# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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. 
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data_LNB304
_database_code_depnum_ccdc_archive 'CCDC 2099681'
loop_
_audit_author_name
_audit_author_address
'David Wragg'
;University of Oslo
Norway
;
_audit_update_record             
;
2021-07-27 deposited with the CCDC.	2021-10-19 downloaded from the CCDC.
;
_audit_creation_date             2021-01-21
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
l.n.berntsen@kjemi.uio.no
david.wragg@smn.uio.no
_chemical_name_common            ?
_chemical_name_systematic        (E)-N-Styrylphthalimide
_chemical_formula_moiety         '2(C16 H11 N O2)'
_chemical_formula_sum            'C32 H22 N2 O4'
_chemical_formula_weight         498.51
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   28.5959(19)
_cell_length_b                   7.4128(5)
_cell_length_c                   11.4628(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2429.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9881
_cell_measurement_temperature    104.6
_cell_measurement_theta_max      29.36
_cell_measurement_theta_min      2.28
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.973
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1189 before and 0.0397 after correction.
The Ratio of minimum to maximum transmission is 0.9296.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16187
_diffrn_reflns_point_group_measured_fraction_full 0.843
_diffrn_reflns_point_group_measured_fraction_max 0.829
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_min         2.277
_diffrn_ambient_temperature      104.6
_diffrn_detector                 'Bruker Photon 100 area detector'
_diffrn_detector_area_resol_mean 10.42
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ shutterless scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.582
_reflns_Friedel_fraction_full    0.675
_reflns_Friedel_fraction_max     0.644
_reflns_number_gt                3926
_reflns_number_total             4117
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 1389 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.867
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         4117
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0320
_refine_ls_restrained_S_all      0.866
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0937
_refine_ls_wR_factor_ref         0.0969
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13),
 C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C21(H21), C22(H22), C25(H25),
  C26(H26), C27(H27), C30(H30), C31(H31), C32(H32)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.56961(5) 0.73214(18) 0.52392(13) 0.0205(3) Uani 1 1 d . . . . .
O2 O 0.58674(5) 1.06256(18) 0.18836(13) 0.0186(3) Uani 1 1 d . . . . .
O3 O 0.58144(4) 0.56148(19) 0.81122(12) 0.0197(3) Uani 1 1 d . . . . .
O4 O 0.57424(5) 0.23845(19) 0.47039(13) 0.0203(3) Uani 1 1 d . . . . .
N1 N 0.59058(5) 0.88206(19) 0.35457(14) 0.0132(4) Uani 1 1 d . . . . .
N2 N 0.59082(5) 0.39261(19) 0.64226(14) 0.0128(4) Uani 1 1 d . . . . .
C1 C 0.42946(7) 0.9024(3) 0.3830(2) 0.0200(5) Uani 1 1 d . . . . .
H1 H 0.398910 0.880459 0.412301 0.024 Uiso 1 1 calc R U . . .
C2 C 0.46786(6) 0.8334(3) 0.44312(18) 0.0177(4) Uani 1 1 d . . . . .
H2 H 0.464296 0.764548 0.512434 0.021 Uiso 1 1 calc R U . . .
C3 C 0.51163(6) 0.8708(2) 0.39635(18) 0.0151(4) Uani 1 1 d . . . . .
C4 C 0.55884(6) 0.8162(2) 0.43733(17) 0.0139(4) Uani 1 1 d . . . . .
C5 C 0.63878(6) 0.8476(2) 0.36657(18) 0.0145(4) Uani 1 1 d . . . . .
H5 H 0.648423 0.788779 0.436149 0.017 Uiso 1 1 calc R U . . .
C6 C 0.67210(6) 0.8891(2) 0.29047(19) 0.0158(4) Uani 1 1 d . . . . .
H6 H 0.663172 0.948603 0.220540 0.019 Uiso 1 1 calc R U . . .
C7 C 0.72193(6) 0.8485(2) 0.30773(18) 0.0147(4) Uani 1 1 d . . . . .
C8 C 0.75384(7) 0.9041(2) 0.22256(18) 0.0177(4) Uani 1 1 d . . . . .
H8 H 0.742857 0.964728 0.154892 0.021 Uiso 1 1 calc R U . . .
C9 C 0.80120(7) 0.8717(3) 0.2356(2) 0.0208(5) Uani 1 1 d . . . . .
H9 H 0.822405 0.910314 0.176897 0.025 Uiso 1 1 calc R U . . .
C10 C 0.81798(7) 0.7833(2) 0.3339(2) 0.0208(4) Uani 1 1 d . . . . .
H10 H 0.850517 0.761462 0.342869 0.025 Uiso 1 1 calc R U . . .
C11 C 0.43473(6) 1.0026(3) 0.2809(2) 0.0185(4) Uani 1 1 d . . . . .
H11 H 0.407783 1.046430 0.241577 0.022 Uiso 1 1 calc R U . . .
C12 C 0.51711(6) 0.9717(2) 0.29545(19) 0.0142(4) Uani 1 1 d . . . . .
C13 C 0.47912(6) 1.0396(3) 0.23568(18) 0.0160(4) Uani 1 1 d . . . . .
H13 H 0.482963 1.108724 0.166548 0.019 Uiso 1 1 calc R U . . .
C14 C 0.56775(6) 0.9840(2) 0.26764(18) 0.0129(4) Uani 1 1 d . . . . .
C15 C 0.78650(7) 0.7270(2) 0.41910(19) 0.0200(4) Uani 1 1 d . . . . .
H15 H 0.797641 0.666435 0.486634 0.024 Uiso 1 1 calc R U . . .
C16 C 0.73904(7) 0.7589(2) 0.40609(19) 0.0181(4) Uani 1 1 d . . . . .
H16 H 0.717901 0.719312 0.464684 0.022 Uiso 1 1 calc R U . . .
C17 C 0.81772(6) 0.3005(3) 0.5760(2) 0.0190(4) Uani 1 1 d . . . . .
H17 H 0.850835 0.290786 0.578463 0.023 Uiso 1 1 calc R U . . .
C18 C 0.79341(7) 0.3811(2) 0.66790(19) 0.0190(4) Uani 1 1 d . . . . .
H18 H 0.810136 0.427878 0.732791 0.023 Uiso 1 1 calc R U . . .
C19 C 0.74511(7) 0.3932(2) 0.66517(18) 0.0183(4) Uani 1 1 d . . . . .
H19 H 0.729022 0.448658 0.728188 0.022 Uiso 1 1 calc R U . . .
C20 C 0.71975(7) 0.3248(2) 0.57089(18) 0.0156(4) Uani 1 1 d . . . . .
C21 C 0.66829(6) 0.3260(3) 0.56356(18) 0.0170(4) Uani 1 1 d . . . . .
H21 H 0.654255 0.276313 0.495668 0.020 Uiso 1 1 calc R U . . .
C22 C 0.64005(6) 0.3922(2) 0.64589(18) 0.0140(4) Uani 1 1 d . . . . .
H22 H 0.654443 0.443625 0.712791 0.017 Uiso 1 1 calc R U . . .
C23 C 0.56465(6) 0.4847(3) 0.72819(17) 0.0134(4) Uani 1 1 d . . . . .
C24 C 0.51482(6) 0.4641(2) 0.69442(18) 0.0140(4) Uani 1 1 d . . . . .
C25 C 0.47475(6) 0.5267(3) 0.74842(18) 0.0168(4) Uani 1 1 d . . . . .
H25 H 0.476241 0.595224 0.818358 0.020 Uiso 1 1 calc R U . . .
C26 C 0.43200(7) 0.4852(3) 0.69605(19) 0.0182(4) Uani 1 1 d . . . . .
H26 H 0.403785 0.526503 0.730690 0.022 Uiso 1 1 calc R U . . .
C27 C 0.43013(7) 0.3840(3) 0.59369(19) 0.0181(4) Uani 1 1 d . . . . .
H27 H 0.400618 0.357123 0.559838 0.022 Uiso 1 1 calc R U . . .
C28 C 0.51288(6) 0.3642(2) 0.59247(17) 0.0142(4) Uani 1 1 d . . . . .
C29 C 0.56140(6) 0.3198(2) 0.55612(18) 0.0142(4) Uani 1 1 d . . . . .
C30 C 0.79307(6) 0.2352(2) 0.4815(2) 0.0197(4) Uani 1 1 d . . . . .
H30 H 0.809340 0.181510 0.418079 0.024 Uiso 1 1 calc R U . . .
C31 C 0.74456(7) 0.2474(2) 0.47852(19) 0.0177(4) Uani 1 1 d . . . . .
H31 H 0.728043 0.202516 0.412740 0.021 Uiso 1 1 calc R U . . .
C32 C 0.47090(6) 0.3213(3) 0.53990(18) 0.0163(4) Uani 1 1 d . . . . .
H32 H 0.469756 0.252068 0.470198 0.020 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C4 1.212(2) . ?
O2 C14 1.208(2) . ?
O3 C23 1.208(2) . ?
O4 C29 1.210(2) . ?
N1 C4 1.401(2) . ?
