# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
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# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
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data_180603xcc1_0m
_database_code_depnum_ccdc_archive 'CCDC 1877710'
_audit_update_record             
;
2018-11-08 deposited with the CCDC.
2019-02-12 downloaded from the CCDC.
;
_audit_creation_date             2018-06-04
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H20 Br N3 O4'
_chemical_formula_sum            'C22 H20 Br N3 O4'
_chemical_formula_weight         470.31
_chemical_absolute_configuration ad
_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 0.0030 0.0020 '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 -0.2900 2.4600 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.2282(14)
_cell_length_b                   9.1743(14)
_cell_length_c                   12.829(2)
_cell_angle_alpha                90
_cell_angle_beta                 109.724(3)
_cell_angle_gamma                90
_cell_volume                     1022.4(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2544
_cell_measurement_temperature    120.15
_cell_measurement_theta_max      23.361
_cell_measurement_theta_min      2.381
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.045
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5699
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/3 (Bruker,2014/3) was used for absorption correction. wR2(int) was 0.0824 before and 0.0595 after correction. The Ratio of minimum to maximum transmission is 0.7644. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_unetI/netI     0.0782
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6118
_diffrn_reflns_point_group_measured_fraction_full 0.936
_diffrn_reflns_point_group_measured_fraction_max 0.899
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         2.788
_diffrn_ambient_temperature      120.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.734
_reflns_Friedel_fraction_full    0.865
_reflns_Friedel_fraction_max     0.812
_reflns_number_gt                3248
_reflns_number_total             4202
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details 
;
 Flack x determined using 1115 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.019(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.839
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4202
_refine_ls_number_restraints     58
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0326
_refine_ls_restrained_S_all      0.843
_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)] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0660
_refine_ls_wR_factor_ref         0.0730
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O3A) \\sim Ueq, Uanis(O3) \\sim Ueq, Uanis(O4A) \\sim Ueq, Uanis(O4)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Rigid body (RIGU) restrains
 O3, O4, N3, O3A, O4A, C17
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Fixed Sof: O3(0.5) O4(0.5) O3A(0.5) O4A(0.5)
5.a Ternary CH refined with riding coordinates:
 C4(H4), C15(H15), C16(H16)
5.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C13(H13A,H13B), C14(H14A,H14B), C17(H17A,H17B)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C19(H19), C21(H21),
 C22(H22)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.39697(5) 0.10238(5) 0.24007(3) 0.06132(16) Uani 1 1 d . . . . .
O1 O 0.1714(3) -0.5385(3) 0.1572(2) 0.0463(7) Uani 1 1 d . . . . .
O2 O 0.0452(3) -0.3237(3) 0.1095(2) 0.0468(7) Uani 1 1 d . . . . .
O3 O -0.081(2) -0.477(2) -0.5019(17) 0.129(8) Uani 0.5 1 d . U P A 1
O4 O 0.0916(16) -0.6419(13) -0.4461(12) 0.109(4) Uani 0.5 1 d . U P A 1
N1 N 0.1585(3) -0.2345(3) -0.1193(2) 0.0337(7) Uani 1 1 d . . . . .
N2 N 0.1395(3) -0.4458(3) -0.0087(2) 0.0335(7) Uani 1 1 d . . . . .
N3 N 0.0456(5) -0.5171(5) -0.4501(3) 0.0598(10) Uani 1 1 d . U . . .
C1 C 0.3579(4) 0.0403(4) 0.0909(3) 0.0419(9) Uani 1 1 d . . . . .
C2 C 0.2666(4) -0.0809(4) 0.0534(3) 0.0362(8) Uani 1 1 d . . . . .
H2 H 0.2244 -0.1347 0.0995 0.043 Uiso 1 1 calc R . . . .
C3 C 0.2406(4) -0.1191(4) -0.0562(3) 0.0353(8) Uani 1 1 d . . . . .
C4 C 0.0647(4) -0.3568(3) -0.1040(3) 0.0338(8) Uani 1 1 d . . . . .
H4 H -0.0396 -0.3242 -0.1059 0.041 Uiso 1 1 calc R . . . .
C5 C 0.1119(4) -0.4269(4) 0.0872(3) 0.0368(9) Uani 1 1 d . . . . .
C6 C 0.1713(5) -0.5166(5) 0.2684(3) 0.0515(10) Uani 1 1 d . . . . .
H6A H 0.1898 -0.6110 0.3081 0.062 Uiso 1 1 calc R . . . .
H6B H 0.0690 -0.4804 0.2656 0.062 Uiso 1 1 calc R . . . .
