# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1412465'
_audit_update_record             
;
2015-07-13 deposited with the CCDC.
2015-10-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
3-(benzylamino)-4-(((1S)-(6-methoxyquinolin-4-yl)((2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)amino)cyclobut-3-ene-1,2-dione
_chemical_name_common            
;
squaramide based cinchona catalyst
;
_chemical_melting_point          497(2)
_chemical_formula_moiety         'C31 H32 N4 O3'
_chemical_formula_sum            'C31 H32 N4 O3'
_chemical_formula_weight         508.60

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   8.7790(2)
_cell_length_b                   11.6400(2)
_cell_length_c                   26.194(1)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2676.7(1)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    21339
_cell_measurement_theta_min      6.50
_cell_measurement_theta_max      71.50

_exptl_crystal_description       platelet
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_F_000             1080
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.659
_shelx_estimated_absorpt_T_min   0.853
_shelx_estimated_absorpt_T_max   0.968
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.826
_exptl_absorpt_correction_T_max  0.941
_exptl_absorpt_process_details   'Rigaku, (2007)'
_exptl_absorpt_special_details   
;
'Num abs corr by T. Higashi (Rigaku, 2007)'
;
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'NORMAL-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  RAXIS-RAPID
_diffrn_measurement_method       dtprofit.ref
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            23228
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         6.538
_diffrn_reflns_theta_max         56.906
_diffrn_reflns_theta_full        56.906
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3579
_reflns_number_gt                2886
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.723
_reflns_Friedel_fraction_max     0.990
_reflns_Friedel_fraction_full    0.990

_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.
;

_computing_data_collection       'Crystal Clear V.1.4.1 (Rigaku/MSC, 2007)'
_computing_cell_refinement       'Crystal Clear V.1.4.1 (Rigaku/MSC, 2007)'
_computing_data_reduction        'Crystal Clear V.1.4.1 (Rigaku/MSC, 2007)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0240P)²+0.9144P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0033(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1031 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(5)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         3579
_refine_ls_number_parameters     345
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0333
_refine_ls_wR_factor_ref         0.0900
_refine_ls_wR_factor_gt          0.0657
_refine_ls_goodness_of_fit_ref   1.192
_refine_ls_restrained_S_all      1.192
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.7744(3) 0.6853(3) 0.13054(11) 0.0585(8) Uani 1 1 d . . . . .
O2 O 0.3504(4) 0.5890(3) 0.22545(11) 0.0600(9) Uani 1 1 d . . . . .
O3 O 0.5653(4) 0.5814(3) 0.32493(11) 0.0659(9) Uani 1 1 d . . . . .
N1 N 0.1442(4) 0.2868(3) 0.20623(11) 0.0445(9) Uani 1 1 d . . . . .
N1A N 0.4596(3) 0.3304(3) 0.19346(10) 0.0388(8) Uani 1 1 d . . . . .
H1A H 0.4689 0.2481 0.1970 0.047 Uiso 1 1 d R U . . .
N1B N 0.6791(4) 0.3213(3) 0.29470(12) 0.0487(9) Uani 1 1 d . . . . .
H1B H 0.6854 0.2398 0.2745 0.058 Uiso 1 1 d R U . . .
N11 N 0.5917(4) 0.3306(3) 0.00564(12) 0.0586(10) Uani 1 1 d . . . . .
C2 C 0.0342(5) 0.1917(4) 0.20785(16) 0.0580(12) Uani 1 1 d . . . . .
H2A H -0.0152 0.1910 0.2410 0.070 Uiso 1 1 calc R U . . .
H2B H 0.0885 0.1196 0.2040 0.070 Uiso 1 1 calc R U . . .
C3 C -0.0899(5) 0.2004(4) 0.16540(17) 0.0613(13) Uani 1 1 d . . . . .
H3 H -0.1900 0.1981 0.1819 0.074 Uiso 1 1 calc R U . . .
C3A C -0.0818(7) 0.1040(5) 0.1282(2) 0.0872(18) Uani 1 1 d . . . . .
