# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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. 
# 
#######################################################################

data_rdb_1_33i2_0m
_database_code_depnum_ccdc_archive 'CCDC 2093794'
loop_
_audit_author_name
_audit_author_address
'Colin Seaton'
;University of Bradford
United Kingdom
;
_audit_update_record             
;
2021-07-01 deposited with the CCDC.	2021-09-16 downloaded from the CCDC.
;
_audit_creation_date             2021-04-15
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        2,3-bis(3-iodophenyl)quinoxaline
_chemical_formula_moiety         'C20 H12 I2 N2'
_chemical_formula_sum            'C20 H12 I2 N2'
_chemical_formula_weight         534.12
_chemical_melting_point          459
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'
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'

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

_cell_length_a                   8.6398(5)
_cell_length_b                   19.4072(10)
_cell_length_c                   10.7039(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.237(3)
_cell_angle_gamma                90
_cell_volume                     1760.36(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7326
_cell_measurement_temperature    99.87
_cell_measurement_theta_max      31.50
_cell_measurement_theta_min      2.21
_shelx_estimated_absorpt_T_max   0.716
_shelx_estimated_absorpt_T_min   0.284
_exptl_absorpt_coefficient_mu    3.576
_exptl_absorpt_correction_T_max  0.7551
_exptl_absorpt_correction_T_min  0.3066
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.0686 before and 0.0512 after correction.
The Ratio of minimum to maximum transmission is 0.4060.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.015
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_av_unetI/netI     0.0600
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            39187
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         35.441
_diffrn_reflns_theta_min         2.623
_diffrn_ambient_temperature      99.87
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5176
_reflns_number_total             7651
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         2.947
_refine_diff_density_min         -1.615
_refine_diff_density_rms         0.188
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         7651
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0854
_refine_ls_R_factor_gt           0.0461
_refine_ls_restrained_S_all      1.022
_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)+(0.0423P)²+3.3897P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.1067
_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:
 C18(H18), C19(H19), C20(H20), C12(H12), C14(H14), C10(H10), C16(H16), C2(H2),
 C13(H13), C1(H1), C3(H3), C6(H6)
;
_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
N2 N 0.0620(4) 0.35250(15) 0.5225(3) 0.0204(6) Uani 1 1 d . . . . .
N1 N 0.3593(4) 0.41745(16) 0.5675(3) 0.0228(6) Uani 1 1 d . . . . .
C17 C 0.7120(4) 0.34701(18) 0.8700(3) 0.0200(7) Uani 1 1 d . . . . .
C18 C 0.7556(4) 0.27864(19) 0.8566(4) 0.0218(7) Uani 1 1 d . . . . .
H18 H 0.851838 0.261151 0.904347 0.026 Uiso 1 1 calc R U . . .
C19 C 0.6555(5) 0.23669(19) 0.7721(4) 0.0235(7) Uani 1 1 d . . . . .
H19 H 0.683471 0.189998 0.761648 0.028 Uiso 1 1 calc R U . . .
C11 C 0.0141(4) 0.16120(18) 0.6964(4) 0.0203(7) Uani 1 1 d . . . . .
C9 C 0.1430(4) 0.27068(18) 0.6882(3) 0.0193(7) Uani 1 1 d . . . . .
C20 C 0.5149(4) 0.26240(18) 0.7026(4) 0.0214(7) Uani 1 1 d . . . . .
H20 H 0.445188 0.232753 0.647596 0.026 Uiso 1 1 calc R U . . .
C15 C 0.4755(4) 0.33121(18) 0.7132(3) 0.0193(7) Uani 1 1 d . . . . .
C7 C 0.1791(4) 0.32977(17) 0.6109(3) 0.0187(7) Uani 1 1 d . . . . .
C12 C 0.0683(4) 0.1567(2) 0.8282(4) 0.0243(8) Uani 1 1 d . . . . .
H12 H 0.043539 0.118050 0.875072 0.029 Uiso 1 1 calc R U . . .
C8 C 0.3337(4) 0.36145(18) 0.6296(3) 0.0190(7) Uani 1 1 d . . . . .
C14 C 0.1964(4) 0.2672(2) 0.8195(4) 0.0229(7) Uani 1 1 d . . . . .
H14 H 0.258435 0.303702 0.862116 0.028 Uiso 1 1 calc R U . . .
C10 C 0.0485(4) 0.21670(18) 0.6269(4) 0.0194(7) Uani 1 1 d . . . . .
H10 H 0.008625 0.218691 0.537707 0.023 Uiso 1 1 calc R U . . .
C16 C 0.5749(4) 0.37430(17) 0.7984(3) 0.0199(7) Uani 1 1 d . . . . .
H16 H 0.548732 0.421390 0.806861 0.024 Uiso 1 1 calc R U . . .
C2 C -0.0129(5) 0.4977(2) 0.3034(3) 0.0233(7) Uani 1 1 d . . . . .
H2 H -0.096325 0.516404 0.241603 0.028 Uiso 1 1 calc R U . . .
C13 C 0.1600(4) 0.2111(2) 0.8888(4) 0.0244(8) Uani 1 1 d . . . . .
H13 H 0.197733 0.209526 0.978306 0.029 Uiso 1 1 calc R U . . .
C1 C 0.1330(5) 0.5329(2) 0.3330(4) 0.0237(7) Uani 1 1 d . . . . .
H1 H 0.145008 0.575680 0.292759 0.028 Uiso 1 1 calc R U . . .
C3 C -0.0352(4) 0.43770(19) 0.3620(4) 0.0220(7) Uani 1 1 d . . . . .
H3 H -0.133469 0.414372 0.340996 0.026 Uiso 1 1 calc R U . . .
C4 C 0.0890(4) 0.40971(18) 0.4551(3) 0.0206(7) Uani 1 1 d . . . . .
C5 C 0.2365(4) 0.44450(19) 0.4816(3) 0.0203(7) Uani 1 1 d . . . . .
C6 C 0.2564(5) 0.5065(2) 0.4182(4) 0.0233(7) Uani 1 1 d . . . . .
H6 H 0.355175 0.529666 0.434789 0.028 Uiso 1 1 calc R U . . .
I2 I 0.85807(3) 0.40930(2) 1.00487(2) 0.02570(7) Uani 1 1 d . . . . .
I1 I -0.12306(3) 0.07987(2) 0.60344(3) 0.02566(7) 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
N2 C7 1.319(5) . ?
N2 C4 1.369(5) . ?
N1 C8 1.315(5) . ?
N1 C5 1.366(5) . ?
C17 C18 1.394(5) . ?
C17 C16 1.385(5) . ?
C17 I2 2.104(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.387(5) . ?
C19 H19 0.9500 . ?
C19 C20 1.388(5) . ?
C11 C12 1.400(5) . ?
C11 C10 1.374(5) . ?
C11 I1 2.104(3) . ?
C9 C7 1.483(5) . ?
C9 C14 1.392(5) . ?
C9 C10 1.410(5) . ?
C20 H20 0.9500 . ?
C20 C15 1.388(5) . ?
C15 C8 1.490(5) . ?
C15 C16 1.401(5) . ?
C7 C8 1.448(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.401(5) . ?
C14 H14 0.9500 . ?
