# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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 
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# 
#######################################################################

data_a171020b_twin1_hklf5
_database_code_depnum_ccdc_archive 'CCDC 1837163'
_audit_update_record             
;
2018-04-16 deposited with the CCDC.
2018-07-31 downloaded from the CCDC.
;
_audit_creation_date             2017-10-30
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H22 N4 O6'
_chemical_formula_sum            'C25 H22 N4 O6'
_chemical_formula_weight         474.46
_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                   7.6583(9)
_cell_length_b                   11.7333(12)
_cell_length_c                   25.007(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.687(11)
_cell_angle_gamma                90
_cell_volume                     2236.0(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1640
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.3700
_cell_measurement_theta_min      4.0320
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76154
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0693
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            4249
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.010
_diffrn_reflns_theta_max         25.010
_diffrn_reflns_theta_min         3.356
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2740
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -9.00  85.00   1.00    5.26    --   11.08  38.00 -60.00   94
  2  ω     53.00  80.00   1.00    5.26    --   11.08 178.00 150.00   27
  3  ω    -21.00  38.00   1.00    5.26    --   11.08 -57.00 -60.00   59
  4  ω    -10.00  32.00   1.00    5.26    --   11.08 -57.00 150.00   42
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0554531000
_diffrn_orient_matrix_UB_12      0.0183585000
_diffrn_orient_matrix_UB_13      -0.0228031000
_diffrn_orient_matrix_UB_21      0.0690143000
_diffrn_orient_matrix_UB_22      -0.0090651000
_diffrn_orient_matrix_UB_23      -0.0164326000
_diffrn_orient_matrix_UB_31      -0.0287747000
_diffrn_orient_matrix_UB_32      -0.0568814000
_diffrn_orient_matrix_UB_33      -0.0047286000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3363
_reflns_number_total             4249
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         4249
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0527
_refine_ls_restrained_S_all      1.031
_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)+(0.0677P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1199
_refine_ls_wR_factor_ref         0.1239
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.6299(14)
 0.3701(14)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C8(H8)
3.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C19(H19A,H19B)
3.c Aromatic/amide H refined with riding coordinates:
 N3(H3), C2(H2), C3(H3A), C5(H5), C6(H6), C14(H14), C15(H15), C16(H16),
 C17(H17), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
3.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_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 0.4116(4) 0.93597(18) 0.70332(9) 0.0229(6) Uani 1 1 d . . . . .
O2 O 0.3937(4) 0.80800(19) 0.76454(9) 0.0237(6) Uani 1 1 d . . . . .
O3 O 0.7727(4) 0.59010(19) 0.50705(9) 0.0222(6) Uani 1 1 d . . . . .
O4 O 0.9551(3) 0.16223(19) 0.54015(10) 0.0228(6) Uani 1 1 d . . . . .
O5 O 0.6929(3) 0.11664(18) 0.49737(9) 0.0202(6) Uani 1 1 d . . . . .
O6 O 1.0276(3) 0.49350(19) 0.64796(10) 0.0252(6) Uani 1 1 d . . . . .
N1 N 0.7119(4) 0.5116(2) 0.58974(10) 0.0132(7) Uani 1 1 d . . . . .
N2 N 0.4290(4) 0.8374(2) 0.71956(11) 0.0148(7) Uani 1 1 d . . . . .
N3 N 0.9795(4) 0.3147(2) 0.67656(10) 0.0171(7) Uani 1 1 d . . . . .
H3 H 0.9160 0.2544 0.6715 0.020 Uiso 1 1 calc R . . . .
N4 N 0.6886(4) 0.2080(2) 0.63006(10) 0.0142(7) Uani 1 1 d . . . . .
C1 C 0.4971(5) 0.7525(3) 0.68525(12) 0.0115(7) Uani 1 1 d . . . . .
C2 C 0.5336(5) 0.6440(3) 0.70558(13) 0.0158(8) Uani 1 1 d . . . . .
H2 H 0.5094 0.6251 0.7402 0.019 Uiso 1 1 calc R . . . .
