# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_pbnpdH14DITFB
_database_code_depnum_ccdc_archive 'CCDC 1976306'
loop_
_audit_author_name
_audit_author_address
'Michael Pfrunder'
;The University of Queensland, Queensland University of Technology
Australia
;
_audit_update_record             
;
2020-01-09 deposited with the CCDC.	2020-02-11 downloaded from the CCDC.
;
_audit_creation_date             2020-01-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 F4 I2, 2(C17 H10 N2 O2)'
_chemical_formula_sum            'C40 H20 F4 I2 N4 O4'
_chemical_formula_weight         950.40
_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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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                   3.9340(8)
_cell_length_b                   14.576(3)
_cell_length_c                   16.601(3)
_cell_angle_alpha                71.17(3)
_cell_angle_beta                 87.33(3)
_cell_angle_gamma                82.84(3)
_cell_volume                     893.9(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    12077
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.371
_cell_measurement_theta_min      1.630
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.829
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   'XDS (Kabsch, 1993)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.765
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             462
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_Laue_measured_fraction_full 0.883
_diffrn_reflns_Laue_measured_fraction_max 0.882
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12077
_diffrn_reflns_point_group_measured_fraction_full 0.883
_diffrn_reflns_point_group_measured_fraction_max 0.882
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         1.630
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.883
_diffrn_measured_fraction_theta_max 0.882
_diffrn_measurement_device_type  'ADSC Quantum 210r'
_diffrn_measurement_method       'Phi Scan'
_diffrn_radiation_monochromator  'Silicon Double Crystal'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.7108
_diffrn_source                   'MX1 Beamline Australian Synchrotron'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3116
_reflns_number_total             3205
_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       'XDS (Kabsch, 1993)'
_computing_data_collection       'BluIce (McPhillips, 2002)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.624
_refine_diff_density_min         -1.505
_refine_diff_density_rms         0.111
_refine_ls_extinction_coef       0.095(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3205
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0297
_refine_ls_restrained_S_all      1.044
_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)+(0.0648P)²+0.6028P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0840
_refine_ls_wR_factor_ref         0.0844
_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. Restrained distances
 H2-O2
 0.87 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C15(H15), C16(H16), C6(H6), C13(H13), C7(H7), C12(H12), C3(H3), C4(H4), C9(H9)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     'intrinsic phasing'
_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
I1 I 1.08271(4) -0.26333(2) 0.46210(2) 0.02177(14) Uani 1 1 d . . . . .
F2 F 1.4925(5) -0.37134(12) 0.34010(11) 0.0338(4) Uani 1 1 d . . . . .
F1 F 1.1927(6) -0.44953(13) 0.63200(12) 0.0352(5) Uani 1 1 d . . . . .
O1 O -0.3314(6) 0.53933(14) 0.04702(13) 0.0266(5) Uani 1 1 d . . . . .
O2 O -0.2095(6) 0.35789(14) 0.10062(13) 0.0252(4) Uani 1 1 d D . . . .
H2 H -0.298(10) 0.4136(19) 0.068(2) 0.038 Uiso 1 1 d DR . . . .
C19 C 1.3306(7) -0.40424(18) 0.48472(18) 0.0201(6) Uani 1 1 d . . . . .
N2 N 0.7223(7) -0.06705(19) 0.42787(19) 0.0329(6) Uani 1 1 d . . . . .
C15 C 0.4214(7) 0.18195(19) 0.35370(19) 0.0236(6) Uani 1 1 d . . . . .
H15 H 0.515821 0.178987 0.406246 0.028 Uiso 1 1 calc R . . . .
C18 C 1.4939(7) -0.43386(19) 0.41988(18) 0.0223(6) Uani 1 1 d . . . . .
C16 C 0.2732(7) 0.27045(18) 0.29790(18) 0.0225(6) Uani 1 1 d . . . . .
H16 H 0.271243 0.328485 0.312357 0.027 Uiso 1 1 calc R . . . .
C11 C 0.1288(7) 0.27512(18) 0.22180(17) 0.0210(6) Uani 1 1 d . . . . .
C14 C 0.4273(7) 0.09747(18) 0.33008(18) 0.0228(6) Uani 1 1 d . . . . .
C17 C 0.5916(8) 0.0054(2) 0.3857(2) 0.0254(6) Uani 1 1 d . . . . .
C8 C -0.1643(7) 0.54500(19) 0.10704(17) 0.0202(6) Uani 1 1 d . . . . .
C10 C -0.0345(7) 0.36842(18) 0.16200(17) 0.0204(6) Uani 1 1 d . . . . .
C20 C 1.3432(8) -0.4729(2) 0.56551(19) 0.0230(5) Uani 1 1 d . . . . .
C6 C -0.0051(7) 0.66179(19) 0.18071(18) 0.0233(6) Uani 1 1 d . . . . .
H6 H 0.085799 0.607954 0.227100 0.028 Uiso 1 1 calc R . . . .
C13 C 0.2807(8) 0.10092(19) 0.25404(19) 0.0260(6) Uani 1 1 d . . . . .
H13 H 0.283507 0.043032 0.239308 0.031 Uiso 1 1 calc R . . . .
N1 N -0.1177(8) 1.01117(19) 0.11654(19) 0.0364(6) Uani 1 1 d . . . . .