C14 C13 1.388(6) . ?
C10 H10 0.9500 . ?
C16 H16 0.9500 . ?
C2 H2 0.9500 . ?
C2 C1 1.414(5) . ?
C2 C3 1.354(5) . ?
C13 H13 0.9500 . ?
C1 H1 0.9500 . ?
C1 C6 1.362(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.422(5) . ?
C4 C5 1.420(5) . ?
C5 C6 1.408(5) . ?
C6 H6 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
C7 N2 C4 117.6(3) . . ?
C8 N1 C5 118.2(3) . . ?
C18 C17 I2 118.6(3) . . ?
C16 C17 C18 121.7(3) . . ?
C16 C17 I2 119.6(3) . . ?
C17 C18 H18 120.7 . . ?
C19 C18 C17 118.6(3) . . ?
C19 C18 H18 120.7 . . ?
C18 C19 H19 119.7 . . ?
C18 C19 C20 120.5(3) . . ?
C20 C19 H19 119.7 . . ?
C12 C11 I1 118.5(3) . . ?
C10 C11 C12 122.0(3) . . ?
C10 C11 I1 119.5(3) . . ?
C14 C9 C7 122.5(3) . . ?
C14 C9 C10 118.8(3) . . ?
C10 C9 C7 118.7(3) . . ?
C19 C20 H20 119.8 . . ?
C19 C20 C15 120.3(3) . . ?
C15 C20 H20 119.8 . . ?
C20 C15 C8 121.1(3) . . ?
C20 C15 C16 119.9(3) . . ?
C16 C15 C8 118.9(3) . . ?
N2 C7 C9 116.4(3) . . ?
N2 C7 C8 121.0(3) . . ?
C8 C7 C9 122.6(3) . . ?
C11 C12 H12 121.0 . . ?
C11 C12 C13 117.9(4) . . ?
C13 C12 H12 121.0 . . ?
N1 C8 C15 115.4(3) . . ?
N1 C8 C7 121.5(3) . . ?
C7 C8 C15 123.0(3) . . ?
C9 C14 H14 119.6 . . ?
C13 C14 C9 120.9(3) . . ?
C13 C14 H14 119.6 . . ?
C11 C10 C9 119.8(3) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C17 C16 C15 118.8(3) . . ?
C17 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C3 C2 C1 120.8(3) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.6(4) . . ?
C14 C13 H13 119.7 . . ?
C2 C1 H1 119.5 . . ?
C6 C1 C2 121.1(4) . . ?
C6 C1 H1 119.5 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.8(3) . . ?
C4 C3 H3 120.1 . . ?
N2 C4 C3 119.8(3) . . ?
N2 C4 C5 121.2(3) . . ?
C5 C4 C3 118.9(3) . . ?
N1 C5 C4 120.0(3) . . ?
N1 C5 C6 120.0(3) . . ?
C6 C5 C4 119.9(3) . . ?
C1 C6 C5 119.4(4) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?

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
N2 C7 C8 N1 6.1(5) . . . . ?
N2 C7 C8 C15 -170.0(3) . . . . ?
N2 C4 C5 N1 6.0(5) . . . . ?
N2 C4 C5 C6 -174.6(4) . . . . ?
N1 C5 C6 C1 -179.9(4) . . . . ?
C17 C18 C19 C20 -0.1(6) . . . . ?
C18 C17 C16 C15 2.0(6) . . . . ?
C18 C19 C20 C15 2.5(6) . . . . ?
C19 C20 C15 C8 173.6(4) . . . . ?
C19 C20 C15 C16 -2.7(6) . . . . ?
C11 C12 C13 C14 -0.4(6) . . . . ?
C9 C7 C8 N1 -174.0(3) . . . . ?
C9 C7 C8 C15 9.8(5) . . . . ?
C9 C14 C13 C12 -0.2(6) . . . . ?
C20 C15 C8 N1 -126.9(4) . . . . ?
C20 C15 C8 C7 49.5(5) . . . . ?
C20 C15 C16 C17 0.5(6) . . . . ?
C7 N2 C4 C3 -177.7(3) . . . . ?
C7 N2 C4 C5 -1.6(5) . . . . ?
C7 C9 C14 C13 179.9(4) . . . . ?
C7 C9 C10 C11 179.7(3) . . . . ?
C12 C11 C10 C9 1.1(5) . . . . ?
C8 N1 C5 C4 -4.2(5) . . . . ?
C8 N1 C5 C6 176.5(3) . . . . ?
C8 C15 C16 C17 -175.9(3) . . . . ?
C14 C9 C7 N2 -137.6(4) . . . . ?
C14 C9 C7 C8 42.5(5) . . . . ?
C14 C9 C10 C11 -1.6(5) . . . . ?
C10 C11 C12 C13 0.0(6) . . . . ?
C10 C9 C7 N2 41.0(5) . . . . ?
C10 C9 C7 C8 -138.8(4) . . . . ?
C10 C9 C14 C13 1.2(6) . . . . ?
C16 C17 C18 C19 -2.2(6) . . . . ?
C16 C15 C8 N1 49.4(5) . . . . ?
C16 C15 C8 C7 -134.2(4) . . . . ?
C2 C1 C6 C5 -2.5(6) . . . . ?
C2 C3 C4 N2 174.1(4) . . . . ?
C2 C3 C4 C5 -2.1(6) . . . . ?
C1 C2 C3 C4 0.4(6) . . . . ?
C3 C2 C1 C6 2.0(6) . . . . ?
C3 C4 C5 N1 -177.8(3) . . . . ?
C3 C4 C5 C6 1.5(5) . . . . ?
C4 N2 C7 C9 175.9(3) . . . . ?
C4 N2 C7 C8 -4.2(5) . . . . ?
C4 C5 C6 C1 0.8(6) . . . . ?
C5 N1 C8 C15 174.8(3) . . . . ?
C5 N1 C8 C7 -1.6(5) . . . . ?
I2 C17 C18 C19 177.0(3) . . . . ?
I2 C17 C16 C15 -177.2(3) . . . . ?
I1 C11 C12 C13 179.7(3) . . . . ?
I1 C11 C10 C9 -178.7(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol/water'
####################################################################### 
# 
# 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_rdb_33cl_2_0m
_database_code_depnum_ccdc_archive 'CCDC 2093796'
loop_
_audit_author_name
_audit_author_address
'Colin Seaton'
;University of Bradford
United Kingdom
;
_audit_update_record             
;
2021-07-01 deposited with the CCDC.	2021-09-16 downloaded from the CCDC.
;
_audit_creation_date             2021-04-15
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        2,3-bis(3-chlorophenyl)quinoxaline
_chemical_formula_moiety         'C20 H12 Cl2 N2'
_chemical_formula_sum            'C20 H12 Cl2 N2'
_chemical_formula_weight         351.22
_chemical_melting_point          458
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   13.368(3)
_cell_length_b                   7.5374(12)
_cell_length_c                   16.175(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.640(9)
_cell_angle_gamma                90
_cell_volume                     1576.9(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1974
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      25.44
_cell_measurement_theta_min      2.28
_shelx_estimated_absorpt_T_max   0.960
_shelx_estimated_absorpt_T_min   0.746
_exptl_absorpt_coefficient_mu    0.414
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6630
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.0547 before and 0.0466 after correction.