C7 C 0.2922(4) -0.4098(6) 0.3306(3) 0.0435(8) Uani 1 1 d . . . . .
C8 C 0.2584(5) -0.2927(5) 0.3855(4) 0.0632(12) Uani 1 1 d . . . . .
H8 H 0.1552 -0.2769 0.3821 0.076 Uiso 1 1 calc R . . . .
C9 C 0.3725(7) -0.1976(6) 0.4456(4) 0.0781(16) Uani 1 1 d . . . . .
H9 H 0.3481 -0.1194 0.4853 0.094 Uiso 1 1 calc R . . . .
C10 C 0.5201(6) -0.2166(6) 0.4478(4) 0.0716(14) Uani 1 1 d . . . . .
H10 H 0.5987 -0.1514 0.4887 0.086 Uiso 1 1 calc R . . . .
C11 C 0.5544(6) -0.3293(6) 0.3912(5) 0.0743(14) Uani 1 1 d . . . . .
H11 H 0.6569 -0.3414 0.3916 0.089 Uiso 1 1 calc R . . . .
C12 C 0.4413(5) -0.4262(5) 0.3329(4) 0.0604(12) Uani 1 1 d . . . . .
H12 H 0.4669 -0.5048 0.2941 0.072 Uiso 1 1 calc R . . . .
C13 C 0.2129(5) -0.5771(4) -0.0357(3) 0.0421(9) Uani 1 1 d . . . . .
H13A H 0.1602 -0.6669 -0.0248 0.051 Uiso 1 1 calc R . . . .
H13B H 0.3229 -0.5826 0.0106 0.051 Uiso 1 1 calc R . . . .
C14 C 0.1945(5) -0.5564(4) -0.1561(4) 0.0442(10) Uani 1 1 d . . . . .
H14A H 0.1746 -0.6511 -0.1955 0.053 Uiso 1 1 calc R . . . .
H14B H 0.2889 -0.5133 -0.1634 0.053 Uiso 1 1 calc R . . . .
C15 C 0.0561(4) -0.4526(4) -0.2046(3) 0.0354(8) Uani 1 1 d . . . . .
H15 H -0.0431 -0.5078 -0.2317 0.042 Uiso 1 1 calc R . . . .
C16 C 0.0713(4) -0.3460(4) -0.2939(3) 0.0383(9) Uani 1 1 d . . . . .
H16 H -0.0332 -0.3071 -0.3365 0.046 Uiso 1 1 calc R . . . .
C17 C 0.1446(4) -0.4034(7) -0.3755(3) 0.0473(8) Uani 1 1 d . U . . .
H17A H 0.1607 -0.3217 -0.4208 0.057 Uiso 1 1 calc R . . . .
H17B H 0.2465 -0.4459 -0.3343 0.057 Uiso 1 1 calc R . . . .
C18 C 0.1652(4) -0.2251(4) -0.2245(3) 0.0380(8) Uani 1 1 d . . . . .
C19 C 0.2520(4) -0.1093(4) -0.2331(3) 0.0422(9) Uani 1 1 d . . . . .
H19 H 0.2744 -0.0797 -0.2970 0.051 Uiso 1 1 calc R . . . .
C20 C 0.3033(4) -0.0405(4) -0.1262(3) 0.0381(8) Uani 1 1 d . . . . .
C21 C 0.3965(4) 0.0810(5) -0.0818(3) 0.0456(9) Uani 1 1 d . . . . .
H21 H 0.4397 0.1362 -0.1267 0.055 Uiso 1 1 calc R . . . .
C22 C 0.4248(4) 0.1193(5) 0.0261(3) 0.0458(10) Uani 1 1 d . . . . .
H22 H 0.4900 0.1998 0.0569 0.055 Uiso 1 1 calc R . . . .
O3A O -0.0886(16) -0.5219(18) -0.4732(14) 0.080(4) Uani 0.5 1 d . U P A 2
O4A O 0.1121(14) -0.5929(13) -0.4966(10) 0.094(4) Uani 0.5 1 d . U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.911(4) . ?
O1 C5 1.350(4) . ?
O1 C6 1.441(5) . ?
O2 C5 1.215(4) . ?
O3 N3 1.193(17) . ?
O4 N3 1.217(12) . ?
N1 C3 1.391(5) . ?
N1 C4 1.471(4) . ?
N1 C18 1.374(5) . ?
N2 C4 1.438(4) . ?
N2 C5 1.349(5) . ?
N2 C13 1.479(5) . ?
N3 C17 1.500(6) . ?
N3 O3A 1.173(14) . ?