C7 C 0.0000(8) 0.7560(2) 0.18286(19) 0.0251(6) Uani 1 1 d . . . . .
H7 H 0.091359 0.766984 0.230474 0.030 Uiso 1 1 calc R . . . .
C12 C 0.1306(7) 0.18958(19) 0.19991(19) 0.0237(6) Uani 1 1 d . . . . .
H12 H 0.029473 0.192312 0.148205 0.028 Uiso 1 1 calc R . . . .
C2 C -0.1324(7) 0.83475(19) 0.11337(19) 0.0241(6) Uani 1 1 d . . . . .
C3 C -0.2692(8) 0.81920(19) 0.04346(19) 0.0253(6) Uani 1 1 d . . . . .
H3 H -0.357664 0.872994 -0.003292 0.030 Uiso 1 1 calc R . . . .
C4 C -0.2750(8) 0.72459(19) 0.04284(18) 0.0234(6) Uani 1 1 d . . . . .
H4 H -0.369728 0.713403 -0.004299 0.028 Uiso 1 1 calc R . . . .
C5 C -0.1413(7) 0.64513(18) 0.11170(17) 0.0211(6) Uani 1 1 d . . . . .
C9 C -0.0032(7) 0.45930(18) 0.16890(18) 0.0210(5) Uani 1 1 d . . . . .
H9 H 0.123777 0.464663 0.214155 0.025 Uiso 1 1 calc R . . . .
C1 C -0.1244(8) 0.9333(2) 0.1154(2) 0.0281(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C19 2.085(3) . ?
F2 C18 1.343(3) . ?
F1 C20 1.348(3) . ?
O1 C8 1.249(4) . ?
O2 H2 0.855(19) . ?
O2 C10 1.315(4) . ?
C19 C18 1.387(4) . ?
C19 C20 1.389(4) . ?
N2 C17 1.136(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.398(4) . ?
C15 C14 1.405(4) . ?
C18 C20 1.379(4) 2_846 ?
C16 H16 0.9500 . ?
C16 C11 1.387(4) . ?
C11 C10 1.489(4) . ?
C11 C12 1.406(4) . ?
C14 C17 1.452(4) . ?
C14 C13 1.396(5) . ?
C8 C5 1.500(4) . ?
C8 C9 1.432(4) . ?
C10 C9 1.387(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.388(4) . ?
C6 C5 1.388(4) . ?
C13 H13 0.9500 . ?
C13 C12 1.391(4) . ?
N1 C1 1.145(4) . ?
C7 H7 0.9500 . ?
C7 C2 1.404(4) . ?
C12 H12 0.9500 . ?
C2 C3 1.395(5) . ?
C2 C1 1.452(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.385(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.405(4) . ?
C9 H9 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
C10 O2 H2 110(3) . . ?
C18 C19 I1 121.6(2) . . ?
C18 C19 C20 116.6(2) . . ?
C20 C19 I1 121.7(2) . . ?
C16 C15 H15 120.9 . . ?
C16 C15 C14 118.3(3) . . ?
C14 C15 H15 120.9 . . ?
F2 C18 C19 120.0(2) . . ?
F2 C18 C20 118.2(3) . 2_846 ?
C20 C18 C19 121.8(3) 2_846 . ?
C15 C16 H16 119.4 . . ?
C11 C16 C15 121.2(3) . . ?
C11 C16 H16 119.4 . . ?
C16 C11 C10 122.1(2) . . ?
C16 C11 C12 119.7(3) . . ?
C12 C11 C10 118.2(3) . . ?
C15 C14 C17 119.1(3) . . ?
C13 C14 C15 121.1(3) . . ?
C13 C14 C17 119.8(3) . . ?
N2 C17 C14 178.7(3) . . ?
O1 C8 C5 117.2(2) . . ?
O1 C8 C9 121.2(2) . . ?
C9 C8 C5 121.6(3) . . ?
O2 C10 C11 114.3(2) . . ?
O2 C10 C9 122.2(3) . . ?
C9 C10 C11 123.5(3) . . ?
F1 C20 C19 120.2(3) . . ?
F1 C20 C18 118.2(3) . 2_846 ?
C18 C20 C19 121.6(3) 2_846 . ?
C7 C6 H6 119.5 . . ?
C7 C6 C5 120.9(3) . . ?
C5 C6 H6 119.5 . . ?
C14 C13 H13 120.2 . . ?
C12 C13 C14 119.7(3) . . ?
C12 C13 H13 120.2 . . ?
C6 C7 H7 120.6 . . ?
C6 C7 C2 118.8(3) . . ?
C2 C7 H7 120.6 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 119.9(3) . . ?
C13 C12 H12 120.0 . . ?
C7 C2 C1 118.8(3) . . ?
C3 C2 C7 121.0(3) . . ?
C3 C2 C1 120.3(3) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 C2 119.4(3) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.2(3) . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C8 123.3(2) . . ?
C6 C5 C4 119.7(2) . . ?
C4 C5 C8 116.9(3) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 C8 119.3(3) . . ?
C10 C9 H9 120.4 . . ?
N1 C1 C2 179.7(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 C19 C18 F2 -0.5(4) . . . . ?
I1 C19 C18 C20 -179.7(2) . . . 2_846 ?