The Ratio of minimum to maximum transmission is 0.8887.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Needle
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.54
_exptl_crystal_size_min          0.10
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_unetI/netI     0.0774
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.744
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8785
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.744
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.470
_diffrn_reflns_theta_min         2.603
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.744
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2285
_reflns_number_total             3565
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3565
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0917
_refine_ls_R_factor_gt           0.0450
_refine_ls_restrained_S_all      1.012
_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)+(0.0389P)²+0.2122P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0847
_refine_ls_wR_factor_ref         0.1008
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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
Cl2 Cl -0.08671(5) -0.04438(7) 0.38457(4) 0.02139(17) Uani 1 1 d . . . . .
Cl1 Cl 0.17266(5) 0.55000(9) 0.66995(4) 0.03040(19) Uani 1 1 d . . . . .
N1 N 0.40687(15) 0.2833(2) 0.46981(13) 0.0152(4) Uani 1 1 d . . . . .
N2 N 0.34878(15) 0.0621(2) 0.32451(12) 0.0145(4) Uani 1 1 d . . . . .
C15 C 0.16869(18) 0.1006(3) 0.31490(15) 0.0139(5) Uani 1 1 d . . . . .
C9 C 0.23346(17) 0.3815(3) 0.45339(15) 0.0137(5) Uani 1 1 d . . . . .
C7 C 0.30920(18) 0.2639(3) 0.42737(15) 0.0142(5) Uani 1 1 d . . . . .
C8 C 0.27915(18) 0.1438(3) 0.35587(15) 0.0135(5) Uani 1 1 d . . . . .
C5 C 0.47949(17) 0.1930(3) 0.44010(15) 0.0145(5) Uani 1 1 d . . . . .
C16 C 0.09944(19) 0.0597(3) 0.36358(16) 0.0152(5) Uani 1 1 d . . . . .
C14 C 0.16184(19) 0.4776(3) 0.39208(16) 0.0161(5) Uani 1 1 d . . . . .
C17 C -0.00129(18) 0.0135(3) 0.32304(16) 0.0160(5) Uani 1 1 d . . . . .
C4 C 0.45070(18) 0.0889(3) 0.36502(15) 0.0152(5) Uani 1 1 d . . . . .
C18 C -0.0356(2) 0.0073(3) 0.23516(16) 0.0171(6) Uani 1 1 d . . . . .
C20 C 0.13454(19) 0.0954(3) 0.22604(16) 0.0156(5) Uani 1 1 d . . . . .
C19 C 0.03273(19) 0.0508(3) 0.18676(17) 0.0175(6) Uani 1 1 d . . . . .
C10 C 0.23742(19) 0.4055(3) 0.53995(17) 0.0172(5) Uani 1 1 d . . . . .
C11 C 0.16876(18) 0.5219(3) 0.56231(15) 0.0176(5) Uani 1 1 d . . . . .
C3 C 0.52836(19) 0.0098(3) 0.33212(17) 0.0180(6) Uani 1 1 d . . . . .
C13 C 0.09525(19) 0.5949(3) 0.41667(17) 0.0184(6) Uani 1 1 d . . . . .
C12 C 0.09770(19) 0.6177(3) 0.50207(17) 0.0188(6) Uani 1 1 d . . . . .
C6 C 0.58513(19) 0.2118(3) 0.48229(17) 0.0184(6) Uani 1 1 d . . . . .
C2 C 0.6302(2) 0.0330(3) 0.37361(17) 0.0199(6) Uani 1 1 d . . . . .
C1 C 0.6589(2) 0.1331(3) 0.44928(17) 0.0194(6) Uani 1 1 d . . . . .
H2 H 0.682(2) -0.018(3) 0.3492(17) 0.027(7) Uiso 1 1 d . . . . .
H19 H 0.0093(19) 0.050(3) 0.1285(16) 0.019(7) Uiso 1 1 d . . . . .
H18 H -0.104(2) -0.029(3) 0.2094(17) 0.027(7) Uiso 1 1 d . . . . .
H10 H 0.2829(18) 0.341(3) 0.5828(16) 0.016(6) Uiso 1 1 d . . . . .
H16 H 0.1208(18) 0.065(3) 0.4211(15) 0.012(6) Uiso 1 1 d . . . . .
H13 H 0.0492(17) 0.659(3) 0.3742(15) 0.012(6) Uiso 1 1 d . . . . .
H3 H 0.5084(18) -0.059(3) 0.2802(16) 0.018(6) Uiso 1 1 d . . . . .
H6 H 0.6028(18) 0.290(3) 0.5330(17) 0.022(7) Uiso 1 1 d . . . . .
H12 H 0.0504(18) 0.696(3) 0.5190(16) 0.023(7) Uiso 1 1 d . . . . .
H1 H 0.7320(19) 0.151(3) 0.4785(15) 0.021(7) Uiso 1 1 d . . . . .
H20 H 0.1770(18) 0.126(3) 0.1930(16) 0.017(7) Uiso 1 1 d . . . . .
H14 H 0.1638(16) 0.470(2) 0.3354(14) 0.003(5) Uiso 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
Cl2 C17 1.749(3) . ?
Cl1 C11 1.742(2) . ?
N1 C7 1.321(3) . ?
N1 C5 1.368(3) . ?
N2 C8 1.320(3) . ?
N2 C4 1.369(3) . ?
C15 C8 1.494(3) . ?
C15 C16 1.393(3) . ?
C15 C20 1.394(3) . ?
C9 C7 1.484(3) . ?
C9 C14 1.395(3) . ?
C9 C10 1.400(3) . ?
C7 C8 1.443(3) . ?
C5 C4 1.415(3) . ?
C5 C6 1.412(3) . ?
C16 C17 1.385(3) . ?
C16 H16 0.90(2) . ?
C14 C13 1.382(3) . ?
C14 H14 0.92(2) . ?
C17 C18 1.380(3) . ?
C4 C3 1.413(3) . ?
C18 C19 1.384(4) . ?
C18 H18 0.95(3) . ?
C20 C19 1.390(3) . ?
C20 H20 0.90(2) . ?
C19 H19 0.91(2) . ?
C10 C11 1.382(3) . ?
C10 H10 0.94(2) . ?
C11 C12 1.380(3) . ?
C3 C2 1.369(3) . ?
C3 H3 0.97(2) . ?
C13 C12 1.384(3) . ?
C13 H13 0.93(2) . ?
C12 H12 0.95(2) . ?
C6 C1 1.369(3) . ?
C6 H6 0.99(2) . ?
C2 C1 1.406(4) . ?
C2 H2 0.96(3) . ?
C1 H1 0.98(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 C5 117.3(2) . . ?
C8 N2 C4 117.4(2) . . ?
C16 C15 C8 121.4(2) . . ?
C16 C15 C20 119.0(2) . . ?
C20 C15 C8 119.5(2) . . ?
C14 C9 C7 120.2(2) . . ?
C14 C9 C10 119.3(2) . . ?
C10 C9 C7 120.3(2) . . ?
N1 C7 C9 116.2(2) . . ?