C3 C 0.6057(5) 0.5654(3) 0.67373(13) 0.0146(8) Uani 1 1 d . . . . .
H3A H 0.6309 0.4925 0.6869 0.018 Uiso 1 1 calc R . . . .
C4 C 0.6418(5) 0.5937(3) 0.62169(12) 0.0124(8) Uani 1 1 d . . . . .
C5 C 0.6037(5) 0.7033(2) 0.60150(13) 0.0127(8) Uani 1 1 d . . . . .
H5 H 0.6262 0.7224 0.5667 0.015 Uiso 1 1 calc R . . . .
C6 C 0.5324(5) 0.7824(3) 0.63373(13) 0.0146(8) Uani 1 1 d . . . . .
H6 H 0.5080 0.8557 0.6210 0.018 Uiso 1 1 calc R . . . .
C7 C 0.7760(5) 0.5159(3) 0.54037(13) 0.0167(8) Uani 1 1 d . . . . .
C8 C 0.8473(5) 0.3947(3) 0.54561(12) 0.0157(8) Uani 1 1 d . . . . .
H8 H 0.9756 0.3926 0.5474 0.019 Uiso 1 1 calc R . . . .
C9 C 0.7791(5) 0.3959(3) 0.60359(13) 0.0135(8) Uani 1 1 d . . . . .
C10 C 0.7619(5) 0.3113(3) 0.50449(12) 0.0174(8) Uani 1 1 d . . . . .
H10A H 0.6354 0.3167 0.5040 0.021 Uiso 1 1 calc R . . . .
H10B H 0.7929 0.3320 0.4691 0.021 Uiso 1 1 calc R . . . .
C11 C 0.8180(5) 0.1902(3) 0.51657(13) 0.0161(8) Uani 1 1 d . . . . .
C12 C 0.7345(5) -0.0025(3) 0.50764(16) 0.0260(9) Uani 1 1 d . . . . .
H12A H 0.6398 -0.0491 0.4921 0.039 Uiso 1 1 calc GR . . . .
H12B H 0.7512 -0.0154 0.5457 0.039 Uiso 1 1 calc GR . . . .
H12C H 0.8401 -0.0217 0.4920 0.039 Uiso 1 1 calc GR . . . .
C13 C 0.6346(5) 0.3113(3) 0.61174(12) 0.0121(8) Uani 1 1 d . . . . .
C14 C 0.4600(5) 0.3360(3) 0.59717(13) 0.0173(8) Uani 1 1 d . . . . .
H14 H 0.4269 0.4082 0.5845 0.021 Uiso 1 1 calc R . . . .
C15 C 0.3352(5) 0.2528(3) 0.60156(13) 0.0205(9) Uani 1 1 d . . . . .
H15 H 0.2173 0.2675 0.5914 0.025 Uiso 1 1 calc R . . . .
C16 C 0.3893(5) 0.1466(3) 0.62144(13) 0.0177(8) Uani 1 1 d . . . . .
H16 H 0.3085 0.0888 0.6254 0.021 Uiso 1 1 calc R . . . .
C17 C 0.5652(5) 0.1293(3) 0.63503(13) 0.0160(8) Uani 1 1 d . . . . .
H17 H 0.6008 0.0583 0.6486 0.019 Uiso 1 1 calc R . . . .
C18 C 0.9397(5) 0.4059(3) 0.64615(13) 0.0149(8) Uani 1 1 d . . . . .
C19 C 1.1272(5) 0.3134(3) 0.71812(13) 0.0217(9) Uani 1 1 d . . . . .
H19A H 1.2126 0.3697 0.7094 0.026 Uiso 1 1 calc R . . . .
H19B H 1.1831 0.2392 0.7184 0.026 Uiso 1 1 calc R . . . .
C20 C 1.0730(5) 0.3381(3) 0.77330(13) 0.0167(8) Uani 1 1 d . . . . .
C21 C 1.0817(5) 0.4477(3) 0.79382(14) 0.0206(8) Uani 1 1 d . . . . .