I1 C19 C20 F1 0.1(4) . . . . ?
I1 C19 C20 C18 179.7(2) . . . 2_846 ?
O1 C8 C5 C6 170.9(3) . . . . ?
O1 C8 C5 C4 -7.3(4) . . . . ?
O1 C8 C9 C10 -0.2(4) . . . . ?
O2 C10 C9 C8 -0.4(4) . . . . ?
C15 C16 C11 C10 179.2(3) . . . . ?
C15 C16 C11 C12 0.0(4) . . . . ?
C15 C14 C13 C12 1.0(4) . . . . ?
C18 C19 C20 F1 179.5(3) . . . . ?
C18 C19 C20 C18 -0.8(5) . . . 2_846 ?
C16 C15 C14 C17 177.7(3) . . . . ?
C16 C15 C14 C13 -1.7(4) . . . . ?
C16 C11 C10 O2 -168.9(2) . . . . ?
C16 C11 C10 C9 12.0(4) . . . . ?
C16 C11 C12 C13 -0.8(4) . . . . ?
C11 C10 C9 C8 178.7(2) . . . . ?
C14 C15 C16 C11 1.3(4) . . . . ?
C14 C13 C12 C11 0.3(4) . . . . ?
C17 C14 C13 C12 -178.5(3) . . . . ?
C10 C11 C12 C13 180.0(2) . . . . ?
C20 C19 C18 F2 -180.0(3) . . . . ?
C20 C19 C18 C20 0.8(5) . . . 2_846 ?
C6 C7 C2 C3 0.5(4) . . . . ?
C6 C7 C2 C1 -179.5(3) . . . . ?
C7 C6 C5 C8 -178.0(3) . . . . ?
C7 C6 C5 C4 0.2(4) . . . . ?
C7 C2 C3 C4 0.1(4) . . . . ?
C12 C11 C10 O2 10.3(3) . . . . ?
C12 C11 C10 C9 -168.8(3) . . . . ?
C2 C3 C4 C5 -0.6(4) . . . . ?
C3 C4 C5 C8 178.7(2) . . . . ?
C3 C4 C5 C6 0.4(4) . . . . ?
C5 C8 C9 C10 179.5(2) . . . . ?
C5 C6 C7 C2 -0.6(4) . . . . ?
C9 C8 C5 C6 -8.8(4) . . . . ?
C9 C8 C5 C4 173.0(3) . . . . ?
C1 C2 C3 C4 -179.9(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

# start Validation Reply Form
_vrf_PLAT029_\^a\/E?p-bnpdH.1,4-DITFB\^a\/E? 
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low . 0.883 Why?
RESPONSE: Due to poor diffraction, a synchrotron radiation source was required to collect data adequate to allow structure solution and refinement. 
Due to mechanical limitations of the synchrotron, data was collected over only a single rotation axis leading to low completeness and missed cusps of data.  
;
_vrf_PLAT058_\^a\/E?p-bnpdH.1,4-DITFB\^a\/E? 
;
PROBLEM: Maximum Transmission Factor Missing ............ ?
RESPONSE: This is not reported by the Australian Synchrotron
;
_vrf_PLAT059_\^a\/E?p-bnpdH.1,4-DITFB\^a\/E? 
;
PROBLEM: Minimum Transmission Factor Missing ............ ?
RESPONSE: This is not reported by the Australian Synchrotron
;
_vrf_PLAT430_\^a\/E?p-bnpdH.1,4-DITFB\^a\/E? 
;
PROBLEM: Short Inter D...A Contact O1 ..O1 . 2.69 Ang.
RESPONSE: Hydrogen bond
;
_vrf_PLAT911_\^a\/E?p-bnpdH.1,4-DITFB\^a\/E? 
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L= 0.600 362 Report
RESPONSE: Due to poor diffraction, a synchrotron radiation source was required to collect data adequate to allow structure solution and refinement. 
Due to mechanical limitations of the synchrotron, data was collected over only a single rotation axis leading to low completeness and missed cusps of data.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_pbnpdhTHF
_database_code_depnum_ccdc_archive 'CCDC 1976896'
loop_
_audit_author_name
_audit_author_address
'Kasun S Athukorala Arachchige'
;The University of Queensland
Australia
;
_audit_update_record             
;
2020-01-11 deposited with the CCDC.	2020-02-11 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_pbnpdhTHF           
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.862 Why?
RESPONSE: The data was collected at Australian Synchrotron, and the crystal was weakly diffracting. Thus, low completeness was obtained
;
_vrf_PLAT430_pbnpdhTHF           
;
PROBLEM: Short Inter D...A Contact  O4       ..O4       .       2.75 Ang.