H3A H 0.0079 0.0972 0.1095 0.105 Uiso 1 1 calc R U . . .
C3B C -0.1833(9) 0.0311(8) 0.1194(3) 0.180(4) Uani 1 1 d . . . . .
H3BA H -0.2751 0.0341 0.1370 0.217 Uiso 1 1 calc R U . . .
H3BB H -0.1668 -0.0261 0.0952 0.217 Uiso 1 1 calc R U . . .
C4 C -0.0698(5) 0.3199(4) 0.14103(16) 0.0548(13) Uani 1 1 d . . . . .
H4 H -0.1505 0.3332 0.1158 0.066 Uiso 1 1 calc R U . . .
C5 C -0.0773(5) 0.4108(4) 0.18243(17) 0.0637(13) Uani 1 1 d . . . . .
H5A H -0.1708 0.4029 0.2018 0.076 Uiso 1 1 calc R U . . .
H5B H -0.0751 0.4869 0.1674 0.076 Uiso 1 1 calc R U . . .
C6 C 0.0620(5) 0.3936(4) 0.21758(16) 0.0577(12) Uani 1 1 d . . . . .
H6A H 0.1308 0.4582 0.2136 0.069 Uiso 1 1 calc R U . . .
H6B H 0.0282 0.3922 0.2528 0.069 Uiso 1 1 calc R U . . .
C7 C 0.0863(4) 0.3289(4) 0.11529(14) 0.0523(12) Uani 1 1 d . . . . .
H7A H 0.1056 0.4077 0.1050 0.063 Uiso 1 1 calc R U . . .
H7B H 0.0892 0.2807 0.0851 0.063 Uiso 1 1 calc R U . . .
C8 C 0.2085(4) 0.2892(4) 0.15399(13) 0.0393(10) Uani 1 1 d . . . . .
H8 H 0.2364 0.2102 0.1451 0.047 Uiso 1 1 calc R U . . .
C9 C 0.3542(4) 0.3617(3) 0.15149(13) 0.0368(10) Uani 1 1 d . . . . .
H9 H 0.3255 0.4425 0.1559 0.044 Uiso 1 1 calc R U . . .
C10A C 0.4876(5) 0.4009(3) 0.23207(13) 0.0385(10) Uani 1 1 d . . . . .
C10B C 0.5829(5) 0.3979(3) 0.27561(14) 0.0409(10) Uani 1 1 d . . . . .
C10C C 0.4380(5) 0.5174(4) 0.24463(15) 0.0447(11) Uani 1 1 d . . . . .
C10D C 0.5366(5) 0.5140(4) 0.29005(16) 0.0486(11) Uani 1 1 d . . . . .
C12 C 0.4860(6) 0.2586(4) 0.02023(17) 0.0698(15) Uani 1 1 d . . . . .
H12 H 0.4608 0.1991 -0.0019 0.084 Uiso 1 1 calc R U . . .
C13 C 0.4080(5) 0.2649(4) 0.06685(15) 0.0554(12) Uani 1 1 d . . . . .
H13 H 0.3347 0.2100 0.0747 0.066 Uiso 1 1 calc R U . . .
C14 C 0.4384(4) 0.3506(3) 0.10072(13) 0.0371(10) Uani 1 1 d . . . . .
C14A C 0.5549(4) 0.4312(4) 0.08702(13) 0.0379(10) Uani 1 1 d . . . . .
C15 C 0.6018(5) 0.5240(3) 0.11841(14) 0.0417(11) Uani 1 1 d . . . . .
H15 H 0.5535 0.5367 0.1495 0.050 Uiso 1 1 calc R U . . .
C16 C 0.7179(5) 0.5950(4) 0.10331(15) 0.0432(10) Uani 1 1 d . . . . .
C17 C 0.7887(5) 0.5797(4) 0.05549(16) 0.0534(12) Uani 1 1 d . . . . .
H17 H 0.8666 0.6289 0.0454 0.064 Uiso 1 1 calc R U . . .