N3 O4A 1.210(11) . ?
C1 C2 1.380(5) . ?
C1 C22 1.394(6) . ?
C2 C3 1.389(5) . ?
C3 C20 1.419(5) . ?
C4 C15 1.541(5) . ?
C6 C7 1.497(6) . ?
C7 C8 1.376(6) . ?
C7 C12 1.375(6) . ?
C8 C9 1.384(7) . ?
C9 C10 1.364(8) . ?
C10 C11 1.361(7) . ?
C11 C12 1.383(6) . ?
C13 C14 1.508(6) . ?
C14 C15 1.546(5) . ?
C15 C16 1.548(5) . ?
C16 C17 1.520(5) . ?
C16 C18 1.501(5) . ?
C18 C19 1.357(5) . ?
C19 C20 1.436(5) . ?
C20 C21 1.405(5) . ?
C21 C22 1.365(6) . ?

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
C5 O1 C6 114.6(3) . . ?
C3 N1 C4 137.0(3) . . ?
C18 N1 C3 109.1(3) . . ?
C18 N1 C4 113.8(3) . . ?
C4 N2 C13 112.9(3) . . ?
C5 N2 C4 121.2(3) . . ?
C5 N2 C13 124.1(3) . . ?
O3 N3 O4 125.4(12) . . ?
O3 N3 C17 114.3(11) . . ?
O4 N3 C17 119.9(8) . . ?
O3A N3 C17 123.5(9) . . ?
O3A N3 O4A 121.5(11) . . ?
O4A N3 C17 114.4(7) . . ?
C2 C1 Br1 118.4(3) . . ?
C2 C1 C22 123.5(4) . . ?
C22 C1 Br1 118.1(3) . . ?
C1 C2 C3 115.7(4) . . ?
N1 C3 C20 106.0(3) . . ?
C2 C3 N1 131.0(3) . . ?
C2 C3 C20 123.0(3) . . ?
N1 C4 C15 100.9(3) . . ?
N2 C4 N1 114.3(3) . . ?
N2 C4 C15 105.2(2) . . ?
O2 C5 O1 124.0(3) . . ?
O2 C5 N2 125.5(3) . . ?
N2 C5 O1 110.4(3) . . ?
O1 C6 C7 111.7(3) . . ?
C8 C7 C6 121.8(4) . . ?
C12 C7 C6 120.0(4) . . ?
C12 C7 C8 118.2(4) . . ?
C7 C8 C9 121.0(4) . . ?
C10 C9 C8 119.8(5) . . ?
C11 C10 C9 119.8(5) . . ?
C10 C11 C12 120.6(5) . . ?
C7 C12 C11 120.5(5) . . ?
N2 C13 C14 103.6(3) . . ?
C13 C14 C15 106.4(3) . . ?
C4 C15 C14 102.3(3) . . ?
C4 C15 C16 105.5(3) . . ?
C14 C15 C16 114.7(3) . . ?
C17 C16 C15 117.6(3) . . ?
C18 C16 C15 101.9(3) . . ?
C18 C16 C17 111.3(3) . . ?
N3 C17 C16 111.3(3) . . ?
N1 C18 C16 109.1(3) . . ?
C19 C18 N1 110.6(3) . . ?
C19 C18 C16 140.2(3) . . ?
C18 C19 C20 106.3(3) . . ?
C3 C20 C19 107.9(3) . . ?
C21 C20 C3 118.1(3) . . ?
C21 C20 C19 134.0(4) . . ?
C22 C21 C20 119.8(4) . . ?
C21 C22 C1 119.9(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
Br1 C1 C2 C3 179.1(3) . . . . ?
Br1 C1 C22 C21 -178.3(3) . . . . ?
O1 C6 C7 C8 129.0(4) . . . . ?
O1 C6 C7 C12 -50.3(5) . . . . ?
O3 N3 C17 C16 57.6(13) . . . . ?
O4 N3 C17 C16 -115.4(9) . . . . ?
N1 C3 C20 C19 1.9(4) . . . . ?
N1 C3 C20 C21 -178.2(3) . . . . ?
N1 C4 C15 C14 92.4(3) . . . . ?
N1 C4 C15 C16 -27.9(3) . . . . ?
N1 C18 C19 C20 -0.2(4) . . . . ?
N2 C4 C15 C14 -26.7(3) . . . . ?
N2 C4 C15 C16 -147.0(3) . . . . ?
N2 C13 C14 C15 -23.5(4) . . . . ?
C1 C2 C3 N1 178.5(4) . . . . ?
