# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_2jand_0m
_database_code_depnum_ccdc_archive 'CCDC 1554251'
_audit_update_record             
;
2017-06-01 deposited with the CCDC.
2017-08-22 downloaded from the CCDC.
;
_audit_creation_date             2017-06-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        'azido acetate'
_chemical_formula_moiety         'C21 H23 N3 O5, C H Cl3'
_chemical_formula_sum            'C22 H24 Cl3 N3 O5'
_chemical_formula_weight         516.79
_chemical_absolute_configuration RS
_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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.8335(4)
_cell_length_b                   14.0885(6)
_cell_length_c                   17.7805(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2463.30(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8477
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      25.42
_cell_measurement_theta_min      2.37
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.410
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5924
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             996
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_unetI/netI     0.0507
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            22921
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.986
_diffrn_reflns_theta_min         2.291
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       empirical
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.773
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4150
_reflns_number_total             5371
_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         1.069
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.083
_refine_ls_abs_structure_details 
;
 Flack x determined using 1444 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.201
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         5371
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0866
_refine_ls_R_factor_gt           0.0616
_refine_ls_restrained_S_all      1.201
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1616
_refine_ls_wR_factor_ref         0.1772
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C1(H1), C22(H22)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C13(H13A,H13B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C18(H18), C17(H17), C16(H16), C15(H15), C12(H12), C8(H8), C9(H9),
 C10(H10), C11(H11)
2.d Fitted hexagon refined as free rotating group:
 C19(C18,C17,C16,C15,C14), C12(C7,C8,C9,C10,C11)
2.e Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_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
Cl2 Cl 0.15372(14) 0.56384(12) 0.67912(9) 0.0486(4) Uani 1 1 d . . . . .
Cl3 Cl 0.40500(16) 0.52770(13) 0.75644(9) 0.0526(5) Uani 1 1 d . . . . .
Cl1 Cl 0.2955(3) 0.38673(12) 0.65847(11) 0.0849(8) Uani 1 1 d . . . . .
O7 O 0.4516(3) 0.5340(2) 0.41877(17) 0.0237(7) Uani 1 1 d . . . . .
O4 O 0.4835(3) 0.7909(2) 0.4237(2) 0.0290(8) Uani 1 1 d . . . . .
O5 O 0.5460(4) 0.5640(3) 0.56749(18) 0.0335(9) Uani 1 1 d . . . . .
O6 O 0.4666(3) 0.7553(3) 0.5816(2) 0.0384(10) Uani 1 1 d . . . . .
N1 N 0.3624(4) 0.6963(3) 0.3406(2) 0.0260(9) Uani 1 1 d . . . . .
N2 N 0.3775(4) 0.7487(3) 0.2853(2) 0.0279(9) Uani 1 1 d . . . . .
O8 O 0.2592(4) 0.4964(3) 0.4789(3) 0.0551(12) Uani 1 1 d . . . . .
N3 N 0.3783(5) 0.7938(4) 0.2334(3) 0.0480(13) Uani 1 1 d . . . . .
C3 C 0.4784(4) 0.6989(3) 0.3925(2) 0.0209(10) Uani 1 1 d . . . . .
H3 H 0.563022 0.684678 0.365685 0.025 Uiso 1 1 calc R . . . .
C4 C 0.4533(5) 0.6257(3) 0.4537(2) 0.0220(10) Uani 1 1 d . . . . .
H4 H 0.366726 0.638132 0.479135 0.026 Uiso 1 1 calc R . . . .
C20 C 0.3479(5) 0.4753(4) 0.4354(3) 0.0287(11) Uani 1 1 d . . . . .
C5 C 0.5710(5) 0.6306(4) 0.5095(3) 0.0258(11) Uani 1 1 d . . . . .
H5 H 0.655196 0.612934 0.483493 0.031 Uiso 1 1 calc R . . . .
C1 C 0.5851(5) 0.7313(4) 0.5390(3) 0.0322(12) Uani 1 1 d . . . . .
H1 H 0.665805 0.735895 0.571067 0.039 Uiso 1 1 calc R . . . .
C19 C 0.6680(2) 0.3815(2) 0.5207(2) 0.0383(13) Uani 1 1 d . . . . .
H19 H 0.575186 0.375678 0.529648 0.046 Uiso 1 1 calc R . . . .
