666 1.016230 0.708987 0.058 Uiso 0.5 1 calc R . . . .
H36C H -0.141680 1.013578 0.735274 0.058 Uiso 0.5 1 calc R . . . .
C37 C -0.0612(7) 0.8990(6) 0.71226(16) 0.0328(15) Uani 0.5 1 d . . . . .
H36D H -0.062804 0.979198 0.703216 0.049 Uiso 0.5 1 calc R . . . .
H34B H -0.011332 0.850506 0.696197 0.049 Uiso 0.5 1 calc R . . . .
H34C H -0.149791 0.869376 0.712460 0.049 Uiso 0.5 1 calc R . . . .
N1 N 0.3521(3) 0.9599(3) 0.72885(8) 0.0459(8) Uani 1 1 d . . . . .
H1A H 0.354560 0.919317 0.749198 0.055 Uiso 1 1 calc R . . . .
H1B H 0.381977 1.031265 0.729001 0.055 Uiso 1 1 calc R . . . .
C2 C 0.3015(3) 0.9118(3) 0.69683(8) 0.0293(7) Uani 1 1 d . . . . .
C3 C 0.2530(3) 0.7959(3) 0.69656(9) 0.0312(8) Uani 1 1 d . . . . .
H3 H 0.258954 0.752369 0.718650 0.037 Uiso 1 1 calc R . . . .
C4 C 0.1969(3) 0.7440(3) 0.66495(9) 0.0316(8) Uani 1 1 d . . . . .
H4 H 0.165465 0.666777 0.666186 0.038 Uiso 1 1 calc R . . . .
C5 C 0.1858(3) 0.8044(3) 0.63081(8) 0.0261(7) Uani 1 1 d . . . . .
C6 C 0.2364(3) 0.9239(2) 0.63029(8) 0.0209(7) Uani 1 1 d . . . . .
C7 C 0.2932(3) 0.9774(3) 0.66284(8) 0.0247(7) Uani 1 1 d . . . . .
C8 C 0.3445(3) 1.0938(3) 0.66007(8) 0.0268(7) Uani 1 1 d . . . . .
H8 H 0.384085 1.129078 0.681354 0.032 Uiso 1 1 calc R . . . .
C9 C 0.3382(3) 1.1553(3) 0.62783(8) 0.0236(7) Uani 1 1 d . . . . .
H9 H 0.371943 1.231968 0.627549 0.028 Uiso 1 1 calc R . . . .
C10 C 0.2801(3) 1.1049(3) 0.59372(8) 0.0227(7) Uani 1 1 d . . . . .
C11 C 0.2285(3) 0.9863(2) 0.59541(8) 0.0193(6) Uani 1 1 d . . . . .
C12 C 0.1722(3) 0.9324(3) 0.56239(8) 0.0256(7) Uani 1 1 d . . . . .
C13 C 0.1236(3) 0.8148(3) 0.56454(9) 0.0295(8) Uani 1 1 d . . . . .
H13 H 0.086349 0.778569 0.543121 0.035 Uiso 1 1 calc R . . . .
C14 C 0.1305(3) 0.7546(3) 0.59714(9) 0.0267(7) Uani 1 1 d . . . . .
H14 H 0.097818 0.677575 0.597505 0.032 Uiso 1 1 calc R . . . .
C15 C 0.2735(3) 1.1644(3) 0.55984(8) 0.0275(7) Uani 1 1 d . . . . .
H15 H 0.306999 1.241013 0.558519 0.033 Uiso 1 1 calc R . . . .
C16 C 0.2175(3) 1.1109(3) 0.52788(9) 0.0309(8) Uani 1 1 d . . . . .
H16 H 0.213603 1.152257 0.505396 0.037 Uiso 1 1 calc R . . . .
C17 C 0.1675(3) 0.9977(3) 0.52883(8) 0.0288(7) Uani 1 1 d . . . . .
H17 H 0.130189 0.963758 0.507039 0.035 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
O18 H18 0.8200 . ?
O18 C20 1.279(3) . ?
O19 C20 1.245(3) . ?
O27 N29 1.221(3) . ?
O28 N29 1.230(3) . ?
O30 N32 1.225(3) . ?
O31 N32 1.231(3) . ?
N29 C25 1.477(4) . ?
N32 C23 1.466(4) . ?
C20 C21 1.486(4) . ?
C21 C22 1.388(4) . ?
C21 C26 1.394(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.378(4) . ?
C23 C24 1.374(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.375(4) . ?
C25 C26 1.380(4) . ?
C26 H26 0.9300 . ?
O33 C34 1.319(7) 2_556 ?
O33 C34 1.319(7) . ?
N35 C34 1.345(6) . ?
N35 C36 1.467(7) . ?
N35 C37 1.455(6) . ?
C34 H34A 0.9300 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C37 H36D 0.9600 . ?
C37 H34B 0.9600 . ?
C37 H34C 0.9600 . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N1 C2 1.343(4) . ?
C2 C3 1.397(5) . ?