N1 C5 1.408(2) . ?
N1 C14 1.411(2) . ?
N2 C22 1.409(2) . ?
N2 C23 1.413(2) . ?
N2 C29 1.405(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.393(3) . ?
C1 C11 1.394(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.390(3) . ?
C3 C4 1.485(2) . ?
C3 C12 1.386(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.328(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.470(2) . ?
C7 C8 1.398(3) . ?
C7 C16 1.397(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.383(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.389(3) . ?
C10 H10 0.9500 . ?
C10 C15 1.392(3) . ?
C11 H11 0.9500 . ?
C11 C13 1.399(3) . ?
C12 C13 1.379(3) . ?
C12 C14 1.486(2) . ?
C13 H13 0.9500 . ?
C15 H15 0.9500 . ?
C15 C16 1.386(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C17 C18 1.397(3) . ?
C17 C30 1.380(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.384(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.397(3) . ?
C20 C21 1.474(2) . ?
C20 C31 1.398(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.335(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.484(2) . ?
C24 C25 1.382(2) . ?
C24 C28 1.385(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.396(3) . ?
C26 H26 0.9500 . ?
C26 C27 1.394(3) . ?
C27 H27 0.9500 . ?
C27 C32 1.398(3) . ?
C28 C29 1.486(2) . ?
C28 C32 1.380(3) . ?
C30 H30 0.9500 . ?
C30 C31 1.391(3) . ?
C31 H31 0.9500 . ?
C32 H32 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
C4 N1 C5 120.32(16) . . ?
C4 N1 C14 111.42(14) . . ?
C5 N1 C14 128.24(16) . . ?
C22 N2 C23 120.65(16) . . ?
C29 N2 C22 128.21(16) . . ?
C29 N2 C23 111.00(15) . . ?
C2 C1 H1 119.2 . . ?
C2 C1 C11 121.70(18) . . ?
C11 C1 H1 119.2 . . ?
C1 C2 H2 121.8 . . ?
C3 C2 C1 116.5(2) . . ?
C3 C2 H2 121.8 . . ?
C2 C3 C4 129.96(19) . . ?
C12 C3 C2 122.09(18) . . ?
C12 C3 C4 107.95(16) . . ?
O1 C4 N1 124.69(17) . . ?
O1 C4 C3 129.07(18) . . ?
N1 C4 C3 106.24(16) . . ?
N1 C5 H5 116.7 . . ?
C6 C5 N1 126.59(18) . . ?
C6 C5 H5 116.7 . . ?
C5 C6 H6 118.0 . . ?
C5 C6 C7 124.06(18) . . ?
C7 C6 H6 118.0 . . ?
C8 C7 C6 118.59(18) . . ?
C16 C7 C6 123.05(17) . . ?
C16 C7 C8 118.36(17) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 C7 120.82(19) . . ?
C9 C8 H8 119.6 . . ?
C8 C9 H9 119.7 . . ?
C8 C9 C10 120.50(19) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 120.4 . . ?
C9 C10 C15 119.15(18) . . ?
C15 C10 H10 120.4 . . ?
C1 C11 H11 119.5 . . ?
C1 C11 C13 120.91(18) . . ?
C13 C11 H11 119.5 . . ?
C3 C12 C14 108.81(17) . . ?
C13 C12 C3 121.48(17) . . ?
C13 C12 C14 129.69(19) . . ?
C11 C13 H13 121.3 . . ?
C12 C13 C11 117.33(19) . . ?
C12 C13 H13 121.3 . . ?
O2 C14 N1 125.55(16) . . ?
O2 C14 C12 128.99(18) . . ?
N1 C14 C12 105.46(16) . . ?
C10 C15 H15 119.8 . . ?
C16 C15 C10 120.45(19) . . ?
C16 C15 H15 119.8 . . ?
C7 C16 H16 119.6 . . ?
C15 C16 C7 120.72(18) . . ?
C15 C16 H16 119.6 . . ?
C18 C17 H17 120.4 . . ?
C30 C17 H17 120.4 . . ?
C30 C17 C18 119.21(17) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.49(18) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 119.6 . . ?
C18 C19 C20 120.80(18) . . ?
C20 C19 H19 119.6 . . ?
C19 C20 C21 124.08(18) . . ?
C19 C20 C31 118.12(17) . . ?
C31 C20 C21 117.79(17) . . ?
C20 C21 H21 117.8 . . ?
C22 C21 C20 124.44(18) . . ?
C22 C21 H21 117.8 . . ?
N2 C22 H22 117.1 . . ?
C21 C22 N2 125.75(18) . . ?
C21 C22 H22 117.1 . . ?
O3 C23 N2 124.48(17) . . ?
O3 C23 C24 129.44(18) . . ?
N2 C23 C24 106.07(15) . . ?
C25 C24 C23 130.11(18) . . ?
C25 C24 C28 121.61(18) . . ?
C28 C24 C23 108.27(16) . . ?
C24 C25 H25 121.3 . . ?
C24 C25 C26 117.33(19) . . ?
C26 C25 H25 121.3 . . ?
C25 C26 H26 119.5 . . ?
C27 C26 C25 120.95(19) . . ?
C27 C26 H26 119.5 . . ?
C26 C27 H27 119.4 . . ?
C26 C27 C32 121.21(18) . . ?
C32 C27 H27 119.4 . . ?
C24 C28 C29 108.53(16) . . ?
C32 C28 C24 121.78(18) . . ?
C32 C28 C29 129.69(18) . . ?
O4 C29 N2 125.48(17) . . ?
O4 C29 C28 128.43(18) . . ?
N2 C29 C28 106.08(16) . . ?
C17 C30 H30 119.8 . . ?
C17 C30 C31 120.37(18) . . ?
C31 C30 H30 119.8 . . ?
C20 C31 H31 119.5 . . ?
C30 C31 C20 120.99(18) . . ?
C30 C31 H31 119.5 . . ?
C27 C32 H32 121.4 . . ?
C28 C32 C27 117.12(18) . . ?
C28 C32 H32 121.4 . . ?

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
O3 C23 C24 C25 0.0(3) . . . . ?
O3 C23 C24 C28 -179.70(19) . . . . ?
N1 C5 C6 C7 -179.64(17) . . . . ?
N2 C23 C24 C25 179.51(18) . . . . ?
N2 C23 C24 C28 -0.22(19) . . . . ?
C1 C2 C3 C4 -179.05(18) . . . . ?
C1 C2 C3 C12 0.2(3) . . . . ?
C1 C11 C13 C12 0.6(3) . . . . ?
C2 C1 C11 C13 -0.7(3) . . . . ?
C2 C3 C4 O1 -3.2(3) . . . . ?
C2 C3 C4 N1 176.87(19) . . . . ?
C2 C3 C12 C13 -0.4(3) . . . . ?
C2 C3 C12 C14 -178.92(17) . . . . ?
C3 C12 C13 C11 0.0(3) . . . . ?
C3 C12 C14 O2 -178.53(19) . . . . ?
C3 C12 C14 N1 1.7(2) . . . . ?
C4 N1 C5 C6 174.23(18) . . . . ?
C4 N1 C14 O2 176.86(18) . . . . ?
C4 N1 C14 C12 -3.3(2) . . . . ?
C4 C3 C12 C13 179.02(16) . . . . ?
C4 C3 C12 C14 0.5(2) . . . . ?
C5 N1 C4 O1 2.0(3) . . . . ?
C5 N1 C4 C3 -178.08(15) . . . . ?
C5 N1 C14 O2 -1.3(3) . . . . ?
C5 N1 C14 C12 178.56(17) . . . . ?
C5 C6 C7 C8 -178.09(19) . . . . ?
C5 C6 C7 C16 1.1(3) . . . . ?
C6 C7 C8 C9 178.95(18) . . . . ?
C6 C7 C16 C15 -178.76(18) . . . . ?
C7 C8 C9 C10 0.0(3) . . . . ?
C8 C7 C16 C15 0.4(3) . . . . ?
C8 C9 C10 C15 0.2(3) . . . . ?
C9 C10 C15 C16 0.0(3) . . . . ?
C10 C15 C16 C7 -0.3(3) . . . . ?
C11 C1 C2 C3 0.4(3) . . . . ?
C12 C3 C4 O1 177.44(19) . . . . ?
C12 C3 C4 N1 -2.5(2) . . . . ?
C13 C12 C14 O2 3.1(3) . . . . ?
C13 C12 C14 N1 -176.73(18) . . . . ?
C14 N1 C4 O1 -176.28(17) . . . . ?
C14 N1 C4 C3 3.6(2) . . . . ?
C14 N1 C5 C6 -7.8(3) . . . . ?
C14 C12 C13 C11 178.20(19) . . . . ?
C16 C7 C8 C9 -0.3(3) . . . . ?
C17 C18 C19 C20 0.2(3) . . . . ?
C17 C30 C31 C20 -0.3(3) . . . . ?
C18 C17 C30 C31 -0.8(3) . . . . ?
C18 C19 C20 C21 177.48(17) . . . . ?