C18 C 0.7344(3) 0.3153(2) 0.4758(2) 0.0461(15) Uani 1 1 d G . . . .
H18 H 0.685956 0.265140 0.454809 0.055 Uiso 1 1 calc R . . . .
C17 C 0.8731(3) 0.3239(2) 0.4625(2) 0.0434(14) Uani 1 1 d G . . . .
H17 H 0.917468 0.279611 0.432454 0.052 Uiso 1 1 calc R . . . .
C16 C 0.9454(2) 0.3988(2) 0.4939(2) 0.0370(13) Uani 1 1 d G . . . .
H16 H 1.038212 0.404620 0.484937 0.044 Uiso 1 1 calc R . . . .
C15 C 0.8790(3) 0.4650(2) 0.53874(18) 0.0322(12) Uani 1 1 d G . . . .
H15 H 0.927446 0.515159 0.559775 0.039 Uiso 1 1 calc R . . . .
C14 C 0.7403(3) 0.4564(2) 0.55213(17) 0.0299(12) Uani 1 1 d G . . . .
C2 C 0.5999(5) 0.7979(4) 0.4724(3) 0.0302(11) Uani 1 1 d . . . . .
H2A H 0.608942 0.862663 0.490278 0.036 Uiso 1 1 calc R . . . .
H2B H 0.681482 0.781898 0.444491 0.036 Uiso 1 1 calc R . . . .
C21 C 0.3611(6) 0.3845(3) 0.3950(3) 0.0330(12) Uani 1 1 d . . . . .
H21A H 0.447456 0.356262 0.406578 0.050 Uiso 1 1 calc GR . . . .
H21B H 0.355193 0.395673 0.341811 0.050 Uiso 1 1 calc GR . . . .
H21C H 0.289394 0.342486 0.410173 0.050 Uiso 1 1 calc GR . . . .
C13 C 0.6684(5) 0.5289(5) 0.6018(3) 0.0383(13) Uani 1 1 d . . . . .
H13A H 0.646079 0.499667 0.649670 0.046 Uiso 1 1 calc R . . . .
H13B H 0.729350 0.581560 0.611565 0.046 Uiso 1 1 calc R . . . .
C22 C 0.3124(6) 0.5076(4) 0.6738(3) 0.0377(13) Uani 1 1 d . . . . .
H22 H 0.363012 0.535028 0.631598 0.045 Uiso 1 1 calc R . . . .
C12 C 0.3300(5) 0.9221(4) 0.6548(2) 0.065(2) Uani 1 1 d . . . . .
H12 H 0.374798 0.948169 0.613649 0.078 Uiso 1 1 calc R . . . .
C7 C 0.3729(3) 0.8360(3) 0.6846(2) 0.0538(19) Uani 1 1 d G . . . .
C8 C 0.3059(4) 0.7971(2) 0.7461(2) 0.0474(16) Uani 1 1 d G . . . .
H8 H 0.334689 0.739421 0.766045 0.057 Uiso 1 1 calc R . . . .
C9 C 0.1959(4) 0.8443(4) 0.7779(2) 0.061(2) Uani 1 1 d G . . . .
H9 H 0.151048 0.818242 0.819048 0.073 Uiso 1 1 calc R . . . .
C10 C 0.1529(4) 0.9304(4) 0.7481(3) 0.070(3) Uani 1 1 d G . . . .
H10 H 0.079280 0.962027 0.769352 0.084 Uiso 1 1 calc R . . . .
C11 C 0.2199(6) 0.9694(2) 0.6866(3) 0.071(3) Uani 1 1 d G . . . .
H11 H 0.191153 1.026992 0.666653 0.085 Uiso 1 1 calc R . . . .
C6 C 0.4949(7) 0.7785(6) 0.6566(4) 0.068(2) Uani 1 1 d . . . . .
H6A H 0.577600 0.815848 0.659838 0.081 Uiso 1 1 calc R . . . .
H6B H 0.506271 0.721436 0.686418 0.081 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
Cl2 C22 1.753(6) . ?
Cl3 C22 1.751(6) . ?
Cl1 C22 1.733(6) . ?
O7 C4 1.433(5) . ?
O7 C20 1.346(6) . ?
O4 C3 1.412(5) . ?
O4 C2 1.439(6) . ?
O5 C5 1.415(6) . ?
O5 C13 1.437(6) . ?
O6 C1 1.430(6) . ?