H21 H 1.1238 0.5064 0.7737 0.025 Uiso 1 1 calc R . . . .
C22 C 1.0285(5) 0.4710(3) 0.84390(14) 0.0226(9) Uani 1 1 d . . . . .
H22 H 1.0346 0.5449 0.8574 0.027 Uiso 1 1 calc R . . . .
C23 C 0.9660(5) 0.3833(3) 0.87392(14) 0.0219(9) Uani 1 1 d . . . . .
H23 H 0.9290 0.3986 0.9075 0.026 Uiso 1 1 calc R . . . .
C24 C 0.9586(5) 0.2733(3) 0.85420(13) 0.0200(8) Uani 1 1 d . . . . .
H24 H 0.9170 0.2145 0.8744 0.024 Uiso 1 1 calc R . . . .
C25 C 1.0133(5) 0.2514(3) 0.80420(13) 0.0180(8) Uani 1 1 d . . . . .
H25 H 1.0099 0.1771 0.7911 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
O1 N2 1.229(3) . ?
O2 N2 1.232(3) . ?
O3 C7 1.203(4) . ?
O4 C11 1.198(4) . ?
O5 C11 1.343(4) . ?
O5 C12 1.451(4) . ?
O6 C18 1.227(4) . ?
N1 C4 1.393(4) . ?
N1 C7 1.374(4) . ?
N1 C9 1.481(4) . ?
N2 C1 1.445(4) . ?
N3 H3 0.8600 . ?
N3 C18 1.330(4) . ?
N3 C19 1.458(4) . ?
N4 C13 1.347(4) . ?
N4 C17 1.335(4) . ?
C1 C2 1.389(4) . ?
C1 C6 1.388(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.370(4) . ?
C3 H3A 0.9300 . ?
C3 C4 1.397(4) . ?
C4 C5 1.402(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.377(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.524(4) . ?
C8 H8 0.9800 . ?
C8 C9 1.589(4) . ?
C8 C10 1.520(4) . ?
C9 C13 1.515(5) . ?
C9 C18 1.549(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.506(4) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.382(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.378(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.390(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.371(5) . ?
C17 H17 0.9300 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.508(5) . ?
C20 C21 1.384(5) . ?
C20 C25 1.383(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.382(5) . ?
C22 H22 0.9300 . ?
C22 C23 1.387(5) . ?
C23 H23 0.9300 . ?
C23 C24 1.380(5) . ?
C24 H24 0.9300 . ?
C24 C25 1.382(5) . ?
C25 H25 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O5 C12 114.8(3) . . ?
C4 N1 C9 130.2(3) . . ?
C7 N1 C4 133.0(3) . . ?
C7 N1 C9 95.6(2) . . ?
O1 N2 O2 122.6(3) . . ?
O1 N2 C1 119.1(3) . . ?
O2 N2 C1 118.3(2) . . ?
C18 N3 H3 118.9 . . ?
C18 N3 C19 122.2(3) . . ?
C19 N3 H3 118.9 . . ?
C17 N4 C13 117.3(3) . . ?
C2 C1 N2 119.0(3) . . ?
C6 C1 N2 119.5(3) . . ?
C6 C1 C2 121.4(3) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 C1 118.9(3) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 H3A 119.7 . . ?
C2 C3 C4 120.6(3) . . ?
C4 C3 H3A 119.7 . . ?
N1 C4 C3 119.5(3) . . ?
N1 C4 C5 120.4(3) . . ?
C3 C4 C5 120.0(3) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 C4 119.2(3) . . ?
C6 C5 H5 120.4 . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 119.9(3) . . ?
C5 C6 H6 120.0 . . ?
O3 C7 N1 131.6(3) . . ?
O3 C7 C8 135.8(3) . . ?
N1 C7 C8 92.6(2) . . ?
C7 C8 H8 112.1 . . ?
C7 C8 C9 85.6(2) . . ?
C9 C8 H8 112.1 . . ?
C10 C8 C7 114.6(3) . . ?
C10 C8 H8 112.1 . . ?
C10 C8 C9 117.7(3) . . ?