RESPONSE: Hydrogen bonding
;
_vrf_PLAT911_pbnpdhTHF           
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.588        660 Report
RESPONSE: The data was collected at Australian Synchrotron, and the crystal was weakly diffracting. Thus, low completeness was obtained
;
# Added during the CSD deposition process: Saturday 11 January 2020 12:42 AM
# end Validation Reply Form

_audit_creation_date             2020-01-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C17 H10 N2 O2), 0.25(C4 H8 O)'
_chemical_formula_sum            'C35 H22 N4 O4.25'
_chemical_formula_weight         566.56
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.8500(8)
_cell_length_b                   14.124(3)
_cell_length_c                   26.384(5)
_cell_angle_alpha                93.98(3)
_cell_angle_beta                 91.69(3)
_cell_angle_gamma                92.08(3)
_cell_volume                     1429.5(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4229
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.708
_cell_measurement_theta_min      1.548
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.991
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  24.708
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   'XDS (Kabsch, 1993)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             588
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   24.708
_exptl_transmission_factor_min   1.548
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_Laue_measured_fraction_full 0.862
_diffrn_reflns_Laue_measured_fraction_max 0.862
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -3
_diffrn_reflns_number            4229
_diffrn_reflns_point_group_measured_fraction_full 0.862
_diffrn_reflns_point_group_measured_fraction_max 0.862
_diffrn_reflns_theta_full        24.708
_diffrn_reflns_theta_max         24.708
_diffrn_reflns_theta_min         1.548
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.862
_diffrn_measured_fraction_theta_max 0.862
_diffrn_measurement_device_type  'MX1 Beamline Australian Synchrotron'
_diffrn_measurement_method       'Phi Scan'
_diffrn_radiation_monochromator  'Silicon Double Crystal'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.7108
_diffrn_source                   Synchrotron
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3266
_reflns_number_total             4229
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_collection       'BluIce (McPhillips, 2002)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_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         0.546
_refine_diff_density_min         -0.477
_refine_diff_density_rms         0.120
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     400
_refine_ls_number_reflns         4229
_refine_ls_number_restraints     69
_refine_ls_R_factor_all          0.1383
_refine_ls_R_factor_gt           0.1192
_refine_ls_restrained_S_all      1.141
_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)+(0.0965P)²+11.0815P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3540
_refine_ls_wR_factor_ref         0.3645
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.742(6)
 0.258(6)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3. Restrained distances
 O1-H1
 0.97 with sigma of 0.02
 O2-H1
 1.67 with sigma of 0.02
 H3-O3
 0.87 with sigma of 0.02
 C37-C36 \\sim C36-C35 \\sim C35-C34
 with sigma of 0.02
 O5-C37 \\sim O5-C34
 with sigma of 0.02
 O5-C36 \\sim O5-C35
 with sigma of 0.04
 C36-C34 \\sim C37-C35
 with sigma of 0.04
4. Uiso/Uaniso restraints and constraints
O5 \\sim C37 \\sim C36 \\sim C35 \\sim C34: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08
Uanis(C35) = Uanis(C34) = Uanis(O5) = Uanis(C37) = Uanis(C36)
5. Rigid body (RIGU) restrains
 O5, C37, C36, C35, C34
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Fixed Sof: O5(0.25) C37(0.25) H37A(0.25) H37B(0.25) C36(0.25) H36A(0.25)
 H36B(0.25) C35(0.25) H35A(0.25) H35B(0.25) C34(0.25) H34A(0.25) H34B(0.25)
7.a Free rotating group:
 O5(C37,C36,C35,C34)
7.b Secondary CH2 refined with riding coordinates:
 C37(H37A,H37B), C36(H36A,H36B), C35(H35A,H35B), C34(H34A,H34B)
7.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C22(H22), C32(H32), C9(H9), C20(H20), C19(H19), C29(H29), C31(H31),
 C3(H3A), C6(H6), C28(H28), C25(H25), C23(H23), C16(H16), C7(H7), C15(H15),
 C13(H13), C12(H12)
;
_atom_sites_solution_hydrogens   mixed
_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
O3 O -0.3281(15) 0.3823(5) 0.9397(2) 0.0393(15) Uani 1 1 d D . . . .
O4 O -0.3084(15) 0.5552(4) 0.9694(2) 0.0393(15) Uani 1 1 d . . . . .
O2 O 0.3424(16) 0.7747(4) 0.5690(2) 0.0455(16) Uani 1 1 d D . . . .
O1 O 0.6535(16) 0.9196(5) 0.5433(2) 0.0434(16) Uani 1 1 d D . . . .
N4 N 0.480(2) 1.0360(6) 0.9303(3) 0.047(2) Uani 1 1 d . . . . .
N3 N 0.346(2) 0.0207(6) 0.7508(3) 0.053(2) Uani 1 1 d . . . . .
N2 N -0.500(2) 0.5491(6) 0.7861(3) 0.051(2) Uani 1 1 d . . . . .
C5 C 0.749(2) 1.0588(6) 0.5976(3) 0.036(2) Uani 1 1 d . . . . .
C21 C -0.038(2) 0.3249(6) 0.8674(3) 0.0344(19) Uani 1 1 d . . . . .
C10 C 0.304(2) 0.8185(6) 0.6136(3) 0.037(2) Uani 1 1 d . . . . .
C27 C -0.002(2) 0.6733(6) 0.9288(3) 0.0355(19) Uani 1 1 d . . . . .
C8 C 0.611(2) 0.9592(7) 0.5877(3) 0.037(2) Uani 1 1 d . . . . .
C4 C 0.757(2) 1.1048(7) 0.6459(4) 0.041(2) Uani 1 1 d . . . . .
H4 H 0.670066 1.073678 0.672993 0.049 Uiso 1 1 calc R . . . .
C22 C -0.117(2) 0.2332(6) 0.8813(3) 0.036(2) Uani 1 1 d . . . . .