O6 C6 1.401(8) . ?
N1 N2 1.238(6) . ?
N1 C3 1.468(6) . ?
N2 N3 1.121(6) . ?
O8 C20 1.203(6) . ?
C3 H3 0.9800 . ?
C3 C4 1.518(6) . ?
C4 H4 0.9800 . ?
C4 C5 1.526(7) . ?
C20 C21 1.473(7) . ?
C5 H5 0.9800 . ?
C5 C1 1.520(7) . ?
C1 H1 0.9800 . ?
C1 C2 1.517(7) . ?
C19 H19 0.9300 . ?
C19 C18 1.3900 . ?
C19 C14 1.3900 . ?
C18 H18 0.9300 . ?
C18 C17 1.3900 . ?
C17 H17 0.9300 . ?
C17 C16 1.3900 . ?
C16 H16 0.9300 . ?
C16 C15 1.3900 . ?
C15 H15 0.9300 . ?
C15 C14 1.3900 . ?
C14 C13 1.524(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C22 H22 0.9800 . ?
C12 H12 0.9300 . ?
C12 C7 1.3900 . ?
C12 C11 1.3900 . ?
C7 C8 1.3900 . ?
C7 C6 1.531(8) . ?
C8 H8 0.9300 . ?
C8 C9 1.3900 . ?
C9 H9 0.9300 . ?
C9 C10 1.3900 . ?
C10 H10 0.9300 . ?
C10 C11 1.3900 . ?
C11 H11 0.9300 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C20 O7 C4 117.9(4) . . ?
C3 O4 C2 109.1(3) . . ?
C5 O5 C13 113.1(4) . . ?
C6 O6 C1 113.4(4) . . ?
N2 N1 C3 113.1(4) . . ?
N3 N2 N1 173.1(5) . . ?
O4 C3 N1 107.3(4) . . ?
O4 C3 H3 110.4 . . ?
O4 C3 C4 110.4(4) . . ?
N1 C3 H3 110.4 . . ?
N1 C3 C4 107.9(4) . . ?
C4 C3 H3 110.4 . . ?
O7 C4 C3 107.7(3) . . ?
O7 C4 H4 110.5 . . ?
O7 C4 C5 109.3(4) . . ?
C3 C4 H4 110.5 . . ?
C3 C4 C5 108.2(4) . . ?
C5 C4 H4 110.5 . . ?
O7 C20 C21 111.0(4) . . ?
O8 C20 O7 122.6(5) . . ?
O8 C20 C21 126.3(5) . . ?
O5 C5 C4 108.2(4) . . ?
O5 C5 H5 108.8 . . ?
O5 C5 C1 112.5(4) . . ?
C4 C5 H5 108.8 . . ?
C1 C5 C4 109.6(4) . . ?
C1 C5 H5 108.8 . . ?
O6 C1 C5 109.2(4) . . ?
O6 C1 H1 109.6 . . ?
O6 C1 C2 110.2(4) . . ?
C5 C1 H1 109.6 . . ?
C2 C1 C5 108.5(4) . . ?
C2 C1 H1 109.6 . . ?
C18 C19 H19 120.0 . . ?
C18 C19 C14 120.0 . . ?
C14 C19 H19 120.0 . . ?
C19 C18 H18 120.0 . . ?
C17 C18 C19 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C17 H17 120.0 . . ?
C18 C17 C16 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C16 H16 120.0 . . ?
C15 C16 C17 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C15 H15 120.0 . . ?
C14 C15 C16 120.0 . . ?
C14 C15 H15 120.0 . . ?
C19 C14 C13 120.3(3) . . ?
C15 C14 C19 120.0 . . ?
C15 C14 C13 119.7(3) . . ?
O4 C2 C1 110.5(4) . . ?
O4 C2 H2A 109.5 . . ?
O4 C2 H2B 109.5 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O5 C13 C14 111.9(4) . . ?
O5 C13 H13A 109.2 . . ?
O5 C13 H13B 109.2 . . ?
C14 C13 H13A 109.2 . . ?
C14 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
Cl2 C22 H22 108.4 . . ?
Cl3 C22 Cl2 110.2(3) . . ?
Cl3 C22 H22 108.4 . . ?
Cl1 C22 Cl2 111.5(3) . . ?
Cl1 C22 Cl3 109.9(3) . . ?
Cl1 C22 H22 108.4 . . ?