N1 C9 C8 86.1(2) . . ?
N1 C9 C13 112.9(3) . . ?
N1 C9 C18 109.0(3) . . ?
C13 C9 C8 115.3(3) . . ?
C13 C9 C18 119.9(3) . . ?
C18 C9 C8 108.5(3) . . ?
C8 C10 H10A 109.2 . . ?
C8 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C11 C10 C8 112.1(3) . . ?
C11 C10 H10A 109.2 . . ?
C11 C10 H10B 109.2 . . ?
O4 C11 O5 124.0(3) . . ?
O4 C11 C10 125.2(3) . . ?
O5 C11 C10 110.8(3) . . ?
O5 C12 H12A 109.5 . . ?
O5 C12 H12B 109.5 . . ?
O5 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N4 C13 C9 115.6(3) . . ?
N4 C13 C14 122.3(3) . . ?
C14 C13 C9 121.9(3) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 C13 119.4(3) . . ?
C15 C14 H14 120.3 . . ?
C14 C15 H15 120.7 . . ?
C14 C15 C16 118.7(4) . . ?
C16 C15 H15 120.7 . . ?
C15 C16 H16 120.9 . . ?
C17 C16 C15 118.1(3) . . ?
C17 C16 H16 120.9 . . ?
N4 C17 C16 124.2(3) . . ?
N4 C17 H17 117.9 . . ?
C16 C17 H17 117.9 . . ?
O6 C18 N3 124.0(3) . . ?
O6 C18 C9 118.9(3) . . ?
N3 C18 C9 116.9(3) . . ?
N3 C19 H19A 109.0 . . ?
N3 C19 H19B 109.0 . . ?
N3 C19 C20 112.7(3) . . ?
H19A C19 H19B 107.8 . . ?
C20 C19 H19A 109.0 . . ?
C20 C19 H19B 109.0 . . ?
C21 C20 C19 120.7(3) . . ?
C25 C20 C19 120.4(3) . . ?
C25 C20 C21 118.9(3) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 C20 120.8(3) . . ?
C22 C21 H21 119.6 . . ?
C21 C22 H22 120.2 . . ?
C21 C22 C23 119.5(3) . . ?
C23 C22 H22 120.2 . . ?
C22 C23 H23 119.9 . . ?
C24 C23 C22 120.3(3) . . ?
C24 C23 H23 119.9 . . ?
C23 C24 H24 120.3 . . ?
C23 C24 C25 119.5(3) . . ?
C25 C24 H24 120.3 . . ?
C20 C25 H25 119.5 . . ?
C24 C25 C20 121.0(3) . . ?
C24 C25 H25 119.5 . . ?

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 N2 C1 C2 173.5(3) . . . . ?
O1 N2 C1 C6 -3.5(5) . . . . ?
O2 N2 C1 C2 -5.2(5) . . . . ?
O2 N2 C1 C6 177.9(3) . . . . ?
O3 C7 C8 C9 177.6(4) . . . . ?
O3 C7 C8 C10 -63.8(6) . . . . ?
N1 C4 C5 C6 179.2(3) . . . . ?
N1 C7 C8 C9 -2.6(3) . . . . ?
N1 C7 C8 C10 115.9(3) . . . . ?
N1 C9 C13 N4 -173.1(3) . . . . ?
N1 C9 C13 C14 11.9(4) . . . . ?
N1 C9 C18 O6 -26.6(4) . . . . ?
N1 C9 C18 N3 157.4(3) . . . . ?
N2 C1 C2 C3 -177.0(3) . . . . ?
N2 C1 C6 C5 177.5(3) . . . . ?
N3 C19 C20 C21 -94.5(4) . . . . ?
N3 C19 C20 C25 85.3(4) . . . . ?
N4 C13 C14 C15 0.3(5) . . . . ?
C1 C2 C3 C4 -0.1(5) . . . . ?
C2 C1 C6 C5 0.6(5) . . . . ?
C2 C3 C4 N1 -178.7(3) . . . . ?