N1 C7 C8 121.6(2) . . ?
C8 C7 C9 122.0(2) . . ?
N2 C8 C15 116.2(2) . . ?
N2 C8 C7 121.4(2) . . ?
C7 C8 C15 122.4(2) . . ?
N1 C5 C4 120.9(2) . . ?
N1 C5 C6 119.5(2) . . ?
C6 C5 C4 119.5(2) . . ?
C15 C16 H16 119.4(15) . . ?
C17 C16 C15 119.6(2) . . ?
C17 C16 H16 121.0(15) . . ?
C9 C14 H14 119.2(13) . . ?
C13 C14 C9 120.3(2) . . ?
C13 C14 H14 120.3(13) . . ?
C16 C17 Cl2 119.3(2) . . ?
C18 C17 Cl2 118.91(19) . . ?
C18 C17 C16 121.7(2) . . ?
N2 C4 C5 121.0(2) . . ?
N2 C4 C3 119.6(2) . . ?
C3 C4 C5 119.4(2) . . ?
C17 C18 C19 118.7(2) . . ?
C17 C18 H18 119.6(16) . . ?
C19 C18 H18 121.6(16) . . ?
C15 C20 H20 120.8(16) . . ?
C19 C20 C15 120.4(2) . . ?
C19 C20 H20 118.7(16) . . ?
C18 C19 C20 120.6(2) . . ?
C18 C19 H19 118.6(16) . . ?
C20 C19 H19 120.9(16) . . ?
C9 C10 H10 121.8(15) . . ?
C11 C10 C9 119.0(2) . . ?
C11 C10 H10 119.2(15) . . ?
C10 C11 Cl1 118.99(19) . . ?
C12 C11 Cl1 118.92(19) . . ?
C12 C11 C10 122.1(2) . . ?
C4 C3 H3 119.1(14) . . ?
C2 C3 C4 119.8(2) . . ?
C2 C3 H3 121.1(14) . . ?
C14 C13 C12 120.8(2) . . ?
C14 C13 H13 118.2(14) . . ?
C12 C13 H13 121.0(14) . . ?
C11 C12 C13 118.6(2) . . ?
C11 C12 H12 120.5(15) . . ?
C13 C12 H12 120.9(15) . . ?
C5 C6 H6 117.5(14) . . ?
C1 C6 C5 119.9(2) . . ?
C1 C6 H6 122.4(14) . . ?
C3 C2 C1 120.9(2) . . ?
C3 C2 H2 118.3(16) . . ?
C1 C2 H2 120.7(15) . . ?
C6 C1 C2 120.5(2) . . ?
C6 C1 H1 118.6(14) . . ?
C2 C1 H1 120.9(14) . . ?

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
Cl2 C17 C18 C19 -179.12(17) . . . . ?
Cl1 C11 C12 C13 179.86(18) . . . . ?
N1 C7 C8 N2 -7.0(3) . . . . ?
N1 C7 C8 C15 171.1(2) . . . . ?
N1 C5 C4 N2 -6.2(3) . . . . ?
N1 C5 C4 C3 174.6(2) . . . . ?
N1 C5 C6 C1 -174.9(2) . . . . ?
N2 C4 C3 C2 -178.5(2) . . . . ?
C15 C16 C17 Cl2 178.04(17) . . . . ?
C15 C16 C17 C18 -0.3(3) . . . . ?
C15 C20 C19 C18 -1.4(3) . . . . ?
C9 C7 C8 N2 168.6(2) . . . . ?
C9 C7 C8 C15 -13.3(3) . . . . ?
C9 C14 C13 C12 -0.6(4) . . . . ?
C9 C10 C11 Cl1 179.28(17) . . . . ?
C9 C10 C11 C12 -1.3(3) . . . . ?
C7 N1 C5 C4 2.4(3) . . . . ?
C7 N1 C5 C6 178.9(2) . . . . ?
C7 C9 C14 C13 -176.3(2) . . . . ?
C7 C9 C10 C11 177.2(2) . . . . ?
C8 N2 C4 C5 3.2(3) . . . . ?
C8 N2 C4 C3 -177.6(2) . . . . ?
C8 C15 C16 C17 -177.42(19) . . . . ?
C8 C15 C20 C19 178.3(2) . . . . ?
C5 N1 C7 C9 -171.90(19) . . . . ?
C5 N1 C7 C8 3.9(3) . . . . ?
C5 C4 C3 C2 0.7(3) . . . . ?
C5 C6 C1 C2 -0.2(4) . . . . ?
C16 C15 C8 N2 132.5(2) . . . . ?
C16 C15 C8 C7 -45.7(3) . . . . ?
C16 C15 C20 C19 0.3(3) . . . . ?
C16 C17 C18 C19 -0.8(3) . . . . ?
C14 C9 C7 N1 130.2(2) . . . . ?
C14 C9 C7 C8 -45.6(3) . . . . ?
C14 C9 C10 C11 1.2(3) . . . . ?
C14 C13 C12 C11 0.6(4) . . . . ?
C17 C18 C19 C20 1.6(3) . . . . ?
C4 N2 C8 C15 -175.16(19) . . . . ?
C4 N2 C8 C7 3.1(3) . . . . ?
C4 C5 C6 C1 1.6(3) . . . . ?
C4 C3 C2 C1 0.7(4) . . . . ?
C20 C15 C8 N2 -45.4(3) . . . . ?
C20 C15 C8 C7 136.4(2) . . . . ?
C20 C15 C16 C17 0.5(3) . . . . ?
C10 C9 C7 N1 -45.8(3) . . . . ?
C10 C9 C7 C8 138.4(2) . . . . ?
C10 C9 C14 C13 -0.2(3) . . . . ?
C10 C11 C12 C13 0.4(4) . . . . ?
C3 C2 C1 C6 -1.0(4) . . . . ?
C6 C5 C4 N2 177.3(2) . . . . ?
C6 C5 C4 C3 -1.9(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol/Water'
####################################################################### 
# 
# 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_rdb_1_33f2_0m
_database_code_depnum_ccdc_archive 'CCDC 2093795'
loop_
_audit_author_name
_audit_author_address
'Colin Seaton'
;University of Bradford
United Kingdom
;
_audit_update_record             
;
2021-07-01 deposited with the CCDC.	2021-09-16 downloaded from the CCDC.
;
_audit_creation_date             2021-04-15
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        2,3-bis(3-fluorophenyl)quinoxaline
_chemical_formula_moiety         'C20 H12 F2 N2'
_chemical_formula_sum            'C20 H12 F2 N2'
_chemical_formula_weight         318.32
_chemical_melting_point          408
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   12.7621(18)
_cell_length_b                   7.6916(9)
_cell_length_c                   15.439(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.230(7)
_cell_angle_gamma                90
_cell_volume                     1486.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2134
_cell_measurement_temperature    99.82
_cell_measurement_theta_max      23.06
_cell_measurement_theta_min      2.30
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.962
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6713
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.0617 before and 0.0530 after correction.