C7 C12 H12 120.0 . . ?
C7 C12 C11 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C7 C8 120.0 . . ?
C12 C7 C6 125.2(5) . . ?
C8 C7 C6 114.8(5) . . ?
C7 C8 H8 120.0 . . ?
C7 C8 C9 120.0 . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.0 . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C11 120.0 . . ?
C11 C10 H10 120.0 . . ?
C12 C11 H11 120.0 . . ?
C10 C11 C12 120.0 . . ?
C10 C11 H11 120.0 . . ?
O6 C6 C7 106.1(5) . . ?
O6 C6 H6A 110.5 . . ?
O6 C6 H6B 110.5 . . ?
C7 C6 H6A 110.5 . . ?
C7 C6 H6B 110.5 . . ?
H6A C6 H6B 108.7 . . ?

_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_28augb_0m
_database_code_depnum_ccdc_archive 'CCDC 1554252'
_audit_update_record             
;
2017-06-01 deposited with the CCDC.
2017-08-22 downloaded from the CCDC.
;
_audit_creation_date             2017-05-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            'Galctose diazide'
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C27 H28 N6 O4'
_chemical_formula_sum            'C27 H28 N6 O4'
_chemical_formula_weight         500.55
_chemical_absolute_configuration unknown
_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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.8746(7)
_cell_length_b                   9.3560(6)
_cell_length_c                   12.7699(9)
_cell_angle_alpha                90
_cell_angle_beta                 108.166(2)
_cell_angle_gamma                90
_cell_volume                     1234.49(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4239
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.82
_cell_measurement_theta_min      2.75
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.981
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1277 before and 0.0538 after correction.
The Ratio of minimum to maximum transmission is 0.8084.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             528.0
_exptl_crystal_size_max          .2
_exptl_crystal_size_mid          .18
_exptl_crystal_size_min          .16
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_unetI/netI     0.0882
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12546
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.342
_diffrn_reflns_theta_min         1.971
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.872
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.979
_reflns_number_gt                4257
_reflns_number_total             6100
_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-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 
;
 Flack x determined using 1450 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         6100
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1039
_refine_ls_R_factor_gt           0.0572
_refine_ls_restrained_S_all      1.032
_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)+(0.0646P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1351
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C23(H23), C21(H21), C22(H22), C20(H20), C19(H19)
2.b Secondary CH2 refined with riding coordinates:
 C011(H01A,H01B), C012(H01C,H01D), C016(H01E,H01F), C024(H02A,H02B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C11(H11), C10(H10), C9(H9), C8(H8), C17(H17), C16(H16), C15(H15),
 C13(H13), C18(H18), C4(H4), C5(H5), C1(H1), C2(H2), C3(H3)
2.d Fitted hexagon refined as free rotating group:
 C7(C12,C11,C10,C9,C8), C17(C16,C15,C14,C13,C18), C4(C5,C6,C1,C2,C3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.0632(2) 0.2130(3) 0.8074(2) 0.0232(6) Uani 1 1 d . . . . .
O3 O 0.7884(2) 0.0647(3) 1.07046(19) 0.0187(6) Uani 1 1 d . . . . .
O2 O 1.0181(2) -0.0119(3) 1.0047(2) 0.0192(6) Uani 1 1 d . . . . .
O4 O 0.8528(2) -0.0886(3) 0.7841(2) 0.0209(6) Uani 1 1 d . . . . .
N2 N 0.5997(3) -0.0308(4) 0.6422(3) 0.0270(8) Uani 1 1 d . . . . .
N4 N 0.6259(3) -0.1503(3) 0.9435(3) 0.0264(8) Uani 1 1 d . . . . .
N1 N 0.6264(3) -0.0312(4) 0.7433(3) 0.0257(8) Uani 1 1 d . . . . .
C7 C 1.20215(17) -0.0346(2) 1.16956(18) 0.0193(8) Uani 1 1 d . . . . .
C12 C 1.23076(19) -0.0951(3) 1.27383(18) 0.0234(8) Uani 1 1 d G . . . .
H12 H 1.168251 -0.097292 1.309610 0.028 Uiso 1 1 calc R . . . .
C11 C 1.3528(2) -0.1523(3) 1.32463(16) 0.0284(9) Uani 1 1 d G . . . .
H11 H 1.371954 -0.192806 1.394395 0.034 Uiso 1 1 calc R . . . .