C18 C19 C20 C31 -1.3(3) . . . . ?
C19 C20 C21 C22 0.0(3) . . . . ?
C19 C20 C31 C30 1.4(3) . . . . ?
C20 C21 C22 N2 -178.89(17) . . . . ?
C21 C20 C31 C30 -177.48(16) . . . . ?
C22 N2 C23 O3 -3.1(3) . . . . ?
C22 N2 C23 C24 177.40(15) . . . . ?
C22 N2 C29 O4 2.2(3) . . . . ?
C22 N2 C29 C28 -177.58(16) . . . . ?
C23 N2 C22 C21 -172.74(18) . . . . ?
C23 N2 C29 O4 177.85(17) . . . . ?
C23 N2 C29 C28 -1.95(19) . . . . ?
C23 C24 C25 C26 -179.70(19) . . . . ?
C23 C24 C28 C29 -0.9(2) . . . . ?
C23 C24 C28 C32 179.44(17) . . . . ?
C24 C25 C26 C27 0.3(3) . . . . ?
C24 C28 C29 O4 -178.02(18) . . . . ?
C24 C28 C29 N2 1.78(19) . . . . ?
C24 C28 C32 C27 0.4(3) . . . . ?
C25 C24 C28 C29 179.29(16) . . . . ?
C25 C24 C28 C32 -0.3(3) . . . . ?
C25 C26 C27 C32 -0.2(3) . . . . ?
C26 C27 C32 C28 -0.1(3) . . . . ?
C28 C24 C25 C26 0.0(3) . . . . ?
C29 N2 C22 C21 2.5(3) . . . . ?
C29 N2 C23 O3 -179.10(17) . . . . ?
C29 N2 C23 C24 1.39(19) . . . . ?
C29 C28 C32 C27 -179.16(18) . . . . ?
C30 C17 C18 C19 0.9(3) . . . . ?
C31 C20 C21 C22 178.76(18) . . . . ?
C32 C28 C29 O4 1.5(3) . . . . ?
C32 C28 C29 N2 -178.65(19) . . . . ?

_olex2_date_sample_data_collection 2021-01-20
_olex2_date_sample_submission    2021-01-20
_olex2_exptl_crystal_mounting_method 'Frozen on a cryoloop using Paretone oil.'
_olex2_submission_original_sample_id LNB304
_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_LNB387_bis_twin
_database_code_depnum_ccdc_archive 'CCDC 2099684'
loop_
_audit_author_name
_audit_author_address
'David Wragg'
;University of Oslo
Norway
;
_audit_update_record             
;
2021-07-27 deposited with the CCDC.	2021-10-19 downloaded from the CCDC.
;
_audit_creation_date             2021-04-29
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
l.n.berntsen@kjemi.uio.no
david.wragg@smn.uio.no
_chemical_name_common            ?
_chemical_name_systematic        
(Z)-(5-(2-bromobenzylidene))-(E,E)-1,3-distyrylhydantoin
_chemical_formula_moiety         'C26 H19 Br N2 O2'
_chemical_formula_sum            'C26 H19 Br N2 O2'
_chemical_formula_weight         471.34
_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                   9.2065(11)
_cell_length_b                   10.3700(13)
_cell_length_c                   12.0590(15)
_cell_angle_alpha                77.804(3)
_cell_angle_beta                 72.890(3)
_cell_angle_gamma                73.581(3)
_cell_volume                     1045.1(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5140
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      25.05
_cell_measurement_theta_min      2.38
_shelx_estimated_absorpt_T_max   0.857
_shelx_estimated_absorpt_T_min   0.218
_exptl_absorpt_coefficient_mu    1.993
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_correction_T_min  0.464
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 20573 reflections, Rint = 0.0739
 (14415 with I > 3sig(I), Rint = 0.0630)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             480
_exptl_crystal_size_max          1.1
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0779
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_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       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3678
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.134
_diffrn_reflns_theta_max         25.134
_diffrn_reflns_theta_min         2.068
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker Photon 100 area detector'
_diffrn_detector_area_resol_mean 10.42
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ shutterless scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3024
_reflns_number_total             3678
_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       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.811
_refine_diff_density_min         -0.626
_refine_diff_density_rms         0.127
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3678
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0531
_refine_ls_restrained_S_all      1.029
_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)+(0.0784P)²+1.0318P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1253
_refine_ls_wR_factor_ref         0.1383
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.700(3)
 0.300(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C20(H20), C23(H23), C19(H19), C7(H7), C12(H12), C11(H11), C14(H14), C4(H4),
 C25(H25), C9(H9), C24(H24), C26(H26), C16(H16), C8(H8), C22(H22), C18(H18),
 C10(H10), C15(H15), C17(H17)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.72303(6) 0.97127(5) 0.71358(4) 0.02480(18) Uani 1 1 d . . . . .
O1 O 0.6670(4) 0.3412(3) 0.5486(3) 0.0255(8) Uani 1 1 d . . . . .
O2 O 0.3580(4) 0.6525(3) 0.7903(3) 0.0275(8) Uani 1 1 d . . . . .
N1 N 0.6667(4) 0.5654(3) 0.5483(3) 0.0161(8) Uani 1 1 d . . . . .
N2 N 0.4864(4) 0.4715(4) 0.6858(3) 0.0190(8) Uani 1 1 d . . . . .
C21 C 0.2344(5) 0.2626(5) 0.9158(4) 0.0199(10) Uani 1 1 d . . . . .
C3 C 0.5750(5) 0.6661(4) 0.6192(4) 0.0180(10) Uani 1 1 d . . . . .
C6 C 0.7370(5) 0.9684(4) 0.5530(4) 0.0162(9) Uani 1 1 d . . . . .
C13 C 1.0277(5) 0.5228(4) 0.2951(4) 0.0183(10) Uani 1 1 d . . . . .
C20 C 0.2943(5) 0.3765(5) 0.8426(4) 0.0220(10) Uani 1 1 d . . . . .
H20 H 0.238002 0.465446 0.858378 0.026 Uiso 1 1 calc R U . . .
C2 C 0.4590(5) 0.6024(5) 0.7105(4) 0.0209(10) Uani 1 1 d . . . . .
C23 C 0.2687(6) 0.0252(5) 0.9979(4) 0.0236(10) Uani 1 1 d . . . . .
H23 H 0.334322 -0.063633 1.004822 0.028 Uiso 1 1 calc R U . . .
C19 C 0.4225(5) 0.3639(5) 0.7553(4) 0.0206(10) Uani 1 1 d . . . . .
H19 H 0.475654 0.274704 0.738275 0.025 Uiso 1 1 calc R U . . .
C7 C 0.8178(5) 1.0543(5) 0.4705(4) 0.0232(10) Uani 1 1 d . . . . .
H7 H 0.861514 1.113921 0.493728 0.028 Uiso 1 1 calc R U . . .
C12 C 0.8833(5) 0.5009(4) 0.3803(4) 0.0196(10) Uani 1 1 d . . . . .
H12 H 0.839880 0.431229 0.372807 0.024 Uiso 1 1 calc R U . . .
C11 C 0.8092(5) 0.5744(4) 0.4685(4) 0.0187(10) Uani 1 1 d . . . . .
H11 H 0.858773 0.639008 0.477479 0.022 Uiso 1 1 calc R U . . .
C5 C 0.6702(5) 0.8795(4) 0.5245(4) 0.0193(10) Uani 1 1 d . . . . .
C14 C 1.0801(5) 0.6406(5) 0.2798(4) 0.0208(10) Uani 1 1 d . . . . .
H14 H 1.023575 0.708486 0.328761 0.025 Uiso 1 1 calc R U . . .
C4 C 0.5786(5) 0.7944(4) 0.6146(4) 0.0188(10) Uani 1 1 d . . . . .
H4 H 0.511466 0.837446 0.679614 0.023 Uiso 1 1 calc R U . . .
C25 C 0.0160(5) 0.1782(5) 1.0471(4) 0.0229(10) Uani 1 1 d . . . . .
H25 H -0.091500 0.194573 1.087439 0.027 Uiso 1 1 calc R U . . .
C9 C 0.7690(5) 0.9649(5) 0.3208(4) 0.0236(10) Uani 1 1 d . . . . .
H9 H 0.780817 0.963229 0.240109 0.028 Uiso 1 1 calc R U . . .
C24 C 0.1109(6) 0.0488(5) 1.0581(4) 0.0248(11) Uani 1 1 d . . . . .
H24 H 0.068871 -0.023781 1.106365 0.030 Uiso 1 1 calc R U . . .
C26 C 0.0776(5) 0.2837(5) 0.9774(4) 0.0218(10) Uani 1 1 d . . . . .
H26 H 0.011839 0.372520 0.971277 0.026 Uiso 1 1 calc R U . . .
C1 C 0.6140(5) 0.4462(5) 0.5887(4) 0.0201(10) Uani 1 1 d . . . . .
C16 C 1.2978(5) 0.5612(5) 0.1223(4) 0.0264(11) Uani 1 1 d . . . . .