H22 H -0.234611 0.224399 0.911064 0.044 Uiso 1 1 calc R . . . .
C32 C 0.159(2) 0.7065(6) 0.8856(4) 0.038(2) Uani 1 1 d . . . . .
H32 H 0.190927 0.664918 0.857326 0.046 Uiso 1 1 calc R . . . .
C9 C 0.431(2) 0.9105(6) 0.6248(3) 0.038(2) Uani 1 1 d . . . . .
H9 H 0.397621 0.940540 0.656685 0.046 Uiso 1 1 calc R . . . .
C26 C -0.123(2) 0.5722(6) 0.9316(3) 0.037(2) Uani 1 1 d . . . . .
C33 C 0.364(2) 0.9585(7) 0.9290(3) 0.039(2) Uani 1 1 d . . . . .
C20 C 0.127(2) 0.3382(7) 0.8216(3) 0.038(2) Uani 1 1 d . . . . .
H20 H 0.173898 0.399155 0.811633 0.046 Uiso 1 1 calc R . . . .
C30 C 0.231(2) 0.8626(6) 0.9279(3) 0.037(2) Uani 1 1 d . . . . .
C19 C 0.221(2) 0.2596(6) 0.7913(3) 0.036(2) Uani 1 1 d . . . . .
H19 H 0.335236 0.268008 0.761331 0.043 Uiso 1 1 calc R . . . .
C18 C 0.145(2) 0.1681(6) 0.8055(3) 0.038(2) Uani 1 1 d . . . . .
C29 C 0.072(2) 0.8307(6) 0.9707(3) 0.0365(19) Uani 1 1 d . . . . .
H29 H 0.046331 0.872025 0.999263 0.044 Uiso 1 1 calc R . . . .
C31 C 0.269(2) 0.8003(6) 0.8853(4) 0.038(2) Uani 1 1 d . . . . .
H31 H 0.369759 0.822294 0.856534 0.046 Uiso 1 1 calc R . . . .
C2 C 1.020(2) 1.2445(7) 0.6132(4) 0.044(2) Uani 1 1 d . . . . .
C3 C 0.893(2) 1.1966(7) 0.6539(4) 0.045(2) Uani 1 1 d . . . . .
H3A H 0.900971 1.226686 0.686446 0.054 Uiso 1 1 calc R . . . .
C24 C -0.135(2) 0.4076(6) 0.9012(3) 0.036(2) Uani 1 1 d . . . . .
N1 N 1.300(2) 1.4131(7) 0.6304(4) 0.072(3) Uani 1 1 d . . . . .
C6 C 0.877(2) 1.1054(6) 0.5573(3) 0.039(2) Uani 1 1 d . . . . .
H6 H 0.874734 1.074465 0.525018 0.046 Uiso 1 1 calc R . . . .
C28 C -0.048(2) 0.7368(6) 0.9705(3) 0.037(2) Uani 1 1 d . . . . .
H28 H -0.160378 0.716100 0.998625 0.045 Uiso 1 1 calc R . . . .
C25 C -0.036(2) 0.4999(6) 0.8955(3) 0.036(2) Uani 1 1 d . . . . .
H25 H 0.091412 0.514985 0.867567 0.043 Uiso 1 1 calc R . . . .
C14 C -0.198(2) 0.6485(7) 0.7202(3) 0.041(2) Uani 1 1 d . . . . .
C23 C -0.021(2) 0.1547(6) 0.8506(3) 0.038(2) Uani 1 1 d . . . . .
H23 H -0.067358 0.093582 0.860312 0.046 Uiso 1 1 calc R . . . .
C16 C 0.003(2) 0.6695(7) 0.6363(4) 0.042(2) Uani 1 1 d . . . . .
H16 H 0.026122 0.646209 0.602767 0.050 Uiso 1 1 calc R . . . .
C17 C 0.254(2) 0.0867(7) 0.7751(4) 0.042(2) Uani 1 1 d . . . . .
C7 C 1.012(2) 1.1992(7) 0.5650(4) 0.045(2) Uani 1 1 d . . . . .
H7 H 1.094084 1.230808 0.537695 0.054 Uiso 1 1 calc R . . . .
C011 C -0.363(2) 0.5920(7) 0.7564(4) 0.045(2) Uani 1 1 d . . . . .
C15 C -0.156(2) 0.6116(6) 0.6709(4) 0.041(2) Uani 1 1 d . . . . .
H15 H -0.231628 0.549709 0.660856 0.049 Uiso 1 1 calc R . . . .
C13 C -0.085(2) 0.7417(7) 0.7352(4) 0.040(2) Uani 1 1 d . . . . .
H13 H -0.118544 0.766566 0.768143 0.048 Uiso 1 1 calc R . . . .
C12 C 0.077(2) 0.7966(7) 0.7011(4) 0.041(2) Uani 1 1 d . . . . .
H12 H 0.155155 0.858238 0.711262 0.050 Uiso 1 1 calc R . . . .
C11 C 0.124(2) 0.7600(6) 0.6514(3) 0.036(2) Uani 1 1 d . . . . .
C1 C 1.175(2) 1.3377(7) 0.6227(4) 0.052(3) Uani 1 1 d . . . . .