The Ratio of minimum to maximum transmission is 0.8997.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Plate
_exptl_crystal_F_000             656
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1.00 0.00 2.00 0.0930
-1.00 0.00 -2.00 0.0950
-1.00 1.00 -1.00 0.1610
1.00 -1.00 1.00 0.1110
-2.00 2.00 -1.00 0.1770
2.00 -2.00 1.00 0.1200
-1.00 0.00 2.00 0.0910
1.00 0.00 -2.00 0.0150
1.00 2.00 1.00 0.1620
-1.00 -2.00 -1.00 0.1510
-2.00 0.00 1.00 0.0640
2.00 0.00 -1.00 0.0130

_exptl_crystal_size_max          0.378
_exptl_crystal_size_mid          0.208
_exptl_crystal_size_min          0.128
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1004
_diffrn_reflns_av_unetI/netI     0.1129
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            22288
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.578
_diffrn_reflns_theta_min         2.690
_diffrn_ambient_temperature      99.82
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2366
_reflns_number_total             4452
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         4452
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1424
_refine_ls_R_factor_gt           0.0592
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0452P)²+0.0213P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1002
_refine_ls_wR_factor_ref         0.1237
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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
F2 F -0.07814(9) -0.03083(15) 0.39471(7) 0.0252(3) Uani 1 1 d . . . . .
F1 F 0.16909(11) 0.56546(17) 0.66045(8) 0.0372(4) Uani 1 1 d . . . . .
N2 N 0.34784(13) 0.0616(2) 0.32306(10) 0.0162(4) Uani 1 1 d . . . . .
N1 N 0.40832(13) 0.2810(2) 0.47079(10) 0.0170(4) Uani 1 1 d . . . . .
C8 C 0.27627(15) 0.1447(2) 0.35803(11) 0.0145(4) Uani 1 1 d . . . . .
C17 C -0.01062(15) 0.0130(2) 0.33946(12) 0.0165(4) Uani 1 1 d . . . . .
C16 C 0.09168(15) 0.0629(2) 0.37708(13) 0.0163(4) Uani 1 1 d . . . . .
C9 C 0.23057(15) 0.3854(2) 0.45943(12) 0.0148(4) Uani 1 1 d . . . . .
C5 C 0.48249(15) 0.1878(3) 0.43778(12) 0.0160(4) Uani 1 1 d . . . . .
C7 C 0.30743(15) 0.2647(2) 0.43025(12) 0.0148(4) Uani 1 1 d . . . . .
C15 C 0.16217(15) 0.1018(2) 0.32104(12) 0.0147(4) Uani 1 1 d . . . . .
C4 C 0.45332(15) 0.0854(2) 0.36078(12) 0.0156(4) Uani 1 1 d . . . . .
C20 C 0.12662(16) 0.0928(3) 0.22972(12) 0.0166(4) Uani 1 1 d . . . . .
C10 C 0.23432(16) 0.4148(3) 0.54947(13) 0.0192(4) Uani 1 1 d . . . . .
C18 C -0.04800(16) 0.0031(3) 0.24988(13) 0.0185(4) Uani 1 1 d . . . . .
C19 C 0.02180(16) 0.0455(3) 0.19468(13) 0.0191(5) Uani 1 1 d . . . . .
C14 C 0.15975(16) 0.4811(3) 0.39679(13) 0.0178(4) Uani 1 1 d . . . . .
C3 C 0.53277(16) 0.0030(3) 0.32344(13) 0.0196(4) Uani 1 1 d . . . . .
C6 C 0.59137(16) 0.2006(3) 0.47820(13) 0.0200(5) Uani 1 1 d . . . . .
C13 C 0.09353(16) 0.6039(3) 0.42337(14) 0.0215(5) Uani 1 1 d . . . . .
C11 C 0.16646(17) 0.5371(3) 0.57266(13) 0.0227(5) Uani 1 1 d . . . . .
C1 C 0.66728(17) 0.1186(3) 0.44197(14) 0.0228(5) Uani 1 1 d . . . . .
C2 C 0.63789(17) 0.0202(3) 0.36315(14) 0.0215(5) Uani 1 1 d . . . . .
C12 C 0.09575(17) 0.6334(3) 0.51271(15) 0.0242(5) Uani 1 1 d . . . . .
H2 H 0.6946(16) -0.033(3) 0.3341(13) 0.021(5) Uiso 1 1 d . . . . .
H18 H -0.1224(17) -0.034(2) 0.2256(13) 0.021(5) Uiso 1 1 d . . . . .
H19 H 0.0000(16) 0.042(2) 0.1313(13) 0.019(5) Uiso 1 1 d . . . . .
H12 H 0.0474(16) 0.717(3) 0.5337(13) 0.020(5) Uiso 1 1 d . . . . .
H13 H 0.0417(15) 0.668(2) 0.3802(11) 0.010(5) Uiso 1 1 d . . . . .
H3 H 0.5115(17) -0.067(3) 0.2696(14) 0.030(6) Uiso 1 1 d . . . . .
H10 H 0.2834(16) 0.350(3) 0.5953(13) 0.024(6) Uiso 1 1 d . . . . .
H1 H 0.7449(18) 0.133(3) 0.4715(13) 0.031(6) Uiso 1 1 d . . . . .
H20 H 0.1757(16) 0.124(3) 0.1902(13) 0.023(6) Uiso 1 1 d . . . . .
H6 H 0.6109(16) 0.275(3) 0.5344(14) 0.025(6) Uiso 1 1 d . . . . .
H16 H 0.1113(15) 0.065(2) 0.4406(13) 0.015(5) Uiso 1 1 d . . . . .
H14 H 0.1581(16) 0.464(3) 0.3348(14) 0.022(6) Uiso 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
F2 C17 1.367(2) . ?
F1 C11 1.367(2) . ?
N2 C8 1.314(2) . ?
N2 C4 1.371(2) . ?
N1 C5 1.363(2) . ?
N1 C7 1.323(2) . ?
C8 C7 1.443(3) . ?
C8 C15 1.494(3) . ?
C17 C16 1.376(3) . ?
C17 C18 1.374(3) . ?
C16 C15 1.397(3) . ?
C16 H16 0.964(19) . ?
C9 C7 1.483(3) . ?
C9 C10 1.400(3) . ?
C9 C14 1.398(3) . ?
C5 C4 1.414(3) . ?
C5 C6 1.411(3) . ?
C15 C20 1.396(3) . ?
C4 C3 1.411(3) . ?
C20 C19 1.390(3) . ?
C20 H20 0.98(2) . ?
C10 C11 1.372(3) . ?
C10 H10 0.98(2) . ?
C18 C19 1.386(3) . ?
C18 H18 0.99(2) . ?
C19 H19 0.96(2) . ?
C14 C13 1.382(3) . ?
C14 H14 0.96(2) . ?
C3 C2 1.369(3) . ?
C3 H3 0.98(2) . ?
C6 C1 1.364(3) . ?
C6 H6 1.03(2) . ?
C13 C12 1.393(3) . ?
C13 H13 0.978(18) . ?
C11 C12 1.376(3) . ?
C1 C2 1.420(3) . ?
C1 H1 1.01(2) . ?
C2 H2 1.01(2) . ?
C12 H12 0.99(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N2 C4 117.64(16) . . ?
C7 N1 C5 117.15(16) . . ?
N2 C8 C7 121.33(17) . . ?
N2 C8 C15 116.06(17) . . ?