H16 H 1.388340 0.575085 0.062861 0.032 Uiso 1 1 calc R U . . .
C8 C 0.8338(5) 1.0516(5) 0.3533(4) 0.0237(10) Uani 1 1 d . . . . .
H8 H 0.889534 1.109537 0.294921 0.028 Uiso 1 1 calc R U . . .
C22 C 0.3288(5) 0.1312(5) 0.9284(4) 0.0234(10) Uani 1 1 d . . . . .
H22 H 0.436483 0.114775 0.888379 0.028 Uiso 1 1 calc R U . . .
C18 C 1.1144(5) 0.4248(5) 0.2224(4) 0.0224(10) Uani 1 1 d . . . . .
H18 H 1.080687 0.343904 0.230735 0.027 Uiso 1 1 calc R U . . .
C10 C 0.6869(5) 0.8804(5) 0.4048(4) 0.0221(10) Uani 1 1 d . . . . .
H10 H 0.641384 0.822385 0.381241 0.027 Uiso 1 1 calc R U . . .
C15 C 1.2131(5) 0.6598(5) 0.1946(4) 0.0256(11) Uani 1 1 d . . . . .
H15 H 1.246920 0.740823 0.185105 0.031 Uiso 1 1 calc R U . . .
C17 C 1.2489(6) 0.4438(5) 0.1381(4) 0.0264(11) Uani 1 1 d . . . . .
H17 H 1.307939 0.374921 0.090750 0.032 Uiso 1 1 calc R U . . .


_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 C6 1.909(4) . ?
O1 C1 1.200(6) . ?
O2 C2 1.213(6) . ?
N1 C3 1.410(6) . ?
N1 C11 1.395(6) . ?
N1 C1 1.395(6) . ?
N2 C2 1.389(6) . ?
N2 C19 1.407(6) . ?
N2 C1 1.403(6) . ?
C21 C20 1.456(6) . ?
C21 C26 1.393(7) . ?
C21 C22 1.398(6) . ?
C3 C2 1.479(6) . ?
C3 C4 1.329(6) . ?
C6 C7 1.378(6) . ?
C6 C5 1.387(6) . ?
C13 C12 1.464(6) . ?
C13 C14 1.394(7) . ?
C13 C18 1.395(6) . ?
C20 H20 0.9500 . ?
C20 C19 1.325(7) . ?
C23 H23 0.9500 . ?
C23 C24 1.397(7) . ?
C23 C22 1.378(7) . ?
C19 H19 0.9500 . ?
C7 H7 0.9500 . ?
C7 C8 1.384(6) . ?
C12 H12 0.9500 . ?
C12 C11 1.340(6) . ?
C11 H11 0.9500 . ?
C5 C4 1.466(6) . ?
C5 C10 1.405(6) . ?
C14 H14 0.9500 . ?
C14 C15 1.381(7) . ?
C4 H4 0.9500 . ?
C25 H25 0.9500 . ?
C25 C24 1.383(7) . ?
C25 C26 1.381(7) . ?
C9 H9 0.9500 . ?
C9 C8 1.382(7) . ?
C9 C10 1.383(7) . ?
C24 H24 0.9500 . ?
C26 H26 0.9500 . ?
C16 H16 0.9500 . ?
C16 C15 1.392(7) . ?
C16 C17 1.372(7) . ?
C8 H8 0.9500 . ?
C22 H22 0.9500 . ?
C18 H18 0.9500 . ?
C18 C17 1.385(7) . ?
C10 H10 0.9500 . ?
C15 H15 0.9500 . ?
C17 H17 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
C11 N1 C3 123.8(4) . . ?
C11 N1 C1 124.6(4) . . ?
C1 N1 C3 110.0(4) . . ?
C2 N2 C19 128.2(4) . . ?
C2 N2 C1 110.8(4) . . ?
C1 N2 C19 120.0(4) . . ?
C26 C21 C20 119.6(4) . . ?
C26 C21 C22 117.9(4) . . ?
C22 C21 C20 122.5(4) . . ?
N1 C3 C2 106.1(4) . . ?
C4 C3 N1 132.1(4) . . ?
C4 C3 C2 121.8(4) . . ?
C7 C6 Br1 117.2(3) . . ?
C7 C6 C5 123.4(4) . . ?
C5 C6 Br1 119.4(3) . . ?
C14 C13 C12 122.8(4) . . ?
C14 C13 C18 118.0(4) . . ?
C18 C13 C12 119.2(4) . . ?
C21 C20 H20 117.9 . . ?
C19 C20 C21 124.2(5) . . ?
C19 C20 H20 117.9 . . ?
O2 C2 N2 125.9(4) . . ?
O2 C2 C3 128.2(4) . . ?
N2 C2 C3 105.9(4) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C22 C23 C24 119.7(4) . . ?
N2 C19 H19 117.2 . . ?
C20 C19 N2 125.5(4) . . ?
C20 C19 H19 117.2 . . ?
C6 C7 H7 120.8 . . ?
C6 C7 C8 118.5(4) . . ?
C8 C7 H7 120.8 . . ?
C13 C12 H12 118.4 . . ?
C11 C12 C13 123.3(4) . . ?
C11 C12 H12 118.4 . . ?
N1 C11 H11 116.7 . . ?
C12 C11 N1 126.5(4) . . ?
C12 C11 H11 116.7 . . ?
C6 C5 C4 121.9(4) . . ?
C6 C5 C10 116.8(4) . . ?
C10 C5 C4 121.2(4) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 C13 120.9(4) . . ?
C15 C14 H14 119.6 . . ?
C3 C4 C5 129.8(4) . . ?
C3 C4 H4 115.1 . . ?
C5 C4 H4 115.1 . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C26 C25 C24 120.0(4) . . ?
C8 C9 H9 119.7 . . ?
C8 C9 C10 120.6(4) . . ?
C10 C9 H9 119.7 . . ?
C23 C24 H24 120.1 . . ?
C25 C24 C23 119.8(4) . . ?
C25 C24 H24 120.1 . . ?
C21 C26 H26 119.3 . . ?
C25 C26 C21 121.3(4) . . ?
C25 C26 H26 119.3 . . ?
O1 C1 N1 126.9(5) . . ?
O1 C1 N2 125.9(4) . . ?
N1 C1 N2 107.1(4) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C17 C16 C15 119.2(4) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.2(4) . . ?
C9 C8 H8 119.9 . . ?
C21 C22 H22 119.4 . . ?
C23 C22 C21 121.3(4) . . ?
C23 C22 H22 119.4 . . ?
C13 C18 H18 119.6 . . ?
C17 C18 C13 120.8(5) . . ?
C17 C18 H18 119.6 . . ?
C5 C10 H10 119.7 . . ?
C9 C10 C5 120.6(4) . . ?
C9 C10 H10 119.7 . . ?
C14 C15 C16 120.4(5) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C16 C17 C18 120.7(4) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C6 C7 C8 178.1(3) . . . . ?
Br1 C6 C5 C4 4.7(5) . . . . ?
Br1 C6 C5 C10 -178.8(3) . . . . ?
N1 C3 C2 O2 179.4(4) . . . . ?
N1 C3 C2 N2 -1.7(4) . . . . ?
N1 C3 C4 C5 7.7(8) . . . . ?
C21 C20 C19 N2 -177.6(4) . . . . ?
C3 N1 C11 C12 -163.1(4) . . . . ?
C3 N1 C1 O1 -179.4(4) . . . . ?
C3 N1 C1 N2 0.5(5) . . . . ?
C6 C7 C8 C9 0.3(7) . . . . ?
C6 C5 C4 C3 -140.1(5) . . . . ?
C6 C5 C10 C9 1.2(6) . . . . ?
C13 C12 C11 N1 175.7(4) . . . . ?
C13 C14 C15 C16 -0.3(7) . . . . ?
C13 C18 C17 C16 -1.6(7) . . . . ?
C20 C21 C26 C25 179.5(4) . . . . ?
C20 C21 C22 C23 -179.7(4) . . . . ?
C2 N2 C19 C20 18.9(7) . . . . ?
C2 N2 C1 O1 178.3(4) . . . . ?
C2 N2 C1 N1 -1.6(5) . . . . ?
C2 C3 C4 C5 -171.8(4) . . . . ?
C19 N2 C2 O2 -10.7(7) . . . . ?
C19 N2 C2 C3 170.3(4) . . . . ?
C19 N2 C1 O1 8.9(7) . . . . ?
C19 N2 C1 N1 -171.0(3) . . . . ?
C7 C6 C5 C4 -177.0(4) . . . . ?
C7 C6 C5 C10 -0.6(6) . . . . ?
C12 C13 C14 C15 -176.9(4) . . . . ?
C12 C13 C18 C17 177.9(4) . . . . ?
C11 N1 C3 C2 -165.5(4) . . . . ?
C11 N1 C3 C4 14.9(7) . . . . ?
C11 N1 C1 O1 -13.3(7) . . . . ?
C11 N1 C1 N2 166.6(4) . . . . ?
C5 C6 C7 C8 -0.2(7) . . . . ?