C2 C7 1.423(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.368(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.399(4) . ?
C5 C6 1.442(4) . ?
C5 C14 1.417(4) . ?
C6 C7 1.406(4) . ?
C6 C11 1.433(4) . ?
C7 C8 1.418(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.346(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.442(4) . ?
C10 C11 1.438(4) . ?
C10 C15 1.386(4) . ?
C11 C12 1.420(4) . ?
C12 C13 1.419(4) . ?
C12 C17 1.408(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.349(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C15 C16 1.387(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.374(4) . ?
C17 H17 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C20 O18 H18 109.5 . . ?
O27 N29 O28 124.4(3) . . ?
O27 N29 C25 118.5(2) . . ?
O28 N29 C25 117.1(3) . . ?
O30 N32 O31 123.8(3) . . ?
O30 N32 C23 118.3(2) . . ?
O31 N32 C23 117.9(3) . . ?
O18 C20 C21 116.1(2) . . ?
O19 C20 O18 124.6(3) . . ?
O19 C20 C21 119.3(3) . . ?
C22 C21 C20 120.8(3) . . ?
C22 C21 C26 120.0(3) . . ?
C26 C21 C20 119.2(2) . . ?
C21 C22 H22 120.5 . . ?
C23 C22 C21 119.1(3) . . ?
C23 C22 H22 120.5 . . ?
C22 C23 N32 118.7(3) . . ?
C24 C23 N32 119.0(3) . . ?
C24 C23 C22 122.4(3) . . ?
C23 C24 H24 121.4 . . ?
C23 C24 C25 117.3(3) . . ?
C25 C24 H24 121.4 . . ?
C24 C25 N29 118.9(3) . . ?
C24 C25 C26 122.9(3) . . ?
C26 C25 N29 118.2(3) . . ?
C21 C26 H26 120.8 . . ?
C25 C26 C21 118.4(3) . . ?
C25 C26 H26 120.8 . . ?
C34 O33 C34 63.8(5) 2_556 . ?
C34 N35 C36 119.7(4) . . ?
C34 N35 C37 61.0(4) . . ?
C37 N35 C36 60.9(4) . . ?
O33 C34 N35 116.9(5) . . ?
O33 C34 H34A 121.6 . . ?
N35 C34 H34A 121.6 . . ?
N35 C36 H36A 109.5 . . ?
N35 C36 H36B 109.5 . . ?
N35 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
N35 C37 H36D 109.5 . . ?
N35 C37 H34B 109.5 . . ?
N35 C37 H34C 109.5 . . ?
H36D C37 H34B 109.5 . . ?
H36D C37 H34C 109.5 . . ?
H34B C37 H34C 109.5 . . ?
H1A N1 H1B 120.0 . . ?
C2 N1 H1A 120.0 . . ?
C2 N1 H1B 120.0 . . ?
N1 C2 C3 120.0(3) . . ?
N1 C2 C7 121.4(3) . . ?
C3 C2 C7 118.5(3) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 C2 122.3(3) . . ?
C4 C3 H3 118.9 . . ?
C3 C4 H4 119.2 . . ?
C3 C4 C5 121.6(3) . . ?
C5 C4 H4 119.2 . . ?
C4 C5 C6 117.1(3) . . ?
C4 C5 C14 124.0(3) . . ?
C14 C5 C6 118.9(3) . . ?
C7 C6 C5 121.2(3) . . ?
C7 C6 C11 120.8(3) . . ?
C11 C6 C5 118.0(3) . . ?
C6 C7 C2 119.2(3) . . ?
C6 C7 C8 118.2(3) . . ?
C8 C7 C2 122.5(3) . . ?
C7 C8 H8 118.7 . . ?
C9 C8 C7 122.6(3) . . ?
C9 C8 H8 118.7 . . ?
C8 C9 H9 119.3 . . ?
C8 C9 C10 121.4(3) . . ?
C10 C9 H9 119.3 . . ?
C11 C10 C9 117.5(3) . . ?
C15 C10 C9 123.2(3) . . ?
C15 C10 C11 119.2(3) . . ?
C6 C11 C10 119.5(3) . . ?
C12 C11 C6 121.0(3) . . ?
C12 C11 C10 119.5(3) . . ?
C13 C12 C11 118.6(3) . . ?
C17 C12 C11 118.7(3) . . ?
C17 C12 C13 122.7(3) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 C12 121.1(3) . . ?
C14 C13 H13 119.4 . . ?
C5 C14 H14 118.8 . . ?
C13 C14 C5 122.4(3) . . ?
C13 C14 H14 118.8 . . ?
C10 C15 H15 119.7 . . ?
C10 C15 C16 120.6(3) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 119.4 . . ?
C17 C16 C15 121.2(3) . . ?
C17 C16 H16 119.4 . . ?
C12 C17 H17 119.6 . . ?
C16 C17 C12 120.8(3) . . ?
C16 C17 H17 119.6 . . ?