C1 C2 C3 C20 0.3(5) . . . . ?
C2 C1 C22 C21 2.5(6) . . . . ?
C2 C3 C20 C19 -179.5(3) . . . . ?
C2 C3 C20 C21 0.3(5) . . . . ?
C3 N1 C4 N2 -52.9(5) . . . . ?
C3 N1 C4 C15 -165.2(4) . . . . ?
C3 N1 C18 C16 -177.7(3) . . . . ?
C3 N1 C18 C19 1.5(4) . . . . ?
C3 C20 C21 C22 0.4(5) . . . . ?
C4 N1 C3 C2 2.4(7) . . . . ?
C4 N1 C3 C20 -179.2(4) . . . . ?
C4 N1 C18 C16 0.2(4) . . . . ?
C4 N1 C18 C19 179.3(3) . . . . ?
C4 N2 C5 O1 168.6(3) . . . . ?
C4 N2 C5 O2 -12.5(5) . . . . ?
C4 N2 C13 C14 6.4(4) . . . . ?
C4 C15 C16 C17 150.3(3) . . . . ?
C4 C15 C16 C18 28.4(3) . . . . ?
C5 O1 C6 C7 -74.0(4) . . . . ?
C5 N2 C4 N1 98.3(4) . . . . ?
C5 N2 C4 C15 -152.0(3) . . . . ?
C5 N2 C13 C14 171.2(3) . . . . ?
C6 O1 C5 O2 -9.1(5) . . . . ?
C6 O1 C5 N2 169.9(3) . . . . ?
C6 C7 C8 C9 177.9(4) . . . . ?
C6 C7 C12 C11 -179.2(4) . . . . ?
C7 C8 C9 C10 2.3(8) . . . . ?
C8 C7 C12 C11 1.5(7) . . . . ?
C8 C9 C10 C11 -0.2(8) . . . . ?
C9 C10 C11 C12 -1.1(8) . . . . ?
C10 C11 C12 C7 0.5(7) . . . . ?
C12 C7 C8 C9 -2.9(7) . . . . ?
C13 N2 C4 N1 -96.4(3) . . . . ?
C13 N2 C4 C15 13.3(4) . . . . ?
C13 N2 C5 O1 4.9(5) . . . . ?
C13 N2 C5 O2 -176.2(3) . . . . ?
C13 C14 C15 C4 31.2(4) . . . . ?
C13 C14 C15 C16 144.9(3) . . . . ?
C14 C15 C16 C17 38.5(4) . . . . ?
C14 C15 C16 C18 -83.4(3) . . . . ?
C15 C16 C17 N3 66.9(5) . . . . ?
C15 C16 C18 N1 -18.0(4) . . . . ?
C15 C16 C18 C19 163.3(5) . . . . ?
C16 C18 C19 C20 178.5(4) . . . . ?
C17 C16 C18 N1 -144.2(3) . . . . ?
C17 C16 C18 C19 37.1(6) . . . . ?
C18 N1 C3 C2 179.5(4) . . . . ?
C18 N1 C3 C20 -2.1(4) . . . . ?
C18 N1 C4 N2 130.1(3) . . . . ?
C18 N1 C4 C15 17.7(4) . . . . ?
C18 C16 C17 N3 -176.1(4) . . . . ?
C18 C19 C20 C3 -1.1(4) . . . . ?
C18 C19 C20 C21 179.1(4) . . . . ?
C19 C20 C21 C22 -179.8(4) . . . . ?
C20 C21 C22 C1 -1.7(6) . . . . ?
C22 C1 C2 C3 -1.7(5) . . . . ?
O3A N3 C17 C16 27.2(12) . . . . ?
O4A N3 C17 C16 -162.0(8) . . . . ?

_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_180603xcc2_0m
_database_code_depnum_ccdc_archive 'CCDC 1877711'
_audit_update_record             
;
2018-11-08 deposited with the CCDC.
2019-02-12 downloaded from the CCDC.