C10 C 1.44624(17) -0.1490(3) 1.27116(19) 0.0275(9) Uani 1 1 d G . . . .
H10 H 1.527896 -0.187294 1.305149 0.033 Uiso 1 1 calc R . . . .
C9 C 1.41763(19) -0.0885(3) 1.16689(19) 0.0284(9) Uani 1 1 d G . . . .
H9 H 1.480137 -0.086268 1.131117 0.034 Uiso 1 1 calc R . . . .
C8 C 1.2956(2) -0.0313(3) 1.11609(15) 0.0226(8) Uani 1 1 d G . . . .
H8 H 1.276435 0.009247 1.046330 0.027 Uiso 1 1 calc R . . . .
C23 C 0.7479(3) -0.1041(4) 0.9254(3) 0.0189(8) Uani 1 1 d . . . . .
H23 H 0.817322 -0.167150 0.968340 0.023 Uiso 1 1 calc R . . . .
C011 C 1.0697(3) 0.0297(4) 1.1180(3) 0.0236(9) Uani 1 1 d . . . . .
H01A H 1.012027 -0.002062 1.157911 0.028 Uiso 1 1 calc R . . . .
H01B H 1.075532 0.133021 1.122953 0.028 Uiso 1 1 calc R . . . .
C012 C 1.1921(3) 0.2353(4) 0.8039(3) 0.0243(9) Uani 1 1 d . . . . .
H01C H 1.249108 0.166800 0.852585 0.029 Uiso 1 1 calc R . . . .
H01D H 1.220193 0.330113 0.831947 0.029 Uiso 1 1 calc R . . . .
C21 C 0.9170(3) 0.0787(4) 0.9406(3) 0.0183(8) Uani 1 1 d . . . . .
H21 H 0.941473 0.178617 0.958917 0.022 Uiso 1 1 calc R . . . .
C22 C 0.7869(3) 0.0497(4) 0.9600(3) 0.0178(8) Uani 1 1 d . . . . .
H22 H 0.721574 0.114414 0.913555 0.021 Uiso 1 1 calc R . . . .
C016 C 0.7792(4) 0.2101(4) 1.1027(3) 0.0252(9) Uani 1 1 d . . . . .
H01E H 0.702739 0.254893 1.052977 0.030 Uiso 1 1 calc R . . . .
H01F H 0.854613 0.263600 1.100241 0.030 Uiso 1 1 calc R . . . .
C20 C 0.8996(3) 0.0539(4) 0.8186(3) 0.0204(8) Uani 1 1 d . . . . .
H20 H 0.836174 0.122885 0.775273 0.025 Uiso 1 1 calc R . . . .
N5 N 0.5441(3) -0.0555(4) 0.9333(3) 0.0285(8) Uani 1 1 d . . . . .
C17 C 0.7540(2) 0.1964(3) 1.43065(15) 0.0311(10) Uani 1 1 d . . . . .
H17 H 0.748258 0.192118 1.501748 0.037 Uiso 1 1 calc R . . . .
C16 C 0.64315(19) 0.1816(3) 1.3405(2) 0.0317(10) Uani 1 1 d G . . . .
H16 H 0.563313 0.167330 1.351241 0.038 Uiso 1 1 calc R . . . .
C15 C 0.65167(17) 0.1880(3) 1.23421(17) 0.0272(9) Uani 1 1 d G . . . .
H15 H 0.577536 0.178068 1.173876 0.033 Uiso 1 1 calc R . . . .
C14 C 0.7710(2) 0.2093(3) 1.21812(14) 0.0214(8) Uani 1 1 d G . . . .
C13 C 0.88181(17) 0.2241(3) 1.30829(18) 0.0246(9) Uani 1 1 d G . . . .
H13 H 0.961651 0.238383 1.297522 0.030 Uiso 1 1 calc R . . . .
C18 C 0.8733(2) 0.2177(3) 1.41456(15) 0.0315(9) Uani 1 1 d G . . . .
H18 H 0.947430 0.227645 1.474888 0.038 Uiso 1 1 calc R . . . .
C024 C 1.0225(4) 0.0693(4) 0.7886(3) 0.0226(8) Uani 1 1 d . . . . .
H02A H 1.088734 0.005991 0.833574 0.027 Uiso 1 1 calc R . . . .