_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_Bromopyrene
_database_code_depnum_ccdc_archive 'CCDC 1909046'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2019-06-19 deposited with the CCDC.	2019-06-20 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT201_Bromopyrene         
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......         16 Report
RESPONSE: Due to the severe positional disorder 60:40 of the bromopyrene
the carbon atoms of the disordered pyrene molecule could not be refine 
anisotropically
;
_vrf_PLAT220_Bromopyrene         
;
PROBLEM: Non-Solvent  Resd 3  C   Ueq(max)/Ueq(min) Range       10.0 Ratio 
RESPONSE: Due to the severe positional disorder 60:40 of the bromopyrene molecule

;
# end Validation Reply Form

_audit_creation_date             2019-02-25
_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         '2(C16 H9 Br), C7 H4 N2 O6'
_chemical_formula_sum            'C39 H22 Br2 N2 O6'
_chemical_formula_weight         774.40
_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      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                   8.6941(2)
_cell_length_b                   10.2148(3)
_cell_length_c                   17.2379(4)
_cell_angle_alpha                99.498(2)
_cell_angle_beta                 90.396(2)
_cell_angle_gamma                97.114(2)
_cell_volume                     1497.68(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    22512
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.997
_cell_measurement_theta_min      1.198
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.764
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yelloe
_exptl_crystal_density_diffrn    1.717
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             776
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            22512
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         1.198
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  
'D8 Quest (Photon II detector/ Chi and Kappa scans)'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4610
_reflns_number_total             5260
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.327
_refine_diff_density_min         -0.828
_refine_diff_density_rms         0.138
_refine_ls_extinction_coef       0.0098(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     413
_refine_ls_number_reflns         5260
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0640
_refine_ls_restrained_S_all      1.120
_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)+(0.0619P)²+9.8682P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1625
_refine_ls_wR_factor_ref         0.1691
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2. Others
 Fixed Sof: Br0A(0.6) C7CA(0.6) H7CA(0.6) C5(0.6) C7(0.6) C8(0.6) C9(0.6)
 H9(0.6) C4(0.6) H4(0.6) C0BA(0.6) H0BA(0.6) C9AA(0.6) C1BA(0.6) C3(0.6)
 H3(0.6) C2BA(0.6) C3BA(0.6) H3BA(0.6) C4BA(0.6) H4BA(0.6) C6BA(0.6) H6BA(0.6)
 C7BA(0.6) Br2(0.4) C1(0.6) H1(0.6) C3CA(0.4) H3CA(0.4) C5CA(0.4) H5CA(0.4)
 C8CA(0.4) H8CA(0.4) C10(0.4) C9CA(0.4) C0DA(0.4) H0DA(0.4) C2DA(0.4) H2DA(0.4)
 C1DA(0.4) H1DA(0.4) C6CA(0.4) C6(0.4) C2CA(0.4) C0CA(0.4) C8BA(0.4) C5BA(0.4)
 H5BA(0.4) C9BA(0.4) H9BA(0.4) C1CA(0.4) H1CA(0.4)
3.a Aromatic/amide H refined with riding coordinates:
 C18(H18), C20(H20), C22(H22), C13(H13), C12(H12), C5AA(H5AA), C2AA(H2AA),
 C8AA(H8AA), C1AA(H1AA), C4CA(H4CA), C4AA(H4AA), C7AA(H7AA), C7CA(H7CA), C9(H9),
  C4(H4), C0BA(H0BA), C3(H3), C3BA(H3BA), C4BA(H4BA), C6BA(H6BA), C1(H1),
 C3CA(H3CA), C5CA(H5CA), C8CA(H8CA), C0DA(H0DA), C2DA(H2DA), C1DA(H1DA),
 C5BA(H5BA), C9BA(H9BA), C1CA(H1CA)
3.b Fitted hexagon refined as free rotating group:
 C10(C9CA,C0DA,C2DA,C1DA,C6CA), C6(C2CA,C0CA,C8BA,C5BA,C9BA)
3.c Idealised tetrahedral OH refined as rotating group:
 O5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.62685(7) 0.21702(6) 1.02761(3) 0.0284(2) Uani 1 1 d . . . . .
O5 O 1.0669(4) -0.0622(4) 0.9025(2) 0.0206(8) Uani 1 1 d . . . . .
H5 H 1.097589 -0.032868 0.947906 0.031 Uiso 1 1 calc GR . . . .
O6 O 0.8338(4) -0.0682(4) 0.9574(2) 0.0208(8) Uani 1 1 d . . . . .
O2 O 0.4064(5) -0.3189(4) 0.6604(2) 0.0268(9) Uani 1 1 d . . . . .
O4 O 1.1129(5) -0.1875(4) 0.6240(2) 0.0326(10) Uani 1 1 d . . . . .
O1 O 0.3776(4) -0.2401(4) 0.7841(2) 0.0258(9) Uani 1 1 d . . . . .
O3 O 0.9101(6) -0.2635(4) 0.5490(2) 0.0356(11) Uani 1 1 d . . . . .