;
_audit_creation_date             2018-06-04
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H24 N2 O7'
_chemical_formula_sum            'C21 H24 N2 O7'
_chemical_formula_weight         416.42
_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 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.6264(13)
_cell_length_b                   10.8580(14)
_cell_length_c                   11.2163(14)
_cell_angle_alpha                90
_cell_angle_beta                 113.736(2)
_cell_angle_gamma                90
_cell_volume                     1073.2(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1710
_cell_measurement_temperature    120.15
_cell_measurement_theta_max      20.967
_cell_measurement_theta_min      2.311
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6814
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/3 (Bruker,2014/3) was used for absorption correction. wR2(int) was 0.0479 before and 0.0367 after correction. The Ratio of minimum to maximum transmission is 0.9139. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6528
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.607
_diffrn_reflns_theta_min         2.730
_diffrn_ambient_temperature      120.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.900
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                3074
_reflns_number_total             4646
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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         0.120
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.9(18)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         4646
_refine_ls_number_restraints     31
_refine_ls_R_factor_all          0.0865
_refine_ls_R_factor_gt           0.0496
_refine_ls_restrained_S_all      1.057
_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)+(0.0501P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.1161
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 1.9(18)
 -0.9(18)
2. 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
3. Rigid body (RIGU) restrains
 O6, C13, C14, O6A, C13A, C14A, C12
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(O6A)=Sof(C13A)=Sof(H13C)=Sof(H13D)=Sof(C14A)=Sof(H14D)=Sof(H14E)=
 Sof(H14F)=1-FVAR(1)
 Sof(O6)=Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(H14C)=
 FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C2(H2), C7(H7), C16(H16)
5.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C10(H10A,H10B), C13(H13A,H13B), C15(H15A,H15B), C13A(H13C,H13D)
5.c Aromatic/amide H refined with riding coordinates:
 C17(H17), C18(H18), C19(H19), C20(H20)
5.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C14(H14A,H14B,H14C), C21(H21A,H21B,H21C), C14A(H14D,H14E,
 H14F)
;
_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 0.9294(4) 0.2504(3) 0.6834(3) 0.0911(9) Uani 1 1 d . . . . .
O2 O 0.8376(4) 0.0852(3) 0.5814(4) 0.1247(15) Uani 1 1 d . . . . .
O3 O 0.5366(2) 0.62718(19) 0.5429(2) 0.0478(6) Uani 1 1 d . . . . .
O4 O 0.6997(3) 0.7896(2) 0.4721(2) 0.0600(6) Uani 1 1 d . . . . .
O5 O 0.9119(3) 0.6812(3) 0.5826(3) 0.0826(9) Uani 1 1 d . . . . .
O6 O 0.8198(19) 0.7965(16) 0.7845(15) 0.079(3) Uani 0.55(2) 1 d . U P A 1
O7 O 0.5784(4) 0.7402(3) 0.7642(3) 0.0931(10) Uani 1 1 d . . . . .
N1 N 0.8537(4) 0.1954(3) 0.5843(4) 0.0740(9) Uani 1 1 d . . . . .
N2 N 0.7035(3) 0.4876(3) 0.2469(3) 0.0583(8) Uani 1 1 d . . . . .
C1 C 0.7743(4) 0.2648(3) 0.4605(3) 0.0564(9) Uani 1 1 d . . . . .
H1A H 0.6697 0.2328 0.4160 0.068 Uiso 1 1 calc R . . . .
H1B H 0.8277 0.2511 0.4025 0.068 Uiso 1 1 calc R . . . .
C2 C 0.7679(4) 0.4027(3) 0.4839(3) 0.0493(8) Uani 1 1 d . . . . .
H2 H 0.8727 0.4370 0.5285 0.059 Uiso 1 1 calc R . . . .
C3 C 0.6823(4) 0.4708(3) 0.3602(3) 0.0488(8) Uani 1 1 d . . . . .
C4 C 0.5842(5) 0.5593(3) 0.1654(4) 0.0607(10) Uani 1 1 d . . . . .
C5 C 0.4862(4) 0.5862(3) 0.2289(3) 0.0547(9) Uani 1 1 d . . . . .
C6 C 0.5540(4) 0.5273(3) 0.3527(3) 0.0472(8) Uani 1 1 d . . . . .
C7 C 0.5305(4) 0.5113(3) 0.4751(3) 0.0468(8) Uani 1 1 d . . . . .
H7 H 0.4337 0.4663 0.4583 0.056 Uiso 1 1 calc R . . . .
C8 C 0.6890(4) 0.6473(3) 0.6288(3) 0.0506(8) Uani 1 1 d . . . . .
C9 C 0.7816(4) 0.7070(3) 0.5601(4) 0.0561(9) Uani 1 1 d . . . . .
C10 C 0.7698(5) 0.8406(4) 0.3897(4) 0.0794(13) Uani 1 1 d . . . . .
H10A H 0.8052 0.7732 0.3494 0.095 Uiso 1 1 calc R . . . .
H10B H 0.8584 0.8916 0.4425 0.095 Uiso 1 1 calc R . . . .
C11 C 0.6558(6) 0.9170(5) 0.2869(5) 0.0956(15) Uani 1 1 d . . . . .