C14 C13 C12 C11 -16.2(7) . . . . ?
C14 C13 C18 C17 0.4(6) . . . . ?
C4 C3 C2 O2 -1.0(7) . . . . ?
C4 C3 C2 N2 177.9(4) . . . . ?
C4 C5 C10 C9 177.6(4) . . . . ?
C24 C23 C22 C21 -0.7(7) . . . . ?
C24 C25 C26 C21 0.9(7) . . . . ?
C26 C21 C20 C19 -158.8(5) . . . . ?
C26 C21 C22 C23 1.1(7) . . . . ?
C26 C25 C24 C23 -0.4(7) . . . . ?
C1 N1 C3 C2 0.7(4) . . . . ?
C1 N1 C3 C4 -178.8(5) . . . . ?
C1 N1 C11 C12 32.7(6) . . . . ?
C1 N2 C2 O2 -179.0(4) . . . . ?
C1 N2 C2 C3 2.1(5) . . . . ?
C1 N2 C19 C20 -173.7(4) . . . . ?
C8 C9 C10 C5 -1.1(7) . . . . ?
C22 C21 C20 C19 22.0(7) . . . . ?
C22 C21 C26 C25 -1.2(7) . . . . ?
C22 C23 C24 C25 0.3(7) . . . . ?
C18 C13 C12 C11 166.4(4) . . . . ?
C18 C13 C14 C15 0.6(6) . . . . ?
C10 C5 C4 C3 43.6(7) . . . . ?
C10 C9 C8 C7 0.3(7) . . . . ?
C15 C16 C17 C18 1.9(7) . . . . ?
C17 C16 C15 C14 -1.0(7) . . . . ?

_olex2_date_sample_data_collection 2021-04-15
_olex2_date_sample_submission    2021-04-15
_olex2_exptl_crystal_mounting_method 
'Frozen on a Mitegen cryoloop in Paretone oil.'
_olex2_submission_original_sample_id LNB387_bis
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.700(3)
2 0.300(3)

####################################################################### 
# 
# 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_LNB348
_database_code_depnum_ccdc_archive 'CCDC 2099682'
loop_
_audit_author_name
_audit_author_address
'David Wragg'
;University of Oslo
Norway
;
_audit_update_record             
;
2021-07-27 deposited with the CCDC.	2021-10-19 downloaded from the CCDC.
;
_audit_creation_date             2021-02-14
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6257)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
l.n.berntsen@kjemi.uio.no
david.wragg@smn.uio.no
_chemical_name_common            ?
_chemical_name_systematic        N-(1,1-cyclopentenyl)phthalimide
_chemical_formula_moiety         'C13 H11 N O2'
_chemical_formula_sum            'C13 H11 N O2'
_chemical_formula_weight         213.23
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.9019(13)
_cell_length_b                   11.4470(13)
_cell_length_c                   7.4837(8)
_cell_angle_alpha                90
_cell_angle_beta                 101.078(3)
_cell_angle_gamma                90
_cell_volume                     1000.59(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9691
_cell_measurement_temperature    103.7
_cell_measurement_theta_max      33.09
_cell_measurement_theta_min      2.49
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.936
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.6902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1423 before and 0.0467 after correction.
The Ratio of minimum to maximum transmission is 0.9246.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            20966
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.504
_diffrn_reflns_theta_min         2.491
_diffrn_ambient_temperature      103.7
_diffrn_detector                 'Bruker Photon 100 area detector'
_diffrn_detector_area_resol_mean 10.42
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ shutterless scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2616
_reflns_number_total             3055
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.502
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         3055
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0461
_refine_ls_restrained_S_all      1.046
_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)+(0.0709P)²+0.4322P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1215
_refine_ls_wR_factor_ref         0.1272
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C10(H10A,H10B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C13(H13)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.29156(7) 0.56810(7) 0.11260(12) 0.01727(19) Uani 1 1 d . . . . .
O2 O 0.29912(7) 0.23944(8) 0.46716(13) 0.0226(2) Uani 1 1 d . . . . .
N1 N 0.26323(7) 0.40806(8) 0.29110(12) 0.01174(19) Uani 1 1 d . . . . .
C11 C -0.05066(11) 0.35614(12) 0.2376(3) 0.0320(3) Uani 1 1 d . . . . .
H11A H -0.084672 0.326604 0.339625 0.038 Uiso 1 1 calc R U . . .
H11B H -0.098774 0.329825 0.121692 0.038 Uiso 1 1 calc R U . . .
C10 C 0.06994(11) 0.31133(12) 0.2535(2) 0.0284(3) Uani 1 1 d . . . . .
H10A H 0.090704 0.259968 0.361195 0.034 Uiso 1 1 calc R U . . .
H10B H 0.077761 0.266477 0.143412 0.034 Uiso 1 1 calc R U . . .
C9 C 0.14290(9) 0.41431(9) 0.27234(15) 0.0126(2) Uani 1 1 d . . . . .
C1 C 0.32915(9) 0.48734(9) 0.20934(14) 0.0116(2) Uani 1 1 d . . . . .
C2 C 0.45024(9) 0.44933(9) 0.26719(14) 0.0116(2) Uani 1 1 d . . . . .
C3 C 0.55006(9) 0.49852(10) 0.23251(15) 0.0146(2) Uani 1 1 d . . . . .
H3 H 0.548750 0.567261 0.161013 0.018 Uiso 1 1 calc R U . . .
C4 C 0.65322(9) 0.44268(10) 0.30729(16) 0.0166(2) Uani 1 1 d . . . . .
H4 H 0.723375 0.473912 0.285787 0.020 Uiso 1 1 calc R U . . .
C12 C -0.04367(10) 0.49042(11) 0.24334(17) 0.0188(2) Uani 1 1 d . . . . .
H12A H -0.087060 0.524740 0.129295 0.023 Uiso 1 1 calc R U . . .
H12B H -0.074629 0.521601 0.347412 0.023 Uiso 1 1 calc R U . . .
C5 C 0.65460(9) 0.34213(10) 0.41263(16) 0.0167(2) Uani 1 1 d . . . . .
H5 H 0.725675 0.305763 0.461072 0.020 Uiso 1 1 calc R U . . .
C6 C 0.55341(9) 0.29378(10) 0.44836(15) 0.0153(2) Uani 1 1 d . . . . .
H6 H 0.554166 0.225786 0.521368 0.018 Uiso 1 1 calc R U . . .
C7 C 0.45188(9) 0.34925(9) 0.37274(14) 0.0122(2) Uani 1 1 d . . . . .
C8 C 0.33255(9) 0.32024(10) 0.38758(15) 0.0136(2) Uani 1 1 d . . . . .
C13 C 0.08266(10) 0.51703(11) 0.26501(18) 0.0210(3) Uani 1 1 d . . . . .
H13 H 0.115280 0.593038 0.272397 0.025 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2061(13) . ?
O2 C8 1.2081(14) . ?
N1 C9 1.4137(13) . ?
N1 C1 1.4134(13) . ?
N1 C8 1.4084(14) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C10 1.5073(18) . ?
C11 C12 1.5395(18) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C9 1.4549(16) . ?
C9 C13 1.3728(16) . ?
C1 C2 1.4879(14) . ?
C2 C3 1.3836(14) . ?
C2 C7 1.3896(15) . ?
C3 H3 0.9500 . ?
C3 C4 1.4019(15) . ?
C4 H4 0.9500 . ?
C4 C5 1.3934(17) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.5120(16) . ?
C5 H5 0.9500 . ?
C5 C6 1.3971(16) . ?
C6 H6 0.9500 . ?
C6 C7 1.3859(15) . ?
C7 C8 1.4834(15) . ?
C13 H13 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
C1 N1 C9 124.09(9) . . ?
C8 N1 C9 124.71(9) . . ?
C8 N1 C1 111.16(9) . . ?
H11A C11 H11B 108.6 . . ?
C10 C11 H11A 110.3 . . ?
C10 C11 H11B 110.3 . . ?
C10 C11 C12 106.98(10) . . ?
C12 C11 H11A 110.3 . . ?
C12 C11 H11B 110.3 . . ?
C11 C10 H10A 110.6 . . ?
C11 C10 H10B 110.6 . . ?
H10A C10 H10B 108.7 . . ?
C9 C10 C11 105.87(11) . . ?
C9 C10 H10A 110.6 . . ?
C9 C10 H10B 110.6 . . ?
N1 C9 C10 122.89(10) . . ?
C13 C9 N1 123.96(10) . . ?
C13 C9 C10 113.12(10) . . ?
O1 C1 N1 125.40(10) . . ?
O1 C1 C2 128.73(10) . . ?
N1 C1 C2 105.87(9) . . ?
C3 C2 C1 130.17(10) . . ?
C3 C2 C7 121.56(10) . . ?
C7 C2 C1 108.27(9) . . ?
C2 C3 H3 121.4 . . ?
C2 C3 C4 117.21(10) . . ?
C4 C3 H3 121.4 . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.11(10) . . ?
C5 C4 H4 119.4 . . ?