N1 N 0.9740(6) -0.2212(4) 0.6135(3) 0.0221(10) Uani 1 1 d . . . . .
N3 N 0.4575(5) -0.2648(4) 0.7260(3) 0.0195(10) Uani 1 1 d . . . . .
C19 C 0.8487(6) -0.1449(5) 0.8208(3) 0.0154(10) Uani 1 1 d . . . . .
C18 C 0.9428(6) -0.1616(5) 0.7560(3) 0.0153(10) Uani 1 1 d . . . . .
H18 H 1.049986 -0.141677 0.762022 0.018 Uiso 1 1 calc R . . . .
C2 C 0.9152(6) -0.0886(5) 0.9005(3) 0.0163(11) Uani 1 1 d . . . . .
C0AA C 0.5764(7) 0.1698(5) 0.9180(3) 0.0215(12) Uani 1 1 d . . . . .
C17 C 0.8743(6) -0.2083(5) 0.6825(3) 0.0179(11) Uani 1 1 d . . . . .
C21 C 0.6272(6) -0.2278(5) 0.7358(3) 0.0184(11) Uani 1 1 d . . . . .
C20 C 0.6879(6) -0.1773(5) 0.8117(3) 0.0156(11) Uani 1 1 d . . . . .
H20 H 0.623585 -0.165658 0.854520 0.019 Uiso 1 1 calc R . . . .
C22 C 0.7170(6) -0.2444(5) 0.6710(3) 0.0165(11) Uani 1 1 d . . . . .
H22 H 0.673644 -0.278658 0.621168 0.020 Uiso 1 1 calc R . . . .
C14 C 0.6944(7) 0.1715(5) 0.8627(3) 0.0220(12) Uani 1 1 d . . . . .
C13 C 0.8544(7) 0.2140(5) 0.8819(3) 0.0242(12) Uani 1 1 d . . . . .
H13 H 0.885479 0.245000 0.934141 0.029 Uiso 1 1 calc R . . . .
C12 C 0.9603(7) 0.2103(5) 0.8263(3) 0.0250(13) Uani 1 1 d . . . . .
H12 H 1.063620 0.238781 0.841143 0.030 Uiso 1 1 calc R . . . .
C11 C 0.9215(7) 0.1641(5) 0.7446(3) 0.0250(13) Uani 1 1 d . . . . .
C16 C 0.7623(7) 0.1228(5) 0.7232(3) 0.0244(13) Uani 1 1 d . . . . .
C5AA C 0.5590(8) 0.0309(6) 0.6233(4) 0.0347(15) Uani 1 1 d . . . . .
H5AA H 0.529289 -0.001881 0.571074 0.042 Uiso 1 1 calc R . . . .
C6AA C 0.7178(8) 0.0755(6) 0.6433(4) 0.0297(14) Uani 1 1 d . . . . .
C2AA C 0.3782(7) 0.0856(6) 0.8185(4) 0.0266(13) Uani 1 1 d . . . . .
H2AA H 0.274174 0.058350 0.804795 0.032 Uiso 1 1 calc R . . . .
C15 C 0.6484(7) 0.1273(5) 0.7824(3) 0.0214(12) Uani 1 1 d . . . . .
C8AA C 0.9936(10) 0.1128(6) 0.6056(4) 0.0404(18) Uani 1 1 d . . . . .
H8AA H 1.068465 0.109613 0.567323 0.048 Uiso 1 1 calc R . . . .
C1AA C 1.0314(8) 0.1575(6) 0.6857(4) 0.0304(14) Uani 1 1 d . . . . .
H1AA H 1.135145 0.184234 0.700310 0.036 Uiso 1 1 calc R . . . .
C4CA C 0.4229(7) 0.1289(6) 0.8975(4) 0.0272(13) Uani 1 1 d . . . . .
H4CA H 0.348738 0.130092 0.936187 0.033 Uiso 1 1 calc R . . . .
C4AA C 0.4494(8) 0.0355(6) 0.6798(4) 0.0292(13) Uani 1 1 d . . . . .
H4AA H 0.346092 0.006658 0.665009 0.035 Uiso 1 1 calc R . . . .
C3AA C 0.4890(7) 0.0829(5) 0.7600(4) 0.0256(13) Uani 1 1 d . . . . .
C7AA C 0.8325(9) 0.0726(6) 0.5868(4) 0.0388(17) Uani 1 1 d . . . . .
H7AA H 0.802389 0.042995 0.534296 0.047 Uiso 1 1 calc R . . . .