H11A H 0.6218 0.9837 0.3275 0.143 Uiso 1 1 calc GR . . . .
H11B H 0.5688 0.8657 0.2347 0.143 Uiso 1 1 calc GR . . . .
H11C H 0.7016 0.9520 0.2307 0.143 Uiso 1 1 calc GR . . . .
C12 C 0.6842(5) 0.7293(4) 0.7378(4) 0.0645(10) Uani 1 1 d . U . . .
C13 C 0.8409(16) 0.8817(14) 0.8908(15) 0.092(4) Uani 0.55(2) 1 d . U P A 1
H13A H 0.7431 0.9213 0.8774 0.110 Uiso 0.55(2) 1 calc R . P A 1
H13B H 0.9139 0.9469 0.8933 0.110 Uiso 0.55(2) 1 calc R . P A 1
C14 C 0.900(2) 0.811(2) 1.0170(13) 0.149(8) Uani 0.55(2) 1 d . U P A 1
H14A H 0.9977 0.7735 1.0302 0.223 Uiso 0.55(2) 1 calc GR . P A 1
H14B H 0.8274 0.7470 1.0138 0.223 Uiso 0.55(2) 1 calc GR . P A 1
H14C H 0.9140 0.8678 1.0891 0.223 Uiso 0.55(2) 1 calc GR . P A 1
C15 C 0.7505(4) 0.5185(3) 0.6810(3) 0.0591(9) Uani 1 1 d . . . . .
H15A H 0.8621 0.5151 0.7098 0.071 Uiso 1 1 calc R . . . .
H15B H 0.7243 0.4955 0.7548 0.071 Uiso 1 1 calc R . . . .
C16 C 0.6706(4) 0.4337(3) 0.5632(3) 0.0515(8) Uani 1 1 d . . . . .
H16 H 0.6367 0.3562 0.5915 0.062 Uiso 1 1 calc R . . . .
C17 C 0.3575(5) 0.6571(4) 0.1648(4) 0.0735(11) Uani 1 1 d . . . . .
H17 H 0.2916 0.6771 0.2063 0.088 Uiso 1 1 calc R . . . .
C18 C 0.3264(6) 0.6981(5) 0.0405(4) 0.0999(16) Uani 1 1 d . . . . .
H18 H 0.2373 0.7450 -0.0047 0.120 Uiso 1 1 calc R . . . .
C19 C 0.4239(7) 0.6716(6) -0.0196(4) 0.1096(19) Uani 1 1 d . . . . .
H19 H 0.4007 0.7020 -0.1049 0.131 Uiso 1 1 calc R . . . .
C20 C 0.5529(6) 0.6026(5) 0.0406(4) 0.0873(14) Uani 1 1 d . . . . .
H20 H 0.6187 0.5850 -0.0016 0.105 Uiso 1 1 calc R . . . .
C21 C 0.8336(5) 0.4497(4) 0.2214(4) 0.0739(11) Uani 1 1 d . . . . .
H21A H 0.8960 0.3925 0.2895 0.111 Uiso 1 1 calc GR . . . .
H21B H 0.8940 0.5222 0.2211 0.111 Uiso 1 1 calc GR . . . .
H21C H 0.7986 0.4088 0.1365 0.111 Uiso 1 1 calc GR . . . .
O6A O 0.810(2) 0.769(2) 0.8206(17) 0.085(5) Uani 0.45(2) 1 d . U P A 2
C13A C 0.807(2) 0.8392(16) 0.9332(15) 0.081(5) Uani 0.45(2) 1 d . U P A 2
H13C H 0.7180 0.8947 0.9050 0.097 Uiso 0.45(2) 1 calc R . P A 2
H13D H 0.8021 0.7825 1.0004 0.097 Uiso 0.45(2) 1 calc R . P A 2
C14A C 0.9467(15) 0.9098(19) 0.9840(15) 0.107(7) Uani 0.45(2) 1 d . U P A 2
H14D H 0.9684 0.9416 0.9115 0.160 Uiso 0.45(2) 1 calc GR . P A 2
H14E H 1.0303 0.8568 1.0390 0.160 Uiso 0.45(2) 1 calc GR . P A 2
H14F H 0.9357 0.9788 1.0359 0.160 Uiso 0.45(2) 1 calc GR . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.213(5) . ?
O2 N1 1.206(5) . ?
O3 C7 1.459(4) . ?
O3 C8 1.410(4) . ?
O4 C9 1.332(4) . ?
O4 C10 1.456(4) . ?
O5 C9 1.208(4) . ?