C11 C12 H12A 110.8 . . ?
C11 C12 H12B 110.8 . . ?
H12A C12 H12B 108.9 . . ?
C13 C12 C11 104.56(10) . . ?
C13 C12 H12A 110.8 . . ?
C13 C12 H12B 110.8 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.24(10) . . ?
C6 C5 H5 119.4 . . ?
C5 C6 H6 121.4 . . ?
C7 C6 C5 117.15(10) . . ?
C7 C6 H6 121.4 . . ?
C2 C7 C8 108.54(9) . . ?
C6 C7 C2 121.72(10) . . ?
C6 C7 C8 129.73(10) . . ?
O2 C8 N1 125.68(10) . . ?
O2 C8 C7 128.24(10) . . ?
N1 C8 C7 106.07(9) . . ?
C9 C13 C12 109.43(10) . . ?
C9 C13 H13 125.3 . . ?
C12 C13 H13 125.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 3.11(19) . . . . ?
O1 C1 C2 C7 -177.67(11) . . . . ?
N1 C9 C13 C12 179.61(10) . . . . ?
N1 C1 C2 C3 -177.13(11) . . . . ?
N1 C1 C2 C7 2.09(11) . . . . ?
C11 C10 C9 N1 179.94(11) . . . . ?
C11 C10 C9 C13 -1.73(17) . . . . ?
C11 C12 C13 C9 -0.32(15) . . . . ?
C10 C11 C12 C13 -0.71(16) . . . . ?
C10 C9 C13 C12 1.30(16) . . . . ?
C9 N1 C1 O1 -1.12(17) . . . . ?
C9 N1 C1 C2 179.11(9) . . . . ?
C9 N1 C8 O2 -0.30(18) . . . . ?
C9 N1 C8 C7 -179.41(9) . . . . ?
C1 N1 C9 C10 141.53(12) . . . . ?
C1 N1 C9 C13 -36.62(17) . . . . ?
C1 N1 C8 O2 -178.17(11) . . . . ?
C1 N1 C8 C7 2.72(12) . . . . ?
C1 C2 C3 C4 179.57(10) . . . . ?
C1 C2 C7 C6 -179.32(10) . . . . ?
C1 C2 C7 C8 -0.48(12) . . . . ?
C2 C3 C4 C5 -0.25(16) . . . . ?
C2 C7 C8 O2 179.61(12) . . . . ?
C2 C7 C8 N1 -1.31(12) . . . . ?
C3 C2 C7 C6 -0.02(16) . . . . ?
C3 C2 C7 C8 178.82(10) . . . . ?
C3 C4 C5 C6 -0.37(17) . . . . ?
C4 C5 C6 C7 0.78(16) . . . . ?
C12 C11 C10 C9 1.42(17) . . . . ?
C5 C6 C7 C2 -0.59(16) . . . . ?
C5 C6 C7 C8 -179.16(10) . . . . ?
C6 C7 C8 O2 -1.7(2) . . . . ?
C6 C7 C8 N1 177.40(11) . . . . ?
C7 C2 C3 C4 0.45(16) . . . . ?
C8 N1 C9 C10 -36.08(17) . . . . ?
C8 N1 C9 C13 145.77(12) . . . . ?
C8 N1 C1 O1 176.77(11) . . . . ?
C8 N1 C1 C2 -3.00(11) . . . . ?

_olex2_date_sample_data_collection 2021-02-12
_olex2_date_sample_submission    2021-02-02
_olex2_exptl_crystal_mounting_method 
'Frozen on a Mitegen cryoloop in Paretone oil.'
_olex2_submission_original_sample_id LNB348
_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_LNB381_twin
_database_code_depnum_ccdc_archive 'CCDC 2099683'
loop_
_audit_author_name
_audit_author_address
'David Wragg'
;University of Oslo
Norway
;
_audit_update_record             
;
2021-07-27 deposited with the CCDC.	2021-10-19 downloaded from the CCDC.
;
_audit_creation_date             2021-07-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
l.n.berntsen@kjemi.uio.no
david.wragg@smn.uio.no
_chemical_name_common            ?
_chemical_name_systematic        (E,E)-1,3-distyryl-5-fluorouracil
_chemical_formula_moiety         'C20 H15 F N2 O2'
_chemical_formula_sum            'C20 H15 F N2 O2'
_chemical_formula_weight         334.34
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      trigonal
_space_group_IT_number           161
_space_group_name_H-M_alt        'R 3 c'
_space_group_name_Hall           'R 3 -2"c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-y, -x, z+1/2'
'-x+y, y, z+1/2'
'x, x-y, z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'-y+2/3, -x+1/3, z+5/6'
'-x+y+2/3, y+1/3, z+5/6'
'x+2/3, x-y+1/3, z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-y+1/3, -x+2/3, z+7/6'
'-x+y+1/3, y+2/3, z+7/6'
'x+1/3, x-y+2/3, z+7/6'

_cell_length_a                   33.8915(10)
_cell_length_b                   33.8915(10)
_cell_length_c                   7.0535(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     7016.4(14)
_cell_formula_units_Z            18
_cell_measurement_reflns_used    1455
_cell_measurement_temperature    99.9
_cell_measurement_theta_max      24.69
_cell_measurement_theta_min      2.40
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.957
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_correction_T_min  0.700
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 31204 reflections, Rint = 0.0562
 (21115 with I > 3sig(I), Rint = 0.0420)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             3132
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0633
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5543
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.387
_diffrn_reflns_theta_min         2.082
_diffrn_ambient_temperature      99.9
_diffrn_detector                 'Bruker Photon 100 area detector'
_diffrn_detector_area_resol_mean 10.42
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ shutterless scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.919
_reflns_Friedel_fraction_full    0.968
_reflns_Friedel_fraction_max     0.927
_reflns_number_gt                4523
_reflns_number_total             5543
_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       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 
;
 Flack x determined using 982 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         5543
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0537
_refine_ls_restrained_S_all      1.052
_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)+(0.0410P)²+4.9561P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.1076
_refine_special_details          ?
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.34163
 0.26796 0.39041
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C16(H16), C17(H17), C6(H6), C5(H5), C13(H13), C12(H12), C11(H11), C14(H14),
 C00J(H00J), C19(H19), C18(H18), C4(H4), C8(H8), C9(H9), C10(H10)
;
_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
F1 F 0.02236(9) 0.32037(9) 0.5801(4) 0.0237(7) Uani 1 1 d . . . . .
O1 O 0.05297(10) 0.26365(11) 0.6900(5) 0.0197(8) Uani 1 1 d . . . . .
O2 O 0.19727(10) 0.36854(11) 0.4896(5) 0.0226(8) Uani 1 1 d . . . . .
N1 N 0.12543(12) 0.31391(12) 0.5825(5) 0.0130(9) Uani 1 1 d . . . . .
N2 N 0.14091(12) 0.38585(12) 0.4682(6) 0.0141(9) Uani 1 1 d . . . . .
C2 C 0.07894(15) 0.30017(15) 0.6173(7) 0.0148(10) Uani 1 1 d . . . . .
C15 C 0.20396(15) 0.51277(15) 0.3740(6) 0.0131(10) Uani 1 1 d . . . . .
C16 C 0.24424(15) 0.52291(15) 0.2790(6) 0.0131(10) Uani 1 1 d . . . . .
H16 H 0.251042 0.499313 0.256380 0.016 Uiso 1 1 calc R . . . .
C7 C 0.18884(16) 0.24869(15) 0.6730(6) 0.0152(10) Uani 1 1 d . . . . .
C3 C 0.15731(14) 0.35661(14) 0.5119(7) 0.0150(10) Uani 1 1 d . . . . .
C17 C 0.27424(15) 0.56658(14) 0.2176(6) 0.0158(11) Uani 1 1 d . . . . .
H17 H 0.301521 0.572871 0.154314 0.019 Uiso 1 1 calc R . . . .
C1 C 0.06677(14) 0.33317(16) 0.5580(7) 0.0150(10) Uani 1 1 d . . . . .
C6 C 0.17932(15) 0.28504(15) 0.6192(7) 0.0153(10) Uani 1 1 d . . . . .
H6 H 0.203905 0.312968 0.574190 0.018 Uiso 1 1 calc R . . . .
C5 C 0.13846(16) 0.28115(15) 0.6299(6) 0.0157(11) Uani 1 1 d . . . . .
H5 H 0.114709 0.252735 0.675221 0.019 Uiso 1 1 calc R . . . .
C13 C 0.17395(15) 0.43030(15) 0.4068(7) 0.0150(10) Uani 1 1 d . . . . .
H13 H 0.199494 0.433744 0.337285 0.018 Uiso 1 1 calc R . . . .
C12 C 0.23409(16) 0.25932(16) 0.6907(7) 0.0180(11) Uani 1 1 d . . . . .
H12 H 0.257806 0.289416 0.663881 0.022 Uiso 1 1 calc R . . . .
C11 C 0.24510(17) 0.22691(16) 0.7467(7) 0.0187(11) Uani 1 1 d . . . . .