Br0A Br 0.37158(12) 0.32306(10) 0.55575(5) 0.0291(3) Uani 0.6 1 d . . P A 1
C7CA C 0.4754(12) 0.4163(9) 0.7345(7) 0.017(3) Uiso 0.6 1 d . . P A 1
H7CA H 0.374203 0.389469 0.715278 0.020 Uiso 0.6 1 calc R . P A 1
C5 C 0.7532(10) 0.4527(8) 0.7109(5) 0.0122(17) Uiso 0.6 1 d . . P A 1
C7 C 0.6017(13) 0.4138(9) 0.6801(5) 0.0145(19) Uiso 0.6 1 d . . P A 1
C8 C 0.7820(10) 0.4953(8) 0.7929(6) 0.0147(17) Uiso 0.6 1 d . . P A 1
C9 C 0.5018(13) 0.4569(9) 0.8128(7) 0.015(2) Uiso 0.6 1 d . . P A 1
H9 H 0.418672 0.457942 0.846517 0.018 Uiso 0.6 1 calc R . P A 1
C4 C 0.706(2) 0.3778(19) 0.5498(9) 0.045(7) Uiso 0.6 1 d . . P A 1
H4 H 0.689249 0.353053 0.495706 0.054 Uiso 0.6 1 calc R . P A 1
C0BA C 0.8474(13) 0.4127(10) 0.5787(6) 0.027(2) Uiso 0.6 1 d . . P A 1
H0BA H 0.929437 0.410755 0.544350 0.033 Uiso 0.6 1 calc R . P A 1
C9AA C 0.8793(12) 0.4527(9) 0.6589(6) 0.025(2) Uiso 0.6 1 d . . P A 1
C1BA C 0.5745(11) 0.3770(9) 0.6006(5) 0.0198(19) Uiso 0.6 1 d . . P A 1
C3 C 1.0392(14) 0.5005(12) 0.6967(8) 0.029(3) Uiso 0.6 1 d . . P A 1
H3 H 1.124782 0.503466 0.664676 0.034 Uiso 0.6 1 calc R . P A 1
C2BA C 0.9372(12) 0.5376(10) 0.8232(6) 0.027(2) Uiso 0.6 1 d . . P A 1
C3BA C 1.0591(13) 0.5351(10) 0.7675(6) 0.031(2) Uiso 0.6 1 d . . P A 1
H3BA H 1.160249 0.561684 0.786797 0.038 Uiso 0.6 1 calc R . P A 1
C4BA C 0.9581(16) 0.5814(13) 0.9093(8) 0.037(3) Uiso 0.6 1 d . . P A 1
H4BA H 1.057437 0.606981 0.931327 0.045 Uiso 0.6 1 calc R . P A 1
C6BA C 0.6875(11) 0.5439(9) 0.9266(5) 0.023(2) Uiso 0.6 1 d . . P A 1
H6BA H 0.605480 0.546194 0.960985 0.027 Uiso 0.6 1 calc R . P A 1
C7BA C 0.6592(12) 0.4991(8) 0.8450(5) 0.0128(17) Uiso 0.6 1 d . . P A 1
Br2 Br 0.7354(2) 0.58727(16) 0.99898(9) 0.0367(4) Uani 0.4 1 d . . P B 2
C1 C 0.8380(13) 0.5843(10) 0.9549(7) 0.032(2) Uiso 0.6 1 d . . P A 1
H1 H 0.854807 0.614844 1.008494 0.039 Uiso 0.6 1 calc R . P A 1
C3CA C 0.560(2) 0.4723(15) 0.8319(10) 0.023(4) Uiso 0.4 1 d . . P B 2
H3CA H 0.509861 0.483872 0.879707 0.028 Uiso 0.4 1 calc R . P B 2
C5CA C 0.4769(18) 0.4254(15) 0.7638(13) 0.019(4) Uiso 0.4 1 d . . P B 2
H5CA H 0.369803 0.405108 0.765346 0.022 Uiso 0.4 1 calc R . P B 2
C8CA C 0.935(2) 0.4517(18) 0.6104(12) 0.044(4) Uiso 0.4 1 d . . P B 2
H8CA H 0.980883 0.443695 0.561497 0.053 Uiso 0.4 1 calc R . P B 2
C10 C 0.7092(12) 0.4366(10) 0.6854(5) 0.018(3) Uiso 0.4 1 d . . P B 2
C9CA C 0.7762(11) 0.4190(13) 0.6121(7) 0.045(4) Uiso 0.4 1 d G . P B 2
C0DA C 0.6839(15) 0.3718(16) 0.5447(5) 0.018(7) Uiso 0.4 1 d G . P B 2
H0DA H 0.728724 0.360064 0.495636 0.022 Uiso 0.4 1 calc R . P B 2
C2DA C 0.5244(15) 0.3422(15) 0.5507(5) 0.067(6) Uiso 0.4 1 d G . P B 2
H2DA H 0.462610 0.310645 0.505637 0.080 Uiso 0.4 1 calc R . P B 2
C1DA C 0.4574(11) 0.3598(12) 0.6241(7) 0.042(4) Uiso 0.4 1 d G . P B 2
H1DA H 0.350681 0.339983 0.628063 0.050 Uiso 0.4 1 calc R . P B 2
C6CA C 0.5497(12) 0.4070(11) 0.6914(5) 0.027(4) Uiso 0.4 1 d G . P B 2
C6 C 0.9597(11) 0.5143(11) 0.7507(4) 0.036(4) Uiso 0.4 1 d . . P B 2
C2CA C 0.8000(11) 0.4859(9) 0.7562(5) 0.019(3) Uiso 0.4 1 d G . P B 2
C0CA C 0.7319(8) 0.5051(9) 0.8292(6) 0.009(2) Uiso 0.4 1 d G . P B 2
C8BA C 0.8235(10) 0.5528(9) 0.8968(4) 0.027(3) Uiso 0.4 1 d G . P B 2
C5BA C 0.9832(9) 0.5812(10) 0.8913(5) 0.006(3) Uiso 0.4 1 d G . P B 2
H5BA H 1.044536 0.613079 0.936518 0.008 Uiso 0.4 1 calc R . P B 2
C9BA C 1.0513(8) 0.5619(10) 0.8183(6) 0.034(4) Uiso 0.4 1 d G . P B 2
H9BA H 1.158191 0.580957 0.814598 0.041 Uiso 0.4 1 calc R . P B 2
C1CA C 1.0243(17) 0.4929(14) 0.6722(10) 0.013(3) Uiso 0.4 1 d . . P B 2
H1CA H 1.130975 0.509023 0.666641 0.015 Uiso 0.4 1 calc R . P B 2


_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 C0AA 1.905(5) . ?