H02B H 1.006920 0.044612 0.711782 0.027 Uiso 1 1 calc R . . . .
C4 C 1.2585(2) 0.0828(2) 0.5506(2) 0.0293(10) Uani 1 1 d . . . . .
H4 H 1.284606 -0.002806 0.527242 0.035 Uiso 1 1 calc R . . . .
C5 C 1.2453(2) 0.0929(2) 0.65519(18) 0.0236(9) Uani 1 1 d G . . . .
H5 H 1.262640 0.014009 0.701795 0.028 Uiso 1 1 calc R . . . .
C6 C 1.2062(2) 0.2209(3) 0.69011(15) 0.0206(8) Uani 1 1 d G . . . .
C1 C 1.1803(2) 0.3389(2) 0.62045(19) 0.0241(9) Uani 1 1 d G . . . .
H1 H 1.154186 0.424536 0.643814 0.029 Uiso 1 1 calc R . . . .
C2 C 1.1935(3) 0.3288(2) 0.51587(18) 0.0298(9) Uani 1 1 d G . . . .
H2 H 1.176152 0.407724 0.469261 0.036 Uiso 1 1 calc R . . . .
C3 C 1.2326(3) 0.2008(3) 0.48095(15) 0.0295(10) Uani 1 1 d G . . . .
H3 H 1.241362 0.194055 0.410973 0.035 Uiso 1 1 calc R . . . .
N3 N 0.5660(4) -0.0179(5) 0.5499(3) 0.0474(11) Uani 1 1 d . . . . .
N6 N 0.4617(4) 0.0192(5) 0.9285(3) 0.0450(10) Uani 1 1 d . . . . .
C19 C 0.7356(3) -0.1224(4) 0.8039(3) 0.0211(8) Uani 1 1 d . . . . .
H19 H 0.713605 -0.222205 0.782921 0.025 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 C012 1.432(4) . ?
O1 C024 1.413(5) . ?
O3 C22 1.412(4) . ?
O3 C016 1.434(4) . ?
O2 C011 1.432(4) . ?
O2 C21 1.427(4) . ?
O4 C20 1.446(4) . ?
O4 C19 1.411(4) . ?
N2 N1 1.232(4) . ?
N2 N3 1.126(4) . ?
N4 C23 1.480(4) . ?
N4 N5 1.234(4) . ?
N1 C19 1.471(5) . ?
C7 C12 1.3900 . ?
C7 C8 1.3900 . ?
C7 C011 1.509(4) . ?
C12 H12 0.9300 . ?
C12 C11 1.3900 . ?
C11 H11 0.9300 . ?
C11 C10 1.3900 . ?
C10 H10 0.9300 . ?
C10 C9 1.3900 . ?
C9 H9 0.9300 . ?
C9 C8 1.3900 . ?
C8 H8 0.9300 . ?
C23 H23 0.9800 . ?
C23 C22 1.526(5) . ?
C23 C19 1.525(5) . ?
C011 H01A 0.9700 . ?
C011 H01B 0.9700 . ?
C012 H01C 0.9700 . ?
C012 H01D 0.9700 . ?
C012 C6 1.514(4) . ?
C21 H21 0.9800 . ?
C21 C22 1.534(5) . ?
C21 C20 1.528(5) . ?
C22 H22 0.9800 . ?
C016 H01E 0.9700 . ?
C016 H01F 0.9700 . ?
C016 C14 1.503(4) . ?
C20 H20 0.9800 . ?
C20 C024 1.508(5) . ?
N5 N6 1.123(5) . ?
C17 H17 0.9300 . ?
C17 C16 1.3900 . ?
C17 C18 1.3900 . ?
C16 H16 0.9300 . ?
C16 C15 1.3900 . ?
C15 H15 0.9300 . ?
C15 C14 1.3900 . ?
C14 C13 1.3900 . ?
C13 H13 0.9300 . ?
C13 C18 1.3900 . ?
C18 H18 0.9300 . ?
C024 H02A 0.9700 . ?
C024 H02B 0.9700 . ?
C4 H4 0.9300 . ?
C4 C5 1.3900 . ?
C4 C3 1.3900 . ?
C5 H5 0.9300 . ?
C5 C6 1.3900 . ?
C6 C1 1.3900 . ?
C1 H1 0.9300 . ?
C1 C2 1.3900 . ?
C2 H2 0.9300 . ?