H11 H 0.276133 0.234935 0.759495 0.022 Uiso 1 1 calc R . . . .
C14 C 0.17097(15) 0.46706(15) 0.4413(6) 0.0140(10) Uani 1 1 d . . . . .
H14 H 0.145865 0.463607 0.514203 0.017 Uiso 1 1 calc R . . . .
C00J C 0.26454(15) 0.60123(15) 0.2484(7) 0.0163(11) Uani 1 1 d . . . . .
H00J H 0.284931 0.631181 0.204421 0.020 Uiso 1 1 calc R . . . .
C19 C 0.19508(15) 0.54841(14) 0.4051(7) 0.0155(11) Uani 1 1 d . . . . .
H19 H 0.168045 0.542452 0.469591 0.019 Uiso 1 1 calc R . . . .
C18 C 0.22506(15) 0.59216(15) 0.3433(7) 0.0182(11) Uani 1 1 d . . . . .
H18 H 0.218589 0.615982 0.365878 0.022 Uiso 1 1 calc R . . . .
C4 C 0.09580(15) 0.37344(16) 0.4879(7) 0.0160(10) Uani 1 1 d . . . . .
H4 H 0.085636 0.393843 0.451114 0.019 Uiso 1 1 calc R . . . .
C8 C 0.15497(16) 0.20426(16) 0.7101(7) 0.0180(11) Uani 1 1 d . . . . .
H8 H 0.123904 0.196178 0.698043 0.022 Uiso 1 1 calc R . . . .
C9 C 0.16571(16) 0.17158(15) 0.7644(7) 0.0196(11) Uani 1 1 d . . . . .
H9 H 0.142045 0.141293 0.788488 0.023 Uiso 1 1 calc R . . . .
C10 C 0.21093(16) 0.18280(16) 0.7841(7) 0.0187(11) Uani 1 1 d . . . . .
H10 H 0.218319 0.160416 0.822785 0.022 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
F1 C1 1.351(5) . ?
O1 C2 1.217(5) . ?
O2 C3 1.214(5) . ?
N1 C2 1.423(6) . ?
N1 C3 1.395(5) . ?
N1 C5 1.425(6) . ?
N2 C3 1.391(6) . ?
N2 C13 1.423(5) . ?
N2 C4 1.375(6) . ?
C2 C1 1.434(6) . ?
C15 C16 1.400(6) . ?
C15 C14 1.464(6) . ?
C15 C19 1.400(6) . ?
C16 H16 0.9500 . ?
C16 C17 1.381(6) . ?
C7 C6 1.471(6) . ?
C7 C12 1.395(6) . ?
C7 C8 1.388(6) . ?
C17 H17 0.9500 . ?
C17 C00J 1.386(6) . ?
C1 C4 1.316(6) . ?
C6 H6 0.9500 . ?
C6 C5 1.326(6) . ?
C5 H5 0.9500 . ?
C13 H13 0.9500 . ?
C13 C14 1.322(6) . ?
C12 H12 0.9500 . ?
C12 C11 1.382(6) . ?
C11 H11 0.9500 . ?
C11 C10 1.384(6) . ?
C14 H14 0.9500 . ?
C00J H00J 0.9500 . ?
C00J C18 1.386(7) . ?
C19 H19 0.9500 . ?
C19 C18 1.384(6) . ?
C18 H18 0.9500 . ?
C4 H4 0.9500 . ?
C8 H8 0.9500 . ?
C8 C9 1.381(6) . ?
C9 H9 0.9500 . ?
C9 C10 1.389(6) . ?
C10 H10 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
C2 N1 C5 115.4(4) . . ?
C3 N1 C2 123.9(4) . . ?
C3 N1 C5 120.7(4) . . ?
C3 N2 C13 116.0(4) . . ?
C4 N2 C3 122.6(4) . . ?
C4 N2 C13 121.4(4) . . ?
O1 C2 N1 121.7(4) . . ?
O1 C2 C1 124.9(4) . . ?
N1 C2 C1 113.4(4) . . ?
C16 C15 C14 123.4(4) . . ?
C19 C15 C16 117.8(4) . . ?
C19 C15 C14 118.8(4) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 C15 121.2(4) . . ?
C17 C16 H16 119.4 . . ?
C12 C7 C6 118.7(4) . . ?
C8 C7 C6 123.3(4) . . ?
C8 C7 C12 118.0(4) . . ?
O2 C3 N1 123.2(4) . . ?
O2 C3 N2 120.7(4) . . ?
N2 C3 N1 116.1(4) . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C00J 120.0(4) . . ?
C00J C17 H17 120.0 . . ?
F1 C1 C2 115.1(4) . . ?
C4 C1 F1 120.8(4) . . ?
C4 C1 C2 124.1(4) . . ?
C7 C6 H6 118.0 . . ?
C5 C6 C7 123.9(4) . . ?
C5 C6 H6 118.0 . . ?
N1 C5 H5 115.7 . . ?
C6 C5 N1 128.6(4) . . ?
C6 C5 H5 115.7 . . ?
N2 C13 H13 118.3 . . ?
C14 C13 N2 123.5(4) . . ?
C14 C13 H13 118.3 . . ?
C7 C12 H12 119.4 . . ?
C11 C12 C7 121.3(5) . . ?
C11 C12 H12 119.4 . . ?
C12 C11 H11 120.0 . . ?
C12 C11 C10 120.0(5) . . ?
C10 C11 H11 120.0 . . ?
C15 C14 H14 118.0 . . ?
C13 C14 C15 124.0(4) . . ?
C13 C14 H14 118.0 . . ?
C17 C00J H00J 120.0 . . ?
C17 C00J C18 120.0(4) . . ?
C18 C00J H00J 120.0 . . ?
C15 C19 H19 119.5 . . ?
C18 C19 C15 121.0(4) . . ?
C18 C19 H19 119.5 . . ?
C00J C18 H18 120.0 . . ?
C19 C18 C00J 120.0(4) . . ?
C19 C18 H18 120.0 . . ?
N2 C4 H4 120.2 . . ?
C1 C4 N2 119.7(4) . . ?
C1 C4 H4 120.2 . . ?
C7 C8 H8 119.5 . . ?
C9 C8 C7 121.1(4) . . ?
C9 C8 H8 119.5 . . ?
C8 C9 H9 119.8 . . ?
C8 C9 C10 120.3(4) . . ?
C10 C9 H9 119.8 . . ?
C11 C10 C9 119.3(4) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?

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
F1 C1 C4 N2 179.5(4) . . . . ?
O1 C2 C1 F1 -2.9(7) . . . . ?
O1 C2 C1 C4 176.6(5) . . . . ?
N1 C2 C1 F1 176.9(4) . . . . ?
N1 C2 C1 C4 -3.6(7) . . . . ?
N2 C13 C14 C15 -178.1(4) . . . . ?
C2 N1 C3 O2 177.1(5) . . . . ?
C2 N1 C3 N2 -2.4(6) . . . . ?
C2 N1 C5 C6 -177.4(5) . . . . ?
C2 C1 C4 N2 0.0(8) . . . . ?
C15 C16 C17 C00J -0.5(7) . . . . ?
C15 C19 C18 C00J 0.2(7) . . . . ?
C16 C15 C14 C13 -5.5(7) . . . . ?
C16 C15 C19 C18 0.2(6) . . . . ?
C16 C17 C00J C18 1.0(7) . . . . ?
C7 C6 C5 N1 179.8(5) . . . . ?
C7 C12 C11 C10 0.8(7) . . . . ?
C7 C8 C9 C10 0.4(7) . . . . ?
C3 N1 C2 O1 -175.4(4) . . . . ?
C3 N1 C2 C1 4.9(6) . . . . ?
C3 N1 C5 C6 1.0(7) . . . . ?
C3 N2 C13 C14 -147.8(5) . . . . ?
C3 N2 C4 C1 2.9(7) . . . . ?
C17 C00J C18 C19 -0.8(7) . . . . ?
C6 C7 C12 C11 177.9(4) . . . . ?
C6 C7 C8 C9 -178.5(4) . . . . ?
C5 N1 C2 O1 3.0(6) . . . . ?
C5 N1 C2 C1 -176.8(4) . . . . ?
C5 N1 C3 O2 -1.2(7) . . . . ?
C5 N1 C3 N2 179.3(4) . . . . ?
C13 N2 C3 O2 -3.1(7) . . . . ?
C13 N2 C3 N1 176.4(4) . . . . ?
C13 N2 C4 C1 -175.1(4) . . . . ?
C12 C7 C6 C5 -167.8(5) . . . . ?
C12 C7 C8 C9 0.5(7) . . . . ?
C12 C11 C10 C9 0.1(7) . . . . ?
C14 C15 C16 C17 179.8(4) . . . . ?
C14 C15 C19 C18 -179.6(4) . . . . ?
C19 C15 C16 C17 -0.1(6) . . . . ?
C19 C15 C14 C13 174.4(4) . . . . ?
C4 N2 C3 O2 178.8(5) . . . . ?
C4 N2 C3 N1 -1.7(7) . . . . ?