C18 C 0.7438(5) 0.4941(4) 0.02438(16) 0.0521(12) Uani 1 1 d . . . . .
H18 H 0.7901 0.4857 -0.0073 0.063 Uiso 1 1 calc R U . . .
C18A C 0.6274(5) 0.4165(4) 0.03906(14) 0.0446(11) Uani 1 1 d . . . . .
C19 C 0.7095(5) 0.7082(4) 0.17925(16) 0.0641(13) Uani 1 1 d . . . . .
H19A H 0.7250 0.6432 0.2012 0.096 Uiso 1 1 calc R U . . .
H19B H 0.6023 0.7221 0.1755 0.096 Uiso 1 1 calc R U . . .
H19C H 0.7574 0.7746 0.1939 0.096 Uiso 1 1 calc R U . . .
C20 C 0.7723(5) 0.3451(4) 0.34034(15) 0.0610(13) Uani 1 1 d . . . . .
H20A H 0.7731 0.4273 0.3466 0.073 Uiso 1 1 calc R U . . .
H20B H 0.8764 0.3213 0.3338 0.073 Uiso 1 1 calc R U . . .
C21 C 0.7152(5) 0.2850(4) 0.38702(16) 0.0555(12) Uani 1 1 d . . . . .
C22 C 0.5864(6) 0.3229(5) 0.41204(19) 0.0724(15) Uani 1 1 d . . . . .
H22 H 0.5355 0.3876 0.4000 0.087 Uiso 1 1 calc R U . . .
C23 C 0.5314(8) 0.2664(7) 0.4548(2) 0.099(2) Uani 1 1 d . . . . .
H23 H 0.4441 0.2925 0.4712 0.118 Uiso 1 1 calc R U . . .
C24 C 0.6071(10) 0.1716(7) 0.4725(2) 0.104(3) Uani 1 1 d . . . . .
H24 H 0.5712 0.1330 0.5012 0.125 Uiso 1 1 calc R U . . .
C25 C 0.7351(9) 0.1334(5) 0.4482(2) 0.095(2) Uani 1 1 d . . . . .
H25 H 0.7861 0.0691 0.4604 0.114 Uiso 1 1 calc R U . . .
C26 C 0.7889(6) 0.1895(5) 0.40565(18) 0.0722(15) Uani 1 1 d . . . . .
H26 H 0.8760 0.1626 0.3893 0.087 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C16 1.363(5) . ?
O1 C19 1.422(5) . ?
O2 C10C 1.240(5) . ?
O3 C10D 1.230(4) . ?
N1 C6 1.468(5) . ?
N1 C2 1.470(5) . ?
N1 C8 1.481(4) . ?
N1A C10A 1.326(4) . ?
N1A C9 1.482(4) . ?
N1A H1A 0.9667 . ?
N1B C10B 1.326(5) . ?
N1B C20 1.475(5) . ?
N1B H1B 1.0882 . ?
N11 C12 1.308(5) . ?
N11 C18A 1.365(5) . ?
C2 C3 1.560(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C3A 1.489(7) . ?
C3 C4 1.540(6) . ?
C3 H3 0.9800 . ?
C3A C3B 1.252(8) . ?
C3A H3A 0.9300 . ?
C3B H3BA 0.9300 . ?
C3B H3BB 0.9300 . ?
C4 C5 1.517(6) . ?
C4 C7 1.531(5) . ?
C4 H4 0.9800 . ?
C5 C6 1.544(6) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.546(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.534(5) . ?
C8 H8 0.9800 . ?
C9 C14 1.527(5) . ?
C9 H9 0.9800 . ?
C10A C10B 1.415(5) . ?
C10A C10C 1.461(6) . ?
C10B C10D 1.461(6) . ?
C10C C10D 1.472(6) . ?
C12 C13 1.402(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.361(5) . ?
C13 H13 0.9300 . ?
C14 C14A 1.434(5) . ?
C14A C15 1.418(5) . ?
C14A C18A 1.419(5) . ?
C15 C16 1.371(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.410(5) . ?
C17 C18 1.347(6) . ?