C2 C3 1.3900 . ?
C3 H3 0.9300 . ?
C19 H19 0.9800 . ?

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
C024 O1 C012 113.0(3) . . ?
C22 O3 C016 113.7(3) . . ?
C21 O2 C011 114.0(3) . . ?
C19 O4 C20 113.8(3) . . ?
N3 N2 N1 172.2(4) . . ?
N5 N4 C23 115.2(3) . . ?
N2 N1 C19 116.2(3) . . ?
C12 C7 C8 120.0 . . ?
C12 C7 C011 118.6(2) . . ?
C8 C7 C011 121.4(2) . . ?
C7 C12 H12 120.0 . . ?
C11 C12 C7 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C11 H11 120.0 . . ?
C12 C11 C10 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C10 H10 120.0 . . ?
C11 C10 C9 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C9 H9 120.0 . . ?
C8 C9 C10 120.0 . . ?
C8 C9 H9 120.0 . . ?
C7 C8 H8 120.0 . . ?
C9 C8 C7 120.0 . . ?
C9 C8 H8 120.0 . . ?
N4 C23 H23 108.0 . . ?
N4 C23 C22 114.3(3) . . ?
N4 C23 C19 109.1(3) . . ?
C22 C23 H23 108.0 . . ?
C19 C23 H23 108.0 . . ?
C19 C23 C22 109.2(3) . . ?
O2 C011 C7 110.7(3) . . ?
O2 C011 H01A 109.5 . . ?
O2 C011 H01B 109.5 . . ?
C7 C011 H01A 109.5 . . ?
C7 C011 H01B 109.5 . . ?
H01A C011 H01B 108.1 . . ?
O1 C012 H01C 108.7 . . ?
O1 C012 H01D 108.7 . . ?
O1 C012 C6 114.2(3) . . ?
H01C C012 H01D 107.6 . . ?
C6 C012 H01C 108.7 . . ?
C6 C012 H01D 108.7 . . ?
O2 C21 H21 109.0 . . ?
O2 C21 C22 112.7(3) . . ?
O2 C21 C20 108.8(3) . . ?
C22 C21 H21 109.0 . . ?
C20 C21 H21 109.0 . . ?
C20 C21 C22 108.1(3) . . ?
O3 C22 C23 107.4(3) . . ?
O3 C22 C21 114.8(3) . . ?
O3 C22 H22 108.9 . . ?
C23 C22 C21 107.9(3) . . ?
C23 C22 H22 108.9 . . ?
C21 C22 H22 108.9 . . ?
O3 C016 H01E 110.1 . . ?
O3 C016 H01F 110.1 . . ?
O3 C016 C14 107.9(3) . . ?
H01E C016 H01F 108.4 . . ?
C14 C016 H01E 110.1 . . ?
C14 C016 H01F 110.1 . . ?
O4 C20 C21 111.8(3) . . ?
O4 C20 H20 108.5 . . ?
O4 C20 C024 105.4(3) . . ?
C21 C20 H20 108.5 . . ?
C024 C20 C21 114.0(3) . . ?
C024 C20 H20 108.5 . . ?
N6 N5 N4 171.8(4) . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C18 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C16 H16 120.0 . . ?
C17 C16 C15 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C15 H15 120.0 . . ?
C14 C15 C16 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C14 C016 119.3(2) . . ?
C15 C14 C13 120.0 . . ?
C13 C14 C016 120.7(2) . . ?
C14 C13 H13 120.0 . . ?
C14 C13 C18 120.0 . . ?
C18 C13 H13 120.0 . . ?
C17 C18 H18 120.0 . . ?
C13 C18 C17 120.0 . . ?
C13 C18 H18 120.0 . . ?
O1 C024 C20 107.6(3) . . ?
O1 C024 H02A 110.2 . . ?
O1 C024 H02B 110.2 . . ?
C20 C024 H02A 110.2 . . ?
C20 C024 H02B 110.2 . . ?
H02A C024 H02B 108.5 . . ?
C5 C4 H4 120.0 . . ?
C5 C4 C3 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C012 121.1(2) . . ?
C1 C6 C012 118.9(2) . . ?
C1 C6 C5 120.0 . . ?
C6 C1 H1 120.0 . . ?
C2 C1 C6 120.0 . . ?
C2 C1 H1 120.0 . . ?
C1 C2 H2 120.0 . . ?