C4 N2 C13 C14 30.4(7) . . . . ?
C8 C7 C6 C5 11.1(8) . . . . ?
C8 C7 C12 C11 -1.1(7) . . . . ?
C8 C9 C10 C11 -0.7(8) . . . . ?

_olex2_date_sample_data_collection 2021-04-16
_olex2_date_sample_submission    2021-04-16
_olex2_submission_original_sample_id LNB381
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.34163
2 0.26796
3 0.39041

####################################################################### 
# 
# 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_TNS4_14
_database_code_depnum_ccdc_archive 'CCDC 2099686'
loop_
_audit_author_name
_audit_author_address
'David Wragg'
;University of Oslo
Norway
;
_audit_update_record             
;
2021-07-27 deposited with the CCDC.	2021-10-19 downloaded from the CCDC.
;
_audit_creation_date             2021-07-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;

loop_
_audit_author_email
l.n.berntsen@kjemi.uio.no
david.wragg@smn.uio.no
_chemical_formula_moiety         'C9 H9 N O3 S'
_chemical_formula_sum            'C9 H9 N O3 S'
_chemical_formula_weight         211.24
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2
5 -x,-y,-z
6 -x-1/2,y-1/2,z
7 x,-y-1/2,z-1/2
8 x-1/2,y,-z-1/2

_symmetry_Int_Tables_number      61
_cell_length_a                   13.5471(10)
_cell_length_b                   7.5236(5)
_cell_length_c                   18.4113(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1876.5(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8689
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      30.37
_cell_measurement_theta_min      2.68
_exptl_absorpt_coefficient_mu    0.323
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.7032
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0824 before and 0.0444 after correction. The Ratio of minimum to maximum transmission is 0.9425. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     ?
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.4953
_exptl_crystal_description       block
_exptl_crystal_F_000             881.4544
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.15
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            18385
_diffrn_reflns_theta_full        30.5675
_diffrn_reflns_theta_max         30.57
_diffrn_reflns_theta_min         2.68
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker Photon 100 area detector'
_diffrn_detector_area_resol_mean 10.42
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.9830
_diffrn_measured_fraction_theta_max 0.9830
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ shutterless scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              18
_reflns_limit_h_min              0
_reflns_limit_k_max              10
_reflns_limit_k_min              0
_reflns_limit_l_max              26
_reflns_limit_l_min              0
_reflns_number_gt                2348
_reflns_number_total             2826
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.5089
_refine_diff_density_min         -0.3274
_refine_diff_density_rms         0.0835
_refine_ls_d_res_high            0.6988
_refine_ls_d_res_low             7.6141
_refine_ls_goodness_of_fit_ref   1.0526
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    23
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2826
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0326
_refine_ls_restrained_S_all      1.0526
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0385P)²+0.7002P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0753
_refine_ls_wR_factor_ref         0.0804
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C1) = Uanis(S1A)
Uanis(S1) = Uanis(C1A)
3. Others
 Sof(H4b)=Sof(S1A)=Sof(C1A)=Sof(H1A)=Sof(H2b)=Sof(H4b)=Sof(H1A)=1-FVAR(1)
 Sof(S1)=Sof(C1)=Sof(H1)=Sof(H4a)=Sof(H2)=Sof(H2a)=Sof(H1)=Sof(H4a)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C2(H2a), C2(H2b), C1(H1), C4(H4a), C4(H4b), C1A(H1A)
4.b Idealised Me refined as rotating group:
 C8(H8a,H8b,H8c), C9(H9a,H9b,H9c)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
_atom_site_disorder_group
S1 S 0.60900(3) 0.60081(4) 0.530841(17) 0.01667(9) Uani 0.85605(19) . 1
O1 O 0.62490(5) 0.74115(9) 0.85687(4) 0.01518(17) Uani 1.000000 . .
O3 O 0.55998(6) 0.36213(9) 0.75669(4) 0.01730(18) Uani 1.000000 . .
O2 O 0.68255(6) 0.92614(9) 0.77117(5) 0.01981(19) Uani 1.000000 . .
N1 N 0.62545(6) 0.64355(10) 0.74236(5) 0.01150(18) Uani 1.000000 . .
C1 C 0.71149(13) 0.71337(15) 0.55589(12) 0.0207(2) Uani 0.85605(19) . 1
C3 C 0.63809(7) 0.64822(11) 0.66607(6) 0.0122(2) Uani 1.000000 . .
C5 C 0.64809(7) 0.78591(12) 0.78806(6) 0.0134(2) Uani 1.000000 . .
C6 C 0.58624(7) 0.50311(12) 0.78084(6) 0.0120(2) Uani 1.000000 . .
C7 C 0.58210(7) 0.56245(12) 0.85963(6) 0.0127(2) Uani 1.000000 . .
C8 C 0.47618(7) 0.57791(12) 0.88562(6) 0.0165(2) Uani 1.000000 . .
H8a H 0.47493(7) 0.63509(12) 0.93343(6) 0.0248(3) Uiso 1.000000 GR .
H8b H 0.43824(7) 0.64956(12) 0.85102(6) 0.0248(3) Uiso 1.000000 GR .
H8c H 0.44695(7) 0.45908(12) 0.88918(6) 0.0248(3) Uiso 1.000000 GR .
C4 C 0.57231(8) 0.57261(12) 0.61867(6) 0.0151(2) Uani 1.000000 . .
C2 C 0.71964(7) 0.73011(12) 0.63162(6) 0.0164(2) Uani 1.000000 . .
C9 C 0.64539(8) 0.44618(13) 0.90803(6) 0.0187(2) Uani 1.000000 . .
H9a H 0.71426(8) 0.45248(13) 0.89195(6) 0.0280(3) Uiso 1.000000 GR .
H9b H 0.64057(8) 0.48788(13) 0.95833(6) 0.0280(3) Uiso 1.000000 GR .
H9c H 0.62228(8) 0.32295(13) 0.90511(6) 0.0280(3) Uiso 1.000000 GR .
S1A S 0.72065(17) 0.72615(18) 0.54933(17) 0.0207(2) Uani 0.14395(19) . 2
C1A C 0.60372(19) 0.5990(2) 0.54884(19) 0.01667(9) Uani 0.14395(19) . 2
H2a H 0.77228(7) 0.78802(12) 0.65617(6) 0.0196(3) Uiso 0.85605(19) R 1
H2b H 0.77108(7) 0.78473(12) 0.65867(6) 0.0196(3) Uiso 0.14395(19) R 2
H1 H 0.75827(13) 0.76003(15) 0.52251(12) 0.0249(3) Uiso 0.85605(19) R 1
H4a H 0.51383(8) 0.51227(12) 0.63292(6) 0.0181(3) Uiso 0.85605(19) R 1
H4b H 0.51385(8) 0.51127(12) 0.63222(6) 0.0181(3) Uiso 0.14395(19) R 2
H1A H 0.57055(19) 0.5582(2) 0.50655(19) 0.02001(11) Uiso 0.14395(19) R 2


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
S1 C1 1.6904(17) . ?
S1 C4 1.7049(11) . ?
O1 C5 1.3481(13) . ?
O1 C7 1.4650(11) . ?
O3 C6 1.2039(11) . ?
O2 C5 1.1949(12) . ?
N1 C3 1.4154(13) . ?
N1 C5 1.3961(12) . ?
N1 C6 1.3786(12) . ?
C1 C2 1.404(2) . ?
C3 C4 1.3709(14) . ?
C3 C2 1.4150(14) . ?
C6 C7 1.5188(14) . ?
C7 C8 1.5170(14) . ?
C7 C9 1.5146(14) . ?
C4 C1A 1.369(4) . ?
C2 S1A 1.515(3) . ?
S1A C1A 1.851(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O1 C5 110.74(7) . . ?
C5 N1 C3 123.53(8) . . ?
C6 N1 C3 125.15(8) . . ?
C6 N1 C5 111.27(8) . . ?
C4 C3 N1 122.87(9) . . ?
C2 C3 N1 123.37(9) . . ?
C2 C3 C4 113.75(10) . . ?
O2 C5 O1 123.79(9) . . ?
N1 C5 O1 108.88(8) . . ?
N1 C5 O2 127.33(10) . . ?
N1 C6 O3 126.82(10) . . ?
C7 C6 O3 126.93(9) . . ?
C7 C6 N1 106.25(8) . . ?
C6 C7 O1 102.83(7) . . ?
C8 C7 O1 108.35(7) . . ?
C8 C7 C6 111.02(8) . . ?
C9 C7 O1 109.05(8) . . ?
C9 C7 C6 111.79(8) . . ?
C9 C7 C8 113.21(8) . . ?

_olex2_date_sample_completion    2021-07-08
_olex2_date_sample_data_collection 2021-07-08
_olex2_exptl_crystal_mounting_method 
'Frozen on Mitegen cryoloop with Paretone oil'
_olex2_submission_special_instructions 'No special instructions were received'
_chemical_name_systematic        
5,5-Dimethyl-3-(3-thiophenyl)-2,4-oxazolidinedione