C7 C8 C15 122.56(17) . . ?
F2 C17 C16 117.82(17) . . ?
F2 C17 C18 118.46(17) . . ?
C18 C17 C16 123.71(19) . . ?
C17 C16 C15 118.09(18) . . ?
C17 C16 H16 118.2(12) . . ?
C15 C16 H16 123.7(12) . . ?
C10 C9 C7 120.42(17) . . ?
C14 C9 C7 119.75(17) . . ?
C14 C9 C10 119.62(19) . . ?
N1 C5 C4 121.26(17) . . ?
N1 C5 C6 119.60(18) . . ?
C6 C5 C4 119.06(18) . . ?
N1 C7 C8 121.49(18) . . ?
N1 C7 C9 115.95(16) . . ?
C8 C7 C9 122.43(16) . . ?
C16 C15 C8 120.53(17) . . ?
C20 C15 C8 119.86(18) . . ?
C20 C15 C16 119.55(18) . . ?
N2 C4 C5 120.50(17) . . ?
N2 C4 C3 119.39(17) . . ?
C3 C4 C5 120.09(18) . . ?
C15 C20 H20 119.5(11) . . ?
C19 C20 C15 120.32(19) . . ?
C19 C20 H20 120.1(11) . . ?
C9 C10 H10 121.8(12) . . ?
C11 C10 C9 117.95(19) . . ?
C11 C10 H10 120.3(12) . . ?
C17 C18 C19 117.82(18) . . ?
C17 C18 H18 121.0(11) . . ?
C19 C18 H18 121.2(11) . . ?
C20 C19 H19 117.9(12) . . ?
C18 C19 C20 120.48(18) . . ?
C18 C19 H19 121.6(12) . . ?
C9 C14 H14 120.2(12) . . ?
C13 C14 C9 120.32(19) . . ?
C13 C14 H14 119.5(12) . . ?
C4 C3 H3 119.3(13) . . ?
C2 C3 C4 119.6(2) . . ?
C2 C3 H3 121.2(13) . . ?
C5 C6 H6 117.9(12) . . ?
C1 C6 C5 120.2(2) . . ?
C1 C6 H6 121.8(12) . . ?
C14 C13 C12 120.7(2) . . ?
C14 C13 H13 121.1(11) . . ?
C12 C13 H13 118.2(11) . . ?
F1 C11 C10 118.24(19) . . ?
F1 C11 C12 117.86(19) . . ?
C10 C11 C12 123.91(19) . . ?
C6 C1 C2 120.5(2) . . ?
C6 C1 H1 118.5(12) . . ?
C2 C1 H1 121.0(12) . . ?
C3 C2 C1 120.5(2) . . ?
C3 C2 H2 119.2(12) . . ?
C1 C2 H2 120.2(12) . . ?
C13 C12 H12 122.5(11) . . ?
C11 C12 C13 117.5(2) . . ?
C11 C12 H12 119.9(11) . . ?

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
F2 C17 C16 C15 177.73(16) . . . . ?
F2 C17 C18 C19 -179.10(18) . . . . ?
F1 C11 C12 C13 179.97(18) . . . . ?
N2 C8 C7 N1 -7.9(3) . . . . ?
N2 C8 C7 C9 167.73(17) . . . . ?
N2 C8 C15 C16 131.26(19) . . . . ?
N2 C8 C15 C20 -45.9(2) . . . . ?
N2 C4 C3 C2 -177.12(18) . . . . ?
N1 C5 C4 N2 -7.5(3) . . . . ?
N1 C5 C4 C3 174.21(18) . . . . ?
N1 C5 C6 C1 -175.02(18) . . . . ?
C8 N2 C4 C5 3.7(3) . . . . ?
C8 N2 C4 C3 -177.92(17) . . . . ?
C8 C15 C20 C19 177.16(18) . . . . ?
C17 C16 C15 C8 -175.71(18) . . . . ?
C17 C16 C15 C20 1.4(3) . . . . ?
C17 C18 C19 C20 1.3(3) . . . . ?
C16 C17 C18 C19 0.2(3) . . . . ?
C16 C15 C20 C19 0.0(3) . . . . ?
C9 C10 C11 F1 179.46(17) . . . . ?
C9 C10 C11 C12 -0.6(3) . . . . ?
C9 C14 C13 C12 -0.4(3) . . . . ?
C5 N1 C7 C8 4.2(3) . . . . ?
C5 N1 C7 C9 -171.77(16) . . . . ?
C5 C4 C3 C2 1.2(3) . . . . ?
C5 C6 C1 C2 0.3(3) . . . . ?
C7 N1 C5 C4 3.2(3) . . . . ?
C7 N1 C5 C6 179.79(17) . . . . ?
C7 C8 C15 C16 -46.3(3) . . . . ?
C7 C8 C15 C20 136.56(19) . . . . ?
C7 C9 C10 C11 175.37(18) . . . . ?
C7 C9 C14 C13 -174.90(18) . . . . ?
C15 C8 C7 N1 169.53(17) . . . . ?
C15 C8 C7 C9 -14.8(3) . . . . ?
C15 C20 C19 C18 -1.4(3) . . . . ?
C4 N2 C8 C7 3.6(3) . . . . ?
C4 N2 C8 C15 -174.06(16) . . . . ?
C4 C5 C6 C1 1.7(3) . . . . ?
C4 C3 C2 C1 0.7(3) . . . . ?
C10 C9 C7 N1 -45.0(3) . . . . ?
C10 C9 C7 C8 139.14(19) . . . . ?
C10 C9 C14 C13 -0.1(3) . . . . ?
C10 C11 C12 C13 0.0(3) . . . . ?
C18 C17 C16 C15 -1.5(3) . . . . ?
C14 C9 C7 N1 129.72(19) . . . . ?
C14 C9 C7 C8 -46.2(3) . . . . ?
C14 C9 C10 C11 0.7(3) . . . . ?
C14 C13 C12 C11 0.5(3) . . . . ?
C6 C5 C4 N2 175.92(17) . . . . ?
C6 C5 C4 C3 -2.4(3) . . . . ?
C6 C1 C2 C3 -1.5(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol/water'
####################################################################### 
# 
# 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_rdb_1_33me_0m
_database_code_depnum_ccdc_archive 'CCDC 2093797'
loop_
_audit_author_name
_audit_author_address
'Colin Seaton'
;University of Bradford
United Kingdom
;

_audit_update_record             
;
2021-07-01 deposited with the CCDC.	2021-09-16 downloaded from the CCDC.
;
_audit_creation_date             2021-04-15
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        2,3-di-m-tolylquinoxaline
_chemical_formula_moiety         'C22 H18 N2'
_chemical_formula_sum            'C22 H18 N2'
_chemical_formula_weight         310.38
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   12.313(4)
_cell_length_b                   7.563(2)
_cell_length_c                   17.916(5)
_cell_angle_alpha                90
_cell_angle_beta                 102.333(11)
_cell_angle_gamma                90
_cell_volume                     1630.0(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2615
_cell_measurement_temperature    99.78
_cell_measurement_theta_max      25.57
_cell_measurement_theta_min      2.33
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5537
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.1005 before and 0.0788 after correction.