O5 H5 0.8200 . ?
O5 C2 1.312(6) . ?
O6 C2 1.220(6) . ?
O2 N3 1.227(6) . ?
O4 N1 1.218(6) . ?
O1 N3 1.232(6) . ?
O3 N1 1.227(6) . ?
N1 C17 1.474(7) . ?
N3 C21 1.478(7) . ?
C19 C18 1.390(7) . ?
C19 C2 1.482(7) . ?
C19 C20 1.398(7) . ?
C18 H18 0.9300 . ?
C18 C17 1.381(7) . ?
C0AA C14 1.405(8) . ?
C0AA C4CA 1.374(8) . ?
C17 C22 1.375(8) . ?
C21 C20 1.398(7) . ?
C21 C22 1.368(8) . ?
C20 H20 0.9300 . ?
C22 H22 0.9300 . ?
C14 C13 1.425(8) . ?
C14 C15 1.422(8) . ?
C13 H13 0.9300 . ?
C13 C12 1.333(8) . ?
C12 H12 0.9300 . ?
C12 C11 1.433(9) . ?
C11 C16 1.424(9) . ?
C11 C1AA 1.399(8) . ?
C16 C6AA 1.417(8) . ?
C16 C15 1.426(8) . ?
C5AA H5AA 0.9300 . ?
C5AA C6AA 1.421(10) . ?
C5AA C4AA 1.366(9) . ?
C6AA C7AA 1.399(9) . ?
C2AA H2AA 0.9300 . ?
C2AA C4CA 1.397(9) . ?
C2AA C3AA 1.399(9) . ?
C15 C3AA 1.434(8) . ?
C8AA H8AA 0.9300 . ?
C8AA C1AA 1.403(9) . ?
C8AA C7AA 1.430(11) . ?
C1AA H1AA 0.9300 . ?
C4CA H4CA 0.9300 . ?
C4AA H4AA 0.9300 . ?
C4AA C3AA 1.413(8) . ?
C7AA H7AA 0.9300 . ?
Br0A C1BA 1.901(9) . ?
C7CA H7CA 0.9300 . ?
C7CA C7 1.449(15) . ?
C7CA C9 1.355(14) . ?
C5 C7 1.402(14) . ?
C5 C8 1.419(13) . ?
C5 C9AA 1.422(13) . ?
C7 C1BA 1.371(13) . ?
C8 C2BA 1.432(13) . ?
C8 C7BA 1.400(13) . ?
C9 H9 0.9300 . ?
C9 C7BA 1.459(13) . ?
C4 H4 0.9300 . ?
C4 C0BA 1.31(2) . ?
C4 C1BA 1.441(18) . ?
C0BA H0BA 0.9300 . ?
C0BA C9AA 1.392(14) . ?
C9AA C3 1.520(16) . ?
C3 H3 0.9300 . ?
C3 C3BA 1.218(17) . ?
C2BA C3BA 1.434(14) . ?
C2BA C4BA 1.481(16) . ?
C3BA H3BA 0.9300 . ?
C4BA H4BA 0.9300 . ?
C4BA C1 1.311(18) . ?
C6BA H6BA 0.9300 . ?
C6BA C7BA 1.416(12) . ?
C6BA C1 1.382(15) . ?
Br2 C8BA 1.923(7) . ?
C1 H1 0.9300 . ?
C3CA H3CA 0.9300 . ?
C3CA C5CA 1.36(3) . ?
C3CA C0CA 1.50(2) . ?
C5CA H5CA 0.9300 . ?
C5CA C6CA 1.40(2) . ?
C8CA H8CA 0.9300 . ?
C8CA C9CA 1.38(2) . ?
C8CA C1CA 1.29(3) . ?
C10 C9CA 1.3900 . ?
C10 C6CA 1.3900 . ?
C10 C2CA 1.432(10) . ?