O6 C12 1.400(15) . ?
O6 C13 1.458(17) . ?
O7 C12 1.176(5) . ?
N1 C1 1.492(5) . ?
N2 C3 1.378(4) . ?
N2 C4 1.383(5) . ?
N2 C21 1.452(5) . ?
C1 C2 1.526(5) . ?
C2 C3 1.493(5) . ?
C2 C16 1.566(4) . ?
C3 C6 1.352(5) . ?
C4 C5 1.422(5) . ?
C4 C20 1.390(5) . ?
C5 C6 1.426(5) . ?
C5 C17 1.388(5) . ?
C6 C7 1.489(4) . ?
C7 C16 1.560(5) . ?
C8 C9 1.537(5) . ?
C8 C12 1.528(5) . ?
C8 C15 1.539(5) . ?
C10 C11 1.484(6) . ?
C12 O6A 1.269(18) . ?
C13 C14 1.50(3) . ?
C15 C16 1.539(5) . ?
C17 C18 1.377(6) . ?
C18 C19 1.388(7) . ?
C19 C20 1.373(7) . ?
O6A C13A 1.48(2) . ?
C13A C14A 1.45(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
C8 O3 C7 107.6(2) . . ?
C9 O4 C10 116.1(3) . . ?
C12 O6 C13 116.0(12) . . ?
O1 N1 C1 119.9(3) . . ?
O2 N1 O1 122.5(4) . . ?
O2 N1 C1 117.6(4) . . ?
C3 N2 C4 107.0(3) . . ?
C3 N2 C21 127.1(3) . . ?
C4 N2 C21 125.6(3) . . ?
N1 C1 C2 112.2(3) . . ?
C1 C2 C16 112.5(3) . . ?
C3 C2 C1 111.8(3) . . ?
C3 C2 C16 100.9(3) . . ?
N2 C3 C2 133.8(3) . . ?
C6 C3 N2 110.6(3) . . ?
C6 C3 C2 115.6(3) . . ?
N2 C4 C5 109.1(3) . . ?
N2 C4 C20 129.8(4) . . ?
C20 C4 C5 121.1(4) . . ?
C4 C5 C6 105.0(3) . . ?
C17 C5 C4 119.2(3) . . ?
C17 C5 C6 135.7(3) . . ?
C3 C6 C5 108.3(3) . . ?
C3 C6 C7 111.3(3) . . ?
C5 C6 C7 140.4(3) . . ?
O3 C7 C6 113.0(3) . . ?
O3 C7 C16 107.0(2) . . ?
C6 C7 C16 103.5(2) . . ?
O3 C8 C9 112.1(3) . . ?
O3 C8 C12 106.2(3) . . ?
O3 C8 C15 104.7(3) . . ?
C9 C8 C15 111.2(3) . . ?
C12 C8 C9 111.4(3) . . ?
C12 C8 C15 110.8(3) . . ?
O4 C9 C8 111.4(3) . . ?
O5 C9 O4 124.5(3) . . ?
O5 C9 C8 124.1(4) . . ?
O4 C10 C11 108.6(4) . . ?
O6 C12 C8 106.2(7) . . ?
O7 C12 O6 128.7(8) . . ?
O7 C12 C8 124.6(4) . . ?
O7 C12 O6A 116.7(10) . . ?
O6A C12 C8 117.2(10) . . ?
O6 C13 C14 108.8(14) . . ?
C16 C15 C8 103.5(3) . . ?
C7 C16 C2 108.6(2) . . ?
C15 C16 C2 114.2(3) . . ?
C15 C16 C7 103.1(2) . . ?
C18 C17 C5 119.2(4) . . ?
C17 C18 C19 120.7(5) . . ?
C20 C19 C18 121.9(4) . . ?
C19 C20 C4 117.8(4) . . ?
C12 O6A C13A 117.2(16) . . ?
C14A C13A O6A 105.9(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
O1 N1 C1 C2 -14.5(5) . . . . ?
O2 N1 C1 C2 164.5(4) . . . . ?
O3 C7 C16 C2 -122.0(3) . . . . ?
O3 C7 C16 C15 -0.5(3) . . . . ?
O3 C8 C9 O4 37.7(4) . . . . ?
O3 C8 C9 O5 -141.7(3) . . . . ?
O3 C8 C12 O6 -152.1(8) . . . . ?
O3 C8 C12 O7 20.7(5) . . . . ?
O3 C8 C12 O6A -173.6(13) . . . . ?
O3 C8 C15 C16 35.9(3) . . . . ?