The Ratio of minimum to maximum transmission is 0.7421.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0977
_diffrn_reflns_av_unetI/netI     0.0973
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            22160
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.550
_diffrn_reflns_theta_min         2.934
_diffrn_ambient_temperature      99.78
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2769
_reflns_number_total             4920
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.749
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.105
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4920
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1509
_refine_ls_R_factor_gt           0.0850
_refine_ls_restrained_S_all      1.036
_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)+(0.1350P)²+0.0296P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2017
_refine_ls_wR_factor_ref         0.2449
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.25323(16) 0.7211(3) 0.65503(12) 0.0185(4) Uani 1 1 d . . . . .
N2 N 0.44372(16) 0.5741(3) 0.61539(11) 0.0180(4) Uani 1 1 d . . . . .
C8 C 0.43208(18) 0.5762(3) 0.68683(14) 0.0175(5) Uani 1 1 d . . . . .
C5 C 0.26243(18) 0.7132(3) 0.58046(14) 0.0177(5) Uani 1 1 d . . . . .
C7 C 0.33659(18) 0.6606(3) 0.70739(14) 0.0168(5) Uani 1 1 d . . . . .
C16 C 0.52023(18) 0.4866(3) 0.74442(14) 0.0174(5) Uani 1 1 d . . . . .
C18 C 0.71695(18) 0.4241(3) 0.79302(14) 0.0188(5) Uani 1 1 d . . . . .
C17 C 0.63191(19) 0.5045(3) 0.73977(14) 0.0188(5) Uani 1 1 d . . . . .
C6 C 0.1767(2) 0.7830(3) 0.52323(15) 0.0216(5) Uani 1 1 d . . . . .
C4 C 0.35997(18) 0.6443(3) 0.56079(14) 0.0179(5) Uani 1 1 d . . . . .
C3 C 0.3682(2) 0.6441(4) 0.48341(15) 0.0220(5) Uani 1 1 d . . . . .
C9 C 0.32782(18) 0.6945(3) 0.78762(14) 0.0177(5) Uani 1 1 d . . . . .
C10 C 0.2316(2) 0.6474(3) 0.81215(15) 0.0199(5) Uani 1 1 d . . . . .
C11 C 0.2184(2) 0.6884(3) 0.88565(15) 0.0218(5) Uani 1 1 d . . . . .
C21 C 0.49337(19) 0.3798(3) 0.80147(14) 0.0193(5) Uani 1 1 d . . . . .
C20 C 0.5774(2) 0.2947(4) 0.85284(14) 0.0219(5) Uani 1 1 d . . . . .
C2 C 0.2831(2) 0.7117(4) 0.42884(15) 0.0239(6) Uani 1 1 d . . . . .
C12 C 0.3030(2) 0.7805(4) 0.93390(15) 0.0234(6) Uani 1 1 d . . . . .
C14 C 0.4117(2) 0.7868(3) 0.83705(14) 0.0206(5) Uani 1 1 d . . . . .
C19 C 0.6881(2) 0.3184(4) 0.84942(15) 0.0221(5) Uani 1 1 d . . . . .
C1 C 0.1871(2) 0.7826(4) 0.44876(15) 0.0232(6) Uani 1 1 d . . . . .
C13 C 0.3986(2) 0.8297(4) 0.90977(15) 0.0242(6) Uani 1 1 d . . . . .
C22 C 0.8373(2) 0.4533(4) 0.78889(18) 0.0250(6) Uani 1 1 d . . . . .
C15 C 0.1144(2) 0.6331(4) 0.91154(19) 0.0307(7) Uani 1 1 d . . . . .
H14 H 0.479(2) 0.822(4) 0.8204(14) 0.016(6) Uiso 1 1 d . . . . .
H2 H 0.292(2) 0.718(4) 0.3764(15) 0.016(7) Uiso 1 1 d . . . . .
H3 H 0.436(2) 0.598(4) 0.4678(16) 0.034(8) Uiso 1 1 d . . . . .
H6 H 0.110(2) 0.826(4) 0.5377(15) 0.023(7) Uiso 1 1 d . . . . .
H21 H 0.416(2) 0.369(4) 0.8062(16) 0.027(7) Uiso 1 1 d . . . . .
H19 H 0.751(3) 0.266(4) 0.8900(17) 0.032(8) Uiso 1 1 d . . . . .
H1 H 0.128(2) 0.829(4) 0.4065(15) 0.018(7) Uiso 1 1 d . . . . .
H13 H 0.459(2) 0.897(4) 0.9458(16) 0.026(8) Uiso 1 1 d . . . . .
H17 H 0.650(2) 0.575(4) 0.6977(15) 0.020(7) Uiso 1 1 d . . . . .
H10 H 0.173(3) 0.592(5) 0.7781(17) 0.036(9) Uiso 1 1 d . . . . .
H22A H 0.890(3) 0.413(5) 0.837(2) 0.052(10) Uiso 1 1 d . . . . .
H22B H 0.856(3) 0.408(6) 0.743(2) 0.059(11) Uiso 1 1 d . . . . .
H20 H 0.555(2) 0.215(4) 0.8940(15) 0.019(7) Uiso 1 1 d . . . . .
H22C H 0.860(3) 0.589(5) 0.7859(19) 0.051(10) Uiso 1 1 d . . . . .
H12 H 0.295(2) 0.813(4) 0.9881(17) 0.034(8) Uiso 1 1 d . . . . .
H15A H 0.128(3) 0.593(7) 0.964(2) 0.080(15) Uiso 1 1 d . . . . .
H15B H 0.060(4) 0.720(7) 0.901(3) 0.093(17) Uiso 1 1 d . . . . .
H15C H 0.080(3) 0.521(6) 0.885(2) 0.069(13) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C5 1.366(3) . ?
N1 C7 1.316(3) . ?
N2 C8 1.318(3) . ?
N2 C4 1.368(3) . ?
C8 C7 1.453(3) . ?
C8 C16 1.491(3) . ?
C5 C6 1.408(3) . ?
C5 C4 1.421(3) . ?
C7 C9 1.487(3) . ?
C16 C17 1.402(3) . ?
C16 C21 1.397(3) . ?
C18 C17 1.396(3) . ?
C18 C19 1.393(3) . ?
C18 C22 1.516(3) . ?
C17 H17 0.99(3) . ?
C6 C1 1.367(4) . ?
C6 H6 0.97(3) . ?
C4 C3 1.411(3) . ?
C3 C2 1.370(4) . ?
C3 H3 1.00(3) . ?
C9 C10 1.395(3) . ?
C9 C14 1.395(3) . ?
C10 C11 1.396(3) . ?
C10 H10 0.94(3) . ?
C11 C12 1.390(4) . ?
C11 C15 1.511(4) . ?
C21 C20 1.388(4) . ?
C21 H21 0.98(3) . ?
C20 C19 1.389(3) . ?
C20 H20 1.03(3) . ?
C2 C1 1.412(4) . ?
C2 H2 0.97(3) . ?
C12 C13 1.389(4) . ?
C12 H12 1.03(3) . ?
C14 C13 1.385(3) . ?
C14 H14 0.98(3) . ?
C19 H19 1.02(3) . ?
C1 H1 1.00(3) . ?