C9CA C0DA 1.3900 . ?
C0DA H0DA 0.9300 . ?
C0DA C2DA 1.3900 . ?
C2DA H2DA 0.9300 . ?
C2DA C1DA 1.3900 . ?
C1DA H1DA 0.9300 . ?
C1DA C6CA 1.3900 . ?
C6 C2CA 1.3900 . ?
C6 C9BA 1.3900 . ?
C6 C1CA 1.462(17) . ?
C2CA C0CA 1.3900 . ?
C0CA C8BA 1.3900 . ?
C8BA C5BA 1.3900 . ?
C5BA H5BA 0.9300 . ?
C5BA C9BA 1.3900 . ?
C9BA H9BA 0.9300 . ?
C1CA H1CA 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O5 H5 109.5 . . ?
O4 N1 O3 124.5(5) . . ?
O4 N1 C17 118.2(5) . . ?
O3 N1 C17 117.2(5) . . ?
O2 N3 O1 124.7(5) . . ?
O2 N3 C21 117.5(4) . . ?
O1 N3 C21 117.9(4) . . ?
C18 C19 C2 121.1(5) . . ?
C18 C19 C20 120.4(5) . . ?
C20 C19 C2 118.5(5) . . ?
C19 C18 H18 120.6 . . ?
C17 C18 C19 118.8(5) . . ?
C17 C18 H18 120.6 . . ?
O5 C2 C19 113.5(4) . . ?
O6 C2 O5 124.5(5) . . ?
O6 C2 C19 122.0(5) . . ?
C14 C0AA Br1 120.1(4) . . ?
C4CA C0AA Br1 116.7(4) . . ?
C4CA C0AA C14 123.1(5) . . ?
C18 C17 N1 118.6(5) . . ?
C22 C17 N1 118.6(5) . . ?
C22 C17 C18 122.8(5) . . ?
C20 C21 N3 117.9(5) . . ?
C22 C21 N3 118.9(5) . . ?
C22 C21 C20 123.2(5) . . ?
C19 C20 H20 121.2 . . ?
C21 C20 C19 117.6(5) . . ?
C21 C20 H20 121.2 . . ?
C17 C22 H22 121.4 . . ?
C21 C22 C17 117.2(5) . . ?
C21 C22 H22 121.4 . . ?
C0AA C14 C13 124.6(5) . . ?
C0AA C14 C15 116.8(5) . . ?
C15 C14 C13 118.7(5) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 C14 121.1(5) . . ?
C12 C13 H13 119.4 . . ?
C13 C12 H12 118.6 . . ?
C13 C12 C11 122.7(6) . . ?
C11 C12 H12 118.6 . . ?
C16 C11 C12 117.6(5) . . ?
C1AA C11 C12 123.5(6) . . ?
C1AA C11 C16 118.9(6) . . ?
C11 C16 C15 119.9(5) . . ?
C6AA C16 C11 119.9(5) . . ?
C6AA C16 C15 120.2(6) . . ?
C6AA C5AA H5AA 119.6 . . ?
C4AA C5AA H5AA 119.6 . . ?
C4AA C5AA C6AA 120.8(6) . . ?
C16 C6AA C5AA 119.1(6) . . ?
C7AA C6AA C16 118.7(6) . . ?
C7AA C6AA C5AA 122.1(6) . . ?
C4CA C2AA H2AA 119.8 . . ?
C4CA C2AA C3AA 120.5(6) . . ?
C3AA C2AA H2AA 119.8 . . ?
C14 C15 C16 119.9(5) . . ?
C14 C15 C3AA 120.9(5) . . ?
C16 C15 C3AA 119.1(5) . . ?
C1AA C8AA H8AA 122.2 . . ?
C1AA C8AA C7AA 115.7(6) . . ?
C7AA C8AA H8AA 122.2 . . ?
C11 C1AA C8AA 123.6(7) . . ?
C11 C1AA H1AA 118.2 . . ?
C8AA C1AA H1AA 118.2 . . ?
C0AA C4CA C2AA 119.9(5) . . ?
C0AA C4CA H4CA 120.0 . . ?
C2AA C4CA H4CA 120.0 . . ?
C5AA C4AA H4AA 119.1 . . ?
C5AA C4AA C3AA 121.7(6) . . ?
C3AA C4AA H4AA 119.1 . . ?
C2AA C3AA C15 118.8(5) . . ?
C2AA C3AA C4AA 122.3(6) . . ?
C4AA C3AA C15 119.0(6) . . ?
C6AA C7AA C8AA 123.3(6) . . ?
C6AA C7AA H7AA 118.4 . . ?
C8AA C7AA H7AA 118.4 . . ?
C7 C7CA H7CA 119.4 . . ?
C9 C7CA H7CA 119.4 . . ?
C9 C7CA C7 121.3(9) . . ?
C7 C5 C8 121.0(8) . . ?
C7 C5 C9AA 119.3(9) . . ?
C8 C5 C9AA 119.6(9) . . ?