O7 C12 O6A C13A -8(2) . . . . ?
N1 C1 C2 C3 -177.5(3) . . . . ?
N1 C1 C2 C16 -64.7(4) . . . . ?
N2 C3 C6 C5 -0.6(4) . . . . ?
N2 C3 C6 C7 -179.3(3) . . . . ?
N2 C4 C5 C6 0.3(4) . . . . ?
N2 C4 C5 C17 -179.8(3) . . . . ?
N2 C4 C20 C19 179.2(4) . . . . ?
C1 C2 C3 N2 -61.9(5) . . . . ?
C1 C2 C3 C6 116.5(3) . . . . ?
C1 C2 C16 C7 -116.0(3) . . . . ?
C1 C2 C16 C15 129.6(3) . . . . ?
C2 C3 C6 C5 -179.4(3) . . . . ?
C2 C3 C6 C7 1.9(4) . . . . ?
C3 N2 C4 C5 -0.7(4) . . . . ?
C3 N2 C4 C20 179.7(4) . . . . ?
C3 C2 C16 C7 3.3(3) . . . . ?
C3 C2 C16 C15 -111.1(3) . . . . ?
C3 C6 C7 O3 115.8(3) . . . . ?
C3 C6 C7 C16 0.4(4) . . . . ?
C4 N2 C3 C2 179.3(3) . . . . ?
C4 N2 C3 C6 0.8(4) . . . . ?
C4 C5 C6 C3 0.2(4) . . . . ?
C4 C5 C6 C7 178.2(4) . . . . ?
C4 C5 C17 C18 1.0(6) . . . . ?
C5 C4 C20 C19 -0.4(6) . . . . ?
C5 C6 C7 O3 -62.2(6) . . . . ?
C5 C6 C7 C16 -177.6(4) . . . . ?
C5 C17 C18 C19 -1.5(8) . . . . ?
C6 C5 C17 C18 -179.1(5) . . . . ?
C6 C7 C16 C2 -2.4(3) . . . . ?
C6 C7 C16 C15 119.1(3) . . . . ?
C7 O3 C8 C9 83.4(3) . . . . ?
C7 O3 C8 C12 -154.7(3) . . . . ?
C7 O3 C8 C15 -37.3(3) . . . . ?
C8 O3 C7 C6 -89.4(3) . . . . ?
C8 O3 C7 C16 23.8(3) . . . . ?
C8 C12 O6A C13A -174.6(12) . . . . ?
C8 C15 C16 C2 97.1(3) . . . . ?
C8 C15 C16 C7 -20.5(3) . . . . ?
C9 O4 C10 C11 172.4(3) . . . . ?
C9 C8 C12 O6 -29.8(9) . . . . ?
C9 C8 C12 O7 143.1(4) . . . . ?
C9 C8 C12 O6A -51.2(13) . . . . ?
C9 C8 C15 C16 -85.4(3) . . . . ?
C10 O4 C9 O5 6.9(5) . . . . ?
C10 O4 C9 C8 -172.5(3) . . . . ?
C12 O6 C13 C14 82.5(19) . . . . ?
C12 C8 C9 O4 -81.2(4) . . . . ?
C12 C8 C9 O5 99.4(4) . . . . ?
C12 C8 C15 C16 150.0(3) . . . . ?
C12 O6A C13A C14A -160(2) . . . . ?
C13 O6 C12 O7 7.8(18) . . . . ?
C13 O6 C12 C8 -179.7(10) . . . . ?
C15 C8 C9 O4 154.6(3) . . . . ?
C15 C8 C9 O5 -24.8(5) . . . . ?
C15 C8 C12 O6 94.7(9) . . . . ?
C15 C8 C12 O7 -92.5(5) . . . . ?
C15 C8 C12 O6A 73.2(13) . . . . ?
C16 C2 C3 N2 178.3(3) . . . . ?
C16 C2 C3 C6 -3.3(4) . . . . ?
C17 C5 C6 C3 -179.7(4) . . . . ?
C17 C5 C6 C7 -1.7(8) . . . . ?
C17 C18 C19 C20 1.0(9) . . . . ?
C18 C19 C20 C4 0.0(8) . . . . ?
C20 C4 C5 C6 180.0(4) . . . . ?
C20 C4 C5 C17 -0.1(6) . . . . ?
C21 N2 C3 C2 -6.9(6) . . . . ?
C21 N2 C3 C6 174.7(3) . . . . ?
C21 N2 C4 C5 -174.7(3) . . . . ?
C21 N2 C4 C20 5.8(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1.9(18)
2 -0.9(18)