C13 H13 1.01(3) . ?
C22 H22A 1.00(4) . ?
C22 H22B 0.96(4) . ?
C22 H22C 1.07(4) . ?
C15 H15A 0.96(4) . ?
C15 H15B 0.93(5) . ?
C15 H15C 1.02(5) . ?

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 N1 C5 117.8(2) . . ?
C8 N2 C4 117.90(19) . . ?
N2 C8 C7 120.9(2) . . ?
N2 C8 C16 116.9(2) . . ?
C7 C8 C16 122.2(2) . . ?
N1 C5 C6 119.3(2) . . ?
N1 C5 C4 120.6(2) . . ?
C6 C5 C4 119.9(2) . . ?
N1 C7 C8 121.5(2) . . ?
N1 C7 C9 115.0(2) . . ?
C8 C7 C9 123.4(2) . . ?
C17 C16 C8 119.6(2) . . ?
C21 C16 C8 121.2(2) . . ?
C21 C16 C17 119.2(2) . . ?
C17 C18 C22 120.1(2) . . ?
C19 C18 C17 118.4(2) . . ?
C19 C18 C22 121.5(2) . . ?
C16 C17 H17 119.0(15) . . ?
C18 C17 C16 121.3(2) . . ?
C18 C17 H17 119.7(15) . . ?
C5 C6 H6 118.5(16) . . ?
C1 C6 C5 119.9(2) . . ?
C1 C6 H6 121.6(16) . . ?
N2 C4 C5 120.9(2) . . ?
N2 C4 C3 120.1(2) . . ?
C3 C4 C5 119.0(2) . . ?
C4 C3 H3 121.1(17) . . ?
C2 C3 C4 119.8(2) . . ?
C2 C3 H3 119.2(17) . . ?
C10 C9 C7 120.2(2) . . ?
C10 C9 C14 119.4(2) . . ?
C14 C9 C7 120.2(2) . . ?
C9 C10 C11 121.2(2) . . ?
C9 C10 H10 119.9(18) . . ?
C11 C10 H10 118.8(18) . . ?
C10 C11 C15 120.3(2) . . ?
C12 C11 C10 118.4(2) . . ?
C12 C11 C15 121.3(2) . . ?
C16 C21 H21 119.9(18) . . ?
C20 C21 C16 119.6(2) . . ?
C20 C21 H21 120.5(18) . . ?
C21 C20 C19 120.7(2) . . ?
C21 C20 H20 118.1(14) . . ?
C19 C20 H20 121.2(14) . . ?
C3 C2 C1 121.0(2) . . ?
C3 C2 H2 119.0(15) . . ?
C1 C2 H2 119.9(15) . . ?
C11 C12 H12 120.0(17) . . ?
C13 C12 C11 120.9(2) . . ?
C13 C12 H12 119.2(17) . . ?
C9 C14 H14 120.2(15) . . ?
C13 C14 C9 119.7(2) . . ?
C13 C14 H14 120.1(15) . . ?
C18 C19 H19 118.0(18) . . ?
C20 C19 C18 120.7(2) . . ?
C20 C19 H19 121.2(17) . . ?
C6 C1 C2 120.4(2) . . ?
C6 C1 H1 122.4(15) . . ?
C2 C1 H1 117.3(15) . . ?
C12 C13 H13 119.6(16) . . ?
C14 C13 C12 120.4(2) . . ?
C14 C13 H13 120.0(16) . . ?
C18 C22 H22A 112(2) . . ?
C18 C22 H22B 114(2) . . ?
C18 C22 H22C 114.3(19) . . ?
H22A C22 H22B 113(3) . . ?
H22A C22 H22C 102(3) . . ?
H22B C22 H22C 101(3) . . ?
C11 C15 H15A 114(3) . . ?
C11 C15 H15B 111(3) . . ?
C11 C15 H15C 113(2) . . ?
H15A C15 H15B 113(4) . . ?
H15A C15 H15C 99(4) . . ?
H15B C15 H15C 106(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
N1 C5 C6 C1 177.2(2) . . . . ?
N1 C5 C4 N2 4.2(4) . . . . ?
N1 C5 C4 C3 -177.7(2) . . . . ?
N1 C7 C9 C10 51.8(3) . . . . ?
N1 C7 C9 C14 -122.8(2) . . . . ?
N2 C8 C7 N1 7.2(4) . . . . ?
N2 C8 C7 C9 -169.2(2) . . . . ?
N2 C8 C16 C17 40.3(3) . . . . ?
N2 C8 C16 C21 -137.4(2) . . . . ?
N2 C4 C3 C2 178.8(2) . . . . ?
C8 N2 C4 C5 -1.5(3) . . . . ?
C8 N2 C4 C3 -179.6(2) . . . . ?
C8 C7 C9 C10 -131.5(3) . . . . ?
C8 C7 C9 C14 53.8(3) . . . . ?
C8 C16 C17 C18 179.4(2) . . . . ?
C8 C16 C21 C20 178.2(2) . . . . ?
C5 N1 C7 C8 -4.4(3) . . . . ?
C5 N1 C7 C9 172.3(2) . . . . ?
C5 C6 C1 C2 0.3(4) . . . . ?
C5 C4 C3 C2 0.7(4) . . . . ?
C7 N1 C5 C6 -177.5(2) . . . . ?
C7 N1 C5 C4 -1.0(3) . . . . ?
C7 C8 C16 C17 -140.4(2) . . . . ?
C7 C8 C16 C21 42.0(3) . . . . ?
C7 C9 C10 C11 -175.7(2) . . . . ?
C7 C9 C14 C13 175.0(2) . . . . ?
C16 C8 C7 N1 -172.1(2) . . . . ?
C16 C8 C7 C9 11.5(4) . . . . ?
C16 C21 C20 C19 1.8(4) . . . . ?
C17 C16 C21 C20 0.6(4) . . . . ?
C17 C18 C19 C20 -0.4(4) . . . . ?
C6 C5 C4 N2 -179.3(2) . . . . ?
C6 C5 C4 C3 -1.2(4) . . . . ?
C4 N2 C8 C7 -3.9(3) . . . . ?
C4 N2 C8 C16 175.4(2) . . . . ?
C4 C5 C6 C1 0.7(4) . . . . ?
C4 C3 C2 C1 0.3(4) . . . . ?
C3 C2 C1 C6 -0.8(4) . . . . ?
C9 C10 C11 C12 1.0(4) . . . . ?
C9 C10 C11 C15 -178.9(3) . . . . ?
C9 C14 C13 C12 0.4(4) . . . . ?
C10 C9 C14 C13 0.3(4) . . . . ?
C10 C11 C12 C13 -0.3(4) . . . . ?
C11 C12 C13 C14 -0.4(4) . . . . ?
C21 C16 C17 C18 -2.9(4) . . . . ?
C21 C20 C19 C18 -1.9(4) . . . . ?
C14 C9 C10 C11 -1.0(4) . . . . ?
C19 C18 C17 C16 2.8(4) . . . . ?
C22 C18 C17 C16 -176.9(2) . . . . ?
C22 C18 C19 C20 179.3(2) . . . . ?
C15 C11 C12 C13 179.6(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol/Water'