C5 C7 C7CA 118.1(8) . . ?
C1BA C7 C7CA 121.3(9) . . ?
C1BA C7 C5 120.7(10) . . ?
C5 C8 C2BA 120.3(9) . . ?
C7BA C8 C5 120.5(8) . . ?
C7BA C8 C2BA 119.2(9) . . ?
C7CA C9 H9 119.6 . . ?
C7CA C9 C7BA 120.8(8) . . ?
C7BA C9 H9 119.6 . . ?
C0BA C4 H4 119.5 . . ?
C0BA C4 C1BA 121.1(14) . . ?
C1BA C4 H4 119.5 . . ?
C4 C0BA H0BA 118.9 . . ?
C4 C0BA C9AA 122.3(11) . . ?
C9AA C0BA H0BA 118.9 . . ?
C5 C9AA C3 116.1(9) . . ?
C0BA C9AA C5 118.4(9) . . ?
C0BA C9AA C3 125.6(10) . . ?
C7 C1BA Br0A 122.3(7) . . ?
C7 C1BA C4 118.3(11) . . ?
C4 C1BA Br0A 119.3(10) . . ?
C9AA C3 H3 118.9 . . ?
C3BA C3 C9AA 122.3(11) . . ?
C3BA C3 H3 118.9 . . ?
C8 C2BA C3BA 117.3(9) . . ?
C8 C2BA C4BA 117.2(10) . . ?
C3BA C2BA C4BA 125.5(10) . . ?
C3 C3BA C2BA 124.5(11) . . ?
C3 C3BA H3BA 117.7 . . ?
C2BA C3BA H3BA 117.7 . . ?
C2BA C4BA H4BA 119.7 . . ?
C1 C4BA C2BA 120.7(11) . . ?
C1 C4BA H4BA 119.7 . . ?
C7BA C6BA H6BA 120.3 . . ?
C1 C6BA H6BA 120.3 . . ?
C1 C6BA C7BA 119.5(9) . . ?
C8 C7BA C9 118.3(8) . . ?
C8 C7BA C6BA 120.6(9) . . ?
C6BA C7BA C9 121.1(9) . . ?
C4BA C1 C6BA 122.8(11) . . ?
C4BA C1 H1 118.6 . . ?
C6BA C1 H1 118.6 . . ?
C5CA C3CA H3CA 120.4 . . ?
C5CA C3CA C0CA 119.2(14) . . ?
C0CA C3CA H3CA 120.4 . . ?
C3CA C5CA H5CA 119.4 . . ?
C3CA C5CA C6CA 121.2(14) . . ?
C6CA C5CA H5CA 119.4 . . ?
C9CA C8CA H8CA 117.8 . . ?
C1CA C8CA H8CA 117.8 . . ?
C1CA C8CA C9CA 124.4(17) . . ?
C9CA C10 C6CA 120.0 . . ?
C9CA C10 C2CA 121.8(8) . . ?
C6CA C10 C2CA 118.2(8) . . ?
C8CA C9CA C10 116.9(11) . . ?
C8CA C9CA C0DA 123.1(11) . . ?
C10 C9CA C0DA 120.0 . . ?
C9CA C0DA H0DA 120.0 . . ?
C2DA C0DA C9CA 120.0 . . ?
C2DA C0DA H0DA 120.0 . . ?
C0DA C2DA H2DA 120.0 . . ?
C0DA C2DA C1DA 120.0 . . ?
C1DA C2DA H2DA 120.0 . . ?
C2DA C1DA H1DA 120.0 . . ?
C2DA C1DA C6CA 120.0 . . ?
C6CA C1DA H1DA 120.0 . . ?
C10 C6CA C5CA 122.0(10) . . ?
C1DA C6CA C5CA 118.0(10) . . ?
C1DA C6CA C10 120.0 . . ?
C2CA C6 C9BA 120.0 . . ?
C2CA C6 C1CA 117.4(9) . . ?
C9BA C6 C1CA 122.6(9) . . ?
C6 C2CA C10 118.5(8) . . ?
C6 C2CA C0CA 120.0 . . ?
C0CA C2CA C10 121.5(8) . . ?
C2CA C0CA C3CA 117.9(9) . . ?
C8BA C0CA C3CA 122.1(9) . . ?
C8BA C0CA C2CA 120.0 . . ?
C0CA C8BA Br2 121.9(5) . . ?
C0CA C8BA C5BA 120.0 . . ?
C5BA C8BA Br2 118.1(5) . . ?
C8BA C5BA H5BA 120.0 . . ?
C9BA C5BA C8BA 120.0 . . ?
C9BA C5BA H5BA 120.0 . . ?
C6 C9BA H9BA 120.0 . . ?
C5BA C9BA C6 120.0 . . ?
C5BA C9BA H9BA 120.0 . . ?
C8CA C1CA C6 120.9(15) . . ?
C8CA C1CA H1CA 119.6 . . ?
C6 C1CA H1CA 119.6 . . ?

_olex2_submission_special_instructions 'No special instructions were received'