C17 H17 0.9300 . ?
C18 C18A 1.417(5) . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.495(6) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C26 1.377(6) . ?
C21 C22 1.380(6) . ?
C22 C23 1.386(8) . ?
C22 H22 0.9300 . ?
C23 C24 1.369(9) . ?
C23 H23 0.9300 . ?
C24 C25 1.366(9) . ?
C24 H24 0.9300 . ?
C25 C26 1.374(7) . ?
C25 H25 0.9300 . ?
C26 H26 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
C16 O1 C19 117.9(3) . . ?
C6 N1 C2 108.0(3) . . ?
C6 N1 C8 111.0(3) . . ?
C2 N1 C8 107.0(3) . . ?
C10A N1A C9 122.0(3) . . ?
C10A N1A H1A 121.6 . . ?
C9 N1A H1A 111.6 . . ?
C10B N1B C20 122.2(4) . . ?
C10B N1B H1B 115.8 . . ?
C20 N1B H1B 122.0 . . ?
C12 N11 C18A 116.4(4) . . ?
N1 C2 C3 112.9(3) . . ?
N1 C2 H2A 109.0 . . ?
C3 C2 H2A 109.0 . . ?
N1 C2 H2B 109.0 . . ?
C3 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
C3A C3 C4 113.8(4) . . ?
C3A C3 C2 112.6(4) . . ?
C4 C3 C2 106.0(4) . . ?
C3A C3 H3 108.1 . . ?
C4 C3 H3 108.1 . . ?
C2 C3 H3 108.1 . . ?
C3B C3A C3 126.7(6) . . ?
C3B C3A H3A 116.6 . . ?
C3 C3A H3A 116.6 . . ?
C3A C3B H3BA 120.0 . . ?
C3A C3B H3BB 120.0 . . ?
H3BA C3B H3BB 120.0 . . ?
C5 C4 C7 107.8(4) . . ?
C5 C4 C3 109.2(4) . . ?
C7 C4 C3 110.3(4) . . ?
C5 C4 H4 109.8 . . ?
C7 C4 H4 109.8 . . ?
C3 C4 H4 109.8 . . ?
C4 C5 C6 107.6(4) . . ?
C4 C5 H5A 110.2 . . ?
C6 C5 H5A 110.2 . . ?
C4 C5 H5B 110.2 . . ?
C6 C5 H5B 110.2 . . ?
H5A C5 H5B 108.5 . . ?
N1 C6 C5 112.2(4) . . ?
N1 C6 H6A 109.2 . . ?
C5 C6 H6A 109.2 . . ?
N1 C6 H6B 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C4 C7 C8 108.2(3) . . ?
C4 C7 H7A 110.1 . . ?
C8 C7 H7A 110.1 . . ?
C4 C7 H7B 110.1 . . ?
C8 C7 H7B 110.1 . . ?
H7A C7 H7B 108.4 . . ?
N1 C8 C9 111.6(3) . . ?
N1 C8 C7 110.3(3) . . ?
C9 C8 C7 112.7(3) . . ?
N1 C8 H8 107.3 . . ?
C9 C8 H8 107.3 . . ?
C7 C8 H8 107.3 . . ?
N1A C9 C14 108.8(3) . . ?
N1A C9 C8 110.7(3) . . ?
C14 C9 C8 113.2(3) . . ?
N1A C9 H9 108.0 . . ?
C14 C9 H9 108.0 . . ?
C8 C9 H9 108.0 . . ?
N1A C10A C10B 135.2(4) . . ?
N1A C10A C10C 133.7(4) . . ?
C10B C10A C10C 91.0(3) . . ?
N1B C10B C10A 134.2(4) . . ?
N1B C10B C10D 134.6(4) . . ?
C10A C10B C10D 91.2(4) . . ?
O2 C10C C10A 135.8(4) . . ?
O2 C10C C10D 135.2(4) . . ?
C10A C10C C10D 89.0(3) . . ?
O3 C10D C10B 136.5(4) . . ?
O3 C10D C10C 134.7(4) . . ?