H3 H -0.36(4) 0.432(7) 0.960(5) 0.13(6) Uiso 1 1 d D . . . .
H1 H 0.47(4) 0.871(11) 0.540(6) 0.28(14) Uiso 1 1 d D . . . .
O5 O -0.205(5) 0.6131(14) 0.4988(8) 0.040(3) Uani 0.25 1 d D U P A -1
C37 C -0.537(5) 0.5633(17) 0.4981(12) 0.040(3) Uani 0.25 1 d DG U P A -1
H37A H -0.693579 0.587490 0.473001 0.048 Uiso 0.25 1 calc R . P A -1
H37B H -0.640129 0.571009 0.531140 0.048 Uiso 0.25 1 calc R . P A -1
C36 C -0.469(8) 0.4586(16) 0.4844(11) 0.040(3) Uani 0.25 1 d DG U P A -1
H36A H -0.477063 0.444237 0.447884 0.048 Uiso 0.25 1 calc R . P A -1
H36B H -0.635245 0.417024 0.499836 0.048 Uiso 0.25 1 calc R . P A -1
C35 C -0.100(8) 0.4500(18) 0.507(2) 0.040(3) Uani 0.25 1 d DG U P A -1
H35A H -0.104433 0.440766 0.543136 0.048 Uiso 0.25 1 calc R . P A -1
H35B H 0.018523 0.398292 0.489856 0.048 Uiso 0.25 1 calc R . P A -1
C34 C 0.069(5) 0.547(2) 0.497(2) 0.040(3) Uani 0.25 1 d DG U P A -1
H34A H 0.247304 0.565123 0.523134 0.048 Uiso 0.25 1 calc R . P A -1
H34B H 0.174894 0.543747 0.464272 0.048 Uiso 0.25 1 calc R . P A -1


_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
O3 C24 1.336(10) . ?
O3 H3 0.87(2) . ?
O4 C26 1.274(10) . ?
O2 C10 1.305(11) . ?
O1 C8 1.280(11) . ?
O1 H1 0.97(2) . ?
N4 C33 1.165(11) . ?
N3 C17 1.166(12) . ?
N2 C011 1.151(12) . ?
C5 C8 1.487(12) . ?
C5 C4 1.389(12) . ?
C5 C6 1.382(12) . ?
C21 C22 1.397(12) . ?
C21 C20 1.404(12) . ?
C21 C24 1.485(12) . ?
C10 C9 1.380(12) . ?
C10 C11 1.508(12) . ?
C27 C32 1.415(12) . ?
C27 C26 1.493(12) . ?
C27 C28 1.389(12) . ?
C8 C9 1.419(12) . ?
C4 H4 0.9300 . ?
C4 C3 1.381(13) . ?
C22 H22 0.9300 . ?
C22 C23 1.396(12) . ?
C32 H32 0.9300 . ?
C32 C31 1.378(12) . ?
C9 H9 0.9300 . ?
C26 C25 1.404(12) . ?
C33 C30 1.429(12) . ?
C20 H20 0.9300 . ?
C20 C19 1.387(12) . ?
C30 C29 1.395(12) . ?
C30 C31 1.392(12) . ?
C19 H19 0.9300 . ?
C19 C18 1.393(12) . ?
C18 C23 1.388(12) . ?
C18 C17 1.437(13) . ?
C29 H29 0.9300 . ?
C29 C28 1.387(12) . ?
C31 H31 0.9300 . ?
C2 C3 1.399(14) . ?
C2 C7 1.383(13) . ?
C2 C1 1.428(13) . ?
C3 H3A 0.9300 . ?
C24 C25 1.366(12) . ?
N1 C1 1.155(12) . ?
C6 H6 0.9300 . ?
C6 C7 1.404(12) . ?
C28 H28 0.9300 . ?
C25 H25 0.9300 . ?
C14 C011 1.437(13) . ?
C14 C15 1.382(13) . ?
C14 C13 1.398(13) . ?
C23 H23 0.9300 . ?
C16 H16 0.9300 . ?
C16 C15 1.406(13) . ?
C16 C11 1.373(12) . ?
C7 H7 0.9300 . ?
C15 H15 0.9300 . ?
C13 H13 0.9300 . ?
C13 C12 1.374(12) . ?
C12 H12 0.9300 . ?
C12 C11 1.395(13) . ?
O5 C37 1.4362 . ?
O5 C34 1.4362 . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C37 C36 1.5321 . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C36 C35 1.5357 . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C35 C34 1.5318 . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?

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 O3 H3 109(10) . . ?
C8 O1 H1 103(10) . . ?
C4 C5 C8 121.9(8) . . ?
C6 C5 C8 118.4(8) . . ?
C6 C5 C4 119.6(9) . . ?
C22 C21 C20 120.0(8) . . ?
C22 C21 C24 119.2(7) . . ?
C20 C21 C24 120.8(8) . . ?
O2 C10 C9 121.5(8) . . ?
O2 C10 C11 114.9(8) . . ?
C9 C10 C11 123.6(8) . . ?
C32 C27 C26 122.5(8) . . ?
C28 C27 C32 118.9(8) . . ?
C28 C27 C26 118.6(8) . . ?
O1 C8 C5 116.9(8) . . ?
O1 C8 C9 120.8(8) . . ?