C2 C3 C4 C5 -0.3(5) . . . . ?
C3 C4 C5 C6 0.7(5) . . . . ?
C4 N1 C7 O3 -9.7(7) . . . . ?
C4 N1 C7 C8 170.5(4) . . . . ?
C4 N1 C9 C8 -170.9(3) . . . . ?
C4 N1 C9 C13 73.2(4) . . . . ?
C4 N1 C9 C18 -62.7(4) . . . . ?
C4 C5 C6 C1 -0.9(5) . . . . ?
C6 C1 C2 C3 -0.1(5) . . . . ?
C7 N1 C4 C3 -172.6(4) . . . . ?
C7 N1 C4 C5 9.0(6) . . . . ?
C7 N1 C9 C8 -2.7(3) . . . . ?
C7 N1 C9 C13 -118.6(3) . . . . ?
C7 N1 C9 C18 105.6(3) . . . . ?
C7 C8 C9 N1 2.4(3) . . . . ?
C7 C8 C9 C13 116.0(3) . . . . ?
C7 C8 C9 C18 -106.3(3) . . . . ?
C7 C8 C10 C11 -171.5(3) . . . . ?
C8 C9 C13 N4 90.1(3) . . . . ?
C8 C9 C13 C14 -84.9(4) . . . . ?
C8 C9 C18 O6 65.7(4) . . . . ?
C8 C9 C18 N3 -110.3(3) . . . . ?
C8 C10 C11 O4 -27.6(5) . . . . ?
C8 C10 C11 O5 152.2(3) . . . . ?
C9 N1 C4 C3 -8.7(5) . . . . ?
C9 N1 C4 C5 172.9(3) . . . . ?
C9 N1 C7 O3 -177.4(4) . . . . ?
C9 N1 C7 C8 2.8(3) . . . . ?
C9 C8 C10 C11 -73.2(4) . . . . ?
C9 C13 C14 C15 174.9(3) . . . . ?
C10 C8 C9 N1 -113.1(3) . . . . ?
C10 C8 C9 C13 0.4(4) . . . . ?
C10 C8 C9 C18 138.1(3) . . . . ?
C12 O5 C11 O4 0.5(5) . . . . ?
C12 O5 C11 C10 -179.3(3) . . . . ?
C13 N4 C17 C16 1.7(5) . . . . ?
C13 C9 C18 O6 -158.9(3) . . . . ?
C13 C9 C18 N3 25.1(4) . . . . ?
C13 C14 C15 C16 1.0(5) . . . . ?
C14 C15 C16 C17 -0.9(5) . . . . ?
C15 C16 C17 N4 -0.5(5) . . . . ?
C17 N4 C13 C9 -176.5(3) . . . . ?
C17 N4 C13 C14 -1.6(4) . . . . ?
C18 N3 C19 C20 96.9(4) . . . . ?
C18 C9 C13 N4 -42.5(4) . . . . ?
C18 C9 C13 C14 142.5(3) . . . . ?
C19 N3 C18 O6 4.4(5) . . . . ?
C19 N3 C18 C9 -179.8(3) . . . . ?
C19 C20 C21 C22 178.6(3) . . . . ?
C19 C20 C25 C24 -178.2(3) . . . . ?
C20 C21 C22 C23 0.1(6) . . . . ?
C21 C20 C25 C24 1.7(5) . . . . ?
C21 C22 C23 C24 0.6(6) . . . . ?
C22 C23 C24 C25 -0.2(6) . . . . ?
C23 C24 C25 C20 -1.0(6) . . . . ?
C25 C20 C21 C22 -1.3(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.347
_oxdiff_exptl_absorpt_empirical_full_min 0.733
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.6299(14) 385 12644 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.3701(14) 383 12644 nmt 1.0001 -0.0000 -0.0001 0.0001 -0.9999 -0.0000
-0.6418 -0.0057 -0.9985

_twin_special_details            
;
Component 2 rotated by -179.8575° 
 around [0.95 -0.00 -0.31] (reciprocal) or [1.00 -0.00 0.00] (direct)
;