C10B C10D C10C 88.8(3) . . ?
N11 C12 C13 124.6(4) . . ?
N11 C12 H12 117.7 . . ?
C13 C12 H12 117.7 . . ?
C14 C13 C12 120.7(4) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C14A 117.2(3) . . ?
C13 C14 C9 122.3(4) . . ?
C14A C14 C9 120.5(3) . . ?
C15 C14A C18A 118.4(4) . . ?
C15 C14A C14 124.1(3) . . ?
C18A C14A C14 117.5(3) . . ?
C16 C15 C14A 120.5(4) . . ?
C16 C15 H15 119.7 . . ?
C14A C15 H15 119.7 . . ?
O1 C16 C15 125.8(4) . . ?
O1 C16 C17 113.7(4) . . ?
C15 C16 C17 120.5(4) . . ?
C18 C17 C16 120.2(4) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C18A 121.2(4) . . ?
C17 C18 H18 119.4 . . ?
C18A C18 H18 119.4 . . ?
N11 C18A C18 117.3(4) . . ?
N11 C18A C14A 123.6(4) . . ?
C18 C18A C14A 119.1(4) . . ?
O1 C19 H19A 109.5 . . ?
O1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N1B C20 C21 112.9(3) . . ?
N1B C20 H20A 109.0 . . ?
C21 C20 H20A 109.0 . . ?
N1B C20 H20B 109.0 . . ?
C21 C20 H20B 109.0 . . ?
H20A C20 H20B 107.8 . . ?
C26 C21 C22 118.4(5) . . ?
C26 C21 C20 120.7(5) . . ?
C22 C21 C20 120.9(5) . . ?
C21 C22 C23 121.2(6) . . ?
C21 C22 H22 119.4 . . ?
C23 C22 H22 119.4 . . ?
C24 C23 C22 119.2(7) . . ?
C24 C23 H23 120.4 . . ?
C22 C23 H23 120.4 . . ?
C25 C24 C23 120.2(6) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C24 C25 C26 120.4(6) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C25 C26 C21 120.6(6) . . ?
C25 C26 H26 119.7 . . ?
C21 C26 H26 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C2 C3 64.7(4) . . . . ?
C8 N1 C2 C3 -54.9(4) . . . . ?
N1 C2 C3 C3A 115.7(5) . . . . ?
N1 C2 C3 C4 -9.4(5) . . . . ?
C4 C3 C3A C3B -120.8(8) . . . . ?
C2 C3 C3A C3B 118.6(8) . . . . ?
C3A C3 C4 C5 -179.0(4) . . . . ?
C2 C3 C4 C5 -54.7(4) . . . . ?
C3A C3 C4 C7 -60.7(5) . . . . ?
C2 C3 C4 C7 63.5(4) . . . . ?
C7 C4 C5 C6 -54.3(5) . . . . ?
C3 C4 C5 C6 65.5(4) . . . . ?
C2 N1 C6 C5 -53.6(4) . . . . ?
C8 N1 C6 C5 63.4(4) . . . . ?
C4 C5 C6 N1 -9.2(5) . . . . ?
C5 C4 C7 C8 68.9(4) . . . . ?
C3 C4 C7 C8 -50.2(5) . . . . ?
C6 N1 C8 C9 78.1(4) . . . . ?
C2 N1 C8 C9 -164.3(3) . . . . ?
C6 N1 C8 C7 -48.0(4) . . . . ?
C2 N1 C8 C7 69.6(4) . . . . ?
C4 C7 C8 N1 -15.7(5) . . . . ?
C4 C7 C8 C9 -141.2(4) . . . . ?
C10A N1A C9 C14 124.6(4) . . . . ?
C10A N1A C9 C8 -110.3(4) . . . . ?
N1 C8 C9 N1A 48.0(4) . . . . ?
C7 C8 C9 N1A 172.7(3) . . . . ?
N1 C8 C9 C14 170.5(3) . . . . ?
C7 C8 C9 C14 -64.7(4) . . . . ?
C9 N1A C10A C10B -177.6(4) . . . . ?