C9 C8 C5 122.2(8) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 C5 120.5(9) . . ?
C3 C4 H4 119.8 . . ?
C21 C22 H22 120.0 . . ?
C23 C22 C21 120.0(8) . . ?
C23 C22 H22 120.0 . . ?
C27 C32 H32 120.0 . . ?
C31 C32 C27 120.0(8) . . ?
C31 C32 H32 120.0 . . ?
C10 C9 C8 120.1(8) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
O4 C26 C27 115.6(8) . . ?
O4 C26 C25 121.8(8) . . ?
C25 C26 C27 122.6(8) . . ?
N4 C33 C30 178.5(10) . . ?
C21 C20 H20 120.3 . . ?
C19 C20 C21 119.4(8) . . ?
C19 C20 H20 120.3 . . ?
C29 C30 C33 119.3(8) . . ?
C31 C30 C33 120.6(8) . . ?
C31 C30 C29 120.0(8) . . ?
C20 C19 H19 119.7 . . ?
C20 C19 C18 120.6(8) . . ?
C18 C19 H19 119.7 . . ?
C19 C18 C17 120.5(8) . . ?
C23 C18 C19 120.2(8) . . ?
C23 C18 C17 119.2(8) . . ?
C30 C29 H29 120.2 . . ?
C28 C29 C30 119.5(8) . . ?
C28 C29 H29 120.2 . . ?
C32 C31 C30 120.5(9) . . ?
C32 C31 H31 119.8 . . ?
C30 C31 H31 119.8 . . ?
C3 C2 C1 119.2(9) . . ?
C7 C2 C3 119.8(9) . . ?
C7 C2 C1 121.0(9) . . ?
C4 C3 C2 120.1(9) . . ?
C4 C3 H3A 119.9 . . ?
C2 C3 H3A 119.9 . . ?
O3 C24 C21 112.7(7) . . ?
O3 C24 C25 122.3(8) . . ?
C25 C24 C21 125.0(8) . . ?
C5 C6 H6 119.8 . . ?
C5 C6 C7 120.3(9) . . ?
C7 C6 H6 119.8 . . ?
C27 C28 H28 119.5 . . ?
C29 C28 C27 121.0(8) . . ?
C29 C28 H28 119.5 . . ?
C26 C25 H25 119.8 . . ?
C24 C25 C26 120.5(8) . . ?
C24 C25 H25 119.8 . . ?
C15 C14 C011 120.3(9) . . ?
C15 C14 C13 120.5(8) . . ?
C13 C14 C011 119.1(9) . . ?
C22 C23 H23 120.1 . . ?
C18 C23 C22 119.8(8) . . ?
C18 C23 H23 120.1 . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
C11 C16 C15 120.7(9) . . ?
N3 C17 C18 178.9(11) . . ?
C2 C7 C6 119.7(9) . . ?
C2 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
N2 C011 C14 177.9(11) . . ?
C14 C15 C16 118.7(8) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 H15 120.6 . . ?
C14 C13 H13 120.0 . . ?
C12 C13 C14 119.9(9) . . ?
C12 C13 H13 120.0 . . ?
C13 C12 H12 119.9 . . ?
C13 C12 C11 120.2(9) . . ?
C11 C12 H12 119.9 . . ?
C16 C11 C10 119.1(8) . . ?
C16 C11 C12 119.8(8) . . ?
C12 C11 C10 121.1(8) . . ?
N1 C1 C2 179.9(14) . . ?
C37 O5 C34 110.1 . . ?
O5 C37 H37A 110.5 . . ?
O5 C37 H37B 110.5 . . ?
O5 C37 C36 106.3 . . ?
H37A C37 H37B 108.7 . . ?
C36 C37 H37A 110.5 . . ?
C36 C37 H37B 110.5 . . ?
C37 C36 H36A 111.4 . . ?
C37 C36 H36B 111.4 . . ?
C37 C36 C35 101.8 . . ?
H36A C36 H36B 109.3 . . ?
C35 C36 H36A 111.4 . . ?
C35 C36 H36B 111.4 . . ?
C36 C35 H35A 111.4 . . ?
C36 C35 H35B 111.4 . . ?
H35A C35 H35B 109.3 . . ?
C34 C35 C36 101.8 . . ?
C34 C35 H35A 111.4 . . ?
C34 C35 H35B 111.4 . . ?
O5 C34 C35 106.3 . . ?
O5 C34 H34A 110.5 . . ?
O5 C34 H34B 110.5 . . ?
C35 C34 H34A 110.5 . . ?
C35 C34 H34B 110.5 . . ?
H34A C34 H34B 108.7 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.742(6)
2 0.258(6)

####################################################################### 
# 
# 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_csn13m_tw
_database_code_depnum_ccdc_archive 'CCDC 1976701'
loop_
_audit_author_name
_audit_author_address
'Aidan J. Brock'
;Queensland University of Technology
Australia
;
_audit_update_record             
;
2020-01-10 deposited with the CCDC.	2020-02-11 downloaded from the CCDC.