C1 C2 C3 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 H3 120.0 . . ?
C2 C3 C4 120.0 . . ?
C2 C3 H3 120.0 . . ?
O4 C19 N1 113.7(3) . . ?
O4 C19 C23 111.1(3) . . ?
O4 C19 H19 108.8 . . ?
N1 C19 C23 105.7(3) . . ?
N1 C19 H19 108.8 . . ?
C23 C19 H19 108.8 . . ?

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 C012 C6 C5 -95.3(3) . . . . ?
O1 C012 C6 C1 85.1(3) . . . . ?
O3 C016 C14 C15 -83.7(3) . . . . ?
O3 C016 C14 C13 93.9(3) . . . . ?
O2 C21 C22 O3 58.1(4) . . . . ?
O2 C21 C22 C23 -61.6(4) . . . . ?
O2 C21 C20 O4 66.0(3) . . . . ?
O2 C21 C20 C024 -53.5(4) . . . . ?
O4 C20 C024 O1 172.5(3) . . . . ?
N2 N1 C19 O4 58.1(4) . . . . ?
N2 N1 C19 C23 -179.8(3) . . . . ?
N4 C23 C22 O3 53.5(4) . . . . ?
N4 C23 C22 C21 177.7(3) . . . . ?
N4 C23 C19 O4 -176.1(3) . . . . ?
N4 C23 C19 N1 60.2(4) . . . . ?
C7 C12 C11 C10 0.0 . . . . ?
C12 C7 C8 C9 0.0 . . . . ?
C12 C7 C011 O2 -135.7(2) . . . . ?
C12 C11 C10 C9 0.0 . . . . ?
C11 C10 C9 C8 0.0 . . . . ?
C10 C9 C8 C7 0.0 . . . . ?
C8 C7 C12 C11 0.0 . . . . ?
C8 C7 C011 O2 45.7(4) . . . . ?
C011 O2 C21 C22 -77.6(4) . . . . ?
C011 O2 C21 C20 162.5(3) . . . . ?
C011 C7 C12 C11 -178.6(3) . . . . ?
C011 C7 C8 C9 178.6(3) . . . . ?
C012 O1 C024 C20 167.9(3) . . . . ?
C012 C6 C1 C2 179.5(2) . . . . ?
C21 O2 C011 C7 -160.0(3) . . . . ?
C21 C20 C024 O1 -64.5(4) . . . . ?
C22 O3 C016 C14 175.5(3) . . . . ?
C22 C23 C19 O4 58.3(4) . . . . ?
C22 C23 C19 N1 -65.4(3) . . . . ?
C22 C21 C20 O4 -56.8(4) . . . . ?
C22 C21 C20 C024 -176.2(3) . . . . ?
C016 O3 C22 C23 -159.7(3) . . . . ?
C016 O3 C22 C21 80.4(4) . . . . ?
C016 C14 C13 C18 -177.5(3) . . . . ?
C20 O4 C19 N1 62.4(4) . . . . ?
C20 O4 C19 C23 -56.6(4) . . . . ?
C20 C21 C22 O3 178.4(3) . . . . ?
C20 C21 C22 C23 58.8(3) . . . . ?
N5 N4 C23 C22 32.5(4) . . . . ?
N5 N4 C23 C19 -90.1(4) . . . . ?
C17 C16 C15 C14 0.0 . . . . ?
C16 C17 C18 C13 0.0 . . . . ?
C16 C15 C14 C016 177.6(3) . . . . ?
C16 C15 C14 C13 0.0 . . . . ?
C15 C14 C13 C18 0.0 . . . . ?
C14 C13 C18 C17 0.0 . . . . ?
C18 C17 C16 C15 0.0 . . . . ?
C024 O1 C012 C6 69.9(4) . . . . ?
C4 C5 C6 C012 -179.5(2) . . . . ?
C4 C5 C6 C1 0.0 . . . . ?
C5 C4 C3 C2 0.0 . . . . ?
C5 C6 C1 C2 0.0 . . . . ?
C6 C1 C2 C3 0.0 . . . . ?
C1 C2 C3 C4 0.0 . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C19 O4 C20 C21 56.7(4) . . . . ?
C19 O4 C20 C024 -179.0(3) . . . . ?
C19 C23 C22 O3 176.0(3) . . . . ?
C19 C23 C22 C21 -59.8(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