C9 N1A C10A C10C -2.2(6) . . . . ?
C20 N1B C10B C10A 176.1(4) . . . . ?
C20 N1B C10B C10D -1.4(7) . . . . ?
N1A C10A C10B N1B -1.4(8) . . . . ?
C10C C10A C10B N1B -178.0(4) . . . . ?
N1A C10A C10B C10D 176.9(4) . . . . ?
C10C C10A C10B C10D 0.2(3) . . . . ?
N1A C10A C10C O2 3.0(8) . . . . ?
C10B C10A C10C O2 179.8(5) . . . . ?
N1A C10A C10C C10D -176.9(4) . . . . ?
C10B C10A C10C C10D -0.2(3) . . . . ?
N1B C10B C10D O3 -2.3(9) . . . . ?
C10A C10B C10D O3 179.4(5) . . . . ?
N1B C10B C10D C10C 178.0(4) . . . . ?
C10A C10B C10D C10C -0.2(3) . . . . ?
O2 C10C C10D O3 0.6(9) . . . . ?
C10A C10C C10D O3 -179.5(5) . . . . ?
O2 C10C C10D C10B -179.8(5) . . . . ?
C10A C10C C10D C10B 0.2(3) . . . . ?
C18A N11 C12 C13 0.6(7) . . . . ?
N11 C12 C13 C14 0.6(8) . . . . ?
C12 C13 C14 C14A -1.4(6) . . . . ?
C12 C13 C14 C9 178.9(4) . . . . ?
N1A C9 C14 C13 108.5(4) . . . . ?
C8 C9 C14 C13 -15.1(5) . . . . ?
N1A C9 C14 C14A -71.2(4) . . . . ?
C8 C9 C14 C14A 165.2(3) . . . . ?
C13 C14 C14A C15 -178.9(4) . . . . ?
C9 C14 C14A C15 0.8(5) . . . . ?
C13 C14 C14A C18A 0.9(5) . . . . ?
C9 C14 C14A C18A -179.4(3) . . . . ?
C18A C14A C15 C16 -2.1(5) . . . . ?
C14 C14A C15 C16 177.7(4) . . . . ?
C19 O1 C16 C15 0.7(6) . . . . ?
C19 O1 C16 C17 179.6(4) . . . . ?
C14A C15 C16 O1 -178.8(4) . . . . ?
C14A C15 C16 C17 2.4(6) . . . . ?
O1 C16 C17 C18 -179.7(4) . . . . ?
C15 C16 C17 C18 -0.7(6) . . . . ?
C16 C17 C18 C18A -1.2(6) . . . . ?
C12 N11 C18A C18 178.8(4) . . . . ?
C12 N11 C18A C14A -1.0(6) . . . . ?
C17 C18 C18A N11 -178.5(4) . . . . ?
C17 C18 C18A C14A 1.4(6) . . . . ?
C15 C14A C18A N11 -179.9(4) . . . . ?
C14 C14A C18A N11 0.3(6) . . . . ?
C15 C14A C18A C18 0.3(5) . . . . ?
C14 C14A C18A C18 -179.6(3) . . . . ?
C10B N1B C20 C21 105.0(5) . . . . ?
N1B C20 C21 C26 104.5(5) . . . . ?
N1B C20 C21 C22 -74.6(5) . . . . ?
C26 C21 C22 C23 -0.3(7) . . . . ?
C20 C21 C22 C23 178.8(4) . . . . ?
C21 C22 C23 C24 0.3(8) . . . . ?
C22 C23 C24 C25 -0.1(9) . . . . ?
C23 C24 C25 C26 -0.2(9) . . . . ?
C24 C25 C26 C21 0.2(8) . . . . ?
C22 C21 C26 C25 0.0(7) . . . . ?
C20 C21 C26 C25 -179.1(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1A H1A O3 0.97 2.05 2.947(4) 154 4_645
N1B H1B O2 1.09 1.78 2.768(4) 148 4_645

_refine_diff_density_max         0.183
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.043


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol/acetone'