;
_audit_creation_date             2020-01-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H10 N2 O2'
_chemical_formula_sum            'C17 H10 N2 O2'
_chemical_formula_weight         274.27
_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                   7.1360(14)
_cell_length_b                   12.568(3)
_cell_length_c                   14.975(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.29(3)
_cell_angle_gamma                90
_cell_volume                     1339.2(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1584
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.867
_cell_measurement_theta_min      2.728
_shelx_estimated_absorpt_T_max   0.999
_shelx_estimated_absorpt_T_min   0.999
_exptl_absorpt_coefficient_mu    0.091
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.01
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0482
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1584
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.244
_diffrn_reflns_theta_max         27.867
_diffrn_reflns_theta_min         2.728
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'ADSC Quantum 315r'
_diffrn_measurement_method       'Phi scans'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.7108
_diffrn_source                   'MX1 Beamline Australian Synchrotron'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1354
_reflns_number_total             1584
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_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    ?
_refine_diff_density_max         0.488
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.124
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.282
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1584
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1153
_refine_ls_R_factor_gt           0.1062
_refine_ls_restrained_S_all      1.282
_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)+(0.0878P)²+7.1120P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3106
_refine_ls_wR_factor_ref         0.3161
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.814(9)
 0.186(9)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3. Others
 Fixed Sof: H001(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C003(H003), C004(H004), C006(H006), C00A(H00A), C00B(H00B)
;
_atom_sites_solution_hydrogens   mixed
_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
O001 O 0.8399(4) 0.6924(3) 0.7136(2) 0.0376(8) Uani 1 1 d . . . . .
N002 N 0.0506(5) 0.3541(4) 0.5152(3) 0.0421(10) Uani 1 1 d . . . . .
C003 C 0.3611(6) 0.5535(4) 0.5972(3) 0.0331(10) Uani 1 1 d . . . . .
H003 H 0.255774 0.596451 0.578411 0.040 Uiso 1 1 calc R . . . .
C004 C 0.6703(6) 0.4271(4) 0.6512(3) 0.0335(10) Uani 1 1 d . . . . .
H004 H 0.776176 0.384380 0.669385 0.040 Uiso 1 1 calc R . . . .
C005 C 0.6762(6) 0.5364(4) 0.6658(3) 0.0311(9) Uani 1 1 d . . . . .
C006 C 0.5216(6) 0.5995(4) 0.6369(3) 0.0329(10) Uani 1 1 d . . . . .
H006 H 0.527505 0.674446 0.644771 0.039 Uiso 1 1 calc R . . . .
C007 C 0.3543(6) 0.4448(4) 0.5848(3) 0.0312(10) Uani 1 1 d . . . . .
C008 C 0.8454(6) 0.5901(4) 0.7112(3) 0.0312(9) Uani 1 1 d . . . . .
C009 C 0.1845(6) 0.3936(4) 0.5450(3) 0.0356(10) Uani 1 1 d . . . . .
C00A C 0.5103(6) 0.3805(4) 0.6101(3) 0.0345(10) Uani 1 1 d . . . . .
H00A H 0.506235 0.306032 0.599232 0.041 Uiso 1 1 calc R . . . .
C00B C 1.000000 0.5338(5) 0.750000 0.0318(13) Uani 1 2 d S T P . .
H00B H 1.000001 0.458232 0.749999 0.038 Uiso 1 2 calc RS T P . .
H001 H 0.955(15) 0.716(7) 0.760(8) 0.038 Uiso 0.5 1 d R . . A -1


_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
O001 C008 1.287(6) . ?
O001 H001 1.07(13) . ?
N002 C009 1.138(6) . ?
C003 H003 0.9500 . ?
C003 C006 1.378(6) . ?
C003 C007 1.380(7) . ?
C004 H004 0.9500 . ?
C004 C005 1.391(6) . ?
C004 C00A 1.386(6) . ?
C005 C006 1.400(6) . ?
C005 C008 1.501(6) . ?
C006 H006 0.9500 . ?
C007 C009 1.459(6) . ?
C007 C00A 1.405(6) . ?
C008 C00B 1.400(5) . ?
C00A H00A 0.9500 . ?
C00B H00B 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
C008 O001 H001 105(5) . . ?
C006 C003 H003 120.2 . . ?
C006 C003 C007 119.5(4) . . ?
C007 C003 H003 120.2 . . ?
C005 C004 H004 120.0 . . ?
C00A C004 H004 120.0 . . ?
C00A C004 C005 120.1(4) . . ?
C004 C005 C006 119.8(4) . . ?
C004 C005 C008 121.9(4) . . ?
C006 C005 C008 118.3(4) . . ?
C003 C006 C005 120.4(4) . . ?
C003 C006 H006 119.8 . . ?
C005 C006 H006 119.8 . . ?
C003 C007 C009 120.7(4) . . ?
C003 C007 C00A 121.0(4) . . ?
C00A C007 C009 118.3(4) . . ?
O001 C008 C005 115.9(4) . . ?
O001 C008 C00B 121.2(4) . . ?
C00B C008 C005 122.9(4) . . ?
N002 C009 C007 178.8(5) . . ?
C004 C00A C007 119.1(4) . . ?
C004 C00A H00A 120.4 . . ?
C007 C00A H00A 120.4 . . ?
C008 C00B C008 119.3(6) 2_756 . ?
C008 C00B H00B 120.4 2_756 . ?
C008 C00B H00B 120.4 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.814(9)
2 0.186(9)

